[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO2016096942A1 - Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress - Google Patents

Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress Download PDF

Info

Publication number
WO2016096942A1
WO2016096942A1 PCT/EP2015/079926 EP2015079926W WO2016096942A1 WO 2016096942 A1 WO2016096942 A1 WO 2016096942A1 EP 2015079926 W EP2015079926 W EP 2015079926W WO 2016096942 A1 WO2016096942 A1 WO 2016096942A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
carbonyl
substituted
radicals
Prior art date
Application number
PCT/EP2015/079926
Other languages
German (de)
French (fr)
Inventor
Lars ARVE
Frank Ziemer
Fabien Poree
Dirk Schmutzler
Jan Dittgen
Harry STREK
Udo Bickers
Original Assignee
Bayer Cropscience Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Aktiengesellschaft filed Critical Bayer Cropscience Aktiengesellschaft
Publication of WO2016096942A1 publication Critical patent/WO2016096942A1/en

Links

Classifications

    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the invention relates to substituted pyridone carboxamides and their analogues, to processes for their preparation and to their use for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • EP 0544151 describes the effect of hydroxy-substituted pyridone carboxamides as herbicides.
  • EP 1 987 717 describes selected pyridone derivatives and their use as safeners, i. for the reduction of phytotoxic effects of agrochemicals, in particular of herbicides, on useful plants.
  • WO2001 / 14339 describes selected heterocyclic aromatic amides and their fungicidal action.
  • WO2013 / 037955 describes the use of compounds from the group of acylsulfonamides, in particular N- [4- (cyclopropylcarbamoyl) phenylsulfonyl] -2-methoxybenzamide (Cyprosulfamide) to increase the yield in crops, either alone or in combination with drugs of different classes of agents.
  • Pyridone carboxamides are mentioned in generic form as possible mixing partners.
  • representatives with pharmacological properties are known.
  • WO 2001/0551 15 discloses nicotinanilides as inducers of apoptosis, in US 2004/01 16479 dialkylnicotinamides as inhibitors of angiogenesis and in JP 2007186434
  • EP 0522392 describes 6-trifluoromethyl-substituted pyridone carboxamides as precursors for the synthesis of herbicidally active sulfonylureas.
  • N-benzyl-5,6-dimethyl-2-oxo-dihydropyridine-3-carboxamide is described as a reaction product.
  • a use of such compounds to increase the tolerance to abiotic, not by pesticides, preferably not caused by herbicides stress in plants is not yet known.
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones, the vesicles, proteins and
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or
  • SAR systemic acquired resistance
  • 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). Also, the effect of antioxidants, e.g.
  • Naphtols and xanthines for increasing the abiotic stress tolerance in plants have already 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
  • plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress.
  • the object of the present invention was to provide further compounds that increase the tolerance to natural, ie not by pesticides, preferably not triggered by herbicides abiotic stress in plants.
  • the present invention accordingly provides for the use of substituted pyridone carboxamides of the general formula (I) or salts thereof
  • R 1 is (C 3 -C 6) cycloalkyl, aryl or hetaryl, each of the three residues
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, which is
  • Aryl, heteroaryl, or heterocyclyl where each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) Haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfoxy, (C 1 -C 4 ) -alkylsulfone, (C 1 -C 4 ) Haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci-C) -haloalkylsulfone, (Ci-C) -alkoxycarbonyl, (Ci-C 4 ) -
  • R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • R 5 is hydrogen or (C 1 -C 6 ) -alkyl
  • R 6 and R 7 independently of one another are hydrogen or (C 1 -C 6 ) -alkyl, or R 6 ,
  • R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and R 8 and R 9 independently of one another are hydrogen or (C 1 -C 6) -alkyl and n is 0, 1 or 2.
  • the compounds of the general formula (I) and their salts are in some cases also referred to briefly as "compounds (I)" used according to the invention or according to the invention.
  • the compounds of the general formula (I) also include tautomers which can be formed by hydrogen displacement and which structurally formally do not fall under the general formula (I).
  • these tautomers are considered to be encompassed by the definition of the inventive compounds of general formula (I).
  • the definition of the compounds of the general formula (I) includes the tautomeric structures of the general formula (Ia) (2-hydroxy-pyridine-3-carboxamides) or salts thereof,
  • R 1 , R 2 , R 3 and R 4 are as defined in the general formula (I).
  • R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,
  • Hydrogen means and R 4 independently of one another are hydrogen, (C 1 -C 12) -alkyl, (C 2 -C 12) -alkenyl or (C 2 -C 12) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or represented by one or more radicals from the group consisting of halogen, hydroxy , Cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, hydroxycarbonyl , [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6)
  • Phenyl, heteroaryl, or heterocyclyl wherein each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C ) -Alkoxy, (Ci-C) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -haloalkylthio, (Ci- C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl, or is substituted
  • R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • R 5 is hydrogen or (Ci-Ce) alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
  • R 6 and R 7 together with the directly bonded N atom form a five-bissiebengliedrigen, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and n is 0, 1 or 2.
  • R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or halogen by one or more radicals , (Ci-C 4 ) - alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) -haloalkoxy is substituted,
  • R 2 is hydrogen
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 8) -alkyl, (C 2 -C 5) -alkenyl or (C 2 -C 8) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which is un
  • Phenyl, heteroaryl, or heterocyclyl where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( C 1 -C 10 -haloalkoxy, C 1 -C -alkylthio, C 1 -C -alkylsulfoxy, C 1 -C -alkylsulfone, C 1 -C -haloalkylthio, C 1 -C -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl,
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly attached N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or R 3 and R 4 together with the directly bonded N atom form four- to eight-membered carbocyclic or heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and
  • -N CR 5 -NR 6 R 7 , wherein is hydrogen or (Ci-Ce) alkyl R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
  • n 0, 1 or 2.
  • R 1 is (C3-C6) -cycloalkyl, phenyl or pyridinyl, each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, (Ci-C 4) - substituted alkyl, (Ci-C 4) -haloalkyl is
  • R 2 is hydrogen
  • R 3 and R 4 independently of one another are hydrogen, (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (Ci-C 4 ) -
  • Phenyl, heteroaryl, or heterocyclyl where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( Ci-C) haloalkoxy, (Ci-C) alkylthio, (Ci-C) - alkylsulfoxy, (Ci-C) alkylsulfone, (Ci-C) alkoxy-carbonyl, (C3-C6) -cycloalkyl, is substituted,
  • R 3 is hydrogen or (C 1 -C 6) -alkyl
  • R 4 is (C 1 -C 6 ) -alkyl-SO 2 , or
  • R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
  • R 5 is hydrogen or (C 1 -C 6) -alkyl
  • R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
  • n 0 or 1.
  • substituted pyridone carboxamides of the general formula (I) or salts thereof
  • R 1 is (C 3 -C 6) -cycloalkyl, phenyl or hetaryl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) - Alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfoxy, (C 1 -C 4 ) - Alkylsulfone, (C 1 -C 6) -haloalkylthio, (C 1 -C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulf
  • R 2 is hydrogen
  • R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
  • R 10 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl, each of the last-named 3 radicals being unsubstituted or by one or more radicals from the group consisting of halogen , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4 ) - alkyl] -amino, hydroxycarbonyl, [(C1-
  • R 8 R 9 is N-carbonyl substituted
  • R 8 and R 9 independently of one another denote hydrogen or (C 1 -C 6) -alkyl
  • R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,
  • R 2 is hydrogen
  • R 3 is ethyl
  • R 4 is CH 2 CH 2 -R 10 and
  • R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
  • Phenyl, heteroaryl, or heterocyclyl wherein each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C ) -Alkoxy, (Ci-C) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -haloalkylthio, (Ci- C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl, is substituted,
  • R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkyl -C) -alkoxy, (Ci-C) -haloalkoxy is substituted,
  • R 2 is hydrogen
  • R 3 is ethyl
  • R 4 is CH 2 CH 2 -R 10 and
  • R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
  • radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (C1-C4) -alkyl alkylthio, (Ci- C 4) alkylamino, di [(Ci-C 4) -alkyl] amino, hydroxycarbonyl, [(C1-C4) -alkoxy] carbonyl, is [(Ci-C4) -haloalkoxy] carbonyl, substituted mean, or
  • Phenyl, heteroaryl, or heterocyclyl where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( C 1 -C 10 -haloalkoxy, C 1 -C -alkylthio, C 1 -C -alkylsulfoxy, C 1 -C -alkylsulfone, C 1 -C -haloalkylthio, C 1 -C -haloalkylsulfoxy,
  • R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
  • R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
  • each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylsulfoxy, (C 1 -C 4) -alkylsulfone, (C 1 -C 4) -alkoxycarbonyl, (C 3 -C 6 ) -cycloalkyl , is substituted,
  • R 1 is (C 3 -C 6 ) -cycloalkyl or phenyl
  • R 2 is hydrogen
  • R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
  • R 10 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl
  • a further subject of the invention is also a spray solution for
  • halogen means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a remainder, then "halogen" means
  • Alkyl means according to the invention a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio or nitro groups, particular preference is given to fluorine, chlorine, bromine or iodine.
  • Fluoroalkyl means a straight-chain or branched, open-chain, saturated and fluorine-substituted hydrocarbon radical, at least one fluorine atom being in one of the possible positions.
  • Perfluoroalkyl means a straight-chain or branched, open-chain, saturated and completely fluorine-substituted hydrocarbon radical, for example CF 3, CF 2 CF 3,
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, the corresponding fluorine atoms being present as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine, bromine or iodine.
  • the corresponding halogen atoms may be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkyl, alkenyl and alkynyl mean the same or different
  • Perhaloalkyl such. CCI 3 , CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF 2 CCIFCF 3 ; Polyhaloalkyl such. CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl
  • polyhaloalkyl also encompasses the terms partially fluorinated alkyl and partially fluorinated haloalkyl.
  • 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;
  • (C 1 -C 4 ) -alkyl denotes a short notation for alkyl having one to four carbon atoms corresponding to the range given for C atoms, ie 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.
  • (Ci-C6) -alkyl accordingly also include straight-chain or branched
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond.
  • 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 cumulene radicals having one or more cumulative 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, e.g.
  • alkynyl also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds such as 1, 3-butatrienyl and 3-penten-1-yn-1-yl.
  • (C 2 -C 6) alkynyl means ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl, 2-pentynyl or
  • 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
  • Cyclohexenyl 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl,
  • aryl means a 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 optionally mono- or polysubstituted by a radical from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy , (Ci-C) -haloalkoxy, (Ci-C) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -alkylamino, di [(Ci-C) -alkyl ] amino, [(Ci-C) alkoxy] carbonyl, [(Ci-C) -alky
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, wherein the
  • Binding site on the aromatic system is.
  • aryl is also encompassed by the term “optionally substituted phenyl”.
  • Optionally substituted aryl (phenyl) is preferably aryl (phenyl) which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, nitro, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) -haloalkoxy, (Ci-C) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci -C) -haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci-C 4 ) -haloalkylsulfone, (Ci-C 4 ) -alkoxycarbonyl, (Ci-C 4 ) -
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic and unsubstituted or, for example, with a radical selected from the group consisting of halogen, nitro, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -
  • heterocyclic radical may be e.g. a heteroaromatic radical or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms,
  • pyridyl for example, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl.
  • substituents for a substituted is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl.
  • Heterocyclic radical are the substituents mentioned below in question, in addition also oxo.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. at N and S, occur.
  • Alkoxy is an alkyl radical bonded via an oxygen atom
  • alkenyloxy is an alkynyl radical bonded via an oxygen atom
  • alkynyloxy is an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy is a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy is a cycloalkenyl radical bonded via an oxygen atom.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Alkenylthio represents an alkenyl radical bonded via a sulfur atom
  • alkynylthio represents an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
  • AI kylsulfinyl - alone or as part of a chemical group - kylsulfinyl straight or branched Al, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl , Isobutylsulfinyl, sec- Butylsulfinyl and tert-butylsulfinyl.
  • Al kylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, for example substituted by halogen, alkyl, haloalkyl, haloalkoxy or alkoxy groups.
  • sulfilimine means a group having a nitrogen-sulfur double bond in which nitrogen and sulfur are further substituted, the nitrogen atom preferably by a further substituted carbonyl group and the sulfur preferably by two identical or mixed alkyl, aryl and
  • Cycloalkyl substituents for example in the form of an N- (di-n-butyl-sulfanylidene), N- (di-iso-propyl-sulfanyliden), N- (di-n-propyl-sulfanyliden), N- (di-n-pentyl -sulfanylidene), N- (diisobutylsulfanylidene), N- (cyclobutylisopropylsulfanylidene), N- (n-propylisopropylsulfanylidene), N- (cyclopropylisopropyl) sulfanylidene) or N- (iso-butylisopropylsulfanylidene) unit.
  • 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 general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, are one or more asymmetric
  • Stereoisomers can be detected from the mixtures obtained in the preparation obtained 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 prepared by using stereoselective reactions using optically active
  • Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting and in each case required for the preparation
  • crops refers to crops used as plants for the production of food, feed or for technical purposes.
  • the compounds of the general formula (I) can be prepared by, for example,
  • R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above definition and "alkyl” is an alkyl radical, for example methyl or ethyl, with an amine of general formula (III) or its salt,
  • R 3 and R 4 are as defined in the compound of general formula (I) to be prepared according to the above definition, to give the compound of general formula (I) or (c) a carboxylic acid halide or anhydride of general formula (V), wherein R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above definition and Hal is a halogen atom, for example chlorine, or an acyloxy, with an amine of general formula (III) or its salt,
  • R 1 and R 2 are as defined in the compound of general formula (I) to be prepared according to the above definition of the radical and "alkyl” is an alkyl radical, for example methyl or ethyl,
  • the amide formations according to variant (a) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 0 ° C and 50 ° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, z.
  • diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • the amide formations according to variant (b) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 50 ° C and 100 ° C.
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. For example, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as
  • the amide formations according to variant (c) can, for example, in the presence of an acid-binding agent in an inert organic solvent in a
  • Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
  • Acid-binding agents are, for example, alkali metal or alkaline earth metal carbonates such as.
  • alkali metal or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide
  • alkali metal hydrides or amides such as sodium or potassium hydride or amide
  • organic bases such as triethylamine, pyridine, dimethylaminopyridine, DBU (1,8-diazabicyclo [5.4.0] undec-7-ene), DBN (1,5-diazabicyclo [4.3.0] non-5-ene) and 1,4-diazabicyclo [2.2.2] octane ,
  • the malonamide may typically be converted to a reactive salt in an organic anhydrous polar protic or aprotic solvent, for example in an alcohol, with a strong base such as an alkali metal, alkali metal hydride or alkali metal alcoholate and then reacted with the compound of general formula (VI) ,
  • the reaction with the compound (VI) can be carried out usually in a temperature range between 0 ° C and the boiling point of the solvent (depending on the solvent about to 150 ° C).
  • the compounds of general formulas (II), (III), (IV) and (V) are either commercially available or can be prepared by or analogously to methods known to the person skilled in the art (for example Helv. Chim. Acta 71 (1988) 596, EP 502740, EP 522392).
  • R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above radical definition,
  • the compounds of the general formula (IV) in which R 2 represents a halogen atom can be prepared by conventional halogenations from the compounds of the general formula (IVa).
  • R cycloalkyl, vinyl 30 ° C, 16 h
  • 6-Cyclopropyl-2-oxo-1H-pyridine-3-carbonitrile (6.20 g, 34.6 mmol) were placed in 200 ml of 10 N sodium hydroxide solution and heated at 120 ° C for 4h.
  • Reaction mixture was adjusted to pH 1 with 6N HCl and water was added. The resulting solid was filtered off with suction and i.Vak. dried.
  • Neopentylamine (203 mg, 2.33 mmol, 2.00 ml) was dissolved and stirred at room temperature for 16 h. The reaction mixture was adjusted to pH 1 with 1 N HCl, the resulting solid was filtered off with suction and concentrated by evaporation in vacuo. dried. 373 mg (97% of theory) were obtained as a colorless solid.
  • 6- (4-Chlorophenyl) -2-oxo-1H-pyridine-3-carboxamide (3.49 g, 14.0 mmol) was placed in 100 ml of 10 N sodium hydroxide solution and heated at 120 ° C for 4 h. The Reaction mixture was adjusted to pH 1 with 6N HCl and water was added. The resulting solid was filtered off with suction and i.Vak. dried. 3.28 g (94% of theory) were obtained as a colorless solid.
  • reaction mixture was adjusted to pH 1 with 2N HCl and the resulting solid was filtered off with suction and concentrated by evaporation in a vacuum. dried. There were obtained 227 mg (74% of theory) of a colorless solid.
  • Example 1 102 according to the following Table A N-methyl-2-oxo-6- (2-pyridyl) -1H-pyridine-3-carboxamide 1 102.1) 2-oxo-6- (2-pyridyl) -1 H- pyridine-3-carboxamide
  • reaction mixture was adjusted to pH 1 with 2N HCl and the resulting solid was filtered off with suction and concentrated by evaporation in a vacuum. dried. There were obtained 227 mg (74% of theory) of a colorless solid.
  • numeric indices in the formula expressions are not subscripted in Table A, but arranged in the same row height and font size as the atomic symbols.
  • the formula corresponds to CF3 in the table of the formula CF3 according to conventional notation with subscript or the formula CH2CH (CH2CH3) 2 of the formula CH 2 CH (CH 2 CH 3 ) 2 subscripts with subscripts.
  • NMR data of selected compounds listed in Table A are listed either in classical form ( ⁇ values, number of H atoms, multiplet splitting) or as NMR peak lists. The assignment of the mentioned in Table A.
  • the ⁇ -value-signal intensity-number pairs of different signal peaks are listed separated by semicolons.
  • the peak list therefore has the following form: ⁇ (intensity i); 82 (intensity.2); ; ⁇ , (intensity, ';; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of signal intensities Center of the signal and its relative intensity compared to the most intense signal in the spectrum are shown.
  • Tetramethylsilane and / or the chemical shift of the solvent used 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 1 H NMR peaks are similar to the classical 1 H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. Moreover, like classical 1 H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
  • Solvent peaks for example peaks of DMSO in DMSO- and the peak of water, which are usually of high intensity on average.
  • Impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help the reproduction of our manufacturing process by "by-product fingerprints".
  • Example 576: 1 H-NMR (400.0 MHz, de-DMSO): ⁇ 12.757 (4.0); 9.849 (2.4); 8.386 (9.8); 8.368 (10.2); 7.881 ( 0.5), 7.859 (0.9), 7.836 (8.2), 7.815 (9.8), 7.654 (0.6), 7.632 (0.8), 7.616 (15.9), 7.594 (13.3); 6.837 (2.7); 6.820 (2.7); 5.979 (1.0); 5.966 (2.2); 5.953 (2.2); 5.940 (2.6
  • RV9 R7f 9V9 fifWf) RV9 ⁇ 1 ⁇ 4V9 "WM 1 9 W) tf ⁇ RV9 ⁇ mA 4V9 ⁇ R ⁇ fi RV9 ⁇ fVfil 7V9 'liWn ⁇ i 1 VV9 ⁇ fllMrfi 9V9 iQR ⁇ T RV9 AQM ⁇ R ⁇
  • the present invention accordingly provides for the use of at least one compound selected from the group consisting of substituted
  • abiotic not by pesticides, preferably not by herbicides-induced stress, in particular to enhance plant growth and / or increase the plant yield.
  • Another object of the present invention is a spray solution for the treatment of plants, containing a plant effective against abiotic, not by pesticides, preferably not triggered by herbicides stress effective amount of at least one compound selected from the group consisting of substituted Pyridoncarboxamiden of the general formula (I).
  • a plant effective against abiotic, not by pesticides preferably not triggered by herbicides stress effective amount of at least one compound selected from the group consisting of substituted Pyridoncarboxamiden of the general formula (I).
  • Use of the compounds of general formula (I) according to the invention is preferably carried out with a dosage between 0.0005 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha.
  • abscisic acid is used simultaneously with substituted pyridone carboxamides of the general formula (I), for example in the context of a common preparation or formulation, the addition of abscisic acid is preferably carried out at a dosage of between 0.001 and 3 kg / ha, more preferably between 0.005 and 2 kg / ha, particularly preferably between 0.01 and 1 kg / ha.
  • 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 and depth increased tailing or assembly, stronger and more productive foothills and tillers,
  • Sprout 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 components of any kind or better digestibility, improved storage stability of the crop, improved tolerance against unfavorable temperatures, improved tolerance to drought and dryness, as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soils and water, increased
  • At least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • 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 desired combination of two or more effects.
  • a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
  • the spray solution may be other common
  • constituents such as solvents, formulation auxiliaries, especially water.
  • Other ingredients may include agrochemical agents, which are further described below.
  • Another object of the present invention is the use of
  • Fertilizers as defined below are possible on plants or in their environment.
  • potassium salts preferably chlorides, sulfates, nitrates
  • phosphoric acid salts and / or salts of phosphorous acid preferably potassium salts and ammonium salts.
  • NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2SO 4 NH 4 NO 3), ammonium phosphate and ammonium sulphate.
  • 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,
  • fertilizers Containing 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 fertilizer.
  • Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
  • 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, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
  • the general composition of the fertilizers which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
  • nitrogen, potassium or phosphorus may vary within a wide range.
  • a content of 1 to 30 wt .-% of nitrogen preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) 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.
  • the fertilizer and the compounds of the general formula (I) can be used simultaneously, i. synchronously, administered. However, it is also possible to use first the fertilizer and then a compound of the general formula (I) or first a compound of the general formula (I) and then the fertilizer. In the case of non-simultaneous application of a compound of the general formula (I) and of the fertilizer, however, the application is carried out in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours , even more special 4 hours, even more special within 2 hours. In very particular embodiments of the present invention, the use of the compound of the general 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.
  • the active compounds to be used according to the invention can, optionally in
  • plants from the group of crops, 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.
  • crops as used herein refers to
  • Among the useful plants include z.
  • the following plant species Triticale, Durum
  • Durum wheat turf, vines, cereals, for example wheat, barley, rye, oats, hops, rice, corn and millet
  • Beets for example sugar beets and fodder beets
  • Fruits such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries,
  • Raspberries, blackberries Raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucumber plants,
  • Laurel family such as avocado, cinnamonum, camphor, or as plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
  • Oats, rye, triticale, durum, bamboo wool, aubergine, turf, pome fruit, stone fruit, berry fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals are to be regarded as particularly suitable target cultures for the application of the method according to the invention , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
  • Examples of trees which can be improved according to the process 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 ..
  • 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 tree 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.
  • the present invention may also be practiced on any turfgrasses, including "cool season turfgrasses” and “warm season turfgrasses.”
  • 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 Sibth.), “velvet bentgrass” (Agrostis canina L),
  • Lolium ryegrasses, Lolium spp.
  • Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “smooth bromegrass” (Bromus inermis leyss.), reeds (“cattails”) such as “Timothy” (Phleum pratense 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 Munrohack.), “Carpetgrass” (Axonopus affinis chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm.) , “Blue gramma” (Bouteloua gracilis (HBK) lag.
  • plants of the respective commercially available or in use plant cultivars are grown with new properties ("traits"), which have been bred either by conventional breeding, by mutagenesis or by means of recombinant DNA techniques.
  • Crop plants can accordingly be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety protection rights.
  • the treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
  • Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (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 that are preferably treated according to the invention include all plants which have genetic material that these plants
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. For example, drought, cold and heat conditions, osmotic stress, waterlogging, elevated water levels, etc. can all contribute to abiotic stress
  • Soil salt content increased exposure to minerals, ozone conditions, High light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients or avoidance of shadows.
  • Plants and plant varieties which can also be treated 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
  • Plant development such as water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size,
  • Other income characteristics include
  • Seed composition such as carbohydrate content, protein content, oil content and
  • Oil composition Oil composition, nutritional value, reduction of nontoxic compounds, improved processability and improved shelf life.
  • Plants which can also be treated according to the invention are:
  • Hybrid plants that already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be removed (eg in maize) by delaving (i.e., mechanical removal of the males)
  • Sex organs or the male flowers are produced; however, it is more common for male sterility to be due to genetic determinants in the plant genome based. In this case, especially if it is the desired
  • Determinants responsible for the pollensity of the poll include restorative. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been reported, for example
  • Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072).
  • 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 is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069).
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can also be treated 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.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • 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.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme as described in US Pat
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. WO 2002/036782, WO
  • 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 2001/024615 or WO 2003/013226.
  • 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.
  • an effective detoxifying enzyme is, for example, an enzyme suitable for
  • 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 and US 7,112,665. Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD).
  • HPPD hydroxyphenylpyruvate dioxygenase
  • hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants that are tolerant to HPPD inhibitors can be used with a gene coding for a naturally occurring resistant HPPD enzyme or a gene coding for a mutant HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999/024586.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that promote the formation of HPPD inhibitors
  • 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.
  • ALS acetolactate synthase
  • known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
  • Acetohydroxy acid synthase known
  • Other sulfonylurea and imidazolinone tolerant plants are also disclosed in e.g. WO 2007/024782 described.
  • plants which are tolerant to imidazolinone and / or sulphonylurea may be induced by induced mutagenesis, selection in cell cultures in the presence of the Herbicides or by mutational breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001 / 065922 is described.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated 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 obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • 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:
  • 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 Environment Microb. (2006), 71, 1765-1774); or
  • an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. B. the Protein Cry1A.105 produced by maize event MON98034 (WO
  • amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
  • VIP3Aa Proteins of protein class VIP3Aa:
  • 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 1994/21795); or
  • 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
  • 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.
  • 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 develop a protein
  • Plants or plant varieties which can also be treated according to the invention, are tolerant to abiotic stressors. 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 which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
  • Biosynthetic pathway including nicotinamidase
  • Nicotinate phosphoribosyltransferase nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as this z.
  • Nicotinate phosphoribosyltransferase nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as this z.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the
  • Harvested product and / or altered properties of certain components of the harvested product such as: 1) transgenic plants synthesizing a modified starch which, in terms of their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, of the
  • Viscosity behavior the gel strength, the starch grain size and / or
  • Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering), which can also be treated 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, which have an altered form of
  • Cellulosesynthasegenen contain, as described in WO 1998/000549, b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219; c) plants such as cotton plants with an increased expression of the
  • Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, for example by
  • Plants or plant varieties which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. 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 rape plants, the oil with a low saturated
  • transgenic plants which can be treated according to the invention are plants having one or more genes coding for one or more toxins, the transgenic plants being one of the following Commercial names: YIELD GARD® (for example, corn, cotton, soybeans), KnockOut® (for example, corn), BiteGard® (for example, corn), BT-Xtra® (for example, corn), StarLink® (for example, corn) , 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®
  • Herbicide-resistant plants plants traditionally grown for herbicide tolerance
  • Clearfield® for example corn
  • transgenic plants which can be treated according to the invention are plants which contain transformation events, or a combination of transformation events, and which are for example included in the files of
  • the compounds of the general 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 ingredient-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
  • 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 ingredient-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-
  • the present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress.
  • a spray formulation is described in more detail:
  • the formulations for spray application are prepared in a known manner, for example by mixing the compounds of general formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and or foam-producing agents.
  • extenders ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and or foam-producing agents.
  • customary additives such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants,
  • Emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and also water may optionally 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.
  • spray mixtures for example spray mixtures
  • typical aids are:
  • Hydrocarbons such as paraffins, 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
  • Poly ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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, strong polar solvents such as dimethyl sulfoxide, and water.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • 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.
  • nonionic, anionic and cationic dispersants into consideration.
  • agrochemical active ingredients conventional nonionic, anionic and cationic dispersants into consideration.
  • nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are in particular ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • 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 As preservatives can be used in the invention
  • Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and
  • Agrochemical agents usable substances in question Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • 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.
  • 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%, of the compound of general formula (I).
  • the active substance according to the invention can be used in its commercially available formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides,
  • general formula (I) to support the plant's own defenses by additional treatment with insecticidal, fungicidal or bactericidal agents.
  • Preferred times for the application of compounds of the general formula (I) for the seizure of the resistance to abiotic stress are soil, stem and / or leaf treatments with the permitted application rates.
  • the duration of the respective stress phases mainly depends on the condition of the stressed control plants. It was terminated (by irrigation and transfer to a greenhouse with good growth conditions) as soon as irreversible damage to the stressed control plants was observed.
  • Tables 1-3 The values given in Tables 1-3 below are averages of at least one test involving at least two replicates. Effects of selected compounds of general formula (I) under dry stress (Tables 1 to 3): Table 1
  • BRSNS Brassica napus
  • TRZAS Triticum aestivum
  • ZEAMX Zea mays Similar results could also be obtained with other compounds of the general formula (I) even when applied to other plant species.

Landscapes

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

Abstract

The invention relates to the use of substituted pyridone carboxamides of general formula (I) or the salts thereof, the groups in general formula (I) being defined as cited in the description, for raising the stress tolerance of plants with respect to abiotic stress, for strengthening plant growth and/or for increasing plant yield.

Description

Verwendung ausgewählter Pyridoncarboxamide oder deren Salzen als Wirkstoffe gegen abiotischen Pflanzenstress  Use of selected pyridone carboxamides or their salts as active ingredients against abiotic plant stress
Beschreibung description
Die Erfindung betrifft substituierte Pyridoncarboxamide und deren Analoge, Verfahren zu deren Herstellung und ihre Verwendung zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, insbesondere zur Stärkung des The invention relates to substituted pyridone carboxamides and their analogues, to processes for their preparation and to their use for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the
Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. Plant growth and / or increase the plant yield.
Es ist bekannt, dass bestimmte Pyridoncarboxamide nutzpflanzenschützende Wirkung gegen Agrochemikalien, welche allein appliziert Schäden an den Nutzpflanzen verursachen, entfalten können (vergl. WO2008/131860 (PCT/EP2008/003016)). It is known that certain pyridone carboxamides can exert a crop protection effect against agrochemicals which alone cause damage to the crop plants (see WO2008 / 131860 (PCT / EP2008 / 003016)).
Weiterhin sind Wirkstoffe aus der chemischen Klasse der Pyridone mit Pestiziden Furthermore, active substances from the chemical class of pyridones with pesticides
Eigenschaften aus der Literatur bekannt. Es werden unterschiedliche biologischeProperties known from the literature. There are different biological
Wirkungen beschrieben; so ist z.B. in WO 2001/014339 die fungizide Wirkung bestimmter substituierter Pyridoncarboxamide erwähnt, WO 2005/042492 und WOEffects described; such as e.g. WO 2001/014339 mentions the fungicidal action of certain substituted pyridone carboxamides, WO 2005/042492 and WO
2005/042493 beschreiben u.a. die fungizide Wirkung von Heterocyclylcarboxamiden.2005/042493 describe i.a. the fungicidal action of heterocyclylcarboxamides.
EP 0544151 beschreibt die Wirkung von hydroxysubstituierten Pyridoncarboxamiden als Herbizide. EP 0544151 describes the effect of hydroxy-substituted pyridone carboxamides as herbicides.
EP 1 987 717 beschreibt ausgewählte Pyridonderivate sowie deren Verwendung alsSafener, d.h. zur Reduktion phytotoxischer Wirkungen von Agrochemikalien, insbesondere von Herbiziden, an Nutzpflanzen.  EP 1 987 717 describes selected pyridone derivatives and their use as safeners, i. for the reduction of phytotoxic effects of agrochemicals, in particular of herbicides, on useful plants.
WO2001/14339 beschreibt ausgewählte heterocyclische aromatische Amide sowie deren fungizide Wirkung.  WO2001 / 14339 describes selected heterocyclic aromatic amides and their fungicidal action.
WO2013/037955 beschreibt die Verwendung von Verbindungen aus der Gruppe der Acylsulfonamide, insbesondere N-[4-(cyclopropylcarbamoyl)phenylsulfonyl]-2- methoxybenzamide (Cyprosulfamide) zur Ertragssteigerung in Kulturpflanzen, entweder in alleiniger Anwendung oder in kombinierter Anwendung mit Wirkstoffen unterschiedlicher Wirktstoffklassen. Pyridoncarboxamide werden in generischer Form als mögliche Mischungspartner genannt. Weiterhin sind Vertreter mit pharmakologischen Eigenschaften bekannt. So werden in WO 2001/0551 15 Nicotinanilide als Induktoren der Apoptose, in US 2004/01 16479 Dialkylnicotinamide als Inhibitoren der Angiogenese und in JP 2007186434 WO2013 / 037955 describes the use of compounds from the group of acylsulfonamides, in particular N- [4- (cyclopropylcarbamoyl) phenylsulfonyl] -2-methoxybenzamide (Cyprosulfamide) to increase the yield in crops, either alone or in combination with drugs of different classes of agents. Pyridone carboxamides are mentioned in generic form as possible mixing partners. Furthermore, representatives with pharmacological properties are known. Thus, WO 2001/0551 15 discloses nicotinanilides as inducers of apoptosis, in US 2004/01 16479 dialkylnicotinamides as inhibitors of angiogenesis and in JP 2007186434
Pyridinanaloge als vaskuläre endotheliale Stickoxid Promotoren beschrieben. Pyridine analogs described as vascular endothelial nitric oxide promoters.
Ferner beschreibt EP 0522392 6-Trifluormethyl-substituierte Pyridoncarboxamide als Vorprodukte zur Synthese herbizid wirksamer Sulfonylharnstoffe. In Chemistry of Heterocyclic Compounds, Vol 40, No. 9, 2004, 1 155-1 161 wird N-Benzyl-5,6-dimethyl- 2-oxo-dihydropyridin-3-carboxamid als Reaktionsprodukt beschrieben. Eine Verwendung derartiger Verbindungen zur Erhöhung der Toleranz gegenüber abiotischem, nicht durch Pestizide, bevorzugt nicht durch Herbizide ausgelöstem Stress, in Pflanzen ist noch nicht bekannt. Furthermore, EP 0522392 describes 6-trifluoromethyl-substituted pyridone carboxamides as precursors for the synthesis of herbicidally active sulfonylureas. In Chemistry of Heterocyclic Compounds, Vol. 9, 2004, 1 155-1 161 N-benzyl-5,6-dimethyl-2-oxo-dihydropyridine-3-carboxamide is described as a reaction product. A use of such compounds to increase the tolerance to abiotic, not by pesticides, preferably not caused by herbicides stress in plants is not yet known.
Es ist bekannt, dass Pflanzen auf natürliche, d.h. nicht durch Pestizide ausgelöste Stressbedingungen, wie beispielsweise Kälte, Hitze, Trockenheit, Verwundung, Pathogenbefall (Viren, Bakterien, Pilze, Insekten) etc. aber auch auf Herbizide mit spezifischen oder unspezifischen Abwehrmechanismen reagieren [Pflanzenbiochemie, S. 393-462 , Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996.; Biochemistry and Molecular Biology of Plants, S. 1 102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. It is known that plants are naturally, i. not caused by pesticides stress conditions such as cold, heat, drought, wounding, pathogen infestation (viruses, bacteria, fungi, insects) etc. but also respond to herbicides with specific or nonspecific defense mechanisms [Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag , Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, p. 1 102-1203, 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. lonentransport, Entgiftung reaktiver Sauerstoff- Spezies). Zu den Signalkettengenen der abiotischen Stressreaktion gehören u.a. In plants, numerous proteins and the genes encoding them are involved, which are involved in abiotic stress defense reactions (e.g., cold, heat, drought, salt, flooding). These partially belong to signal transduction chains (e.g., transcription factors, kinases, phosphatases) or cause a physiological response of the plant cell (e.g., ion transport, detoxification of reactive oxygen species). The signal chain genes of the abiotic stress reaction include, among others.
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 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 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. For example, sucrose synthase and proline transporters are involved here (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and Dryness partly uses the same molecular mechanisms. The accumulation of so-called Late Embryogenesis Abundant Proteins (LEA proteins), which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones, the vesicles, proteins and
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). Stabilize membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). Moreover, induction of aldehyde dehydrogenases, which detoxify the reactive oxygen species (ROS) produced by oxidative stress, is often used (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 pflanzenendogener Signalstoffe, die in die Stresstoleranz bzw. die A series of plant endogenous signaling substances that are in the stress tolerance or the
Pathogenabwehr involviert sind, sind bereits bekannt. Zu nennen sind hier Pathogen defense are already known. To call here are
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 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
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]. 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 Blattspritzung oder durch Bodenbehandung appliziert. So wird eine Erhöhung der abiotischen Stresstoleranz von Kulturpflanzen durch Behandlung mit Elicitoren der Systemic Acquired Resistance (SAR) oder Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, increasing the abiotic stress tolerance of crops by treatment with systemic acquired resistance (SAR) or
Abscisinsäure-Derivaten beschrieben (Schading and Wei, WO-200028055, Abrams and Gusta, US-5201931 , Churchill et al., 1998, Plant Growth Regul 25: 35-45) oder Azibenzolar-S-methyl. 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 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). Desweiteren wurden Effekte von Wachstumsregulatoren auf die Stresstoleranz von Kulturpflanzen beschrieben (Morrison and Andrews, 1992, J Plant Growth Regul 1 1 : 1 13-1 17, RD-259027). Bei osmotischem Stress ist eine Schutzwirkung durch Abscisic acid derivatives (Schading and Wei, WO200028055, Abrams and Gusta, US 5201931, Churchill et al., 1998, Plant Growth Regul 25: 35-45) or azibenzolar-S-methyl. Even with the use of fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors similar effects are observed, which are often associated with an 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). Furthermore, effects of growth regulators on the stress tolerance of crop plants have been described (Morrison and Andrews, 1992, J Plant Growth Regul 1 1: 1 13-1 17, RD-259027). When osmotic stress is a protective effect through
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.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). Also, the effect of antioxidants, e.g.
Naphtole 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. Naphtols and xanthines for increasing the abiotic stress tolerance in plants have already 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 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, 2005, 41 , 95; Levine et al., FEBS Lett. 1998, 440, 1 ; WO0004173; WO04090140). It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2005, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO0004173, WO04090140).
Somit ist bekannt, dass Pflanzen über mehrere endogene Reaktionsmechanismen verfügen, die eine wirksame Abwehr gegenüber verschiedensten Schadorganismen und/oder natürlichem abiotischen Stress bewirken können. Thus, it is known that plants have a number of endogenous reaction mechanisms that can effect effective defense against a variety of harmful organisms and / or natural abiotic stress.
Da sich aber die ökologischen und ökonomischen Anforderungen an moderne But since the ecological and economic requirements of modern
Pflanzenbehandlungsmittel laufend erhöhen, beispielsweise was Toxizität, Selektivität, Aufwandmenge, Rückstandsbildung und günstige Herstellbarkeit angeht, besteht die ständige Aufgabe, neue Pflanzenbehandlungsmittel zu entwickeln, die zumindest in Teilbereichen Vorteile gegenüber den bekannten aufweisen. Constantly increase plant treatment, for example, as regards toxicity, selectivity, application 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.
Daher bestand die Aufgabe der vorliegenden Erfindung darin, weitere Verbindungen bereitzustellen, die die Toleranz gegenüber natürlichem, d.h. nicht durch Pestizide, bevorzugt nicht durch Herbizide ausgelöstem abiotischen Stress in Pflanzen erhöhen. Gegenstand der vorliegenden Erfindung ist demnach die Verwendung substituierter Pyridoncarboxamide der allgemeinen Formel (I) oder deren Salze Therefore, the object of the present invention was to provide further compounds that increase the tolerance to natural, ie not by pesticides, preferably not triggered by herbicides abiotic stress in plants. The present invention accordingly provides for the use of substituted pyridone carboxamides of the general formula (I) or salts thereof
Figure imgf000006_0001
zur Toleranzerhöhung gegenüber abiotischem Stress in Pflanzen, wobei R1 (C3-C6)-Cycloalkyl, Aryl oder Hetaryl bedeutet, wobei jeder der drei Reste
Figure imgf000006_0001
to increase tolerance to abiotic stress in plants, wherein R 1 is (C 3 -C 6) cycloalkyl, aryl or hetaryl, each of the three residues
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C )-Haloalkylsulfon, (Ci-C )- Alkoxy-carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-unsubstituted or by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (Ci-C) -haloalkoxy, (Ci-C) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci -C) -Haloalkylsulfon, (Ci-C) - alkoxy-carbonyl, (Ci-C 4) haloalkoxy-carbonyl, (Ci-C 4) -alkyl carboxy, (C3-C6) -
Cycloalkyl, (C3-C6)-Cycloalkyl (Ci-C6)-alkyl, (Ci-C )-Alkoxy-carbonyl-(Ci-C )- alkyl, Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, R2 Wasserstoff bedeutet und Cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl, R 8 R 9 is N-carbonyl substituted, R 2 is hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, (Ci-Ci6)-Alkyl, (C2-Ci6)-Alkenyl oder (C2-Ci6)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)- Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )- alkylj-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]- carbonyl, (C3-C6)-Cycloalkyl, das unsubstituiert oder substituiert ist, Aryl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, R 3 and R 4 independently of one another are hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 16) -alkenyl or (C 2 -C 16) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl, which is unsubstituted or substituted, aryl which is unsubstituted or substituted, Heteroaryl which is unsubstituted or substituted or substituted heterocyclyl which is unsubstituted or substituted,
oder [(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-Ci6)-Alkylcarbonyl, (Ci-Ci6)-Haloalkylcarbonyl bedeuten, oder or [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 16) ) Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)-Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten (C3-C6) -cycloalkyl, (C 4 -C 6) cycloalkenyl, (C3-C6) -cycloalkyl, which on one side of the ring with a 4 to 6-membered saturated or unsaturated
carbocyclischen Ring kondensiert ist, oder (C4-C6)-Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )- Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci- C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)-Cycloalkyl, Aryl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, carbocyclic ring, or (C 4 -C 6) -cycloalkenyl fused on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 radicals being unsubstituted or substituted by one or more radicals the group halogen, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) - haloalkoxy, (Ci-C) -alkylthio, (Ci -C) -alkylamino, di [(C 1 -C 4 ) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) Cycloalkyl, aryl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocyclyl which is unsubstituted or substituted,
oder or
Aryl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)- Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )- Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C )-Haloalkylsulfon, (Ci-C )-Alkoxy- carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl (Ci-C6)-alkyl, (Ci-C )-Alkoxy-carbonyl-(Ci-C )-alkyl, Aryl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) Haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfoxy, (C 1 -C 4 ) -alkylsulfone, (C 1 -C 4 ) Haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci-C) -haloalkylsulfone, (Ci-C) -alkoxycarbonyl, (Ci-C 4 ) -haloalkoxycarbonyl, (Ci-C 4 ) -alkylcarboxy, ( C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4) -alkyl,
Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, bedeuten, oder Hydroxycarbonyl, hydroxycarbonyl (Ci-C 4 ) -alkyl, R 8 R 9 N-carbonyl is substituted, mean, or
Wasserstoff oder (Ci-Ce)-Alkyl bedeutet und R4 (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)- Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder Is hydrogen or (C 1 -C 6) -alkyl and R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen Aminosäurerest und zwar die natürlich vorkommenden in ihrer racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly attached N atom form a four-bis
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der  form eight-membered carbocyclic or heterocyclic ring, which may contain in addition to the N atom also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and the
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]-carbonyl , (Ci-C )-Alkoxy, (Ci- C4)-Haloalkoxy, (Ci-C4)-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann oder R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe unsubstituted or by one or more radicals from the group halogen, (Ci-C) -alkyl, (Ci-C) -haloalkyl, [(Ci-C) -alkoxy] -carbonyl, (Ci-C) -alkoxy, (Ci - C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, hydroxy is substituted and wherein a heterocyclic ring n can contain oxo groups or R 3 and R 4 together with the directly attached nitrogen atom, the group
-N=CR5-NR6R7 bedeuten und wobei -N = CR 5 -NR 6 R 7 and wherein
R5 für Wasserstoff oder (Ci-Ce)-Alkyl steht, R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R6, R 5 is hydrogen or (C 1 -C 6 ) -alkyl, R 6 and R 7 independently of one another are hydrogen or (C 1 -C 6 ) -alkyl, or R 6 ,
R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und R8 und R9 unabhängig voneinander Wasserstoff oder (Ci-C6)-Alkyl bedeuten und n für 0, 1 oder 2 steht. Im Folgenden werden die Verbindungen der allgemeinen Formel (I) und ihre Salze in einigen Fällen auch kurz als erfindungsgemäß verwendete oder erfindungsgemäße „Verbindungen (I)" bezeichnet. R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and R 8 and R 9 independently of one another are hydrogen or (C 1 -C 6) -alkyl and n is 0, 1 or 2. In the following, the compounds of the general formula (I) and their salts are in some cases also referred to briefly as "compounds (I)" used according to the invention or according to the invention.
Die Verbindungen der allgemeinen Formel (I) umfassen auch Tautomere, welche durch Wasserstoffverschiebung gebildet werden können und welche strukturell formal nicht unter die allgemeine Formel (I) fallen. Gleichwohl gelten diese Tautomere als von der Definition der erfindergemäßen Verbindungen der allgemeinen Formel (I) umfasst. Insbesondere umfasst sind von der Definition der Verbindungen der allgemeinen Formel (I) die tautomeren Strukturen der allgemeinen Formel (la) (2-Hydroxy-pyridin-3- carboxamide) oder deren Salze, The compounds of the general formula (I) also include tautomers which can be formed by hydrogen displacement and which structurally formally do not fall under the general formula (I). However, these tautomers are considered to be encompassed by the definition of the inventive compounds of general formula (I). In particular, the definition of the compounds of the general formula (I) includes the tautomeric structures of the general formula (Ia) (2-hydroxy-pyridine-3-carboxamides) or salts thereof,
Figure imgf000009_0001
Figure imgf000009_0001
R1 , R2, R3 und R4 wie in der allgemeinen Formel (I) definiert sind. R 1 , R 2 , R 3 and R 4 are as defined in the general formula (I).
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Preference is given to the use according to the invention of compounds of the general formula (I) or salts thereof, in which
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (C3- C6)-Cycloalkyl substituiert ist, R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,
Wasserstoff bedeutet und R4 unabhängig voneinander Wasserstoff, (Ci-Ci2)-Alkyl, (C2-Ci2)-Alkenyl oder (C2-Ci2)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)- Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )- alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]- carbonyl, (C3-C6)-Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, Hydrogen means and R 4 independently of one another are hydrogen, (C 1 -C 12) -alkyl, (C 2 -C 12) -alkenyl or (C 2 -C 12) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or represented by one or more radicals from the group consisting of halogen, hydroxy , Cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, hydroxycarbonyl , [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or substituted heterocyclyl which is unsubstituted or substituted,
oder  or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) ) -Haloalkylcarbonyl,
oder  or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Alkylthio, Phenyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder (C 3 -C 6) -cycloalkyl, (C 4 -C 6) -cycloalkenyl, where each of the latter two radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (Ci-C) -Alkoxy, (Ci-C) -Alkylthio, phenyl, which is unsubstituted or substituted, mean, or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci- C4)-Al kylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci- C4)-Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)- Cycloalkyl, substituiert ist, oder Phenyl, heteroaryl, or heterocyclyl, wherein each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C ) -Alkoxy, (Ci-C) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -haloalkylthio, (Ci- C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl, or is substituted
Wasserstoff oder (Ci-Ce)-Alkyl bedeutet und R4 (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)- Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder Is hydrogen or (C 1 -C 6) -alkyl and R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen Aminosäurerest und zwar die natürlich vorkommenden in ihrer racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly attached N atom form a four-bis
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der  form eight-membered carbocyclic or heterocyclic ring, which may contain in addition to the N atom also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and the
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]-carbonyl , (Ci-C )-Alkoxy, (Ci- C4)-Haloalkoxy, (Ci-C4)-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann unsubstituted or by one or more radicals from the group halogen, (Ci-C) -alkyl, (Ci-C) -haloalkyl, [(Ci-C) -alkoxy] -carbonyl, (Ci-C) -alkoxy, (Ci - C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, hydroxy is substituted and wherein a heterocyclic ring n can contain oxo groups
oder  or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe R 3 and R 4 together with the directly attached N atom, the group
-N=CR5-NR6R7 bedeuten, wobei R5 für Wasserstoff oder (Ci-Ce)-Alkyl steht und -N = CR 5 -NR 6 R 7 , wherein R 5 is hydrogen or (Ci-Ce) alkyl and
R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
R6 und R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bissiebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und n für 0, 1 oder 2 steht. Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I) oder deren Salze, worin R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)- Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy substituiert ist, R 6 and R 7 together with the directly bonded N atom form a five-bissiebengliedrigen, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and n is 0, 1 or 2. Particular preference is given to the use according to the invention of compounds of the general formula (I) or salts thereof in which R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or halogen by one or more radicals , (Ci-C 4 ) - alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) -haloalkoxy is substituted,
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, (Ci-C8)-Alkyl, (C2-Cs)-Alkenyl oder (C2-C8)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)- Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )- alkylj-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]- carbonyl, (C3-C6)-Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, R 3 and R 4 independently of one another are hydrogen, (C 1 -C 8) -alkyl, (C 2 -C 5) -alkenyl or (C 2 -C 8) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4) -alkyl] -amino, Hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(C 1 -C 4 ) -haloalkoxy] -carbonyl, (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, Heteroaryl which is unsubstituted or substituted or substituted heterocyclyl which is unsubstituted or substituted,
oder  or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) ) -Haloalkylcarbonyl,
oder  or
(C3-C6)-Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )- Alkylthio, Phenyl, das unsubstituiert oder substituiert ist, substituiert ist bedeutet, oder (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) - Alkylthio, phenyl which is unsubstituted or substituted, is substituted, or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( C 1 -C 10 -haloalkoxy, C 1 -C -alkylthio, C 1 -C -alkylsulfoxy, C 1 -C -alkylsulfone, C 1 -C -haloalkylthio, C 1 -C -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl,
oder R3 Wasserstoff oder (Ci-Ce)-Alkyl bedeutet und or R 3 is hydrogen or (C 1 -C 6) -alkyl and
R4 (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)- Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder R 4 is (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C2-C6) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 6) - haloalkoxy, or ( Ci-C 6 ) -alkyl-SO 2 , or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen Aminosäurerest und zwar die natürlich vorkommenden in ihrer racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der R 3 and R 4 together with the directly attached N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or R 3 and R 4 together with the directly bonded N atom form four- to eight-membered carbocyclic or heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]-carbonyl , (Ci-C )-Alkoxy, (Ci- unsubstituted or by one or more radicals from the group halogen, (Ci-C) -alkyl, (Ci-C) -haloalkyl, [(Ci-C) -alkoxy] -carbonyl, (Ci-C) -alkoxy, (Ci -
C4)-Haloalkoxy, (Ci-C4)-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, hydroxy, and wherein a heterocyclic ring may contain n oxo groups
oder R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe or R 3 and R 4 together with the directly attached N atom, the group
-N=CR5-NR6R7 bedeuten, wobei für Wasserstoff oder (Ci-Ce)-Alkyl steht R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-C6)-Alkyl bedeuten, oder -N = CR 5 -NR 6 R 7 , wherein is hydrogen or (Ci-Ce) alkyl R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
R6 und R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis R 6 and R 7 , together with the directly attached N atom, form a five-bis
siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und n für 0, 1 oder 2 steht.  seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and n is 0, 1 or 2.
Ganz besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Very particular preference is given to the use according to the invention of compounds of the general formula (I) or salts thereof, in which
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)- Alkyl, (Ci-C4)-Haloalkyl substituiert ist, R 1 is (C3-C6) -cycloalkyl, phenyl or pyridinyl, each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, (Ci-C 4) - substituted alkyl, (Ci-C 4) -haloalkyl is
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-R 3 and R 4 independently of one another are hydrogen, (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or halogen by one or more radicals , Hydroxy, cyano, (Ci-C 4 ) -
Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )- alkylj-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]- carbonyl, (C3-C6)-Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, Alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylamino, di [(C 1 -C 4 ) -alkylamino, hydroxycarbonyl, [(C 1 -C 4 ) -alkoxy] carbonyl, [(C 1 -C 4 ) -haloalkoxy] carbonyl, (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocyclyl which is unsubstituted or substituted, is substituted,
oder  or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C4)-alkyl- carbonyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Haloalkylcarbonyl bedeuten, [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 6) -alkylcarbonyl, C6) -haloalkylcarbonyl,
oder (C3-C6)-Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Alkoxy, (Ci-C )-Alkylthio substituiert ist bedeutet, or (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy and (C 1 -C 4) -alkylthio,
oder  or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( Ci-C) haloalkoxy, (Ci-C) alkylthio, (Ci-C) - alkylsulfoxy, (Ci-C) alkylsulfone, (Ci-C) alkoxy-carbonyl, (C3-C6) -cycloalkyl, is substituted,
oder  or
R3 Wasserstoff oder (Ci-Ce)-Alkyl bedeutet und R 3 is hydrogen or (C 1 -C 6) -alkyl and
R4 (Ci-C6)-Alkyl-SO2 bedeutet, oder R 4 is (C 1 -C 6 ) -alkyl-SO 2 , or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen Aminosäurerest und zwar die natürlich vorkommenden in ihrer racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder R 3 and R 4 together with the directly bound N atom represent an amino acid residue, namely the naturally occurring in their racemic and in their respective D and L form, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly attached N atom form a four-bis
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der  form eight-membered carbocyclic or heterocyclic ring, which may contain in addition to the N atom also further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and the
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]-carbonyl , (Ci-C )-Alkoxy, (Ci- C4)-Haloalkoxy, (Ci-C4)-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann, oder unsubstituted or by one or more radicals from the group halogen, (Ci-C) -alkyl, (Ci-C) -haloalkyl, [(Ci-C) -alkoxy] -carbonyl, (Ci-C) -alkoxy, (Ci C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, hydroxy, and where a heterocyclic ring may contain n oxo groups, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe R 3 and R 4 together with the directly attached N atom, the group
-N=CR5-NR6R7 bedeuten, wobei -N = CR 5 -NR 6 R 7 , where
R5 für Wasserstoff oder (Ci-Ce)-Alkyl steht und R 5 is hydrogen or (C 1 -C 6) -alkyl and
R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R 6 and R 7 independently of one another denote hydrogen or (C 1 -C 6) -alkyl, or
R6 und R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis R 6 and R 7 , together with the directly attached N atom, form a five-bis
siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und und n für 0 oder 1 steht.  seven-membered, preferably saturated heterocyclic ring such as piperidinyl, pyrrolidinyl or morpholinyl and and n is 0 or 1.
Zum Teil sind die zuvor genannten substituierten Pyridoncarboxamide der allgemeinen Formel (I) noch nicht beschrieben worden. In some cases, the abovementioned substituted pyridone carboxamides of the general formula (I) have not yet been described.
Somit gelten als weiterer Teil der Erfindung substituierte Pyridoncarboxamide der allgemeinen Formel (I) oder deren Salze, Thus, as a further part of the invention, substituted pyridone carboxamides of the general formula (I) or salts thereof,
Figure imgf000016_0001
worin R1 (C3-C6)-Cycloalkyl, Phenyl oder Hetaryl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C )-Haloalkylsulfon, (Ci-C )- Alkoxy-carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl (Ci-C6)-alkyl, (Ci-C )-Alkoxy-carbonyl-(Ci-C )- alkyl, Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist,
Figure imgf000016_0001
wherein R 1 is (C 3 -C 6) -cycloalkyl, phenyl or hetaryl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) - Alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfoxy, (C 1 -C 4 ) - Alkylsulfone, (C 1 -C 6) -haloalkylthio, (C 1 -C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) -haloalkoxycarbonyl, C 4 ) -alkylcarboxy, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl , Hydroxycarbonyl- (C 1 -C 4 ) -alkyl, R 8 R 9 is N-carbonyl substituted,
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 Ethyl bedeutet und R4 CH2CH2-R10 bedeutet und R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
R10 Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C1- C4)-Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(C1-R 10 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl or (C 2 -C 8 ) -alkynyl, each of the last-named 3 radicals being unsubstituted or by one or more radicals from the group consisting of halogen , Hydroxy, cyano, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylamino, di [(C 1 -C 4 ) - alkyl] -amino, hydroxycarbonyl, [(C1-
C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl substituiert ist bedeuten, oder C 4 ) -alkoxy] -carbonyl, [(Ci-C 4 ) -haloalkoxy] -carbonyl is substituted, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-Ci6)-Alkylcarbonyl, (Ci-Ci6)-Haloalkylcarbonyl bedeuten, oder [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 16) ) Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (C1-(C 3 -C 6) -cycloalkyl, (C 4 -C 6) -cycloalkenyl where each of the latter two radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) Haloalkyl, (Ci-C) -alkoxy, (C1-
C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)-Cycloalkyl, Phenyl, Heteroaryl oder Heterocyclyl substituiert ist bedeuten, C) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylamino, di [(C 1 -C 4 ) -alkyl] -amino, [(C 1 -C 4 ) -alkoxy] -carbonyl, [(Ci -C 4 ) -haloalkoxy] carbonyl, (C 3 -C 6 ) -cycloalkyl, phenyl, heteroaryl or heterocyclyl is substituted,
oder Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)- Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )- Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C )-Haloalkylsulfon, (Ci-C )-Alkoxy- carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl (Ci-C6)-alkyl, (Ci-C )-Alkoxy-carbonyl-(Ci-C )-alkyl, or Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or represented by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) Haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -alkylsulfoxy, (C 1 -C 4 ) -alkylsulfone, (C 1 -C 4 ) Haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci-C) -haloalkylsulfone, (Ci-C) -alkoxycarbonyl, (Ci-C 4 ) -haloalkoxycarbonyl, (Ci-C 4 ) -alkylcarboxy, ( C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -alkoxycarbonyl- (C 1 -C 4) -alkyl,
Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, Hydroxycarbonyl, hydroxycarbonyl- (C 1 -C 4 ) -alkyl, R 8 R 9 is N-carbonyl substituted,
R8 und R9 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten R 8 and R 9 independently of one another denote hydrogen or (C 1 -C 6) -alkyl
Bevorzugt sind Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Preference is given to compounds of the general formula (I) or salts thereof, in which
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (C3- C6)-Cycloalkyl substituiert ist, R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 Ethyl bedeutet und R 3 is ethyl and
R4 CH2CH2-R10 bedeutet und R 4 is CH 2 CH 2 -R 10 and
R10 Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, wobei jeder der R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C1- C4)-Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(C1- C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, substituiert ist bedeuten, oder the latter 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 ) alkoxy, (Ci-C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (Ci-C 4) alkylamino, di [(Ci-C 4) -alkyl] amino, hydroxycarbonyl, [(C1-C4) -alkoxy] carbonyl, is [(Ci-C4) -haloalkoxy] carbonyl, substituted mean , or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, oder [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) ) -Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Alkylthio, Phenyl substituiert ist bedeuten, (C 3 -C 6) -cycloalkyl, (C 4 -C 6) -cycloalkenyl, where each of the latter two radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) -alkylthio, phenyl is substituted,
oder  or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci- C4)-Al kylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci- C4)-Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)- Cycloalkyl, substituiert ist, Phenyl, heteroaryl, or heterocyclyl, wherein each of the three radicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C ) -Alkoxy, (Ci-C) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -haloalkylthio, (Ci- C 4 ) -haloalkylsulfoxy, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl, is substituted,
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Particular preference is given to compounds of the general formula (I) or salts thereof, in which
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy substituiert ist, R 1 is (C 3 -C 6) -cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkyl -C) -alkoxy, (Ci-C) -haloalkoxy is substituted,
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 Ethyl bedeutet und R 3 is ethyl and
R4 CH2CH2-R10 bedeutet und R 4 is CH 2 CH 2 -R 10 and
R10 Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, wobei jeder der R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C1- C4)-Al kylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(C1- C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, substituiert ist bedeuten, oder last 3 radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (C1-C4) -alkyl alkylthio, (Ci- C 4) alkylamino, di [(Ci-C 4) -alkyl] amino, hydroxycarbonyl, [(C1-C4) -alkoxy] carbonyl, is [(Ci-C4) -haloalkoxy] carbonyl, substituted mean, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)-alkyl- carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, [(C 1 -C 4 ) -alkoxy] -carbonyl-carbonyl, [(C 1 -C 4 ) -alkoxy] -carbonyl- (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) -alkylcarbonyl, (C 1 -C 8) ) -Haloalkylcarbonyl,
oder  or
(C3-C6)-Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )- Alkylthio substituiert ist bedeutet, (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) - alkylthio is substituted,
oder  or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy,Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, ( C 1 -C 10 -haloalkoxy, C 1 -C -alkylthio, C 1 -C -alkylsulfoxy, C 1 -C -alkylsulfone, C 1 -C -haloalkylthio, C 1 -C -haloalkylsulfoxy,
(Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, (C 1 -C 4 ) -haloalkylsulfone, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 6) -cycloalkyl,
Ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Very particular preference is given to compounds of the general formula (I) or salts thereof, in which
(C3-C6)-Cycloalkyl oder Phenyl bedeutet, wobei jeder der beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen (Ci-C )-Alkyl, (Ci-C )-Haloalkyl substituiert ist, (C 3 -C 6) -cycloalkyl or phenyl, where each of the two radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl,
Wasserstoff bedeutet und Hydrogen means and
R3 Ethyl bedeutet und R4 CH2CH2-R10 bedeutet und R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
R10 Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, wobei jeder der R 10 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where each of the
letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy substituiert ist bedeuten, the last-mentioned 3 unsubstituted or by one or more radicals the group halogen, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy is substituted,
oder (C3-C6)-Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Alkoxy, (Ci-C )-Alkylthio substituiert ist bedeutet,  or (C 3 -C 6) -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy and (C 1 -C 4) -alkylthio,
oder Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C4)-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, or phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylsulfoxy, (C 1 -C 4) -alkylsulfone, (C 1 -C 4) -alkoxycarbonyl, (C 3 -C 6 ) -cycloalkyl , is substituted,
Insbesondere ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I) oder deren Salze, worin Very particular preference is given to compounds of the general formula (I) or salts thereof, in which
R1 (C3-C6)-Cycloalkyl oder Phenyl bedeutet, R 1 is (C 3 -C 6 ) -cycloalkyl or phenyl,
R2 Wasserstoff bedeutet und R 2 is hydrogen and
R3 Ethyl bedeutet und R4 CH2CH2-R10 bedeutet und R 3 is ethyl and R 4 is CH 2 CH 2 -R 10 and
R10 Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl R 10 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl
Somit gilt als weiterer Gegenstand der Erfindung auch eine Sprühlösung zur Thus, a further subject of the invention is also a spray solution for
Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge einer oder mehrer der zuvor genannten substituierten Pyridoncarboxamide. Inn Hinblick auf die vorstehend genannten Verbindungen der allgemeinen Formel (I) werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: Treatment of plants containing an amount of one or more of the abovementioned substituted pyridone carboxamides effective to increase the resistance of plants to abiotic stresses. With respect to the above compounds of the general formula (I), 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:
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a remainder, then "halogen" means
beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. Alkyl bedeutet erfindungsgemäß einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio- oder Nitrogruppen, besonders bevorzugt sind Fluor, Chlor, Brom oder lod. for example, a fluorine, chlorine, bromine or iodine atom. Alkyl means according to the invention a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio or nitro groups, particular preference is given to fluorine, chlorine, bromine or iodine.
Fluoralkyl bedeutet einen geradkettigen oder verzweigten offenkettigen, gesättigten und durch Fluor substituierten Kohlenwasserstoffrest, wobei sich mindestens ein Fluoratom an einer der möglichen Positionen befindet. Perfluoralkyl bedeutet einen geradkettigen oder verzweigten offenkettigen, gesättigten und vollständig durch Fluor substituierten Kohlenwasserstoffrest wie z.B. CF3, CF2CF3,
Figure imgf000022_0001
Fluoroalkyl means a straight-chain or branched, open-chain, saturated and fluorine-substituted hydrocarbon radical, at least one fluorine atom being in one of the possible positions. Perfluoroalkyl means a straight-chain or branched, open-chain, saturated and completely fluorine-substituted hydrocarbon radical, for example CF 3, CF 2 CF 3,
Figure imgf000022_0001
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 Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, the corresponding fluorine atoms being present as substituents on one or more
verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten different carbon atoms of the straight-chain or branched
Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
Teilfluoriertes Haloalkyl bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor, Brom oder lod. 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 Halogen atoms are selected from the group fluorine, chlorine, bromine or iodine. The corresponding halogen atoms may be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the
vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.
Haloalkyl, -alkenyl und -alkinyl bedeuten durch gleiche oder verschiedene Haloalkyl, alkenyl and alkynyl mean the same or different
Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Halogen atoms, partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH 3 , CH 2 Cl, CH 2 F;
Perhaloalkyl wie z. B. CCI3, CCIF2, CFCI2,CF2CCIF2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFCI, CF2CCIFH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl, und der Begriff Polyhaloalkyl umfasst auch die Begriffe teilfluoriertes Alkyl und teilfluoriertes Haloalkyl. Perhaloalkyl such. CCI 3 , CCIF 2 , CFCI 2 , CF 2 CCIF 2 , CF 2 CCIFCF 3 ; Polyhaloalkyl such. CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also encompasses the term perfluoroalkyl, and the term polyhaloalkyl also encompasses the terms partially fluorinated alkyl and partially fluorinated haloalkyl.
Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; 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;
Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. The same applies to haloalkenyl and other halogen-substituted radicals.
Der Ausdruck "(Ci-C4)-Alkyl" bedeutet eine Kurzschreibweise für Alkyl mit einem bis vier Kohlenstoffatomen entsprechend der 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 gradkettige oder verzweigte The term "(C 1 -C 4 ) -alkyl" denotes a short notation for alkyl having one to four carbon atoms corresponding to the range given for C atoms, ie 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. As "(Ci-C6) -alkyl", accordingly also include straight-chain or branched
Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
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. Dreifachbindung. Carbon skeletons, for example having 1 to 6 carbon atoms or in unsaturated groups having 2 to 6 carbon atoms, are preferred. Alkyl radicals, including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond.
Alkenyl schließt insbesondere auch geradkettige oder verzweigte offenkettige 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. Prop-1 -en-1 -yl, But-1 -en-1 -yl, Allyl, 1 - Methyl-prop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, 1 -Methyl-but-3-en-1 -yl und 1 -Methyl-but-2-en-1 -yl, 2-Methylprop-1 -en-1 -yl, 1 -Methylprop-1 -en-1 -yl, Hydrocarbon radicals having more than one double bond, such as 1, 3-butadienyl and 1, 4-pentadienyl, but also allenyl or cumulene radicals having one or more cumulative 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, e.g. Prop-1 -en-1-yl, but-1-en-1-yl, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, But-2-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methylprop-1 -ene-1-yl, 1-methylprop-1-ene-1-yl,
1 -Methylprop-2-en-1 -yl, 2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, But-3-en-1 -yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,
1 - Methyl-but-3-en-1 -yl oder 1 -Methyl-but-2-en-1 -yl, Pentenyl, 2-Methylpentenyl oder Hexenyl.  1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl, pentenyl, 2-methylpentenyl or hexenyl.
Alkinyl schließt insbesondere auch geradkettige oder verzweigte offenkettige In particular, alkynyl 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-1 -in-1 -yl. (C2-C6)-Alkinyl bedeutet beispielsweise Ethinyl, Propargyl, 1 -Methyl-prop-2-in-1 -yl, 2-Butinyl, 2-Pentinyl oderHydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds, such as 1, 3-butatrienyl and 3-penten-1-yn-1-yl. For example, (C 2 -C 6) alkynyl means ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl, 2-pentynyl or
2- Hexinyl, vorzugsweise Propargyl, But-2-in-1 -yl, But-3-in-1 -yl oder 2-hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or
1 -Methyl-but-3-in-1 -yl. 1-methyl-but-3-yn-1-yl.
Der Begriff„Cycloalkyl" bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. The term "cycloalkyl" means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
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-Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl,
Der Begriff„Aryl" bedeutet ein 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 gegebenenfalls einfach oder mehrfach mit einem Rest der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci-C )-Alkoxy]-carbonyl, [(Ci-C )-Haloalkoxy]-carbonyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl (Ci-C6)-alkyl, [(Ci-C )-Alkoxy]-carbonyl, [(Ci-C )-Alkoxy]-carbonyl-(Ci-C )- alkyl, Hydroxycarbonyl oder Hydroxycarbonyl-(Ci-C4)-alkyl substituiertesPhenyl. The term "aryl" means a 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 optionally mono- or polysubstituted by a radical from the group halogen, nitro, hydroxy, cyano, (Ci-C) -alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy , (Ci-C) -haloalkoxy, (Ci-C) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci-C) -alkylamino, di [(Ci-C) -alkyl ] amino, [(Ci-C) alkoxy] carbonyl, [(Ci-C) -haloalkoxy] carbonyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6 ) -alkyl, [(C 1 -C 4) -alkoxy] -carbonyl, [(C 1 -C 4) -alkoxy] -carbonyl- (C 1 -C 4 ) -alkyl, hydroxycarbonyl or hydroxycarbonyl- (C 1 -C 4 ) -alkyl-substituted phenyl ,
Vom Begriff„gegebenenfalls substituierte Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, wherein the
Bindungsstelle am aromatischen System ist. Binding site on the aromatic system is.
Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff„gegebenenfalls substituiertes Phenyl" umfasst. As a rule, "aryl" is also encompassed by the term "optionally substituted phenyl".
Gegebenenfalls substituiertes Aryl (Phenyl) ist vorzugsweise Aryl (Phenyl), das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C4)- Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci- C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)- Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl (Ci-C6)-alkyl, (Ci-C )-Alkoxy- carbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyl, 2-, 3- und Optionally substituted aryl (phenyl) is preferably aryl (phenyl) which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, nitro, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (Ci-C) -haloalkyl, (Ci-C) -alkoxy, (Ci-C) -haloalkoxy, (Ci-C) -alkylthio, (Ci-C) -alkylsulfoxy, (Ci-C) -alkylsulfone, (Ci -C) -haloalkylthio, (Ci-C) -haloalkylsulfoxy, (Ci-C 4 ) -haloalkylsulfone, (Ci-C 4 ) -alkoxycarbonyl, (Ci-C 4 ) -haloalkoxycarbonyl, (Ci-C 4 ) - alkylcarboxy, (C3-C6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C) alkoxy carbonyl (Ci-C 4) alkyl, hydroxycarbonyl , Hydroxycarbonyl (Ci-C 4 ) -alkyl, for example, o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and
4-Trifluor- und -Trichlorphenyl, 2,4-, 3,5-, 2,5- und 2,3-Dichlorphenyl, o-, m- oder p-Methoxyphenyl. 4-trifluoro- and trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- or p-methoxyphenyl.
Ein heterocyclischer Rest oder Ring (Heterocyclyl) kann gesättigt, ungesättigt oder heteroaromatisch und unsubstituiert oder beispielsweise mit einem Rest aus der Gruppe bestehend aus Halogen, Nitro, Hydroxy, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic and unsubstituted or, for example, with a radical selected from the group consisting of halogen, nitro, hydroxy, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -
Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci-C )-Alkoxy]- carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl (C1-C6)- alkyl, [(Ci-C )-Alkoxy]-carbonyl, [(Ci-C )-Alkoxy]-carbonyl-(Ci-C )-alkyl, Hydroxycarbonyl oder Hydroxycarbonyl-(Ci-C4)-alkyl substituiert sein; er enthält vorzugsweise ein oder mehrere Heteroatome im Ring, vorzugsweise aus der Gruppe N, O und S; er ist ein aliphatischer Heterocyclylrest mit 3 bis 7 Ringatomen oder ein heteroaromatischer Rest mit 5 oder 6 Ringatomen und enthält 1 , 2 oder 3 Haloalkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 4) -alkylthio, (C 1 -C 4) -alkylsulfoxy, (C 1 -C 4) -alkylsulfone, (C 1 -C 4) -alkylamino, Di [(C 1 -C 4) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6) ) -Cycloalkyl (C 1 -C 6) -alkyl, [(C 1 -C 4) -alkoxy] -carbonyl, [(C 1 -C 4) -alkoxy] -carbonyl (C 1 -C 4) -alkyl, Hydroxycarbonyl or hydroxycarbonyl- (C 1 -C 4 ) -alkyl; it preferably contains one or more heteroatoms in the ring, preferably from the group N, O and S; it is an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3
Heteroatome. Der heterocyclische Rest kann z.B. ein heteroaromatischer Rest oder Ring (Heteroaryl) sein, wie z.B. ein mono-, bi- oder polycyclisches aromatisches System, in dem mindestens 1 Ring ein oder mehrere Heteroatome enthält, Hetero atoms. The heterocyclic radical may be e.g. a heteroaromatic radical or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least one ring contains one or more heteroatoms,
beispielsweise Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Oxazolyl, Furyl, Pyrrolyl, Pyrazolyl und Imidazolyl, oder ist ein partiell oder vollständig hydrierter Rest wie Oxiranyl, Oxetanyl, Pyrrolidyl, Piperidyl, Piperazinyl, Dioxolanyl, Morpholinyl, Tetrahydrofuryl. Als Substituenten für einen substituierten for example, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. As substituents for a substituted
heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten. Heterocyclic radical are the substituents mentioned below in question, in addition also oxo. The oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. at N and S, occur.
Alkoxy bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest, Cycloalkyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. Alkoxy is an alkyl radical bonded via an oxygen atom, alkenyloxy is an alkynyl radical bonded via an oxygen atom, alkynyloxy is an alkynyl radical bound via an oxygen atom, cycloalkyloxy is a cycloalkyl radical bonded via an oxygen atom, and cycloalkenyloxy is a cycloalkenyl radical bonded via an oxygen atom.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methylthio, Ethylthio, n- Propylthio, Isopropylthio, n-Butylthio, Isobutylthio, sec-Butylthio und tert-Butylthio. Alkenylthio bedeutet ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkenylrest. According to the invention, "alkylthio" - alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio. Alkenylthio represents an alkenyl radical bonded via a sulfur atom, alkynylthio represents an alkynyl radical bonded via a sulfur atom, cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom, and cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom.
Erfindungsgemäß steht "AI kylsulfinyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes AI kylsulfinyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen wie beispielsweise Methylsulfinyl, Ethylsulfinyl, n-Propylsulfinyl, Isopropylsulfinyl, n-Butylsulfinyl, Isobutylsulfinyl, sec- Butylsulfinyl und tert-Butylsulfinyl. According to the invention "AI kylsulfinyl" - alone or as part of a chemical group - kylsulfinyl straight or branched Al, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl , Isobutylsulfinyl, sec- Butylsulfinyl and tert-butylsulfinyl.
Erfindungsgemäß steht "AI kylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen wie beispielsweise Methylsulfonyl,According to the invention "Al kylsulfonyl" - alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
Ethylsulfonyl, n-Propylsulfonyl, Isopropylsulfonyl, n-Butylsulfonyl, Isobutylsulfonyl, sec- Butylsulfonyl und tert-Butylsulfonyl. Ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl.
Erfindungsgemäß steht "Cycloalkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für gegebenenfalls substituiertes Cycloalkylsulfonyl, vorzugsweise mit 3 bis 6 Kohlenstoffatomen wie beispielsweise Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl oder Cyclohexylsulfonyl.  According to the invention "cycloalkylsulfonyl" - alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
Erfindungsgemäß steht "Arylsulfonyl" für gegebenenfalls substituiertes Phenylsulfonyl oder gegebenenfalls substituiertes polycyclisches Arylsulfonyl, beispielsweise substituiert durch Halogen, Alkyl, Haloalkyl, Haloalkoxy oder Alkoxygruppen. According to the invention "arylsulfonyl" is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, for example substituted by halogen, alkyl, haloalkyl, haloalkoxy or alkoxy groups.
Der Begriff„Sulfilimin" steht für eine Gruppe mit einer Stickstoff- Schwefeldoppelbindung, bei der Stickstoff und Schwefel weiter substituiert sind, das Stickstoffatom bevorzugt durch eine weiter substituierte Carbonylgruppe und der Schwefel bevorzugt durch zwei gleiche oder gemischte Alkyl, Aryl und The term "sulfilimine" means a group having a nitrogen-sulfur double bond in which nitrogen and sulfur are further substituted, the nitrogen atom preferably by a further substituted carbonyl group and the sulfur preferably by two identical or mixed alkyl, aryl and
Cycloalkylsubstituenten, beispielsweise in Form einer N-(Di-n-butyl-sulfanyliden), N- (Di-iso-propyl-sulfanyliden), N-(Di-n-propyl-sulfanyliden), N-(Di-n-pentyl-sulfanyliden), N-(Di-iso-butyl-sulfanyliden), N-(Cyclobutyl-iso-propyl-sulfanyliden), N-(n-Propyl-iso- propyl-sulfanyliden), N-(Cyclopropyl-iso-propyl-sulfanyliden) oder N-(lso-Butyl-iso- propyl-sulfanyliden) Einheit.  Cycloalkyl substituents, for example in the form of an N- (di-n-butyl-sulfanylidene), N- (di-iso-propyl-sulfanyliden), N- (di-n-propyl-sulfanyliden), N- (di-n-pentyl -sulfanylidene), N- (diisobutylsulfanylidene), N- (cyclobutylisopropylsulfanylidene), N- (n-propylisopropylsulfanylidene), N- (cyclopropylisopropyl) sulfanylidene) or N- (iso-butylisopropylsulfanylidene) unit.
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E- Isomere sind alle von der allgemeinen Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische 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 general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, are one or more asymmetric
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 Carbon atoms present, so enantiomers and diastereomers may occur. Stereoisomers can be detected from the mixtures obtained in the preparation obtained 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. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active
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. Die oben angeführten allgemeinen oder in Vorzugsbereichen angeführten  Starting and / or auxiliaries are selectively prepared. 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 general or preferred ones mentioned above
Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- und  Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting and in each case required for the preparation
Zwischenprodukte. Diese Restedefinitionen können untereinander, als auch zwischen den angegebenen bevorzugten Bereichen vertauscht werden. Intermediates. These residue definitions can be interchanged with each other as well as between the specified preferred ranges.
Der Begriff„Nutzpflanzen", wie hier verwendet, bezeichnet Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln oder für technische Zwecke eingesetzt werden. The term "crops" as used herein refers to crops used as plants for the production of food, feed or for technical purposes.
Die Verbindungen der allgemeinen Formel (I) können hergestellt werden, indem man beispielsweise The compounds of the general formula (I) can be prepared by, for example,
(a) eine Carbonsäure der allgemeinen Formel (II) (a) a carboxylic acid of the general formula (II)
Figure imgf000028_0001
worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel
Figure imgf000028_0001
wherein R 1 and R 2 as in the compound of general formula
(I) gemäß obiger Restedefinition definiert sind, (I) are defined according to the above definition of the residue,
mit einem Amin der allgemeinen Formel (III) oder dessen Salz, R3 with an amine of the general formula (III) or its salt, R 3
R4 worin R3 und R4 wie in der herzustellenden Verbindung der allgenneinen Formel (I) gemäß obiger Restdefinition definiert sind, R 4 in which R 3 and R 4 are defined as in the compound of general formula (I) according to the above definition,
gegebenenfalls in Gegenwart eines carbonsäureaktivierenden Reagenzes, beispielsweise Ν,Ν-Carbonyldiimidazol (CDI), oder eines wasserentziehenden Mittels, beispielsweise Dicyclohexylcarbodiimid (DCC), zur Verbindung der allgmeinen Formel (I) umsetzt oder (b) einen Carbonsäureester der allgemeinen Formel (IV)  if appropriate in the presence of a carboxylic acid-activating reagent, for example Ν, Ν-carbonyldiimidazole (CDI), or of a dehydrating agent, for example dicyclohexylcarbodiimide (DCC), to give the compound of the general formula (I) or (b) a carboxylic acid ester of the general formula (IV)
Figure imgf000029_0001
worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind und„Alkyl" einen Alkylrest, beispielsweise Methyl oder Ethyl, bedeutet, mit einem Amin der allgemeinen Formel (III) oder dessen Salz,
Figure imgf000029_0001
wherein R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above definition and "alkyl" is an alkyl radical, for example methyl or ethyl, with an amine of general formula (III) or its salt,
R R
I  I
worin R3 und R4 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind, zur Verbindung der allgemeinen Formel (I) umsetzt oder (c) ein Carbonsäurehalogenid oder -anhydrid der allgemeinen Formel (V),
Figure imgf000030_0001
worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind und Hai ein Halogenatom, beispielsweise Chlor, oder einen Acyloxyrest bedeutet, mit einem Amin der allgemeinen Formel (III) oder dessen Salz, wherein R 3 and R 4 are as defined in the compound of general formula (I) to be prepared according to the above definition, to give the compound of general formula (I) or (c) a carboxylic acid halide or anhydride of general formula (V),
Figure imgf000030_0001
wherein R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above definition and Hal is a halogen atom, for example chlorine, or an acyloxy, with an amine of general formula (III) or its salt,
R3 R 3
I  I
H %4 (Hl) worin R3 und R4 wie in der herzustellenden Verbindung der allgemeinen Formel (I) definiert sind, zur Verbindung der allgemeinen Formel (I) umsetzt, im Falle, dass R3 und R4 in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition jeweils Wasserstoff bedeutet, eine Verbindung der allgemeinen Formel (VI), In which R 3 and R 4 are as defined in the compound of general formula (I) to be prepared, to give the compound of general formula (I), in the case where R 3 and R 4 in the compound to be prepared general formula (I) according to the above radical definition in each case hydrogen, a compound of general formula (VI),
Figure imgf000030_0002
worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert ist und "Alkyl" einen Alkylrest, beispielsweise Methyl oder Ethyl, bedeutet,
Figure imgf000030_0002
wherein R 1 and R 2 are as defined in the compound of general formula (I) to be prepared according to the above definition of the radical and "alkyl" is an alkyl radical, for example methyl or ethyl,
mit Malonsäurediamid zur Verbindung der allgemeinen Formel (I) umsetzt.  reacted with Malonsäurediamid to the compound of general formula (I).
Die Amidbildungen nach Variante (a) können beispielsweise in einem inerten organischen Lösungsmittel in einem Temperaturbereich zwischen 0 °C und 150 °C, vorzugsweise 0 °C und 50 °C durchgeführt werden. Als organische Lösungsmittel eignen sich beispielsweise polare protische oder aprotische Lösungsmittel wie Ether, z. B. Diethylether, Tetrahydrofuran und Dioxan, oder Nitrile wie Acetonitril, oder Amide wie Dimethylformamid. The amide formations according to variant (a) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 0 ° C and 50 ° C. Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, z. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
Die Amidbildungen nach Variante (b) können beispielsweise in einem inerten organischen Lösungsmittel in einem Temperaturbereich zwischen 0 °C und 150 °C, vorzugsweise 50 °C und 100 °C durchgeführt werden. Als organische Lösungsmittel eignen sich beispielsweise polare protische oder aprotische Lösungsmittel wie Ether, z. B. Tetrahydrofuran und Dioxan, oder Nitrile wie Acetonitril, oder Amide wie The amide formations according to variant (b) can be carried out, for example, in an inert organic solvent in a temperature range between 0 ° C and 150 ° C, preferably 50 ° C and 100 ° C. Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. For example, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as
Dimethylformamid. Bevorzugt ist jedoch die Amidbildung nach Variante (b) bei erhöhten Temperaturen durch Umsetzung der Reaktionspartner in Substanz. Dimethylformamide. Preferably, however, the amide formation according to variant (b) at elevated temperatures by reaction of the reactants in substance.
Die Amidbildungen nach Variante (c) können beispielsweise in Gegenwart eines säurebindenden Mittels in einem inerten organischen Lösungsmittel in einem The amide formations according to variant (c) can, for example, in the presence of an acid-binding agent in an inert organic solvent in a
Temperaturbereich zwischen 0 °C und 150 °C, vorzugsweise 0 °C und 50 °C Temperature range between 0 ° C and 150 ° C, preferably 0 ° C and 50 ° C.
durchgeführt werden. Als organische Lösungsmittel eignen sich beispielsweise polare protische oder aprotische Lösungsmittel wie Ether, z. B. Diethylether, Tetrahydrofuran und Dioxan, oder Nitrile wie Acetonitril, oder Amide wie Dimethylformamid. be performed. Suitable organic solvents are, for example, polar protic or aprotic solvents such as ethers, eg. As diethyl ether, tetrahydrofuran and dioxane, or nitriles such as acetonitrile, or amides such as dimethylformamide.
Säurebindende Mittel sind beispielsweise Alkali- oder Erdalkalimetallcarbonate wie z. B. Natrium-, Kalium- oder Calciumcarbonat, Alkali- oder Erdalkalimetallhydroxide, wie Natrium-, Kalium oder Calciumhydroxid, oder Alkalimetallhydride oder-amide, wie Natrium- oder Kaliumhydrid oder-amid, oder auch organische Basen, wie Triethylamin, Pyridin, Dimethylaminopyridin, DBU (1 ,8-Diazabicyclo[5.4.0]-undec-7-en), DBN (1 ,5- Diazabicyclo[4.3.0]non-5-en) und 1 ,4-Diazabicyclo[2.2.2]octan. Acid-binding agents are, for example, alkali metal or alkaline earth metal carbonates such as. Example, sodium, potassium or calcium carbonate, alkali metal or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide, or alkali metal hydrides or amides such as sodium or potassium hydride or amide, or organic bases such as triethylamine, pyridine, dimethylaminopyridine, DBU (1,8-diazabicyclo [5.4.0] undec-7-ene), DBN (1,5-diazabicyclo [4.3.0] non-5-ene) and 1,4-diazabicyclo [2.2.2] octane ,
Die Amidbildungen nach Variante (d) können analog den Verfahren durchgeführt werden, wie sie in EP 522392 und Helv. Chim. Acta 71 (1988) 596-601 und GB The amide formations according to variant (d) can be carried out analogously to the methods described in EP 522392 and Helv. Chim. Acta 71 (1988) 596-601 and GB
2305174 beschrieben sind. Das Malonsäurediamid kann in der Regel in einem organischen wasserfreien polaren protischen oder aprotischen Lösungsmittel, beispielsweise in einem Alkohol, mit einer starken Base wie einem Alkalimetall, Alkalimetallhydrid oder Alkalimetallalkoholat in ein reaktives Salz überführt und dann mit der Verbindung der allgemeinen Formel (VI) umgesetzt werden. Die Umsetzung mit der Verbindung (VI) kann in der Regel in einem Temperaturbereich zwischen 0 °C und dem Siedepunkt des Lösungsmittels (je nach Lösungsmittel etwa bis 150 °C) durchgeführt werden. Die Verbindungen der allgenneinen allgenneinen Formeln (II), (III), (IV) und (V) sind entweder kommerziell erhältlich oder können nach oder analog dem Fachmann bekannten Methoden hergestellt werden (z. B. Helv. Chim. Acta 71 (1988) 596; EP 502740; EP 522392). 2305174 are described. The malonamide may typically be converted to a reactive salt in an organic anhydrous polar protic or aprotic solvent, for example in an alcohol, with a strong base such as an alkali metal, alkali metal hydride or alkali metal alcoholate and then reacted with the compound of general formula (VI) , The reaction with the compound (VI) can be carried out usually in a temperature range between 0 ° C and the boiling point of the solvent (depending on the solvent about to 150 ° C). The compounds of general formulas (II), (III), (IV) and (V) are either commercially available or can be prepared by or analogously to methods known to the person skilled in the art (for example Helv. Chim. Acta 71 (1988) 596, EP 502740, EP 522392).
So sind beisp inen Formel (IVa), For example, formula (IVa),
Figure imgf000032_0001
worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind ,
Figure imgf000032_0001
wherein R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above radical definition,
durch Umsetzung von Alkoxyvinylethern der allgemeinen Formel (VI), worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind, mit Malonsäurealkylester-amiden der allgemeinen Formel (VII) zugänglich. by reaction of alkoxyvinyl ethers of the general formula (VI) in which R 1 and R 2 are defined as described in the compound of the general formula (I) according to the above definition, with malonic acid alkyl ester amides of the general formula (VII).
Figure imgf000032_0002
(VI) (VII)
Figure imgf000032_0002
(VI) (VII)
Die Edukte der allgemeinen Formel (VI), worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden (z. B. Synthesis 2000, 738-742; J. Fluor. Chem., 107, 2001 , 285- 300; Organometallics 15, 1996, 5374-5379). The starting materials of general formula (VI) wherein R 1 and R 2 are defined as in the compound of general formula (I) according to the above definition are either commercially available or can be prepared by known methods (eg Synthesis 2000 , 738-742, J. Fluor. Chem., 107, 2001, 285-300, Organometallics 15, 1996, 5374-5379).
Die Verbindungen der allgemeinen Formel (IV), worin R2 ein Halogenatom bedeutet, lassen sich durch übliche Halogenierungen aus den Verbindungen der allgemeinen allgemeinen Formel (IVa) herstellen. The compounds of the general formula (IV) in which R 2 represents a halogen atom can be prepared by conventional halogenations from the compounds of the general formula (IVa).
Als Halogenierungsmittel für Pyridine finden beispielsweise Chlor (J. Org. Chem. 23, 1958, 1614), Brom (Synth. Commun. 19, 1989, 553-560; US P 2532055), lod (Tetrahedron Lett. 45, 2004, 6633-6636), Natriumhypochlorit (J. Org. Chem. 49, 1984, 4784-4786; J. Med. Chem. 36, 1993, 2676-2688, US P 4960896), Natriumhypobromit (J. Med. Chem. 32, 1989, 2178-2199), Thionylchlorid (Organic Letters, 6, 2004, 3-5), N-Chlorsuccinimid (J. Med. Chem. 46, 2003, 702-715), N-Bromsuccinimid (Chem. Pharm. Bull. 48, 2000, 1847-1853), N-Iodsuccinimid (J. Med. Chem. 36, 1993, 2676- 2788) Verwendung. Chlorine (J. Org. Chem., 23, 1958, 1614), bromine (Synth., Commun., 19, 1989, 553-560, US Pat (Tetrahedron Lett. 45, 2004, 6633-6636), sodium hypochlorite (J. Org. Chem. 49, 1984, 4784-4786; J. Med. Chem. 36, 1993, 2676-2688, USP 4960896), sodium hypobromite ( J. Med. Chem. 32, 1989, 2178-2199), thionyl chloride (Organic Letters, 6, 2004, 3-5), N-chlorosuccinimide (J. Med. Chem. 46, 2003, 702-715), N- Bromosuccinimide (Chem. Pharm. Bull. 48, 2000, 1847-1853), N-iodosuccinimide (J. Med. Chem. 36, 1993, 2676-2788).
Ferner können die Verbindungen der allgemeinen allgemeinen Formel (IV), worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind, aus den Verbindungen der allgemeinen Further, the compounds of the general general formula (IV) wherein R 1 and R 2 are defined as in the compound of the general formula (I) according to the above definition can be prepared from the compounds of the general formula (IV)
allgemeinen Formel (IVa), worin R1 und R2 wie in der herzustellenden Verbindung der allgemeinen Formel (I) gemäß obiger Restdefinition definiert sind, sukzessive durch Nitrierung (z. B. J. Med. Chem. 36, 1993, 2676-2688; J. Heterocycl. Chem. 33, 1996, 287-294), Reduktion (z. B. J. Med. Chem. 33, 1990, 1859-1865), Diazotierung und anschließender Umsetzung der Diazoniumsalze mittels Sandmeyer- bzw. general formula (IVa) in which R 1 and R 2 are defined as in the compound of general formula (I) to be prepared according to the above definition, successively by nitration (for example J. Med. Chem., 36, 1993, 2676-2688; Heterocycl Chem., 33, 1996, 287-294), reduction (eg J. Med. Chem., 33, 1990, 1859-1865), diazotization and subsequent reaction of the diazonium salts by means of Sandmeyer or
Schiemannn-Reaktion hergestellt werden.  Schiemannn reaction are produced.
Die Verbindungen der allgemeinen Formel (IVa), worin R Aryl oder Hetaryl und R" Wasserstoff oder Halogen bedeutet, lassen sich gemäß dem folgendenThe compounds of the general formula (IVa) in which R is aryl or hetaryl and R "is hydrogen or halogen can be prepared according to the following
):  ):
Figure imgf000033_0001
Figure imgf000033_0001
R' = H, Me, Et
Figure imgf000033_0002
R ' = H, Me, Et
Figure imgf000033_0002
Die Verbindungen der allgemeinen Formel (IVa), worin R1 Cycloalkyl oder Vinyl und R2 Wasserstoff oder Halogen bedeutet, lassen sich gemäß dem folgenden The compounds of the general formula (IVa) in which R 1 is cycloalkyl or vinyl and R 2 is hydrogen or halogen may be obtained according to the following
Reaktionschema herstellen:
Figure imgf000034_0001
Produce reaction scheme:
Figure imgf000034_0001
80 °C, 2 h  80 ° C, 2 h
HBr/AcOH (1 :2 v/v HBr / AcOH (1: 2 v / v
R = cycloalkyl, vinyl 30 °C, 16 h R = cycloalkyl, vinyl 30 ° C, 16 h
Figure imgf000034_0002
Figure imgf000034_0002
Die 1H-NMR-spektroskopischen Daten, die für die im nachfolgenden Abschnitt beschriebenen chemischen Beispiele angegeben sind (400 MHz bei 1H-NMR, The 1 H NMR spectroscopic data given for the chemical examples described in the following section (400 MHz at 1 H NMR,
Lösungsmittel CDCI3 oder DMSO-d6 (nachfolgend gleichermaßen auch als DMSO bezeichnet), interner Standard: Tetrametylsilan δ = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten. Die bezeichneten Signale haben die nachfolgend Solvent CDCl 3 or DMSO-d6 (hereinafter also referred to as DMSO), internal standard: tetramethylsilane δ = 0.00 ppm), were obtained with a device from Bruker. The designated signals have the following
aufgeführten Bedeutungen: br. = breit(es); s = Singulett, d = Dublett, t = Triplett, m = Multiplett, q = Quartett, sext = Sextett, sept = Septett. meanings listed: br. = broad (it); s = singlet, d = doublet, t = triplet, m = multiplet, q = quartet, sext = sextet, sept = septet.
Herstellungsbeispiele (Bsp.) Beispiel 15, gemäß nachstehender Tabelle A Preparation Examples (Ex.) Example 15, according to Table A below
6-Cyclopropyl-N-(2,2-dimethylpropyl)-2-oxo-1 H-pyridin-3-carboxamid 15.1 ) 6-Cyclopropyl -2-OXO-1 H-pyridin-3-carbonitril 6-Cyclopropyl-N- (2,2-dimethylpropyl) -2-oxo-1H-pyridine-3-carboxamide 15.1) 6-Cyclopropyl-2-OXO-1H-pyridine-3-carbonitrile
1 -Cyclopropyl-3-N,N-dimethylaminopropenon (1 .00 g, 7.18 mmol) und Cyanacetamid (0.60 g, 7.18 mmol) wurden in 100 ml Wasser vorgelegt, mit einem Tropfen konz. 1 -Cyclopropyl-3-N, N-dimethylaminopropenone (1 .00 g, 7.18 mmol) and cyanoacetamide (0.60 g, 7.18 mmol) were placed in 100 ml of water, with a drop of concentrated.
Essigsäure versetzt und 16h bei 100 °C erhitzt. Das Reaktionsgemisch wurde in Dichlormethan aufgenommen und extrahiert. Nach Entfernen des Lösungsmittels wurde der Rückstand in Essigester/Heptan ausgerührt, der entstandene Feststoff abgesaugt und i.Vak. getrocknet. Es wurden 0.95 g (75% d. Th.) eines farblosen Feststoffs erhalten. Added acetic acid and heated at 100 ° C for 16 h. The reaction mixture was taken up in dichloromethane and extracted. After removal of the solvent, the residue was stirred in ethyl acetate / heptane, the resulting solid sucked off and i.Vak. dried. 0.95 g (75% of theory) of a colorless solid were obtained.
1H-NMR (400 MHz, DMSO-de): δ = 12.7 (br. S, 1 H), 7.95 (d, 1 H), 5.95 (d, 1 H), 1 .92 (m, 1 H), 1 .13 (m, 2H), 0.96 (m, 2H). 1 H-NMR (400 MHz, DMSO-de): δ = 12.7 (br. S, 1H), 7.95 (d, 1H), 5.95 (d, 1H), 1.92 (m, 1H) , 1 .13 (m, 2H), 0.96 (m, 2H).
15.2) 6-Cyclopropyl-2-oxo-1 H-pyridin-3-carbonsäure 15.2) 6-Cyclopropyl-2-oxo-1H-pyridine-3-carboxylic acid
6-Cyclopropyl-2-oxo-1 H-pyridin-3-carbonitril (6.20 g, 34.6 mmol) wurden in 200 ml 10 N Natriumhydroxidlösung vorgelegt und für 4h bei 120 °C erhitzt. Das 6-Cyclopropyl-2-oxo-1H-pyridine-3-carbonitrile (6.20 g, 34.6 mmol) were placed in 200 ml of 10 N sodium hydroxide solution and heated at 120 ° C for 4h. The
Reaktionsgemisch wurde mit 6N HCl auf pH 1 gestellt und mit Wasser versetzt. Der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet.  Reaction mixture was adjusted to pH 1 with 6N HCl and water was added. The resulting solid was filtered off with suction and i.Vak. dried.
Es wurden 5.15 g (86% d. Th.) als farbloser Feststoff erhalten. 5.15 g (86% of theory) were obtained as a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 14.6 (br. S, 1 H), 13.4 (br. S, 1 H), 8.21 (d, 1 H), 6.27 (d, 1 H), 2.05 (m, 1 H), 1 .19 (m, 2H), 1 .03 (m, 2H). 1 H-NMR (400 MHz, DMSO-de): δ = 14.6 (br. S, 1 H), 13.4 (br. S, 1 H), 8.21 (d, 1 H), 6.27 (d, 1 H) , 2.05 (m, 1H), 1 .19 (m, 2H), 1 .03 (m, 2H).
15.3) 6-Cyclopropyl-N-(2,2-dimethylpropyl)-2-oxo-1 H-pyridin-3-carboxamid 6-Cyclopropyl-2-oxo-1 H-pyridin-3-carbonsäure (300 mg, 1 .55 mmol) wurde in 15.3) 6-Cyclopropyl-N- (2,2-dimethylpropyl) -2-oxo-1H-pyridine-3-carboxamide 6-Cyclopropyl-2-oxo-1H-pyridine-3-carboxylic acid (300 mg, 1. 55 mmol) was added in
Neopentylamin (203 mg, 2.33 mmol, 2.00 ml) gelöst und für 16h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit 1 N HCl auf pH 1 gestellt, der entstandene Feststoff abgesaugt und i.Vak. getrocknet. Es wurden 373 mg, (97% d. Th.) als farbloser Feststoff erhalten.  Neopentylamine (203 mg, 2.33 mmol, 2.00 ml) was dissolved and stirred at room temperature for 16 h. The reaction mixture was adjusted to pH 1 with 1 N HCl, the resulting solid was filtered off with suction and concentrated by evaporation in vacuo. dried. 373 mg (97% of theory) were obtained as a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 12.5 (br. S, 1 H), 9.85 (m, 1 H), 8.17 (d, 1 H), 6.06 (d, 1 H), 3.12 (s, 2H), 1 .97 (m, 1 H9, 1 .09 (m, 2H), 0.92 (m, 2H), 0.89 (s, 9H). 1H-NMR (400 MHz, DMSO-de): δ = 12.5 (br. S, 1H), 9.85 (m, 1H), 8.17 (d, 1H), 6.06 (d, 1H), 3.12 ( s, 2H), 1 .97 (m, 1 H9, 1 .09 (m, 2H), 0.92 (m, 2H), 0.89 (s, 9H).
Beispiel 463, gemäß nachstehender Tabelle A Example 463, according to Table A below
N-lsopentyl-2-oxo-6-phenyl-1 H-pyridin-3-carboxamid N-isopentyl-2-oxo-6-phenyl-1H-pyridine-3-carboxamide
463.1 ) 3-(N,N-Dimethylamino)-1 -phenylprop-2-en-1 -on Acetophenone (600 g, 5.00 mol) wurde in 11 DMF-Dimethylacetal vorgelegt und für 36h bei 95 °C gerührt. Der Überschuss and DMF-Dimethylacetal wurde i.Vak. abdestilliert und der Rückstand in MTBE (methyl tert-butyl ether) ausgerührt, abfiltriert und mit MTBE gewaschen. Es wurden 700 g (80% d. Th.) als gelblicher Feststoff erhalten. 1H-NMR (400 MHz, CDCIs): δ = 7.88 (m, 3H), 7.45 (m, 3H), 5.72 (d, 1 H), 3.12 (br. S, 3H), 2.95 (br. S, 3H). 463.1) 3- (N, N-dimethylamino) -1-phenylprop-2-en-1-one Acetophenone (600 g, 5.00 mol) was placed in 11 DMF-dimethylacetal and stirred for 36 h at 95 ° C. The excess of DMF-dimethylacetal was added i.vak. distilled off and the residue in MTBE (methyl tert-butyl ether) stirred, filtered off and washed with MTBE. 700 g (80% of theory) were obtained as a yellowish solid. 1 H-NMR (400 MHz, CDCIs): δ = 7.88 (m, 3H), 7.45 (m, 3H), 5.72 (d, 1H), 3.12 (br. S, 3H), 2.95 (br. S, 3H).
463.2) 2-Oxo-6-phenyl-1 H-pyridin-3-carbonsäuremethylester 463.2) 2-Oxo-6-phenyl-1H-pyridine-3-carboxylic acid methyl ester
Zu einer Lösung von 3-(N,N-Dimethylamino)-1 -phenylprop-2-en-1 -on (600 g, 3.43 mol) in 1 .8L Methanol wurde 2-Cyanoessigsäuremethylester (1 .02 kg, 10.3 mol) gegeben und die Reaktionsmischung für 12 h auf 70 °C erhitzt. Nach Abdestillieren des To a solution of 3- (N, N-dimethylamino) -1-phenylprop-2-en-1-one (600 g, 3.43 mol) in 1 .8 L methanol was added 2-cyanoacetate (1.02 kg, 10.3 mol). and the reaction mixture heated to 70 ° C for 12 h. After distilling off the
Lösungsmittels i.Vak. wurde der entstandene Feststoff mit MTBA ausgerührt, abfiltriert und mit MTBE gewaschen. Dann wurde der Feststoff Eisessig (490 ml) und Toluol (2 x 750 ml) azeotrop destilliert. Nach Abdestillieren des Lösungsmittels wurde der entstandene Feststoff mit MTBE gewaschen und i.Vak. getrocknet. Es wurden 120 g (15% d. Th.) als gelblicher Feststoff erhalten. Solvent i.Vak. The resulting solid was triturated with MTBA, filtered off and washed with MTBE. The solid was then azeotroped with glacial acetic acid (490 ml) and toluene (2 x 750 ml). After distilling off the solvent, the resulting solid was washed with MTBE and i.Vak. dried. 120 g (15% of theory) were obtained as a yellowish solid.
1H-NMR (400 MHz, DMSO-de): δ = 12.3 (br. S), 8.15 (m, 1 H), 7.72 (m, 2H), 7.50 (m, 3H), 6.80 (br. S, 1 H), 3.76 (s, 3H). 1 H-NMR (400 MHz, DMSO-de): δ = 12.3 (br. S), 8.15 (m, 1H), 7.72 (m, 2H), 7.50 (m, 3H), 6.80 (br. S, 1 H), 3.76 (s, 3H).
463.3) 2-Oxo-6-phenyl-1 H-pyridin-3-carbonsäure 2-Oxo-6-phenyl-1 H-pyridin-3-carbonsäuremethylester (3.00 g, 13.1 mmol) wurde in 150 ml THF vorgelegt, mit Lithiumhydroxid (565 mg, 26.2 mmol) versetzt und 16h bei Raumtemperatur gerührt. Nach Abdestillieren des Lösungsmittels i. Vak. wurde der Rückstand mit 2N HCl auf pH 1 gestellt. Der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 2.73 g (97% d. Th.) als farbloser Feststoff erhalten. 1H-NMR (400 MHz, DMSO-de): δ = 14.8 (br. S, 1 H), 13.5 (br. S, 1 H), 8.42 (d, 1 H), 7.85 (m, 2H), 7.55 (m, 3H), 7.03 (d, 1 H), 463.4) N-lsopentyl-2-oxo-6-phenyl-1 H-pyridin-3-carboxamid 463.3) 2-Oxo-6-phenyl-1H-pyridine-3-carboxylic acid 2-Oxo-6-phenyl-1H-pyridine-3-carboxylic acid methyl ester (3.00 g, 13.1 mmol) was initially charged in 150 ml of THF, with lithium hydroxide (565 mg, 26.2 mmol) and stirred for 16 h at room temperature. After distilling off the solvent i. Vak. the residue was adjusted to pH 1 with 2N HCl. The resulting solid was filtered off with suction and i.Vak. dried. 2.73 g (97% of theory) were obtained as a colorless solid. 1 H-NMR (400 MHz, DMSO-de): δ = 14.8 (br. S, 1 H), 13.5 (br. S, 1 H), 8.42 (d, 1 H), 7.85 (m, 2H), 7.55 (m, 3H), 7.03 (d, 1 H), 463.4) N-isopentyl-2-oxo-6-phenyl-1H-pyridine-3-carboxamide
2-Oxo-6-phenyl-1 H-pyridin-3-carbonsäure (200 mg, 0.93 mmol) wurde in 5 ml THF vorgelegt, mit CDI (301 mg, 1 .86 mmol) versetzt und 1 h bei Raumtemperatur gerührt. Dann wurde Isoamylamin (162 mg, 1 .83 mmol) zugegeben und 16h bei 2-Oxo-6-phenyl-1H-pyridine-3-carboxylic acid (200 mg, 0.93 mmol) was initially charged in 5 ml of THF, combined with CDI (301 mg, 1.86 mmol) and stirred at room temperature for 1 h. Then, isoamylamine (162 mg, 1.83 mmol) was added and added at 16 h
Raumtemperatur gerührt. Die Reaktionsmischung wurde mit Wasser versetzt und mit Ethylacetat extrahiert. Nach chromatographischer Reinigung wurden 90 mg (34% d. Th.) eines farblosen Öls erhalten.  Room temperature stirred. The reaction mixture was added with water and extracted with ethyl acetate. After chromatographic purification, 90 mg (34% of theory) of a colorless oil were obtained.
1H-NMR (400 MHz, DMSO-de): δ =12.7 (br. s, 1 H), 9.73 (m, 1 H), 8.36 (d. 1 H), 7.79 (m, 2H), 7.54 (m, 3H), 6.81 (d, 1 H), 3.36 (t, 2H), 1 .63 (sept., 1 H), 1 .42 (q, 2H), 0.90 (d, 6H). 1 H-NMR (400 MHz, DMSO-de): δ = 12.7 (br.s, 1H), 9.73 (m, 1H), 8.36 (i.e., 1H), 7.79 (m, 2H), 7.54 ( m, 3H), 6.81 (d, 1H), 3.36 (t, 2H), 1.63 (sec., 1H), 1.42 (q, 2H), 0.90 (d, 6H).
Beispiel 597, gemäß nachstehender Tabelle A 6-(4-Chlorphenyl)-N-(2-methoxyethyl)-2-oxo-1 H-pyridin-3-carboxamid Example 597, according to Table A below: 6- (4-chlorophenyl) -N- (2-methoxyethyl) -2-oxo-1H-pyridine-3-carboxamide
597.1 ) 6-(4-Chlorphenyl)-2-oxo-1 H-pyridin-3-carboxamid 597.1) 6- (4-chlorophenyl) -2-oxo-1H-pyridine-3-carboxamide
Unter einer Argonatmosphäre wurde Natrium (645 mg, 28.0 mmol) bei Under an argon atmosphere, sodium (645 mg, 28.0 mmol) was added
Raumtemperatur in 245 ml Ethanol gelöst. Nach Zugabe von Malonsäurediamid (3.58 g, 35.1 mmol) wurde für 30 min zum Rückfluss erhitzt. Daraufhin wurde 1 -(4- chlorphenyl)-3-(dimethylamino)prop-2-en-1 -on (4.90 g, 23.4 mmol) zugegeben und für 48 h zum Rückfluss erhitzt. Nach Entfernen des Lösungsmittels wurde der Rückstand in Wasser aufgenommen und mit 2N HCl auf pH 2 gestellt. Der entstandene Feststoff wurde abgesaugt, mit Ethylacetat/Heptan ausgerührt, erneut abgesaugt und i.Vak. getrocknet. Es wurden 3.49 g (60% d. Th.) eines farblosen Feststoffs erhalten. Room temperature dissolved in 245 ml of ethanol. Malonic acid diamide (3.58 g, 35.1 mmol) was added and refluxed for 30 min. Then 1 - (4-chlorophenyl) -3- (dimethylamino) prop-2-en-1-one (4.90 g, 23.4 mmol) was added and heated to reflux for 48 h. After removal of the solvent, the residue was taken up in water and adjusted to pH 2 with 2N HCl. The resulting solid was filtered off with suction, stirred with ethyl acetate / heptane, filtered off with suction again and concentrated by evaporation in a vacuum. dried. There was obtained 3.49 g (60% of theory) of a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 12.8 (br. s 1 H), 9.05 (br. s, 1 H), 8.37 (d, 1 H), 7.81 (d, 2H), 7.61 (d, 2H), 6.82 (m, 1 H). 597.2) 6-(4-Chlorphenyl)-2-oxo-1 H-pyridin-3-carbonsäure 1H-NMR (400 MHz, DMSO-de): δ = 12.8 (br. S 1 H), 9.05 (br. S, 1 H), 8.37 (d, 1 H), 7.81 (d, 2H), 7.61 ( d, 2H), 6.82 (m, 1H). 597.2) 6- (4-chlorophenyl) -2-oxo-1H-pyridine-3-carboxylic acid
6-(4-Chlorphenyl)-2-oxo-1 H-pyridin-3-carboxamid (3.49 g, 14.0 mmol) wurden in 100 ml 10 N Natriumhydroxidlösung vorgelegt und für 4h bei 120 °C erhitzt. Das Reaktionsgemisch wurde mit 6N HCl auf pH 1 gestellt und mit Wasser versetzt. Der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 3.28 g (94% d. Th.) als farbloser Feststoff erhalten. 6- (4-Chlorophenyl) -2-oxo-1H-pyridine-3-carboxamide (3.49 g, 14.0 mmol) was placed in 100 ml of 10 N sodium hydroxide solution and heated at 120 ° C for 4 h. The Reaction mixture was adjusted to pH 1 with 6N HCl and water was added. The resulting solid was filtered off with suction and i.Vak. dried. 3.28 g (94% of theory) were obtained as a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 14.8 (br.s, 1 H), 13.5 (br. s, 1 H), 8.42 (d, 1 H), 7.85 (d, 2H), 7.65 (d, 2H), 7.04 (d, 1 H). 1 H-NMR (400 MHz, DMSO-de): δ = 14.8 (br.s, 1H), 13.5 (br.s, 1H), 8.42 (d, 1H), 7.85 (d, 2H), 7.65 (d, 2H), 7.04 (d, 1H).
597.3) 6-(4-Chlorphenyl)-N-(2-methoxyethyl)-2-oxo-1 H-pyridin-3-carboxamid 597.3) 6- (4-chlorophenyl) -N- (2-methoxyethyl) -2-oxo-1H-pyridine-3-carboxamide
6-(4-Chlorphenyl)-2-oxo-1 H-pyridin-3-carbonsäure (250 mg, 1 .00 mmol) wurde in 2.00 ml Methoxyethylamin (1 .73 g, 23.0 mmol) gelöst und 16 h bei 50 °C gerührt. Die6- (4-Chlorophenyl) -2-oxo-1H-pyridine-3-carboxylic acid (250 mg, 1 .00 mmol) was dissolved in 2.00 ml of methoxyethylamine (1.73 g, 23.0 mmol) and heated at 50 ° for 16 h C stirred. The
Reaktionsmischung wurde mit 2N HCl auf pH 1 gestellt und der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 227 mg (74% d. Th.) eines farblosen Feststoffs erhalten. The reaction mixture was adjusted to pH 1 with 2N HCl and the resulting solid was filtered off with suction and concentrated by evaporation in a vacuum. dried. There were obtained 227 mg (74% of theory) of a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 12.8 (br. s), 1 H), 9.80 (br. s, 1 H), 8.48 (d, 1 H), 7.81 (d, 2H), 7.61 (d. 2H), 6.82 (d, 1 H), 3.50 (m, 2H), 3.31 (m, 2H), 3.28 (s, 3H). 1 H-NMR (400 MHz, DMSO-de): δ = 12.8 (br. S), 1 H), 9.80 (br. S, 1 H), 8.48 (d, 1 H), 7.81 (d, 2H) , 7.61 (i.e., 2H), 6.82 (d, 1H), 3.50 (m, 2H), 3.31 (m, 2H), 3.28 (s, 3H).
Beispiel 1 102, gemäß nachstehender Tabelle A N-Methyl-2-oxo-6-(2-pyridyl)-1 H-pyridin-3-carboxamid 1 102.1 ) 2-Oxo-6-(2-pyridyl)-1 H-pyridin-3-carboxamid Example 1 102, according to the following Table A N-methyl-2-oxo-6- (2-pyridyl) -1H-pyridine-3-carboxamide 1 102.1) 2-oxo-6- (2-pyridyl) -1 H- pyridine-3-carboxamide
Unter einer Argonatmosphäre wurde Natrium (2.35 g, 102 mmol) bei Raumtemperatur in 750 ml Ethanol gelöst. Nach Zugabe von Malonsäurediamid (13.0 g, 127 mmol) wurde für 30 min zum Rückfluss erhitzt. Daraufhin wurde 1 -(2-Pyridyl)-3- (dimethylamino)prop-2-en-1 -on (15.0 g, 85.1 mmol) zugegeben und für 48 h zum Rückfluss erhitzt. Nach Entfernen des Lösungsmittels wurde der Rückstand in Wasser aufgenommen und mit 2N HCl auf pH 2 gestellt. Der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 8.52 g (47% d. Th.) eines farblosen Feststoffs erhalten. Under an argon atmosphere, sodium (2.35 g, 102 mmol) was dissolved in 750 ml of ethanol at room temperature. Malonic acid diamide (13.0 g, 127 mmol) was added and refluxed for 30 min. Then 1 - (2-pyridyl) -3- (dimethylamino) prop-2-en-1-one (15.0 g, 85.1 mmol) was added and heated to reflux for 48 h. After removal of the solvent, the residue was taken up in water and adjusted to pH 2 with 2N HCl. The resulting solid was filtered off with suction and i.Vak. dried. This gave 8.52 g (47% of theory) of a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ =9.02 (br s, 1 H), 8.75 (m, 1 H),8.45 (m, 1 H), 8.25 (m, 1 H), 8.05 (m, 1 H), 7.71 (m, 1 H), 7.60 (m, 1 H).. 1 102.2) 2-Oxo-6-(2-pyridyl)-1 H-pyridin-3-carbonsäure 2-Oxo-6-(2-pyridyl)-1 H-pyridin-3-carboxamid (8.00 g, 37.2 mmol) wurden in 250 ml 10 N Natriumhydroxidlösung vorgelegt und für 4h bei 120 °C erhitzt. Das 1 H-NMR (400 MHz, DMSO-de): δ = 9.02 (br s, 1 H), 8.75 (m, 1 H), 8.45 (m, 1 H), 8.25 (m, 1 H), 8.05 ( m, 1H), 7.71 (m, 1H), 7.60 (m, 1H). 1 102.2) 2-Oxo-6- (2-pyridyl) -1H-pyridine-3-carboxylic acid 2-Oxo-6- (2-pyridyl) -1H-pyridine-3-carboxamide (8.00 g, 37.2 mmol) were placed in 250 ml of 10 N sodium hydroxide solution and heated at 120 ° C for 4h. The
Reaktionsgemisch wurde mit 6N HCl auf pH 1 gestellt und mit Wasser versetzt. Der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 6.29 g (78% d. Th.) als farbloser Feststoff erhalten. Reaction mixture was adjusted to pH 1 with 6N HCl and water was added. The resulting solid was filtered off with suction and i.Vak. dried. There was obtained 6.29 g (78% of theory) as a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 14.7 (br. s, 1 H), 13.1 (br. s, 1 H), 8.80 (m, 1 H), 8.50 (m, 1 H), 8.25 (m, 1 H), 8.05 (m, 1 H), 7.61 (m, 1 H), 7.47 (m, 1 H). 1H-NMR (400 MHz, DMSO-de): δ = 14.7 (br.s, 1H), 13.1 (br.s, 1H), 8.80 (m, 1H), 8.50 (m, 1H), 8.25 (m, 1H), 8.05 (m, 1H), 7.61 (m, 1H), 7.47 (m, 1H).
1 102.3) N-Methyl-2-oxo-6-(2-pyridyl)-1 H-pyridin-3-carboxamid 2-Oxo-6-(2-pyridyl)-1 H-pyridin-3-carbonsäure (281 .1 mg, 1 .30 mmol) wurde in 2.00 ml Methanamin (2.16 g, 69.5 mmol) gelöst und 16 h bei 50 °C gerührt. Die 1 102.3) N-methyl-2-oxo-6- (2-pyridyl) -1H-pyridine-3-carboxamide 2-oxo-6- (2-pyridyl) -1H-pyridine-3-carboxylic acid (281. 1 mg, 1 .30 mmol) was dissolved in 2.00 ml of methanamine (2.16 g, 69.5 mmol) and stirred at 50 ° C for 16 h. The
Reaktionsmischung wurde mit 2N HCl auf pH 1 gestellt und der entstandene Feststoff wurde abgesaugt und i.Vak. getrocknet. Es wurden 227 mg (74% d. Th.) eines farblosen Feststoffs erhalten. The reaction mixture was adjusted to pH 1 with 2N HCl and the resulting solid was filtered off with suction and concentrated by evaporation in a vacuum. dried. There were obtained 227 mg (74% of theory) of a colorless solid.
1H-NMR (400 MHz, DMSO-de): δ = 12.0 (br. s, 1 H), 9.60 (br. s, 1 H), 8.75 (m, 1 H), 8.45 (m, 1 H), 8.23 (m, 1 H), 8.05 (m, 1 H), 7.55 (m, 1 H), 7.31 (m, 1 H), 2.85 (d, 3H). 1H-NMR (400 MHz, DMSO-de): δ = 12.0 (br.s, 1H), 9.60 (br.s, 1H), 8.75 (m, 1H), 8.45 (m, 1H), 8.23 (m, 1H), 8.05 (m, 1H), 7.55 (m, 1H), 7.31 (m, 1H), 2.85 (d, 3H).
In der nachfolgenden Tabelle A sind beispielhaft eine Reihe weiterer Verbindungen der allgemeinen Formel (I) aufgeführt, die in analoger Weise zu den obigen Beispielen und den weiter oben erwähnten Methoden erhalten werden können. Table A below lists by way of example a series of further compounds of the general formula (I) which can be obtained analogously to the above examples and the methods mentioned above.
In der Tabelle bedeuten In the table mean
Bsp. = Beispiel  Example = example
Bu = Butyl Ethyl  Bu = butyl ethyl
Me = Methyl Phenyl  Me = methyl phenyl
Pr = Propyl  Pr = propyl
i = iso sekundär i = iso secondary
t = tertiär cyclo Entsprechendes gilt für die zusammengesetzten Ausdrücke wie t = tertiary cyclo The same applies to the compound expressions such as
iPr = Isopropyl iPr = isopropyl
iBu = Isobutyl iBu = isobutyl
sBu = sec.-Butyl sBu = sec-butyl
tBu tert.-Butyl tBu tert-butyl
cPr = Cyclopropyl cPr = cyclopropyl
cPentyl = Cyclopentyl cpentyl = cyclopentyl
cHexyl = Cyclohexyl cHexyl = cyclohexyl
cBu = Cyclobutyl cBu = cyclobutyl
Ist in Tabelle A ein Alkylrest ohne weitere Kennzeichnung aufgeführt, so handelt es sich um den geradkettigen Alkylrest, d. h. beispielsweise Bu = n-Bu = n-Butyl. If an alkyl radical without further labeling is listed in Table A, it is the straight-chain alkyl radical, ie. H. for example, Bu = n-Bu = n-butyl.
Die Zahlenindizes in den Formelausdrücken sind in Tabelle A nicht tiefgestellt, sondern in derselben Zeilenhöhe und Schriftgröße wie die Atomsymbole angeordnet. The numeric indices in the formula expressions are not subscripted in Table A, but arranged in the same row height and font size as the atomic symbols.
Beispielsweise entspricht die Formel CF3 in der Tabelle der Formel CF3 gemäß üblicher Schreibweise mit tiefgestelltem Index oder die Formel CH2CH(CH2CH3)2 der Formel CH2CH(CH2CH3)2 mit tiefgestellten Indices. For example, the formula corresponds to CF3 in the table of the formula CF3 according to conventional notation with subscript or the formula CH2CH (CH2CH3) 2 of the formula CH 2 CH (CH 2 CH 3 ) 2 subscripts with subscripts.
Tabelle A: Verbindungen der allgemeinen Formel (I) Table A: Compounds of the general formula (I)
Figure imgf000040_0001
Figure imgf000040_0001
Figure imgf000040_0002
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000040_0002
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000063_0001
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
Figure imgf000071_0001
Figure imgf000072_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000073_0001
Figure imgf000074_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000090_0001
NMR-Daten ausgewählter in obiger Tabelle A genannter Verbindungen  NMR data of selected compounds mentioned in Table A above
Die NMR-Daten ausgewählter, in Tabelle A genannter Verbindungen werden entweder in klassischer Form (δ-Werte, Anzahl der H-Atome, Multiplettaufspaltung) oder als NMR-Peak-Listen aufgeführt. Die Zuordnung der in Tabelle A genannten The NMR data of selected compounds listed in Table A are listed either in classical form (δ values, number of H atoms, multiplet splitting) or as NMR peak lists. The assignment of the mentioned in Table A.
Verbindungen erfolgt über die Beispielnummern gemäß Tabelle A. Connections are made using the example numbers according to Table A.
Wenn die 1H-NMR-Daten ausgewählter Beispiele in Form von 1H-NMR-Peaklisten notiert werden, wird zu jedem Signalpeak erst der δ-Wert in ppm und dann die When the 1 H-NMR data of selected examples are noted in the form of 1 H-NMR peak lists, the δ-value in ppm and then the
Signalintensität in runden Klammern aufgeführt. Die δ-Wert - Signal intensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste hat daher die nachfolgend dargestellte Form: δι (Intensitäti); 82 (lntensität.2); ; δ, (Intensität,'; ; δη (lntensitätn) 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. Signal intensity listed in parentheses. The δ-value-signal intensity-number pairs of different signal peaks are listed separated by semicolons. The peak list therefore has the following form: δι (intensity i); 82 (intensity.2); ; δ, (intensity, ';; δ η (intensity n ) The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of signal intensities Center of the signal and its relative intensity compared to the most intense signal in the spectrum are shown.
Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren wirf To calibrate the chemical shift of 1 H NMR spectra wirf
Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels benutzt, besonders im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Tetramethylsilane and / or the chemical shift of the solvent used, 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.
Die Listen der 1H-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 Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. The lists of 1 H NMR peaks are similar to the classical 1 H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. Moreover, like classical 1 H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in den Listen von 1H-NMR-Peaks die gewöhnlichen When indicating connection signals in the delta range of solvents and / or water, the lists of 1 H NMR peaks are the usual ones
Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO- und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von  Solvent peaks, for example peaks of DMSO in DMSO- and the peak of water, which are usually of high intensity on average. The peaks of stereoisomers of the target compounds and / or peaks of
Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). 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 Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help the reproduction of our manufacturing process by "by-product fingerprints".
Ein Fachmann, der die Peaks der Zielverbindungen mit bekannten Verfahren A person skilled in the art, the peaks of the target compounds by known methods
(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 ist ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR-lnterpretation gegeben. (MestreC, ACD simulation, but also with empirically evaluated expected values), can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation is similar to peak picking in the classical 1 H NMR interpretation.
Weitere Details zu 1 H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on 1 H NMR peaks can be found in Research Disclosure Database Number 564025.
Beispiel 1 : 1H-NMR(601 ,6 MHz, de-DMSO): δ= 12,472(2,0);9,015(3,4);8,158(15,6);8,146(16,0 );7,379(3,6);6,025(6,0);6,013(5,9);3,323(118,1); 2,617(1 ,0);2,614(1 ,3);2,611(0,9);2,523(2,2);2,520(2,8);2,517(2,6);2,508(70,7);2,505(150,4);2, 502(204,4);2,499(149,4);2,496(69,5);2,389(0,9);Example 1: 1 H-NMR (601, 6 MHz, de-DMSO): δ = 12.472 (2.0), 9.015 (3.4), 8.158 (15.6), 8.146 (16.0), 7.379 ( 3.6); 6,025 (6.0); 6,013 (5.9); 3,323 (118.1); 2,617 (1, 0), 2,614 (1,3), 2,611 (0,9), 2,523 (2,2), 2,520 (2,8), 2,517 (2,6), 2,508 (70,7), 2,505 (150.4); 2.502 (204.4); 2.499 (149.4); 2.496 (69.5); 2.389 (0.9);
9 1 9 IRIin QV1 QR7 4V1 QW} 1V1 -1 QAAIR, 1Vf,1 QW} 7V1 QW} I 1 Q99 1 RV1 R7fMf) fiV1 1Π9Π 1V1 flQ- Q RV1 nQfMlf)9 1 9 IRIin QV1 QR7 4V1 QW} 1V1 -1 QAAIR, 1Vf, 1 QW} 7V1 QW} I 1 Q99 1 RV1 R7fMf) fiV1 1Π9Π 1V1 flQ-Q RV1 nQfMlf)
8);1 ,080(10,1);1 ,076(9,9);1 ,069(3,7);1 ,058(0,4);1 ,044(0,4);0,951(0,4);0,942(0,4);0,925(4,5);0, 318(12,9);0,914(12,6);0,910(12,0);0,906(13,6);0 ,899(3,5);0,005(0,5);0,000(14,1);-0,006(0,5) 8); 1, 080 (10.1); 1, 076 (9.9); 1, 069 (3.7); 1, 058 (0.4); 1, 044 (0.4); 0.951 ( 0.942 (0.4); 0.925 (4.5); 0.3118 (12.9); 0.914 (12.6); 0.910 (12.0); 0.906 (13.6); 0 , 899 (3.5); 0,005 (0.5); 0,000 (14.1) - 0.006 (0.5)
Beispiel 4: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,674(0,8);8,171 (4,0);8,152(4,2);6,048(1 ,9);6,028(1 ,8);3,454(16,0);3,260(1 ,5);3,243(2,7);3,22 8(2,7);3,211(1 ,5);2,524(0,7);2,519(1 ,1);2,511 (15,5);2,506(34,0);2,502(47,6);2,497(33,1);2,492(14,8);1 ,978(0,6);1 ,970(0,7);1 ,957(1 ,4);1 ,945(0, 8); 1 , 936(0,7); 1 , 523(1 ,6);1 ,505(2,9);1 ,487(2,9);1 , 469(1 ,7);1 ,116(0,8);1 ,104(2,1);1 ,098(2,4);1 , 087(1 ,3);1 ,083(2,2);1 ,077(2,2);1 ,066(0,9);0,928(1 ,1);0,918(2,5);0,911(2,5);0,905(8,2);0,899(2,9);0,887(13,4);0,868(5,3) Example 4: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.674 (0.8); 8.171 (4.0); 8.152 (4.2); 6.048 (1, 9); 6.028 ( 1, 8); 3.454 (16.0); 3.260 (1, 5); 3.243 (2.7); 3.22 8 (2.7); 3.211 (1, 5); 2.524 (0.7); 2.519 (1, 1), 2.511 (15.5), 2.506 (34.0), 2.502 (47.6), 2.497 (33.1), 2.492 (14.8), 1.978 (0.6) ; 1, 970 (0.7); 1, 957 (1, 4); 1, 945 (0, 8); 1, 936 (0.7); 1, 505 (2.9); 1, 487 (2.9); 1, 469 (1, 7); 1, 116 (0.8); 1, 104 (2 , 1); 1, 098 (2,4); 1, 087 (1, 3); 1, 083 (2,2); 1, 077 (2,2); 1, 066 (0,9); 0,928) (1, 1); 0.918 (2.5); 0.911 (2.5); 0.905 (8.2); 0.899 (2.9); 0.887 (13.4); 0.868 (5.3)
Beispiel 6: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,549(3,1);9,669(4,4);9,658(4,4);8,169(15,4) 8,149(16,0);6,048(9,0);6,029(8,9);3,331(62,3);3 ,307(0,8);2,836(0,9);2,826(2,5);2,816(3,1);2,808(5,3);2,798(5,4);2,790(3,2);2,780(2,6);2,769(C ,9);2,678(0,4);2,673(0,5);2,669(0,4);2,527(1 ,2); 2,522(1 ,8);2,513(31 ,8);2,509(70,4);2,504(98,1);2,500(70,1);2,495(32,1);2,336(0,4);2,331 (0,5) 2,327(0,4);1 ,987(1 ,2);1 ,974(2,7);1 ,966(2,9);1 ,9Example 6: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.549 (3.1); 9.699 (4.4); 9.658 (4.4); 8.169 (15.4) 8.149 (16 , 0), 6.048 (9.0), 6.029 (8.9), 3.331 (62.3), 3, 307 (0.8), 2.836 (0.9), 2.826 (2.5), 2.816 ( 2.1), 2.808 (5.3), 2.798 (5.4), 2.790 (3.2), 2.780 (2.6), 2.769 (C, 9), 2.678 (0.4), 2.673 (0 , 5); 2,669 (0.4); 2.527 (1, 2); 2.522 (1, 8), 2.513 (31, 8), 2.509 (70.4), 2.504 (98.1), 2.500 (70.1), 2.495 (32.1), 2.336 (0.4), 2.331 (0.5) 2.237 (0.4); 1, 987 (1, 2); 1, 974 (2.7); 1, 966 (2.9); 1, 9
^ΛΙ^ -1 Q-ΜΠ 1V1 mi QV1 Q9f)M 4V1 191^9 SV1 1fWR 4V1 1fWQ 7V1 O Wi 1V1 ORRIR 7 vi ns9^s svi n7in RVI rvwn -ivi OWIO AYO^ ΛΙ ^ -1 Q-ΜΠ 1V1 mi QV1 Q9f) M 4V1 191 ^ 9 SV1 1fWR 4V1 1fWQ 7V1 O Wi 1V1 ORRIR 7 vi ns9 ^ s svi n7in RVI rvwn -ivi OWIO AYO
966(0,4);0,952(0,4);0,927(4,0);0,917(10,4);0,911(9,9);0,905(9,8);0,898(11 ,2);0,887(3,0);0,876 (0,4);0,740(3,5);0,727(9,4);0,722(12,3);0,710(1 2,1);0,705(9,8);0,693(4,3);0,671 (0,5);0,653(0,4);0,531 (0,4);0,521(0,4);0,492(4,0);0,481(10,6); 0,475(10,1);0,470(9,5);0,465(10,1);0,453(3,3);0, 008(0,9) 966 (0.4), 0.952 (0.4), 0.927 (4.0), 0.917 (10.4), 0.911 (9.9), 0.905 (9.8), 0.898 (11, 2), 0.887 (3.0); 0.876 (0.4); 0.740 (3.5); 0.727 (9.4); 0.722 (12.3); 0.710 (1 2.1); 0.705 (9.8); 0.693 (4.3); 0.671 (0.5); 0.653 (0.4); 0.531 (0.4); 0.521 (0.4); 0.492 (4.0); 0.481 (10.6); 0.475 (10.1); 0.470 (9.5); 0.465 (10.1); 0.453 (3.3); 0.008 (0.9)
Beispiel 15: 1H-NMR(400,1 MHz, de-DMSO): δ= 8,182(1 , 1);8,163(1 ,1);6,066(0,8);6,047(0,8);3 ,330(4,4);3,122(1 ,6);3,106(1 ,6);2,513(2,4);2,50Example 15: 1 H-NMR (400.1 MHz, de-DMSO): δ = 8.182 (1, 1); 8.163 (1, 1); 6.066 (0.8); 6.047 (0.8); 3, 330 (4.4); 3.122 (1, 6); 3.106 (1, 6); 2.513 (2.4); 2.50
Ql^ 1V9 ^,ΟΑΠ 9V94<Wi 9V9 AW 4V1 QfWn 4V1 11fMf) RV1 IfWO 7V1 fKWfl -lVI flR f) fil 1 ns9^n Rvn Q9R^n svn wrvn 7vn Qi4^n svn QQl ^ 1V9 ^, ΟΑΠ 9V9 4 <Wi 9V9 AW 4V1 QfWn 4 V1 11fMf) RV1 IfWO 7V1 fKWfl -VVI flR f) fil 1 ns9 ^ n Rvn Q9R ^ n svn wrvn 7vn Qi 4 ^ n svn Q
08(0,9);0,894(16,0) 08 (0.9); 0.894 (16.0)
Beispiel 23: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,166(2,2);8,147(2,3);6,046(0,9);6,027(0,9);3 ,407(18,0);3,316(0,8);3,301 (1 ,1);3,298(1 ,1);3,2 84(1 ,1);3,281(1 ,1);3,265(0,8);2,524(0,5);2,519(0,8);2,511(10,4);2,506(22,4);2,501(31 ,3);2,497 (21 ,9);2,492(9,7); 1 ,956(0,7);1 ,615(0,5); 1 , 599(0,Example 23: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.166 (2.2); 8.147 (2.3); 6.046 (0.9); 6.027 (0.9); 3, 407 (18.0), 3.316 (0.8), 3.301 (1, 1), 3.298 (1, 1), 3.2 84 (1, 1), 3.281 (1, 1), 3.265 (0.8 2.524 (0.5), 2.519 (0.8), 2.511 (10.4), 2.506 (22.4), 2.501 (31, 3), 2.497 (21, 9), 2.492 (9.7) ; 1, 956 (0.7); 1, 615 (0.5); 1, 599 (0,
7);1 ,582(0,6);1 ,410(0,9);1 , 393(1 , 6);1 , 374(1 ,7);1 ,357(0,7);1 , 103(1 ,2);1 , 097(1 , 3);1 ,086(0,7);1 ,0 32(1 ,2);1 ,076(1 ,2);1 ,065(0,5);0,926(0,6);0,916(1 ,4);0,909(1 ,7);0,903(16,0);0,898(2,1);0,886(14,5) 1, 582 (0.6); 1, 410 (0.9); 1, 393 (1, 6); 1, 374 (1, 7); 1, 357 (0.7); 1, 103 (1, 2); 1, 097 (1, 3); 1, 086 (0.7); 1, 0 32 (1, 2); 1, 076 (1, 2); 1, 065 (0, 5), 0.926 (0.6), 0.916 (1, 4), 0.909 (1, 7), 0.903 (16.0), 0.898 (2.1), 0.886 (14.5)
Beispiel 32: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,494(1 ,6);9,577(1 ,6);9,557(1 ,6);8,164(5,5) 8,145(5,7);6,045(2,3);6,041(2,1);6,026(2,2);6,0 21(2,1);5,760(0,4);3,990(0,5);3,973(1 ,1);3,956(1 ,3);3,937(1 ,2);3,920(0,6);3,379(0,4);3,329(44 1);3,306(0,4);3,280(0,3);2,672(0,3);2,558(0,4);2 ,553(0,5);2,526(0,6);2,521 (0,9);2,512(18,6);2,508(41 ,7);2,503(58,4);2,499(42,1);2,494(19,6);2 ,463(0,5);2,459(0,5);2,454(0,5);2,330(0,3);1 ,99 7(0,4);1 ,984(0,9);1 ,976(1 ,0);1 ,963(1 ,9);1 ,951 (1 ,1);1 ,942(1 ,0);1 ,930(0,5);1 ,466(0,8);1 ,459(0,9) 1 ,450(1 ,5); 1 ,442(2,7); 1 ,433(1 ,4); 1 ,425(3,0);1 ,4 I , 04 U,4J, I , OU U 1 I 1 I 1 i y( ,UJ, I , UÖ I ,/ J, I , U 1 I , θο I ,^. 1 ,Example 32: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.494 (1, 6); 9.577 (1, 6); 9.557 (1, 6); 8.164 (5.5) 8.145 (5 , 7); 6.045 (2.3); 6.041 (2.1); 6.026 (2.2); 6.0.21 (2.1); 5.760 (0.4); 3.990 (0.5); 3.973 (1, 1); 3.956 (1, 3); 3.937 (1, 2); 3.920 (0.6); 3.379 (0.4); 3.329 (44 1); 3.306 (0.4); 3.280 (0 , 3); 2,672 (0.3); 2.558 (0.4); 2, 553 (0.5); 2.526 (0.6); 2.521 (0.9); 2.512 (18.6); 2.508 ( 41, 7), 2.503 (58.4), 2.499 (42.1), 2.494 (19.6), 2.463 (0.5), 2.459 (0.5), 2.454 (0.5), 2.330 (0.3); 1, 99.7 (0.4); 1, 984 (0.9); 1, 976 (1, 0); 1, 963 (1, 9); 1, 951 (1, 1 1, 942 (1, 0); 1, 930 (0.5); 1, 466 (0.8); 1.4459 (0.9) 1.450 (1.5); 1, 442 (2,7); 1, 433 (1, 4); 1, 425 (3,0); 1, 4 I, 04 U, 4J, I, OU U 1 I 1 I 1 iy (, UJ, I, UOS I, / J, I, U 1 I, θο I, ^. 1,
122(13,3);1 , 105(16,0);1 ,099(4,3);1 ,089(2,1);1 ,085(3,2);1 ,078(3,2);1 , 068(1 , 3);0,923(1 ,5);0,912 (3,5);0,906(3,4);0,900(3,5);0,892(8,9);0,883(1 ,5 );0,873(15,4);0,855(6,1);0,008(0,5);0,000(20,3) 122 (13.3); 1, 105 (16.0); 1, 099 (4.3); 1, 089 (2.1); 1, 085 (3.2); 1, 078 (3.2 1, 068 (1, 3), 0.923 (1, 5), 0.912 (3.5), 0.906 (3.4), 0.900 (3.5), 0.892 (8.9), 0.883 (1, 5), 0.873 (15.4), 0.855 (6.1), 0.008 (0.5), 0.000 (20.3)
Beispiel 36: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,459(1 ,4);9,548(1 ,3);9,528(1 ,3);8,166(5,8) 8,147(6,0);6,044(1 ,9);6,041(1 ,6);6,025(1 ,9);6,0Example 36: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.459 (1, 4), 9.548 (1.3), 9.528 (1.3), 8.166 (5.8) 8.147 (6 , 0); 6.044 (1, 9); 6.041 (1, 6); 6.025 (1, 9); 6.0
99 RV4 ORQIO AVA 0^10 7V4 OARIO SV4 0X710 7YA Π1 Μ 9V4 OMIO QV4 f)1 MO 7V3 Q<Wf) / VI W\0 ^-9 'Ό^ίΟ -9 'ΌΟίΟ 7V9 ^19^19 9V99 RV4 ORQIO AVA 0 ^ 10 7V4 OARIO SV4 0X710 7YA Π1 Μ 9V4 OMIO QV4 f) 1 MO 7V3 Q <Wf) / VI W \ 0 ^ -9 'Ό ^ ίΟ -9' ΌΟίΟ 7V9 ^ 19 ^ 19 9V
2,507(27,1);2,502(38,1);2,498(27,2);2,493(12,6);1 ,998(0,4);1 ,986(0,9);1 , 977(1 ,0);1 ,974(0,8);1 ,965(2,0);1 ,956(0,7); 1 ,952(1 ,1);1 ,944(1 ,0);1 ,93 1(0,5);1 ,636(0,5);1 ,619(0,9);1 ,616(0,8);1 ,603(1 ,1);1 ,600(1 ,1);1 ,583(1 ,1);1 ,567(0,7);1 ,433(0,9) 1 ,418(0,8);1 ,411(0,9);1 ,399(1 ,5);1 ,384(1 ,3);1 ,3 77(1 ,4);1 ,362(1 ,2);1 ,301 (1 ,3);1 ,286(1 ,5);1 ,280(1 ,3);1 ,266(2,0);1 ,252(0,9);1 ,247(0,9);1 ,232(0,£ ); 1 ,148(0,3); 1 ,116(13,5); 1 , 100(14,5);1 ,086(1 ,9); 1 ,082(3,2);1 ,075(3,1);1 , 065(1 , 3);0,922(1 ,5);0,912(3,4);0,905(3,5);0,900(3,4);0,894(3,4);0,883 16,0);0,874(15,3);0,866(15,0);0,857(14,2)2.507 (27.1); 2.502 (38.1); 2.498 (27.2); 2.493 (12.6); 1, 998 (0.4); 1, 986 (0.9); 1, 977 ( 1, 0); 1, 974 (0.8); 1.965 (2.0); 1.956 (0.7); 1, 952 (1, 1); 1, 944 (1, 0); 1, 93 1 (0.5); 1, 636 (0.5); 1, 619 (0.9); 1, 616 ( 0.8); 1, 603 (1, 1); 1, 600 (1, 1); 1, 583 (1, 1); 1, 567 (0.7); 1, 433 (0.9) 1 , 418 (0.8), 1, 411 (0.9), 1, 399 (1, 5), 1, 384 (1, 3), 1, 3, 77 (1, 4), 1, 362 (1 , 2); 1, 301 (1, 3); 1, 286 (1, 5); 1, 280 (1, 3); 1, 266 (2.0); 1, 252 (0.9); 1 , 247 (0.9); 1, 232 (0, £); 1, 148 (0.3); 1, 116 (13.5); 1, 100 (14.5); 1, 086 (1, 9); 1, 082 (3,2); 1, 075 (3,1); 1, 065 (1, 3); 0.922 (1, 5); 0.912 (3.4); 0.905 (3.5); 0.900 (1) 3.4), 0.894 (3.4), 0.883 16.0), 0.874 (15.3), 0.866 (15.0), 0.857 (14.2)
Beispiel 45: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,530(4,7);9,764(2,4);9,751 (4,5);9,737(2,6);8,180(15,3);8,161(16,0);6,039(6,0);6,020(6,0);4 ,771 (2,2);3,497(5,1 );3,482(11 ,4);3,469(7,5);3,366(6,5);3,352(16,^ Example 45: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.530 (4.7), 9.764 (2.4), 9.751 (4.5), 9.737 (2.6), 8.180 ( 15.3), 8.161 (16.0), 6.039 (6.0), 6.020 (6.0), 4, 771 (2.2), 3.497 (5.1), 3.482 (11, 4), 3.469 (7.5); 3,366 (6.5); 3,352 (16, ^
44,6);2,505(61 ,6);2,500(44,7);2,496(21 ,3);2,332(0,4);1 ,992(1 ,2);1 ,979(2,7);1 ,971 (3,0);1 ,958(5,6);1 ,946(3,3);1 ,937(3,0);1 ,925(1 ,5);1 ,121(2,9);
Figure imgf000093_0001
);1 ,421(2,8);1 ,404(2,8);1 ,385(2,3);1 ,368(0,9);0,905(16,0);0,888(15,9);0,874(3,4) 2.505 (61.6), 2.500 (44.7), 2.496 (21, 3), 2.322 (0.4), 1.992 (1, 2), 1.979 (2.7) 1,971 (3,0); 1,958 (5,6); 1,946 (3,3); 1,937 (3,0); 1,925 (1,5); 1,121 ( 2.9);
Figure imgf000093_0001
1, 421 (2,8), 1, 404 (2,8), 1, 385 (2,3), 1, 368 (0,9), 0,905 (16,0), 0,888 (15.9 ); 0.874 (3.4)
Beispiel 197: 1H-NMR(400,0 MHz, CDC ): δ= Example 197: 1 H-NMR (400.0 MHz, CDC): δ =
Beispiel 198: 1H-NMR(400,0 MHz, CDC ): δ= 8,590(3,0);8,571(3,1);7,262(36,1);6,445(1 ,3);6,426(1 ,3);4,454(1 ,2);4,436(4,1);4,418(4,3);4,417 (2,6);4,400(1 ,6);4,399(2,1);4,381(0,6);3,274(0,6);2,007(16,0);1 ,767(1 ,1);1 ,751 (1 ,8);1 ,748(1 ,5);1 ,746(1 ,8);1 ,745(1 ,7);1 ,741 (1 ,2);1 ,730(1 ,5);1 ,6 00(1 ,5);1 ,590(1 ,2);1 ,585(1 ,8);1 ,582(1 ,5);1 ,579(1 ,8);1 ,564(1 ,0);1 ,436(4,2);1 ,431 (2,1);1 ,422(0,6);1 ,418(9,2);1 ,413(4,4);1 ,400(4,3);1 ,395(2,1);0, 000(10,9) Example 198: 1 H-NMR (400.0 MHz, CDC): δ = 8.590 (3.0), 8.571 (3.1), 7.262 (36.1), 6.445 (1.3), 6.426 (1, 4,454 (1, 2), 4,436 (4,1), 4,418 (4,3), 4,417 (2,6), 4,400 (1,6), 4,399 (2,1), 4,381 (0,6 3, 774 (0.6); 2.007 (16.0); 1, 767 (1, 1); 1, 751 (1, 8); 1, 748 (1, 5); 1, 746 (1, 8); 1, 745 (1, 7); 1, 741 (1, 2); 1, 730 (1, 5); 1, 6 00 (1, 5); 1, 590 (1, 2); 1, 585 (1, 8); 1, 582 (1, 5); 1, 579 (1, 8); 1, 564 (1, 0); 1, 436 (4.2); 1, 431 (2.1 1, 422 (0.6), 1, 418 (9.2), 1, 413 (4.4), 1, 400 (4.3), 1, 395 (2.1), 0.000 (10.9)
Beispiel 202: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,294(0,6);7,516(2,9);6,396(0,6);3,592(14,5);3,570(15,5);3,552(16,0);3,383(2,1);3,334(11Example 202: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.294 (0.6), 7.516 (2.9), 6.396 (0.6), 3.592 (14.5), 3.570 ( 15.5) 3,552 (16.0); 3,383 (2.1); 3,334 (11
0,8);3,287(2,3);3,276(1 ,3);3,198(10,7);2,675(1 ,2);2,671(1 ,7);2,666(1 ,1);2,556(2,7);2,552(4,0);2,547(3,2);2,542(2,0);2,537(1 ,3);2,52^^3.287 (2.3); 3.287 (2.3); 3.377 (2.3); 3.276 (1.3); 3.198 (10.7); 2.675 (1, 2); 2.671 (1, 7); 2.666 (1, 1); 2.556 (2 , 7), 2.552 (4.0), 2.547 (3.2), 2.542 (2.0), 2.537 (1, 3), 2.52 ^^
1(109,9);2,506(219,3);2,502(286,0);2,497(200,1);2,492(93,4);2,469(6,9);2,464(6,7);2,458(6,3);2,453(5,6);2,448(4,3);2,444(3,7^ 1 (109.9); 2.506 (219.3); 2.502 (286.0); 2.497 (200.1); 2.492 (93.4); 2,469 (6.9); 2,464 (6.7); 2,458 (6.3); 2,453 (5.6); 2,448 (4.3); 2,444 (3.7 ^
33(1 ,3);2,328(1 ,7);2,324(1 ,2); 1 ,489(5,4); 1 ,399(11 ,6);0,000(8,2)  33 (1, 3); 2,328 (1, 7); 2,324 (1,2); 1, 489 (5.4); 1, 399 (11, 6); 0.000 (8.2)
Beispiel 203: 1H-NMR(400,0 MHz, de-DMSO): δ= 4,403(0,7);4,386(0,7);3,651(16,0);3,549(0,5);3,532(0,9);3,515(0,6);3,443(4,4);3,385(1 ,7);3, 348(24,5);3,134(1 ,1);3,122(1 ,4);3,116(3,6);3,104(3,8);3,098(3,8);3,086(3,7);3,080(1 ,4);3,068(1 ,2);2,675(0,6);2,671 (0 Example 203: 1 H-NMR (400.0 MHz, de-DMSO): δ = 4.403 (0.7); 4.386 (0.7); 3.651 (16.0); 3.549 (0.5); 3.532 ( 3.915 (1, 7); 3, 348 (24.5); 3.134 (1, 1); 3.122 (1, 4); 3.116) (3.6); 3.104 (3.8); 3.098 (3.8); 3.086 (3.7); 3.080 (1, 4); 3.068 (1, 2); 2.675 (0.6); 2.671 ( 0
2,524(3,6);2,510(50,5);2,506(99,0);2,501(129,5);2,497(91 ,3);2,492(43,4);2,454(2,2);2,390(1 ,1);2,386(1 ,0);2,333(0,7);2,328(0,9) 2.524 (3.6), 2.510 (50.5), 2.506 (99.0), 2.501 (129.5), 2.497 (91, 3), 2.492 (43.4), 2.454 (2.2), 2.390 (1, 1); 2.386 (1, 0); 2.333 (0.7); 2.328 (0.9)
265(0,5);2,244(0,8);2,233(0,8);2,215(0,7);1 ,903(0,9);1 ,886(1 ,5);1 ,865(2,3);1 ,857(2,2);1 ,845(1 ,4);1 ,829(0,9);1 ,409(1 ,6);1 ,193(7,3);1 ,175(15,2); 1 ,157(7,2);0,000(3,9) 265 (0.5); 2.244 (0.8); 2.233 (0.8); 2.215 (0.7); 1, 903 (0.9); 1, 886 (1, 5); 1, 865 ( 2,3); 1, 857 (2,2); 1, 845 (1,4); 1, 829 (0,9); 1,409 (1,6); 1, 193 (7,3); 1, 175 (15,2); 1, 157 (7,2); 0,000 (3,9)
Beispiel 204: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,410(0,7);5,194(1 ,3);4,412(0,6);4,378(0,6);4,247(0,7);4,230(1 ,0);4,184(1 ,6);4,166(4,9);4,1 49(5,3);4,131(2,1);4,119(1 ,7);4,101 (1 ,9);4,098(1 ,7);4,080(1 ,6);4,071(0,5);4,062(0,5);3,464(15,5);3,356(1 ,0);3,322(1 ,0);3,119(0,6);3,092(1 ,0);3 ,061 (0,5);2,737(0,6);2,675(1 ,0);2,670(1 ,4);2,666(1 ,0);2,555(1 ,8);2,550(4,1);2,546(4,2);2,541 (3,1);2,524(4,4);2,519(6,3);2,511(87,7);2,506(185 ,6);2,501(250,0);2,497(176,4);2,492(82,8);2,466(6,1);2,459(4,4);2,454(1 ,7);2,337(0,5);2,333(1 ,^ Example 204: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.410 (0.7), 5.194 (1.3), 4.412 (0.6), 4.378 (0.6), 4.247 ( 0.7), 4.230 (1, 0), 4.184 (1, 6), 4.166 (4.9), 4.1, 49 (5.3), 4.131 (2.1), 4.119 (1, 7); 4.101 (1, 9), 4.098 (1, 7), 4.080 (1, 6), 4.071 (0.5), 4.062 (0.5), 3.464 (15.5), 3.356 (1.0), 3.322 (1, 0); 3,119 (0.6); 3.092 (1, 0); 3, 061 (0.5); 2.737 (0.6); 2.675 (1.0); 2.670 (1, 4); 2,666 (1, 0); 2,555 (1, 8), 2,550 (4,1), 2,546 (4,2), 2,541 (3,1), 2,524 (4,4), 2,519 (6,3), 2,511 (87.7); 2.506 (185.6); 2.501 (250.0); 2.497 (176.4); 2.492 (82.8); 2.466 (6.1); 2.459 (4.4); 2.454 ( 1, 7); 2,337 (0.5); 2,333 (1, ^
2,086(6,3);2,066(0,6);2,032(0,7);1 ,687(2,8);1 ,658(3,2);1 ,612(0,8);1 ,534(2,0); 1 ,488(1 ,6);1 ,404(3,3);1 ,329(0,8);1 ,291(1 ,0);1 ,272(0,7);1 ,263(1 ,2) 2.086 (6.3); 2.066 (0.6); 2.032 (0.7); 1, 687 (2.8); 1, 658 (3.2); 1, 612 (0.8); 1, 534 (2.0); 1, 488 (1, 6); 1, 404 (3.3); 1, 329 (0.8); 1, 291 (1, 0); 1, 272 (0.7); 1, 263 (1 2)
;1 ,241 (7,9);1 ,224(16,0);1 ,206(7,7);1 ,184(4,2);1 ,167(7,9);1 ,149(3,8);0,000(8,0) 1, 241 (7.9); 1, 224 (16.0); 1, 206 (7.7); 1, 184 (4.2); 1, 167 (7.9); 1, 149 ( 0.000 (8.0), 3.8)
Beispiel 206: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,500(1 ,0);3,406(3,9);3,390(7,3);3,373(4,7);3,325(107,8);3,278(4,5);3,262(7,4);3,247(3,8);3Example 206: 1 H NMR (400.0 MHz, de-DMSO): δ = 7,500 (1, 0); 3.406 (3.9); 3.390 (7.3); 3.373 (4.7); 3.325 ( 107.8); 3,278 (4.5); 3,262 (7.4); 3,247 (3.8); 3
,203(0,6);3,101(4,7);2,676(0,8);2,671(1 ,0);2,666(0,8);2,556(0,6);2,551(1 ,2);2,547(1 ,5);2,511(69,2);2,506(133,2);2,502(172,9);2,497(121 ^, 203 (0.6); 3.101 (4.7); 2.676 (0.8); 2.671 (1.0); 2.666 (0.8); 2.556 (0.6); 2.551 (1, 2); 2.547 (1, 5), 2.511 (69.2), 2.506 (133.2), 2.502 (172.9), 2.497 (121 ^
493(56,9);2,459(2,6);2,454(2,1);2,449(1 ,8);2,444(1 ,8);2,432(2,1);2,429(2,1);2,383(1 ,4);2,333(0,8);2,329(1 ,0);2,3 493 (56.9), 2.459 (2.6), 2.454 (2.1), 2.449 (1.8), 2.444 (1.8), 2.432 (2.1), 2.429 (2.1), 2.383 (1, 4); 2.333 (0.8); 2.329 (1, 0); 2.3
);1 ,847(6,2);1 ,845(6,2);1 ,837(16,0);1 ,829(9,0);1 ,827(8,7);1 ,819(11 ,6);1 ,815(10,3);1 ,797(7,0);1 ,781(3,5);1 ,482(2,3);1 ,400(5,0);0,000(4,9) 1, 847 (6.2); 1, 845 (6.2); 1, 837 (16.0); 1, 829 (9.0); 1, 827 (8.7); 1, 819) (11, 6); 1, 815 (10.3); 1, 797 (7.0); 1, 781 (3.5); 1, 482 (2.3); 1, 400 (5.0) ; 0,000 (4.9)
Beispiel 216: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,447(3,2);6,618(0,6);3,430(1 ,1);3,412(3,1);3,395(3,2);3,377(1 ,3);3,155(1 ,3);3,138(3,7);3,1Example 216: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.447 (3.2); 6.618 (0.6); 3.430 (1.1); 3.412 (3.1); 3.355 ( 3,2), 3,377 (1,3), 3,155 (1,3), 3,138 (3,7), 3,1
20(3,8);3,103(1 ,5);2,893(16,0);2,829(0,8);2,817(0,8);2,791(12,9);2,543(0,6);2,526(0,8);2,521(1 ,2);2,512(20,7);2,508(45,3);2,503(62,2^20 (3.8), 3.103 (1.5), 2.893 (16.0), 2.829 (0.8), 2.817 (0.8), 2.791 (12.9), 2.543 (0.6), 2.526 (0.8), 2.521 (1.2), 2.512 (20.7), 2.508 (45.3), 2.503 (62.2 ^
44,3);2,494(21 ,0);2,466(1 ,3);2,461(1 ,2);2,456(1 ,1);2,451(0,9);1 ,516(2,4);1 ,495(8,6);1 ,482(4,7);1 ,452(1 ,7);1 ,44 44.3); 2,494 (21, 0); 2,466 (1,3); 2,461 (1,2); 2,456 (1,1); 2,451 (0,9); 1,516 (2,4); 1 , 495 (8,6); 1, 482 (4,7); 1, 452 (1, 7); 1, 44
378(3,3);1 ,099(3,3);1 ,082(7,0);1 ,064(4,2);1 ,046(5,0);1 ,028(8,6);1 ,011 (4,3);0,000(2,0)  378 (3,3); 1, 099 (3,3); 1, 082 (7,0); 1, 064 (4,2); 1, 046 (5,0); 1, 028 (8,6 ); 1, 011 (4.3); 0.000 (2.0)
Beispiel 218: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,424(1 ,8);3,406(13,4);3,388(11 ,2);3,370(8,9);3,353(4,0);3,142(2,4);3,124(6,3);3,107(6,5);3 ,089(2,6);2,935(0,6);2,923(0,6);2,675(0,7);2,671(1 ,0);2,666(0,8);2,552(0,5);2,524(2,5);2,519(3,7);2,511(59,4);2,506(129,2);2,502(177,3);2,49 7(125,6);2,492(59,4);2,457(2,9);2,452(3,2);2,448(3,1);2,389(0,5);2,333(0,8);2,328(1 ,1);2,324(0 Example 218: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.424 (1, 8); 3.406 (13.4); 3.388 (11, 2); 3.370 (8.9); 3.353 ( 4.0); 3.142 (2.4); 3.124 (6.3); 3.107 (6.5); 3, 089 (2.6); 2.935 (0.6); 2.923 (0.6); 2.675 (0.7); 2.671 (1, 0); 2.666 (0.8); 2.552 (0.5); 2.524 (2.5); 2.519 (3.7); 2.511 (59.4); 2.506 ( 129.2), 2.502 (177.3), 2.49 7 (125.6), 2.492 (59.4), 2.457 (2.9), 2.452 (3.2), 2.488 (3.1); 2.389 (0.5), 2.333 (0.8), 2.328 (1, 1), 2.324 (0
1 ,157(4,0);1 ,139(1 ,9);1 ,115(7,6);1 ,097(16,0);1 ,080(8,6);1 ,031(7,6);1 ,014(14,2);0,996(7,3);0,000(6,1)  1, 157 (4.0); 1, 139 (1, 9); 1, 115 (7.6); 1, 097 (16.0); 1, 080 (8.6); 1, 031 (7 , 6); 1, 014 (14,2); 0,996 (7,3); 0,000 (6,1)
Beispiel 220: 1H-NMR(400,0 MHz, de-DMSO): δ= 4,195(4,1);4,038(2,2);3,677(16,0);3,627(0,8);3,599(10,4);3,515(8,1);2,959(6,0);2,889(9,4);2 ,675(0,7);2,671 (0,9);2,666(0,7);2,561 (1 ,4);2,557(1 ,8);2,552(1 ,7);2,547(0,7);2,524(2,9);2,511 (59,3);2,506(118,7);2,501 (157,3);2,497(111 ,5);2, 492(53,6);2,461(4,0);2,457(4,4);2,452(4,4);2,447(3,3);2,443(2,4);2,422(2,0);2,333(0,7);2,328(1 ,0);2,324(0,7)2 Example 220: 1 H-NMR (400.0 MHz, de-DMSO): δ = 4.195 (4.1), 4.038 (2.2), 3.677 (16.0), 3.627 (0.8), 3.599 ( 10.4); 3.515 (8.1); 2.959 (6.0); 2.889 (9.4); 2.675 (0.7); 2.671 (0.9); 2.666 (0.7); 2.561 (1, 4); 2,557 (1, 8); 2,552 (1, 7); 2,547 (0,7); 2,524 (2,9); 2,511 (59,3); 2,506 (118,7); 2,501 ( 2,497 (111, 5), 2, 492 (53.6), 2.461 (4.0), 2.457 (4.4), 2.452 (4.4), 2.447 (3.3), 2.443 (2.4); 2.422 (2.0); 2.333 (0.7); 2.328 (1.0); 2.324 (0.7) 2
0,000(4,6) 0.000 (4.6)
Beispiel 221 : 1H-NMR(400,1 MHz, de-DMSO): δ= 8,879(1 ,6);8,827(0,4);8,401(0,6);8,382(0,6);8,346(0,5);8,326(0,6);8,319(0,5);8,309(15,7);8,Example 221: 1 H-NMR (400.1 MHz, de-DMSO): δ = 8.879 (1, 6), 8.827 (0.4), 8.401 (0.6), 8.382 (0.6), 8.346 ( 0.5); 8,326 (0.6); 8,319 (0.5); 8,309 (15.7); 8,
290(16,0);7,634(1 ,8);7,245(0,3);7,227(0,4);7,218(0,4);7,196(0,3);7,192(0,4);7,164(0,8);7,146(0,8);7,091 (0,4);7,062(0,5);7,046(0,5);7,037(0,5)290 (16.0), 7.634 (1.8), 7.245 (0.3), 7.227 (0.4), 7.218 (0.4), 7.196 (0.3), 7.192 (0.4), 7.164 (0.8); 7.146 (0.8); 7.091 (0.4); 7.062 (0.5); 7.046 (0.5); 7.037 (0.5)
7,008(0,5);6,964(0,5);6,943(0,5);6,927(0,5);6,834(0,6);6,818(0,6);6,792(0,8);6,773(0,8);6,757(0,6);6,752(0,6)^ 7,008 (0.5); 6,964 (0.5); 6,943 (0.5); 6,927 (0.5); 6,834 (0.6); 6,818 (0.6); 6,792 (0.8); 6,773 (0.8); 6,757 (0.6); 6,752 (0.6) ^
;6,622(9,2);6,603(9,1);6,574(0,6);6,555(0,5);6,522(0,5);6,492(0,4);6,469(0,4);6,428(0,4);6,405(0,4);6,388(^  ; 6,622 (9.2); 6,603 (9.1); 6,574 (0.6); 6,555 (0.5); 6,522 (0.5); 6,492 (0.4); 6,469 (0.4); 6,428 (0.4); 6,405 (0.4); 6,388 (^
);2,674(0,6);2,669(0,5);2,560(0,8);2,555(1 ,0);2,551(0,6);2,527(1 ,6);2,522(2,4);2,514(38,3);2,509(83,4);2,50^  2,674 (0,6), 2,669 (0,5), 2,560 (0,8), 2,555 (1, 0), 2,551 (0,6), 2,527 (1,6), 2,522 (2,4) ; 2,514 (38.3); 2,509 (83.4); 2.50 ^
,464(0,9);2,460(1 ,1);2,455(1 ,1);2,451(0,7);2,336(0,5);2,332(0,7);2,327(0,5);1 ,568(2,5);1 ,553(5,9);1 ,549(5,6);1 ,545(7,0);1 ,541(5,0);1 ,530(4,3); 1 ,520(2,6);1 ,507(3,3);1 ,503(4,6);1 ,500(5,4);1 ,497(6,7);1 ,493(5,2);1 ,483(4,9);1 ,476(1 ,3);1 ,450(1 ,5);1 ,439(1 ,5);1 ,430(4,2);1 ,419(4,9);1 , 415(7,2) , 464 (0.9), 2.460 (1, 1), 2.455 (1, 1), 2.451 (0.7), 2.336 (0.5), 2.332 (0.7), 2.327 (0.5); 1, 568 (2.5); 1, 553 (5.9); 1, 549 (5.6); 1, 545 (7.0); 1, 541 (5.0); 1, 530 (4 , 3); 1, 520 (2,6); 1, 507 (3,3); 1, 503 (4,6); 1, 500 (5,4); 1, 497 (6,7); 1, 493 (5 , 2); 1, 483 (4,9); 1,476 (1,3); 1,450 (1,5); 1,439 (1,5); 1,430 (4,2); 1 , 419 (4.9); 1, 415 (7.2)
;1 ,411 (5,9);1 ,407(9,8);1 ,396(5,5);1 ,392(9,2);1 ,389(5,9);1 ,385(4,7);1 ,382(3,4);1 ,368(2,5);1 ,347(1 ,2);1 ,331 (1 ,2);0,008(0,6) 1, 411 (5.9); 1, 407 (9.8); 1, 396 (5.5); 1, 392 (9.2); 1, 389 (5.9); 1, 385 ( 4.7); 1, 382 (3.4); 1, 368 (2.5); 1, 347 (1, 2); 1, 331 (1, 2); 0.008 (0.6)
Beispiel 222: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,361(0,4);9,487(0,4);8,338(0,4);8,318(0,4);8,303(5,1);8,284(5,2);6,525(0,5);3,380(0,6);3, 327(28,4);3,277(0,8);3,171(0,4);2,833(15,8);2,821(16,0);2,512(8,8);2,508(19,1);2,503(26,7);2,499(19,4);2,494(9,2);2,453(0,3);2,384(0,5^ 9(0,5);2,073(0,4);1 ,565(0,9);1 ,549(1 ,9);1 ,545(2,0);1 ,541(2,3);1 ,537(1 ,8);1 ,527(1 ,5);1 ,517(0,9);1 ,504(1 ,0);1 ,500(1 ,6);1 ,496(2,0);1 ,494(2,3);1 ,4 92(2,3);1 ,489(1 ,9);1 ,479(2,1);1 ,463(0,4);1 ,451(0,4);1 ,432(1 ,1);1 ,416(2,1);1 ,409(2,5);1 ,393(2,5);1 ,369(0,6) Example 222: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.361 (0.4), 9.487 (0.4), 8.338 (0.4), 8.318 (0.4), 8.303 ( 5.1), 8.284 (5.2), 6.525 (0.5), 3.380 (0.6), 3.327 (28.4), 3.277 (0.8), 3.171 (0.4), 2.833 (15.8) 2,821 (16.0); 2,512 (8.8); 2,508 (19.1); 2.503 (26.7); 2,499 (19.4); 2,494 (9.2); 2,453 ( 0.3); 2.384 (0.5 ^ 9 (0.5); 2.073 (0.4); 1.565 (0.9); 1. 549 (1, 9); 1. 545 (2.0 1, 541 (2, 3), 1, 537 (1, 8), 1, 527 (1, 5), 1, 517 (0.9), 1, 504 (1, 0), 1, 500 (1, 6); 1, 496 (2,0); 1,494 (2,3); 1,4,9 (1,3); 1,489 (1,9); 1,479 (2,1); 1, 463 (0.4); 1, 451 (0.4); 1, 432 (1, 1); 1, 416 (2.1); 1, 409 (2.5); 1, 393) (2.5); 1, 369 (0.6)
Beispiel 223: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,363(0,5);9,604(0,4);8,305(4,3);8,286(4,4);6,523(0,5);3,349(1 ,8);3,323(77,0);3,299(5,0);3Example 223: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.363 (0.5), 9.604 (0.4), 8.305 (4.3), 8.286 (4.4), 6.523 ( 0.5), 3.349 (1.8), 3.323 (77.0), 3.299 (5.0), 3
,296(2,6);3,281(1 ,6);3,171(0,5);2,525(0,4);2,521(0,6);2,512(10,7);2,507(23,4);2,503(32,9);2,498(23,8);2,494(11 ,3);2,073(0,4) , 296 (2.6); 3.281 (1, 6); 3.171 (0.5); 2.525 (0.4); 2.521 (0.6); 2.512 (10.7); 2.507 (23.4); 2.503 (32.9), 2.498 (23.8), 2.494 (11, 3), 2.073 (0.4)
0(1 ,9);1 , 546(1 ,9);1 ,543(2,2);1 , 538(1 , 7);1 , 528(1 ,4);1 ,517(0,8);1 , 505(1 ,0);1 , 501 (1 ,5);1 , 498(1 , 9);1 , 495(2 ,2); 1 ,493(2, 1 ); 1 ,490(1 ,7); 1 ,480(1 ,6);1 ,4 0 (1, 9); 1, 546 (1, 9); 1, 543 (2, 2); 1, 538 (1, 7); 1, 528 (1, 4); 1, 517 (0.8 1, 505 (1, 0), 1, 501 (1, 5), 1, 498 (1, 9), 1, 495 (2, 2); 1, 493 (2, 1); 1,490 (1, 7); 1, 480 (1, 6); 1, 4
48(0,3);1 ,436(0,6);1 ,428(0,9);1 ,412(1 ,9);1 ,405(2,4);1 ,389(2,4);1 ,366(0,6);1 ,135(7,4);1 ,116(16,0);1 ,098(7,3) 48 (0.3); 1, 436 (0.6); 1, 428 (0.9); 1, 412 (1, 9); 1, 405 (2.4); 1, 389 (2.4 1, 366 (0.6); 1, 135 (7.4); 1, 116 (16.0); 1, 098 (7.3)
Beispiel 224: 1H-NMR(400,1 MHz, de-DMSO): δ= 12,373(1 , 1);9,677(1 ,0);8,309(4,0);8,306(4,3);8,290(4,1);8,287(4,4);6,526(1 ,1);3,418(0,4);3, 368(2,5);3,323(414,6);3,319(444,4);3,290(4,6);3,285(4,4);3,271(7,4);3,254(6,3);3,240(2,5);3,236(2,5);3,174(1 ,0);3,170(1 ,1);2,675(1 ,0);2,671( 1 ,0);2,666(0,6);2,550(0,8);2,546(0,9);2,541(0,8)£ Example 224: 1 H-NMR (400.1 MHz, de-DMSO): δ = 12.373 (1, 1), 9.677 (1.0), 8.309 (4.0), 8.306 (4.3), 8.290 ( 4.1), 8.287 (4.4), 6.526 (1, 1), 3.418 (0.4), 3.368 (2.5), 3.323 (414.6), 3.319 (444.4), 3.290 (4,6); 3,285 (4.4); 3,271 (7,4); 3,254 (6,3); 3,240 (2,5); 3,236 (2,5); 3,174 (1, 0); 3,170 ( 1, 1), 2.675 (1.0), 2.671 (1.0), 2.666 (0.6), 2.550 (0.8), 2.546 (0.9), 2.541 (0.8) pounds
,5);2,077(1 ,2);2,072(1 ,6);1 , 567(1 , 1);1 ,544(5,7);1 ,523(5,4);1 ,505(6,7);1 ,495(4,3);1 ,490(4,1);1 ,486(3,7);1 , 473(1 ,0);1 ,451 (0,6);1 ,429(1 ,3);1 ,410( 3,7);1 ,391 (3,7);1 ,370(0,8);0,923(0,7);0,916(7,0);0,912(8,0);0,905(1 ,7);0,898(13,8);0,893(16,0);0,879(6,4);0,875(6,9);0,005(2,6)  , 5), 2.077 (1, 2), 2.072 (1, 6), 1, 567 (1, 1), 1, 544 (5, 7), 1, 523 (5, 4), 1, 505 (6 , 7); 1, 495 (4,3); 1,490 (4,1); 1, 486 (3,7); 1, 473 (1, 0); 1, 451 (0,6); 1 , 429 (1, 3); 1, 410 (3.7); 1, 391 (3.7); 1, 370 (0.8); 0.923 (0.7); 0.916 (7.0); 0.912 (8.0); 0.905 (1, 7); 0.898 (13.8); 0.883 (16.0); 0.879 (6.4); 0.875 (6.9); 0.005 (2.6)
Beispiel 226: 1H-NMR(400,1 MHz, CDCb): δ= 12,212(0,3);9,308(0,6);9,290(0,6);8,580(2,6);8,561 (2,6);7,265(13,0);6,374(3,2);6,354(3,2);4,30 2(0,6);4,285(0,9);4,266(0,9);4,250(0,6);1 ,727(0,5);1 ,709(1 ,4);1 ,705(1 ,5);1 ,701 (0,9);1 ,688(0,8);1 ,680(0,7);1 ,663(1 ,6);1 ,662(1 ,6);1 ,657(1 ,9);1 ,6Example 226: 1 H-NMR (400.1 MHz, CDCb): δ = 12.212 (0.3); 9.308 (0.6); 9.290 (0.6); 8.580 (2.6); 8.561 (2, 6), 7.265 (13.0), 6.374 (3.2), 6.354 (3.2), 4.30 2 (0.6), 4.285 (0.9), 4.266 (0.9), 4.250 ( 0.6); 1, 727 (0.5); 1, 709 (1, 4); 1, 705 (1, 5); 1, 701 (0.9); 1, 688 (0.8); 1, 680 (0.7), 1, 663 (1, 6), 1, 662 (1, 6), 1, 657 (1, 9), 1, 6
53(1 ,4);1 ,641(1 ,1);1 ,476(0,7);1 ,464(0,9);1 ,459(1 ,6);1 ,454(2,1);1 ,441(1 ,0);1 ,437(2,1);1 ,431 (1 ,5);1 ,414(0,5);1 ,265(15,9);1 ,249(16,0) 53 (1, 4); 1, 641 (1,1); 1,476 (0,7); 1,464 (0,9); 1,459 (1,6); 1,454 (2,1); 1, 441 (1, 0), 1, 437 (2.1), 1, 431 (1, 5), 1, 414 (0.5), 1, 265 (15.9), 1, 249 (16.0)
Beispiel 233: 1H-NMR(400,1 MHz, de-DMSO): δ= 8,094(0,4);8,075(0,4);3,104(16,0);2,985(0,4);2,969(0,6);2,953(0,5);2,292(1 ,5);2,288(3,2);2, 284(4,4);2,280(3,3);2,276(1 ,6);0,241 (0,4);0,236(0,4);0,221 (0,4);0,217(0,4);0,000(0,5)
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Beispiel 576: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,757(4,0);9,849(2,4);8,386(9,8);8,368(10,2);7,881(0,5);7,859(0,9);7,836(8,2);7,815(9,8);7 ,654(0,6);7,632(0,8);7,616(15,9);7,594(13,3);6,837(2,7);6,820(2,7);5,979(1 ,0);5,966(2,2);5,953(2,2);5,940(2,6);5,937(1 ,9);5,923(2,9);5^ 5);5,897(2,6);5,885(1 ,3);5,220(4,9);5,216(5,2);5,177(4,4);5,173(4,7);5,135(5,2);5,131(5,3);5,109(4,8);5,105(4,9^ Example 233: 1 H-NMR (400.1 MHz, de-DMSO): δ = 8.094 (0.4), 8.075 (0.4), 3.104 (16.0), 2.985 (0.4), 2.969 ( 0.6), 2.953 (0.5), 2.292 (1.5), 2.288 (3.2), 2.284 (4.4), 2.280 (3.3), 2.276 (1.6), 0.241 (0.4), 0.236 (0.4), 0.221 (0.4), 0.217 (0.4), 0.000 (0.5)
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Example 576: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.757 (4.0); 9.849 (2.4); 8.386 (9.8); 8.368 (10.2); 7.881 ( 0.5), 7.859 (0.9), 7.836 (8.2), 7.815 (9.8), 7.654 (0.6), 7.632 (0.8), 7.616 (15.9), 7.594 (13.3); 6.837 (2.7); 6.820 (2.7); 5.979 (1.0); 5.966 (2.2); 5.953 (2.2); 5.940 (2.6); 5.937 ( 1, 9), 5.923 (2.9), 5 ^ 5), 5.897 (2.6), 5.885 (1.3), 5.220 (4.9), 5.216 (5.2), 5.177 (4.4 5.105 (4,9 ^); 5,173 (4.7); 5,135 (5.2); 5,131 (5.3); 5,109 (4.8)
0,4);3,967(5,9);3,904(16,0);3,501(0,4);3,492(0,4);3,349(838,3);3,168(1 ,2);2,673(1 ,9);2,508(245,1);2,503(310,5);2,499(246,5);2,^ 3.967 (5.9), 3.904 (16.0), 3.501 (0.4), 3.492 (0.4), 3.349 (838.3), 3.168 (1, 2), 2.673 (1 , 9); 2,508 (245.1); 2.503 (310.5); 2,499 (246.5); 2, ^
3(0,3);0,000(6,5)  3 (0.3); 0,000 (6.5)
Beispiel 583: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,664(1 ,9);9,662(0,9);9,647(0,9);8,364(5,9);8,345(6,2);7,820(3,4);7,799(4,1);7,622(1 ,2);7, 616(9,2);7,599(2,6);7,594(7,4);6,813(1 ,2);6,796(1 ,2);4,035(0,6);4,018(1 ,3);4,000(1 ,6);3,982(1 ,3);3,965(0,6);3,904(11 ,8);3,505(0,4);3,364(640, 5);2,678(0,8);2,674(1 ,1);2,669(0,8);2,527(3,2);2,513(66,4);2,509(131 ,1);2,505(169,0);2,500(123,1);2,496(60,8^ Example 583: 1 H NMR (400.0 MHz, de-DMSO): δ = 12.664 (1.9); 9.662 (0.9); 9.647 (0.9); 8.364 (5.9); 8.345 ( 6.2); 7.820 (3.4); 7.799 (4.1); 7.622 (1, 2); 7, 616 (9.2); 7.599 (2.6); 7.594 (7.4); 6.813 (1,2), 6,796 (1,2), 4,035 (0,6), 4,018 (1,3), 4,000 (1,6), 3,982 (1,3), 3,965 (0,6), 3,904 ( 11, 8), 3.505 (0.4), 3.364 (640, 5), 2.678 (0.8), 2.674 (1, 1), 2.669 (0.8), 2.527 (3.2), 2.513 (66 , 4), 2.509 (131, 1), 2.505 (169.0), 2.500 (123.1), 2.496 (60.8 ^
0);2,327(0,7);1 ,501 (0,9);1 ,495(1 ,1);1 ,484(1 ,8);1 ,478(3,1);1 ,460(4,1);1 ,443(2,4);1 ,382(0,5);1 ,365(1 ,4);1 ,347(2,4);1 ,333(2,2);1 ,329(2,8);1 ,311(2 ,2);1 ,294(1 ,1);1 ,283(0,3);1 ,277(0,4);1 ,157(13,6);1 ,140(13,5);0,909(7,8);0,891(16,0);0,872(6,5);0,000(1 ,5)  1, 495 (1, 1); 1, 484 (1, 8); 1, 478 (3,1); 1, 460 (1); 4.1); 1, 443 (2.4); 1, 382 (0.5); 1, 365 (1, 4); 1, 347 (2.4); 1, 333 (2.2); 1, 329 (2,8); 1, 311 (2, 2); 1, 294 (1, 1); 1, 283 (0.3); 1, 277 (0.4); 1, 157 (13 , 6), 1, 140 (13.5), 0.909 (7.8), 0.881 (16.0), 0.872 (6.5), 0.000 (1, 5)
Beispiel 597: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,690(2,4);9,830(1 ,5);8,423(0,7);8,404(0,7);8,376(8,3);8,357(8,6);7,880(0,9);7,859(1 ,2);7, 829(5,9);7,808(7,2);7,654(1 ,3);7,632(1 ,2);7,615(12,7);7,594(10,5);7,048(0,5);7,029(0,5);6,822(1 ,7);6,804(1 ,8);3,904(16,0);3,548(0,5);3,508(1 , 9);3,496(5,4);3,483(7,8);3,472(7,5);3,465(11 ,5);3,455(9,8);3,443(4,0);3,437(3,2);3,373(429,2);3,361(533,6);3,305(t Example 597: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.690 (2.4); 9.830 (1.5), 8.423 (0.7), 8.404 (0.7), 8.376 ( 8.3), 8.357 (8.6), 7.880 (0.9), 7.859 (1, 2), 7, 829 (5.9), 7.808 (7.2), 7.654 (1, 3), 7.632 (1,2), 7,615 (12,7), 7,594 (10,5), 7,048 (0,5), 7,029 (0,5), 6,822 (1, 7), 6,804 (1, 8), 3,904 ( 16.0), 3.548 (0.5), 3.508 (1.9), 3.496 (5.4), 3.483 (7.8), 3.472 (7.5), 3.455 (11, 5), 3.455 (9 , 8); 3,443 (4.0); 3,437 (3.2); 3,373 (429.2); 3,361 (533.6); 3.305 (t
3,107(0,4);2,678(1 ,1);2,673(1 ,5);2,669(1 ,1);2,551(0,4);2,526(4,0);2,513(95,7);2,509(190,0);2,504(248,3);2,500(186,6);2 3.107 (0.4); 2.678 (1, 1); 2.673 (1, 5); 2.669 (1, 1); 2.551 (0.4); 2.526 (4.0); 2.513 (95.7); 2.509 (190.0) 2.504 (248.3); 2,500 (186.6); 2
,326(1 ,1);0,000(1 ,6)  , 326 (1, 1); 0.000 (1, 6)
Beispiel 603: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,665(1 ,8);9,790(1 ,1);9,775(1 ,1);8,425(0,7);8,406(0,7);8,370(6,9);8,351 (7,3);7,879(1 ,0);7, 858(1 , 2);7,823(4,9);7,802(6,0);7,654(1 ,3);7,632(1 ,2);7,617(10,3);7,595(8,6);7,048(0,5);7,029(0,5);6,816(1 ,5);6,799(1 ,5);4,1^ Example 603: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.665 (1, 8); 9.790 (1, 1); 9.775 (1, 1); 8.425 (0.7); 8.406 ( 0.7); 8.370 (6.9); 8.351 (7.3); 7.879 (1, 0); 7, 858 (1, 2); 7.823 (4.9); 7.802 (6.0); 7.654 (1, 3); 7.632 (1, 2); 7.617 (10.3); 7.595 (8.6); 7.048 (0.5); 7.029 (0.5); 6.816 (1, 5); 6.799 ( 1, 5), 4,1 ^
4,158(1 ,7);4,141(1 ,3);4,128(0,7);3,904(16,0);3,530(0,5);3,523(0,5);3,466(1 ,3);3,422(5,5);3,409(8,6);3,37 4.158 (1, 7), 4.141 (1, 3), 4.128 (0.7), 3.904 (16.0), 3.530 (0.5), 3.523 (0.5), 3.466 (1.3), 3.442 (5.5); 3,409 (8.6); 3.37
332(7,0);3,319(4,7);3,293(46,0);3,169(1 ,0);3,114(0,3);2,679(1 ,0);2,674(1 ,3);2,670(1 ,0);2,527(3,6);2 3,319 (4,7), 3,293 (46,0), 3,169 (1, 0), 3,114 (0,3), 2,679 (1, 0), 2,674 (1, 3), 2,670 (1, 0); 2.527 (3.6); 2
36(0,9);2,332(1 ,3);2,327(1 ,0);1 ,170(16,0);1 ,153(15,9);1 ,125(0,4);0,000(2,0) 36 (0.9), 2.332 (1.3), 2.327 (1.0), 1.170 (16.0), 1.153 (15.9), 1.125 (0.4), 0.000 ( 2.0)
Beispiel 643: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,835(1 ,4);7,625(1 ,7);7,606(1 ,8);7,573(6,6);7,551(5,7);3,586(3,1);3,305(103,8);2,669(2,0);2Example 643: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.835 (1, 4), 7.625 (1, 7), 7.606 (1, 8), 7.573 (6.6), 7.551 ( 5.7); 3,586 (3.1); 3,305 (103.8); 2,669 (2.0); 2
,523(7,5);2,518(10,1);2,509(137,1);2,505(294,6);2,500(410,1);2,496(284,5);2,491(127,5);2,327(2,1);2,085(16,0);0,000(14,7) , 523 (7.5); 2,518 (10.1); 2.509 (137.1); 2.505 (294.6); 2,500 (410.1); 2.496 (284.5); 2.491 (127.5); 2,327 (2.1); 2,085 (16.0); 0.000 (14.7)
Beispiel 644: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,828(1 ,4);7,603(1 ,5);7,580(5,0);7,576(3,0);7,558(4,1);7,500(0,9);7,481(0,9);4,430(0,9);4,4 09(0,9);4,400(0,9);3,666(16,0);3,577(0,7);3,558(1 ,2);3,541(1 ,2);3,525(0,8);3,466(6,3);3,326(14,9);3,135(0,7);3,117(2,3);3,105(2,3);3,0 3,086(2,2);3,068(0,6);2,669(0,7);2,510(45,3);2,505(97,1);2,501(134,6);2,496(94,3);2,491(42,8);2,327(0,8);2,239(0,6);1 ,887(1 ,8);^ 176(9,3);1 , 158(4 ,4);0,000(3,5) Example 644: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.828 (1, 4), 7.603 (1.5), 7.580 (5.0), 7.576 (3.0), 7.558 ( 4.1), 7.500 (0.9), 7.481 (0.9), 4.430 (0.9), 4.4 09 (0.9), 4.400 (0.9), 3.666 (16.0); 3.577 (0.7), 3.558 (1.2), 3.541 (1.2), 3.525 (0.8), 3.466 (6.3), 3.326 (14.9), 3.135 (0.7), 3.117 (2,3); 3,105 (2,3); 3,0 3,086 (2,2); 3,068 (0,6); 2,669 (0,7); 2,510 (45,3); 2,505 (97,1) 2.501 (134.6), 2.496 (94.3), 2.491 (42.8), 2.327 (0.8), 2.239 (0.6), 1.887 (1, 8), ^ 176 (9, 3); 1, 158 (4, 4); 0.000 (3.5)
Beispiel 647: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,821(2,9);7,612(3,5);7,594(3,3);7,571(16,0);7,566(4,4);7,549(13,0);3,434(3,6);3,417(6,7);3 ,400(4,0);3,351(3,7);3,337(7,1);3,307(176,5);2,670(3,3);2,523(10,3);2,518(14,3);2,510(192,9);2,505(417,8);2,500(582,5);2,496(405,2);2,4Example 647: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.821 (2.9), 7.612 (3.5), 7.594 (3.3), 7.571 (16.0), 7.566 ( 4.4), 7.549 (13.0), 3.434 (3.6), 3.417 (6.7), 3, 400 (4.0), 3.351 (3.7), 3.337 (7.1), 3.307 (176.5); 2,670 (3.3); 2,523 (10.3); 2,518 (14.3); 2,510 (192.9); 2.505 (417.8); 2,500 (582.5); 2.496 ( 405.2), 2.4
182,0);2,327(3,2);1 ,836(6,8);0,000(28,8) 182.0); 2,327 (3,2); 1, 836 (6,8); 0,000 (28,8)
Beispiel 659: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,825(3,1);7,565(16,0);7,543(13,8);7,525(3,1);7,506(3,4);3,414(5,0);3,397(4,9);3,308(428,5Example 659: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.825 (3.1); 7.565 (16.0); 7.543 (13.8); 7.525 (3.1); 7.506 ( 3.4); 3,414 (5.0); 3,397 (4.9); 3,308 (428.5
);3,259(1 ,9);3,195(4,0);3,177(4,5);2,670(3,2);2,509(206,8);2,505(423,5);2,500(575,4);2,496(405,4);2,491(186,9);2,450(2,3);2,327P3.259 (1, 9), 3.195 (4.0), 3.177 (4.5), 2.670 (3.2), 2.509 (206.8), 2.505 (423.5), 2.500 (575.4) ; 2,496 (405.4); 2.491 (186.9); 2,450 (2.3); 2,327P
5,6);1 ,121 (10,7);1 ,104(5,6);1 ,068(5,7);1 ,051(9,9);1 ,033(4,5);0,008(3,9);0,000(99,2);-0,008(3,5) 1, 121 (10.7); 1, 104 (5.6); 1, 068 (5.7); 1, 051 (9.9); 1, 033 (4.5); 0.008 (3.9) 0.000 (99.2) - 0.008 (3.5)
Beispiel 661 : 1H-NMR(601 ,6 MHz, de-DMSO): δ= 9,048(1 ,5);8,431(0,5);8,419(0,5);8,357(13,1);8,345(13,7);8,050(0,3);8,041(0,4);8,035(0,3);8Example 661: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.048 (1.5), 8.431 (0.5), 8.419 (0.5), 8.357 (13.1), 8.345 ( 13.7) 8,050 (0.3); 8.041 (0.4); 8,035 (0.3); 8
,026(0,3);7,871(4,6);7,583(1 ,8);7,442(0,3);7,428(0,6);7,413(0,3);7,391(8,3);7,387(2,9);7,376(16,0);7,365(2,9);7,361(7,8);7,356(1 ,0);7,^, 0.26 (0.3), 7.871 (4.6), 7.583 (1.8), 7.442 (0.3), 7.428 (0.6), 7.413 (0.3), 7.391 (8.3); 7.377 (2.9), 7.376 (16.0), 7.365 (2.9), 7.361 (7.8), 7.356 (1, 0), 7, ^
;7,324(0,5);6,775(1 ,2);3,324(88,5);2,617(0,9);2,614(1 ,2);2,611(0,9);2,577(0,4);2,535(2,1);2,523(2,0);2,520(2,6);2,517(^ 7.324 (0.5), 6.775 (1, 2), 3.324 (88.5), 2.617 (0.9), 2.614 (1.2), 2.611 (0.9), 2.577 (0.4); 2,535 (2.1); 2,523 (2.0); 2,520 (2.6); 2,517 (^
137,2);2,502(185,2);2,499(135,8);2,496(63,4);2,389(0,9);2,386(1 ,2);2,383(0,8);1 ,909(1 ,2);0,000(7,9)  137.2), 2.502 (185.2), 2.499 (135.8), 2.496 (63.4), 2.389 (0.9), 2.386 (1.2), 2.383 (0.8), 1.909 (1, 2); 0.000 (7.9)
Beispiel 664: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,750(0,8);8,362(6,4);8,344(6,6);7,879(2,2);7,866(2,5);7,857(2,5);7,844(2,1);7,397(4,1);7,3Example 664: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.750 (0.8), 8.362 (6.4), 8.344 (6.6), 7.879 (2.2), 7.866 ( 2.5); 7,857 (2.5); 7,844 (2.1); 7,397 (4.1); 7.3
91(1 ,3);7,375(7,4);7,369(1 ,3);7,358(1 ,3);7,353(3,5);6,792(1 ,0);6,775(0,9);3,313(80,4);3,294(8,5);3,276(5,3);3,259(2,7);2,747(0,7);2,727(0,5);291 (1,3), 7,375 (7,4), 7,369 (1,3), 7,358 (1,3), 7,353 (3,5), 6,792 (1, 0), 6,775 (0,9), 3,313 (80.4) 3,294 (8.5); 3,276 (5.3); 3,259 (2.7); 2,747 (0.7); 2,727 (0.5); 2
,674(1 ,3);2,670(1 ,8);2,6650 ,3);2,523(8,2);2,518(11 ,4);2,510(102,5);2,505(210,6);2,501(288,1);2,496(202,8);2,491(92,^ , 674 (1, 3), 2,670 (1,8), 2,6650, 3), 2,523 (8,2), 2,518 (11, 4), 2,510 (102,5), 2,505 (210,6); 2.501 (288.1); 2.496 (202.8); 2,491 (92, ^
);2,327(1 ,6);2,323(1 ,1);2,085(3,5);1 ,575(0,6);1 ,557(2,4);1 ,539(4,4);1 ,521(4,3);1 ,503(2,5);1 ,485(0,8);1 ,390(1 ,3);0,930(8,0);0,922(2,3);0,911 (16 2,327 (1,6); 2,323 (1,1); 2,085 (3,5); 1, 575 (0,6); 1, 557 (2,4); 1, 539 (4,4); 1, 521 (4.3); 1, 503 (2.5); 1, 485 (0.8); 1, 390 (1, 3); 0.930 (8.0); 0.922 (2.3); 0.911 (16
,0);0,904(3,4);0,893(7,0);0,885(1 ,5);0,000(4,2) , 0), 0.904 (3.4), 0.883 (7.0), 0.885 (1, 5), 0.000 (4.2)
Beispiel 683: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,357(1 ,3);8,338(1 ,4);7,397(0,9);7,375(1 ,5);7,353(0,7);5,653(0,6);3,364(0,9);3,346(1 ,5);3,3 14(25,3);2,999(0,8);2,984(1 ,3);2,964(1 ,3);2,949(0,8);2,674(0,8);2,669(1 ,2);2,665(0,9);2,523(5,9);2,518(8,0);2,509(67,9);2,505(139,5);2,500(1 90,8);2,496(134,4);2,491(61 ,1);2,448(0,5);2,332(0,8);2,327(1 ,1);2,323(0,8);1 ,564(0,7);1 ,547(0,9);1 ,531(0,8);1 ,445(0,5);1 ,427(1 ,1);1 ,408(1 ,1); 1 ,262(1 ,1);1 ,251(0,9);1 ,244(2,2);1 ,226(2,1);1 ,208(1 ,5);1 ,176(1 ,0);0,921(7,2);0,904(7,0);0,891(3,9);0,874(3,9);0,^ Example 683: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.357 (1.3), 8.338 (1, 4), 7.397 (0.9), 7.375 (1.5), 7.353 ( 0.7), 5.653 (0.6), 3.364 (0.9), 3.346 (1.5), 3.3 (25.3), 2.999 (0.8), 2.984 (1, 3); 2.964 (1, 3), 2.949 (0.8), 2.674 (0.8), 2.669 (1.2), 2.665 (0.9), 2.523 (5.9), 2.518 (8.0), 2.509 (67.9); 2.555 (139.5); 2.500 (1 90.8); 2.496 (134.4); 2.491 (61.1); 2.448 (0.5); 2.332 (0.8); 2.327 (1, 1); 2,323 (0.8); 1, 564 (0.7); 1, 547 (0.9); 1, 531 (0.8); 1, 445 (0.5); 1 , 427 (1, 1); 1, 408 (1, 1); 1, 262 (1, 1), 1, 251 (0,9), 1, 244 (2,2), 1, 226 (2,1), 1, 208 (1, 5), 1, 176 (1 , 0); 0,921 (7.2); 0.904 (7.0) 0.891 (3.9) 0.874 (3.9) 0, ^
,4);0,000(69,3);-0,009(2,4) , 4); 0.000 (69.3) - 0.009 (2.4)
Beispiel 754: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,859(2,2);7,517(2,5);7,362(3,6);7,339(7,1);7,317(3,6);5,204(1 ,8);4,401(1 ,2);4,352(1 ,3);4,1 99(1 ,8);4,181(5,7);4,163(5,8);4,146(2,3);4,130(1 ,7);4,113(1 ,8);4,103(1 ,8);4,086(1 ,7);3,701 (1 ,2);3,427(1 ,6);3,308(446,5);3,133(1 ,3);2,766(1 ,1); 2,674(6,7);2,669(9,1);2,665(6,9);2,523(41 ,5);2,518(56,2);2,509(522,4);2,505(1093,8);2,500(1518,6);2,496(1082,7);2,491(503,7);2,451(5,0);2, 332(6,6);2,327(9,0);2,322(6,5);2,180(1 ,2);2,150(1 ,3);2,085(1 ,8);1 ,671(3,2);1 ,554(1 ,8);1 ,255(7,7);1 ,237( 16,0); 1 ,220(7,0); 1 ,191(4,1);1 ,173(8,2);Example 754: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.859 (2.2); 7.517 (2.5); 7.362 (3.6); 7.339 (7.1); 7.317 ( 3, 6), 5.204 (1, 8), 4.401 (1, 2), 4.352 (1, 3), 4.1 99 (1, 8), 4.181 (5.7), 4.163 (5.8); 4,146 (2,3), 4,130 (1, 7), 4,113 (1, 8), 4,103 (1, 8), 4,086 (1, 7), 3,701 (1,2), 3,427 (1,6), 3,308 (446.5); 3.133 (1, 3); 2.766 (1, 1); 2.654 (6.7), 2.669 (9.1), 2.665 (6.9), 2.523 (41, 5), 2.518 (56.2), 2.509 (522.4), 2.505 (1093.8), 2.500 (1518.6); 2.496 (1082.7); 2.491 (503.7); 2.451 (5.0); 2.332 (6.6); 2.327 (9.0); 2.322 (6.5); 2,180 (1,2), 2,150 (1,3), 2,085 (1,8), 1,671 (3,2), 1, 554 (1, 8), 1, 255 (7,7), 1, 237 (16.0); 1, 220 (7.0); 1, 191 (4,1); 1, 173 (8,2);
1 ,156(4,2);0,146(2,7);0,008(21 ,4);0,000(679,3);-0,009(25,0);-0,050(1 ,8);-0,150(2,7) 1, 156 (4.2), 0.146 (2.7), 0.008 (21, 4), 0.000 (679.3), - 0.009 (25.0), - 0.050 (1.8), - 0.150 (2 , 7)
Beispiel 768: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,963(2,1);7,855(3,5);7,510(3,5);7,490(3,5);7,351(9,0);7,329(16,0);7,307(7,5);3,413(6,2);3,Example 768: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.963 (2.1), 7.855 (3.5), 7.510 (3.5), 7.490 (3.5), 7.351 ( 9.0); 7,329 (16.0); 7,307 (7.5); 3,413 (6.2); 3,
395(7,5);3,309(510,6);3,201(5,6);3,181 (5,2);2,674(10,9);2,669(14,3);2,665(10,4);2,552(12,9);2,523(72,8);2,518(97,2);2,50^ 395 (7.5), 3.309 (510.6), 3.201 (5.6), 3.181 (5.2), 2.674 (10.9), 2.669 (14.3), 2.665 (10.4), 2.552 (12.9) 2,523 (72.8); 2,518 (97.2); 2.50 ^
2,1);2,500(2343,1);2,496(1660,3);2,491(762,4);2,456(10,1);2,452(10,4);2,396(2,4);2,332(10,4);2,327(13,6);2,323(9,9);2,085  2.1), 2.500 (2343.1) 2.496 (1660.3) 2.491 (762.4); 2.456 (10.1); 2.452 (10.4); 2,396 (2.4); 2,332 (10 , 4); 2,327 (13.6); 2,323 (9.9); 2,085
,487(3,0);1 , 235(1 ,9);1 ,175(2,5);1 ,138(6,8);1 ,120(12,3);1 ,103(6,6);1 ,070(6,3);1 , 053(11 ,8);1 ,034(5,8);0,942(4,6);0,924(2,6);0,146(3,9);0,008(37 , 487 (3.0); 1, 235 (1, 9); 1, 175 (2.5); 1, 138 (6.8); 1, 120 (12.3); 1, 103 (6, 6); 1, 070 (6,3); 1, 053 (11, 8); 1, 034 (5,8); 0,942 (4,6); 0,924 (2,6); 0,146 (3,9) 0.008 (37
,2);0,000(1090,3);-0,009(38,3);-0,049(3,2);-0, 150(4, 1 ) , 2), 0.000 (1090.3), - 0.009 (38.3), - 0.049 (3.2), - 0, 150 (4, 1)
Beispiel 770: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,861(1 ,3);7,571(1 ,2);7,552(1 ,1);7,523(1 ,2);7,504(1 ,2);7,365(2,3);7,357(2,0);7,343(4,2);7,3 35(3,2);7,321(2,1);7,313(1 ,4);4,213(5,1);4,115(3,5);3,690(16,0);3,606(10,5);3,334(110,9);2,984(8,4);2,957(12,9);2,674(2,9^ Example 770: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.861 (1.3), 7.571 (1.2), 7.552 (1.1), 7.523 (1.2), 7.504 ( 1, 2); 7,365 (2,3); 7,357 (2,0); 7,343 (4,2); 7,335 (3,2); 7,321 (2,1); 7,313 (1, 4); 4,213 (5.1); 4,115 (3.5); 3,690 (16.0); 3.606 (10.5); 3.334 (110.9); 2,984 (8.4); 2,957 (12.9); 2.674 (2.9 ^
2,8);2,660(1 ,4);2,604(0,7);2,555(1 ,3);2,551(1 ,4);2,546(0,9);2,523 0,7);2,518(16,5);2,509(223,4);2,505(480,0);2,500(666,0);2,495(464^ 91(209,0);2,455(2,3);2,450(2,4);2,446(1 ,5);2,416(0,6);2,332(2,8);2,327(4,0);2,322(2,9);2,318(1 ,4);2,085(4,4^ 2.68), 2.660 (1,4), 2,604 (0,7), 2,555 (1,3), 2,551 (1,4), 2,546 (0,9), 2,523, 0,7), 2,518 (16, 5), 2.509 (223.4), 2.505 (480.0), 2.500 (666.0), 2.495 (464 ^ 91 (209.0), 2.455 (2.3), 2.450 (2.4), 2.446 (1, 5); 2,416 (0.6); 2,332 (2,8); 2,327 (4,0); 2,322 (2,9); 2,318 (1,4); 2,085 (4,4)
1 ,158(0,7);0,008(0,6);0,000(22,7);-0,009(0,8)  1, 158 (0.7), 0.008 (0.6), 0.000 (22.7), - 0.009 (0.8)
Beispiel 771 : 1H-NMR(400,0 MHz, de-DMSO): δ= 12,805(6,0);9,059(2,9);8,973(0,3);8,576(0,5);8,456(0,5);8,437(0,5);8,393(15,5);8,374(16,0);Example 771: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.805 (6.0), 9.059 (2.9), 8.973 (0.3), 8.576 (0.5), 8.456 ( 0.5); 8,437 (0.5); 8,393 (15.5); 8,374 (16.0);
8,319(0,4);8,280(0,4);8,276(0,5);8,255(0,9);8,180(7,1);8,113(4,2);8,098(4,2);8,026(0,4);7,995(0,4);7,973(0,5);7,955(0,5);7,913(7,9)8,319 (0.4); 8,280 (0.4); 8.276 (0.5); 8,255 (0.9); 8,180 (7.1); 8,113 (4.2); 8,098 (4.2); 8.026 (0.4); 7,995 (0.4); 7,973 (0.5); 7,955 (0.5); 7,913 (7.9)
3);7,866(0,5);7,844(0,5);7,825(0,6);7,785(7,8);7,766(12,3);7,746(5,3);7,643(3,3);7,552(0,6);7,533(0,5);7,211(0,3)
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Beispiel 1235: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,286(0,8);9,837(0,7);8,461 (5,5);8,442(5,8);8,228(3,1);8,209(3,6);7,988(2,5);7,968(4,9);7 ,949(2,8);7,862(0,3);7,829(4,6);7,809(3,6);7,255(0,9);7,245(0,9);5,985(0,6);5,972(1 ,2);5,959(1 ,2);5,946(1 ,4);5,942(0,9);5,933(0,8);5,929( 5,916(1 ,3);5,903(1 ,5);5,890(0,7);5,228(2,5);5,224(2,7);5,185^ 3); 7,866 (0.5); 7,844 (0.5); 7,825 (0.6); 7,785 (7.8); 7,766 (12.3); 7.746 (5.3) 7.643 (3.3 ); 7,552 (0.6); 7,533 (0.5); 7,211 (0.3)
Figure imgf000101_0001
Figure imgf000102_0001
Figure imgf000103_0001
Example 1235: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.286 (0.8); 9.837 (0.7); 8.461 (5.5); 8.442 (5.8); 8.228 ( 3.1), 8.209 (3.6), 7.988 (2.5), 7.968 (4.9), 7.949 (2.8), 7.862 (0.3), 7.829 (4.6), 7.809 (3.6); 7.255 (0.9); 7.245 (0.9); 5.985 (0.6); 5.972 (1, 2); 5.959 (1, 2); 5.946 (1, 4); 5.942 ( 5.933 (0.8); 5.929 (5.916 (1.3); 5.903 (1.5); 5.890 (0.7); 5.228 (2.5); 5.224 (2.7); 5.185) ^
;3,988(5,0);3,979(2,2);3,975(2,8);3,904(16,0);3,394(460,1);3,383(722,5);3,170(1 ,1);2,679(1 ,0);2,675(  3.988 (5.0), 3.979 (2.2), 3.975 (2.8), 3.904 (16.0), 3.394 (460.1), 3.383 (722.5), 3.170 (1, 1); 2,679 (1, 0); 2,675 (
2);2,501 (154,3);2,337(1 ,0);2,333(1 ,3);2,328(1 ,0);1 ,234(0,4);0,000(4,7)  2), 2,501 (154,3), 2,337 (1,0), 2,333 (1,3), 2,328 (1,0), 1,234 (0,4), 0,000 (4,7)
Beispiel 1242: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,175(1 ,4);9,638(0,8);8,439(5,7);8,420(6,0);8,221(2,7);8,202(3,2)7,988(2,6)7,968(5,2)7Example 1242: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.175 (1, 4), 9.638 (0.8), 8.439 (5.7), 8.420 (6.0), 8.221 ( 8.202 (3.2) 7.988 (2.6) 7.968 (5.2) 7; 2.7)
,948(2,9);7,828(4,5);7,808(3,4)7,234(0,9);7,222(0,9);4,043(0,5);4,025(1 ,2);4,007(1 ,5);3,990(1 ,2);3,973(0,5);3,904(13,7);3,350(563,9);3,267(0, 948 (2.9), 7.828 (4.5), 7.808 (3.4) 7.234 (0.9), 7.222 (0.9), 4.043 (0.5), 4.025 (1, 2), 4.007 (1, 5), 3.990 (1.2), 3.973 (0.5), 3.904 (13.7), 3.350 (563.9), 3.267 (0
,4);3,168(0,5);2,677(0,8);2,673(1 ,1);2,668(0,9);2,526(3,0);2,512(73,0);2,508(145,2);2,504(188,3);2,499(138,1);2,^ , 4); 3.168 (0.5); 2.677 (0.8); 2.673 (1, 1); 2.668 (0.9); 2.526 (3.0); 2.512 (73.0); 2.508 (145); 2); 2.504 (188.3); 2,499 (138.1); 2, ^
,2);2,326(0,9);1 ,513(0,8);1 ,504(1 ,0);1 ,497(1 ,5);1 ,488(2,6);1 ,471 (2,9);1 ,456(1 ,5);1 ,452(1 ,7);1 ,434(0,3);1 ,387(0,5);1 ,369(1 ,4);1 ,351(2,3);1 ,333( , 2); 2,326 (0.9); 1, 513 (0.8); 1, 504 (1, 0); 1, 497 (1, 5); 1, 488 (2.6); 1, 471 (2.9); 1, 456 (1, 5); 1, 452 (1, 7); 1, 434 (0.3); 1, 387 (0.5); 1, 369 (1, 4) 1, 351 (2, 3); 1, 333 (
2.7) ;1 ,315(2,1 );1 ,305(0,7);1 ,298(1 ,2);1 ,287(0,4);1 ,281 (0,4);1 ,234(0,4);1 ,166(13,4);1 ,149(13,4);0,911 (7,7);0,893(16,0);0,875(6,6);0,000(1 ,9) Beispiel 1256: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,207(2,9);9,823(1 ,8);8,451(13,0);8,432(13,7);8,254(0,4);8,228(6,9);8,209(8,0);7,988(5,9 )7,969(11 ,6)7,949(6,5);7,829(10,1);7,809(7,8);7,240(2,1)7,225(2,0);3,904(16,0);3,523(1 ,6);3,518(2,2);3,506(7,4);3^^^ 1, 315 (2.1); 1, 305 (0.7); 1, 298 (1, 2); 1, 287 (0.4); 1, 281 (0.4); 1, 234 (0.4); 1, 166 (13.4); 1, 149 (13.4); 0.911 (7.7); 0.883 (16.0); 0.875 (6.6); 0.000 (1, 9) Example 1256: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.207 (2.9); 9.823 (1, 8); 8.451 (13.0); 8.432 (13.7); 8.254 (0.4), 8.228 (6.9), 8.209 (8.0), 7.988 (5.9) 7.969 (11, 6) 7.949 (6.5), 7.829 (10.1), 7.809 (7 , 8), 7.240 (2.1) 7.225 (2.0), 3.904 (16.0), 3.523 (1.6), 3.518 (2.2), 3.506 (7.4), 3 ^^^
475(16,0);3,464(13,2);3,453(4,0);3,447(2,6);3,340(755,2);3,289(92,1);3,251 (0,4);3,168(0,4);3,111(0,5);2,677(1 ,8);2,672(2,4);2,668 (0,4);2,525(6,7);2,512(157,0);2,508(309,4);2,503(399,4);2,499(295,2);2,494(150,2);2,334(1 ,8);2,330(2,5) 475 (16.0), 3.464 (13.2), 3.453 (4.0), 3.447 (2.6), 3.340 (755.2), 3.289 (92.1), 3.251 (0.4), 3.168 (0.4); 3.111 (0.5); 2.677 (1, 8); 2.672 (2.4); 2.668 (0.4); 2.525 (6.7); 2.512 (157.0); 2.508 ( 2,509 (399.4); 2,499 (295,2); 2,494 (150,2); 2,334 (1, 8); 2,330 (2,5)
00(9,3)  00 (9.3)
Beispiel 1262: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,169(0,9);9,767(0,8);8,445(5,9);8,426(6,3);8,224(3,1);8,205(3,8);7,989(2,7);7,970(5,4)7 ,950(3,1);7,830(4,8);7,810(3,8);7,223(0,9);4,199(0,5);4,186(1 ,0);4,169(1 ,3);4,150(1 ,1);4,136(0,5);3,904(16,0);3,825(0,4);3,470 Example 1262: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.169 (0.9); 9.767 (0.8); 8.445 (5.9); 8.426 (6.3); 8.224 ( 3.1), 8.205 (3.8), 7.989 (2.7), 7.970 (5.4) 7, 950 (3.1), 7.830 (4.8), 7.810 (3.8), 7.223 ( 4.199 (0.5), 4.199 (0.5), 4.186 (1, 0), 4.169 (1.3), 4.150 (1, 1), 4.166 (0.5), 3.904 (16.0), 3.825 (0 , 4); 3,470
;3,418(2,0);3,406(3,8);3,394(4,1);3,369(7,6);3,347(551 ,3);3,296(41 ,8);3,168(0,5);3,118(0,3);2,677(1 ,0);2,6 3.348 (2.0), 3.406 (3.8), 3.394 (4.1), 3.369 (7.6), 3.347 (551, 3), 3.296 (41, 8), 3.168 (0.5); 3.118 (0.3), 2.677 (1.0), 2.6
(83,7);2,508(166,4);2,503(215,4);2,499(157,9);2,495(78,3);2,335(0,9);2,330(1 ,3);2,326(0,9);1 ^ (83.7); 2.508 (166.4); 2.503 (215.4); 2.499 (157.9); 2.495 (78.3); 2.335 (0.9); 2.330 (1, 3); 2.326 ( 0.9); 1 ^
Beispiel 1321 : 1H-NMR(601 ,6 MHz, de-DMSO): δ= 19,974(0,6);9,085(1 ,0);8,841(3,9);8,368(9,6);8,356(9,9);8,341(0,7);8,329(0,8);8,276(2,7);8 ,264(2,7);8,204(1 ,0);8,108(0,5);7,703(11 ,0)7,688(10,6)7,622(1 ,3);6,938(0,8);6,923(0,9);6,370(0,4);4,383(1 ,0);4,371 (1 ,0);3,324(865,7);3,172( 0,7);3,122(0,7);2,948(0,5);2,667(2,2);2,627(1 ,0);2,616(7,8);2,613(10,7);2,610(7,8);2,522(18,6);2,519(23,6);2^ Example 1321: 1 H-NMR (601.6 MHz, de-DMSO): δ = 19.974 (0.6); 9.085 (1.0); 8.841 (3.9); 8.368 (9.6); 8.356 ( 9.9), 8.341 (0.7), 8.329 (0.8), 8.276 (2.7), 8, 264 (2.7), 8.204 (1, 0), 8.108 (0.5), 7.703 (11, 0) 7.688 (10.6) 7.622 (1, 3), 6.938 (0.8), 6.923 (0.9), 6.370 (0.4), 4.383 (1, 0), 4.371 (1, 3.344 (865.7), 3.172 (0.7), 3.122 (0.7), 2.948 (0.5), 2.667 (2.2), 2.627 (1.0), 2.616 (7.8) 2.613 (10.7), 2.610 (7.8), 2.522 (18.6), 2.519 (23.6), 2 ^
82,3);2,501(1764,8);2,498(1284,2);2,495(592,5);2,394(4,7);2,389(7,9);2,386(10,6);2,383(7,6);1 ,908(16,0);1 ,354(1 ,1);t 82.3) 2.501 (1764.8) 2.498 (1284.2) 2.495 (592.5); 2,394 (4.7); 2,389 (7.9); 2,386 (10.6); 2.383 (7 , 6); 1, 908 (16,0); 1, 354 (1, 1); t
235(1 ,9);0,987(0,6);0,854(0,5);0,005(1 ,5);0,000(47,8);-0,006(1 ,6)  235 (1, 9), 0.987 (0.6), 0.854 (0.5), 0.005 (1, 5), 0.000 (47.8), - 0.006 (1, 6)
Beispiel 1431 : 1H-NMR(601 ,6 MHz, de-DMSO): δ= 12,936(0,7);9,354(0,4);9,170(3,3);9,024(1 ,2);8,498(2,8);8,488(2,8);8,419(15,3);8,407(16,0Example 1431: 1 H-NMR (601, 6 MHz, de-DMSO): δ = 12.936 (0.7); 9.354 (0.4); 9.170 (3.3); 9.024 (1, 2); 8.498 ( 2.8) 8.488 (2.8) 8.419 (15.3); 8,407 (16.0
);8,092(12,9);8,078(12,3);8,065(0,6)7,983(0,4)7,970(0,4)7,699(1 ,4)7,415(0,6)7,402(0,6);6,973(0,8);4,035(0,5);4,023(0,6);3,325(450,^8,092 (12.9), 8,078 (12.3), 8,065 (0.6) 7,983 (0.4) 7,970 (0.4) 7,699 (1,4) 7,415 (0.6) 7,402 (0, 6); 6.973 (0.8); 4,035 (0.5); 4,023 (0.6); 3,325 (450, ^
97(0,3);2,617(1 ,7);2,614(2,4);2,611(1 ,7);2,523(4^ 97 (0.3), 2.617 (1, 7), 2.614 (2.4), 2.611 (1, 7), 2.523 (4 ^
2,389(1 ,7);2,386(2,3);2,383(1 ,7);2,358(0,3);1 ,989(2,4);1 ,909(4,0);1 ,187(0,6);1 , 175(1 ,3);1 ,163(0,6);1 ,098(0,5);1 ,088(0,4);0,005(0,7);0,000(21 , 2.389 (1, 7); 2.386 (2.3); 2.383 (1, 7); 2.358 (0.3); 1, 989 (2.4); 1, 909 (4.0); 1, 187 ( 0.6); 1, 175 (1, 3); 1, 163 (0.6); 1, 098 (0.5); 1, 088 (0.4); 0.005 (0.7); 0.000 ( 21,
7);-0,006(0,7) 7) - 0.006 (0.7)
Beispiel 1432: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 12,980(0,6);9,626(0,5);9,165(2,5);8,495(1 ,6);8,481(1 ,7);8,404(6,1);8,391 (6,3);8,083(4,7);8Example 1432: 1 H-NMR (601.6 MHz, de-DMSO): δ = 12.980 (0.6), 9.626 (0.5), 9.165 (2.5), 8.495 (1, 6), 8.481 ( 1, 7); 8,404 (6,1); 8,391 (6,3); 8,083 (4,7); 8
,070(4,4);6,985(0,6);3,322(129,1);2,864(16,0);2,856(16,0);2,616(0,9);2,613(1 ,2);2,610(0,9);2,523(2,1);2,519(2,7);2 , 070 (4.4), 6.985 (0.6), 3.322 (129.1), 2.864 (16.0), 2.856 (16.0), 2.616 (0.9), 2.613 (1, 2); 2,610 (0.9); 2,523 (2.1); 2,519 (2.7); 2
4(136,9);2,501(188,5);2,499(138,7);2,496(65,7);2,389(0,9);2,386(1 ,2);2,383(0,9);1 ,909(1 ,5);0,005(0,4);0,000(12,4);-0,006(0,5)  4 (136.9); 2.501 (188.5); 2.499 (138.7); 2.496 (65.7); 2.389 (0.9); 2.386 (1, 2); 2.383 (0.9); 1 , 909 (1, 5), 0.005 (0.4), 0.000 (12.4), - 0.006 (0.5)
Beispiel 1435: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 9,154(1 ,4);8,483(0,8);8,470(0,9);8,398(2,8);8,385(2,9);8,086(2,3);8,072(2,1);4,082(0,6);4,Example 1435: 1 H-NMR (601, 6 MHz, de-DMSO): δ = 9.154 (1, 4), 8.483 (0.8), 8.470 (0.9), 8.398 (2.8), 8.385 ( 2.9); 8,086 (2.3); 8,072 (2.1); 4,082 (0.6); 4,
071(0,9);4,059(0,9);4,048(0,6);3,322(34,1);2,616(0,3);2,6^ 071 (0.9); 4,059 (0.9); 4,048 (0.6); 3,322 (34.1); 2,616 (0.3); 2.6 ^
9.8) ;2,499(50,9);2,496(23,9);2,386(0,4);1 ,909(0,9);1 ,193(16,0);1 ,182(16,0);0,000(2,1)  9.8); 2,499 (50.9); 2.496 (23.9); 2.386 (0.4); 1, 909 (0.9); 1, 193 (16.0); 1, 182 (16.0) ; 0,000 (2.1)
Beispiel 1462: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 12,933(0,4);9,693(0,4);9,152(2,1);8,481(1 ,3);8,467(1 ,4);8,401(4,8);8,389(5,1);8,090(4,0);8 ,077(3,8);6,969(0,5);5,431(0,3);5,417(0,3);4,036(0,5);4,024(1 ,1);4,012(1 ,5);4,001(1 ,1);3,989(0,5);3,322(60,3);2,617(0,5);2,6 Example 1462: 1 H-NMR (601, 6 MHz, de-DMSO): δ = 12.933 (0.4), 9.693 (0.4), 9.152 (2.1), 8.481 (1.3), 8.467 ( 1, 4), 8.401 (4.8), 8.389 (5.1), 8.090 (4.0), 8.077 (3.8), 6.969 (0.5), 5.431 (0.3), 5.417 (0.3), 4.036 (0.5), 4.024 (1, 1), 4.012 (1.5), 4.001 (1, 1), 3.989 (0.5), 3.322 (60.3), 2.617 ( 0.5), 2.6
;2,523(1 ,3);2,520(1 ,6);2,517(1 ,6);2,508(40,0);2,505(85,0);2,502(115,7);2,499(84,8);2,496(39,5);2,389(0,5);2,386(0,7);2,383(0,5);1 ,909(1 ,2);1 , 502(0,9);1 ,492(1 ,5);1 ,486(1 ,5);1 ,482(2,0);1 ,479(2,1 );1 ,475(1 ,8);1 ,472(1 ,8);1 ,469(2,0);1 ,464(1 ,2);1 ,458(1 , 3);1 ,446(0,4);1 ,375(0,5);1 , 363(1 ,2);1 ,351(1 ,5);1 ,347(1 ,2);1 ,338(1 ,4);1 ,335(1 ,6);1 ,331(1 ,0);1 ,323(1 ,3);1 ,319(1 ,2);1 ,308(1 ,0);1 ,300(0,5);1 ,297(0,5);1 ,286(0,4);1 ,277(0,6);1 , 266(0,6); 1 ,251(0,5);1 ,163(13,3);1 ,152(13,3);0,976(2,5);0,965(2,5);0,906(7,5);0,894(16,0);0,882(7,0);0,862(0,8);0^ 2.523 (1, 3); 2.520 (1, 6); 2.517 (1, 6); 2.508 (40.0); 2.555 (85.0); 2.502 (115.7); 2.499 (84.8); 2.496 (39.5); 2.389 (0.5); 2.386 (0.7); 2.383 (0.5); 1, 909 (1, 2); 1, 502 (0.9); 1, 492 ( 1, 5); 1, 486 (1, 5); 1, 482 (2.0); 1, 479 (2.1); 1, 475 (1, 8); 1, 472 (1, 8); 1, 469 (2,0), 1,464 (1,2), 1,458 (1,3), 1,446 (0,4), 1,375 (0,5), 1,363 (1 , 2); 1, 351 (1, 5); 1, 347 (1, 2); 1, 338 (1, 4); 1, 335 (1, 6); 1, 331 (1, 0); 1 , 323 (1, 3); 1, 319 (1, 2); 1, 308 (1, 0); 1, 300 (0.5); 1, 297 (0.5); 1, 286 (0, 4); 1, 277 (0.6); 1, 266 (0.6); 1, 251 (0.5); 1, 163 (13.3); 1, 152 (13.3); 0.976 (2.5); 0.965 (2.5); 0.906 (7.5); 0.894 ( 16.0), 0.882 (7.0), 0.862 (0.8), 0 ^
7,5) 7,5)
Beispiel 1476: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 12,953(1 ,7 );9,851(1 ,2);9,158(5,9);8,487(3,6);8,475(3,8);8,416(15,2);8,404(16,0);8,092(10, 3);8,079(9,6);6,976(1 ,5);3,515(2,7);3,506(9,2);3,497(12,5);3,489(7,1);3,471(12,9);3,463(15,0);3,455(4,7);3,452(4,2);3,404(0,6);3,322(184,2);3 ,289(115,8);3,170(0,6);2,616(1 ,3);2,613(1 ,8);2,610(1 ,3);2,523 (3,9);2,520(5,4);2,516(6,2);2,508(101 ,1);2,505(209,4);2,502(283,9);2,499(204,9 );2,496(95,4);2,389(1 ,3);2,386(1 ,8);2,383(1 ,3);1 ,909(2,3);0,005(0,8);0,000(22,1);-0,006(0,7) Example 1476: 1 H-NMR (601.6 MHz, de-DMSO): δ = 12.953 (1, 7), 9.851 (1.2), 9.158 (5.9), 8.487 (3.6), 8.475 ( 3.8), 8.416 (15.2), 8.404 (16.0), 8.092 (10, 3), 8.079 (9.6), 6.976 (1.5), 3.515 (2.7), 3.506 (9 , 2), 3,497 (12.5); 3,489 (7.1); 3,471 (12.9); 3,463 (15.0); 3,455 (4.7); 3,452 (4.2); 3,404 (0, 6), 3,322 (184,2), 3,289 (115,8), 3,170 (0,6), 2,616 (1,3), 2,613 (1,8), 2,610 (1,3), 2,523 (3 , 9), 2.520 (5.4), 2.516 (6.2), 2.508 (101, 1), 2.505 (209.4), 2.502 (283.9), 2.499 (204.9), 2.496 (95, 4); 2.389 (1, 3); 2.386 (1, 8); 2.383 (1, 3); 1, 909 (2, 3); 0.005 (0.8); 0.000 (22.1); - 0.006 ( 0,7)
Beispiel 1535: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 9,214(0,7) 8,509(0,8);8,059(4,6);8,045(4,3)7,673(1 ,1);7,662(1 ,1);3,322(128,4);2,969(15,8 );2,883(16,0);2,616(0,7);2,613(1 ,0);2,610(0,7);2,523(1 ,6);2,520(2,0);2,516(2,0);2,508(54,3);2,505(114,9);2,502(155,9);2,499(114,1);2,496(52, 9);2,389(0,7);2,386(1 ,0);2,383(0,7);1 ,909(1 ,2);0,005(0,3);0,000(11 ,1);-0,006(0,4) Example 1535: 1 H-NMR (601, 6 MHz, de-DMSO): δ = 9.214 (0.7) 8,509 (0.8); 8,059 (4,6); 8,045 (4.3) 7,673 (1, 1), 7.662 (1, 1), 3.322 (128.4), 2.969 (15.8), 2.883 (16.0), 2.616 (0.7), 2.613 (1.0), 2.610 (0.7 2.523 (1, 6), 2.520 (2.0), 2.516 (2.0), 2.508 (54.3), 2.505 (114.9), 2.502 (155.9), 2.499 (114.1) 2.496 (52, 9), 2.389 (0.7), 2.386 (1, 0), 2.383 (0.7), 1.909 (1, 2), 0.005 (0.3), 0.000 (11, 1 ) - 0.006 (0.4)
Beispiel 1538: 1H-NMR(601 ,6 MHz, de-DMSO): δ= 9,220(1 ,7) 8,509(1 ,6);8,052(7,9);8,038(7,4)7,637(2,1)7,626(2,1);3,440(2,2);3,428(6,2);3, 417(6,3);3,405(2,2);3,351(0,3);3,323(207,4);3,203(2,1);3,191( 5,9);3, 180(5,9);3, 168(2 , 1 );2,617(1 , 1 );2,614(1 ,4);2 ,611 (1 ,0);2,523(2,8);2,520(3,8 );2,517(4,5);2,508(80,3);2,505(167,6);2,502(229,0);2,499(165 9);2,496(76,4);2,389(1 ,0);2,386(1 ,4);2,383(1 ,0);1 , 909(1 ,9);1 , 172(1 , 1);1 , 160(2,4 );1 ,145(8,0);1 ,134(16,0);1 ,122(7,7);1 ,065(7,2);1 ,053(14,3);1 ,041(6,9);0,005(0,7);0,000(18,8);-0,006(0,6) Example 1538: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.220 (1, 7) 8.509 (1, 6), 8.052 (7.9), 8.038 (7.4) 7.637 (2, 1) 7.626 (2.1), 3.440 (2.2), 3.428 (6.2), 3.417 (6.3), 3.405 (2.2), 3.351 (0.3), 3.323 (207, 4); 3.203 (2.1); 3.191 (5.9); 3, 180 (5.9); 3, 168 (2, 1); 2.617 (1, 1); 2.614 (1, 4); 2 , 611 (1, 0), 2.523 (2.8), 2.520 (3.8), 2.517 (4.5), 2.508 (80.3), 2.505 (167.6), 2.502 (229.0); 2,499 (165 9); 2,496 (76,4); 2,389 (1,0); 2,386 (1,4); 2,383 (1,0); 1,909 (1,9); 1,172 (1,1) 1, 160 (2.4); 1, 145 (8.0); 1, 134 (16.0); 1, 122 (7.7); 1, 065 (7.2); 1, 053 (14.3); 1, 041 (6.9); 0.005 (0.7); 0.000 (18.8); - 0.006 (0.6)
Beispiel 1541 : 1H-NMR(400,0 MHz, de-DMSO): δ= 12,271(1 ,0 );9,730(0,7);9,716(1 ,2);9,703(0,7);8,269(5,4);8,250(5,7);6,406(1 ,8);6,403(1 ,8);6 ,387(1 ,8);6,384(1 ,8);3,489(1 ,0);3,468(1 ,5);3,446(1 ,0);3,305(3i S,7);3,269(2,0);3,252(3,7);3,237(3,6);3,220(2,0);2,670(0,5);2,523(1 ,4);2,519(2,0) ;2,510(28,3);2,505(61 ,4);2,501(86,1);2,496(60,9);2,492(27,5); 2,328(0,5);2,293(0,6);2,279(1 ,0);2,272(1 ,8);2,264(1 ,1);2,256(1 ,2);2,250(2,3);2,2 43(1 ,5);2,235(0,7);2,229(1 ,0);2,222(0,8);2,203(0,5);2,179(1 ,9) ;2,173(1 ,3);2,156(2,6);2,150(2,2);2,133(1 ,6);2,127(1 ,6);1 ,992(0,8);1 ,988(0,7);1 , 967(1 ,1);1 ,965(1 ,1);1 ,943(1 ,4);1 ,920(0,8);1 ,807(0,9);1 ,805(0,i ));1 ,800(0,7);1 ,785(0,7);1 ,781(0,7);1 ,778(0,7);1 ,526(2,1);1 ,508(3,9);1 ,490(3,9);1 ,472(2,3);1 ,454(0,5);0,906(7,5);0,887(16,0);0,869(6,6);0,008(C ),9);0,000(30,5);-0,009(0,9) Example 1541: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.271 (1, 0), 9.730 (0.7), 9.716 (1.2), 9.703 (0.7), 8.269 ( 5,4), 8,250 (5,7), 6,406 (1, 8), 6,403 (1, 8), 6, 387 (1, 8), 6,384 (1, 8), 3,489 (1, 0), 3,468 (1, 5); 3.346 (1, 0); 3.305 (3i S, 7); 3.269 (2.0); 3.252 (3.7); 3.237 (3.6); 3.220 (2.0); 2.670 (0.5); 2.523 (1, 4), 2.519 (2.0), 2.510 (28.3), 2.505 (61, 4), 2.501 (86.1), 2.496 (60.9), 2.492 ( 27.5); 2.238 (0.5), 2.293 (0.6), 2.279 (1, 0), 2.272 (1, 8), 2.264 (1, 1), 2.256 (1, 2), 2.250 (2.3), 2 , 2 43 (1, 5), 2.235 (0.7), 2.229 (1, 0), 2.222 (0.8), 2.203 (0.5), 2.179 (1, 9), 2.173 (1, 3) 2.156 (2.6); 2.125 (2.2); 2.133 (1, 6); 2.127 (1, 6); 1, 992 (0.8); 1, 988 (0.7); 1, 967 (1, 1); 1, 965 (1, 1); 1, 943 (1, 4); 1, 920 (0.8); 1, 807 (0.9); 1, 805 (0, i) 1, 800 (0.7), 1, 785 (0.7), 1, 781 (0.7), 1, 778 (0.7), 1, 526 (2,1), 1, 508 (3.9); 1, 490 (3.9); 1, 472 (2.3); 1, 454 (0.5); 0.906 (7.5); 0.887 (16.0); 0.869 (6 , 6), 0.008 (C), 9), 0.000 (30.5), - 0.009 (0.9)
Beispiel 1542: 1H-NMR(400,0 MHz, de-DMSO): δ= 5,652(0,5);3,306(3,4);3,001(0,8);2,986(1 ,2);2,983(1 ,1);2,969(1 ,1);2,965(1 ,2);2,951(0,8);2,Example 1542: 1 H-NMR (400.0 MHz, de-DMSO): δ = 5.652 (0.5); 3.306 (3.4); 3.001 (0.8); 2.986 (1.2); 2.983 ( 1, 1); 2.969 (1, 1); 2.965 (1, 2); 2.951 (0.8); 2,
510(3,0);2,506(6,6);2,501(9,2);2,496(6,4);2,492(2,8);1 ,565(0,7);1 ,548(0,8);1 ,532(0,7);1 ,263(1 ,0);1 ,245(1 ,8);1 ,227(1 ,8);1 ,210 510 (3.0), 2.506 (6.6), 2.501 (9.2), 2.496 (6.4), 2.492 (2.8), 1, 565 (0.7), 1, 548 (0, 8); 1, 532 (0.7); 1, 263 (1, 0); 1, 245 (1, 8); 1, 227 (1, 8); 1, 210
,887(2,8);0,862(16,0);0,846(15,2);0,000(3,8)  , 887 (2.8); 0.862 (16.0); 0.846 (15.2); 0,000 (3.8)
Beispiel 1543: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,732(2,8);7,393(2,5);7,375(3,1);7,366(3,1);7,349(2,8);6,113(2,6);3,390(5,9);3,372(7,2);3Example 1543: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 732 (2.8), 7.393 (2.5), 7.375 (3.1), 7.366 (3.1); 7,349 (2.8); 6,113 (2.6); 3,390 (5.9); 3,372 (7.2); 3
|,319(128,2);3,172(1 ,6);3,155(3,8);3,138(3,8);3,120(1 ,4);2,870(16,0);2,804(14,5);2,667(3,3);2,500(393,1);2,375(1 ,3);2,327(2,7);2,232(4,3);2
Figure imgf000105_0001
Figure imgf000106_0001
151(1 ,0);7,137(1 ,3);7,131(0,9);7,063(0,9);7,055(0,7);7,046(1 ,4);7,037(1 ,0);7,027(0,7);7,018(0,5);6,360(0,6);4,204(3,8);4,123(3,0);3,819(14,3);3,172 (1,6), 3,155 (3,8), 3,138 (3,8), 3,120 (1, 4), 2,870 (16,0), 2,804 (14,5) 2,667 (3,3), 2,500 (393,1), 2,375 (1,3), 2,327 (2,7), 2,232 (4,3), 2
Figure imgf000105_0001
Figure imgf000106_0001
151 (1, 0), 7,137 (1,3), 7,131 (0,9), 7,063 (0,9), 7,055 (0,7), 7,046 (1, 4), 7,037 (1, 0), 7,027 (0.7); 7,018 (0.5); 6,360 (0.6); 4,204 (3.8); 4,123 (3.0); 3,819 (14.3);
3,811(9,5);3,687(14,4);3,615(9,8);3,466(16,0);2,979(8,4);2,966(14,3);2,674(0,9);2,669(1 ,2);2,665(0,8);2,523(3,1);2,518(4,6);2 3,811 (9.5); 3,687 (14.4); 3,615 (9.8); 3,466 (16.0); 2,979 (8.4); 2,966 (14.3); 2,674 (0.9); 2,669 (1,2), 2,665 (0,8), 2,523 (3,1), 2,518 (4,6), 2
5(152,8);2,500(216,3);2,496(150,3);2,491(66,1);2,456(1 ,2);2,451(1 ,1);2,332(0,9);2,327(1 ,3);2,0  5 (152.8), 2.500 (216.3), 2.496 (150.3), 2.491 (66.1), 2.456 (1, 2), 2.451 (1, 1), 2.322 (0.9), 2.327 (1, 3), 2.0
Beispiel 1576: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,851(0,5);7,542(3,3);7,524(3,4);7,479(0,7);7,475(0,8);7,461(0,9);7,458(1 ,0);7,456(1 ,1);7Example 1576: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 851 (0.5); 7.542 (3.3); 7.524 (3.4); 7.499 (0.7); 7.475 (0.8); 7.461 (0.9); 7.458 (1, 0); 7.456 (1, 1); 7
,454(1 ,1);7,440(0,9);7,435(1 ,0);7,400(0,7);7,381(0,8);7,151 (1 ,6);7,132(1 ,4);7,058(1 ,0);7,055(1 ,0);7,039(1 ,8);7,036(1 ,7);7,020(0,9);7,018(0,8);, 454 (1, 1); 7,440 (0.9); 7,435 (1, 0); 7,400 (0.7); 7,381 (0.8); 7,151 (1, 6); 7,132 (1, 4); 7.058 (1.0), 7.055 (1.0), 7.039 (1.8), 7.036 (1.7), 7.020 (0.9), 7.018 (0.8);
3,815(16,0);3,424(0,9);3,407(2,1);3,391(1 ,0);3,372(1 ,0);3,356(2,3);3,340(1 ,0);3,310(13,8);3,256(0,8);3 3.815 (16.0), 3.424 (0.9), 3.407 (2.1), 3.391 (1, 0), 3.372 (1.0), 3.356 (2.3), 3.340 (1.0), 3.310 (13.8) 3,256 (0.8); 3
,8);3,101(0,8);2,523(1 ,3);2,518(1 ,9);2,509(24,5);2,505(52,9);2,500(74,0);2,495(51 ,6);2,491(23,^  , 8), 3,101 (0,8), 2,523 (1,3), 2,518 (1, 9), 2,509 (24,5), 2,505 (52,9), 2,500 (74,0), 2,495 (51, 6); 2,491 (23, ^
1 ,838(4,5);1 ,832(2,6);1 ,821 (2,4);1 ,805(0,7);1 ,756(0,8);1 ,746(0,6);1 ,739(2,2);1 ,732(0,6);1 ,722(0,7);0,000(15,3)  1, 838 (4.5); 1, 832 (2.6); 1, 821 (2.4); 1, 805 (0.7); 1, 756 (0.8); 1, 746 (0 , 6); 1, 739 (2.2); 1, 732 (0.6); 1, 722 (0.7); 0.000 (15.3)
Beispiel 1577: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,798(0, 7);7,484(2,5);7,475(0,8);7,470(1 ,0);7,467(2,7);7,456(0,9);7,452(1 ,1);7,450(1 ,0);7 ,435(0,8);7,431(1 ,0);7,402(0,5);7,383(0,6);7,148(1 ,7);7,129(1 ,4);7,054(1 ,0);7,052(1 ,0);7,035(1 ,8);7,033(1 ,7);7,017(0,9);7,014(0,8);3,815(16,0) ;3,542(1 ,1);3,304(60,0);3,245(0,9);3,231(1 ,2);2,674(0,7);2,669(1 ,0);2,664(0,7);2,523(3,0);2,518(4,2);2,509(55,3);2,505(120,4);2,500(168,7);2, 495(118,1);2,491(53,6);2,331(0,7);2,327(1 ,0);2,322(0,7);1 ,602(0,9);1 ,590(1 ,0);1 ,511(1 ,7);0,008(1 ,0);0,000(34,3);-0,009(1 ,1) Example 1577: 1 H NMR (400.0 MHz, de-DMSO): δ = 11, 798 (0, 7); 7.484 (2.5); 7.475 (0.8); 7.470 (1.0); 7.467 (2.7); 7.456 (0.9); 7.452 (1, 1); 7.450 (1, 0); 7, 435 (0.8); 7.431 (1, 0); 7.402 (0.5) 7,383 (0,6); 7,148 (1, 7); 7,129 (1, 4); 7,054 (1, 0); 7,052 (1, 0); 7,035 (1, 8); 7,033 (1, 7); 7.017 (0.9), 7.014 (0.8), 3.815 (16.0), 3.542 (1, 1), 3.304 (60.0), 3.245 (0.9), 3.231 (1, 2), 2.674 (0.7), 2.669 (1.0), 2.664 (0.7), 2.523 (3.0), 2.518 (4.2), 2.509 (55.3), 2.505 (120.4), 2.500 ( 168.7); 2.495 (118.1); 2.491 (53.6); 2.331 (0.7); 2.327 (1.0); 2.322 (0.7); 1.602 (0.9) ; 1, 590 (1, 0); 1, 511 (1, 7); 0.008 (1, 0); 0.000 (34.3); - 0.009 (1, 1)
Beispiel 1578: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,867(0, 7);7,562(2,9);7,544(3,1);7,481(0,7);7,477(0,8);7,458(1 ,2);7,456(1 ,1);7,442(0,8);7 ,438(0,9);7,398(0,6);7,380(0,6);7,153(1 ,7);7,134(1 ,5);7,059(1 ,1);7,056(1 ,0);7,040(1 ,9);7,037(1 ,8);7,021 (0,9);7,019(0,9);3,814(16,0);3,768(1 ,0) 7W ηνί Ί Ί,Ι^ ηνί ROR Q T ^SQH η τ ΎΠΙΑΑ -^ 9R Ij AY^ 1RQM IV} 1fWf) 7V9 R7AI0 RV9 fifiQM 1V9 RRAIO RV9 <ϊ99Π ^ 9 RExample 1578: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 867 (0, 7), 7.562 (2.9), 7.544 (3.1), 7.481 (0.7); 7.477 (0.8), 7.458 (1, 2), 7.456 (1, 1), 7.442 (0.8), 7, 438 (0.9), 7.398 (0.6), 7.380 (0.6) 7,153 (1, 7); 7,134 (1, 5); 7,059 (1, 1); 7,056 (1, 0); 7,040 (1, 9); 7,037 (1, 8); 7,021 (0,9); 7,019 (0,9); 3,814 (16,0); 3,768 (1, 0) 7W ηνί Ί Ί, Ι ^ ηνί ROR QT ^ SQH η τ ΎΠΙΑΑ - ^ 9R Ij AY ^ 1RQM IV} 1fWf) 7V9 R7AI0 RV9 fifiQM 1V9 RRAIO RV9 <ϊ99Π ^ 9 R
8);2,509(58,2);2,505(124,6);2,500(173,2);2,495(121 ,8);2,491 (55,7);2,331(0,7);2,327(1 ,0);2,322(0,7);1 ,163(0,6);0,008(0,9);0,000(31 ,4);- 0,009(1 ,1) 8); 2,509 (58,2); 2,505 (124,6); 2,500 (173,2); 2,495 (121,8); 2,491 (55,7); 2,331 (0,7); 2,327 (1,0) 2,322 (0,7); 1, 163 (0,6); 0,008 (0,9); 0,000 (31, 4); - 0,009 (1, 1)
Beispiel 1579: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,543(1 ,3);7,525(1 ,3);7,466(0,5);7,465(0,6);7,462(0,6);7,438(0,7);7,420(0,7);7,158(0,7);7, 137(0,6);7,045(0,7);7,043(0,7);3,818(5,7);3,808(2,8);3,661(6,6);3,551(0,5);3,487(3,0);3,318(2,1);3,104(0,5);3,098(0,5);2,509(6,3);2,^ 2,500(19,2);2,496(13,4);2,491 (6,1);2,085(16,0);1 ,899(0,5);1 ,890(0,6);1 ,879(0,6);1 ,195(1 ,3);1 ,176(2,8);1 ,158(1 ,3);0,000(3,8) Example 1579: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.543 (1.3), 7.525 (1.3), 7.466 (0.5), 7.465 (0.6), 7.462 ( 7.438 (0.7); 7.720 (0.7); 7.158 (0.7); 7, 137 (0.6); 7.045 (0.7); 7.043 (0.7); 3.818) (5.7); 3,808 (2.8); 3,661 (6.6); 3,551 (0.5); 3,487 (3.0); 3,318 (2.1); 3,104 (0.5); 3,098 ( 0.5), 2.509 (6.3), 2, 2.500 (19.2), 2.496 (13.4), 2.491 (6.1), 2.085 (16.0), 1.899 (0.5 1, 890 (0.6), 1, 879 (0.6), 1, 195 (1, 3), 1, 176 (2.8), 1, 158 (1, 3), 0.000 (3 ,8th)
Beispiel 1580: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,876(0, 3);7,480(3,0);7,472(3,1);7,461(3,8);7,454(3,7);7,444(1 ,1);7,440(1 ,6);7,395(1 ,2);7 ,156(2,3);7,136(1 ,9);7,060(1 ,1);7,055(0,8);7,041(2,0);7,036(1 ,3);7,022(1 ,0);6,357(0,6);5,203(1 ,0);5,190(0,9);4,359(0,7);4,196(1 ,1);4,179(3,7);Example 1580: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 876 (0, 3), 7.480 (3.0), 7.472 (3.1), 7.461 (3.8); 7,454 (3,7); 7,444 (1, 1); 7,440 (1, 6); 7,395 (1, 2); 7,156 (2,3); 7,136 (1,9); 7,060 (1, 1) 7.055 (0.8), 7.041 (2.0), 7.036 (1, 3), 7.022 (1, 0), 6.357 (0.6), 5.203 (1, 0), 5.190 (0.9); 4.359 (0.7), 4.196 (1, 1), 4.179 (3.7);
A 1fi" 4 f)V 14^1 ςΥ4 1W1 9V4 11RM RV4 1f)1M IV? R9DC 1fi fl ? R19iQ -^ ARQIft RV? 4f)' 9fi R ? 14f)if) RV9 ( AICi 7V9 RRQM 1V9 fififiinA 1fi "4 f) V 14 ^ 1 ςΥ4 1W1 9V4 11RM RV4 1f) 1M IV? R9DC 1fi fl? R19iQ - ^ ARQIft RV? 4f) '9 f i R? 14f) if) RV9 (AICi 7V9 RRQM 1V9 fifi f iin
,8);2,523(2,9);2,518(4,2);2,509(60,7);2,505(132,9);2,500(186 ,5);2,496(129,9);2,491(58,1);2,332(0,8);2,327(1 ,1);2,322(0,8);2,174(0,6);2,145(0 ,6);2,085(16,0);2,072(0,6);1 ,704(1 ,3);1 ,676(1 ,6);1 ,566(0,7);1 307(0,5);1 ,273(0,7);1 ,254(4,8);1 ,236(10,0);1 ,218(4,5);1 ,198(2,6);1 ,180(5,1);1 ,16 2(2,4);0,008(0,6);0,000(20,6);-0,009(0,6) , 8), 2.523 (2.9), 2.518 (4.2), 2.509 (60.7), 2.505 (132.9), 2.500 (186, 5), 2.496 (129.9), 2.491 (58, 1), 2,332 (0.8), 2,327 (1,1), 2,322 (0,8), 2,174 (0,6), 2,145 (0, 6), 2,085 (16,0), 2,072 (0,6 1, 704 (1, 3); 1, 676 (1, 6); 1, 566 (0.7); 1 307 (0.5); 1, 273 (0.7); 1, 254 ( 1, 236 (10.0); 1, 218 (4.5); 1, 198 (2.6); 1, 180 (5.1); 1, 16 2 (2.4) 0.008 (0.6); 0,000 (20.6) - 0.009 (0.6)
Beispiel 1581 : 1H-NMR(400,0 MHz, de-DMSO): δ= 12,774(1 ,8);9,750(1 ,4);8,385(6,3);8,367(6,5);7,825(3,4);7,823(5,8);7,820(3,5);7,582(13,4); 7,579(13,4);6,529(1 ,7);6,511(1 ,7);3,365(0,7);3,348(1 ,1);3,336(1 ,7);3,313(183,4);3,292(4,8);3,285(1 ,2);3,278(4,5);3,260(2^ Example 1581: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.774 (1, 8); 9.750 (1, 4); 8.385 (6.3); 8.367 (6.5); 7.825 ( 3.4); 7,823 (5.8); 7,820 (3.5); 7,582 (13.4); 7.559 (13.4), 6.529 (1, 7), 6.511 (1, 7), 3.365 (0.7), 3.348 (1, 1), 3.336 (1, 7), 3.313 (183.4), 3.292 (4.8); 3.285 (1, 2); 3.288 (4.5); 3.260 (2 ^
0,8);2,666(0,5);2,546(1 ,0);2,510(41 ,9);2,505(85,8);2,501(117,2);2,496(84,6);2,492(40,1);2,332(0,5);2,328(0,7);2,323(0,5);1 ,555(2,^ 4);1 ,519(4,5);1 ,501 (2,4);1 ,483(0,6);0,928(7,8);0,909(16,0);0,891(6,8);0,000(6,1) 0.8), 2.666 (0.5), 2.546 (1, 0), 2.510 (41, 9), 2.505 (85.8), 2.501 (117.2), 2.496 (84.6), 2.492 (40 , 1); 2,332 (0,5); 2,328 (0,7); 2,323 (0,5); 1, 555 (2, ^ 4); 1, 519 (4,5); 1, 501 (2, 4), 1, 483 (0.6), 0.928 (7.8), 0.909 (16.0), 0.881 (6.8), 0.000 (6.1)
Beispiel 1582: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,757(0,9);9,714(0,6);8,380(3,0);8,362(3,1);7,825(1 ,6);7,823(2,8);7,820(1 ,7);7,581(5,9);7 ,579(6,3);6,527(0,8);6,508(0,8);3,367(0,8);3,360(0,6);3,350(1 ,9);3,333(2,2);3,311(85,5);2,523(1 ,6);2,510(18,6);2,505(38,3);2,501(52,4);2,496 37,7);2,492(17,9);1 ,641 (0,7);1 ,624(0,9);1 ,608(0,8);1 ,442(1 ,0);1 ,424(2,2);1 ,406(2,2);1 ,389(0,8);0,919(16,0);0,902(15,2);0,000(2,9)Example 1582: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.757 (0.9), 9.714 (0.6), 8.380 (3.0), 8.362 (3.1), 7.825 ( 1, 6), 7.823 (2.8), 7.820 (1, 7), 7.581 (5.9), 7.579 (6.3), 6.527 (0.8), 6.508 (0.8), 3.367 (0.8), 3.360 (0.6), 3.350 (1.9), 3.333 (2.2), 3.311 (85.5), 2.523 (1.6), 2.510 (18.6), 2.555 ( 38.3); 2.501 (52.4); 2.496 37.7); 2.492 (17.9); 1.641 (0.7); 1.624 (0.9); 1.608 (0.8 1, 442 (1, 0), 1, 424 (2.2), 1, 406 (2.2), 1.389 (0.8), 0.919 (16.0), 0.902 (15.2 ); 0,000 (2.9)
Beispiel 1584: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,160(0, 7);7,784(6,5);7,781(6,1);7,575(1 ,3);7,553(16,0);7,549(9,7);7,532(0,9);7,528(1 ,3); 7,506(3,2);7,489(3,0);3,430(1 ,8);3,412(5,5);3,395(5,8);3,376( 2,9);3,320(188, 1 );3,273(3, 1 );3,217(2,0);3,200(5,1 );3, 182(5 ,2);3, 164(1 ,7);2,674(0Example 1584: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.160 (0, 7); 7.784 (6.5); 7.781 (6.1); 7.575 (1.3); 16.0), 7.549 (9.7), 7.532 (0.9), 7.528 (1, 3); 7.506 (3.2); 7.489 (3.0); 3,430 (1, 8); 3,412 (5.5); 3,395 (5,8); 3,376 (2,9); 3,320 (188,1); 3,273 (3, 1); 3,217 (2,0); 3,200 (5,1); 3, 182 (5, 2); 3, 164 (1, 7); 2,674 (0
RV9 R7f) 9V9 fifWf) RV9 <ϊβ1Μ 4V9 "WM 1 9 W)tf\ RV9 <ϊ mA 4V9 ιR^fi RV9 ιfVfil 7V9 'liWn ι i 1 ιV9 ^fllMRfi 9V9 iQR ^T RV9 AQM ι R^RV9 R7f) 9V9 fifWf) RV9 <ϊβ1Μ 4V9 "WM 1 9 W) tf \ RV9 <ϊ mA 4V9 ιR ^ fi RV9 ιfVfil 7V9 'liWn ι i 1 VV9 ^ fllMrfi 9V9 iQR ^ T RV9 AQM ι R ^
,2);2,461(2,2);2,456(2,4);2,452(2,0);2,332(0,8);2,327(1 ,2);2,3 23(0,8);1 ,134(6,6);1 ,117(14,1);1 ,099(6,7);1 ,081(6,4);1 ,064(13,2);1 ,046(5,8);0,00 0(10,8) , 2), 2,461 (2,2), 2,456 (2,4), 2,452 (2,0), 2,332 (0.8), 2,327 (1,2), 2,3,23 (0,8), 1 , 134 (6,6); 1,117 (14,1); 1, 099 (6,7); 1, 081 (6,4); 1, 064 (13,2); 1, 046 (5, 8); 0.00 0 (10.8)
Beispiel 1585: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,302(0,5);7,795(2,9);7,792(2,1);7,786(2,0);7,564(7,0);7,550(4,9);7,547(4,5);7,515(0,9);7 ,497(1 ,0);4,215(4,5);4,113(3,4);3,689(16,0);3,611(10,5);3,373(2,3);3,325(223,2);3,271(1 ,3);2,987(8,1);2,957(14,1);2,674^ Example 1585: 1 H NMR (400.0 MHz, de-DMSO): δ = 12,302 (0.5), 7.795 (2.9), 7.792 (2.1), 7.786 (2.0), 7.564 ( 7.0), 7.550 (4.9), 7.547 (4.5), 7.515 (0.9), 7, 497 (1, 0), 4.215 (4.5), 4.113 (3.4), 3.689 (16.0); 3,611 (10.5); 3,373 (2,3); 3,325 (223,2); 3,271 (1, 3); 2,987 (8,1); 2,957 (14.1); 2,674 ^
5(0,9);2,554(0,8);2,550(1 ,8);2,545(2,1);2,540(2,2);2,523(5,7);2^ 5 (0.9), 2.554 (0.8), 2.550 (1.8), 2.545 (2.1), 2.540 (2.2), 2.523 (5.7), 2 ^
9(0,6);2,444(0,8);2,440(0,7);2,332(0,9);2,327(1 ,2);2,323(0,9);0,000(7,2) 9 (0.6), 2.444 (0.8), 2.440 (0.7), 2.332 (0.9), 2.327 (1.2), 2.323 (0.9), 0.000 (7.2)
Beispiel 1590: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,792(4,2 ;7,788(4,8);7,586(1 ,0);7,576(0,8);7,565(8,8);7,559(7,6);7,556(7,1);7,551(3,4);7, 543(0,7);7,539(0,9);7,530(0,6);7,522(3,4);7,510(2,5);7,504(3 6);7,493(2,3);6,386(0,8);5,218(1 ,7);5,206(1 ,5);4,436(0,6);4,402(0,6);4,334(1 ,0);4 ,323(1 ,0);4,199(1 ,8);4,181(5,9);4,163(6,4);4,153(1 ,0);4,145(2 ,8);4,136(1 ,9);4,124(2,1);4,118(1 ,9);4,106(1 ,7);4,100(0,8);4,088(0,5);3,430(17,4)Example 1590: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.792 (4.2, 7.788 (4.8); 7.586 (1.0); 7.576 (0.8); 7.565 (8 , 8); 7,559 (7.6); 7,556 (7,1); 7,551 (3,4); 7,543 (0,7); 7,539 (0.9); 7,530 (0,6); 7,522 ( 3.4), 7.510 (2.5), 7.504 (36), 7.493 (2.3), 6.386 (0.8), 5.218 (1, 7), 5.206 (1, 5), 4.436 (0, 4,402 (0,6); 4,334 (1, 0); 4,323 (1, 0); 4,199 (1, 8); 4,181 (5,9); 4,163 (6,4); 4,153 (1 4,145 (2, 8), 4,136 (1, 9), 4,124 (2,1), 4,118 (1, 9), 4,106 (1, 7), 4,100 (0,8), 4,088 (0, 3,430 (17.4), 5)
■ ,1, 177^1 7V1 1 \ ^1 \ C1 n T 191 CD RV9 77RI0 RV9 ^MO RV9 <vlfi Ι( RV9 <ϊ94Μ RV9 <ϊ9ίν9 ^ 9 1MQ 4V9 ^ORIAO ^V9 cin9icici -9 4Q7HQ ^ 9 4Q ■ , 1, 177 ^ 1 7V1 1 \ ^ 1 \ C1 n T 191 CD RV9 77RI0 RV9 ^ MO RV9 <vlfi Ι (RV9 <ϊ9 4 Μ RV9 <ϊ9ίν9 ^ 9 1MQ 4V9 ^ ORIAO ^ V9 c in9i c i c i -9 4Q7HQ ^ 9 4Q
3(17,9);2,182(0,9);2,149(0,9);2,096(0,7);2,086(1 ,8);2,072(4,6 );2,065(0,9);1 ,751 (0,5);1 ,709(2,3);1 ,696(1 ,8);1 ,678(2,7);1 ,650(0,8);1 ,636(0,8);1 , 626(0,7);1 ,608(0,9);1 ,571 (1 ,2);1 ,506(0,7);1 ,474(0,6);1 ,349(0 6);1 ,337(0,7);1 ,313(1 ,0);1 ,278(1 ,2);1 ,254(8,0);1 ,236(16,0);1 ,219(7,4);1 ,210(2,4); 1 , 194(4,7); 1 , 192(5,5); 1 , 177(8,6); 1 , 159(3,9);0,000(2,4) 3 (17.9); 2.182 (0.9); 2.149 (0.9); 2.096 (0.7); 2.086 (1, 8); 2.072 (4.6); 2.065 (0.9); 1 , 751 (0.5); 1, 709 (2.3); 1, 696 (1, 8); 1, 678 (2.7); 1, 650 (0.8); 1, 636 (0, 1), 626 (0.7), 1, 608 (0.9), 1, 571 (1, 2), 1, 506 (0.7), 1, 474 (0.6), 1, 349 (0 6); 1, 337 (0.7); 1, 313 (1, 0); 1, 278 (1, 2); 1, 254 (8.0); 1, 236 (16.0) 1, 219 (7,4); 1, 210 (2,4); 1, 194 (4,7); 1, 192 (5.5); 1, 177 (8,6); 1, 159 (3,9); 0,000 (2,4)
Beispiel 1591 : 1H-NMR(400,0 MHz, de-DMSO): δ= 7,793(3,3);7,790(4,1);7,784(1 ,9);7,563(7,8);7,559(5,5);7,553(8,8);7,536(2,4);7,489(2,1);7,Example 1591: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.793 (3.3); 7.790 (4.1); 7.784 (1.9); 7.563 (7.8); 7.559 ( 5.5); 7,553 (8.8); 7,536 (2.4); 7,489 (2.1); 7,
471(2,2);4,115(4,2);4,000(4,6);3,365(0,5);3,314(89,5);2,967(11 ,4);2,939(16,0);2,670(0,7);2,523(2,5);2,519(3,6);2,510(36,8);2,505(78,0)471 (2.2), 4.115 (4.2), 4.000 (4.6), 3.365 (0.5), 3.314 (89.5), 2.967 (11, 4), 2.939 (16.0), 2.670 (0.7); 2,523 (2.5); 2,519 (3.6); 2,510 (36.8); 2.505 (78.0)
(108,4);2,496(77,0);2,492(35,3);2,469(0,6);2,328(0,7);0,000(4,1) (108.4) 2.496 (77.0); 2.492 (35.3); 2,469 (0.6); 2,328 (0.7); 0,000 (4.1)
Beispiel 1592: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,577(8,0);7,555(7,5);4,116(5,9);4,001(4,9);3,310(1003,2);2,968(11 ,6);2,935(16,0);2,669( 8,5);2,522(46,0);2,509(570,6);2,505(1184,8);2,500(1630,9);2,496(1154,8);2,491(533,0);2,455(6,1);2,327(8,5);2,085(4,1);0,00 Example 1592: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.577 (8.0); 7.555 (7.5); 4.116 (5.9); 4.001 (4.9); 3.310 ( 2.968 (11, 6), 2.935 (16.0), 2.669 (8.5), 2.522 (46.0), 2.509 (570.6), 2.505 (1184.8), 2.500 (1630 , 9); 2.496 (1154.8) 2.491 (533.0); 2,455 (6.1); 2,327 (8.5); 2,085 (4.1); 0.00
Beispiel 1596: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,745(1 ,0 ;7,724(2,3);7,707(2,3);7,685(1 ,1);7,556(2,3);7,540(3,9);7,523(2,8);7,456(2,0);7, 449(2,1);7,432(2,3);7,427(3,4);7,422(2,3);7,405(2,0);7,398(2 0);7,257(1 ,8);7,255(1 ,9);7,250(1 ,8);7,234(3,3);7,228(3,2);7,214(1 ,7);7,212(1 ,7);7 ,208(1 ,6);6,524(1 ,3);3,455(0,9);3,437(2,9);3,419(2,9);3,401(1 ,0);3,306(16,4);3,227(1 , 1 );3 ,209(3,2) ;3, 191 (3,2);3, 174(1 , 1 );2,943(0,9);2,924(4,2)Example 1596: 1 H NMR (400.0 MHz, de-DMSO): δ = 7.745 (1.0, 7.724 (2.3); 7.707 (2.3); 7.685 (1, 1); 7.556 (2 , 3); 7,540 (3.9); 7,523 (2,8); 7,456 (2,0); 7,449 (2,1); 7,432 (2,3); 7,427 (3,4); 7,422 ( 7, 355 (1, 8); 7,255 (1, 9); 7,250 (1, 8); 7,205 (3,3); 7,228 (3, 3); 7,218 (1,6), 6,524 (1,3), 3,455 (0,9), 3,437 (2,9), 3,419 (2), 7,214 (1, 7), 7,212 (1, 7); , 9); 3,401 (1,0); 3,306 (16,4); 3,227 (1,1); 3,209 (3,2); 3,191 (3,2); 3,174 (1, 1); ); 2,943 (0.9); 2,924 (4.2)
;2,917(16,0);2,906(3,6);2,888(1 ,1);2,855(13,8);2,675(0,5);2,6 70(0,7);2,542(12,8);2,523(2,1);2,519(3,0);2,510(39,2);2,506(84,6);2,501(118,4); 2,496(82,9);2,492(37,2);2,332(0,5);2,328(0,7);1 ,167(2,7);1 ,1' 19(5,4);1 ,131(2,7);1 ,120(3,3);1 ,103(7,0);1 ,086(6,6);1 ,069(8,1);1 ,051(3,6);0,008(1 ,0);0,000(32,3);-0,009(1 ,0) 2.917 (16.0), 2.906 (3.6), 2.888 (1, 1), 2.855 (13.8), 2.675 (0.5), 2.670 (0.7), 2.542 (12, 8); 2,523 (2.1); 2,519 (3.0); 2,510 (39.2); 2,506 (84.6); 2.501 (118.4); 2.496 (82.9), 2.492 (37.2), 2.322 (0.5), 2.328 (0.7), 1, 167 (2.7), 1, 1 ', 19 (5.4), 1, 131 (2,7); 1, 120 (3,3); 1, 103 (7,0); 1, 086 (6,6); 1, 069 (8,1); 1, 051 (3,6 0.008 (1, 0), 0.000 (32.3), - 0.009 (1, 0)
Beispiel 1598: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,714(0,6);7,582(1 ,3);7,564(1 ,4);7,531(1 ,2);7,513(1 ,2);7,467(0,6);7,461(0,8);7,438(1 ,1);7, 410(0,8);7,258(0,8);7,244(1 ,0);7,238(1 ,4);7,216(0,7);4,216(47);4,110(3,5);3,689(16,0);3,611(10,3);3,305(46,3);2,986(8,2);2,955(14,2);2,674^ 1 ,0);2,669(1 ,4);2,665(1 ,1);2,523(4,3);2,518(6,0);2,509(80,2);2,505(175,2);2,500(244,6);2,496(171 ,6);2,491(77,9);2,332(1 ,0);2,327(1 ,5);2,322(
Figure imgf000108_0001
Figure imgf000109_0001
5.3) ;3,213(7,6);2,674(2,2);2,670(3,1);2,665(2,4);2,523(17,9);2,518^ Example 1598: 1 H NMR (400.0 MHz, de-DMSO): δ = 7.714 (0.6), 7.582 (1.3), 7.564 (1.4), 7.531 (1.2), 7.513 ( 1, 2), 7.467 (0.6), 7.461 (0.8), 7.438 (1, 1), 7, 410 (0.8), 7.258 (0.8), 7.244 (1.0), 7.238 (1, 4); 7.216 (0.7); 4.216 (47); 4.110 (3.5); 3.689 (16.0); 3.611 (10.3); 3.305 (46.3); 2.986 (8, 2); 2,955 (14,2); 2,674 ^ 1, 0); 2,669 (1,4), 2,665 (1,1), 2,523 (4,3), 2,518 (6,0), 2,509 (80,2 2.505 (175.2), 2.500 (244.6), 2.496 (171, 6), 2.491 (77.9), 2.322 (1, 0), 2.327 (1, 5), 2.322 (
Figure imgf000108_0001
Figure imgf000109_0001
5.3), 3.213 (7.6), 2.674 (2.2), 2.670 (3.1), 2.665 (2.4), 2.523 (17.9), 2.518 ^
,439(5,4);2,418(1 ,9);2,410(2,4);2,332(2,1);2,327(2,8);2,323(2,1);1 ,821 (5,8);1 ,787(10,8);1 ,750(6,4);1 ,678(3,1);1 ,650(2,9);1 ,436(1 ,9);1 ,405(5,3) ;1 ,377(5,7);1 ,351(3,0);1 ,324(2,5);1 ,293(4,9);1 ,262(5,4);1 ,230(4,9);1 ,199(3,0);1 ,167(2,0);1 ,137(0,7);0,008(2,3);0,000(71 ,2);-0,009(3,5) Beispiel 1633: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 , 856(0,5)7,443(2,5)7,425(2,6)7,339(1 , 4)7,321 (1 ,4);6,090(0,6);6,070(0,8);4,373(0,8);4 ,363(0,7);4,352(0,8);4,342(0,8);3,641(16,0);3,532(2,5);3,514(3,6);3,508(3,2);3,498(3,0);3,427(7,8);3,414(0,6);3,400(07);3,388(0,6);3,374(0,6^ ;3,117(1 ,2);3,104(1 ,2);3,098(1 ,2);3,086(1 ,2);2,669(0,5);2,523(1 ,8);2,518(2,6);2,510(33,8);2,505(72,9);2,500(101 ,2);2,496(70,2);2,491(31 ,6);2, 463(0,5);2,454(0,7);2,444(0,7);2,327(0,6);2,229(0,6);2,210(0,6);2,085(3,0);1 ,889(0,7);1 ,872(1 ,4);1 ,857(1 ,8);1 ,852(1 ,8);1 ,841(1 ,8);1 ,821(1 ,2);1 ,790(1 ,6);1 ,754(1 ,4);1 ,679(0,6);1 ,652(0,6);1 ,399(0,8);1 ,371(0,8);1 ,329(0,5);1 ,298(0,9);1 ,266(1 ,1);1 ,234(0,9);1 ,194(2,7);1 ,176(5,1);1 ,158(2,4); 0,000(3,8) , 439 (5.4); 2.418 (1, 9); 2.410 (2.4); 2.332 (2.1); 2.327 (2.8); 2.233 (2.1); 1, 821 (5.8) 1, 787 (10.8); 1, 750 (6.4); 1, 678 (3.1); 1, 650 (2.9); 1, 436 (1, 9); 1, 405) (5,3); 1, 377 (5,7); 1, 351 (3,0); 1, 324 (2,5); 1, 293 (4,9); 1, 262 (5,4) 1, 230 (4.9), 1, 199 (3.0), 1, 167 (2.0), 1, 137 (0.7), 0.008 (2.3), 0.000 (71, 2) -0.009 (3.5) Example 1633: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 856 (0.5) 7.443 (2.5) 7.425 (2.6) 7.339 ( 1, 4), 7.321 (1, 4), 6.090 (0.6), 6.070 (0.8), 4.373 (0.8), 4, 363 (0.7), 4.352 (0.8), 4.322 ( 0.8); 3,641 (16.0); 3,532 (2.5); 3,514 (3.6); 3,508 (3.2); 3,498 (3.0); 3,427 (7.8); 3,414 (0 , 6); 3,400 (07); 3,388 (0,6); 3,374 (0,6 ^; 3,117 (1, 2); 3,104 (1,2); 3,098 (1,2); 3,086 (1,2)) 2.659 (0.5), 2.523 (1, 8), 2.518 (2.6), 2.510 (33.8), 2.505 (72.9), 2.500 (101, 2), 2.496 (70.2); 2.491 (31, 6); 2.463 (0.5); 2.454 (0.7); 2.444 (0.7); 2.327 (0.6); 2.229 (0.6); 2.210 (0.6) , 2,085 (3,0); 1,889 (0,7); 1,872 (1,4); 1, 857 (1, 8); 1, 852 (1, 8); 1, 841 (1, 841); 1, 821 (1, 2); 1, 790 (1, 6); 1, 754 (1, 4); 1, 679 (0.6); 1, 652 (0.6); 1, 399 (0.8); 1, 371 (0.8); 1, 329 (0.5); 1, 298 (0.9); 1, 266 (1, 1); 1, 234 ( 0.9); 1, 194 (2.7); 1, 176 (5.1); 1, 158 (2.4); 0.000 (3.8)
Beispiel 1634: 1H-NMR(400,0 MHz, de-DMSO): δ= 4,159(5,8);4,140(6,7);3,406(11 ,3);3,373(5,0);3,361(12,2);3,357(13,9);3,338(30,5);3,306(6Example 1634: 1 H-NMR (400.0 MHz, de-DMSO): δ = 4.159 (5.8), 4.140 (6.7), 3.406 (11, 3), 3.373 (5.0), 3.361 ( 12.2) 3,357 (13.9); 3.338 (30.5); 3.306 (6
141 ,1);3,277(15,7);3,274(10,2);3,268(6,9);3,257(20,1);3,222(4,4);2,678(14,4);2,674(31 ,1);2,669(45,4);2,665(32,7);2,660(14,3);2,605(7,3141, 1), 3.277 (15.7), 3.274 (10.2), 3.268 (6.9), 3.257 (20.1), 3.222 (4.4), 2.678 (14.4), 2.674 (31 , 1), 2,669 (45.4); 2,665 (32.7); 2,660 (14.3); 2,605 (7.3
00(10,0);2,555(15,2);2,551(15,3);2,546(9,1);2,523(126,2);2,518(182,2);2,509(2499,0);2,505(5442,3);2,500(7647,9);2,496(5374,8);2,491(241300 (10.0); 2.555 (15.2); 2,551 (15.3); 2,546 (9.1); 2,523 (126.2); 2.518 (182.2); 2.509 (2499.0); 2,505 (5442.3) 2.500 (7647.9) 2.496 (5374.8); 2,491 (2413
,6);2,473(23,3);2,468(14,5);2,457(13,0);2,452(11,6);2,447(6,6);2,435(4,3);2,336(14,9);2,332(33,8);2,327(46,5);2,322(33,5);2,318(15,2);2,072(, 6); 2.473 (23.3); 2,468 (14.5); 2,457 (13.0); 2.452 (11.6); 2,447 (6.6); 2,435 (4.3); 2,336 (14, (2.072; 9); 2.332 (33.8); 2,327 (46.5); 2,322 (33.5); 2.318 (15.2)
13,1);1 ,802(5,3);1 ,648(5,6);1 ,236(9,5);1 ,219(16,0);1 ,201 (8,4);1 ,155(8,2);0,886(9,0);0,008(40,0);0,000(1357 13.1); 1, 802 (5.3); 1, 648 (5.6); 1, 236 (9.5); 1, 219 (16.0); 1, 201 (8.4); 1, 155 (8.2), 0.886 (9.0), 0.008 (40.0), 0.000 (1357
Beispiel 1635: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,778(0,8);9,764(1 ,4);9,750(0,7);8,353(6,8);8,334(7,2);7,713(5,5);7,709(1 , 9)7,697(2,0)7,Example 1635: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.778 (0.8); 9.764 (1, 4); 9.750 (0.7); 8.353 (6.8); 8.344 ( 7.2), 7.713 (5.5), 7.709 (1.9) 7.697 (2.0) 7,
692(6,3);7,632(1 ,9);7,344(4,8);7,325(4,3);7,010(1 ,5);6,790(5,3);6,771(5,3);3,314(17,1);3,290(3,8);3,275(3,6);3,257(1 ,9);2,524(0,9);2,520(692 (6.3), 7.632 (1, 9), 7.344 (4.8), 7.325 (4.3), 7.010 (1.5), 6.790 (5.3), 6.771 (5.3), 3.314 (17,11); 3,290 (3,8); 3,275 (3,6); 3,257 (1,9), 2,524 (0,9), 2,520 (
2,511(16,6);2,506(35,9);2,502(49,9);2,497(34,8);2,493(15,5);2,374(15,4);1 ,556(2,0);1 ,538(3,8);1 ,520(3,8);1 ^ 2.511 (16.6), 2.506 (35.9), 2.502 (49.9), 2.497 (34.8), 2.493 (15.5), 2.374 (15.4), 1.556 (2.0) ; 1, 538 (3,8); 1, 520 (3,8); 1 ^
,893(6,5);0,000(4,1)  , 893 (6.5); 0,000 (4.1)
Beispiel 1636: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,785(0,6);8,337(3,0);8,318(3,1);7,714(2,5);7,698(0,9);7,693(2,8);7,339(2,2);7,320(2,0);6,Example 1636: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.785 (0.6); 8.337 (3.0); 8.318 (3.1); 7.714 (2.5); 7.698 ( 0.9); 7,693 (2.8); 7,339 (2.2); 7,320 (2.0); 6,
782(1 ,5);6,763(1 ,5);3,361(0,8);3,343(1 ,4);3,325(2,1);3,311(3,1);2,511(5,1);2,507(10,9);2,502(15,2);2,497(10,7);2,493(4,9);2,37 782 (1, 5); 6,763 (1,5), 3,361 (0,8), 3,343 (1,4), 3,325 (2,1), 3,311 (3,1), 2,511 (5,1), 2,507 (10.9) 2,502 (15.2); 2.497 (10.7); 2,493 (4.9); 2.37
6);1 ,629(0,8);1 ,612(0,7);1 ,442(0,9);1 ,425(1 ,8);1 ,406(1 ,8);1 ,389(0,8);0,921(16,0);0,904(15,2);0,000(1 ,0)  6); 1, 629 (0.8); 1, 612 (0.7); 1, 442 (0.9); 1, 425 (1, 8); 1, 406 (1, 8); 1, 389 (0.8); 0.921 (16.0); 0.904 (15.2); 0.000 (1, 0)
Beispiel 1638: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,019(0,5);8,413(2,9);7,888(1 ,8);7,883(1 ,8);7,690(8,4);7,670(9,1);7,647(1 ,0);7,642(0,9);7Example 1638: 1 H NMR (400.0 MHz, de-DMSO): δ = 12.019 (0.5), 8.413 (2.9), 7.888 (1.8), 7.8383 (1, 8), 7.690 ( 8.4); 7.670 (9.1); 7.647 (1.0); 7.642 (0.9); 7
,626(2,0);7,621(2,0);7,597(2,6);7,576(1 ,1);7,482(12,5);7,464(13,2);7,306(15,5);7,286(13,9);6,627(1 ,4);3,772(0,8);3,394(38,9);3,222(2,6);3,20, 626 (2.0); 7.621 (2.0); 7.597 (2.6); 7.576 (1, 1); 7.482 (12.5); 7.464 (13.2); 7.306 (15.5); 7,286 (13.9), 6.627 (1, 4), 3.772 (0.8), 3.394 (38.9), 3.222 (2.6), 3.20
5(6,6);3,187(6,6);3,171(2,4);2,944(3,5);2,784(2,1);2,679(0,6);2,674(1 ,4);2,670(2,0);2,665(1 ,4);2,660(0,6);2,523(6^ 5 (6.6); 3.187 (6.6); 3.171 (2.4); 2.944 (3.5); 2.784 (2.1); 2.679 (0.6); 2.674 (1, 4); 2.670 (2.0), 2.665 (1, 4), 2.660 (0.6), 2.523 (6 ^
,505(240,2);2,501 (337,2);2,496(236,9);2,491 (106,5);2,450(0,9);2,358(49,6);2,337(1 ,0);2,332(1 ,6);2,327(2,2);2,323(1 ,6);2,072(0,6);1 ,956(2,4); , 505 (240.2); 2.501 (337.2); 2.496 (236.9); 2.491 (106.5); 2.450 (0.9); 2.358 (49.6); 2.377 (1.0); 2,332 (1,6), 2,327 (2,2,2), 2,323 (1,6), 2,072 (0,6), 1, 956 (2,4);
1 ,950(0,7);1 ,913(8,9);1 ,136(7,7);1 ,119(16,0);1 ,101 (8,3);1 ,073(8,1);1 ,056(15,3);1 ,038(7,1);0,008(1 ,0);0,000(33,6);-0,009(0,9) 1, 950 (0.7); 1, 913 (8.9); 1, 136 (7.7); 1, 119 (16.0); 1, 101 (8.3); 1, 073 (8 , 1); 1, 056 (15.3); 1, 038 (7.1); 0.008 (1, 0); 0.000 (33.6); - 0.009 (0.9)
Beispiel 1639: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,683(2,2);7,552(2,2);7,534(2,4);7,510(1 ,8);7,492(1 ,9);7,318(3,2);7,311(2,6);7,298(3,0);7, 290(2,2);4,206(5,1);4,120(3,8);3,688(16,0);3,603(11 ,1);3,506(8,0);2,981(8,9);2,961(14,6);2,674(0,7);2,669(1 ,1);2,665^ Example 1639: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.683 (2.2), 7.552 (2.2), 7.534 (2.4), 7.510 (1.8), 7.492 ( 1, 9); 7,318 (3,2); 7,311 (2,6); 7,298 (3,0); 7,290 (2,2); 4,206 (5,1); 4,120 (3,8); 3,688 (16.0), 3.603 (11, 1), 3.506 (8.0), 2.981 (8.9), 2.961 (14.6), 2.674 (0.7), 2.669 (1, 1), 2.665 ^
1) ;2,509(66,2);2,505(145,4);2,500(203,9);2,496(142,4);2,491 (64,1);2,449(0,6);2,362(11 ,5);2,332(0,9);2,327(1 ,2);2,322(0,9);2,^  1), 2.509 (66.2), 2.505 (145.4), 2.500 (203.9), 2.496 (142.4), 2.491 (64.1), 2.449 (0.6), 2.362 (11, 5 2,332 (0.9); 2,327 (1,2); 2,322 (0,9); 2, ^
(2,3);0,000(78,0);-0,009(2,2) (2.3); 0,000 (78.0) - 0.009 (2.2)
Beispiel 1644: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,083(0,7);7,679(3,6);7,505(6,9);7,487(7,2);7,315(6,4);7,294(5,9);6,658(0,6);5,207(1 ,8);5 ,196(1 ,6);4,432(0,7);4,399(0,7);4,369(1 ,2);4,197(1 ,9);4,180(5,9);4,162(6,2);4,144(2,4);4,129(1 ,6);4,119(0,8);4,111 (1 ,7);4,101(1 ,6);4,093(0,8); 4,083(1 ,5);4,074(0,6);4,056(0,6);3,487(1 ,0);3,456(1 ,2);3,325(56,4);3,161(0,7);3,135(1 ,1);3,105(0,6);2,771(0,7);2,674(1 ,2);2,670(1 ,8);2,665(1 ,Example 1644: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.083 (0.7), 7.679 (3.6), 7.555 (6.9), 7.487 (7.2), 7.315 ( 6.4); 7.294 (5.9); 6.658 (0.6); 5.207 (1, 8); 5, 196 (1, 6); 4.432 (0.7); 4.399 (0.7); 4.369 (1,2), 4,197 (1, 9), 4,180 (5,9), 4,162 (6,2), 4,144 (2,4), 4,129 (1,6), 4,119 (0,8), 4,111 ( 1, 7); 4.101 (1, 6); 4.093 (0.8); 4.083 (1.5), 4.074 (0.6), 4.056 (0.6), 3.487 (1.0), 3.456 (1.2), 3.325 (56.4), 3.161 (0.7), 3.135 (1, 1), 3.105 (0.6), 2.771 (0.7), 2.674 (1, 2), 2.670 (1, 8), 2.665 (1,
2) ;2,660(0,6);2,538(0,9);2,534(1 ,0);2,523(4,8);2,518(7,2);2,510(97,3);2,505(210,7);2,501(295,1);2,496(207,4 2), 2.660 (0.6), 2.538 (0.9), 2.534 (1.0), 2.523 (4.8), 2.518 (7.2), 2.510 (97.3), 2.555 (210.7 ); 2.501 (295.1); 2.496 (207.4
6);2,361(23,0);2,337(0,9);2,332(1 ,5);2,327(1 ,9);2,323(1 ,4);2,178(1 ,0);2,147(1 ,1);2,085(0,8);2,072(1 ,0);2,051(0,9);1 ,753(0,6);1 ,699(2,3);1 ,671 ( 3,2);1 ,554(1 ,5);1 ,515(0,8);1 ,484(0,6);1 ,393(0,5);1 ,355(0,6);1 ,329(0,7);1 ,306(1 ,0);1 ,271(1 ,3);1 ,255(7,7);1 ,237(16,0);1 ,226(1 ,7);1 ,219(7,4);1 ,20 8(0,9);1 ,189(4,3);1 ,171 (8,5);1 ,154(4,0);0,008(0,8);0,000(26,5);-0,009(0,8)  2.361 (23.0), 2.327 (0.9), 2.322 (1.5), 2.327 (1.9), 2.323 (1.4), 2.178 (1.0), 2.147 (1, 1) 2.085 (0.8), 2.072 (1.0), 2.051 (0.9), 1.753 (0.6), 1.699 (2.3), 1.671 (3.2); 1, 554 (1, 5); 1, 515 (0.8); 1, 484 (0.6); 1, 393 (0.5); 1, 355 (0.6); 1, 329 (0 , 7); 1, 306 (1, 0); 1, 271 (1, 3); 1, 255 (7.7); 1, 237 (16.0); 1, 226 (1, 7); 1 , 219 (7.4); 1, 20 8 (0.9); 1, 189 (4.3); 1, 171 (8.5); 1, 154 (4.0); 0.008 (0.8 ); 0,000 (26.5) - 0.009 (0.8)
Beispiel 1645: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,678(1 ,0);9,753(0,8);8,369(6,7);8,350(7,2);7,894(1 , 8)7,765(0,9)7,748(1 ,0)7,617(1 ,2)7Example 1645: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.678 (1, 0); 9.753 (0.8); 8.369 (6.7); 8.350 (7.2); 7.894 ( 1, 8) 7.765 (0.9) 7.748 (1, 0) 7.617 (1, 2) 7
,599(1 ,9)7,595(2,4)7,591 (1 ,7);7,570(3,4);7,550(3,9);7,531 (1 ,4);6,836(0,8);3,432(0,9);3,427(0,9);3,406(0,7);3,394(0,7);3,360(2,5);3,356(1 ,2);, 599 (1, 9) 7.595 (2.4) 7.551 (1, 7), 7.570 (3.4), 7.550 (3.9), 7.531 (1.4), 6.836 (0.8), 3.432 ( 0.9), 3.437 (0.9), 3.406 (0.7), 3.394 (0.7), 3.360 (2.5), 3.356 (1, 2);
3,342(2,5);3,308(587,2);3,276(4,1);3,262(1 ,0);3,256(1 ,6);3,246(0,8);3,207(1 ,2);2,674(2,4);2,669(3,3);2,665( 3.322 (2.5), 3.308 (587.2), 3.276 (4.1), 3.262 (1, 0), 3.256 (1, 6), 3.246 (0.8), 3.207 (1, 2), 2.674 (2.665 (2.4); 2,669 (3.3)
,5);2,555(1 ,3);2,550(2,2);2,546(2,1);2,541(2,1);2,523(10,4);2,518(14,8);2,510(188,4);2,505(407,4);2,500(570,0)i  , 5), 2.555 (1, 3), 2.550 (2.2), 2.546 (2.1), 2.541 (2.1), 2.523 (10.4), 2.518 (14.8), 2.510 (188, 4); 2.505 (407.4); 2,500 (570.0) i
449(0,6);2,444(0,8);2,400(0,7);2,336(1 ,1);2,332(2,5);2,327(3,4);2,322(2,4);2,318(1 ,1);2,085(1 ,1);2,072(0,8);1 ,^  449 (0.6), 2.444 (0.8), 2.400 (0.7), 2.336 (1, 1), 2.322 (2.5), 2.327 (3.4), 2.322 (2.4), 2.318 (1, 1); 2.085 (1, 1); 2.072 (0.8); 1, ^
,506(2,1);0,930(7,4);0,912(16,0);0,893(6,5);0,008(1 ,2);0,000(44,8);-0,009(1 ,3)  , 506 (2.1), 0.930 (7.4), 0.912 (16.0), 0.893 (6.5), 0.008 (1, 2), 0.000 (44.8), - 0.009 (1, 3)
Beispiel 1646: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,364(3,1);8,345(3,3);7,894(0,9);7,616(0,6);7,599(1 ,0);7,596(1 ,1);7,594(1 ,1);7,591(0,9);7, 570(1 ,6)7,550(1 ,8)7,531 (0,7);3,367(0,8);3,350(1 ,3);3,333(1 ,5);3,308(94,2);2,670(0,6);2,523(1 ,7);2,518(2,5);2,510(31 ,0);2,505(66,8);2,501 (9Example 1646: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.364 (3.1); 8.345 (3.3); 7.894 (0.9); 7.616 (0.6); 7.599 ( 1, 0), 7.596 (1, 1), 7.594 (1, 1), 7.551 (0.9), 7, 570 (1, 6), 7.550 (1, 8), 7.531 (0.7), 3.367 (0 , 3,350 (1,3), 3,333 (1, 5), 3,308 (94,2), 2,670 (0,6), 2,523 (1, 7), 2,518 (2,5), 2,510 (31, 0); 2,505 (66,8); 2,501 (9
3.4) ;2,496(65,4);2,491 (29,3);2,327(0,6);1 ,644(0,6);1 ,627(0,8);1 ,610(0,6);1 ,447(0,9);1 ,430(1 ,7);1 ,411 (1 ,7);1 ,394(0,7);0,922(16,0);0,905(15,2); 0,000(8,5) 3.4), 2.496 (65.4), 2.491 (29.3), 2.327 (0.6), 1. 644 (0.6), 1.627 (0.8), 1.610 (0.6) 1, 447 (0.9), 1, 430 (1, 7), 1, 411 (1, 7), 1, 394 (0.7), 0.922 (16.0), 0.905 (15.2) ; 0.000 (8.5)
Beispiel 1648: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,420(4,6);8,401 (4,8);7,957(2,1);7,953(3,8);7,948(2,3);7,917(3,1);7,818(1 ,8);7,814(1 ,5);7, 798(3,2);7,794(2,9);7,668(1 ,1);7,666(1 ,3);7,663(1 ,1);7,661(1 ,1);7,648(2,0);7,646(1 ,9);7,643(2,1);7,640(1 ,7);7,606(2,9);7,586(3 Example 1648: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.420 (4.6); 8.401 (4.8); 7.957 (2.1); 7.953 (3.8); 7.948 ( 2.3); 7.917 (3.1); 7.818 (1, 8); 7.814 (1.5); 7, 798 (3.2); 7.794 (2.9); 7.668 (1, 1); 7.666 (1, 3); 7,663 (1, 1); 7,661 (1, 1); 7,648 (2,0); 7,646 (1,9); 7,643 (2,1); 7,640 (1, 7); 7,606 ( 2.9); 7,586 (3
,549(2,1)7,544(2,4)7,534(9,5)7,530(16,0)7,524(6,6)7,518(4,7)7,513(8,0)7,493(1 ,8)7,090(1 ,9)7,071(t , 549 (2.1) 7.544 (2.4) 7.534 (9.5) 7.530 (16.0) 7.524 (6.6) 7.518 (4.7) 7.513 (8.0) 7.493 (1, 8) 7.090 (1, 9) 7,071 (t
;3,383(2,2);3,362(1 ,4);3,311(226,6);3,248(0,8);3,210(1 ,8);3,193(4,7);3,176(4,5);3,159(1 ,6);2,679(0,7);2,674(17^ 3,383 (2,2), 3,362 (1,4), 3,311 (226,6), 3,248 (0.8), 3,210 (1, 8), 3,193 (4,7), 3,176 (4,5); 3.159 (1, 6); 2.679 (0.7); 2.674 (17 ^
0,8);2,556(0,8);2,551(1 ,0);2,547(0,8);2,523(7,4);2,519(10,4);2,510(131 ,7);2,505(286,6);2,501(401 ,8);2,496(282,6);2,491(127,3);2,461(0,7);2, 438(0,6);2,337(0,8);2,332(1 ,8);2,327(2,4);2,323(1 ,7);2,318(0,8);2,085(1 ,5);2,072(3,9);1 ,142(5,4);1 ,124(11 ,2);1 ,106(5,6);1 ,067(5,5);1 ,050(10,5 );1 ,032(4,9);0,008(0,8);0,000(27,7);-0,009(0,8)  0.8), 2.556 (0.8), 2.551 (1.0), 2.547 (0.8), 2.523 (7.4), 2.519 (10.4), 2.510 (131, 7), 2.505 (286 , 6); 2,501 (401, 8); 2,496 (282,6); 2,491 (127,3); 2,461 (0,7); 2, 438 (0,6); 2,337 (0,8); 2,332 ( 1, 8), 2,327 (2,4), 2,323 (1,7), 2,318 (0,8), 2,085 (1,5), 2,072 (3,9), 1, 142 (5,4), 1 , 124 (11, 2); 1, 106 (5.6); 1, 067 (5.5); 1, 050 (10.5); 1, 032 (4.9); 0.008 (0.8) ; 0,000 (27.7) - 0.009 (0.8)
Beispiel 1649: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,925(1 ,5);7,905(1 ,1);7,804(0,8);7,786(1 ,2);7,765(0,6);7,589(2,2);7,571(2,6);7,567(1 ,2);7, 562(1 ,0)7,557(0,6)7,551(1 ,9)7,546(4,4)7,542(4,5)7,535(3,3)7^ Example 1649: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.925 (1.5), 7.905 (1, 1), 7.804 (0.8), 7.786 (1.2), 7.765 ( 7.659 (2.2); 7.571 (2.6); 7.567 (1, 2); 7, 562 (1, 0), 7.557 (0.6), 7.551 (1, 9), 7.546 (4); 4) 7.542 (4.5) 7.535 (3.3) 7 ^
);3,426(6,2);2,989(8,7);2,952(14,9);2,524(1 ,4);2,519(2,0);2,511 (23,4);2,506(50,4);2,501(70,4);2,497(49,3);2,492(22,0)  3.446 (6.2), 2.989 (8.7), 2.952 (14.9), 2.524 (1, 4), 2.519 (2.0), 2.511 (23.4), 2.506 (50.4) ; 2,501 (70.4); 2.497 (49.3); 2.492 (22.0)
Beispiel 1654: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,360(1 ,3)7,912(1 ,3)7,787(1 ,0);7,626(0,7);7,612(0,8);7,604(0,8);7,590(0,8);7,540(9,5);7,
Figure imgf000111_0001
Beispiel 1679: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,777(1 ,2);7,756(1 ,5);7,538(1 ,5);7,520(1 ,6);7,499(1 ,2);7,480(1 ,2);7,060(2,9);7,052(2,2);7,Example 1654: 1 H NMR (400.0 MHz, de-DMSO): δ = 8.362 (1.3) 7.912 (1.3) 7.787 (1.0); 7.626 (0.7); 7.612 (0, 8); 7,604 (0.8); 7,590 (0.8); 7,540 (9.5); 7,
Figure imgf000111_0001
Example 1679: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.777 (1.2), 7.756 (1.5), 7.538 (1.5), 7.520 (1.6), 7.499 ( 1, 2), 7,480 (1,2), 7,060 (2,9), 7,052 (2,2), 7,
038(2,8);7,030(1 ,9);4,202(3,5);4,122(2,5);3,822(16,0);3,819(12,4);3,687(10,3);3,603(6,8);2,979(5,7);2,962(9,4);2,674(0,7);2,669(1 ,0);2,^038 (2.8), 7.030 (1.9), 4.202 (3.5), 4.122 (2.5), 3.822 (16.0), 3.819 (12.4), 3.687 (10.3), 3.603 (6.8); 2.979 (5.7); 2.962 (9.4); 2.674 (0.7); 2.699 (1, 0); 2, ^
7);2,523(3,0);2,518(4,3);2,509(53,8);2,505(116,5);2,500(162,7);2,496(114,2);2,491(51 ,8);2,332(0,7);2,327(1 ,^ 2.523 (3.0), 2.518 (4.3), 2.509 (53.8), 2.505 (116.5), 2.500 (162.7), 2.496 (114.2), 2.491 (51, 8 2,332 (0,7); 2,327 (1, ^
1 ,0);0,000(36,3);-0,009(1 ,1)  1, 0), 0.000 (36.3), - 0.009 (1, 1)
Beispiel 1680: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,766(2,3)7,762(0,8)7,749(0,8)7,744(2,4)7,565(2,5)7,547(2,7)7,053(3,4)7,047(1 ,0)7,Example 1680: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.766 (2.3) 7.762 (0.8) 7.749 (0.8) 7.744 (2.4) 7.565 (2.5) 7,547 (2,7) 7,053 (3,4) 7,047 (1, 0) 7,
036(0,9);7,030(3,2);3,819(16,0);3,427(0,7);3,410(1 ,6);3,394(0,9);3,371(0,9);3,355(1 ,9);3,339(1 ,1);2,510(4,8);2,506(10 036 (0.9), 7.030 (3.2), 3.819 (16.0), 3.427 (0.7), 3.410 (1.6), 3.394 (0.9), 3.371 (0.9), 3.355 (1, 9), 3.339 (1, 1), 2.510 (4.8), 2.506 (10
9);2,492(4,4);1 ,864(0,5); 1 ,846(1 ,1);1 ,837(1 ,3);1 ,829(1 ,6);1 ,815(1 ,2);0,000(3,0)  9); 2,492 (4.4); 1, 864 (0.5); 1, 846 (1, 1); 1, 837 (1, 3); 1, 829 (1, 6); 1, 815 (1, 2); 0.000 (3.0)
Beispiel 1681 : 1H-NMR(400,0 MHz, de-DMSO): δ= 7,760(1 ,5)7,738(1 ,6)7,505(2,0)7,487(2,1 );7,049(3,3)7,044(0,9)7,032(0,9)7,027(3,0);3, 817(16,0);3,543(0,6);3,228(0,6);2,523(0,6);2,510(12,6);2,505(27,1);2,501 (37,7);2,496(26,5);2,492(11 ,9);1 ,597(0,8);1 ,585(0,8);1 ^ Example 1681: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.760 (1.5) 7.738 (1.6) 7.555 (2.0) 7.487 (2.1); 7.049 (3.3 ) 7.044 (0.9) 7.032 (0.9) 7.027 (3.0); 3, 817 (16.0); 3.543 (0.6); 3.228 (0.6); 2.523 (0.6); 2.510 (12.6), 2.505 (27.1), 2.501 (37.7), 2.496 (26.5), 2.492 (11, 9), 1, 597 (0.8), 1, 585 (0, 8); 1 ^
0(9,2)  0 (9.2)
Beispiel 1682: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,762(1 ,8)7,740(1 ,8)7,579(2,5)7,560(2,6)7,054(3,5)7,048(1 ,0)7,037(1 , 0)7,031 (3,3);3, 818(16,0);3,605(1 ,4);3,586(2,0);3,282(0,9);2,523(0,7);2,518(1 ,0);2,510(9,8);2,505(20,4);2,501(27,9);2,496(19,5);2,491(8,8);0,000(6,5)Example 1682: 1 H NMR (400.0 MHz, de-DMSO): δ = 7.762 (1.8) 7.740 (1.8) 7.579 (2.5) 7.560 (2.6) 7.054 (3.5) 7.048 (1, 0) 7.037 (1.0) 7.031 (3.3); 3, 818 (16.0); 3.605 (1, 4); 3.586 (2.0); 3.282 (0.9); 2.523 (0.7); 2.518 (1, 0), 2.510 (9.8), 2.505 (20.4), 2.501 (27.9), 2.496 (19.5), 2.491 (8.8), 0.000 ( 6.5)
Beispiel 1683: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,777(1 ,6)7,755(2,1)7,737(0,9)7,560(2,1)7,542(2,3)7,459(1 ,0)7,441(1 ,1)7,060(3,3)7,Example 1683: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.777 (1.6) 7.755 (2.1) 7.737 (0.9) 7.560 (2.1) 7.542 (2.3) 7,459 (1, 0) 7,441 (1,1) 7,060 (3,3) 7,
056(2,2)7,043(0,9);7,038(3,3);7,034(1 ,6);4,418(07);4,408(0,6);4,397(0,7);4,387(0,7);3,823(16,0);3,662(13,2);3,571 (1 ,0);3,553(1 ,4);3,536(0,8056 (2.2) 7.043 (0.9); 7.038 (3.3); 7.034 (1, 6); 4.418 (07); 4.408 (0.6); 4.397 (0.7); 4.387 (0); 7); 3.823 (16.0); 3.662 (13.2); 3.571 (1.0); 3.553 (1, 4); 3.536 (0.8
);3,464(5,8);2,523(0,7);2,519(1 ,0);2,510(13,0);2,505(28,2);2,501(39,5);2,496(27,8);2,491(12,6);2,253(0,5);1 ,91^ 3.444 (5.8), 2.523 (0.7), 2.519 (1, 0), 2.510 (13.0), 2.505 (28.2), 2.501 (39.5), 2.496 (27.8) 2.491 (12.6); 2.253 (0.5); 1, 91 ^
886(1 , 4);1 , 879(1 ,4);1 , 875(1 , 1);1 , 869(1 , 1);0,000(10,9)  886 (1, 4); 1, 879 (1, 4); 1, 875 (1, 1); 1, 869 (1, 1); 0.000 (10.9)
Beispiel 1684: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,773(2,0)7,764(1 ,6)7,751(2,2)7,742(1 ,4)7,494(4,5)7,476(4,9)7,058(3,0)7,051(2,4)7,Example 1684: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.773 (2.0) 7.764 (1.6) 7.751 (2.2) 7.742 (1.4) 7.494 (4.5) 7.476 (4.9) 7.058 (3.0) 7.051 (2.4) 7,
035(3,0);7,029(1 ,8);6,631(0,6);5,205(0,7);5,194(0,6);4,376(0,5);4,197(0,7);4,179(2,3);4,161(2,4);4,144(1 ,0);4,128(0,7);4 035 (3.0), 7.029 (1.8), 6.631 (0.6), 5.205 (0.7), 5.194 (0.6), 4.376 (0.5), 4.197 (0.7), 4.179 (2,3); 4,161 (2,4); 4,144 (1, 0); 4,128 (0,7); 4
,083(0,6);3,831(1 ,0);3,821(16,0);2,520(0,7);2,511(9,7);2,506(21 ,4);2,502(30,1);2,497(21 ,3);2,492(9,7);^  , 083 (0.6), 3.831 (1, 0), 3.821 (16.0), 2.520 (0.7), 2.511 (9.7), 2.506 (21, 4), 2.502 (30.1); 2,497 (21, 3); 2,492 (9,7); ^
1 ,2);1 ,553(0,6);1 ,283(0,5);1 ,270(0,5);1 ,265(0,5);1 ,254(2,9);1 ,237(5,9);1 ,219(2,7);1 , 189(1 , 6);1 , 171(3,1);1 ,154(1 ,5);0,000(8,0)  1, 2); 1, 553 (0.6); 1, 283 (0.5); 1, 270 (0.5); 1, 265 (0.5); 1, 254 (2.9); 1, 237 (5.9); 1, 219 (2.7); 1, 189 (1, 6); 1, 171 (3.1); 1, 154 (1, 5); 0.000 (8.0 )
Beispiel 1685: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,907(0,8);8,330(5,3);8,311(5,5);7,639(2,8)7,633(3,9);7,617(3,4);7,612(2,6);7,443(1 ,0);7,Example 1685: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.907 (0.8), 8.330 (5.3), 8.31 (5.5), 7.639 (2.8) 7.633 (3 , 9); 7.617 (3.4); 7.612 (2.6); 7.433 (1, 0); 7,
426(1 ,3)7,420(1 ,9)7,397(1 ,0);7,009(0,9);6,935(1 ,7);6,916(1 ,7);3,307(75,4);3,287(5,3);3,272(4,4);3,255(2,3);2,670(1 ,3);2,665(1 ,0);2,523(4,8);426 (1, 3) 7,420 (1, 9) 7,397 (1, 0); 7,009 (0,9); 6,935 (1, 7); 6,916 (1, 7); 3,307 (75,4); 3,287 (5 , 3); 3,272 (4,4); 3,255 (2,3); 2,670 (1,3); 2,665 (1,0); 2,523 (4,8);
2,510(79,6);2,505(165,6);2,501(226,6);2,496(159,4);2,491(72,6);2,332(0,9);2,327(1 ,3);2,072(0,6);1 ,555(2,2);1 ,537(4,2);1 ,520(4,3);^ 2.510 (79.6), 2.505 (165.6), 2.501 (226.6), 2.496 (159.4), 2.491 (72.6), 2.332 (0.9), 2.327 (1, 3), 2.072 (0.6); 1, 555 (2.2); 1, 537 (4.2); 1, 520 (4.3); ^
1 ,483(0,6);0,928(7,6);0,910(16,0);0,891(6,8);0,008(0,8);0,000(25,1);-0,009(0,8)  1, 483 (0.6), 0.928 (7.6), 0.910 (16.0), 0.891 (6.8), 0.008 (0.8), 0.000 (25.1), - 0.009 (0.8 )
Beispiel 1686: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,365(2,7);8,346(2,9);7,631(0,6);7,612(0,6);3,368(0,7);3,351 (1 ,1);3,333(1 ,4);3,312(20,1);3Example 1686: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.365 (2.7), 8.346 (2.9), 7.631 (0.6), 7.612 (0.6), 3.368 ( 0.7), 3.351 (1, 1), 3.333 (1, 4), 3.312 (20.1), 3
,305(12,2);2,524(0,7);2,519(1 ,0);2,510(14,2);2,506(30,9);2,501 (43,6);2,496(30,5);2,492(13,4);1 ,642(0,6);1 ,625(0,7^ , 305 (12.2), 2.524 (0.7), 2.519 (1.0), 2.510 (14.2), 2.506 (30.9), 2.501 (43.6), 2.496 (30.5); 2,492 (13.4); 1, 642 (0.6); 1, 625 (0.7 ^
30(1 ,5);1 ,411(1 ,6);1 ,394(0,7);0,921(16,0);0,904(15,3);0,000(9,2)  30 (1, 5); 1, 411 (1, 6); 1, 394 (0.7); 0.921 (16.0); 0.904 (15.3); 0.000 (9.2)
Beispiel 1688: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,371(0,9);8,352(1 ,0)7,652(5,2)7,635(5,4)7,573(4,2)7,554(4,3)7,382(2,4)7,365(3,2)7, 359(4,7);7,336(2,3);3,439(2,6);3,422(7,0);3,404(7,1);3,386(3,0);3,314(171 ,4);3,267(1 ,1);3,199(2,5);3,182(6,5);3,163(6,5)^ Example 1688: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.371 (0.9); 8.352 (1.0) 7.652 (5.2) 7.635 (5.4) 7.573 (4.2 ) 7,554 (4.3) 7,382 (2,4) 7,365 (3,2) 7, 359 (4,7); 7,336 (2,3); 3,439 (2,6); 3,422 (7,0); 3,404 (7.1); 3.386 (3.0); 3.314 (171.4); 3.267 (1, 1); 3.199 (2.5); 3.182 (6.5); 3.163 (6.5) ^
);2,670(3,0);2,665(2,1);2,551(1 ,4);2,523(9,6);2,518(13,8);2,510(175,5);2,505(375,8);2,501 (522,5);2,496(363,6);2,49 2.670 (3.0), 2.665 (2.1), 2.551 (1.4), 2.523 (9.6), 2.518 (13.8), 2.510 (175.5), 2.555 (375.8) 2.501 (522.5), 2.496 (363.6), 2.49
(2,3);2,327(3,1);2,323(2,2);2,072(0,8);1 ,143(7,9);1 ,136(5,6);1 ,126(16,0);1 ,108(8,0);1 ,061(7,8);1 ,043(14,9);^ (2,3); 2,327 (3,1); 2,323 (2,2); 2,072 (0.8); 1, 143 (7,9); 1, 136 (5,6); 1, 126 (16 , 0); 1, 108 (8,0); 1, 061 (7,8); 1, 043 (14,9); ^
0,009(2,1)  0.009 (2.1)
Beispiel 1689: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,299(1 ,1);8,183(0,5);8,163(0,6);7,696(0,5);7,661(2,0);7,643(3,0);7,623(1 ,6);7,612(2,7);7, 594(27)7,551 (1 ,7)7,533(1 ,8)7,404(1 ,0)7,381(1 ,8)7,358(0,9)7,319(3^ Example 1689: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.299 (1, 1), 8.183 (0.5), 8.163 (0.6), 7.696 (0.5), 7.661 ( 2.0); 7.643 (3.0); 7.623 (1, 6); 7.612 (2.7); 7, 594 (27) 7.551 (1, 7) 7.533 (1, 8) 7.404 (1, 0) 7.381 (1, 8) 7.358 (0.9) 7.319 (3 ^
,809(2,8);3,749(3,6);3,694(16,0);3,648(13,3);3,609(10,4);3,507(0,6);2,993(8,6);2,975(1 ,3);2,943(14,9);2,925(1 ,6);2,671(0,6);2,57^ , 809 (2.8); 3,749 (3.6); 3,694 (16.0); 3,648 (13.3); 3,609 (10.4); 3,507 (0.6); 2,993 (8.6); 2.975 (1, 3), 2.943 (14.9), 2.925 (1.6), 2.671 (0.6), 2.57 ^
27,0);2,525(1 ,9);2,520(2,6);2,512(32,1);2,507(68,5);2,502(94,8);2,498(67,2);2,493(31 ,0);2,329(0,6);2,073(0,8);0,008 2.525 (1, 9), 2.520 (2.6), 2.512 (32.1), 2.507 (68.5), 2.502 (94.8), 2.498 (67.2), 2.493 (31 , 0); 2,329 (0.6); 2,073 (0.8); 0,008
0,009(0,5)  0.009 (0.5)
Beispiel 1694: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,639(2,6)7,571 (1 ,3)7,551 (1 ,9)7,530(1 , 1)7,396(1 , 2)7,373(2,3)7,350(1 , 2);5,229(1 ,6);5,Example 1694: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.639 (2.6) 7.571 (1, 3) 7.551 (1.9) 7.530 (1.1) 7.396 (1, 2) 7,373 (2,3) 7,350 (1,2), 5,229 (1,6), 5,
220(1 ,4);4,447(0,6);4,411(0,6);4,326(0,9);4,202(1 ,7);4,185(5,3);4,167(5,7);4,150(2,2);4,134(1 ,5);4,123(0,7);4,116(1 ,5^ 220 (1,4); 4,447 (0,6); 4,411 (0,6); 4,326 (0,9); 4,202 (1, 7); 4,185 (5,3); 4,167 (5,7); 4,150 (2,2); 4,134 (1, 5); 4,123 (0,7); 4,116 (1, 5 ^
,088(1 ,4);4,079(0,6);4,061(0,5);3,435(0,9);3,404(1 ,1);3,359(0,8);3,344(0,6);3,339(0,9);3,306(189,6);3,27  0.088 (1, 4), 4.079 (0.6), 4.061 (0.5), 3.435 (0.9), 3.404 (1.1), 3.359 (0.8), 3.344 (0.6); 3,339 (0.9); 3,306 (189.6), 3.27
6);3,141(1 ,0);3,110(0,6);2,768(0,7);2,679(0,6);2,674(1 ,5);2,670(2,1);2,665(1 ,5);2,660(0,7);2,556(0,5^  3,141 (1, 0), 3,110 (0,6), 2,768 (0,7), 2,679 (0,6), 2,674 (1,5), 2,670 (2,1), 2,665 (1, 5 2.556 (0.5 ^); 2,660 (0.7)
5(252,2);2,501(354,3);2,496(249,9);2,491(112,1);2,456(0,8);2,452(0,7);2,337(0,7);2,332(1 ,5);2,327(2,1^  5 (252.2); 2.501 (354.3); 2.496 (249.9); 2.491 (112.1); 2,456 (0.8); 2,452 (0.7); 2,337 (0.7); 2,332 (1, 5); 2,327 (2,1 ^
3(1 ,0);2,085(0,6);2,072(1 ,9);2,055(0,7);1 ,710(2,3);1 ,677(2,8);1 ,583(0,6);1 ,551 (1 ,1);1 ,490(0,7);1 ,457(0,6);1 ,361(0,5);1 ,340(0,6);1 ,314(0,9);1 ,2 76(1 ,1);1 ,258(7,7);1 ,240(16,0);1 ,222(7,3);1 ,194(4,0);1 ,176(8,1);1 ,158(3,7);0,008(1 ,5);0,000(54,9);-0,009(1 ,6)  3 (1, 0); 2.085 (0.6); 2.072 (1, 9); 2.055 (0.7); 1, 710 (2.3); 1, 677 (2.8); 1, 583 ( 0.6); 1, 551 (1, 1); 1, 490 (0.7); 1, 457 (0.6); 1, 361 (0.5); 1, 340 (0.6); 1, 314 (0.9); 1, 2 76 (1, 1); 1, 258 (7.7); 1, 240 (16.0); 1, 222 (7.3); 1, 194 ( 4.0); 1, 176 (8.1); 1, 158 (3.7); 0.008 (1, 5); 0.000 (54.9); - 0.009 (1, 6)
Beispiel 1695: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,697(0,7);9,733(0,6);8,362(5,9);8,343(6,3)7,895(2,8)7,793(3,2);6,906(0,7);3,357(0,8);3Example 1695: 1 H NMR (400.0 MHz, de-DMSO): δ = 12.697 (0.7); 9.733 (0.6); 8.362 (5.9); 8.343 (6.3) 7.895 (2 , 8) 7,793 (3.2); 6,906 (0.7); 3,357 (0.8); 3
,354(1 ,3);3,339(2,3);3,305(424,8);3,278(4,0);3,261 (1 ,7);3,254(0,9);3,246(0,6);2,678(1 ,5);2,674(3,2);2,669(4,4);2,665(3,2);2,660(1 ,5);2,523(14, 354 (1, 3); 3,339 (2,3); 3,305 (424,8); 3,278 (4.0); 3,261 (1, 7); 3,254 (0.9); 3,246 (0.6); 2,678 (1,5), 2,674 (3,2), 2,669 (4,4), 2,665 (3,2), 2,660 (1,5), 2,523 (14
,1);2,518(20,1);2,509(251 ,9);2,505(544,5);2,500(761 ,4);2,496(535,6);2,491(242,4);2,444(1 ,1);2,336(1 ,5);2,332(3,3);2,327(4,5^ , 1), 2.518 (20.1), 2.509 (251, 9), 2.505 (544.5), 2.500 (761, 4), 2.496 (535.6), 2.491 (242.4), 2.444 (1, 1), 2,336 (1,5), 2,332 (3,3), 2,327 (4,5)
18(1 ,5);2,072(1 ,1);1 ,578(0,5); ,559(1 ,8); ,541 (3,5);1 ,524(3,6);1 ,506(2,0); ,488(0,6);0,928(7,3);0,909(16,0);0,891(6,5);0,008(1 ,3);0,000(45,5); 18 (1, 5): 2.072 (1,1); 1, 578 (0.5); , 559 (1, 8); , 541 (3.5); 1, 524 (3.6); 1, 506 (2.0); , 488 (0.6), 0.928 (7.3), 0.909 (16.0), 0.881 (6.5), 0.008 (1.3), 0.000 (45.5);
-0,009(1 ,4) -0.009 (1, 4)
Beispiel 1696: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,680(0,5);8,357(2,9);8,338(3,1);7,895(2,2);7,795(1 ,3);7,791(2,1);7,787(1 ,0);3,367(0,9);3Example 1696: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.680 (0.5), 8.357 (2.9), 8.338 (3.1), 7.895 (2.2), 7.795 ( 1, 3); 7,791 (2,1); 7,787 (1, 0); 3,367 (0,9); 3
,350(1 ,5);3,332(1 ,7);3,306(32,2);2,523(1 ,5);2,518(2,2);2,510(21 ,9);2,505(45,5);2,501(62,1);2,496(43,7);2,492(20,0);1 ,640(0^ , 350 (1,5), 3,332 (1,7), 3,306 (32,2), 2,523 (1,5), 2,518 (2,2), 2,510 (21, 9), 2,505 (45,5); 2,501 (62,1); 2,496 (43,7); 2,492 (20,0); 1,640 (0 ^
07(0,7);1 ,447(1 ,0);1 ,429(2,0);1 ,411(2,0);1 ,394(0,8);0,920(16,0);0,904(15,3);0,000(2,9)  07 (0.7); 1, 447 (1, 0); 1, 429 (2.0); 1, 411 (2.0); 1, 394 (0.8); 0.920 (16.0); 0.904 (15.3); 0,000 (2.9)
Beispiel 1698: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,405(1 ,2);8,386(1 ,3);8,362(1 ,1);8,343(1 ,3);7,955(13,6);7,951 (13,6);7,904(1 ,3);7,840(1 ,5); 7,791(1 ,0);7,713(8,2);7,708(14,4);7,703(7,3);7,572(4,9);7,554(5,3);7,152(0,8);3,588(0,7);3,440(2,5);3,422(6,9);3,405(7,0);3,387(2,9);3,310 9,5);3,195(2,6);3,177(6,3);3,160(6,3);3,142(2,3);2,674(2,4);2,670(3,3);2,665(2,2);2,523(9,6);2,518(14,1);2,510(184,9);2 Example 1698: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.405 (1.2), 8.386 (1.3), 8.362 (1, 1), 8.343 (1.3), 7.955 ( 13.6), 7.951 (13.6), 7.904 (1, 3), 7.840 (1.5); 7,791 (1, 0); 7,713 (8,2); 7,708 (14.4); 7,703 (7,3); 7,572 (4,9); 7,554 (5,3); 7,152 (0.8); 3,588 (0.7), 3.440 (2.5), 3.422 (6.9), 3.405 (7.0), 3.387 (2.9), 3.310 9.5), 3.195 (2.6), 3.177 (6 , 3); 3,160 (6.3); 3,142 (2.3); 2,674 (2.4); 2,670 (3.3); 2,665 (2.2); 2,523 (9.6); 2,518 (14, 1); 2,510 (184.9); 2
,8);2,496(391 ,2);2,491(174,3);2,451(1 ,2);2,332(2,3);2,327(3,3);2,323(2,1);2,085(2,5);2,072(4,2);1 ,14 , 8); 2,496 (391,2), 2,491 (174,3), 2,451 (1,2), 2,332 (2,3), 2,327 (3,3), 2,323 (2,1), 2,085 (2, 5); 2,072 (4,2); 1, 14
1 ,057(7,6);1 ,039(14,9);1 ,021(6,9);0,008(0,9);0,000(29,5)  1, 057 (7.6); 1, 039 (14.9); 1, 021 (6.9); 0.008 (0.9); 0.000 (29.5)
Beispiel 1699: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,960(1 ,5)7,729(3,3)7,609(0,9)7,590(1 ,0);7,544(0,8);7,527(0,8);4,227(5,2);4,092(3,3);3, 693(16,0);3,607(9,9);3,360(0,8);3,341(0,6);3,306(148,1);3,258(0,8);2,991(7,7);2,937(13,3);2,679(0,5);2,674(1 ,2);2,670(1 ,7);2,665(1 ,2);2,6 0,5);2,523(5,1);2,518(7,3);2,510(94,0);2,505(203,9);2,500(284,7);2,496(200,2);2,491(90,6);2,468(0,7);2,460(0,5);2,455(0,7 Example 1699: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.960 (1.5) 7.729 (3.3) 7.609 (0.9) 7.590 (1.0); 7.544 (0.8 7.527 (0.8); 4.227 (5.2); 4.092 (3.3); 3, 693 (16.0); 3.607 (9.9); 3.360 (0.8); 3.341 (0, 3.306 (148.1), 3.258 (0.8), 2.991 (7.7), 2.937 (13.3), 2.679 (0.5), 2.674 (1, 2), 2.670 (1, 7 2.665 (1, 2), 2.6 0.5), 2.523 (5.1), 2.518 (7.3), 2.510 (94.0), 2.505 (203.9), 2.500 (284.7 ); 2.496 (200.2); 2,491 (90.6); 2,468 (0.7); 2,460 (0.5); 2,455 (0.7
0,6);2,336(0,5);2,332(1 ,2);2,327(1 ,7);2,323(1 ,2);2,072(0,6);0,000(15,0) 0.6), 2.336 (0.5), 2.332 (1.2), 2.327 (1, 7), 2.233 (1.2), 2.072 (0.6), 0.000 (15.0)
Beispiel 1704: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,958(4,6)7,935(3,0)7,721 (5,9)7,572(2,2)7,553(2,6)7,546(2,0)7,527(1 ,6);5,231(1 ,6);5, 220(1 ,5);4,446(0,6);4,415(0,7);4,319(1 ,0);4,309(1 ,0);4,203(1 ,8);4,186(5,5);4,168(5,9);4,150(2,2);4,144(0,8);4,135(1 ,5);4
Figure imgf000113_0001
Figure imgf000114_0001
2);2,496(700,4);2,491 (308,2);2,451(1 ,8);2,332(4,0);2,327(5,9);2,323(4,0);0,008(1 ,5);0,000(49,5);-0,009(1 ,4) Example 1704: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.958 (4.6) 7.935 (3.0) 7.721 (5.9) 7.572 (2.2) 7.553 (2.6) 7,546 (2,0) 7,527 (1,6); 5,231 (1,6); 5,220 (1,5); 4,446 (0,6); 4,415 (0,7); 4,319 (1, 0); 4,309 (1, 0); 4,203 (1, 8); 4,186 (5,5); 4,168 (5,9); 4,150 (2,2); 4,144 (0.8); 4,135 (1, 5); 4
Figure imgf000113_0001
Figure imgf000114_0001
2), 2.496 (700.4), 2.491 (308.2), 2.451 (1.8), 2.322 (4.0), 2.327 (5.9), 2.233 (4.0), 0.008 (1.5 ); 0.000 (49.5); - 0.009 (1, 4)
Beispiel 1764: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,006 5,1);7,998(6,7);7,992(2,7);7,895(6,9);7,887(5,9);7,695(2,8);7,676(5,6);7,655(1 ,5);7, 640(4,2);7,621 (1 ,9);7,597(1 ,7);7,578(0,9);5,259(1 ,6);5,247(1 ,5);4,468(0,6);4,432(0,5);4,281(0,9);4,207(1 ,5);4,189(4,7);4,172(5,0);4,154(2,0);4 ,137(0,5);4,128(1 ,2);4,107(1 ,4);4,090(1 ,2);3,387(0,7);3,3£ 3(1 ,0);3,165(0,6);3,140(1 ,0);3,133(1 ,1);3,107(0,5);2,671(0,7);2,525(1 ,8);2,520(2,8); 2,511(46,5);2,507(102,4);2,502(143,6);2,498(101 ,1);2,493(46,4);2,334(0,7);2,329(0,9);2,325(0,7);2,197(0,9);2,162(1 ,0);2,086(16,0);2,074(0,6 );2,051(0,6);1 ,706(2,3);1 ,684(2,6);1 ,675(2,5);1 ,582(0,7);1 ,550(1 , 2);1 , 539(1 ,2); 1 , 532(0,9); 1 , 517(1 ,5);1 , 512(1 , 4);1 , 508(1 ,6);1 , 505(1 , 8);1 , 499(6, 5);1 ,496(4,8);1 ,489(7,0);1 ,477(3,4);1 ,472(3,9);1 , 469(5,4) 1 ,467(5,0);1 ,462(3,9);1 ,459(3,8);1 ,454(2,6);1 ,450(2,4);1 ,447(2,2); 1 ,436(1 ,8);1 ,429(1 ,3);1 ,391 (0,6);1 ,359(0,6); 1 ,320(0,7); 1 ,279(1 , 1 ); 1 ,260(6,5) ;1 ,242(13,3);1 ,225(6,3);1 ,188(2,9);1 ,170(5,6);1 ,152(2,7);0,961(4,6);0,958(5,8);0,944 (13,0);0,940(11 ,3);0,926(6,7);0,922(3,6);0,008(1 ,6);0,000 (58,5);-0,009(1 ,9) Example 1764: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.006 5.1); 7.998 (6.7); 7.992 (2.7); 7.895 (6.9); 7.877 (5 , 9); 7.695 (2.8); 7.676 (5.6); 7.655 (1, 5); 7, 640 (4.2); 7.621 (1, 9); 7.577 (1, 7); 5.975 (1, 6), 5.249 (1.5), 4.468 (0.6), 4.432 (0.5), 4.281 (0.9), 4.207 (1.5), 4.189 (4 4.172 (5.0); 4.154 (2.0); 4, 137 (0.5); 4.128 (1, 2); 4.107 (1, 4); 4.090 (1, 2); 3.387 (4) 0.7), 3.3 pounds 3 (1, 0), 3.165 (0.6), 3.140 (1, 0), 3.133 (1, 1), 3.107 (0.5), 2.671 (0.7) 2.525 (1.8), 2.520 (2.8); 2.511 (46.5), 2.507 (102.4), 2.502 (143.6), 2.498 (101, 1), 2.493 (46.4), 2.334 (0.7), 2.329 (0.9), 2.325 (0.7); 2.197 (0.9); 2.162 (1, 0); 2.086 (16.0); 2.074 (0.6); 2.051 (0.6); 1, 706 (2.3); 1, 684 (2,6); 1, 675 (2,5); 1, 582 (0.7); 1, 550 (1, 2); 1, 539 (1, 2); 1, 532 (0.9); 1, 517 (1, 5), 1, 512 (1, 4), 1, 508 (1, 6), 1, 505 (1, 8), 1, 499 (6, 5), 1, 496 (4 , 8); 1, 489 (7.0); 1, 477 (3.4); 1, 472 (3.9); 1, 469 (5.4) 1, 467 (5.0); 1, 462 (3.9); 1, 459 (3.8); 1, 454 (2.6); 1.450 (2.4); 1.447 (2.2); 1, 436 (1, 8); 1, 429 (1, 3); 1, 391 (0.6); 1, 359 (0.6); 1, 320 (0.7); 1, 279 (1, 1); 1, 260 (6.5); 1, 242 (13.3); 1, 225 (6.3); 1, 188 (2.9); 1, 170 (5.6); 1, 152 (2 , 0.961 (4.6), 0.958 (5.8), 0.944 (13.0), 0.940 (11, 3), 0.926 (6.7), 0.922 (3.6), 0.008 (1, 6); 0.000 (58.5); - 0.009 (1, 9)
Beispiel 1765: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,702 14,7);8,698(9,1);8,691(9,0);8,687(16,0);7,834(6,2);7,820(6,1);7,624(5,0);7,606(5,3); 7,361(0,5);7,024(0,8);3,559(3,5);3,311(8,8);3,210(3,5);3,C )28(2,5);3,015(3,6);3,000(2,7);2,671(0,7);2,524(2,3);2,519(3,4);2,510(47,3);2,506(10Example 1765: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.702 14.7), 8.698 (9.1), 8.691 (9.0), 8.687 (16.0), 7.834 (6 , 2), 7,820 (6.1); 7,624 (5.0); 7,606 (5.3); 7.361 (0.5), 7.024 (0.8), 3.559 (3.5), 3.311 (8.8), 3.210 (3.5), 3, C) 28 (2.5), 3.015 (3, 6); 3,000 (2.7); 2,671 (0.7); 2,524 (2.3); 2,519 (3.4); 2,510 (47.3); 2,506 (10
2,7);2,501 (143,4);2,497(101 ,3);2,492(46,2);2,328(0,9);1,e 72(0,9);1 ,644(3,6);1 ,630(3,3);1 ,605(3,8);1 ,593(3,8);1 ,579(2,9);1 ,565(2,3);1 ,512(4,4) ;0,008(1 ,9);0,000(58,5);-0,009(1 ,8) 2.71), 2.501 (143.4), 2.497 (101, 3), 2.492 (46.2), 2.328 (0.9), 1, e 72 (0.9), 1, 644 (3.6 1, 630 (3,3); 1, 605 (3,8); 1, 593 (3,8); 1, 579 (2,9); 1, 565 (2,3); 1, 512 (4.4); 0.008 (1, 9); 0.000 (58.5); - 0.009 (1, 8)
Beispiel 1766: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,166(1 ,2);8,148(1 ,3);7,837(3,4);7,817(3,4);7,596(4,1);7,574(4,6);7,566(16,0);7,561(5,5);7Example 1766: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.166 (1.2), 8.148 (1.3), 7.837 (3.4), 7.817 (3.4), 7.596 ( 4.1); 7,574 (4.6); 7,566 (16.0); 7,561 (5.5); 7
,557(5,2);7,549(4,8);7,545(13,3);7,538(5,6);3,789(5,8);3,553(3,1);3,305(58,2);3,214(3,2);2,669(2,0);2,523(6,9);2,518(10,0);2,510(125,8)^, 557 (5.2); 7,549 (4.8); 7,545 (13.3); 7,538 (5.6); 3,789 (5.8); 3,553 (3.1); 3,305 (58.2); 3,214 (3.2); 2,669 (2.0); 2,523 (6.9); 2,518 (10.0); 2,510 (125.8) ^
5(268,5);2,500(371 ,3);2,496(259,5);2,491(117,4);2,328(2,0);2,072(2,9);1 ,600(3,4);1 ,504(5,1);0,000(63,4) 5 (268.5), 2.500 (371, 3), 2.496 (259.5), 2.491 (117.4), 2.328 (2.0), 2.072 (2.9), 1. 600 (3.4) ; 1, 504 (5.1); 0.000 (63.4)
Beispiel 1767: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,774 4,1);7,543(7,0);7,525(7,6);7,507(2,4);7,498(9,1);7,495(8,1);7,487(13,6);7,481 (16,0); 7,471(1 ,7);6,665(0,8);3,550(3,3);3,325(14,1);3,229(3,5);2 670(1 , 1);2,523(3,7);2,518(5,5);2,510(76,8);2,505(165,6);2,500(229,8);2,496(161 ,1); 2,491 (72,9);2,332(1 ,2);2,327(1 ,4);1 ,601 (3,7);1 ,591 (3,7);1 510(5,7);0,008(2,8);0,000(85,7);-0,009(2,4) Example 1767: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.774 4.1); 7.543 (7.0); 7.525 (7.6); 7.507 (2.4); 7.498 (9 , 1); 7,495 (8,1); 7,487 (13,6); 7,481 (16,0); 7.471 (1, 7), 6.665 (0.8), 3.550 (3.3), 3.325 (14.1), 3.229 (3.5), 2 670 (1, 1), 2.523 (3.7); 2.518 (5.5), 2.510 (76.8), 2.555 (165.6), 2.500 (229.8), 2.496 (161, 1); 2.491 (72.9), 2.332 (1,2), 2,327 (1,4), 1,601 (3,7), 1, 591 (3,7), 1,510 (5,7), and 0,008 (2 , 8); 0.000 (85.7) - 0.009 (2.4)
Beispiel 1768: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,282(0,6);8,009(0,6 );7,522(3,7);7,505(3,8);7,445(0,6);7,442(0,9);7,439(0,6 );7,031(0,6);3, 531(4,4);3,449(1 ,1);3,435(1 ,2);3,386(0,7);3,333(28,9);3,153(4,4);3,012( 4,6);2,676(0,8);2,671(1 ,1);2,667(0,8);2,563(0,6);2,559( 0,7);2,525(1 ,8); 2,520(3,0);2,511(60,0);2,507(131 ,2);2,502(181 ,1);2,497(131 ,9);2,493(6, 5,3);2,456(4,5);2,452(4,6);2,395(0,8);2,390(0,7);2,333( D,8);2,329(1 ,1);Example 1768: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.282 (0.6), 8.009 (0.6), 7.522 (3.7), 7.555 (3.8), 7.445 ( 0.6), 7.442 (0.9), 7.439 (0.6), 7.031 (0.6), 3.531 (4.4), 3.449 (1.1), 3.435 (1.2), 3.386 (0.7); 3.333 (28.9); 3.153 (4.4); 3.012 (4.6); 2.676 (0.8); 2.671 (1, 1); 2.667 (0.8); 2.563 ( 0.6), 2.559 (0.7), 2.525 (1, 8); 2.520 (3.0), 2.511 (60.0), 2.507 (131, 2), 2.502 (181, 1), 2.497 (131, 9), 2.493 (6, 5.3), 2.456 (4.5) 2.452 (4.6); 2.355 (0.8); 2.390 (0.7); 2.333 (D, 8); 2.329 (1, 1);
2,324(0,8);2,086(0,7);1 ,671 (1 ,1 );1 ,656(2,8);1 ,643(5 ,4); 1 ,629(4,5); 1 ,614 3,4);1 ,585(8,5);1 ,573(9,3);1 ,533(3,0);1 ,495(9,6);1 ,480 (15,2);1 , 473(16 ,0);1 ,460(10,8);1 ,449(7,6);1 ,432(8,2); 1 ,425(9,3); 1 ,412(5,2);1 ,388(1 ,5);1 365(1 ,7); 1 ,344(4, 1 ); 1 ,329(8,2); 1 , 321 (11 ,2);1 , 306(10,5 );1 ,301(7,2);1 ,2 84(3,0);0,000(14,8);-0,009(0,7) 2,324 (0.8); 2.086 (0.7); 1, 671 (1, 1); 1, 656 (2.8); 1, 643 (5, 4); 1, 629 (4,5); 1, 614, 3.4); 1, 585 (8.5); 1, 573 (9.3); 1, 533 (3.0); 1, 495 (9.6); 1, 480 (15, 2); 1, 473 (16, 0); 1, 460 (10.8); 1, 449 (7.6); 1, 432 (8.2); 1, 425 (9,3); 1, 412 (5.2); 1, 388 (1, 5); 1 365 (1, 7); 1, 344 (4, 1); 1, 329 (8,2); 1, 321 (11, 2); 1, 306 (10.5); 1, 301 (7.2); 1, 2 84 (3.0); 0.000 (14.8); - 0.009 (0.7 )
Beispiel 1769: 1H-NMR(400,0 MHz, de-DMSO): δ= 11 ,666(0,8);7,347(2, 2);7,329(2,4);6,073(0,9);3,503(2,9);3,324(26,9);3,276(( ),7);3,158(3,2); 3,027(2,0);3,014(2,9);2,999(2,3);2,556(0,6);2,552(0,8);2,525(0,9);2,520 1 ,4);2,511 (26,5);2,507(57,9);2,502(79,8);2,497(56,9);2 ,493(27,2);2,4 63(2,0);2,458(2,1);2,453(1 ,9);2,449(1 ,4);2,444(0,9);1 ,671 (0,6);1 ,657(1 ,4 );1 ,642(2,7);1 ,629(2,2);1 ,614(1 ,2);1 ,576(3,9);1 ,563(4 l);1 , 550(3,0); 1 , 470(4,5);1 ,339(16,0);0,939(3,3);0,703(2,4);0,692(6,5);0,688(6,8);0,677( 2,2);0,008(0,9);0,000(32,6);-0,009(1 ,2) Example 1769: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11, 666 (0.8); 7.347 (2, 2); 7.329 (2.4); 6.073 (0.9); 3.303 (2.9), 3.324 (26.9), 3.276 ((), 7), 3.158 (3.2); 3.027 (2.0), 3.014 (2.9), 2.999 (2.3), 2.556 (0.6), 2.552 (0.8), 2.525 (0.9), 2.520 1, 4); 2.507 (57.9), 2.502 (79.8), 2.497 (56.9), 2.493 (27.2), 2.4 63 (2.0), 2.458 (2.1 2,443 (1, 9), 2,449 (1,4), 2,444 (0,9), 1, 671 (0,6), 1,657 (1,4), 1,642 (2,7); 1, 629 (2.2); 1, 614 (1, 2); 1, 576 (3.9); 1, 563 (4 l); 1, 550 (3.0); 1, 470 (4.5), 1, 339 (16.0), 0.939 (3.3), 0.703 (2.4), 0.692 (6.5), 0.688 (6.8), 0.677 (2, 2), 0.008 (0.9), 0.000 (32.6), - 0.009 (1, 2)
Beispiel 1770: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,270(0,9);8,250(0, 9)7,408(1 ,5);6,352(1 ,0);3,651 (0,7);3,520(7,2);3,396(6 0);3,344(168,2 );3,296(7,6);3,242(2,5);3,147(7,1);3,015(6,3);2,987(2,5);2,675(3,4);2,67 D(4,5);2,666(3,3);2,602(1 ,9);2,561(10,5);2,557(14,2);2, 552(13,7);2,54 8(6,9);2,543(2,2);2,524(28,8);2,510(290,7);2,506(562,6);2,501(730,1);2 497(514,0);2,492(243,9);2,461(23,8);2,456(26,0);2,452(25,0);2,447(1 7,5);2,443(11 ,2);2,401 (9,0);2,337(2,1);2,333(3,4);2,328(4,4);2,324(3,2); 2,086(16,0);1 ,669(2,0);1 ,641(7,5);1 ,627(6,4);1 ,614(4,9 );1 , 583(11 ,0);1 , 569(11 ,6);1 ,475(14,3);1 ,391 (7,9);1 ,193(0,7);1 ,175(1 ,4);1 ,157(1 ,3);0,008 (0,9);0,000(22,6);-0,009(1 ,1);-0,050(0,6) Example 1770: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.270 (0.9), 8.250 (0.9) 7.408 (1.5), 6.352 (1.0), 3.651 (0 , 7), 3.520 (7.2), 3.396 (6 0), 3.344 (168.2), 3.296 (7.6), 3.242 (2.5), 3.147 (7.1), 3.015 (6.3 2.987 (2.5), 2.675 (3.4), 2.67 D (4.5), 2.666 (3.3), 2.602 (1.9), 2.561 (10.5), 2.557 (14 , 2), 2, 552 (13.7), 2.54 8 (6.9), 2.543 (2.2), 2.524 (28.8), 2.510 (290.7), 2.506 (562.6) 2.501 (730.1), 2 497 (514.0), 2.492 (243.9), 2.461 (23.8), 2.456 (26.0), 2.452 (25.0), 2.447 (1 7.5 2,443 (11, 2); 2,401 (9,0); 2,337 (2,1); 2,333 (3,4); 2,328 (4,4); 2,324 (3,2); 2.086 (16.0); 1.669 (2.0); 1.641 (7.5); 1.627 (6.4); 1.614 (4.9); 1.583 (11.10) 1, 569 (11, 6), 1, 475 (14.3), 1, 391 (7.9), 1, 193 (0.7), 1, 175 (1, 4), 1, 157 (1, 3); 0.008 (0.9); 0.000 (22.6); - 0.009 (1, 1); - 0.050 (0.6)
Gegenstand der vorliegenden Erfindung ist demnach die Verwendung mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus substituierten The present invention accordingly provides for the use of at least one compound selected from the group consisting of substituted
Pyridoncarboxamiden der allgemeinen Formel (I), sowie von beliebigen Mischungen dieser erfindungsgemäß substituierten Pyridoncarboxamide der allgemeinen Formel (I) mit ein oder mehreren agrochemischen Wirkstoffen entsprechend der unten stehenden Definition, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber Pyridonecarboxamiden of the general formula (I), and of any mixtures of these inventively substituted pyridone carboxamides of the general formula (I) with one or more agrochemical active ingredients as defined below, to increase the resistance of plants
abiotischem, nicht durch Pestizide, bevorzugt nicht durch Herbizide ausgelösten Stress, insbesondere zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. abiotic, not by pesticides, preferably not by herbicides-induced stress, in particular to enhance plant growth and / or increase the plant yield.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem, nicht durch Pestizide, bevorzugt nicht durch Herbizide ausgelösten Stresswirksame Menge von mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus substituierten Pyridoncarboxamiden der allgemeinen Formel (I). Zu den dabei relativierbaren abiotischen Stressbedingungen können zum Beispiel Dürre, Kälte- und Hitzebedingungen, osmotischer Stress, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Another object of the present invention is a spray solution for the treatment of plants, containing a plant effective against abiotic, not by pesticides, preferably not triggered by herbicides stress effective amount of at least one compound selected from the group consisting of substituted Pyridoncarboxamiden of the general formula (I). For example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions,
Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen zählen. High light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
In einer Ausführungsform kann beispielsweise vorgesehen sein, dass die For example, in one embodiment, it may be provided that the
erfindungsgemäß genannten substituierten Pyridoncarboxamide der allgemeinen Formel (I), durch eine Sprühapplikation auf entsprechende zu behandelnde Pflanzen oder Pflanzenteile aufgebracht werden. Die erfindungsgemäß vorgesehene Substituted Pyridoncarboxamide according to the invention of the general formula (I), be applied by a spray application to appropriate plants or plant parts to be treated. The inventively provided
Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) erfolgt vorzugsweise mit einer Dosierung zwischen 0,0005 und 3 kg/ha, besonders bevorzugt zwischen 0,001 und 2 kg/ha, insbesondere bevorzugt zwischen 0,005 und 1 kg/ha. Wenn im Rahmen der vorliegenden Erfindung Abscisinsäure gleichzeitig mit substituierten Pyridoncarboxamiden der allgemeinen Formel (I), beispielsweise in Rahmen einer gemeinsamen Zubereitung oder Formulierung verwendet wird, so erfolgt die Zumischung von Abscisinsäure dabei vorzugsweise in einer Dosierung zwischen 0,001 und 3 kg/ha, besonders bevorzugt zwischen 0,005 und 2 kg/ha, insbesondere bevorzugt zwischen 0,01 und 1 kg/ha. Use of the compounds of general formula (I) according to the invention is preferably carried out with a dosage between 0.0005 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha. If abscisic acid is used simultaneously with substituted pyridone carboxamides of the general formula (I), for example in the context of a common preparation or formulation, the addition of abscisic acid is preferably carried out at a dosage of between 0.001 and 3 kg / ha, more preferably between 0.005 and 2 kg / ha, particularly preferably between 0.01 and 1 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: verbessertesIn 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
Wurzelwachstum hinsichtlich Oberfläche und Tiefe, vermehrte Ausläuferbildung oder Bestückung, stärkere und produktivere Ausläufer und Bestockungstriebe, Root growth in terms of surface and depth, increased tailing or assembly, stronger and more productive foothills and tillers,
Verbesserung des Sproßwachstums, erhöhte Standfestigkeit, vergrößerte Improvement of shoot growth, increased stability, increased
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 Sprout 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 components of any kind or better digestibility, improved storage stability of the crop, improved tolerance against unfavorable temperatures, improved tolerance to drought and dryness, as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soils and water, increased
Toleranz gegenüber Ozonstress, verbesserte Verträglichkeit gegenüber Herbiziden und anderen Pflanzenbehandlungsmitteln, verbesserte Wasseraufnahme und Tolerance to ozone stress, improved tolerance to herbicides and other plant treatment agents, 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. 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.
Insbesondere zeigt die erfindungsgemäße Verwendung in der Sprühapplikation auf Pflanzen und Pflanzenteilen die beschriebenen Vorteile. Kombinationen der erfindungsmäß substituierten Pydridoncarboxamide der allgemeinen Formel (I) unter anderem mit Insektiziden, Lockstoffen, Akariziden, Fungiziden, Nematiziden, wachstumsregulierenden Stoffen, Safenern, die Pflanzenreife beeinflussenden Stoffen und Bakteriziden können bei der Bekämpfung von Pflanzenkrankheiten im Rahmen der vorliegenden Erfindung ebenfalls Anwendung finden. Die kombinierte Verwendung von entsprechenden substituierten Pydridoncarboxamiden der allgemeinen Formel (I) mit gentechnisch veränderten Sorten in Bezug auf erhöhte abiotische Stresstoleranz ist darüber hinaus ebenfalls möglich. In particular, the use according to the invention in the spray application to plants and parts of plants shows the advantages described. Combinations of the invention substituted Pydridoncarboxamide the general formula (I), inter alia with insecticides, attractants, acaricides, fungicides, nematicides, growth regulators, safeners, the plant maturity affecting substances and bactericides can also be used in the control of plant diseases in the present invention. The combined use of corresponding substituted Pydridoncarboxamiden 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. Solche Begriffe sind beispielsweise die nachfolgend aufgeführten The various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Such terms are, for example, those listed below
Bezeichnungen: phytotonischer Effekt, Widerstandsfähigkeit gegenüber Terms: phytotonic effect, resistance to
Stressfaktoren, weniger Pflanzenstress, Pflanzengesundheit, gesunde Pflanzen, Pflanzenfitness, („Plant Fitness"),„Plant Wellness",„Plant Concept",„Vigor Effect", „Stress Shield", Schutzschild,„Crop Health",„Crop Health Properties",„Crop Health Products",„Crop Health Management",„Crop Health Therapy",„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. Inn Rahmen der vorliegenden Erfindung wird unter einem guten Effekt auf die 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 Management", "Plant Health Therapy", Greening Effect (" Greening effect "or" re-greening effect ")," Freshness "or other terms that are well known to a person skilled in the art. Inn frame of the present invention is under a good effect on the
Widerstandsfähigkeit gegenüber abiotischem Stress nicht beschränkend mindestens ein um im Allgemeinen 3 %, insbesondere größer als 5 %, besonders bevorzugt größer als 10 % verbessertes Auflaufen, Resistance to abiotic stress not limited to at least one accumulation, generally improved by 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,  at least one generally 3%, in particular greater than 5%, particularly preferably greater than 10% increased yield,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 %, besonders bevorzugt größer als 10 % verbesserte Wurzelentwicklung,  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 %, · At least one in general 3%, in particular greater than 5%,
besonders bevorzugt größer als 10 % ansteigende Sproßgröße,  more preferably greater than 10% increasing shoot size,
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 generally improved by 3%, in particular greater than 5%, more preferably greater than 10%, photosynthesis 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.  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 desired combination of two or more effects.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge von mindestens einer A further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
Verbindung der allgemeinen Formel (I). Die Sprühlösung kann andere übliche Compound of the general formula (I). The spray solution may be other common
Bestandteile aufweisen, wie Lösungsmittel, Formulierhilfsstoffe, insbesondere Wasser, enthalten. Weitere Bestandteile können unter anderem agrochemische Wirkstoffe sein, welche unten noch weiter beschrieben werden. Have constituents such as 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 Another object of the present invention is the use of
entsprechenden Sprühlösungen zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. Die nachfolgenden Ausführungen gelten sowohl für die erfindungsgemäße Verwendung der Verbindungen der allgemeinen Formel (I) an sich als auch für die entsprechenden Sprühlösungen. corresponding spray solutions to increase the resistance of plants to abiotic stress factors. The following explanations apply both for the inventive use of the compounds of general formula (I) per se and for the corresponding spray solutions.
Erfindunsgemäß wurde darüber hinaus gefunden, dass die Anwendung der According to the invention, it has also been found that the application of the
Verbindungen der allgemeinen Formel (I) in Kombination mit mindestens einemCompounds of general formula (I) in combination with at least one
Düngemittel wie weiter unten stehend definiert auf Pflanzen oder in deren Umgebung möglich ist. Fertilizers as defined below are possible on plants or in their environment.
Düngemittel, die erfindungsgemäß zusammen mit den oben näher erläuterten Fertilizers according to the invention together with the above explained in more detail
Verbindungen der allgemeinen Formel (I) verwendet werden können, sind im Compounds of the general formula (I) can be used are in
Allgemeinen organische und anorganische Stickstoff-haltige Verbindungen wie beispielsweise Harnstoffe, Harnstoff-Formaldehyd-Kondensationsprodukte, General organic and inorganic nitrogen-containing compounds such as, for example, ureas, urea-formaldehyde condensation products,
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 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). To name in particular are in this
Zusammenhang die NPK-Dünger, d.h. Düngemittel, die Stickstoff, Phosphor und Kalium enthalten, Kalkammonsalpeter, d.h. Düngemittel, die noch Calcium enthalten, Ammonsulfatsalpeter (Allgemeine Formel (NH4)2SO4 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. Related to NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2SO 4 NH 4 NO 3), ammonium phosphate and ammonium sulphate. 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 B1 und Indol-(lll)essigsäure) oder Gemische davon enthalten. Erfindungsgemäß eingesetzte Düngemittel können auch weitere Salze wie Monoammoniumphosphat (MAP), Diammoniumphosphat (DAP), Kaliumsulfat, 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,
Kaliumchlorid, Magnesiumsulfat enthalten. Geeignete Mengen für die sekundären Nährstoffe oder Spurenelemente sind Mengen von 0,5 bis 5 Gew.-%, bezogen auf das gesamte Düngemittel. Weitere mögliche Inhaltsstoffe sind Pflanzenschutzmittel, Insektizide oder Fungizide, Wachstumsregulatoren oder Gemische davon. Hierzu folgen weiter unten weitergehende Ausführungen. 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 Stickstoffdüngemittel eingesetzt werden. Weitere mögliche Inhaltsstoffe für Düngemittel sind beispielsweise in Ullmann's Containing 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 fertilizer. Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below. 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, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, 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,  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 described. The general composition of the fertilizers, which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
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. 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% by weight) 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 kann das Düngemittel sowie die Verbindungen der allgemeinen Formel (I) zeitgleich, d.h. synchron, verabreicht werden. Es ist jedoch auch möglich, zunächst das Düngemittel und dann eine Verbindung der allgemeinen Formel (I) oder zunächst eine Verbindung der allgemeinen Formel (I) und dann das Düngemittel anzuwenden. Bei nicht zeitgleicher Anwendung einer Verbindung 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 der erfindungsgemäßen Verbindung der allgemeinen 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.  In the context of the present invention, the fertilizer and the compounds of the general formula (I) can be used simultaneously, i. synchronously, administered. However, it is also possible to use first the fertilizer and then a compound of the general formula (I) or first a compound of the general formula (I) and then the fertilizer. In the case of non-simultaneous application of a compound of the general formula (I) and of the fertilizer, however, the application is carried out in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours , even more special 4 hours, even more special within 2 hours. In very particular embodiments of the present invention, the use of the compound of the general 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.
Die erfindungsgemäß zu verwendenden Wirkstoffe können, gegebenenfalls in The active compounds to be used according to the invention can, optionally in
Kombination mit Düngemitteln, bevorzugt an folgenden Pflanzen angewendet werden, wobei die folgende Aufzählung nicht beschränkend ist. Bevorzugt sind 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 Combined with fertilizers, preferably applied to the following plants, the following list is not limiting. Preference is given to plants from the group of crops, 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
Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln, Treibstoffe oder für technische Zwecke eingesetzt werden.  Crop plants used as plants for the production of food, feed, fuel or for technical purposes.
Zu den Nutzpflanzen zählen z. B. folgende Pflanzenarten: Triticale, Durum Among the useful plants include z. For example, the following plant species: Triticale, Durum
(Hartweizen), Turf, Reben, Getreide, beispielsweise Weizen, Gerste, Roggen, Hafer, Höpen, Reis, Mais und Hirse; Rüben, beispielsweise Zuckerrüben und Futterrüben; Früchte, beispielsweise Kernobst, Steinobst und Beerenobst, beispielsweise Äpfel, Birnen, Pflaumen, Pfirsiche, Mandeln, Kirschen und Beeren, z. B. Erdbeeren, (Durum wheat), turf, vines, cereals, for example wheat, barley, rye, oats, hops, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries,
Himbeeren, Brombeeren; Hülsenfrüchte, beispielsweise Bohnen, Linsen, Erbsen und Sojabohnen; Ölkulturen, beispielsweise Raps, Senf, Mohn, Oliven, Sonnenblumen, Kokos, Castorölpflanzen, Kakaobohnen und Erdnüsse; Gurkengewächse, Raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucumber plants,
beispielsweise Kürbis, Gurken und Melonen; Fasergewächse, beispielsweise for example, pumpkin, cucumbers and melons; Fiber plants, for example
Baumwolle, Flachs, Hanf und Jute; Citrusfrüchte, beispielsweise Orangen, Zitronen, Pampelmusen und Mandarinen; Gemüsesorten, beispielsweise Spinat, (Kopf)-Salat, Spargel, Kohlarten, Möhren, Zwiebeln, Tomaten, Kartoffeln und Paprika; Cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers;
Lorbeergewächse, beispielsweise Avocado, Cinnamonum, 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.  Laurel family, such as avocado, cinnamonum, camphor, or as plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
Als besonders geeignete Zielkulturen für die Anwendung des erfindungsgemäßen Verfahrens sind folgende Pflanzen anzusehen: Hafer, Roggen, Triticale, Durum, Bamwolle, 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. Oats, rye, triticale, durum, bamboo wool, aubergine, turf, pome fruit, stone fruit, berry fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals are to be regarded as particularly suitable target cultures for the application of the method according to the invention , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
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.. Examples of trees which can be improved according to the process 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. 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 tree 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. 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. nitens, E. obliqua, E. regnans, E. pilularus.
Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen As particularly preferred trees, according to the invention
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. Methods can be improved can be mentioned: From the tree 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 As particularly preferred trees, according to the invention
Verfahren verbessert werden können, können genannt werden: Rosskastanie, Procedures can be improved: horse chestnut,
Platanengewächs, Linde und Ahornbaum. Sycamore plant, linden and maple tree.
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); 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 Sibth.), "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.), "smooth bromegrass" (Bromus inermis Leyss.), Schilf ("cattails") wie "Timothy" (Phleum pratense L.), "sand cattail" (Phleum subulatum L.), 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.), reeds ("cattails") such as "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.). "orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) and "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 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 Use is generally preferred Bleach grass, ostrich grass and "redtop", fescue and lolk are particularly preferred
insbesondere bevorzugt. especially preferred.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten ver- steht 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 Optimierungsmethoden oder durch biotechno- logische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Among plant varieties plants are grown with new properties ("traits"), which have been bred either by conventional breeding, by mutagenesis or by means of recombinant DNA techniques. Crop plants can accordingly be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety protection rights.
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 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 that is provided or assembled outside the plant and that when introduced into the plant
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 erfindungsgemäß behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (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 that are preferably treated according to the invention include all plants which have genetic material that these plants
besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Pflanzen und Pflanzensorten, die ebenfalls erfindungsgemäß behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Stressfaktoren resistent sind. Zu den abiotischen Stressbedingungen können zum Beispiel Dürre, Kälte- und Hitzebedingungen, osmotischer Stress, Staunässe, erhöhter gives particularly advantageous, useful features (regardless of whether this was achieved through breeding and / or biotechnology). Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors. For example, drought, cold and heat conditions, osmotic stress, waterlogging, elevated water levels, etc. can all contribute to abiotic stress
Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen. Pflanzen und Pflanzensorten, die ebenfalls erfindungsgemäß behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Soil salt content, increased exposure to minerals, ozone conditions, High light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients or avoidance of shadows. Plants and plant varieties which can also be treated 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 Plant physiology, improved plant growth and improved
Pflanzenentwicklung, wie Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserterPlant development, such as water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved
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, Photosynthesis, increased germination and accelerated Abreife based. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling vigor, plant size,
Internodienzahl und -abstand, Wurzelwachstum, Samengröße, Fruchtgröße, Internode number and distance, root growth, seed size, fruit size,
Schotengröße, Schoten- oder Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen  Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability. Other income characteristics include
Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehalt, Ölgehalt und Seed composition such as carbohydrate content, protein content, oil content and
Ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit. Oil composition, nutritional value, reduction of nontoxic compounds, improved processability and improved shelf life.
Pflanzen, die erfindungsgemäß ebenfalls behandelt werden können, sind Plants which can also be treated according to the invention are
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 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 Hybrid plants that already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be removed (eg in maize) by delaving (i.e., mechanical removal of the males)
Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Pollensterilität auf genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Sex organs or the male flowers) are produced; however, it is more common for male sterility to be due to genetic determinants in the plant genome based. In this case, especially if it is the desired
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 It is usually beneficial to ensure that product is harvested from the hybrid plants that are the seeds, to ensure that pollen fertility is fully restored in hybrid plants that contain the genetic determinants responsible for male sterility. This can be achieved by ensuring that the male cross-breeding partners possess appropriate fertility restorer genes capable of controlling the pollen fertility in hybrid plants that are the genetic source
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 Determinants responsible for the pollensity of the poll include restorative. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been reported, for example
Brassica-Arten beschrieben (WO 1992/005251 , WO 1995/009910, WO 1998/27806, 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 Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 1991/002069).  Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, 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 is selectively expressed in the tapetum cells in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 1991/002069).
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die erfindungsgemäß ebenfalls 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 methods of plant biotechnology, such as genetic engineering) which can also be treated 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. Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. 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 Bakteriums 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 2000/066747 oder WO 2002/026995 beschrieben ist. Plants tolerant to the herbicide glyphosate or its salts. 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 responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481). , for an EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280- 4289) or for an EPSPS from Eleusine (WO 2001/66704) encode. It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 2000/066746, WO 2000/066747 or WO 2002/026995.
Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme as described in US Pat
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 5,776,760 and US 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. WO 2002/036782, WO
2003/092360, WO 2005/012515 und WO 2007/024782 beschrieben ist, kodiert. 2003/092360, WO 2005/012515 and WO 2007/024782.
Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 2001/024615 oder WO 2003/013226 beschrieben sind, enthalten, selektiert. 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 2001/024615 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 5,739,082; US 5,908,810 und US 7,1 12,665 beschrieben. Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes HPPD-Enzym gemäß WO 1996/038567, WO 1999/024585 und WO 1999/024586 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 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 and US 7,112,665. Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). The hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants that are tolerant to HPPD inhibitors can be used with a gene coding for a naturally occurring resistant HPPD enzyme or a gene coding for a mutant HPPD enzyme according to WO 1996/038567, WO 1999/024585 and WO 1999/024586. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that promote the formation of HPPD inhibitors
Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 1999/034008 und WO  Allow homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 1999/034008 and 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. 2002/36787 described. 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.
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, 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)benzoate und/oder Sulfonylaminocarbonyltriazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als 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 Acetohydroxy acid synthase, AHAS, known) a tolerance to
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 5,605,01 1 , 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 5,605,01 1 ; US 5,013,659; US 5,141 ,870; US 5,767,361 ; different herbicides or groups of herbicides, as described, for example, by Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US Pat. Nos. 5,605,011, 5,378,824, 5,141,870 and 5,013,659. is described. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011 1; 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 5,731,180; US 5,304,732; US 4,761,373; US 5,331, 107; US 5,928,937; and
US 5,378,824; sowie in der internationalen Veröffentlichung WO 1996/033270 beschrieben. Weitere imidazolinontolerante Pflanzen sind auch in z. B. US 5,378,824; as well as in international publication WO 1996/033270. Other imidazolinontolerante plants are also in z. B.
WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, 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 imidazolinontolerante Pflanzen sind auch in z.B. WO 2007/024782 beschrieben. WO 2006/007373, WO 2006/015376, WO 2006/024351 and WO 2006/060634. Other sulfonylurea and imidazolinone tolerant plants are also disclosed in e.g. WO 2007/024782 described.
Weitere Pflanzen, die gegenüber Imidazolinon und/oder Sulfonylharnstoff 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 1997/41218, für die Zuckerrübe in US 5,773,702 und WO 1999/057965, für Salat in US 5,198,599 oder für die Sonnenblume in WO 2001/065922 beschrieben ist. Other plants which are tolerant to imidazolinone and / or sulphonylurea may be induced by induced mutagenesis, selection in cell cultures in the presence of the Herbicides or by mutational breeding, as for example for the soybean in US 5,084,082, for rice in WO 1997/41218, for the sugar beet in US 5,773,702 and WO 1999/057965, for salad in US 5,198,599 or for the sunflower in WO 2001 / 065922 is described.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Insektenresistenz verleiht, erhalten werden. Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated 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 obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
Der Begriff "insektenresistente transgene Pflanze" umfaßt im vorliegenden The term "insect-resistant transgenic plant" as used herein
Zusammenhang jegliche Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfaßt, die für folgendes kodiert: Relates to any 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, Cryl F, Cry2Ab, Cry3Ae oder Cry3Bb oder Insektizide Teile davon; oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, 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. Biotechnol. (2001 ), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71 , 1765-1774); oder 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 Environment Microb. (2006), 71, 1765-1774); or
3) ein Insektizides Hybridprotein, das Teile von zwei unterschiedlichen Insektiziden 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 Cry1A.105, das von dem Mais-Event MON98034 produziert wird (WO 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. B. the Protein Cry1A.105 produced by maize event MON98034 (WO
2007/027777); oder 2007/027777); or
4) ein Protein gemäß einem der Punkte 1 ) bis 3) oben, in dem einige, 4) a protein according to any one of items 1) to 3) above, in which some,
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 Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden, wie das Protein Cry3Bb1 in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 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 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative
insektentoxischen Proteine (vegetative insecticidal proteins, VIP), die unter folgendem Link angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa: insecticidal proteins (VIP) listed 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 1994/21795); 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 1994/21795); or
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 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, 8) a protein according to any one of items 1) to 3) above, in which some,
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 Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden (wobei die Kodierung für ein Insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll-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 Ausführungsform 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 In particular, 1 to 10, amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation (retaining coding for an insecticidal protein) such as protein VIP3Aa in cotton event COT 102. 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 develop a protein
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 To delay insect resistance to plants by using different proteins which are insecticidal for the same target insect species, but a different mode of action, such as binding to different ones
Rezeptorbindungsstellen im Insekt, aufweisen. Receptor binding sites in the insect.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind gegenüber abiotischen Stressfaktoren tolerant. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Stressresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Stresstoleranz zählen folgende: 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 Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant to abiotic stressors. 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 which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
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  To reduce plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5. b. Plants that contain a stress tolerance enhancing transgene that the
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-To reduce expression and / or activity of PARG-encoding genes of plants or plant cells, as described e.g. in WO 2004/090140 is described; c. Plants containing a stress tolerance enhancing transgene which is useful for a plant functional enzyme of the nicotinamide adenine dinucleotide salvage
Biosynthesewegs kodiert, darunter Nicotinamidase, Biosynthetic pathway, including nicotinamidase,
Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotid-adenyltransferase, Nicotinamidadenindinukleotidsynthetase oder Nicotinamidphosphoribosyl-transferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist. Nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as this z. 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 erfindungsgemäß behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the
Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel: 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 Harvested product and / or altered properties of certain components of the harvested product, such as: 1) transgenic plants synthesizing a modified starch which, in terms of their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, of the
durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des average chain length, the distribution of side chains, the
Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Viscosity behavior, the gel strength, the starch grain size and / or
Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Starch grain morphology in comparison with the synthesized starch 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 0571427,  Wild-type plant cells or plants, so that this modified starch is better suited for certain applications. These transgenic plants which synthesize a modified starch are described, for example, in EP 0571427,
WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581 , WO 1996/27674, WO 1997/1 1 188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO 1996/27674, WO 1997/1 1 188, WO 1997/26362, WO 1997/32985, WO 1997/42328, WO
1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO  1997/44472, WO 1997/45545, WO 1998/27212, WO 1998/40503, WO 99/58688, WO 1999/58690, WO 1999/58654, 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 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO
2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO
2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, 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 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 1995/26407, WO 1996/34968, WO 1998/20145, 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 1995/26407, WO 1996/34968, WO 1998/20145,
WO 1999/12950, WO 1999/66050, WO 1999/53072, US 6,734,341 , WO 2000/1 1 192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO  WO 1999/12950, WO 1999/66050, WO 1999/53072, US Pat. No. 6,734,341, WO 2000/1 1 192, WO 1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO
2005/002359, US 5,824,790, US 6,013,861 , WO 1994/004693, WO 1994/009144, WO 1994/1 1520, WO 1995/35026 bzw. WO 1997/20936 beschrieben. 2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu 2005/002359, US 5,824,790, US 6,013,861, WO 1994/004693, WO 1994/009144, WO 1994/1 1520, WO 1995/35026 and WO 1997/20936, respectively. 2) Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are compared to
Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 1996/001904, Wo 1996/021023, WO 1998/039460 und WO Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460 and WO
1999/024593 beschrieben ist, Pflanzen, die alpha-1 ,4-Glucane produzieren, wie dies in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997/047808 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. 1999/024593, plants which produce alpha-1, 4-glucans, as described in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO 1997 / 047808 and WO 2000/14249, plants producing 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.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, 3) Transgenic plants which produce hyaluronan, as described, for example, in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316,
JP 2006/304779 und WO 2005/012529 beschrieben ist.  JP 2006/304779 and WO 2005/012529.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß 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 Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering), which can also be treated 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, which have an altered form of
Cellulosesynthasegenen enthalten, wie dies in WO 1998/000549 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  Cellulosesynthasegenen contain, as described in WO 1998/000549, b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, as described in WO 2004/053219; 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 02/45485 beschrieben ist; e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z.B. durch Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of sucrose synthase, as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, for example by
Herunterregulieren der faserselektiven ß-1 ,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.  Down-regulating the fiber-selective β-1,3-glucanase as described in WO 2005/017157; f) plants such as cotton plants with altered reactivity fibers, e.g. by expression of the N-acetylglucosamine transferase gene, including nodC, and of 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 erfindungsgemäß behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen: 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 Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. 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 rape plants, the oil with a low saturated
Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist. Produce fatty acid content, as z. As described in US 5,434,283.
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® (Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® Particularly useful transgenic plants which can be treated according to the invention are plants having one or more genes coding for one or more toxins, the transgenic plants being one of the following Commercial names: YIELD GARD® (for example, corn, cotton, soybeans), KnockOut® (for example, corn), BiteGard® (for example, corn), BT-Xtra® (for example, corn), StarLink® (for example, corn) , 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® (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). (Phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS® (Sylfonylurea tolerance), for example maize. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von Particularly useful transgenic plants which can be treated according to the invention are plants which contain transformation events, or a combination of transformation events, and which are for example included in the files of
verschiedenen nationalen oder regionalen Behörden angeführt sind. various national or regional authorities.
Die erfindungsgemäß zu verwendenden Verbindungen der allgemeinen Formel (I) können in üblichen 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 synthetische Stoffe, Düngemittel sowie Feinstverkapselungen in polymeren Stoffen. Im Rahmen der vorliegenden Erfindung ist es insbesondere bevorzugt, wenn die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in der Form einer Sprühformulieruing verwendet werden. The compounds of the general 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 ingredient-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances. In the context of the present invention, it is particularly preferred if the compounds of the general formula (I) according to the invention are used in the form of a spray formulation.
Die vorliegende Erfindung betrifft daher darüber hinaus auch eine Sprühformulierung zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem Stress. Im Folgenden wird eine Sprühformulierung näher beschrieben: Die Formulierungen zur Sprühapplikation werden in bekannter Weise hergestellt, z.B. durch Vermischen der erfindungsgemäß zu verwendenden Verbindungen der allgemeinen 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, The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress. In the following, a spray formulation is described in more detail: The formulations for spray application are prepared in a known manner, for example by mixing the compounds of general formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and or foam-producing agents. Further customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants,
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. Emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and also water may optionally be used. The preparation of the formulations is carried out either in suitable systems or before or during use.
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: 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. As typical aids are:
Streckmittel, Lösemittel und Trägerstoffe. Extenders, solvents and carriers.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic
Kohlenwasserstoffe (wie Paraffine, 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).  Hydrocarbons (such as paraffins, 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, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, 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: 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, Methyl isobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylsulfoxid, sowie Wasser. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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, strong polar solvents such as dimethyl sulfoxide, and water.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
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. 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.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von As dispersants and / or emulsifiers, which may be contained in the formulations usable according to the invention, all come to the formulation of
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 agrochemical active ingredients conventional nonionic, anionic and cationic dispersants into consideration. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants are in particular ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and
Tristryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat-Formaldehydkondensate. Als Entschäumer können in den erfindungsgemäß verwendbaren Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und  Tristryrylphenolpolyglykolether and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates. 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
Magnesiumstearat. Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Magnesium stearate. As preservatives can be used in the invention
Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und  Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and
Benzylalkoholhemiformal. Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Benzyl alcohol. As secondary thickening agents, which can be used in the invention
Formulierungen enthalten sein können, kommen alle für derartige Zwecke in Formulations may be included, all come in for such purposes
agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Agrochemical agents usable substances in question. 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. 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.
Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline A1 , A3 (= Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. As gibberellins which may be present in the formulations which can be used according to the invention, the gibberellins A1, A3 (=
Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinic acid), A4 and A7 in question, particularly preferably using the
Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler„Chemie der Gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der
Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401 -412). Phytosanitary and Pesticides ", 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. 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.
Die Formulierungen enthalten im Allgemeinen zwischen 0,01 und 98 Gew.-%, vorzugsweise zwischen 0,5 und 90 %, der Verbindung der allgemeinen Formel (I). The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I).
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akari- ziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, The active substance according to the invention can be used in its commercially available formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides,
Safenern, Düngemitteln oder Semiochemicals vorliegen. Safeners, fertilizers or semiochemicals.
Ferner lässt sich die beschriebene positive Wirkung der Verbindungen der Furthermore, the described positive effect of the compounds of the
allgemeinden Formel (I) auf die pflanzeneigenen Abwehrkräfte durch eine zusätzliche Behandlung mit insektziden, fungiziden oder bakteriziden Wirkstoffen unterstützen. Bevorzugte Zeitpunkte für die Applikation von Verbindungen der allgemeinen Formel (I) zur Seigerung der Resistanz gegenüber abiotischem Stress sind Boden-, Stamm- und/oder Blattbehandlungen mit den zugelassenen Aufwandmengen. general formula (I) to support the plant's own defenses by additional treatment with insecticidal, fungicidal or bactericidal agents. Preferred times for the application of compounds of the general formula (I) for the seizure of the resistance to abiotic stress are soil, stem and / or leaf treatments with the permitted application rates.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können im The compounds of general formula (I) according to the invention can be described in
Allgemeinen darüber hinaus in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischungen mit ein oder mehreren Wirkstoffen aus der Gruppe bestehend aus Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, die Pflanzenreife beeinflussenden Stoffe, oder Safenern vorliegen. Moreover, in their commercial formulations as well as in the formulations prepared from these formulations in mixtures with one or more active substances from the group consisting of insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators, the plant ripeness affecting substances, or safeners ,
Biologische Beispiele: Biological examples:
Samen von mono- bzw. dikotylen Kulturpflanzen wurden in Plastik- oder Seeds of monocotyledonous or dicotyledonous crops were grown in plastic or
Holzfasertöpfen in sandigem Lehmboden ausgesät, mit Erde oder Sand abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Die Wood fiber pots seeded in sandy loam soil, covered with soil or sand and grown in the greenhouse under good growth conditions. The
Behandlung der Versuchspflanzen erfolgte im frühen Laubblattstadium (BBCH10 - BBCH13). Zur Gewährleistung einer uniformen Wasserversorgung vor Stressbeginn wurden die bepflanzten Töpfe vor Substanzapplikation durch Anstaubewässerung mit Wasser versorgt. Treatment of the test plants took place in the early leaf foliage stage (BBCH10 - BBCH13). To ensure a uniform water supply before the onset of stress, the planted pots were supplied with water before being applied with substance by means of dewatering.
Die in Form von benetzbaren Pulvern (WP) formulierten erfindungsgemässen The formulated according to the invention in the form of wettable powders (WP)
Verbindungen wurden als wässrige Suspension mit einer Wasseraufwandmenge von umgerechnet 600 l/ha unter Zusatz von 0,2% Netzmittel (z.B. Agrotin) auf die grünen Pflanzenteile gesprüht. Unmittelbar nach Substanzapplikation erfolgte die Compounds were sprayed onto the green parts of plants as an aqueous suspension at a rate of 600 l / ha converted with the addition of 0.2% wetting agent (e.g., agrotin). Immediately after substance administration was the
Stressbehandlung der Pflanzen. Die Holzfasertöpfe wurden dazu in Plastikeinsätze transferiert, um anschliessendes, zu schnelles Abtrocknen zu verhindern. Stress treatment of the plants. The wood fiber pots were transferred to plastic inserts to prevent subsequent, too rapid drying.
Der Trockenstress wurde durch langsames Abtrocknen unter folgenden Bedingungen induziert: The dry stress was induced by slow drying under the following conditions:
„Tag": 14 Stunden beleuchtet bei ~ 26-30°C „Nacht": 10 Stunden ohne Beleuchtung bei ~ 18-20°C. "Day": 14 hours lit at ~ 26-30 ° C "Night": 10 hours without lighting at ~ 18-20 ° C.
Die Dauer der jeweiligen Stressphasen richtete sich hauptsächlich nach dem Zustand der gestressten Kontrollpflanzen. Sie wurde (durch Wiederbewässerung und Transfer in ein Gewächshaus mit guten Wachstumsbedingungen) beendet, sobald irreversible Schäden an den gestressten Kontrollpflanzen zu beobachten waren. The duration of the respective stress phases mainly depends on the condition of the stressed control plants. It was terminated (by irrigation and transfer to a greenhouse with good growth conditions) as soon as irreversible damage to the stressed control plants was observed.
Nach Beendigung der Stressphase folgte eine ca. 4-7 tägige Erholungsphase, während der die Pflanzen abermals unter guten Wachstumsbedingungen im After completion of the stress phase followed by a 4-7 day recovery period during which the plants again under good growth conditions in
Gewächshaus gehalten wurden. Die Dauer der Erholungsphase richtete sich Greenhouse were kept. The duration of the recovery phase was directed
hauptsächlich danach, wann die Versuchspflanzen einen Zustand erreicht hatten, der eine visuelle Bonitur potenzieller Effekte ermöglichte, und ist daher variabel. mainly according to when the experimental plants reached a state that allowed a visual assessment of potential effects and is therefore variable.
Wenn dieser Zeitpunkt erreicht war, wurden die Schadintensitäten visuell im Vergleich zu unbehandelten, ungestressten Kontrollen gleichen Alters bonitiert. When this time was reached, the levels of damage were scored visually compared to untreated, unstressed controls of the same age.
Verfahrensmodus A zur Erfassung der Wirksamkeit der getesteten Verbindungen Process mode A to record the effectiveness of the tested compounds
Die Erfassung der Schadintensität erfolgte zunächst in Prozent. Aus diesen Werten wurde sodann der Wirkungsgrad der Testverbindungen nach folgender Formel ermittelt:
Figure imgf000140_0001
The detection of the damage intensity was initially in percent. From these values, the efficiency of the test compounds was then determined according to the following formula:
Figure imgf000140_0001
SU  SU
WG: Wirkungsgrad (Efficacy) = Reduktion der Schadintensität durch Behandlung mit Testsubstanz WG: Efficacy = Reduction of the damage intensity by treatment with test substance
Sls: Schadintensität der gestressten Kontrollpflanzen Sl s : Harmful intensity of stressed control plants
S : Schadintensität der mit Testverbindung behandelten Pflanzen S: damage intensity of the test compound-treated plants
Bei den in unten stehenden Tabellen 1 -3 angegebenen Werten handelt es sich um Mittelwerte aus mindestens einem Versuch mit mindestens zwei Replikaten. Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter Trockenstress (Tabellen 1 bis 3): Tabelle 1 The values given in Tables 1-3 below are averages of at least one test involving at least two replicates. Effects of selected compounds of general formula (I) under dry stress (Tables 1 to 3): Table 1
Figure imgf000141_0001
Figure imgf000141_0001
Tabelle 2  Table 2
Figure imgf000141_0002
Figure imgf000141_0002
Tabelle 3 Table 3
No. Bsp. Dosierung Einheit WG (TRZAS) No. Eg dosage unit WG (TRZAS)
1 1321 100 g/ha > 51 1321 100 g / ha> 5
2 442 250 g/ha > 5 Verfahrensmodus B zur Erfassung der Wirksamkeit der getesteten Verbindungen 2 442 250 g / ha> 5 Process mode B to record the effectiveness of the tested compounds
Das Erscheinungsbild der mit Testsubstanzen behandelten Pflanzen im Vergleich zu den gestressten Kontrollpflanzen wurde nach folgenden Kategorien erfasst: The appearance of the plants treated with test substances in comparison to the stressed control plants was recorded according to the following categories:
0 kein positiver Effekt 0 no positive effect
10 schwach/grenzwertig positiver Effekt  10 weak / borderline positive effect
20 deutlich positiver Effekt  20 clearly positive effect
30 stark positiver Effekt  30 strong positive effect
Pro Substanz und Dosierung wurden jeweils 3-4 Töpfe behandelt und ausgewertet. Die jeweiligen Wirkungsbereiche sind in unten stehenden Tabellen 4 und 5 angegeben. Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) unter For each substance and dosage 3-4 pots were treated and evaluated. The respective ranges of effect are given in Tables 4 and 5 below. Effects of selected compounds of general formula (I) under
Trockenstress (Tabellen 4 und 5): Drought stress (Tables 4 and 5):
Tabelle 4 Table 4
No. Bsp. Dosierung Einheit BRSNSNo. Ex. Dosage unit BRSNS
1 1 194 25 g/ha 10-201 1 194 25 g / ha 10-20
2 108 25 g/ha 10-202 108 25 g / ha 10-20
3 1210 250 g/ha 10-303 1210 250 g / ha 10-30
4 1562 25 g/ha 20-304 1562 25 g / ha 20-30
5 1 123 25 g/ha 10-305 1 123 25 g / ha 10-30
6 1 104 25 g/ha 10-206 1 104 25 g / ha 10-20
7 1582 250 g/ha 10-207 1582 250 g / ha 10-20
8 1582 25 g/ha 10-208 1582 25 g / ha 10-20
9 1590 250 g/ha 10-209 1590 250 g / ha 10-20
10 1593 25 g/ha 10-3010 1593 25 g / ha 10-30
1 1 1604 250 g/ha 20-301 1 1604 250 g / ha 20-30
12 1604 25 g/ha 10-2012 1604 25 g / ha 10-20
13 1594 25 g/ha 10-20 No. Bsp. Dosierung Einheit BRSNS13 1594 25 g / ha 10-20 No. Ex. Dosage unit BRSNS
14 1555 25 g/ha 10-2014 1555 25 g / ha 10-20
15 94 25 g/ha 10-2015 94 25 g / ha 10-20
16 1560 25 g/ha 10-3016 1560 25 g / ha 10-30
17 1565 250 g/ha 10-2017 1565 250 g / ha 10-20
18 1570 250 g/ha 2018 1570 250 g / ha 20
19 1570 25 g/ha 2019 1570 25 g / ha 20
20 1608 250 g/ha 10-2020 1608 250 g / ha 10-20
21 1608 25 g/ha 2021 1608 25 g / ha 20
22 988 250 g/ha 10-2022 988 250 g / ha 10-20
23 988 25 g/ha 10-2023 988 25 g / ha 10-20
24 974 25 g/ha 10-2024 974 25 g / ha 10-20
25 1618 250 g/ha 2025 1618 250 g / ha 20
26 1542 250 g/ha 2026 1542 250 g / ha 20
27 1625 250 g/ha 10-2027 1625 250 g / ha 10-20
28 1625 25 g/ha 10-2028 1625 25 g / ha 10-20
29 1544 25 g/ha 10-2029 1544 25 g / ha 10-20
30 1606 25 g/ha 10-2030 1606 25 g / ha 10-20
31 1628 250 g/ha 10-2031 1628 250 g / ha 10-20
32 1629 25 g/ha 2032 1629 25 g / ha 20
33 1634 250 g/ha 10-2033 1634 250 g / ha 10-20
34 1634 25 g/ha 10-2034 1634 25 g / ha 10-20
35 1545 25 g/ha 10-2035 1545 25 g / ha 10-20
36 1636 250 g/ha 10-2036 1636 250 g / ha 10-20
37 1635 250 g/ha 10-2037 1635 250 g / ha 10-20
38 1646 250 g/ha 10-2038 1646 250 g / ha 10-20
39 1638 25 g/ha 10-2039 1638 25 g / ha 10-20
40 1644 25 g/ha 10-2040 1644 25 g / ha 10-20
41 1639 250 g/ha 10-2041 1639 250 g / ha 10-20
42 1656 25 g/ha 10-2042 1656 25 g / ha 10-20
43 1669 250 g/ha 10-2043 1669 250 g / ha 10-20
44 1669 25 g/ha 10-20 No. Bsp. Dosierung Einheit BRSNS44 1669 25 g / ha 10-20 No. Ex. Dosage unit BRSNS
45 1674 250 g/ha 2045 1674 250 g / ha 20
46 1664 250 g/ha 10-2046 1664 250 g / ha 10-20
47 1659 250 g/ha 10-2047 1659 250 g / ha 10-20
48 1655 250 g/ha 10-2048 1655 250 g / ha 10-20
49 1678 25 g/ha 10-2049 1678 25 g / ha 10-20
50 1695 250 g/ha 20-3050 1695 250 g / ha 20-30
51 1689 25 g/ha 10-2051 1689 25 g / ha 10-20
52 1709 250 g/ha 10-2052 1709 250 g / ha 10-20
53 1716 25 g/ha 20-3053 1716 25 g / ha 20-30
54 1715 250 g/ha 20-3054 1715 250 g / ha 20-30
55 1724 25 g/ha 10-2055 1724 25 g / ha 10-20
56 1728 250 g/ha 10-2056 1728 250 g / ha 10-20
57 1755 250 g/ha 10-2057 1755 250 g / ha 10-20
58 1013 25 g/ha 10-2058 1013 25 g / ha 10-20
59 1627 25 g/ha 10-2059 1627 25 g / ha 10-20
60 1633 250 g/ha 10-2060 1633 250 g / ha 10-20
61 973 250 g/ha 10-2061 973 250 g / ha 10-20
62 1765 25 g/ha 10-2062 1765 25 g / ha 10-20
63 1543 25 g/ha 10-2063 1543 25 g / ha 10-20
64 1566 25 g/ha 10-2064 1566 25 g / ha 10-20
65 1613 25 g/ha 10-2065 1613 25 g / ha 10-20
66 1621 25 g/ha 10-2066 1621 25 g / ha 10-20
67 1569 25 g/ha 10-20 67 1569 25 g / ha 10-20
Tabelle 5 Table 5
No. Bsp. Dosierung Einheit TRZASNo. Ex. Dosage Unit TRZAS
1 1624 250 g/ha 10-201 1624 250 g / ha 10-20
2 988 25 g/ha 10-202 988 25 g / ha 10-20
3 974 25 g/ha 203 974 25 g / ha 20
4 1609 250 g/ha 10-204 1609 250 g / ha 10-20
5 1614 25 g/ha 10-20 No. Bsp. Dosierung Einheit TRZAS5 1614 25 g / ha 10-20 No. Ex. Dosage Unit TRZAS
6 536 250 g/ha 10-206,536 250 g / ha 10-20
7 536 25 g/ha 10-207 536 25 g / ha 10-20
8 532 250 g/ha 10-208 532 250 g / ha 10-20
9 1610 250 g/ha 10-209 1610 250 g / ha 10-20
10 1607 25 g/ha 20 10 1607 25 g / ha 20
1 1 643 250 g/ha 10-20  1 1 643 250 g / ha 10-20
In den zuvor genannten Tabellen 1 - 5 bedeuten: Bsp. = Verbindung entsprechend dem Bsp. aus Tabelle 1 In the above-mentioned Tables 1 to 5: Ex. = Compound corresponding to Ex. From Table 1
BRSNS = Brassica napus  BRSNS = Brassica napus
TRZAS = Triticum aestivum  TRZAS = Triticum aestivum
ZEAMX = Zea mays Ähnliche Ergebnisse konnten auch noch mit weiteren Verbindungen der allgemeinen Formel (I) auch bei Applikation auf andere Pflanzenarten erzielt werden.  ZEAMX = Zea mays Similar results could also be obtained with other compounds of the general formula (I) even when applied to other plant species.

Claims

Patentansprüche Patent claims
Verwendung substituierter Pyridoncarboxamide der allgemeinen Formel deren Salze Use of substituted pyridonecarboxamides of the general formula and their salts
Figure imgf000146_0001
zur Toleranzerhöhung gegenüber abiotischem Stress in Pflanzen, wobei
Figure imgf000146_0001
to increase tolerance to abiotic stress in plants, whereby
R1 (C3-C6)-Cycloalkyl, Aryl oder Hetaryl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )- Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci- C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloal kyl (C1 -C6)-al kyl , (C1 -C )-Al koxy-carbonyl-(Ci -C )-al kyl , Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, R 1 means (C3-C6)-cycloalkyl, aryl or hetaryl, each of the three radicals being unsubstituted or by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (Ci-C)-alkyl , (Ci-C )-haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, ( Ci-C )-haloalkylthio, (Ci-C )-haloalkylsulfoxy, (Ci-C 4 )-haloalkylsulfone, (Ci-C 4 )-alkoxy-carbonyl, (Ci-C 4 )-haloalkoxy-carbonyl, (Ci-C 4 )-Alkylcarboxy, (C3-C6)-cycloalkyl, (C3-C 6 )-cycloalkyl (C1 -C 6 )-alkyl, (C1 -C )-Al koxy-carbonyl-(Ci -C )-al kyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C 4 )-alkyl, R 8 R 9 N-carbonyl is substituted,
R2 Wasserstoff bedeutet und R 2 means hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, (Ci-Ci6)-Alkyl, (C2-Ci6)-Alkenyl oder (C2-Ci6)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)- Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)- Cycloalkyl, das unsubstituiert oder substituiert ist, Aryl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder R 3 and R 4 are independently hydrogen, (Ci-Ci6)-alkyl, (C2-Ci6)-alkenyl or (C2-Ci6)-alkynyl, each of the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen , hydroxy, cyano, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-alkylamino, di[(Ci-C 4 )- alkyl]-amino, hydroxycarbonyl, [(Ci-C 4 )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl that is unsubstituted or substituted, aryl, that is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocyclyl, which is unsubstituted or substituted, is substituted, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)- alkyl-carbonyl, (Ci-Ci6)-Alkylcarbonyl, (Ci-Ci6)-Haloalkylcarbonyl bedeuten, oder [(Ci-C 4 )-Alkoxy]-carbonyl-carbonyl, [(Ci-C 4 )-Alkoxy]-carbonyl-(Ci-C8)-alkyl-carbonyl, (Ci-Ci6)-alkylcarbonyl, (Ci-Ci6 )-Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)-Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder (C3-C6)-cycloalkyl, (C 4 -C6)cycloalkenyl, (C3-C6)-cycloalkyl, which is on one side of the ring with a 4 to 6-membered saturated or
ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)- Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)- Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )- Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci-C )-Alkoxy]- carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)-Cycloalkyl, Aryl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder unsaturated carbocyclic ring is fused, or (C 4 -C6)-cycloalkenyl which is fused on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 )-alkyl, (Ci-C )-haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylamino, di[(Ci-C )-alkyl]-amino, [(Ci-C )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]-carbonyl, (C3-C6 )-Cycloalkyl, aryl that is unsubstituted or substituted, heteroaryl that is unsubstituted or substituted or heterocyclyl that is unsubstituted or substituted, substituted, or
Aryl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )- Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci- C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloal kyl (Ci -C6)-al kyl , (Ci -C )-Al koxy-carbonyl-(Ci -C )-al kyl , Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, Aryl, heteroaryl, or heterocyclyl, each of the three radicals being unsubstituted or by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (Ci-C)-alkyl, (Ci-C)-haloalkyl , (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, ( Ci-C )-haloalkylsulfoxy, (Ci-C 4 )-haloalkylsulfone, (Ci-C 4 )-alkoxy-carbonyl, (Ci-C 4 )-haloalkoxy-carbonyl, (Ci-C 4 )-alkylcarboxy, (C3- C6)-cycloalkyl, (C3- C 6 )-Cycloalkyl (Ci -C 6 )-alkyl, (Ci -C )-Al koxy-carbonyl-(Ci -C )-alkyl, hydroxycarbonyl, hydroxycarbonyl-(Ci-C 4 )-alkyl, R 8 R 9 N-carbonyl is substituted,
bedeuten, oder mean, or
Wasserstoff oder (Ci-Ce)-Alkyl bedeutet means hydrogen or (Ci-Ce)-alkyl
R4 (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)-Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder R 4 (Ci-C 6 )-alkyl, (Ci-Ce)-alkoxy, (C2-C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 6 )-haloalkoxy or (Ci -C 6 )-alkyl-SO 2 means, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen R 3 and R 4 together with the directly bound N atom
Aminosäurerest und zwar die natürlich vorkommenden in ihrer Amino acid residue, namely the naturally occurring ones in their
racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder racemic and in their respective D and L forms, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly bound N atom form a four - to
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]- carbonyl , (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann oder R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe form an eight-membered carbocyclic or heterocyclic ring which, in addition to the N atom, can also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S and which is unsubstituted or has one or more radicals from the group halogen, (Ci- C )-alkyl, (Ci-C )-haloalkyl, [(Ci-C )-alkoxy]-carbonyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, hydroxy is substituted and where a heterocyclic ring can contain n oxo groups or R 3 and R 4 together with the directly bound N atom form the group
-N=CR5-NR6R7 bedeuten undwobei für Wasserstoff oder (Ci-Ce)-Alkyl steht, -N=CR 5 -NR 6 R 7 andwhere represents hydrogen or (Ci-Ce)-alkyl,
R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R6, R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und R 6 and R 7 independently represent hydrogen or (Ci-Ce)-alkyl, or R 6 , R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or Morpholinyl and
R8 und R9 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten und n für 0, 1 oder 2 steht. R 8 and R 9 independently represent hydrogen or (Ci-Ce)-alkyl and n represents 0, 1 or 2.
Verwendung gemäß Anspruch 1 , wobei in Formel (I) Use according to claim 1, wherein in formula (I)
(C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C4)-Haloalkoxy, (C3-C6)-Cycloalkyl substituiert ist, (C3-C6)-cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, cyano, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci -C )-alkoxy, (Ci-C 4 )-haloalkoxy, (C3-C6)-cycloalkyl is substituted,
R2 Wasserstoff bedeutet und R 2 means hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, R 3 and R 4 are independently hydrogen,
(Ci-Ci2)-Alkyl, (C2-Ci2)-Alkenyl oder (C2-Ci2)-Alkinyl, wobei jeder der letztgenannten 3 Reste (Ci-Ci2)-alkyl, (C2-Ci2)-alkenyl or (C2-Ci2)-alkynyl, each of the latter having 3 radicals
unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)- Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)- Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocydyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )- Alkylamino, di[(Ci-C 4 )-alkyl]-amino, hydroxycarbonyl, [(Ci-C 4 )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]-carbonyl, (C3-C6)- Cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocydyl which is unsubstituted or substituted means substituted, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)- alkyl-carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, oder [(Ci-C 4 )-Alkoxy]-carbonyl-carbonyl, [(Ci-C 4 )-Alkoxy]-carbonyl-(Ci-C8)-alkyl-carbonyl, (Ci-C8)-alkylcarbonyl, (Ci-C8 )-Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C4)-Alkylthio, Phenyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder (C3-C6)-cycloalkyl, (C 4 -C6)cycloalkenyl, where each of the latter two radicals is unsubstituted or replaced by one or more radicals from the group halogen, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C )-alkoxy, (Ci-C 4 )-alkylthio, phenyl, which is unsubstituted or substituted, is substituted, or
Phenyl, Heteroaryl, oder Heterocydyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci- C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci- C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, oder Phenyl, heteroaryl, or heterocydyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, (Ci-C )- Haloalkylsulfoxy, (Ci-C 4 )-haloalkyl sulfone, (Ci-C 4 )-alkoxy-carbonyl, (C3-C6)-cycloalkyl, is substituted, or
Wasserstoff oder (Ci-Ce)-Alkyl bedeutet und R4 (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)-Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder Hydrogen or (Ci-Ce)-alkyl means and R 4 (Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, (C2-C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 6 )-haloalkoxy or ( Ci-C 6 )-alkyl-SO 2 means, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen R 3 and R 4 together with the directly bound N atom
Aminosäurerest und zwar die natürlich vorkommenden in ihrer Amino acid residue, namely the naturally occurring ones in their
racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder racemic and in their respective D and L forms, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly bound N atom form a four - to
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]- carbonyl , (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann oder form an eight-membered carbocyclic or heterocyclic ring which, in addition to the N atom, can also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S and which is unsubstituted or has one or more radicals from the group halogen, (Ci- C )-alkyl, (Ci-C )-haloalkyl, [(Ci-C )-alkoxy]-carbonyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, hydroxy is substituted and where a heterocyclic ring can contain n oxo groups or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe R 3 and R 4 together with the directly bound N atom form the group
-N=CR5-NR6R7 bedeuten, wobei -N=CR 5 -NR 6 R 7 , where
R5 für Wasserstoff oder (Ci-Ce)-Alkyl steht und R 5 represents hydrogen or (Ci-Ce)-alkyl and
R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R6 und R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und n für 0, 1 oder 2 steht. R 6 and R 7 independently represent hydrogen or (Ci-Ce)-alkyl, or R 6 and R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and n is 0, 1 or 2.
3. Verwendung gemäß Anspruch 1 , wobei in Formel (I) 3. Use according to claim 1, wherein in formula (I)
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci- C4)-Haloalkoxy substituiert ist, R 1 means (C3-C6)-cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci -C )-alkoxy, (Ci-C 4 )-haloalkoxy is substituted,
R2 Wasserstoff bedeutet und R 2 means hydrogen and
R3 und R4 unabhängig voneinander Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)- Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]-carbonyl, (C3-C6)- Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heteroaryl, das unsubstituiert oder substituiert ist oder Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist bedeuten, oder [(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)- alkyl-carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, R 3 and R 4 are independently hydrogen, (Ci-C8)-alkyl, (C2-C8)-alkenyl or (C2-C8)-alkynyl, each of the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen , hydroxy, cyano, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-alkylamino, di[(Ci-C 4 )- alkyl]-amino, hydroxycarbonyl, [(Ci-C 4 )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted, phenyl, the is unsubstituted or substituted, heteroaryl which is unsubstituted or substituted or heterocyclyl which is unsubstituted or substituted is substituted, or [(Ci-C 4 )-Alkoxy]-carbonyl-carbonyl, [(Ci-C 4 )-Alkoxy]-carbonyl-(Ci-C8)-alkyl-carbonyl, (Ci-C8)-alkylcarbonyl, (Ci-C8 )-Haloalkylcarbonyl means,
oder or
(C3-C6)-Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )- Alkoxy, (Ci-C4)-Alkylthio, Phenyl, das unsubstituiert oder substituiert ist, substituiert ist bedeutet, oder (C3-C6)-cycloalkyl, which is unsubstituted or replaced by one or more radicals from the group halogen, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C)-alkoxy, (Ci-C 4 )-Alkylthio, phenyl which is unsubstituted or substituted, is substituted, or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )- Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-C )-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist, oder Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, (Ci-C )-alkyl, (Ci-C )-haloalkyl, (Ci-C )-alkoxy, (Ci -C )- Haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, (Ci-C )-haloalkylsulfoxy, (Ci-C )-haloalkylsulfone, (Ci-C 4 )-alkoxy-carbonyl, (C3-C6)-cycloalkyl, is substituted, or
R3 Wasserstoff oder (Ci-C6)-Alkyl bedeutet und R 3 is hydrogen or (Ci-C6)-alkyl and
R4 (Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Alkinyloxy oder (C2-C6)-Haloalkoxy oder (Ci-C6)-Alkyl-SO2 bedeutet, oder R 4 (Ci-C 6 )-alkyl, (Ci-C 6 )-alkoxy, (C2-C 6 )-alkenyloxy, (C2-C 6 )-alkynyloxy or (C 2 -C 6 )-haloalkoxy or (Ci -C 6 )-alkyl-SO2 means, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen R 3 and R 4 together with the directly bound N atom
Aminosäurerest und zwar die natürlich vorkommenden in ihrer Amino acid residue, namely the naturally occurring ones in their
racemischen und in ihrer jeweiligen D- und L-Form bedeuten, oder racemic and in their respective D and L forms mean, or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom einen vier - bis R 3 and R 4 together with the directly bound N atom form a four - to
achtgliedrigen carbocyclischen oder heterocyclischen Ring bilden, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, [(Ci-C )-Alkoxy]- carbonyl , (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, Hydroxy substituiert ist und wobei ein heterocyclischer Ring n Oxogruppen enthalten kann oder form an eight-membered carbocyclic or heterocyclic ring which, in addition to the N atom, can also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S and which is unsubstituted or has one or more radicals from the group halogen, (Ci- C )-alkyl, (Ci-C )-haloalkyl, [(Ci-C )-alkoxy]-carbonyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, hydroxy is substituted and where a heterocyclic ring can contain n oxo groups or
R3 und R4 zusammen mit dem direkt gebundenen N-Atom die Gruppe R 3 and R 4 together with the directly bound N atom form the group
-N=CR5-NR6R7 bedeuten, wobei -N=CR 5 -NR 6 R 7 , where
R5 für Wasserstoff oder (Ci-Ce)-Alkyl steht und R 5 represents hydrogen or (Ci-Ce)-alkyl and
R6 und R7 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten, oder R 6 and R 7 independently represent hydrogen or (Ci-Ce)-alkyl, or
R6 und R7 bilden zusammen mit dem direkt gebundenen N-Atom einen fünf- bis siebengliedrigen, vorzugsweise gesättigten heterocyclischen Ring, wie beispielsweise Piperidinyl, Pyrrolidinyl oder Morpholinyl und n für 0, 1 oder 2 steht. R 6 and R 7 together with the directly bonded N atom form a five- to seven-membered, preferably saturated heterocyclic ring, such as piperidinyl, pyrrolidinyl or morpholinyl and n is 0, 1 or 2.
4. Behandlung von Pflanzen, umfassend die Applikation einer zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksamen, nicht-toxischen Menge einer oder mehrere der Verbindungen der allgemeinen Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3. 4. Treatment of plants, comprising the application of a non-toxic amount of one or more of the compounds of the general formula (I), or their salts according to one of claims 1 to 3, which is effective for increasing the resistance of plants to abiotic stress factors.
5. Behandlung gemäß Anspruch 4, wobei die abiotischen Streßbedingungen einer oder mehrer Bedingungen ausgewählt aus der Gruppe von Dürre, Kälte- und 5. Treatment according to claim 4, wherein the abiotic stress conditions are one or more conditions selected from the group of drought, cold and
Hitzebedingungen, Trockenstress, osmotischem Streß, Staunässe, erhöhtem Heat conditions, drought stress, osmotic stress, waterlogging, increased
Bodensalzgehalt, erhöhtem Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkter Verfügbarkeit von Stickstoffnährstoffen, beschränkter Verfügbarkeit von Phosphornährstoffen entsprechen. Soil salinity, increased exposure to minerals, ozone conditions, strong light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
6. Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I), oder 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, 6. Use of one or more compounds of the general formula (I), or their salts according to one of claims 1 to 3, in spray application on plants and parts of plants in combinations with one or more active ingredients selected from the group of insecticides, attractants, acaricides, fungicides ,
Nematizide, Herbizide, wachstumsregulatorische Stoffe, Safener, die Pflanzenreife beeinflussende Stoffe und Bakterizide. Nematicides, herbicides, growth regulators, safeners, substances that influence plant maturity and bactericides.
7. Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I), oder deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit Düngemitteln. 7. Use of one or more compounds of the general formula (I) or their salts according to one of claims 1 to 3 in spray application on plants and parts of plants in combinations with fertilizers.
8. Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I), oder deren Salze gemäß einem der Ansprüche 1 bis 3 zur Applikation auf 8. Use of one or more compounds of the general formula (I) or their salts according to one of claims 1 to 3 for application
gentechnisch veränderten Sorten, deren Saatgut, oder auf Anbauflächen auf denen diese Sorten wachsen. genetically modified varieties, their seeds, or on areas where these varieties grow.
9. Verwendung von Sprühlösungen, die eine oder mehrere Verbindungen der allgemeinen Formel (I), oder deren Salze gemäß einem der Ansprüche 1 bis 3 enthalten, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. 9. Use of spray solutions which contain one or more compounds of the general formula (I), or their salts according to one of claims 1 to 3, to increase the resistance of plants to abiotic stress factors.
10. Verfahren zur Erhöhung der Stresstoleranz bei Pflanzen ausgewählt aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, oder Bäumen, welches die Applikation einer ausreichenden, nicht-toxischen Menge einer oder mehrerer 10. Process for increasing stress tolerance in plants selected from the group of crops, ornamental plants, lawns, or trees, which involves the application of a sufficient, non-toxic amount of one or more
Verbindungen der allgemeinen 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. Compounds of the general formula (I), or their salts according to one of claims 1 to 3, on the area where the corresponding effect is desired, comprising application to the plants, their seeds or to the area on which the plants grow.
1 1 . 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. 1 1 . Method according to claim 10, wherein the resistance of the plants treated in this way to abiotic stress is increased by at least 3% compared to untreated plants under otherwise identical physiological conditions.
12. Substituierte Pyridoncarboxamide der Formel (I), oder deren Salze, 12. Substituted pyridone carboxamides of the formula (I), or their salts,
Figure imgf000156_0001
worin
Figure imgf000156_0001
wherein
(C3-C6)-Cycloalkyl, Phenyl oder Hetaryl bedeutet, wobei jeder der drei(C3-C6)-cycloalkyl, phenyl or hetaryl, each of the three
Reste unsubstituiert oder durch einen oder mehrere Reste aus derResidues unsubstituted or by one or more residues from the
Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C )-Alkyl, (Ci-C )- Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (Ci-C )-alkyl, (Ci-C )-haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, (Ci-C )-
Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci- C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloal kyl (C1 -C6)-al kyl , (C1 -C )-Al koxy-carbonyl-(Ci -C )-al kyl ,Haloalkylsulfoxy, (Ci-C 4 )-haloalkyl sulfone, (Ci-C 4 )-alkoxy-carbonyl, (Ci-C 4 )-haloalkoxy-carbonyl, (Ci-C 4 )-alkylcarboxy, (C3-C6)-cycloalkyl, (C3- C6 )-Cycloalkyl (C1- C6 )-alkyl, (C1-C)-Alkoxy-carbonyl-(Ci-C)-alkyl,
Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist Hydroxycarbonyl, hydroxycarbonyl-(Ci-C 4 )-alkyl, R 8 R 9 N-carbonyl is substituted
Wasserstoff bedeutet und Ethyl bedeutet und Hydrogen means and Ethyl means and
CH2CH2-R10 bedeutet und CH2CH2-R 10 means and
Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl oder (C2-C8)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)- Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci- C4)-alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)- Haloalkoxy]-carbonyl substituiert ist bedeuten, oder Hydrogen, (Ci-C 8 )-alkyl, (C 2 -C 8 )-alkenyl or (C 2 -C 8 )-alkynyl, each of the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy , cyano, (Ci-C 4 )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylamino, di[(Ci-C 4 )-alkyl]-amino, Hydroxycarbonyl, [(Ci-C 4 )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]-carbonyl is substituted, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)- alkyl-carbonyl, (Ci-Ci6)-Alkylcarbonyl, (Ci-Ci6)-Haloalkylcarbonyl bedeuten, oder [(Ci-C 4 )-Alkoxy]-carbonyl-carbonyl, [(Ci-C 4 )-Alkoxy]-carbonyl-(Ci-C8)-alkyl-carbonyl, (Ci-Ci6)-alkylcarbonyl, (Ci-Ci6 )-Haloalkylcarbonyl, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylamino, Di[(Ci-C )-alkyl]-amino, [(Ci-C )-Alkoxy]-carbonyl, [(Ci-C )-Haloalkoxy]- carbonyl, (C3-C6)-Cycloalkyl, Phenyl, Heteroaryl oder Heterocyclyl substituiert ist bedeuten, oder (C3-C6)-cycloalkyl, (C 4 -C6)cycloalkenyl, where each of the latter two radicals is unsubstituted or replaced by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C 4 )-alkyl, (Ci-C 4 )-Haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylamino, di[(Ci-C )-alkyl]-amino, [(Ci-C)-alkoxy]-carbonyl, [(Ci-C)-haloalkoxy]-carbonyl, (C3-C6)-cycloalkyl, phenyl, heteroaryl or heterocyclyl substituted means, or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, NR8R9, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )- Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )- Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci- C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloal kyl (C1 -C6)-al kyl , (C1 -C )-Al koxy-carbonyl-(Ci -C )-al kyl , Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R8R9N-carbonyl substituiert ist, und Phenyl, heteroaryl, or heterocyclyl, each of the three radicals being unsubstituted or by one or more radicals from the group halogen, nitro, hydroxy, cyano, NR 8 R 9 , (Ci-C)-alkyl, (Ci-C)-haloalkyl , (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, ( Ci-C )- Haloalkylsulfoxy, (Ci-C 4 )-haloalkyl sulfone, (Ci-C 4 )-alkoxy-carbonyl, (Ci-C 4 )-haloalkoxy-carbonyl, (Ci-C 4 )-alkylcarboxy, (C3-C6)-cycloalkyl, (C3-C 6 )-Cycloalkyl (C1 -C 6 )-alkyl , (C1 -C )-Al koxy-carbonyl-(Ci -C )-alkyl , hydroxycarbonyl, hydroxycarbonyl-(Ci-C 4 )- alkyl, R 8 R 9 N-carbonyl is substituted, and
R8 und R9 unabhängig voneinander Wasserstoff oder (Ci-Ce)-Alkyl bedeuten. R 8 and R 9 independently represent hydrogen or (Ci-Ce)-alkyl.
13. Substutiierte Pyridoncarboxamide gemäß Anspruch 12, wobei 13. Substituted pyridone carboxamides according to claim 12, wherein
R1 (C3-C6)-Cycloalkyl, Phenyl oder Pyridinyl bedeutet, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C4)-Haloalkoxy, (C3-C6)-Cycloalkyl substituiert ist, R 1 means (C3-C6)-cycloalkyl, phenyl or pyridinyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, cyano, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C)-alkoxy, (Ci-C 4 )-haloalkoxy, (C3-C6)-cycloalkyl is substituted,
R2 Wasserstoff bedeutet und R 2 means hydrogen and
R3 Ethyl bedeutet und R 3 means ethyl and
R4 CH2CH2-R10 bedeutet und R 4 CH2CH2-R 10 means and
R10 Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)-Alkoxy, (Ci-C4)- Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylamino, Di[(Ci-C4)-alkyl]-amino, Hydroxycarbonyl, [(Ci-C4)-Alkoxy]-carbonyl, [(Ci-C4)-Haloalkoxy]- carbonyl, substituiert ist bedeuten, oder R 10 hydrogen, (Ci-C 6 )-alkyl, (C2-C 6 )-alkenyl, (C2-C 6 )-alkynyl, each of the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy , cyano, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy, (Ci-C 4 )-alkylthio, (Ci-C 4 )-alkylamino, di[(Ci-C 4 )-alkyl] -amino, hydroxycarbonyl, [(Ci-C 4 )-alkoxy]-carbonyl, [(Ci-C 4 )-haloalkoxy]- carbonyl, substituted means, or
[(Ci-C4)-Alkoxy]-carbonyl-carbonyl, [(Ci-C4)-Alkoxy]-carbonyl-(Ci-C8)- alkyl-carbonyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl bedeuten, oder [(Ci-C 4 )-Alkoxy]-carbonyl-carbonyl, [(Ci-C 4 )-Alkoxy]-carbonyl-(Ci-C8)-alkyl-carbonyl, (Ci-C8)-alkylcarbonyl, (Ci-C8 )-Haloalkylcarbonyl means, or
(C3-C6)-Cycloalkyl, (C4-C6)Cycloalkenyl, wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci-C )-Alkoxy, (Ci-C4)-Alkylthio, Phenyl substituiert ist bedeuten, oder (C3-C6)-cycloalkyl, (C 4 -C6)cycloalkenyl, where each of the latter two radicals is unsubstituted or replaced by one or more radicals from the group halogen, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C )-alkoxy, (Ci-C 4 )-alkylthio, phenyl substituted means, or
Phenyl, Heteroaryl, oder Heterocyclyl, wobei jeder der drei Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Hydroxy, Cyano, (Ci-C )-Alkyl, (Ci-C )-Haloalkyl, (Ci- C )-Alkoxy, (Ci-C )-Haloalkoxy, (Ci-C )-Alkylthio, (Ci-C )-Alkylsulfoxy, (Ci-C )-Alkylsulfon, (Ci-C )-Haloalkylthio, (Ci-C )-Haloalkylsulfoxy, (Ci-Phenyl, heteroaryl, or heterocyclyl, where each of the three radicals is unsubstituted or replaced by one or more radicals from the group halogen, nitro, hydroxy, cyano, (Ci-C)-alkyl, (Ci-C)-haloalkyl, (Ci-C )-alkoxy, (Ci-C )-haloalkoxy, (Ci-C )-alkylthio, (Ci-C )-alkylsulfoxy, (Ci-C )-alkylsulfone, (Ci-C )-haloalkylthio, (Ci-C )- Haloalkylsulfoxy, (Ci-
C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (C3-C6)-Cycloalkyl, substituiert ist. C 4 )-haloalkylsulfone, (Ci-C 4 )-alkoxy-carbonyl, (C3-C6)-cycloalkyl, is substituted.
14. Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge einer oder mehrerer der substituierten Pyridoncarboxamide gemäß einem der Ansprüche 12 oder 13. 14. Spray solution for the treatment of plants, containing an effective amount of one or more of the substituted pyridone carboxamides according to one of claims 12 or 13 to increase the resistance of plants to abiotic stress factors.
PCT/EP2015/079926 2014-12-18 2015-12-16 Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress WO2016096942A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14198834.5 2014-12-18
EP14198834 2014-12-18

Publications (1)

Publication Number Publication Date
WO2016096942A1 true WO2016096942A1 (en) 2016-06-23

Family

ID=52338865

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2015/079926 WO2016096942A1 (en) 2014-12-18 2015-12-16 Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress

Country Status (2)

Country Link
AR (1) AR103024A1 (en)
WO (1) WO2016096942A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018190350A1 (en) * 2017-04-10 2018-10-18 三井化学アグロ株式会社 Pyridone compound, and agricultural and horticultural fungicide having this as active component
WO2019039429A1 (en) * 2017-08-22 2019-02-28 日本曹達株式会社 Cyclic amine compound and pest control agent
WO2021003295A1 (en) * 2019-07-02 2021-01-07 Regeneron Pharmaceuticals, Inc. Modulators of hsd17b13 and methods of use thereof
US11178872B2 (en) 2016-05-09 2021-11-23 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent

Citations (182)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US947A (en) 1838-09-25 Machine fob dyeing yarn from the beam
US6063A (en) 1849-01-30 Improvement in baking apparatus
US2532055A (en) 1945-04-03 1950-11-28 Wyeth Corp Pyridone derivatives
DE1905834A1 (en) 1969-02-06 1970-09-03 Basf Ag Salts and fertilizers provided with a coating to avoid dusting and caking
DE3534948A1 (en) 1985-10-01 1987-04-09 Bayer Ag FUNGICIDES AND GROWTH REGULATORY AGENTS
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
WO1989010396A1 (en) 1988-04-28 1989-11-02 Plant Genetic Systems N.V. Plants with modified stamen cells
DD277835A1 (en) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS
DD277832A1 (en) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS
US4960896A (en) 1985-11-26 1990-10-02 A. H. Robins Company, Inc. Process for the preparation of 5-chloro and 5-bromo-2-hydroxynicotinic acids
WO1991002069A1 (en) 1989-08-10 1991-02-21 Plant Genetic Systems N.V. Plants with modified flowers
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
WO1992005251A1 (en) 1990-09-21 1992-04-02 Institut National De La Recherche Agronomique Dna sequence imparting cytoplasmic male sterility, mitochondrial genome, nuclear genome, mitochondria and plant containing said sequence and process for the preparation of hybrids
DE4103253A1 (en) 1991-02-04 1992-08-06 Bitterfeld Wolfen Chemie Agent to increase stress tolerance of crops and forests - contains synergistic mixt. of choline chloride and N-(2-hydroxy-ethyl)-piperazine
EP0502740A1 (en) 1991-03-07 1992-09-09 E.I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamide
EP0522392A1 (en) 1991-07-11 1993-01-13 E.I. Du Pont De Nemours And Company Substituted pyridines and a process for their preparation
DE4128828A1 (en) 1991-08-30 1993-03-04 Basf Ag AMMONIUM OR UREA-CONTAINED DISPENSERS AND METHOD FOR THEIR PRODUCTION
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
US5201931A (en) 1988-12-01 1993-04-13 Her Majesty The Queen In Right Of Canada, As Represented By The National Research Council Of Canada Abscisic acid-related plant growth regulators - germination promoters
EP0544151A1 (en) 1991-11-26 1993-06-02 BASF Aktiengesellschaft Hydroxypyridone carboxylic acid amides, their preparation and use as herbicides
EP0571427A1 (en) 1991-02-13 1993-12-01 Hoechst Schering AgrEvo GmbH Plasmids containing dna-sequences that cause changes in the carbohydrate concentration and the carbohydrate composition in plants, as well as plant cells and plants containing these plasmids
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
WO1994004693A2 (en) 1992-08-26 1994-03-03 Zeneca Limited Novel plants and processes for obtaining them
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
WO1994009144A1 (en) 1992-10-14 1994-04-28 Zeneca Limited Novel plants and processes for obtaining them
WO1994011520A2 (en) 1992-11-09 1994-05-26 Zeneca Limited Novel plants and processes for obtaining them
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
WO1994021795A1 (en) 1993-03-25 1994-09-29 Ciba-Geigy Ag Novel pesticidal proteins and strains
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
WO1995004826A1 (en) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants
WO1995009910A1 (en) 1993-10-01 1995-04-13 Mitsubishi Corporation Gene that identifies sterile plant cytoplasm and process for preparing hybrid plant by using the same
US5434283A (en) 1990-04-04 1995-07-18 Pioneer Hi-Bred International, Inc. Edible endogenous vegetable oil extracted from rapeseeds of reduced stearic and palmitic saturated fatty acid content
EP0663956A1 (en) 1992-08-12 1995-07-26 Hoechst Schering AgrEvo GmbH Dna sequences which lead to the formation of polyfructans (levans), plasmids containing these sequences as well as a process for preparing transgenic plants
WO1995026407A1 (en) 1994-03-25 1995-10-05 National Starch And Chemical Investment Holding Corporation Method for producing altered starch from potato plants
US5463175A (en) 1990-06-25 1995-10-31 Monsanto Company Glyphosate tolerant plants
WO1995031553A1 (en) 1994-05-18 1995-11-23 Institut Für Genbiologische Forschung Berlin Gmbh DNA SEQUENCES CODING FOR ENZYMES CAPABLE OF FACILITATING THE SYNTHESIS OF LINEAR α-1,4 GLUCANS IN PLANTS, FUNGI AND MICROORGANISMS
WO1995035026A1 (en) 1994-06-21 1995-12-28 Zeneca Limited Novel plants and processes for obtaining them
WO1996001904A1 (en) 1994-07-08 1996-01-25 Stichting Scheikundig Onderzoek In Nederland Production of oligosaccharides in transgenic plants
WO1996015248A1 (en) 1994-11-10 1996-05-23 Hoechst Schering Agrevo Gmbh Dna molecules that code for enzymes involved in starch synthesis, vectors, bacteria, transgenic plant cells and plants containing said molecules
WO1996019581A1 (en) 1994-12-22 1996-06-27 Hoechst Schering Agrevo Gmbh Dna molecules coding for debranching enzymes derived from plants
EP0719338A1 (en) 1993-09-09 1996-07-03 Hoechst Schering AgrEvo GmbH Combination of dna sequences which enable the formation of modified starch in plant cells and plants, processes for the production of these plants and the modified starch obtainable therefrom
WO1996021023A1 (en) 1995-01-06 1996-07-11 Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
EP0728213A1 (en) 1993-11-09 1996-08-28 E.I. Du Pont De Nemours And Company Transgenic fructan accumulating crops and methods for their production
WO1996027674A1 (en) 1995-03-08 1996-09-12 Hoechst Schering Agrevo Gmbh Modified starch from plants, plants synthesizing this starch, and process for its preparation
US5561236A (en) 1986-03-11 1996-10-01 Plant Genetic Systems Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
WO1996033270A1 (en) 1995-04-20 1996-10-24 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996034968A2 (en) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plant starch composition
WO1996038567A2 (en) 1995-06-02 1996-12-05 Rhone-Poulenc Agrochimie Dna sequence of a gene of hydroxy-phenyl pyruvate dioxygenase and production of plants containing a gene of hydroxy-phenyl pyruvate dioxygenase and which are tolerant to certain herbicides
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
WO1997011188A1 (en) 1995-09-19 1997-03-27 Planttec Biotechnologie Gmbh Plants which synthesise a modified starch, process for the production thereof and modified starch
GB2305174A (en) 1995-09-15 1997-04-02 Zeneca Ltd Chemical process
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
WO1997020936A1 (en) 1995-12-06 1997-06-12 Zeneca Limited Modification of starch synthesis in plants
WO1997026362A1 (en) 1996-01-16 1997-07-24 Planttec Biotechnologie Gmbh Nucleic acid molecules from plants coding enzymes which participate in the starch synthesis
WO1997032985A1 (en) 1996-03-07 1997-09-12 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules coding for debranching enzymes from maize
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997042328A1 (en) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleic acid molecules which code the potato debranching enzyme
WO1997044472A1 (en) 1996-05-17 1997-11-27 Planttec Biotechnologie Gmbh Nucleic acid molecules coding soluble maize starch synthases
WO1997045545A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nucleic acid molecules encoding enzymes from wheat which are involved in starch synthesis
WO1997047807A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047806A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047808A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1998000549A1 (en) 1996-06-27 1998-01-08 The Australian National University MANIPULATION OF CELLULOSE AND/OR β-1,4-GLUCAN
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
DE19631764A1 (en) 1996-08-06 1998-02-12 Basf Ag Use of poly acids to treat mineral fertilisers - where the fertiliser contains nitrification inhibitor in mineral fertiliser, especially new or known pyrazole compound, to reduce volatility
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
EP0837944A2 (en) 1995-07-19 1998-04-29 Rhone-Poulenc Agrochimie Mutated 5-enol pyruvylshikimate-3-phosphate synthase, gene coding for said protein and transformed plants containing said gene
WO1998020145A2 (en) 1996-11-05 1998-05-14 National Starch And Chemical Investment Holding Corporation Improvements in or relating to starch content of plants
WO1998022604A1 (en) 1996-11-20 1998-05-28 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
WO1998027212A1 (en) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Novel nucleic acid molecules from maize and their use for the production of modified starch
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998027806A1 (en) 1996-12-24 1998-07-02 Pioneer Hi-Bred International, Inc. Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility
WO1998032326A2 (en) 1997-01-24 1998-07-30 Pioneer Hi-Bred International, Inc. Methods for $i(agrobacterium)-mediated transformation
WO1998039460A1 (en) 1997-03-04 1998-09-11 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules from artichoke ($i(cynara scolymus)) encoding enzymes having fructosyl polymerase activity
WO1998040503A1 (en) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding starch phosphorylase from maize
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
US5840946A (en) 1987-12-31 1998-11-24 Pioneer Hi-Bred International, Inc. Vegetable oil extracted from rapeseeds having a genetically controlled unusually high oleic acid content
WO1999012950A2 (en) 1997-09-06 1999-03-18 National Starch And Chemical Investment Holding Corporation Improvements in or relating to stability of plant starches
WO1999024593A1 (en) 1997-11-06 1999-05-20 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules which encode proteins having fructosyl transferase activity and methods for producing long-chain inulin
WO1999024585A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Mutated hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining herbicide-tolerant plants containing such gene
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
WO1999034008A1 (en) 1997-12-24 1999-07-08 Aventis Cropscience S.A. Method for enzymatic preparation of homogentisate
US5928937A (en) 1995-04-20 1999-07-27 American Cyanamid Company Structure-based designed herbicide resistant products
US5965755A (en) 1993-10-12 1999-10-12 Agrigenetics, Inc. Oil produced from the Brassica napus
US5969169A (en) 1993-04-27 1999-10-19 Cargill, Incorporated Non-hydrogenated canola oil for food applications
WO1999053072A1 (en) 1998-04-09 1999-10-21 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
WO1999058688A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999057965A1 (en) 1998-05-14 1999-11-18 Aventis Cropscience Gmbh Sulfonylurea-tolerant sugar beet mutants
WO1999058654A2 (en) 1998-05-13 1999-11-18 Planttec Biotechnologie Gmbh Forschung & Entwicklung Transgenic plants with a modified activity of a plastidial adp/atp translocator
WO1999058690A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999066050A1 (en) 1998-06-15 1999-12-23 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plants and plant products
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
WO2000004173A1 (en) 1998-07-17 2000-01-27 Aventis Cropscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
WO2000008185A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid molecule coding for beta-amylase, plants synthesizing a modified starch, method of production and applications
WO2000008184A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Plants which synthesize a modified starch, methods for producing the plants, their use, and the modified starch
WO2000011192A2 (en) 1998-08-25 2000-03-02 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
WO2000014249A1 (en) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding an amylosucrase
WO2000022140A1 (en) 1998-10-09 2000-04-20 Planttec Biotechnologie Gmbh Forschung & Entwicklung NUCLEIC ACID MOLECULES WHICH CODE A BRANCHING ENZYME FROM BACTERIA OF THE GENUS NEISSERIA, AND A METHOD FOR PRODUCING α-1,6-BRANCHED α-1,4-GLUCANS
WO2000028052A2 (en) 1998-11-09 2000-05-18 Planttec Biotechnologie Gmbh Nucleic acid molecules from rice encoding an r1 protein and their use for the production of modified starch
WO2000028055A2 (en) 1998-11-05 2000-05-18 Eden Bioscience Corporation Hypersensitive response elicitor-induced stress resistance
WO2000047727A2 (en) 1999-02-08 2000-08-17 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules encoding alternansucrase
WO2000066746A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000066747A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000073422A1 (en) 1999-05-27 2000-12-07 Planttec Biotechnologie Gmbh Genetically modified plant cells and plants with an increased activity of an amylosucrase protein and a branching enzyme
WO2000077229A2 (en) 1999-06-11 2000-12-21 Aventis Cropscience Gmbh R1 protein from wheat and the use thereof for the production of modified strach
WO2001012826A2 (en) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nucleic acid molecules derived from plants which code for enzymes which are involved in the synthesis of starch
WO2001012782A2 (en) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgenically modified plant cells and plants having modified gbssi- and be-protein activity
WO2001014339A2 (en) 1999-08-20 2001-03-01 Dow Agrosciences Llc Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
WO2001014569A2 (en) 1999-08-20 2001-03-01 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
WO2001017333A1 (en) 1999-09-10 2001-03-15 Texas Tech University Transgenic fiber producing plants with increased expression of sucrose phosphate synthase
WO2001019975A2 (en) 1999-09-15 2001-03-22 National Starch And Chemical Investment Holding Corporation Plants having reduced activity in two or more starch-modifying enzymes
WO2001024615A1 (en) 1999-10-07 2001-04-12 Valigen (Us), Inc. Non-transgenic herbicide resistant plants
US6229072B1 (en) 1995-07-07 2001-05-08 Adventa Technology Ltd Cytoplasmic male sterility system production canola hybrids
WO2001055115A1 (en) 2000-01-27 2001-08-02 Cytovia, Inc. Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
WO2001066704A2 (en) 2000-03-09 2001-09-13 Monsanto Technology Llc Methods for making plants tolerant to glyphosate and compositions thereof
WO2001065922A2 (en) 2000-03-09 2001-09-13 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower plants
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
WO2001098509A2 (en) 2000-06-21 2001-12-27 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
WO2002026995A1 (en) 2000-09-29 2002-04-04 Syngenta Limited Herbicide resistant plants
WO2002034923A2 (en) 2000-10-23 2002-05-02 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
WO2002036782A2 (en) 2000-10-30 2002-05-10 Maxygen, Inc. Novel glyphosate n-acetyltransferase (gat) genes
WO2002036787A2 (en) 2000-10-30 2002-05-10 Bayer Cropscience S.A. Herbicide-tolerant plants through bypassing metabolic pathway
WO2002045485A1 (en) 2000-12-08 2002-06-13 Commonwealth Scienctific And Industrial Research Organisation Modification of sucrose synthase gene expression in plant tissue and uses therefor
WO2002079410A2 (en) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Glucan chain length domains
WO2002101059A2 (en) 2001-06-12 2002-12-19 Bayer Cropscience Gmbh Transgenic plants synthesising high amylose starch
WO2003013226A2 (en) 2001-08-09 2003-02-20 Cibus Genetics Non-transgenic herbicide resistant plants
WO2003033540A2 (en) 2001-10-17 2003-04-24 Basf Plant Science Gmbh Starch
WO2003071860A2 (en) 2002-02-26 2003-09-04 Bayer Cropscience Gmbh Method for generating maize plants with an increased leaf starch content, and their use for making maize silage
WO2003092360A2 (en) 2002-04-30 2003-11-13 Verdia, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2004024928A2 (en) 2002-09-11 2004-03-25 Bayer Cropscience S.A. Transformed plants with enhanced prenylquinone biosynthesis
US6734341B2 (en) 1999-09-02 2004-05-11 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
WO2004040012A2 (en) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides
US20040116479A1 (en) 2002-10-04 2004-06-17 Fortuna Haviv Method of inhibiting angiogenesis
WO2004053219A2 (en) 2002-12-05 2004-06-24 Jentex Corporation Abrasive webs and methods of making the same
WO2004056999A1 (en) 2002-12-19 2004-07-08 Bayer Cropscience Gmbh Plant cells and plants which synthesize a starch with an increased final viscosity
WO2004078983A2 (en) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Enhanced amylose production in plants
WO2004090140A2 (en) 2003-04-09 2004-10-21 Bayer Bioscience N.V. Methods and means for increasing the tolerance of plants to stress conditions
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005002359A2 (en) 2003-05-22 2005-01-13 Syngenta Participations Ag Modified starch, uses, methods for production thereof
WO2005002324A2 (en) 2003-07-04 2005-01-13 Institut National De La Recherche Agronomique Method of producing double low restorer lines of brassica napus having a good agronomic value
WO2005012515A2 (en) 2003-04-29 2005-02-10 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2005012529A1 (en) 2003-07-31 2005-02-10 Toyo Boseki Kabushiki Kaisha Plant producing hyaluronic acid
WO2005017157A1 (en) 2003-08-15 2005-02-24 Commonwealth Scientific And Industrial Research Organisation (Csiro) Methods and means for altering fiber characteristics in fiber-producing plants
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005030942A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with reduced activity of a class 3 branching enzyme
WO2005030941A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with increased activity of a class 3 branching enzyme
WO2005042493A1 (en) 2003-10-23 2005-05-12 Bayer Cropscience Aktiengesellschaft Hexyl carboxanilides and their use for controlling undesirable micro-organisms
WO2005042492A1 (en) 2003-10-23 2005-05-12 Bayer Cropscience Aktiengesellschaft 1,3-dimethylbutyl carboxanilides for controlling undesirable micro-organisms
WO2005093093A2 (en) 2004-03-22 2005-10-06 Basf Aktiengesellschaft Methods and compositions for analyzing ahasl genes
WO2005095619A1 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of multiple starch phosphorylating enzymes
WO2005095632A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Methods for identifying proteins with starch phosphorylating enzymatic activity
WO2005095617A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of a starch phosphorylating enzyme
WO2005095618A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with reduced activity of the starch phosphorylating enzyme phosphoglucan, water dikinase
WO2005123927A1 (en) 2004-06-21 2005-12-29 Bayer Cropscience Gmbh Plants that produce amylopectin starch with novel properties
WO2006007373A2 (en) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides encoding mature ahasl proteins for creating imidazolinone-tolerant plants
WO2006015376A2 (en) 2004-08-04 2006-02-09 Basf Plant Science Gmbh Monocot ahass sequences and methods of use
WO2006018319A1 (en) 2004-08-18 2006-02-23 Bayer Cropscience Gmbh Plants with increased plastidic activity of r3 starch-phosphorylating enzyme
WO2006021972A1 (en) 2004-08-26 2006-03-02 Dhara Vegetable Oil And Foods Company Limited A novel cytoplasmic male sterility system for brassica species and its use for hybrid seed production in indian oilseed mustard brassica juncea
WO2006024351A1 (en) 2004-07-30 2006-03-09 Basf Agrochemical Products B.V. Herbicide-resistant sunflower plants, plynucleotides encoding herbicide-resistant acetohydroxy acid synthase large subunit proteins, and methods of use
WO2006032538A1 (en) 2004-09-23 2006-03-30 Bayer Cropscience Gmbh Methods and means for producing hyaluronan
WO2006060634A2 (en) 2004-12-01 2006-06-08 Basf Agrochemical Products, B.V. Novel mutation involved in increased tolerance to imidazolinone herbicides in plants
WO2006063862A1 (en) 2004-12-17 2006-06-22 Bayer Cropscience Ag Transformed plant expressing a dextransucrase and synthesizing a modified starch
WO2006072603A2 (en) 2005-01-10 2006-07-13 Bayer Cropscience Ag Transformed plant expressing a mutansucrase and synthesizing a modified starch
WO2006103107A1 (en) 2005-04-01 2006-10-05 Bayer Cropscience Ag Phosphorylated waxy potato starch
WO2006108702A1 (en) 2005-04-08 2006-10-19 Bayer Cropscience Ag High-phosphate starch
JP2006304779A (en) 2005-03-30 2006-11-09 Toyobo Co Ltd Plant producing hexosamine in high productivity
WO2006133827A2 (en) 2005-06-15 2006-12-21 Bayer Bioscience N.V. Methods for increasing the resistance of plants to hypoxic conditions
WO2006136351A2 (en) 2005-06-24 2006-12-28 Bayer Bioscience N.V. Methods for altering the reactivity of plant cell walls
WO2007009823A1 (en) 2005-07-22 2007-01-25 Bayer Cropscience Ag Overexpression of starch synthase in plants
WO2007024782A2 (en) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions providing tolerance to multiple herbicides and methods of use thereof
WO2007027777A2 (en) 2005-08-31 2007-03-08 Monsanto Technology Llc Nucleotide sequences encoding insecticidal proteins
WO2007039315A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with an increased production of hyaluronan ii
WO2007039316A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Improved methods and means for producings hyaluronan
WO2007039314A2 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with increased hyaluronan production
JP2007186434A (en) 2006-01-12 2007-07-26 Astellas Pharma Inc Medicinal composition
EP1987717A1 (en) 2007-04-30 2008-11-05 Bayer CropScience AG Pyridon carboxamides, agents containing these but not impacting useful plants and method for their manufacture and application
WO2013037955A1 (en) 2011-09-16 2013-03-21 Bayer Intellectual Property Gmbh Use of acylsulfonamides for improving plant yield

Patent Citations (193)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6063A (en) 1849-01-30 Improvement in baking apparatus
US947A (en) 1838-09-25 Machine fob dyeing yarn from the beam
US2532055A (en) 1945-04-03 1950-11-28 Wyeth Corp Pyridone derivatives
DE1905834A1 (en) 1969-02-06 1970-09-03 Basf Ag Salts and fertilizers provided with a coating to avoid dusting and caking
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
DE3534948A1 (en) 1985-10-01 1987-04-09 Bayer Ag FUNGICIDES AND GROWTH REGULATORY AGENTS
US4960896A (en) 1985-11-26 1990-10-02 A. H. Robins Company, Inc. Process for the preparation of 5-chloro and 5-bromo-2-hydroxynicotinic acids
US5648477A (en) 1986-03-11 1997-07-15 Plant Genetic Systems, N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US7112665B1 (en) 1986-03-11 2006-09-26 Bayer Bioscience N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5646024A (en) 1986-03-11 1997-07-08 Plant Genetic Systems, N.V. Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5561236A (en) 1986-03-11 1996-10-01 Plant Genetic Systems Genetically engineered plant cells and plants exhibiting resistance to glutamine synthetase inhibitors, DNA fragments and recombinants for use in the production of said cells and plants
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5141870A (en) 1987-07-27 1992-08-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5840946A (en) 1987-12-31 1998-11-24 Pioneer Hi-Bred International, Inc. Vegetable oil extracted from rapeseeds having a genetically controlled unusually high oleic acid content
WO1989010396A1 (en) 1988-04-28 1989-11-02 Plant Genetic Systems N.V. Plants with modified stamen cells
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
US5201931A (en) 1988-12-01 1993-04-13 Her Majesty The Queen In Right Of Canada, As Represented By The National Research Council Of Canada Abscisic acid-related plant growth regulators - germination promoters
DD277835A1 (en) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS
DD277832A1 (en) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit MEANS FOR INCREASING THE STRESSTOLERANCE OF CULTURAL PLANTS
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
WO1991002069A1 (en) 1989-08-10 1991-02-21 Plant Genetic Systems N.V. Plants with modified flowers
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
US5434283A (en) 1990-04-04 1995-07-18 Pioneer Hi-Bred International, Inc. Edible endogenous vegetable oil extracted from rapeseeds of reduced stearic and palmitic saturated fatty acid content
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
US5463175A (en) 1990-06-25 1995-10-31 Monsanto Company Glyphosate tolerant plants
US5776760A (en) 1990-06-25 1998-07-07 Monsanto Company Glyphosate tolerant plants
WO1992005251A1 (en) 1990-09-21 1992-04-02 Institut National De La Recherche Agronomique Dna sequence imparting cytoplasmic male sterility, mitochondrial genome, nuclear genome, mitochondria and plant containing said sequence and process for the preparation of hybrids
DE4103253A1 (en) 1991-02-04 1992-08-06 Bitterfeld Wolfen Chemie Agent to increase stress tolerance of crops and forests - contains synergistic mixt. of choline chloride and N-(2-hydroxy-ethyl)-piperazine
EP0571427A1 (en) 1991-02-13 1993-12-01 Hoechst Schering AgrEvo GmbH Plasmids containing dna-sequences that cause changes in the carbohydrate concentration and the carbohydrate composition in plants, as well as plant cells and plants containing these plasmids
EP0502740A1 (en) 1991-03-07 1992-09-09 E.I. Du Pont De Nemours And Company Herbicidal pyridine sulfonamide
EP0522392A1 (en) 1991-07-11 1993-01-13 E.I. Du Pont De Nemours And Company Substituted pyridines and a process for their preparation
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
US5767361A (en) 1991-07-31 1998-06-16 American Cyanamid Company Imidazolinone resistant AHAS mutants
DE4128828A1 (en) 1991-08-30 1993-03-04 Basf Ag AMMONIUM OR UREA-CONTAINED DISPENSERS AND METHOD FOR THEIR PRODUCTION
EP0544151A1 (en) 1991-11-26 1993-06-02 BASF Aktiengesellschaft Hydroxypyridone carboxylic acid amides, their preparation and use as herbicides
EP0663956A1 (en) 1992-08-12 1995-07-26 Hoechst Schering AgrEvo GmbH Dna sequences which lead to the formation of polyfructans (levans), plasmids containing these sequences as well as a process for preparing transgenic plants
WO1994004693A2 (en) 1992-08-26 1994-03-03 Zeneca Limited Novel plants and processes for obtaining them
WO1994009144A1 (en) 1992-10-14 1994-04-28 Zeneca Limited Novel plants and processes for obtaining them
WO1994011520A2 (en) 1992-11-09 1994-05-26 Zeneca Limited Novel plants and processes for obtaining them
WO1994021795A1 (en) 1993-03-25 1994-09-29 Ciba-Geigy Ag Novel pesticidal proteins and strains
US5969169A (en) 1993-04-27 1999-10-19 Cargill, Incorporated Non-hydrogenated canola oil for food applications
WO1995004826A1 (en) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Debranching enzymes and dna sequences coding them, suitable for changing the degree of branching of amylopectin starch in plants
EP0719338A1 (en) 1993-09-09 1996-07-03 Hoechst Schering AgrEvo GmbH Combination of dna sequences which enable the formation of modified starch in plant cells and plants, processes for the production of these plants and the modified starch obtainable therefrom
WO1995009910A1 (en) 1993-10-01 1995-04-13 Mitsubishi Corporation Gene that identifies sterile plant cytoplasm and process for preparing hybrid plant by using the same
US5965755A (en) 1993-10-12 1999-10-12 Agrigenetics, Inc. Oil produced from the Brassica napus
US6169190B1 (en) 1993-10-12 2001-01-02 Agrigenetics Inc Oil of Brassica napus
EP0728213A1 (en) 1993-11-09 1996-08-28 E.I. Du Pont De Nemours And Company Transgenic fructan accumulating crops and methods for their production
US5908975A (en) 1993-11-09 1999-06-01 E. I. Du Pont De Nemours And Company Accumulation of fructans in plants by targeted expression of bacterial levansucrase
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
WO1995026407A1 (en) 1994-03-25 1995-10-05 National Starch And Chemical Investment Holding Corporation Method for producing altered starch from potato plants
WO1995031553A1 (en) 1994-05-18 1995-11-23 Institut Für Genbiologische Forschung Berlin Gmbh DNA SEQUENCES CODING FOR ENZYMES CAPABLE OF FACILITATING THE SYNTHESIS OF LINEAR α-1,4 GLUCANS IN PLANTS, FUNGI AND MICROORGANISMS
WO1995035026A1 (en) 1994-06-21 1995-12-28 Zeneca Limited Novel plants and processes for obtaining them
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
WO1996001904A1 (en) 1994-07-08 1996-01-25 Stichting Scheikundig Onderzoek In Nederland Production of oligosaccharides in transgenic plants
WO1996015248A1 (en) 1994-11-10 1996-05-23 Hoechst Schering Agrevo Gmbh Dna molecules that code for enzymes involved in starch synthesis, vectors, bacteria, transgenic plant cells and plants containing said molecules
WO1996019581A1 (en) 1994-12-22 1996-06-27 Hoechst Schering Agrevo Gmbh Dna molecules coding for debranching enzymes derived from plants
WO1996021023A1 (en) 1995-01-06 1996-07-11 Centrum Voor Plantenveredelings- En Reproduktieonderzoek (Cpro - Dlo) Dna sequences encoding carbohydrate polymer synthesizing enzymes and method for producing transgenic plants
WO1996027674A1 (en) 1995-03-08 1996-09-12 Hoechst Schering Agrevo Gmbh Modified starch from plants, plants synthesizing this starch, and process for its preparation
US5928937A (en) 1995-04-20 1999-07-27 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996033270A1 (en) 1995-04-20 1996-10-24 American Cyanamid Company Structure-based designed herbicide resistant products
WO1996034968A2 (en) 1995-05-05 1996-11-07 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plant starch composition
WO1996038567A2 (en) 1995-06-02 1996-12-05 Rhone-Poulenc Agrochimie Dna sequence of a gene of hydroxy-phenyl pyruvate dioxygenase and production of plants containing a gene of hydroxy-phenyl pyruvate dioxygenase and which are tolerant to certain herbicides
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US20020031826A1 (en) 1995-06-07 2002-03-14 Nichols Scott E. Glucan-containing compositions and paper
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US6229072B1 (en) 1995-07-07 2001-05-08 Adventa Technology Ltd Cytoplasmic male sterility system production canola hybrids
EP0837944A2 (en) 1995-07-19 1998-04-29 Rhone-Poulenc Agrochimie Mutated 5-enol pyruvylshikimate-3-phosphate synthase, gene coding for said protein and transformed plants containing said gene
GB2305174A (en) 1995-09-15 1997-04-02 Zeneca Ltd Chemical process
WO1997011188A1 (en) 1995-09-19 1997-03-27 Planttec Biotechnologie Gmbh Plants which synthesise a modified starch, process for the production thereof and modified starch
WO1997020936A1 (en) 1995-12-06 1997-06-12 Zeneca Limited Modification of starch synthesis in plants
WO1997026362A1 (en) 1996-01-16 1997-07-24 Planttec Biotechnologie Gmbh Nucleic acid molecules from plants coding enzymes which participate in the starch synthesis
WO1997032985A1 (en) 1996-03-07 1997-09-12 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules coding for debranching enzymes from maize
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997042328A1 (en) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleic acid molecules which code the potato debranching enzyme
WO1997044472A1 (en) 1996-05-17 1997-11-27 Planttec Biotechnologie Gmbh Nucleic acid molecules coding soluble maize starch synthases
WO1997045545A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nucleic acid molecules encoding enzymes from wheat which are involved in starch synthesis
WO1997047808A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047806A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1997047807A1 (en) 1996-06-12 1997-12-18 Pioneer Hi-Bred International, Inc. Substitutes for modified starch in paper manufacture
WO1998000549A1 (en) 1996-06-27 1998-01-08 The Australian National University MANIPULATION OF CELLULOSE AND/OR β-1,4-GLUCAN
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE19631764A1 (en) 1996-08-06 1998-02-12 Basf Ag Use of poly acids to treat mineral fertilisers - where the fertiliser contains nitrification inhibitor in mineral fertiliser, especially new or known pyrazole compound, to reduce volatility
WO1998020145A2 (en) 1996-11-05 1998-05-14 National Starch And Chemical Investment Holding Corporation Improvements in or relating to starch content of plants
WO1998022604A1 (en) 1996-11-20 1998-05-28 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
WO1998027212A1 (en) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Novel nucleic acid molecules from maize and their use for the production of modified starch
WO1998027806A1 (en) 1996-12-24 1998-07-02 Pioneer Hi-Bred International, Inc. Oilseed brassica containing an improved fertility restorer gene for ogura cytoplasmic male sterility
WO1998032326A2 (en) 1997-01-24 1998-07-30 Pioneer Hi-Bred International, Inc. Methods for $i(agrobacterium)-mediated transformation
WO1998039460A1 (en) 1997-03-04 1998-09-11 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules from artichoke ($i(cynara scolymus)) encoding enzymes having fructosyl polymerase activity
WO1998040503A1 (en) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding starch phosphorylase from maize
WO1999012950A2 (en) 1997-09-06 1999-03-18 National Starch And Chemical Investment Holding Corporation Improvements in or relating to stability of plant starches
WO1999024593A1 (en) 1997-11-06 1999-05-20 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nucleic acid molecules which encode proteins having fructosyl transferase activity and methods for producing long-chain inulin
WO1999024586A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Chimeric hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining plants containing such a gene, with herbicide tolerance
WO1999024585A1 (en) 1997-11-07 1999-05-20 Aventis Cropscience S.A. Mutated hydroxy-phenyl pyruvate dioxygenase, dna sequence and method for obtaining herbicide-tolerant plants containing such gene
WO1999034008A1 (en) 1997-12-24 1999-07-08 Aventis Cropscience S.A. Method for enzymatic preparation of homogentisate
WO1999053072A1 (en) 1998-04-09 1999-10-21 E.I. Du Pont De Nemours And Company Starch r1 phosphorylation protein homologs
WO1999058688A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058690A2 (en) 1998-05-08 1999-11-18 Aventis Cropscience Gmbh Nucleic acid molecules which code for enzymes derived from wheat and which are involved in the synthesis of starch
WO1999058654A2 (en) 1998-05-13 1999-11-18 Planttec Biotechnologie Gmbh Forschung & Entwicklung Transgenic plants with a modified activity of a plastidial adp/atp translocator
WO1999057965A1 (en) 1998-05-14 1999-11-18 Aventis Cropscience Gmbh Sulfonylurea-tolerant sugar beet mutants
WO1999066050A1 (en) 1998-06-15 1999-12-23 National Starch And Chemical Investment Holding Corporation Improvements in or relating to plants and plant products
WO2000004173A1 (en) 1998-07-17 2000-01-27 Aventis Cropscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
WO2000008185A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Nucleic acid molecule coding for beta-amylase, plants synthesizing a modified starch, method of production and applications
WO2000008184A1 (en) 1998-07-31 2000-02-17 Aventis Cropscience Gmbh Plants which synthesize a modified starch, methods for producing the plants, their use, and the modified starch
WO2000011192A2 (en) 1998-08-25 2000-03-02 Pioneer Hi-Bred International, Inc. Plant glutamine: fructose-6-phosphate amidotransferase nucleic acids
WO2000014249A1 (en) 1998-09-02 2000-03-16 Planttec Biotechnologie Gmbh Nucleic acid molecules encoding an amylosucrase
WO2000022140A1 (en) 1998-10-09 2000-04-20 Planttec Biotechnologie Gmbh Forschung & Entwicklung NUCLEIC ACID MOLECULES WHICH CODE A BRANCHING ENZYME FROM BACTERIA OF THE GENUS NEISSERIA, AND A METHOD FOR PRODUCING α-1,6-BRANCHED α-1,4-GLUCANS
WO2000028055A2 (en) 1998-11-05 2000-05-18 Eden Bioscience Corporation Hypersensitive response elicitor-induced stress resistance
WO2000028052A2 (en) 1998-11-09 2000-05-18 Planttec Biotechnologie Gmbh Nucleic acid molecules from rice encoding an r1 protein and their use for the production of modified starch
WO2000047727A2 (en) 1999-02-08 2000-08-17 Planttec Biotechnologie Gmbh Forschung & Entwicklung Nucleic acid molecules encoding alternansucrase
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
WO2000066746A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000066747A1 (en) 1999-04-29 2000-11-09 Syngenta Limited Herbicide resistant plants
WO2000073422A1 (en) 1999-05-27 2000-12-07 Planttec Biotechnologie Gmbh Genetically modified plant cells and plants with an increased activity of an amylosucrase protein and a branching enzyme
WO2000077229A2 (en) 1999-06-11 2000-12-21 Aventis Cropscience Gmbh R1 protein from wheat and the use thereof for the production of modified strach
WO2001012826A2 (en) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nucleic acid molecules derived from plants which code for enzymes which are involved in the synthesis of starch
WO2001012782A2 (en) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgenically modified plant cells and plants having modified gbssi- and be-protein activity
WO2001014569A2 (en) 1999-08-20 2001-03-01 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
WO2001014339A2 (en) 1999-08-20 2001-03-01 Dow Agrosciences Llc Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
US6734341B2 (en) 1999-09-02 2004-05-11 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
WO2001017333A1 (en) 1999-09-10 2001-03-15 Texas Tech University Transgenic fiber producing plants with increased expression of sucrose phosphate synthase
WO2001019975A2 (en) 1999-09-15 2001-03-22 National Starch And Chemical Investment Holding Corporation Plants having reduced activity in two or more starch-modifying enzymes
WO2001024615A1 (en) 1999-10-07 2001-04-12 Valigen (Us), Inc. Non-transgenic herbicide resistant plants
WO2001055115A1 (en) 2000-01-27 2001-08-02 Cytovia, Inc. Substituted nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof
WO2001065922A2 (en) 2000-03-09 2001-09-13 E. I. Du Pont De Nemours And Company Sulfonylurea-tolerant sunflower plants
WO2001066704A2 (en) 2000-03-09 2001-09-13 Monsanto Technology Llc Methods for making plants tolerant to glyphosate and compositions thereof
WO2001098509A2 (en) 2000-06-21 2001-12-27 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
WO2002026995A1 (en) 2000-09-29 2002-04-04 Syngenta Limited Herbicide resistant plants
WO2002034923A2 (en) 2000-10-23 2002-05-02 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
WO2002036782A2 (en) 2000-10-30 2002-05-10 Maxygen, Inc. Novel glyphosate n-acetyltransferase (gat) genes
WO2002036787A2 (en) 2000-10-30 2002-05-10 Bayer Cropscience S.A. Herbicide-tolerant plants through bypassing metabolic pathway
WO2002045485A1 (en) 2000-12-08 2002-06-13 Commonwealth Scienctific And Industrial Research Organisation Modification of sucrose synthase gene expression in plant tissue and uses therefor
WO2002079410A2 (en) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Glucan chain length domains
WO2002101059A2 (en) 2001-06-12 2002-12-19 Bayer Cropscience Gmbh Transgenic plants synthesising high amylose starch
WO2003013226A2 (en) 2001-08-09 2003-02-20 Cibus Genetics Non-transgenic herbicide resistant plants
WO2003033540A2 (en) 2001-10-17 2003-04-24 Basf Plant Science Gmbh Starch
WO2003071860A2 (en) 2002-02-26 2003-09-04 Bayer Cropscience Gmbh Method for generating maize plants with an increased leaf starch content, and their use for making maize silage
WO2003092360A2 (en) 2002-04-30 2003-11-13 Verdia, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2004024928A2 (en) 2002-09-11 2004-03-25 Bayer Cropscience S.A. Transformed plants with enhanced prenylquinone biosynthesis
US20040116479A1 (en) 2002-10-04 2004-06-17 Fortuna Haviv Method of inhibiting angiogenesis
WO2004040012A2 (en) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions and methods for identifying plants having increased tolerance to imidazolinone herbicides
WO2004053219A2 (en) 2002-12-05 2004-06-24 Jentex Corporation Abrasive webs and methods of making the same
WO2004056999A1 (en) 2002-12-19 2004-07-08 Bayer Cropscience Gmbh Plant cells and plants which synthesize a starch with an increased final viscosity
WO2004078983A2 (en) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Enhanced amylose production in plants
WO2004090140A2 (en) 2003-04-09 2004-10-21 Bayer Bioscience N.V. Methods and means for increasing the tolerance of plants to stress conditions
WO2005012515A2 (en) 2003-04-29 2005-02-10 Pioneer Hi-Bred International, Inc. Novel glyphosate-n-acetyltransferase (gat) genes
WO2005002359A2 (en) 2003-05-22 2005-01-13 Syngenta Participations Ag Modified starch, uses, methods for production thereof
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005002324A2 (en) 2003-07-04 2005-01-13 Institut National De La Recherche Agronomique Method of producing double low restorer lines of brassica napus having a good agronomic value
WO2005012529A1 (en) 2003-07-31 2005-02-10 Toyo Boseki Kabushiki Kaisha Plant producing hyaluronic acid
WO2005017157A1 (en) 2003-08-15 2005-02-24 Commonwealth Scientific And Industrial Research Organisation (Csiro) Methods and means for altering fiber characteristics in fiber-producing plants
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2005030942A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with reduced activity of a class 3 branching enzyme
WO2005030941A1 (en) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Plants with increased activity of a class 3 branching enzyme
WO2005042493A1 (en) 2003-10-23 2005-05-12 Bayer Cropscience Aktiengesellschaft Hexyl carboxanilides and their use for controlling undesirable micro-organisms
WO2005042492A1 (en) 2003-10-23 2005-05-12 Bayer Cropscience Aktiengesellschaft 1,3-dimethylbutyl carboxanilides for controlling undesirable micro-organisms
WO2005095619A1 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of multiple starch phosphorylating enzymes
WO2005095632A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Methods for identifying proteins with starch phosphorylating enzymatic activity
WO2005095617A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with increased activity of a starch phosphorylating enzyme
WO2005095618A2 (en) 2004-03-05 2005-10-13 Bayer Cropscience Gmbh Plants with reduced activity of the starch phosphorylating enzyme phosphoglucan, water dikinase
WO2005093093A2 (en) 2004-03-22 2005-10-06 Basf Aktiengesellschaft Methods and compositions for analyzing ahasl genes
WO2006007373A2 (en) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides encoding mature ahasl proteins for creating imidazolinone-tolerant plants
WO2005123927A1 (en) 2004-06-21 2005-12-29 Bayer Cropscience Gmbh Plants that produce amylopectin starch with novel properties
WO2006024351A1 (en) 2004-07-30 2006-03-09 Basf Agrochemical Products B.V. Herbicide-resistant sunflower plants, plynucleotides encoding herbicide-resistant acetohydroxy acid synthase large subunit proteins, and methods of use
WO2006015376A2 (en) 2004-08-04 2006-02-09 Basf Plant Science Gmbh Monocot ahass sequences and methods of use
WO2006018319A1 (en) 2004-08-18 2006-02-23 Bayer Cropscience Gmbh Plants with increased plastidic activity of r3 starch-phosphorylating enzyme
WO2006021972A1 (en) 2004-08-26 2006-03-02 Dhara Vegetable Oil And Foods Company Limited A novel cytoplasmic male sterility system for brassica species and its use for hybrid seed production in indian oilseed mustard brassica juncea
WO2006032538A1 (en) 2004-09-23 2006-03-30 Bayer Cropscience Gmbh Methods and means for producing hyaluronan
WO2006060634A2 (en) 2004-12-01 2006-06-08 Basf Agrochemical Products, B.V. Novel mutation involved in increased tolerance to imidazolinone herbicides in plants
WO2006063862A1 (en) 2004-12-17 2006-06-22 Bayer Cropscience Ag Transformed plant expressing a dextransucrase and synthesizing a modified starch
WO2006072603A2 (en) 2005-01-10 2006-07-13 Bayer Cropscience Ag Transformed plant expressing a mutansucrase and synthesizing a modified starch
JP2006304779A (en) 2005-03-30 2006-11-09 Toyobo Co Ltd Plant producing hexosamine in high productivity
WO2006103107A1 (en) 2005-04-01 2006-10-05 Bayer Cropscience Ag Phosphorylated waxy potato starch
WO2006108702A1 (en) 2005-04-08 2006-10-19 Bayer Cropscience Ag High-phosphate starch
WO2006133827A2 (en) 2005-06-15 2006-12-21 Bayer Bioscience N.V. Methods for increasing the resistance of plants to hypoxic conditions
WO2006136351A2 (en) 2005-06-24 2006-12-28 Bayer Bioscience N.V. Methods for altering the reactivity of plant cell walls
WO2007009823A1 (en) 2005-07-22 2007-01-25 Bayer Cropscience Ag Overexpression of starch synthase in plants
WO2007024782A2 (en) 2005-08-24 2007-03-01 Pioneer Hi-Bred International, Inc. Compositions providing tolerance to multiple herbicides and methods of use thereof
WO2007027777A2 (en) 2005-08-31 2007-03-08 Monsanto Technology Llc Nucleotide sequences encoding insecticidal proteins
WO2007039315A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with an increased production of hyaluronan ii
WO2007039316A1 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Improved methods and means for producings hyaluronan
WO2007039314A2 (en) 2005-10-05 2007-04-12 Bayer Cropscience Ag Plants with increased hyaluronan production
JP2007186434A (en) 2006-01-12 2007-07-26 Astellas Pharma Inc Medicinal composition
EP1987717A1 (en) 2007-04-30 2008-11-05 Bayer CropScience AG Pyridon carboxamides, agents containing these but not impacting useful plants and method for their manufacture and application
WO2008131860A2 (en) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridonecarboxamides crop protection agents containing the same method for production and use thereof
WO2013037955A1 (en) 2011-09-16 2013-03-21 Bayer Intellectual Property Gmbh Use of acylsulfonamides for improving plant yield

Non-Patent Citations (49)

* Cited by examiner, † Cited by third party
Title
"Biochemistry and Molecular Biology of Plants", 2000, AMERICAN SOCIETY OF PLANT PHYSIOLOGISTS, pages: 1102 - 1203
"Biochemistry and Molecular Biology of Plants", 2000, AMERICAN SOCIETY OF PLANT PHYSIOLOGISTS, pages: 850 - 929
"Pflanzenbiochemie", 1996, SPEKTRUM AKADEMISCHER VERLAG, pages: 393 - 462
"Ullmann's Encyclopedia of Industrial Chemistry", vol. A 10, 1987, pages: 363 - 401
"Ullmann's Encyclopedia of Industrial Chemistry", vol. A 10, 1987, VERLAGSGESELLSCHAFT, pages: 323 - 431
BARRY ET AL., CURR. TOPICS PLANT PHYSIOL., vol. 7, 1992, pages 139 - 145
BARTLETT ET AL., PEST MANAG SCI, vol. 60, 2002, pages 309
BRAY, PLANT PHYSIOL, vol. 103, 1993, pages 1035 - 1040
CEDERGREEN, ENV. POLLUTION, vol. 156, 2008, pages 1099
CHEM. HET. COMP., 2004, pages 1155
CHEM. PHARM. BULL., vol. 48, 2000, pages 1847 - 1853
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 40, no. 9, 2004, pages 1155 - 1161
CHEN ET AL., PLANT CELL ENVIRON, vol. 23, 2000, pages 609 - 618
CHURCHILL ET AL., PLANT GROWTH REGUL, vol. 25, 1998, pages 35 - 45
CLOSE, PHYSIOL PLANT, vol. 100, 1997, pages 291 - 296
COMAI ET AL., SCIENCE, vol. 221, 1983, pages 370 - 371
CRICKMORE ET AL., MICROBIOLOGY AND MOLECULAR BIOLOGY REVIEWS, vol. 62, 1998, pages 807 - 813
DE BLOCK ET AL., THE PLANT JOURNAL, vol. 41, 2005, pages 95
GASSER ET AL., J. BIOL. CHEM., vol. 263, 1988, pages 4280 - 4289
HASEGAWA ET AL., ANNU REV PLANT PHYSIOL PLANT MOL BIOL, vol. 51, 2000, pages 463 - 499
HELV. CHIM. ACTA, vol. 71, 1988, pages 596
HELV. CHIM. ACTA, vol. 71, 1988, pages 596 - 601
INGRAM; BARTELS, ANNU REV PLANT PHYSIOL PLANT MOL BIOL, vol. 47, 1996, pages 277 - 403
J. FLUOR. CHEM., vol. 107, 2001, pages 285 - 300
J. HETEROCYCL. CHEM., vol. 33, 1996, pages 287 - 294
J. MED. CHEM., vol. 32, 1989, pages 2178 - 2199
J. MED. CHEM., vol. 33, 1990, pages 1859 - 1865
J. MED. CHEM., vol. 36, 1993, pages 2676 - 2688
J. MED. CHEM., vol. 36, 1993, pages 2676 - 2788
J. MED. CHEM., vol. 46, 2003, pages 702 - 715
J. ORG. CHEM., vol. 23, 1958, pages 1614
J. ORG. CHEM., vol. 49, 1984, pages 4784 - 4786
JAGLO-OTTOSEN ET AL., SCIENCE, vol. 280, 1998, pages 104 - 106
KIRCH ET AL., PLANT MOL BIOL, vol. 57, 2005, pages 315 - 332
LEVINE ET AL., FEBS LETT, vol. 440, 1998, pages 1
MOELLENBECK ET AL., NAT. BIOTECHNOL., vol. 19, 2001, pages 668 - 72
MORRISON; ANDREWS, J PLANT GROWTH REGUL, vol. 11, 1992, pages 113 - 117
ORGANIC LETTERS, vol. 6, 2004, pages 3 - 5
ORGANOMETALLICS, vol. 15, 1996, pages 5374 - 5379
R. WEGLER: "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", vol. 2, 1970, SPRINGER VERLAG, pages: 401 - 412
SCHNEPF ET AL., APPLIED ENVIRONM. MICROB., vol. 71, 2006, pages 1765 - 1774
SEMBDNER; PARTHIER, ANN. REV. PLANT PHYSIOL. PLANT MOL. BIOL., vol. 44, 1993, pages 569 - 589
SHAH ET AL., SCIENCE, vol. 233, 1986, pages 478 - 481
SYN. COMM., 1982, pages 35
SYNTH. COMMUN., vol. 19, 1989, pages 553 - 560
SYNTHESIS, 2000, pages 738 - 742
TETRAHEDRON LETT., vol. 45, 2004, pages 6633 - 6636
TRANEL; WRIGHT, WEED SCIENCE, vol. 50, 2002, pages 700 - 712
YU ET AL., MOL CELLS, vol. 19, 2005, pages 328 - 333

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11178872B2 (en) 2016-05-09 2021-11-23 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
WO2018190350A1 (en) * 2017-04-10 2018-10-18 三井化学アグロ株式会社 Pyridone compound, and agricultural and horticultural fungicide having this as active component
JPWO2018190350A1 (en) * 2017-04-10 2020-03-26 三井化学アグロ株式会社 Pyridone compounds and fungicides for agricultural and horticultural use containing the same as active ingredients
US11147272B2 (en) 2017-04-10 2021-10-19 Mitsui Chemicals Argro, Inc. Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients
JP7168556B2 (en) 2017-04-10 2022-11-09 三井化学アグロ株式会社 Pyridone compound and agricultural and horticultural fungicide containing it as an active ingredient
WO2019039429A1 (en) * 2017-08-22 2019-02-28 日本曹達株式会社 Cyclic amine compound and pest control agent
EP3674291A4 (en) * 2017-08-22 2020-12-23 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
EP3889137A1 (en) * 2017-08-22 2021-10-06 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
WO2021003295A1 (en) * 2019-07-02 2021-01-07 Regeneron Pharmaceuticals, Inc. Modulators of hsd17b13 and methods of use thereof
US11957687B2 (en) 2019-07-02 2024-04-16 Regeneron Pharmaceuticals, Inc. Modulators of HSD17B13 and methods of use thereof

Also Published As

Publication number Publication date
AR103024A1 (en) 2017-04-12

Similar Documents

Publication Publication Date Title
WO2014037340A1 (en) Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress
WO2013041602A1 (en) Use of 4-substituted 1-phenyl-pyrazole-3-carboxylic-acid derivatives as agents against abiotic plant stress
EP3051946B1 (en) Use of substituted dihydrooxindolylsulfonamides or their salts for increasing stress tolerance in plants
EP2658376A1 (en) Use of substituted spirocyclic sulfonamidocarboxylic acids, carboxylic esters thereof, carboxamides thereof and carbonitriles thereof or salts thereof for enhancement of stress tolerance in plants
EP2729007A1 (en) Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants
WO2012139890A1 (en) Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ines as active agents against abiotic stress in plants
EP2892344A1 (en) Use of substituted benzodiazepinones and benzazepinones or the salts thereof as active substances against abiotic plant stress
WO2014086751A1 (en) Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress
EP2928297A1 (en) Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-bicycloalkanols as active agents against abiotic plant stress
EP3325446A1 (en) Substituted aryl and heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants
EP3128841A1 (en) Use of substituted oxo tetrahydroquinoline sulfonamides or salts thereof for raising stress tolerance of plants
WO2015004040A1 (en) Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress
EP2542533B1 (en) Fluoralkyl-substituted 2-amidobenzimidazoles and their use for increasing stress tolerance in plants
WO2016096942A1 (en) Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress
WO2017009321A1 (en) Substituted oxo-tetrahydroquinolinyl-phosphinic acid and phosphinic acid amides or salts thereof and use thereof to increase stress tolerance in plants
WO2017012965A1 (en) Substituted heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants
WO2016128365A1 (en) Substituted 1-cycloalkyl-2-oxotetrahydroquinolin-6-yl-sulfonamides or salts thereof and use thereof to increase stress tolerance in plants
WO2018108627A1 (en) Use of substituted indolinylmethyl sulfonamides, or the salts thereof for increasing the stress tolerance of plants
EP2510786A1 (en) Substituted Prop-2-in-1-ol and Prop-2-en-1-ol derivatives
EP3325466A1 (en) Substituted cyclic aryl and heteroaryl carboxylic acid hydrazides or salts thereof and use thereof to increase stress tolerance in plants
EP3172187A1 (en) Substituted cyano cycloalkyl penta-2,4-dienes, cyano cycloalkyl pent-2-en-4-ynes, cyano heterocyclyl penta-2,4-dienes and cyano heterocyclyl pent-2-en-4-ynes as active substances against abiotic plant stress
EP3332645A1 (en) Use of substituted pyrimidine diones or their salts as agents to combat abiotic plant stress
EP2740356A1 (en) Substituted (2Z)-5(1-Hydroxycyclohexyl)pent-2-en-4-inic acid derivatives
EP2555626A2 (en) Use of derivatives of the (1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15810624

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15810624

Country of ref document: EP

Kind code of ref document: A1