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WO2016096942A1 - Utilisation de pyridone-carboxamides sélectionnés ou de leurs sels comme principes actifs contre le stress abiotique des plantes - Google Patents

Utilisation de pyridone-carboxamides sélectionnés ou de leurs sels comme principes actifs contre le stress abiotique des plantes Download PDF

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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
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alkyl
alkoxy
carbonyl
substituted
radicals
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Inventor
Lars ARVE
Frank Ziemer
Fabien Poree
Dirk Schmutzler
Jan Dittgen
Harry STREK
Udo Bickers
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Bayer CropScience AG
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Bayer CropScience AG
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    • 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.

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

Utilisation de pyridone-carboxamides substitués de formule générale (I) ou de leurs sels, les groupes de la formule générale (I) ayant les définitions figurant dans la description, pour augmenter la tolérance des plantes au stress abiotique, renforcer la croissance des plantes et/ou augmenter le rendement des plantes.
PCT/EP2015/079926 2014-12-18 2015-12-16 Utilisation de pyridone-carboxamides sélectionnés ou de leurs sels comme principes actifs contre le stress abiotique des plantes Ceased WO2016096942A1 (fr)

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WO2019039429A1 (fr) * 2017-08-22 2019-02-28 日本曹達株式会社 Composé amine cyclique et agent de lutte contre les organismes nuisibles
WO2021003295A1 (fr) * 2019-07-02 2021-01-07 Regeneron Pharmaceuticals, Inc. Modulateurs de hsd17b13 et leurs procédés d'utilisation
US11178872B2 (en) 2016-05-09 2021-11-23 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent

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