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EP3325466A1 - Hydrazides cycliques substitués d'acide arylcarboxylique et hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux - Google Patents

Hydrazides cycliques substitués d'acide arylcarboxylique et hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux

Info

Publication number
EP3325466A1
EP3325466A1 EP16738415.5A EP16738415A EP3325466A1 EP 3325466 A1 EP3325466 A1 EP 3325466A1 EP 16738415 A EP16738415 A EP 16738415A EP 3325466 A1 EP3325466 A1 EP 3325466A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
cio
heteroaryl
heterocyclyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP16738415.5A
Other languages
German (de)
English (en)
Inventor
Jens Frackenpohl
Guido Bojack
Marco BRÜNJES
Hendrik Helmke
Stefan Lehr
Isabelle Adelt
Jan Dittgen
Udo Bickers
Martin Jeffrey Hills
Dirk Schmutzler
Ines Heinemann
Juan Pedro RUIZ-SANTAELLA MORENO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 AG filed Critical Bayer CropScience AG
Publication of EP3325466A1 publication Critical patent/EP3325466A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/50—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/98—Nitrogen atom
    • 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
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • 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
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D401/14—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 three or more hetero rings
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    • 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
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07D417/12—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 chain containing hetero atoms as chain links
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Definitions

  • the invention relates to substituted cyclic aryl and Heteroarylcarbonklare- hydrazides or their salts and their use for increasing the stress tolerance in plants to abiotic stress, and to increase the
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • substituted azinylcarboxamides such as, for example, substituted 4- (trifluoromethyl) nicotinamides, possess insecticidal properties (cf., for example, EP185256, WO2001 / 014373, WO2002 / 022583, JP07010841, JP07025853, WO2005 / 1 13553).
  • N-substituted Azinylalkylazincarboxamide and their insecticidal activity are described in DE102008041214, wherein as N-substituents of the amides in question, for example, alkyl, arylcarbonyl, alkylcarbonyl,
  • 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 700: 291-296). These are chaperones, the vesicles, proteins and 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).
  • ROS reactive oxygen species
  • 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
  • naphthylsulfonamide (4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071).
  • a naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline) exhibits a mode of action in biochemical receptor tests which are Bromine-N- (pyridin-2-ylmethyl) -naphthalene-1-sulfonamide (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1, 102-1, 108).
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
  • Xanthines for increasing the abiotic stress tolerance in plants has already been described (Bergmann et al., DD277832, Bergmann et al., DD277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide compounds which further increase the tolerance to abiotic stress in plants, cause a strengthening of plant growth and / or contribute to the increase of the plant yield.
  • tolerance to abiotic stress for example, tolerance to cold, heat,
  • Drought stress stress caused by drought and / or lack of water
  • salting and flooding understood.
  • substituted cyclic aryl- and heteroarylcarboxylic acid hydrazides can be used to increase the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase plant yield.
  • the present invention accordingly provides substituted cyclic aryl and heteroarylcarboxylic acid hydrazides of the general formula (I) or salts thereof,
  • R 1 , R 2 and R 38 independently of one another represent hydrogen, halogen, cyano, nitro,
  • (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl- (C 1 -C 8 ) -alkyl, COOR 42 , CONR 39 R 40 , COR 41 , -C NOR 41 , R 41 OOC- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkynyl, heteroaryl- (C 1 -C 8 ) -alkynyl, heterocyclyl- (C 1 -C 8 ) -alkynyl, tris [(C 1 -C 8 ) alkyl] silyl (C 2 -C 8 ) alkynyl, bis - [(C 1 -C 8 ) alkyl] (aryl) silyl (C 2 -C 8 ) alkynyl, bis-aryl [(
  • Aryl diazo tris - [(C 1 -C 8 ) alkyl] silyl, bis - [(C 1 -C 8 ) alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) alkyl] silyl,
  • X 1 , X 2 , X 3 and X 4 are the same or different and are independently N
  • W is O (oxygen) or S (sulfur),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or CR 38 , but in no case are more than two N atoms adjacent, and R 38 in the grouping C-R 38 has the same or different meanings as defined above,
  • R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 are each as defined in the have the following definitions and wherein the arrow represents a bond to the N atom of the hydrazide group,
  • R 3 , R 4 , R 17 , R 18 , R 19 and R 20 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, NR 39 R 40 , S (O) n R 42 , cyano, nitro, cyano (Ci-C 8) -alkyl, (C3-C10) - cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C 4 -Cio) - Halocycloalkenyl, (Ci-Cio) Haloalkyl, aryl, aryl- (C 1 -C 8) -alkyl, heteroaryl,
  • R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 independently of one another represent hydrogen, cyano, nitro, halogen, hydroxy, (C 1 -C 8) -alkyl, (C 1 -C 5) -alkoxy, ( C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -haloalkylthio, (C 3 -C 10) -cycloalkyl, (C 1 -C 10) -haloalkyl, aryl, aryl- (C 1 -C 8 ) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) - cycloalkyl, (Ci-C 8) alkyl, (C 2 -C 8) haloalkynyl, (C 2 - C 8) alkyn
  • R 39 and R 40 are the same or different and are independently of each other
  • Alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, heterocyclyl (Ci-C 8) alkyl represents hydrogen, (Ci-Cs) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl , (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 10) -cycloalkenyl, (C 1 -C 10) -cycloalkenyl, (C 1 -C 10) -
  • R 42 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 8 ) -cycloalkenyl, Cio) -
  • Y for a bond or for the groupings Y-1 to Y-7
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 are each the
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl, ( C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) haloalkynyl, (C 3 -Cio) cycloalkyl, aryl, aryl (Ci-Cs) - alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alk
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or completely unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 3 and R 4 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring
  • R 3 and R 23 with the atoms to which they form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring
  • R 9 and R 10 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring
  • R 15 and R 16 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring.
  • the compounds of general formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4, HSPO 4 or HNO 3, or organic acids, eg.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Sulfonic acids certain sulfonic acid amides or carboxylic acids are present, internal salts can in turn form protonatable groups, such as amino groups.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
  • Hydrogen is replaced by a cation suitable for agriculture
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to Each R d is independently one
  • alkylsulfonium and Alkylsulfoxoniumsalze represent organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and Alkylsulfoxoniumsalze such as (Ci-C4) - trialkylsulfonium and (Ci-C 4) -Trialkylsulfoxoniumsalze.
  • Heteroarylcarboxylic acid hydrazides of formula (I) may be present in various tautomeric structures, all of which are of general formula (I), depending on external conditions such as pH, solvent and temperature and X 1 , X 2 , X 3 and X 4 should.
  • the compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • R 1 , R 2 and R 38 independently of one another represent hydrogen, halogen, cyano, nitro,
  • (Ci-C7) -alkyl (Ci-C7) -alkyl, (Ci-C7) -alkyl alkoxy- (Ci-C7) -alkyl, (Ci-C 7) -Al kylth io- (Ci-C7) -alkyl .
  • (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl- (C 1 -C 7 ) -alkyl, COOR 42 , CONR 39 R 40 , COR 41 , -C NOR 41 , R 41 is OOC- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkynyl, heteroaryl- (C 1 -C 7 ) -alkynyl, heterocyclyl- (C 1 -C 7 ) -alkynyl, Tris - [(C 1 -C 7 ) alkyl] silyl (C 2 -C 7 ) alkynyl, bis - [(C 1 -C 7 ) alkyl] (aryl) silyl (C 2 -C 7 ) alkynyl , bis-
  • Aryldiazo tris - [(C 1 -C 7 ) alkyl] silyl, bis - [(C 1 -C 7 ) alkyl] (aryl) silyl, bis-aryl [(C 1 -C 7 ) alkyl] silyl,
  • X 1 , X 2 , X 3 and X 4 are the same or different and are independently N
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or CR 38 , but in no case are more than two N atoms adjacent, and R 38 in the grouping C-
  • R 38 has the same or different meanings as defined above, together with the group CR 3 R 4 and the nitrogen atom to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 3 -7-membered ring forms and further for the groupings Q-1 to Q-15
  • R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 are each the Have meaning as defined below and wherein the arrow represents a bond to the N atom of the hydrazide group, R 4 , R 17 , R 18 , R 19 and R 20 independently of one another are hydrogen, halogen,
  • NR 39 R 40 S (O) n R 42 , cyano, nitro, cyano- (C 1 -C 7 ) -alkyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -Cio ) Cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 10) -haloalkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 2 -C 7) haloalkynyl, (C 2 -C 7) -alkynyl, (C 2 -C 7) - alkenyl, (C 2 - C 7)
  • R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 independently of one another represent hydrogen, cyano, nitro, halogen, hydroxy, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy , (Ci-C7) -alkylthio, (Ci-C7) haloalkoxy, (Ci-C 7) haloalkylthio, (C 3 -Cio) cycloalkyl, (C1-C10) - Haloalkyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) - cycloalkyl- (Ci-C7) alkyl, (C 2 -C 7 ) -haloalkynyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7
  • R 42 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (C1-C7) - cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, Cio) - halocycloalkenyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, aryl, aryl- (C 1 -C 7
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 are each the
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, ( C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -Cio) cycloalkyl, aryl, aryl (Ci-C7) - alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl , heterocyclyl, heterocyclyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7)
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 3 and R 4 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring
  • R 3 and R 23 with the atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring
  • R 9 and R 10 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring, and
  • R 15 and R 16 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring.
  • R 1 , R 2 and R 38 independently of one another represent hydrogen, halogen, cyano, nitro,
  • Aryldiazo tris - [(C 1 -C 6 ) alkyl] silyl, bis - [(C 1 -C 6 ) alkyl] (aryl) silyl, bis-aryl [(C 1 -C 6 ) alkyl] silyl, X 1 , X 2 , X 3 and X 4 are the same or different and are independently N
  • W is O (oxygen) or S (sulfur)
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and independently of one another represent N (nitrogen) or the group CR 38 , but in none If more than two N atoms are adjacent, and where R 38 in the grouping C-R 38 has the same or different meanings as defined above,
  • R 7, R 8, R 9, R 10, R 1 1, R 12, R 13, R 14, R 15, R 16, R 17, R 18, R 19, R 20, R 21, R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 are each the same meaning have the following definitions and wherein the arrow represents a bond to the N atom of the hydrazide group,
  • R 3, R 4, R 17, R 18, R 19 and R 20 are independently hydrogen, halogen,
  • NR 39 R 40 S (O) n R 42 , cyano, nitro, cyano- (C 1 -C 6 ) -alkyl, (C 3 -Cio) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -Cio ) Cycloalkenyl, (C 4 -C 10) -halocycloalkenyl,
  • R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 independently of one another represent hydrogen, cyano, nitro, halogen, hydroxy, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkylthio,
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 are each the
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, ( C2-C6) alkenyl, (C2-C6) -alkynyl, (Ci-Cio) -haloalkyl, (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, (C 3 -Cio) - Cycloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (Ci -C 6) alkyl, (Ci-
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they belong
  • R 3 and R 4 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 3 and R 23 with the atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 9 and R 10 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7-membered ring, and
  • R 15 and R 16 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring.
  • Very particular preference is given to compounds of the general formula (I) which are described by the formulas (Ia) to (Iu)
  • R 2 and R 38 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, NR 39 R 40 , OR 41 , S (O) n R 42 , thiocyanato, isothiocyanato, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1 - dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1 - dimethylpropyl, 1, 2-dimethylpropyl , 2,2-dimethylpropyl, 1-ethylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally substituted phenyl, heteroaryl, heterocyclyl, cyclopropyl, cyclobutyl, cycl
  • X 1 , X 2 , X 3 and X 4 are the same or different and are independently N
  • W is O (oxygen) or S (sulfur), preferably O (oxygen),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or CR 38 , but in no case are more than two N atoms adjacent, and R 38 in the grouping C-R 38 has the same or different meanings as defined above,
  • R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2 Methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl,
  • Hydrogen methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-thymethylpropyl, 1, 2, 2-thmethylpropyl, 1-ethyl-1-
  • Difluoromethoxy-n-propyl 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2,2,2- Trifluoroethoxy-n-propyl, pentafluoroethoxymethyl, pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl, trifluoromethylthiomethyl,
  • Methoxycarbonylmethyl ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
  • Methoxycarbonylmethyl ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl,
  • Heteroaryl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl (Ci-C 6 ) -alkyl, NR 39 R 40 stands for a bond or for the groups Y-1 to Y-7
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 are each the
  • R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 and R 54 independently of one another are hydrogen, fluorine, methyl, ethyl, n-propyl, iso Propyl, n-butyl, iso-butyl, tert-butyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 - propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 - Methyl-2-propynyl, trifluoromethyl, pentafluoroe
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and X 2 , when both represent a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, form optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring, and A 2 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally Heteroatoms form interrupted and optionally further substituted 5-7 membered ring, and A 3 , when both represent a group CR 7 , with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered form a
  • a 3 and A 4 when both represent a group CR 7 , with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring.
  • R 2 and R 38 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
  • X 1 , X 2 , X 3 and X 4 are the same or different and are independently N
  • R 1 and R 2 are not simultaneously hydrogen when X 1 , X 2 , X 3 and X 4 are CR 2 ,
  • W is O (oxygen) or S (sulfur), preferably O (oxygen),
  • a 1 , A 2 , A 3 , A 4 and A 5 are the same or different and are independently N (nitrogen) or CR 38 , but in no case are more than two N atoms adjacent, and R 38 in the grouping C-R 38 has the same or different meanings as defined above,
  • R 5 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1 -
  • Y is a bond or groups Y-1 to Y-2
  • R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are each as defined below, and wherein the arrow for binding to the 6-membered ring having the groups A 1 , A 2 , A 3 , A 4 and A 5 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are each independently hydrogen, methyl
  • R 5 and R 6 with the atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5-7 membered ring,
  • R 1 and X 1 when X 1 is a group CR 2 , with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X 1 and X 2 when both represent a group CR 2 , with the atoms to which they belong
  • a 1 and A 2 when both represent a group CR 7 , with the atoms to which they belong
  • a 2 and A 3 when both represent a group CR 7 , with the atoms to which they belong
  • Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl 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, for example (but not limited to) (Ci- C6) -alkylsulfonyl such as methylsulfonyl , Ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl , 1, 2-dimethylpropylsulfonyls,
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4 ) -alkylthio, for example (but not limited to) (C 1 -C 4 ) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethyl thio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethyl
  • Alkenylthio means according to the invention a bonded via a sulfur atom
  • Alkenyl radical, 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.
  • alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, Pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl-propylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methyl
  • alkenylsulfonyl and alkynylsulfonyl are defined according to the invention as alkenyl or alkynyl radicals which are linked to the skeleton via -S (OO) 2, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • -S (OO) 2 such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -) C) -alkenylsulfonyl or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C) -alkynylsulfonyl.
  • Alkoxy means an alkyl radical attached via an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy , 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-
  • Oxygen-bonded alkenyl radical, alkynyloxy means one over one
  • Oxygen-bonded alkynyl such as (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (Cs-Ce) - or (C 3 -C) -alkynoxy ,
  • Cycloalkyloxy means a cycloalkyl radical bonded through an oxygen atom, and cycloalkenyloxy represents a cycloalkenyl radical attached via an oxygen atom.
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyl group.
  • alkenylcarbonyl and “alkynylcarbonyl” are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (OO) -, such as (C 2 -C 10) -, ( C 2 -C 6) - or (C 2 -C 4 ) -alkenylcarbonyl or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • Alkoxycarbonyl (alkyl-OC ( O) -), unless otherwise defined elsewhere:
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl” are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (OO) -, such as (C 2 -C 10) - , (C 2 -C 6) - or (C 2 -C 4 ) -alkenyloxycarbonyl or (C 3 -C 10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkynyloxycarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
  • alkenylcarbonyloxy and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (OO) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -C 6) - or (C 2 -C 4 ) -alkenylcarbonyloxy or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4 ) -alkynylcarbonyloxy.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally substituted phenyl ".
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • spirocyclic systems are also included, such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless otherwise defined, it contains heterocyclic ring preferably 3 to 9 ring atoms, in particular 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl;
  • Examples of structures optionally further substituted heterocycles are also listed below:
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N and S for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • the term "heteroaryl" is heteroaromatic
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinoline-7 yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinoline-7 yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • pyridopyrimidines Pyridopyridazine; pteridines; Pyrimidopyrimidine.
  • Heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1 H-indol-1-yl, 1 H-indol-2-yl, 1 H-indol-3-yl, 1 H-indol-4-yl, 1 H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl , 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1 Benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-ind
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and, in the latter case, is referred to as "substituted alkyl".
  • Substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio,
  • Haloalkylthio, amino or nitro groups particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • the prefix "bis" also includes the combination of different alkyl radicals, for example, methyl (ethyl) or
  • Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range given for C atoms include general alkyl radicals having a larger specified range of C atoms Atoms, z.
  • (Ci-C6) -alkyl accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not
  • (C 2 -C 6) alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl , 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 -
  • Methyl 3-butenyl 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
  • (C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4 pentynyl, 2-methyl-3-pentynyl,
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl,
  • Haloalkyl amino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • substituents having a double bond on
  • Cycloalkyl, z As an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl it also encompasses polycyclic aliphatic systems such as, for example, bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentane 1 -yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl,
  • (C 3 -C 7) -cycloalkyl means a
  • cycloalkyl having three to 7 carbon atoms corresponding to the range for C atoms.
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, for example a
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • the compounds of the general formula (I) can, depending on the nature and linkage of Substituents exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • Substituted cyclic aryl and heteroarylcarboxylic acid hydrazides of general formula (I) can be prepared by known methods (see Tetrahedron 2003, 59, 7733, J. Organomet Chem 2001, 617, J. Org. Chem. 1962, 27, 2640;
  • Heteroarylcarbonklare chloride if this is not commercially available, and this with a correspondingly 1, 1 '-disubstituted cyclic hydrazine using a suitable base (eg triethylamine (Et ⁇ N)), di-iso-propylethylamine) in a suitable polar aprotic solvent (eg
  • THF Tetrahydrofuran
  • DCM dichloromethane
  • substituted cyclic aryl or heteroarylcarboxylic acid hydrazide (A) can also be prepared by direct reaction with suitable reagents (eg 1-hydroxybenzotriazoles (HOBt), N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride (EDC) or 2,4 , 6-Tripropyl-1, 3,5,2,4,6-trioxatri-phosphorinane-2,4,6-trioxide (T3P) together with a suitable base such as triethylamine or di-iso-propylethylamine) mediated coupling of an optionally further substituted aryl or heteroarylcarboxylic acid with a corresponding 1, 1 'disubstituted cyclic hydrazine in a suitable polar aprotic solvent (eg dichloromethane, acetonitrile or tetrahydrofuran) are prepared.
  • the optionally further substituted cyclic aryl or heteroarylcarboxylic acid hydrazide (A) is prepared using an appropriately substituted arylalkyl halide or heteroarylalkyl halide and a suitable base (eg, sodium hydride or triethylamine (EtsN)) in a suitable solvent (eg, tetrahydrofuran, ⁇ , ⁇ Dimethylformamide (DMF) or dichloromethane) into a substituted cyclic aryl or
  • a suitable base eg, sodium hydride or triethylamine (EtsN)
  • a suitable solvent eg, tetrahydrofuran, ⁇ , ⁇ Dimethylformamide (DMF) or dichloromethane
  • a suitable reagent eg triethylsilane, BH3, sodium cyanoborohydride, sodium borohydride or hydrogen on palladium / carbon
  • a suitable solvent eg triethylsilane, BH3, sodium cyanoborohydride, sodium borohydride or hydrogen on palladium / carbon
  • Hydrazin concept (C) which in the final reaction step with an optionally further substituted aryl or heteroarylcarboxylic acid chloride in a suitable polar aprotic solvent (eg., Tetrahydrofuran or
  • Heteroarylcarbonklad (I) is transferred (Scheme 2).
  • R 1 , R 3 , R 4 and R 5 and A 1 , A 2 , A 3 , A 4 , A 5 , X 1 , X 2 , X 3 , Q and Y have the meanings defined above and W is exemplified, but not limiting, in scheme 2 below for oxygen.
  • Example numbers are as shown in Tables A1 through XX below mentioned numbering.
  • dt double triplet.
  • N- (3-methoxyazetidin-1-yl) -2- (trifluoromethyl) benzamide 110 mg, 0.40 mmol was dissolved in abs. Dissolved tetrahydrofuran (5 ml) under argon and at room temperature with sodium hydride (24 mg, 0.60 mmol, 60% dispersion). After stirring for 30 minutes at room temperature, 2- (chloromethyl) -3,5-dimethyl-4-methoxypyridine (102 mg, 0.55 mmol) was added, and the resulting reaction mixture was allowed to stand for 3 hours
  • N- (pyrrolidin-1-yl) -2- (trifluoromethyl) benzamide as a colorless solid (2160 mg, 52% of theory).
  • 1 H-NMR 400 MHz, CDCIs ⁇ , ppm) 7.71-7.67 (m, 1H), 7.62-7.48 (m, 3H), 6.41 (br.s, 1H, NH), 3.5-3.00 (m, 4H), 1 .96-1 .89 (m, 4H).
  • N- (pyrrolidin-1-yl) -2- (trifluoromethyl) benzamide 1000 mg, 3.87 mmol was dissolved in abs. Tetrahydrofuran (15 ml) was dissolved under argon and at
  • 2,6-Difluorobenzoic acid (1 equiv) was dissolved in abs. Dissolved dichloromethane (10 ml / mmol) and treated with triethylamine (3 equiv.). After stirring at room temperature for 5 minutes, 1-aminopyrrolidine (1: 3 equiv) and 2,4,6-tripropyl-1,3,2,2,4,6-trioxatriphosphorinane-2,4,6-trioxide were added (1 .5 equiv, 50% solution in
  • N- (pyrrolidin-1-yl) -4- (trifluoromethyl) nicotinamide 100 mg, 0.39 mmol was dissolved in abs.
  • Tetrahydrofuran (6 ml) was dissolved under argon and treated at room temperature with sodium hydride (17 mg, 0.42 mmol, 60% pure). After stirring at room temperature for 30 minutes, 2-chlorobenzyl chloride (62 mg, 0.39 mmol) was added, and the resulting reaction mixture was stirred under reflux conditions for two and a half hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added.
  • N- (pyrrolidin-1-yl) -4- (trifluoromethyl) nicotinamide (100 mg, 0.39 mmol) was dissolved in abs. Tetra hydrofu ran (6 ml) under argon and treated at room temperature with sodium hydride (17 mg, 0.42 mmol, 60% pure). After stirring at room temperature for 30 minutes, 2-chloromethylbenzonitrile (58 mg, 0.39 mmol) was added and the resulting reaction mixture was stirred at reflux for two and a half hours. After cooling to room temperature, sat. Sodium bicarbonate solution, water and dichloromethane added.
  • N- (morpholinyl-4-yl) -4- (trifluoromethyl) -nicotinamide could be isolated as a colorless solid (530 mg, 37% of theory).
  • N- (morpholin-4-yl) -4- (trifluoromethyl) nicotinamide 200 mg, 0.73 mmol was dissolved in a mixture of abs.
  • N, N-dimethylformamide (5 ml, 4: 1) was dissolved under argon and treated at room temperature with sodium hydride (41 mg, 1 .02 mmol, 60% purity). After stirring at room temperature for 30 minutes, 2-bromomethylbenzonitrile (143 mg, 0.73 mmol) and sodium iodide (22 mg, 0.15 mmol) were added, and the resulting reaction mixture was stirred at a temperature of 70 ° C for four hours. After cooling to room temperature, sat.
  • 2-chloronicotinic acid (1 equiv) was dissolved in abs. Dissolved dichloromethane (10 ml / mmol) and treated with triethylamine (3 equiv). After stirring at room temperature for 5 minutes, 1-aminopyrrolidine (1: 3 equiv) and 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide were added (1 .5 equiv, 50% solution in tetrahydrofuran). The resulting reaction mixture was stirred for 30 minutes at room temperature and then washed with water, sat. Sodium bicarbonate solution and dichloromethane. The aqueous phase was repeatedly intensively with
  • Chloro-N- (pyrrolidin-1-yl) nicotinamide can be isolated in the form of a colorless solid. 2-Chloro-N- (pyrrolidin-1-yl) nicotinamide (180 mg, 0.79 mmol) was then dissolved in abs. Dissolved N, N-dimethylformamide (10 ml) under argon and at room temperature with
  • N- (pyrrolidin-1-yl) -3- (trifluoromethyl) pyridine-2-carboxamide as a colorless solid.
  • N- (pyrrolidin-1-yl) -3- (trifluoromethyl) pyridine-2-carboxamide (200 mg, 0.77 mmol) was then dissolved in abs.
  • N, N-dimethylformamide (10 ml) was dissolved under argon and treated at room temperature with sodium hydride (50 mg, 1 .16 mmol, 60% purity).

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Abstract

L'invention concerne des hydrazides cycliques substitués d'acide arylcarboxylique et hétéroarylcarboxylique de formule générale (I) ou leurs sels, les restes de la formule (I) répondant aux définitions mentionnées dans la description, pour augmenter la tolérance des plantes au stress abiotique et pour renforcer la croissance des plantes et/ou pour augmenter le rendement des plantes.
EP16738415.5A 2015-07-17 2016-07-12 Hydrazides cycliques substitués d'acide arylcarboxylique et hétéroarylcarboxylique ou leurs sels, et leur utilisation pour accroître la tolérance au stress chez les végétaux Withdrawn EP3325466A1 (fr)

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