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EP3172187A1 - Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes - Google Patents

Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes

Info

Publication number
EP3172187A1
EP3172187A1 EP15738663.2A EP15738663A EP3172187A1 EP 3172187 A1 EP3172187 A1 EP 3172187A1 EP 15738663 A EP15738663 A EP 15738663A EP 3172187 A1 EP3172187 A1 EP 3172187A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
bis
alkoxy
aryl
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Withdrawn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
EP15738663.2A
Other languages
German (de)
English (en)
Inventor
Jens Frackenpohl
Lothar Willms
Jan Dittgen
Dirk Schmutzler
Martin Jeffrey Hills
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 EP3172187A1 publication Critical patent/EP3172187A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • 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
    • A—HUMAN NECESSITIES
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    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
    • A01N55/04—Tin
    • C—CHEMISTRY; METALLURGY
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    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
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    • 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
    • C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings 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 atoms
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Definitions

  • the invention relates to substituted cyano-cycloalkylpenta-2,4-dienes, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-enes, processes for their preparation and their use for increasing the stress tolerance in plants to abiotic stress and / or for increasing the yield of plants.
  • Epoxycarotenoid dioxygenase and as germination inhibitors is described in US2010 / 0160166.
  • (2Z, 4E) -5 - [(1S, 6S) -1-hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid and (2Z, 4E) -5- [(1R, 6R) -1 -HydrOxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid interact with cytochrome P707A (see Current Med. Chem., 2010, 17, 3230).
  • abscisic acid and its derivatives can be used as pharmaceutical agents for the regulation of calcium transport (see EP240257). It is also known that certain cyanocyclopropyl-substituted
  • Aryltriazolylethanoles (see JP02286668) can be used as agrochemical active substances for controlling pathogenic fungi. Furthermore, only a few
  • Cyanocycloalkyl-substituted alkenols as described, for example, 1 - [(2E) -1-hydroxy-1,3-diphenylprop-2-en-1-yl] cyclopentanecarbonitrile (in Dokl. Bolgarsk, Akad. Nauk 1971, 24, 621) and 1 - [(2E) -1-hydroxy-3-phenylprop-2-en-1-yl] cyclohexanecarbonitrile (in J. Organomt. Chem. 1973, 57, C36-C38).
  • abiotic stress for example, cold, heat, drought stress, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998,
  • the response to salt stress involves phosphatases of the ATPK and MP2C types. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and
  • 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
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants, in particular to effect a strengthening of plant growth and / or contribute to increasing the plant yield.
  • the present invention accordingly provides cyano-cycloalkylpenta-2,4-dienes, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-ines general formula (I) or salts thereof,
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective grouping [XY],
  • R 1 is hydrogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl, haloalkoxyalkyl, alkylthioalkyl, arylalkyl, heterocyclylalkyl, halocycloalkyl, cycloalkenyl,
  • R 2 is hydrogen, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkenyl, alkynyl,
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 independently of one another represent hydrogen, alkyl, halogen, cycloalkyl, alkoxy, aryl, heterocyclyl, heteroaryl, arylalkyl, alkylthio, haloalkyl, haloalkyloxy, haloalkylthio, alkoxyalkyl, alkylthioalkyl, heteroarylalkyl, heterocyclylalkyl,
  • Cycloalkylalkyl cycloalkenyl, alkynyl, alkenyl, haloalkenyl, haloalkynyl,
  • R 5 and R 6 independently of one another represent hydrogen, halogen, alkyl, haloalkyl,
  • R 7 represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, haloalkoxyalkyl,
  • R 6 and R 7 with the atoms to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
  • R 8 is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroarylalkyl, bis-arylalkyl, tris-arylalkyl, alkenyl, cycloalkenylalkyl, alkynylalkyl, trialkylsilylalkoxy kalk, alkoxyalkoxyalkyl, alkylthioalkyl, haloalkyl, arylsulfonylalkyl, trialkylsilyl, AI kyl- (bis-aryl) silyl, Al kyl- (bis-al kyl) silyl, bis-alkylaminoalkyl, heterocyclylalkyl, alkynyl, cyanoalkyl, heterocyclyl,
  • R 9 is hydrogen, alkyl, cycloalkyl, halogen, alkynylalkyl, haloalkyl, alkynyl, alkenyl, cyanoalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkenylalkyloxycarbonyl,
  • AI koxycarbonylcycloalkyl, hydroxycarbonylcycloalkyl
  • Arylalkoxycarbonylcycloalkyl AI kenyloxycarbonylcycloalkyl
  • AI kenyloxycarbonylheterocyclyl AI kenylal koxycarbonylheterocyclyl
  • Cycloalkylaminocarbonylheterocyclyl arylalkylaminocarbonylheterocyclyl, alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclylalkyl,
  • AI koxycarbonylheterocyclylalkyl, hydroxycarbonylcycloalkyl kylal
  • AI koxycarbonylcycloal kylal kyl, hydroxy, alkoxy, heterocyclyl, heterocyclylalkyl,
  • R 10 is hydrogen, alkyl, cycloalkyl, halogen, haloalkyl, alkynyl, alkenyl,
  • Cyanoalkyl arylalkyl, heteroarylalkyl, alkylcarbonyl, alkoxycarbonyl,
  • Cycloalkylsulfinyl, alkoxycarbonylalkyl, or R 9 and R 10 with the nitrogen to which they are attached are optionally halogen, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylkoxycarbonyl, alkenyloxycarbonyl, hydroxycarbonyl,
  • Arylalkylaminocarbonyl form substituted three to eight membered ring, which is optionally interrupted by O, S or N, or
  • R 9 and R 10 together form part of an optionally substituted sulfilimine or amidine group or form an iminophosphorane and
  • R 11 is hydrogen, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl.
  • the compounds of formula (I) can form salts. Salt formation can through
  • Sulfonamide group contains -NHSO2-.
  • suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or 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, for example metal salts, especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , in which R 1 to R'"each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl, Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4) -trialkylsulfonium and Ci-C4) -Trialkylsulfoxoniumsalze.
  • metal salts especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) am
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each have the meaning of the definitions below and wherein the arrow represents a bond to the respective moiety [XY],
  • R 1 is hydrogen , (C 1 -C 8) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C10) - cycloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C 2 C 8 ) alkynyl (C 1 -C 8 ) alkyl, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, hydroxy (C 1 -C 8 ) alkyl, ( C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8
  • R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl,
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyloxy, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) - alkyl, heterocyclyl (C 1 -C 8 ) alkyl, (
  • R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
  • R 5 and R 6 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - Cycloalkyl- (C 1 -C 8 ) -alkyl,
  • R 7 represents hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -haloalkoxy- (C 1 C 8 ) alkyl, (C 1 -C 8 ) haloalkoxy (C 1 -C 8 ) haloalkyl, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) haloalkyl, (C 1 -C 8 ) -alkynyloxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkenyloxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, ( C 1 -C 8 ) haloalkylthio, optionally substituted
  • R 6 and R 7 with the atoms to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
  • R 8 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, bis-aryl- (C 1 C 8 ) alkyl, tris-aryl (C 1 -C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 4 -C 8 ) cycloalkenyl (C 1 -C 8 ) alkyl, ( C 2 -C 8 ) alkynyl (C 1 -C 8 ) alkyl, tri (C 1
  • R 9 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, halogen, (C 2 -C 8 ) -alkynyl
  • R 9 and R 10 with the nitrogen to which they are attached are optionally substituted by halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, Hydroxycarbonyl, aminocarbonyl,
  • R 9 and R 10 together form an N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) - alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) alkyl (C 3 -C 7 ) cycloalkyl) sulfanylidene group or an N , N-di (C 1 -C 6 ) alkylformylidene group and R 11 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 8 ) -haloalkyl , (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, (C 1 -C 8 ) alkyl
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective grouping [XY],
  • R 1 is hydrogen, (C 1 -C 7) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C10) - cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl , (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) Haloalkenyl, (C 1 -C 7 ) haloalkoxy (C 1 -C 7 ) alkyl, (C 1 -C 7 ) alkylthio (C 1 -C 7 ) alkyl, aryl (C 1 -C 7 ) -alkyl,
  • R 2 is hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 7 ) -cycloalkylcarbonyl, (C 2 -C 7 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) -alkenyloxycarbonyl, aryloxy- (C 1
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 7) alkyl, halogen, (C 3 -C 7) - cycloalkyl, (C 1 -C 7) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyloxy, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) - alkyl, heterocyclyl (C 1 -C 7 ) alkyl, (
  • R 7 represents hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -Alkynyloxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -
  • R 6 and R 7 form, with the atoms to which they are attached, a fully saturated, optionally heteroatom-interrupted and optionally further substituted 3 to 6-membered ring
  • R 8 is hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, optionally substituted phenyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, bis-aryl- (C 1 -C 7 ) -alkyl, tris-aryl- (C 1 -) C 7 ) alkyl, (C 2 -C 7 ) alkenyl, (C 4 -C
  • Alkylaminocarbonylheterocyclyl bis (C 1 -C 7 ) -alkylaminocarbonylheterocyclyl,
  • Alkoxycarbonyl (C 3 -C 7 ) -cycloalkyl (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -alkoxy,
  • R 10 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halogen, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl, cyano- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) Alkylcarbonyl, (C 1 -C 7 ) alkoxycarbonyl, (C 1 -C 7 ) - Alkylsulfonyl, arylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl, (C 1 -C 7 ) -alkylsulfinyl
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective moiety [XY], is 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,
  • I'-b is cyclopropyl ⁇ -yl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1 Vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, 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-propen
  • Methoxyethoxyethyl methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl, is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl , Dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert -hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, n-propyl, iso -propyl, n Butyl, iso-butyl
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl , Cyclopentyl, cyclohexyl, cyclopropylcyclopropyl,
  • Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-chloro 2,2-difluoroethyl, difluoro-tert-butyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, difluoromethoxymethyl, difluoromethoxyethyl,
  • 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, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop -2-en-1-yl, but-2-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl -prop-1 -en-1-yl, but-3-en-1-yl, Pentenyl, 2-methylpentenyl, hexenyl, ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl
  • R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
  • R 5 and R 6 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, n-butyl, isobutyl, isopropyl, n-pentyl, n-hexyl, isopentyl, Trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl,
  • R 7 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
  • R 9 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, halogen, (C 2 -C 6 ) -alkynyl
  • R 10 is hydrogen, (C 1 -C 6) alkyl, (C3-C6) -cycloalkyl, halogen, (C 1 -C 6) -haloalkyl, (C 2 -C 6) -alkynyl, (C 2 - C 6 ) alkenyl, cyano (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl,
  • Heteroaryl (C 1 -C 6) alkyl, (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) Al koxycarbonyl, (C 1 -C 6) - alkylsulfonyl, arylsulfonyl, (C 3 -C 6 ) cycloalkylsulfonyl, (C 1 -C 6 ) -alkylsulfinyl,
  • R 9 and R 10 with the nitrogen to which they are attached form a optionally substituted by fluorine, chlorine, bromine, iodine, (C 1 -C 6 J-alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6 ) alkoxy,
  • R 9 and R 10 together represent N- (di-n-butyl-sulfanylidene), N- (di-iso-propyl-sulfanylidene), N- (di-n-propyl-sulfanylidene), N- (di-n- pentyl-sulfanylidene), N- (di-isobutyl-sulfanylidene), N- (cyclobutyl-isopropyl-sulfanylidene), N- (n-propyl-isopropyl-sulfanylidene), N- (cyclopropyl-iso- propyl-sulfanylidene), N- (iso-butyl-isopropyl-sulfanylidene), ⁇ , ⁇ -dimethylformylidene, R 11 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 2 , V, W independently represent a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl,
  • Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
  • R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and Q is one of the groups described in the following table Q-1.1 to Q-3.55 stands
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
  • Methylpropyl 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
  • R 2 represents hydrogen, tert-butyldimethylsilyl, Trimethylsilyl, triethylsilyl, tri (iso -propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, diethylisopropylsilyl, isopropyldimethylsilyl, tert -hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2 - (trimethylsilyl) ethyl, methyl,
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 1 , V, W independently of one another represent a group CR 3 R 4 ,
  • a 2 is a group CR 3 R 4 or oxygen, m is 0, n is 0, 1,
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, Heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2- Trifluoroethoxy, trifluoromethylthio, methoxymethyl, ethoxymethyl,
  • R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and Q is one of the groups Q-1.1 described in the table above until Q-3.55
  • Residue definitions apply both to the end products of the formula (I) and
  • R 1 is hydrogen, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl , (C 2 -C 8 ) -alkynyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy) (C 1 -C 8 ) -alkyl, HydrOxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) - Haloalkoxy (C 1 -C 8 ) alkyl.
  • R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl, (C 2 -C 8 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) --alkyl,
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl,
  • R 1 is hydrogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl,
  • R 2 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 6 ) -cycloalkylcarbonyl, (C 2 -C 6 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, aryloxy- (C 1
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 6) alkyl, halogen, (C 3 -C 6) - cycloalkyl, (C 1 -C 6) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkyloxy, (C 1 -C 6 ) -haloalkylthio, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) - alkyl, heterocyclyl - (C 1 -C 6 ) -al
  • R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring.
  • R 1 is 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-trimethylpropyl, 1, 2 , 2-trimethylpropyl, 1-e
  • R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, tert-butyloxy, iso-butyloxy, n-pentyloxy, optionally substituted phenyl, Heterocyclyl, heteroaryl, benzyl, p-CI-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio
  • Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
  • Cyclohexylmethyl optionally substituted phenyl, heteroaryl, Heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5- yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.
  • R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 1 , V, W independently of one another are a group CR 3 R 4 , a group CR 3 R 4 or oxygen, m is 0, n is 0, 1,
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, trifluoromethylthio, methoxy methyl, ethoxymethyl,
  • R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring.
  • R 1 is hydrogen, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl , (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, hydroxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) alkylthio (C 1 -C 8) al
  • R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl, (C 2 -C 8 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, aryloxy- (C 1 -
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyloxy, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) - alkyl, heterocyclyl - (C 1 -C 8 ) -al
  • R 1 is hydrogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) alkylthio (C 1 -C 6) al
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
  • R 3 and R 4 are independently hydrogen, (C 1 -C 6) alkyl, halogen, (C 3 -C 6) - cycloalkyl, (C 1 -C 6) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkyloxy, (C 1 -C 6 ) -haloalkylthio,
  • R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and [M] for tris - [(C 1 -C 6 ) -alkyl] stannyl, tris - [(C 3 -C 6 ) -cycloalkyl] stannyl, tris-KC 1 -C 6 ) -alkyl] germanyl, tris [ (C 3 -C 6 ) -cycloalkyl] germanyl, bis (cyclopentadienyl) zirconyl, bis (1, 2,3,4,5-pentamethylcyclopentadienyl) zirconyl, bis (cyclopentadienyl) hafnyl, bis (1, 2, 3,4,5
  • R 1 is 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-trimethylpropyl, 1, 2 , 2-trimethylpropyl, 1-e
  • R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
  • Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1, R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, tert-butyloxy, iso-butyloxy, n-pentyloxy, optionally substituted phenyl,
  • Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
  • [M] is trimethylstannyl, triethylstannyl, tris (n-propyl) stannyl, tris (isopropyl) stannyl, tris (n-butyl) stannyl, tris (sec-butyl) stannyl, tris (tert-butyl)
  • R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
  • R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
  • Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
  • a 1 , V, W independently of one another represent a group CR 3 R 4 ,
  • a 2 is a group CR 3 R 4 or oxygen, m is 0, n is 0, 1, R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, trifluoromethylthio, methoxy methyl, ethoxymethyl,
  • R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and
  • [M] is trimethylstannyl, triethylstannyl, tris (n-propyl) stannyl, tris (isopropyl) stannyl, tris (n-butyl) stannyl, tris (sec-butyl) stannyl, tris (tert-butyl) stannyl, tris (n-pentyl) stannyl, tris (n-hexyl) stannyl, for
  • 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,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • 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 - represents straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl , sec-butylsulfonyl and tert-butylsulfonyl.
  • heteroarylsulfonyl is optionally substituted
  • 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, 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
  • Alkoxy represents an alkyl radical bonded via an oxygen atom
  • alkenyloxy denotes an alkynyl radical bound via an oxygen atom
  • alkynyloxy denotes an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • 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 ".
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 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 - or 2- or 3- or 4- or
  • 5- or 6-yl 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
  • 6- or 7-yl 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-
  • 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; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
  • 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 known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring.
  • N (O) also known as SO
  • S (O) 2 also abbreviated to SO 2
  • 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-pyrazol-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, these are annelated 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, I H -indol-2-yl, I H -indol-3-yl, 1 H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl , 1-Benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-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-
  • 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 is referred to in the latter case 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.
  • Haloalkyl means the same or different
  • 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. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • 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 possibly existing ones
  • 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;
  • (C 1 -C 4) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range for C atoms, ie, the radicals include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. B. "(C 1 -C 6 ) -alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals with 5 and 6 C 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 in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, eg prop-1-en-1 yl, but-1-en-1-yl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-ene-1 yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl-prop-1-en-1-yl,
  • 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-yne 1-yl.
  • C 2 -C 6 ) -alkynyl is, for example, 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 1-methyl-but-3-yn-1-yl.
  • cycloalkyl means a carbocyclic, saturated and optionally substituted ring system having preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents wherein also
  • 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
  • Cycloalkyl identi means a carbocyclic radical which is bonded via a double bond.
  • stannyl represents a further substituted radical which is a tin atom "Germanyl” is analogous to a further substituted radical, the one
  • Zeroconyl represents a further substituted radical containing a zirconium atom.
  • Hafnyl represents a further substituted radical containing a hafnium atom.
  • Boryl represents a further substituted radical containing a hafnium atom.
  • Boryl is further substituted and optionally cyclic groups, each containing a boron atom.
  • Plumbanyl represents a further substituted radical containing a lead atom.
  • Haldrargyl represents a further substituted radical containing a mercury atom.
  • Alignyl represents a further substituted radical containing an aluminum atom.
  • Magnnesyl represents a further substituted radical containing a magnesium atom.
  • Zincyl represents a further substituted radical containing a zinc atom.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). 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.
  • the substituted cyano-cycloalkylpenta-2,4-dienes according to the invention, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-cyclohexanone Heterocyclylpent-2-en-4-ines of the general formula (I) can be prepared by known methods.
  • the known and structurally related natural plant substance abscisic acid can be obtained on various synthetic routes (see Hanson et al., J. Chem. Res. (S), 2003, 426; Constantino et al., J. Org. Chem. 1986, 51, 253; Constantino et al., 1989, 54, 681; Marsh et al., Org. Biomol.
  • the first key intermediate for the synthesis of the compounds of the general formula (I) according to the invention is an optionally further substituted 1- (2-hydroxybut-3-yn-2-yl) cycloalkylcarbonitrile of the general formula (II).
  • Solvent eg tetrahydrofuran or in two steps by reaction with trimethylsilylacetylene and LDA (lithium diisopropylamide) in a temperature range from -78 ° C to 0 ° C in a suitable polar aprotic solvent (eg.
  • Tetrahydrofuran and subsequent cleavage of the trimethylsilyl group with the aid of a suitable trialkylammonium fluoride (eg tetrabutylammonium fluoride) in a polar aprotic solvent or with a suitable carbonate base (eg.
  • a suitable trialkylammonium fluoride eg tetrabutylammonium fluoride
  • a suitable carbonate base eg.
  • a 1 , A 2 , V, W, R 1 , R 2 , R 5 , R 6 , R 7 and R 8 in the following Scheme 2 have the meanings defined above.
  • substituted cyano-cycloalkylpent-2-en-4-ene-1 (a) according to the invention can also be obtained by reaction of a suitable substituted ketone with
  • Transition metal-catalyzed coupling of a trialkylsilyl alkyne and a (Z) -iodoalkanoic acid derivative (compare J. Chem. Res. (S), 2003, 426, J. Chem. Soc, Perkin Trans., 2001, 47) using a suitable palladium catalyst (for example bis (triphenylphosphine) palladium dichloride) and a suitable copper (I) halide (eg copper (I) iodide) in a suitable solvent mixture of an amine and a polar aprotic solvent (eg diisopropylamine and toluene or
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
  • HOBt stands for hydroxybenzotriazole in this context.
  • R 5 , R 6 , R 7 , R 8 , R 9 and R 10 have in the following Scheme 3 the meanings defined above.
  • the substituted cyano-cycloalkylpent-2-en-4-carboxylic acid amides 1 (b) according to the invention are therefore accessible via two possible synthetic routes (Scheme 4), a) the conversion of the substituted cyano-cycloalkylpent-2-en-4-amino acids 1 ( a) by reaction with thionyl chloride and
  • a suitable palladium catalyst eg bis (triphenylphosphine) palladium dichloride
  • a suitable copper (I) halide eg copper (I) iodide
  • a suitable solvent mixture of an amine and a polar aprotic solvent eg diisopropylamine and toluene or triethylamine and tetrahydrofuran.
  • a 1 , A 2 , V, W, R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 and m and n have the previously defined meanings in the following Scheme 4.
  • the substituted (E, Z) -configured cyano-cycloalkylpenta-2,4-dienes 1 (c) according to the invention can be prepared by reducing the alkyne group of the inventive
  • lithium dissolved in a mixture of ethylamine and tert-butanol eg Helvetica Chimica Acta 1986, 69, 368
  • a suitable trialkoxysilane in the presence of a suitable transition metal catalyst (eg tris (acetonitrile) ruthenium 1, 2,3,4,5-pentamethylcyclopentadienylhexafluoro-phosphate or tris (acetonitrile) ruthenium-cyclopentadienylhexafluorophosphate, see J. Am.
  • a suitable transition metal catalyst eg tris (acetonitrile) ruthenium 1, 2,3,4,5-pentamethylcyclopentadienylhexafluoro-phosphate or tris (acetonitrile) ruthenium-cyclopentadienylhexafluorophosphate, see J. Am.
  • substituted 1 - [(3E) -2-hydroxy-4- [M] -but-3-en-2-yl] cycloalkylcarbonitriles may be prepared by coupling with a corresponding substituted (Z) -haloalkanoic acid derivative in a suitable solvent (e.g. Tetrahydrofuran or ⁇ , ⁇ -dimethylformamide) using appropriate
  • Transition metal catalysts e.g., bis (triphenylphosphine) palladium dicyanide, tetrakis (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride
  • E, Z -configured cyano-cycloalkylpenta-2,4-dienes of this invention (c ) (Scheme 6).
  • a 1 , A 2 , V, W, [M], R 1 , R 2 , R 5 , R 6 , R 7 and R 8, and m and n have the meanings defined above in the following Scheme 6.
  • Transition-metal catalyst such as Lindlars catalyst with hydrogen in a suitable polar aprotic solvent (such as n-butanol) (see Tetrahedron 1987, 43, 4107, Tetrahedron 1983, 39, 2315, J. Org. Synth. 1983, 48, 4436 and J. Am. Chem. Soc. 1984, 106, 2735) (Scheme 9).
  • a suitable polar aprotic solvent such as n-butanol
  • Transition metal catalysts eg bis (triphenylphosphine) palladium dicyanide
  • Example numbers given correspond to the numbering mentioned in Tables 1 to 5 below.
  • N-cyclopropylpent-2-ynamide (1 equiv) was concentrated in conc.
  • Dissolved acetic acid (2 ml / mmol) treated with finely powdered sodium iodide (3 equiv) and stirred for 4 hours at a temperature of 110 ° C.
  • MTBE methyl tert-butyl ether
  • the aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • ethyl (2Z) -6- (1-cyancyclopropyl) -6-hydroxy-3-methyl-6-phenylhex-2-ene-4-ynate (320 mg, 42% of theory ) isolated in the form of a colorless oil.
  • Ethyl 3-ethylprop-2-ynate (700 mg, 5.55 mmol) was concentrated in conc. Acetic acid (7 ml) was added, mixed with finely powdered sodium iodide (2.49 g, 16.65 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases dried over magnesium sulfate, filtered and under
  • Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
  • reaction mixture was stirred for 3 hours at room temperature and then treated with water.
  • the aqueous phase was extracted several times with dichloromethane.
  • the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
  • Pent-2-carboxylic acid (1500 mg, 15.2 mmol) was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (6876 mg, 45.8 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Ethyl 2-butynoate (3.00 g, 26.76 mmol) was concentrated in conc.
  • Acetic acid 25 ml was dissolved, mixed with finely powdered sodium iodide (12.03 g, 80.27 mmol) and stirred at a temperature of 110 ° C for 3 h.
  • MTBE methyl tert-butyl ether
  • the aqueous phase was extracted several times with MTBE and the combined organic phases dried over magnesium sulfate, filtered and under
  • Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
  • Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Ethyl 4,4,4-trifluorobut-2-ynoate 500 mg, 3.01 mmol was concentrated in conc.
  • Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h.
  • Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
  • reaction mixture was stirred for 3 hours at room temperature and then treated with water.
  • the aqueous phase was extracted several times with dichloromethane.
  • the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
  • Residue was treated with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the crude product obtained (gradient ethyl acetate / heptane) 1 - (3-hydroxy-4-methylpent-1 -yn-3-yl) cyclopropanecarbonitrile (2.59 g, 54% of theory) was isolated as a colorless solid.
  • Residue was treated with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography of the crude product obtained (gradient ethyl acetate / heptane) isolated 1- (1-cyclopentyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (2.55 g, 25% of theory) as a colorless solid.
  • Residue was treated with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) 1 - (1-hydroxy-1-phenylprop-2-yn-1-yl) cyclobutancarbonitril (740 mg, 6% of theory) was isolated as a colorless waxy solid.
  • Tetrakis (triphenylphosphine) palladium (0) (198 mg, 0.17 mmol) was placed under argon in a heated round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (3-hydroxy-4-methylpent-1-yn-3-yl) cyclopropanecarbonitrile (560 mg, 3.41 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
  • No. III.1 -5 1 - [(2E) -1-Cyclopropyl-1-hydroxy-3- (tributylstannyl) prop-2-en-1-yl] cyclopropanecarbonitrile
  • Tetrakis (triphenylphosphine) palladium (0) (107 mg, 0.09 mmol) was placed under argon in a heated round bottom flask and washed with abs.
  • Tetrahydrofuran (10 ml) and 1- (1-cyclopropyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (370 mg, 2.29 mmol) were added.
  • tributyltin hydride (0.74 ml, 2.75 mmol) was added.
  • the resulting reaction mixture was stirred for 1 hour at room temperature and for 30 minutes at a temperature of 50 ° C and then added with water.
  • the aqueous phase was extracted several times thoroughly with dichloromethane and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • No. III.1-76 1 - [(2E) -1-cyclopentyl-1-hydroxy-3- (tributylstannyl) prop-2-en-1-yl] cyclopropanecarbonitrile
  • Tetrakis (triphenylphosphine) palladium (0) (464 mg, 0.40 mmol) was placed under argon in a baked round bottom flask and washed with abs. Tetrahydrofuran (30 ml) and 1- (1-cycloentyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (1900 mg, 10.04 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
  • Tetrakis (triphenylphosphine) palladium (0) (242 mg, 0.21 mmol) was placed under argon in a baked round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (4-ethyl-3-hydroxyhex-1-yn-3-yl) cyclopropanecarbonitrile (1.00 g, 5.23 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
  • No. III.2-2 1 - [(1E) -3-hydroxy-4-methyl-1- (tributylstannyl) pent-1-en-3-yl] cyclobutanecarbonitrile
  • Tetrakis (triphenylphosphine) palladium (0) (261 mg, 0.23 mmol) was placed under argon in a heated round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (3-hydroxy-4-methylpent-1-yn-3-yl) cyclobutanecarbonitrile (1000 mg, 5.64 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
  • Another object of the present invention is the use of at least one compound of the invention selected from the group consisting of substituted cyano-cycloalkylpenta-2,4-serve and cyano-cycloalkylpent-2-en-4-inden of the general formula (I), and of any mixtures of these
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • 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
  • Stress conditions may include, for example, heat, drought, cold and dry stress (stress caused by drought and / or lack of water), osmotic stress,
  • Nitrogen nutrients limited availability of phosphorus nutrients.
  • Cyano-cycloalkylpenta-2,4-dienes substituted according to the invention, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-ines of the general formula (I ) are applied by spray application to appropriate plants or plant parts to be treated.
  • the use according to the invention of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha,
  • the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased lagging or tillering, stronger and more productive shoots and tillers,
  • Photosynthesis beneficial plant properties, such as
  • Non-limiting resistance to abiotic stress ⁇ at least one in general 3%, in particular greater than 5%
  • At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • 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 have other common ingredients, such as solvents,
  • Formulation aids especially water, included.
  • Other ingredients may include agrochemical agents, which are further described below.
  • Another object of the present invention is the use of
  • inventive compounds of the general formula (I) per se and for the corresponding spray solutions are inventive compounds of the general formula (I) per se and for the corresponding spray solutions.
  • Fertilizers which, according to the invention, can be used together with the compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing
  • Phosphoric acid preferably potassium salts and ammonium salts.
  • NPK fertilizers ie fertilizers
  • Ammonium nitrate (general formula (NH 4 ) 2 SO 4 ) contains nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium
  • the fertilizers may also contain salts of micronutrients (preferably calcium,
  • 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 one or more compounds of the general formula (I) according to the invention can be administered at the same time.
  • Embodiments of the present invention use one or more compounds of the formula (I) and the fertilizer according to the invention in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
  • 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, such as wheat, barley, rye, oats, 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
  • Legumes such as beans, lentils, peas and soybeans
  • Oil crops such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
  • Castor oil plants cocoa beans and peanuts; Cucumber plants, for example Pumpkin, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or 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.
  • Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
  • Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
  • 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),
  • Fescue Fescues, Festucu spp.
  • red fescue Festuca rubra L. spp. Rubra
  • creeping fescue Festuca rubra L
  • chewings fescue Festuca rubra commutata Gaud.
  • Sheep fescue (Festuca ovina L),” hard fescue “(Festuca longifolia Thuill.),” hair fescue “(Festucu capillata Lam.),” tall fescue “(Festuca arundinacea Schreb.) and” meadow fescue "(Festuca elanor L) ;
  • 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.), “sand cattail “(Phleum subulatum L.) “orchardgrass” (Dactylis glomerata L.), “weeping alkaligrass” (Puccinellia distans (L.) Pari.) and “crested dog's-tail” (Cynosurus cristatus L.).
  • Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus affin is Chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm. ), “Blue gramma” (Bouteloua gracilis (HBK) lag.
  • Bermudagrass Cronodon spp., LC Rieh
  • Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by 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 breeders' 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
  • 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.
  • Compounds of general formula (I) include all plants which have genetic material conferring on these plants particularly advantageous, useful characteristics (whether obtained by breeding and / or biotechnology).
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. To the abiotic stress factors,
  • Stress conditions can include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased 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 shade.
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
  • Plant growth and improved plant development such as
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
  • Root growth seed size, fruit size, pod size, pods or Ear number, number of seeds per pod or ear, seed mass, strengthened
  • Stability Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
  • Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
  • 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 produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • the desired product as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
  • Pollen sterility may be localized in the cytoplasm.
  • CMS cytoplasmic male sterility
  • Brassica species WO 92/005251, WO 95/009910, WO 98/27806, WO2005 / 002324, WO2006 / 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 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 91/002069).
  • Plants or plant varieties which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
  • herbicide-tolerant plants d. 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. (1992), 7, 139-145
  • the genes responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481).
  • an EPSPS from the tomato Gasser et al., J. Biol. Chem. (1988), 263, 4280-4,289) or for an EPSPS from Eleusine (WO2001 / 66704).
  • It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 00/066746, WO 2000/66747 or WO2002 / 026995.
  • 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. WO2002 / 036782,
  • Glyphosate-tolerant plants can also be obtained by Plants which select for naturally occurring mutations of the abovementioned genes, as described, for example, in WO2001 / 024615 or WO2003 / 013226.
  • Other herbicide-resistant plants are, for example, plants opposite
  • Herbicides that inhibit the enzyme glutamine synthase such as bialaphos, phosphinotricin or glufosinate, have been tolerated. 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.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenases
  • HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme, or a gene encoding a mutant HPPD enzyme as described in WO 96/038567, WO 99/024585 and WO 99/1998 / 024586, are transformed.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
  • Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
  • Acetohydroxy acid synthase known
  • Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
  • Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • insect-resistant transgenic plants ie 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.
  • insect-resistant transgenic plant as used herein includes any plant containing at least one transgene comprising a coding sequence encoding:
  • 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:
  • insecticidal parts thereof e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or 2) a crystal protein from Bacillus thuringiensis or a part thereof which is present in
  • Presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof is insecticidal, 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.
  • the protein Cry1A.105 produced by the corn event MON98034 WO

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Abstract

Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2-èn-4-ynes de formule générale (I) ou leurs sels, [X-Y], Q, R1, R2, A1, A2, V, W, m et n étant tels que définis dans la description, procédé pour leur préparation et leur utilisation pour accroître la tolérance des plantes au stress abiotique, et/ou pour augmenter le rendement des plantes.
EP15738663.2A 2014-07-22 2015-07-17 Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes Withdrawn EP3172187A1 (fr)

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PCT/EP2015/066402 WO2016012362A1 (fr) 2014-07-22 2015-07-17 Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes

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WO2016008862A1 (fr) * 2014-07-18 2016-01-21 Bayer Cropscience Aktiengesellschaft Vinyl- et alcinylcycloalcanols substitués ainsi que vinyl- et alcinylcyanohétérocyclylalcanols substitués comme substances actives contre le stress abiotique des végétaux

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US20170210701A1 (en) 2017-07-27
CA2955798A1 (fr) 2016-01-28
AR101214A1 (es) 2016-11-30
AU2015294110A1 (en) 2017-02-02
TW201617311A (zh) 2016-05-16
BR112017001144A2 (pt) 2018-01-30
JP2017528432A (ja) 2017-09-28
WO2016012362A1 (fr) 2016-01-28
US10322995B2 (en) 2019-06-18

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