EP2658376A1 - Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes. - Google Patents

Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.

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Publication number
EP2658376A1
EP2658376A1 EP11811349.7A EP11811349A EP2658376A1 EP 2658376 A1 EP2658376 A1 EP 2658376A1 EP 11811349 A EP11811349 A EP 11811349A EP 2658376 A1 EP2658376 A1 EP 2658376A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
cycloalkyl
alkoxy
heteroaryl
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Withdrawn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
EP11811349.7A
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German (de)
English (en)
Inventor
Jens Frackenpohl
Lothar Willms
Thomas Müller
Stefan Lehr
Pascal VON KOSKULL-DÖRING
Ines Heinemann
Christopher Hugh Rosinger
Isolde HÄUSER-HAHN
Martin Jeffrey Hills
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 Intellectual Property GmbH
Original Assignee
Bayer Intellectual Property GmbH
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Filing date
Publication date
Application filed by Bayer Intellectual Property GmbH filed Critical Bayer Intellectual Property GmbH
Priority to EP11811349.7A priority Critical patent/EP2658376A1/fr
Publication of EP2658376A1 publication Critical patent/EP2658376A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen as the ring 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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

Definitions

  • the invention relates to the use of substituted spircocyclic compounds
  • arylsulfonamides such as, for example, 2-cyanobenzenesulfonamides possess insecticidal properties (cf., for example, EP0033984 and WO2005035486, WO2006056433, WO2007060220).
  • 2-Cyanobenzenesulfone amides with particular heterocyclic substituents are described in EP2065370. It is further known that certain substituted 2-cyanobenzenesulfonamides as insecticides in the context of soil and
  • Seed applications can be used (see WO2006100271 and
  • Sulfamidoalkanecarbonitriles are described in DE847006.
  • the use of selected arylsulfonamides having alkylcarboxyl substituents as growth regulators, in particular for limiting the growth length of rice and wheat plants with the aim of resistance to flaying is described in DE2544859, while the fungicidal action of certain N-Cyanoalkylsulfonamiden in EP176327 is described.
  • substituted N-sulfonylamino-acetonitriles can be used to control parasites in warm-blooded animals (see WO2004000798).
  • substituted arylsulfonamides cf.
  • Hetarylsulfonamides can be used as pharmaceutical active ingredients.
  • WO2003007931 also describes the pharmaceutical use of substituted naphthylsulfonamides, while in Eur. J. Med. Chem. 2010, 45, 1760 naphthylsulfonyl-substituted ones
  • Antiinfectives in the treatment of hepatitis C can be used.
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE4103253). Also, the effect of antioxidants such as Naphtole and
  • Xanthines have already been used to increase the abiotic stress tolerance in plants (Bergmann et al., DD277832, Bergmann et al., DD277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown. It is further known that the tolerance of plants to abiotic stress can be increased by a modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) (de Block et al. , The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1, WO0004173, WO04090140).
  • 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, cause a strengthening of plant growth and / or to increase the
  • Abiotic stress for example, tolerance to cold, heat, drought stress (stress caused by drought and / or lack of water),
  • Salting and flooding but explicitly not understood the increased resistance to repositioning of the plants or components thereof, such as during or after heavy rains and thunderstorms.
  • the subject of the present invention is therefore the use of
  • a 1 , A 2 , A 3 are the same or different and are independently N
  • each represent hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8 ) alkynyl, aryl, aryl- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 6 ) -alkoxy, heteroaryl, (C 1 -C 6 ) -alkoxy- (C 1 -C 8) -alkyl, (Ci C 8 ) haloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 1 -C 8 ) -alkoxy,
  • Hydroxy- (Ci-C8) alkylcarbonylamino represents H, nitro, amino, cyano, halogen, (Ci-Cs) alkyl, (C 3 -C 8) cycloalkyl, (C 2 -C 8) alkenyl , (C 2 -C 8) alkynyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, (Ci-C8) - alkoxy (Ci-C 8) alkyl, (Ci-Cs) - haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-Cs) alkoxy, (Ci-Cs) haloalkoxy, (Ci-C8) alkylthio, (Ci-Cs) haloalkylthio, (Ci-C 8 ) - alkoxycarbonyl, (C 1 -C 6 ) -alkoxycarbonyl- (C
  • R 2 is H, nitro, amino, cyano, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) -cycloalkyl,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by
  • X is a direct bond or a grouping (CHR 3 ) n , and wherein R 3 in the grouping (CHR 3 ) n are each the same or different
  • n 0, 1
  • R 3 is H, (Ci -Ce) alkyl, (C2 -Ce) alkenyl (Ci -Ce) alkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) - cycloalkyl, ( C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 4) -alkyl C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -
  • R 4 is H, (Ci -Cs) alkyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (C 2 -C 8) -alkynyl, (Ci-C 8) - alkylcarbonyl , (C3-C8) cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C8) alkoxycarbonyl, aryl (Ci-C8) alkoxycarbonyl, (C3-C8) - cycloalkoxycarbonyl, (C3-C8) - cycloalkyl (Ci-C8) alkoxycarbonyl, (Ci-C 8) - alkylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 8) - alkoxycarbonylcarbonyl, aryl (Ci-C
  • R 19 , R 21 independently of one another are H, halogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, aryl, heteroaryl, heterocyclyl, aryl- (C 1 -C 8 ) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C 8) - haloalkyl, (C 2 -C 8) haloalkenyl group,
  • R 22 , R 25 independently of one another are H, halogen, nitro, cyano, (C 1 -C 5) -alkyl,
  • R 23 is H, halogen, (Ci-Cs) alkyl, (C 2 -C 8) alkenyl, Aryi, heteroaryl, heterocyclyl, aryl (Ci-C8) alkyl, (C 3 -C 8) - Cycloalkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl,
  • a 7 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 8) -alkyl, N- (C 3 -C 8) cycloalkyl, N- (C 3 -C 8) cycloalkyl (Ci-C 8) alkyl, N-aryl (Ci-C 8) -alkyl, N- (Ci-C8) - alkoxycarbonyl, N-aryl (Ci-C8) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-Cs) - alkylcarbonyl or the group CR 24 , and wherein R 24 in the
  • Group C-R 24 each have the meaning according to the following
  • R 24 is H, halogen, nitro, cyano, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl- (C 1 -C 8 ) -alkyl,
  • R 28 is H, halogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, aryl (Ci-C8) alkyl, (C 3 -C 8) - cycloalkyl, (Ci C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl,
  • a 8 is O (oxygen), S (sulfur), NH, N- (C 1 -C 8 ) -alkyl, N- (C 3 -C 8) cycloalkyl, N- (C 3 -C 8) -cycloalkyl- (Ci-C 8) alkyl, N-aryl (Ci-C 8) -alkyl, N- (Ci-Cs) - alkoxycarbonyl, N -Aryl- (Ci-C8) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-Cs) - al
  • a 9 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 8) -alkyl, N- (C 3 -C 8) cycloalkyl, N- (C 3 -C 8) cycloalkyl (C 1 -C 8 ) -alkyl, N-aryl- (C 1 -C 8 ) -alkyl, N- (C 1 -C 8 ) -alkoxycarbonyl, N-aryl- (C 1 -C 8 ) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-Cs) - alkylcarbonyl or the group CR 30 , and wherein R 30 in the
  • Grouping C-R 30 has the meaning as defined below, A 8 and A 9 are simultaneously a heteroatom in the case of N (nitrogen) or, further, according to the definition of substituted N,
  • R 29 is H, halogen, nitro, cyano, (Ci-C 8) -alkyl, (C2 -Ce) alkenyl (Ci-Ce) alkyl, (C2-C8) alkynyl (C 8 ) -alkyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -alkenyl, aryl, heteroaryl,
  • a 11 in the case of N (nitrogen) or further as defined for the definition of N simultaneously represent a heteroatom, for H, halogen, nitro, cyano, (C 1 -C 8) -alkyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) alkenyl, aryl, heteroaryl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) cycloalkyl, (Ci-C 8) - haloalkyl, (C -Cs) -alkoxy, hydroxy, hydrothio, (C 1 -C 8 ) -haloalkoxy, heteroaryl- (C 1 -C 8 )
  • R 35 is H, halogen, nitro, cyano, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl- (C 1 -C 8 ) -alkyl,
  • R 36 , R 38 independently of one another are H, halogen, nitro, cyano, (C 1 -C 5) -alkyl,
  • R 40 and R 41 independently of one another are H, hydroxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, cyano- (C 1 -C 8 ) -alkyl, amino- (C 1 -C 8 ) -alkyl , (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyloxy- (C 1 -C 8 ) -alkyl, arylsulfonyloxy- (C 1 -C 8 ) -alkyl, (Ci -C 8) - alkylcarbonyloxy (Ci-C8) alkyl, arylcarbonyloxy (Ci-C 8) alkyl,
  • Y is cyano, cyano (Ci-C 8) alkyl, hydroxy (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, hydroxycarbonyl, (Ci-Cs) Alkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 8 ) -alkoxycarbonyl, aminocarbonyl, bis (Ci-C 8) alkylaminocarbonyl, (Ci-C 8) - alkyl [(Ci-C 8) alkoxy] aminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, aryl (Ci-C 8) alkylaminocarbonyl, heteroaryl (Ci
  • the compounds of formula (I) can form salts. Salt formation may be effected by the action of a base on those compounds of formula (I) bearing an acidic hydrogen atom, e.g. in the case that Y contains a COOH group.
  • Suitable bases are, for example, organic amines, such as trialkylamines,
  • Alkaline earth metal hydroxides, carbonates and bicarbonates in particular
  • Potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else
  • Ammonium salts salts with organic amines or quaternary (quaternary)
  • Ammonium salts for example with cations of the formula [NRR ' R ' R '' ] + , where R 1 to R '' each independently of one another are an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3 , or organic acids, e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, internal salts can be protonated in turn
  • a 1 , A 2 , A 3 are the same or different and are independently N
  • W each represent hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6 ) alkynyl, aryl, aryl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkoxy, heteroaryl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C 6) alkoxy, (Ci-C6) haloalkoxy, aryloxy, heteroaryloxy, (C3-C6) cycloalkyloxy, (C3 -C 6)
  • R 1 is H, nitro, amino, cyano, halogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl,
  • R 2 is H, nitro, amino, cyano, halogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by
  • R 1 and A 3 when A 3 is a group CW, with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X is a direct bond or a grouping (CHR 3 ) n , and wherein R 3 in the grouping (CHR 3 ) n are each the same or different
  • n 0, 1
  • R 3 is H, (Ci-C 6) -alkyl, (C2-C6) alkenyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) - cycloalkyl , (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy-, (Ci-C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6 ) Haloalkylthio (C 1 -C 6 ) -alkyl, R 4 is H, (Ci-
  • R 18 , R 20 independently of one another are H, halogen, nitro, cyano, (C 1 -C 6) -alkyl,
  • R 21 are each independently H, halogen, (Ci-C6) alkyl, (C2-C6) alkenyl, aryl, heteroaryl, heterocyclyl, aryl (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 6) - haloalkyl, (C 2 -C 6) haloalkenyl group,
  • R 22 , R 25 independently of one another are H, halogen, nitro, cyano, (C 1 -C 6) -alkyl,
  • Heterocyclyl (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, amino, (Ci-C 6) - alkylamino, bis (Ci-C6) alkylamino, (Ci-C6) alkoxycarbonylamino, ( C1-C6) - Alkoxycarbonyl, hydroxycarbonyl, (C 1 -C 6) -alkylcarbonyl, arylcarbonyl, (C 3 -C 6) -cycloalkylcarbonyl,
  • R 23 is H, halogen, (Ci-Ce) alkyl, (C2-C6) alkenyl, aryl, heteroaryl, heterocyclyl, aryl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl , (Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl group,
  • a 7 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 6) -alkyl, N- (C 3 -C 6) -cycloalkyl, N- (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, N-aryl- (C 1 -C 6 ) -alkyl, N- (C 1 -C 6 ) -alkoxycarbonyl, N-aryl- (C 1 -C 6 ) -alkoxycarbonyl, N-arylcarbonyl, N - (Ci-C6) - alkylcarbonyl or the group CR 24 , and wherein R 24 in the
  • Group C-R 24 each have the meaning according to the following
  • R 24 is H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl,
  • R 26 is H, halogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, aryl, heteroaryl, heterocyclyl, arylalkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) Haloalkyl, (C 2 -C 6 ) haloalkenyl,
  • R 27 is H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, aryl, heteroaryl, aryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy,
  • a 8 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 6) -alkyl, N- (C 3 -C 6) -cycloalkyl, N- (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, N-aryl- (C 1 -C 6 ) -alkyl, N- (C 1 -C 6 ) -alkoxycarbonyl, N-aryl- (C 1 -C 6 ) -alkoxycarbonyl, N-arylcarbonyl, N - (Ci-C6) - alkylcarbonyl or the group CR 29 , and wherein R 29 in the
  • Grouping C-R 29 each has the meaning according to the following
  • a 9 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 6) -alkyl, N- (C 3 -C 6) -cycloalkyl, N- (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, N-aryl- (C 1 -C 6 ) -alkyl, N- (C 1 -C 6 ) -alkoxycarbonyl, N-aryl- (C 1 -C 6 ) -alkoxycarbonyl, N-arylcarbonyl, N - (Ci-C6) - alkylcarbonyl or the group CR 30 , and wherein R 30 in the
  • Grouping C-R 30 each has the meaning according to the following
  • R 29 is H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl,
  • R 30 is H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl,
  • (Ci-C6) alkylcarbonyl, arylcarbonyl, (C3-C6) cycloalkylcarbonyl represents H, halogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, aryl (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, for H, halogen, nitro, cyano, (C 1 -C 6 ) - alkyl, (C2-C6) alkenyl, aryl, heteroaryl, aryl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -haloalkyl, (Ci-C 6 ) alkoxy,
  • a 10 and A 1 1 are simultaneously a heteroatom in the case of N (nitrogen) or, further, according to the definition of substituted N,
  • R 34 represents H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl,
  • R 35 is H, halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl,
  • R 38 independently of one another are H, halogen, nitro, cyano, (C 1 -C 6) -alkyl,
  • (C 1 -C 6 ) -haloalkyl (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) haloalkenyl,
  • R 37, R 39 are each independently H, halogen, (Ci-C6) alkyl, (C2-C6) alkenyl, aryl (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, ( Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl stand,
  • R 40 and R 41 independently of one another are H, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, cyano- (C 1 -C 6 ) -alkyl, amino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyloxy- (C 1 -C 6 ) -alkyl, arylsulfonyloxy- (C 1 -C 6 ) -alkyl, C 6 ) -alkylcarbonyloxy- (C 1 -C 6 ) -alkyl, arylcarbonyloxy- (C 1 -C 6 ) -alkyl,
  • a 1 , A 2 , A 3 are the same or different and are independently N
  • W is in each case hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4 ) - alkenyl,
  • phenyl unsubstituted phenyl, aryl (Ci-C 4) alkyl, heteroaryl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C 4) alkoxy, (Ci-C4) - haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkoxycarbonyl, (C -C 4) alkoxycarbonyl (Ci-C 4) alkyl, hydroxycarbonyl, aminocarbonyl,
  • R 2 is H, nitro, amino, cyano, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -cycloalkyl, C 4 ) alkynyl, substituted or
  • phenyl unsubstituted phenyl, aryl (Ci-C 4) alkyl, heteroaryl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C 4) alkoxy, (Ci-C4) - haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkoxycarbonyl,
  • R 1 and A 3 when A 3 is a group CW, with the atoms to which they are attached, a fully saturated, partially saturated or completely can form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
  • X is a direct bond or a grouping (CHR 3 ) n , and wherein R 3 in the grouping (CHR 3 ) n are each the same or different
  • R 3 is H, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C -C 4) -haloalkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 4) alkyl, aryl (Ci-C 4) alkyl, heteroaryl ( C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) alkylthio (Ci-C 4) alkyl, (Ci-C 4) -Haloalkylthio- (Ci-C 4) alkyl, (Ci-C
  • Alkylaminothiocarbonyl (Ci-C4) alkylaminocarbonyl, aryl (Ci-C 4) alkyl, Hetaroaryl- (Ci-C 4) alkyl, cyano (Ci-C 4) alkyl, (Ci-C4) haloalkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 4) alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl,
  • R 18 , R 20 independently of one another are H, fluorine, chlorine, bromine, iodine, nitro, cyano,
  • R 19 , R 21 independently of one another are H, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl,
  • (C 2 -C 4 ) -alkenyl substituted or unsubstituted phenyl, heteroaryl, heterocyclyl, aryl- (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) - haloalkenyl,
  • R 22 , R 25 independently of one another are H, fluorine, chlorine, bromine, iodine, nitro, cyano,
  • R 23 is H, fluoro, chloro, bromo, iodo, (Ci-C 4) alkyl, (C 2 -C 4 ) alkenyl, substituted or unsubstituted phenyl, heteroaryl, heterocyclyl, aryl (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) Halalkenyl stands,
  • a 7 represents 0 (oxygen), S (sulfur), NH, N- (C 1 -C 4 ) -alkyl, N- (C 3 -C 6 ) -cycloalkyl, N- (C 3 -C 6 ) -cycloalkyl- (Ci-C 4) alkyl, N-aryl (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N-aryl- (Ci-C 4) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-C 4 ) - alkylcarbonyl or the group CR 24 , and wherein R 24 in the
  • Group C-R 24 each have the meaning according to the following
  • R 24 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C 2 -C 4 ) -alkynyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (C 1 -C 4 ) - alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, aryl (Ci-C 4) alkoxy hydroxy, Hydrothio, (Ci-C 4) -haloalkoxy , (C 1 -C 4 ) -
  • R 26 is H, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, heterocyclyl, arylalkyl, (C 3 -C 6 ) -cycloalkyl , (Ci-C 4) -haloalkyl, (C 2 -C 4) haloalkenyl group,
  • R 27 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (Ci-C 4 ) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) -haloalkoxy, (C 2 -C 4) haloalkenyl , Heterocyclyl, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, amino, (C 1 -C 4 ) -alkylamino, bis (C 1 -C 4 ) -alkylamino, (C 1 -C 4 ) - Alkoxycarbon
  • R 28 is H, fluoro, chloro, bromo, iodo, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, aryl (Ci-C4) - alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) haloalkenyl group,
  • a 8 represents O (oxygen), S (sulfur), NH, N- (C 1 -C 4 ) -alkyl, N- (C 3 -C 6 ) -cycloalkyl, N- (C 3 -C 6 ) -cycloalkyl (Ci-C 4) alkyl, N-aryl (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N-aryl- (Ci-C 4) -alkoxycarbonyl, N-arylcarbonyl, N- (C 1 -C 4 ) -alkylcarbonyl or the grouping CR 29 , and where R 29 in the grouping C-R 29 in each case has the meaning as defined below,
  • a 9 is 0 (oxygen), S (sulfur), NH, N- (Ci-C 6) -alkyl, N- (C 3 -C 6) -cycloalkyl, N- (C 3 -C 6) cycloalkyl (Ci-C 4) alkyl, N-aryl (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N-aryl- (Ci-C 4) -alkoxycarbonyl, N-arylcarbonyl, N- (C 1 -C 4 ) -alkylcarbonyl or the grouping CR 30 , and wherein R 30 in the Grouping C-R 30 has the meaning as defined below,
  • a 8 and A 9 are simultaneously a heteroatom in the case of N (nitrogen) or, further, according to the definition of substituted N,
  • R 29 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C 2 -C 4 ) -alkynyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (C 1 -C 4 ) - alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, hydroxy, Hydrothio, (C 1 -C 4 ) -haloalkoxy,
  • R 30 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C 2 -C 4 ) -alkynyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (C 1 -C 4 ) - alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, hydroxy, Hydrothio, (Ci-C 4) haloalkoxy, (Ci-C 4) - alkylthio, (Ci-C4) haloalky
  • R 31 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (Ci-C 4 ) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) -haloalkoxy, (C 2 -C 4) haloalkenyl , Heterocyclyl, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, amino, (C 1 -C 4 ) -alkylamino, bis (C 1 -C 4 ) -alkylamino, (C 1 -C 4 ) - Alkoxycarbon
  • R 32 is H, fluoro, chloro, bromo, iodo, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, aryl (Ci-C4) - alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) haloalkenyl group,
  • R 33 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (Ci-C 4 ) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) haloalkoxy, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 -C 4) -
  • (C 1 -C 4 ) -alkylamino bis (C 1 -C 4 ) -alkylamino, (C 1 -C 4 ) -alkoxycarbonylamino, (C 1 -C 4 ) -alkoxycarbonyl, hydroxycarbonyl, (C 1 -C 4 ) -alkylcarbonyl, arylcarbonyl .
  • a 10 represents 0 (oxygen), S (sulfur), NH, N- (C 1 -C 4 ) -alkyl, N- (C 3 -C 6 ) -cycloalkyl, N- (C 3 -C 6 ) -cycloalkyl- (Ci-C 4) alkyl, N-aryl (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N-aryl- (Ci-C 4) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-C 4 ) -
  • a 11 is 0 (oxygen), S (sulfur) , N, N- (C 1 -C 4 ) -alkyl, N- (C 3 -C 6 ) -cycloalkyl, N- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 4 ) -alkyl, N-aryl - (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N-aryl- (Ci-C 4) -alkoxycarbonyl, N-arylcarbonyl, N- (Ci-C4) - alkylcarbonyl, N - (C 3 -C 6) cycloalkylcarbonyl, N- (Ci-C 4)
  • a 10 and A 1 1 are only in the case of N (nitrogen) or further according to the definition of substituted N simultaneously a heteroatom and
  • R 34 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C 2 -C 4 ) -alkynyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (C 1 -C 4 ) - alkyl, heteroaryl (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, hydroxy, Hydrothio, (Ci-C 4 ) haloalkoxy, heteroaryl (Ci-C 4) al
  • Arylcarbonyloxy (C3-C6) cycloalkylcarbonyloxy, (CiC 4) alkoxy- (CiC 4) - alkoxy, (C 2 -C 4) alkenyloxy group,
  • R 35 is H, fluorine, chlorine, bromine, iodine, nitro, cyano, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (C 2 -C 4 ) -alkynyl- (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- (C 1 -C 4 ) - alkyl, heteroaryl (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, hydroxy, Hydrothio, (Ci-C 4 ) haloalkoxy, (Ci-C 4) alkylthi
  • Arylcarbonyloxy, (C3-C6) cycloalkylcarbonyloxy, (CiC 4) alkoxy- (CiC 4) - alkoxy, (C 2 -C 4) alkenyloxy group, R 36 , R 38 independently of one another are H, fluorine, chlorine, bromine, iodine, nitro, cyano, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, substituted or unsubstituted phenyl, heteroaryl, aryl- Ci-C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) - alkoxy, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4) haloalkoxy, (Ci-C
  • R 37 , R 39 independently of one another are H, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl,
  • R 40 and R 41 independently of one another are H, hydroxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, cyano- (C 1 -C 4 ) -alkyl, amino- (C 1 -C 4 ) - alkyl, (C 1 -C 4 ) -alkylamino- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyloxy- (C 1 -C 4 ) -alkyl, arylsulfonyloxy- (C 1 -C 4 ) -alkyl, ( C 1 -C 4 ) -alkylcarbonyloxy- (C 1 -C 4 ) -alkyl, arylcarbonyloxy- (C 1 -C 4 ) -alkyl,
  • Y is cyano, cyano (Ci-C 4) alkyl, hydroxy (Ci-C 4) alkyl, (Ci-C 4) alkoxy- (Ci-C4) - alkyl, hydroxycarbonyl, (Ci-C 4 ) alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, (C 3 -C 6) -cycloalkyl- (C 1 -C 4 ) -alkoxycarbonyl, aryloxycarbonyl, aryl- (C 1 -C 4 ) - alkoxycarbonyl, aminocarbonyl, bis (Ci-C4) alkylaminocarbonyl, (Ci-C 4) - alkyl [(Ci-C 4) -alkoxy] aminocarbonyl, (C3-C6) cycloalkylaminocarbonyl, aryl (Ci-C 4 ) -alkylaminocarbonyl, hetero
  • a 1 , A 2 , A 3 are the same or different and are independently N
  • W each represent hydrogen, nitro, amino, cyano, fluorine, chlorine, bromine, iodine, (Ci-C 4) - alkyl, (C 2 -C 4) alkenyl, aryl (Ci-C 4) alkoxy, heteroaryl , (Ci-C 4) alkoxy- (Ci-C4) - alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, aryloxy, (C 3 -C 6) - cycloalkyloxy, (C3-C6) cycloalkyl (Ci-C 4) alkoxy, (Ci-C 4) alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, (C3- C6) - cycloalkylaminocarbonyl, cyano (Ci-C4) alky
  • R 1 represents H, nitro, amino, cyano, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl, ( Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C4) - haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) - haloalkylthio, (Ci-C 4) alkoxycarbonyl, (Ci-C 4) alkoxycarbonyl (Ci-C 4) alkyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 4) - alkylaminocarbonyl, (Ci-C4) - alkylamino
  • R 2 is H, nitro, amino, cyano, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4 ) -alkenyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy, C 4) haloalkoxy, (Ci-C4) - alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkoxycarbonyl, (Ci-C4) - alkoxycarbonyl, (Ci-C 4) -
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or fully unsaturated, optionally by Heteroatoms can form interrupted and optionally further substituted by W substituted 5 to 7-membered ring,
  • R 1 and A 3 when A 3 is a group CW, with the atoms to which they are attached, a fully saturated, partially saturated or completely
  • X is a direct bond or a grouping (CHR 3 ) n , and wherein R 3 in the grouping (CHR 3 ) n are each the same or different
  • n 0, or 1
  • R 3 is H, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) - Cycloalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
  • R 4 is H, (Ci-C 4) -alkyl, (C 2 -C 4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) alkylcarbonyl,
  • R 18, R 20 are each independently H, fluoro, cyano, (Ci-C 4) alkyl, hydroxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (Ci-C 4) Haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy,
  • R 19 is H, fluorine, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (Ci-C 4) independently of one another - are haloalkyl,
  • R 22 , R 25 independently of one another are H, fluorine, (C 1 -C 4 ) -alkyl, R 23 is H, fluorine, (C 1 -C 4 ) -alkyl, A 7 is 0 (oxygen) or the group CR 24 , and wherein R 24 in the grouping C-R 24 each has the meaning defined below, R 24 is H, fluorine, chlorine, cyano, (C 1 -C 4 ) -Alkyl, (C 1 -C 4 ) -alkoxy, hydroxy, aryl- (C 1 -C 4 ) -alkoxy,
  • R 26 is H, fluorine, (C 1 -C 4 ) -alkyl
  • R 27 is H, (C 1 -C 4 ) -alkyl
  • R 28 is H, fluorine, (C 1 -C 4 ) -alkyl
  • a 8 is O (oxygen), S (sulfur), NH, N-aryl- (C 1 -C 4 ) -alkyl, N- (C 1 -C 4 ) -alkoxycarbonyl or the grouping CR 29 , and wherein R 29 is in of the
  • Grouping C-R 29 has the meaning as defined below,
  • a 9 is O (oxygen), S (sulfur), NH, N-aryl- (C 1 -C 4 ) -alkyl, N- (C 1 -C 4 ) -alkoxycarbonyl or the grouping CR 30 , and wherein R 30 is in of the
  • Grouping C-R 30 has the meaning as defined below,
  • a 8 and A 9 are simultaneously a heteroatom in the case of N (nitrogen) or, further, according to the definition of substituted N,
  • R 29 is H, fluoro, chloro, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C4) - alkoxy- (Ci-C 4 ) Alkyl, hydroxy, is H, fluorine, chlorine, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy - (C 1 -C 4 ) -alkyl, hydroxy,
  • R 31 is H, (C 1 -C 4 ) -alkyl
  • R 32 is H, fluorine, (C 1 -C 4 ) -alkyl
  • R 33 is H, fluorine, chlorine, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy,
  • a 10 represents 0 (oxygen), S (sulfur) or the group CR 34 , and wherein R 34 in the grouping C-R 34 each have the meaning according to the
  • a 11 is O (oxygen), S (sulfur), NH, N- (C 1 -C 4 ) -alkyl, N- (C 3 -C 6 ) -cycloalkyl, N- (C 3 -C 6 ) -cycloalkyl- (Ci-C4) alkyl, N-aryl (Ci-C 4) alkyl, N- (Ci-C4) - alkoxycarbonyl, N- (Ci-C 4) -alkoxy, N- Bis- (Ci-C 4 ) alkylamino, C-spiroheterocyclyl or the group CR 35 , and wherein R 35 in the grouping C-R 35 each have the meaning according to the following
  • a 10 and A 11 are both heteroatom only in the case of N (nitrogen) or further as defined for N and R 34 is H, fluoro, chloro, (C 1 -C 4 ) alkyl, substituted or unsubstituted phenyl, aryl - (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy, hydroxy, (Ci-C4) - haloalkoxy, (C 3 -C 6) -cycloalkyl- ( Ci-C 4) alkoxy, (Ci-C 4) alkylthio, (Ci-C 4) - haloalkylthio, (Ci-C 4) alkoxy (Ci-C 4) alkyl, aryl (Ci-C 4 ) -alkyloxy, bis- (C 1 -C 4 ) -alkylamino, (C 1 -C 4 ) -alkoxy
  • R 35 is H, fluorine, chlorine, (C 1 -C 4 ) -alkyl, substituted or unsubstituted phenyl, aryl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) - alkoxy, hydroxy, (Ci-C4) - haloalkoxy, (C 3 -C 6) -cycloalkyl- (Ci-C 4) alkoxy, (Ci-C 4) alkylthio, (Ci-C 4) - haloalkylthio, (Ci-C 4) alkoxy (Ci-C 4) alkyl, aryl (Ci-C 4) alkyloxy, (Ci-C4) - alkoxy- (Ci-C 4) alkoxy, (C 2 -C 4 ) alkenyloxy,
  • R 36 , R 38 independently of one another are H, fluorine, chlorine, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy (C 1 -C 4 ) -alkyl, R 37 , R 39 independently of one another represent H, fluorine, (C 1 -C 4 ) -alkyl,
  • R 40 and R 41 independently of one another are H, hydroxy (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, cyano- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyloxy (C 1 -C 4 ) -alkyl, arylcarbonyloxy- (C 1 -C 4 ) -alkyl,
  • Y is cyano, cyano- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
  • arylsulfonyl is optionally substituted
  • 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 - is straight-chain or branched S-alkyl, preferably with 1 to 8, or having 1 to 6 carbon atoms, such as 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 aikynyl 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 means an alkyl radical bonded via an oxygen atom
  • alkenyloxy represents an aikyl radical bonded via an oxygen atom
  • alkynyloxy denotes an aikyl radical linked 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 ".
  • the heterocyclyl or the heterocyclic ring optionally
  • cyclic systems such as 8-azabicyclo [3.2.1] octanyl, 8- Aza-bicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • spirocyclic systems are also included, such as 1-oxa-5-aza-spiro [2.3] hexyl.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, 0, and S, but not two oxygen atoms should be directly adjacent, such as with a heteroatom from the group N, 0 and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3 -yl, 2,3-dihydro-1H-pyrrole-1 - or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyridine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1, 2,3,4
  • azepanyl 2,3,4,5-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1H-azepine-1 - or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2,7-dihydro-1H-azepine-1 - or -2- or 3- or 4-yl; 2,3-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-y
  • Preferred 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 consisting of 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-
  • 6- or 7-yl 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-
  • 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 6 or 7-yl; 6,7-dihydro-5H-1,2,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-1, 4,2-dioxazepin-2 or 3 or 5 or 6 or
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also occur on the hetero ring atoms, which may exist in different oxidation states, eg at N and S. and then form, for example, the divalent groups N (0), S (0) (also short SO) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • N (0), S (0) (also short SO) and S (O) 2 also short SO2
  • both enantiomers are included.
  • the term "heteroaryl" is heteroaromatic
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1,2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); Isoquinolines (eg.
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-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-
  • halogen means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a remainder, then "halogen" means
  • alkyl means a straight-chain or branched one
  • substituents are halogen, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • monohaloalkyl such as, for example, CH 2 CH 2 Cl, CH 2 CH 2 Br, CH 3 CH 3, CH 2 Cl, CH 2 F
  • perhaloalkyl such as CCI 3 , CCIF 2 , CFCl 2 , CF 2 CCIF 2 , CF 2 CC
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 4 C atoms or with unsaturated groups having 2 to 4 C atoms, preferred.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained.
  • radicals having a double bond or triple bond 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 Kumulenyl residues with one or more cumulative 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, for example prop-1-en-1-yl, but-1-en-1-yl, allyl, 1-methyl-prop-2-en-1 - yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-ene 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
  • 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,
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl
  • substituents also have one
  • alkylidene group such as methylidene
  • polycyclic aliphatic systems such as bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1-0] pentane -1 -yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantan-1-yl and adamantan-2-yl.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
  • substituted cycloalkyl spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partial
  • unsaturated ring system having preferably 4-8 C atoms, e.g. 1 -cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents with a Double bond at
  • Cycloalkenylrest As an alkylidene group such as methylidene, are included.
  • alkylidene group such as methylidene
  • substituted cycloalkyl the explanations for substituted cycloalkyl apply correspondingly.
  • 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 to determine the enantiomeric excess and the
  • 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 their
  • the substituted spirocyclic sulfonamidocarboxylic acids, carboxylic acid esters, carboxamides and carbonitriles of the general formula (I) according to the invention can be prepared by known processes (compare Eur J. Med Bioorg Med Med Chem., 2007, 15, 7553, EP2065370).
  • the synthetic routes used and investigated are based on commercially available or easily manufactured ones
  • Aryl and heteroarylsulfonyl chloride precursors can be prepared, for example, by direct chlorosulfonation of the corresponding substituted aromatics and heteroaromatics (see Eur J. Med. Chem., 2010, 45, 1760) or via diazotization of an amino-substituted aromatic or heteroaromatic compound and subsequent chlorosulfonation (cf., WO2005035486 ).
  • the synthesis routes used are shown in the following scheme 1 by way of example of corresponding spiro-cyclopropanecarboxylic acids, spiro-cyclopropanecarboxylic acid esters, spiro-cyclopropanecarboxamides and spiro-cyclopropylnitriles according to the invention and are transferable to the other spirocyclic sulfonamidocarboxylic acids, -carboxylic acid esters, -carboxamides and -carbonitriles according to the invention.
  • Tetramethylsilane ⁇ 0.00 ppm
  • the present invention accordingly provides for the use of at least one compound selected from the group consisting of substituted spirocyclic sulfonamidocarboxylic acids, carboxylic acid esters, carboxamides and carbonitriles of the general formula (I) and of any desired mixtures of these substituted spirocyclic sulfonamidocarboxylic acids, -carboxylic esters according to the invention , -carboxylic acid amides and carbonitriles of the general formula (I) with agrochemical active substances as defined below, for increasing the resistance of plants to abiotic stress factors, preferably drought stress, as well as for strengthening plant growth and / or increasing the plant yield.
  • agrochemical active substances as defined below
  • Another object of the present invention is a spray solution for
  • substituted spirocyclic sulfonamidocarboxylic acids carboxylic acid esters, - carboxamides and carbonitriles, the general formula (I).
  • drought, heat, cold and dry stress stress caused by dryness and / or drought
  • Spray application can be applied to appropriate plants or plant parts to be treated.
  • Compounds of general formula (I) or salts thereof are preferably carried out at a dosage of between 0.00005 and 3 kg / ha, more preferably between
  • abscisic acid is used simultaneously with substituted spirocyclic sulfonamidocarboxylic acids, -carboxylic acid esters, -carboxamides and -carbonitriles of the general formula (I), for example in the context of a common preparation or formulation, the admixture of abscisic acid is preferably carried out in one dosage between 0.001 and 3 kg / ha, more preferably between 0.005 and 2 kg / ha, particularly preferably between 0.01 and 1 kg / ha.
  • 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 tailing or stocking, stronger and more productive shoots and tillers,
  • Mycotoxins reduced levels of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and drought, as well as lack of oxygen due to excess water, improved tolerance to increased salt levels in soils and water, enhanced Tolerance to ozone stress, improved tolerance to herbicides and other plant treatment products, improved water absorption and photosynthetic performance, beneficial plant properties, such as acceleration of maturation,
  • Plant-maturing substances and bactericides can also be used in the control of plant diseases in the context of the present invention
  • a good effect on the abiotic stress resistance is not limited to at least one emergence, which is improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10%.
  • At least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • Another object of the present invention is a spray solution for
  • the spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.
  • Another object of the present invention is the use of appropriate spray solutions to increase the resistance of plants to abiotic stress factors. The following remarks apply both for the inventive use of the compounds of the general formula (I) per se and for the corresponding spray solutions.
  • potassium salts preferably chlorides, sulfates, nitrates
  • phosphoric acid salts and / or salts of phosphorous acid preferably potassium salts and ammonium salts.
  • phosphorous acid preferably potassium salts and ammonium salts.
  • NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium
  • calcium ammonium nitrate ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2 SO 4 NH 4 NO 3)
  • Ammonium phosphate and ammonium sulfate are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
  • the fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indole (III) acetic acid) or mixtures included.
  • Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP),
  • Potassium sulfate, 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.
  • Other 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 described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 , The general composition of the fertilizers, which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example 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 wt .-%) 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 application of the inventive compound of formula (I) and the fertilizer is carried out in one time frame of less than 1 hour, preferably less than 30
  • 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
  • Crops used as plants for the production of food are Crops used as plants for the production of food,
  • 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 rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucumber plants,
  • Laurel family such as avocado, Cinnamomum, camphor, or as plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
  • 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, soft fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, pepper, beans, soybeans, rapeseed, tomato, peppers, 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. nitens, E. obliqua, E. regnans, E. pilularus.
  • horse chestnut, sycamore, linden and maple tree As particularly preferred trees that can be improved according to the method of the invention can be mentioned: horse chestnut, sycamore, linden and maple tree.
  • 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 sib.),” Velvet bentgrass “(Agrostis canina L) , "South German Mixed
  • 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)
  • Lolchs ryegrasses", Lolium spp.
  • orchardgrass (Dactylis glomerata L.), "weeping alkaligrass” (Puccinellia distans (L.) Pari.) and “crested dog's-tail” (Cynosurus cristatus L.).
  • Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus affinis chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum laundering, ex Chiov.), “Buffalo grass”
  • Particularly preferred according to the invention are plants of each
  • Plant varieties are understood as meaning plants with new properties ("traits”), either by conventional breeding, by mutagenesis or with the aid of
  • Crop plants can accordingly be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety protection rights.
  • the treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
  • Plant nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also known as Transgenic called.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology). Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals,
  • Nitrogen nutrients limited availability of phosphorus nutrients or avoiding shadows.
  • Plants and plant varieties which can likewise be treated according to the invention are those plants which have increased yield properties
  • Yield can 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, germination vigor,
  • Seed failure reduced pod popping and stability.
  • To further Yield characteristics include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability and improved
  • Plants which can also be treated according to the invention are:
  • Hybrid plants that already express the properties of the heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be removed (eg in maize) by delaving (i.e., mechanical removal of the males)
  • Sex organs or the male flowers are produced; however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • 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 achieved by ensuring that the male cross-breeding partners possess appropriate fertility restorer genes capable of controlling the pollen fertility in hybrid plants that are the genetic source
  • CMS cytoplasmic male sterility
  • determinants of male sterility may also be localized in the nuclear genome. Pollen sterile plants can also be used with methods of plant
  • Biotechnology such as genetic engineering.
  • a particularly favorable remedy for Generation of male sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can also be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be either by genetic transformation or by selection of
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts.
  • 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
  • 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 that are useful for EPSPS from the petunia (Shah et al., Science (1986), 233, 478-481). , for an EPSPS from the tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704) encode.
  • 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
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO 07/024782.
  • Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO 03/013226.
  • herbicide-resistant plants are, for example, plants which are resistant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos,
  • Phosphinotricin or glufosinate have been tolerant.
  • 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 encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants that are 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.
  • herbicide tolerant plants are also plants that are compared to the
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to 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: In addition to a gene coding for an HPPD-tolerant enzyme, plants are transformed with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004/024928. Other herbicide-resistant plants are plants that are opposite
  • Acetolactate synthase (ALS) inhibitors have been made tolerant.
  • ALS inhibitors include sulfonylurea, imidazolinone,
  • Triazolopyrimidines pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants which are tolerant to ALS inhibitors in particular to imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones, can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutagenesis, 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 can also be treated according to the invention are insect-resistant transgenic plants, ie plants which 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.
  • Insecticidal crystal proteins from Bacillus thuringiensis such as, for example, 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 2007/027777); or 4) a protein according to any one of items 1) to 3) above, in which some,
  • amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative
  • VIP3Aa Proteins of protein class VIP3Aa:
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1 A and VIP2A (WO 94/21795); or
  • an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or 8) a protein according to any one of items 1) to 3) above, in which some,
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
  • Biosynthetic pathway including nicotinamidase
  • Nicotinate phosphoribosyltransferase nicotinic acid mononucleotide adenyltransferase, Nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase as described e.g. In EP 04077624.7 or WO 2006/133827 or
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the harvested product and / or altered properties of certain
  • Components of the crop such as:
  • Viscosity behavior the gel strength, the starch grain size and / or
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering, which can also be treated according to the invention, are plants such as cotton plants with altered
  • Fiber properties Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
  • cellulose synthase genes Contain cellulose synthase genes, as described in WO 98/000549, b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3-homologous nucleic acids, as described in WO 2004/053219; c) plants such as cotton plants with an increased expression of the
  • Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants, the oil with a high oleic acid content
  • transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities.
  • transgenic plants that can be treated according to the invention are exemplified.
  • Plants with one or more genes encoding one or more toxins are the transgenic plants offered under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • Herbicide-tolerant plants to be mentioned are, for example, maize varieties, cotton varieties and
  • Roundup Ready® glyphosate tolerance, for example corn, cotton, soybean
  • Liberty Link® phosphinotricin tolerance, for example rapeseed
  • IMI® imidazolinone tolerance
  • SCS® sylphonylurea tolerance
  • Plants to be mentioned include the varieties offered under the name Clearfield® (for example corn).
  • the compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granulated granules, suspension-emulsion concentrates, active substance-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and Feinstverkapselitch in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granulated granules, suspension-emulsion concentrates, active substance-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and Feinstverkapselitch in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powder
  • the present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress.
  • a spray formulation is described in more detail:
  • the formulations for spray application are prepared in a known manner, e.g. by mixing the compounds of the general formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Other common additives such as usual
  • Extenders as well as solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and also water, may optionally also be used.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • Hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified can), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such dimethyl sulphoxide).
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols , such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
  • Solvents such as dimethyl sulfoxide, as well as water.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
  • dispersants and / or emulsifiers which in the invention
  • nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated To name derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Defoamers which may be present in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal.
  • Agrochemical agents usable substances in question Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • Further additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc may be stabilizers such as cold stabilizers, antioxidants,
  • the formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I).
  • the active ingredient according to the invention may be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
  • Preferred times for the application of compounds of the general formula (I) for the seizure of the resistance to abiotic stress are soil, stem and / or leaf treatments with the permitted application rates.
  • the active compounds of the general formula (I) can generally also be used in their commercial formulations and in the formulations prepared from these formulations in mixtures with other active ingredients, such as
  • Insecticides attractants, sterilants, acaricides, nematicides, fungicides,
  • Bactericides, growth-regulating substances, the plant maturity affecting substances, safeners or herbicides are present.
  • Particularly favorable mixing partners are, for example, the following groupwise called active ingredients of
  • fungicides different classes, without setting a preference by their order:
  • F1 inhibitors of nucleic acid synthesis e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;
  • B. Amesulbrom, Azoxystrobin, Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoximethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Pyribencarb, Picoxystrobin, Trifloxystrobin, (2E) -2- (2 - ⁇ [6- (3-Chloro) 2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy ⁇ phenyl) -2- (methoxyimino) -N-methylethaneamide, (2E) -2- (ethoxyimino) -N-methyl-2- (2 - ⁇ [( ⁇ (1E) -1 - [3- (trifluoromethyl) phenyl] ethylidene ⁇ amino) oxy] methyl ⁇ phenyl) ethanamide
  • F6 inhibitors of ATP production e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
  • F8 inhibitors of signal transduction e.g. Fenpiclonil, fludioxonil, quinoxyfen F9 inhibitors of fat and membrane synthesis, e.g. B. chlozolinate, iprodione,
  • Propamocarb, propamocarb hydrochloride F10) inhibitors of ergosterol biosynthesis e.g. Fenhexamid, azaconazole,
  • Bitertanol bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole,
  • F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,
  • F12 inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole F13) resistance induction, e.g. Acibenzolar-S-methyl, probenazole, tiadinil
  • Iminoctadinal besylate iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations
  • bactericides Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and xylylcarb; or organophosphates, e.g.
  • AChE Acetylcholinesterase
  • Isofenphos isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mecarbam, methamidophos, methidathione, mevinphos, monocrotophos, naled, omethoates, oxydemeton-methyl, parathion (-methyl), phenthoates, phorates, phosalones, phosmet, phosphamidone, Phoxim, pirimiphos (-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone and vamidothion.
  • GABA-controlled chloride channel antagonists such as
  • Organochlorines e.g. Chlordane and endosulfan (alpha); or Fiprole
  • Sodium channel modulators / voltage-dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin (d-cis-trans, d-trans), biphenol, bioallethrin, bioallethrin-S-cyclopentenyl, bioresmethrin, cycloprothrin , Cy fluthrin (beta), cyhalothrin (gamma, lambda), cypermethrin (alpha, beta, theta, zeta), cyphenothrin [(IR) -frans-isomers], deltamethrin, dimefluthrin, empenthrin [(EZ) - (1R) -isomers], esfenvalerates, etofenprox, fen
  • nicotinergic acetylcholine receptor agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid,
  • Allosteric acetylcholine receptor modulators such as spinosyns, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or
  • Active ingredients with unknown or non-specific mechanisms of action such as fumigants, e.g. Methyl bromide and other alkyl halides; or
  • chloropicrin sulfuryl fluoride
  • Borax Tartar emetic.
  • mite growth inhibitors eg clofentezine, diflovidazine, hexythiazox, etoxazole.
  • mite growth inhibitors eg clofentezine, diflovidazine, hexythiazox, etoxazole.
  • Microbial disruptors of insect intestinal membrane such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus
  • thuringiensis subspecies tenebrionis and BT plant proteins, e.g. CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.
  • diafenthiuron for example, diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
  • organotin compounds e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetradifon.
  • nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocyclam, and thiosultap (-sodium).
  • inhibitors of chitin biosynthesis type 0, such as benzoylureas, e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • benzoylureas e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moisture-disrupting agents such as cyromazines.
  • ecdysone agonists / disruptors such as diacylhydrazines, e.g.
  • Chromafenozide Halofenozide, Methoxyfenozide and Tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • I20 complex III electron transport inhibitors such as
  • complex I electron transport inhibitors for example from the group of the METI acaricides, eg fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or Rotenone (Derris).
  • METI acaricides eg fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or Rotenone (Derris).
  • METI acaricides eg fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; or Rotenone (Derris).
  • Voltage-dependent sodium channel blockers eg indoxacarb; Metaflumizone.
  • inhibitors of acetyl-CoA carboxylase such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • ryanodine receptor effectors such as diamides, e.g. Flubendiamide, chlorantraniliprole (Rynaxypyr), cyantraniliprole (Cyazypyr) and 3-bromo-N- ⁇ 2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl ⁇ -1 - (3-chloropyridin-2-yl ) -1-H-pyrazole-5-carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2- ( ⁇ [3-bromo-1- (3-chloropyridin-2-yl) -] 1 H-pyrazol-5-yl] carbonyl ⁇ amino) benzoyl] -1, 2-dimethylhydrazinecarboxylate (known from WO2007 / 043677).
  • diamides e.g. Flubendiamide, chlorant
  • Triazole-5-amines (known from WO 2006/043635), [(3S, 4aR, 12R, 12aS, 12bS) -3- [(cyclopropylcarbonyl) oxy] -6,12-dihydroxy-4,12b-dimethyl-11 -oxo-9- (pyridin-3-yl) -1,4,4,4a, 5,6,6a, 12,12a, 12b-decahydro-2H, 1: 1 H-benzo [f] pyrano [4,3 -b] chromen-4-yl] methylcyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3- (difluoromethoxy ) -N-methylbenzenesulfonamide (known from
  • ⁇ is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having from 1 to 3 hetero ring N and O groups, at least one N atom and at most one O atom in the ring, preferably one Remainder of the group (WA 1 ) to (W A 4 ),
  • RA 2 is ORA 3 , SRA 3 or N RA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group 0 and S, via the N Atom with the
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RA 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (C 1 -C 4 ) alkyl, (Ci-C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-Ce) hydroxyalkyl, (C3 -Ci2) cycloalkyl or tri- (Ci-C4) - alkyl-silyl; RA 6 , RA 7 , RA 8 are identical or different hydrogen, (Ci-C-8) alkyl, (Ci-C-8) haloalkyl, (C 3 -
  • Ci2 cycloalkyl or substituted or unsubstituted phenyl; preferably:
  • S1 c derivatives of 1, 5-diphenylpyrazole-3-carboxylic acid (S1 c), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1 -5), 1 - (2-chlorophenyl ) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described, for example, in EP-A-268554;
  • R B 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, nitro or (Ci-C 4 ) haloalkyl;
  • ⁇ is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is OR B 3 , SRB 3 or NR B 3 RB 4 or a saturated one
  • substituted phenyl preferably a radical of the formula ORB 3 , NHRB 4 or N (CH 3) 2, in particular of the formula ORB 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C 4 ) alkyl radicals or by [(Ci-C3) alkoxy] carbonyl; preferably:
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C3-C7) cycloalkyl, preferably dichloromethyl;
  • Rc 2 , Rc 3 are identical or different hydrogen, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (Ci-C4) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (Ci-C 4) alkyl, (Ci-C 4) alkoxy (Ci-C 4 ) alkyl, dioxolanyl- (C 1 -C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form one
  • substituted or unsubstituted heterocyclic ring preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or
  • benzoxazine ring preferably: active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-active safeners), such as “Dichloromid” (N, N-diallyl-2,2-dichloroacetamide) (S3-1), “R-29148” (3-dichloroacetyl) 2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer ( S3-3), "benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292” (N-allyl-N- [ (1,3-dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG Industries (S
  • X D is CH or N
  • RD 1 is CO-NRD 5 RD 6 or N HCO-RD 7 ;
  • RD 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl,
  • R D 3 is hydrogen, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl or (C 2 -C 4) alkynyl;
  • RD 4 is halogen, nitro, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy,
  • RD 5 is hydrogen, (Ci-Ce) alkyl, (C 3 -C 6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C5-C6) cycloalkenyl, phenyl or 3- to 6 heterocyclyl-containing hetero-hetero atoms from the group consisting of nitrogen, oxygen and sulfur, where the last seven radicals are represented by VD substituents from the group halogen, (C 1 -C 6 ) alkoxy, (C 1 -C
  • C6 cycloalkyl, (Ci-C 4) alkoxycarbonyl, (Ci-C are substituted 4) alkylcarbonyl and phenyl and, in the case of cyclic radicals, also (Ci-C4) alkyl and (Ci-C4) haloalkyl;
  • RD 6 is hydrogen, (Ci-C 6) alkyl, (C 2 -C 6) alkenyl or (C2-C6) -alkynyl, where the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy,
  • RD 7 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (Ci-C 6) alkyl,
  • (C3-C6) cycloalkyl where the 2 last-mentioned radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (Ci-C6) haloalkoxy and (Ci-C 4 ) alkylthio and in the case of cyclic radicals also (Ci -C 4) alkyl and (Ci-C4) haloalkyl groups;
  • VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
  • RD 7 (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, where the 2 last-mentioned radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 4 ) -alkoxy, (C 1 -C 6) -haloalkoxy and (C 1 -C 4 ) Alkylthio and in the case of cyclic radicals are also (Ci-C 4 ) alkyl and (Ci-C 4 ) haloalkyl substituted;
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
  • VD is 0, 1, 2 or 3; and Acylsulfamoylbenzoeklaamide, for example, the following formula (S4 b ), the z. B. are known from WO-A-99/16744,
  • RD 8 and RD 9 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl,
  • mD is 1 or 2; for example 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • Ethyl triacetoxybenzoate 3,5-di-methoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005/015994, WO-A-2005/016001.
  • E 1 are independently halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkyl, (Ci-C 4) Alkylamino, di- (C 1 -C 4 ) alkylamino, nitro;
  • a E is Coore 3 or 4 COSRE RE 3 , RE 4 are each independently hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 4 ) alkynyl, cyanoalkyl, (C 1 -C 4 ) haloalkyl, phenyl, nitrophenyl, benzyl,
  • ⁇ 1 is 0 or 1
  • ⁇ 2 , ⁇ 3 are each independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1). S8) compounds of the formula (S8) as described in WO-A-98/27049
  • nF N, an integer from 0 to 4.
  • Phenyl optionally substituted phenoxy
  • RF 2 is hydrogen or (Ci-C 4 ) alkyl
  • RF 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably substituted into three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, preferably compounds wherein XF CH,
  • riF is an integer from 0 to 2
  • RF 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, RF 2 is hydrogen or (Ci-C 4) alkyl,
  • R F 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted, mean
  • S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. 1,2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS No. 95855-00-8), as described in WO-A-1999/000020.
  • S9 1,2-Dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1, 2-dihydro-4-hydroxy-1 -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS No. 95855-00-8), as described in WO-A-1999/000020.
  • YG, ZG independently of one another O or S,
  • nG is an integer from 0 to 4,
  • R G 2 is (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, RG 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Oxabetrinil ((Z) -1,3-dioxolan-2-ylmethoxyimino- (phenyl) acetonitrile) (S1 1 -1), known as millet safener for millet against damage by metolachlor, "Fluxofenim” ( 1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S1 1 -2), which was used as a seed dressing safener for millet is known to be susceptible to damage by metolachlor, and "Cyometrinil” or “CGA-43089” ((Z) - cyanomethoxyimino (phenyl) acetonitrile) (S1 1 -3), which is known as millet safener for millet against damage by metolachlor.
  • S12 active substances from the class of the isothiochromanones (S12), such as, for example, methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121 -04- 6) (S12-1) and related compounds of WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): “naphthalene anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed safener for corn against damage by thiocarbamate herbicides, "fenclorim” (4,6 Dichloro-2-phenylpyrimidine) (S13-2) known as safener for pretilachlor in seeded rice, "flurazole” (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13 -3) known as seeding safener for millet against damage by alachlor and metolachlor, "CL 304415” (CAS reg. No.
  • RH 1 is a (Ci-C6) haloalkyl radical
  • RH 2 is hydrogen or halogen
  • RH 3, RH 4 are independently hydrogen, (Ci-Ci6) alkyl, (C2-Ci6) alkenyl or (C2-Ci6) alkynyl, where each of the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy cyano, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) alkylamino, di [(Ci-C 4) alkyl] amino,
  • RH 4 is hydrogen or (C 1 -C 4 ) -alkyl or
  • RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered one
  • heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy and (Ci-C 4) alkylthio means.
  • Plant-maturing substances Plant-maturing substances
  • Mixture formulations or in the tank mix are known, for example Active ingredients which are based on an inhibition of, for example, 1-aminocyclopropane-1-carboxylate synthase, 1 -aminocyclopropane-1-carboxylate oxidase and the
  • Ethylene receptors e.g. As ETR1, ETR2, ERS1, ERS2 or EIN4, are based, can be used as z. B. in biotechnology. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin. 199, 40, 1-7 or Plant Growth Reg. 1993, 13, 41-46 and references cited therein.
  • Use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • isomers such as stereoisomers and optical isomers.
  • Rhizobitoxin 2-amino-ethoxy-vinylglycine (AVG), methoxyvinylglycine (MVG),
  • Jasmonic acid methyl jasmonate, jasmonate.
  • Plant health and germination affecting substances As a combination partner for the compounds of general formula (I) in

Abstract

Utilisation d'acides sulfonamido-carboxyliques spirocycliques, de tels esters d'acide carboxylique, de tels amides d'acide carboxylique et de tels carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes. L'invention concerne l'utilisation d'acides sulfonamido-carboxyliques spirocycliques, de tels esters d'acide carboxylique, de tels amides d'acide carboxylique et de tels carbonitriles ou de leurs sels répondant à la formule générale (I) dans laquelle les différents substituants ont les significations indiquées dans la description, pour augmenter la tolérance au stress chez des plantes, par rapport au stress abiotique, ainsi que pour augmenter la croissance des plantes et/ou pour augmenter le rendement des plantes.
EP11811349.7A 2010-12-30 2011-12-27 Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes. Withdrawn EP2658376A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11811349.7A EP2658376A1 (fr) 2010-12-30 2011-12-27 Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP10197395A EP2471363A1 (fr) 2010-12-30 2010-12-30 Utilisation d'acides aryl-, hétéroaryl- et benzylsulfonaminés, d'esters d'acide aminé, d'amides d'acide aminé et carbonitrile ou leurs sels pour l'augmentation de la tolérance au stress dans des plantes
US201161429618P 2011-01-04 2011-01-04
PCT/EP2011/074072 WO2012089721A1 (fr) 2010-12-30 2011-12-27 Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.
EP11811349.7A EP2658376A1 (fr) 2010-12-30 2011-12-27 Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.

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EP2658376A1 true EP2658376A1 (fr) 2013-11-06

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EP10197395A Withdrawn EP2471363A1 (fr) 2010-12-30 2010-12-30 Utilisation d'acides aryl-, hétéroaryl- et benzylsulfonaminés, d'esters d'acide aminé, d'amides d'acide aminé et carbonitrile ou leurs sels pour l'augmentation de la tolérance au stress dans des plantes
EP11808217.1A Withdrawn EP2658375A2 (fr) 2010-12-30 2011-12-27 Utilisation d'acides, d'esters et d'amides d'acide arylcarboxylique, hétéroarylcarboxylique et benzylsulfonamidocarboxylique et d'arylcarbonitriles, d'hétéroarylcarbonitriles et de benzylsulfonamidocarbonitriles à chaîne ouverte ou de leurs sels pour augmenter la tolérance des plantes au stress
EP11811349.7A Withdrawn EP2658376A1 (fr) 2010-12-30 2011-12-27 Utilisation d'acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d'acide carboxylique, de leurs amides d'acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.

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EP10197395A Withdrawn EP2471363A1 (fr) 2010-12-30 2010-12-30 Utilisation d'acides aryl-, hétéroaryl- et benzylsulfonaminés, d'esters d'acide aminé, d'amides d'acide aminé et carbonitrile ou leurs sels pour l'augmentation de la tolérance au stress dans des plantes
EP11808217.1A Withdrawn EP2658375A2 (fr) 2010-12-30 2011-12-27 Utilisation d'acides, d'esters et d'amides d'acide arylcarboxylique, hétéroarylcarboxylique et benzylsulfonamidocarboxylique et d'arylcarbonitriles, d'hétéroarylcarbonitriles et de benzylsulfonamidocarbonitriles à chaîne ouverte ou de leurs sels pour augmenter la tolérance des plantes au stress

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US (2) US20140038822A1 (fr)
EP (3) EP2471363A1 (fr)
CN (2) CN103491776A (fr)
BR (2) BR112013016981A2 (fr)
RU (2) RU2013135330A (fr)
WO (2) WO2012089721A1 (fr)

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WO2012089722A2 (fr) 2012-07-05
US20140011682A1 (en) 2014-01-09
EP2471363A1 (fr) 2012-07-04
RU2013135330A (ru) 2015-02-10
US20140038822A1 (en) 2014-02-06
WO2012089722A3 (fr) 2012-09-27
EP2658375A2 (fr) 2013-11-06
CN103476254A (zh) 2013-12-25
CN103491776A (zh) 2014-01-01
BR112013016839A2 (pt) 2016-07-12
RU2013135328A (ru) 2015-02-10
WO2012089721A1 (fr) 2012-07-05

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