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WO2018108627A1 - Utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes - Google Patents

Utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes Download PDF

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WO2018108627A1
WO2018108627A1 PCT/EP2017/081511 EP2017081511W WO2018108627A1 WO 2018108627 A1 WO2018108627 A1 WO 2018108627A1 EP 2017081511 W EP2017081511 W EP 2017081511W WO 2018108627 A1 WO2018108627 A1 WO 2018108627A1
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alkyl
methyl
aryl
butenyl
heteroaryl
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PCT/EP2017/081511
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German (de)
English (en)
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Jens Frackenpohl
Hendrik Helmke
Jana FRANKE
Dirk Schmutzler
Peter Lümmen
Fabien Poree
Susana Manon GONZALEZ FERNANDEZ-NINO
Linn SCHNEIDER
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Bayer Cropscience Aktiengesellschaft
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Publication of WO2018108627A1 publication Critical patent/WO2018108627A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—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

Definitions

  • the invention relates to the use of substituted indolinylmethylsulfonamides or their salts for increasing the stress tolerance in plants to abiotic stress, to increase the
  • Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
  • arylsulfonamides for example 2-cyanobenzenesulfonamides
  • have insecticidal properties compare, for example, EP0033984 and WO2005 / 035486, WO2006 / 056433, WO2007 / 060220.
  • 2-Cyanobenzenesulfonamides having particular heterocyclic substituents are described in EP2065370.
  • certain aryl- and heteroaryl-substituted sulfonamides can be used as active substances against abiotic plant stress (cf.
  • Benzylsulfonamidocarboxylic acids, carboxylic acid esters, carboxamides and carbonitriles against abiotic plant stress are described in WO 2012/089721 and WO 2012/089722.
  • the preparation of sulfamidoalkanecarboxylic acids and sulfamidoalkanecarbonitrile is described in DE847006.
  • the use of selected arylsulfonamides having alkylcarboxyl substituents as growth regulators, especially for limiting the growth length of rice and wheat plants with the aim of minimizing the weather-related kinking is described in DE2544859, while the fungicidal action of certain N-Cyanoalkylsulfonamide in EP 176327 AI is described. It is also known that substituted N-sulfonylaminoacetonitriles can be used to control parasites in warm-blooded animals (see WO2004 / 000798).
  • WO2006 / 124875, WO96 / 36595) and substituted hetarylsulfonamides can be used as pharmaceutical active ingredients.
  • WO2003 / 007931 likewise describes the pharmaceutical use of substituted naphthylsulfonamides, while in Eur. J. Med. Chem. 2010, 45, 1760 naphthylsulfonyl-substituted glutamic acid amides and their antitumor action are described.
  • pyrrolidinyl-substituted arylsulfonamides can be used as cathepsin C inhibitors in the treatment of respiratory diseases (WO2009 / 026197) or as anti-infective agents in the treatment of hepatitis C (WO2007 / 092588).
  • the pharmaceutical use of N-arylsulfonyl derivatives of various other amino acids, for example as urokinase inhibitors (see WO2000 / 05214), as Agents for the treatment of diabetes (see WO2003 / 091211), as analgesics (see WO2008 / 131947) and as D-secretase modulators (see WO2010 / 108067) is also described.
  • Dihydrooxindolylsulfonamiden is described. It is also known that certain substituted oxindolyl derivatives, such as.
  • pyrrolobenzimidazolones can be used as pharmaceutical agents, for example as antiproliferative substances (cf .. EP 1598353 AI), as CB2 agonists (see WO2010 / 077839) or as antiarrhythmic and cardiotonic agents (see.
  • EP 0431943 AI shows synthetic routes for the preparation of substituted amino-dihydrooxindoles. It is furthermore known that oxotetrahydroquinolinylsulfonamides can be used as Rho-kinase inhibitors (compare Eur. J. Med. Chem. 2008, 43, 1730). It is known that plants are affected by natural stress conditions, such as cold, heat, drought stress (stress caused by drought and / or lack of water), wounding,
  • Pathogen infestation (viruses, bacteria, fungi, insects) etc. but also on herbicides with specific or nonspecific defense mechanisms can react [Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, pp. 1102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000].
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • LSA Proteins Embryogenesis Abundant Proteins
  • ROS reactive oxygen species
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Naphthylsulfamidocarboxylic acid N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline
  • 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).
  • the action of antioxidants such as naphthols and xanthines to increase the abiotic stress tolerance in plants has also been described (Bergmann et al., DD277832, Bergmann et al., DD277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • substituted dihydrooxindolylsulfonamides can lead to an increase in the resistance of plants to abiotic stress factors
  • the object of the present invention to provide compounds which further increase the tolerance to abiotic stress in plants, a strengthening of the
  • Plant growth and / or contribute to increase the plant yield Plant growth and / or contribute to increase the plant yield.
  • tolerance to abiotic stress is associated with tolerance to cold, heat, drought stress (stress caused by drought and / or lack of water), salting and flooding, but not explicitly the increased resistance to buckling of the plants or components thereof such as, for example understood during or after heavy rains and thunderstorms.
  • substituted Indolmylmethylsulfonamide or salts thereof can be used to increase the tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase the plant yield.
  • R 1 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylsulfonylalkyl, hydroxy (Ci-C 8) alkyl, cyano (Ci-C 8) alkyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 2 -C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) - alkyl, heterocyclyl- (Ci-C 8) alkyl, (Ci- C 8) alkoxy (Ci-C 8) alkyl, (Ci-C
  • R 5 independently of one another represent hydrogen, halogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (C 3 -Cg) -Halocycloalkyl, (C 3 -Cg) -cycloalkyl, (C 3 -Cg) - Cycloalkyl- (Ci-Cg) -alkyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl hydroxy- (Ci-Cg) -alkyl, cyano (Ci-Cg) -alkyl, (Ci-Cg) -alkoxy (Ci-Cg) -alkyl, (Ci-Cg) -alkylthio (Ci-Cg) -alkyl,
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) alkyl, heterocyclyl (Ci-C8) alkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) cycloalkyl (C 2 -C 8) alkyl, (Ci-C8) alkoxy (Ci-C8) alkoxy (Ci-C 8) alkyl, (C 4 -C 8) - cycloalkenyl, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, aryl (C 2 -C 8) alkenyl, heteroaryl (C 2 -C 8) alkenyl, (C 3 -C
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, hydroxy- (C 1 -C 8 ) -alkyl, cyano- (C 1 -C 8 ) -alkyl, (C 3 -C 8) cycloalkyl, (Ci-C8) alkoxy- (Ci-C 8) alkyl, (Ci-C 8) - Alkylthio (Ci-C8) alkyl, ammonium (Ci-C 8) alkyl, (Ci-C 8) alkylamino (Ci-C8) alkyl, (C 3 -C 8) - (cycloalkylamino C 1 -C 8) -alkyl, aryl- (C 1 -C 8) -alkylamino- (C 1 -C 8) -alkyl, heteroaryl- (C 1 -C
  • Heterocyclyl (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, ( C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkynyl, aryl, heteroaryl,
  • Heterocyclyl and R 15 are identical or different and are each, independently of one another, hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -cycloalkyl, (C 1 -C 10) -haloalkyl, (C 3 -C 10) -cycloalkyl, (C 3 -Cio) halocycloalkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (Ci-C 8) alkyl, (Ci-C 8 ) alkylthio (Ci-C8) - alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, (C 3 -Cio) cycloalkyl- (Ci-C
  • Heteroaryl is, and stands for oxygen or sulfur.
  • the compounds of the general formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, for example 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. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which in deprotonated form, such as sulfonic acids, certain
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and 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 ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • R 1 represents hydrogen, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylsulfonylalkyl, hydroxy- ( Ci-C7) alkyl, cyano (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl, halo (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl - (C 2 -C 7) alkyl, aryl (Ci-C7) alkyl, heteroaryl (Ci-C7) - alkyl, heterocyclyl- (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) -alkylthio
  • R 2 and R 3 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, aryl (Ci-C7) - alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl hydroxy- ( Ci-C7) alkyl, cyano (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl (C 2 -C 7) alkenyl, (C 2 -C 7 ) alkynyl, aryl,
  • R 4 and R 5 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, aryl (Ci-C7) - alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl hydroxy- ( Ci-C7) alkyl, cyano (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl (C 2 -C 7) alkenyl, (C 2 -C 7 ) alkynyl, aryl,
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl 7 ) -alkyl, heterocyclyl (Ci-C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 2 -C 7 ) -alkyL (Ci-C 7 ) alkoxy (Ci-C7) alkoxy (Ci-C7) alkyl (C4-C7) - cycloalkenyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl, aryl - (C 2 -C 7 ) -alkenyl, heteroary
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, or
  • R 11 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 9 ) -halocycloalkyl, (C 3 -C 7 ) -
  • R 12 is (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl (Ci-C7) haloalkyl, ( C 3 -C 7) halocycloalkyl, aryl (Ci-C7) alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) - alkyl, (Ci-C7) alkoxy - (Ci-C 7 ) -alkyL (Ci-C 7 ) -Alkoxy- (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -Alkoxy- (Ci-C 7 ) -alkoxy- (Ci-C 7 ) alkyl, aryloxy (Ci-C7) alkyl, heteroaryloxy- (Ci-C7) alkyl, (C 4 -
  • Heterocyclyl (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -haloalkenyl, (C 4 -C 9 ) -cycloalkenyl, (C 4 -C 9 ) -halocycloalkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkynyl, aryl, heteroaryl, heterocyclyl, and R 15 are identical or different and independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 4 ) -alkyl 7) cyanoalkyl, (Ci-C 9) -haloalkyl, (C 3 -C 9) -cycloalkyl, (C 3 -C 9) halocycloalkyl, (Ci-C7) alkoxy (C
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, hydroxy (Ci-C 6) alkyl, cyano (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, halo- (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (C 2 -C 6) alkyl, aryl (Ci-C 6) - alkyl, heteroaryl (C -C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6 ) alkyl, amino (Ci-C 6) alkyl, (Ci-C6) alkylamino (Ci)
  • R 2 and R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cycloalkyl, (C3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, hydroxy (Ci C6) alkyl, cyano (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, aryl,
  • R 4 and R 5 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, aryl (Ci-C 6) - alkyl, heteroaryl (Ci-C6) alkyl, heterocyclyl (Ci-C6) alkyl hydroxy- ( Ci-C6) alkyl, cyano (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6 ) alkynyl, aryl,
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 1 -C 6 ) -cycloalkyl, C 6 ) -alkylthio, OR 13 , C (O) R 13 ,
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, or with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 7-membered monocyclic or bicyclic ring, or together with the atom to which they are attached form a carbonyl group, represents hydrogen, (Ci-C6) alkyl, is (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) halocycloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) - alkyl, (C 1 -C 6 ) -alkoxy-
  • Heterocyclyl (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 4 -C 8 ) -cycloalkenyl, (C 4 -C 8 ) -halocycloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, aryl, heteroaryl, heterocyclyl, and R 15 are identical or different and independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6 ) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C
  • R 16 is (C 1 -C 6 ) -alkyl , (Ci-C 6) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -
  • Halocycloalkyl (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, aryl (Ci-C 6) - alkyl, heteroaryl (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 8 ) -cycloalkenyl- (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) haloalkenyl, (C 4 -C 8) - cycloalkenyl, (C 4 -C 8) -Halocycloalkenyl, ( C 2 -C 6) alkynyl, (C 2 -
  • X is oxygen or sulfur, preferably oxygen.
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, aryl, (C 3 -C 6) cycloalkyl (C 2 -C 6) -alkyl, R 2, R 3 are hydrogen,
  • R 4 , R 5 independently of one another represent hydrogen or (C 1 -C 6 ) -alkyl
  • R 6 , R 7 , R 8 independently of one another represent hydrogen
  • R 9 , R 10 represent hydrogen
  • R 11 represents hydrogen
  • R 12 is (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) halocycloalkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) - alkyl, (Ci-C 6) - Alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (ci) C 6 ) -alkyl, aryloxy- (C 1 -C 6 )
  • Heterocyclyl (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 4 -C 8 ) -cycloalkenyl, (C 4 -C 8 ) -halocycloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, aryl, heteroaryl, heterocyclyl, and R 15 are identical or different and independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 1 -C 6 ) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C
  • R 1 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
  • R 4 , R 5 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2 Methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • R 6 , R 7 , R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine or iodine,
  • R 9 , R 10 are hydrogen
  • R 11 is hydrogen
  • R 12 is methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-
  • Ethyl butyl 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2 Methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl,
  • R 1 is hydrogen, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -
  • R 2 and R 3 are each independently hydrogen, halogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C 8) alkyl, aryl (Ci-C8) - alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C8) - alkyl hydroxy- (C 1 -C 8 ) -alkyl, cyano- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio- (C 1 -C 8 ) -alkyl,
  • R 5 independently represent hydrogen, halogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (C 3 -C 8) cycloalkyl, (C3- C 8) cycloalkyl (Ci-C8) alkyl, aryl (Ci-C8) - alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C8) alkyl hydroxy ( C 1 -C 8 ) -alkyl, cyano- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl 8 ) -alkyl, heterocyclyl (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkyl, (Ci-C 8) alkoxy- (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) al
  • R 9, R 10 are independently hydrogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, hydroxy (Ci-C 8) - alkyl, cyano- (Ci-C 8) alkyl, ( C 3 -C 8) cycloalkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, amino (Ci- C 8) alkyl, (Ci-C 8) alkylamino (Ci-C8) alkyl, (C 3 -C 8) - cycloalkylamino (Ci-C 8) alkyl, aryl (Ci-C 8 ) -alkylamino- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkylamino- (C 1 -C 8 ) -
  • R 11 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 10) -hio-cycloalkyl, (C 3 -C 8 ) -
  • Heterocyclyl (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, ( C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkynyl, aryl, heteroaryl,
  • Heterocyclyl, and R 15 are identical or different and are each, independently of one another, hydrogen, (C 1 -C 5) -cycloalkyl, (C 1 -C 10) -haloalkyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) haloalkoxy (Ci-C 8) alkyl, (Ci-C8) alkylthio (Ci-C 8 ) alkyl, (Ci-C 8) - Haloalkylthio- (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-C 8) alkyl, (C 3 -Cio) cycloalkyl (Ci-C8) alkyl, (C 4 -Cio) cycloalkeny
  • R is (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -cyanoalkyl, (C 1 -C 10) -haloalkyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -
  • R 1 is hydrogen, (C 1 -C 4) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -
  • R 2 and R 3 are each independently hydrogen, halogen, (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 3 -C 7) halocycloalkyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, aryl (Ci-C7) - alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) - alkyl hydroxy- (Ci-C7) alkyl, cyano (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C 2 -C 7) alkenyl , (C 2 -C 7 ) -alkynyl, aryl,
  • R 4 and R 5 are independently hydrogen, halogen, (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 3 -C 7) halocycloalkyl, (C 3 -C 7) cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, aryl (Ci-C7) - alkyl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl hydroxy- (Ci-C7) alkyl, cyano (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7 ) alkynyl, aryl,
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl 7 ) alkyl, heterocyclyl (Ci-C 7 ) alkyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl (C 2 -C 7 ) alkyl, (Ci-C 7) alkoxy (Ci-C7) alkoxy (Ci-C7) alkyl, (C4-C7) - cycloalkenyl (Ci-C7) alkyl, (C 2 -C 7) alkenyl, Aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, or
  • Heterocyclyl (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -haloalkenyl, (C 4 -C 9 ) -cycloalkenyl, (C 4 -C 9 ) -halocycloalkenyl , (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkynyl, aryl, heteroaryl, heterocyclyl, and R 15 are identical or different and independently of one another represent hydrogen, (C 1 -C 7 ) -cycloalkyl, ( Ci-C 9 ) -haloalkyl, (C 3 -C 9 ) -cycloalkyl, (C 3 -C 9 ) -halocycloalkyl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl,
  • R 16 is (Ci-Cv) alkyl, (Ci-Cv) cyanoalkyl, (Ci-C 9) -haloalkyl, (C 3 -C 9) -cycloalkyl, (C3-C9) -
  • Halocycloalkyl (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl (Ci-C7) - alkyl, heteroaryl (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 3 -C 9 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 4 -C 9 ) -cycloalkenyl- (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) haloalkenyl, (C4-C9) - cycloalkenyl, (C4-C9) -Halocycloalkenyl, (C 2 - C 7 ) alkynyl, (C 2 -C 7 ) haloalkyn
  • X is oxygen or sulfur
  • R 1 represents hydrogen, (Ci-C 6) -haloalkyl, hydroxy (Ci-C 6) alkyl, cyano (Ci-C 6) alkyl, halo (C 3 -C 6) - cycloalkyl, (C3 C6) cycloalkyl (C 2 -C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, ( C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, amino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) ) alkylamino (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 4 -
  • R 2 and R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, aryl (Ci-C 6) - alkyl, heteroaryl (Ci-C6) alkyl, heterocyclyl (Ci-C6) alkyl hydroxy- ( Ci-C6) alkyl, cyano (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 - C 6 ) alkynyl, aryl,
  • R 4 and R 5 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, aryl (Ci-C 6) - alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy - (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkyn
  • R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 1 -C 6 ) -cycloalkyl, C 6) alkylthio, OR 13, C (0) R 13, C (0) OR 13, C (0) NR 14 R 15, NR 14 R 15, S0 2 R 16,
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, or
  • Halocycloalkyl (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, aryl (Ci-C 6) - alkyl, heteroaryl (Ci-C 6) alkyl, (C3-C8) -cycloalkyl- (Ci-C 6) alkyl, (C 4 -C 8) cycloalkenyl (Ci-C6) alkyl, (Ci-C6) Alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- (Ci C6) alkyl,
  • Heterocyclyl (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 4 -C 8 ) -cycloalkenyl, (C 4 -C 8 ) -halocycloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, aryl, heteroaryl, heterocyclyl,
  • R 14 and R 15 are identical or different and are each independently hydrogen, (Ci-Ce) - cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) - Halocycloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (ci) C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 - C 8) cycloal
  • R 16 is (Ci-C 6) -alkyl, (Ci-C 6) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -
  • Halocycloalkyl (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, aryl (Ci-C 6) - alkyl, heteroaryl (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 8 ) -cycloalkenyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 4 -C 8) - cycloalkenyl, (C 4 -C 8) -Halocycloalkenyl, ( C 2 -C 6) alkynyl, (C 2 -C
  • X is oxygen or sulfur, preferably oxygen.
  • R represents hydrogen, (Ci-C 6) -haloalkyl, (C 3 -C 6) cycloalkyl (C 2 -C 6) alkyl 1
  • R 2 , R 3 are hydrogen
  • R 4 , R 5 independently of one another represent hydrogen
  • R 6 , R 7 , R 8 independently of one another represent hydrogen or halogen
  • R 9 , R 10 represent hydrogen
  • R 11 represents hydrogen
  • R 12 is (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) -
  • R 13 is (Ci-C 6) -alkyl, (Ci-C 6) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -
  • Halocycloalkyl (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, aryl (Ci-C 6) - alkyl, heteroaryl - (Ci-C 6) alkyl, (C3-C8) -cycloalkyl- (Ci-C 6) alkyl, (C 4 -C 8) cycloalkenyl (Ci-C6) alkyl, (Ci-C6 ) -Alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- (Ci C6) alkyl,
  • Heterocyclyl (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 4 -C 8 ) -cycloalkenyl, (C 4 -C 8 ) -halocycloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, aryl, heteroaryl, heterocyclyl,
  • R 14 and R 15 are identical or different and are each independently hydrogen, (Ci-Ce) - cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) - Halocycloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (ci) C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 - C 8 ) cyclo
  • R 16 is (Ci-C 6) -alkyl, (Ci-C 6) cyanoalkyl, (Ci-C8) -haloalkyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -
  • Halocycloalkyl (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl, aryl (Ci-C 6) - alkyl, heteroaryl (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 8 ) -cycloalkenyl- (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 4 -C 8) - cycloalkenyl, (C 4 -C 8) -Halocycloalkenyl, ( C 2 -C 6) alkynyl, (C 2 -C
  • R 1 is hydrogen, trifluoromethyl, pentafluoroethyl, 1, 1, 2,2-tetrafluoroethyl, heptafluoropropyl,
  • Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoro-n-propyl, 3, 3,3-trifluoro-n-propyl, 4,4-difluoro-n-butyl, 4,4,4-trifluoro-n-butyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
  • R 2 , R 3 are hydrogen
  • R 4 , R 5 independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2 Methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2 Trimethylpropyl, 1, 2,2-trimethyl
  • R 11 is hydrogen
  • R 12 is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1, 1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl,
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally
  • substituted naphthylsulfonyl for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • cycloalkylsulfonyl alone or as part of a chemical group - represents optionally substituted cycloalkylsulfonyl, preferably of 3 to 6
  • Carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms for example (but not limited to) (C 1 -C 6) alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2 Methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpent
  • heteroarylsulfonyl is optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally 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.
  • alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (CI-C ⁇ ) - or (Ci-C4) -alkylthio, e.g. (but not limited to) (ci-Ce) alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethyl
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom
  • alkenylsulfinyl and alkynylsulfinyl defined according to the invention as alkenyl or
  • alkenylsulfonyl and alkynylsulfonyl are defined according to the invention as alkenyl or
  • Alkoxy means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2 Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 - Ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio , Haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkylsilyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • heterocyclic radical contains at least one heterocyclic ring
  • ( carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, more cyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl also become
  • 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, O, and S, but not two
  • Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or completely hydrogenated heterocyclic radical having two heteroatoms from the group consisting of N, O and S, such as, for example, 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
  • 6-yl 1, 4,5, 6-tetrahydropyridazine-1 - or 3 or 4 or 5 or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1 - or 3- or 4- or 5- or 6-yl;
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • 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 be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring.
  • N (O) also known as SO
  • S (O) 2 also abbreviated to SO 2
  • heteroaryl stands for heteroaromatic compounds, ie.
  • heteroaryls are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine
  • 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-indol-4-yl, 1H- Indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran 5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated
  • Hydrocarbon radical which is optionally mono- or polysubstituted.
  • Preferred substituents are halogen, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or
  • Nitro groups particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • the prefix "bis” also includes the combination of different alkyl radicals, eg.
  • Haloalkyl denote by identical or different halogen atoms, partially or completely substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl
  • ( Monohaloalkyl) such.
  • B. CH 2 CH 2 C1, CH 2 CH 2 Br, CHCICH3, CH 2 C1, CH 2 F; Perhaloalkyl such.
  • Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl is a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, wherein the corresponding fluorine atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as. B. CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and 0CH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
  • Range indication 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.
  • the lower carbon skeletons for example having 1 to 6 carbon atoms or in unsaturated groups having 2 to 6 carbon atoms, are preferred.
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the alkyl radicals corresponding possible unsaturated radicals, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or
  • alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as, for example, 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 (but not limited to) (C 2 -C 6) alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3
  • Butenyl 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 - Methyl 3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2 propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-
  • Hexenyl 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2- pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3 - butenyl, 1, 2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-1-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-1- 2 -butenyl, 1,
  • alkynyl in particular also includes straight-chain or branched open-chain
  • C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 - ethyl
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring carbon atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl
  • optionally substituted cycloalkyl includes cyclic systems having substituents, wherein also substituents having a double bond on the cycloalkyl, z.
  • substituents such as methylidene
  • substituents having a double bond on the cycloalkyl, z As an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl also more cyclic aliphatic systems are included, such as, for example, bicyclo [1.1.0] butan-1-yl,
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
  • substituents having a double bond on the cycloalkenyl radical for example an alkylidene group such as methylidene
  • the compounds of general formula (I) may vary depending on the nature and linkage of the substituents exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be distinguished from those in 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 mixtures thereof.
  • Substituted indolinylmethylsulfonamides of the general formula (I) can be prepared by the methods described below.
  • the starting materials for the preparation of the compounds indicated are either commercially available or listed by the following
  • the optionally further substituted indolinylphthalimides of the general formula (V) according to the invention can be prepared by known processes.
  • the synthetic routes used and investigated are based on commercially available or easily produced indolines of type (I).
  • the indolines of type (II) are either commercially available or can be prepared by synthesis methods according to known methods: a) Y. Miyake, Y. Kikugawa, J. Heterocyclic. Chem. 1983, 20, 349; b) WO2014 / 089324.
  • indolinylphthalimides of type (V) For the preparation of the indolinylphthalimides of type (V), the nitrogen of the indoline of type (II) is first formylated as described in Scheme 1. The corresponding reaction product of type (III) is then subjected to a Cherniac unicorn reaction using an acid catalyst such as. HF, H2SO4 or CF3SO3H converted to indolinylphthalimides of type (IV).
  • an acid catalyst such as. HF, H2SO4 or CF3SO3H converted to indolinylphthalimides of type (IV).
  • the preparation of the substituted indolinylmethylamines (VII-2) as described in Scheme 3 can be started from an optionally further substituted indoline of type (II) via Friedel-Crafts acylation followed by reductive amination or formation of the nitrile of the type (X. ) respectively.
  • 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., WO2005 / 035486).
  • Ia-128 isopropyl H H H 3 - (trifluoromethyl) phenyl
  • Ia-354 isobutyl H H H 3 -bromo-2-thienyl
  • Ia-361 isobutyl H H H 4,5-dichloro-2-thienyl
  • Ia-378 isobutyl H H H 2- (4-chlorophenyl) ethyl

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Abstract

L'invention concerne l'utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels représentés par la formule générale (I), dans laquelle les groupes sont tels que définis dans la description, pour accroître la tolérance des plantes au stress abiotique et/ou augmenter le rendement des plantes.
PCT/EP2017/081511 2016-12-12 2017-12-05 Utilisation d'indolinylméthylsulfonamides substitués ou de leurs sels pour accroître la tolérance au stress chez les plantes WO2018108627A1 (fr)

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CN114213310A (zh) * 2021-12-31 2022-03-22 中国药科大学 吲哚啉化合物及其衍生物、制备方法、药物组合物和应用
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

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