WO2022268520A1 - Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes - Google Patents

Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes Download PDF

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WO2022268520A1
WO2022268520A1 PCT/EP2022/065728 EP2022065728W WO2022268520A1 WO 2022268520 A1 WO2022268520 A1 WO 2022268520A1 EP 2022065728 W EP2022065728 W EP 2022065728W WO 2022268520 A1 WO2022268520 A1 WO 2022268520A1
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alkyl
aryl
heteroaryl
heterocyclyl
cycloalkyl
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Jens Frackenpohl
Lars ARVE
Hendrik Helmke
Birgit Kuhn
Jana Schmidt
Jan Dittgen
Dirk Schmutzler
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Bayer Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P21/00—Plant growth regulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • Bayer AG Use of substituted pyrrolidinones or their salts to increase stress tolerance in plants.
  • Description The invention relates to the use of substituted pyrrolidinones or salts thereof to increase the stress tolerance in plants to abiotic stress and to increase plant growth and/or to increase plant yield.
  • certain substituted pyrrolidin-2-one-4-carboxamides and pyrrolidin-2-one-4-acetic acid amides can be used as active pharmaceutical ingredients, e.g. B. as beta-secretase inhibitors (cf. e.g. WO2009/038412) or as P2X7 modulators for the treatment of inflammatory and neurodegenerative diseases (cf. e.g.
  • Selected pyrrolidinone-substituted ureas are described as lead structures for identifying TRPV1 modulators (cf. Future Med. Chem.2015, 7, 243) or ERK inhibitors (cf. WO2016/100050).
  • TRPV1 modulators cf. Future Med. Chem.2015, 7, 243
  • ERK inhibitors cf. WO2016/100050.
  • the use of certain pyrrolidin-2-one-4-carboxamides as lead structures for identifying antituberculosis drugs or G protein-coupled receptor kinase inhibitors has also been described (Bioorg. Med. Chem.2010, 18, 6914; Bioorg. Med. Chem. Lett. 2018, 28, 1507).
  • N-sulfonyl-aminoacetonitriles can be used to control parasites in warm-blooded animals (see WO2004/000798).
  • the use of 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4- tetrahydroquinolin-6-yl)methanesulfonamide against drought stress in Arabidopsis thaliana and soya is described in Proc. national Acad. Sci. 2013, 110(29), 12132-12137.
  • WO2013/148339 also claims (2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamides with unsubstituted N-cycloalkyl radicals, while WO2015/155154 examines the effect of specially substituted (2-oxo-1, 2,3,4-tetrahydroquinolin-6-yl)methanesulfonamides against abiotic stress and the agonistic effect of the substances in question on abscisic acid receptors is described. WO2015/049351 describes the effect of dihydrooxindolylsulfonamides against abiotic stress in plants.
  • abiotic stresses eg cold, heat, drought, salt, flooding.
  • Some of these belong to signal transduction chains (eg transcription factors, kinases, phosphatases) or cause a physiological response in the plant cell (eg ion transport, detoxification of reactive oxygen species).
  • the signal chain genes of the abiotic stress response include, inter alia, transcription factors of the classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106).
  • ATPK and MP2C type phosphatases are involved in the response to salt stress.
  • salt stress often activates the biosynthesis of osmolytes such as proline or sucrose.
  • Sucrose synthase and proline transporters are involved here (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499).
  • the plants' defense against stress against cold and drought partly uses the same molecular mechanisms.
  • the accumulation of so-called Late Embryogenesis Abundant Proteins (LEA proteins) is known, to which the dehydrins belong as an important class (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plants 100: 291-296).
  • LSA proteins Late Embryogenesis Abundant Proteins
  • naphthylsulfonamide (4-bromo-N-(pyridin-2-ylmethyl)naphthalene-1-sulfonamide) affects the germination of plant seeds in the same way as abscisic acid (Park et al. Science 2009, 324, 1068-1071).
  • a naphthylsulfamidocarboxylic acid (N-[(4-bromo-1-naphthyl)sulfonyl]-5-methoxynorvaline) shows a mode of action in biochemical receptor tests that is comparable to 4-bromo-N-(pyridin-2-ylmethyl)naphthalene-1-sulfonamide is comparable (Melcher et al. Nature Structural & Molecular Biology 2010, 17, 1102-1108).
  • antioxidants such as naphthols and xanthines
  • DD 277832 the molecular causes of the anti-stress effect of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly-(ADP-ribose) glycohydrolases
  • tolerance to abiotic stress is understood to mean, for example, tolerance to cold, heat, drought stress (stress caused by drought and/or lack of water), salts and flooding.
  • substituted pyrrolidinones can be used to increase the stress tolerance in plants to abiotic stress and to increase plant growth and/or to increase plant yield.
  • R 1 is hydrogen, NR 30 R 31 , OR 32 , S(O) m R 33 , (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )- Alkynyl, (C 1 -C 10 )haloalkyl, (C 2 -C 8 )haloalkenyl, (C 2 -C 8 )haloalkynyl, (C 3 -C 10 )cycloalkyl, (C 3 -C 10 )- Halocycloalkyl, (C 4 -C 10 )cycloalkenyl, (C 4 -C 10 )halocycloalkenyl, aryl, aryl-(C 1
  • R 30 and R 31 with the nitrogen atom to which they are attached form a fully saturated or partially saturated 3 to 10-membered monocyclic or bicyclic ring which is optionally interrupted by heteroatoms and optionally further substituted,
  • R 32 is hydrogen, (C 1 -C 8 )- alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkyl, (C 2 -C 8 )alkynyloxycarbonyl-(C 1 -C 8 )alkyl, aryl-(C 1 -C 8 )alkoxycarbonyl-(C 1 -C 8 )- alkyl, heteroaryl-(C 1 -C 8 )-alkoxycarbonyl-(C 1 -C 8 )-alkyl, heterocyclyl-(C 1 -C 8 ) -alkoxycarbonyl-(C1-C8)-alkyl , or R
  • R 34 is hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, aryl-(C 1 -C 8 )alkyl, aryl, heteroaryl, heteroaryl-(C C 1 -C 8 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8 )-alkyl, R 32 O-(C 1 -C 8 )-alkyl, R 30 R 31 N-(C 1 -C 8 )- alkyl, NR 30 R 31 , (C 3 -C 10 )cycloalkyl-(C 1 -C 8 )alkyl, S(O)mR 33 represents, R 35 represents hydrogen, NR 30 R 31 , OR 32 , (C C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, aryl, aryl
  • the compounds of general formula (I) can be synthesized by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, eg. B. 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 a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids eg. B.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid
  • Suitable substituents which are in deprotonated form can form inner salts with groups which in turn can be protonated, such as amino groups. Salt formation can also take place by the action of a base on compounds of the general formula (I).
  • Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, 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 [NR a R b R c R d ] + , in which R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • an agriculturally suitable cation 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 [NR a R b R c R d ] + , in which R a to R d each independently represent an organic radical, in particular al
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts.
  • a preferred subject of the invention is the use of compounds of the general formula (I) in which R 1 is hydrogen, NR 30 R 31 , OR 32 , S(O)mR 33 , (C 1 -C 7 )-alkyl, (C 2 -C 7 )alkenyl, (C 2 -C 7 )alkynyl, (C 1 -C 7 )haloalkyl, (C 2 -C 7 )haloalkenyl, (C 2 -C 7 )haloalkynyl, (C 3 -C 7 )cycloalkyl, (C 3 -C 7 )halocycloalkyl, (C 4 -C 7 )cycloalkenyl, (C 4 -C 7 )halocycloalkenyl, aryl, aryl(C 1 -C 7 )alkyl, heteroaryl , heteroaryl(C 1 -C 7 )alkyl, heterocyclyl, heterocyclyl(C
  • C 7 )alkyl (C 1 -C 7 )alkoxy-(C 1 -C 7 )alkoxy-(C 1 -C 7 )alkoxy-(C 1 -C 7 )alkyl, (C 1 -C 7 )- alkoxy-(C 1 -C 7 )-alkoxy-(C 1 -C 7 )-alkoxy-(C 1 -C 7 )-alkoxy-(C 1 -C 7 )-alkyl, aryl, aryl-( C 1 -C 7 )alkyl, aryl(C 1 -C 7 )alkoxy(C 1 -C 7 )alkyl, heteroaryl, heteroaryl(C 1 -C 7 )alkyl, (C 3 -C 7 )cycloalkyl(C 1 -C 7 )alkyl, (C 4 -C 7 )cycloalkenyl(C 1 -C 7 )alkyl, bis
  • R 34 is hydrogen, (C 1 -C 7 )alkyl, (C 2 -C 7 )alkenyl, aryl-(C 1 -C 7 )alkyl, aryl, heteroaryl, heteroaryl-(C C 1 -C 7 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 7 )-alkyl, R 32 O-(C 1 -C 7 )-alkyl, R 30 R 31 N-(C 1 -C 7 )- alkyl, NR 30 R 31 , (C 3 -C 7 )cycloalkyl-(C 1 -C 7 )alkyl, S(O) m R 33 , R 35 is hydrogen, NR 30 R 31 , OR 32 , (C 1 -C 7 )alkyl, (C 2 -C 7 )alkenyl, (C 2 -C 7 )alkynyl, aryl, aryl
  • a particularly preferred subject of the invention is the use of compounds of the general formula (I) in which R 1 is hydrogen, NR 30 R 31 , OR 32 , S(O) m R 33 , (C 1 -C 6 )-alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )haloalkynyl, (C 3 -C 6 cycloalkyl, (C 3 -C 6 )halocycloalkyl, (C 4 -C 6 )cycloalkenyl, (C 4 -C 6 )halocycloalkenyl, aryl, aryl-(C 1 -C 6 )alkyl , heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocycl
  • N-morpholinyl R 34 for hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, aryl-(C 1 -C 6 )-alkyl, aryl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, R 32 O-(C 1 -C 6 )-alkyl, R 30 R 31 N-(C 1 -C 6 )-alkyl, NO 30 R 31 , (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, S(O) m R 33 stands, R 35 for hydrogen, NO 30 R 31 , OR 32 , (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, ary
  • a very particularly preferred subject of the invention is the use of compounds of the general formula (I) in which R 1 for hydrogen, NO 30 R 31 , OR 32 , S(O) m R 33 , (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 4 -C 6 )-halocycloalkenyl, aryl, aryl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-al
  • N-morpholinyl R 34 for hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, aryl-(C 1 -C 6 )-alkyl, aryl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, R 32 O-(C 1 -C 6 )-alkyl, R 30 R 31 N-(C 1 -C 6 )-alkyl, NO 30 R 31 , (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, S(O) m R 33 stands, R 35 for hydrogen, NO 30 R 31 , OR 32 , (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, ary
  • a particularly preferred subject of the invention is the use of the following compounds described by general formula (I): 2-[1-[(3-chloro-2-fluorophenyl)methyl]-5-oxopyrrolidin-2-yl]acetic acid, 2-[ 1-[(2,3-difluorophenyl)methyl]-5-oxopyrrolidin-2-yl]-N-(1-methyl-1H-1,2,4-triazol-5-yl)acetamide, 2-[1- [(2,3-difluorophenyl)methyl]-5-oxopyrrolidin-2-yl]acetic acid, 2-[1-[(2,3-difluorophenyl)methyl]-5-oxopyrrolidin-2-yl]-N-(1 -methyl-1H-tetrazol-5-yl)acetamide, (2S,3S)-2-[[2-[(2S)-1-[(2,3- difluorophenyl)methyl]-5-ox
  • substituted N-pyrrolidinones of the general formula (I) are also not yet known in the prior art.
  • substituted N-pyrrolidinones of the general formula (I) or their salts apply, wherein R 1 for (C 1 -C 8th )-alkyl, (C 2 -C 8th )-alkenyl, (C 2 -C 8th )-alkynyl, (C 1 -C 10 )-haloalkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-halocycloalkyl, (C 4 -C 10 )-cycloalkenyl, aryl, aryl-(C 1 -C 8th )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8th )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8th )-alkyl-alkyl-alkyl, heterocycly
  • substituted N-pyrrolidinones of the general formula (I) or their salts apply, wherein R 1 for (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-methylphenyl)methyl, (3-trifluoromethylphenyl)methyl, (4-trifluoroethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (3-chlorophenyl)methyl, (4-chlorophenyl)methyl, (3-fluorophenyl)methyl, (4-fluorophenyl)methyl, (2-fluorophenyl)methyl, (3,4-difluorophenyl)methyl, (3,4-dichlorophenyl)methyl, (3-fluoro -4-chlorophenyl)methyl, (3-chloro-4-fluorophen
  • R 7 R represents hydrogen 3 , R 4 independently for hydrogen, (C 1 -C 8th )-alkyl, (C 1 -C 10 )-haloalkyl, (C 3 -C 10 )-cycloalkyl, aryl-(C 1 -C 8th )-alkyl, aryl, R 5 , R 6 independently for hydrogen, (C 1 -C 8th )-alkyl, (C 2 -C 8th )-alkenyl, (C 1 -C 10 )-haloalkyl, (C 3 -C 10 )-cycloalkyl, aryl-(C 1 -C 8th )-alkyl, aryl, heteroaryl, heteroaryl-(C 1 -C 8th )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8th )-alkyl, R 32 O-(C 1 -C 8th )-alkyl, R 30 R 31 N-(
  • R 35 for hydrogen, NO 30 R 31 , OR 32 , (C 1 -C 8th )-alkyl, (C 2 -C 8th )-alkenyl, (C 2 -C 8th )-alkynyl, aryl, aryl-(C 1 -C 8th )-alkyl, heteroaryl, heteroaryl-(C 1 -C 8th )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 8th )-alkyl, R 32 O-(C 1 -C 8th )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 10 )-cycloalkyl-(C 1 -C 8th )-alkyl, S(O) m R 33 , R 32 (O )C-(C 1 -C 8th )-alkyl, R 32 O(O)C-(C 1 -C 8th )-alkyl
  • R 7 R represents hydrogen 3 , R 4 independently for hydrogen, (C 1 -C 7 )-alkyl, (C 1 -C 7 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, aryl-(C 1 -C 7 )-alkyl, aryl, R 5 , R 6 independently for hydrogen, (C 1 -C 7 )-alkyl, (C 2 -C 7 )-alkenyl, (C 1 -C 7 )-haloalkyl, (C 3 -C 7 )-cycloalkyl, aryl-(C 1 -C 7 )-alkyl, aryl, heteroaryl, heteroaryl-(C 1 -C 7 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 7 )-alkyl, R 32 O-(C 1 -C 7 )-alkyl, R 30 R 31 N-(C 1 -C 7 )
  • R 35 for hydrogen, NO 30 R 31 , OR 32 , (C 1 -C 7 )-alkyl, (C 2 -C 7 )-alkenyl, (C 2 -C 7 )-alkynyl, aryl, aryl-(C 1 -C 7 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 7 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 7 )-alkyl, R 32 O-(C 1 -C 7 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 3 -C 7 )-cycloalkyl-(C 1 -C 7 )-alkyl, S(O)mR 33 , R 32 (O )C-(C 1 -C 7 )-alkyl, R 32 O(O)C-(C 1 -C 7 )-alkyl, R 30 R
  • N-morpholinyl, R 35 for hydrogen, NO 30 R 31 , OR 32 , (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, aryl, aryl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, R 32 O-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, S(O)mR 33 , R 32 (O )C-(C 1 -C 6 )-alkyl, R 32 O(O)C-(C 1 -C 6 )-alkyl, R 30 R
  • the following compounds of the general formula (I) are particularly preferred: 4-[2-[2-[1-[(4-methylphenyl)methyl]-5-oxopyrrolidin-2-yl]acetyl]oxyethoxy]benzoic acid, 2-( 4-formylphenoxy)ethyl 2-[1-[(4-methylphenyl)methyl]-5-oxopyrrolidin-2-yl]acetate, (2R)-2-[[2-[1-[(4-methylphenyl)methyl] -5-oxopyrrolidin-2-yl]acetyl]amino]-4-methylsulfanylbutyric acid, 2-(4-ethylphenoxy)ethyl 2-[1-[(4-methylphenyl)methyl]-5-oxopyrrolidin-2-yl]acetate, 2-(4-methylphenoxy)ethyl 2-[1-[(4-methylphenyl)methyl]-5-oxopyrrolidin-2-yl]
  • radicals given above in general or in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, ie also between the specified preferred ranges.
  • compounds of the formula (I) according to the invention or their salts or their use according to the invention are of particular interest, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
  • the designations used above and below are explained.
  • heterocyclyl- (C 1 -C 8th )-alkyl or R 32 O(O)C-(C 1 -C 8th )-alkyl the term “alkyl” therefore also stands for an alkylene group.
  • 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, e.g.
  • (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-methylpentylsulfonyl
  • heteroarylsulfonyl represents 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 on its own or as part of a chemical group—is straight-chain or branched S-alkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C 1 -C 10 )-, (C 1 -C 6 )- or (C 1 -C 4 )-alkylthio, e.g.
  • 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
  • (but not limited to) (C 1 -C 6 )-alkylsulphinyl such as methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentyl
  • Alkoxy means an alkyl radical bonded through an oxygen atom, e.g. B.
  • (but not limited to) (C 1 -C 6 )-Alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl- 1-methyl-propoxy and 1-ethyl-2-methylpropoxy.
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom such as (C 2 -C 10 )-, (C 2 -C 6 )- or (C 2 -C 4 )-alkenoxy or (C 3 -C 10 )-, (C 3 -C 6 )- or (C 3 -C 4 )-alkynoxy.
  • Cycloalkyloxy means an oxygen-bonded cycloalkyl radical and cycloalkenyloxy means an oxygen-bonded cycloalkenyl radical.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyl group.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, stand for alkenyl or alkynyl radicals which are bonded to the skeleton via —O—C( O)—, such as (C 2 -C 10 )-, (C 2 -C 6 )- or (C 2 -C 4 )-alkenyloxycarbonyl or (C 3 -C 10 )-, (C 3 -C 6 )- or (C 3 -C 4 )- alkynyloxycarbonyl.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • C(O)R 12 , C(O)OR 12 , OC(O)NO 10 R 11 , or C(O)NO 10 R 11 the abbreviation O given in brackets stands for an oxygen atom bonded to the adjacent carbon atom via a double bond.
  • OC(S)OR 12 , OC(S)SR 13 , OC(S)NO 10 R 11 the abbreviation S given in brackets stands for a sulfur atom bonded to the neighboring carbon atom via a double bond.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10, ring carbon 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 and biphenylyl, the binding site being on the aromatic system. Systematically, “aryl” is generally also included in the term “optionally substituted phenyl”.
  • 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-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris-[
  • heterocyclyl radical or heterocyclic ring When the heterocyclyl radical or heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, such as, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl.
  • spirocyclic systems are also included, such as 1-oxa-5-azaspiro[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 im heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should 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-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydr; 1,2,3,
  • 3-ring and 4-ring heterocycles are 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazol-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-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as 1,4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepine-2- or 3- or 5- or 6-
  • heterocycles listed above are preferably substituted, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkynyl, Alkynylalkyl, Alkylalkynyl, Tris-alkylsilylalkyny
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, as well as 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. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, e.g. with N and S, and then form, for example, the divalent groups N(O), S(O) (also short SO) and S(O) 2 (also short SO 2 ) in the heterocyclic ring.
  • N(O), S(O) (also short SO) and S(O) 2 (also short SO 2 ) in the heterocyclic ring.
  • -N(O)- and -S(O)- groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, i. H. completely unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N.
  • heteroaryls are 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-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-pyrrol-1-
  • heteroaryl groups according to the invention can also be substituted with one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • fused heteroaromatic systems such as benzo-fused or multiply fused heteroaromatics.
  • Preferred are, for example, 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.
  • 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-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5- yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halo means, for example, fluoro, chloro, bromo or iodo.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and, in the latter case, is referred to as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • bis also includes the combination of different alkyl radicals, e.g. methyl(ethyl) or ethyl(methyl).
  • "Haloalkyl”, "-alkenyl” and “alkynyl” mean alkyl, alkenyl or alkynyl, e.g. B.
  • perhaloalkyl such as e.g. B. CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl such as e.g. e.g., CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3;
  • perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is substituted one or more times by fluorine, where the corresponding fluorine atoms can be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as e.g.
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon substituted by various halogen atoms having at least one fluorine atom, with all other optionally present halogen atoms being selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms can be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes complete substitution of the straight or branched chain with halogen involving at least one fluorine atom.
  • haloalkoxy is OCF 3 , OCHF 2 , OH 2 F, OCF 2 CF 3 , OH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other radicals substituted by halogen.
  • (C 1 -C 4 )-Alkyl means an abbreviation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to the range specified for carbon atoms, i.e.
  • alkyl radicals with a larger specified range of carbon atoms e.g. "(C 1 -C 6 )-Alkyl” accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, i.e. according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, also in compound radicals, which preferably have lower carbon structures, for example with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms e.g., methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl , 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, where at least one double bond or triple bond is present.
  • radicals having a double bond or triple bond Preference is given to radicals having a double bond or triple bond.
  • alkenyl concludes esp especial also straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as allenyl (1,2 -propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which can 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
  • alkynyl also includes in particular straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-pentene-1-in-1 -yl.
  • (C 2 -C 6 )-Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl , 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl , 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3 -p
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alcocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • cyclic systems with substituents are included, with substituents having a double bond on the cycloalkyl radical, e.g. an alkylidene group such as methylidene.
  • polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl , bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1 ]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantane -2-yl, but also systems such.
  • 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, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 carbon atoms, e.g.
  • C 1 -C 10 )-Alkylidene means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkylidene means a carbocyclic radical bonded via a double bond.
  • Cycloalkylalkyloxy means an oxygen-bonded cycloalkylalkyl radical and "arylalkyloxy” means an oxygen-bonded arylalkyl radical.
  • Alkoxyalkyl means an alkoxy radical bonded through an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded through an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded through an alkyl group and “alkylthioalkylthio” means an alkylthioalkyl radical bonded through an oxygen atom.
  • Arylalkoxyalkyl means an aryloxy radical bonded through an alkyl group and “heteroaryloxyalkyl” means a heteroaryloxy radical bonded through an alkyl group.
  • Haloalkoxyalkyl means a linked haloalkoxy radical and "haloalkylthioalkyl” means a haloalkylthio radical linked through an alkyl group.
  • Arylalkyl means an aryl radical bonded through an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded through an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded through an alkyl group.
  • Cycloalkylalkyl represents a cycloalkyl radical bonded via an alkyl group, e.g. B.
  • Arylalkenyl means an aryl radical bonded through an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical bonded through an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical bonded through an alkenyl group
  • Arylalkynyl means an aryl radical bonded through an alkynyl group
  • heteroarylalkynyl means a heteroaryl radical bonded through an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl radical bonded through an alkynyl group
  • haloalkylthio on its own or as part of a chemical group—is straight-chain or branched S-haloalkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C 1 -C 8th )-, (C 1 -C 6 )- or (C 1 -C 4 )-haloalkylthio such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio .
  • Halocycloalkyl and halocycloalkenyl denote identical or different halogen atoms, such as e.g. B. F, Cl and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • Trialkylsilyl - alone or as part of a chemical group - for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as tri-[(C 1 -C 8th )-, (C 1 -C 6 )- or (C 1 -C 4 )-alkyl]silyl, such as (but not limited to) trimethylsilyl, triethylsilyl
  • Trialkylsilylalkynyl represents a trialkylsilyl radical bonded through an alkynyl group. If the compounds can form tautomers by hydrogen shift which would not be formally covered by formula (I) structurally, then these tautomers are nevertheless within the definition of the compounds of the formula (I) according to the invention, unless a specific tautomer is the subject of consideration. For example, many carbonyl compounds can exist in both the keto form and the enol form, both forms being encompassed by the definition of the compound of formula (I). Depending on the type and linkage of the substituents, the compounds of the general formula (I) can be present as stereoisomers.
  • 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 can occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods. The chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess and on a preparative scale to produce test specimens for biological testing.
  • stereoisomers can be prepared selectively by using stereoselective reactions using optically active starting materials and/or auxiliaries.
  • the invention thus also relates to all stereoisomers which are covered by the general formula (I) but are not specified with their specific stereo form, and mixtures thereof. If the compounds are obtained as solids, they can also be purified by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the routes described below, they can be prepared by derivatizing other compounds (I). Suitable methods for isolating, purifying and separating stereoisomers of compounds of the formula (I) are methods which are generally known to the person skilled in the art from analogous cases, e.g.
  • any remaining mixtures can usually be separated by chromatographic separation, e.g. on chiral solid phases.
  • processes such as crystallization, e.g. Synthesis
  • the compounds of the general formula (I) according to the invention can be prepared via various synthesis routes described in the literature, starting from starting substances that are commercially available or easily prepared.
  • the substituted pyrrolidinones of the general formula (I.1) can be prepared using a synthesis described in the literature (J. Org.
  • the pyrrolidinone (I.1a) resulting from the ring-closure reaction can then be 5.2 ⁇ 5 ,4 ⁇ 5 ,6 ⁇ 5 -trioxatriphosphinan-2,4,6-trioxide (T3P), hydroxybenzotriazole (HOBt)] using a suitable base (e.g. triethylamine or diisopropylethylamine) in a suitable polar-aprotic solvent (e.g. dichloromethane) into the corresponding esters (I.1b) or amides (I.1c) are converted.
  • a suitable base e.g. triethylamine or diisopropylethylamine
  • a suitable polar-aprotic solvent e.g. dichloromethane
  • oxopyrrolidinyl esters (I.1d) using a two-stage Chain extension from the corresponding oxopyrrolidinyl carboxylates (C) are prepared.
  • the carboxylic acid ester (C) in question is first converted into the intermediate alcohol (D) using a suitable reducing agent (e.g. sodium or lithium borohydride), which is then converted to the desired target product (I.1d ) (Chemistry - A European Journal (2017), 23, 7428-7432I).
  • a suitable reducing agent e.g. sodium or lithium borohydride
  • the substituted pyrrolidinones of the general formulas (I.3), (I.4) and (I.5) can also be prepared via synthesis routes described in the literature (cf. WO2012098132).
  • a suitable, optionally further substituted itaconic acid (E) with a suitable, optionally further substituted amine, preferably an alkyl, cycloalkyl, aryl or heteroarylmethylamine, at elevated temperature (e.g. 150° C.), the corresponding 5-oxopyrrolidinyl-3 -carboxylic acid (F) obtained (scheme 3).
  • the ring-closure reaction can be carried out in a conventional synthesis apparatus with a heating bath or in a suitable sealed vessel under microwave conditions.
  • the intermediate carboxylic acid (E) resulting from the ring-closure reaction can then be synthesized using suitable coupling reagents [e.g. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1,3,5,2 ⁇ 5 ,4 ⁇ 5 ,6 ⁇ 5 -trioxatriphosphinan-2,4,6-trioxide (T3P), hydroxybenzotriazole (HOBt)] using a suitable base (e.g. triethylamine or diisopropylethylamine) together with the corresponding optionally further substituted amine in a suitable polar-aprotic solvent (e.g.
  • suitable coupling reagents e.g. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1,3,5,2 ⁇ 5 ,4 ⁇ 5 ,
  • the carboxylic acid (E) can be synthesized by suitable reagents [e.g. diphenylphosphoryl azide (DPPA), triethylamine and tert. Butanol]-mediated degradation reaction carried out at elevated temperature (e.g. 80 °C) can be converted into the corresponding protected amine (F).
  • suitable reagents e.g. diphenylphosphoryl azide (DPPA), triethylamine and tert. Butanol
  • DPPA diphenylphosphoryl azide
  • Butanol e.g. diphenylphosphoryl azide
  • Butanol tert. Butanol
  • Removal of the relevant protecting group here by way of example but not limitation a tert-butyloxycarbonyl (Boc) protecting group] using a suitable reagent (e.g.
  • amine (G) (optionally also as a salt, e.g. by way of example but not limitation as the HCl salt).
  • the amine (G) can with the help of suitable coupling partners (example, but not limiting with an optionally further substituted acetic acid chloride, an optionally further substituted isocyanate or an optionally further substituted isothiocyanate) using a suitable base (e.g. triethylamine or diisopropylethylamine) in a suitable polar-aprotic solvent (e.g.
  • the optionally further substituted intermediate (G) can also be prepared starting from a further substituted glycine ester (H) in a multi-stage reaction via acylation, subsequent cyclization using a suitable base (e.g. sodium hydride) in a suitable polar aprotic solvent (e.g. tetrahydrofuran), oxime formation using hydroxylamine hydrochloride and a suitable base in a suitable polar aprotic solvent (e.g. dichloromethane) and final reduction of the oxime using a suitable reducing agent (e.g. sodium cyanoborohydride and hydrogen over palladium on carbon) (Scheme 4) .
  • a suitable base e.g. sodium hydride
  • a suitable polar aprotic solvent e.g. tetrahydrofuran
  • oxime formation using hydroxylamine hydrochloride and a suitable base in a suitable polar aprotic solvent e.g. dichloromethane
  • the optionally further substituted ureas of the general formula (I.4) can be prepared starting from a substituted amino acid (J) provided with suitable protective groups (cf. WO2006063113).
  • the base-mediated reaction of the amino acid (J) with a suitable isocyanate to form an optionally further substituted intermediate (K) takes place first.
  • the intermediate, optionally further substituted carboxylic acid (K) obtained in this way can then be 2 ⁇ 5 ,4 ⁇ 5 ,6 ⁇ 5 -trioxatriphosphinan-2,4,6-trioxide (T3P), hydroxybenzotriazole (HOBt)] using a suitable base (e.g. triethylamine or diisopropylethylamine) together with the appropriate amine R 1 -NH2 in a suitable polar-aprotic solvent (e.g.
  • the compounds of type I.2 could also be prepared analogously to the instructions from patent application WO2011/35332 (Scheme 6).
  • the corresponding pyrrolidonecarboxylic acids (O) are prepared by condensation of the corresponding anilines with itaconic acid derivatives (M). After esterification of the acids (O), e.g. using orthoesters or other methods, the corresponding carboxylic acid esters (P) are obtained. After deprotonation with a strong base such as e.g with an alkylating agent such as an alkyl halide such as methyl iodide or dimethyl sulfate to give the alkylated pyrrolidone carboxylic acid esters (Q).
  • a strong base such as e.g with an alkylating agent such as an alkyl halide such as methyl iodide or dimethyl sulfate
  • reaction mixture was stirred at room temperature for 1 hour. This was followed by the dropwise addition of triethylamine (376.0 mg, 0.52 mL, 3.71 mmol, 5.0 eq.) and the addition of DMAP (18.0 mg, 0.14 mmol.0.2 eq.), and the resulting reaction mixture was stirred at room temperature for 16 h. Then water (20 mL) was added and the aqueous phase was thoroughly extracted with dichloromethane (3 x 50 mL). The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Trans-3-hexenedioic acid 300 mg, 2.08 mmol
  • 1-(2,3,6-trifluorophenyl)methylamine 335 mg, 2.08 mmol
  • the pressure rose to 18 bar. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.
  • reaction mixture was stirred at room temperature for 1 h and then triethylamine (0.37 mL, 2.62 mmol, 3.0 eq.) was added dropwise.
  • the resulting reaction mixture was stirred at room temperature for a further 8 h and then treated with water (20 mL) and thoroughly extracted several times with dichloromethane (3 x 50 mL). The combined organic phases were dried over magnesium sulfate, filtered off and concentrated under reduced pressure.
  • I.2-33 1-[3,5-Bis(trifluoromethyl)phenyl]-N- ⁇ [2-(ethylamino)pyrimidin-4-yl]methyl ⁇ -5-oxopyrrolidine-3-carboxamide
  • the pH of the remaining aqueous phase was adjusted to 3-4 with 2N hydrochloric acid and the aqueous phase was extracted twice with 500 mL ethyl acetate each time. After drying the combined ethyl acetate phases over sodium sulfate, it was filtered and the Solvent removed in vacuo. The residue was suspended in 50 mL hexane (5 h), filtered off and washed with hexane. 5.40 g (purity 98%, 76% of theory) of the desired 1-(3,5-dichlorophenyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid were obtained as a colorless solid.
  • 1-(2-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid was obtained in the form of a colorless solid by recrystallization from ethyl acetate and used in the next reaction step without further purification.
  • 1-(2-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid (48.8 mmol, 1 equiv.) was dissolved in tert. Butanol (100 mL) and treated with diphenylphosphoryl azide (58.8 mmol, 1.2 equiv) and triethylamine (146.4 mmol, 3.0 equiv). The resulting reaction mixture was stirred at 80° C.
  • Butanol (100 mL) and treated with diphenylphosphoryl azide (58.8 mmol, 1.2 equiv) and triethylamine (146.4 mmol, 3.0 equiv).
  • the resulting reaction mixture was stirred at 80° C. for 2 h, concentrated under reduced pressure after cooling to room temperature and the crude product obtained was taken up without further purification in a mixture of hydrochloric acid and ethyl acetate (100 mL) and stirred at room temperature for 16 h. The precipitated solid was filtered off and dried.
  • 4-amino-1-cyclopropylpyrrolidin-2-one as a hydrochloride salt in the form of a Colorless solid be obtained.4-amino-1-cyclopropyl-pyrrolidin-2-one hydrochloride salt (150 mg, 0.85 mmol) was abs in a heated round bottom flask. Dissolved dichloromethane (5 mL) and treated with triethylamine (0.30 mL, 2.12 mmol). After stirring at room temperature for 10 minutes, 2,5-dichlorophenylacetic acid chloride (209 mg, 0.93 mmol) was added. The resulting reaction mixture was stirred at room temperature for 2 h, treated with water and dichloromethane and thoroughly extracted.
  • N-Phenylglycine ethyl ester (60 mmol, 1 equiv) and diisopropylethylamine (120 mmol, 2 equiv) were placed together in a heated round bottom flask, dissolved in abs. Dissolved dichloromethane (150 mL) and treated with propionyl chloride (120 mmol, 2 equiv.). The resulting reaction mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. After addition of saturated sodium bicarbonate solution and ethyl acetate, the aqueous phase was extracted three times with ethyl acetate (200 mL in total).
  • N-propionyl-N-phenylglcin ethyl ester was obtained and used in the next reaction step without further purification.
  • N-Propionyl-N-phenylglcin ethyl ester (60 mmol, 1.0 equiv.) was dissolved in abs. Dissolved tetrahydrofuran and carefully treated with sodium hydride (180 mmol, 3 equiv.). The resulting reaction mixture was stirred at a temperature of 65°C for 48 hours. After cooling to room temperature, the reaction mixture was quenched by adding ethanol dropwise and then concentrated under reduced pressure.
  • 1-phenyl-3,5-dioxo-4-methylpyrrolidine was obtained in the form of a colorless solid.1-Phenyl-3,5-dioxo-4-methylpyrrolidine (30.0 mmol , 1 equiv.) was dissolved in dichloromethane (100 mL) and treated with hydroxylamine hydrochloride (36.0 mmol, 1.2 equiv.) and diisopropylethylamine (60 mmol, 2.0 equiv.).
  • the resulting reaction mixture was stirred at room temperature for 16 h, concentrated under reduced pressure and the crude product obtained without further purification taken up in methanol (100 mL), treated with palladium on carbon (1.0 g) and stirred at room temperature under a hydrogen atmosphere (1 bar) for 16 h. Thereafter, the reaction mixture was filtered through Celite and concentrated under reduced pressure. The residue was taken up in acetic acid (50 mL) and treated with sodium cyanoborohydride (60 mmol, 2 equiv). The reaction mixture was stirred at room temperature for a further 16 h and again concentrated.
  • I.4-36 1-(5-Chloro-2-methylphenyl)-3-[1-phenyl-5-oxopyrrolidin-3-yl]urea. Itaconic acid (100 mmol, 1 equiv) and aniline (100 mmol, 1 equiv) were placed together in a heated round bottom flask and stirred at a temperature of 150 °C for 16 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.
  • Table I.1 Preferred for the use of compounds of formula (I.1) are the compounds I.1-1 to I.1-605, wherein R 1 , R 4 , R 13 and X have the meanings of Table I.1 given in the respective row and R 3 , R 5 , R 6 , R 7 and R 14 are hydrogen and where X is a moiety O-R 36 or N(R 15 )r 35 stands.
  • the stereochemistry at carbon C-2 is defined by "RAC” for a mixture of both stereo configurations at carbon C-2, "Ent-1” and “Ent-2” for one enantiomer (or diastereomer if there are several stereocenters in the molecule) with one Stereo configuration given at carbon C-2.
  • Table I.1 The stereochemistry at carbon C-2 is defined by "RAC” for a mixture of both stereo configurations at carbon C-2, "Ent-1” and “Ent-2” for one enantiomer (or diastereomer if there are several stereocenters in the molecule) with one Stereo configuration given at carbon C-2.
  • Table I.2 Preferred for the use of compounds of formula (I.2) are the compounds I.2-1 to I.2-182, wherein R 1 , R 3 , R 4 , R 5 , R 20 , R 21 and R 37 have the meanings given in Table I.2 in the respective row and R 2 , R 6 and R 22 are hydrogen.
  • the bonds marked with an asterisk (*) of the groups formed jointly by R3 and R5 indicate the bonds to the pyrrolidinone ring.
  • R 21 and R 37 together with the carbon atom to which they are attached form a ring system which can optionally also be bicyclic. The ring system formed in this way, including the carbon atom, is then indicated accordingly in a common column for R 21 and R 37 .
  • Table I.2 Preferred for the use of compounds of formula (I.2) are the compounds I.2-1 to I.2-182, wherein R 1 , R 3 , R 4 , R 5 , R 20 , R 21 and R 37 have the meanings given in Table I.
  • Table I.3 Preferred for the use of compounds of the formula (I.3) are the compounds I.3-1 to I.3-37, in which R 1 , R 3 , R 5 , R 10 and R 37 are in have the meanings of Table I.3 given in the respective row and R 2 , R 4 , R 6 , R 11 and R 12 are hydrogen. Table I.3
  • Table I.4 Preferred for the use of compounds of the formula (I.4) are the compounds I.4-1 to I.4-141, in which R 1 , R 3 , R 5 and R 37 are those in the respective line have the meanings given in Table I.4 and R 2 , R 4 , R 6 , R 8 and R 9 are hydrogen. Table I.4
  • Table I.5 Preferred for the use of compounds of the formula (I.5) are the compounds I.5-1 to I.5-34, in which R 1 , R 3 , R 5 and R 37 are those in the respective line have the meanings given in Table I.5 and R 2 , R 4 and R 6 are hydrogen. , Table I.5 4
  • Spectroscopic data of selected examples in the table were obtained either via classical NMR interpretation and/or via 1 H NMR peak list method evaluated.
  • I.4-32 1 H NMR (400 MHz, i.e 6 -DMSO) ⁇ ppm 8.89 (s, 1H), 8.43 (d, 1H), 7.97-7.93 (m, 1H), 7.59 (d, 1H), 7.46-7.38 (m, 4H), 7.01 (m, 1H) , 4.52-4.45 (m, 1H), 4.02-3.97 (m, 1H), 3.59-3.54 (dd, 1H), 2.89-2.82 (dd, 1H), 2.45-2.38 (dd, 1H).
  • Example No. I.4-34 1 H NMR (400 MHz, d6-DMSO) ⁇ ppm 9.26 (s, 1H), 8.93 (br.
  • the peak list of an example therefore has the form: ⁇ 1 (intensity1 ) ; ⁇ 2 (intensity2);........; ⁇ i (intensityi ) ; whil; ⁇ n (intensitiesn)
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • To calibrate the chemical shift of 1 H-NMR spectra use tetramethylsilane and/or solvent chemical shift, especially in the case of spectra measured in DMSO.
  • the tetramethylsilane peak can therefore appear in NMR peak lists, but it does not have to.
  • the lists of 1 H NMR peaks are similar to classic 1H NMR plots and thus usually include all peaks listed in a classic NMR interpretation.
  • they can show signals from solvents, signals from stereoisomers of the target compounds, which are also the subject of the invention, and/or peaks from impurities.
  • our lists of 1H NMR peaks are the usual solvent peaks, for example peaks from DMSO in DMSO-D 6 and the peak of water, which usually have high intensity on average.
  • the peaks of stereoisomers of the target compounds and/or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (e.g. with a purity of >90%). Such stereoisomers and/or impurities can be typical of the particular production process. Their peaks can thus help identify the reproduction of our manufacturing process using “by-product fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods can isolate the peaks of the target compounds as required, with additional intensity filters being used if necessary. This isolation would be similar to the peak picking involved in classical 1H NMR interpretation. More details about 1 H NMR peak lists can be found in Research Disclosure Database Number 564025.
  • Another subject of the present invention is a spray solution for treating plants, containing an amount of at least one compound selected from the group consisting of at least one of the substituted pyrrolidinones according to the invention, of the general formula (I ).
  • the abiotic stress conditions that can be put into perspective include, for example, heat, drought, cold and drought stress (stress caused by drought and/or lack of water), osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, strong light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
  • the corresponding pyrrolidinones of the general formula (I) substituted according to the invention can be applied by spray application to plants or parts of plants to be treated accordingly.
  • the compounds of the general formula (I) or their salts are preferably used at a dosage of between 0.00005 and 3 kg/ha, particularly preferably between 0.0001 and 2 kg/ha, particularly preferably between 0.0005 and 1 kg/ha. ha, especially preferably between 0.001 and 0.25 kg/ha.
  • the term resistance or resilience to abiotic stress is understood to mean various advantages for plants.
  • Such advantageous properties are expressed, for example, in the improved plant characteristics mentioned below: improved root growth in terms of surface and depth, increased stolon formation or tillering, stronger and more productive stolons and tillers, improvement in shoot growth, increased stability, increased shoot base diameter, increased leaf area, higher yields of nutrients and ingredients such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibres, better fiber quality, earlier flowering, increased number of flowers, reduced levels of toxic products such as mycotoxins, reduced levels of residues or unfavorable components 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 water starvation excess, improved tolerance to increased salt levels in soil and water, increased tolerance to ozone stress, improved tolerance to herbicides and other plant treatment products, improved water absorption and photosynthetic performance, advantageous plant properties, such as accelerated ripening, more even ripening, greater attraction for beneficial organisms, improved pollination or other advantages well known
  • Such terms are, for example, the terms listed below: phytotonic effect, resistance to stress factors, less plant stress, plant health, healthy plants, plant fitness (“Plant Fitness”), “Plant Wellness”, “Plant Concept”, “Vigor Effect”, “Stress Shield, Crop Health, Crop Health Properties, Crop Health Products, Crop Health Management, Crop Health Therapy, Plant Health, Plant Health Properties, Plant Health Products, Plant Health Management", “Plant Health Therapy”, “Greening Effect” or “Re-greening Effect”), "Freshness” or other terms well known to a person skilled in the art.
  • a good effect on abiotic stress resistance is not limited • at least one emergence improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, • at least one yield increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, • at least one by im Generally 3%, in particular greater than 5%, particularly preferably greater than 10% improved root development, • at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, • at least one by generally 3%, in particular greater than 5%, particularly preferably greater than 10%, • at least one photosynthesis performance improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10% and/or • at least one by generally 3%, in particular greater understood as 5% particularly preferably greater than 10% improved flower formation, the effects being individual or in any combination ion of two or more effects can occur.
  • the present invention further provides a spray solution for treating plants, containing an amount of at least one compound from the group of substituted pyrrolidinones of the general formula (I) effective to increase the resistance of plants to abiotic stress factors.
  • the spray solution can contain other customary components, such as solvents, formulation auxiliaries, in particular water. Other components can be, inter alia, agrochemical active ingredients, which are described in more detail below.
  • Another object of the present invention is the use of corresponding spray solutions to increase the resistance of plants to abiotic stress factors. The statements below apply both to the use of one or more compounds of the general formula (I) according to the invention per se and to the corresponding spray solutions.
  • Fertilizers which can be used according to the invention together with the compounds of the general formula (I) according to the invention explained in more detail above are generally organic and inorganic nitrogen-containing compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates), phosphoric acid salts and/or salts of phosphorous acid (preferably potassium salts and ammonium salts).
  • NPK fertilizers i.e.
  • fertilizers that contain nitrogen, phosphorus and potassium, calcium ammonium nitrate, i.e. fertilizers that also contain calcium, ammonium sulphate nitrate (general formula (NH4)2SO4 NH4NO3), ammonium phosphate and ammonium sulphate.
  • NH42SO4 NH4NO3 calcium, ammonium sulphate nitrate
  • ammonium phosphate and ammonium sulphate generally 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 can also contain salts from micronutrients (preferably calcium, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (e.g.
  • Fertilizers used according to the invention can also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate, potassium chloride, magnesium sulfate.
  • MAP monoammonium phosphate
  • DAP diammonium phosphate
  • Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5% by weight, based on the fertilizer as a whole.
  • Other possible ingredients are crop protection agents, insecticides, fungicides, safeners or growth regulators or mixtures thereof. Further explanations on this follow below.
  • the fertilizers can be used, for example, in the form of powders, granules, prills or compacts.
  • the fertilizers can also be used in liquid form, dissolved in an aqueous medium.
  • diluted aqueous ammonia can also be used as a 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 4128828, DE-A 1905834 and DE-A 19631764.
  • the general composition of the fertilisers which in the context of the present invention can be straight and/or complex fertilizers, for example nitrogen, potassium or phosphorus, can vary within a wide range.
  • a content of 1 to 30% by weight nitrogen (preferably 5 to 20% by weight), 1 to 20% by weight potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight phosphorus (preferably 3 to 10% by weight) is advantageous.
  • the content of microelements is usually in the ppm range, preferably in the range from 1 to 1000 ppm.
  • the fertilizer and one or more compounds of the general formula (I) according to the invention can be administered simultaneously. However, it is also possible first to use the fertilizer and then to use one or more compounds of the general formula (I) according to the invention, or first to use one or more compounds of the general formula (I) and then to use the fertilizer.
  • one or more compounds of the general formula (I) and the fertilizer are not used at the same time, the application in the context of the present invention takes place in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, particularly preferably 12 hours, specifically 6 hours, even more special 4 hours, even more special within 2 hours.
  • one or more compounds of the formula (I) according to the invention and the fertilizer are applied within a time frame of less than 1 hour, preferably less than 30 minutes, particularly preferably less than 15 minutes.
  • Forest stock includes trees for the manufacture of wood, pulp, paper and products made from parts of the trees.
  • useful plants as used here, refers to crop plants that are used as plants for the production of food, animal feed, fuel or for technical purposes.
  • the useful plants include B.
  • triticale durum (hard wheat), turf, vines, cereals, for example wheat, barley, rye, oats, rice, maize and millet
  • Beet for example sugar beet and fodder beet
  • Fruits for example pome fruit, stone fruit and berries, for example apples, pears, plums, peaches, almonds, cherries and berries, e.g. B.
  • strawberries, raspberries, blackberries legumes such as beans, lentils, peas and soybeans
  • Oil crops for example rapeseed, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and peanuts
  • cucumber plants such as squash, cucumbers and melons
  • fiber crops such as cotton, flax, hemp and jute
  • citrus fruits e.g.
  • vegetables for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers
  • Laurel plants for example avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grapevines, hops, bananas, natural rubber plants and ornamental plants, for example flowers, shrubs, deciduous trees and conifers such as conifers. This list does not represent a limitation.
  • the following plants are to be regarded as particularly suitable target crops for the application of the method according to the invention: oats, rye, triticale, durum, cotton, eggplant, turf, pome fruit, stone fruit, soft fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , pear, pepper, beans, soybeans, canola, tomato, pepper, melon, cabbage, potato and apple.
  • trees that can be improved according to the method of the present invention can be named: 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 species 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.
  • Particularly preferred trees which can be improved according to the method according to the invention can be mentioned: From the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis.
  • horse chestnut As particularly preferred trees which can be improved according to the method of the present invention, there can be mentioned: horse chestnut, sycamore, linden and maple tree.
  • the present invention can also be practiced on any turfgrasses, including cool season turfgrasses and warm season turfgrasses.
  • Examples of lawn types for the cold season 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.); Bentgrass (Agrostis spp.), such as creeping bentgrass (Agrostis palustris Huds.), colonial bentgrass (Agrostis tenuis Sibth.), velvet bentgrass (Agrostis canina L.), South German Mixed Bentgrass ' (Agrostis spp.
  • Agrostis tenius Sibth. including Agrostis tenius Sibth., Agrostis canina L., and Agrostis palustris Huds.), and 'redtop' (Agrostis alba L.); Fescues ("Fescues", Festucu spp.), such as “red fescue” (Festuca rubra L. spp.
  • Examples of other “cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “smooth bromegrass” (Bromus inermis Leyss.), “cattails” like “Timothy” (Phleum pratense L.), “sand cattail (Phleum subulatum L.), orchardgrass (Dactylis glomerata L.), weeping alkaligrass (Puccinellia distans (L.) Parl.) and crested dog's-tail (Cynosurus cristatus L.).
  • Examples of warm season turfgrasses are Bermudagrass (Cynodon spp. L.C.
  • crop plants can 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 transgenic plants and including plant varieties which can or cannot be protected by plant variety rights.
  • the treatment method according to the invention can thus also be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds can be used.
  • GMOs genetically modified organisms
  • Genetically modified plants (or transgenic plants) are plants in which a heterologous gene is stable in the genome has been integrated.
  • heterologous gene essentially means a gene that is provided or assembled outside of the plant and, when introduced into the nuclear genome, chloroplast genome, or hypochondriacal genome, confers new or improved agronomic or other traits on the transformed plant by producing a trait of interest protein or polypeptide, or that it downregulates or shuts down another gene(s) present in the plant (e.g., using antisense technology, co-suppression technology, or RNA interference [RNAi] technology) .
  • a heterologous gene that is present in the genome is also called a transgene.
  • a transgene that is defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • Plants and plant varieties that are preferably treated with the compounds of the general formula (I) according to the invention include all plants that have genetic material that gives these plants particularly advantageous, useful traits (regardless of whether this is achieved by breeding and/or biotechnology would).
  • Plants and plant cultivars which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions can include, for example, heat, drought, cold and drought stress, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, or avoidance of shade.
  • Plants and plant cultivars which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield-related properties.
  • An increased yield can be achieved with these plants e.g. B. based on improved plant physiology, improved plant growth and improved plant development, such as water use efficiency, water holding efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, enhanced germination and accelerated ripening.
  • Yield can be further influenced by improved plant architecture (under stressed and non-stressed conditions) including early flowering, control of flowering for hybrid seed production, seedling vigour, plant size, internodal number and spacing, root growth, seed size, fruit size, Pod size, number of pods or spikes, number of seeds per pod or spike, seed mass, increased seed filling, reduced seed loss, reduced pod bursting and stability.
  • plant architecture under stressed and non-stressed conditions
  • Other yield traits include seed composition such as carbohydrate content, protein content, oil content and oil composition, Nutritional value, reduction of anti-nutritional compounds, improved processability and improved shelf life.
  • Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which already express the properties of heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stressors.
  • Such plants are typically produced by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent).
  • the hybrid seed is typically harvested from the male-sterile plants and sold to propagators.
  • Male-sterile plants can sometimes (e.g., in maize) be produced by detasseling (i.e., mechanically removing the male reproductive organs or male flowers); however, it is more common that male sterility is due to genetic determinants in the plant genome.
  • cytoplasmic male sterility have been described for example for Brassica species (WO92/005251, WO95/009910, WO98/27806, WO2005/002324, WO2006/021972 and US6,229,072).
  • male-sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly useful means of producing male-sterile plants is described in WO 89/10396, where for example a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression of a ribonuclease inhibitor such as Barstar in the tapetum cells (e.g. WO91/002069).
  • Plants or plant cultivars which can also be treated with the compounds of general formula (I) according to the invention are herbicide-tolerant plants, i. H. Plants that have been made tolerant to one or more specified herbicides. Such plants can be obtained either by genetic transformation or by selection from plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants that have been made 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
  • Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol.
  • Glyphosate tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme as described in US5,776,760 and US5,463,175. Glyphosate tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. B. WO2002/036782, WO2003/092360, WO2005/012515 and WO2007/024782. Glyphosate tolerant plants can also be obtained by selecting plants containing naturally occurring mutations of the genes mentioned above, as described for example in WO01/024615 or WO2003/013226.
  • herbicide-resistant plants are, for example, plants which have been made tolerant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of the enzyme glutamine synthase that is resistant to inhibition.
  • a potent detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species).
  • Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US5,561,236; US5,648,477; US5,646,024; US5,273,894; US5,637,489; US5,276,268; US5,739,082; US5,908,810 and US7,112,665.
  • Other herbicide-tolerant plants are also plants that have been made tolerant to the herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD).
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted into homogentisate.
  • Plants that are tolerant to HPPD inhibitors can be endowed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO96/038567, WO99/024585 and WO99/024586 , to be transformed.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding encode 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 WO99/034008 and WO2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO2004/024928 is described.
  • Other herbicide resistant plants are plants that have been made tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates and/or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • WO2004/040012 WO2004/106529, WO2005/020673, WO2005/093093, WO2006/007373, WO2006/015376, WO2006/024351 and WO2006/060634 are described.
  • Other sulfonylurea- and imidazolinone-tolerant plants are also described, for example, in WO2007/024782.
  • plants that 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 mutation breeding, as is the case, for example, for the soybean in US5,084,082 , for rice in WO97/41218, for sugar beet in US5,773,702 and WO99/057965, for lettuce in US5,198,599 or for sunflower in WO2001/065922.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can also be treated with the compounds of general formula (I) according to the invention are insect-resistant transgenic plants, i.e. plants which are resistant to infestation by certain target insects were made. Such plants can be obtained by genetic transformation or by selection from plants containing a mutation conferring such insect resistance.
  • insect resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence encoding: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal part thereof, such as the insecticidal crystal proteins that by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, e.g.
  • the protein Cry1A.105 produced by the maize event MON98034 (WO2007/027777); or 4) a protein according to any one of points 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve higher insecticidal activity against a target insect species and / or to the spectrum of to expand corresponding target insect species and/or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in 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 insecticidal proteins (VIP) listed at the following link, e.g.
  • VIP vegetative insecticidal proteins
  • an insecticidal hybrid protein comprising parts of different secreted proteins from 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 points 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve higher insecticidal activity against a target insect species and / or to the spectrum of corresponding target insect species and/or because of changes induced in the coding DNA during cloning or transformation (while preserving the coding for an insecticidal protein), such as the protein VIP3Aa in the cotton event COT 102.
  • one of the insect-resistant transgenic plants in the present context also includes any plant comprising a combination of genes encoding the proteins of any of classes 1 to 8 above.
  • an insect-resistant plant contains more than one transgene encoding a protein according to any one of the above 1 to 8 in order to broaden the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by employs different proteins that are insecticidal to 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 cultivars obtained by methods of plant biotechnology, such as genetic engineering which can also be treated with the compounds of general formula (I) according to the invention are tolerant to abiotic stress factors.
  • Such plants can be obtained by genetic transformation or by selection from plants containing a mutation conferring such stress resistance.
  • Particularly useful stress tolerant plants include the following: a. Plants containing a transgene capable of reducing the expression and/or activity of the gene for poly(ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO2000/004173 or EP04077984.5 or EP06009836. 5 is described.
  • b Plants which contain a stress tolerance-promoting transgene which is able to reduce the expression and/or activity of the PARG-encoding genes of the plants or plant cells, as described, for example, in WO2004/090140; c.
  • Plants containing a stress tolerance promoting transgene encoding a plant functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including Nicotinamidase, nicotinate phosphoribosyl transferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyl transferase, as z. in EP04077624.7 or WO2006/133827 or PCT/EP07/002433.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering, which can also be treated with the compounds of the general formula (I) according to the invention, have a changed quantity, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product, such as: 1) Transgenic plants that synthesize a modified starch that differ in terms of their chemical-physical properties, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch granule size and/or starch granule morphology compared to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • a modified starch that differ in terms of their chemical-physical properties, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains
  • transgenic plants synthesizing a modified starch are for example in EP0571427, WO95/004826, EP0719338, WO96/15248, WO96/19581, WO96/27674, WO97/11188, WO97/26362, WO97/32985, WO97/42328 , WO97/44472, WO97/45545, WO98/27212, WO98/40503, WO99/58688, WO99/58690, WO99/58654, WO2000/008184, WO2000/008185, WO2000/28052, WO2000/77229, WO20001/2 /12826, WO2002/1059, WO2003/071860, WO2004/056999, WO2005/030941, WO2005/095632 , WO2006/108702, WO2007/009823, WO2000/22140, WO2006/072603, WO2002/034923, EP06090228.5, EP
  • Transgenic plants that synthesize non-starch carbohydrate polymers, or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification.
  • Examples are plants producing polyfructose, particularly of the inulin and levan types as described in EP0663956, WO96/001904, WO96/021023, WO98/039460 and WO99/024593, plants producing alpha-1,4-glucans , as described in WO95/031553, US2002/031826, US6,284,479, US5,712,107, WO97/047806, WO97/047807, WO97/047808 and WO2000/14249, plants producing alpha-1,6-branched alpha-1,4-glucans as described in WO2000/73422 and plants producing alternan as described in WO2000/ 047727, EP06077301.7, US5,908,975 and EP0728213.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering) which can also be treated with the compounds of the general formula (I) 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 from plants containing a mutation conferring such altered fiber properties; these include: a) plants such as cotton plants containing an altered form of cellulose synthase genes as described in WO98/000549, b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO2004 /053219; c) plants such as cotton plants with increased expression of sucrose phosphate synthase, as described in WO2001/017333; d) plants such as cotton plants with increased expression of sucrose synthase, as described in WO2002/45485; e) Plants such as cotton plants in which the timing of gating of the plasmodesmata at the base of the fiber cell is altered, e.g.
  • plants such as cotton plants with fibers with altered reactivity, e.g. B. by expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes, as described in WO2006/136351.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering) which are also treated with the compounds of the general formula (I) according to the invention can be treated are crops such as oilseed rape or related Brassica crops with altered oil composition properties.
  • Such plants can be obtained by genetic transformation or by selection from plants containing a mutation conferring such altered oil properties; these include: a) plants such as rape plants which produce oil with a high oleic acid content, as described for example in US5,969,169, US5,840,946 or US6,323,392 or US6,063,947; b) Plants such as rape plants which produce oil with a low linolenic acid content as described in US6,270828, US6,169,190 or US5,965,755. c) Plants, such as rapeseed, which produce oil with a low saturated fatty acid content, e.g. as described in US5,434,283.
  • Particularly useful transgenic plants which can be treated with the compounds of general formula (I) according to the invention are plants which contain transformation events, or a combination of transformation events, and which are, for example, in the files of various national or regional authorities are listed.
  • Particularly useful transgenic plants which can be treated with the compounds of general formula (I) according to the invention are exemplified by plants having one or more genes which code for one or more toxins are the transgenic plants which are offered under the following trade names: YIELD GARD ⁇ (e.g. corn, cotton, soybeans), KnockOut ⁇ (e.g. corn), BiteGard ⁇ (e.g. corn), BT-Xtra ⁇ (e.g. corn), StarLink ⁇ (e.g.
  • Herbicide tolerant crops to mention are, for example, corn varieties, cotton varieties and soybean varieties sold under the following trade names: Roundup Ready ⁇ (glyphosate tolerance, e.g. corn, cotton, soybean), Liberty Link ⁇ (phosphinotricin tolerance, e.g. canola) , IMI ⁇ (imidazolinone tolerance) and SCS ⁇ (sylphonylurea tolerance), for example corn.
  • Roundup Ready ⁇ glyphosate tolerance, e.g. corn, cotton, soybean
  • Liberty Link ⁇ phosphinotricin tolerance, e.g. canola
  • IMI ⁇ imidazolinone tolerance
  • SCS ⁇ sylphonylurea tolerance
  • 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-based and oil-based suspensions, Powders, dusts, pastes, soluble powders, soluble granules, scattered granules, suspension emulsion concentrates, natural substances impregnated with active substances, synthetic substances impregnated with active substances, fertilizers and very fine encapsulations in polymeric substances.
  • the compounds of the general formula (I) are used in the form of a spray formulation.
  • the present invention therefore also relates to a spray formulation for increasing the resistance of plants to abiotic stress.
  • a spray formulation is described in more detail below:
  • 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, i.e. liquid solvents and/or solid carriers, if appropriate using surface-active agents, ie emulsifiers and/or dispersants and/or foam-forming agents.
  • customary additives such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water, can optionally also be used.
  • the formulations are produced either in suitable systems or else before or during use.
  • Substances that are suitable for imparting special properties to the agent itself or and/or preparations derived from it (e.g. spray mixtures), such as certain technical properties and/or also special biological properties, can be used as auxiliaries.
  • auxiliaries that can be used are: extenders, solvents and carriers.
  • Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and/or may be esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified
  • organic solvents can also be used as auxiliary solvents.
  • Dyes such as inorganic pigments, e.g., iron oxide, titanium oxide, ferrocyanide, 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 can be used.
  • Suitable wetting agents which can be present in the formulations which can be used according to the invention are all substances which promote wetting and which are customary for the formulation of agrochemical active ingredients.
  • Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates can preferably be used.
  • Suitable dispersants and/or emulsifiers which can be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemically active compounds.
  • Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates. All foam-inhibiting substances customary for the formulation of agrochemically active compounds can be present as antifoams in the formulations which can be used according to the invention. Silicone defoamers and magnesium stearate can preferably be used.
  • the gibberellins are known (cf. R. Wegler "Chemistry of plant protection and pest control agents", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • additives can be fragrances, mineral or vegetable oils, optionally modified, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, antioxidants, light stabilizers or other agents that improve chemical and/or physical stability can also be present.
  • the formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90% by weight. %, of the compound of general formula (I).
  • the compounds of the general formula (I) according to the invention can be used in commercial formulations and in the use forms prepared from these formulations as a mixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or Semiochemicals present. Furthermore, the described positive effect of the compounds of the formula (I) on the plants' own defenses can be supported by additional treatment with insecticidal, fungicidal or bactericidal active ingredients. Preferred times for the application of the compounds of the general formula (I) according to the invention or their salts to increase the resistance to abiotic stress are soil, stem and/or leaf treatments with the permitted application rates.
  • the compounds of the general formula (I) according to the invention or their salts can generally also be used in their commercial formulations and in the use forms prepared from these formulations in mixtures with other active ingredients such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth-regulating substances, substances that affect plant maturity, safeners or herbicides.
  • the active ingredients of the general formula (I) can generally also in their commercial formulations and in the use forms prepared from these formulations in mixtures with other active ingredients such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth-regulating substances that Plant maturity influencing substances, safeners or herbicides are present.
  • Particularly favorable mixing partners are, for example, the active ingredients of the various classes listed below in groups, without any preference being set based on their order:
  • F1 Inhibitors of nucleic acid synthesis, eg. B. benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacone, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;
  • F2 Inhibitors of mitosis and cell division, e.g. B.
  • Inhibitors of ATP production e.g. fentin acetate, fentin chloride, fentin hydroxide, silthiofam F7) inhibitors of amino acid and protein biosynthesis, e.g. andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil F8) inhibitors of signal transduction, e. B. fenpiclonil, fludioxonil, quinoxyfen F9) Inhibitors of fat and membrane synthesis, z.
  • Inhibitors of ATP production e.g. fentin acetate, fentin chloride, fentin hydroxide, silthiofam F7
  • inhibitors of amino acid and protein biosynthesis e.g. andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim,
  • chlozolinate iprodione, procymidone, vinclozolin, ampropylfos, potassium ampropylfos, edifenphos, iprobefos (IBP), isoprothiolane, pyrazophos, tolclofos-methyl, biphenyl, iodocarb, propamocarb, propamocarb hydrochloride F10) Inhibitors of ergosterol biosynthesis, e.g. B.
  • Insecticides / acaricides / nematicides The active ingredients mentioned here by their "common name” are known and are described, for example, in the pesticide manual ("The Pesticide Manual” 14th Ed., British Crop Protection Council 2006) or can be researched on the Internet (e.g. http://www .alanwood.net/pesticides).
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g.
  • GABA-gated chloride channel antagonists such as cyclodiene-organochlorins, e.g., Chlordane and Endosulfan, or phenylpyrazoles (Fiprole), e.g., Ethiprole and Fipronil.
  • GABA-gated chloride channel antagonists such as cyclodiene-organochlorins, e.g., Chlordane and Endosulfan, or phenylpyrazoles (Fiprole), e.g., Ethiprole and Fipronil.
  • Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids e.g.
  • Nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g., spinetoram and spinosad.
  • Chloride channel activators such as avermectins/milbemycins, e.g., abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogues, e.g., hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
  • Drugs with unknown or non-specific mechanisms of action such as alkyl halides, e.g., methyl bromide and other alkyl halides; or chloropicrine, or sulfuryl fluoride, or borax, or tartar emetic.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
  • Inhibitors of chitin biosynthesis type O such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • Inhibitors of chitin biosynthesis, type 1 such as buprofezin.
  • Ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • Complex III electron transport inhibitors such as hydramethylnon or acequinocyl or fluacrypyrim.
  • Complex I electron transport inhibitors for example METI acaricides, e.g., fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or Rotenone (Derris).
  • Voltage-gated sodium channel blockers e.g., indoxacarb or metaflumizone.
  • Inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g., spirobudiclofen, spirodiclofen, spiromesifen and spirotetramat.
  • Complex IV electron transport inhibitors such as phosphines, e.g., aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • Ryanodine receptor effectors such as diamides, e.g., chlorantraniliproles, cyantraniliproles, flubendiamides and tetrachlorantraniliproles.
  • Other active ingredients with an unknown or ambiguous mechanism of action such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluazaindolizine, fluensulfone, flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafone, Fluopyram, Fluralaner, Fluxametamide, Fuf
  • Safeners are preferably selected from the group consisting of: S1) compounds of formula (S1), where the symbols and indices have the following meanings: nA 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 saturated or aromatic five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom is contained in the ring, preferably one Rest of the group (WA 1 ) to (WA 4 ), mA is 0 or 1; RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N
  • RB 1 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl
  • nB is a natural number from 0 to 5, preferably 0 to 3
  • RB 2 is ORB 3 , SRB 3 or NRA 3 RB 4 or a saturated one or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected to the carbonyl group in (S2) via the N atom and is unsubstituted or substituted by radicals of the group (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl, preferably a radical of the formula OR B 3 , NHR B 4 or N(
  • R C 1 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 7 )-cycloalkyl, preferably dichloromethyl;
  • R C 2 , R C 3 are identical or different hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 4 )-alkylcarbamoyl-(C 1 -C 4 )-alkyl, (C 2 - C 4 )-alkenylcarbam
  • XD is CH or N;
  • RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-alkoxycarbonyl or (C 1 -C 4 )-alkylcarbonyl;
  • R D 3 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;
  • R D 4 is
  • the e.g. B. are known from WO-A-97/45016 wherein RD 7 (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, where the 2 last-mentioned radicals are replaced by vD substituents from the group halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 -C 4 )-alkylthio and in the case of cyclic radicals also (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl; RD 4 halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ; mD 1 or 2; v D is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides,
  • S5 Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 3,5-di-methoxy-4- hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001.
  • S6 Active substances from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • R E 1 , R E 2 are independently halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, nitro;
  • AE is COORE 3 or COSRE 4 RE 3
  • R.E 4 are 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, halobenzyl, pyridinylalkyl and
  • S9 Active substances 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.Nr.219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-quinolone (CAS Reg.Nr.95855-00- 8) as described in WO-A-1999/000020.
  • S9 3-(5-tetrazolylcarbonyl)-2-quinolones
  • S11 Active substances of the type of oxyimino compounds (S11), which are known as seed dressings, such as. B. "Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1) known as a seed dressing safener for millet against damage from metolachlor, "Fluxofenim” (1- (4-Chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2) used as a seed dressing safener for sorghum against damage from metolachlor, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for sorghum against damage from metolachlor.
  • S12 Active substances from the class of isothiochromanone (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6 ) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanone
  • S13 One or more compounds from group (S13): "Naphthalic anhydride” (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), known as a seed dressing safener for corn against damage from thiocarbamate herbicides, "Fenclorim” (4.6 -dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in seeded rice, "Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13 -3) known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS Reg.No.31541-57-8) (4-carboxy-3,4-dihydro-2H- 1- benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolin
  • Substances influencing plant maturity are, for example, known active substances 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. B. ETR1, ETR2, ERS1, ERS2 or EIN4, can be used, as z. B. in Biotechn. Adv. 2006, 24, 357-367; Bot. Bull. Acad. Sin.199, 40, 1-7 or Plant Growth Reg.1993, 13, 41-46 and the literature cited there.
  • known active substances 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. B. ETR1, ETR2, ERS1, ERS2 or EIN4, can be used, as z. B.
  • Known substances that influence plant maturity and which can be combined with the compounds of the general formula (I) include, for example, the following active ingredients (the compounds are either given the "common name” according to the International Organization for Standardization (ISO) or indicated by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • rhizobitoxin 2-amino-ethoxy-vinylglycine (AVG), methoxyvinylglycine (MVG), vinylglycine, aminooxyacetic acid, sinefungin, S-adenosylhomocysteine, 2-keto-4-methylthiobutyrate, (isopropylidene )-aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)-aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)-aminooxyacetic acid 2-(isopropyloxy)-2-oxoethyl ester, putrescine, spermidine, Spermine, 1,8-diamino-4-aminoethyloctane, L-canalin, daminozide, 1-amin
  • Substances influencing plant health and germination As combination partners for the compounds of the general formula (I) in mixture formulations or in the tank mix, for example, known active substances that influence plant health or germination can be used (the compounds are either identified by the "common name" after of the International Organization for Standardization (ISO) or with the chemical name or with the code number and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers): sarcosine, phenylalanine, tryptophan, N'-methyl-1 - phenyl-1-N,N-diethylaminomethanesulfonamide, apio-galacturonanes as described in WO2010017956, 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, 4- ⁇ [2-(1H-indole-3- yl)ethyl]amino ⁇ -4-oxobutanoic acid, 4-[
  • Herbicides or plant growth regulators as combination partners for the compounds of general formula (I) in mixture formulations or in the tank mix are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3 -phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or act as plant growth regulators, such as those from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc.
  • herbicides or plant growth regulators which can be combined with compounds of the general formula (I)
  • the following active ingredients are to be mentioned, for example (the compounds are either identified by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or denoted by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • acetochlor acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3- Chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid- dimethylammonium, Aminopyralid-tripromine, Amitrole, Ammonium sulfamate, Anilofos, Asulam, Asulam Potassium, Asulam Sodium, Atrazine, Azafenidin, Azim
  • Dicamba-biproamine Dicamba-N,N-bis(3-aminopropyl)methylamine, Dicamba- butotyl, Dicamba-choline, Dicamba-Diglycolamine, Dicamba-dimethylammonium, Dicamba- Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba-isopropylammonium, Dicamba-methyl, dicamba monoethanolamine, dicamba olamine, dicamba potassium, dicamba sodium, dicamba triethanolamine), dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2 -(2,5-Dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, Dichloroprop, Dichloropropbutotyl, Dichloropropdimethylammonium, Dichloropropetexyl, Dichloroprope
  • TCA trifluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazine -6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g., TCA-ammonium, TCA-calcium, TCA-ethyl, TCA - Magnesium, TCA Sodium, Tebuthiuron, Tefuryltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Terbumetone, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazone-Methyl, Thifensulfuron, Thife nsulfuron-methyl, thioben
  • the plants were stress treated immediately after the application of the substance.
  • the wood fiber pots were transferred to plastic inserts to prevent them from drying too quickly afterwards.
  • Drought stress was induced by slow drying under the following conditions: "Day”: 14 hours illuminated at ⁇ 26-30°C "Night": 10 hours without illumination at ⁇ 18-20°C.
  • the duration of the respective stress phases mainly depended on the condition of the stressed control plants. It was terminated (by re-watering and transfer to a greenhouse with good growing conditions) as soon as irreversible damage to the stressed control plants was observed. After the end of the stress phase, a 4-7 day recovery phase followed, during which the plants were again kept in the greenhouse under good growth conditions.
  • Table A-2 Table A-3 In Vivo Analysis - Part B Seeds of monocotyledonous and dicotyledonous crops were sown in sandy loam soil in plastic pots, covered with soil or sand and grown in the greenhouse under good growth conditions. The test plants were treated in the early leaf stage (BBCH10 – BBCH13). In order to ensure a uniform water supply before the onset of stress, the planted pots were supplied with water by means of dam irrigation before the substance was applied. The compounds according to the invention were first formulated as wettable powders (WP) or dissolved in a solvent mixture. Further dilution was carried out with water with the addition of 0.2% wetting agent (eg Agrotin).
  • WP wettable powders
  • 0.2% wetting agent eg Agrotin
  • the finished spray mixture was sprayed onto the green parts of the plant with a water application rate of the equivalent of 600 l/ha.
  • the plants were stress treated immediately after the application of the substance. Drought stress was induced by slow drying under the following conditions: "Day”: 14 hours illuminated at ⁇ 26-30°C "Night": 10 hours without illumination at ⁇ 18-20°C.
  • the duration of the respective stress phases mainly depended on the condition of the stressed control plants. It was terminated (by re-watering and transfer to a greenhouse with good growing conditions) as soon as irreversible damage to the stressed control plants was observed. After the end of the stress phase, a 4-7 day recovery phase followed, during which the plants were again kept in the greenhouse under good growth conditions.
  • BRSNS Brassica napus
  • ZEAMX Zea mays
  • TRZAS Triticum aestivum

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Abstract

L'invention concerne l'utilisation de pyrrolidinones substituées de formule générale (I), ou leurs sels, les groupes dans la formule générale (I) étant définis comme indiqué dans la description, pour augmenter la tolérance au stress des plantes vis-à-vis du stress abiotique et/ou pour augmenter le rendement des plantes.
PCT/EP2022/065728 2021-06-21 2022-06-09 Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes WO2022268520A1 (fr)

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Cited By (1)

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WO2024081762A1 (fr) * 2022-10-12 2024-04-18 Corteva Agriscience Llc Cycles à 5 chaînons substitués et leur utilisation en tant que pesticides

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