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WO2019025156A1 - Pyrrolidinones substituées, leurs sels et leur utilisation comme agents herbicides - Google Patents

Pyrrolidinones substituées, leurs sels et leur utilisation comme agents herbicides Download PDF

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Publication number
WO2019025156A1
WO2019025156A1 PCT/EP2018/069001 EP2018069001W WO2019025156A1 WO 2019025156 A1 WO2019025156 A1 WO 2019025156A1 EP 2018069001 W EP2018069001 W EP 2018069001W WO 2019025156 A1 WO2019025156 A1 WO 2019025156A1
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alkyl
compounds
alkoxy
ring
aryl
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English (en)
Inventor
Uwe Döller
Hendrik Helmke
Stefan Lehr
Michael Mcleod
Thomas Müller
Olaf Peters
Hansjörg Dietrich
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
Dirk Schmutzler
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Bayer AG
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Bayer AG
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—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
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    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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    • 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
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Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops. Specifically, this invention relates to substituted pyrrolidinones and their salts, processes for their preparation and their use as herbicides.
  • WO2016 / 182780 describes substituted bicyclic compounds having herbicidal properties which carry aryls or substituted heteroaryls substituted on the amide bond. It is further known that certain substituted pyrrolidinones can be prepared enantioselectively (see Chemmical Communications, 2012, 48 (61), 7571-7573; Advanced Synthesis & Catalysis 2012, 354 (11-12), 2151-2156, S2151 / 1-S2151 / 99). The use of substituted pyrrolidinones or their salts as herbicidal active ingredients which carry a substituted sulfonamide radical on the amide bond, however, has not yet been described.
  • substituted pyrrolidinones or their salts as herbicidal active compounds which carry a substituted sulfonamide radical on the amide bond are particularly suitable as herbicides.
  • the present invention thus provides substituted pyrrolidinones of the general formula (I) or salts thereof
  • Y is -C (R 7 ) (R 8 ) -, oxygen, or NR 1 ,
  • W 1 and W 2 independently of one another, represent oxygen or sulfur, hydrogen, amino, hydroxyl, cyano, formyl, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 5) -cycloalkyl, ( C 1 -C 8 ) -hydroxyalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (Ci-C 8) alkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8) alkyl, (C 3 -C 8) halocycloalkyl, (C 3 - C 8) -Halocyclo
  • R 7 and R 8 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 8) -alkyl, (C 1 -C 5) -
  • Haloalkyl (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl, (Ci-C 8) alkoxyalkyl, (Ci-C 8) -Haloalkoxyalkyl, (Ci-C8) alkylthio (C -C 8) alkyl, (Ci-C8) -Alkylsulfmyl- (Ci-C8) alkyl, (Ci-C8) alkylsulfonyl (Ci-C 8) alkyl, (Ci-C8) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 3 -C 8) cycloalkylcarbonyl,
  • inorganic or organic acid such as mineral acids, such as HCl, HBr, H2SO4, HsPO i or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, e.g. Sulfonic acids, certain
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the azide hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • the substituted pyrrolidinones of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (I).
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • Q is (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 8 ) - Halocycloalkenyl, (C 1 -C 8 ) -alkylcarbonyl or (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl,
  • Y is -C (R 7 ) (R 8 ) -, oxygen, or NR 1 ,
  • W 1 and W 2 are independently oxygen or sulfur, is hydrogen, amino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) - Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, C6) -alkoxycarbonyl, (C 2
  • R 7 and R 8 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -
  • Haloalkyl (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (Ci-C 6) alkoxyalkyl, (Ci-C 6) -Haloalkoxyalkyl, (Ci-C 6) alkylthio ( Ci-C 6 ) -alkyl.
  • Q is an optionally substituted aryl or heteroaryl, (C3-Cg) -cycloalkyl or (C3-C8) -
  • Y is -C (R 7 ) (R 8 ) -
  • W 1 and W 2 are independently oxygen or sulfur, is hydrogen, amino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C 6 ) - alkoxy- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 - C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C6) - alkyl, (Ci-C6) alkylcarbonyl, (Ci-C6) -alkoxy
  • R 7 and R 8 independently of one another are hydrogen, hydroxyl, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6 ) -alkyl.
  • Q is an optionally substituted aryl or heteroaryl, (C3-C 7) -cycloalkyl or (C3-C7) - cycloalkenyl, wherein each ring or ring system may be optionally substituted with up to 5 substituents from the group R 6; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10 membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms independently of one another up to 2 O, up to 2 S and up to 5 N atoms containing up to three carbon ring atoms independently of each other
  • Q is (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -halocycloalkenyl, (C 1 -C 7 ) -alkylcarbonyl or (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl,
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen,
  • R 1 is hydrogen, amino, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl,
  • R 2 is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) alkoxyalkyl, R represents hydrogen, fluorine, chlorine, (C 1 -C 4 ) -alkyl,
  • R 4 is an optionally substituted aryl or heteroaryl, (C 3 -C 4) -cycloalkyl or (C 3 -C 7) -
  • R 4 is (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) Halocycloalkenyl, (C 1 -C 6 ) -alkylcarbonyl or (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, represents hydrogen, formyl, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C 6) alkoxy (Ci- C 6 )
  • R 7 is hydrogen, hydroxy, halogen, (Ci-C 3) alkyl, (Ci-C 3) -haloalkyl, (C 2 -C 3) alkenyl, (C2-C3) -
  • Q is an optionally substituted aryl or heteroaryl, (C3-Cv) -cycloalkyl or (C3-C7) -
  • Q is (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -halocycloalkenyl, (C 1 -C 6) -alkylcarbonyl or (C 1 -C 6) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 4) -
  • Haloalkoxy- (Ci-C6) -alkyl stands,
  • Y is -CH 2 -
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen are;
  • R 1 represents hydrogen, amino, (Ci-C 3) alkyl, aryl (Ci-C 3) alkyl, heteroaryl (Ci-C 3) alkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 3) alkyl, (Ci-C 4) alkylcarbonyl, (Ci-C 4) alkoxycarbonyl, (C 2 -C 4) alkenyl, (C 2 -C 4 ) -alkynyl,
  • R 2 is hydrogen, is hydrogen, fluorine or chlorine
  • R 4 is optionally substituted for aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -alkyl, wherein each ring or each ring system is optionally substituted with up to 5 substituents from the group R 6 , or for (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -halocycloalkenyl (C 1 -C 6) -alkylcarbonyl or (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkoxy- (C 1 -C 6) -alkyl, represents hydrogen, formyl, C 6) al
  • Y is -CH 2 -
  • W 1 and W 2 are oxygen
  • R 1 is hydrogen, amino, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl
  • R is hydrogen
  • R 3 is hydrogen, fluorine or chlorine.
  • Z is the groups Z1 to Z-4.2, Y is -CH 2 -,
  • W 1 and W 2 are oxygen
  • R 1 is hydrogen, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl,
  • R 2 is hydrogen and R 3 is hydrogen.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms e.g. (but not limited to) (C 1 -C 6) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpent
  • heteroarylsulfonyl is optionally substituted pyridylsulfonyl
  • Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (CI-C ⁇ ) - or (Ci-C-alkylthio, for example (but not limited to) (Ce) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio , 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1
  • Alkoxy means an alkyl radical bonded through an oxygen atom, for example (but not limited to) (C 1 -C 6) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy , 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy , 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethylbut
  • Alkenyloxy means an alkenyl radical bonded through an oxygen atom
  • alkynyloxy means an above an alkynyl radical bonded to 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 ) -Alkmoxy.
  • Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom.
  • the number of C atoms here refers to the alkyl radical in the
  • the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkynyloxycarbonyl the number of carbon atoms refers to the alkenyl and alkynyl in the alkene or
  • alkyl radicals attached to the skeleton via a carbonyloxy group such as (C1-C10) -, (CI-C ⁇ ) - or (Ci-C i) alkylcarbonyloxy.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, 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 [alkyl] silylalkyny
  • heterocyclic radical contains at least one heterocyclic ring
  • ( carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted , wherein the binding site to a ring atom is located.
  • the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • optionally substituted heterocyclyl also become
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered ring and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N,
  • O and S such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2 or
  • 6-yl 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
  • Hexahydropyrimidine-1 or 2 or 3 or 4-yl 1,4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,6-dihydropyrimidine-I or 2- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N (O) and -S (0) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie.
  • heteroaryls are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine
  • heteroaryl are also 5- or 6-membered benzo-fused Rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indole-6 yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophene-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1 Benzothiophene-7-yl, 1H-indazol-1-yl, 1H-
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated
  • Hydrocarbon radical which is optionally monosubstituted or polysubstituted and which is referred to in the latter case as "substituted alkyl.”
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particular preference is given to methoxy , Methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
  • ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CC1F 2, CFC1 2 CF 2 CC1F 2, CF 2 CC1FCF 3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3.
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CHFCF 2 CF 3.
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optional halogen atoms being selected from the group consisting of fluorine, chlorine or bromine, iodine Partially fluorinated haloalkyl also includes the complete substitution of halogen for the straight-chain or branched chain with the participation of at least one fluorine atom.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl, and the same applies to haloalkenyl and other radicals substituted by halogen.
  • (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
  • Range indication for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
  • alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1, 3-butadienyl and 1, 4-pentadienyl, but also allenyl or cumulene radicals having one or more cumulative double bonds, such as allenyl (1, 2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (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-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl
  • alkynyl in particular also includes straight-chain or branched open-chain
  • -alkynyl means e.g. 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,
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
  • 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 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
  • substituents having a double bond on the cycloalkenyl radical for example an alkylidene group such as methylidene
  • Alkoxyalkyl means an alkoxy group attached via an alkyl group
  • alkoxyalkoxy means an alkoxyalkyl group bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group and
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy group bonded via an alkyl group.
  • Haloalkoxyalkyl means a haloalkoxy radical attached and "haloalkylthioalkyl” means a haloalkylthio radical attached via an alkyl group.
  • Arylalkyl means an aryl group attached via an alkyl group
  • heteroarylalkyl means a heteroaryl group bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
  • Cycloalkylalkyl means a cycloalkyl group attached via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl 1 -yl, 3-cyclopropylprop-1-yl.
  • haloalkylthio - alone or as part of a chemical group - represents straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cs) -, (CI-C ⁇ ) - or (Ci-C4) haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • haloalkylthio e.g. (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” mean by the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-Cg) -, (Ci-Ce) - or (Ci-C4) -alkyl] silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, Tri- (2-methylprop-1-yl) silyl, tri (1,1-dimethyleth-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
  • the compounds of general formula (I) may vary depending on the nature and linkage of the substituents exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be distinguished from those in the
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • the purification can also by
  • Suitable isolation, purification and stereoisomer separation methods of compounds of general formula (I) are those which are well known to those skilled in the art from analogous cases, e.g. by physical methods such as crystallization, chromatographic methods, especially column chromatography and HPLC (high performance liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, residual mixtures may optionally be removed by chromatographic separation, e.g. at chiral solid phases, to be separated.
  • chromatographic separation e.g. at chiral solid phases
  • the substituted pyrrolidinones of the general formula (I) according to the invention can be prepared starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily prepared amines, of appropriately substituted
  • the synthesis of the compounds of the general formula (Ia) according to the invention is carried out via a coupling of an acid of the general formula (II) with a sulfonamide of the general formula (III) in the presence of an amide coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl ) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of peptide Synthsis, Ed. ⁇ .
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 1).
  • an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate
  • a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 1).
  • the synthesis of the acid of the general formula (II) can be prepared by saponification of the compound of the general formula (IV) according to or analogously to methods known to those skilled in the art.
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium), and the saponification reaction preferably takes place in the temperature range between room temperature and 100 ° C.
  • the Lewis acid may be boron tribromide, and the reaction may be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the compound of the general formula (IV) can be prepared by reduction of the compound of the general formula (V) and subsequent in situ cyclization of the resulting amine intermediate according to or analogously to those skilled in the known methods (see Scheme 3).
  • the literature describes the reduction of aliphatic nitro groups by catalytic hydrogenolysis in the presence of palladium on carbon or Raney nickel, iron or zinc in an acidic medium (see, for example, reports of the Deutsche Chemischen Deutschen 1961 1904, 37, 3520-3525), and lithium alanate , The reduction can also be carried out with samarium (II) iodide in the presence of a proton source such as methanol (see, for example, Tetrahedron Letters 1991, 32 (14), 1699-1702).
  • a proton source such as methanol
  • reduction of the aliphatic nitro group with sodium borohydride can be carried out in the presence of nickel (II) acetate or nickel (II) chloride (see, for example, Tetrahedron Letters 1985, 26 (52), 6413-6416).
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 4 describes the synthesis of the compound of the general formula (V) by reacting a diester of the general formula (VI) with a nitroalkane of the general formula (VII) in the presence of a base.
  • the base may be an alkoxide salt of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • the reaction may be carried out with bases such as lithium hexa-methyldisilazane, sodium hexamethyldisilazane or lithium diisopropylamide in an adequate solvent such as tetrahydrofuran.
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (VI) can be prepared by Knoevenagel condensation of an aldehyde of general formula (VIII) and malonic esters of general formula (IX) (see Scheme 5, G. Jones, Oric Reactions Volume 15, John Wiley and Sons, 1967).
  • R ' (C 1 -C 4 ) -alkyl.
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate), in an adequate solvent such as methanol or ethanol, or bases such as lithium hexamethyldisilazane,
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (X) can be prepared by condensation of an aldehyde of general formula (VIII) and compounds of general formula (XI) in the presence of a base such as sodium hydride in an adequate solvent such as tetrahydrofuran (see Scheme 7) ).
  • the compounds of the general formula (Ia) can be prepared by reduction of the compound of the general formula (XII) and subsequent in situ cyclization of the resulting amine intermediate according to methods known to those skilled in the art (see Scheme 8).
  • the literature describes the reduction of aliphatic nitro groups by catalytic hydrogenolysis in the presence of palladium on carbon or RaneyNickel.
  • Nickel (II) chloride
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 9 describes the synthesis of the compound of general formula (XII) by reaction of a malonic ester of general formula (XIII) with a nitro olefin of general formula (X) in the presence of a base.
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • an alkanolate salt or hydroxide of an alkali metal such as sodium methylate or sodium ethylate
  • an adequate solvent such as methanol or ethanol.
  • bases like Lithiumhexamethyldisilazan, Natriumhexamethyldisilazan or lithium diisopropylamide, in an adequate Lösun sstoff such as tetrahydrofuran perform.
  • R ' (C 1 -C 4 ) -alkyl.
  • Monomalonateklarechlorides of the general formula (XIV) with a sulfonamide of the general formula (III) in the presence of a base see Scheme 10).
  • the base can be triethylamine or
  • Diisopropylethylamine and the reaction can be carried out in an adequate solvent such as dichloromethane or tetrahydrofuran.
  • R ' (C 1 -C 4 ) -alkyl.
  • the reaction mixture was stirred overnight at room temperature and then sat.
  • Ammonium chloride solution (20 ml) and ethyl acetate (20 ml) were added and stirred for a further hour at room temperature. The insoluble constituents were filtered off over Celite and the phases were subsequently separated. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with sat. Ammonium chloride solution and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
  • the resulting crude product was dissolved in ethanol (40 ml) and treated with a solution of sodium hydroxide (1.12 g, 27.8 mmol, 3.0 equiv) in water (40 ml).
  • the resulting reaction mixture was stirred overnight at room temperature and then water (50 ml) and diethyl ether (50 ml) were added.
  • the organic phase was discarded and the aqueous phase with conc. HCl to pH 2.
  • the aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
  • Preferred compounds of the formula (L I) are the compounds 1.1-1 to 1.1-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-270 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.2-1 to 1.2-270 of Table 1.2 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.3-1 to 1.3-270 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.4-1 to 1.4-270 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.5-1 to 1.5-346 of Table 1.5 are thus by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-270, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.6-1 to 1.6-270 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-270 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-270, in which Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.8-1 to 1.8-270 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-270 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.10-1 to 1.10-270 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11 - 1 to 1.11 -270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds LI 1-1 to LI 1-270 of Table LI 1 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.12-1 to 1.12-270 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.13-1 to 1.13-270 of Table 1.13 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.14-1 to 1.14-270 of Table 1.14 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-270 of Table 1.15 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.16-1 to 1.16-270 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-270, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.17-1 to 1.17-270 of Table 1.17 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.18-1 to 1.18-270 of Table 1.18 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.19-1 to 1.19-270 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.20-1 to 1.20-270 of Table 1.20 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.21-1 to 1.21-270 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.22-1 to 1.22-270 of Table 1.22 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.23-1 to 1.23-270 of Table 1.23 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.24-1 to 1.24-270 of Table 1.24 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.25-1 to 1.25-270 of Table 1.25 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.26-1 to 1.26-270 of Table 1.26 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.27-1 to 1.27-270 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.28-1 to 1.28-270 of Table 1.28 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.29-1 to 1.29-270 of Table 1.29 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-270 of Table 1.30 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.31-1 to 1.31-270 of Table 1.31 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.32-1 to 1.32-270 of Table 1.32 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.33 Preferred compounds of the formula (I. 33) are the compounds I. 33-1 to I. 33-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 33-1 to I. 33-270 of Table I. 33 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.34 Preferred compounds of the formula (I. 34) are the compounds I. 34-1 to I. 34-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds I. 34-1 to I. 34-270 of Table I. 34 are thus by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.35 Preferred compounds of the formula (I. 35) are the compounds I. 35-1 to I. 35-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 35-1 to I. 35-270 of Table I. 35 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.36 Preferred compounds of the formula (I. 36) are the compounds I. 36-1 to I. 36-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 36-1 to I. 36-270 of Table I. 36 are thus by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.37 Preferred compounds of the formula (I. 37) are the compounds I. 37-1 to I. 37-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 37-1 to I. 37-270 of Table I. 37 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Preferred compounds of the formula (I. 38) are the compounds I. 38-1 to I. 38-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 38-1 to I. 38-270 of Table I. 38 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Preferred compounds of the formula (I. 39) are the compounds I. 39-1 to I. 39-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 39-1 to I. 39-270 of Table I. 39 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.40 Preferred compounds of the formula (I. 40) are the compounds I. 40-1 to I. 40-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 40-1 to I. 40-270 of Table I. 40 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-270, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.41-1 to 1.41-270 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.42-1 to 1.42-270 of Table 1.42 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-270 of Table 1.43 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.44-1 to 1.44-270 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.45-1 to 1.45-270 of Table 1.45 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • the 1H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity i ) ; 82 (intensity 2);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity ”)
  • 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 can be shown compared to the most intense signal in the spectrum.
  • To calibrate the chemical shift of 1H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • 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 (for example with a purity of> 90%).
  • stereoisomers and / or impurities may be typical of each
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
  • ⁇ 10.3410 (0.8); 8.1724 (1.8); 8.1691 (2.0); 8.1525 (2.0); 8.1491 (2.1); 7.5315 (0.9); 7.5281 (0.9); 7.5180 (1.5); 7.5127 (2.2); 7.5093 (2.2); 7.4939 (1.6); 7.4901 (2.0); 7.4858 (3.0); 7.4696 (2.5); 7.4568 (1.4); 7.3921 (1.3); 7.3737 (1.9); 7.3536 (1.0); 7.3158 (2.2); 7.3084 (0.7); 7.2967 (2.0); 7.2728 (0.7); 7.2664 (1.7); 7.2592 (234.1); 7.2255 (0.9); 7.2207 (0.8); 7.2087 (0.7); 7.2002 (0.6); 7.1912 (1.4); 7.1669 (2.1); 7.1430 (1.1); 6.9951 (1.3); 5.9387 (1.2); 4.0700 (0.6); 4.0477 (1.5); 4.0233 (1.6); 4,0007 (0.8); 3.7794 (1.1); 3.7767 (1.1); 3.7538 (2.3); 3.7311 (1.1); 3.7284 (1.2
  • ⁇ 10.3416 (1.3); 8.1127 (5.3); 8.1077 (2.7); 8.1002 (6.0); 8.0952 (3.8); 8.0903 (6.4); 8.0827 (2.8); 8.0778 (5.7); 7.8484 (0.5); 7.8365 (0.6); 7.5437 (2.9); 7.5183 (3.1); 7.5109 (6.2); 7.4856 (9.5); 7.4716 (3.5); 7.4530 (0.7); 7.3091 (0.8); 7.2595 (311.9); 7.2270 (1.3); 7.2222 (5.4); 7.2009 (8.7); 7.1844 (2.5); 7.1793 (5.9); 7.0186 (0.7); 6.9956 (2.0); 6.0125 (2.4); 5.2984 (16.0); 4.1091 (1.0); 4.0865 (2.8); 4.0631 (3.1); 4.0402 (1.4); 3.8033 (1.9); 3.7790 (3.8); 3.7552
  • ⁇ 10.3327 (5.0); 8.1 171 (1.7); 8.1096 (15.0); 8.1043 (6.1); 8.0971 (16.0); 8.0920 (8.3); 8.0870 (15.6); 8.0798 (6.9); 8.0744 (14.6); 8.0670 (2.4); 7.5181 (8.2); 7.5032 (12.0); 7.4896 (1 1.2); 7.4842 (9.0); 7.4728 (4.8); 7.3590 (1.2); 7.3239 (0.8); 7.3151 (0.8); 7.3128 (0.8); 7.3079 (1.4); 7.3017 (1.4); 7.2977 (1.6); 7.2937 (2.8); 7.2930 (2.6); 7.2890
  • ⁇ 10.6299 (1.2); 8.1 170 (3.1); 8.1020 (3.2); 8.0965 (4.1); 8.0814 (4.0); 8.0745 (3.2); 8.0594 (3.2); 7.5181 (7.0); 7.4947 (8.2); 7.4812 (9.4); 7.4622 (3.1); 7.3598 (0.7); 7.3099 (1.0); 7.2971 (0.8); 7.2871 (2.1); 7.2592 (1224.7); 7.2240 (1.6); 7.2093 (2.0); 7.2010 (3.8); 7.1803 (4.8); 7.1553 (2.6); 7.0662 (2.2); 7.0635 (2.2); 7.0602 (2.5); 7.0442
  • the present invention furthermore relates to the use of one or more
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention furthermore relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one the embodiment characterized as being preferred or particularly preferred, in particular one or more compounds of the general formulas (LI) to (1.45) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, to the (Schad) Plants, (harmful) plant seeds, the soil in which or on the
  • the present invention also provides a process for controlling undesirable plants, preferably in crops, characterized in that an effective amount of one or more compounds of general formula (I) and / or salts thereof, as defined above, preferably in one of Preferred or particularly preferred embodiment marked, in particular one or more compounds of formulas (LI) to (1.45) and / or their salts, each as defined above, or an agent according to the invention, as defined below, on undesirable plants (eg harmful plants such as mono - or dicotyledonous weeds or unwanted crops), the seed of the undesirable plants (ie plant seeds, eg grains, seeds or vegetative propagules such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (eg the soil cultivated land or non-cultivated land) or the area under cultivation (ie F surface on which the unwanted plants will grow) is applied.
  • undesirable plants eg harmful plants such as mono - or dicotyledonous weeds or unwanted crops
  • the seed of the undesirable plants ie plant seeds, eg
  • the present invention further provides methods for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount - one or more compounds of general formula (I) and / or their salts, as defined above, preferably in a the embodiment characterized as being preferred or particularly preferred, in particular one or more compounds of the formulas (LI) to (1.45) and / or salts thereof, each as defined above, or - an agent according to the invention, as defined below, the plant, the seed the plant (ie, plant seeds, eg, grains, seeds, or vegetative propagules, such as tubers or sprouts with buds), the soil in or on which the plants grow (eg, the soil of cultivated land or non-cultivated land), or the acreage (ie, area on which the plants will grow) is applied.
  • an effective amount - one or more compounds of general formula (I) and / or their salts as defined above, preferably in a the embodiment characterized as being preferred or particularly preferred, in particular one or more compounds of the formulas (LI) to (
  • inventive agent e.g. in Vorsaat- (possibly also by incorporation into the soil), pre-emergence and / or Nachauflaufmaschine be applied.
  • inventive agent e.g. in Vorsaat- (possibly also by incorporation into the soil), pre-emergence and / or Nachauflaufmaschine be applied.
  • some representatives of the monocotyledonous and dicotyledonous weed flora are mentioned, which are characterized by those of the invention
  • Connections can be controlled without the restriction being restricted to certain species.
  • one or more compounds of the general formula (I) and / or their salts are employed for controlling harmful plants or regulating growth in crops of crops or ornamental plants, the crops or ornamentals in a preferred embodiment are transgenic plants.
  • the compounds of the general formula (I) according to the invention and / or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
  • the compounds according to the invention are applied to the surface of the earth (weeds and / or weeds) prior to germination (pre-emergence method), either the emergence of the weed seedlings or weed seedlings is completely prevented or they grow up to the cotyledon stage, but then grow and eventually die off after three to four weeks.
  • the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous genera Allium, pineapple , Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in crops such as
  • Plant ingredients and harvest relief such as by triggering desiccation and stunting can be used. Furthermore, they are also suitable for general control and Inhibition of unwanted vegetative growth without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented. Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi,
  • Bacteria or viruses Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • transgenic cultures is the use of the compounds of the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
  • cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the invention may also be used as herbicides in
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Other special properties may include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
  • abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
  • Preference is given to the use of the compounds of general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and corn or also Cultures of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • Conventional ways of producing new plants which have modified properties in comparison with previously occurring plants consist, for example, in classical methods
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • Base exchanges are made, partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments.
  • RNA for example, be achieved by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a Cosuppressions freees or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But the localization in one
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species i. both monocotyledonous and dicotyledonous plants.
  • the compounds of general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. Dicamba or against herbicides containing essential plant enzymes, e.g.
  • Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), respectively, which are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogues.
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
  • cereals preferably corn, wheat, barley, rye, oats, millet, or rice, in the pre- or post-emergence.
  • Preference is also the use in soy in the pre or postemergence.
  • Growth regulation of plants also includes the case where the active ingredient of general formula (I) or its salt is formed from a precursor substance ("prodrug”) only after plant, plant or soil application.
  • the invention also provides the use of one or more compounds of the general formula (I) or salts thereof or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or salts thereof on the plants (harmful plants, optionally together with the useful plants) plant seeds, the soil in which or on which the plants grow, or the cultivated area.
  • the invention also provides a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.45) and / or salts thereof, each as defined above,
  • the other agrochemically active substances of constituent (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 are mentioned.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries customary in plant protection (ii) selected from Group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffering agents, antifoaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar, water-miscible organic solvents in any proportion.
  • formulation auxiliaries customary in plant protection selected from Group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffering agents
  • the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain compounds of the general formula (I) and / or salts thereof.
  • the compounds of the general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. As formulation options are for example in question:
  • WP Wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonsaures Sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • emulsifiers can be used for example: Alkylarylsulfonsaure calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylenesorbitanester such. Polyoxyethylene.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, through
  • Emulsions e.g. Oil-in-water emulsions (EW), for example, by means of stirrers,
  • Solvents and optionally surfactants such as e.g. listed above for the other formulation types.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying for the preparation of plate, fluidized bed, extruder and spray granules, see, for example, the procedure in "Spray-Drying Handbook" 3rd ed. 1979, G.
  • the agrochemical preparations preferably herbicidal or plant growth-regulating agents of the present invention, preferably contain a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight), of active compounds of the general formula (I) and their salts.
  • the active ingredient concentration is, for example, about 10 to 90% by weight>, the remainder to 100% by weight> consists of customary formulation constituents.
  • the active ingredient concentration is, for example, about 10 to 90% by weight>, the remainder to 100% by weight> consists of customary formulation constituents.
  • the active ingredient concentration is, for example, about 10 to 90% by weight>, the remainder to 100% by weight> consists of customary formulation constituents.
  • the active ingredient concentration is, for example, about 10 to 90% by weight>, the remainder to 100% by weight> consists of customary formulation constituents.
  • Active ingredient concentration about 1 to 90, preferably 5 to 80 wt.%> Be. Powdery
  • Formulations contain 1 to 30 wt.%> Active ingredient, preferably usually 5 to 20 wt.%> Of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-%> active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of general formula (I) or their salts according to the invention can be used as such or in the form of their formulations (formulations) combined with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators be used, eg as finished formulation or as
  • Tank mixes The combination formulations can be prepared on the basis of the above-mentioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mix are known active compounds which are based on 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 are based, can be used, such as in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Crops occur.
  • combinations of compounds (I) according to the invention of particular interest which contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest.
  • the safeners which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals.
  • the weight ratios of herbicide (mixture) to safener generally depends on the
  • herbicide and the effectiveness of each safener may vary within wide limits, for example in the range of 200: 1 to 1: 200, preferably 100: 1 to 1: 100, especially 20: 1 to 1: 20.
  • the safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides / pesticides and provided and used as ready-to-use formulation or tank mixture with the herbicides.
  • the present in commercial form herbicidal or herbicidal safener formulations are optionally diluted in the usual manner, for example in wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use. External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of general formula (I) and / or their salts.
  • Application rate can vary within wide limits.
  • the total amount of compounds of general formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in Range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications.
  • Plant growth regulator for example as Halmverkürzer in crops, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, most preferably in the range of 20 to 250 g / ha. This applies to both the application in the
  • Halmverkürzer can be done in various stages of growth of the plants.
  • the application is preferred after placement at the beginning of
  • Length growth when used as a plant growth regulator, the treatment of the
  • Seed which includes the different seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • combination partners for the compounds of the general formula (I) according to the invention eg mixture formulations or in tank mix
  • known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvyl shikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or
  • herbicidal mixture partners examples include:
  • methabenzothiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiar
  • plant growth regulators as possible mixing partners are:
  • Strigolactone tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
  • Fenchlorazole ethyl ester
  • ethyl ester i. 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -l, 2,4-triazole-3-carboxylic acid ethyl ester (SI-7), and related compounds as described in EP-A-174562 and EP-A- A-346620;
  • Sl e compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from the company Nitrokemia and Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • RA 1 (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, where the 2 last-mentioned radicals are represented by VA
  • RA 2 halogen (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; niA 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl,
  • R B 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy and niB is 1 or 2, for example those in which
  • RB 1 cyclopropyl
  • R B 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe (S4-2)
  • RB 1 isopropyl
  • R B 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe is (S4-4) and
  • RB 1 isopropyl
  • R B 2 hydrogen
  • (RB 3 ) 2-OMe (S4-5);
  • R c 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 and mc are 1 or 2; for example
  • R D 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; mD 1 or 2;
  • R D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl.
  • RD 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, is hydrogen or (Ci-C 4) alkyl,
  • RE is hydrogen, (Ci-Cg) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts, is an integer of 0 to 2.
  • YE, ZE independently of one another O or S, ⁇ an integer from 0 to 4,
  • R E 2 is (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (Ci-C6) alkyl.
  • oxyimino compound type compounds known as seed dressing agents, such as, for example, B.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl 1-1), which is known as millet safener for millet against damage by metolachlor,
  • Seed pickling safener for millet against damage from metolachlor is known.
  • Isothiochromanone (S12) class agents e.g. Methyl- [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A- 1998/13361.
  • S13) One or more compounds from group (S13):
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
  • Cyanamide which is known as safener for maize against damage of imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • Active substances which, in addition to having a herbicidal action against harmful plants, also have safener action on cultivated plants such as rice, such as, for example, rice.
  • CSB (1-Bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Registry No. 54091-06-4), which is known as a safener against damage of some herbicides in rice.
  • RH 1 is a (Ci-C6) haloalkyl radical and RH 2 is hydrogen or halogen and
  • RH 3 , RH 4 independently of one another hydrogen, (C 1 -C 16) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, wherein each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) Alkylamino, di [(C 1 -C 4 ) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocycl
  • RH 3 is (C 1 -C 4 ) -alkoxy, (C 2 -C 4 ) -alkenyloxy, (C 2 -C 6) -alkinyloxy or (C 2 -C 4 ) -haloalkoxy and RH 4 is hydrogen or (C 1 -C 4 ) -alkyl or
  • RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered one
  • heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted, means.
  • Preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or salts thereof, in particular with the compounds of the formulas (LI) to (1.45) and / or salts thereof are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, Isoxadifen ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Seeds of monocotyledonous or dicotyledonous weeds or crops are in plastic or
  • Postemergence treatment good herbicidal activity against selected weeds such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica or Viola tricolor at an application rate of 1.28 kg of active ingredient or less per hectare.
  • some of the compounds of the invention showed a high selectivity and are therefore suitable in the postemergence process for controlling undesired plant growth in
  • Seeds of monocotyledonous or dicotyledonous weeds and crops are in plastic or
  • Wood fiber pots designed and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a water application rate of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • the pots are placed in the greenhouse and kept under good growth conditions for the test plants.
  • Pre-emergence treatment has good herbicidal activity against selected harmful plants such as e.g. Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica or Viola tricolor at an application rate of 1.28 kg of active substance or less per hectare.
  • harmful plants such as e.g. Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharitis purpurea, Polygonum convolvulus, Setaria

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Abstract

L'invention concerne des pyrrolidinones substituées de formule générale (I) et leur utilisation comme herbicides, en particulier pour lutter contre les plantes adventices et/ou les mauvaises herbes dans les cultures de plantes utiles et/ou comme régulateurs de croissance végétale pour influencer la croissance des cultures de plantes utiles. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance végétale comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2018/069001 2017-08-03 2018-07-12 Pyrrolidinones substituées, leurs sels et leur utilisation comme agents herbicides Ceased WO2019025156A1 (fr)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
WO2020161148A3 (fr) * 2019-02-05 2020-09-17 Syngenta Crop Protection Ag Dérivés de pyrazole
CN113631551A (zh) * 2018-11-08 2021-11-09 南特大学 昆虫烟碱型乙酰胆碱受体的新型竞争性调节剂
EP4483714A2 (fr) 2021-12-15 2025-01-01 Adama Agan Ltd. Composés utiles pour la préparation de divers produits agrochimiques et marqueurs associés

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EP2336104A1 (fr) 2008-09-02 2011-06-22 Nissan Chemical Industries, Ltd. Dérivé halogénoalkylsulfonanilide ortho-substitué et herbicide
WO2015084796A1 (fr) 2013-12-03 2015-06-11 E. I. Du Pont De Nemours And Company Pyrrolidinones servant d'herbicides
WO2016094117A1 (fr) 2014-12-08 2016-06-16 E. I. Du Pont De Nemours And Company 3-oxo-3-(arylamino)propanoates, leur procédé de préparation et leur utilisation dans la préparation de pyrrolidinones
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WO2016182780A1 (fr) 2015-05-12 2016-11-17 E I Du Pont De Nemours And Company Composés bicycliques substitués par un aryle à titre d'herbicides
WO2016196593A1 (fr) 2015-06-02 2016-12-08 E I Du Pont De Nemours And Company Amides cycliques substitués et leur utilisation en tant qu'herbicides
WO2016196019A1 (fr) 2015-05-29 2016-12-08 E I Du Pont De Nemours And Company Amides cycliques substitués utilisés comme herbicides

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WO1998027049A1 (fr) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Nouveaux derives d'acide 2-fluoroacrylique, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
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WO2002034048A1 (fr) 2000-10-23 2002-05-02 Syngenta Participations Ag Compositions agrochimiques avec des phytoprotecteurs a base de quinoline
WO2004037787A1 (fr) 2002-10-18 2004-05-06 Basf Aktiengesellschaft 1-phenylpyrrolidine-2-one-3-carboxamides
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023719A1 (fr) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire l'attaque chimique et composition herbicide produisant une attaque chimique réduite
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits
WO2008131860A2 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation
WO2008131861A1 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Utilisation de pyridin-2-oxy-3-carbonamides comme phytoprotecteurs
EP2336104A1 (fr) 2008-09-02 2011-06-22 Nissan Chemical Industries, Ltd. Dérivé halogénoalkylsulfonanilide ortho-substitué et herbicide
CN101838227A (zh) 2010-04-30 2010-09-22 孙德群 一种苯甲酰胺类除草剂的安全剂
WO2015084796A1 (fr) 2013-12-03 2015-06-11 E. I. Du Pont De Nemours And Company Pyrrolidinones servant d'herbicides
WO2016094117A1 (fr) 2014-12-08 2016-06-16 E. I. Du Pont De Nemours And Company 3-oxo-3-(arylamino)propanoates, leur procédé de préparation et leur utilisation dans la préparation de pyrrolidinones
WO2016164201A1 (fr) 2015-04-10 2016-10-13 E I Du Pont De Nemours And Company Amides cycliques susbtitués utilisés comme herbicides
WO2016182780A1 (fr) 2015-05-12 2016-11-17 E I Du Pont De Nemours And Company Composés bicycliques substitués par un aryle à titre d'herbicides
WO2016196019A1 (fr) 2015-05-29 2016-12-08 E I Du Pont De Nemours And Company Amides cycliques substitués utilisés comme herbicides
WO2016196593A1 (fr) 2015-06-02 2016-12-08 E I Du Pont De Nemours And Company Amides cycliques substitués et leur utilisation en tant qu'herbicides

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113631551A (zh) * 2018-11-08 2021-11-09 南特大学 昆虫烟碱型乙酰胆碱受体的新型竞争性调节剂
WO2020161148A3 (fr) * 2019-02-05 2020-09-17 Syngenta Crop Protection Ag Dérivés de pyrazole
US11059806B2 (en) 2019-02-05 2021-07-13 Syngenta Crop Protection Ag Pyrazole derivatives
CN113412254A (zh) * 2019-02-05 2021-09-17 先正达农作物保护股份公司 吡唑衍生物
US11680057B2 (en) 2019-02-05 2023-06-20 Syngenta Crop Protection Ag Pyrazole derivatives
CN113412254B (zh) * 2019-02-05 2024-11-29 先正达农作物保护股份公司 吡唑衍生物
US12454523B2 (en) 2019-02-05 2025-10-28 Syngenta Crop Protection Ag Pyrazole derivatives
EP4483714A2 (fr) 2021-12-15 2025-01-01 Adama Agan Ltd. Composés utiles pour la préparation de divers produits agrochimiques et marqueurs associés

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