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WO2018178008A1 - Isoazolidin-5-ones substituées et leurs sels et leur utilisation comme agents herbicides - Google Patents

Isoazolidin-5-ones substituées et leurs sels et leur utilisation comme agents herbicides Download PDF

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Publication number
WO2018178008A1
WO2018178008A1 PCT/EP2018/057635 EP2018057635W WO2018178008A1 WO 2018178008 A1 WO2018178008 A1 WO 2018178008A1 EP 2018057635 W EP2018057635 W EP 2018057635W WO 2018178008 A1 WO2018178008 A1 WO 2018178008A1
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Prior art keywords
alkyl
compounds
cycloalkyl
alkoxy
aryl
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PCT/EP2018/057635
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German (de)
English (en)
Inventor
Thomas Müller
Hendrik Helmke
Olaf Peters
Michael Charles MCLEOD
Uwe Döller
Stefan Lehr
Hansjörg Dietrich
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
Dirk Schmutzler
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Bayer Aktiengesellschaft
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Publication of WO2018178008A1 publication Critical patent/WO2018178008A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—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 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

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 isoazolidin-5-ones and their salts, processes for their preparation and their use as herbicides.
  • substituted isoazolidin-5-ones or their salts as herbicidal active ingredients which carry a substituted phenyl radical, heteroaryl radical, cycloalkyl radical or alkyl radical on the amide bond, however, has not yet been described.
  • substituted isoazolidin-5-ones or their salts containing a substituted phenyl radical on the amide bond
  • Heteroaryl, cycloalkyl or alkyl carry, as herbicides are particularly well suited.
  • the present invention thus provides substituted isoazolidin-5-ones of the general formula (I) or salts thereof
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cio) -cycloalkyl or (C3-C10) -
  • W 1 and W 2 are independently oxygen or sulfur; represents hydrogen, cyano, formyl, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl, (Ci-C 8) cyanoalkyl, (Ci-C8) hydroxyalkyl, (Ci-C 8) - alkoxy (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (Ci-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) -Halocycloalkyl- (Ci-C 8) alkyl, (Ci-C 8) alkylcarbonyl, (Ci-C8)
  • each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 5 , or, for a (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -Halocycloalkyl, (C 3 -Cio) -cyanocycloalkyl, (Ci-Cio) -alkyl- (C 3 -Cio) -cycloalkyl, (Ci-Cio) -alkoxy- (C 3 -Cio) -cycloalkyl, (Ci-Cio ) -Haloalkoxy- (C 3 -C 10) -cycloalkyl, (C 1 -C 10) -alkylthio (C 3 -C 10) -cycloalkyl, aryl- (C 3 -C 10) -cycloalkyl, heteroaryl-
  • the compounds of general formula (I) can be prepared by addition of a suitable organic compound.
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H2SO4, ftPO.sub.i or HNO.sub.3, or organic acids, e.g. As 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 especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • Q is an optionally substituted aryl, heteroaryl, (C3-C9) -cycloalkyl or (C3-C9) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 ; 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
  • W 1 and W 2 are independently oxygen or sulfur
  • R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyl , aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C 6) -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, (Ci C6) -alkoxycarbonyl, (C2 -Ce
  • R 2 represents hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - hydroxyalkyl, (Ci-C 6) alkoxy ( Ci-C 6 ) -alkyl,
  • R 3 is an optionally substituted aryl and heteroaryl, where each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 5 , or, for an optionally substituted (C3-C9) -cycloalkyl, (C3-C9) C9) -halocycloalkyl, (C3-C9) -cyanocycloalkyl, (Ci-C9) -alkyl- (C3-C9) -cycloalkyl, (Ci-C9) -alkoxy- (C3-C9) -cycloalkyl, (Ci-C9) haloalkoxy (C3-C9) cycloalkyl, (Ci-C 9) -alkylthio- (C 3 -C9) cycloalkyl, aryl (C3-C9) - cycloalkyl, heteroaryl (C3-C9) cycloalkyl , (C 1 -C 9) alkoxycarbon
  • R 4 is hydrogen, amino, amino (C 1 -C 6 ) -alkyl, aminobis (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -) C 6) alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) - alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 4 -alkyl) 6 ) -alkyl
  • R 5 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 7 ) -alkyl,
  • (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, aryl, aryl (Ci-C7) alkyl, aryl (C 2 -C 7) - alkenyl, aryl- (C 2 -C 7) alkynyl, aryl (Ci-C7) alkoxy, heteroaryl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C -C 7) hydroxyalkyl, (Ci-C7) haloalkyl, (C 3 -C 7) halocycloalkyl, (Ci-C7) alkoxy, (C1-C7) - haloalkoxy, aryloxy, heteroaryloxy, (C3- C 7 ) -cycloalkyloxy, hydroxy, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7
  • Q is an optionally substituted aryl, heteroaryl, (C3-C8) -cycloalkyl or (C3-C8) - represents cycloalkenyl, wherein each ring or ring system with up to 5 substituents selected from the group R may be optionally substituted 5; 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
  • Halocycloalkenyl or (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl,
  • Z for the group W 1 and W 2 are independently oxygen or sulfur
  • R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyl , aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C 6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) halocycloalkyl, (C 3 -C 6) - Halocycloalkyl- (Ci-C 6) alkyl, (Ci-C 6) alkylcarbonyl, (Ci-C 6) -alkoxycarbonyl, (C 2 -C 6) -
  • R 2 represents hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - hydroxyalkyl, (Ci-C 6) alkoxy ( Ci-C 6 ) -alkyl,
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 , or an optionally substituted (C 3 -Cg) -cycloalkyl, (C 3 -Cg) -halocycloalkyl, (C 3 -Cg) -cyanocycloalkyl, (Ci-Cg) -alkyl - (C 3 -Cg) -cycloalkyl, (Ci-Cg) -alkoxy- (C 3 -Cg) -cycloalkyl, ( Ci-Cg) -haloalkoxy- (C 3 -Cg) -cycloalkyl, (Ci-Cg) -alkylthio (C 3 -Cg) -cycloalkyl, aryl- (C 3 -Cg) -cycloalkyl, heteroaryl- (C 3 - Cg) cyclo
  • R 4 is hydrogen, amino, amino (C 1 -C 5 ) -alkyl, aminobis (C 1 -C 5 ) -alkyl, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -) C 6) alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) - alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 4 -alkyl) 6 ) -alkyl
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cv) -cycloalkyl or (C3-C7) -
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen are;
  • R 1 is hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 -alkyl), 4) alkyl, heterocyclyl (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) - alkyl, (C3-C6) - Halocyclo- (Ci-C 4) alkyl, (Ci-C6) alkylcarbonyl, (Ci-C6) alkoxycarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, tris [ (Ci-C6) alkyl] silyl (C 2 -C 6) alkynyl
  • R 2 is hydrogen, fluorine, chlorine, (C 1 -C 4 ) -alkyl
  • R 3 is an optionally substituted aryl and heteroaryl, where each ring or each ring system may optionally be substituted by up to 5 substituents from the group R 5 , or represents an optionally substituted (C 3 -C 7 ) -cycloalkyl, (C 3 -C 4 ) -cycloalkyl C 7) halocycloalkyl, (C3-C7) - Cyanocycloalkyl, (Ci-C 7) alkyl - (C 3 -C 7) cycloalkyl, (Ci-C7) alkoxy (C 3 -C 7) - cycloalkyl, (Ci-C7) haloalkoxy (C 3 -C 7) cycloalkyl, (Ci-C 7) alkylthio (C 3 -C 7) cycloalkyl, aryl (C 3 -C 7) - cycloalkyl, heteroaryl- (C 3 -C 7 )
  • R 5 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) -alkyl,
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cv) -cycloalkyl or (C3-C7) -
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen are;
  • R 1 represents hydrogen, (Ci-C 3) alkyl, aryl (Ci-C 3) alkyl, heteroaryl (Ci-C 3) alkyl, (C 3 -C 6) -
  • Cycloalkyl (C 3 -C 5) cycloalkyl (Ci-C 3) alkyl, (Ci-C 6) alkylcarbonyl, (Ci-C 6) -alkoxycarbonyl, (C 2 -C 6) alkenyl, ( C 2 -C 6 ) alkynyl, or trimethylsilyl,
  • R 2 is hydrogen, fluorine or chlorine.
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 , or an optionally substituted (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7) halocycloalkyl, (C 3 -C 7) - Cyanocycloalkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) alkoxy (C 3 - C 7) cycloalkyl, (C 1 -6 haloalkoxy (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio (C 3 -C 7) cycloalkyl, aryl (C 3 -C 7 ) -cycloalkyl, heteroaryl- (C 3 -C 7 )
  • R 5 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) -alkyl,
  • W 1 and W 2 are oxygen;
  • R 1 is hydrogen, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl or
  • R is hydrogen, fluorine or chlorine.
  • Z stands for the groups Z-1.1 to Z-1.97,
  • W 1 and W 2 are oxygen
  • R 1 is hydrogen, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl or
  • Trimethylsilyl is, and
  • R 2 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-methylpentyl
  • 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 (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4) -alkylthio, for example (but not limited to) (C 1 -C 6) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3 Methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio
  • Cycloalkylthio means according to the invention a bonded via a sulfur atom
  • 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 a bonded via an oxygen atom alkynyl group such as (C 2 -C 1 0) -, (C 2 -C 6) - or (C 2 -C 4) alkenoxy, and (C3-C10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -alkoxy.
  • Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom.
  • the number of C atoms refers to the alkyl radical in the
  • the number of C atoms here refers to the alkyl radical in the alkoxycarbonyl group, analogously “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C ( O), such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) - alkenyloxycarbonyl or (C3-C10) -, (C 3 -C 6) - or (C3-C4)
  • the number of carbon 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
  • 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-1H-pyrrole 1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-I - or 2- or 3- or 4-yl; 2,3-dihydropyridine-2 or 3 or 4 or 5 or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or
  • 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
  • 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
  • 1,2-dithiin-3 or 4-yl 1,2-dithiin-3 or 4-yl; l, 2-dithiin-3 or 4-yl; l, 3-dithian-2 or 4 or 5-yl; 4H-l, 3-dithiin-2 or 4 or 5 or 6-yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • 6- or 7-yl 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l,
  • 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, 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, particularly preferred are 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; The term 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, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optional halogen atoms 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 cumulenyl radicals having one or more cumulated double bonds, such as, for example, allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6) -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2 Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-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 radical 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 stands alone or as part of a chemical
  • Group - represents straight-chain or branched S-haloalkyl, preferably of 1 to 8, or of 1 to 6 carbon atoms, such as (C 1 -C 8) -, (C 1 -C 6) - or (C 1 -C 4) -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 isoazolidin-5-ones 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, on appropriately substituted aldehydes and on commercially available chemicals such as malonic acid derivatives and
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as methanol or ethanol (see Scheme 1).
  • the cis isomer can be detected in small amounts by NMR in some cases.
  • R ' (C 1 -C 4 ) -alkyl or aryl- (C 1 -C 4 ) -alkyl.
  • the synthesis of the nitrone of general formula (II) can be carried out by condensation of an aldehyde of general formula (IV) with a hydroxylamine of general formula (V) in the presence of a base such as sodium bicarbonate and a Lewis acid such as magnesium sulfate.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in a suitable solvent such as, for example, dichloromethane.
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 4 describes the synthesis of the compound of the general formula (Ib) by reacting a monoamide of the general formula (IX) with a hydroxylamine of the general formula (VIII) in the presence of a Lewis acid such as, for example, scandium triflate.
  • a Lewis acid such as, for example, scandium triflate.
  • the crude product is treated with a fluoride source such as tetrabutylammonium fluoride.
  • the reaction preferably takes place in the temperature range between -70 ° C and 20 ° C, in an adequate solvent such as dichloromethane.
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (IX) can be prepared by Knoevenagel condensation of an aldehyde of general formula (IV) with malonic esters of general formula (X) (see Scheme 5, G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
  • R ' (C 1 -C 4 ) -alkyl.
  • Table LI Preferred compounds of the formula (LI) are the compounds 1.1-1 to 1.1-292, wherein Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-292 of the table LI are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (LI) are the compounds 1.1-1 to 1.1-292, wherein Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-292 of the table LI are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (LI) are the compounds 1.1-1 to 1.1-292, wherein Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-292 of the table LI are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1 Preferred compounds of the formula (LI) are the compounds 1.1-1
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.2-1 to 1.2-292 of Table 1.2 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.3-1 to 1.3-292 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.4-1 to 1.4-292 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-292, 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 292 are defined for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.6-1 to 1.6-292 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-292 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.8-1 to 1.8-292 of Table 1.8 are therefore affected by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-292 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-292, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.10-1 to 1.10-292 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11 - 1 to 1.11-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections LI 1-1 to LI 1-292 of Table LI 1 are thus by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.12-1 to 1.12-292 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.13-1 to 1.13-292 of Table 1.13 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.14-1 to 1.14-292 of Table 1.14 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-292 of Table 1.15 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.16-1 to 1.16-292 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-292, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.17-1 to 1.17-292 of Table 1.17 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.18-1 to 1.18-292 of Table 1.18 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.19-1 to 1.19-292 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.20-1 to 1.20-292 of Table 1.20 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.21-1 to 1.21-292 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-292, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.22-1 to 1.22-292 of Table 1.22 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.23-1 to 1.23-292 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.24-1 to 1.24-292 of Table 1.24 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.25-1 to 1.25-292 of Table 1.25 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.26-1 to 1.26-292 of Table 1.26 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.27-1 to 1.27-292 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.28-1 to 1.28-292 of Table 1.28 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-292, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.29-1 to 1.29-292 of Table 1.29 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-292 of Table 1.30 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.31-1 to 1.31-292 of Table 1.31 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.32-1 to 1.32-292 of Table 1.32 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.33-1 to 1.33-292 of Table 1.33 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.34-1 to 1.34-292 of Table 1.34 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.35-1 to 1.35-292 of Table 1.35 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.36-1 to 1.36-292 of Table 1.36 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.37-1 to 1.37-292 of Table 1.37 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.38-1 to 1.38-292 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.39-1 to 1.39-292 of Table 1.39 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.40-1 to 1.40-292 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.41-1 to 1.41-292 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.42-1 to 1.42-292 of Table 1.42 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-292 of Table 1.43 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.44-1 to 1.44-292 of Table 1.44 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.45-1 to 1.45-292 of Table 1.45 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-292, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.46-1 to 1.46-292 of Table 1.46 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.47-1 to 1.47-292 of Table 1.47 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.48-1 to 1.48-292 of Table 1.48 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.49-1 to 1.49-292 of Table 1.49 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.50-1 to 1.50-292 of Table 1.50 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.51-1 to 1.51-292 of Table 1.51 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.45-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.52-1 to 1.52-292 of Table 1.52 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.53-1 to 1.53-292 of Table 1.53 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.54-1 to 1.54-292 of Table 1.54 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-292, in which Q has the meanings given in Table 1 of each Table.
  • the connections 1.55-1 to 1.55-292 of Table 1.55 are therefore affected by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.56-1 to 1.56-292 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.57-1 to 1.57-292 of Table 1.57 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.58-1 to 1.58-270 of Table 1.58 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.59-1 to 1.59-292 of Table 1.59 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.60-1 to 1.60-292 of Table 1.60 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.6-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.61-1 to 1.61-292 of Table 1.61 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.62-1 to 1.62-292 of Table 1.62 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.63-1 to 1.63-292 of Table 1.63 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.64-1 to 1.64-292 of Table 1.64 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.65-1 to 1.65-292 of Table 1.65 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-292, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.66-1 to 1.66-292 of Table 1.66 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.67-1 to 1.67-292 of Table 1.67 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.68-1 to 1.68-292 of Table 1.68 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-292, wherein Q has the meanings given in Table 1 of each line.
  • the compounds 1.69-1 to 1.69-292 of Table 1.69 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.70-1 to 1.70-292 of Table 1.70 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.71-1 to 1.71-292 of Table 1.71 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.72-1 to 1.72-292 of Table 1.72 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.73-1 to 1.73-292 of Table 1.18 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.74-1 to 1.74-292 of Table 1.74 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.75-1 to 1.75-292 of Table 1.75 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.76-1 to 1.76-292 of Table 1.76 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.77-1 to 1.77-292 of Table 1.77 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.78-1 to 1.78-292 of Table 1.78 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.79-1 to 1.79-292 of Table 1.79 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.80-1 to I.80-292 of Table 1.80 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.81-1 to 1.81-292 of Table 1.81 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.82-1 to 1.82-292 of Table 1.82 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.83-1 to 1.83-292 of Table 1.83 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.29-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.84-1 to 1.84-292 of Table 1.84 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.85-1 to 1.85-292 of Table 1.85 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.86-1 to 1.86-292 of Table 1.86 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.87-1 to 1.87-292 of Table 1.87 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.88-1 to 1.88-292 of Table 1.88 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.89-1 to 1.89-292 of Table 1.89 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-292, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.90-1 to 1.90-292 of Table 1.90 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.91-1 to 1.91-292 of Table 1.91 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.92 Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.92-1 to 1.92-292 of Table 1.92 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.93-1 to 1.93-292 of Table 1.93 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.94-1 to 1.94-292 of Table 1.94 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.95-1 to 1.95-292 of Table 1.95 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.96-1 to 1.96-292 of Table 1.96 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.97 Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.97-1 to 1.97-292 of Table 1.97 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.98 Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.98-1 to 1.98-292 of Table 1.98 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.99-1 to 1.99-292 of Table 1.99 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.100 Preferred compounds of the formula (1.100) are the compounds 1.100-1 to 1.100-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connection 1.100-1 to 1.100-292 of Table 1.100 are thus determined by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.101 Preferred compounds of the formula (1.101) are the compounds 1.101-1 to 1.101-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.101-1 to 1.101-346 of Table 1.101 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.102 Preferred compounds of the formula (1.102) are the compounds 1.102-1 to 1.102-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.102-1 to 1.102-292 of Table 1.102 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.103 Preferred compounds of the formula (1.103) are the compounds 1.103-1 to 1.103-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.103-1 to 1.103-292 of Table 1.103 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.104 Preferred compounds of the formula (1.104) are the compounds 1.104-1 to 1.104-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.104-1 to 1.104-292 of Table 1.104 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.105 Preferred compounds of the formula (1.105) are the compounds 1.105-1 to 1.105-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.105-1 to 1.105-292 of Table 1.105 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.106 Preferred compounds of the formula (1.106) are the compounds 1.106-1 to 1.106-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.106-1 to 1.106-292 of Table 1.106 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.107 Preferred compounds of the formula (1.107) are the compounds 1.107-1 to 1.107-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.107-1 to 1.107-292 of Table 1.107 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.108 Preferred compounds of the formula (1.108) are the compounds 1.108-1 to 1.108-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.108-1 to 1.108-292 of Table 1.108 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.109 Preferred compounds of the formula (1.109) are the compounds 1.109-1 to 1.109-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.109-1 to 1.109-292 of Table 1.109 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table LI 10 Preferred compounds of the formula (LI 10) are the compounds L I 10-1 to L I 10-292, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compound L I 10-1 to LI 10-292 of the table LI 10 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (1.111) are the compounds 1.111-1 to 1.111-292, in which Q has the meanings given in Table 1 in the respective line.
  • the compound L I 11-1 to LI 11-292 of Table LI 11 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table LI 12 Preferred compounds of the formula (LI 12) are the compounds LI 12-1 to LI 12-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds LI 12-1 to LI 12-292 of Table LI 12 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table LI 13 Preferred compounds of the formula (LI 13) are the compounds L I 13-1 to L I 13-292, wherein Q has the meanings given in Table 1 of each Table.
  • the connection L I 13-1 to LI 13-292 of the table LI 13 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table LI 14 Preferred compounds of the formula (LI 14) are the compounds L I 14-1 to L I 14-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the connection L I 14-1 to LI 14-292 of the table LI 14 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table LI 15 Preferred compounds of the formula (LI 15) are the compounds LI 15-1 to LI 15-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds LI 15-1 to LI 15-292 of Table LI 15 are thus by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Preferred compounds of the formula (I-16) are the compounds I-16-1 to I-16- 292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compound L I 16-1 to L I 16-292 of the table L I 16 are thus by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Preferred compounds of the formula (L I 17) are the compounds 1,117-1 to 1,117-292, in which Q has the meanings given in Table 1 of each Table.
  • the compound L I 17-1 to L I 17-292 of the table L I 17 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.118 Preferred compounds of the formula (1.118) are the compounds 1.118-1 to 1.118-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds LI 18-1 to LI 18-292 of Table LI 18 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Preferred compounds of the formula (I-19) are the compounds I-19-1 to I-19-292 in which Q has the meanings given in Table 1.
  • the compound L I 19-1 to L I 19-292 of the table L I 19 are thus by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.120 Preferred compounds of the formula (1.120) are the compounds 1,120-1 to 1,120-292, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.120-1 to 1.120-292 of Table 1.120 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.121 Preferred compounds of the formula (1.121) are the compounds 1.121-1 to 1.121-292, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.121-1 to 1.121-292 of Table 1.121 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.122 Preferred compounds of the formula (1.122) are the compounds 1.122-1 to 1.122-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.122-1 to 1.122-292 of Table 1.122 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.123 Preferred compounds of the formula (1.123) are the compounds 1.123-1 to 1.123-292, in which Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.123-1 to 1.123-292 of Table 1.123 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.124 Preferred compounds of the formula (1.124) are the compounds 1.124-1 to 1.124-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.124-1 to 1.124-292 of Table 1.124 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.125 Preferred compounds of the formula (1.125) are the compounds 1.125-1 to 1.125-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.125-1 to 1.125-292 of Table 1.125 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.126 Preferred compounds of the formula (1.126) are the compounds 1.126-1 to 1.126-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.126-1 to 1.126-292 of Table 1.126 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.127 Preferred compounds of the formula (1.127) are the compounds 1.127-1 to 1.127-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.127-1 to 1.127-292 of Table 1.127 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.128 Preferred compounds of the formula (1.128) are the compounds 1.128-1 to 1.128-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.128-1 to 1.128-292 of Table 1.128 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.129 Preferred compounds of the formula (1.129) are the compounds 1.129-1 to 1.129-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.129-1 to 1.129-292 of Table 1.129 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.130 Preferred compounds of the formula (1.130) are the compounds 1.130-1 to 1.130-292, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.130-1 to 1.130-292 of Table I. 130 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.131 Preferred compounds of the formula (1.131) are the compounds 1.131-1 to 1.131-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.131-1 to 1.131-292 of Table 1.131 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.132 Preferred compounds of the formula (1.132) are the compounds 1.132-1 to 1.132-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.132-1 to 1.132-292 of Table 1.132 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.133 Preferred compounds of the formula (1.133) are the compounds 1.133-1 to 1.313-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.133-1 to 1.133-292 of Table 1.133 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.134 Preferred compounds of the formula (1.134) are the compounds 1.134-1 to 1.134-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.134-1 to 1.134-292 of Table 1.134 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.135 Preferred compounds of the formula (1.135) are the compounds 1.135-1 to 1.135-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.135-1 to 1.135-292 of Table 1.135 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.136 Preferred compounds of the formula (1.136) are the compounds 1.136-1 to 1.136-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.136-1 to 1.136-292 of Table 1.136 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.137 Preferred compounds of the formula (1.137) are the compounds 1.137-1 to 1.137-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.137-1 to 1.137-292 of Table 1.137 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.138 Preferred compounds of the formula (1.138) are the compounds 1.138-1 to 1.138-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.138-1 to 1.138-292 of Table 1.138 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.139 Preferred compounds of the formula (1.139) are the compounds 1.139-1 to 1.139-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.139-1 to 1.139-292 of Table 1.139 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.140 Preferred compounds of the formula (1.140) are the compounds 1.140-1 to 1.140-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connection 1.140-1 to 1.140-292 of Table 1.140 are thus by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.141 Preferred compounds of the formula (1.141) are the compounds 1.141-1 to 1.141-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.141-1 to 1.141-292 of Table 1.141 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.142 Preferred compounds of the formula (1.142) are the compounds 1.142-1 to 1.142-292, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.142-1 to 1.142-292 of Table 1.142 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.143 Preferred compounds of the formula (1.143) are the compounds 1.143-1 to 1.143-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.143-1 to 1.143-292 of Table 1.143 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.144 Preferred compounds of the formula (1.144) are the compounds 1.144-1 to 1.144-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.144-1 to 1.144-292 of Table 1.144 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.145 Preferred compounds of the formula (1.145) are the compounds 1.145-1 to 1.145-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.145-1 to 1.145-292 of Table 1.145 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.146 Preferred compounds of the formula (1.146) are the compounds 1.146-1 to 1.146-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.146-1 to 1.146-292 of Table 1.146 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.147 Preferred compounds of the formula (1.147) are the compounds 1.147-1 to 1.147-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.147-1 to 1.147-292 of Table 1.147 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.148 Preferred compounds of the formula (1.148) are the compounds 1.148-1 to 1.148-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.148-1 to 1.148-292 of Table 1.148 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.149 Preferred compounds of the formula (1.149) are the compounds 1.149-1 to 1.149-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.149-1 to 1.149-292 of Table 1.149 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.150 Preferred compounds of the formula (1.150) are the compounds 1.150-1 to 1.150-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.150-1 to 1.150-292 of Table 1.150 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.151 Preferred compounds of the formula (1.151) are the compounds 1.151-1 to 1.151-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.151-1 to 1.151-292 of Table 1.151 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.152 Preferred compounds of the formula (1.152) are the compounds 1.152-1 to 1.152-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.152-1 to 1.152-292 of Table 1.152 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.153 Preferred compounds of the formula (1.153) are the compounds 1.153-1 to 1.153-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.153-1 to 1.153-270 of Table 1.153 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.154 Preferred compounds of the formula (1.154) are the compounds 1.154-1 to 1.154-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.154-1 to 1.154-292 of Table 1.154 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.155 Preferred compounds of the formula (1.155) are the compounds 1.155-1 to 1.155-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.155-1 to 1.155-292 of Table 1.155 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.156 Preferred compounds of the formula (1.156) are the compounds 1.156-1 to 1.156-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.156-1 to 1.156-292 of Table 1.156 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.157 Preferred compounds of the formula (1.157) are the compounds 1.157-1 to 1.157-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.157-1 to 1.157-292 of Table 1.157 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.158 Preferred compounds of the formula (1.158) are the compounds 1.158-1 to 1.158-292, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.158-1 to 1.158-292 of Table 1.158 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.159 Preferred compounds of the formula (1.159) are the compounds 1.159-1 to 1.159-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.159-1 to 1.159-292 of Table 1.159 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.160 Preferred compounds of the formula (1.160) are the compounds 1.160-1 to 1.160-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connection 1.160-1 to 1.160-292 of Table 1.160 are thus by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.161 Preferred compounds of the formula (1.161) are the compounds 1.161-1 to 1.161-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.161-1 to 1.161-292 of Table 1.161 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.162 Preferred compounds of the formula (1.162) are the compounds 1.162-1 to 1.162-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.162-1 to 1.162-292 of Table 1.162 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.163 Preferred compounds of the formula (1.163) are the compounds 1.163-1 to 1.163-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.163-1 to 1.163-292 of Table 1.163 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.164 Preferred compounds of the formula (1.164) are the compounds 1.164-1 to 1.164-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.164-1 to 1.164-292 of Table 1.164 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.165 Preferred compounds of the formula (1.165) are the compounds 1.165-1 to 1.165-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.165-1 to 1.165-292 of Table 1.165 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.166 Preferred compounds of the formula (1.166) are the compounds 1.166-1 to 1.166-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.166-1 to 1.166-292 of Table 1.166 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.167 Preferred compounds of the formula (1.167) are the compounds 1.167-1 to 1.167-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.167-1 to 1.167-292 of Table 1.167 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.168 Preferred compounds of the formula (1.168) are the compounds 1.168-1 to 1.168-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.168-1 to 1.216-292 of Table 1.168 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.169 Preferred compounds of the formula (1.169) are the compounds 1.169-1 to 1.169-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.169-1 to 1.169-292 of Table 1.169 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.170 Preferred compounds of the formula (1.170) are the compounds 1.170-1 to 1.170-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connection 1.170-1 to 1.170-292 of Table 1.170 are thus by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.171 Preferred compounds of the formula (1.171) are the compounds 1.171-1 to 1.171-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.171-1 to 1.171-292 of Table 1.171 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.172 Preferred compounds of the formula (1.172) are the compounds 1.172-1 to 1.172-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.172-1 to 1.172-292 of Table 1.172 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.173 Preferred compounds of the formula (1.173) are the compounds 1.173-1 to 1.173-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.173-1 to 1.173-292 of Table 1.173 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.174 Preferred compounds of the formula (1.174) are the compounds 1.174-1 to 1.174-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.174-1 to 1.174-292 of Table 1.174 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.175 Preferred compounds of the formula (1.175) are the compounds 1.175-1 to 1.175-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.175-1 to I.175-292 of Table 1.175 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.176 Preferred compounds of the formula (1.176) are the compounds 1.176-1 to 1.176-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.176-1 to 1.176-292 of Table 1.176 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.177 Preferred compounds of the formula (1.177) are the compounds 1.177-1 to 1.177-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.177-1 to 1.177-292 of Table 1.177 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.178 Preferred compounds of the formula (1.178) are the compounds 1.178-1 to 1.178-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.178-1 to 1.178-292 of Table 1.178 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.179 Preferred compounds of the formula (1.179) are the compounds 1.179-1 to 1.179-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.179-1 to 1.179-292 of Table 1.179 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.180 Preferred compounds of the formula (1.180) are the compounds 1,180-1 to 1,180-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connection 1.180-1 to 1.180-292 of Table 1.180 are thus by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.181 Preferred compounds of the formula (1.181) are the compounds 1.181-1 to I. 181-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.181-1 to 1.261-181 of Table 1.181 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table I. 182 Preferred compounds of the formula (I. 182) are the compounds 1.182-1 to I. 182-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.182-1 to 1.182-292 of Table 1.182 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.183 Preferred compounds of the formula (1.183) are the compounds 1.183-1 to 1.183-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.183-1 to 1.183-292 of Table 1.183 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.184 Preferred compounds of the formula (1.184) are the compounds 1.184-1 to 1.184-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.184-1 to 1.184-292 of Table 1.184 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.185 Preferred compounds of the formula (1.185) are the compounds 1.185-1 to 1.185-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.185-1 to 1.185-292 of Table 1.185 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.186 Preferred compounds of the formula (1.186) are the compounds 1.186-1 to 1.186-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.186-1 to 1.186-292 of Table 1.186 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.187 Preferred compounds of the formula (1.187) are the compounds 1.187-1 to 1.187-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.187-1 to 1.187-292 of Table 1.187 are thus distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.188 Preferred compounds of the formula (1.188) are the compounds 1.188-1 to 1.188-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.188-1 to 1.188-292 of Table 1.188 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.189 Preferred compounds of the formula (1.189) are the compounds 1.189-1 to 1.189-292, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.189-1 to 1.189-292 of Table 1.189 are thus characterized by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.190 Preferred compounds of the formula (1.190) are the compounds 1.190-1 to 1.190-292, wherein Q has the meanings given in Table 1 of each Table.
  • the connection 1.190-1 to 1.190-292 of Table 1.190 are thus by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.191 Preferred compounds of the formula (1.191) are the compounds 1.191-1 to 1.191-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.191-1 to 1.191-292 of Table 1.191 are therefore distinguished by the meaning of the respective entries no. 1 to 292 for Q of Table 1 above.
  • Table 1.192 Preferred compounds of the formula (1.192) are the compounds 1.192-1 to 1.192-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.192-1 to 1.192-292 of Table 1.192 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.193 Preferred compounds of the formula (1.193) are the compounds 1.193-1 to 1.193-292, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.193 -1 to 1.193 -292 of Table 1.193 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.194 Preferred compounds of the formula (1.194) are the compounds 1.194-1 to 1.194-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.194-1 to 1.194-292 of Table 1.194 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.195 Preferred compounds of the formula (1.195) are the compounds 1.195-1 to 1.195-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.195-1 to 1.195-292 of Table 1.195 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.196 Preferred compounds of the formula (1.196) are the compounds 1.196-1 to 1.196-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.196-1 to 1.196-292 of Table 1.196 are thus characterized by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.197 Preferred compounds of the formula (1.197) are the compounds 1.197-1 to 1.197-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.197-1 to 1.197-292 of Table 1.197 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.198 Preferred compounds of the formula (1.198) are the compounds 1.198-1 to 1.198-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.198-1 to 1.198-292 of Table 1.198 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.199 Preferred compounds of the formula (1.199) are the compounds 1.199-1 to 1.199-292, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.199-1 to 1.199-292 of Table 1.199 are thus distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.200 Preferred compounds of the formula (1.200) are the compounds 1,200-1 to 1,200-292, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.200-1 to 1.200-292 of the table 1.200 are thus by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.201 Preferred compounds of the formula (1.201) are the compounds 1.201-1 to 1.201-292, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.201-1 to 1.201-292 of Table 1.201 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • Table 1.202 Preferred compounds of the formula (1.202) are the compounds 1.202-1 to 1.202-292, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.202-1 to 1.202-292 of Table 1.202 are therefore distinguished by the meaning of the respective entries no. 1 to 292 are defined for Q of Table 1.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. 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 ⁇ ; 82 (intensity 2);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n ))
  • 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, with broad signals showing multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum.
  • the lists of the IH-NMR peaks are similar to the classical IH-NMR prints and thus usually contain all the peaks that are listed in a classical NMR interpretation. In addition, they can, like classic IH-NMR prints solvent signals, signals from
  • Stereoisomers of the target compounds which are also the subject of the invention, and / or show peaks of impurities.
  • 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%).
  • Such 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.
  • ⁇ 8.8952 (0.7); 8.1314 (0.7); 8.1258 (0.8); 8.1100 (0.6); 7.8736 (1.7); 7.8030 (0.9); 7.7836 (1.0); 7.6573 (0.8); 7.6377 (1.2); 7,5683 (1.0); 7.5489 (1.5); 7.5295 (0.6); 7.2590 (26.5); 7.1194 (0.8); 7.1144 (0.5); 7.1110 (1.5); 7.1087 (2.4); 7.1055 (2.0); 7.1019 (1.0); 7.0960 (2.2); 7.0906 (2.3); 7.0877 (2.6); 7.0821 (1.0); 7.0.789 (0.7); 7.0766 (0.6); 4.6450 (1.5); 4.6153 (1.6); 4.0809 (3.1); 4.0511 (2.8); 2.8954 (16.0); 2.0429 (1.6); 1.5370 (2.2); 1.2759 (1.0); 1.2649 (1.6); 1.2581 (1.7); 1.2402 (0.6);
  • ⁇ 8.7480 (0.8); 7.8711 (1.8); 7.8026 (0.9); 7.7833 (1.1); 7.6614 (0.8); 7.6419 (1.2); 7.5734 (1.0); 7.5540 (1.5); 7.5345 (0.6); 7.4643 (0.6); 7.4587 (1.1); 7.4531 (0.7); 7.4377 (0.6); 7.4321 (1.1); 7.4265 (0.7); 7.2955 (0.7); 7.2797 (0.7); 7.2750 (1.6); 7.2592 (49.4); 7.2386 (1.0); 7.1445 (1.1); 7.1416 (1.0); 7.1242 (0.8); 7.1213 (0.8); 6.8414 (0.9); 6.8393 (0.9); 6.8352 (0.9); 6.8332 (0.9); 4.6274 (1.6); 4.5977 (1.8); 4.0334 (3.1); 4.0037 (2.8); 2.8962 (16.0); 1.5367 (1.3); 1.2558 (0.6); 0.0080 (0.8); -
  • 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 formulas (LI) to (1.202) and / or salts thereof, each as defined above, or of an agent according to the invention, as defined below, on the (harmful) plants, (harmful) plant seeds, the soil in which or on which the (harmful) plants grow, or the cultivated area is applied.
  • 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 formulas (LI) to (1.202) and / or salts thereof, each as defined above, or of an agent according to the invention, as defined below, on the (harmful) plants, (harmful)
  • 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 the general formula (I) and / or salts thereof, as defined above, preferably in one of preferred or particularly preferred marked
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.202) and / or salts thereof, 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 sprouts with buds), the soil in which or on which the undesirable plants grow (eg, the soil of cultivated land or non-cultivated land ) or the area under cultivation (ie area on which the unwanted plants will grow) is applied.
  • the present invention is also a method for controlling

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des isoazolidin-5-ones 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 des plantes pour influencer la croissance des cultures de plantes utiles. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance des plantes comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2018/057635 2017-03-30 2018-03-26 Isoazolidin-5-ones substituées et leurs sels et leur utilisation comme agents herbicides WO2018178008A1 (fr)

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EP17163794 2017-03-30

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128419A (zh) * 2019-05-17 2019-08-16 南开大学 一类二氟吡唑杂环甲酰胺类衍生物及其制备方法和用途
CN114401956A (zh) * 2019-07-22 2022-04-26 拜耳公司 取代的n-苯基尿嘧啶、其盐以及作为除草剂的用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4020446A1 (de) * 1990-06-27 1992-01-02 Bayer Ag Verwendung von substitutierten isoxazolin-5-onen als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung
WO2016176082A1 (fr) * 2015-04-27 2016-11-03 E I Du Pont De Nemours And Company Butyrolactones utilisées 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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4020446A1 (de) * 1990-06-27 1992-01-02 Bayer Ag Verwendung von substitutierten isoxazolin-5-onen als arzneimittel, neue verbindungen und verfahren zu ihrer herstellung
WO2016176082A1 (fr) * 2015-04-27 2016-11-03 E I Du Pont De Nemours And Company Butyrolactones utilisées 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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128419A (zh) * 2019-05-17 2019-08-16 南开大学 一类二氟吡唑杂环甲酰胺类衍生物及其制备方法和用途
CN114401956A (zh) * 2019-07-22 2022-04-26 拜耳公司 取代的n-苯基尿嘧啶、其盐以及作为除草剂的用途

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AR111302A1 (es) 2019-06-26
UY37653A (es) 2018-10-31

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