EP3383874A1 - Mesoionic halogenated 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate derivatives and related compounds as insecticides - Google Patents

Mesoionic halogenated 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate derivatives and related compounds as insecticides

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Publication number
EP3383874A1
EP3383874A1 EP16801802.6A EP16801802A EP3383874A1 EP 3383874 A1 EP3383874 A1 EP 3383874A1 EP 16801802 A EP16801802 A EP 16801802A EP 3383874 A1 EP3383874 A1 EP 3383874A1
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
cyano
spp
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP16801802.6A
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German (de)
French (fr)
Inventor
Markus Heil
Daniela Portz
Kerstin Ilg
Ulrich Görgens
Silvia Cerezo-Galvez
Marc Mosrin
Sascha EILMUS
Andreas Turberg
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP3383874A1 publication Critical patent/EP3383874A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants

Definitions

  • the present invention relates to novel mesoionic imidazole derivatives, to processes for their preparation and to their use for controlling animal pests, in particular arthropods and in particular insects, arachnids and nematodes.
  • the object of the present invention was to provide compounds which broaden the pesticide composition in various aspects and / or improve its activity.
  • the present invention therefore relates to compounds of the general formula (I)
  • Q 1 and Q together represent one of the radicals A 1 to A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
  • G is a bond, -C (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
  • U is a cycle of the series U-1 to U-28 stands
  • U-26 U-27 U-28 X a for halogen, nitro, OH.
  • R ', R 2 , R “, R 4 each independently represent hydrogen, halogen, cyano, nitro, SF 5, SCN, amino, G-Ce-alkyiamino, di (C 1 -G) -alkylamino, hydroxy, COOH, G-Ce-Alkyi, GG-cycloalkyl, GG-haloalkyl, G-C t -alkoxy, GG-haloalkoxy, C3-C6-
  • Halocycloallcyl C3-C6-halocycloalkyl-C1-C6-alkyl, GG-aikoxy-GG-alkyl, G-Ce-haloalkoxy-G-Ce-alkyl, G-Ce-alkoxy-G-Ce-allcyloxy, cyano-G -C6 -alkyl, GG-cycloalkyl-G-C6-alkyl, GG-alkenyl, C 2 -C 6 -alkenyloxy, C; -G -alkynyl, Cs-Ce-alkynyloxy, Si l.
  • G-Ce-alkylthio GC "alkylsulfmyl, GC 6 -alkylsulfonyl, GG-haloalkylsulfonyl, G-Ce-alkylcarbonyl, Cs-Ce-cycloalkylcarbonyi, GG-haloalkylcarbonyl.
  • GC 6 - Haiogenalkoxy or GG-alkylthio may be substituted
  • R 3 and R 4 each together form a 5- or 6-membered aliphatic, aromatic, heteroaromatic or heterocyclic ring which optionally has 1 to 2 atoms from the May contain O, S and N and which may optionally be monosubstituted or polysubstituted by halogen or by G-G-alkyl,
  • C i -G - halo may
  • R 5 is C 3 -C 6 -cycloalkyl or C 1 -C -heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, or simply by cyano, GG-alkyl, G-halogenoalkyl, G-C 1 -alkoxy , G-halogenoalkoxy C 3 -C 12 -cycloalkyl, GC 6 -alkylthio, GG-alkylsulfinyl, G-Ce-alkylsulfonyl, aryl, hetaryl.
  • Aryl-G-G, -alkyl or H et aary 1 -G -G -a 1 ky I may be substituted, wherein aryl, hetaryl, Arvl-G -G -alkyl and hetaryl-G-ce-alicyi in each case simple to trisubstituted by halogen, cyano, nitro, G -CVAlkyl, C1-C4 Halogenalkyi, C i - 4-haloalkoxy may be substituted (.i-alkoxy or GC ', or
  • R 5 is aryl or hetaryl, where the aforementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF 5, SCN, GG-alkylamino, di- (GG) -alkylamino , Hydroxy, COOK, GG-alkyl, GG-cycloalkyl, G-haloalkyl, G-G-alkoxy, GC 6 -haloalkoxy.
  • alkyl G-Ce-alkoxy-C i -C (alkyl, GG-haloalkoxy-GG-alkyl, G-Ce-alkoxy-G-ce-alkyloxy, cyano-GC «- alkyl, C 3 -C 6 cycloalkyl-Ci-C 6 alkyl, C 2 -C 6 alkenyl, GG, alkynyl, SH. G -C -alkylthio. GC "- alkylcarbonyl, G-Ce-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C * -C, -haloalkylcarbon vi.
  • R 51 is hydrogen or C 1 -C 6 -alkyl, GG-alkenyl, C 2 -C 6 -alkyl, GG-cycloalkyl or CVCY.-Hetert yelyl. wherein the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen or simply by nitro, cyano, C 3 -C 6 -cycloalkyl, G-G, -alkoxy, C 1 -C -haloalkoxy, G-C 1 -alkylthio, C 1 -C 6 Alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, G -G-alkoxy-imino-C 1, -G -alkvl, C 3 -C 6 -cycloalkylcarbonyl, GG-alkenyle
  • R 51 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di (C 1 -C 4) .
  • R 52 represents G-Ce-Aikyl, C 2 -C 6 -Aikenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -Cycloalkyi or C 3 -C 6 -Heterocyclyi, where the abovementioned radicals are optionally mono- to trisubstituted may be substituted and the substituents are independently selected from halogen, nitro, cyano, C 3 -Ce- cycloalkyl, GC 6 alkoxy, GC 6 haloalkoxy, VG -Alkylthio, GG-alkylsulfinyl, GC 6 - alkylsulfonyl, Ci-Cö Alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbon
  • R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di- (C 1 -C 4 -alkyl) C 6) -alkylamino, hydroxy, COOK, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, G-C 6 -haloalkyl, G-C 6 -alkoxy, G-C 6 -haloalkoxy, C 1 -C 6 -halocycloalkyl, C 3 -C 6 -Halocycloalkyl-C 1 -C 6 -alkyl, G-Ce-alkoxy-G-G-alkyl, G-G 1 algC-dialkoxy-G Y-
  • R 53 is hydrogen, G-Ce-Aikyl, C ⁇ -Ce-Alkenyi, C 2 -C 6 -Alkinyi, -C-cycloalkyl, Ci-C 4 -Aikoxy, C i -C; -A!
  • R 54 is hydrogen or Ci-Ce-Alkyi, C: -, - alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl or Cs-Ce-cycloalkyl-C 1 -C 6 -alkyl, wherein the abovementioned radicals optionally substituted independently one to five times (by halogen or monosubstituted by cyano, nitro, hydroxy, CV t-alkyl, Cs-Ce-cycloalkyl, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 - Aikylthio, C 1 -C 4 alkylsulfmyl, C 1 -C 4 alkylsulfonyl, C s -C f - A 1 koxy carbony 1, G-Ce-Alkylcarbonyi or Cs-Ce-triaikylsilyl may be substituted
  • R 54 is aryl, hetaryl, Arvl-CVC-alkyl or heteroaryl-i-C, -alkyl, where the abovementioned radicals may optionally be substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C; -Ct.-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkylamino, Vd-alkoxy, C 1 -C 4 -haloalkyl, C 1 -C -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 - alkylsulfonyl, C1-C4 -Alkylsulfimino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl, or R 53 and R 54 may be connected to each other via two to six carbon atoms and form a ring which may optional
  • R 55 represents GG-alkyl, C 3 -G-cycloalkyl, C 1 -C 6 -haloalkyl, GG-halogenocycloalkyl, GG-cycloalkyl-C 1 -C 6 -alkyl, GG-halogenocycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 4 -alkyl, C 6 alkyl, GC 6 -Aikoxy, Ci-C6-haloalkoxy, Ci-Ce-Aikoxy-Ci-Ce-aikyl, GG, haloalkoxy C ⁇ -G -alkyl.
  • Aryl Aryl.
  • R 56 is G-G-alkyl, C 3 -C 6 -cycloalkyl, G -H-haloalkyl.
  • R 6 is G-Ce-alkyl, GG-cycloalkyl, GG-haloalkyl.
  • C 3 -C 6 -halocycloalkyl or; (-, "- alkoxy; -G.-alkyl may be substituted
  • R 7 represents hydrogen, G 6 -alkyl, GG-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, G-G-alkoxy,] - (.t-alkoxy-C 1 -G- Alkyl, C 1 -G -alkoxycarbonyl or C 1 -G, -alkylcarbonyl,
  • R 7a is hydrogen, GG-alkyl, GG-alkenyl, GG-alkynyl, C 3 -Ce-cycloalkyl, GC 4 -alkoxy-G-G, -alkyl, G-G-alkoxycarbonyl or C 1 -G-alkylcarbonyl,
  • R 8 is hydrogen or G-G-alkyl, C - G - alkenyl or GG-alkynyl, where the abovementioned radicals, where appropriate, independently of one another, can be monosubstituted to five times by halogen or simply by cyano, nitro, hydroxy, G- Alkyl, GG-cycloalkyl, G-G-alkoxy, GG-haloalkoxy, G -G- Alkylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -alkylsulfimino, GC 4 -alkyl sul fimino-C 1 - Valkyl.
  • R 8 is aryl-C 1 -C 6 -alkyl, heteroaryl-GG-alkyl.
  • Ci-C4-haloalkoxy Ci-C 4 -Aikyithio, GG-alkylsulfinyl, Ci-C 4 alkylsulfonyl, GG alkyl sul fimino, C 2 -C 6 Aikoxycarbonyi or GG-alkylcarbonyl, or
  • R 8 is an optionally mono- or polysubstituted by identical or different substituents 5- or 6-membered aromatic or heteroaromatic ring, a 4- to ⁇ -membered partially saturated ring or saturated heterocyclic ring, or a saturated or aromatic hetero-bicyclic ring, which may optionally contain one to three heteroatoms from the series O, S or N and which may optionally be mono- or polysubstituted, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, Ci-Ce-alkyl , C 2 -C 6 alkynyl, G -C, -haloalkyl.
  • GG-cycloalkyl GG-cycloalkylamino, Ci-C 4 alkoxy, haloalkoxy 4 GC, GC 4 alkylthio, Ci-C 4 -Alkylsulfmyl, GG-alkylsulfonyl, Ci-C4-Aikylsuifimino, GG-Aikoxycai-carbonyl or GG Alkylcarbonyl, or
  • R and R 8 may be connected to each other via two to six carbon atoms and form a ring optionally additionally containing a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with GG-alkyl, halogen, cyano, amino or G-C Alkoxy may be substituted,
  • R 9 represents hydrogen, fluorine, chlorine, GC 4 alkyl, C 3 -C 6 cycloalkyl or C 4 is haloalkyl
  • R 9a is hydrogen, fluorine, chlorine, GC -Alkyi 4, C 3 -C 6 -Cycloaikyl or C is 4 -Halogenalkyi,
  • R i0 is hydrogen, fluorine, chlorine or GC 4 alkyl
  • R i o a hydrogen, fluorine, chlorine or GC 4 alkyl.
  • the compounds of formula (I) also include optionally present diastereomers or enantiomers and E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
  • the substituted mesoionic imidazole derivatives are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below.
  • a further embodiment (embodiment 1-1) are compounds of the formula (I) in which
  • T is R 5 , -OK' .
  • T is -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
  • G is a bond, -C (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
  • U is a cycle of the series U1 to U- 28 stands,
  • X a for halogen, nitro, oil.
  • Ce-haloalkoxy-C 1 -C 6 -alkyl C 1 - ( ') -Alkoxy-C 1 -C -alkenyl, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C -C-alkenyl, Cs-Ce-alkynedi, Ci-Ce-alkylthio, G-Ce-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C> -G haloalkylcarbonyl, G-Ce-alkoxycarbonyl , C 1 -G -Alkoxy-1-C 1 -C 1 -alkyl, C 1 -C 6 -alkenylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1
  • Ky, C ' i-Ci-haloalkyl, Ci-C4-alkoxy or C ' iC s -haloalkoxy can be substituted and wherein the ring N-atoms in Ul 7, Ul 8, Ul 9, U-26, U-27 and U-28 not by halogen, Nitro, OH. Cyano, SCN, SF 5 , GG-alkoxy, G-Ce-haloalkoxy, G-C-alkylthio. GG-alkylsulfinyl or C ⁇ -Ci-alkoxy-C ⁇ -G-alkyloxy are substituted, n is 0, 1, 2 or 3,
  • R 1 , R-. R 3 , R 4 are each independently of one another hydrogen, halogen, cyano, nitro, SF 5 , SCN, amino, GG-alkylamino, di- (C 1 -C 6) -alkylamino, hydroxy, COOH, G-G-alkyl, GG-
  • Alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl, GC 6 alkoxy, Ci-C 6 -haloalkyl, Ci-C 6 - Haiogenaikoxy or G-Ce-alkylthio may be substituted, or
  • R 5 is G-Cö-cycloalkyl or C 3 -G heterocyclyl, where the abovementioned radicals optionally independently of one another, are monosubstituted to trisubstituted by halogen, or simply by cyano, GG-alkyl, GG-haloalkyl, GG-alkoxy, CVG -haloalkoxy C 3 -G-cycloalkyl, GC 6 - alkylthio.
  • G-Ce-alkylsulfmyl, GC 6 alkylsulfonyl, aryl, hetaryl, aryl-G-Ce-alkyl or H etary 1 - ' i -G -al ky 1 may be substituted, wherein aryl, hetaryl.
  • Aryl-C i - alkyl and hetaryl-G -G-alkyl in each case monosubstituted to trisubstituted by halogen, cyano, nitro, G -Cs-alkyl, G-C4-haloalkyl, G-Aikoxy or i-4-haloalkoxy can be, or
  • R 5 is aryl or hetaryl, where the aforementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF% SCN, GG-alkylamino, di- (GG) -alkylamino , Hydroxy, COOK, G-Galkyl, GG-cycloalkyl, GG-haloalkyl, G-Ce-alkoxy, GG-haloalkoxy, Cs-Ce-halocycle, C3-C6-halocycloalkyl-C 1 -G-alkyl, i - (,, - alkoxy G -G -alkvl, C i -G haloalkoxy-C i -G alkyl, C; -G - Al koxy-C; -G -alkyloxy, cyano-G-C6-alkyl,
  • R 51 is hydrogen or G-G-alkyl, GG.-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C -heterocyclyl, where the abovementioned radicals, where appropriate, being independent of one another, are simple up to three times by halogen or simply by nitro, cyano, C 3 -G -cycloalkyl, G -C "-alkoxy, GG-Haiogenaikoxy, G-Ce-alkylthio, C 1 -C 6 -alkylsulfmyl, G-Ce-alkylsulfonyl, C 1 -ce-alkylcarbonyl, C: Y-alkoxy-imino-C 1 -G-alkyl, GG-cycloalkylcarbonyl, C 1 -C 10 -alkenylcarbonyl, GG-haloalkylcarbon
  • R 51 represents aryl or hetaryl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di (C 1 -C 4) C6) -alkylamino, hydroxy, COOK, GG-alkyl, GG-cycloalkyl, GG-haloalkyl, GG-alkoxy, GG-haloalkoxy, C -.- ( ' , -halocycloalkyl, C -, - ( ' , -Ha!
  • R 52 is C 1 -C 6 -acylyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted may be substituted and the substituents are independently selected from halogen, nitro, cyano, C3-C6-cycloalkyl, GC 6 alkoxy, (VC.
  • R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, Sf.sup.1, SCN, (VO.-alkylanino, di (C 1 -C 4) C 6 ) -alkylamino, hydroxy, COOH, C 1 -C 6 -acyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C -halocycloalkyl, C 2 -C 5 -alkyl Ce-halocycloalkyl-Ci-Ce-alkyl, G-Ce-alkoxy-Ci-Ce alkyl, C, -C, haloalkoxy-C
  • R 53 is hydrogen, G-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -G -alkoxy-C 1 -G -alk l, GG-alkoxycarbonyl, GG-Alkyiearbonyl, aryl, hetaryl, arylcarbonyl or hetarylcarbonyl, wherein aryl and hetaryl each one to three times by halogen, cyano, nitro, G-alkyl, GG-haloalkyl.
  • GG-alkoxy or GG-haloalkoxy may be substituted,
  • R 54 is hydrogen or GG-alkyl, GG-Alkenyi, C.-C, -alkynyl. GG-cycloalkyl or GG-cycloalkyl-C 1 -G-alkyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to five times by halogen or simply by cyano, nitro, hydroxy, GG-alkyl, GG-cycloalkyl, GC 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkylthio, GG-alkylsulfmyl, GG-alkylsulfonyl, GG-alkoxycarbonyl, GG-alkylcarbonyl or C3-C6-trialkylsilyl, or
  • R - and R 54 may be connected to each other via two to six carbon atoms and form a ring, which optionally additionally contains another atom from the series OS or N and optionally monosubstituted to four times with G-alkyl, halogen, cyano, amino or G -G alkoxy may be substituted,
  • R 55 is GG-alkyl, GG-cycloalkyl, G-Ce-haloalkyl, GG-halio-cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -G -alkyl, GG-halo-cycloalkyl-C 1 -G-alkyl, cyano -C 1 -G alkyl.
  • Aryl is GG-alkyl, GG-cycloalkyl, G-Ce-haloalkyl, GG-halio-cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -G -alkyl, GG-halo-cycloalkyl-C 1 -G-alkyl, cyano
  • G-G haloalkoxy, GG-halocycloalkyl or G-Ce-alkoxy-G-Ce-alkyl may be substituted, R 56 for Ci-Ce alkyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 3 -C 6 halocycloalkyl, GG - cycloalkyl-C i -G alkyl. C 3 -C 6 -halocycloalkyl-C 1 -G -alkyl. Cyano-C i -G alkyl.
  • R represents C 1 -C 6 -alkyl, C 3 -G-cycloalkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 6 -C 6 -halocycloalkyl-C 1 -C 6 alkyl, cyano-C iC 6 alkyl, Ci-C 6 -...
  • R 7 is hydrogen, CVG-alkyl, GG-alkenyl, GG-alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -j-alkoxy-C 1 -G -alkyl, G-Ce-alkoxycarbonyl or C 1-Ce-alkylcarbonyl,
  • R 7a is hydrogen
  • G is -C ( , -alkyl, C 1 -G, -alkenyl, C 2 -C 6 -alkynyl, C 3 -C -cycloalkyl
  • G is -G-alkoxy-G - Ct-alkyl
  • G- Ce-alkoxycarbonyl or Ci-Ce-Aikyicarbonyi stands,
  • R 8 is hydrogen or C i - ( ' (alkyl, ( ' , - ) , - AI kenyl or C 2 -Ce-Aikinyi, where the abovementioned radicals are optionally independently from one another up to five times by halogen or simply by cyano , nitro, hydroxy, -G- G alkyl, C-C., - ( 'ycloalkyl, GC 4 alkoxy, haloalkoxy 4 GC, GC 4 - alkylthio, Ci-C 4 -Alkyisulflnyi, GC 4 alkylsulfonyl, GC 4 Alkylsulfimino, GC 4 -alkyl-sulfimino-C 1 -gi-alkyl, C 1 -C 4 -alkylsulfimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alky
  • R 8 is aryl-G-G-alkyl, heteroaryl-C; -G alkyl. C 3 -C 2 cycloalkyl, (- i - ( 'ycloiilkyl-G-G-C 4 alkyl or -Ci2-Bicycloalkyi, where the abovementioned radicals can be optionally substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C i - ( ' »alkyl, GG-cycloalkyl, GG-cycloalkylamino, G -Ct-alkoxy, GC 4 -Haioaikoxy, GC 4 alkylthio, Ci-C 4 -Alkylsuifinyl, GC 4 Alkylsulfonyl, GC 4 -alkylsulfimino, C 2 -Ce-alkoxycarbonyi or C 2 -C 6 -al
  • R 8 represents a mono- or polysubstituted by identical or different substituent 5 or 6-membered aromatic or heteroaromatic ring, a 4- to 6-membered partially saturated ring or saturated heterocyclic ring, or a saturated or aromatic heterocyclic ring, which optionally contains one to three heteroatoms from the series O, S or
  • N May contain N and may optionally be mono- or polysubstituted, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, GG-alkyl, GC ⁇ -Cycloalkvl, C3 -G -cycloalkylamino, G -G Alkoxy, GG-haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsuifinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfimino, GG-alkoxycarbonyl or C 2 -C 6 -alkyicarbonyl, or
  • R and R 8 may be connected to each other via two to six carbon atoms and form a ring which optionally additionally contains a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with GG-alkyl, halogen, cyano, amino or G-G Alkoxy may be substituted,
  • R 9 is hydrogen, fluorine, chlorine, GC 4 -alkyi, GG-cycloalkyl or GC 4 -Haloaikyi
  • R 9a is hydrogen, fluorine, chlorine, G-alkyl, C 3 -C 6 -cycloalkyl or GG-haloalkyl
  • R 10 is hydrogen, fluorine, chlorine or GG-alkyl
  • R 10a is hydrogen, fluorine, chlorine or GG-alkyl.
  • Preferred (embodiment 2-2) are the compounds of the formula (I) in which
  • Q 1 and Q together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
  • T is R 1 -OR 6 , -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ), W is O,
  • U is a cycle of the series U-1, U-2, U-5, U-6, U-9, U-10, U-20 or U-23,
  • X a is halogen, nitro, cyano, SF 5 , GC 4 alkyl, GC 4 haloalkyl, GG alkoxy, GG haloalkoxy, GC 4 alkoxy GC 4 alkyl, cyano GC 4 alkyl, GG alkenyl , GG-alkynyl, CV alkylthio.
  • R 1 , R 2 , R. R 4 each unabliängig another represent hydrogen, halogen, cyano, CVC 'i-alkyl, C3-Ce-cycloalkyl, C -C haloalkyl .i. CVC.; - alkoxy, C ' i -C i - halogenal kxy.
  • Ci-C are 4 alkylsulfonyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, C1-C4 alkoxycarbonyl, aryl or Hetaiyl, where aryl and hetaryl which is optionally mono- to trisubstituted by identical or different by halogen, cyano, C VCV alkyl, C i -C ⁇ -alkoxy, C VC .i-haloalkyl. May be substituted by 1-C haloalkoxy or C 1 -C 4 -alkylthio,
  • R 5 is CH 2 Y
  • ring N atoms in Y-13, Y-14 and Y-16 are not substituted by halogen, nitro, cyano, GG-alkoxy, G-Gi-haloalkoxy or G - Cis-alkoxy-C 1-6 alkyloxy, is 0, 1 or 2, is 0, 1 or 2, R 51 is hydrogen or GG-alkyl, C 2 -C 4 -arycyl, GG-alkynyl, GG-cycloalkyl or GG-heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, C 3 -C 4 -alkyl.
  • R 51 is aryl or Hetaryi, where the aforementioned radicals optionally may be mono- to trisubstituted and the substituents are independently selected from halo, nitro, cyano, Ci-C 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkylthio or GC 4 -alkylsulfonyl,
  • R 52 is G-G-alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkyny, GG-cycloalkyl or GG-heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano , GC 4 -Aikylthio, GC 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, C i -C 4 alkylcarbonyl, Ci-C4--Aikoxyimino GC 4 -alkyl 4 alkoxy, GC 4 -Halogenaikoxy, GC, G, C 4 alkoxycarbonyl, C i -C 4 alkylsulfonyl, C i -C 4 haloalkylsulfonyl, GG-
  • Alkylaminocarbonyl, aryl or hetaryi may be substituted, wherein aryl and hetaryi may each be monosubstituted to trisubstituted by halogen, cyano, nitro, G-G-alkyl, G-G-haloalkyl, G-G-alkoxy or G -Gi-haloalkoxy, or
  • R 52 represents aryl or hetaryin, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, GG-acyl, GC 4 -haloalkyl, GG-alkoxy, GG-haloalkoxy, GC 4 -alkyl or GG-alkylsulfonyl,
  • R 53 is hydrogen, G is -Gh-alkyl, C 1 -C 4 -alkoxycarbonyl, GC 6 -Aikylcarbonyi, aryl, hetaryi, arylcarbonyl or hetarylcarbonyl, wherein aryl, hetaryic, arylcarbonyl or hetarylcarbonyl each just to three times by halogen, cyano , Nitro, G-alkyl, GG-haloalkyl, G-C 4 -alkoxy or G-Gi-haloalkoxy,
  • R 7 is hydrogen, C 1 -C 4 -alkyi, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, (i -CVAI koxy-C ⁇ -i-Aiky l, C ⁇ -C AI koxycarbonyl or Ci-C4-alkylcarbonyl,
  • R 7a 4 -alkoxycarbonyl or C i -C 4 alkylcarbonyl hydrogen, G-CVAlkyl, Ci-C,
  • R 8 is hydrogen or C jC ' -i-alkyl, CyCVAlkenyl or C.-Ci-alkynyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen, or simply by cyano, GC 4 -alkoxy, GC 4 - Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkyisulfinyl, GC 4 - alkylsulphonyl, C i -C 4 alkoxy carbonyl, or Ci-C4-alkylcarbonyl can be substituted or
  • R 8 is phenyimethyl, phenylethyl, pyridylmethyl, Cs-Ce-cycloalkyl, C 3 -C 6 -cycloalkyl> -Ci-C 4 -alkyi or C .iC s- Bi eye loa! kyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C i -C alkyl, C s -C i alkoxy, C1 -C4 haloalkoxy.
  • CVC i-alkylthio Ci-C 4 -Aikylsulflnyl, C 1 -C 4 alkylsulfonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 alkylcarbonyl, or
  • R 8 for Phenyl, Pyridy! , Pyrimidinyl, thia / olyl, thiadiazolyl, oxa / olyl, pyra / olyl, thienyl or furanyi, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are independently selected from halogen, cyano, nitro , hydroxy, amino, C i -C i-alkyl, -CVAIkinyl, C 1 -C 4 - Haiogenalkyi, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 - Alkylsulfmyl or Ci- C 4 alkylsulfonyl, C 2 -Ce-Alkoxycarbonyi or C 2 -C 6 -alkylcarbonyl,
  • R 9 is hydrogen, fluorine, chlorine or C OAikyl
  • R 9a is hydrogen, fluorine, chlorine or Ci-C 4 alkyl
  • R 10 is hydrogen, fluorine, chlorine or Ci-C 4 alkyl
  • RIOA represents hydrogen, fluorine, chlorine or G-CVAlkyl.
  • Q 1 and Q 2 together represent the radical Al which, together with the C and N atoms to which it is attached, forms a 6-membered aromatic ring
  • T represents R 5 , -Oir. -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ),
  • G is a bond, for -C (R 9 ) (R 10 ) -, or for C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
  • U is a cycle of the series Ul, U- 2, U-5, U-6, U-9, U-20 or U-23,
  • X a is halogen, nitro, cyano, SF 5 , C 1 -C 4 -alkyl, C 1 -C 4 -Haiogenalkyl, Ci-C 4 -alkoxy, GC 4 - haloalkoxy, Ci-C 4 -alkoxy-GC 4 -aikyl, cyano -C. -C-alkyl.
  • R 1 , R 2 , R 3 , R 4 are each independently hydrogen, halogen, cyano, GC 4 -alkyl, G-G-cycloalkyl, G-C 4 -haloalkyl, GC 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkoxy-GC 4 - alkyl.
  • C is -G-alkenyl, C 2 -C 4 -alkenyloxy, C 3 -C 4 -alkynyl, C 3 -C 4 -alkynyloxy, GC 4 -alkylthio, Ci-C 4 -alkylsulfmyl, Ci-C 4 -alkylsulfonyl, Ci -C 4 -alkoxyimino-GC 4 -alkyl, GC 4 -
  • X b is halogen, nitro, cyano, GG-alkyl, C 3 -C 6 -cycloalkyl, GG-haloalkyl.
  • R 51 is hydrogen or C 4 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are optionally independent monosubstituted to trisubstituted by halogen or simply by cyano, G-CVAlkoxy, Ci-CJ-halogeno, C; -C; -alkylthio, G-C4-alkylsulfinyl, G-C4-alkylsulfonyl, -Ci AI kylcarbony 1, C ⁇ : -C - A 1 kxy ⁇ -C 1 - (-alkenyl, C 1 -C 4 -alkoxycarbonyl, C 1 -G -alkylsulfonyl, C 1 -C 4 -hal
  • Alkylaminocarbonyl, aryl or hetaryl may be substituted, wherein aryl and hetaryl may each be monosubstituted to trisubstituted by halogen, cyano, nitro, G-G-alkyl, G-G-Haloalkyi, G-G-alkoxy or G-G; -haloalkoxy, or
  • R 51 represents aryl or hetaryin, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, cyano, GG-alkyl, C •, -G -haloalkyl. GG-alkoxy, ⁇ -G - H al ogenal kxy.
  • Ci-i-alkylthio or GC 4 -alkylsulfonyl R 52 is C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are, if desired, independently of one another simply up to three times by halogen or simply by cyano, G -CVAlkoxy, C -G - H al ogena 1 ko x y.
  • Alkylaminocarbonyl, aryl or hetaryl can be substituted, wherein aryl and hetaryl each one to three times by halogen, cyano, nitro, Ci-C 4 alkyl, GC 4 -Haloaikyl, C ' s -C ' t-alkoxy or C ' iC.
  • R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 - Ci-haloalkyl, GC 4 -alkoxy, C -alkoxy 4 -Halogena!, C 4 alkylthio or C 4 alkylsulfonyl,
  • R 53 is hydrogen, G -C -alkyl.
  • GG-alkoxy or C 1 -C 4 -haloalkoxy may be substituted,
  • R 54 4 alkyl, C -G-alkenyl, C 2 -C 4 -Alkinyi or C 3 -C 4 -Cycioaikyi hydrogen or GC, where the abovementioned radicals are optionally substituted independently of one another mono- to pentasubstituted by halogen or monosubstituted by cyano , C 4 alkyl, C -.- C i-Cy loalkyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, G CVAlkylthio Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl or phenyl can be substituted
  • R 6 is -G-G alkyl, Ci-C4 haloalkyl, cycloalkyl GG -, -G-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, aryl-Ci-C4-alkyl or hetaryl C 1 -C 4 -alkyl, where aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl are optionally mono- to trisubstituted by identical or different halo, cyano, nitro, or
  • C 1-alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or G-G-H- ⁇ -o-1-koxy may be substituted
  • R 7 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, i - (-; -alkoxy-C -C . Alkyl, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylcarbonyl,
  • R 7a is hydrogen, Ci-C 4 -alkyl, Ci-C 4 alkoxy carbonyl or Ci-C is 4 alkylcarbonyl
  • R 8 represents hydrogen or GC 4 -A! Kyl, C 2 -C 4 alkenyl or C C 2 -C 4 -alkynyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, or simply by Cyano, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, GC 4 - alkylsulphonyl, C i -C 4 alkoxy carbonyl, or Ci-C 4 - Alkylcarbonyl may be substituted, or phenylmetfayl, Phenylethyi, pyridylmethyl, CVG cycloalky
  • radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents independently of one another are selected from halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, GG-haloalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl C 1 -C 4 -alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -alkylcarbonyl, or
  • R 8 represents phenyl, pyridyl, pyrimidinyl, thia / olyl, oxazolyl, pyrazolyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently from halogen, cyano, nitro , hydroxy, amino, GC 4 -Alkyi, GC 4 -alkoxy, GC 4 -Haioaikoxy, GG-alkylthio, Ci-C 4 -Alkylsulfmyl or C i -C 4 -alkylsulfonyl, or GG-GG Alkoxyearbonyi
  • R 9 is hydrogen, fluorine, chlorine or GC 4 -acyl
  • R 9a is hydrogen, fluorine, chlorine or G-alkyl
  • R 10 is hydrogen, fluorine, chlorine or GC 4 -alkyi
  • T represents R ⁇ -OR '-N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ),
  • G is a bond or -C (R 9 ) (R 10 ) -,
  • U is a cycle of the series U-2, U-9, U-10 or U-23
  • X a is halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl
  • n is 0, 1 or 2
  • R 1 , R 2 , R 4 and R 4 each independently of one another represent a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C -haloalkyl, (C 1 -C 4) -alkoxy, C -C -alkyl Haloalkoxy, G -C -alkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, C 3 -C 4 -alkynyl, GG-alkynyloxy, GC 4 -alkylthio, C i - C 4 alkylsulfinyl or C i -C 4 alkylsulfonyl,
  • R 5 is CH 2 Y.
  • Y is hydrogen, Cl, Br, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y -5, Y-6 or Y-7,
  • X b is halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methylamino carbonyl, methylcarbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, m is 0, 1 or 2, p is 0, 1 or 2 stands,
  • R 51 is hydrogen or C j -Ch-alkyl, C 2 -C 4 -alkenyl, GG-alkynyl or C 3 -C 6 -cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, Cs-Cene or Cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, G-G-alkylthio.
  • Ci-C 4 -Alkylsulfmyl, C i -C 4 alkylsulfonyl, C i -C 4 alkylcarbonyl, C ⁇ -C 4 alk oxy carboxylic y is 1 or C ⁇ -G-Al can be alkyl substituted sui fonyl, or just may be substituted by phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, which may in turn be substituted, independently of each other, simply to three times by halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or
  • R 51 represents phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy G is -G-alkyl or C 3 -C 6 -cycloalkyl, wherein the aforesaid groups optionally may be mono- to trisubstituted and the substituents are independently selected from halogen, cyano, C i -Ct-alkoxy, Ci- C4-haloalkoxy, Ci-C4-alkylthio, Ci-C 4 -Alkylsulfmyl , Ci-C 4 alkylsulfonyl, GC 4 - alkylcarbonyl, Ci-C 4 -
  • Ci-C 4 -alkoxy-GC 4 alkyl for hydrogen, GC 4 -alkyl, Ci-C 4 alkoxy, Ci-C 4 alkoxy-Ci-C -Aikyi, Ci-C 4 -alkoxycarbonyl or Ci-C4-alkylcarbonyl, represents hydrogen, GC 4 -Alkyi, C i -C 4 alkoxy carbonyl, or Ci-C 4 is -Aikylearbonyl, hydrogen or Ci-C 4 -alkyl, C - t Alkenyl or C.-C.
  • Alkynyl the abovementioned radicals optionally being independently of one another monosubstituted to trisubstituted by halogen or simply by cyano, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfmy l, methylsulfonyl or ethylsulfonyl, or R 8 is phenylmethyl.
  • R 8 is phenyl, pyridyl, pyrimidinyl, thia / olyl. Thiadiazolyl, oxa / olyl. Pyrazolyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently of one another from halogen, cyano, nitro, methyl, ethyl, ethynyl, trifluoromethyl, pentafluoroethyl,
  • R and R 8 together represent a ( ' , - * * alkyl chain
  • R 9 is hydrogen, fluorine, chlorine, methyl or ethyl
  • R ! 0 is hydrogen, fluorine, chlorine, methyl or ethyl.
  • Q 1 and Q 2 together represent the rest of Al, the to which it is attached together with the carbon and nitrogen atom, form a 6-membered aromatic ring,
  • G is a bond or -C (R 9 ) (R 10 ) -,
  • U is a cycle of the series U-2, U-9 or U-23
  • X 1 is halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl
  • n is 0 , 1 or 2
  • R 3 , R 4 are each independently a radical selected from the group of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C -alkoxy, C 1 -C 5 -haloalkoxy.
  • R 5 is CH 2 Y.
  • Y is hydrogen, C 1, Br, OW-S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5, Y-6 or Y-7 stands,
  • X b is halogen, cyano, methyl, ethyl, trifluoromethyl, methylamino carbonyl, methylcarbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, m is 0, I or 2, p is 0, 1 or 2 stands,
  • R 51 represents hydrogen or C 1 -C 4 -alkyl, GG-alkenyl or G-Gi-alkynyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, GC 4 -alkoxy, G-C 4 -haloalkoxy , Ci-C 4 -Alkylsulfinyi, Ci-C 4 alkylsulfonyl, GC 4 4 alkylthio, Ci-C - alkylcarbonyl, Ci-C 4 -alkoxycarbonyl or C i -C 4 alkylsulfonyl may be substituted, or simply by phenyl, Thienyi, pyridyl, pyrimidinyl or pyrazolyl may be substituted, which in turn may each independently be monosubstituted to trisubstituted by halogen, cyano, methyl, ethy
  • R 51 is phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
  • R 52 is GC 4 -alkyl or GG-cycloalkyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, GC 4 -alkoxy, G-C 4 -haloakoxy, GC - Alkyithio, Ci-C 4 -Aikylsuifinyl, GC 4 alkylsulfonyl, GC 4 - alkylcarbonyl, GC 4 alkoxycarbonyl or> -G- alkylsulfonyl and from phenyl, thienyi, pyridyl, pyrimidinyl, pyrazolyl, each independently from one another to trisubstituted by Halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or
  • R 52 is phenyi, thienyl, pyridyl, pyrimidinyl or pyiazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy .
  • R 53 is hydrogen, CVC-alkyl, C; -C 4 - Al koxycarbonyl or Ci-Ce-Aikylcarbonyl,
  • R 54 is hydrogen or C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen, or simply may be substituted by cyano, methyl, ethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or phenyi,
  • R 6 is Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 -Cycloallcyi-Ci-C 4 -alk> d, Ci-C4-alkoxy-Ci-C 4 -alkyl,
  • R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -acoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyi or C 1 -C 4 -alkylcarbonyl,
  • R 7a 4 alkyl, Ci-C 4 -Alkoxycarbonyi or C i -C 4 alkylcarbonyl, hydrogen, Ci-C,
  • R 8 is hydrogen or C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 1 -C 6 -alkynyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, methoxy, ethoxy, difluoromethoxy, Trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or
  • R 8 is phenyimethyl, phenylethyl, pyridylmethyl, pyridylethyl, CVG-cycloalkyl or C 3 -C 6 -cycloalkyl-C i -C 4 -alkyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, or
  • R 8 is phenyl, pyridyl, pyrimidinyl, thiazolyl, oxazolyl, pyrazolyl, thienyl or furanyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, Trifluoromethyl, methoxy, ethoxy, trifuormethoxy, methylthio,
  • R 9 is hydrogen, fluorine, chlorine, methyl or ethyl
  • R 10 is hydrogen, fluorine, chlorine, methyl or ethyl.
  • Particularly preferred (embodiment 4-2) are the compounds of formula (I) in which
  • Q 1 and O together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
  • T is R 1 -OR "or -N (R 7 ) (R 8 ),
  • W is O
  • G is a bond or -C (R 9 ) (R 10 ) -
  • U stands for U-2, U-9, U-10 or U-23,
  • X a is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy or cyano
  • n is 0, 1 or 2
  • R 1 , R ⁇ R 3 , R 4 are each independently a radical from the series Are hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy,
  • R 5 is CHY
  • Y is hydrogen
  • C is chloro.
  • X b represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl and isopropyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2,
  • R is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pent-3-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl , Cyclohexylmethyl, 2,2,2-trifluoroethyl, 2-methoxyethyl,
  • Methoxycarbonylmethyl phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, phenylmethyl, 4-fluoro-phenylmethyl, 3 Fluorophenylmethyl, 2-fluoro-phenylmethyl, pyrid-3-yl, 6-chloro-pyrid-3-yl, pyridyl-2-yl or 1-methylpyrazol-5-yl,
  • R 52 is methyl, ethyl, n- or iso-propyl. Phenyl or phenylmethyl,
  • R 53 is hydrogen, methyl, ethyl, methylcarbonyl or ethylcarbonyl,
  • R 54 is methyl, ethyl, n- or iso-propyl, cyclopropyl or phenylmethyl,
  • R 6 is methyl, ethyl or n- or isopropyl
  • R is hydrogen, methyl or ethyl
  • R 8 is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, trifluoroethyl, cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, cyanocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanocyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl , optionally mono- to disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, cyano or nitro-substituted phenyl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted phenyl
  • Bromine methyl, trifluoromethyl, cyano, nitro or ethynyl-substituted pyridyl-2-yi, optionally mono- to disubstituted independently of each other by fluorine-chlorine or methoxy-substituted pyrid-4-yl. optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 1, 3-pyrimidin-2-yl.
  • R 10 is hydrogen
  • T is R 1 -OR 6 or -N (R 7 ) (R 8 ),
  • G is a bond or - € (R 9 ) (R 10 ) -, U is U-2, U-9 or U-23,
  • X a is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy or cyano, n is 0, 1 or 2,
  • R 1 , R ⁇ R 3 , R 4 are each independently a radical selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso -
  • R 5 stands for C ITY
  • Y is hydrogen, chlorine, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2. Y-3, Y-4, Y-5, Y-6 or Y-7,
  • X b is fluorine, chlorine, bromine, cyano, methyl, ethyl, n- and iso-propyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0 , 1 or 2, R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, 2-methoxyethyl, methoxy carbonylmethyl, phenyl, 2-F-phenyl, 3-F-Phenyi, 4-F-phenyl, 2-Cl-phenyl, 3-Cl-phenyl, 4-Cl-Pheny !, phenylmethyl, 4-F-phenylmethyl, 3-F-phenylmethyl, 2-F-phenylmethyl, pyrid
  • R 52 is methyl, ethyl, n- or iso-propyl, phenyl or phenylmethyl,
  • R 53 is hydrogen, methyl, ethyl, methylcarbonyl or ethylcarbonyl,
  • R 1 is methyl, ethyl, n- or iso-propyl, cyclopropyl or phenylmethyl,
  • R ' is methyl, ethyl or n- or isopropyl
  • R is hydrogen, methyl or ethyl
  • R 8 is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl. Trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, optionally substituted by fluorine or chlorine-substituted phenyl, optionally substituted by fluorine or chlorine-substituted phenylmethyl, optionally substituted by fluorine or chlorine-substituted 1-phenyl ethyl, optionally substituted by fluorine or chlorine-substituted 2-phenylethyl, optionally fluorine or chlorine-substituted pyrid-3-yl, optionally fluorine- or chlorine-substituted pyridyl-2-yl or optionally fluorine- or chlorine-substituted pyrid-4-yl,
  • R 9 is hydrogen or methyl
  • R 10 is hydrogen
  • Q 1 and Q- together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
  • T is R 1 -OR "or -N (R 7 ) (R 8 ),
  • G is -C (R 9 ) (R 10 ) -,
  • U stands for U-2, U-9, U-10 or U-23,
  • X a is fluorine, chlorine, methyl, trifluoromethyl or methoxy
  • n is 0, 1 or 2
  • R 3 , R 4 each independently represent a radical from the series consisting of hydrogen, fluorine, chlorine, cyano, methyl, methoxy, ethoxy, methylthio, trifluoromethyl or trifluoromethoxy,
  • R 5 is CHY
  • Y is hydrogen, chlorine.
  • X b is chlorine, cyano, methyl, methoxy, methylthio, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2,
  • R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, t-butyl, pent-3-yl, cyclopentyl, cyclohexyl, 2,2,2-trifluoroethylene, 2-methoxyethyl, methoxycarbonylmethyl, phenyl, 4-fluoro Phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl. Phenylmethyl, 4-fluoro-phenylmethyl, pyrid-3-yl. 6 is chloro-pyrid-3-yl, pyrid-2-yl or 1-methylpyrazoi-5-yl, R 52 is methyl, ethyl, isopropyl, phenyl or phenylmethyl,
  • R 53 is hydrogen, methylcarbonyl or ethylcarbonyl
  • R 54 is methyl, ethyl, cyclopropyl or phenylmethyl
  • R is hydrogen
  • R 8 is methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, trifluoroethyl, cyclopropyl, 1-cyanocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyano-cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl , optionally mono- to disubstituted independently of one another by fluorine, chlorine.
  • 2-phenylethyl optionally mono- to disubstituted independently of one another by chlorine or methyl-substituted pyrid-3-yl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted pyrid-2-yl, optionally simply by bromine, methyl, trifluoromethyl, cyano, nitro or ethynyl-substituted pyrid-2-yl.
  • R ! 0 is hydrogen
  • T is R 1 -Oir or -N (R 7 ) (R 8 ),
  • G is -C (R 9 ) (R 10 ) -, U is U-2, U-9 or U-23,
  • X a is chlorine, trifluoromethyl or methoxy, n is 0, 1 or 2,
  • R 1 , R 2 , R 4 independently of one another each represent a radical from the group consisting of hydrogen, fluorine, chlorine, cyano, methyl, ethoxy, methylthio, trifluoromethyl or trifluoromethoxy, IV represents CH: Y,
  • Y is hydrogen, chlorine, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5 , Y-6 stands,
  • X b is chlorine, cyano, methyl, methoxy, methylthio, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2, R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, 2-methoxyethyl, methoxycarbonylmethyl,
  • R 52 is methyl, ethyl, iso-propyl, phenyl or phenylmethyl
  • R 53 is hydrogen, methylcarbonyl or ethylcarbonyi
  • R 54 is methyl, ethyl, cyclopropyl or phenylmethyl
  • R is hydrogen
  • R 8 represents methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, optionally chlorine-substituted phenyl, optionally phenyl-substituted chlorine, optionally chlorine-substituted 1 - Phenylethyl, optionally chlorine-substituted 2-phenylethyl or optionally chlorine-substituted pyrid-3-yl,
  • R ' is hydrogen or methyl
  • R 10 is hydrogen
  • the invention relates to the compounds of the formula (I) in which W is O.
  • the invention relates to the compounds of the formula (I) in which W stands for S.
  • U is U-2, U-9, U-10 or U-23, all other groups, radicals and substituents being those described above in the embodiment (1-1) or in the embodiment ( 1-2) or in embodiment (2-1) or in embodiment (2-2) or in embodiment (3-1) or in embodiment (3-2) or in embodiment (4-1) or in embodiment (4-2) 2) or in the embodiment (5-1) or in the embodiment (5-2) have meaning described.
  • the invention relates to the compounds of the formula (I-
  • the invention relates to the compounds of the formula (I-2).
  • the invention relates to the compounds of the formula (I-3).
  • the invention relates to the compounds of the formula (I-
  • the invention relates to the compounds of the formula (I-5)
  • the invention relates to the compounds of the formula (I-6)
  • the invention relates to the compounds of the formula (I-7)
  • the invention relates to the compounds of the formula (I)
  • Preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above is preferred, wherein each embodiment described above as preferred represents an independent combination, in particular a combination as described in embodiment 2-1 or in embodiment 2-2 , Compounds of the formula (I) which contain a combination of the definitions given above as being more preferred are also preferred according to the invention, wherein each embodiment described above as further preferred represents an independent combination, in particular a combination as described in embodiment 3-1 or in an embodiment 3-2.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • the compounds of formula (I) are mesoionic internal salts.
  • Internal salts also known as zwitterions, are electronically neutral molecules that formally express positive and negative charges carry different atoms.
  • the compounds of formula (I) can be formally represented by various structures carrying the positive and negative charges on different atoms. The following figure shows 4 possible forms of presentation without excluding other possible forms of representation. All structural representations are equivalent. For reasons of simplification, only one possible structural representation is selected here in each case. This representation is representative of all valence bond structure representations.
  • the compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. are present as geometric and / or optical isomers or isomer mixtures in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
  • alkyl either alone or in combination with other terms such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso -Pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, hex
  • alkenyl is a linear or branched C 2 -C 12 -alkenyl radical which has at least one double bond, for example vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1, 3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexene vi, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, of which preferred are C 2 -C 6 -alkenyl radicals and particularly preferred are C 2 -C 4 -alkenyl radicals.
  • alkynyl is according to the invention a linear or branched C 2 -C 12 -alkynyl radical which has at least one triple bond, for example ethynyl, Propionyl and propargyl, understood, are preferred C3-C6-alkynyl radicals and particularly preferred are C3-C4-Aikinylreste.
  • the alkynyl radical may also have at least one double bond.
  • cycloalkyl either in isolation or in combination with further terms, according to the invention is understood to mean a C 3 -C 8 -cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, Preference is given here to C 3 -C 6 -cycloalkyl radicals.
  • aryl an aromatic radical having 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or
  • Phenanthrenyl particularly preferably phenyl, understood.
  • aralkyl is understood to mean a combination of radicals "aryl” and “alkyl” defined according to the invention, the radical generally being bound via the alkyl group, examples of which are benzyl, phenylethyl or Methylbenzyl, with benzyi being particularly preferred.
  • hetaryl means a mono-, bi- or tricyclic heterocyclic group of C atoms and at least one heteroatom, wherein at least one cycle is aromatic.
  • the hetaryl group contains 3, 4, 5 or 6 carbon atoms selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1 .2.4-Triazoly 1, oxazolyl, isoxazolyl, thiazolyi , Isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl , 1, 3, 4-thiadiazolyl, 1, 2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl,
  • heterocyclyl means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring of C atoms and at least one heteroatom in the ring
  • the heterocyclyl group contains 3, 4, 5 or 6 C atoms and 1 or 2 heteroatoms from the series oxygen, sulfur or nitrogen
  • heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, T etrahydro furyl.
  • halo-substituted radicals for example "haloalkyl” are radicals which are mono- or polysubstituted to the maximum possible number of substituents halogenated radicals can be identical or different halogen halogen atoms.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
  • alkoxy either alone or in combination with other terms such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “aikyl” having the meaning given above.
  • the compounds of the formula (I) can be synthesized, for example, by the methods given in Schemes 1 to 10.
  • the radicals indicated in the formulas R 1 , R 2 , R 3 , R 4 , R ⁇ R ', R have.
  • Amines of the formula (V) are commercially available or known in the literature.
  • Compounds of formula (Id) can be obtained as shown in Scheme 4 from compounds of formula (Ia) by well-known methods by reaction with alcoholates or alcohols in the presence of a base such as sodium hydride.
  • Compounds of formulas (VI) and (VII) are commercially available or known in the literature.
  • Compounds of formula (Ii) may be prepared by generally known methods from compounds of formula (Ia) by reactions with thiolates or thiols in the presence of a base such as sodium hydride as shown in Scheme 5.
  • Compounds of formula (Ii) can then be prepared by generally known methods with an oxidizing agent, such as meta-C Ii! Rperben zoeklare be oxidized to sulfoxides and sulfones of the formula (Ig).
  • Compounds of formula (Ih) may be obtained from compounds of formula (Ia) by reactions with amino compounds of formula (IX) according to well-known procedures in the presence of a base such as triethylamine as shown in Scheme 6. In the same way, other amino compounds such as hydrazines can be implemented.
  • Formula (XII) are reacted in the presence of a base.
  • compounds of formula (I) can be prepared by the methods described above. If individual compounds can not be prepared by the methods described above, the synthesis is possible by derivatization of other compounds of formula (I) or by individual modifications of the methods described. For example, it may be advantageous to prepare certain compounds of formula (I) from other compounds of formula (I), for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, oxygenation, ilogenation. Acylation, alkylation and the like.
  • the processes according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using a diluent. As a diluent for Implementation of the method according to the invention in addition to water, all inert solvents in question.
  • Halogenated hydrocarbons eg, chlorohydrocarbons, such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (eg Methanol, ethanol, isopropanol, butanol), ethers (eg, ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether, di
  • reaction temperatures can be varied within a substantial range when carrying out the processes according to the invention. In general, temperatures between 30.degree. C. and + 150.degree. C., preferably between -10.degree. C. and + 100.degree. C., are used.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 bar and 15 bar. To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in to use a larger surplus.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, optionally also under a
  • Inert gas atmosphere e.g., under nitrogen, argon or helium
  • the reaction mixture is generally stirred for several hours at the required temperature.
  • the work-up is carried out by customary methods (see the preparation examples).
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • amidine bases or guanidine bases eg 7-methyl-1,5,7-triaza -bicyclo (4.4.0) dec-5-ene (MTBD); diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1, 8-diazabicyclo (5.4.0) undecene ( DBU), cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-l, 8-naphthalenediamine,
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • Pentamethylpiperidine and amines, in particular tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, ⁇ , ⁇ -dimethyl-toluidine, N, N-dimethyl-p- aminopyridine, N-methyl-pyrrolidine, N-methylpiperidine, N-methyl-imidazole, N-methylpyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, Quinoline, oc-picoline, ⁇ -picoline, pyrimidine, acridine, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylenediamine, ⁇ , ⁇ , ⁇
  • mineral acids for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids for example aluminum (III) chloride, boron trifluoride or etherate
  • Titanium (IV) chloride, tin (IV) chloride eg formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid
  • mineral acids for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids for example aluminum (III)
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises both pure stereoisomers and any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as insecticides, in particular herbicides.
  • insecticides in particular herbicides.
  • pest control always always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the crop and to control animal pests, in particular insects , Arachnids, helminths, in particular nematodes, and mollusks, which are found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in storage and materials protection and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.
  • measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
  • the term “hygiene sector” covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry etc.
  • the term “hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
  • hygiene pests include the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as a chelating agent. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Blatta orientalis Blattparta asahinai, Blattelia germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., Z. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Chaetocnema confmis Chaetocnema denticulata
  • Chaetocnema ectypa Cleonus mendicus, Conoderus spp.
  • Cosmopolites spp. E.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g.
  • Curculio caryae Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes fermgineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., E.g.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diioboderus spp., Epicaerus spp., Epilachna spp., E.g. Epiiachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Heiluia and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajuius, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemiineata, Leucoptera spp., E.g.
  • Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oumema spp., E.g. Oulema melanopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyilophaga spp., Phyllophaga. Phyllotreta spp., Z.
  • Phyllotreta armoraciae Phyllotreta pusi lla, Phyllotreta ramosa, Phyllotreta striolata, Popiliia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Delia antiqua Delia coarctata, Delia floriiega, Deiia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophia melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g.
  • Acizzia acaciaebaileyanae Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. Acyrthosiphon pisum, Acrogonia spp., Aeneoiamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g.
  • Macrosiphum spp. E.g. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praeionga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. Psylla buxi, Psyila mali, Psylla pyri.
  • Pteromalus spp. Pulvinaria spp., Pyri IIa spp., Quadraspidiotus spp., E.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopaiosiphum spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Saissetia coffeae Saissetia miranda, Saissetia negiecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. B.
  • Trioza spp. Trioza diospyri Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahl mountains!
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis. Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia pomoneila Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp.
  • Heliothis virescens Hofmannophila pseudospretella Homoeosoma spp., Homona spp., Hyponomeuta padeila, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
  • Leucoptera coffeella Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphiis spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera z. B.
  • Damalia spp. Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera z. Lepinotus spp., Liposceiis spp .; from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephaiides spp., E.g.
  • Ctenocephalides canis, Ctenocephalides felis, Pul ex irritans, Tunga penetrans, Xenopsyila cheopis; from the order of Thysanoptera z.
  • Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigereila spp., Z. B. Scutigerella immaculata;
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemeila curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g.
  • Pratyienchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radophoius spp. Radopholus citrophiius, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g.
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as an anti-MLO (mycoplasma like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as S cbirdlingsb ehimmp fungsmittel such. B. drench, drip and fuel / brew, comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-enhancing adjuvants such as
  • Penetration conveyor z.
  • vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soy aölmethylester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • these are formulations or application forms, which auxiliary agents such as extenders, solvents, spontaneity, excipients, emulsifiers, dispersants.
  • auxiliary agents such as extenders, solvents, spontaneity, excipients, emulsifiers, dispersants.
  • Antifreeze, biocides, thickeners and / or other adjuvants such as adjuvants included.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that require retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for shaping the formulation of the compounds of the formula (I) or the formulations prepared from these formulations (such as, for example, ready-to-use pesticides, such as spray liquors or seed dressing), such as certain physical, technical and / or to confer biological properties.
  • Suitable extenders z As water, polar and nonpolar organic chemical liquids such. B. from the classes of aromatic and non-aromati see hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, Cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • the alcohols and polyols which may also be substituted, etherified and / or esterified
  • liquid solvents are essentially in question: aromatics such as Xyloi, Tokyo! or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg. As petroleum fractions, mineral and vegetable oils.
  • Alcohols such as butanol or lycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • Suitable solvents are, for example, aromatic hydrocarbons such.
  • xylene, toluene or alkylnaphthalenes chlorinated aromatic or chlorinated aliphatic hydrocarbons such.
  • chlorobenzene chloroethylene, or methylene chloride, aliphatic hydrocarbons such.
  • cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • z As ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapuigite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, har / e. Waxes and / or solid fertilizers. Mixtures of such carriers can also be used. As carriers for granules are in question: z.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane. Nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with Fatty amines, with substituted phenols (preferably aikylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
  • alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin Suifitablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
  • dyes such as inorganic pigments, eg., iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as kite stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability may also be present. It may also contain foam-forming agents or defoamers.
  • auxiliaries and adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be contained in the formulations and the application forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention agents, stabilizers, sequestering agents, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances considered that the dynamic
  • Reduce surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or Soy aölmethylester, F ettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the application forms prepared from the formulations (in particular chelating agents) may vary within wide ranges.
  • the concentration of the compound of the formula (I) in the application forms can usually be between 0.00000001 and 95 wt .-% of the compound of formula (1), preferably between 0.00001 and 1 wt .-%, based on the weight of Application form, lie.
  • the application is done in a forms adapted to the application customary way. mongrels
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides.
  • Useful insects, herbicides, fertilizers, Vogelrepeilentien, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators are used to such.
  • B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance.
  • drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensaizgehalt.
  • the flowering and fruit behavior can be improved, the germination and rooting can be optimized, the harvest can be improved and the harvest yield can be improved increase the quality and / or the nutritional value of the emmentary products, extend the shelf life and / or improve the workability of the harvested products.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • Formula (I) to improve the Pfianzenigenschaften such as growth, yield and quality of the crop are used.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb.
  • carbamates e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, ox
  • organophosphates e.g. Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos
  • GABA-controlled chloride channel blockers such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
  • sodium channel modulators such as pyrethroids, e.g.
  • Fenvalerate flucythrinate, flumethrin. tau-fluvalinate, Halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR) -trans-isomer], prallethrin.
  • Pyrethrins pyrethrum
  • resmethrin silafluofen
  • tefluthrin tetramethrin
  • tetramethrin tetramethrin
  • DDT methoxychlor
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • AUotic nicotinic acetylcholine receptor (nAChR) modulators such as spinosyn, e.g. B. spinetoram and spinosad.
  • AUosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chioropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
  • alkyl halides e.g. Methyl bromide and other alkyl halides
  • chioropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Microbial disruptors of insect intestinal membrane such.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors, such as diafenthiuron or organo-innine compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
  • ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • octopamine receptor agonists such as amitraz.
  • Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
  • inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. B. Cyenopv rates and Cyflumetofen and carboxanilides, such as Pyflubumid.
  • ryanodine receptor modulators such as diamides, e.g. B.
  • active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifena
  • Fungicides The active ingredients specified here by their "common name” are known and described, for example, in the "Pesticide Manual” (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) ,
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin.
  • Isopyrazam (mixture of syn-epimeric racemate 1 RS.4SR.9RS and anti-epimeric racemate I RS.4SR.9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1 R.4S.9R), (2.015 ) Isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.016) isopyrazam (syn-epimeric racemate I RS.4SR.9RS).
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl ) -6-methylpyridazine, (4.01 l) 3-chloro-5 - (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluoro-henyl) pyridazine, (4.012) 4- ( 2-bromo-4-fluorophenyl)
  • Inhibitors of amino acid and / or protein biosynthesis for example, (7,001) cyprodinil, (7,002) kasugamycin, (7,003) kasugamycin hydrochloride hydrate, (7,004) oxytetracycline (7,005)
  • Inhibitors of ATP production for example, (8,001) silthiofam.
  • inhibitors of cell wall synthesis for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
  • Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) Tolclofos-Methyi.
  • Inhibitors of melanin biosynthesis for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • compounds which may act as decouplers for example (14.001) fluazinam, (14.002) meptyldinocap.
  • Cyflufenamid (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (15.013) Fosetyl-calcium, (15.014) Fosetyl-sodium, (15.015)
  • Methyl isothiocyanate (15,016) Metrafenone, (15,017) Mildiomycin, (15,018) Natamycin, (15,019)
  • Ni ckel dimethyldithiocarbamate (15.020) nitrothal isopropyl, (15.021) oxamocarb, (15.022) Oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pynofenone (Chlazafenone) (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide , (15.031) l - (4- ⁇ 4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole 2-yl ⁇ piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-
  • Bio Pesticides as Mixture Components The compounds of formula (I) may be combined with biological chelating agents.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological damage control agents include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231 179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No ATCC 700814) and strain QST2808 (Accession No. R RL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-1 4).
  • Strain AM65-52 (Accession No. ATCC 1276), oiler B. thuringiensis subsp. aizawai, in particular strain ABTS-1 57 (SD-1372), or 13. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91 -8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain U RO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanif), especially strain KV01,
  • Metarhizium anisopliae in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fimosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P.
  • lilacinus strain 251 AGAL 89/030550
  • Talaromyces flavus in particular strain VI 17b
  • Trichoderma atroviride in particular strain SCI (Accession Number CBS 122089)
  • Trichoderma harzianum in particular T. harzianum rifai T39 (Accession Number CNCM 1 -952).
  • viruses that can be used or used as biological pesticides are: Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus
  • NPV Spodoptera exigua
  • mNPV Spodoptera frugiperda
  • mNPV Spodoptera frugiperda
  • Spodoptem littoralis Africann cottonworm
  • bacteria and fungi which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flura / ols. Fluxofenim, Filla / oie.
  • safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flura / ols. Fluxofenim, Filla / oie.
  • plants are understood as meaning all plants and plant populations, such as desirable and unwanted wild plants or crop plants (including naturally occurring crop plants), For example, cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugar cane, tomatoes, peppers, cucumber, melon, carrots, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soy, potato, sugar beets, sugar cane, tomatoes, peppers, cucumber, melon, carrots, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants
  • Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant protectable or non-protectable plant varieties. Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants. Sharpening P lanzen is to be understood as meaning all aboveground and subterranean parts and organs of the plants such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhi / oi ne be listed. The plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as hybridization or protoplast fusion and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties (“traits”) have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • transgenic plants or plant species to be treated according to the invention are all plants which have obtained genetic material by the genetic engineering modification and which give these plants particularly advantageous valuable properties ("Traits").
  • Traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottling, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • the genes which confer the desired properties can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane.
  • Tomatoes Tomatoes, peas and other vegetables, cotton, tobacco. Rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) mentioned, with corn. Soya, wheat, rice, potato, cotton, sugarcane, tobacco and oilseed rape are particularly emphasized. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • Crop protection - types of treatment The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by affecting their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, evaporation, sputtering, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and Vennehrungsmaterial, especially in seeds, continue bykowskibei / en, wet pickling, Schlämmbeizen It is also possible to apply the compounds of the formula (I) by the ultra-low volume method or to inject the application form or compound of the formula (I) itself into the soil ,
  • a preferred direct treatment of the plants is foliar application, ie the compounds of formula (I) are applied to the foliage, the frequency of treatment and the rate should be adjusted to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i , Ii.
  • the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In the case of water crops, this can also be achieved by adding the compound of formula (I) in a solid form (eg as granules) to a flooded paddy field.
  • seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention. The invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component. For seeds which have been treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onion and lettuce), fruit plants, turf and ornamental plants.
  • Cereals such as wheat, barley, rye and oats
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary formulating formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • These formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes.
  • water-insoluble pigments and water-soluble dyes are useful in this case.
  • examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 1 12 and CI Solvent Red 1.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryryiphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the present invention are all formulations which are customary for the formulation of agrochemical active substances and which contain anti-foaming substances.
  • Defoamers which may be present in the present invention are all formulations which are customary for the formulation of agrochemical active substances and which contain anti-foaming substances.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention.
  • dichlorophene and benzyl alcohol are mentioned.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to C ellulo s ederivate, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, p.
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape.
  • the case-sensitive formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of formula (I) which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual developmental stages of the parasites.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and, in particular, dogs, cats, stubenvögei; Reptiles, amphibians or aquarium fish.
  • the compounds of the formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds or, in particular, poultry.
  • controlling or “controlling” in the present context means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced. More specifically, “combating” in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Maliophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damali na spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chropot
  • Meiophagus spp. Meiophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Phiiipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .;
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp. Dermacentor spp., Haemaphysaiis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Omithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp. Dermacentor spp., Haemaphysaiis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (
  • Myobia spp. Neotrombicula spp., Ornitrocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
  • parasitic protozoa include, but are not limited to:
  • Mastigophora (Flagellata), like:
  • Metamonada from the order Vaccinia spp., Spironucleus spp.
  • Parabasal a from the order Trichomonadida / for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, / for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveolata such as Apicomplexa (Sporozoa): z.
  • Cryptosporidium spp . from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida z. Ii.
  • Microspores such as Encephalitozoon spp., Enterocytocoon spp., Globidium spp., Nosema spp. B. Myxozoa spp.
  • Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea z.
  • Dactylogyrus spp. Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
  • Cestodes from the order Pseudophyilidea for example: Bothridium spp., Diphyliobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Om
  • Parabronema spp. Parafiaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skj rabin ema spp., Spirocerca spp., Stephano fiiaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
  • Another aspect relates to the compounds of formula (I) for use as antiendoparasitic.
  • Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
  • Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
  • veterinary formulations which comprise an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as herein described, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, in particular with pharmaceutically acceptable ones conventionally used in veterinary formulations Excipients and / or adjuvants conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, the same requirement.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of formula (I) with other active ingredients are provided herein for the veterinary field.
  • “blending" not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances are formulated in a common formulation, or all the active substances are formulated in separate formulations, also conceivable mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
  • B Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyratluprol. Pyripro !. Vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fiuralaner;
  • Pyrethroids e.g. B. (cis, trans) metofluthrin, protluthrin. Flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrine, cis-cypermethrin, cis-permethrin, clocythrin, cyhalothrin (lambda), chlovaporthrin, or halogenated cabbage s he links (HCHs),
  • Neonicotinoids e.g. B. Nithiazine
  • Dicloromezotiaz, triflumezopyrim, macrocyclic lactones e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
  • Bios, hormones or pheromones for example natural products, e.g. Thuringiensin, codlemon or neem components
  • Dinitrophenols e.g. Dinocap, dinobuton, binapacryl
  • Benzoylureas eg. Fluazuron, penfluron
  • Amidine derivatives e.g. B. Chlormebuform, cymiazole, demiditraz
  • Hive varroa acaricides for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides, as a mixture partner include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestocidal agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin,
  • hydroxyzine from the class of tetracyclines for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes for example: Bunamidine.
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toitrazuril; from the class Poiyletherionophor for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides, for example: imi
  • all said mixing partners can optionally form salts with suitable bases or acids.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are:

Abstract

The invention relates to mesoionic halogenated 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate derivatives and related compounds of the formula (I) which are suitable for combating animal pests, including arthropods and in particular insects, arachnids, and nematodes, and in which the structural elements Q1, Q2, W, T, Y, G, and U have the meanings given in the description. The invention also relates to a method for producing same and to the use thereof as insecticides.

Description

MESOLONISCHE HALOGENIERTE  MESOLONIC HALOGENATED
3-(ACETYL)-1 -[(1 ,3-THIAZOL-5-YL)METHYL]-1 H-IMIDAZO[1 ,2-A]PYRIDIN-4-IUM-2-OLAT DERIVATE  3- (ACETYL) -1 - [(1,3-THIAZOL-5-YL) METHYL] -1 H -IMIDAZO [1,2-A] PYRIDINE-4-IUM-2-OLAT DERIVATIVES
UND VERWANDTE VERBINDUNGEN ALS INSEKTIZIDE  AND RELATED COMPOUNDS AS INSECTICIDES
Die vorliegende Erfindung betrifft neue mesoionische Imidazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen, vor allem von Arthropoden und insbesondere von Insekten, Spinnentieren und Nematoden. The present invention relates to novel mesoionic imidazole derivatives, to processes for their preparation and to their use for controlling animal pests, in particular arthropods and in particular insects, arachnids and nematodes.
Bestimmte mesoionische Imidazolderivate sind bereits bekannt, siehe zum Beispiel J. Chem. Soc. Perkin Trans I, 1984, 69-73; Tetrahedron 1990, 46. 6033-6046; Can. J. Chem. 1971, 49, 668-671 ; Tetrahedron 1986, 42, 1169-1177; Tetrahedron 2009, 65, 7591-7596; Tetrahedron 1998, 54, 9689-9700; Acta Crystallographica, Section E: Structure Reports Online (2011), 67(10), 2814. Eine biologische Wirkung wurde in den genannten Publikationen nicht beschrieben. Einige Beispiele sind in der folgenden Tabelle genannt: Certain mesoionic imidazole derivatives are already known, see, for example, J. Chem. Soc. Perkin Trans I, 1984, 69-73; Tetrahedron 1990, 46. 6033-6046; Can. J. Chem. 1971, 49, 668-671; Tetrahedron 1986, 42, 1169-1177; Tetrahedron 2009, 65, 7591-7596; Tetrahedron 1998, 54, 9689-9700; Acta Crystallographica, Section E: Structure Reports Online (2011), 67 (10), 2814. A biological effect has not been described in the cited publications. Some examples are given in the following table:
Struktur CAS-No. /Lit. Structure CAS-No. / Lit.
cture cture
Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombi nierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nie als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Issues of toxicity, of combinability with other active substances or formulation auxiliaries play a role, as well as the question of the effort required for the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can never be considered complete and there is a constant need for new compounds with improved properties over the known compounds, at least with respect to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spelctrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. The object of the present invention was to provide compounds which broaden the pesticide composition in various aspects and / or improve its activity.
Es wurde nun überraschend gefunden, dass bestimmte neue mesoionische Imidazolderivate starke Insektizide Eigenschaften bei gleichzeitig guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit besitzen. Die erfindungsgemäßen neuen Verbindungen wurden bislang nicht offenbart. It has now surprisingly been found that certain new mesoionic imidazole derivatives have strong insecticidal properties combined with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility. The novel compounds of the invention have not been disclosed.
Gegenstand der vorliegenden Erfindung sind daher Verbindungen der allgemeinen Formel (I) The present invention therefore relates to compounds of the general formula (I)
(I), worin (Ausgestaltung 1 -2)  (I), wherein (Embodiment 1 -2)
Q1 und Q zusammen für einen der Reste A-l bis A-5 stehen, die zusammen mit dem C - und N-Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q 1 and Q together represent one of the radicals A 1 to A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
A-l A-2 A-3 A-4 A-5 A-1 A-2 A-3 A-4 A-5
T für R\ -OR' . -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und W für O steht, oder T ffir -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und T for R \ -OR '. -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and W is O, or T is -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
W für S steht, W stands for S,
G für eine Bindung, für -C(R9)(R10)- , oder für C(R9)(R10)C(R9a)(R10a) steht, U für einen Cyclus der Reihe U-1 bis U-28 steht G is a bond, -C (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ), U is a cycle of the series U-1 to U-28 stands
<* δ U- 1 λ U5-2 <*a U3-3 λ5 U-4 Λδ U-5 <* δ U- 1 λ U 5 -2 <* a U 3 -3 λ5 U-4 Λδ U-5
-6 -7 U-8 Λό U-9 (χ, U)-1Ν0 -6 -7 U-8 Λό U-9 (χ, U) -1 Ν 0
U-26 U-27 U-28 Xa für Halogen, Nitro, OH. Cyano, SCN, SF5, G-G-Alkyl, C3-C6-Cycloalkyl, G -G,-Halogenalkyl, G -G- Alkoxy, C ι -G -Halogenalkoxy. G-G-Halogeneycloalkyl, G-G-Alkoxy-G-G-alkyi, G- C, -Halogenalkoxy-Ci-C , -alkyl. C i -G -Alkoxy-C ι -G-alkyloxy, Cyano-C i -C6-alkyl, G-G- Cycloalkyl-G-G-alkyi, C2-C6-Alkenyi, C3-C6-Aikinyl, G-G-Alkylthio, G-G-Alkylcarbonyl, G-G-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, G-G-Halogenaikyicarbonyl, G-G- Alkoxycarbonyl, G-G-Alkoxyimino-G-G-alkyl, G-G-Alkylsulfinyl, G-G-Alkyisulfonyi, C 1 -G-Halogenalkylsulfonyl, G-G-Alkylaminocarbonyl oder Di-(Ci -C6)-alkylaminocarbonyl, Aryi, Hetaryl, Ary l -G-G -alkyl oder Hetaryi-G-G-aikyi steht, wobei Aryl, Hetaryl, Aryl-G- Ce-aikyi und Hetaryl -C 1 -Ce -alkyl j eweils einfach bis dreifach durch Halogen, Cyano, Nitro, G- CVAlkyl, ' i-Ci-Haloalkyl. C i -C' -Alkoxy oder Ci-Ci-Haloalkoxy substituiert sein können und wobei die Ring-N-Atome in U-17, U-18, U-19, U-26, U-27 und U-28 nicht durch Halogen, Nitro, OH. Cyano, SCN, SF5, G-C6-Alkoxy, G -C -Halogenalkoxy, G-C6-Alkylthio, G-C6- Alkylsulfinyl oder C' i-C .;-Alkoxy- ' ! -( .; -alkyloxy substituiert sind, n für 0, 1 , 2 oder 3 steht, U-26 U-27 U-28 X a for halogen, nitro, OH. Cyano, SCN, SF 5 , GG-alkyl, C 3 -C 6 -cycloalkyl, G -G, -haloalkyl, G -G- alkoxy, C ι -G haloalkoxy. GG-halogeno-cycloalkyl, GG-alkoxy-GG-alkyl, G-C, -haloalkoxy-Ci-C, -alkyl. C 1 -G alkoxy C 1 -G -alkyloxy, cyano-C 1 -C 6 -alkyl, GG-cycloalkyl-GG-alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, GG-alkylthio , GG-alkylcarbonyl, GG-cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, GG-haloalkylcarbonyl, GG-alkoxycarbonyl, GG-alkoxyimino-GG-alkyl, GG-alkylsulfinyl, GG-alkylsulfonyi, C 1 -G -haloalkylsulfonyl, GG-alkylaminocarbonyl or di- (C 1 -C 6) -alkylaminocarbonyl, aryl, hetaryl, aryl-GG-alkyl or hetaryic-GG-aikyl, where aryl, hetaryl, aryl-G-ce-aikyl and hetaryl-C 1 -C -alkyl j easily in each case up to three times by halogen, cyano, nitro, G- CVAlkyl, 'i-C haloalkyl. C i -C ' alkoxy or C 1 -C 12 haloalkoxy and wherein the ring N atoms in U-17, U-18, U-19, U-26, U-27 and U-28 are not substituted by Halogen, nitro, OH. Cyano, SCN, SF 5 , GC 6 -alkoxy, G -C -haloalkoxy, GC 6 -alkylthio, GC 6 -alkylsulfinyl or C ' iC., - alkoxy- ' ! - (.; Alkyloxy are substituted, n is 0, 1, 2 or 3,
R', R2, R ". R4 jeweils unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, SF5, SCN, Amino, G-Ce-Alkyiamino, Di-{C 1 -G)-alkylamino, Hydroxy, COOH, G-Ce-Alkyi, G-G - Cycloalkyl, G-G -Halogenalkyl, G -Ct - Alkoxy. G-G -Halogenalkoxy. C3-C6-R ', R 2 , R ", R 4 each independently represent hydrogen, halogen, cyano, nitro, SF 5, SCN, amino, G-Ce-alkyiamino, di (C 1 -G) -alkylamino, hydroxy, COOH, G-Ce-Alkyi, GG-cycloalkyl, GG-haloalkyl, G-C t -alkoxy, GG-haloalkoxy, C3-C6-
Halogencycloallcyl, C3-C6-Halogencycloalkyl-C 1 -C6-alkyl, G-G-Aikoxy-G-G-alkyl, G-Ce- Halogenalkoxy-G-Ce-alkyl, G-Ce-Alkoxy-G-Ce-allcyloxy, Cyano-G-C6-alkyl, G-G- Cycioalkyl-G-C6-alkyl, G-G -Alkenyl, C2-C6-Alkenyloxy, C ;-G -Alkinyl, Cs-Ce-Alkinyloxy, Si l. G-Ce-Alkylthio, G-C«-Alkylsulfmyl, G-C6-Aikylsulfonyl, G-G-Halogenalkylsulfonyl, G-Ce-Alkylcarbonyl, Cs-Ce-Cycloalkylcarbonyi, G-G -Halogenalkylcarbonyl. G-Ce- Alkoxyimino-G-G-aikyi, G-Ce-Alkoxycarbonyl, G-Ce-Alkylaminocarbonyl, Di-(G-Ce)- alkylaminocarbonyl, Aryl, Hetaryl, Aryl-C 1 -Ce -alkyl oder Hetaryl-G -G -alkyl stehen, wobei Aryl, Hetaryl, Aryl-CVCt -alkyl und Hetaryl-G -G -alkyl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G -G-Alkyl, G-G- Alkenyl, G-G-Alkinyl, C3-C6-Cycloalkyl, G-C6-Alkoxy, C i -G -Halogenalkyl. G-C6- Haiogenalkoxy oder G-G-Alkylthio substituiert sein können, oder Halocycloallcyl, C3-C6-halocycloalkyl-C1-C6-alkyl, GG-aikoxy-GG-alkyl, G-Ce-haloalkoxy-G-Ce-alkyl, G-Ce-alkoxy-G-Ce-allcyloxy, cyano-G -C6 -alkyl, GG-cycloalkyl-G-C6-alkyl, GG-alkenyl, C 2 -C 6 -alkenyloxy, C; -G -alkynyl, Cs-Ce-alkynyloxy, Si l. G-Ce-alkylthio, GC "alkylsulfmyl, GC 6 -alkylsulfonyl, GG-haloalkylsulfonyl, G-Ce-alkylcarbonyl, Cs-Ce-cycloalkylcarbonyi, GG-haloalkylcarbonyl. G-Ce-alkoxyimino-GG-aikyl, G-Ce-alkoxycarbonyl, G-Ce-alkylaminocarbonyl, di- (G-Ce) -alkylaminocarbonyl, aryl, hetaryl, aryl-C 1 -C -alkyl or hetaryl-G -G alkyl, where aryl, hetaryl, aryl-alkyl and hetaryl CVC t -G-G alkyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, hydroxyl, G -G alkyl, alkenyl GG, GG-alkynyl, C 3 -C 6 -cycloalkyl, GC 6 -alkoxy, C i -G -haloalkyl. GC 6 - Haiogenalkoxy or GG-alkylthio may be substituted, or
R1 und R - oder R 1 and R - or
R - und R3 oder R and R 3 or
R3 und R4 jeweils zusammen einen 5- oder 6 gliedrigen aliphatischen, aromatischen, heteroaromatischen oder heterocyclischen Ring bilden, welcher gegebenenfalls 1 bis 2 Atome aus der Reihe O, S und N enthalten kann und der gegebenenfalls ein- oder mehrfach durch Halogen oder durch G -G-Alkyl substituiert sein kann, R 3 and R 4 each together form a 5- or 6-membered aliphatic, aromatic, heteroaromatic or heterocyclic ring which optionally has 1 to 2 atoms from the May contain O, S and N and which may optionally be monosubstituted or polysubstituted by halogen or by G-G-alkyl,
R für Wasserstoff oder für G-G-Alkyl, C-C -Alkenyl oder G -G -Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis zu fünfach durch Halogen oder einfach durch Nitro, Cyano, G-G-Cycloalkyi, 0-R\ -S(0)p-R52, -N(R53)(R ), -C(=0)N(R53)(R54), -0-C(=0)- R55, -C(=0)-R55, O-SO2-R56, Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl substituiert sein können, wobei Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl wiederum jeweils einfach bis dreifach durch Halogen, Nitro, Cyano, G-G-Alkyl, C3 -C6-Cycloalkyl, G -G -Halogenalkyl. G- C -AI koxy, G-G-Halogenalkoxy, G-C -Halogencycloalkyl, C 1 -G.-Alkoxy-C 1 -G-alkyl, G-C«- Halogenalkoxy-G -G -alkyl. G-G-Alkoxy-G-G-alkyloxy, Cyano-G -G-alkyl, G-CÖ- Cycloalkyi-G -G-alkyl, C2-C6-Alkenyl, -G-Alkinyl, G -G -Alkylthio. G-C6-Alkylcarbonyl, G-G-Cycloalkylcarbonyi, C2-C6-Alkenylcarbonyl, G-G-Halogenalkylearbonyl, G-G- Alkoxycarbonyl, G-G-Alkyisulfonyi, C 1 -G-Halogenalkylsulfonyl, G-G-Alkylaminocarbonyl, Di-(G-C6)-aikylaminocarbonyi, G-C6-Alkylcarbonylamino, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl wiederum gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G-G-Alkyl, G-G-Aikenyl, G -G -Alkinyl, G-Ce-Alkoxy, G -G -I lalogenalkyl. C i -G - H al oge na 1 koxy oder G-G-Alkylthio substituiert sein können, oder R is hydrogen or GG-alkyl, C -C -alkenyl or G-Galkynyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted by halogen or simply by nitro, cyano, G-C-cycloalkyl, O-R-S (0) p -R 52 , -N (R 53 ) (R), -C (= O) N (R 53 ) (R 54 ), -O-C (= O) - R 55 , -C (= 0) -R 55 , O-SO 2 -R 56 , aryl, hetaryl, heterocyclyl or oxoheterocyclyl, where aryl, hetaryl, heterocyclyl or oxoheterocyclyl can in each case be monosubstituted to trisubstituted by halogen, nitro, cyano, GG-alkyl, C 3 - C6-cycloalkyl, G-haloalkyl. G-C 1 -Alkoxy, GG-haloalkoxy, GC -halocycloalkyl, C 1 -G.-alkoxy-C 1 -G -alkyl, GC «- haloalkoxy-G-G-alkyl. GG-alkoxy-GG-alkyloxy, cyano-G-G-alkyl, GC Ö - Cycloalkyi-G-G-alkyl, C 2 -C 6 alkenyl, alkynyl -G, G -G alkylthio. GC 6 -alkylcarbonyl, GG-cycloalkylcarbonyi, C 2 -C 6 -alkenylcarbonyl, GG-haloalkylearbonyl, GG-alkoxycarbonyl, GG-alkylsulfonyi, C 1 -G -haloalkylsulphonyl, GG-alkylaminocarbonyl, di- (G-C6) -acylaminocarbonyi, G- C6-alkylcarbonylamino, aryl or hetaryl can be substituted, wherein aryl and hetaryl in turn optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, hydroxy, GG-alkyl, GG-Aikenyl, G -G alkynyl, G-Ce Alkoxy, G -G -I lalogenalkyl. C i -G - halo may be substituted on 1 koxy or GG-alkylthio, or
R5 für C3-C6-Cycloalkyl oder C ;-G - Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, G-G- Alkyl, G -G -Halogenalkyl, G-Ce-Alkoxy, G -G -Halogenal koxy C3-C«-Cycloalkyl, G-C6- Alkylthio, G-G-Alkylsulfinyl, G-Ce-Alkylsulfonyl, Aryl, Hetaryl. Aryl-G -G,-alkyl oder H et a ry 1 -G -G -a 1 k y I substituiert sein können, wobei Aryl, Hetaryl, Arvl-G -G -alkyl und Hetaryl- G-Ce-alicyi jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G -CVAlkyl, C1-C4- Halogenalkyi, C i -( .i-Alkoxy oder G-C'4-Haloalkoxy substituiert sein können, oder R 5 is C 3 -C 6 -cycloalkyl or C 1 -C -heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, or simply by cyano, GG-alkyl, G-halogenoalkyl, G-C 1 -alkoxy , G-halogenoalkoxy C 3 -C 12 -cycloalkyl, GC 6 -alkylthio, GG-alkylsulfinyl, G-Ce-alkylsulfonyl, aryl, hetaryl. Aryl-G-G, -alkyl or H et aary 1 -G -G -a 1 ky I may be substituted, wherein aryl, hetaryl, Arvl-G -G -alkyl and hetaryl-G-ce-alicyi in each case simple to trisubstituted by halogen, cyano, nitro, G -CVAlkyl, C1-C4 Halogenalkyi, C i - 4-haloalkoxy may be substituted (.i-alkoxy or GC ', or
R5 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, G-G-Alkylamino, Di-(G-G)-alkylamino, Hydroxy, COOK, G-G-Aikyl, G-G-Cycloalkyl, G -G -Halogenalkyl, G -G-Alkoxy, G-C6- Halogenalkoxy. C s-G -Halogencycloal kyl. C-.-Cr-Halogeru ycloalkyl-C i-C. -alkyl, G-Ce-Alkoxy- C i -C(,-alkyl, G-G-Halogenalkoxy-G-G-alkyl, G-Ce-Alkoxy-G-Ce-alkyloxy, Cyano-G-C«- alkyl, C3-C6-Cycloalkyl-Ci-C6-alkyl, C2-C6-Alkenyl, G-G,-Alkinyl, SH. G -C-Alkylthio. G-C«- Alkylcarbonyl, G-Ce-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C * -C, -Halogenalkylcarbon vi. C i -C6-Alkoxycarbonyl, Ci-C6-Alkylsulfonyl, Ci -C6-Halogenalkylsulfonyl, G-Ce- Alkylaminocarbonyl, Di-(C i -C6)-alkylaminocarbonyl oder Tri-(C i -Ce -alkyl)silyl, p für 0, 1 oder 2 steht, R 5 is aryl or hetaryl, where the aforementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF 5, SCN, GG-alkylamino, di- (GG) -alkylamino , Hydroxy, COOK, GG-alkyl, GG-cycloalkyl, G-haloalkyl, G-G-alkoxy, GC 6 -haloalkoxy. C sG halocycloalkyl. C -.- Cr-Halogeru ycloalkyl-C iC. alkyl, G-Ce-alkoxy-C i -C (alkyl, GG-haloalkoxy-GG-alkyl, G-Ce-alkoxy-G-ce-alkyloxy, cyano-GC «- alkyl, C 3 -C 6 cycloalkyl-Ci-C 6 alkyl, C 2 -C 6 alkenyl, GG, alkynyl, SH. G -C -alkylthio. GC "- alkylcarbonyl, G-Ce-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C * -C, -haloalkylcarbon vi. C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6) -alkylaminocarbonyl or tri- (C 1 -C 6 -alkyl) silyl, p 0, 1 or 2 stands,
R51 für Wasserstoff oder für Ci-Ce-Alkyl, G-G -Alkenyl, C2-C6-Alkmyl, G-G-Cycloalkyl oder CVCY.-Hetert yelyl. steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Nitro, Cyano, C3 -Ce -Cycloalkyl, G -G,-Alkoxy, C1-G5- Halogenalkoxy, G-Ce-Alkylthio, C 1 -C6-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, C 1 -C6-Alkylcarbonyl, G -G -Alkoxy imino-C ·, -G -alkvl, C3-C6-Cycloalkylcarbonyl, G-G-Alkenylearbonyl, C1-G5- Halogenalkylcarbonyi, G-G-Alkoxycarbonyl, Ci-C6-Alkylsulfonyl, G-G-Halogenalkylsulfonyl, C 1 -C6-Alkylaminocarbonyl, Di-(Ci-C6)-alkylaminocarbonyi, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, C1-C4- Alk l, C i -C'4-Halogenalkyl. C' i -C'-i-Alkoxy oder Ci -Ci-Haloalkoxy substituiert sein können, oder R 51 is hydrogen or C 1 -C 6 -alkyl, GG-alkenyl, C 2 -C 6 -alkyl, GG-cycloalkyl or CVCY.-Hetert yelyl. wherein the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen or simply by nitro, cyano, C 3 -C 6 -cycloalkyl, G-G, -alkoxy, C 1 -C -haloalkoxy, G-C 1 -alkylthio, C 1 -C 6 Alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, G -G-alkoxy-imino-C 1, -G -alkvl, C 3 -C 6 -cycloalkylcarbonyl, GG-alkenylearbonyl, C 1 -G 5 -haloalkylcarbonyi, GG Alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl, GG-haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6) -alkylaminocarbonyi, aryl or hetaryl, where aryl and hetaryl can each be monosubstituted to trisubstituted by halogen, cyano, Nitro, C1-C4-Alk l, C i -C ' 4-haloalkyl. C ' i -C ' i -alkoxy or Ci -Ci-haloalkoxy may be substituted, or
R51 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, Ci-Ce-Alkyiamino, Di-(Ci-C6)-alkylamino, Hydroxy, COOK, (VC, -Alkyl, C3-C6-Cycloalkyl, CVC -Halogenalk l. Ci-C6-Alkoxy, Ci-C6- Halogenaikoxy, Cs-Ce-Halogencycloalkyl, Cs-Ce-Halogencycloalkyl-Ci-Cö-alkyl, Ci-Ce-Alkoxy- C i -C, -alkyl, C■ -C, -Halogenal koxy-C ·, -C. -alkyl. C ; -C, -Alkoxy-C ; -C, -alkyloxy, Cyano-Ci-C6- alkyl. C ^-G -Cycloalkyl- i -C. -alkyl. C-C-Alkenyl, C3-C6-Alkinyl, Ci-Ce-Aikylthio, Ci-C6- Alkylcarbonyl, Cs-Ce-Cycloaikylcarbonyl, C2-C6-Alkenylcarbonyl, C 1 -C , , - H a 1 o ge n a 1 k y 1 c ar Ix) n y 1 , Ci-Ce-Alkoxycarbonyl, Ci-Ce-Alkylsulfonyl, Ci -C -Halogenalkyls l fonyl. G-Ce- Alkylaminocarbonyl, Di-(Ci-C6)-alkylaminocarbonyl oder Tri-(C 1 -C« -alkyl)silyl, R 51 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di (C 1 -C 4) . C6) alkylamino, hydroxy, COOK, (VC, alkyl, C 3 -C 6 cycloalkyl, CVC -Halogenalk l Ci-C 6 alkoxy, Ci-C 6 - Halogenaikoxy, Cs-Ce-halocycloalkyl, Cs Ce-halocycloalkyl-Ci-COE-alkyl, Ci-Ce-alkoxy C i -C, alkyl, C ■ -C -Halogenal koxy-C ·, -C alkyl C;.. -C, alkoxy C 1 -C 6 -alkyloxy, cyano-C 1 -C 6 -alkyl, C 1 -C 4 -cycloalkyl-C 1 -C 4 -alkyl, C 2 -C -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -acylthio, C 6 -alkylcarbonyl, C 5 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 4 -alkyl- 1 -hydroxybenzyl, C 1 -C 4 -aryl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkyl Alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl. G-Ce-alkylaminocarbonyl, di (Ci-C6) -alkylaminocarbonyl or tri- (C 1 -C "-alkyl) silyl,
R52 für G-Ce-Aikyl, C2-C6-Aikenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyi oder C3-C6-Heterocyclyi steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano , C3-Ce- Cycloalkyl, G-C6-Alkoxy, G-C6-Halogenalkoxy, VG -Alkylthio, G-G-Alkylsulfinyl, G-C6- Alkylsulfonyl, Ci-Cö-Alkylcarbonyl, Ci-Ce-Aikoxyimino-Ci-Ce-alkyl, C3 -Cö-Cycloalkyl carbonyl, C2-C6-Alkenylcarbonyl, G-Ce-Halogenalkylcarbonyl, G-Ce-Alkoxycarbonyl, G-C6- Alkylsulfonyl, Ci -C, -Halogenalkylsulfonyl, G-Ce-Alkylaminocarbonyl, Di-(Ci-Ce)- alkylaminocarbonyl, Aryl oder Hetaryl, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-CVAlkyl, C i -G - H a löge n a Ikv , G -CVAIkoxy oder C < -C i-Haloalkoxy substituiert sein können, oder R 52 represents G-Ce-Aikyl, C 2 -C 6 -Aikenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -Cycloalkyi or C 3 -C 6 -Heterocyclyi, where the abovementioned radicals are optionally mono- to trisubstituted may be substituted and the substituents are independently selected from halogen, nitro, cyano, C 3 -Ce- cycloalkyl, GC 6 alkoxy, GC 6 haloalkoxy, VG -Alkylthio, GG-alkylsulfinyl, GC 6 - alkylsulfonyl, Ci-Cö Alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, G-C 6 -haloalkylcarbonyl, G-C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 - C, -haloalkylsulfonyl, G-Ce-alkylaminocarbonyl, di- (Ci-Ce) - alkylaminocarbonyl, aryl or hetaryl, wherein aryl and hetaryl in each case by simply three times Halogen, cyano, nitro, G-C-C-alkyl, C i -G - H a can be substituted by L-Ikv, G -C -alkoxy or C-C-i-haloalkoxy, or
R52 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, Ci-Cö-Alkylamino, Di-(Ci-C6)-alkylamino, Hydroxy, COOK, Ci-Ce-Alkyi, C3-C«-Cycloalkyl, G-Ce-Halogenalkyl, G-Ce-Aikoxy, G-Ce- Halogenalkoxy, Cs-Ce-Halogencycloaikyl, C3-C6-Halogencycloalkyl-C 1 -C6-alkyl, G-Ce-Alkoxy- G -G -alkyl, G -G 1alogCTialkoxy-G Y-alkyl, C i -G-Alkoxy-C i -G -alkylox , Cyano-G-G- alkyl. CVG eloalkyl-G -G,-alkyl, G-G-Alkenyl, C-.-C , -Alkinyl. G-G-Alkylthio, G-G- Alkylcarbonyl, G-G-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C > -C, -Halogenalkylcarbonyl , Ci-Ce-Alkoxycarbonyi, G-G-Alkylsulfonyl, Ci-Ce-Halogenalkylsulfonyl, Ci-Ce- Alkylaminocarbonyl, Di-(Ci-C6)-alkylaminocarbonyl oder Tri-(C1 -C« -alkyl)silyl, R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di- (C 1 -C 4 -alkyl) C 6) -alkylamino, hydroxy, COOK, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, G-C 6 -haloalkyl, G-C 6 -alkoxy, G-C 6 -haloalkoxy, C 1 -C 6 -halocycloalkyl, C 3 -C 6 -Halocycloalkyl-C 1 -C 6 -alkyl, G-Ce-alkoxy-G-G-alkyl, G-G 1 algC-dialkoxy-G Y-alkyl, C 1 -G-alkoxy-C 1 -G -alkylox, cyano-GG- alkyl. CVG eloalkyl-G-G, -alkyl, GG-alkenyl, C -.- C, -alkynyl. GG-alkylthio, GG-alkylcarbonyl, GG-cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyi, GG-alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6) -alkylaminocarbonyl or tri- (C 1 -C 6 -alkyl) silyl,
R53 für Wasserstoff, G-Ce-Aikyl, C^-Ce-Alkenyi, C2-C6-Alkinyi, -C-Cycloalkyl, Ci-C4-Aikoxy, C i -C ;-A!koxy-C 1 -C„- Alky I, Ci-Ce-Alkoxycarbonyl, Ci-Ce-Aikylcarbonyl, Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Ar l und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-C4-Alkyi, -CVHalogenalkyl, Ci-C4-Alkoxy oder C1-C4- Haloalkoxy substituiert sein können, R 53 is hydrogen, G-Ce-Aikyl, C ^ -Ce-Alkenyi, C 2 -C 6 -Alkinyi, -C-cycloalkyl, Ci-C 4 -Aikoxy, C i -C; -A! Koxy-C 1 -C "- Alky I, Ci-Ce-alkoxycarbonyl, Ci-Ce-Aikylcarbonyl, aryl, hetaryl, arylcarbonyl or hetarylcarbonyl, wherein Ar l and hetaryl each one to three times by halogen, cyano, nitro, G-C4-Alkyi, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy may be substituted,
R54 für Wasserstoff oder für Ci-Ce-Alkyi, C:- ,,-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloaikyl oder Cs-Ce-Cycloalkyl-C 1 -C6- Alkyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy, C V( t -Alkyl, Cs-Ce- Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Haloaikoxy, Ci-C4-Aikylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl, C s -Cf - A 1 koxy carbony 1 , G-Ce-Alkylcarbonyi oder Cs-Ce-Triaikylsilyl substituiert sein können, oder R 54 is hydrogen or Ci-Ce-Alkyi, C: -, - alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl or Cs-Ce-cycloalkyl-C 1 -C 6 -alkyl, wherein the abovementioned radicals optionally substituted independently one to five times (by halogen or monosubstituted by cyano, nitro, hydroxy, CV t-alkyl, Cs-Ce-cycloalkyl, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 - Aikylthio, C 1 -C 4 alkylsulfmyl, C 1 -C 4 alkylsulfonyl, C s -C f - A 1 koxy carbony 1, G-Ce-Alkylcarbonyi or Cs-Ce-triaikylsilyl may be substituted, or
R54 für Aryl, Hetaryl, Arvl-CVC -alkyl oder Heteroaryl - i -C, -al kyl steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, C; -Ct.-A!kyl, Cs-Ce-Cycloaikyl, C3- Ce-Cycloalkyiamino, Vd-Alkoxy, Ci-C4-Haioaikoxy, C i -Ci-Alkyhhio, Ci-C4-Alkylsulfmyl, Ci- C4-Alkylsulfonyl, C1 -C4-Alkylsulfimino, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl, oder R53 und R54 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Atom aus der Reihe O.S oder N enthält und gegebenenfalls einfach bis vierfach mit G -G-Alkyl, Halogen, Cyano, Amino oder G-C2-Alkoxy substituiert sein kann, R 54 is aryl, hetaryl, Arvl-CVC-alkyl or heteroaryl-i-C, -alkyl, where the abovementioned radicals may optionally be substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C; -Ct.-alkyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkylamino, Vd-alkoxy, C 1 -C 4 -haloalkyl, C 1 -C -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 - alkylsulfonyl, C1-C4 -Alkylsulfimino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl, or R 53 and R 54 may be connected to each other via two to six carbon atoms and form a ring which may optionally additionally contain another atom from the series OS or N and optionally monosubstituted to four times with G is -G-alkyl, halogen, cyano, amino or G-C2-alkoxy may be substituted,
R55 für G-G-Alkyl, C3-G-Cycloalkyl, Ci-C6-Halogenalkyl, G-G-Halogencycloalkyl, G-G- Cycloalkyl-Ci-Ce-alkyl, G-G-Halogencycloalkyl-C i -Ce-alkyl, Cyano-Ci-C6-alkyl, G-C6-Aikoxy, Ci-C6-Halogenalkoxy, Ci-Ce-Aikoxy-Ci-Ce-aikyl, G-G,-Halogenalkoxy-C ι -G -alkyl. Aryl. Hetaryl, Aryl-G -G, -alkyl oder Hetaryl-G-G-alkyl steht, wobei Aryl, Hetaryl, Aryl-G -G-alkyl und H etary I -C i -G -al ky 1 gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G-G-Alkyl, G-G-Cycloalkyi, G -C -Halogenalkyl, G-G-Alkoxy, G- G -Halogenalkoxy, G-G -Halogencycloalkyl oder G -G -Alkoxy-C ; -G -alkyl substituiert sein können, R 55 represents GG-alkyl, C 3 -G-cycloalkyl, C 1 -C 6 -haloalkyl, GG-halogenocycloalkyl, GG-cycloalkyl-C 1 -C 6 -alkyl, GG-halogenocycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 4 -alkyl, C 6 alkyl, GC 6 -Aikoxy, Ci-C6-haloalkoxy, Ci-Ce-Aikoxy-Ci-Ce-aikyl, GG, haloalkoxy C ι -G -alkyl. Aryl. Hetaryl, aryl-G-G, -alkyl or hetaryl-GG-alkyl, where aryl, hetaryl, aryl-G-alkyl and H etary I -C i -G -al ky 1 optionally mono- or polysubstituted, identical or different by halogen, cyano, nitro, GG-alkyl, GG-cycloalkyl, G-C-haloalkyl, GG-alkoxy, G-G-haloalkoxy, GG-halocycloalkyl or G-G-alkoxy-C; G -alkyl may be substituted,
R56 für G -G-Alkyl, C3-C6-Cycloalkyl, G -G -Halogenalkyl. C3-C6-Halogencycloaikyl, G-G- Cycloalkyl-C i -G-alkyl, G-G-Halogeneycloalkyl-G-G-aikyl, Cyano-G -G-alkyl, G-Ce-Alkoxy, G- -Halogenalkoxy, G-G-Alkoxy-G- -alkyl, \ -G -Halogenalkoxy-C ι -G,-alkyl, Aryl, Hetaryl oder Aryl-G-G -alkyl steht, wobei Aryl, Hetaryl und Aryi-G -G -alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G -G-Alkyl, G- C6-Cycloalkyl, C ·, -G -Halogenalkyl. Ci-Ce-Alkoxy, G -G-Halogenalkoxy, C3-C6- Halogencycloalkyl oder ; -Ct -Alkoxy- ι - ', -alkyl substituiert sein können, R 56 is G-G-alkyl, C 3 -C 6 -cycloalkyl, G -H-haloalkyl. C 3 -C 6 -halocycloalkyl, GG-cycloalkyl-C i -G-alkyl, GG-halogeno-cycloalkyl-GG-aikyl, cyano-G-g-alkyl, G-Ce-alkoxy, G-haloalkoxy, GG-alkoxy G- alkyl, \ -G Halalalkoxy -C ι -G, -alkyl, aryl, hetaryl or aryl-GG-alkyl, wherein aryl, hetaryl and Aryi-G -G-alkyl optionally mono- or polysubstituted, identical or different by halogen, cyano, nitro, G-alkyl, G-C6-cycloalkyl, C •, -G-haloalkyl. Ci-Ce-alkoxy, G-haloalkoxy, C3-C6-halocycloalkyl or; -C t -Alkoxy- ι - ' , alkyl may be substituted,
R6 für G-Ce-Alkyl, G-G-Cycloalkyl, G-G -Halogenalkyl. C3-C6-Halogencycloalkyl, C3-C6- C ycloalkyl-G -G-alkyl, G-G-Halogencycloalkyl-C 1 -C6-alkyl, Cyano-G -Ce-alkyl, G-C6- Alkoxy-CVCt -alkyl, i -G,-Halogenalkoxy-C i -G -alk l. Aryl, Hetaryl, Aryl-G -Ce-alkyl oder Hetaiyl-G -Ce-alkyl steht, wobei Aryl, Hetaryl, Aryl-G -G-alkyl und Hetaryl-G-Ce-alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G -G-Alkyl , G-G-Cycloalkyl, G-G-Halogenalkyl, G-Ce-Alkoxy, G-G -Halogenalkoxy. C3-C6- Halogencycloalkyl oder ; -( «,-Alkoxy- ; -G.-alkyl substituiert sein können, R 6 is G-Ce-alkyl, GG-cycloalkyl, GG-haloalkyl. C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-G-alkyl, GG-halogenocycloalkyl-C 1 -C 6 -alkyl, cyano-G -Ce-alkyl, GC 6 - alkoxy-CVC t -alkyl, i -G, -haloalkoxy-C i -G -alk l. Aryl, hetaryl, aryl-G -Ce-alkyl or hetaiyl-G -Ce-alkyl, wherein aryl, hetaryl, aryl-G-G-alkyl and hetaryl-G-Ce-alkyl optionally mono- or polysubstituted by identical or different Halogen, cyano, nitro, G-alkyl, GG-cycloalkyl, GG-haloalkyl, G-Ce-alkoxy, GG-haloalkoxy. C 3 -C 6 -halocycloalkyl or; (-, "- alkoxy; -G.-alkyl may be substituted,
R7 für Wasserstoff, G -G -Alkyl, G-G-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, G -G-Alkoxy, ] -( .t- Alkoxy-C 1 -G- Alkyl, C 1 -G-Alkoxycarbonyl oder C 1 -G,-Alkylcarbonyl steht, R 7 represents hydrogen, G 6 -alkyl, GG-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, G-G-alkoxy,] - (.t-alkoxy-C 1 -G- Alkyl, C 1 -G -alkoxycarbonyl or C 1 -G, -alkylcarbonyl,
R7a ffir Wasserstoff, G-G-Alkyl, G-G-Alkenyl, G-G-Alkinyl, C3-Ce-Cycloalkyl, G-C4-Alkoxy-G- G, -Alkyl, G -G-Alkoxycarbonyl oder C 1 -G-Alkylcarbonyl steht, R 7a is hydrogen, GG-alkyl, GG-alkenyl, GG-alkynyl, C 3 -Ce-cycloalkyl, GC 4 -alkoxy-G-G, -alkyl, G-G-alkoxycarbonyl or C 1 -G-alkylcarbonyl,
R8 für Wasserstoff oder für G -G -Alkyl, C.--G - Alkenyl oder G-G-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy, G -G-Alkyl, G-G-Cycloalkyl, G -G-Alkoxy, G-G-Haloalkoxy, G -G- Alkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkylsulfimino, G-C4- Alkyl sul fimino -C 1 - Valkyl. C 1 -C4-Alkylsulfimino-C2-C5-alkylcarbonyl, C 1 -C4-Alkylsulfoximino, C 1 -C4-Alkyl sulfoximino-C 1 -CValkyl, C 1 -C4-Alkylsulfoximino-C2-C5-alkylcarbonyl, C 1 -G - Alkoxycarbonyl, G-G-Alkylcarbonyl oder G-G-Triaikylsilyi substituiert sein können, oder R 8 is hydrogen or G-G-alkyl, C - G - alkenyl or GG-alkynyl, where the abovementioned radicals, where appropriate, independently of one another, can be monosubstituted to five times by halogen or simply by cyano, nitro, hydroxy, G- Alkyl, GG-cycloalkyl, G-G-alkoxy, GG-haloalkoxy, G -G- Alkylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -alkylsulfimino, GC 4 -alkyl sul fimino-C 1 - Valkyl. C 1 -C 4 -alkylsulfimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulfoximino, C 1 -C 4 -alkyl-sulfoximino-C 1 -C -alkyl, C 1 -C 4 -alkylsulfoximino-C 2 -C 5 -alkylcarbonyl, C 1 - G - alkoxycarbonyl, GG-alkylcarbonyl or GG-Triaikylsilyi may be substituted, or
R8 für Aryi-Ci-Ce-alkyl, Heteroaryl-G-G -alkyl. C3-G2-Cycloalkyl, G-Cn-Cycloalkyl-G-G-Alkyl oder C4-Ci2-Bicycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, G-G-Alkyl, C3-G-Cycloalkyl, C3-C6-Cycloalkylamino, G -G-Alkoxv,R 8 is aryl-C 1 -C 6 -alkyl, heteroaryl-GG-alkyl. C 3 -G 2 -cycloalkyl, G-Cn-cycloalkyl-GG-alkyl or C4-Ci2-bicycloalkyl, where the abovementioned radicals may optionally be substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino , GG-alkyl, C 3 -G -cycloalkyl, C 3 -C 6 -cycloalkylamino, G -G-alkoxy,
Ci-C4-Haloalkoxy, Ci-C4-Aikyithio, G-G-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, G-G- Alkyl sul fimino, C2-C6-Aikoxycarbonyi oder G-G-Alkylcarbonyl, oder Ci-C4-haloalkoxy, Ci-C 4 -Aikyithio, GG-alkylsulfinyl, Ci-C 4 alkylsulfonyl, GG alkyl sul fimino, C 2 -C 6 Aikoxycarbonyi or GG-alkylcarbonyl, or
R8 für einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituierten 5- oder 6- gliedrigen aromatischen oder heteroaromatischen Ring, einen 4- bis ό-gliedrigen teilweise gesättigten Ring oder gesättigten heterozyklischen Ring, oder einen gesättigten oder aromatischen hetero-bizyklischen Ring steht, welcher gegebenenfalls ein bis drei Heteroatome aus der Reihe O, S oder N enthalten kann und der gegebenenfalls ein- oder mehrfach substituiert sein kann, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-Ce-Alkyl, C2-C6-Alkinyl, G -C, -Halogenalkyl. G-G-Cycloalkyl, G-G- Cycloalkylamino, Ci-C4-Alkoxy, G-C4-Haloalkoxy, G-C4-Alkylthio, Ci-C4-Alkylsulfmyl, G-G- Alkylsulfonyl, Ci-C4-Aikylsuifimino, G-G-Aikoxycai-bonyl oder G-G-Alkylcarbonyl, oder R 8 is an optionally mono- or polysubstituted by identical or different substituents 5- or 6-membered aromatic or heteroaromatic ring, a 4- to ό-membered partially saturated ring or saturated heterocyclic ring, or a saturated or aromatic hetero-bicyclic ring, which may optionally contain one to three heteroatoms from the series O, S or N and which may optionally be mono- or polysubstituted, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, Ci-Ce-alkyl , C 2 -C 6 alkynyl, G -C, -haloalkyl. GG-cycloalkyl, GG-cycloalkylamino, Ci-C 4 alkoxy, haloalkoxy 4 GC, GC 4 alkylthio, Ci-C 4 -Alkylsulfmyl, GG-alkylsulfonyl, Ci-C4-Aikylsuifimino, GG-Aikoxycai-carbonyl or GG Alkylcarbonyl, or
R und R8 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Stickstoff-, Schwefel- oder Sauerstoffatom enthält und gegebenenfalls einfach bis vierfach mit G-G-Alkyl, Halogen, Cyano, Amino oder G- C-Alkoxy substituiert sein kann, R and R 8 may be connected to each other via two to six carbon atoms and form a ring optionally additionally containing a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with GG-alkyl, halogen, cyano, amino or G-C Alkoxy may be substituted,
R9 für Wasserstoff, Fluor, Chlor, G-C4-Alkyl, C3-C6-Cycloalkyl oder Ci-C4-Halogenalkyl steht, R 9 represents hydrogen, fluorine, chlorine, GC 4 alkyl, C 3 -C 6 cycloalkyl or C 4 is haloalkyl,
R9a für Wasserstoff, Fluor, Chlor, G-C4-Alkyi, C3-C6-Cycloaikyl oder Ci-C4-Halogenalkyi steht, R 9a is hydrogen, fluorine, chlorine, GC -Alkyi 4, C 3 -C 6 -Cycloaikyl or C is 4 -Halogenalkyi,
Ri0 für Wasserstoff, Fluor, Chlor oder G-C4-Alkyl steht, und R i0 is hydrogen, fluorine, chlorine or GC 4 alkyl, and
Rioa Wasserstoff, Fluor, Chlor oder G-C4-Alkyl steht. Die Verbindungen der Formel (I) umfassen ebenfalls gegebenenfalls vorliegende Diastereomere oder Enantiomere sowie E/Z-isomere sowie Salze und N-Oxide von Verbindungen der Formel (I) und deren Anwendung zur Bekämpfung von tierischen Schädlingen. R i o a hydrogen, fluorine, chlorine or GC 4 alkyl. The compounds of formula (I) also include optionally present diastereomers or enantiomers and E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
Die substituierten mesoionischen Imidazolderivate sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formeln sind im Folgenden angegeben. The substituted mesoionic imidazole derivatives are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below.
Eine weitere Ausgestaltung (Ausgestaltung 1-1) sind Verbindungen der Formel (I), in denen A further embodiment (embodiment 1-1) are compounds of the formula (I) in which
Q1 und Q2 zusammen für einen der Reste A-1 bis A-5 stehen, die zusammen mit dem C- und N-Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, T für R5, -OK' . -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und Q 1 and Q 2 together represent one of A-1 to A-5, which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring, T is R 5 , -OK' . -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
W für O steht, oder W stands for O, or
T für -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und T is -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
W für S steht, W stands for S,
G für eine Bindung, für -C(R9)(R10)- , oder für C(R9)(R10)C(R9a)(R10a) steht, U für einen Cyclus der Reihe U-l bis U-28 steht, G is a bond, -C (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ), U is a cycle of the series U1 to U- 28 stands,
Xa für Halogen, Nitro, Ol l. Cyano, SCN, SF5, Ci-C-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenaikyi, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Cs-Ce-Halogencycloalkyl, Ci-Ce-Alkoxy-Ci-Ce-alkyl, Ci-X a for halogen, nitro, oil. Cyano, SCN, SF 5, C-alkyl, C 3 -C 6 cycloalkyl, C 6 -Halogenaikyi, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-halocycloalkyl, Ci-Ce- Alkoxy-C 1 -C 6 -alkyl,
Ce-Halogenalkoxy-Ci-Ce-alkyl, C i -('. -Alkoxy-C > -( ,,-alkyloxy, Cyano-C i -Ce-alkyl, C3-C6- Cycloalkyl-Ci-Ce-alkyl, C;-C«.-Alkenyl, Cs-Ce-Alkinyi, Ci-Ce-Alkylthio, G-Ce-Alkylcarbonyl, C3-C6-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, C > -G -Halogenalkylcarbonyl , G-Ce- Alkoxycarbonyl, C 1 -G - A I koxy i mi no- . 1 -CY-al ky 1, Ci-Ce-Alkj'lsulfinyl, C 1 -Ce-Alkylsulfonyl, Ci-Ce-Halogenalkylsulfonyl, Ci-C6-Alkylaminocarbonyl oder Di-(Ci-C6)-alkylaminocarbonyl,Ce-haloalkoxy-C 1 -C 6 -alkyl, C 1 - ( ') -Alkoxy-C 1 -C -alkenyl, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C -C-alkenyl, Cs-Ce-alkynedi, Ci-Ce-alkylthio, G-Ce-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, C> -G haloalkylcarbonyl, G-Ce-alkoxycarbonyl , C 1 -G -Alkoxy-1-C 1 -C 1 -alkyl, C 1 -C 6 -alkenylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl or (Ci-C6) alkylaminocarbonyl,
Aryl, Hetaryl, Aryl- ' i -C„-alkyl oder Hetaryl-CVG -alkyl steht, wobei Aryl, Hetaryl, Aiyl-Ci- Cö-alkyl und Hetaryl-Ci-Cö-alkyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G- -A!ky , C' i-Ci-Haloalkyl, Ci-C4-Alkoxy oder C'i-C s-Haloalkoxy substituiert sein können und wobei die Ring-N-Atome in U-l 7, U-l 8, U-l 9, U-26, U-27 und U-28 nicht durch Halogen, Nitro, OH. Cyano, SCN, SF5, G-G-Alkoxy, G-Ce-Halogenalkoxy, G -C-Alkylthio. G-G- Alkylsulfinyl oder C ι -Ci-Alkoxy-C ι -G-alkyloxy substituiert sind, n für 0, 1 , 2 oder 3 steht, Aryl, hetaryl, aryl ' i -C' alkyl or hetaryl-CVG-alkyl, wherein aryl, hetaryl, aiyl-Ci- Cö-alkyl and hetaryl-C 1 -C 6 -alkyl in each case mono- to trisubstituted by halogen, cyano, Nitro, G- A! Ky, C ' i-Ci-haloalkyl, Ci-C4-alkoxy or C ' iC s -haloalkoxy can be substituted and wherein the ring N-atoms in Ul 7, Ul 8, Ul 9, U-26, U-27 and U-28 not by halogen, Nitro, OH. Cyano, SCN, SF 5 , GG-alkoxy, G-Ce-haloalkoxy, G-C-alkylthio. GG-alkylsulfinyl or C ι -Ci-alkoxy-C ι -G-alkyloxy are substituted, n is 0, 1, 2 or 3,
R1, R-. R3, R4 jeweils unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, SF5, SCN, Amino, G-G-Aikylamino, Di-(Ci-C6)-alkylamino, Hydroxy, COOH, G -G - Alkyl, G-G-R 1 , R-. R 3 , R 4 are each independently of one another hydrogen, halogen, cyano, nitro, SF 5 , SCN, amino, GG-alkylamino, di- (C 1 -C 6) -alkylamino, hydroxy, COOH, G-G-alkyl, GG-
Cycloalkyl, G -G -Halogenalkyl, G -G-Alkoxy, G-G-Haiogenaikoxy, G-G- Haiogeneycloalkyl, C3-C6-Halogencycloalkyl-C 1 -G-alkyl, G-G-Alkoxy-G-G-alkyl, G-G- Halogenalkoxy-G -G -alkyl, G-G-Alkoxy-G -G-alkyloxy, Cyano-Ci-C6-aikyi, G-G- Cycloalkyl-G-G-aikyl, C2-C6-Aikenyl, C2-C6-Alkenyloxy, G-G -Alkinyl, C3-C6-Alkinyloxy, SH, G-G-Alkylthio, G-G-Alkylsulfinyl, G -G-Alkylsulfonyl, C 1 -C, -Halogena!ky!su! fonyl.Cycloalkyl, G-haloalkyl, G-G-alkoxy, GG-halo-genicoxy, GG-halo-cycloalkyl, C3-C6-halocycloalkyl-C 1 -G-alkyl, GG-alkoxy-GG-alkyl, GG-haloalkoxy-G-G -alkyl, GG-alkoxy-G-G-alkyloxy, cyano-Ci-C6-aikyi, GG-cycloalkyl-GG-aikyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, GG-alkynyl, C C 3 -C 6 alkynyloxy, SH, GG-alkylthio, GG-alkylsulfinyl, G-alkylsulfonyl, C 1 -C, -haloalkyl! fonyl.
G-Ce-Alkylcarbonyl, Cs-Ce-Cyc oalkylcarbonyl, C :-C. -Halogenalkylcarbonyl, CI-CÖ- Alkoxyirnino-Ci-Ce-alkyl, C 1 -Cö-Alkoxycarbonyl, Ci-C6-Aikylaminocarbonyl, Di-(Ci-C6)- alkylaminocarbonyl, Aryl, Hetaryl, Aryl-CVCc -alkyl oder Hentryl-Cj - , -alkyl stehen, wobei Aryl, Hetaryl, Aryi-Ci-Ce-alkyl und H et arv 1-C' s -C t -alkyl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G -Ce-Alkyi, C2-C6-G-Ce-alkylcarbonyl, Cs-Ce-Cyc oalkylcarbonyl, C: -C. -Haloalkylcarbonyl, C Ö - Alkoxyirnino-Ci-Ce-alkyl, C 1 -Cö-alkoxycarbonyl, Ci-C6-Aikylaminocarbonyl, di- (Ci-C6) - alkylaminocarbonyl, aryl, hetaryl, aryl-alkyl or CVCC Hentryl -Cj -, alkyl, wherein aryl, hetaryl, Aryi-Ci-Ce-alkyl and H et arv 1-C ' s -C t -alkyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, hydroxy , G-Ce-Alkyi, C2-C6-
Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl, G-C6-Alkoxy, Ci-C6 -Halogenalkyl, Ci-C6- Haiogenaikoxy oder G-Ce-Alkylthio substituiert sein können, oder Alkenyl, C 2 -C 6 alkynyl, Cs-Ce-cycloalkyl, GC 6 alkoxy, Ci-C 6 -haloalkyl, Ci-C 6 - Haiogenaikoxy or G-Ce-alkylthio may be substituted, or
R1 und R - oder R2 und R3 oder R 1 and R - or R 2 and R 3 or
R3 und R4 jeweils zusammen einen 5- oder 6 giiedrigen aliphatischen, aromatischen, heteroaromatischen oder heterocyclischen Ring bilden, welcher gegebenenfalls 1 bis 2 Atome aus der Reihe O, S und N enthalten kann und der gegebenenfalls ein- oder mehrfach durch Halogen oder durch ( VC 1- Alkyl substituiert sein kann, R5 für Wasserstoff oder für C i -Ct, -Alkyl, C2-C6-Alkenyl oder C2-Ce-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis zu fünfach durch Halogen oder einfach durch Nitro, Cyano, C3-C6-Cycloalkyl, 0-R\ -S(0)p-R52, -N(R53)(R54), -C(=0)N(R53)(R54), -O-Cl <))- R55, -C(=0)-R55, O-SO2-R56, Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl substituiert sein können, wobei Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl wiederum jeweils einfach bis dreifach durch Halogen, Nitro, Cyano, s -C t -Alkyl, C3-C«-Cycloalkyl, C i -G -Halogenalkyl. G- Ce-Alkoxy, G-Ce-Halogenalkoxy, C3 -Cö-Halogencycloalkyl, C ι -G,-Alkoxy-C i -G-alkyl, Ci-Ce- Halogenalkoxy-G- -alkyl, Ci-C6-Alkoxy-Ci-C6-alkyloxy, Cyano-C i -Cö-alkyl, G-G - Cycloalkyl-C i -G-alkyl, C2-G-Alkenyl, G-G-Alkinyl, G-G-Alkylthio, G-G-Alkylcarbonyl, C3-G-Cycloalkyicarbonyl, C2-C6-Alkenylcarbonyl, G-G-Halogenaikylcarbonyl, G-G- Alkoxycarbonyl, Ci-C6-Alkylsulfonyl, G-G-Halogenalkylsulfonyl, G-G-Alkylaminocarbonyi, Di-(C i -C6)-alkylaminocarbonyl, G-G-Alkylcarbonyiamino, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl wiederum gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G -G-Alkyl, G-G -Alkenyl, C2-C6-Alkinyl, G-G-Alkoxy, G-G-Halogenalkyl, G-G-Halogenalkoxy oder G-G-Aikylthio substituiert sein können, oder R 3 and R 4 each together form a 5- or 6-membered aliphatic, aromatic, heteroaromatic or heterocyclic ring which may optionally contain 1 to 2 atoms from the series O, S and N and which may be mono- or polysubstituted by halogen or by (VC 1- alkyl may be substituted, R 5 is hydrogen or C i -Ct, alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, where the abovementioned radicals are optionally independently up to five times by halogen or simply by nitro, cyano, C 3 -C 6 -cycloalkyl, O-R 1 -S (O) p -R 52 , -N (R 53 ) (R 54 ), -C (= O) N (R 53 ) (R 54 ), -O-Cl <)) - R 55 , -C (= 0) -R 55 , O-SO 2 -R 56 , aryl, hetaryl, heterocyclyl or oxoheterocyclyl may be substituted, wherein aryl, hetaryl, heterocyclyl or oxoheterocyclyl, again in each case monosubstituted to trisubstituted by halogen, nitro, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -G -haloalkyl. G-Ce-alkoxy, G-Ce-haloalkoxy, C 3 -C 6 -halocycloalkyl, C 1 -G, -alkoxy-C i -G-alkyl, C 1 -C 6 -alkoxycycloalkyl, Haloalkoxy-G-alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyloxy, cyano-C 1 -C 6 -alkyl, GG-cycloalkyl-C 1 -G-alkyl, C 2 -G-alkenyl, GG-alkynyl, GG-alkylthio, GG-alkylcarbonyl, C 3 -G-cycloalkyicarbonyl, C 2 -C 6 -alkenylcarbonyl, GG-haloalkylcarbonyl, GG-alkoxycarbonyl, C 1 -C 6 -alkylsulfonyl, GG-haloalkylsulfonyl, GG-alkylaminocarbonyi, di (C i - C 6) -alkylaminocarbonyl, GG-alkylcarbonyiamino, aryl or hetaryl may be substituted, where aryl and hetaryl are in turn optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxy, G-alkyl, GG-alkenyl, C 2 - C6-alkynyl, GG-alkoxy, GG-haloalkyl, GG-haloalkoxy or GG-Aikylthio may be substituted, or
R5 für G-Cö-Cycloalkyl oder C3-G-Heterocyclyi steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, G-G- Alkyl, G-G-Halogenalkyl, G-G-Alkoxy, CVG -Halogenalkoxy C3-G-Cycloaikyl, G-C6- Alkylthio. G-Ce-Alkylsulfmyl, G-C6-Alkylsulfonyl, Aryl, Hetaryl, Aryl-G-Ce-alkyl oder H etary 1 - ' i -G -al ky 1 substituiert sein können, wobei Aryl, Hetaryl. Aryl-C i - -alkyl und Hetaryl- G -G -alkyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G -Cs-Alkyl, G-C4- Haloalkyl , G -G-Aikoxy oder i - 4-Haloalkoxy substituiert sein können, oder R 5 is G-Cö-cycloalkyl or C 3 -G heterocyclyl, where the abovementioned radicals optionally independently of one another, are monosubstituted to trisubstituted by halogen, or simply by cyano, GG-alkyl, GG-haloalkyl, GG-alkoxy, CVG -haloalkoxy C 3 -G-cycloalkyl, GC 6 - alkylthio. G-Ce-alkylsulfmyl, GC 6 alkylsulfonyl, aryl, hetaryl, aryl-G-Ce-alkyl or H etary 1 - ' i -G -al ky 1 may be substituted, wherein aryl, hetaryl. Aryl-C i - alkyl and hetaryl-G -G-alkyl in each case monosubstituted to trisubstituted by halogen, cyano, nitro, G -Cs-alkyl, G-C4-haloalkyl, G-Aikoxy or i-4-haloalkoxy can be, or
R5 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF% SCN, G-G-Alkylamino, Di-(G-G)-alkylamino, Hydroxy, COOK, G -G- Alkyl, G-G-Cycloalkyl, G-G -Halogenalkyl, G-Ce-Alkoxy, G-G- Halogenalkoxy, Cs-Ce-Haiogencycloalkyl, C3-C6-Halogencycloalkyl-C 1 -G-alkyl, i -( ,,-Alkoxy- G -G -alkvl, C i -G -Halogenalkoxy-C i -G -alkyl, C ; -G - AI koxy-C ; -G -alkyloxy, Cyano-G-C6- alkyl, C:-G-C ycloalkyl-G -G-alkyl, C2-C6-Alkenyl, C3-C6-Alkinyl, SH. G-G-Alkylthio, G-C6- Alkylcarbonyl, Cs-Ce-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, Ci-Ce-Halogenalkylcarbonyi, G-Ce-Alkoxycarbonyl, C 1 -G - AI ky 1 sul fonyl , G-G-Halogenalkyisulfonyl, G-Ce- Alkylaminocarbonyl, Di-(G-C6)-alkylaminocarbonyl oder Tri-(C 1 -Ca -alkyl)silyl, p für 0, 1 oder 2 steht, R 5 is aryl or hetaryl, where the aforementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF% SCN, GG-alkylamino, di- (GG) -alkylamino , Hydroxy, COOK, G-Galkyl, GG-cycloalkyl, GG-haloalkyl, G-Ce-alkoxy, GG-haloalkoxy, Cs-Ce-halocycle, C3-C6-halocycloalkyl-C 1 -G-alkyl, i - (,, - alkoxy G -G -alkvl, C i -G haloalkoxy-C i -G alkyl, C; -G - Al koxy-C; -G -alkyloxy, cyano-G-C6-alkyl, C :. -GC ycloalkyl-G-G-alkyl, C 2 -C 6 alkenyl, C 3 -C 6 -alkynyl, SH GG-alkylthio, GC 6 - alkylcarbonyl, Cs-Ce-cycloalkylcarbonyl, C2-C6-alkenylcarbonyl, Ci-Ce-Halogenalkylcarbonyi, G-Ce-alkoxycarbonyl, C 1 -G - AI ky 1 sulfonyl, GG-Halogenalkyisulfonyl, G-Ce- alkylaminocarbonyl, di- (G-C6) -alkylaminocarbonyl or tri- (C 1 -Ca alkyl) silyl, p is 0, 1 or 2,
R51 für Wasserstoff oder für G -G-Alkyl, G-G.-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl oder C3-C«-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Nitro, Cyano, C3 -G -Cycloalkyl, G -C„-Alkoxy, G-G- Haiogenaikoxy, G-Ce-Alkylthio, C 1 -C6-Alkylsulfmyl, G-Ce-Alkylsulfonyl, C 1 -Ce-Alkylcarbonyl, C : Y- AI koxy imino-C i -G-alkyl , G-G-Cycloalkylcarbonyl, C;-C,,-Alkenylcarbonyl, G-G- Halogenalkylcarbonyl, G-G-Alkoxycarbonyl, G-G-Alkylsulfonyl, G-G-Halogenalkylsulfonyl, Ci-Ce-Alkylaminocarbonyl, Di-(C 1 -C6)-alkylaminocarbonyl, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, C1-C4- Alkyl, G-CVHaloalkyl, ( VC -i-Aikoxy oder G -CVHaloalkoxy substituiert sein können, oder R 51 is hydrogen or G-G-alkyl, GG.-alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C -heterocyclyl, where the abovementioned radicals, where appropriate, being independent of one another, are simple up to three times by halogen or simply by nitro, cyano, C 3 -G -cycloalkyl, G -C "-alkoxy, GG-Haiogenaikoxy, G-Ce-alkylthio, C 1 -C 6 -alkylsulfmyl, G-Ce-alkylsulfonyl, C 1 -ce-alkylcarbonyl, C: Y-alkoxy-imino-C 1 -G-alkyl, GG-cycloalkylcarbonyl, C 1 -C 10 -alkenylcarbonyl, GG-haloalkylcarbonyl, GG-alkoxycarbonyl, GG-alkylsulfonyl, GG-haloalkylsulfonyl, C 1 -C -alkylaminocarbonyl, Di- (C 1 -C 6) -alkylaminocarbonyl, aryl or hetaryl may be substituted, wherein aryl and hetaryl each one to three times by halogen, cyano, nitro, C 1 -C 4 alkyl, G-CVHaloalkyl, (VC -i-Aikoxy or G -CVHaloalkoxy may be substituted, or
R51 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, Ci-C6-Alkylamino, Di-(Ci-C6)-alkylamino, Hydroxy, COOK, G-G-Alkyl, G-G-Cycloalkyl, G-G-Haiogenaikyi, G-G-Alkoxy, G-G- Halogenalkoxy, C-.-(', -Halogencycloalkyl, C-,-(', -Ha!ogencycloalkyl-( 1 -G -alkyl, C 1 -G-Alkoxy- G -G-alkyl, ( > -G -Halogenalkoxy-C ·, -G -alkyl. ( ;-C, -Alkoxy-C 1 -C-alkyloxy, Cyano-Ci-C6- alkyl, Cs-Ce-Cycioalkyl-Ci -Ce-alkyl, C2-C6-Alkenyl, ( ;-C, -Alkinyl, ( VC, -Alkylthio, Ci-C6- Alkylcarbonyl, C3-C6-Cycloaikylcarbonyl, C2-Ce-Alkenylcarbonyl, (VC. -Halogenalkylcarbonyl. Ci-Ce-Alkoxycarbonyl, Cι-C, - AI kylsul fonyl, Ci-Cö-Halogenalkylsulfonyl, Ci-Ce- Alkylaminocarbonyl, Di-(Ci-C6)-alkylaminocarbonyl oder Tri-(C 1 -C6-alkyl)silyl, R 51 represents aryl or hetaryl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5, SCN, C 1 -C 6 -alkylamino, di (C 1 -C 4) C6) -alkylamino, hydroxy, COOK, GG-alkyl, GG-cycloalkyl, GG-haloalkyl, GG-alkoxy, GG-haloalkoxy, C -.- ( ' , -halocycloalkyl, C -, - ( ' , -Ha! - (1-G-alkyl, C 1 -G -alkoxy-G-alkyl, (> -G -haloalkoxy-C •, -G-alkyl. (-C) -alkoxy-C 1 -C -alkyloxy , cyano-Ci-C6 alkyl, Cs-Ce-Cycioalkyl-Ci -Ce-alkyl, C 2 -C 6 alkenyl, (-C, alkynyl, (VC, alkylthio, Ci-C 6 - alkylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, (C 1 -C 4 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) C 6) -alkylaminocarbonyl or tri- (C 1 -C 6 -alkyl) silyl,
R52 für Ci-Ce-Aikyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl oder C3-C6-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano , C3-C6- Cycloalkyl, G-C6-Alkoxy, (VC. -Halogenalkoxy. Ci-C6- Alkylthio, G-Ce-Alkylsulfinyl, Ci-C6- Alkylsulfonyl, Ci-Cö-Alkylcarbonyl, Ci-Ce-Alkoxyimino-C i-Ce-alkyl, Cs-Ce-Cycloaikylcarbonyl, C2-C6-Aikenylcarbonyi, Ci-Ce-Halogenalkylcarbonyl, Ci-Ce-Alkoxycarbonyl, G-C6- Alkylsulfonyl, (VC- -Halogenalkylsulfonyl, C 1-Cö-Alkyl aminocarbonyl, Di-(Ci-C«)- alkylaminocarbonyl, Aryl oder Hetaryl. wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, (VC-t-Alkyl, (VC Haloalkyl, Ci-('.i-Alkoxy oder ( V( ;-Hak»i!koxy substituiert sein können, oder R 52 is C 1 -C 6 -acylyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted may be substituted and the substituents are independently selected from halogen, nitro, cyano, C3-C6-cycloalkyl, GC 6 alkoxy, (VC. Haloalkoxy, Ci-C 6 - alkylthio, G-Ce-alkylsulfinyl, Ci-C 6 - alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -cycloalkylcarbonyl, C 2 -C 6 -cyclocyclic, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, G-C 6 Alkylsulfonyl, (VC- -haloalkylsulfonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 8 -alkylaminocarbonyl, aryl or hetaryl) where aryl and hetaryl are in each case monosubstituted to trisubstituted by halogen, cyano, nitro, (VC-) t-alkyl, (VC haloalkyl, Ci- ( ' .i-alkoxy or (V (; -Hak »i! koxy may be substituted, or
R52 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, Sf\, SCN, (VO -Alkylaniino. Di-(Ci-C6)-alkylamino, Hydroxy, COOH. Ci-Ce-Aikyl, C3-C6-Cycloalkyl, Ci-Ce-Halogenalkyl, Ci-Ce-Alkoxy, Ci-C«- Haiogenalkoxy, Cs-C -Halogencycloalkyl, Cs-Ce-Halogencycloalkyl-Ci-Ce-alkyl, G-Ce-Alkoxy- Ci-Ce-alkyl, C;-C, -Halogenalkoxy-C;-C, -alkyl, Ci-Cö-Alkoxy-Ci-Ce-alkyloxy, Cyano-Ci-Ce- alkyl, (VG-Cycloalkyl-Ci -G -alkyl, ( -G-Alkenyl, Cs-Ce-Alkinyl, G-Ce-Aikylthio, G -G - Alkylcarbonyl, C3-C6-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyi, G-Ce-Halogenalkylcarbonyl, G-G-Alkoxy carbonyl, G-G-Alkylsulfonyl, Ci-C6-Halogenaikylsulfonyl, G-G- Alkylaminocarbonyl, Di-(Ci-C6)-alkylaminocarbonyl oder Tri-(C 1 - -alkyl)silyl, R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, Sf.sup.1, SCN, (VO.-alkylanino, di (C 1 -C 4) C 6 ) -alkylamino, hydroxy, COOH, C 1 -C 6 -acyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C -halocycloalkyl, C 2 -C 5 -alkyl Ce-halocycloalkyl-Ci-Ce-alkyl, G-Ce-alkoxy-Ci-Ce alkyl, C, -C, haloalkoxy-C -C, alkyl, Ci-COE-alkoxy-Ci-Ce-alkyloxy, Cyano-Ci-Ce- alkyl, (VG-cycloalkyl-Ci -Galkyl, (-G-alkenyl, Cs-Ce-alkynyl, G-Ce-Aikylthio, G -G - alkylcarbonyl, C3-C6-cycloalkylcarbonyl, C2 -C6 alkenylcarbonyi, G-Ce-haloalkylcarbonyl, GG-alkoxycarbonyl, GG-alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, GG-alkylaminocarbonyl, di- (C 1 -C 6) -alkylaminocarbonyl or tri- (C 1 -alkyl) silyl,
R53 für Wasserstoff, G-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, G-G-Cycloalkyl, Ci-C4-Alkoxy, C i -G-Alkoxy-C -G- Alk l, G-G-Alkoxycarbonyl, G-G-Alkyiearbonyl, Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G -G-Alkyl, G-G-Haloalkyl. G -G-Alkoxy oder G-G- Haloalkoxy substituiert sein können, R 53 is hydrogen, G-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -G -alkoxy-C 1 -G -alk l, GG-alkoxycarbonyl, GG-Alkyiearbonyl, aryl, hetaryl, arylcarbonyl or hetarylcarbonyl, wherein aryl and hetaryl each one to three times by halogen, cyano, nitro, G-alkyl, GG-haloalkyl. GG-alkoxy or GG-haloalkoxy may be substituted,
R54 für Wasserstoff oder für G-G-Alkyl, G-G -Alkenyi, C.-C, -Alkinyl. G-G-Cycloalkyl oder G-G-Cycloalkyl-C 1 -G- Alkyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy, G-G-Alkyl, G-G- Cycloalkyl, G-C4-Alkoxy, G-C4-Haloalkoxy, G-C4-Aikylthio, G-G-Alkylsulfmyl, G-G- Alkylsulfonyl, G-G-Alkoxycarbonyl, G-G-Alkylcarbonyl oder C3-C6-Trialkylsilyl substituiert sein können, oder R 54 is hydrogen or GG-alkyl, GG-Alkenyi, C.-C, -alkynyl. GG-cycloalkyl or GG-cycloalkyl-C 1 -G-alkyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to five times by halogen or simply by cyano, nitro, hydroxy, GG-alkyl, GG-cycloalkyl, GC 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkylthio, GG-alkylsulfmyl, GG-alkylsulfonyl, GG-alkoxycarbonyl, GG-alkylcarbonyl or C3-C6-trialkylsilyl, or
R54 fü Aryl, Hetaryl, Aryl-G-Ce-alky! oder Heteroaryl-C' i-G -alkyl steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, G-Ce-Alkyl, - -Cycloalkyl, G-R 54 for Aryl, Hetaryl, Aryl-G-Ce-alky! or heteroaryl-C 'iG -alkyl, where the abovementioned radicals can be optionally substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, G-Ce-alkyl, - cycloalkyl, G
Ce-Cycloaikylamino, G-C4-Alkoxy, G-C4-Haloaikoxy, G-C4-Alkylthio, G-C4-Alkylsulfmyl, G- C4-Alkylsulfonyl, C 1 -G-Alkylsulfimino, C2-C6-Aikoxycarbonyl oder C2-C6-Alkylcarbonyl, oder Ce-cycloalkylamino, GC 4 -alkoxy, GC 4 -haloakoxy, GC 4 -alkylthio, GC 4 -alkylsulfmyl, G-C 4 -alkylsulfonyl, C 1 -G -alkylsulfimino, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -cycloalkylamino Alkylcarbonyl, or
R - und R54 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Atom aus der Reihe O.S oder N enthält und gegebenenfalls einfach bis vierfach mit G -G- Alkyl, Halogen, Cyano, Amino oder G -G-Alkoxy substituiert sein kann, R - and R 54 may be connected to each other via two to six carbon atoms and form a ring, which optionally additionally contains another atom from the series OS or N and optionally monosubstituted to four times with G-alkyl, halogen, cyano, amino or G -G alkoxy may be substituted,
R55 für G -G -Alkyl, G-G-Cycloalkyl, G-Ce-Halogenalkyi, G-G-Haiogencycloalkyl, C3-C6- Cycloalkyl-C 1 -G -alkyl, G-G-Haiogencycloalkyl-C 1 -G-alkyl, Cyano-C 1 -G -alkyl. G -G-Alkoxy, C I -G -Halogenalkoxy, G-G-Alkoxy-G -G-alkyl, C 1 -G -Halogenalkoxy-G -G -alkyl. Aryl. Hetaryl, Ar l-G -G-alk l oder Hetaryl -C 1 -G-alkyl steht, wobei Aryl, Hetaryl, Aryl -G -G-alkyl und Hetaryl-G -G-alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G -G-Alkyl. G-G-Cycloalkyl, G-G-Halogenalkyl, G -G -Alkoxy. G- G -Halogenalkoxy, G-G-Halogencycloalkyl oder G-Ce-Alkoxy-G-Ce-alkyl substituiert sein können, R56 für Ci-Ce-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenalkyl, C3-C6-Halogencycloalkyl, G-G - Cycloalkyl-C i -G -alkyl. C3-C6-Halogencycloalkyl-C i -G -alkyl. Cyano-C i -G -alkyl. G - -Alkoxy, Ci-Ce-Halogenalkoxy, C ι -G-Alkoxy-C ; -G -alkyl, G-( Y-Halogenalkoxy-C . -G -alkyl. Aryl, Hetaryl oder Aryl-G -G -alkyl steht, wobei Aryl, Hetaryl und Aryl-G -G-alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G -G -Alkyl, C3- G-Cycloalkyl, G-G-Halogenalkyl, G-G-Alkoxy, ( 1 -G - Halogenalkoxy. C3-G- Halogencycioalkyl oder C i-G-Alkoxy-C 1 -C6-alkyl substituiert sein können, R 55 is GG-alkyl, GG-cycloalkyl, G-Ce-haloalkyl, GG-halio-cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -G -alkyl, GG-halo-cycloalkyl-C 1 -G-alkyl, cyano -C 1 -G alkyl. GG-alkoxy, CI-G haloalkoxy, GG-alkoxy-G -g-alkyl, C 1 -G haloalkoxy-G-G-alkyl. Aryl. Hetaryl, Ar lG -G-alk l or hetaryl -C 1 -G alkyl, wherein aryl, hetaryl, aryl -G -G alkyl and hetaryl-G -G-alkyl optionally mono- or polysubstituted by identical or different halogen , Cyano, nitro, G-alkyl. GG-cycloalkyl, GG-haloalkyl, G -G alkoxy. G-G haloalkoxy, GG-halocycloalkyl or G-Ce-alkoxy-G-Ce-alkyl may be substituted, R 56 for Ci-Ce alkyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 3 -C 6 halocycloalkyl, GG - cycloalkyl-C i -G alkyl. C 3 -C 6 -halocycloalkyl-C 1 -G -alkyl. Cyano-C i -G alkyl. G - alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C -alkoxy-C; G -alkyl, G- (Y-haloalkoxy-C .G-alkyl. Aryl, hetaryl or aryl-G-G-alkyl, where aryl, hetaryl and aryl-G-G-alkyl optionally mono- or polysubstituted, identical or differently by halogen, cyano, nitro, G-galkyl, C 3 -G -cycloalkyl, GG-haloalkyl, GG-alkoxy, (1 -G - haloalkoxy, C 3 -G- halogeno-cycloalkyl or C iG -alkoxy-C 1-C6-alkyl may be substituted,
R" für Ci-Ce-Alkyl, C3-G-Cycloalkyl, CVC -Halogenalkyl, C3-C6-Halogencycloalkyl, C3-C6- Cycloalkyl-C i -C -alkyl, Cs-Ce-Halogencycloalkyl-C 1 -C6-alkyl, Cyano-C i-C6-alkyl, Ci-C6- Alkoxy- Ci -alkyl, C i-C. -Halogenalkoxy-C i -C. -alkyl. Aryl, Hetaryl, Aryl -CI-CÖ -alkyl oder Hetaryl-C i-C, -alkyl steht, wobei Aryl, Hetaryl, Aryl- i -('„-alkyl und Hetaryl-Ci-C6 -alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, C s -G,- Alkyl, C3-C6-Cycloalkyl, G-C -Halogenalkyl. ( VG-Alkoxy. G-G -Halogenalkoxy. C3-C6- Halogencycloalkyl oder C s -C «, - A 1 k o x y -C s - * -a I k y 1 substituiert sein können, R "represents C 1 -C 6 -alkyl, C 3 -G-cycloalkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 6 -C 6 -halocycloalkyl-C 1 -C 6 alkyl, cyano-C iC 6 alkyl, Ci-C 6 -... alkoxy Ci alkyl, C iC haloalkoxy-C i -C alkyl aryl, hetaryl, aryl-C CI east alkyl, or hetaryl-C 1 -C 4 -alkyl, where aryl, hetaryl, aryl-i- ( ' "-alkyl and hetaryl-C 1 -C 6 -alkyl, optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, C s -G, - alkyl, C 3 -C 6 cycloalkyl, haloalkyl GC (VG-alkoxy GG -haloalkoxy C 3 -C 6 -... halocycloalkyl or C s -C '- A 1 -C s -alkoxy - * -a I ky 1 can be substituted,
R7 für Wasserstoff, CVG-Alkyl, G-G -Alkenyl, G-G -Alkinyl, G-G -C ycloalkyl, Ci-C4-Alkoxy, C i - j-Alkoxy-C 1 -G -Alkyl, G-Ce-Alkoxycarbonyl oder C 1 -Ce -Alkylcarbonyl steht, R 7 is hydrogen, CVG-alkyl, GG-alkenyl, GG-alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -j-alkoxy-C 1 -G -alkyl, G-Ce-alkoxycarbonyl or C 1-Ce-alkylcarbonyl,
R7a für Wasserstoff, G -C (,-Alkyl, C -G,-Alkenyl, C2-C6-Alkinyl, C3-C«-Cycloalkyl, G -G-Alkoxy-G - Ct -Alkyl, G-Ce-Alkoxycarbonyl oder Ci-Ce-Aikyicarbonyi steht, R 7a is hydrogen, G is -C ( , -alkyl, C 1 -G, -alkenyl, C 2 -C 6 -alkynyl, C 3 -C -cycloalkyl, G is -G-alkoxy-G - Ct-alkyl, G- Ce-alkoxycarbonyl or Ci-Ce-Aikyicarbonyi stands,
R8 für Wasserstoff oder für C i -( '( -Alkyl, (';-(', - AI kenyl oder C2-Ce-Aikinyi steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy, G -G- Alkyl, C .-C, -('ycloalkyl, G-C4-Alkoxy, G-C4-Haloalkoxy, G-C4- Alkylthio, Ci-C4-Alkyisulflnyi, G-C4-Alkylsulfonyl, G-C4-Alkylsulfimino, G-C4- Alkyl sul fimino -C 1 -Gi-alkyl. C 1 -C4-Alkylsulfimino-C2-C5-aikylcarbonyl, C 1 -C4-Alkylsulfoximino, C 1 -Gi- AI ky I u I fo imi no-C 1 -C'4-alkyl, C 1 -C4-Alkylsulfoximino-C2-C5-alkylcarbonyl, C 1 -( , - Alkoxycarbonyl, G-Ce-Alkylcarbonyl oder C3-C6-Trialkylsilyl substituiert sein können, oder R 8 is hydrogen or C i - ( ' (alkyl, ( ' , - ) , - AI kenyl or C 2 -Ce-Aikinyi, where the abovementioned radicals are optionally independently from one another up to five times by halogen or simply by cyano , nitro, hydroxy, -G- G alkyl, C-C., - ( 'ycloalkyl, GC 4 alkoxy, haloalkoxy 4 GC, GC 4 - alkylthio, Ci-C 4 -Alkyisulflnyi, GC 4 alkylsulfonyl, GC 4 Alkylsulfimino, GC 4 -alkyl-sulfimino-C 1 -gi-alkyl, C 1 -C 4 -alkylsulfimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulfoximino, C 1 -Gi-Al ky I u I be imi no-C 1 -C ' 4-alkyl, C 1 -C 4 alkylsulfoximino-C 2 -C 5 -alkylcarbonyl, C 1 - (, - alkoxycarbonyl, G-Ce-alkylcarbonyl or C 3 -C 6-trialkylsilyl be substituted can, or
R8 für Aryl-G -G-alkyl, Heteroaryl-C ; -G -alkyl. C3-C!2-Cycloalkyl, ( ;- i -('ycloiilkyl-G -G-Alkyl oder C4-Ci2-Bicycloalkyi steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, C i -('» -Alkyl, G-G-Cycloalkyl, G-G-Cycloalkylamino, G -Ct-Alkoxy, G-C4-Haioaikoxy, G-C4-Alkylthio, Ci-C4-Alkylsuifinyl, G-C4-Alkylsulfonyl, G-C4- Alkyl sul fimino, C2-Ce-Alkoxycarbonyi oder C2-C6-Alkylcarbonyi, oder R 8 is aryl-G-G-alkyl, heteroaryl-C; -G alkyl. C 3 -C 2 cycloalkyl, (- i - ( 'ycloiilkyl-G-G-C 4 alkyl or -Ci2-Bicycloalkyi, where the abovementioned radicals can be optionally substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C i - ( ' »alkyl, GG-cycloalkyl, GG-cycloalkylamino, G -Ct-alkoxy, GC 4 -Haioaikoxy, GC 4 alkylthio, Ci-C 4 -Alkylsuifinyl, GC 4 Alkylsulfonyl, GC 4 -alkylsulfimino, C 2 -Ce-alkoxycarbonyi or C 2 -C 6 -alkylcarbonyi, or
R8 für einen einfach oder mehrfach, gleich oder verschieden substituierten 5- oder 6-gliedrigen aromatischen oder heteroaromatischen Ring, einen 4- bis 6-gliedrigen teilweise gesättigten Ri ng oder gesättigten heterozykiischen Ring, oder einen gesättigten oder aromatischen hetero- bizyklischen Ring steht, welcher gegebenenfalls ein bis drei Heteroatome aus der Reihe O, S oderR 8 represents a mono- or polysubstituted by identical or different substituent 5 or 6-membered aromatic or heteroaromatic ring, a 4- to 6-membered partially saturated ring or saturated heterocyclic ring, or a saturated or aromatic heterocyclic ring, which optionally contains one to three heteroatoms from the series O, S or
N enthalten kann und der gegebenenfalls ein- oder mehrfach substituiert sein kann, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, G-G-Alkyl, G-C^-Cycloalkvl, C3 -G -Cycloalkylamino, G -G-Alkoxy, G-G- Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsuifinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkylsulfimino, G-G-Alkoxycarbonyl oder C2-C6-Alkyicarbonyl, oder May contain N and may optionally be mono- or polysubstituted, wherein the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, GG-alkyl, GC ^ -Cycloalkvl, C3 -G -cycloalkylamino, G -G Alkoxy, GG-haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsuifinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfimino, GG-alkoxycarbonyl or C 2 -C 6 -alkyicarbonyl, or
R und R8 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Stickstoff-, Schwefel- oder Sauerstoffatom enthält und gegebenenfalls einfach bis vierfach mit G-G-Alkyl, Halogen, Cyano, Amino oder G- G-Alkoxy substituiert sein kann, R and R 8 may be connected to each other via two to six carbon atoms and form a ring which optionally additionally contains a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with GG-alkyl, halogen, cyano, amino or G-G Alkoxy may be substituted,
R9 für Wasserstoff, Fluor, Chlor, G-C4-Alkyi, G-G-Cycloalkyl oder G-C4-Haloaikyi steht, R9a für Wasserstoff, Fluor, Chlor, G -G-Alkyl, C3-C6-Cycloalkyl oder G-G-Haloalkyl steht, R10 für Wasserstoff, Fluor, Chlor oder G-G-Alkyl steht, und R10a für Wasserstoff, Fluor, Chlor oder G-G-Alkyl steht. R 9 is hydrogen, fluorine, chlorine, GC 4 -alkyi, GG-cycloalkyl or GC 4 -Haloaikyi, R 9a is hydrogen, fluorine, chlorine, G-alkyl, C 3 -C 6 -cycloalkyl or GG-haloalkyl R 10 is hydrogen, fluorine, chlorine or GG-alkyl, and R 10a is hydrogen, fluorine, chlorine or GG-alkyl.
Bevorzugt (Ausgestaltung 2-2) sind die Verbindungen der Formel (I) in denen Preferred (embodiment 2-2) are the compounds of the formula (I) in which
Q1 und Q zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N- Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q 1 and Q together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR6, -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, W für O steht, T is R 1 -OR 6 , -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ), W is O,
( 1 für eine Bindung, für -C(R9)(R10)-, oder für C(R9)(R10)C(R9a)(R10a) steht, (1 stands for a bond, for -C (R 9 ) (R 10 ) -, or for C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
U für einen Cyclus der Reihe U-i , U-2, U-5, U-6, U-9, U-10, U-20 oder U-23 steht, U is a cycle of the series U-1, U-2, U-5, U-6, U-9, U-10, U-20 or U-23,
Xa für Halogen, Nitro, Cyano, SF5, G-C4-Alkyi, G-C4-Halogenalkyl, G-G-Alkoxy, G-G- Halogenalkoxy, G-C4-Alkoxy-G-C4-alkyl, Cyano-G-C4-alkyl, G-G-Alkenyl, G-G-Alkinyl, CV -Alkylthio. C i -C4-Alkylcarbonyl, C i -C4-Alkoxycarbonyl, C i -C i - A I ko x y i m i n o -C i -C i -a I k y I , C i -O - A 1 ky ! su 1 fi ny ] , Ci-C4-Alkylsulfonyl, CVCVHalogenalkylsulfonyl, Phenyl, Pyridyl, Phenyl-X a is halogen, nitro, cyano, SF 5 , GC 4 alkyl, GC 4 haloalkyl, GG alkoxy, GG haloalkoxy, GC 4 alkoxy GC 4 alkyl, cyano GC 4 alkyl, GG alkenyl , GG-alkynyl, CV alkylthio. C i -C 4 -alkylcarbonyl, C i -C 4 -alkoxycarbonyl, C i -C i - Al ko xyimino -C i -C i -a I ky I, C i -O - A 1 ky! see below), C 1 -C 4 -alkylsulfonyl, C 2 -C 4 -haloalkylsulfonyl, phenyl, pyridyl, phenyl-
Ci-C4-alkyl oder Pyridyl-CVC 4-alkyl steht, wobei Phenyl, Pyridyl, Phenyl-Ci-C4-alkyl und Pyridyi-Ci-C4-alkyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, CVCVAlkyl, Ci- CVHalogenalkyl, CVCVAIkoxy oder C'i -CVHaloalkoxy substituiert sein können, n für 0, 1 , 2 oder 3 steht, C 1 -C 4 -alkyl or pyridyl-C 4 -C 4 -alkyl, where phenyl, pyridyl, phenyl-C 1 -C 4 -alkyl and pyridyl-C 1 -C 4 -alkyl are in each case monosubstituted to trisubstituted by halogen, cyano, nitro, C 2 -C 4 -alkyl, C 1 -C 4 -alkyl - CV haloalkyl, CVCVAIkoxy or C ' i -CVHaloalkoxy may be substituted, n is 0, 1, 2 or 3,
R1, R2, R . R4 jeweils unabliängig voneinander für Wasserstoff, Halogen, Cyano, CVC' i-Alkyl, C3- Ce-Cycloalkyl, C -C .i-Halogenalkyl. CVC .;-Alkoxy, C ' i -C i - H al ogenal k xy . C VC i-Alkoxy-C ·, -C .1- alkyl, C2-C4-Alkenyl, C2-C4-Alkenyloxy, CVCVAlkinyl, C3-C4-Alkinyloxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkoxyimino-Ci-C4-alkyl, C1-C4- Alkoxycarbonyl, Aryl oder Hetaiyl stehen, wobei Aryl und Hetaryl gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen, Cyano, C VCVAlkyl, C i -C ι-Alkoxy, C VC .i-Halogenalkyl. 1 -C Halogenalkoxy oder Ci-C4-Alkylthio substituiert sein können, R 1 , R 2 , R. R 4 each unabliängig another represent hydrogen, halogen, cyano, CVC 'i-alkyl, C3-Ce-cycloalkyl, C -C haloalkyl .i. CVC.; - alkoxy, C ' i -C i - halogenal kxy. C VC i-alkoxy-C ·, -C .1 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, CVCVAlkinyl, C 3 -C 4 alkynyloxy, Ci-C 4 alkylthio, C -C 4 -Alkylsulfmyl, Ci-C are 4 alkylsulfonyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, C1-C4 alkoxycarbonyl, aryl or Hetaiyl, where aryl and hetaryl which is optionally mono- to trisubstituted by identical or different by halogen, cyano, C VCV alkyl, C i -C ι-alkoxy, C VC .i-haloalkyl. May be substituted by 1-C haloalkoxy or C 1 -C 4 -alkylthio,
R5 für CH2Y steht, R 5 is CH 2 Y,
V für Wasserstoff, Halogen, Ci-Ce-Alkyl, Ci-Ce-Halogenaikyi, O-W -S(0)p-R52, -N(R53)(R54), -O- C(=0)-R55, O-SO-R" oder für einen der Reste Y-I bis Y-23 steht, V is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, OW -S (O) p -R 52 , -N (R 53 ) (R 54 ), -O-C (= O) -R 55 , O-SO-R "or represents one of the radicals YI to Y-23,
Y-2 Y-3 Y-4 Y-5 Y-6  Y-2 Y-3 Y-4 Y-5 Y-6
Y-13 Y-14 Y-15 Y-16 Y-17 Y-18  Y-13 Y-14 Y-15 Y-16 Y-17 Y-18
für Halogen, Nitro, Cyano, G-G-Aikyl, -Cycloalkyl, G-G -Halogenalkyl. G-G-Alkoxy, C -G -Halogenalkoxy. G-G-Halogencycloalkyl, C -G-Al koxy-C -G-alkyl, G-G- Halogenalkoxy-G -G-alkyl. G-G-Alkoxy-G-G-alkyloxy, Cyam>-G -G-alkyl, C-.-G- for halogen, nitro, cyano, GG-Aikyl, -cycloalkyl, GG-haloalkyl. GG-alkoxy, C -G -haloalkoxy. GG-halocycloalkyl, C-G-alkoxy-C-G-alkyl, GG-haloalkoxy-G-G-alkyl. GG-alkoxy-GG-alkyloxy, cyam> -G -g-alkyl, C -.-G-
Cycloalkyl-G -G-alkyl, C2-C6-Alkenyl, G-G-Alkinyl, G-G-Alkylthio, G-G-Alkylcarbonyl, -Cycloalkylcarbonyl, G-G-Alkenylcarbonyl, j-G-Halogenalkylcarbony!, G-G- Alkoxycarbonyl, C i -G-Alkylsulfonyl, G-G-Halogenalkylsulfonyi, Ci -Alkylaminocarbonyl, Di-(G )-alkylaminocarbonyl, G -Alkylcarbonylamino, Aryl oder Hetaryl stehen, wobei Aryl und Hetaryl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G-CVAikyl, G-G-Alkenyl, G-G-Alkinyl, G-G-Alkoxy, G -G - H a l o ge n a I k y I . G-G -Halogenalkoxy oder G-G-Alkylthio substituiert sein können und wobei die Ring-N-Atome in Y-13, Y-14 und Y-16 nicht durch Halogen, Nitro, Cyano, G-G- Alkoxy, G-Gi-Halogenalkoxy oder G -Ci- Alkoxy-C -G-alkyloxy substituiert sind, für 0, 1 oder 2 steht, für 0, 1 oder 2 steht, R51 für Wasserstoff oder für G-G-Alkyl, C2-C4-Aikenyl, G-G-Alkinyl, G-G-Cycloalkyl oder G-G-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano , C3-C6-Cycloalkyl, Ci-C4-Alkoxy, G-G-Halogenalkoxy. G- C4-Alkyithio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkylcarbonyl, G-G- Alkoxyimino-C i -C4-alkyl, C i -C4-Alkoxycarbonyl, C i -C4-Alkylsulfonyl, G-G- Halogenalkylsulfonyl, G-G-Aikylaminocarbonyi, Aryl oder Hetaryi substituiert sein können, wobei Aryl und Hetaryi jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, Ci-C4-Alkyl, Ci-C4-Haiogenalkyi, Ci-C4-Alkoxy oder Ci-C4-Haloaikoxy substituiert sein können, oder Cycloalkyl-G-G-alkyl, C 2 -C 6 -alkenyl, GG-alkynyl, GG-alkylthio, GG-alkylcarbonyl, -cycloalkylcarbonyl, GG-alkenylcarbonyl, jG-haloalkylcarbony !, GG-alkoxycarbonyl, C i -G-alkylsulfonyl , GG-Halogenalkylsulfonyi, Ci-alkylaminocarbonyl, di- (G) -alkylaminocarbonyl, G-Alkylcarbonylamino, aryl or hetaryl, wherein aryl and hetaryl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, hydroxy, G-CVAikyl , GG-alkenyl, GG-alkynyl, GG-alkoxy, G-G-halogenated I ky I. Wherein the ring N atoms in Y-13, Y-14 and Y-16 are not substituted by halogen, nitro, cyano, GG-alkoxy, G-Gi-haloalkoxy or G - Cis-alkoxy-C 1-6 alkyloxy, is 0, 1 or 2, is 0, 1 or 2, R 51 is hydrogen or GG-alkyl, C 2 -C 4 -arycyl, GG-alkynyl, GG-cycloalkyl or GG-heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, C 3 -C 4 -alkyl. C 6 -cycloalkyl, C 1 -C 4 -alkoxy, GG-haloalkoxy. G-C 4 -Alkyithio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-alkylcarbonyl, GG alkoxyimino-C i -C 4 alkyl, C i -C 4 -alkoxycarbonyl, C i -C 4 alkylsulfonyl, haloalkylsulfonyl GG, GG-Aikylaminocarbonyi, aryl or Hetaryi may be substituted, wherein aryl and Hetaryi each case monosubstituted to trisubstituted by halogen, cyano, nitro, Ci-C4-alkyl, Ci-C 4 -Haiogenalkyi, Ci-C 4 alkoxy or Ci-C 4 -Haloaikoxy can be substituted, or
R51 für Aryl oder Hetaryi steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, Ci-C4-Aikyi, Ci-C4-Halogenalkyl, Ci-C4-Aikoxy, G-C4-Halogenalkoxy, G-C4-Aikylthio oder G-C4-Alkylsulfonyl, R 51 is aryl or Hetaryi, where the aforementioned radicals optionally may be mono- to trisubstituted and the substituents are independently selected from halo, nitro, cyano, Ci-C 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkylthio or GC 4 -alkylsulfonyl,
R52 für G -G-Alkyl, C2-C4-Aikenyl, C2-C4-Alkinyi, G-G-Cycloalkyl oder G-G-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano , G-C4-Alkoxy, G-C4-Halogenaikoxy, G-C4-Aikylthio, G- C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, C i -C4-Alkylcarbonyl, Ci-C4-Aikoxyimino-G-C4-aikyl, G- C4-Alkoxycarbonyl, C i -C4-Alkylsulfonyl, C i -C4-Halogenalkylsulfonyl, G-G-R 52 is G-G-alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkyny, GG-cycloalkyl or GG-heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano , GC 4 -Aikylthio, GC 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, C i -C 4 alkylcarbonyl, Ci-C4--Aikoxyimino GC 4 -alkyl 4 alkoxy, GC 4 -Halogenaikoxy, GC, G, C 4 alkoxycarbonyl, C i -C 4 alkylsulfonyl, C i -C 4 haloalkylsulfonyl, GG-
Alkylaminocarbonyl, Aryl oder Hetaryi substituiert sein können, wobei Aryl und Hetaryi jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-G-Alkyl , G-G-Halogenalkyl, G-G- Alkoxy oder G -Gi-Haloalkoxy substituiert sein können, oder Alkylaminocarbonyl, aryl or hetaryi may be substituted, wherein aryl and hetaryi may each be monosubstituted to trisubstituted by halogen, cyano, nitro, G-G-alkyl, G-G-haloalkyl, G-G-alkoxy or G -Gi-haloalkoxy, or
R52 für Aryl oder Hetaryi steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, G-G-Aikyl, G-C4-Halogenaikyl, G-G-Alkoxy, G-G-Halogenalkoxy, G-C4-Aikyithio oder G-G-Alkylsulfonyl, R 52 represents aryl or hetaryin, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, GG-acyl, GC 4 -haloalkyl, GG-alkoxy, GG-haloalkoxy, GC 4 -alkyl or GG-alkylsulfonyl,
R53 für Wasserstoff, G -G-Alkyl, C i -C4-Alkoxy carbonyl, G-C6-Aikylcarbonyi, Aryl, Hetaryi, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Aryl, Hetaryi, Arylcarbonyl oder Hetarylcarbonyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G -G-Alkyl, G-G-Halogenalkyl, G- C4-Alkoxy oder G-Gi-Haloalkoxy substituiert sein können, R 53 is hydrogen, G is -Gh-alkyl, C 1 -C 4 -alkoxycarbonyl, GC 6 -Aikylcarbonyi, aryl, hetaryi, arylcarbonyl or hetarylcarbonyl, wherein aryl, hetaryic, arylcarbonyl or hetarylcarbonyl each just to three times by halogen, cyano , Nitro, G-alkyl, GG-haloalkyl, G-C 4 -alkoxy or G-Gi-haloalkoxy,
R54 für Wasserstoff oder für C s -C i-A!kyl, CVCVAIkenyl, C2-C4-Alkinyl oder C3-C4-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, C ; -C.;-Alkyl, ( ·.-( .! - ycloalkyl, G -CVAIkoxy, Ci-C4-Haloaikoxy, G- Ci-Alkylthio. C i -C4-Alkylsul finyl, Ci~C4-Alkylsulfonyi oder Phenyl substituiert sein können, R 54 for hydrogen or C 1 -C 10 -alkyl, C 2 -C 4 -alkynyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to five times by halogen or simply by cyano, C; C 1 -C 4 alkyl, (C 1 -C 4 alkyl), C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyi or phenyl can,
R" für Ci-C4-Aikyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Aryl-C i - ;-alkyl oder H etary 1 -C ·, -C.i -al ky 1 steht, wobei Aryl-CVC Valkyl und H e t ary I -C < -( .; -a 1 k y 1 gegebenenfalls einfach bis dreifach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, O- ' i-Alkyl, C i -Ci-Halogenalkyl, Ci-C4-Alkoxy oder C>-C.!-Ha!ogenalkoxy substituiert sein können, R "is C-C 4 -alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, aryl-C i -; -alkyl or H etary 1 -C ·, -Ci -al ky 1, wherein aryl-CVC Valkyl and H et ary I -C <- (.; -a 1 ky 1 optionally mono- to trisubstituted, identical or different may be substituted by halogen, cyano, nitro, O- 'i-alkyl, Ci-Ci-haloalkyl, Ci-C 4 alkoxy or C> -C!! - Hal genalkoxy,
R7 für Wasserstoff, Ci-C4-Alkyi, C2-C4-Aikenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, Ci-C4-Alkoxy, ( i -CVAI koxy-C ι - i-Aiky l, C ι -C AI koxycarbonyl oder Ci-C4-Alkylcarbonyl steht, R 7 is hydrogen, C 1 -C 4 -alkyi, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, (i -CVAI koxy-C ι-i-Aiky l, C ι -C AI koxycarbonyl or Ci-C4-alkylcarbonyl,
R7a für Wasserstoff, G-CVAlkyl, Ci-C4-Alkoxycarbonyl oder C i -C4-Alkylcarbonyl steht, R 7a 4 -alkoxycarbonyl or C i -C 4 alkylcarbonyl hydrogen, G-CVAlkyl, Ci-C,
R8 für Wasserstoff oder für C j-C'-i-Alkyl, CyCVAlkenyl oder C.-C.i-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, G-C4-Alkoxy, G-C4-Haloaikoxy, Ci-C4-Alkylthio, Ci-C4-Alkyisulfinyl, G-C4- Alkylsulfonyl, C i -C4-Alkoxy carbonyl, oder Ci-C4-Alkylcarbonyl substituiert sein können, oder R 8 is hydrogen or C jC ' -i-alkyl, CyCVAlkenyl or C.-Ci-alkynyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen, or simply by cyano, GC 4 -alkoxy, GC 4 - Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkyisulfinyl, GC 4 - alkylsulphonyl, C i -C 4 alkoxy carbonyl, or Ci-C4-alkylcarbonyl can be substituted or
R8 für Phenyimethyl, Phenylethyl, Pyridylmethyl, Cs-Ce-Cycioaikyl, C3-C6-Cycioaik> -Ci-C4-alkyi oder C .i-C s- Bi eye loa! kyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, C i -CVAlkyl, C s -C i-Alkoxy, C1-C4- Haloalkoxy. CVC i-Alkylthio, Ci-C4-Aikylsulflnyl, C 1 -C4-Alkylsulfonyl, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl, oder R 8 is phenyimethyl, phenylethyl, pyridylmethyl, Cs-Ce-cycloalkyl, C 3 -C 6 -cycloalkyl> -Ci-C 4 -alkyi or C .iC s- Bi eye loa! kyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C i -C alkyl, C s -C i alkoxy, C1 -C4 haloalkoxy. CVC i-alkylthio, Ci-C 4 -Aikylsulflnyl, C 1 -C 4 alkylsulfonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 alkylcarbonyl, or
R8 für Phenyl, Pyridy! , Pyrimidinyl, Thia/olyl, Thiadiazolyl, Oxa/olyl, Pyra/olyl, Thienyl oder Furanyi steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, C i -C i-Alkyl, -CVAIkinyl, C1-C4- Haiogenalkyi, Ci-C4-Alkoxy, Ci-C4-Haloaikoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl oder Ci- C4-Alkylsulfonyl, C2-Ce-Alkoxycarbonyi oder C2-C6-Alkylcarbonyl, oder R und R8 zusammen f r eine C3-C6-Alkylkette stehen, R 8 for Phenyl, Pyridy! , Pyrimidinyl, thia / olyl, thiadiazolyl, oxa / olyl, pyra / olyl, thienyl or furanyi, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are independently selected from halogen, cyano, nitro , hydroxy, amino, C i -C i-alkyl, -CVAIkinyl, C 1 -C 4 - Haiogenalkyi, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 - Alkylsulfmyl or Ci- C 4 alkylsulfonyl, C 2 -Ce-Alkoxycarbonyi or C 2 -C 6 -alkylcarbonyl, or R and R 8 together represent a C 3 -C 6 -alkyl chain,
R9 f r Wasserstoff, Fluor, Chlor oder C OAikyl steht, R9a für Wasserstoff, Fluor, Chlor oder Ci-C4-Alkyl, steht, R10 für Wasserstoff, Fluor, Chlor oder Ci-C4-Alkyl steht, und R 9 is hydrogen, fluorine, chlorine or C OAikyl, R 9a is hydrogen, fluorine, chlorine or Ci-C 4 alkyl, R 10 is hydrogen, fluorine, chlorine or Ci-C 4 alkyl, and
Rioa für Wasserstoff, Fluor, Chlor oder G-CVAlkyl steht. RIOA represents hydrogen, fluorine, chlorine or G-CVAlkyl.
Ebenfalls bevorzugt (Ausgestaltung 2-1) sind die Verbindungen der Formel (I), in denen Also preferred (embodiment 2-1) are the compounds of formula (I) in which
Q1 und Q2 zusammen für den Rest A-l stehen, der zusammen mit dem C- und N-Atom an das er gebunden ist, einen 6-gliedrigen aromatischen Ring bildet, T für R5, -Oir. -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, Q 1 and Q 2 together represent the radical Al which, together with the C and N atoms to which it is attached, forms a 6-membered aromatic ring, T represents R 5 , -Oir. -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für eine Bindung, für -C(R9)(R10)-, oder für C(R9)(R10)C(R9a)(R10a) steht, U für einen Cyclus der Reihe U-l , U-2, U-5, U-6, U-9, U-20 oder U-23 steht, G is a bond, for -C (R 9 ) (R 10 ) -, or for C (R 9 ) (R 10 ) C (R 9a ) (R 10a ), U is a cycle of the series Ul, U- 2, U-5, U-6, U-9, U-20 or U-23,
Xa für Halogen, Nitro, Cyano, SF5, Ci-C4-Alkyl, C i-C4-Haiogenalkyl, Ci-C4-Aikoxy, G-C4- Halogenalkoxy, Ci-C4-Alkoxy-G-C4-aikyl, Cyano-C . -Ci-alkyl. C2-C4-Alkenyi, C3-C4-Alkinyl,X a is halogen, nitro, cyano, SF 5 , C 1 -C 4 -alkyl, C 1 -C 4 -Haiogenalkyl, Ci-C 4 -alkoxy, GC 4 - haloalkoxy, Ci-C 4 -alkoxy-GC 4 -aikyl, cyano -C. -C-alkyl. C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl,
C s -C.t-Alk lthio, C i -C4-Alkylcarbonyl, C i -C4-Alkoxycarbonyl, Ci-C4-Alkoxyimino-Ci-C4-alkyi, C i -C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Halogenalkylsulfonyl, Phenyl, Pyridyl, Phenyl- Ci-C4-alkyl oder Pyridyl-Ci-C4-aikyl steht, wobei Phenyl, Pyridyl, Phenyi-G -C4-alkyi und Pyridyl-Ci-C4-alkyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-C4-Aikyl, G- G-Haloalkyl. G-C4-Alkoxy oder G-C4-Haloaikoxy substituiert sein können, n für 0, 1 , 2 oder 3 steht, C s -Ct-Alk thio, C i -C 4 alkylcarbonyl, C i -C 4 alkoxycarbonyl, Ci-C 4 alkoxyimino-Ci-C 4 -alkyi, C i -C 4 alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylsulfonyl, phenyl, pyridyl, phenyl Ci-C 4 -alkyl represents alkyl or pyridyl-Ci-C 4, where phenyl, pyridyl, phenyl-C 4 G -alkyi and pyridyl-C C 4 alkyl in each case one to three times by halogen, cyano, nitro, GC 4 -alkyl, G-G-haloalkyl. GC 4 -alkoxy or GC 4 -haloalkoxy, n is 0, 1, 2 or 3,
R1, R2, R3, R4 jeweils unabhängig voneinander für Wasserstoff, Halogen, Cyano, G-C4-Aikyl, G- G-Cycloalkyi, G -C4-Halogenaikyi, G-C4-Aikoxy, G-C4 -Halogenalkoxy, G-C4-Aikoxy-G-C4- alkyl. C -G-Alkenyl, C2-C4-Alkenyloxy, C3-C4-Alkinyl, C3-C4-Alkinyloxy, G-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkoxyimino-G-C4-alkyl, G-C4-R 1 , R 2 , R 3 , R 4 are each independently hydrogen, halogen, cyano, GC 4 -alkyl, G-G-cycloalkyl, G-C 4 -haloalkyl, GC 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkoxy-GC 4 - alkyl. C is -G-alkenyl, C 2 -C 4 -alkenyloxy, C 3 -C 4 -alkynyl, C 3 -C 4 -alkynyloxy, GC 4 -alkylthio, Ci-C 4 -alkylsulfmyl, Ci-C 4 -alkylsulfonyl, Ci -C 4 -alkoxyimino-GC 4 -alkyl, GC 4 -
Alkoxycarbonyl, Aryl oderHetaryl stehen, wobei Aryl und Hetaryl gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen, Cyano, G-C4-Aikyl, G-C4-Alkoxy, Ci-C4-Haiogenalkyl, G-C4-Halogenalkoxy oder G-G-Alkylthio substituiert sein können, R5 für C H Y steht, Alkoxycarbonyl, aryl or hetaryl, where aryl and hetaryl are optionally monosubstituted to trisubstituted by identical or different substituents, such as halogen, cyano, GC 4 -alkyl, GC 4 -alkoxy, C 1 -C 4 -haloalkyl, GC 4 -haloalkoxy or GG-alkylthio can, R 5 is CHY,
Y für Wasserstoff, Halogen, G-G-Alkyl, G-G -Haloalkyl, -O-R51, -S(0)P-R52, -N(R53)(R54), -O- C(=0)-R55, O-SO.-R" oder für einen der Reste Y-l bis Y-23 steht, Y is hydrogen, halogen, GG-alkyl, GG-haloalkyl, -OR 51 , -S (O) P- R 52 , -N (R 53 ) (R 54 ), -O-C (= O) -R 55 , O-SO.-R "or represents one of the radicals Yl to Y-23,
Xb für Halogen, Nitro, Cyano, G-G-Alkyl, C3-C6-Cycloalkyl, G-G -Halogenalkyl. G-G-Alkoxy, ( !-C. -Halogenalkoxy. G-G-Halogencycloaikyi, ( ι -G - AI koxy-C ι -C\ -alky 1, G-G- Halogenalkoxy-G-G-alkyl, G -G-Alkoxy-C ·, -G-alkyloxy. Cyano-G-G-alkyl, G-G- Cycloalkyl-C 1 -C6-alkyl, G-G-Alkenyl, G-G-Alkinyl, G-G-Alkylthio, G-G-Alkylearbonyl, Cs-Ce-Cycloalkylcarbonyl, G-G-Alkenylcarbonyl, C 1 -G -Halogenalkylcarbonyl, G-G- Alkoxycarbonyl, ( -G - Alkyl sul onyl, Ci-Ce-Halogenalkylsulfonyl, Ci-Ce-Aikyiaminoearbonyi, Di-(Ci-C6)-alkylaminocarbonyl, Ci-Ce-Alkyicarbonylamino, Aryl oder Hetaryl stehen, wobei Aryl und H taryl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, CVG,-Alkyl, (VG-Alkeriyl, C.-C, -Alkinyl, Ci-Cö-Alkoxy, Ci-C, -Halogenalkyl. Ci-Ce-Halogenalkoxy oder G-Ce-Alkylthio substituiert sein können und wobei die Ring-N-Atome in Y-l 3, Y- l 4 und Y-l 6 nicht durch Halogen, Nitro, Cyano, C1-C4- Alkoxy, Ci-Ci-Halogenalkoxy oder Ci-C4-Aikoxy-G-C4-alkyloxy substituiert sind, m für 0, 1 oder 2 steht, p für 0, 1 oder 2 steht, X b is halogen, nitro, cyano, GG-alkyl, C 3 -C 6 -cycloalkyl, GG-haloalkyl. GG-alkoxy, (! -C! -Haloalkoxy, GG-halogenocycloalkyl, (ι-G-alkoxy-C 1 -C -alky 1, GG-haloalkoxy-GG-alkyl, G-G-alkoxy-C ·, G-alkyloxy, cyano-GG-alkyl, GG-cycloalkyl-C 1 -C 6 -alkyl, GG-alkenyl, GG-alkynyl, GG-alkylthio, GG-alkylearbonyl, Cs-Ce-cycloalkylcarbonyl, GG-alkenylcarbonyl, C 1 -G haloalkylcarbonyl, GG alkoxycarbonyl, (-G - alkyl sul onyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-Aikyiaminoearbonyi, di- (Ci-C6) alkylaminocarbonyl, Ci-Ce-Alkyicarbonylamino, aryl or hetaryl in which aryl and tertiaryl are optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, CVG, -alkyl, (VG-alkeriyl, C 1 -C 4 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkyl , Haloalkyl, Ci-Ce-haloalkoxy or G-Ce-alkylthio may be substituted and wherein the ring N atoms in Yl 3, Y- l 4 and Yl 6 not by halogen, nitro, cyano, C1-C4 alkoxy , Ci-Ci-haloalkoxy or Ci-C4-Aikoxy-G-C4-alkyloxy are substituted, m is 0, 1 or 2, p is 0, 1 or 2 stand t,
R51 für Wasserstoff oder für G-C4-Alkyl, C2-C4-Aikenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl oder C3-C6-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano , G-CVAlkoxy, C i -CJ - H al gena I k xy , C;-C;-Alkylthio, G- C4-Alkylsulfinyl, G-C4-Alkylsulfonyl, -C.i- AI kylcarbony 1, C <: -C - A 1 k x y ϊττιϊη -C 1 -( -al k y 1 , G- C4-Alkoxycarbonyl, C 1 -G-Alkylsulfonyl, C 1 -C4-Halogenalkylsulfonyl, C1-C4-R 51 is hydrogen or C 4 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are optionally independent monosubstituted to trisubstituted by halogen or simply by cyano, G-CVAlkoxy, Ci-CJ-halogeno, C; -C; -alkylthio, G-C4-alkylsulfinyl, G-C4-alkylsulfonyl, -Ci AI kylcarbony 1, C < : -C - A 1 kxy ϊττιϊη -C 1 - (-alkenyl, C 1 -C 4 -alkoxycarbonyl, C 1 -G -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 1 -C 4 -alkyl
Alkylaminocarbonyl, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-G-Alkyl, G-G-Haloalkyi, G-G-Alkoxy oder G-G;-Haloalkoxy substituiert sein können, oder Alkylaminocarbonyl, aryl or hetaryl may be substituted, wherein aryl and hetaryl may each be monosubstituted to trisubstituted by halogen, cyano, nitro, G-G-alkyl, G-G-Haloalkyi, G-G-alkoxy or G-G; -haloalkoxy, or
R51 für Aryl oder Hetaryi steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, G-G-Alkyl, C ·, -G-Halogenalkyl. G-G-Alkoxy, < -G - H al ogenal k x y . Ci- i-Alkylthio oder G-C4-Alkylsulfonyl, R52 für Ci-C4-Alkyl, C2-C4-Aikenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl oder C3-C6-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano , G -CVAlkoxy, C -G - H al ogena 1 ko x y. C VC -Alkylthio, G- C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, C 1 -C4-Alkylcarbonyl, C 1 -C4-Alkoxyimino-C 1 -C4-alkyl, Ci- C4-Alkoxycarbonyi, Ci-C4-Alkyisulfonyl, C 1 -CVHalogenal kylsul fonyl , C1-C4-R 51 represents aryl or hetaryin, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, cyano, GG-alkyl, C •, -G -haloalkyl. GG-alkoxy, <-G - H al ogenal kxy. Ci-i-alkylthio or GC 4 -alkylsulfonyl, R 52 is C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are, if desired, independently of one another simply up to three times by halogen or simply by cyano, G -CVAlkoxy, C -G - H al ogena 1 ko x y. C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyi, C 1 -C 4 - Alkyisulfonyl, C 1 -CVHalogenal kylsul fonyl, C 1 -C 4 -
Alkylaminocarbonyl, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, Ci-C4-Alkyl, G-C4-Haloaikyl, C's -C' t-Alkoxy oder C' i-C .;-Haloalkoxy substituiert sein können, oder R52 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, Ci-C4-Alkyl, Cj -Ci-Halogenalkyl, G-C4-Alkoxy, Ci-C4-Halogena!koxy, Ci-C4-Alkylthio oder Ci-C4-Alkylsulfonyl, Alkylaminocarbonyl, aryl or hetaryl can be substituted, wherein aryl and hetaryl each one to three times by halogen, cyano, nitro, Ci-C 4 alkyl, GC 4 -Haloaikyl, C ' s -C ' t-alkoxy or C ' iC. Or R 52 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 - Ci-haloalkyl, GC 4 -alkoxy, C -alkoxy 4 -Halogena!, C 4 alkylthio or C 4 alkylsulfonyl,
R53 für Wasserstoff, G -CVAlkyl. Ci-C4-Alkoxycarbonyi, G-G-Alkyicarbonyl, Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-G-Alkyl, G -G-Haloalkyl. G-G- Alkoxy oder Ci-C4-Haloalkoxy substituiert sein können, R 53 is hydrogen, G -C -alkyl. C 1 -C 4 -alkoxycarbonyi, GG-alkyicarbonyl, aryl, hetaryl, arylcarbonyl or hetarylcarbonyl, where aryl, hetaryl, arylcarbonyl or hetarylcarbonyl are in each case monosubstituted to trisubstituted by halogen, cyano, nitro, GG-alkyl, G-haloalkyl. GG-alkoxy or C 1 -C 4 -haloalkoxy may be substituted,
R54 für Wasserstoff oder für G-C4-Alkyl, C -G-Alkenyl, C2-C4-Alkinyi oder C3-C4-Cycioaikyi steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Ci-C4-Alkyl, C-.-C i-Cy loalkyl, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy, G- CVAlkylthio, Ci-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl oder Phenyl substituiert sein können, R 54 4 alkyl, C -G-alkenyl, C 2 -C 4 -Alkinyi or C 3 -C 4 -Cycioaikyi hydrogen or GC, where the abovementioned radicals are optionally substituted independently of one another mono- to pentasubstituted by halogen or monosubstituted by cyano , C 4 alkyl, C -.- C i-Cy loalkyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, G CVAlkylthio Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl or phenyl can be substituted
R6 für G -G-Alkyl, Ci-C4-Halogenalkyl, G-G-Cycloalkyl - , -G-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Aryl-Ci-C4-alkyl oder Hetaryl-Ci-C4-alkyl steht, wobei Aryl-Ci-C4-aikyi und Hetaryl-Ci-C4-alkyl gegebenenfalls einfach bis dreifach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G-R 6 is -G-G alkyl, Ci-C4 haloalkyl, cycloalkyl GG -, -G-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, aryl-Ci-C4-alkyl or hetaryl C 1 -C 4 -alkyl, where aryl-C 1 -C 4 -alkyl and hetaryl-C 1 -C 4 -alkyl are optionally mono- to trisubstituted by identical or different halo, cyano, nitro, or
C t-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-A!koxy oder G -G - H a 1 o ge n a 1 k o x y substituiert sein können, C 1-alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or G-G-H-α-o-1-koxy may be substituted,
R7 für Wasserstoff, Ci-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, G-G-Cycloaikyl, Ci-C4-Alkoxy, i -( .;-Alkoxy-C -C.;-Alkyl, C 1 -C4-Alkoxy carbonyl oder C 1 -C4-Alkylcarbonyl steht, R 7 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, GG-cycloalkyl, C 1 -C 4 -alkoxy, i - (-; -alkoxy-C -C . Alkyl, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylcarbonyl,
R7a für Wasserstoff, Ci-C4-Aikyl, Ci-C4-Alkoxy carbonyl oder Ci-C4-Alkylcarbonyl steht, R8 für Wasserstoff oder für G-C4-A!kyl, C2-C4-Alkenyl oder C2-C4-Alkinyi steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, Ci-C4-Alkoxy, Ci-C4-Haloaikoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, G-C4- Alkylsulfonyl, C i -C4-Alkoxy carbonyl, oder Ci-C4-Alkylcarbonyl substituiert sein können, oder für Phenylmetfayl, Phenylethyi, Pyridylmethyl, CVG -Cycloalkyl, G-G-Cycloalky!-G -G-alkyl oder G-G- Bi cycloal kyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-C4-Aikyl, Ci-C4-Alkoxy, G-G- Haloalko y, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C i -C4-Alkylsulfonyl, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl, oder R 7a is hydrogen, Ci-C 4 -alkyl, Ci-C 4 alkoxy carbonyl or Ci-C is 4 alkylcarbonyl, R 8 represents hydrogen or GC 4 -A! Kyl, C 2 -C 4 alkenyl or C C 2 -C 4 -alkynyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, or simply by Cyano, Ci-C 4 alkoxy, Ci-C 4 -Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, GC 4 - alkylsulphonyl, C i -C 4 alkoxy carbonyl, or Ci-C 4 - Alkylcarbonyl may be substituted, or phenylmetfayl, Phenylethyi, pyridylmethyl, CVG cycloalkyl, GG-Cycloalky! -G-alkyl or GG-Bi cycloal kyl, wherein the aforementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents independently of one another are selected from halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, GG-haloalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl C 1 -C 4 -alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -alkylcarbonyl, or
R8 für Phenyi, Pyridyl, Pyrimidinyl, Thia/olyl, Oxazolyl, Pyrazolyl, Thienyl oder Furanyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, G-C4-Alkyi, G-C4-Aikoxy, G-C4-Haioaikoxy, G-G- Alkylthio, Ci-C4-Alkylsulfmyl oder C i -C4-Alkylsulfonyl, G-G-Alkoxyearbonyi oder G-G-R 8 represents phenyl, pyridyl, pyrimidinyl, thia / olyl, oxazolyl, pyrazolyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently from halogen, cyano, nitro , hydroxy, amino, GC 4 -Alkyi, GC 4 -alkoxy, GC 4 -Haioaikoxy, GG-alkylthio, Ci-C 4 -Alkylsulfmyl or C i -C 4 -alkylsulfonyl, or GG-GG Alkoxyearbonyi
Alkylcarbonyl, alkylcarbonyl,
R9 für Wasserstoff, Fluor, Chlor oder G-C4-Aikyl steht, R 9 is hydrogen, fluorine, chlorine or GC 4 -acyl,
R9a für Wasserstoff, Fluor, Chlor oder G -G-Alkyl, steht, R 9a is hydrogen, fluorine, chlorine or G-alkyl,
R10 für Wasserstoff, Fluor, Chlor oder G-C4-Alkyi steht, und R 10 is hydrogen, fluorine, chlorine or GC 4 -alkyi, and
R ioa fl . Wasserstoff, Fluor, Chlor oder G -G-Alky! steht. R i o a fl. Hydrogen, fluorine, chlorine or G -G-Alky! stands.
Weiter bevorzugt (Ausgestaltung 3-2) sind die Verbindungen der Formel (I) in denen Further preferred (embodiment 3-2) are the compounds of formula (I) in which
Q1 und Q zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N- Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, T für R\ -OR' -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, Q 1 and Q together represent one of Al, A-4 or A-5 which together with the C and N atoms to which they are attached form a 5- or 6-membered aromatic ring, T represents R \ -OR '-N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für eine Bindung oder für -C(R9)(R10)- steht, G is a bond or -C (R 9 ) (R 10 ) -,
U für einen Cyclus der Reihe U-2, U-9, U- 10 oder U-23 steht, Xa für Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl steht, n für 0, 1 oder 2 steht, U is a cycle of the series U-2, U-9, U-10 or U-23, X a is halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, n is 0, 1 or 2,
R1, R2, R \ R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, G -Ci-Alkyl, C ι -Ci-Halogenal kyl, (j -C.;-Alkoxy, CVCi-Halogenalkoxy. G -C AIkoxy- Ci-C4-alkyi, C2-C4-Alkenyl, C2-C4-Alkenyloxy, C3-C4-Alkinyl, G-G-Alkinyloxy, G-C4- Alkylthio. C i -C4-Alkylsulfinyl oder C i -C4-Alkylsulfonyl stehen, R 1 , R 2 , R 4 and R 4 each independently of one another represent a radical selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C -haloalkyl, (C 1 -C 4) -alkoxy, C -C -alkyl Haloalkoxy, G -C -alkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, C 3 -C 4 -alkynyl, GG-alkynyloxy, GC 4 -alkylthio, C i - C 4 alkylsulfinyl or C i -C 4 alkylsulfonyl,
R5 für CH2Y steht R 5 is CH 2 Y.
Y für Wasserstoff, Cl, Br, -O-R51, -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4, Y-5, Y-6 oder Y-7 steht, Y is hydrogen, Cl, Br, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y -5, Y-6 or Y-7,
Xb für Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyi, Methylamino carbonyl, Methylcarbonylamino, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl steht, m für 0, 1 oder 2 steht, p für 0, 1 oder 2 steht, X b is halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methylamino carbonyl, methylcarbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, m is 0, 1 or 2, p is 0, 1 or 2 stands,
R51 für Wasserstoff oder für C j -Ch-Alkyl, C2-C4-Alkenyl, G-G-Alkinyl oder C3-C6-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen oder einfach durch Cyano, Cs-Ce-Cycloalkyl, Ci-C4-Alkoxy, Ci-C4-Halogena!koxy, G -G-Alkylthio. Ci-C4-Alkylsulfmyl, C i -C4-Alkylsulfonyl, C i -C4-Alkylcarbonyl, C ι -C 4 -Alk oxy carbon y 1 oder C ι -G-Al kyl sui fonyl substituiert sein können, oder einfach durch Phenyi, Thienyl, Pyridyl, Pyrimidinyl oder Pyrazolyl substituiert sein können, die wiederum j eweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder R 51 is hydrogen or C j -Ch-alkyl, C 2 -C 4 -alkenyl, GG-alkynyl or C 3 -C 6 -cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, Cs-Cene or Cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, G-G-alkylthio. Ci-C 4 -Alkylsulfmyl, C i -C 4 alkylsulfonyl, C i -C 4 alkylcarbonyl, C ι -C 4 alk oxy carboxylic y is 1 or C ι -G-Al can be alkyl substituted sui fonyl, or just may be substituted by phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, which may in turn be substituted, independently of each other, simply to three times by halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or
R51 für Phenyi, Thienyl, Pyridyl, Pyrimidinyl oder Pyrazolyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, für G -G-Al kyl oder C3-C6-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano , C i -Ct-Alkoxy, Ci- C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, G-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyi oder Ci-C4-Alkylsulfonyi sowie aus Phenyl, Thienyl, Pyridyl, Pyrimidinyl, P ra/olyl, die jeweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder für Phenyl, Thienyl, Pyridyl, Pyrimidinyl oder Pyra lyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, für Wasserstoff, G-C4-Aikyi, C i -C4-Alkoxy carbonyl oder G-Ce-Alkyl carbonyl steht, für Wasserstoff oder für G-C4-Alkyl, (':-( -ι-Alkenyl, C:-C,-Alkinyl oder C s-CVCycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen, oder einfach durch Cyano, Methyl, Ethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Phenyl substituiert sein können, für Ci-C4-Alkyl, Ci-C4-Haiogenalkyi, C3-C6-Cycioaikyl-Ci-C4-a!kyl, Ci-C4-Alkoxy-G-C4-alkyl steht, f r Wasserstoff, G-C4-Aikyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C -Aikyi, Ci-C4-Alkoxy carbonyl oder Ci-C4-Alkylcarbonyl steht, für Wasserstoff, G-C4-Alkyi, C i -C4-Alkoxy carbonyl oder Ci-C4-Aikylearbonyl steht, für Wasserstoff oder für Ci-C4-Aikyl, C -- t-Alkenyl oder C.-C.;-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Trifluorethoxy, Methylthio, Ethyl thio, Methylsulfmyl, Ethylsulfmyl, Methylsulfonyl oder Ethylsulfonyl substituiert sein können, oder R8 für Phenyl methyl. Phenylethyl, Pyridylmethyl, Pyridylethyl, C3-C6-Cycloalkyl oder C .-G - Cycloalkyl-Ci-C4-alkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl, oder R 51 represents phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy G is -G-alkyl or C 3 -C 6 -cycloalkyl, wherein the aforesaid groups optionally may be mono- to trisubstituted and the substituents are independently selected from halogen, cyano, C i -Ct-alkoxy, Ci- C4-haloalkoxy, Ci-C4-alkylthio, Ci-C 4 -Alkylsulfmyl , Ci-C 4 alkylsulfonyl, GC 4 - alkylcarbonyl, Ci-C 4 -Alkoxycarbonyi or C 4 -Alkylsulfonyi and from phenyl, thienyl, pyridyl, pyrimidinyl, P ra / olyl, each independently of one another mono- to trisubstituted by halogen , Cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or is phenyl, thienyl, pyridyl, pyrimidinyl or Pyra lyl, wherein the aforementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, is hydrogen, GC 4 -Aikyi, C i -C 4 alkoxycarbonyl or G-Ce-alkyl carbonyl, for Wassersto ff or for GC 4 alkyl, ( ' :-( -ι-alkenyl, C: -C, alkynyl or C s -Cyccycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen, or simply by cyano, methyl, Ethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or phenyl may be substituted for Ci-C 4 alkyl, Ci-C 4 -Haiogenalkyi, C3-C 6 -Cycioaikyl-Ci-C 4 -a! kyl, Ci-C 4 -alkoxy-GC 4 alkyl, for hydrogen, GC 4 -alkyl, Ci-C 4 alkoxy, Ci-C 4 alkoxy-Ci-C -Aikyi, Ci-C 4 -alkoxycarbonyl or Ci-C4-alkylcarbonyl, represents hydrogen, GC 4 -Alkyi, C i -C 4 alkoxy carbonyl, or Ci-C 4 is -Aikylearbonyl, hydrogen or Ci-C 4 -alkyl, C - t Alkenyl or C.-C. Alkynyl, the abovementioned radicals optionally being independently of one another monosubstituted to trisubstituted by halogen or simply by cyano, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfmy l, methylsulfonyl or ethylsulfonyl, or R 8 is phenylmethyl. Phenylethyl, pyridylmethyl, pyridylethyl, C 3 -C 6 -cycloalkyl or C.-G-cycloalkyl-C 1 -C 4 -alkyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano Methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, or
R8 für Phenyl, Pyridyl, Pyrimidinyl, Thia/olyl. Thiadiazolyl, Oxa/olyl. Pyrazolyl, Thienyl oder Furanyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Methyl, Ethyl, Ethinyl, Trifluormethyl, Pentafluorethyl,R 8 is phenyl, pyridyl, pyrimidinyl, thia / olyl. Thiadiazolyl, oxa / olyl. Pyrazolyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently of one another from halogen, cyano, nitro, methyl, ethyl, ethynyl, trifluoromethyl, pentafluoroethyl,
Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfinyl, Methylsulfonyl oder Methoxycarbonyl, oder Methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl, or
R und R8 zusammen für eine (' ;-€* -Alkylkette stehen, R9 für Wasserstoff, Fluor, Chlor, Methyl oder Ethyl steht, und R and R 8 together represent a ( ' , - * * alkyl chain, R 9 is hydrogen, fluorine, chlorine, methyl or ethyl, and
R!0 für Wasserstoff, Fluor, Chlor, Methyl oder Ethyl steht. R ! 0 is hydrogen, fluorine, chlorine, methyl or ethyl.
Ebenfalls weiter bevorzugt (Ausgestaltung 3-1) sind die Verbindungen der Formel (I), in denen Also more preferred (embodiment 3-1) are the compounds of formula (I) in which
Q1 und Q2 zusammen für den Rest A-l stehen, der zusammen mit dem C- und N-Atom an das er gebunden ist, einen 6-gliedrigen aromatischen Ring bildet, Q 1 and Q 2 together represent the rest of Al, the to which it is attached together with the carbon and nitrogen atom, form a 6-membered aromatic ring,
T für R\ -OR6, -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, T R \ -OR 6, -N (R 7) (R 8) or -N (R 7a) -N (R 7) (R 8) group,
W für O steht, W stands for O,
G für eine Bindung oder für -C(R9)(R10)- steht, G is a bond or -C (R 9 ) (R 10 ) -,
U für einen Cyclus der Reihe U-2, U-9 oder U-23 steht, X 1 f r Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfinyl, Methylsulfonyl oder Methoxycarbonyl steht, n für 0, 1 oder 2 steht, R1, R-. R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, G -Ct-Alkyl, Ci-C4-Halogenaikyl, G -Ct-Alkoxy, C i -C s-Halogenalkoxy. G -G-Alkoxy-U is a cycle of the series U-2, U-9 or U-23, X 1 is halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl, n is 0 , 1 or 2, R 1 , R-. R 3 , R 4 are each independently a radical selected from the group of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C -alkoxy, C 1 -C 5 -haloalkoxy. G -G alkoxy
Ci-C4-alkyl, C2-C4-Alkenyl, C2-C4-Alkenyioxy, C3-C4-Alkinyl, C3-C4-Alkinyloxy, G-G- Alkylthio, C i -C4-Alkylsulfinyl oder Ci-C4-Aikylsuifonyi stehen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyioxy, C 3 -C 4 -alkynyl, C 3 -C 4 -alkynyloxy, GG-alkylthio, C 1 -C 4 -alkylsulfinyl or Ci-C 4 -Aikylsuifonyi stand,
R5 für CH2Y steht R 5 is CH 2 Y.
Y für Wasserstoff, Ci, Br, O-W -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4, Y-5, Y-6 oder Y-7 steht, Y is hydrogen, C 1, Br, OW-S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5, Y-6 or Y-7 stands,
Xb für Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methy lamino carbonyl , Methylcarbonylamino, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxy carbonyl steht, m für 0, I oder 2 steht, p für 0, 1 oder 2 steht, X b is halogen, cyano, methyl, ethyl, trifluoromethyl, methylamino carbonyl, methylcarbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, m is 0, I or 2, p is 0, 1 or 2 stands,
R51 für Wasserstoff oder für Ci-C4-Alkyl, G-G-Alkenyl oder G-Gi-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen oder einfach durch Cyano, G-C4-Aikoxy, G- C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfinyi, Ci-C4-Alkylsulfonyl, G-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder C i -C4-Alkylsulfonyl substituiert sein können, oder einfach durch Phenyl, Thienyi, Pyridyl, Pyrimidinyl oder Pyrazolyl substituiert sein können, die wiederum jeweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder R 51 represents hydrogen or C 1 -C 4 -alkyl, GG-alkenyl or G-Gi-alkynyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, GC 4 -alkoxy, G-C 4 -haloalkoxy , Ci-C 4 -Alkylsulfinyi, Ci-C 4 alkylsulfonyl, GC 4 4 alkylthio, Ci-C - alkylcarbonyl, Ci-C 4 -alkoxycarbonyl or C i -C 4 alkylsulfonyl may be substituted, or simply by phenyl, Thienyi, pyridyl, pyrimidinyl or pyrazolyl may be substituted, which in turn may each independently be monosubstituted to trisubstituted by halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or
R51 für Phenyl, Thienyi, Pyridyl, Pyrimidinyl oder Pyrazolyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, R 51 is phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
R52 für G-C4-Alkyl oder G-G-Cycloaikyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano , G-C4-Aikoxy, G- C4-Halogenaikoxy, G-C -Alkyithio, Ci-C4-Aikylsuifinyl, G-C4-Alkylsulfonyl, G-C4- Alkylcarbonyl, G-C4-Alkoxycarbonyl oder > -G- Alkylsul fonyl sowie aus Phenyl, Thienyi, Pyridyl, Pyrimidinyl, Pyrazolyl, die jeweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder R 52 is GC 4 -alkyl or GG-cycloalkyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, GC 4 -alkoxy, G-C 4 -haloakoxy, GC - Alkyithio, Ci-C 4 -Aikylsuifinyl, GC 4 alkylsulfonyl, GC 4 - alkylcarbonyl, GC 4 alkoxycarbonyl or> -G- alkylsulfonyl and from phenyl, thienyi, pyridyl, pyrimidinyl, pyrazolyl, each independently from one another to trisubstituted by Halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or
R52 für Phenyi, Thienyl, Pyridyl, Pyrimidinyl oder Pyi'azolyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, R 52 is phenyi, thienyl, pyridyl, pyrimidinyl or pyiazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy .
R53 für Wasserstoff, CVCVAlkyl, C ; -C4- AI koxycarbonyl oder Ci-Ce-Aikylcarbonyl steht, R 53 is hydrogen, CVC-alkyl, C; -C 4 - Al koxycarbonyl or Ci-Ce-Aikylcarbonyl,
R54 für Wasserstoff oder für Ci-C4-Aikyl, C2-C4-Alkenyi, C2-C4-Alkinyl oder C3-C4-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen, oder einfach durch Cyano, Methyl, Ethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Phenyi substituiert sein können, R 54 is hydrogen or C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen, or simply may be substituted by cyano, methyl, ethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or phenyi,
R6 für Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloallcyi-Ci-C4-alk>d, Ci-C4-Alkoxy-Ci-C4-alkyl steht, R 6 is Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 3 -C 6 -Cycloallcyi-Ci-C 4 -alk> d, Ci-C4-alkoxy-Ci-C 4 -alkyl,
R für Wasserstoff, Ci-C4-Alkyl, Ci-C4-Aikoxy, Ci-C4-Aikoxy-Ci-C4-Alkyl, Ci-C4-Alkoxycarbonyi oder Ci-C4-Alkylcarbonyl steht, R is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -acoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyi or C 1 -C 4 -alkylcarbonyl,
R7a für Wasserstoff, Ci-C4-Alkyl, Ci-C4-Alkoxycarbonyi oder C i -C4-Alkylcarbonyl steht, R 7a 4 alkyl, Ci-C 4 -Alkoxycarbonyi or C i -C 4 alkylcarbonyl, hydrogen, Ci-C,
R8 für Wasserstoff oder für Ci-C4-Alkyl, C2-C4-Alkenyl oder C -Ci-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano, Methoxy, Ethoxy, Difiuormethoxy, Trifluormethoxy, Trifluorethoxy, Methylthio, Ethyl thio, Methylsulfmyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl substituiert sein können, oder R 8 is hydrogen or C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 1 -C 6 -alkynyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, methoxy, ethoxy, difluoromethoxy, Trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or
R8 für Phenyimethyi, Phenylethyl, Pyridylmethyl, Pyridylethyl, CVG -Cycloalkyl oder C3-C6- Cycloalkyl-C i -C4-alkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxy carbonyl, oder R 8 is phenyimethyl, phenylethyl, pyridylmethyl, pyridylethyl, CVG-cycloalkyl or C 3 -C 6 -cycloalkyl-C i -C 4 -alkyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, or
R8 für Phenyl, Pyridyl, Pyrimidinyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl oder Furanyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, TrifSuormethoxy, Methylthio,R 8 is phenyl, pyridyl, pyrimidinyl, thiazolyl, oxazolyl, pyrazolyl, thienyl or furanyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently of one another from halogen, cyano, methyl, ethyl, Trifluoromethyl, methoxy, ethoxy, trifuormethoxy, methylthio,
Methylsulfmyl, Methylsulfonyl oder Methoxy carbonyl, Methylsulfmyl, methylsulfonyl or methoxycarbonyl,
R9 für Wasserstoff, Fluor, Chlor, Methyl oder Ethyl steht, und R 9 is hydrogen, fluorine, chlorine, methyl or ethyl, and
R10 für Wasserstoff, Fluor, Chlor Methyl oder Ethyl steht. Besonders bevorzugt (Ausgestaltung 4-2) sind die Verbindungen der Formel (I) in denen R 10 is hydrogen, fluorine, chlorine, methyl or ethyl. Particularly preferred (embodiment 4-2) are the compounds of formula (I) in which
Q1 und 0 zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N- Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q 1 and O together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR" oder -N(R7)(R8) steht, T is R 1 -OR "or -N (R 7 ) (R 8 ),
W für O steht, G für eine Bindung oder für -C(R9)(R10)- steht, W is O, G is a bond or -C (R 9 ) (R 10 ) -,
U für U-2, U-9, U-10 oder U-23 steht, U stands for U-2, U-9, U-10 or U-23,
Xa für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Trifluormethoxy oder Cyano steht, n für 0, 1 oder 2 steht, R1, R\ R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, n- oder iso-Propyl, Methoxy, Ethoxy, n- oder iso- Propoxy, Methylthio, Ethyl thio, Difiuormethyl, Trifluormethyl, Trifluormethoxy oder Difluormethoxy stehen, X a is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy or cyano, n is 0, 1 or 2, R 1 , R \ R 3 , R 4 are each independently a radical from the series Are hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or isopropoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy,
R5 für C H Y steht, Y für Wasserstoff, C hlor. 0-R . -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4, Y-5, Y-6 oder Y-7 steht, R 5 is CHY, Y is hydrogen, C is chloro. 0-R. -S (0) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5, Y-6 or Y-7,
Xb f r Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- und iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difiuormethyl, Trifluormethyl, Methylaminocarbonyl oder Methylcarbonylamino steht, m für 0 oder 1 steht, p für 0, 1 oder 2 steht, X b represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl and isopropyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2,
R für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pent-3-yl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cy cl op entylmethyl , Cyclohexylmethyl, 2,2,2-Trifluorethyl, 2-Methoxyethyl,R is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pent-3-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl , Cyclohexylmethyl, 2,2,2-trifluoroethyl, 2-methoxyethyl,
Methoxycarbonylmethyl, Phenyl, 2-Fluor-Phenyl, 3-Fiuor-Phenyl, 4-Fluor-Phenyl, 2-Chlor- Phenyl, 3-Chlor-Phenyl, 4-Chlor-Phenyl, Phenylmethyl, 4-Fluor-Phenylmethyl, 3-Fluor- Phenylmethyl, 2-Fluor-Phenylmethyl, Pyrid-3-yl, 6-Chlor-Pyrid-3-yl, Pyridyl-2-yl oder 1- Methylpyrazol-5-yl steht, Methoxycarbonylmethyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, phenylmethyl, 4-fluoro-phenylmethyl, 3 Fluorophenylmethyl, 2-fluoro-phenylmethyl, pyrid-3-yl, 6-chloro-pyrid-3-yl, pyridyl-2-yl or 1-methylpyrazol-5-yl,
R52 für Methyl, Ethyl, n- oder iso-Propyl. Phenyl oder Phenylmethyl steht, R 52 is methyl, ethyl, n- or iso-propyl. Phenyl or phenylmethyl,
R53 für Wasserstoff, Methyl, Ethyl, Methylcarbonyl oder Ethylcarbonyl steht, R 53 is hydrogen, methyl, ethyl, methylcarbonyl or ethylcarbonyl,
R54 für Methyl, Ethyl, n- oder iso-Propyl, Cyclopropyl oder Phenylmethyl steht, R 54 is methyl, ethyl, n- or iso-propyl, cyclopropyl or phenylmethyl,
R6 für Methyl, Ethyl oder n- oder iso-Propyl steht, R 6 is methyl, ethyl or n- or isopropyl,
R für Wasserstoff, Methyl oder Ethyl steht, R is hydrogen, methyl or ethyl,
R8 für Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Trifluorethyl, Cyclopropyl, Fluorcyclopropyl, Chlorcyclopropyl, Cyanocyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanocyclohexyl, Cyclopropylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Methyl, Ethyl, Methoxy, Ethoxy, Trifluormethyl, Pentafluorethyl, Trifluormethoxy, Cyano oder Nitro substituiertes Phenyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes Phenylmethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 1 -Phenylethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 2-Phenylethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor oder Methyl substituiertes Pyrid-3-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor. Brom, Methyl, Trifluormethyl, Cyano, Nitro oder Ethinyl substituiertes Pyridyl-2-yi, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor.Chlor oder Methoxy substituiertes Pyrid-4-yl. gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 1 ,3-Pyrimidin-2-yl. gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes l,3-Pyrimidin-5-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor oder Methyl substituiertes Thia/ol-2-yl, 1 .2.4- Thiadiazol-5-yl oder für gegebenenfalls durch Chlor. Brom oder Methyl substituiertes 1 -Methyl - Pyrazol-5-yi steht, R9 für Wasserstoff oder Methyl steht, und R 8 is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, trifluoroethyl, cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, cyanocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanocyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl , optionally mono- to disubstituted independently of one another by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, cyano or nitro-substituted phenyl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted phenylmethyl, optionally mono- to disubstituted independently 1-phenylethyl substituted by fluorine or chlorine, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 2-phenylethyl, optionally mono- to disubstituted independently of one another by fluorine, chlorine or methyl-substituted pyrid-3-yl, optionally mono- to disubstituted independently of one another by fluorine, Chlorine. Bromine, methyl, trifluoromethyl, cyano, nitro or ethynyl-substituted pyridyl-2-yi, optionally mono- to disubstituted independently of each other by fluorine-chlorine or methoxy-substituted pyrid-4-yl. optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 1, 3-pyrimidin-2-yl. optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 1, 3-pyrimidin-5-yl, optionally mono- to disubstituted independently of one another by fluorine, chlorine or methyl-substituted thia / ol-2-yl, 1 .2.4-thiadiazole-5 yl or optionally chlorine. Bromine or methyl substituted 1-methyl-pyrazol-5-yl, R 9 is hydrogen or methyl, and
R10 für Wasserstoff steht. R 10 is hydrogen.
Ebenfalls besonders bevorzugt (Ausgestaltung 4-1) sind die Verbindungen der Formel (I) in denen Q1 und Q2 zusammen für den Rest A-l stehen, der zusammen mit dem C- und N-Atom an das er gebunden ist, einen 6-giiedrigen aromatischen Ring bildet, Also particularly preferred (embodiment 4-1), the compounds of formula (I) in which Q 1 and Q 2 together represent the balance Al, which it is attached together with the carbon and nitrogen atom to which, a 6- giiedrigen forms aromatic ring,
T für R\ -OR6 oder -N(R7)(R8) steht, T is R 1 -OR 6 or -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für eine Bindung oder für -€(R9)(R10)- steht, U für U-2, U-9 oder U-23 steht, G is a bond or - € (R 9 ) (R 10 ) -, U is U-2, U-9 or U-23,
Xa für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Trifluormethoxy oder Cyano steht, n für 0, 1 oder 2 steht, X a is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy or cyano, n is 0, 1 or 2,
R1, R\ R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, n- oder iso-Propyl, Methoxy, Ethoxy, n- oder iso-R 1 , R \ R 3 , R 4 are each independently a radical selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso -
Propoxy, Methylthio, Ethyl thio, Difluormethyl, Trifluormethyl, Trifluormethoxy oderPropoxy, methylthio, Ethyl thio, difluoromethyl, trifluoromethyl, trifluoromethoxy or
DifSuormethoxy stehen, DifSuormethoxy stand,
R5 für C ITY steht, R 5 stands for C ITY,
Y für Wasserstoff, Chlor, -O-R51, -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2. Y-3, Y-4, Y-5, Y-6 oder Y-7 steht, Y is hydrogen, chlorine, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2. Y-3, Y-4, Y-5, Y-6 or Y-7,
Xb für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- und iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethyl thio, Difluormethyl, Trifluormethyl, Methylaminocarbonyl oder Methylcarbonylamino steht, m für 0 oder 1 steht, p für 0, 1 oder 2 steht, R51 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, 2-Methoxyethyl, Methoxy carbonylmethyl, Phenyl, 2-F-Phenyl, 3-F-Phenyi, 4-F-Phenyl, 2-Cl-Phenyl, 3-Cl-Phenyl, 4-Cl-Pheny!, Phenylmethyl, 4-F -Phenylmethyl, 3 -F -Phenylmethyl, 2-F-Phenylmethyl, Pyrid-3-yl, 6 -C h I o r- Py ri d -3 -y 1. Pvrid-2-yl oder 1 -Methylpyrazol-5 -yl steht, X b is fluorine, chlorine, bromine, cyano, methyl, ethyl, n- and iso-propyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0 , 1 or 2, R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, 2-methoxyethyl, methoxy carbonylmethyl, phenyl, 2-F-phenyl, 3-F-Phenyi, 4-F-phenyl, 2-Cl-phenyl, 3-Cl-phenyl, 4-Cl-Pheny !, phenylmethyl, 4-F-phenylmethyl, 3-F-phenylmethyl, 2-F-phenylmethyl, pyrid-3-yl, 6-C h -or-pyridine-3-yl. Pvrid-2-yl or 1-methylpyrazole-5-yl,
R52 für Methyl, Ethyl, n- oder iso-Propyl, Phenyl oder Phenylmethyl steht, R 52 is methyl, ethyl, n- or iso-propyl, phenyl or phenylmethyl,
R53 für Wasserstoff, Methyl, Ethyl, Methyl carbonyl oder Ethylcarbonyl steht, R 53 is hydrogen, methyl, ethyl, methylcarbonyl or ethylcarbonyl,
R 1 für Methyl, Ethyl, n- oder iso-Propyl, Cyclopropyl oder Phenylmethyl steht, R 1 is methyl, ethyl, n- or iso-propyl, cyclopropyl or phenylmethyl,
R' für Methyl, Ethyl oder n- oder iso-Propyl steht, R 'is methyl, ethyl or n- or isopropyl,
R für Wasserstoff, Methyl oder Ethyl steht, R is hydrogen, methyl or ethyl,
R8 für Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl. Trifluorethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylmethyl, gegebenenfalls durch Fluor oder Chlor substituiertes Phenyl, gegebenenfalls durch Fluor oder Chlor substituiertes Phenylmethyl, gegebenenfalls durch Fluor oder Chlor substituiertes 1 -Phenyl ethyl, gegebenenfalls durch Fluor oder Chlor substituiertes 2-Phenylethyl, gegebenenfalls durch Fluor oder Chlor substituiertes Pyrid-3-yl, gegebenenfalls durch Fluor oder Chlor substituiertes Pyridy!-2-yl oder gegebenenfalls durch Fluor oder Chlor substituiertes Pyrid-4-yl steht, R 8 is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl. Trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, optionally substituted by fluorine or chlorine-substituted phenyl, optionally substituted by fluorine or chlorine-substituted phenylmethyl, optionally substituted by fluorine or chlorine-substituted 1-phenyl ethyl, optionally substituted by fluorine or chlorine-substituted 2-phenylethyl, optionally fluorine or chlorine-substituted pyrid-3-yl, optionally fluorine- or chlorine-substituted pyridyl-2-yl or optionally fluorine- or chlorine-substituted pyrid-4-yl,
R9 für Wasserstoff oder Methyl steht, und R 9 is hydrogen or methyl, and
R10 für Wasserstoff steht. R 10 is hydrogen.
Ganz besonders bevorzugt (Ausgestaltung 5-2) sind die Verbindungen der Formel (I), in denen Very particularly preferred (embodiment 5-2) are the compounds of the formula (I) in which
Q1 und Q- zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N- Atom an das sie gebunden sind, einen 5- oder 6-giiedrigen aromatischen Ring bilden, Q 1 and Q- together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR" oder -N(R7)(R8) steht, T is R 1 -OR "or -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für -C(R9)(R10)- steht, G is -C (R 9 ) (R 10 ) -,
U für U-2, U-9, U-10 oder U-23 steht, U stands for U-2, U-9, U-10 or U-23,
Xa für Fluor, Chlor, Methyl, Trifluormethyl oder Methoxy steht, n für 0, 1 oder 2 steht, R1, R-. R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Cyano, Methyl, Methoxy, Ethoxy, Methylthio, Trifluormethyl oder Trifluormethoxy stehen, X a is fluorine, chlorine, methyl, trifluoromethyl or methoxy, n is 0, 1 or 2, R 1 , R-. R 3 , R 4 each independently represent a radical from the series consisting of hydrogen, fluorine, chlorine, cyano, methyl, methoxy, ethoxy, methylthio, trifluoromethyl or trifluoromethoxy,
R5 für C H Y steht, Y für Wasserstoff, Chlor. 0-R . -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4, Y-5 oder Y-6 steht, R 5 is CHY, Y is hydrogen, chlorine. 0-R. -S (0) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5 or Y-6,
Xb für Chlor, Cyano, Methyl, Methoxy, Methylthio, Trifluormethyl, Methylaminocarbonyl oder Methylcarbonylamino steht, m für 0 oder 1 steht, p für 0, 1 oder 2 steht, X b is chlorine, cyano, methyl, methoxy, methylthio, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2,
R51 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, t-Butyl, Pent-3-yl, Cyclopentyl, Cyclohexyl, 2,2,2-Trifluorethyi, 2-Methoxyethyl, Methoxycarbonylmethyl, Phenyi, 4-Fluor-Phenyl, 2-Chlor- Phenyl, 3-Chlor-Phenyl, 4-Chlor-Phenyl. Phenylmethyl, 4-Fluor-Phenylmethyl , Pyrid-3-yl. 6- Chlor-Pyrid-3-yl , Pyrid-2-yl oder l-Methylpyrazoi-5-yl steht, R52 für Methyl, Ethyl, iso-Propyl, Phenyi oder Phenylmethyl steht, R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, t-butyl, pent-3-yl, cyclopentyl, cyclohexyl, 2,2,2-trifluoroethylene, 2-methoxyethyl, methoxycarbonylmethyl, phenyl, 4-fluoro Phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl. Phenylmethyl, 4-fluoro-phenylmethyl, pyrid-3-yl. 6 is chloro-pyrid-3-yl, pyrid-2-yl or 1-methylpyrazoi-5-yl, R 52 is methyl, ethyl, isopropyl, phenyl or phenylmethyl,
R53 für Wasserstoff, Methylcarbonyl oder Ethylcarbonyl steht, R 53 is hydrogen, methylcarbonyl or ethylcarbonyl,
R54 für Methyl, Ethyl, Cyclopropyl oder Phenylmethyl steht, R 54 is methyl, ethyl, cyclopropyl or phenylmethyl,
R' für Methyl steht, R 'is methyl,
R für Wasserstoff steht, R8 für Methyl, Ethyl, n- oder iso-Propyl, iso-, oder tert-Butyl, Trifluorethyl, Cyclopropyl, 1- Cyanocyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1 -Cyanocyclohexyl, Cyclopropylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor. Methyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Cyano substituiertes Phenyi, gegebenenfalls durch Chlor substituiertes Phenylmethyl, gegebenenfalls durch Chlor substituiertes 1 -Phenyi ethyl, gegebenenfalls durch Chlor substituiertesR is hydrogen, R 8 is methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, trifluoroethyl, cyclopropyl, 1-cyanocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyano-cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl , optionally mono- to disubstituted independently of one another by fluorine, chlorine. Methyl, methoxy, trifluoromethyl, trifluoromethoxy or cyano-substituted phenyl, optionally substituted by chlorine-substituted phenylmethyl, optionally substituted by chlorine-substituted 1-phenylethyl, optionally substituted by chlorine
2-Phenyiethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Chlor oder Methyl substituiertes Pyrid-3-yi, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes Pyrid-2-yl, gegebenenfalls einfach durch Brom, Methyl, Trifluormethyl, Cyano, Nitro oder Ethinyl substituiertes Pyrid-2-yl. s einfach durch Methoxy substituiertes Pyrid-4-yl, l,3-Pyrimidin-2-yl, gegebenenfalls einfach bis zweifach durch Chlor substituiertes l ,3-Pyrimidin-5-yl, gegebenenfalls einfach durch Chlor oder Methyl substituiertes Thia/ol-2-yl, l,2,4-Thiadiazol-5-yl oder gegebenenfalls durch Brom substituiertes 1 -Methyl - Pyrazoi-5-yl steht, oder R7 und R8 zusammen für -(CH2)4- stehen, R9 für Wasserstoff oder Methyl steht, und 2-phenylethyl, optionally mono- to disubstituted independently of one another by chlorine or methyl-substituted pyrid-3-yl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted pyrid-2-yl, optionally simply by bromine, methyl, trifluoromethyl, cyano, nitro or ethynyl-substituted pyrid-2-yl. s simply methoxy-substituted pyrid-4-yl, l, 3-pyrimidin-2-yl, optionally once or twice by chlorine substituted l, 3-pyrimidin-5-yl, optionally monosubstituted by chlorine or methyl thia / ol-2-yl, l, 2,4-thiadiazol-5-yl or optionally substituted by bromine 1-methyl - Pyrazoi-5 yl or R 7 and R 8 together are - (CH 2 ) 4 -, R 9 is hydrogen or methyl, and
R!0 für Wasserstoff steht. R ! 0 is hydrogen.
Ebenfalls ganz besonders bevorzugt (Ausgestaltung 5-1) sind die Verbindungen der Formel (I) in denen Q' und Q zusammen für den Rest A-l stehen, der zusammen mit dem C- und N-Atom an das er gebunden ist, einen 6-gliedrigen aromatischen Ring bildet, Also very particularly preferred (embodiment 5-1) are the compounds of the formula (I) in which Q 'and Q together represent the radical Al which, together with the C and N atoms to which it is bonded, forms a forms a lower aromatic ring,
T für R\ -Oir oder -N(R7)(R8) steht, T is R 1 -Oir or -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für -C(R9)(R10)- steht, U für U-2, U-9 oder U-23 steht, G is -C (R 9 ) (R 10 ) -, U is U-2, U-9 or U-23,
Xa für Chlor, Trifluormethyl oder Methoxy steht, n für 0, 1 oder 2 steht, X a is chlorine, trifluoromethyl or methoxy, n is 0, 1 or 2,
R1, R2, R \ R4 jeweils unabhängig voneinander für für einen Rest aus der Reihe Wasserstoff, Fluor Chlor, Cyano, Methyl, Ethoxy, Methylthio, Trifluormethyl oder Trifluormethoxy stehen, IV für CH:Y steht, R 1 , R 2 , R 4 independently of one another each represent a radical from the group consisting of hydrogen, fluorine, chlorine, cyano, methyl, ethoxy, methylthio, trifluoromethyl or trifluoromethoxy, IV represents CH: Y,
Y für Wasserstoff, Chlor, -O-R51, -S(0)p-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4, Y-5, Y-6 steht, Y is hydrogen, chlorine, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4, Y-5 , Y-6 stands,
Xb für Chlor, Cyano, Methyl, Methoxy, Methylthio, Trifluormethyl, Methylaminocarbonyl oder Methylcarbonylamino steht, m für 0 oder 1 steht, p für 0, 1 oder 2 steht, R51 für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, 2-Methoxyethyl, Methoxycarbonylmethyl,X b is chlorine, cyano, methyl, methoxy, methylthio, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, m is 0 or 1, p is 0, 1 or 2, R 51 represents hydrogen, methyl, ethyl, n- or iso-propyl, 2-methoxyethyl, methoxycarbonylmethyl,
Phenyl, 4-F-Phenyi, 2-Cl-Phenyl, 3-Cl-Phenyl, 4-Cl-Phenyl, Phenylmethyl, 4-F-Phenylmethyl , Pyrid-3-yl, 6-Chlor-Pyrid-3-yl , Pyrid-2-yl oder l -Methylpyrazol-5-yl steht, Phenyl, 4-F-phenyl, 2-Cl-phenyl, 3-Cl-phenyl, 4-Cl-phenyl, phenylmethyl, 4-F-phenylmethyl, pyrid-3-yl, 6-chloro-pyrid-3-yl, Pyrid-2-yl or 1-methylpyrazol-5-yl,
R52 für Methyl, Ethyl, iso-Propyl, Phenyl oder Phenylmethyl steht, R53 für Wasserstoff, Methylcarbonyl oder Ethylcarbonyi steht, R 52 is methyl, ethyl, iso-propyl, phenyl or phenylmethyl, R 53 is hydrogen, methylcarbonyl or ethylcarbonyi,
R54 für Methyl, Ethyl, Cyclopropyl oder Phenylmethyl steht, R 54 is methyl, ethyl, cyclopropyl or phenylmethyl,
R" für Methyl steht, R "is methyl,
R für Wasserstoff steht, R is hydrogen,
R8 für Methyl, Ethyl, n- oder iso-Propyl, iso-, oder tert-Butyl, Trifluorethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclopropylmethyl, gegebenenfalls durch Chlor substituiertes Phenyl, gegebenenfalls durch Chlor substituiertes Phenylmethyl, gegebenenfalls durch Chlor substituiertes 1 -Phenyl ethyl, gegebenenfalls durch Chlor substituiertes 2-Phenylethyl oder gegebenenfalls durch Chlor substituiertes Pyrid-3-yl steht, R 8 represents methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, optionally chlorine-substituted phenyl, optionally phenyl-substituted chlorine, optionally chlorine-substituted 1 - Phenylethyl, optionally chlorine-substituted 2-phenylethyl or optionally chlorine-substituted pyrid-3-yl,
R ' für Wasserstoff oder Methyl steht, und R 'is hydrogen or methyl, and
R10 für Wasserstoff steht. R 10 is hydrogen.
In einer bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I) in der W für O steht. In a preferred embodiment, the invention relates to the compounds of the formula (I) in which W is O.
In einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I) in der W für S steht. In a further preferred embodiment, the invention relates to the compounds of the formula (I) in which W stands for S.
In den folgenden bevorzugten Ausführungsformen I-l bis 1-8 steht U für U-2, U-9, U-10 oder U-23, wobei alle anderen Gruppen, Reste und Substituenten die oben in Ausgestaltung (1-1) oder in Ausgestaltung (1-2) oder in Ausgestaltung (2-1) oder in Ausgestaltung (2-2) oder in Ausgestaltung (3-1) oder in Ausgestaltung (3-2) oder in Ausgestaltung (4-1) oder in Ausgestaltung (4-2) oder in Ausgestaltung (5-1) oder in Ausgestaltung (5-2) beschriebene Bedeutung haben. In the following preferred embodiments II to 1-8, U is U-2, U-9, U-10 or U-23, all other groups, radicals and substituents being those described above in the embodiment (1-1) or in the embodiment ( 1-2) or in embodiment (2-1) or in embodiment (2-2) or in embodiment (3-1) or in embodiment (3-2) or in embodiment (4-1) or in embodiment (4-2) 2) or in the embodiment (5-1) or in the embodiment (5-2) have meaning described.
In einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I-In a further preferred embodiment, the invention relates to the compounds of the formula (I-
1). 1).
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen: Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß alle anderen Strukturelemente gemäß Compounds of the formula with U according to all other structural elements according to
U-2 Ausgestaltung (1-1)  U-2 embodiment (1-1)
U-2 Ausgestaltung (2-1)  U-2 embodiment (2-1)
U-2 Ausgestaltung (3-1)  U-2 Embodiment (3-1)
U-2 Ausgestaltung (4-1)  U-2 embodiment (4-1)
U-2 Ausgestaltung (5-1)  U-2 Embodiment (5-1)
U-2 Ausgestaltung (1-2)  U-2 configuration (1-2)
U-2 Ausgestaltung (2-2)  U-2 Configuration (2-2)
U-2 Ausgestaltung (3-2)  U-2 embodiment (3-2)
U-2 Ausgestaltung (4-2)  U-2 embodiment (4-2)
U-2 Ausgestaltung (5-2)  U-2 embodiment (5-2)
U-9 Ausgestaltung (1-1)  U-9 Embodiment (1-1)
U-9 Ausgestaltung (2-1)  U-9 Embodiment (2-1)
U-9 Ausgestaltung (3-1)  U-9 Embodiment (3-1)
U-9 Ausgestaltung (4-1)  U-9 Embodiment (4-1)
U-9 Ausgestaltung (5-1)  U-9 Embodiment (5-1)
U-9 Ausgestaltung (1-2)  U-9 design (1-2)
U-9 Ausgestaltung (2-2)  U-9 Embodiment (2-2)
U-9 Ausgestaltung (3-2)  U-9 Embodiment (3-2)
U-9 Ausgestaltung (4-2)  U-9 embodiment (4-2)
U-9 Ausgestaltung (5-2)  U-9 Embodiment (5-2)
U-10 Ausgestaltung (1-1)  U-10 embodiment (1-1)
U-10 Ausgestaltung (2-1)  U-10 design (2-1)
U-10 Ausgestaltung (3-1)  U-10 Embodiment (3-1)
U-10 Ausgestaltung (4-1)  U-10 embodiment (4-1)
U-10 Ausgestaltung (5-1)  U-10 Embodiment (5-1)
U-10 Ausgestaltung (1-2)  U-10 design (1-2)
U-10 Ausgestaltung (2-2)  U-10 design (2-2)
U-10 Ausgestaltung (3-2)  U-10 design (3-2)
U-10 Ausgestaltung (4-2) U-10 Ausgestaltung (5-2) U-10 design (4-2) U-10 embodiment (5-2)
U-23 Ausgestaltung (1-1)  U-23 Configuration (1-1)
U-23 Ausgestaltung (2-1)  U-23 Embodiment (2-1)
U-23 Ausgestaltung (3-1)  U-23 Embodiment (3-1)
U-23 Ausgestaltung (4-1)  U-23 Configuration (4-1)
U-23 Ausgestaltung (5-1)  U-23 Embodiment (5-1)
U-23 Ausgestaltung (1-2)  U-23 design (1-2)
U-23 Ausgestaltung (2-2)  U-23 Design (2-2)
U-23 Ausgestaltung (3-2)  U-23 Configuration (3-2)
U-23 Ausgestaltung (4-2)  U-23 Configuration (4-2)
U-23 Ausgestaltung (5-2)  U-23 Configuration (5-2)
In einer weiteren bevorzugten Aus fuhrungs form betrifft die Erfindung die Verbindungen der Formel (I- 2). In a further preferred embodiment, the invention relates to the compounds of the formula (I-2).
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen: Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß alle anderen Stnikturelemente gemäß Compounds of the formula with U according to all other structural elements according to
1-2 U-2 Ausgestaltung (1-1)  1-2 U-2 configuration (1-1)
1-2 U-2 Ausgestaltung (2-1)  1-2 U-2 configuration (2-1)
1-2 U-2 Ausgestaltung (3-1)  1-2 U-2 Configuration (3-1)
1-2 U-2 Ausgestaltung (4-1)  1-2 U-2 configuration (4-1)
1-2 U-2 Ausgestaltung (5-1)  1-2 U-2 configuration (5-1)
1-2 U-2 Ausgestaltung (1-2)  1-2 U-2 configuration (1-2)
1-2 U-2 Ausgestaltung (2-2)  1-2 U-2 Design (2-2)
1-2 U-2 Ausgestaltung (3-2)  1-2 U-2 configuration (3-2)
1-2 U-2 Ausgestaltung (4-2)  1-2 U-2 configuration (4-2)
1-2 U-2 Ausgestaltung (5-2)  1-2 U-2 configuration (5-2)
1-2 U-9 Ausgestaltung (1 -1)  1-2 U-9 configuration (1 -1)
1-2 U-9 Ausgestaltung (2-1)  1-2 U-9 Embodiment (2-1)
1-2 U-9 Ausgestaltung (3-1 )  1-2 U-9 Embodiment (3-1)
1-2 U-9 Ausgestaltung (4-1)  1-2 U-9 configuration (4-1)
1-2 U-9 Ausgestaltung (5-1)  1-2 U-9 configuration (5-1)
1-2 U-9 Ausgestaltung (1-2) 2 U-9 Ausgestaltung (2-2 1-2 U-9 configuration (1-2) 2 U-9 configuration (2-2
2 U-9 Ausgestaltung (3-2  2 U-9 embodiment (3-2
2 U-9 Ausgestaltung (4-2  2 U-9 Design (4-2
2 U-9 Ausgestaltung (5-2  2 U-9 embodiment (5-2
2 U-10 Ausgestaltung (1 -1  2 U-10 design (1 -1
2 U-10 Ausgestaltung (2-1  2 U-10 design (2-1
2 U-10 Ausgestaltung (3-1  2 U-10 Design (3-1
2 U-10 Ausgestaltung (4-1  2 U-10 design (4-1
2 U-10 Ausgestaltung (5-1  2 U-10 Design (5-1
2 U-10 Ausgestaltung (1 -2  2 U-10 design (1 -2
2 U-10 Ausgestaltung (2-2  2 U-10 design (2-2
2 U-10 Ausgestaltung (3-2  2 U-10 design (3-2
2 U-10 Ausgestaltung (4-2  2 U-10 Design (4-2
2 U-10 Ausgestaltung ( 5-2  2 U-10 Design (5-2
2 U-23 Ausgestaltung (1 -1  2 U-23 Design (1 -1
2 U-23 Ausgestaltung (2-1  2 U-23 embodiment (2-1
2 U-23 Ausgestaltung (3-1  2 U-23 Configuration (3-1
2 U-23 Ausgestaltung (4-1  2 U-23 Configuration (4-1
2 U-23 Ausgestaltung (5-1  2 U-23 Configuration (5-1
2 U-23 Ausgestaltung (1 -2  2 U-23 Configuration (1 -2
2 U-23 Ausgestaltung (2-2  2 U-23 Design (2-2
2 U-23 Ausgestaltung (3-2  2 U-23 Design (3-2
2 U-23 Ausgestaltung (4-2  2 U-23 Design (4-2
2 U-23 Ausgestaltung (5-2  2 U-23 Design (5-2
In einer weiteren bevorzugten Aus fuhrungs form betrifft die Erfindung die Verbindungen der Formel (I- 3). In a further preferred embodiment, the invention relates to the compounds of the formula (I-3).
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen : Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß alle anderen Strukturelemente gemäß Compounds of the formula with U according to all other structural elements according to
1-3 U-2 Ausgestaltung (1 -1)  1-3 U-2 configuration (1 -1)
1-3 U-2 Ausgestaltung (2-1)  1-3 U-2 Embodiment (2-1)
1-3 U-2 Ausgestaltung (3-1) 1-3 U-2 Ausgestaltung (4-1)1-3 U-2 Embodiment (3-1) 1-3 U-2 configuration (4-1)
1-3 U-2 Ausgestaltung (5-1)1-3 U-2 Configuration (5-1)
1-3 U-2 Ausgestaltung (1 -2)1-3 U-2 Design (1-2)
1-3 U-2 Ausgestaltung (2-2)1-3 U-2 Configuration (2-2)
1-3 U-2 Ausgestaltung (3-2) i-3 U-2 Ausgestaltung (4-2)1-3 U-2 Configuration (3-2) i-3 U-2 Embodiment (4-2)
1-3 U-2 Ausgestaltung (5-2)1-3 U-2 Configuration (5-2)
1-3 U-9 Ausgestaltung (1 -1)1-3 U-9 embodiment (1 -1)
1-3 U-9 Ausgestaltung (2-1)1-3 U-9 Embodiment (2-1)
1-3 U-9 Ausgestaltung (3-1)1-3 U-9 Embodiment (3-1)
1-3 U-9 Ausgestaltung (4-1)1-3 U-9 Embodiment (4-1)
1-3 U-9 Ausgestaltung (5-1)1-3 U-9 Embodiment (5-1)
1-3 U-9 Ausgestaltung (1 -2) i-3 U-9 Ausgestaltung (2-2)1-3 U-9 Configuration (1-2) i-3 U-9 Embodiment (2-2)
1-3 U-9 Ausgestaltung (3-2)1-3 U-9 Design (3-2)
1-3 U-9 Ausgestaltung (4-2)1-3 U-9 configuration (4-2)
1-3 U-9 Ausgestaltung (5-2)1-3 U-9 Embodiment (5-2)
1-3 U-10 Ausgestaltung (1 -1)1-3 U-10 configuration (1 -1)
1-3 U-10 Ausgestaltung (2-1)1-3 U-10 design (2-1)
1-3 U-10 Ausgestaltung (3-1)1-3 U-10 Embodiment (3-1)
1-3 U-10 Ausgestaltung (4-1)1-3 U-10 design (4-1)
1-3 U-10 Ausgestaltung (5-1)1-3 U-10 design (5-1)
1-3 U-10 Ausgestaltung (1 -2)1-3 U-10 design (1-2)
1-3 U-10 Ausgestaltung (2-2)1-3 U-10 design (2-2)
1-3 U-10 Ausgestaltung (3-2)1-3 U-10 design (3-2)
1-3 U-10 Ausgestaltung (4-2) i-3 U-10 Ausgestaltung (5-2)1-3 U-10 Configuration (4-2) i-3 U-10 Configuration (5-2)
1-3 U-23 Ausgestaltung (1 -1)1-3 U-23 Configuration (1 -1)
1-3 U-23 Ausgestaltung (2-1)1-3 U-23 Configuration (2-1)
1-3 U-23 Ausgestaltung (3-1)1-3 U-23 Configuration (3-1)
1-3 U-23 Ausgestaltung (4-1)1-3 U-23 Configuration (4-1)
1-3 U-23 Ausgestaltung (5-1)1-3 U-23 Configuration (5-1)
1-3 U-23 Ausgestaltung (1 -2)1-3 U-23 Design (1-2)
1-3 U-23 Ausgestaltung (2-2)1-3 U-23 Configuration (2-2)
1-3 U-23 Ausgestaltung (3-2)1-3 U-23 Configuration (3-2)
1-3 U-23 Ausgestaltung (4-2)1-3 U-23 Configuration (4-2)
1-3 U-23 Ausgestaltung (5-2) In einer weiteren bevorzugten Aiisfiihriingsfonn betrifft die Erfindung die Verbindungen der Formel (I- 1-3 U-23 Configuration (5-2) In a further preferred embodiment, the invention relates to the compounds of the formula (I-
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen: Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß alle anderen Strukturelemente gemäß Compounds of the formula with U according to all other structural elements according to
1-4 U-2 Ausgestaltung (1-1)  1-4 U-2 Configuration (1-1)
1-4 U-2 Ausgestaltung (2-1)  1-4 U-2 embodiment (2-1)
1-4 U-2 Ausgestaltung (3-1)  1-4 U-2 Embodiment (3-1)
1-4 U-2 Ausgestaltung (4-1)  1-4 U-2 embodiment (4-1)
1-4 U-2 Ausgestaltung (5-1)  1-4 U-2 embodiment (5-1)
1-4 U-2 Ausgestaltung (1-2)  1-4 U-2 configuration (1-2)
1-4 U-2 Ausgestaltung (2-2)  1-4 U-2 Configuration (2-2)
1-4 U-2 Ausgestaltung (3-2)  1-4 U-2 Configuration (3-2)
1-4 U-2 Ausgestaltung (4-2)  1-4 U-2 Configuration (4-2)
1-4 U-2 Ausgestaltung (5-2)  1-4 U-2 embodiment (5-2)
1-4 U-9 Ausgestaltung (1-1)  1-4 U-9 Embodiment (1-1)
1-4 U-9 Ausgestaltung (2-1)  1-4 U-9 Embodiment (2-1)
1-4 U-9 Ausgestaltung (3-1)  1-4 U-9 Embodiment (3-1)
1-4 U-9 Ausgestaltung (4-1)  1-4 U-9 embodiment (4-1)
1-4 U-9 Ausgestaltung (5-1)  1-4 U-9 Embodiment (5-1)
1-4 U-9 Ausgestaltung (1-2)  1-4 U-9 configuration (1-2)
1-4 U-9 Ausgestaltung (2-2)  1-4 U-9 Configuration (2-2)
1-4 U-9 Ausgestaltung (3-2)  1-4 U-9 Configuration (3-2)
1-4 U-9 Ausgestaltung (4-2)  1-4 U-9 Configuration (4-2)
1-4 U-9 Ausgestaltung (5-2)  1-4 U-9 Embodiment (5-2)
1-4 U-10 Ausgestaltung (1-1)  1-4 U-10 design (1-1)
1-4 U-10 Ausgestaltung (2-1)  1-4 U-10 Embodiment (2-1)
1-4 U-10 Ausgestaltung (3-1)  1-4 U-10 Embodiment (3-1)
1-4 U-10 Ausgestaltung (4-1)  1-4 U-10 design (4-1)
1-4 U-10 Ausgestaltung (5-1)  1-4 U-10 Embodiment (5-1)
1-4 U-10 Ausgestaltung (1-2)  1-4 U-10 design (1-2)
1-4 U-10 Ausgestaltung (2-2)  1-4 U-10 Design (2-2)
1-4 U-10 Ausgestaltung (3-2) 1-4 U-10 Ausgestaltung (4-2) 1-4 U-10 Design (3-2) 1-4 U-10 design (4-2)
1-4 U-10 Ausgestaltung (5-2)  1-4 U-10 Design (5-2)
1-4 U-23 Ausgestaltung (1 -1)  1-4 U-23 Configuration (1 -1)
1-4 U-23 Ausgestaltung (2-1)  1-4 U-23 Embodiment (2-1)
1-4 U-23 Ausgestaltung (3-1)  1-4 U-23 Configuration (3-1)
1-4 U-23 Ausgestaltung (4-1)  1-4 U-23 Configuration (4-1)
1-4 U-23 Ausgestaltung (5-1)  1-4 U-23 Configuration (5-1)
1-4 U-23 Ausgestaltung (1 -2)  1-4 U-23 Design (1-2)
1-4 U-23 Ausgestaltung (2-2)  1-4 U-23 Configuration (2-2)
1-4 U-23 Ausgestaltung (3-2)  1-4 U-23 Configuration (3-2)
1-4 U-23 Ausgestaltung (4-2)  1-4 U-23 Configuration (4-2)
1-4 U-23 Ausgestaltung (5-2)  1-4 U-23 Configuration (5-2)
In einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I- 5) In a further preferred embodiment, the invention relates to the compounds of the formula (I-5)
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen : Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß alle anderen Strukturelemente gemäß Compounds of the formula with U according to all other structural elements according to
1-5 U-2 Ausgestaltung (1 -1)  1-5 U-2 Configuration (1 -1)
1-5 11-2 Ausgestaltung (2-1)  1-5 11-2 Design (2-1)
1-5 U-2 Ausgestaltung (3-1)  1-5 U-2 Configuration (3-1)
1-5 U-2 Ausgestaltung (4-1)  1-5 U-2 Configuration (4-1)
1-5 U-2 Ausgestaltung (5-1)  1-5 U-2 Configuration (5-1)
1-5 U-2 Ausgestaltung (1 -2)  1-5 U-2 Design (1-2)
1-5 U-2 Ausgestaltung (2-2)  1-5 U-2 Configuration (2-2)
1-5 U-2 Ausgestaltung (3-2)  1-5 U-2 Configuration (3-2)
1-5 U-2 Ausgestaltung (4-2)  1-5 U-2 Configuration (4-2)
1-5 U-2 Ausgestaltung (5-2)  1-5 U-2 Configuration (5-2)
1-5 U-9 Ausgestaltung (1 -1)  1-5 U-9 Configuration (1 -1)
1-5 U-9 Ausgestaltung (2-1)  1-5 U-9 Embodiment (2-1)
1-5 U-9 Ausgestaltung (3-1)  1-5 U-9 Configuration (3-1)
1-5 U-9 Ausgestaltung (4-1) 1-5 U-9 Ausgestaltung (5-1) 1-5 U-9 Configuration (4-1) 1-5 U-9 Configuration (5-1)
1-5 U-9 Ausgestaltung (1 -2)  1-5 U-9 Configuration (1-2)
1 -5 U-9 Ausgestaltung (2-2)  1 -5 U-9 Configuration (2-2)
1-5 U-9 Ausgestaltung (3-2)  1-5 U-9 Configuration (3-2)
1-5 U-9 Ausgestaltung (4-2)  1-5 U-9 Configuration (4-2)
[-5 U-9 Ausgestaltung (5-2)  [-5 U-9 Embodiment (5-2)
1-5 U-10 Ausgestaltung (1 -1)  1-5 U-10 Configuration (1 -1)
i-5 U-10 Ausgestaltung (2-1) i-5 U-10 Embodiment (2-1)
1-5 U-10 Ausgestaltung (3-1)  1-5 U-10 Configuration (3-1)
i-5 U-10 Ausgestaltung (4-1) i-5 U-10 Configuration (4-1)
1-5 U-10 Ausgestaltung (5-1)  1-5 U-10 Configuration (5-1)
1 -5 U-10 Ausgestaltung (1 -2)  1 -5 U-10 Configuration (1 -2)
1-5 U-10 Ausgestaltung (2-2)  1-5 U-10 Configuration (2-2)
1 -5 U-10 Ausgestaltung (3-2)  1 -5 U-10 Configuration (3-2)
1-5 U-10 Ausgestaltung (4-2)  1-5 U-10 Design (4-2)
1 -5 U-10 Ausgestaltung (5-2)  1 -5 U-10 Configuration (5-2)
1-5 U-23 Ausgestaltung (1 -1)  1-5 U-23 Configuration (1 -1)
1-5 U-23 Ausgestaltung (2-1)  1-5 U-23 Configuration (2-1)
1-5 U-23 Ausgestaltung (3-1)  1-5 U-23 Configuration (3-1)
1 -5 U-23 Ausgestaltung (4-1)  1 -5 U-23 Configuration (4-1)
1-5 U-23 Ausgestaltung (5-1)  1-5 U-23 Configuration (5-1)
1-5 U-23 Ausgestaltung (1 -2)  1-5 U-23 Configuration (1 -2)
1-5 U-23 Ausgestaltung (2-2)  1-5 U-23 Configuration (2-2)
1-5 U-23 Ausgestaltung (3-2)  1-5 U-23 Configuration (3-2)
1-5 U-23 Ausgestaltung (4-2)  1-5 U-23 Configuration (4-2)
1 -5 U-23 Ausgestaltung (5-2)  1 -5 U-23 Configuration (5-2)
In einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I- 6) In a further preferred embodiment, the invention relates to the compounds of the formula (I-6)
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen : Verbindungen der Formel mit U gemäß alle anderen Strukturelemente gemäß Of these, the following are particularly preferred embodiments: Compounds of the formula with U according to all other structural elements according to
1-6 U-2 Ausgestaltung (1-1) 1-6 U-2 Configuration (1-1)
1-6 U-2 Ausgestaltung (2-1)  1-6 U-2 Embodiment (2-1)
1-6 U-2 Ausgestaltung (3-1)  1-6 U-2 Configuration (3-1)
1-6 U-2 Ausgestaltung (4-1)  1-6 U-2 Configuration (4-1)
1-6 U-2 Ausgestaltung (5-1)  1-6 U-2 Configuration (5-1)
1-6 U-2 Ausgestaltung (1-2)  1-6 U-2 Configuration (1-2)
1-6 U-2 Ausgestaltung (2-2)  1-6 U-2 Configuration (2-2)
1-6 U-2 Ausgestaltung (3-2)  1-6 U-2 Configuration (3-2)
i-6 U-2 Ausgestaltung (4-2) i-6 U-2 Configuration (4-2)
1-6 U-2 Ausgestaltung (5-2)  1-6 U-2 Configuration (5-2)
1-6 U-9 Ausgestaltung (1-1)  1-6 U-9 Configuration (1-1)
1-6 U-9 Ausgestaltung (2-1)  1-6 U-9 Embodiment (2-1)
1-6 U-9 Ausgestaltung (3-1)  1-6 U-9 Configuration (3-1)
1-6 U-9 Ausgestaltung (4-1)  1-6 U-9 Configuration (4-1)
1-6 U-9 Ausgestaltung (5-1)  1-6 U-9 Configuration (5-1)
1-6 U-9 Ausgestaltung (1-2)  1-6 U-9 Configuration (1-2)
i-6 U-9 Ausgestaltung (2-2) i-6 U-9 Configuration (2-2)
1-6 U-9 Ausgestaltung (3-2)  1-6 U-9 Configuration (3-2)
i-6 U-9 Ausgestaltung (4-2) i-6 U-9 Configuration (4-2)
1-6 U-9 Ausgestaltung (5-2)  1-6 U-9 Configuration (5-2)
1-6 U-10 Ausgestaltung (1-1)  1-6 U-10 Design (1-1)
1-6 U-10 Ausgestaltung (2-1)  1-6 U-10 Embodiment (2-1)
1-6 U-10 Ausgestaltung (3-1)  1-6 U-10 Configuration (3-1)
1-6 U-10 Ausgestaltung (4-1)  1-6 U-10 Design (4-1)
1-6 U-10 Ausgestaltung (5-1)  1-6 U-10 Configuration (5-1)
i-6 U-10 Ausgestaltung (1-2) i-6 U-10 Configuration (1-2)
i-6 U-10 Ausgestaltung (2-2) i-6 U-10 Configuration (2-2)
i-6 U-10 Ausgestaltung (3-2) i-6 U-10 Configuration (3-2)
1-6 U-10 Ausgestaltung (4-2)  1-6 U-10 Design (4-2)
i-6 U-10 Ausgestaltung (5-2) i-6 U-10 Configuration (5-2)
1-6 U-23 Ausgestaltung (1-1)  1-6 U-23 Configuration (1-1)
i-6 U-23 Ausgestaltung (2-1) i-6 U-23 Configuration (2-1)
1-6 U-23 Ausgestaltung (3-1)  1-6 U-23 Configuration (3-1)
i-6 U-23 Ausgestaltung (4-1) i-6 U-23 Configuration (4-1)
1-6 U-23 Ausgestaltung (5-1)  1-6 U-23 Configuration (5-1)
1-6 U-23 Ausgestaltung (1-2)  1-6 U-23 Configuration (1-2)
1-6 U-23 Ausgestaltung (2-2) 1-6 U-23 Ausgestaltung (3-2) 1-6 U-23 Configuration (2-2) 1-6 U-23 Configuration (3-2)
1-6 U-23 Ausgestaltung (4-2)  1-6 U-23 Configuration (4-2)
1-6 U-23 Ausgestaltung (5-2)  1-6 U-23 Configuration (5-2)
In einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I- 7) In a further preferred embodiment, the invention relates to the compounds of the formula (I-7)
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen: Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß all anderen Strukturelemente gemäß Compounds of the formula with U according to all other structural elements according to
1-7 U-2 Ausgestaltung (1 -1)  1-7 U-2 Configuration (1 -1)
1-7 U-2 Ausgestaltung (2-1)  1-7 U-2 Embodiment (2-1)
1-7 U-2 Ausgestaltung (3-1)  1-7 U-2 Configuration (3-1)
1-7 U-2 Ausgestaltung (4-1)  1-7 U-2 Configuration (4-1)
1-7 U-2 Ausgestaltung (5-1)  1-7 U-2 Configuration (5-1)
1-7 U-2 Ausgestaltung (1 -2)  1-7 U-2 Configuration (1-2)
1-7 U-2 Ausgestaltung (2-2)  1-7 U-2 Configuration (2-2)
1-7 U-2 Ausgestaltung (3-2)  1-7 U-2 Configuration (3-2)
1-7 U-2 Ausgestaltung (4-2)  1-7 U-2 Configuration (4-2)
1-7 U-2 Ausgestaltung (5-2)  1-7 U-2 Configuration (5-2)
1-7 U-9 Ausgestaltung (1 -1)  1-7 U-9 Configuration (1 -1)
1-7 U-9 Ausgestaltung (2-1)  1-7 U-9 Embodiment (2-1)
1-7 U-9 Ausgestaltung (3-1)  1-7 U-9 Configuration (3-1)
1-7 U-9 Ausgestaltung (4-1)  1-7 U-9 Configuration (4-1)
1-7 U-9 Ausgestaltung (5-1)  1-7 U-9 Configuration (5-1)
1-7 U-9 Ausgestaltung (1 -2)  1-7 U-9 Embodiment (1-2)
1-7 U-9 Ausgestaltung (2-2)  1-7 U-9 Configuration (2-2)
1-7 U-9 Ausgestaltung (3-2)  1-7 U-9 Configuration (3-2)
1-7 U-9 Ausgestaltung (4-2)  1-7 U-9 Configuration (4-2)
1-7 U-9 Ausgestaltung (5-2)  1-7 U-9 Configuration (5-2)
1-7 U-10 Ausgestaltung (1 -1) 1-7 U-10 Ausgestaltung (2-1) 1-7 U-10 Configuration (1 -1) 1-7 U-10 Embodiment (2-1)
1-7 U-10 Ausgestaltung (3-1)  1-7 U-10 Configuration (3-1)
1-7 U-10 Ausgestaltung (4-1)  1-7 U-10 Design (4-1)
1-7 U-10 Ausgestaltung (5-1)  1-7 U-10 Configuration (5-1)
1-7 U-10 Ausgestaltung (1-2)  1-7 U-10 design (1-2)
1-7 U-10 Ausgestaltung (2-2)  1-7 U-10 Configuration (2-2)
1-7 U-10 Ausgestaltung (3-2)  1-7 U-10 Design (3-2)
1-7 U-10 Ausgestaltung (4-2)  1-7 U-10 Design (4-2)
1-7 U-10 Ausgestaltung (5-2)  1-7 U-10 Design (5-2)
1-7 U-23 Ausgestaltung (1-1)  1-7 U-23 Configuration (1-1)
1-7 U-23 Ausgestaltung (2-1)  1-7 U-23 Configuration (2-1)
1-7 U-23 Ausgestaltung (3-1)  1-7 U-23 Configuration (3-1)
1-7 U-23 Ausgestaltung (4-1)  1-7 U-23 Configuration (4-1)
1-7 U-23 Ausgestaltung (5-1)  1-7 U-23 Configuration (5-1)
1-7 U-23 Ausgestaltung (1-2)  1-7 U-23 Configuration (1-2)
1-7 U-23 Ausgestaltung (2-2)  1-7 U-23 Configuration (2-2)
1-7 U-23 Ausgestaltung (3-2)  1-7 U-23 Configuration (3-2)
1-7 U-23 Ausgestaltung (4-2)  1-7 U-23 Configuration (4-2)
1-7 U-23 Ausgestaltung (5-2)  1-7 U-23 Configuration (5-2)
I einer weiteren bevorzugten Aus führungs form betrifft die Erfindung die Verbindungen der Formel (I-In a further preferred embodiment, the invention relates to the compounds of the formula (I)
8) 8th)
Hierunter besonders bevorzugt sind die nachfolgend dargestellten Ausgestaltungen: Of these, the following are particularly preferred embodiments:
Verbindungen der Formel mit U gemäß all anderen Strukturelemente Compounds of the formula with U according to all other structural elements
1-8 U-2 Ausgestaltung (1-1)  1-8 U-2 Configuration (1-1)
1-8 U-2 Ausgestaltung (2-1)  1-8 U-2 Embodiment (2-1)
1-8 U-2 Ausgestaltung (3-1)  1-8 U-2 Configuration (3-1)
1-8 U-2 Ausgestaltung (4-1)  1-8 U-2 Configuration (4-1)
1-8 U-2 Ausgestaltung (5-1)  1-8 U-2 Configuration (5-1)
1-8 U-2 Ausgestaltung (1-2)  1-8 U-2 Design (1-2)
1-8 U-2 Ausgestaltung (2-2) 1-8 U-2 Ausgestaltung (3-2) 1-8 U-2 Configuration (2-2) 1-8 U-2 Configuration (3-2)
1-8 U-2 Ausgestaltung (4-2)  1-8 U-2 Design (4-2)
1-8 U-2 Ausgestaltung (5-2)  1-8 U-2 Configuration (5-2)
1-8 U-9 Ausgestaltung ( 1 -1 )  1-8 U-9 Configuration (1 -1)
1-8 U-9 Ausgestaltung (2-1)  1-8 U-9 Embodiment (2-1)
1-8 U-9 Ausgestaltung (3-1 )  1-8 U-9 Configuration (3-1)
1-8 U-9 Ausgestaltung (4-1 )  1-8 U-9 Configuration (4-1)
1-8 U-9 Ausgestaltung (5-1 )  1-8 U-9 Configuration (5-1)
1-8 U-9 Ausgestaltung (1 -2)  1-8 U-9 Embodiment (1-2)
ί-8 U-9 Ausgestaltung (2-2) ί-8 U-9 Configuration (2-2)
1-8 U-9 Ausgestaltung (3-2)  1-8 U-9 Configuration (3-2)
1-8 U-9 Ausgestaltung (4-2)  1-8 U-9 Configuration (4-2)
1-8 U-9 Ausgestaltung (5-2)  1-8 U-9 Configuration (5-2)
1-8 U-10 Ausgestaltung (1 -1)  1-8 U-10 Configuration (1 -1)
1-8 U-10 Ausgestaltung (2-1 )  1-8 U-10 Embodiment (2-1)
1-8 U-10 Ausgestaltung (3-1 )  1-8 U-10 Configuration (3-1)
1-8 U-10 Ausgestaltung (4-1 )  1-8 U-10 Configuration (4-1)
1-8 U-10 Ausgestaltung (5-1)  1-8 U-10 Configuration (5-1)
1-8 U-10 Ausgestaltung (1 -2)  1-8 U-10 Design (1-2)
1-8 U-10 Ausgestaltung (2-2 )  1-8 U-10 Design (2-2)
1-8 U-1 0 Ausgestaltung (3-2)  1-8 U-1 0 Configuration (3-2)
1-8 U-10 Ausgestaltung (4-2)  1-8 U-10 Configuration (4-2)
1-8 U-10 Ausgestaltung (5-2)  1-8 U-10 Configuration (5-2)
1-8 U-23 Ausgestaltung ( 1 -1 )  1-8 U-23 Configuration (1 -1)
1-8 U-23 Ausgestaltung (2-1 )  1-8 U-23 Configuration (2-1)
1-8 U-23 Ausgestaltung (3-1)  1-8 U-23 Configuration (3-1)
1-8 U-23 Ausgestaltung (4-1 )  1-8 U-23 Configuration (4-1)
1-8 U-23 Ausgestaltung (5-1 )  1-8 U-23 Configuration (5-1)
1-8 U-23 Ausgestaltung ( 1 -2)  1-8 U-23 Configuration (1-2)
1-8 U-23 Ausgestaltung (2-2)  1-8 U-23 Configuration (2-2)
1-8 U-23 Ausgestaltung (3-2)  1-8 U-23 Configuration (3-2)
1-8 U-23 Ausgestaltung (4-2)  1-8 U-23 Configuration (4-2)
1-8 U-23 Ausgestaltung (5-2)  1-8 U-23 Configuration (5-2)
Unter den genannten Ausfülirungsfonrien I-l bis 1-8 sind die Folgenden bevorzugt: I-l , 1-4. 1-5. 1-6, 1-7, 1-8. Unter den genannten Aus führungs formen l- l bis 1-8 sind die Folgenden besonders bevorzugt: 1-6. 1-7, I- 8. Among the aforementioned Ausfülirungsfonrien Il to 1-8, the following are preferred: Il, 1-4. 1-5. 1-6, 1-7, 1-8. Among the above-mentioned embodiments 1-1 to 1-8, the following are particularly preferred: 1-6. 1-7, I-8.
Unter den genannten Ausfuhrungsformen i- 1 bis 1-8 sind die Folgenden ganz besonders bevorzugt: 1-7.Among the above-mentioned embodiments i-1 to 1-8, the following are particularly preferred: 1-7.
1-8. Ebenfalls bevorzugte erfindungsgemäße Verbindungen sind die in Tabelle 1 gezeigten Verbindungen der allgemeinen Formel (I). 1-8. Likewise preferred compounds according to the invention are the compounds of general formula (I) shown in Table 1.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für alle Verbindungen der Formel (I) und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefmitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply correspondingly to all compounds of the formula (I) and to the starting materials and intermediates. These residual definitions can be combined with one another as desired, ie also between the respective preferred ranges.
Erfindungsgemäß bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt, wobei jede vorstehend als bevorzugt beschriebene Ausgestaltung eine eigenständige Kombination darstellt, insbesondere eine Kombination wie beschrieben in Ausgestaltung 2- 1 oder in Ausgestaltung 2-2. Erfindungsgemäß weiter bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als weiter bevorzugt aufgeführten Bedeutungen vorliegt, wobei jede vorstehend als weiter bevorzugt beschriebene Ausgestaltung eine eigenständige Kombination darstellt, insbesondere eine Kombination wie beschrieben in Ausgestaltung 3-1 oder in Ausgestaltung 3-2. Preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above is preferred, wherein each embodiment described above as preferred represents an independent combination, in particular a combination as described in embodiment 2-1 or in embodiment 2-2 , Compounds of the formula (I) which contain a combination of the definitions given above as being more preferred are also preferred according to the invention, wherein each embodiment described above as further preferred represents an independent combination, in particular a combination as described in embodiment 3-1 or in an embodiment 3-2.
Erfindungsgemäß besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt, wobei jede vorstehend als besonders bevorzugt beschriebene Ausgestaltung eine eigenständige Kombination darstellt, insbesondere eine Kombination wie beschrieben in Ausgestaltung 4- 1 oder in Ausgestaltung 4- 2. Particular preference is given in accordance with the invention to compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred, with each embodiment described above as being particularly preferred representing an independent combination, in particular a combination as described in embodiment 4-1 or in a refinement 4- 2.
Erfindungsgemäß ganz besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt, wobei jede vorstehend als ganz besonders bevorzugt beschriebene Ausgestaltung eine eigenständige Kombination darstellt, insbesondere eine Kombination wie beschrieben in Ausgestaltung 5-1 oder in Ausgestaltung 5-2. Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred, each embodiment described above as being very particularly preferred representing an independent combination, in particular a combination as described in embodiment 5-1 or in embodiment 5-2.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
Die Verbindungen der Formel (I) sind mesoionische innere Salze. Innere Salze, auch bekannt als Zwitterionen sind elektronisch neutrale Moleküle die formal positive und negative Ladungen an unterschiedlichen Atomen tragen. Die Verbindungen der Formel (I) können formal durch verschiedene Strukturen dargestellt werden, die die positive und die negative Ladung an unterschiedlichen Atomen tragen. In der nachfolgenden Abbildung sind 4 mögliche Darstellungs formen gezeigt ohne weitere mögliche Darstellungs formen auszuschließen. Alle Strukturdarstellungen sind gleichwertig. Aus Gründen der Vereinfachung wird hier jeweils nur eine mögliche Strukturdarstellung gewählt. Diese Darstellung ist jeweils repräsentativ für alle Valenzbindungsstruktur darstellungen zu verstehen. The compounds of formula (I) are mesoionic internal salts. Internal salts, also known as zwitterions, are electronically neutral molecules that formally express positive and negative charges carry different atoms. The compounds of formula (I) can be formally represented by various structures carrying the positive and negative charges on different atoms. The following figure shows 4 possible forms of presentation without excluding other possible forms of representation. All structural representations are equivalent. For reasons of simplification, only one possible structural representation is selected here in each case. This representation is representative of all valence bond structure representations.
Die Verbindungen der Formel (I) können gegebenenfalls auch in Abhängigkeit von der Art der Substituenten als Stereoisomere, d.h. als geometrische und/oder als optische Isomere oder Isomerengemische in unterschiedlichen Zusammensetzungen vorliegen. Sowohl die reinen Stereoisomeren als auch beliebige Gemische dieser Isomeren sind Gegenstand dieser Erfindung, auch wenn hier im Allgemeinen nur von Verbindungen der Formel (I) die Rede ist. The compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. are present as geometric and / or optical isomers or isomer mixtures in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
Vorzugsweise werden jedoch die optisch aktiven, stereoisomeren Formen der Verbindungen der Formel (I) und deren Salze erfindungsgemäß verwendet. Die Erfindung betrifft daher sowohl die reinen Enantiomeren und Diastereomeren, als auch deren Gemische zur Bekämpfung von tierischen Schädlingen, zu denen Arthropoden und insbesondere Insekten zählen. Preferably, however, the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention. The invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
Die Verbindungen der Formel (I) können gegebenenfalls in verschiedenen polymorphen Formen oder als Mischung verschiedener polymorpher Formen vorliegen. Sowohl die reinen Polymorphe als auch die Poiymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkyi, im Rahmen der vorliegenden Erfindung ein Rest einer gesättigten, aliphatischen Kohlenwasserstoffgruppe mit 1 bis 12 Kohlenstoffatomen verstanden, die verzweigt oder unverzweigt sein kann. Beispiele für Ci- Ci2-Alkylreste sind Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyi, iso-Butyi, sec.-Butyl, tert-Butyl, n- Pentyl, iso-Pentyl, Neopentyl, tert-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 1 -Ethylpropyl, 1 ,2- Dimethyipropyl, Hexyi n-Heptyi, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl und n-Dodecyi. Von diesen Alkylresten sind Ci-Cö-Alkylreste besonders bevorzugt. Insbesondere bevorzugt sind Ci-C4-Alkylreste. The compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention. Unless otherwise defined elsewhere, the term "alkyl", either alone or in combination with other terms such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso -Pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, hexyl-n-heptyi, n-octyl, n-nonyl, n-decyl, n-undecyl and n- Dodecyls Of these alkyl radicals, C 1 -C 6 -alkyl radicals are particularly preferred, C 1 -C 4 -alkyl radicals being particularly preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Aikenyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-C 12-Alkenylrest, welcher mindestens eine Doppelbindung aufweist, beispielsweise Vinyl, Allyl, 1 -Propenyl, Isopropenyl, 1-Butenyl, 2-Butenyi, 3-Butenyl, 1 ,3-Butadienyl, 1 -Pentenyl, 2- Pentenyl, 3-Pentenyl, 4-Pentenyi, 1 ,3-Pentadienyl, 1 -Hexenyl, 2-Hexenyl, 3 -Hexen vi, 4-Hexenyi, 5- Hexenyi und 1,4-Hexadienyl, verstanden. Bevorzugt hiervon sind C2-C6-Alkenylreste und besonders bevorzugt sind C2-C4-Alkenylreste. Unless otherwise defined elsewhere, the term "Aikenyl", either alone or in combination with other terms, according to the invention is a linear or branched C 2 -C 12 -alkenyl radical which has at least one double bond, for example vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1, 3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexene vi, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, of which preferred are C 2 -C 6 -alkenyl radicals and particularly preferred are C 2 -C 4 -alkenyl radicals.
Sofern nicht a anderer Stelle anders definiert, wird unter dem Begriff „Alkinyl". entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-C 12-Alkinylrest, welcher mindestens eine Dreifachbindung aufweist, beispielsweise Ethinyl, 1 -Propin yl und Propargyl, verstanden. Bevorzugt hiervon sind C3-C6-Alkinylreste und besonders bevorzugt sind C3-C4-Aikinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Unless otherwise defined elsewhere, the term "alkynyl", either alone or in combination with other terms, is according to the invention a linear or branched C 2 -C 12 -alkynyl radical which has at least one triple bond, for example ethynyl, Propionyl and propargyl, understood, are preferred C3-C6-alkynyl radicals and particularly preferred are C3-C4-Aikinylreste.The alkynyl radical may also have at least one double bond.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „C ycloalkyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein C3-C8- Cycloalkylrest verstanden, beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl, verstanden. Bevorzugt hiervon sind C3-C6-Cycioalkylreste. Unless otherwise defined elsewhere, the term "cycloalkyl", either in isolation or in combination with further terms, according to the invention is understood to mean a C 3 -C 8 -cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, Preference is given here to C 3 -C 6 -cycloalkyl radicals.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Aryl" erfindungsgemäß ein aromatischer Rest mit 6 bis 14 Kohlenstoffatomen, vorzugsweise Phenyl, Naphthyl, Anthryl oderUnless otherwise defined elsewhere, the term "aryl" according to the invention an aromatic radical having 6 to 14 carbon atoms, preferably phenyl, naphthyl, anthryl or
Phenanthrenyl, besonders bevorzugt Phenyl, verstanden. Phenanthrenyl, particularly preferably phenyl, understood.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff„Arvlalkyl" eine Kombination von erfindungsgemäß definierten Resten „Aryl" und „Alkyl" verstanden, wobei der Rest im Allgemeinen über die Alkylgrupe gebunden wird, Beispiele hierfür sind Benzyi, Phenylethyl oder a- Methylbenzyl, wobei Benzyi besonders bevorzugt ist. Unless otherwise defined elsewhere, the term "aralkyl" is understood to mean a combination of radicals "aryl" and "alkyl" defined according to the invention, the radical generally being bound via the alkyl group, examples of which are benzyl, phenylethyl or Methylbenzyl, with benzyi being particularly preferred.
Sofern nicht an anderer Stelle anders definiert, bedeutet„Hetaryl" eine mono-, bi- oder tricyclische heterocyclische Gruppe aus C -Atomen und mindestens einem Heteroatom, wobei mindestens ein Zyklus aromatisch ist. Bevorzugt enthält die Hetaryl-Gruppe 3, 4, 5 oder 6 C-Atome ausgewählt aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, 1 ,2,3-Triazolyl, 1 .2.4-Triazoly 1, Oxazolyl, Isoxazolyl, Thiazolyi, Isothiazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,3,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1 ,2,3 -Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1 ,3 ,4-Thiadiazolyl, 1 ,2,5-Thiadiazoiyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1 ,2,3-Triazinyl, 1 ,2,4-Triazinyl, 1,3,5-Triazinyl, Benzo furyl, Benzisofuryl, Benzothienyl, Benzisothienyl, Indolyl, Isoindolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzoxazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1 ,3-Benzoxadiazoie, Chinolinyl, Isochinolinyl, Cinnolinyl, Phthaiazinyl, C inazolinyl. Chinoxalinyl, Naphthyridinyl, Benzotriazinyl, P rinyl. Pteridinyl und Indolizinyl. Sofern nicht an anderer Stelle anders definiert, bedeutet „Heterocyclyl" einen monocyclischen, gesättigten oder teilgesättigten 4-, 5-, 6- oder 7-gliedrigen Ring aus C -Atomen und mindestens einem Heteroatom im Ring. Bevorzugt enthält die Heterocyclyl-Gruppe 3, 4, 5 oder 6 C-Atome und 1 oder 2 Heteroatome aus der Reihe Sauerstoff, Schwefel oder Stickstoff. Beispiele für Heterocyclyl sind Azetidinyl, Azolidinyl, Azinanyl, Oxetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiethanyl, Thiolanyl. Thianyl , T etrahydro furyl . Unless otherwise defined elsewhere, "hetaryl" means a mono-, bi- or tricyclic heterocyclic group of C atoms and at least one heteroatom, wherein at least one cycle is aromatic. Preferably, the hetaryl group contains 3, 4, 5 or 6 carbon atoms selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1 .2.4-Triazoly 1, oxazolyl, isoxazolyl, thiazolyi , Isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl , 1, 3, 4-thiadiazolyl, 1, 2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, benzo furyl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazoie, quinolinyl, isoquinolinyl, cinnolinyl, phthaiazinyl, c inazolinyl. Quinoxalinyl, naphthyridinyl, benzotriazinyl, vinylrinyl. Pteridinyl and indolizinyl. Unless otherwise defined elsewhere, "heterocyclyl" means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring of C atoms and at least one heteroatom in the ring Preferably, the heterocyclyl group contains 3, 4, 5 or 6 C atoms and 1 or 2 heteroatoms from the series oxygen, sulfur or nitrogen Examples of heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, T etrahydro furyl.
Sofern nicht an anderer Steile anders definiert, bedeuten „Oxo-Heterocycly!" bzw. „Dioxo- Heterocyclyl" ein Heterocyclyl, das an mindestens einer Position im Ring ein Ring-Atom enthält, das mit einer bzw. zwei (=0) -Gruppen substituiert ist. Bevorzugt ist dabei ein Heteroatom wie beispielsweise Schwefel mit einer oder zwei (=0) -Gruppen substituiert, wobei sich dann die Gruppe - S(=0)- bzw. -S(=0)2- ergibt, wobei das S-Atom Bestandteil des Rings ist. Unless otherwise defined in other parts, "oxo-heterocyclyl" or "dioxo-heterocyclyl" means a heterocyclyl which contains at least one position in the ring a ring atom containing one or two (= 0) groups is substituted. Preference is given to a heteroatom such as sulfur substituted with one or two (= 0) groups, in which case the group - S (= 0) - or -S (= 0) 2- results, wherein the S atom component of the ring.
Im Rahmen der vorliegenden Erfindung werden unter durch Halogensubstituierte Reste, beispielsweise „Halogenaikyl", einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogenierte Reste verstanden. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein.„Halogen" steht dabei für Fluor, Chlor, Brom oder Jod, bevorzugt für Fluor oder Chlor. Unter dem Begriff „Aikoxy". entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkoxy, wird vorliegend ein Rest O-Alkyl verstanden, wobei der Begriff„Aikyl" die oben stehende Bedeutung aufweist. In the context of the present invention, halo-substituted radicals, for example "haloalkyl", are radicals which are mono- or polysubstituted to the maximum possible number of substituents halogenated radicals can be identical or different halogen halogen atoms. "Halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine. The term "aikoxy", either alone or in combination with other terms such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term "aikyl" having the meaning given above.
Erläuterung der Verfahren und Zwischenprodukte Explanation of processes and intermediates
Die Verbindungen der Formel (I) können beispielsweise nach den in Schema 1 bis 10 angegebenen Verfahren synthetisiert werden. Hierbei haben die in den Formeln angegebenen Reste R1, R2, R3, R4, R\ R' , R . R8 R51, R \ R l, R \ G und U soweit nicht anders angegeben j eweils die in den Ausgestaltungen (1-1) bis (5-1) angegebene Bedeutung. The compounds of the formula (I) can be synthesized, for example, by the methods given in Schemes 1 to 10. Here, the radicals indicated in the formulas R 1 , R 2 , R 3 , R 4 , R \ R ', R have. R 8 R 51 , R 1 , R 2 G, and U unless indicated otherwise, all have the meanings given in embodiments (1-1) to (5-1).
Verbindungen der Formel (la) können wie in Schema 1 gezeigt, synthetisiert werden, wobei V für Br, Ci oder für -0-C(=0)CH2-Hal und Hai für Br oder C 1 steht, indem Verbindungen der Formel (II) mit 2 Equivalenten eins Halogenketons oder eines Halogenketonanhydrids der Formel (III) zu Verbindungen der Formel (la) umgesetzt werden (siehe z.B. Canadian Journal of Chemistry (1971), 49(4), 668-671). Compounds of formula (Ia) can be synthesized as shown in Scheme 1, wherein V is Br, Ci or -0-C (= 0) CH 2 -Hal and Hai is Br or C 1, by compounds of formula (II) with 2 equivalents of a haloketone or a Halogenketonanhydrids of formula (III) compounds of the formula (Ia) are reacted (see, for example, Canadian Journal of Chemistry (1971), 49 (4), 668-671).
Schema 1 Scheme 1
(II) (la)  (II) (la)
Verbindungen der Formel I I sind literaturbekannt ( vgl. z.B. WO2009099929, WO20120921 15, WO201 1057022, WO2009099929, WO2011017342) oder können in Analogie zu literaturbekannten Verfahren erhalten werden. Verbindungen der Formel (III) sind käuflich. Compounds of the formula I are known from the literature (cf., for example, WO2009099929, WO20120921 15, WO201 1057022, WO2009099929, WO2011017342) or can be obtained in analogy to processes known from the literature. Compounds of the formula (III) are commercially available.
Verbindungen der Formel (Ib) in der ALK für C1-C4 Alkyl steht, können wie in Schema 2 gezeigt, aus Aminen der Formel (II) durch Umsetzung mit 2-Chlormalonsäuremonochlorid onoestern der Formel (IV) in Gegenwart einer Base, wie z.B. Triethylamin erhalten werden. Schema 2 Compounds of formula (Ib) in the ALK is C 1 -C 4 alkyl, as shown in Scheme 2, from amines of formula (II) by reaction with 2-Chlormalonsäuremonochlorid onoestern of formula (IV) in the presence of a base, such as Triethylamine can be obtained. Scheme 2
(II) (Ib) (II) (Ib)
Verbindungen der Formel (IV) sind in der Literatur bekannt oder können in Analogie zu bekannten Verfahren hergestellt werden ( vgl. Tetrahedron 1993, 49, 9447-9452). Verbindungen der Formel (Ic) können wie in Schema 3 gezeigt, durch Umsetzung von Estern der Formel (Ib) mit Aminoverbindungen der Formel (V) nach allgemein bekannten Verfahren erhalten werden. Für die Umsetzung mit bestimmten Aminen können gegebenenfalls Aktivi erungsreagenzi en, wie z.B. Trimethylaluminium eingesetzt werden. Schema 3 Compounds of the formula (IV) are known in the literature or can be prepared analogously to known processes (see Tetrahedron 1993, 49, 9447-9452). Compounds of the formula (Ic) can be obtained as shown in Scheme 3 by reacting esters of the formula (Ib) with amino compounds of the formula (V) according to generally known methods. For the reaction with certain amines, activating reagents, for example trimethylaluminum, may optionally be used. Scheme 3
(Ib) (Ic) (Ib) (Ic)
Amine der Formel (V) sind käuflich oder in der Literatur bekannt. Amines of the formula (V) are commercially available or known in the literature.
Verbindungen der Formel (Id) können wie in Schema 4 gezeigt aus Verbindungen der Formel (Ia) nach allgemein bekannten Verfahren durch Umsetzungen mit Alkoholaten oder Alkoholen in Gegenwart einer Base, wie z.B. Natriumhydrid erhalten werden. Verbindungen der Formel (Ie) können ausgehend von Verbindungen der Formel (Id; R51=H) nach allgemein bekannten Verfahren durch Umsetzung mit Verbindungen der Formel (VII), wobei L1 für Cl, Br oder -0(=0)R55 steht, in Gegenwart einer Base, wie z.B. Triethylamin, erhalten werden. Compounds of formula (Id) can be obtained as shown in Scheme 4 from compounds of formula (Ia) by well-known methods by reaction with alcoholates or alcohols in the presence of a base such as sodium hydride. Compounds of the formula (Ie) can be prepared starting from compounds of the formula (Id; R 51 = H) by generally known processes by reaction with compounds of the formula (VII) where L 1 is Cl, Br or -O (= O) R 55 is in the presence of a base, such as triethylamine.
Schema 4 Scheme 4
(Ia) (Id) (Ie) (Ia) (Id) (Ie)
Verbindungen der Formeln (VI) und (VII) sind käuflich oder in der Literatur bekannt. Verbindungen der Formel (Ii) können nach allgemein bekannten Verfahren aus Verbindungen der Formel (la) durch Umsetzungen mit Thiolaten oder Thiolen in Gegenwart einer Base, wie z.B. Natriumhydrid erhalten werden, wie in Schema 5 gezeigt. Verbindungen der Formel (Ii) können anschließend nach allgemein bekannten Verfahren mit einem Oxidationsmittel, wie z.B. meta- C Ii ! rperben zoesäure zu Sulfoxiden und Sulfonen der Formel (Ig) oxidiert werden. Compounds of formulas (VI) and (VII) are commercially available or known in the literature. Compounds of formula (Ii) may be prepared by generally known methods from compounds of formula (Ia) by reactions with thiolates or thiols in the presence of a base such as sodium hydride as shown in Scheme 5. Compounds of formula (Ii) can then be prepared by generally known methods with an oxidizing agent, such as meta-C Ii! Rperben zoesäure be oxidized to sulfoxides and sulfones of the formula (Ig).
Schema 5 Scheme 5
Verbindungen der Formel (VIII) sind käuflich oder in der Literatur bekannt. Compounds of formula (VIII) are commercially available or known in the literature.
Verbindungen der Formel (Ih) können aus Verbindungen der Formel (la) durch Umsetzungen mit Aminoverbindungen der Formel (IX) nach allgemein bekannten Verfahren in Gegenwart einer Base, wie z.B. Triethylamin erhalten werden, wie in Schema 6 gezeigt. Auf gleiche Weise lassen sich auch andere Aminoverbindungen, wie z.B. Hydrazine umsetzen. Verbindungen der Formel (Ih, R53= H ) in der L1 für Cl, Br oder -0(=0)R55 steht, können anschließend mit Carbonsäur eäurehalogeniden oder Carbonsäureanhydriden der Formel (VII) in Gegenwart einer Base, wie z.B. Triethylamin weiter zu Verbindungen der Formel (Ii) umgesetzt werden. Compounds of formula (Ih) may be obtained from compounds of formula (Ia) by reactions with amino compounds of formula (IX) according to well-known procedures in the presence of a base such as triethylamine as shown in Scheme 6. In the same way, other amino compounds such as hydrazines can be implemented. Compounds of the formula (Ih, R 53 = H) in which L 1 is Cl, Br or -O (= O) R 55 may subsequently be treated with carboxylic acid acid halides or carboxylic anhydrides of the formula (VII) in the presence of a base, for example triethylamine be further converted to compounds of formula (Ii).
Schema 6 Scheme 6
(la) (Ih) (Ii) Verbindungen der Formel (VII) und (IX) sind käuflich oder in der Literatur bekannt. (la) (Ih) (II) Compounds of formula (VII) and (IX) are commercially available or known in the literature.
Verbindungen der Formel (Ij) können, wie in Schema 7 gezeigt, durch Dehalogenierung von Verbindungen der Formel (Ia) mit aktiviertem Zink erhalten werden (vgl. z.B. Dyes and Pigments 2013, 96, 7-15). Schema 7 Compounds of formula (Ij) can be obtained as shown in Scheme 7 by dehalogenation of compounds of formula (Ia) with activated zinc (see, e.g., Dyes and Pigments 2013, 96, 7-15). Scheme 7
(Ia) (Ij) (Ia) (Ij)
Verbindungen der Formel (Im) können, wie in Schema 8 gezeigt, in Analogie zu allgemein bekannten Verfahren durch Umsetzung von Amiden der Formel (Ic) mit einem Schwefelungsreagenz, wie z.B. P2S5 oder Lawesson's Reagenz erhalten werden. Compounds of the formula (Im) can be obtained, as shown in Scheme 8, analogously to generally known processes by reacting amides of the formula (Ic) with a sulfurizing reagent such as P2S5 or Lawesson 's reagent.
Schema 8 Scheme 8
(Ic) (Im) (Ic) (Im)
Verbindungen der Formel (Ik) können, wie in Schema 9 gezeigt erhalten werden, wobei zunächst in Analogie zum in Schema 3 angegebenen Verfahren Carbonsäureester der Formel (Ib) mit N, O- Dimethylaminohydroxylamin zu einem„Weinreb-Amid" der Formel (Ii) umgesetzt werden. Dieses wird anschließend in Analogie zu bekannten Verfahren [vgl. z.B. WO201 154844, WO2005100301 ] mit einer metallorganischen Verbindung der Formel (XI) wie z.B. einer Alkyl- oder Aryllithiumverbindung oder einer Grignardverbindung zu Verbindungen der Formel (Ik) umgesetzt. Verbindungen der Formel (XI) und (XII) sind käuflich oder in der Literatur bekannt. Schema 9 Compounds of the formula (I) can be obtained as shown in Scheme 9, in which, analogously to the process shown in Scheme 3, carboxylic acid esters of the formula (Ib) with N, O-dimethylaminohydroxylamine are converted into a "Weinreb amide" of the formula (Ii) This is then reacted analogously to known processes [cf., for example, WO20154844, WO2005100301] with an organometallic compound of the formula (XI), for example an alkyl- or aryllithium compound or a Grignard compound, to give compounds of the formula (Ik) Formula (XI) and (XII) are commercially available or known in the literature. Scheme 9
(Ib) (Ii) (Ik) (Ib) (ii) (Ik)
Verbindungen der Formel (Ii) können weiterhin, wie in Schema 10 gezeigt erhalten werden, wobei in Analogie zum in Schema 2 angegebenen Verfahren Amine der Formel (II) mit Säurechloriden derCompounds of the formula (Ii) can furthermore be obtained as shown in Scheme 10, in which, analogously to the process indicated in Scheme 2, amines of the formula (II) with acid chlorides of
Formel (XII) in Gegenwart einer Base umgesetzt werden. Formula (XII) are reacted in the presence of a base.
Verbindungen der Formel (XII) sind entweder als Säurechloride in der Literatur bekannt oder können in Analogie zu bekannten Verfahren aus den entsprechenden Carbonsäuren erhalten werden, [vgl. z.B. EP 37015, DE4301356, JP2006232788]. Schema 10 Compounds of the formula (XII) are known either as acid chlorides in the literature or can be obtained in analogy to known processes from the corresponding carboxylic acids [cf. e.g. EP 37015, DE4301356, JP2006232788]. Scheme 10
(XII) (XII)
Im Allgemeinen können Verbindungen der Formel (I) nach den oben beschriebenen Verfahren hergestellt werden. Falls einzelne Verbindungen nicht nach den oben beschriebenen Verfahren hergestellt werden können, ist die Synthese durch Derivatisierung anderer Verbindungen der Formeln (I) möglich oder durch individuelle Modifikationen der beschriebenen Verfahren. Zum Beispiel kann es Vorteile haben, gewisse Verbindungen der Formel (I) aus anderen Verbindungen der Formel (I) herzustellen z.B. durch Hydrolyse, Verersterung, Amidbildung, Reduktion, Veretherung, Oxidation, Oiefmierung, Ilalogen ierung. Acylierung, Alkylierung und dergleichen. Die erfindungsgemäßen Verfahren zur Herstellung der neuen Verbindungen der Formel (I) werden vorzugsweise unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel zur Durchfuhrung der erfindungsgemäßen Verfahren kommen neben Wasser alle inerten Lösungsmittel in Frage. Als Beispiele sind zu nennen:. Halogenkohlenwasserstoffe (z.B. Chlorkohienwasserstoffe, wie Tetraethylen, Tetrachlorethan, Dichlorpropan, Methylenchlorid, Dichlorbutan, Chloroform, T etrachlorkohlensto ff, Trichlorethan, Trichlorethylen, Pentachlorethan, Difluorbenzol, 1 ,2-Dichlorethan, Chlorbenzol, Brombenzol. Dichlorbenzol, Chlortoluol, Trichlorbenzol), Alkohole (z.B. Methanol, Ethanol, Isopropanol, Butanol), Et her (z.B. Ethylpropylether, Methyl -tert-butylether, Anisol, Phenetol, Cyclohexylmethylether, Dimethylether, Diethylether, Diproplether, Diisopropylether, Di-n-butylether, Diisobutylether, Diisoamyiether, Ethylenglycoldimethylether, Tetrahydrofuran, 1 ,4-Dioxan, Dichlordiethylether und Polyether des Ethylenoxids und/oder Propylenoxids), Amine (z.B. Trimethyl-, Triethyl-, Tripropyl-, Tributylamin, N-Methylmo holin, Pyridin und Tetramethyl endiamin), Nitrokohlenwasserstoffe (z.B. Nitromethan, Nitroethan, Nitropropan, Nitrobenzol, Chloniitrobenzoi, o- Nitrotoluol); Nitrile (wie z.B. Acetonitril, Propionitril, Butyronitril, Isobutyronitril, Benzonitril, m- Chlorbenzonitril), Tetrahydrothiophendioxid, Dimethylsulfoxid, Tetramethylensulfoxid, Dipropylsuifoxid, Benzylmethylsulfoxid, Diisobutylsulfoxid, Dibutylsulfoxid, Diisoamylsulfoxid, Sulfone (z.B. Dimethyl-, Diethyi-, Dipropyl-, Dibutyl-, Diphenyi-, Di hex vi-, Methyiethyl-, Ethylpropyl- , Ethylisobutyl- und Pentamethylensulfon), aliphatische, cycloaliphatische oder aromatische Kohlenwasserstoffe (z.B. Pentan, Hexan, Heptan, Oktan, Nonan und technische Kohlenwasserstoffe), ferner sogenannte "White Spirits" mit Komponenten mit Siedepunkten im Bereich von beispielsweise 40°C bis 250°C, Cymol, Benzinfraktionen innerhalb eines Siedeintervalles von 70°C bis 190°C, Cyclohexan, Methyl cyclohexan, Petrolether, Ligroin, Octan, Benzol, Toluol, Chlorben/ol. Brombenzol, Nitrobenzol, Xylol. Ester (z.B. Methyl-, Ethyl-, Butyl-, Isobutylacetat, Dimethyl-, Dibutyl-, Ethylencarbonat); Amide (z.B. Hexamethylenphosphorsäuretriamid, Formamid, N-Methyl-formamid, Ν,Ν-Dimethyl -formamid, N. -Di propyl-formamid. N,N-Dibutyl-formamid, N-Methyl -Pyrrolidin, N- Methyl-caprolactam, 1 , 3 -Dimethyl -3 ,4,5,6 -tetrahydro-2 ( 1 H)-pyrimidin, Octylpyrrolidon, Octylcaprolactam, 1 ,3 -Dimethyl-2-imidazolindion, N-Formyl -pip eridin, N.N '-Di formyl -pipera/in ) und Ketone (z.B. Aceton, Acetophenon, Methylethylketon, Methylbutylketon) . In general, compounds of formula (I) can be prepared by the methods described above. If individual compounds can not be prepared by the methods described above, the synthesis is possible by derivatization of other compounds of formula (I) or by individual modifications of the methods described. For example, it may be advantageous to prepare certain compounds of formula (I) from other compounds of formula (I), for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, oxygenation, ilogenation. Acylation, alkylation and the like. The processes according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using a diluent. As a diluent for Implementation of the method according to the invention in addition to water, all inert solvents in question. As examples are :. Halogenated hydrocarbons (eg, chlorohydrocarbons, such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (eg Methanol, ethanol, isopropanol, butanol), ethers (eg, ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1 , 4-dioxane, dichloro diethyl ether and polyethers of ethylene oxide and / or propylene oxide), amines (for example trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmoholin, pyridine and tetramethylendiamine), nitrohydrocarbons (eg nitromethane, nitroethane, nitropropane, Nitrobenzene, chloroniitrobenzoi, o-nitrotoluene); Nitriles (such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethylsulfoxide, tetramethylenesulfoxide, dipropylsulfoxide, benzylmethylsulfoxide, diisobutylsulfoxide, dibutylsulfoxide, diisoamylsulfoxide, sulfones (eg dimethyl, diethyi, dipropyl, dibutyl, Diphenyi-, dihex-, methylethyl-, ethylpropyl-, ethylisobutyl- and pentamethylenesulfone), aliphatic, cycloaliphatic or aromatic hydrocarbons (eg pentane, hexane, heptane, octane, nonane and technical hydrocarbons), also so-called "white spirits" with components with boiling points in the range, for example, 40 ° C to 250 ° C, cymene, gasoline fractions within a boiling interval of 70 ° C to 190 ° C, cyclohexane, methyl cyclohexane, petroleum ether, ligroin, octane, benzene, toluene, chloroben / ol. Bromobenzene, nitrobenzene, xylene. Esters (eg methyl, ethyl, butyl, isobutyl acetate, dimethyl, dibutyl, ethylene carbonate); Amides (eg, hexamethylenephosphoric triamide, formamide, N-methylformamide, Ν, Ν-dimethylformamide, N.-di-propylformamide, N, N-dibutyl-formamide, N-methyl-pyrrolidine, N-methyl-caprolactam, 1 , 3 -dimethyl -3, 4,5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone, octylcaprolactam, 1, 3-dimethyl-2-imidazolinedione, N-formyl -Pip eridin, NN '-di formyl - pipera / in) and ketones (eg acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
Selbstverständlich kann man das erfindungsgemäße Verfahren auch in Gemischen der genannten Lösungs- und Verdünnungsmittel durchführen. Of course, the process according to the invention can also be carried out in mixtures of the solvents and diluents mentioned.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen™30°C und +150°C, vorzugsweise zwischen -10°C und +100°C. The reaction temperatures can be varied within a substantial range when carrying out the processes according to the invention. In general, temperatures between 30.degree. C. and + 150.degree. C., preferably between -10.degree. C. and + 100.degree. C., are used.
Die erfindungsgemäßen Verfahren werden im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - im Allgemeinen bei absoluten Drücken zwischen 0,1 bar und 15 bar - durchzuführen. Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe im Allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuss zu verwenden. Die Umsetzung wird im Allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels, gegebenenfalls auch unter einerThe processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 bar and 15 bar. To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in to use a larger surplus. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, optionally also under a
Schutzgas-Atmosphäre (z.B. unter Stickstoff, Argon oder Helium) durchgeführt und das Reaktionsgemisch wird im Allgemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Hersteilungsbeispiele). Inert gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature. The work-up is carried out by customary methods (see the preparation examples).
Als basische Reaktionshilfsmittel zur Durchführung der erfindungsgemäßen Verfahren können alle geeigneten Säurebindemittel eingesetzt werden. Als Beispiele sind zu nennen: Erdalkali- oder Alkalimetallverbindungen (z.B. Hydroxide, Hydride. Oxide und Carbonate des Lithiums, Natriums, Kaliums, Magnesiums, Calciums und Bariums), Amidinbasen oder Guanidinbasen (z.B. 7-M ethyl- 1,5,7- triaza-bicyclo(4.4.0)dec-5-en (MTBD); Diazabicyclo(4.3.0)nonen (DBN), Diazabicyclo(2.2.2)octan (DABCO), 1 ,8-Diazabicyclo(5.4.0)undecen (DBU), Cyclohexyltetrabutyl-guanidin (CyTBG), Cyclohexyltetramethylguanidin (CyTMG), N,N,N,N-Tetramethyl-l,8-naphthalindiamin,As basic reaction auxiliaries for carrying out the process according to the invention, it is possible to use all suitable acid binders. Examples which may be mentioned are: alkaline earth or alkali metal compounds (eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine bases or guanidine bases (eg 7-methyl-1,5,7-triaza -bicyclo (4.4.0) dec-5-ene (MTBD); diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1, 8-diazabicyclo (5.4.0) undecene ( DBU), cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-l, 8-naphthalenediamine,
Pentamethylpiperidin) und Amine, insbesondere tertiäre Amine, (z.B. Triethylamin, Trimethylamin, Tribenzylamin, Triisopropylamin, Tributylamin, Tricyclohexyl amin , Triamylamin, Trihexylamin, N,N- Dimethylanilin, Ν,Ν-Dimethyl-toluidin, N,N-Dimethyl-p-aminopyridin, N-Methyl-pyrrolidin, N- Methyi-piperidin, N-Methyl-imidazol, N-Methyi-pyrazol, N-Methyl-morpholin, N-Methyl- hexamethylendiamin, Pyridin, 4-Pyrrolidinopyridin, 4-Dimethylamino-pyridin, Chinolin, oc-Picolin, ß- Picolin, Pyrimidin, Acridin, Ν,Ν,Ν',Ν'-Tetramethyiendiamin, Ν,Ν,Ν',Ν'-Tetraethylendiamin, Chinoxalin, N-Propyl-diisopropylamin, N-Ethyl-diisopropylamin, Ν,Ν' -Dimethyl-cyclohexylamin, 2,6- Lutidin, 2,4-Lutidin oder Triethyldiamin). Pentamethylpiperidine) and amines, in particular tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, Ν, Ν-dimethyl-toluidine, N, N-dimethyl-p- aminopyridine, N-methyl-pyrrolidine, N-methylpiperidine, N-methyl-imidazole, N-methylpyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, Quinoline, oc-picoline, β-picoline, pyrimidine, acridine, Ν, Ν, Ν ', Ν'-tetramethylenediamine, Ν, Ν, Ν', Ν'-tetraethylenediamine, quinoxaline, N-propyl-diisopropylamine, N-ethyl diisopropylamine, Ν, Ν'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethyldiamine).
Als saure Reaktionshilfsmittel zur Durchführung der erfindungsgemäßen Verfahren können alle Mineralsäuren (z.B. Halogenwasserstoff-säuren wie Fluorwasserstoffsäure, Chlorwasserstoffsäure, Bromwasserstoffsäure oder Iodwasserstoffsäure sowie Schwefelsäure, Phosphorsäure, Phosphorige Säure, Salpetersäure), Lewis Säuren (z.B. Aluminium(III)-chlorid, Bortrifluorid oder sein Etherat, Titan(IV)chlorid, Zinn(IV)-chlorid) und organische Säuren (z.B. Ameisensäure, Essigsäure, Propionsäure, Malonsäure, Milchsäure, Oxalsäure, Fumarsäure, Adipinsäure, Stearinsäure, Weinsäure, Ölsäure, Methansulfonsäure, Benzoesäure, Benzolsulfonsäure oder para-Toluolsulfonsäure) eingesetzt werden. As acidic reaction auxiliaries for carrying out the process according to the invention, it is possible to use all mineral acids (for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid), Lewis acids (for example aluminum (III) chloride, boron trifluoride or etherate) , Titanium (IV) chloride, tin (IV) chloride) and organic acids (eg formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid ) are used.
Isomere Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit sowohl reine Stereoisomere als auch beliebige Gemische dieser Isomere. Verfahren und Verwendungen Isomers Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus comprises both pure stereoisomers and any mixtures of these isomers. Methods and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als S chädlingsbekämp fungsmittel , insbesondere Pflanzens chutzmittel . Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. The invention further relates to the use of the compounds of the formula (I) as insecticides, in particular herbicides. In the context of the present application, the term pest control always always includes the term pesticides.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträgli chkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. The compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the crop and to control animal pests, in particular insects , Arachnids, helminths, in particular nematodes, and mollusks, which are found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in storage and materials protection and in the hygiene sector.
Im Rahmen der vorliegenden Patentanmeldung ist der Begriff „Hygiene" so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauberkeit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder therapeutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
Der Begriff„Hygienesektor" deckt alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen wichtig sind, zum Beispiel im Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. Der Begriff„Hygieneschädling" ist daher so zu verstehen, dass damit ein oder mehrere Tierschädlinge gemeint sind, deren Gegenwart im Hygienesektor problematisch ist, insbesondere aus Gesundheitsgründen. Es ist daher ein Hauptziel, das Vorhandensein von Hygieneschädlingen und/oder das Ausgesetztsein ihnen gegenüber im Hygienesektor zu vermeiden oder auf ein Mindestmaß zu begrenzen. Dies lässt sich insbesondere durch die Anwendung eines Pestizids erreichen, das sich sowohl zum Verhindern eines Befalls als auch zum Verhindern eines bereits vorhandenen Befalls einsetzen lässt. Man kann auch Zubereitungen verwenden, die eine Exposition gegenüber Schädlingen verhindern oder reduzieren. Hygieneschädlinge schließen zum Beispiel die unten erwähnten Organismen ein. The term "hygiene sector" covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry etc. The term "hygiene pest" should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests For example, hygiene pests include the organisms mentioned below.
Der Begriff „Hygieneschutz" deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen aufrechterhalten und/oder verbessert werden. The term 'hygiene protection' thus covers all activities which maintain and / or improve those hygiene measures, rules and procedures.
Die Verbindungen der Formel (I) können vorzugsweise als S chädlingsb ekämp üngsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The compounds of the formula (I) can preferably be used as a chelating agent. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z. B. Acarus spp., z. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z. B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gailinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z. B. Eutetranychus banksi, Eriophyes spp., z. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus coffeae, Oiigonychus coniferarum, Oligonychus ilicis, Oiigonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oiigonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z. B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chiiopoda z. B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z. B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z. B. Blaniulus guttulatus; aus der Klasse der Insecta, z. B. aus der Ordnung der Blattodea z. B. Blatta orientalis, Blatteila asahinai, Blattelia germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z. B. Acaiymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., z. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z. B. Chaetocnema confmis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes fermgineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diioboderus spp., Epicaerus spp., Epilachna spp., z. B. Epiiachna borealis, Epilachna varivestis, Epitrix spp., z. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Heiluia undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajuius, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemiineata, Leucoptera spp., z. B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomoipha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Ou lema spp., z. B. Oulema melanopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyilophaga spp., Phyllophaga hellen. Phyllotreta spp., z. B. Phyllotreta armoraciae, Phyllotreta pusi lla, Phyllotreta ramosa, Phyllotreta striolata, Popiliia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhi/obius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus fermgineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius. Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp.. z. B. Sternechus paludatus, Symphyletes spp., Tanymecus spp.. z. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z. B. Zabrus tenebrioides; aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; aus der Ordnung der Diptera z. B. Aedes spp., z. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z. B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Caliiphora erythrocephala, Caliiphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Del ia spp., z. Ii. Delia antiqua, Delia coarctata, Delia floriiega, Deiia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z. B. Drosphiia melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., z. B. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z. B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbornieila subcincta, Pegomya oder Pegomyia spp., z. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psiia rosae, Rhagoietis spp., z. B. Rhagoletis cingulata, Rhagoletis completa, Rhagoietis fausta, Rhagoletis indifferens, Rhagoietis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; aus der Ordnung der Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z. B. Acyrthosiphon pisum, Acrogonia spp., Aeneoiamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphano Stigma piri. Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp.. Aspidiella spp.. Aspidiotus spp., z. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z. B. Cacopsylla pyricola, Caliigypona marginata, Capulinia spp., Cameocephaia fulgida, Ceratovacuna ianigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Daibulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp.. Doralis spp., Drosicha spp., Dysaphis spp., z. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca Steven si, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp.. Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylia cubana, Heteropsyila spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z. B. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praeionga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psyila mali, Psylla pyri. Pteromalus spp., Pulvinaria spp., Pyri IIa spp., Quadraspidiotus spp., z. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopaiosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia negiecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.. Campylomma livida, Cavelerius spp., Cimex spp., z. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z. B. Lygocoris pabulinus, Lygus spp.. z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahl berge! la singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z. B. Acromyrmex spp., Athalia spp., z. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Di priori spp., z. B. Diprion similis, Hoplocampa spp., z. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis. Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus aseilus, Porceliio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., z. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.. Caloptilia theivora, Capua reticulana, Carpocapsa pomoneila, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambigueila, Cnaphalocerus spp., Cnaphalocrocis medinaiis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana. Cydia pomoneila, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Hel icoverpa spp., z. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padeila, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B. Lyonetia clerkelia, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubiiaiis, Panolis flammea, Parnara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Peri leucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Pluteila maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia inciudens, Pyrausta nubiiaiis, Rachipiusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionelia, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z. B. Gryllotalpa gryllotalpa, Hieroglyphiis spp., Locusta spp., z. B. Locusta migratoria, Melanoplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z. B. Damal i nia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z. B. Lepinotus spp., Liposceiis spp.; aus der Ordnung der Siphonaptera z. B. Ceratophyllus spp., Ctenocephaiides spp., z. B. Ctenocephalides canis, Ctenocephalides felis, Pul ex irritans, Tunga penetrans, Xenopsyila cheopis; aus der Ordnung der Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z. B. Frankliniella fusca, Frankl in iella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigereila spp., z. B. Scutigerella immaculata; Pests from the strain of Arthropoda, in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gailinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Z. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Z. Oligonychus coffeae, Oiigonychus coniferarum, Oligonychus ilicis, Oiigonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oiigonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of Chiiopoda z. Geophilus spp., Scutigera spp .; from the order or class of Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of Diplopoda z. B. Blaniulus guttulatus; from the class of the Insecta, z. B. from the order of Blattodea z. Blatta orientalis, Blattparta asahinai, Blattelia germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., Z. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z. Acaiymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., E.g. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., E.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. Chaetocnema confmis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., E.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes fermgineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., E.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diioboderus spp., Epicaerus spp., Epilachna spp., E.g. Epiiachna borealis, Epilachna varivestis, Epitrix spp., E.g. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Heiluia and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajuius, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemiineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomoipha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., E.g., Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oumema spp., E.g. Oulema melanopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyilophaga spp., Phyllophaga. Phyllotreta spp., Z. Phyllotreta armoraciae, Phyllotreta pusi lla, Phyllotreta ramosa, Phyllotreta striolata, Popiliia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhi / obius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus fermgineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp. B. Sitophilus granarius. Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Starchus spp. B. Starchus paludatus, Symphyletes spp., Tanymecus spp. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera z. B. Aedes spp., Z. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Caliiphora erythrocephala, Caliiphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., E.g. Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp., Z. Ii. Delia antiqua, Delia coarctata, Delia floriiega, Deiia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophia melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., E.g. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterbornieila subcincta, Pegomya or Pegomyia spp., E.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psiia rosae, Rhagoietis spp., E.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoietis fausta, Rhagoletis indifferens, Rhagoietis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., E.g. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., Z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of Hemiptera z. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. Acyrthosiphon pisum, Acrogonia spp., Aeneoiamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphano stigma piri. Aphis spp., Z. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp. Aspidiella spp. Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., e.g. Cacopsylla pyricola, Caliigypona marginata, Capulinia spp., Cameocephaia fulgida, Ceratovacuna ianigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli , Coccus spp., Z. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Daibulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp. Doralis spp. Drosicha spp., Dysaphis spp., Z. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. Empaasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca steven si, Eriosoma spp. Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylia cubana, Heteropsyila spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., E.g. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., E.g. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praeionga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. Psylla buxi, Psyila mali, Psylla pyri. Pteromalus spp., Pulvinaria spp., Pyri IIa spp., Quadraspidiotus spp., E.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopaiosiphum spp., E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. Saissetia coffeae, Saissetia miranda, Saissetia negiecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp. Campylomma livida, Cavelerius spp., Cimex spp., E.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. Eustistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp , B. Lygocoris pabulinus, Lygus spp .. z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahl mountains! la singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Di priori spp., Z. B. Diprion similis, Hoplocampa spp., Z. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis. Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z. Armadillidium vulgare, Oniscus aseilus, Porceliio scaber; from the order of Isoptera z. B. Coptotermes spp., Z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of Lepidoptera z. Achroia grisella, Acronica major, Adoxophyes spp., E.g. Adoxophytes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., Z. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. For example Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. Caloptilia theivora, Capua reticulana, Carpocapsa pomoneila, Carposina niponensis, Cheimatobia brumata , Chilo spp., Z. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodixis chalcites, Clysia ambigueila, Cnaphalocerus spp., Cnaphalocrocis medinaiis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., E.g. B. Cydia nigricana. Cydia pomoneila, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Efoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., E.g. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padeila, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B. Lyonetia clerkelia, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp. Orthaga spp., Ostrinia spp. Ostrinia nubiiaiis, Panolis flammea, Parnara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Peri leucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Pluteila maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia inciudens, Pyrausta nubiiaiis, Rachipiusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g. Scirpophaga innotata, Scotia segetum, Sesamia spp., E.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionelia, Tineola bisselliella, Tortrix spp ., Trichophaga tapetzella, Trichoplusia spp. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphiis spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera z. B. Damalia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera z. Lepinotus spp., Liposceiis spp .; from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephaiides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pul ex irritans, Tunga penetrans, Xenopsyila cheopis; from the order of Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp. B. Frankliniella fusca, Frankl in iella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., e.g. B. Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigereila spp., Z. B. Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.; sowie aus der Klasse der Gastropoda z. B. Arion spp., z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., Z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d. h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z. B. Aglenchus agricola, Anguina spp., z. B. Anguina tritici, Aphelenchoides spp., z. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z. B. Cacopaurus pestis, Criconemella spp., z. B. Criconemeila curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z. B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.. Hopiolaimus spp., Longidorus spp., z. B. Longidorus africanus, Meloidogyne spp., z. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne liapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z. B. Paratrichodorus minor, Paratyienchus spp., Pratylenchus spp., z. B. Pratyienchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radophoius spp., z. B. Radopholus citrophiius, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z. B. Tylenchorhynchus annulatus, Tylenchulus spp. Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. Plant pests from the strain of Nematoda, ie plant parasitic nematodes, in particular Aglenchus spp., Z. Aglenchus agricola, Anguina spp., E.g. Anguina tritici, Aphelenchoides spp., E.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemeila curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., Z. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp. Hopiolaimus spp., Longidorus spp., E.g. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne liapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratyienchus spp., Pratylenchus spp., E.g. B. Pratyienchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radophoius spp. Radopholus citrophiius, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp. The compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as an anti-MLO (mycoplasma like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Formulierungen formulations
Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungs formen als S chädlingsb ekämp fungsmittel wie z. B. Drench-, Drip- und Sprit/brühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wieThe present invention further relates to formulations and application forms prepared therefrom as S chädlingsb ekämp fungsmittel such. B. drench, drip and fuel / brew, comprising at least one compound of formula (I). Optionally, the uses include other pesticides and / or effect-enhancing adjuvants such as
Penetrationsförderer, z. B. pflanzliche Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester pflanzlicher Fettsäuren wie beispielsweise Rapsöl- oder Soj aölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze, z. B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fördernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar-Polymere und/oder Humectants wie z. B. Glycerin und/oder Dünger wie beispielsweise Ammonium, Kalium oder Phosphor enthaltende Dünger. Penetration conveyor, z. For example, vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soy aölmethylester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg. As organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such. As dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such. As glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Specif cations, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einer oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ; These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifcations, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitäts forderer, Trägerstoffe, Emulgiermittel, Dispergiermittel. Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fordern. Preferably, these are formulations or application forms, which auxiliary agents such as extenders, solvents, spontaneity, excipients, emulsifiers, dispersants. Antifreeze, biocides, thickeners and / or other adjuvants such as adjuvants included. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that require retention, spreading behavior, adherence to the leaf surface, or penetration.
Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktiven Stoffen. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungs formen (wie z. B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for shaping the formulation of the compounds of the formula (I) or the formulations prepared from these formulations (such as, for example, ready-to-use pesticides, such as spray liquors or seed dressing), such as certain physical, technical and / or to confer biological properties.
Als Streckmittel eignen sich z. B. Wasser, polare und unpolare organische chemische Flüssigkeiten z. B. aus den Klassen der aromatischen und nicht-aromati sehen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). Suitable extenders z. As water, polar and nonpolar organic chemical liquids such. B. from the classes of aromatic and non-aromati see hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, Cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen in frage: Aromaten wie Xyloi, Tokio! oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohl enwas s er sto ff e wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, mineralische und pflanzliche Öle. Alkohole wie Butanol oder lykol sowie deren Et her und Ester, Ketone wie Aceton, Methylethylketon, Methyli sobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z. B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder chlorierte aliphatische Kohlenwasserstoffe wie z. B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z. B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z. B. Methanol, Ethanol, iso-Propanoi, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z. B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. In the case of using water as an extender z. As well as organic solvents can be used as an auxiliary solvent. As liquid solvents are essentially in question: aromatics such as Xyloi, Tokyo! or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg. As petroleum fractions, mineral and vegetable oils. Alcohols such as butanol or lycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere in frage: z. B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapuigit, Montmorillonit oder Diatomeen erde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Har/e. Wachse und/oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen in frage: z. B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan. Stickstoff und Kohlendioxid. Beispiele für Emulgier- und oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulfonsäure, Salze von Phenolsulfonsäure oder Naphthalmsulfonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Aikylphenole oder Arylphenole), Salze von Sulfobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Poiyolen und Derivate der Verbindungen enthaltend Sulfate, Sulfonate und Phosphate, z. B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Suifitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. In principle, all suitable carriers can be used. As carriers are in particular in question: z. As ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapuigite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, har / e. Waxes and / or solid fertilizers. Mixtures of such carriers can also be used. As carriers for granules are in question: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corncobs and tobacco stems. Also, liquefied gaseous diluents or solvents can be used. In particular, are such extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for. As aerosol propellants such as halogenated hydrocarbons and butane, propane. Nitrogen and carbon dioxide. Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with Fatty amines, with substituted phenols (preferably aikylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g. As alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin Suifitablaugen and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungs formen Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. As further auxiliaries in the formulations and the application derived therefrom dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
Weiterhin enthalten sein können Stabilisatoren wie Käitestabilisatoren, Konservierungsmittel, Oxidations s chutzmittel, Lichtschutzmittel oder andere die chemische und/oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. Stabilizers such as kite stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability may also be present. It may also contain foam-forming agents or defoamers.
Ferner können die Formulierungen und daraus abgeleiteten Anwendungs formen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und pflanzliche Öle sein. Furthermore, the formulations and derived therefrom application forms as additional auxiliaries and adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.
Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungs formen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsforderer, Stabilisatoren, Sequesti ermittel, Komplexbildner, Feuchthaltemittel, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, weicher für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamischeOptionally, further auxiliaries may be contained in the formulations and the application forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention agents, stabilizers, sequestering agents, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes. As retention promoters are all those substances considered that the dynamic
Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar-Polymere. Reduce surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Be- tracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Beweglichkeit der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51 , 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Soj aölmethylester, F ettaminalkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or Soy aölmethylester, F ettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate. The formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungs formen (insbesondere S chädlings b ekämp fungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungs formen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (1), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungs form, liegen. Die Anwendung geschieht in einer den Anwendungs formen angepaßten üblichen Weise. Mischlingen The content of the compound of the formula (I) in the application forms prepared from the formulations (in particular chelating agents) may vary within wide ranges. The concentration of the compound of the formula (I) in the application forms can usually be between 0.00000001 and 95 wt .-% of the compound of formula (1), preferably between 0.00001 and 1 wt .-%, based on the weight of Application form, lie. The application is done in a forms adapted to the application customary way. mongrels
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden. Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika. Nützlingen, Herbiziden, Düngemitteln, Vogelrepeilentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z. B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Des Weiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensaizgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteertrag steigern, die Reife beeinflussen, die Qualität und/oder der Emährungswert der Emteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. The compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides. Acaricides, molluscicides, nematicides, insecticides, microbiologicals. Useful insects, herbicides, fertilizers, Vogelrepeilentien, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators are used to such. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensaizgehalt. In addition, the flowering and fruit behavior can be improved, the germination and rooting can be optimized, the harvest can be improved and the harvest yield can be improved increase the quality and / or the nutritional value of the emmentary products, extend the shelf life and / or improve the workability of the harvested products.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen derFurthermore, the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of
Formel (I) zur Verbesserung der Pfianzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. Formula (I) to improve the Pfianzenigenschaften such as growth, yield and quality of the crop are used.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungs formen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. In a particular embodiment according to the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann, sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Sal/e bilden. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners may optionally form Sal / e with suitable bases or acids.
Insektizide/ Akarizide/Nematizide Insecticides / acaricides / nematicides
Die hier mit ihrem „Common Name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z. B. http://www.alanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen 1 R AC Mode of Action Classification Scheme. The active substances mentioned here by their "common name" are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual" 16th ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: //www.alanwood. net / pesticides). The classification is based on the 1 R AC Mode of Action Classification Scheme valid at the time of filing this patent application.
(1) Acetylcholinesterase(AChE)-Inhibitoren, wie beispielsweise Carbamate, z. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb. Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder Organophosphate, z. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinpho s , Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur. Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0-(methoxyaminothio-phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Mono cro tophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos. Sulfotep, Tebupirimfos. Temephos, Terbufos, Tetrachlorvinpho s , Thiometon, Triazophos, Triclorfon und Vamidothion. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb. Propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC and xylylcarb or organophosphates, e.g. Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chloroforms, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinone, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulphoton , EPN, Ethion, Ethoprophos, Famphur. Fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl-0- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mecarbam, methamidophos, methidathione, mevinphos, mono cro tophos, naled, omethoate, oxydemeton-methyl, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidone, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthione, quinalphos. Sulfotep, Tebupirimfos. Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon and Vamidothion.
(2) GABA-gesteuerte Chlorid-Kanal-Blocker, wie beispielsweise Cyclodien-organochlorine, z. B. Chlordan und Endosulfan oder Phenylpyrazole (Fiprole), z. B. Ethiprol und Fipronil. (3) Natrium-Kanal -Modulatoren, wie beispielsweise Pyrethroide, z. B. Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenotlirin [( 1 R)-trans-Isomer] , Deltamethrin, Empenthrin [(EZ)-(lR)-isomer], Esfenvalerat, Etofenprox, Fenpropathrin. Fenvalerat, Flucythrinat, Flumethrin. tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin. Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(lR)-Isomer], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (2) GABA-controlled chloride channel blockers, such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil. (3) sodium channel modulators, such as pyrethroids, e.g. A-crinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenotlirin [(1R) -trans isomer], deltamethrin, empenthrin [(EZ) (lR) isomer], esfenvalerate, etofenprox , Fenpropathrin. Fenvalerate, flucythrinate, flumethrin. tau-fluvalinate, Halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR) -trans-isomer], prallethrin. Pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(lR) isomer], tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Neonicotinoide, z. B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nicotin oder Sulfoxaflor oder Flupyradifurone. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) AUosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Spinosyne, z. B. Spinetoram und Spinosad. (5) AUotic nicotinic acetylcholine receptor (nAChR) modulators such as spinosyn, e.g. B. spinetoram and spinosad.
(6) AUosterische Modulatoren des Glutamat-abhängigen Chloridkanals(GluCl), wie beispielsweise Avermectine/Milbemycine, z. B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) AUosteric modulators of the glutamate-dependent chloride channel (GluCl), such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
(7) Juvenilhormon-Mimetika, wie beispielsweise Juvenilhormon- Analoge, z. B. Hydropren, Kinopren und Methopren oder Fenoxycarb oder Pyriproxyfen. (7) juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
(8) Verschiedene nicht spezifische (multi-site) Inhibitoren, wie beispielsweise Alkylhalogenide, z. B. Methylbromid und andere Alkylhalogenide; oder Chioropicrin oder Sulfuryl fluorid oder Borax oder Brechweinstein oder Methylisocyanaterzeuger, z. B. Diazomet und Metam. (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chioropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
(9) Modulatoren chordotonaler Organe, z. B. Pymetrozin oder Flonicamid. (9) modulators of chordotonic organs, e.g. As pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, wie z. B. Clofentezin, Hexythiazox und Diflovidazin oder Etoxazol. (10) mite growth inhibitors, such as. Clofentezine, hexythiazox and diflovidazine or etoxazole.
(11) Mikrobielle Disruptoren der Insektendarmmembran, wie z. B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und ü./. -Pflanzenproteine: Gry 1 Ab, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb. Cry34Abl/35Ab l . (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organo/inn Verbindungen, z. B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargit oder Tetradifon. (11) Microbial disruptors of insect intestinal membrane such. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and ü. /. Plant Proteins: Gry 1 Ab, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb. Cry34Abl / 35Ab l. (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors, such as diafenthiuron or organo-innine compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
(13) Entkoppler der oxidativen Phoshoryiierung durch Störung des Protonengradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by disruption of the proton gradient, such as chlorfenapyr, DNOC and sulfluramide.
(14) Blocker des nicotinischen Acetylcholinrezeptorkanals, wie beispielsweise Bensultap, Cartap- hydro chlorid, Thiocyclam und Thiosultap-Natrium. (14) Blockers of the nicotinic acetylcholine receptor channel, such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin.
(17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern), wie beispielsweise Cyromazin. (17) Skinning disruptor (especially in dipterans, i.e., two-winged), such as cyromazine.
(18) Ecdyson-Rezeptor-Agonisten, wie beispielsweise Chromafenozid, Halofenozid, Methoxyfenozid und Tebufenozid. (18) ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Oktopamin-Rezeptor-Agonisten, wie beispielsweise Amitraz. (19) octopamine receptor agonists, such as amitraz.
(20) Mitochondriale Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethymon oder Acequinocyl oder Fluacrypyrim. (20) Mitochondrial Complex III Electron Transport Inhibitors such as Hydramethymone or Acequinocyl or Fluacrypyrim.
(21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, wie beispielsweise METI-Akarizide, z. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenon(21) Mitochondrial Complex I Electron Transport Inhibitors, such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone
(Derris). (Derris).
(22) Blocker des spannungsabhängigen Natriumkanals, wie z. B. Indoxacarb oder Metaflumizone. (22) blocker of the voltage-dependent sodium channel, such. Indoxacarb or metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z. B. Spirodiclofen, Spiromesifen und Spirotetramat. (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
(24) Inhibitoren des mitochondrialen Komplex-IV-Elektronentransports, wie beispielsweise Phosphine, z. B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanide, Calciumcyanid, Kaliumcyanid und Natriumcyanid. (24) inhibitors of mitochondrial complex IV electron transport, such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
(25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, wie beispielsweise beta- Ketonitrilderivate, z. B. Cyenopv raten und Cyflumetofen und Carboxanilide, wie beispielsweise Pyflubumid. (28) Ryanodinrezeptor-Modulatoren, wie beispielsweise Diamide, z. B. Chlorantraniliprol, Cyantraniliprol und Flubendiamid, weitere Wirkstoffe wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximat, Bifenazat, Broflanilid, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclaniliprol, Cycloxaprid, Cyhalodiamid, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindoiizin, Fluensulfon, Flufenerim, Flufenoxystrobin, Fluflprol. Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafiuthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Teflutfarin, Lotilaner, Meperfiuthrin, Paichongding, Pyridalyi, Pyrifiuquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tioxazafen, Thiofiuoximat, Triflumezopyrim und lodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo), sowie folgende Verbindungen: 1- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfi (25) inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, e.g. B. Cyenopv rates and Cyflumetofen and carboxanilides, such as Pyflubumid. (28) ryanodine receptor modulators, such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, flometoquine, fluazaindoicin, fluensulfone, flufenerim, flufenoxystrobin, fluflprol. Fluhexafon, fluopyram, fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafiuthrin, Imidaclothiz, iprodione, kappa bifenthrin, kappa Teflutfarin, Lotilaner, Meperfiuthrin, Paichongding, Pyridalyi, Pyrifiuquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tioxazafen, Thiofiuoximat, Triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfi
(bekannt aus WO2006/043635) (CAS 885026-50-6), { 1 '-[(2E)-3 -(4-Chlorphenyl)prop-2-en- 1 -yl] -5- fluorspiro[indol-3,4'-piperidin]-l(2H)-yl}(2-chloφyridin-4-yl)lΉethanon (bekannt aus WO2003/106457) (CAS 637360-23-7), 2-Chlor-N-[2-{l -[(2E)-3-(4-chioi-phenyl)prop-2-en-l-yi]piperidin-4-yl}-4- (trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494) (CAS 872999-66-1), 3-(4-Chlor- 2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO 2010052161) (CAS 1225292-17-0), 3-(4-Chlor-2, 6-dimethylphenyl)-8-methoxy-2-oxo-l,8- diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS- 1440516-42-6), 4-(But-2- in-1 -yloxy)-6-(3,5-dimethylpiperidin-l -yl)-5-fluo^yrimidin (bekannt aus WO2004/099160) (CAS 792914-58-0), PF1364 (bekannt aus JP2010/018586) (CAS-Reg.No. 1204776-60-2), N-[(2E)-l-[(6- Chlorpyridin-3 -yl)methyl]pyridin-2( 1 H)-yliden] -2,2,2 -trifluoracetamid (bekannt aus WO2012/029672) (CAS 1363400-41-2), (3E)-3 -[ 1 -|<6-Chlor-3 -pyridyl)methyl] -2-pyridyliden]-l ,1,1 -trifluorpropan-2-υη (bekannt aus WO2013/144213) (CAS 1461743-15-6), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-l- methyi-3-(pentafluorethyi)-4-(trifluormethyl)-lH-pyrazoi-5-carboxamid (bekannt aus WO2010/051926) (CAS 1226889-14-0), 5-Brom-4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2- pyridyl)pyrazol-3 -carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5- Dichloφhenyi)-4,5-dihydro-5-(triίluormethyl)-3-isoxazolyl]-2-methyl- -(cis-l-oxido-3- thietanyl)benzamid, 4-[5-(3,5-Dichioφhenyl)-4,5-dihydro-5-(trifίuormethyl)-3-isoxazoiyl]-2-methyl-N- (trans-1 -oxido-3 -thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichloφhenyi)-4,5-dihydro-5-(trifίuormethyl)- 3 -isoxazolyl] -2-methyl-N-(cis- 1 -oxido-3 -thietanyl)benzamid (bekannt aus WO 2013/050317 AI) (CAS 1332628-83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluoφropyl)suίfinyl]propanamid, (+)-N-[3 -Chlor- 1 -(3 -pyridinyl)- 1 H-pyra/ol-4-ylJ -N-ethyl-3 -[(3 ,3,3 - trifluoφropyl)sulfinyl]propanamid und (-)-N-[3 -Chlor- 1 -(3 -pyridinyl)- 1 H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoφropyl)sulfmyl]propanamid (bekannt aus WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 AI) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l-yl]amino]-l-[2,6-dichlor-4- (trifluormethyl)phenyl]-4-[(trifluormem^ (bekannt aus CN 101337937 A) (CAS 1 105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6-(known from WO2006 / 043635) (CAS 885026-50-6), {1 '- [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -5-fluorospiro [indole-3 , 4'-piperidin] -1 (2H) -yl} (2-chloropyridin-4-yl) -ethanone (known from WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N- [2- { l - [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] piperidin-4-yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2-oxo-1,1,8-diazaspiro [4.5] dec-3-en-4-yl ethyl carbonate (known from EP 2647626) (CAS 1440516-42-6), 4- (but-2-yn-1-ylxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoro ^ yrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS Reg. No. 1204776-60-2), N - [(2E) -l - [( 6-chloropyridin-3-yl) methyl] pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3E) -3 - [1 - | <6-chloro-3 - pyridyl) methyl] -2-pyridylidene] -1,1-trifluoropropane-2-υη (known from WO2013 / 144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6- (methylcarbamoyl) phenyl] -2- (3-chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [ 5- (3,5-Dichloro-phenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl- (cis-1-oxido-3-thietanyl) -benzamide, 4- [5- (3,5-Dichio-phenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (trans-1-oxido-3-thietanyl) -benzamide and 4 - [(5S) -5- (3,5-Dichloro-phenyl) -4,5-dihydro-5- (trifluoromethyl) -3 -isoxazolyl] -2-methyl-N- (cis-1-oxy-3-thietanyl) -benzamide (known from WO 2013/050317 AI) (CAS 1332628-83-7), N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3, 3-trifluoropropyl) suίfinyl] propanamide, (+) - N- [3-chloro-1 - (3-pyridinyl) -1 H -pyra-ol-4-ylJ-N ethyl 3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide and (-) - N- [3-chloro-1 - (3-pyridinyl) -1-H-pyrazol-4-yl] -N- ethyl 3 - [(3,3,3-trifluoropropyl) sulfmyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5- [(2E) -3-chloro-2-propen-1-yl] amino] -1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethylene) (known from CN 101337937 A) (CAS 1 105672-77-2), 3-bromo-N- [4-chloro-2-methyl-6-
[(methylamino)thioxomethyl]phen [(Methylamino) thioxomethyl] phen
(Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(l ,l - dimethylethyl)amino]carbonyl]-6-methylphenyl]-l -(3-chlor-2-pyridinyl)-3-(fl^  (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(1, 1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fl ^
5-carboxamid (bekannt aus WO 2012/034403 AI) (CAS 1268277-22-0), N-[2-(5-Amino-l ,3,4- thiadiazol-2-yl)-4-chlor-6-methylphenyl] -3 -brom- 1 -(3 -chlor-2-pyridinyl)- 1 H-pyrazol -5-carboxamid (bekannt aus WO 2011/085575 AI) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-l - yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus N 101337940 A) (CAS 1 108184-52-6); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l -[3-(trifluormethyl)phenyl]ethyiiden]-N-[4- (difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9); Cyclopropancarbonsäure-3 -(2,2-dichlorethenyl)-2,2-dimethyl-4-( 1 H-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-Chlor-2,5-dihydro-2- [ [(methoxycarbonyl)[4-[(trifluormethyi)thio]phenyl]amino] carbonyl]indeno[ 1 ,2-e] [ 1 ,3 ,4]oxadiazin- 4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-0- ethyl-2,4-di-0-methyi-l -[N-[4-[l -[4-(l , 1,2,2,2^ 5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N- [2- (5-amino-1, 3,4-thiadiazol-2-yl) -4-chloro-6 methylphenyl] -3-bromo-1 - (3-chloro-2-pyridinyl) -1 H -pyrazole-5-carboxamide (known from WO 2011/085575 Al) (CAS 1233882-22-8), 4- [3- [2,6-dichloro-4 - [(3,3-dichloro-2-propen-1-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from N 101337940 A) ( CAS 1 108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4- (difluoromethoxy) phenyl] hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3 - (2,2-dichloroethenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester (known from CN 103524422A) (CAS 1542271-46-4); (4aS) -7-chloro-2,5-dihydro-2- [[(methoxycarbonyl) [4 - [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1,2-e] [1,3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1 - [N- [4- [1 - [4- (1, 1, 2, 2, 2, ^
yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014/0275503 AI) (CAS 1 181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3 -(6-trifluormethylpyridazin-3 -yl)-3 - azabicyclo[3.2.1]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4- trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yi)-3-azabicyclo[3.2.1 Joctan (CAS 933798-27- 7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylp yl] phenyl] carbamate] -a-L-mannopyranose (known from US 2014/0275503 Al) (CAS 1 181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-anti) -8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1 Joctane (CAS 933798-27-7), (8-syn) -8- (2- cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluormethylp
azabicyclo[3.2.1 Joctan (bekannt aus WO 2007040280 AI , WO 2007040282 AI) (CAS 934001-66-8) und -[3-Chίor-l -(3-p>τidinyl)-lH-pyrazoί-4-yί]- -ethyl-3-[(3,3,3-trifluoφropyl)thio]-propanamid (bekannt aus WO 2015/058021 AI , WO 2015/058028 AI) (CAS 1477919-27-9). azabicyclo [3.2.1] joctane (known from WO 2007040280 A1, WO 2007040282 Al) (CAS 934001-66-8) and - [3-chloro-l - (3-p> τidinyl) -lH-pyrazo-4-yl] - ethyl-3 - [(3,3,3-trifluoropropyl) thio] -propanamide (known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9).
Fungizide Die hier mit ihrem "Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im "Pesticide Manual" (16. Aufl. British Crop Protection Council) oder im Internet recherchierbar (beispielsweise: http://www.alanwood.net/pesticides) beschrieben. Fungicides The active ingredients specified here by their "common name" are known and described, for example, in the "Pesticide Manual" (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) ,
Alle genannten Mischungspartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Alle genannten fiingiziden Mischungspartner der Klassen (1) bis (15) können gegebenenfalls tautomere Formen einschließen. All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids. All of the above fictitious compounding partners of classes (1) to (15) may optionally include tautomeric forms.
1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin. (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.01 1) Imazalii Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochioraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazol, ( 1.026) ( 1 R.2S.5 S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(1H-1 ,2,4-triazoi- 1 - ylmethyl)cyclopentanol, (1.027) (lS,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH-l,2,4- triazol-1 -ylmethyl)cyclopentanol, (1.028) (2R)-2-(l-Chlorcyclopropyl)-4-[(lR)-2,2-dichlorcyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol (1.029) (2R)-2-(l-Chlorcyclopropyl)-4-[(lS)-2,2- dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.030) (2R)-2-[4-(4-Chlorphenoxy)-2- (trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2 -ol, (1.031) (2 S)-2-( 1 -Chlorcyciopropyi)-4- [( 1 R)-2,2-dichlorcyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.032) (2S)-2-( 1 -Chlorcyclopropyl)- 4-[(lS)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.033) (2S)-2-[4-(4- Ch^henoxy)-2-(trifluonriethyl)phenyi] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.034) (R)-[3 -(4-Chlor-1) inhibitors of ergosterol biosynthesis, for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin. (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.01 1) imazalii sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) Paclobutrazole, (1,016) prochioraz, (1,017) propiconazole, (1,018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) Tebuconazole, (1,022) Tetraconazole, (1,023) Triadimenol, (1,024) Tridemorph, (1,025) Triticonazole, (1,026) (1 R.2S.5 S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2 -methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.027) (1S, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl -l- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1 - (1H-1,2,4-triazol-1-yl) butan-2-ol (1.029) (2R) -2- (1-chlorocyclopropyl) -4 - [(1S) -2,2-dichlorocyclopropyl] - 1 - (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.031) (2S) -2- (1-chlorocyclopropyl) -4- [(1R) -2 , 2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.032) (2S) -2- (1-chlorocyclopropyl) -4 - [(lS ) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.033) (2S) -2- [4- (4-chloro-oxy ) -2- (trifluoronethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1. 034) (R) - [3 - (4-chloro
2- fluorplieny! )-5-( 2.4-ditluorplieny! )-] ,2-oxazol-4-yl] (pyridin-3 -yl)methanol, (1.035) (S)-[3-(4-Chior-2- fluoiphenyi)-5-(2,4-difluoiphenyi)-l,2-oxazoi-4-yl](pyridin-3-yl)methanoi, (1.036) [3-(4-Chior-2- fluol henyl)-5-(2,4-difluoφheny!)-l,2-oxazol-4-yl](pyridin-3-yl)methanoi, (1.037) l-({(2R,4S)-2-[2- Chlor-4-(4-chlo^henoxy)phenyl]-4-methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4^ (1.038) 1- ( {(2S,4S)-2-[2-Chlor-4-(4-chlo henoxy)phenyl]-4-methyl-l ,3-dioxolan-2-yl}methyl)-lH-l ,2,4-triazol, (1.039) l-{[3-(2-Chlo henyi)-2-(2,4-difluoφhenyl)oxiran-2-yϊ]methyl}-lH-l,2,4-triazoi-5-yi- thiocyanat, (1.040) l -{[rel(2R,3R)-3-(2-Chίoφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yi]methyϊ}-lH- 1 ,2,4-triazol-5-yl-thiocyanat, (1.041) l-{[rei(2R,3S)-3-(2-Chioφhenyl)-2-(2,4-difluoφhenyi)oxiran-2- yl]methyl } -1 H- 1 ,2,4-triazol-5 -yl-thiocyanat, (1.042) 2-[( 2R.4R.5 R)- 1 -( 2.4-Dichlorplienyl )-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-l-(2,4- Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yί]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.044) 2- [(2R,4S,5R)-l-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihy^ 2- fluorplieny! ) -5- (2,4-ditluorophenyl!) -], 2-oxazol-4-yl] (pyridin-3-yl) -methanol, (1035) (S) - [3- (4-chloro-2-fluoiphenyi) - 5- (2,4-difluo-phenylene) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanoi, (1.036) [3- (4-chloro-2-fluoro-5-yl) -5- (2 , 4-difluorophenyl!) - 1, 2-oxazol-4-yl] (pyridin-3-yl) -methanoi, (1.037) 1 - ({(2R, 4S) -2- [2-chloro-4- (4 -chloro) -henoxy) -phenyl] -4-methyl-1,3-dioxolan-2-yl} -methyl) -LH-1, 2,4 ^ (1038) 1- ({(2S, 4S) -2- [2 Chloro-4- (4-chloro-oxy) -phenyl] -4-methyl-1,3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole, (1039) 1 - {[3 (2-chloro-ethyl) -2- (2,4-difluoro-phenyl) -oxiran-2-yl] -methyl} -LH-l, 2,4-triazol-5-yi-thiocyanate, (1040) 1 - {[rel ( 2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -H-1,2,4-triazol-5-yl-thiocyanate, (1.041) l - {[ri (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole-5 - yl thiocyanate, (1.042) 2 - [(2R.4R.5R) -1- (2,4-dichloropienyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro- 3H-l, 2,4-triazole-3-thione, (1.043) 2 - [(2R, 4R, 5S) -l- (2,4-dichloro henyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.044) 2- [(2R, 4S , 5R) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4-dihydroergotamine ^
triazol-3-thion, (1.045) 2-[(2R,4S,5S)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l ,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-l -(2,4-Dich^henyl)-5-hydroxy-2,6,6- trimethyiheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-l-(2,4-triazole-3-thione, (1.045) 2 - [(2R, 4S, 5S) -1- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2 , 4-dihydro-3H-1, 2,4-triazole-3-thione, (1.046) 2 - [(2S, 4R, 5R) -1- (2,4-dichloro) -5-hydroxy-2 , 6,6-trimethyiheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1047) 2 - [(2S, 4R, 5S) -l- (2 , 4-
Oichlonihenyl )-5-hydroxy- (1.048) 2-Oichloronihenyl) -5-hydroxy- (1048) 2-
[(2S,4S,5R)-l-(2,4-Dich^henyi)-5-hyi xy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2^ [(2S, 4S, 5R) -1- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2 ^
3- thion, (1.049) 2-[(2S,4S,5S)-l -(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l ,2,4-triazol-3-thion, (1.050) 2-[l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethyiheptan-4- yl] -2,4-dihydro-3H- 1 ,2,4-triazoi-3 -thion, (1.051) 2-[2-Chlor-4-(2,4-dichlorophenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.052) 2-[2- '!ilor-4-(4-chlorphenoxy)phenyl |-l -( 1 H- 1 ,2,4-triazol- 1 - yi)butan-2-oi, (1.053) 2-[4-(4-Ch^henoxy)-2-(trifluonne^ 3-thione, (1.049) 2 - [(2S, 4S, 5S) -1- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4 dihydro-3H-l, 2,4-triazole-3-thione, (1,050) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyiheptan-4-yl] - 2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.051) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1 - (1H-1, 2,4-triazol-1-yl) propan-2-ol, (1.052) 2- [2- ' ] - ilor-4- (4-chlorophenoxy) phenyl | - - (1H-1, 2,4- triazole-1-yl) butan-2-oi, (1.053) 2- [4- (4-chloro-phenoxy) -2- (trifluonne)
2-ol, (1.054) 2-[4-(4-Ch^henoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l -yl)pentan-2-ol, (1.055) 2-[4-(4-Ch^henoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)pro^ (1.056) 2- | [3-( 2-€1ι1θφ1ιοηνΙ )-2-( 2.4Ηΐ!ί1ικ)φ!ιοην1 )οχίΓΗη-2-ν1]ηιο!ΐινΐ ; -2,4-diliy  2-ol, (1.054) 2- [4- (4-Chhenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-l, 2,4-triazol-1-yl) pentan-2-ol , (1.055) 2- [4- (4-Chhenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1, 2,4-triazol-1-yl) pro (1.056) 2- | [3- (2- € 1ι1θφ1ιοηνΙ) -2- (2.4Ηΐ! Ί1ικ) φ! Ιοην1) οχίΓΗη-2-ν1] ηιο! Ϊ́ινΐ; -2,4-diliy
( 1.057) 2- { [rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H- l,2,4-triazol-3 -thion, (1.058) 2-{[rel(2R,3S)-3-(2-Chlorphenyi)-2-(2,4-difluoφhenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.059) 5-(4-Chiorbenzyl)-2-(chlormethyi)-2-methyi- 1 -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (1.060) 5-(Allylsulfanyl)-l -{[3-(2-chlorphenyl)-2-(2,4- difluoφhenyl)oxiran-2-yl]methyl } - 1 H- 1 ,2,4-triazol, (1.061) 5-(Allylsulfanyl)-l - {[rel(2R,3R)-3-(2- chlorphenyl)-2-(2,4-difluorphenyi)oxiran-2-yl]methyl}-lH-l ,2,4-triazol, (1.062) 5-(Allylsulfanyl)-l - { [rel(2R,3 S)-3 -(2-chlo henyl)-2-(2,4-difluo henyl)oxiΓan-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (1.063) N'- (2,5-Dimethyl-4-{[3-(l ,l ,2,2-tetrafluorethoxy)pheriyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)- N-ethyl-N-methylimidoformamid, (1.065) N'-( 2,5-Dimethyl-4- ! [3-( 2,2,3.3- tetrafluo^ropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformam^ (1.066) N'-(2,5-Dimethyl- 4-{[3-(pentafluorethoxy)phenyi]sulfanyi}phenyl)-N-ethyl-N-methyiimidoform (1.067) N'-(2,5- Dimethyl-4-{3-[(l ,l,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyH (1.057) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.058) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} - 2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl- 1 - (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.060) 5- (allylsulfanyl) -1 - [[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole, (1061) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.062) 5- (allylsulfanyl) -1 - {[rel (2R, 3S) -3 - ( 2-chloro-1-yl) -2- (2,4-difluorohexyl) -oxi-2-yl] -methyl} -1 H-1,2,4-triazole, (1063) N '- (2,5-dimethyl-4 - {[3- (l, l, 2,2-tetrafluoroethoxy) pheriyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.064) N '- (2,5-dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) - N-ethyl-N-methylimidoformamide, (1.065) N '- (2,5-dimethyl-4-! [3- (2,2,3,3- tetrafluoroproxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformam ^ (1.066) N '- (2,5-dimethyl-4 - {[3- (pentafluoroethoxy) phenylsulfinyl} phenyl) -N- ethyl N-methylimidoform (1.067) N '- (2,5-dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methyl
( 1.068) N'-(2,5-Dimethyl-4- {3 -[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamid, (1.069) N'-( 2,5- Dimethyl -4- ) 3-[( 2,2,3.3- te1xafluo^ropyi)suifanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformam ( 1.070) N'-(2,5-Dimethyl- 4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformam (1.071) N'-(2,5- Dimethyl-4-phenoxyphenyl)-N-ethyl- -methylimidoformamid, (1.072) N'-(4-{[3- (1.068) N '- (2,5-Dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.069) N' - ( 2,5-dimethyl-4-) 3 - [(2,2,3,3-te1-oxafluoropyropyl) suifanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformam (1.070) N '- (2,5-dimethyl- 4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformam (1.071) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-methylimidoformamide, (1.072 ) N '- (4 - {[3
(Difiuormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'- (4-{3-[(Difiuormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.074) N'-[5-Brom-6-(2 -dihydro-lH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N- methylimidoformamid, (1.075) N'- {4-[(4,5-Di chlor- 1 ,3 -thiazol-2-yl)oxy] -2,5-dimethylphenyl } -N-ethyl- N -methylimidoformamid, (1.076) N'-{5-Brom-6-[(lR)-l -(3,5-difiuorophenyl)ethoxy]-2-methylpyridin- 3-yl}-N-ethyl-N-methylimidoformamid, (1.077) N'-{5-Brom-6-[(l S)-l -(3,5-difluo henyl)ethoxy]-2- methylpyridin-3 -yl } -N-ethyl-N-methylimidoformamid, (1.078) N'-{5-Brom-6-[(cis-4- isopropylcyclohexyl)oxy] -2-methylpyridin-3 -yl } -N-ethyl- -methylimidoformamid, (1.079) N'-{5- Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridm-3-yl} -N-ethyl-N-methylimidoformamid, (1.080) N'-{5-Bromo-6-[l -(3,5-difluoφhenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamid. (Difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1073) N '- (4- {3 - [(Difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) N-ethyl-N-methylimidoformamide, (1.074) N '- [5-bromo-6- (2-dihydro-1H-inden-2-yloxy) -2-methyl-pyridin-3-yl] -N-ethyl-N - methylimidoformamide, (1.075) N '- {4 - [(4,5-dichloro-1, 3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, 1.076) N '- {5-bromo-6 - [(1R) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.077) N '- {5-bromo-6 - [(1S) -1- (3,5-difluorohexyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.078) N' - {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-methylimidoformamide, (1.079) N '- {5-bromo-6 - [( trans-4-isopropylcyclohexyl) oxy] -2-methylpyridm-3-yl} -N-ethyl-N-methylimidoformamide, (1080) N '- {5-bromo-6- [1- (3,5-difluoro-phenyl) -ethoxy ] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide.
2) Inhibitoren der Atmungskette am Komplex I oder I ! beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.01 1) Isopyrazam (anti-epimeres Enantiomer 1 S.4R.9R), (2.012) Isopyrazam (anti- epimeres Racemat 1 RS.4SR.9SR ). (2.013) Isopyrazam (Mischung des syn-epimeren Razemates 1 RS.4SR.9RS und des anti-epimeren Razemates I RS.4SR.9SR ), (2.014) Isopyrazam (syn-epimeres Enantiomer 1 R.4S.9R), (2.015) Isopyrazam (syn-epimeres Enantiomer 1 S,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat I RS.4SR.9RS ). (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) P>Tazifiumid, (2.021) Sedaxane, (2.022) l ,3-Dimethyl-N-(l,l ,3-trimethyl-2,3- dihyilro- ! H-inilen-4-yl )- ! H-pyrazol-4-carboxamid. (2.023) 1 ,3 -Dimethyl-N-[(3R)-1 , 1 ,3 -trimethyl-2,3 - i!ihydro- 1 H-inden-4-yl ]- 1 H-pyrazol-4-carboxamiil, (2.024) 1 ,3-Dimethyl-N-[(3 S)-l , 1 ,3 -trimethyl-2,3 - dihydi -lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.025) 1 -Methyl-3 -(trifluormethyl)-N-[2'- (trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.026) 2-Fluor-6-(trifluoromethyl)-N-( 1,1,3- trimethyl -2 , 3 -dihydro - 1 H -inden-4 -yl)b enzamid, (2.027) 3 -(Di fluormethyl) - 1 -methyl -N-( 1,1,3 -trimethyl - 2,3-dihydro-lH-inden-4-yi)-lH-pyrazol-4-carboxamid, (2.028) 3 -(Difluormethyl)- 1 -methyl-N- [(3 R)- 1,1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.029) 3-( Di luormethyl )- 1 - methyl -N-[(3 S)-l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] -1 H-pyrazol-4-carboxamid, (2.030) 3- (Difluormethyl)-N-(7-fluor- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)-l -methyl- 1 H-pyrazol-4- carboxamid, (2.031) 3-(Difluormethyl)-N-[(3R)-7-fluor-l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 - methyl- lH-pyrazol-4-carboxamid, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluor-l,l,3-trimethyl-2,3- dihydi -lH-inden-4-yi]-l-methyi-l H-pyi-azol-4-carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4-{[4- (trifluormethyi)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5- fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.035) N- (2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyi)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl- 1H- pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l- methyl-lH-pyrazoi-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyi)-N-cyciopropyi-3- (difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazol -4 -carboxamid, (2.039) N-[(lR,4S)-9-(Dichlormethylen 1 ,2,3,4-tetrahydro-l ,4-methanonaphthalen-5-yl]-3 -(difluormethyl)-l -methyl-lH-pyrazol-4 -carboxamid, (2.040) N-[(lS,4R)-9-(Dichiormethyien)-l,2,3,4-tetrahydi -l,4-methanonaphthalen-5-yl]-3- (difluormethyl)-l-methyl-lH-pyrazol-4 -carboxamid, (2.041) -[l-(2,4-Dichloφhenyl)-l- methoxypropan-2-yl] -3 -(difluormethyl)- 1 -methyl- 1 H-pyrazol-4 -carboxamid, (2.042) N-[2-Chlor-6- (trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carbo (2.043) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyi)-5-fluor-l- methyl- lH-pyrazol-4-carboxamid, (2.044) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3- (difluormethyl)-5 -fluor- 1 -methyi-lH-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3 -(difluormethyl)- 5-fluor-l-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-l H-pyrazol -4-carboxamid, (2.046) N- Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l -methyl- 1 H-pyrazol -4- carboxamid, (2.047) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-l- methyl- 1 H-pyrazol -4-carboxamiil. (2.048) N-Cyclopropyl-3 -(difluormethyl)-5 -fluor-N-(2- isopropylbenzyl)-l -methyl- lH-pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3 -(difluoromethyl)-5 - fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3 - (difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.051) N- Cyciopropyi-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyi)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (2.052) N-Cyclopropyl-3-(difluomiethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl-lH- pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l- methyl-lH-pyrazole-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazole-4-carboxamid, (2.055) -Cyclopropyl -N-( 2 -cyclopropyl- 5 -methylbenzyl)-3 -(difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazole-4-carboxamid, (2.056) N- Cyclopropyl-N-(2-cyclopropylbenzyl)-3 -(difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazole-4-carboxamid. 2) respiratory chain inhibitors on complex I or I! for example, (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.01 1) isopyrazam (anti-epimeric enantiomer 1 S.4R.9R), (2.012) isopyrazam (anti-epimeric racemate 1 RS.4SR.9SR). (2.013) Isopyrazam (mixture of syn-epimeric racemate 1 RS.4SR.9RS and anti-epimeric racemate I RS.4SR.9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1 R.4S.9R), (2.015 ) Isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.016) isopyrazam (syn-epimeric racemate I RS.4SR.9RS). (2.017) pentanes, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) P> tazifiumid, (2.021) sedaxanes, (2.022) l, 3-dimethyl-N- (l, l, 3-trimethyl-2,3 - dihyilro-! H-inilen-4-yl) -! H-pyrazole-4-carboxamide. (2.023) 1, 3-Dimethyl-N - [(3R) -1, 1, 3-trimethyl-2,3-i-ihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide , (2.024) 1, 3-dimethyl-N - [(3 S) -l, 1, 3-trimethyl-2,3 - dihydi-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3 - (trifluoromethyl) -N- [2'- (trifluoromethyl) -biphenyl-2-yl] -lH- pyrazole-4-carboxamide, (2.026) 2-fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H -inden-4-yl) -benzamide, (2.027 ) 3 - (Di-fluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.028) 3 (Difluoromethyl) -1-methyl-N- [(3R) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.029) 3- (Diluomethyl) -1-methyl-N - [(3 S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole 4-carboxamide, (2.030) 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -l-methyl-1 H-pyrazole-4-carboxamide, (2.031) 3- (difluoromethyl) -N - [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ] - 1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3- (difluoromethyl) -N - [(3S) -7-fluoro-1,1,3,3-trimethyl-2,3-dihydi-1H- inden-4-yl] -l-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-Difluoro-N- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.034) N (2-Cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N- (2-tert-butyl) 5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1 - methyl-1H-pyrazole-4-carboxamide, (2.038) N- (5-chloro-2-isopropylbenzyl) -N-cyciopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole -4 carboxamide, (2.039) N - [(IR, 4S) -9- (dichloromethylene-1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -l-methyl- lH-pyrazole-4-carboxamide, (2.040) N - [(IS, 4R) -9- (dichloromethyl) -1,3,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- ( difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.041) - [1- (2,4-dichloro-phenyl) -l-meth oxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.042) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3 (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carbo (2.043) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1 -methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1 H- pyrazole -4-carboxamide, (2.046) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (2.047 ) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide. (2.048) N-Cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3 - (difluoromethyl) - 5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (5-fluoro-2-) isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl -LH-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-Cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) -cyclopropyl-N- (2-cyclopropyl) 5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5 fluoro-1-methyl-1H-pyrazole-4-carboxamide.
3) Inhibitoren der Atmungskette am Komplex I I I . beispielsweise (3.001) Ametoctradin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.01 1) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyi, (3.014) Metomino s trobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[( {[(lE)-l -(3-{[(E)-l -Fluor-2- phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.022) (2E,3Z)-5-{[l -(4-Ch^henyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3- enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyi-3-[( {3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl }carbonyl)amino]-6- methyl-4,9-dioxo-l ,5-dioxonan-7-yi-2-methylpropanoat, (3.026) 2- {2-[(2,5- Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.027) N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{[l -(4-Chlor-2-fluorphenyl)- 1 H-pyra/ol -3 -yljoxy} -2-(methoxyimino)-N,3 -dimethylpent-3 -enamid. 3) inhibitors of the respiratory chain on the complex I I I. for example, (3.001) ametoctradine, (3.002) amisulbromo, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamide, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone , (3.01) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyi, (3.014) Metomino s trobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin , (3.020) Trifloxystrobin (3.021) (2E) -2- {2 - [({[(IE) -l- (3 - {[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5 - {[1- (4-chloro-1-yl-1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N- methylacetamide, (3.024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.025) (3S, 6S, 7R, 8R) -8- Benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-meth yl 4,9-dioxo-l, 5-dioxonan-7-yl-2-methylpropanoate, (3.026) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide , (3.027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3.028) (2E, 3Z) -5 - {[1- (4-chloro-2- fluorophenyl) -1 H -pyra-ol-3-yloxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide.
4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, , (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5- phenylpyridazin, (4.010) 3-Chlor-5-(4-chiorphenyl)-4-(2,6-difluorphenyl)-6-methyipyridazin, (4.01 1) 3- Chlor-5 -(6-chlorpyridin-3 -yl)-6-methyl-4-(2,4,6-trifluo henyl)pyridazin, (4.012) 4-(2-Brom-4- fluorphenyl)- -(2,6-difluoφhenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (4.013) 4-(2-Brom-4- fluorphenyί)-N-(2-brom-6-fluoφhenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.014) 4-(2-Brom-4- iluorphenyl )-N-( 2-broniphenyl )- l ,3-iliinethyl- l H-pyrazol-5-amin. (4.015) 4 -( 2 - B r m -4 - fl uo rp h en y 1 ) -N - ( 2- h!or-6-fluorphenyl )- 1 ,3-dimethyl- 1 H-pyrazo!-5-amin. (4.016) 4 -< 2 - B ro m -4 - fl IH > rp h e n y I ) - N -< 2 - cli lorplieny 1 )- 1 ,3 -di met hy I - 1 H -pyra/o! -5 -ami n. (4.017) 4-( 2-Brom-4-tluorphenyl )-N-( 2-tluorplienyl )- ! .3-dimeihyl- l H-pyrazol-5-ami n. (4.018) 4-( 2-Chlor-4-fluorpiieny! )-N-( 2.6-di tluorplienyl )- 1 .3- ilimethyl- 1 H-pyra/ol-5-airiin. (4.019) 4-( 2- 'iilor-4-fliiorp!ienyl )- -( 2-chlor-6-fliiorphenyl )- ! .3- dimethyl- 1 H-pyra/ol-5-ami n. (4.020) 4-(2-Chlor-4-fluoφhenyl)-N-(2-chloφhenyl)-l ,3-dimethyl-lH- pyrazol-5-amin, (4.021) 4-( 2-C'h!or-4-fhiorplienyl )- -( 2-fluorplienyl )- ] ,3-dimethyl- l H-pyrazol-5-aiTiin, (4.022) 4-(4-Chlorplienyl )-5-( 2/i-ili fliK)rplieny! )-3.6-dinie!hy]pyrida/in. (4.023) N-(2-Brom-6- fluorphenyl )-4-( 2-clilor-4-tluorphenyl )- 1 .3-dimethyl- ! i l-pyra/ol-5-amin. (4.024) N-( 2-Bromphenyl )-4- ( 2-chlor-4-fluorplienyl )- 1 .3-di methyl - 1 H -pyra/oi -5 -ami n. (4.025) -( 4- hlor-2.6-ili tluorphenyl )-4-( 2- ehlor-4 -fluoφhenyl) -1 ,3 -dimethyl- 1 H-pyra/ol-5 -amin . 5) Verbindungen mit Befähigung zu Multisite-Aktivität, beispielsweise (5.001) Bordeauxmischung,4) inhibitors of mitosis and cell division, for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl ) -6-methylpyridazine, (4.01 l) 3-chloro-5 - (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluoro-henyl) pyridazine, (4.012) 4- ( 2-bromo-4-fluorophenyl) - - (2,6-difluoro-phenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- ( 2-bromo-6-fluoro-phenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-phenyl) -l, 3 iliine-ethyl-1H-pyrazole-5-amine. (4.015) 4 - (2 - B rm -4 - fl uo rp h en y 1) -N - (2-halo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole! -5- amine. (4.016) 4 - <2 - B ro m -4 - fl IH> rp heny I) - N - <2 - cli lorplieny 1) - 1, 3 - di met hy I - 1 H -pyra / o! -5-n.m. (4.017) 4- (2-bromo-4-tluorophenyl) -N- (2-tluoropienyl) -! 3-Dimethyl-1H-pyrazole-5-amine (4.018) 4- (2-Chloro-4-fluorophenyl) -N- (2,6-di-fluoropienyl) -1,3-dimethyl-1H-pyra / ol-5-airiin. (4.019) 4- (2- ' iilor-4-fluorophenyl) - - (2-chloro-6-fluorophenyl) -! 3-dimethyl-1H-pyra-ol-5-amine (4.020) 4- (2-chloro-4-fluoro-phenyl) -N- (2-chloro-phenyl) -l, 3-dimethyl-1H-pyrazole 5-amine, (4.021) of 4- (2-h C 'or-4-fhiorplienyl!) - - (2-fluorplienyl) -], 3-dimethyl-l H-pyrazol-5-aiTiin, (4022) 4- (4-chloropienyl) -5- (2 / i-ili fliK) rplieny! ) -3.6-Dinie! Hy] pyrida / in. (4.023) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-tluorophenyl) -1,3-dimethyl-! i l-pyra / ol-5-amine. (4.024) N- (2-Bromo-phenyl) -4- (2-chloro-4-fluoro-plienyl) -1,3-di-methyl-1H-pyra-o-5-di-naphtha (4,025) - (4-chloro -2.6 -iliotluorophenyl) -4- (2-chloro-4-fluoro-phenyl) -1,3-dimethyl-1H-pyra-ol-5-amine. 5) Compounds capable of multisite activity, for example (5.001) Bordeaux mixture,
(5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006) Kupfernaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinkmetiram, (5.017) Kupfer-Oxin, (5.018) Propineb, (5.019) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2 +) - sulfate, (5.010) dithianon , (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zincmetiram, (5.017) Copper-Oxine, (5.018) Propineb, (5.019) Sulfur and sulfur compounds including Calcium polysulfide, (5,020) thiram, (5,021) zineb, (5,022) ziram.
6) Verbindungen, die zum Auslösen einer Wirtsabwehr befähigt sind, beispielsweise (6.001) Acibenzolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. 6) Compounds capable of inducing host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
7) Inhibitoren der Aminosäure- und/oder Protein-Biosynthese, beispielsweise (7.001) Cyprodinil, (7.002) Kasugamycin, (7.003) Kasugamycinhydrochlorid-hydrat, (7.004) Oxytetracyclin (7.005)7) Inhibitors of amino acid and / or protein biosynthesis, for example, (7,001) cyprodinil, (7,002) kasugamycin, (7,003) kasugamycin hydrochloride hydrate, (7,004) oxytetracycline (7,005)
Pyrimethanil, (7.006) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolin. Pyrimethanil, (7.006) 3- (5-Fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
(8) Inhibitoren der ATP-Produktion, beispielsweise (8.001) Silthiofam. (8) Inhibitors of ATP production, for example, (8,001) silthiofam.
9) Inhibitoren der Zellwandsynthese, beispielsweise (9.001) Benthiavalicarb, (9.002) Dimethomorph,9) inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
(9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph. (9.007) Valifenalat, (9.008) ( 2E)-3-(4-tert-Buty!phenyl )-3-( 2-ch!orpyridin-4-yl )-! -( morpholin-4-yl )prop-2-en- 1 - on, (9.009) (2Z)-3-(4-tert-Butylphenyl)-3-(2-chloi*pyridin-4-yl)-l -( morpliol in-4-yl )prop-2-en- 1 -on. (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamide, (9.006) Pyrimorph. (9.007) Valifenalate, (9.008) (2E) -3- (4-tert-Butylphenyl) -3- (2-chloropyridin-4-yl) -! - (morpholin-4-yl) prop-2-en-1 - one, (9,009) (2Z) -3- (4-tert-butylphenyl) -3- (2-Chloi * pyridin-4-yl) -l - (morpliol in-4-yl) prop-2-ene-1-one.
10) Inhibitoren der Lipid- und Membran-Synthese, beispielsweise (10.001) Propamocarb, (10.002) Propamocarbhydrochlorid, (10.003) Tolclofos-Methyi. 10) Inhibitors of lipid and membrane synthesis, for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) Tolclofos-Methyi.
11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tricyclazol, (11.002) 2,2,2- Trifluorethyl- {3-methyl-l -[(4-methylbenzoyl)amino]butan-2-yl } carbamat. 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate.
12) Inhibitoren der Nukleinsäuresynthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metaiaxyi, (12.004) Metalaxyl-M (Mefenoxam). 12) inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metaiaxyi, (12.004) metalaxyl-M (mefenoxam).
13) Inhibitoren der Signaltransduktion, beispielsweise (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 14) Verbindungen, die als Entkoppler wirken können, beispielsweise (14.001) Fluazinam, (14.002) Meptyldinocap. 13) inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin. 14) compounds which may act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Weitere Verbindungen, beispielsweise (15.001) Abscisinsäure, (15.002) Benthiazol, (15.003) Bethoxazin, (15.004) Capsimycin, (15.005) Carvon, (15.006) Chinomethionat, (15.007) Cufraneb,15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) Cufraneb,
(15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Flutianil, (15.012) Fosetyl-Aluminium, (15.013) Fosetyl-Calcium, (15.014) Fosetyl-Natrium, (15.015)(15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (15.013) Fosetyl-calcium, (15.014) Fosetyl-sodium, (15.015)
Methylisothiocyanat, (15.016) Metrafenon, (15.017) Mildiomycin, (15.018) Natamycin, (15.019)Methyl isothiocyanate, (15,016) Metrafenone, (15,017) Mildiomycin, (15,018) Natamycin, (15,019)
Ni ckel-Dimethyldithiocarbamat, (15.020) Nitrothal-Isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiprolin, (15.023) Oxyfenthiin, (15.024) Pentachlorphenol und Salze, (15.025) Phosphonsäure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pynofenone (Chlazafenone) (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) l -(4-{4-[(5R)-5-(2,6-Difluorphenyl)- 4,5-dihydro-l ,2-oxazol-3-yl]-l ,3-thiazol-2-yl}piperidin-l -yl)-2-[5-methyl-3-(trifluormethyl)-lH- pyrazol-l -yl]ethanon, (15.032) l -(4-{4-[(5S)-5-(2,6-Difluoi-phenyl)-4,5-dihydro-l ,2-oxazol-3-yl]-l ,3- thiazol-2-yl}piperidin-l -yl)-2-[5-methyl-3-(trifluonnethyl)-lH-pyrazol-l -yl] ethanon, (15.033) 2-(6- Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-lH,5H-[l ,4]dithiino[2,3-c:5,6-c']dipyrrol- l ,3,5,7(2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l -yl]-l -[4-(4-{5-[2-(prop-2-in-l - yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3 -yl} - 1 ,3 -thiazol-2-yl)piperidin- 1 -yljethanon, (15.036) 2-[3,5- Bis(difluormethyl)-lH-pyrazol-l -yl]-l -[4-(4-{5-[2-chlor-6-(prop-2-in-l -yloxy)phenyl]-4,5-dihydro- ,2- oxazol-3 -yl } -1 ,3 -thiazol-2-yl)piperidin- 1 -yl] ethanon, (15.037) 2-[3.5-Bis( difhiormethyl )- l H-pyrazol- 1 - yl]-l -[4-(4- {5-[2-fluor-6-(prop-2-in-l -yloxy)phenyl]-4,5-dihydro-l ,2-oxazol-3-yl}-l ,3-thiazol-2- yl)piperidin- 1 -yl] ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.039) 2-{(5R)-3-[2-(l -{[3,5-Bis(diiluormethyl)-lH-pyrazol-l -yl]acetyl}piperidin-4-yi)-l,3-thiazol-4- yl]-4,5-dihydro-l,2-oxazoi-5-yi}-3-chloiT»henyl methanesulfonat, (15.040) 2-{(5S)-3-[2-(l -{[3,5- Bis(difluormethyl)-l H-pyrazol-1 Ni ckel dimethyldithiocarbamate, (15.020) nitrothal isopropyl, (15.021) oxamocarb, (15.022) Oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pynofenone (Chlazafenone) (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide , (15.031) l - (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole 2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.032) 1 - (4- {4 - [(5S) - 5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5 -methyl-3- (trifluoro-ethyl) -1 -H-pyrazol-1-yl] ethanone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2,6-dimethyl-1H, 5H- [1 , 4] dithiino [2,3-c: 5,6-c '] dipyrrolo, 3,5,7 (2H, 6H) -tetrone, (15,035) 2- [3,5-bis (difluoromethyl) - 1H-pyrazol-1-yl] -1- [4- (4- {5- [2- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazole-3 -yl} - 1, 3-thiazol-2-yl) piperidin-1-yl-ylanone, (15.036) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -l - [4- (4,8 4- {5- [2-chloro-6- (prop-2-yn-1-yloxy ) phenyl] -4,5-dihydro-2-oxazol-3-yl} -1,3-thiazol-2-yl) -piperidine-1-yl] ethanone, (15.037) 2- [3,5-bis (difhi-methyl) 1-H-pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1 , 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1-yl] ethanone, (15.038) 2- [6- (3-fluoro-4-methoxyphenyl) -5-methylpyridine 2-yl] quinazoline, (15.039) 2 - {(5R) -3- [2- (1 - {[3,5-bis (diisoromethyl) -1H-pyrazol-1-yl] -yl] -acetyl} -piperidin-4-yl ) -l, 3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chloro-thylmethanesulfonate, (15.040) 2 - {(5S) -3- [ 2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazole-1
yl} -3-chlorphenyl methanesulfonat, (15.041) 2-{2-[(7,8-Difluor-2-methylquinolin-3-yl)oxy]-6- fluorphenyl}propan-2-ol, (15.042) 2-{2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2- ol, (15.043) 2- {3 -[2-( 1 - { [3 ,5-Bis(difluormethyl)-l H-pyrazol-1 -yl]acetyl}piperidin-4-yl)- 1 ,3 -thiazol-4- yl]-4.5-dihydro- 1 ,2-oxazol-5-yl | -3-ch!orphenyl-methansii!fonat. (15.044) 2-{3-[2-(l -{[3,5-yl} -3-chlorophenyl methanesulfonate, (15.041) 2- {2 - [(7,8-difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} propan-2-ol, (15.042) 2- {2-Fluoro-6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15.043) 2- {3 - [2- (1 - {[3, 5 Bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl -3-ch! Orphenyl-methansii! Sulfonate. (15.044) 2- {3- [2- (l - {[3.5-
Bis(difluormethyl)-l H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-l , 3 -thiazol-4-yl]-4,5-dihydro-l ,2-oxazol-5- yljphenyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-( 4,4. -Tri fl uor-3.3 - dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinolin, (15.047) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisoquinolin-1 -yl)quinolin, (15.048) 4-Amino-5-tluorpyrimitlin-2-ol (Tautomere Form: 4-Amino- 5-fluo yrimidin-2(lH)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino- l ,3,4-thiadiazol-2-thiol, (15.051) 5-Chlor-N'-phenyl-N'-(prop-2-yn-l -yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidm-4-amin, (15.053) 5-Fluor-2-[(4- methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fiuor-2,2-dimethyi-5-(quinolin-3-yl)-2,3-dihydro-l,4- benzoxazepin, (15.055) But-3-yn- ! -yl {6-[( { [(Z)-( 1 -methyl- 1 H-tetrazol-5- yl)(phenyl)methylen]amino }oxy)methyl]pyridin-2-yl } carbamat, (15.056) Ethyl ( 27. )-3-ami ηο-2-cyano- 3-phenylacrylat, (15.057) Phenazin-1 -carbonsäure, (15.058) Propyl 3 ,4,5-trihydroxybenzoat, (15.059) Quinolin-8-οί, (15.060) Quinolin-8-οί sulfat (2: 1), (15.061) tert-Butyl {6-[( {[(l -methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl} carbamat. Bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl-phenylmethanesulfonate , (15.045) 2-phenylphenol and its salts, (15.046) 3- (4,4-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin- 1-yl) quinoline, (15.047) 3- (4, 4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.048) 4-Amino-5-fluoropyrimidin-2-ol (Tautomeric form: 4-amino-5-fluoro-pyrimidine-2 (lH) -one), (15.049) 4-oxo-4 - [(2-phenylethyl) amino] butyric acid, (15.050) 5-amino-l, 3,4-thiadiazole-2-thiol, (15.051) 5- Chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidm-4-amine, (15.053) 5-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15,054) 9-fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3- dihydro-l, 4-benzoxazepine, (15.055) but-3-yn-! -yl {6 - [({[(Z) - (1-methyl-1 H -tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.056) ethyl (27.) -3-amino ηο-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3, 4,5-trihydroxybenzoate, (15.059) quinolin-8-oo, (15.060 ) Quinolin-8-oxy sulfate (2: 1), (15.061) tert-butyl {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) -methylene} -amino} -oxy) -methyl] pyridin-2-yl} carbamate.
Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Die Verbindungen der Formel (I) können mit biologischen S chädlingsb ekämp fungsmitteln kombiniert werden. Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. Biological Pesticides as Mixture Components The compounds of formula (I) may be combined with biological chelating agents. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
Biologische S chädlingsb ekämp fungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological damage control agents include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.
Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of such bacteria which can be used as biological pesticides are:
Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231 179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. R RL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD- 1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, insbesondere B. thuringiensis Subspezies israelensis (Serotyp H- 1 4). Stamm AM65-52 (Accession No. ATCC 1276), oiler B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1 57 (SD-1372), oder 13. thuringiensis subsp. kurstaki Stamm HD-1 , oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Bacillus amyloliquefaciens, strain FZB42 (DSM 231 179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No ATCC 700814) and strain QST2808 (Accession No. R RL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-1 4). Strain AM65-52 (Accession No. ATCC 1276), oiler B. thuringiensis subsp. aizawai, in particular strain ABTS-1 57 (SD-1372), or 13. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts which can be used as biological pesticides are:
Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91 -8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm U RO LEC 12, Lecanicillium lecanii (ehemals bekannt als Verticillium lecanif), insbesondere Stamm KV01,Beauveria bassiana, in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91 -8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain U RO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanif), especially strain KV01,
Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria fiimosorosea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm VI 17b, Trichoderma atroviride, insbesondere Stamm SCI (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39 (Accession Number CNCM 1-952). Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fimosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39 (Accession Number CNCM 1 -952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis VirusExamples of viruses that can be used or used as biological pesticides are: Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus
(NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptem littoralis (Afrikanischer Baumwollwurm) NPV. Es sind auch Bakterien und Pilze umfasst, die als Jnokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptem littoralis (African cottonworm) NPV. It also includes bacteria and fungi, which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrine, Quassia amara, Quercus, Quillaja, Regaiia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinaie, Tanacetum vulgare, Thymol, Triact 70, TriCon. Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regaiia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinaie, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder.
Safener ais Mischungskomponenten Safener ais mixture components
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flura/ole. Fluxofenim, F rila/oie. Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methyicarbamoyl)amino]phenyi}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichioracetyi)-l-oxa-4-azaspiro[4.5]decan (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloracetyl)-l ,3-oxazolidin (CAS 52836-31-4). Pflanzen und Pflanzenteile The compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flura / ols. Fluxofenim, Filla / oie. Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ({4 - [(methyicarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- ( Dichloroacetyl) -l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4) , Plants and plant parts
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika, Gurke, Melone, Möhre, Wassermelone, Zwiebel, Salat, Spinat, Porree, Bohnen, Brassica oleracea (z. B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzr echte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien wie Saatgut, Stecklinge, junge (unausgereifte) Pflanzen bis hin zu ausgereiften Pflanzen verstanden werden. Unter P lanzen teilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rh i /oi ne aufgeführt werden. Zu den Pflanzenteilen gehören auch geerntete Pflanzen oder geerntete Pflanzenteile sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desirable and unwanted wild plants or crop plants (including naturally occurring crop plants), For example, cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugar cane, tomatoes, peppers, cucumber, melon, carrots, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant protectable or non-protectable plant varieties. Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants. Sharpening P lanzen is to be understood as meaning all aboveground and subterranean parts and organs of the plants such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhi / oi ne be listed. The plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, Spritzen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Aus führungs form werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Aus führungs form werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder„Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild species or plant species obtained by conventional biological breeding methods such as hybridization or protoplast fusion and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, weiches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehait, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z. B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z. B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z. B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinone, Sulfonylharnstoffe, Glyphosat oder Phosphinotricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr. Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak. Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen. Zitrusfrüchte und Weintrauben) erwähnt, wobei Mais. Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. Among the preferred transgenic (genetically engineered) plants or plant species to be treated according to the invention are all plants which have obtained genetic material by the genetic engineering modification and which give these plants particularly advantageous valuable properties ("Traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottling, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z. By toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z. For example, systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane. Tomatoes, peas and other vegetables, cotton, tobacco. Rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) mentioned, with corn. Soya, wheat, rice, potato, cotton, sugarcane, tobacco and oilseed rape are particularly emphasized. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
Pflanzenschutz - Behandlungsarten Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vennehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbei/en, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low -Volume -Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Fonnel (I) selbst in den Boden zu injizieren. Crop protection - types of treatment The treatment of plants and plant parts with the compounds of formula (I) is carried out directly or by affecting their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, evaporation, sputtering, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and Vennehrungsmaterial, especially in seeds, continue by Trockenbei / en, wet pickling, Schlämmbeizen It is also possible to apply the compounds of the formula (I) by the ultra-low volume method or to inject the application form or compound of the formula (I) itself into the soil ,
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d. h. die Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d. h. der Standort der Pflanze (z. B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d. Ii. die erfindungsgemäßen Verbindungen der Formel (I) werden in fester Form (z. B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Was s err ei skultur en kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungs form (z. B. als Granulat) in ein überflutetes Reisfeld sein. Saatgutbehandiung A preferred direct treatment of the plants is foliar application, ie the compounds of formula (I) are applied to the foliage, the frequency of treatment and the rate should be adjusted to the infestation pressure of the respective pest. In the case of systemically active substances, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i , Ii. the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In the case of water crops, this can also be achieved by adding the compound of formula (I) in a solid form (eg as granules) to a flooded paddy field. Saatgutbehandiung
Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von S chädlingsb ekämp fungsmitt ein bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen Insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. -toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. The control of animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which obviate or at least significantly reduce the additional application of chelating agents during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. The present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer erfindungsgemäßen Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, weiches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. The invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention. The invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component. For seeds which have been treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating- Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. One of the advantages that occurs when a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted. Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baumwolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z. B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebein und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola. Raps, Gemüse und Reis zu. The compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onion and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of the seed of Cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola. Rapeseed, vegetables and rice too.
Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage"), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example, in water to a certain stage of the rice embryo ("Pigeon Breast Stage"), which stimulates germination and a more uniform emergence.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen B eizmittel -Formuli erungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie /um Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 1 12 und C.I. Solvent Red 1 bekannten Farbstoffe. Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formul ierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalinsulfonate, wie Diisopropyl- oder Diisobutylnaphthalinsulfonate. The compounds of the formula (I) can be converted into the customary formulating formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations. These formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and water. Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 1 12 and CI Solvent Red 1. Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugs weise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stryryiphenolpolygiykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryryiphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Bei/mittei -Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen s chaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Defoamers which may be present in the present invention are all formulations which are customary for the formulation of agrochemical active substances and which contain anti-foaming substances. Preferably usable are silicone defoamers and magnesium stearate.
Als Kons ervi erungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Ben/ylalkoholhemi ormal. As preservatives, all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention. By way of example, dichlorophene and benzyl alcohol are mentioned.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen C ellulo s ederivate , Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to C ellulo s ederivate, acrylic acid derivatives, xanthan, modified clays and finely divided silica. Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibb erellinsäure . Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401-Gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably the gibbellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, p.
412). 412).
Die erfindungsgemäß verwendbaren Beizmittel-Formuiierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zubereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps. Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Bei zmi t i el- Formul i erungen oder deren verdünnte Anwendungs formen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape. Peas, beans, cotton, sunflowers, soybeans and beets or even vegetable seeds of various kinds. The case-sensitive formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formuiierungen oder dem daraus durch Zugabe von Wasser hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im Einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichen oder kontinuierlichen Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formuiierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water, all mixing devices which can usually be used for the dressing can be considered. Specifically, in pickling, the seed is placed in a batch or continuous mixer, adding either desired amount of pickling formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formuiierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
Tiergesundheit Auf dem Gebiet der Tiergesundheit, d. h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwi cklun gs stadi en der Parasiten wirksam. Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; oder Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; oder Fische oder Krustentiere, z. B. in der Aquakultur, oder gegebenenfalls Insekten wie Bienen. Animal health In the field of animal health, ie the field of veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects or acarids. In the field of veterinary medicine, the compounds of formula (I), which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual developmental stages of the parasites. Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögei; Reptilien, Amphibien oder Aquariumfische. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and, in particular, dogs, cats, stubenvögei; Reptiles, amphibians or aquarium fish.
Gemäß einer bestimmten Aus führungs form werden die Verbindungen der Formel (I) an Säugetiere verabreicht. According to a particular embodiment, the compounds of the formula (I) are administered to mammals.
Gemäß einer weiteren bestimmten Aus führungs form werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. According to another specific embodiment, the compounds of the formula (I) are administered to birds, namely caged birds or, in particular, poultry.
Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erziel bar ist. In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable. With regard to the field of animal health, the term "controlling" or "controlling" in the present context means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced. More specifically, "combating" in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.
Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Maliophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damali na spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilla spp., Lutzomyia spp., Meiophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Phiiipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; aus der Ordnung Siphonapterida, zum Beispiel Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. For example, the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Maliophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damali na spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium Spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilla spp., Lutzomyia spp. , Meiophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Phiiipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests and hygiene pests from the order Blattarida.
Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: Further, in arthropods, by way of example and not limitation, the following Akari may be mentioned:
Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Omithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Amblyomma spp.. Dermacentor spp., Haemaphysaiis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaeiaps spp., Varroa spp.; aus der Ordnung Actin edida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp.. Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; und aus der Ordung der Acaridida (Astigmata), /um Beispiel Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. Zu Beispielen für parasitäre Protozoen zählen, ohne hierauf beschränkt zu sein: From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp. Dermacentor spp., Haemaphysaiis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaeiaps spp., Varroa spp .; from the order Actin edida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp. Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. Examples of parasitic protozoa include, but are not limited to:
Mastigophora (Flagellata), wie: Mastigophora (Flagellata), like:
Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. Metamonada: from the order Diplomonadida for example Giardia spp., Spironucleus spp.
Parabasal a: aus der Ordnung Trichomonadida /um Beispiel Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: aus der Ordnung Trypanosomatida zum Beispiel Leishmania spp., Trypanosoma spp. Parabasal a: from the order Trichomonadida / for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
Sarcomastigophora (Rhizopoda), wie Entamoebidae, /um Beispiel Entamoeba spp., Centramoebidae, zum Beispiel Acanthamoeba sp., Euamoebidae, z. B. Hartmanella sp. Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung Piroplasmida z. Ii. Babesia spp., Ciliophora spp., Echinozoon spp., Theiieria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtoneiia spp. Sarcomastigophora (Rhizopoda), such as Entamoebidae, / for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida z. Ii. Babesia spp., Ciliophora spp., Echinozoon spp., Theieria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtoneiia spp.
Micro spora wie Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., und außerdem z. B. Myxozoa spp. Microspores such as Encephalitozoon spp., Enterocytocoon spp., Globidium spp., Nosema spp. B. Myxozoa spp.
Zu den für Menschen oder Tiere pathogenen Helminthen zählen zum Beispiel Acanthocephala, Nematoden, Pentastoma und Platyhelminthen (z.B. Monogenea, Cestodes und Trematodes). Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Exemplary helminths include, but are not limited to:
Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Monogenea: z. For example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
Cestodes: aus der Ordnung Pseudophyilidea zum Beispiel: Bothridium spp., Diphyliobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Cestodes: from the order Pseudophyilidea for example: Bothridium spp., Diphyliobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. For example, from the order Cyclophyllida: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
Trematodes: aus der Klasse Digenea zum Beispiel: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Nematoden: aus der Ordnung Trichinellida zum Beispiel: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. Trematodes: from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyricum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Nematodes: from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp. Aus der Ordnung Rhabditina zum Beispiel: Aeluro strongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippo strongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafüaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. For example, from the order Tylenchida: Micronema spp., Parastrangyloides spp., Strongyloides spp. From the order Rhabditina for example: Aeluro strongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp , Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp. Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippo strongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafüaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp , Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
Aus der Ordnung Spirurida zum Beispiel: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Fiiaria spp., Gnatho Stoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp.. Parabronema spp., Para fiiaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skj rabin ema spp., Spirocerca spp., Stephano fiiaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. For example, from the order Spirurida: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Fiiaria spp., Gnatho stoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp. Parabronema spp., Parafiaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skj rabin ema spp., Spirocerca spp., Stephano fiiaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp., Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
Aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Pentastoma: from the order Porocephalida for example Linguatula spp.
Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphylaktisch oder therapeutisch erfolgen. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
So bezieht sich eine Ausfuhrungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) zur Verwendung als Arzneimittel. Thus, one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) zur Verwendung als Antiendoparasitikum. Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platymelminthizid, Acanthocephalizid oder Pentastomizid. Another aspect relates to the compounds of formula (I) for use as antiendoparasitic. Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antiprotozoikum. Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung als Antiektoparasitikum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
Weitere Aspekte der Erfindung sind veterinärmedizinische Formuli erungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizini s chen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten Hilfsmitteln umfasst. Further aspects of the invention are veterinary formulations which comprise an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations. A related aspect of the invention is a process for the preparation of a veterinary formulation as herein described, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, in particular with pharmaceutically acceptable ones conventionally used in veterinary formulations Excipients and / or adjuvants conventionally used in veterinary formulations.
Ein anderer spezieller Aspekt der Erfindung sind veterinärmedizinische Formulierungen ausgewählt aus der Gruppe ektoparasitizider und endoparasitizider Formulierungen, insbesondere ausgewählt aus der ruppe anthelmintischer, antiprotozolischer und arthropodizider Formulierungen, ganz besonders ausgewählt aus der Gruppe nematizider, platyhelminthizider, acanthocephalizider, pentastomizider, insektizider und akkarizider Formulierungen, gemäß den erwähnten Aspekten, sowie Verfahren zu ihrer Herstellung. Another specific aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wie hier definierten veterinärmedizinischen Formulierung bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung" die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, the same requirement. Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal. In the present veterinary or veterinary context, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment.
Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das veterinärmedizinische Gebiet bereitgestellt. Auf dem Gebiet der Tiergesundheit bedeutet„Mischung" nicht nur, dass zwei (oder mehr) verschiedene Wirkstoffe in einer gemeinsamen Formulierung formuliert werden und entsprechend zusammen angewendet werden, sondern bezieht sich auch auf Produkte, die für jeden Wirkstoff getrennte Formulierungen umfassen. Dementsprechend können, wenn mehr als zwei Wirkstoffe angewendet werden sollen, alle Wirkstoffe in einer gemeinsamen Formulierung formuliert werden oder all Wirkstoffe in getrennten Formulierungen formuliert werden; ebenfalls denkbar sind gemischte Formen, bei denen einige der Wirkstoffe gemeinsam formuliert und einige der Wirkstoffe getrennt formuliert sind. Getrennte Formulierungen erlauben die getrennte oder aufeinanderfolgende Anwendung der in Rede stehenden Wirkstoffe. In a particular embodiment, mixtures of at least one compound of formula (I) with other active ingredients, especially endo and ectoparasiticides, are provided herein for the veterinary field. In the animal health field, "blending" not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances are formulated in a common formulation, or all the active substances are formulated in separate formulations, also conceivable mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
Die hier mit ihrem„Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im „Pesticide Manual" (siehe oben) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). The active ingredients specified herein by their "common name" are known and described, for example, in the "Pesticide Manual" (see above) or searchable on the Internet (e.g., http://www.alanwood.net/pesticides).
Beispielhafte Wirkstoffe aus der Gruppe der Ektoparasitizide als Mischungspartner schließen, ohne dass dies eine Einschränkung darstellen soll, die oben ausführlich aufgelisteten Insektizide und Akkarizide ein. Weitere verwendbare Wirkstoffe sind unten gemäß der oben erwähnten Klassifikation, die auf dem aktuellen IRAC Mode of Action Classification S eherne beruht, aufgeführt: (1) Acetylcholinesterase ( AChE) -Inhibitoren ; (2) GABA-gesteuerte Chlorid-Kanal-Blocker; (3) Natrium-Kanal-Modulatoren; (4) kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (5) allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (6) allosterische Modulatoren des Glutamat-abhängigen Chloridkanals (GluCl); (7) Juvenilhormon-Mimetika; (8) verschiedene nichtspezifische (Multi-Site) Inhibitoren; (9) Modulatoren Chordotonaler Organe; (10) Milbenwachstumsinhibitoren; (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP- Disruptoren; (13) Entkopplet- der oxidativen Phosphorylierung durch Störung des Protonengradienten; (14) Blocker des nicotinischen Acetylcholinrezeptorkanals; (15) Inhibitoren der Chitinbiosynthese, Typ 0; (16) Inhibitoren der Chitinbiosynthese, Typ 1 ; (17) Häutungsdisruptor (insbesondere bei Dipteren, d.h. Zweiflüglern); (18) Ecdyson-Rezeptor-Agonisten; (19) Octopamin-Rezeptor-Agonisten; (21) mitochondriale Komplex-I-Elektronentransportinhibitoren; (25) mitochondriale Komplex-II- El ektronentransportmhibitoren ; (20) mitochondriale Komplex-III-Elektronentransportinhibitoren; (22) Blocker des spannungsabhängigen Natriumkanals; (23) Inhibitoren der Acetyl-CoA-Carboxylase; (28) Ryanodinrezeptor-Modulatoren; Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, z. B. Fentrifanil, Fenoxacrim, Cyciopren, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quinomethionat, Triarathen, Clothiazoben, Tetrasul, Kaliumoleat, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Brompropyiat, Cryolit; Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above. Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of oxidative phosphorylation by disruption of the proton gradient; (14) blocker of the nicotinic acetylcholine receptor channel; (15) inhibitors of chitin biosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1; (17) molting disruptor (especially in dipterans, ie two-winged); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) blocker of the voltage-dependent sodium channel; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; Active substances with unknown or non-specific mechanisms of action, eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlorodimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(- ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton- S -methyl sul fon, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(- ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Organochlorverbindungen, z. B. Camphechlor, Lindan, Heptachlor; oder Phenylpyrazole, z. B. Acetoprol, Pyratluprol. Pyripro!. Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fiuralaner; Compounds from other classes, e.g. Butacarb, dimetilane, cloethocarb, phosphocarb, pirimiphos (- ethyl), parathion (-ethyl), methacrifos, isopropyl-o-salicylate, trichlorofon, sulforos, propaphos, sebufos, pyridathione, prothoate, dichlorofenthione, demeton-S-methyl sulphone, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autothiofos, Aromfenvinfos (-methyl), Azinphos (-ethyl), Chlorpyrifos (- ethyl), Fosmethilane, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Organochlorine compounds, e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyratluprol. Pyripro !. Vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fiuralaner;
Pyrethroide, z. B. (eis-, trans-)Metofluthrin, Protluthrin. Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohl enwas s er sto ffverbindungen (HCHs), Pyrethroids, e.g. B. (cis, trans) metofluthrin, protluthrin. Flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrine, cis-cypermethrin, cis-permethrin, clocythrin, cyhalothrin (lambda), chlovaporthrin, or halogenated cabbage s he links (HCHs),
Neonicotinoide, z. B. Nithiazin Neonicotinoids, e.g. B. Nithiazine
Dicloromezotiaz, Triflumezopyrim makroeyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Dicloromezotiaz, triflumezopyrim, macrocyclic lactones, e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
Tripren, Epofenonan, Diofenolan; Triphene, Epofenonan, Diofenolan;
Biologicals, Hormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Codlemon oder Neem-Komponenten Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, codlemon or neem components
Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Benzoylharnstoffe, z. B. Fluazuron, Penfluron, Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Dinitrophenols, e.g. Dinocap, dinobuton, binapacryl; Benzoylureas, eg. Fluazuron, penfluron, Amidine derivatives, e.g. B. Chlormebuform, cymiazole, demiditraz
Bienenstockvarroa-Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid.
Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Zu den anthelmintischen Wirkstoffen zählen, ohne hierauf beschränkt zu sein, die folgenden nematiziden, trematiziden und/oder cestoziden Wirkstoffe: aus der Klasse der makrocyclischen Lactone zum Beispiel: Eprinomectin, Abamectin, Nemadectin,Exemplary agents from the group of endoparasiticides, as a mixture partner, include, but are not limited to, anthelmintic agents and antiprotozoal agents. The anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestocidal agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin,
Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; aus der Klasse der Benzimidazole und Probenzimidazole zum Beispiel: Oxibendazoi, Mebendazol, Triclabendazol, Thiophanat, Parbendazol, Oxfendazol, Netobimin, Fenbendazol, Febantel, Thiabendazol, Cyclobendazol, Cambendazol, Albendazol-sulfoxid, Albendazol, Flubendazol; aus der Klasse der Depsipeptide, vorzugsweise cyclischen Depsipetide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Levamisol, Tetramisol; aus der Klasse der Aminophenylamidine zum Beispiel: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Aminoacetonitrile zum Beispiel: Monepantel; aus der Klasse der Paraherquamide zum Beispiel: Paraherquamid, Derquantel; aus der Klasse der Salicylanilide zum Beispiel: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; aus der Klasse der substituierten Phenole zum Beispiel: Nitroxynil, Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan; aus der Klasse der Organophosphate zum Beispiel: Trichlorfon, Naphthalofos, Di lil orvos DD V , Crufomat, Coumaphos, Haloxon; aus der Klasse der Piperazinone/Chinoline zum Beispiel: Praziquantel, Epsiprantel; aus der Klasse der Piperazine zum Beispiel: Pipera/in. Hydroxyzin; aus der Klasse der Tetracycline zum Beispiel: Tetracyclin, Chlorotetracyclin, Doxycyclin, Oxytetracyclin, Rolitetracyclin; aus diversen anderen Klassen zum Beispiel: Bunamidin. Niridazol, Resorantel, Omphalotin, Oltipraz. Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon. Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazoi, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipetides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines for example: Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amide shell, deacylated amide shell (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: Monepantel; from the class of Paraherquamide, for example: Paraherquamid, Derquantel; from the class of salicylanilides for example: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, nicolofolane, meniclopholan; from the class of organophosphates, for example: Trichlorfon, Naphthalofos, Di lil orvos DD V, Crufomat, Coumaphos, Haloxon; from the class of piperazinones / quinolines for example: praziquantel, epsiprantel; from the class of piperazines for example: Pipera / in. hydroxyzine; from the class of tetracyclines for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes for example: Bunamidine. Niridazole, Resorantel, Omphalotin, Oltipraz. Nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetoline, emetine, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon.
Antiprotozoische Wirkstoffe, darunter, ohne hierauf beschränkt zu sein, die folgenden Wirkstoffe: aus der Klasse der Triazine zum Beispiel: Diclazuril, Ponazuril, Letrazuril, Toitrazuril; aus der Klasse Poiyletherionophor zum Beispiel: Monensin, Salinomycin, Maduramicin, Narasin; aus der Klasse der makrocyclischen Lactone zum Beispiel: Milbemycin, Erythromycin; aus der Klasse der Chinolone zum Beispiel: Enrofloxacin, Pradofloxacin; aus der Klasse der Chinine zum Beispiel: Chloroquin; aus der Klasse der Pyrimidine zum Beispiel: Pyrimethamin; aus der Klasse der Sulfonamide zum Beispiel: Sulfachinoxalin, Trimethoprim, Sulfaclozin; aus der Klasse der Thiamine zum Beispiel: Amprolium; aus der Klasse der Lincosamide zum Beispiel: Clindamycin; aus der Klasse der Carbanilide zum Beispiel: Imidocarb; aus der Klasse der Nitrofurane zum Beispiel: Nifurtimox; aus der Klasse der Chinazolinonalkaloide zum Beispiel: Halofuginon; aus diversen anderen Klassen zum Beispiel: Oxamniquin, Paromomycin; aus der Klasse der Vak/ine oder Antigene aus Mikroorganismen zum Beispiel: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus. Antiprotozoal agents, including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toitrazuril; from the class Poiyletherionophor for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofurans, for example: nifurtimox; from the class of quinazolinone alkaloids, for example: halofuginone; from various other classes for example: oxamniquine, paromomycin; from the class of vaccines or antigens from microorganisms, for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.
Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Vektorbekämpfung In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids. vector control
Die Verbindungen der Formel (I) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z. B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z. B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: Examples of vectors and their transmitted diseases or pathogens are:
1) Mücken - Anopheles: Malaria, Filariose; 1) Mosquitoes - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von anderen Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms;
- Aedes: Gelbfieber, Dengue-Fieber, weitere virale Erkrankungen, Filariasis; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis;
- Simulien: Übertragung von Würmern, insbesondere Onchocerca volvulus; - Psychodidae: Übertragung von Leishmaniose - Simulia: transmission of worms, in particular Onchocerca volvulus; - Psychodidae: transmission of leishmaniasis
2) Läuse: Hautinfektionen, epidemisches Fleckfieber; 2) lice: skin infections, epidemic typhus;
3) Flöhe: Pest, endemisches Fleckfieber, Bandwürmer; 3) fleas: plague, endemic typhus, tapeworms;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, epidemisches Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephaiitis, Frühsommer-Meningoenzephalitis (FSME), Krim-Kongo-Fieber, Borreliose; 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;
6) Zecken: Boreliiosen wie Borrelia bungdorferi sensu lato., Borrelia duttoni, Frühsommer- Meningoenzephalitis, Q-Fieber (Coxielia burnetii), Babesien (Babesia canis canis), Ehrlichiose. 6) Ticks: Borelioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxielia burnetii), Babesia (Babesia canis canis), Ehrlichiosis.
Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten, zum Beispiel Aphiden. Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Examples of vectors in the context of the present invention are insects, for example aphides. Flies, cicadas or thrips that can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Psychodide wie Phlebotomus, Lutzomyia, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. BA gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans. Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krank eiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorbekämpfung, z. B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorratsund Materialschutz. Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the supply and material protection.
Schutz von technischen Materialen Protection of technical materials
Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z. B. aus den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Hol/. Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. In the present context, technical materials are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, glues, papers and cardboard, leather, wood. Woodworking products and paints. The application of the invention for the protection of wood is particularly preferred.
In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. in einer weiteren Aus führungs form liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d. h., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide. In a further embodiment, the compounds of the formula (I) are present as a ready-to-use pesticide, ie. h., They can be applied to the appropriate material without further changes. As further insecticides or fungicides, in particular those mentioned above come into question.
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderenSurprisingly, it has also been found that the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. Likewise, the compounds of formula (I) may be used alone or in combination with others
Wirkstoffen als Antifouling-Mittel eingesetzt werden. Active ingredients are used as antifouling agents.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorrats schütz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen. Büros, Fahrzeugkabinen, Tierzuchtaniagen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage contactor, especially for controlling insects, arachnids, ticks and mites in indoor areas, such as apartments, factory buildings. Offices, vehicle cabins, Tierzuchtaniagen occur. To combat animal pests, the compounds of Formula (I) used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z. B. Pump- und Zerstäubersprays, Nebelautomaten, Foggem, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propel I ergo! ri ebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. Die folgenden Herstei llings- und Verwendungsbeispiele illustrieren die Erfindung ohne sie zu beschränken. The application is carried out for example in aerosols, non-pressurized sprays, z. B. pump and Zerstäubersprays, fog machines, Foggem, foams, gels, evaporator products with evaporator plates made of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propel I ergo! Ri flat evaporators, energy-less or passive evaporation systems, moth papers, moth sacs and moth gels, as granules or dusts, in straw baits or bait stations. The following examples of manufacture and use illustrate the invention without limiting it.
Herstellungsheispiele Herstellungsheispiele
Synthesebeispiel Nr. 1 -(( hloracetyl)- l (2-chlor-l ,3-thiazol-5-yl)nieI hyl|-l H-iniidazo| l ,2-a|p Synthesis Example No. 1 - ((chloroacetyl) -1 (2-chloro-1,3-thiazol-5-yl) -Nilyl-1H-imidazo | 1, 2-a | p
(Verbindung Nr. 1-1 -002)  (Compound No. 1-1 -002)
Eine Lösung von N-[(2-Chlor-l,3-thiazol-5-yl)methyl]pyridin-2-amin [bekannt aus WO2009099929] (5,00 g, 22,1 mmol) in Dioxan wurde mit Chloressigsäureanhydrid (7,58 g, 44.3 mmol) und Chloressigsäure (4,19 g, 44,3 mmol) versetzt und anschließend 16 Stunden unter Rückfluß erhitzt. Nach Abkühlen wurde das Reaktionsgemisch vorsichtig in ein Gemisch aus 200 mL 10% iger Natriumcarbonatlö sung und 400 mL Eiswasser gegossen. Der ausgefallene Niederschlag wurde abgesaugt und in Dichlormethan aufgenommen. Die organische Phase wurde über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Es wurden 6,48 g (82,9 % d.Th.) 3-(Chloracetyl)-l -[(2-chlor-l ,3-thiazol-5-yl)methyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat erhalten. HPLC-MS: logP = 1 ,69; Masse (m/z): 341,9; »HNMR ÜVDMSO): δ 4.79 (s, 2H), 5.42 (s, 2H), 7.42, (m, 1H), 7.86 (s, 1H), 7.92 (m, 2H), 9.82 (m, 1H). A solution of N - [(2-chloro-1,3-thiazol-5-yl) methyl] pyridin-2-amine [known from WO2009099929] (5.00 g, 22.1 mmol) in dioxane was treated with chloroacetic anhydride ( 7.58 g, 44.3 mmol) and chloroacetic acid (4.19 g, 44.3 mmol) and then heated under reflux for 16 hours. After cooling, the reaction mixture was carefully poured into a mixture of 200 ml of 10% sodium carbonate solution and 400 ml of ice water. The precipitate was filtered off with suction and taken up in dichloromethane. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. There were obtained 6.48 g (82.9% of theory) of 3- (chloroacetyl) -1- [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2 -a] pyridin-4-ium-2-olate. HPLC-MS: logP = 1.69; Mass (m / z): 341.9; »HNMR ÜVDMSO): δ 4.79 (s, 2H), 5.42 (s, 2H), 7.42, (m, 1H), 7.86 (s, 1H), 7.92 (m, 2H), 9.82 (m, 1H).
Synthesebeispiel Nr. 2 l -|(2 hlor- l , -thiazol-5-yl)niethy^ Synthesis Example No. 2 l - | (2-chloro-1-thiazol-5-yl) niethy ^
(Verbindung Nr.I-1 -008)  (Compound No. I-1 -008)
3-(Chloracetyl)-l -[(2-chlor-l ,3-thiazol-5-yi)methyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat 3- (Chloroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridin-4-ium-2-olate
(Verbindung Nr. 1-1 -002) (250 mg, 0,73 mmol) wurde in Methanol/Dichlormethan (1 : 1) (12 mL) vorgelegt und mit Natriummethylat (59,2 mg, 1,09 mmol) versetzt. Das Reaktionsgemisch wurde anschließend bei Raumtemperatur 16 Stunden gerührt. Nach Verdünnen mit Dichlormethan wurde mit Wasser gewaschen, die organische Phase über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wurde auf Kieseigel adsorbiert und mit Die hl on ne! ha n 2 -Propano I (92:8) als Laufmittel chromatographiert. Es wurden 69,0 mg (26 % der Theorie) 1 -[(2-Chlor-l ,3-thiazol-5-yl)methyl] -3 -(methoxyacetyl)- 1 H-imidazo [ 1 ,2-a]pyridin-4-ium-2- olat erhalten. HPLC-MS: logP = 1,23; Masse (m z): 338,0; >HNMR (D6-DMSO): δ 4.53 (s, 2H), 5.39 (s, 2H), 7.38, (m, 1H), 7.88 (m, 3H ). 9.88 (m, 1H). (Compound No. 1-1 -002) (250 mg, 0.73 mmol) was charged in methanol / dichloromethane (1: 1) (12 mL) and sodium methylate (59.2 mg, 1.09 mmol) was added. The reaction mixture was then stirred at room temperature for 16 hours. After dilution with dichloromethane, it was washed with water, the organic phase was dried over magnesium sulfate and the solvent was added distilled off under reduced pressure. The residue was adsorbed on silica gel and washed with the oil. Ha n 2 -Propano I (92: 8) as the eluent chromatographed. There was obtained 69.0 mg (26% of theory) of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (methoxyacetyl) -1H-imidazo [1,2-a] pyridine-4-ium-2-olate. HPLC-MS: log P = 1.23; Mass (mz): 338.0; > HNMR (D 6 -DMSO): δ 4.53 (s, 2H), 5.39 (s, 2H), 7.38, (m, 1H), 7.88 (m, 3H). 9.88 (m, 1H).
Synthesebeispiel Nr. 3 l-[(2-Chlor-l,3-thiazol-5-yl)methyl]-3-(i^ Synthesis Example No. 3 l - [(2-chloro-l, 3-thiazol-5-yl) methyl] -3- (i)
(Verbindung Nr. 1-1 -026)  (Compound No. 1-1-026)
Zu 2-Propanol (2,5 mL) wurde NaH, 60%ig in Öidispersion (21 mg, 0,87 mmol) gegeben und das Gemisch 30 min bei Raumtemperatur gerührt. Diese Lösung wird langsam zu einer Lösung von 3- (Chloracetyl)-l -[(2-chlor-l ,3-thiazoi-5-yl)methyi]-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat (200 mg. 0,58 mmol) (Verbindung Nr.I- 1-002) in 2-Propanol Dichlormethan (1 : 1) (10,0 mL) getropft und anschließend 16 Stunden bei Raumtemperatur gerührt. Nach Verdünnen mit Dichlormethan wurde mit Wasser gewaschen, die organische Phase über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wurde auf Kieselgel adsorbiert und mit Dichlormethan 2-Propanol (92:8) als Laufmittel chromatographi ert . Es wurden 129,0 mg (60 % der Theorie) 1 -[(2 -Chlor- 1 ,3 -thiazol-5-yl)methyl] -3 -(isopropoxyacetyl)-l H-imidazo [1 ,2-a]pyridin-4-ium-2- olat erhalten. HPLC-MS: logP = 1,73; Masse (m/z): 365,9; 'HNMR ( D-D SO): δ 1.14 (d, 611 ). 3.68 (m, 1H), 4.58 (s, 211 ). 5.40 (s, 2H), 7.37, (m, 1H), 7.85 (m, 311 ). 9.88 (m, 1H). To 2-propanol (2.5 mL) was added NaH 60% in oleidispersion (21 mg, 0.87 mmol) and the mixture was stirred at room temperature for 30 min. This solution slowly becomes a solution of 3- (chloroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridine-4-ium 2-olate (200 mg, 0.58 mmol) (Compound No. I-1-002) in 2-propanol dichloromethane (1: 1) (10.0 mL) was added dropwise and then stirred for 16 hours at room temperature. After dilution with dichloromethane, it was washed with water, the organic phase was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was adsorbed onto silica gel and chromatographed with dichloromethane 2-propanol (92: 8) as the eluent. 129.0 mg (60% of theory) of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (isopropoxyacetyl) -1H-imidazo [1,2-a] pyridine-4-ium-2-olate. HPLC-MS: log P = 1.73; Mass (m / z): 365.9; 'HNMR (DD SO): δ 1.14 (d, 611). 3.68 (m, 1H), 4.58 (s, 211). 5.40 (s, 2H), 7.37, (m, 1H), 7.85 (m, 311). 9.88 (m, 1H).
Synthesebeispiel Nr. 4 l -|(2-( hlor- l ^-thiazol-5-yl)niethyl|-3-|(ethyIsulfanyl)acetyI|-l H-im Synthesis Example No. 4 l - | (2- (chloro-1-thiazol-5-yl) -niethyl | -3- | (ethylisulfanyl) acetyl | -IH-im
olat (Verbindung Nr. 1-1 -028) olate (Compound No. 1-1-028)
3-(Chloracetyl)-l -[(2-chlor-l ,3 -thiazol-5-yl)methyl]-l H-imidazo [1 ,2-a]pyridin-4-ium-2 -olat 3- (Chloroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridin-4-ium-2 -olate
(Verbindung Nr. 1-1-002) (255 mg. 0,74 mmol) wurde in DM F (10 mL) vorgelegt und bei 0°C mit einer Lösung von Natriumethanthiolat (93,8 mg, 1,1 1 mmol) in 2 liiL DMF versetzt. Das Reaktionsgemisch wurde anschließend bei Raumtemperatur 16 Stunden gerührt und das DMF daraufhin im Vakuum abdestiliert. Der Rückstand wurde in Di chlormethan/ Wass er aufgenommen, die organische Phase abgetrennt und über Magnesiumsulfat getrocknet. Nach AbdestiUieren des Lösungsmittels unter vermindertem Druck wurde der Rückstand auf Kieseigel adsorbiert und mit Dichlormethan/2-Propanol (92:8) als Laufmittel Chromatographien. Es wurden 205 mg (61,4 % der Theorie) 1 -[(2 -Chlor- 1 ,3- thiazol-5-yl)methyl] -3 -[(ethylsulfanyl)acetyl] - 1 H-imiila/o [ 1 ,2-a]pyridin-4-ium-2-olat erhalten. HPLC- MS: logP = 1 ,99; Masse (m/z): 368,0; 'HNMR ( D -DMSO): δ 1.20 (t, 3H ). 2,50 (q, 2 H ). 3,86 (s, 2H), 5.41 (s, 2H), 7.37, (m, 1H), 7.89 (m, 3H), 9.88 (m, 1H). Synthesebeispiel Nr. 5 l -|(2-( hlor- U-thiazol-5-yl)nu^ (Compound No. 1-1-002) (255 mg, 0.74 mmol) was initially charged in DMF (10 mL) and treated at 0 ° C with a Solution of sodium ethanethiolate (93.8 mg, 1.1 1 mmol) in 2 ml of DMF. The reaction mixture was then stirred at room temperature for 16 hours and then the DMF distilled off in vacuo. The residue was taken up in dichloromethane / water, the organic phase separated and dried over magnesium sulphate. After distilling off the solvent under reduced pressure, the residue was adsorbed on silica gel and chromatographed with dichloromethane / 2-propanol (92: 8) as eluent. There were 205 mg (61.4% of theory) of 1 - [(2-chloro-1, 3-thiazol-5-yl) methyl] -3 - [(ethylsulfanyl) acetyl] - 1 H-imiila / o [1 , 2-a] pyridin-4-ium-2-olate. HPLC-MS: log P = 1.99; Mass (m / z): 368.0; 'HNMR (D -DMSO): δ 1.20 (t, 3H). 2.50 (q, 2H). 3.86 (s, 2H), 5.41 (s, 2H), 7.37, (m, 1H), 7.89 (m, 3H), 9.88 (m, 1H). Synthesis Example No. 5 l - | (2- (chloro-U-thiazol-5-yl) nu ^
olat und l -[(2-C hlor-1 ,3-thia/ol-5-yl)nuthyl| -3- [(ethylsulf onyl)acetyl] -lH-imidazo [1,2-a] yridin-4- ium-2-olat (Verbindung Nr.I- 1 -037 und 1-1 -042) olate and 1 - [(2-chloro-1,3-thia / ol-5-yl) nuthyl -3- [(ethylsulfonyl) acetyl] -1H-imidazo [1,2-a] yridin-4-ium-2-olate (Compound No.I-1 -037 and 1-1-042)
l -[(2-Chlor-l,3-thiazol-5-yl)methyl]-3-[(ethylsulfanyi)acetyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2-o l - [(2-chloro-1,3-thiazol-5-yl) methyl] -3 - [(ethylsulfanyi) acetyl] -1H-imidazo [1,2-a] pyridin-4-ium-2-o
(Verbindung Nr. 1-1 -028) (161 mg. 0,43 mmol) wurde in Dichlormethan (10 mL) vorgelegt und bei 0°C mit meta-Chlorperben/oesäure. 70%ig (146 mg. 0,59 mmol) versetzt. Das Reaktionsgemisch wurde unter Erwärmen auf Raumtemperatur 16 Stunden gerührt, das Reaktionsgemisch daraufhin in Dichlormethan/Wasser aufgenommen, mit gesättigter Natriumhydrogencarbonatlösung gewaschen, die organische Phase abgetrennt und über Magnesiumsulfat getrocknet. Nach AbdestiUieren des Lösungsmittels unter vermindertem Dru k wurde der Rückstand auf Kieselgel adsorbiert und mit Dichlormethan 2-Propanol (92:8) als Laufmittel Chromatographien. Es wurden 82 mg (45 % der Theorie) l-[(2-Chlor-l ,3-thiazol-5-yl)methyl]-3-[(ethylsulfanyl)acetyl]-lH-imidazo[l,2-a]pyridin-4- ium-2-olat und 15 mg (7 % der Theorie) 1 -[(2 -Chlor- 1 ,3 -thiazol-5-yl)methyl] -3 -[(ethylsulfonyl)acetyl] - 1 H-imida/o [ 1 ,2-a]pyridin-4-ium-2-olat erhalten. l -[(2-Chlor-l,3-thiazol-5-yl)methyl]-3-[(ethy : HPLC-MS: logP = 1 ,13; Masse (m/z): 384,0; 'HNMR ( D -DM SO): δ 1.24 (t, 3H), 2,78 (m, 1H), 2.92 (m, 1H), 4,40 (q, 2H), 5.4 1 (s, 2H), 7.40, (m, 1H), 7.86 (s, 1H), 7.92 (m, 2H), 9.84 (m, 1H); l -[(2-Chlor- l ,3-thiazol-5-yl)methyl]-3-[(ethylsulfonyl)acetyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat:HPLC-MS logP = 1 ,38; Masse (m z): 400,0; 'HNMR ( D -DMSO): δ 1.28 (t, 3H), 3,1 (m, 2H), 4,93 (s, 2H), 5.42 (s, 2H), 7.42. (m, 1H), 7.86 (s, 1H), 7.97 (m, 2H), 9.83 (m, 1H); Synthesebeispiel Nr. 6 l-[(2-Chlor-l,3-thiazol-5-yl)methyl]-3-(l^^ (Compound No. 1-1-028) (161 mg, 0.43 mmol) was initially charged in dichloromethane (10 mL) and treated at 0 ° C with meta-chloroperbenzoic acid. 70% (146 mg, 0.59 mmol) was added. The reaction mixture was stirred with warming to room temperature for 16 hours, then the reaction mixture was taken up in dichloromethane / water, washed with saturated sodium bicarbonate solution, the organic phase separated and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was adsorbed onto silica gel and chromatographed with dichloromethane 2-propanol (92: 8) as eluent. 82 mg (45% of theory) of l - [(2-chloro-1,3-thiazol-5-yl) methyl] -3 - [(ethylsulfanyl) acetyl] -1H-imidazo [1,2-a] pyridine-4-ium-2-olate and 15 mg (7% of theory) of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3 - [(ethylsulfonyl) acetyl] -1H -imida / o [1,2-a] pyridine-4-ium-2-olate. l - [(2-chloro-l, 3-thiazol-5-yl) methyl] -3 - [(ethy: HPLC-MS: log P = 1.13; mass (m / z): 384.0; HNMR (D -DM SO): δ 1.24 (t, 3H), 2.78 (m, 1H), 2.92 (m, 1H), 4.40 (q, 2H), 5.4 1 (s, 2H), 7.40, (m, 1H), 7.86 (s, 1H), 7.92 (m, 2H), 9.84 (m, 1H), 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- [(ethylsulfonyl) acetyl] -1H-imidazo [1,2-a] pyridin-4-ium-2-olate: HPLC-MS logP = 1.38; mass (mz): 400.0; 'HNMR (D - DMSO): δ 1.28 (t, 3H), 3.1 (m, 2H), 4.93 (s, 2H), 5.42 (s, 2H), 7.42. (M, 1H), 7.86 (s, 1H) , 7.97 (m, 2H), 9.83 (m, 1H); Synthesis Example No. 6 l - [(2-chloro-l, 3-thiazol-5-yl) methyl] -3- (1)
olat (Verbindung Nr. 1-1 -009) olate (Compound No. 1-1 -009)
3-(Chioracetyl)-l -[(2-chlor-l ,3-thiazol-5-yl)methyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat 3- (Chioroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridin-4-ium-2-olate
(Verbindung Nr. 1-1 -002) (100 mg, 0,74 mmol) wurde zu einer Suspension von Cäsiumcarbonat (190 mg, 0,58 mmol) und Pyrazol (30 mg, 0,43 mmol) in DMF (5 mL) gegeben und anschließend 16 Stunden bei Raumtemp eratur gerührt. Das Reaktionsgemisch wurde in Dichlormethan/Wasser aufgenommen, die organische Phase abgetrennt und über Magnesiumsulfat getrocknet. Nach Abdestillieren des Lösungsmittels unter vermindertem Druck wurde der Rückstand auf Kieselgel adsorbiert und mit Dichlormethan/2-Propanol (92:8) als Laufmittel Chromatographien. Es wurden 64 mg (50,9 % der Theorie) 1 - [(2-Chlor- 1 ,3-thiazol-5-yl)methyl] -3 -( 1 H-pyrazol-1 -ylacetyl)- 1 H-imidazo[ 1 ,2-a]pyridin-4- ium-2-oiat erhalten. HPLC-MS: logP = 1 ,47; Masse (m/z): 374,0; 'HNMR (D6-DMSO): δ 5,49 (s, 2H), 5.52 (s, 2H), 6,27 (s, 1H), 7.38, (m, 2H), 7.73 (s, 1H), 7.87 (m, 3 H ). 9.76 (m, 1H). Synthesebeispiel Nr. 7 l-[(2-Chlor-1 -thiazol-5-yl)methyl]-3-(^ (Compound No. 1-1 -002) (100 mg, 0.74 mmol) was added to a suspension of cesium carbonate (190 mg, 0.58 mmol) and pyrazole (30 mg, 0.43 mmol) in DMF (5 mL ) and then stirred for 16 hours at room temperature. The reaction mixture was taken up in dichloromethane / water, the organic phase separated and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was adsorbed onto silica gel and chromatographed with dichloromethane / 2-propanol (92: 8) as eluent. There were 64 mg (50.9% of theory) of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (1H-pyrazole-1-yl-acetyl) -1H-imidazo [1,2-a] pyridine-4-ium-2-oiat. HPLC-MS: logP = 1.47; Mass (m / z): 374.0; 'HNMR (D 6 -DMSO): δ 5.49 (s, 2H), 5.52 (s, 2H), 6.27 (s, 1H), 7.38, (m, 2H), 7.73 (s, 1H), 7.87 (m, 3H). 9.76 (m, 1H). Synthesis Example No. 7 l - [(2-chloro-1-thiazol-5-yl) methyl] -3 - (^
(Verbindung Nr.I- 1 -021)  (Compound No. I-1 -021)
3-(Chloracetyl)-l -[(2-chlor-l ,3-thiazol-5-yl)methyl]-lH-imidazo[l ,2-a]pyridin-4-ium-2 -olat 3- (Chloroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridin-4-ium-2 -olate
(Verbindung Nr. 1-1 -002) (200 mg, 0,58 mmol) wurde in TH F (10 mL) vorgelegt und mit Ethylamin (66,0 mg, 1,46 mmol) in 1 mL THF versetzt. Das Reaktionsgemisch wurde anschließend bei bei 50°C 16 Stunden gerührt. Das Reaktionsgemisch wurde in Dichlormethan/Wasser aufgenommen, die organische Phase abgetrennt und über Magnesiumsulfat getrocknet. Nach Abdestillieren des Lösungsmittel unter vermindertem Druck wurde der Rückstand auf Kieselgel adsorbiert und mit Dichlormethan/2-Propanol (92:8) als Laufmittel chromatograpliiert. Es wurden 132 mg (60,5 % der Theorie) 1 -[(2 -Chlor- 1 ,3 -thiazol-5 -yl)methyl] -3 -(N-ethylglycyl)- 1 H-imidazo [ 1 ,2-a]pyridin-4-ium-2-olat erhalten. HPLC-MS: logP = 0,57; Masse (m/z): 350,9; 'HNMR ( Π, -DM SO): δ 1.15 (m, 3 H ). 3,02 (m, 2H), 4,27 (s, 2H), 5.43 (s, 2H), 7.45. (m, 1H), 7.87 (s, 1H), 7.96 (m, 2H), 9.76 (m, 1H). (Compound No. 1-1 -002) (200 mg, 0.58 mmol) was initially charged in THF (10 mL) and treated with ethylamine (66.0 mg, 1.46 mmol) in 1 mL THF. The reaction mixture was then stirred at 50 ° C for 16 hours. The reaction mixture was taken up in dichloromethane / water, the organic phase separated and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was adsorbed on silica gel and chromatographed with dichloromethane / 2-propanol (92: 8) as the eluent. There were 132 mg (60.5% of Theory) 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (N-ethylglycyl) -1 H -imidazo [1,2-a] pyridin-4-ium-2 obtained olat. HPLC-MS: log P = 0.57; Mass (m / z): 350.9; 'HNMR (Π, -DM SO): δ 1.15 (m, 3 H). 3.02 (m, 2H), 4.27 (s, 2H), 5.43 (s, 2H), 7.45. (m, 1H), 7.87 (s, 1H), 7.96 (m, 2H), 9.76 (m, 1H).
Svnthesebeispiel Nr. 8 -(N-Acctyl !-cthyl«lycyl)- l^ Synthesis Example No. 8 - (N-Acctyl ! -Cthyl-lycyl) -1-
olat (Verbindung Nr.I-1 -040) olate (compound no. I-1 -040)
l -[(2-Chlor-l,3-thiazol-5-yl)methyl]-3-(N-ethylglycyl)-lH-imidazo[l ,2-a]pyridin-4-ium-2-olat (Verbindung Nr. 1-1 -021) (56,0 mg, 0,16 mmol) wurde in Dichlormethan (5 mL) vorgelegt und mit Triethylamin (19,5 mg, 0,19 mmol) und anschließend mit Acetylchlorid (15,1 mg, 0,19 mmol) versetzt. Das Reaktionsgemisch wurde bei Raumtemperatur 2 Stunden gerührt und dann das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wurde an Isolute adsorbiert und über Aluminiumoxid mit Dichiormethan 2-Propanol (92:8) als Laufmittel chromatographiert. Es wurden 30,0 mg (46,9 % der Theorie) 3-(N-Acetyl-N-ethylglycyl)-l -[(2-chlor-l ,3-thiazol-5-yl)methyl]-lH-imidazo[l ,2-a]pyridin-4- ium-2-olat erhalten. HPLC-MS: logP = 1 ,49; Masse (m/z): 392,9; 'HNMR ( D -DM SO ): δ 1.01 (t, 3H), 2,07 (s, 3H), 3,85 (m, 2H), 4.57 (s, 1H), 4.68 (s, 1H), 5.42 (s, 2H), 7.38, (m, 1H), 7.90 (m, 3H), 9.84 (m, 1H). 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (N-ethylglycyl) -1H-imidazo [1,2-a] pyridin-4-ium-2-olate (Comp No. 1-1 -021) (56.0 mg, 0.16 mmol) was initially charged in dichloromethane (5 mL) and triethylamine (19.5 mg, 0.19 mmol) followed by acetyl chloride (15.1 mg , 0.19 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then the solvent was distilled off under reduced pressure. The residue was adsorbed on isolute and chromatographed on alumina with dichloromethane 2-propanol (92: 8) as eluent. There were 30.0 mg (46.9% of theory) of 3- (N-acetyl-N-ethylglycyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridine-4-ium-2-olate. HPLC-MS: log P = 1.49; Mass (m / z): 392.9; 'HNMR (D -DM SO): δ 1.01 (t, 3H), 2.07 (s, 3H), 3.85 (m, 2H), 4.57 (s, 1H), 4.68 (s, 1H), 5.42 (s, 2H), 7.38, (m, 1H), 7.90 (m, 3H), 9.84 (m, 1H).
Svnthesebeispiel Nr. 9 -Aci-tyl- l -|(2-chlor-l, -thiazol-5-yO (Verbindung Nr.I- 1 -043) Synthesis Example No. 9-Acyl-1 - | (2-chloro-1-thiazol-5-y-O (Compound No.I-1 -043)
3-(Chloracetyl)-l -[(2-chlor-l ,3 -thiazol-5 -yl)methyl]-l H-imidazo [1 ,2-a]pyridin-4-ium-2-olat 3- (Chloroacetyl) -1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -1H-imidazo [1,2-a] pyridin-4-ium-2-olate
(Verbindung Nr. 1-1 -002) (1,53 g, 4.46 mmol) wurde in THF (20 mL) vorgelegt und mit aktiviertem Zinkpulver (875 mg, 13,3 mmol) versetzt. Das Reaktionsgemisch wurde anschließend bei Raumtemperatur 5 Stunden gerührt, über Kieselgur filtriert, der Rückstand mit Dichlormethan nachgewaschen und nacheinander mit Wasser und gesättigter Natriumhydrogencarbonatlösung gewaschen. Nach Trocknen über Magnesiumsulfat und AbdestiUieren des Lösungsmittels unter vermindertem Druck wurde der Rückstand wurde auf Kieselgel adsorbiert und mit Dichlormethan/ 2- Propanol (92:8) als Laufmittel chromatographiert. Es wurden 1 ,02 g (71,7 % der Theorie) 3-Acetyl-l - [(2-chlor- 1 ,3 -thiazol-5-yl)methyl] - 1 H-imidazo [ 1 ,2-a]pyridin-4-ium-2-olat erhalten. HPLC-MS: logP = 1 ,29; Masse (m/z): 308,1 ; 'HNMR ( D -DM SO): δ 2.44 (s, 3H), 5.40 (s, 2H), 7.34, (m, 1H), 7.85 (m, 3H), 9.92 (m, 1H). (Compound No. 1-1 -002) (1.53 g, 4.46 mmol) was initially charged in THF (20 mL) and activated with activated zinc powder (875 mg, 13.3 mmol). The reaction mixture was then added Stirred for 5 hours, filtered through kieselguhr, the residue washed with dichloromethane and washed successively with water and saturated sodium bicarbonate solution. After drying over magnesium sulfate and distilling off the solvent under reduced pressure, the residue was adsorbed onto silica gel and chromatographed with dichloromethane / 2-propanol (92: 8) as eluent. There were 1, 02 g (71.7% of theory) of 3-acetyl-l - [(2-chloro-1, 3-thiazol-5-yl) methyl] - 1 H-imidazo [1, 2-a] pyridin-4-ium-2-olate. HPLC-MS: log P = 1.29; Mass (m / z): 308.1; 'HNMR (D -DM SO): δ 2.44 (s, 3H), 5.40 (s, 2H), 7.34, (m, 1H), 7.85 (m, 3H), 9.92 (m, 1H).
Synthesebeispiel Nr. 10 l -|(2-C hlor- l ^-thiazol-5-yl)nHthyl|-3-(nutho\ycarbonyl)-l H-imid Synthesis Example No. 10 l - | (2-C-Chloro-1-thiazol-5-yl) n -Hethyl | -3- (nuthoylcarbonyl) -1H-imide
(Verbindung Nr.I-1 -085)  (Compound No. I-1 -085)
Zu einer Lösung von N-[(2-Chlor-l ,3-thiazol-5-yl)methyl]pyridin-2-amin (3,14 g, 13,8 mmol) und Triethylamin (1,69 g, 16,6 mmol) in Dichlormethan (50 mL) wurde langsam Methyl-2,3-dichlor-3- oxopropanoat (bekannt aus Tetrahedron 1993, 49, 9447-9452) (2.85 g, 16,6 mmol) gelöst in 20 ml Dichlormethan getropft und anschließend bei Raumtemp eratur 3 Stunden gerührt. Das Reaktionsgemisch wurde mit Dichlormethan verdünnt, mit Wasser gewaschen, die organische Phase abgetrennt und über Magnesiumsulfat getrocknet. Nach AbdestiUieren des Lösungsmittels unter vermindertem Druck wurde der Rückstand wurde auf Kieselgel adsorbiert und mit Dichlormethan/2- Propanol (92:8) als Laufmittel chromatographiert. Es wurden 2,48 g (54,5 % der Theorie) l-[(2-Chlor- 1 ,3-thiazol-5-yl)methyl]-3 -(methoxycarbonyl)- 1 H-imidazo [ 1 ,2-a]pyridin-4-ium-2-olat erhalten. HPLC- MS: logP = 1,23; Masse (m/z): 324,0; 'HNMR ( D -DMSO): δ 3.74 (s, 3H), 5.38 (s, 2H), 7.34, (m, 1H), 7.76 (m, 1H), 7.83 (m, 2H), 9.46 (s, 1H). To a solution of N - [(2-chloro-l, 3-thiazol-5-yl) methyl] pyridin-2-amine (3.14 g, 13.8 mmol) and triethylamine (1.69 g, 16%). 6 mmol) in dichloromethane (50 mL) was slowly added dropwise methyl-2,3-dichloro-3-oxopropanoate (known from Tetrahedron 1993, 49, 9447-9452) (2.85 g, 16.6 mmol) dissolved in 20 ml of dichloromethane and then stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane, washed with water, the organic phase separated and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was adsorbed onto silica gel and chromatographed with dichloromethane / 2-propanol (92: 8) as eluent. There was added 2.48 g (54.5% of theory) of l - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (methoxycarbonyl) -1H-imidazo [1, 2]. a] pyridin-4-ium-2-olate. HPLC-MS: logP = 1.23; Mass (m / z): 324.0; 'HNMR (D-DMSO): δ 3.74 (s, 3H), 5.38 (s, 2H), 7.34, (m, 1H), 7.76 (m, 1H), 7.83 (m, 2H), 9.46 (s, 1H ).
Synthesebeispiel Nr. 11 H(2-C hlor-l , -thiazol-5-yl)niethy^ Synthesis Example No. 11 H (2-chloro-1, -thiazol-5-yl) -niethy ^
olat (Verbindung Nr.I-1 -11 1) olate (Compound No.I-1 -11 1)
Cyclopropylamin (50,0 mg, 0,87 mmol) wurde in TH F vorgelegt, bei 0°C eine 2M Lösung Trimethylaluminium in Tokio! (56,4 mg, 0,78 mmol) zugetropft und anschließend 20 Minuten gerührt. Hieraufhin wurde eine Lösung von 1 - [(2-Chlor- 1 ,3 -thiazol-5 -yl)methyl] -3 -(methoxycarbonyl)- 1 H- imidazo[l ,2-a]pyridin-4-ium-2-olat (Verbindung Nr. 1-1 -085) (101 ,3 mg, 0,31 mmol) in Dichlormethan (5 mL) zugegeben und 4 Stunden bei 40°C gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch zunächst mit 15 mL 10%iger Salzsäure verrührt und anschließend mehrfach mit Dichlormethan extrahiert. Die organische Phase wurde mit Wasser gewaschen und über Magnesiumsulfat getrocknet. Nach AbdestiUieren des Lösungsmittesl unter vermindertem Druck wurde der Rückstand auf Kieselgel adsorbiert und mit Dichlormethan 2-Propanol (92:8) als Laufmittel chromatographiert. Es wurden 99 mg (40,8 % der Theorie) 1 -[(2-Chlor-l ,3 -thiazol-5-yl)methyl] -3 -(cyclopropylcarbamoyl)- 1 H-imidazo [ 1 ,2- a]pyridin-4-ium-2-olat erhalten. HPLC-MS: logP = 1,63; Masse (m/z): 349,0; 'HNMR ( D -DMSO): δ 0.48 (m, 2H), 0.71 (m, 2 H ). 2,76 (m, 1H), 5.43 (s, 2H), 7.32, (m, 1H), 7.71 (m, 1H), 7.84 (m, 1H), 7.94 (m, 1H), 9.63 (m, 1H). Synthesebeispiel Nr. 12 l-[(6-CMorpyridin-3-yI)methy!j-3-(methoxycarbo Cyclopropylamine (50.0 mg, 0.87 mmol) was initially charged in THF, at 0 ° C a 2M solution of trimethylaluminum in Tokyo! (56.4 mg, 0.78 mmol) was added dropwise and then stirred for 20 minutes. This was followed by a solution of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (methoxycarbonyl) -1H-imidazo [1,2-a] pyridin-4-ium-2 -olate (Compound No. 1-1-085) (101, 3 mg, 0.31 mmol) in dichloromethane (5 mL) was added and stirred at 40 ° C for 4 hours. For workup, the reaction mixture was first stirred with 15 mL of 10% hydrochloric acid and then extracted several times with dichloromethane. The organic phase was washed with water and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was adsorbed on silica gel and chromatographed with dichloromethane 2-propanol (92: 8) as the eluent. 99 mg (40.8% of theory) of 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -3- (cyclopropylcarbamoyl) -1H-imidazo [1, 2-a] pyridin-4-ium-2-olate. HPLC-MS: log P = 1.63; Mass (m / z): 349.0; 'HNMR (D-DMSO): δ 0.48 (m, 2H), 0.71 (m, 2H). 2.76 (m, 1H), 5.43 (s, 2H), 7.32, (m, 1H), 7.71 (m, 1H), 7.84 (m, 1H), 7.94 (m, 1H), 9.63 (m, 1H ). Synthesis Example No. 12 l - [(6-CMorphyridin-3-yl) methyl-3- (methoxycarbo
(Verbindung Nr. 1-4-001) (Compound No. 1-4-001)
1. Synthese von N-[(6-Chlo yridin-3-yl)methyl]pyrimidin-2-amin 1. Synthesis of N - [(6-chloro-3-yl) methyl] pyrimidin-2-amine
Eine Lösung von 2-Brompyrimidin (5,00 g, 31 ,5 mmol), Palladiumacetat (0,71 mg, 3,1 mmol), 4,5-Bis- (diphenylpho sphino) -9, 9 -dimethyl xanthen (3,64 g, 6.3 mmol) und Kaliumcarbonat (34,77 g, 25 1.6 mmol) in Dioxan (80 mL) wurde mit 1 -{6-Chlorpyridin-3 -yl)methanamin (6,73 g, 47,2 mmol) versetzt und anschließend auf 100 °C erhitzt. Das Reaktionsgemisch wurde über Celite filtriert und in Dichlormethan aufgenommen. Die organische Phase wurde über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Der Rückstand wurde auf Kieselgel adsorbiert und Chromatographien. Es wurden 1,750 g (23,9 % d.Th.) N-[(6-Chlo yridin-3-yl)methyl] yrimidin-2-amin erhalten. HPLC-MS: logP = 1,36; Masse (m/z): 221,1; 'HNMR (D6-DMSO): δ 8.32 (m, 4H), 7.76 (m, 2H), 7.46 (m, 1H), 6.60 (m, 1H), 4.49 (d, 2H). A solution of 2-bromopyrimidine (5.00 g, 31.5 mmol), palladium acetate (0.71 mg, 3.1 mmol), 4,5-bis (diphenylphosphino) -9,9-dimethyl xanthene (3 , 64 g, 6.3 mmol) and potassium carbonate (34.77 g, 25.6 mmol) in dioxane (80 mL) was treated with 1- {6-chloropyridin-3-yl) methanamine (6.73 g, 47.2 mmol). added and then heated to 100 ° C. The reaction mixture was filtered through Celite and taken up in dichloromethane. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was adsorbed on silica gel and chromatographies. This gave 1.750 g (23.9% of theory) of N - [(6-chloro-3-yl-yl) -methyl] -rimidin-2-amine. HPLC-MS: log P = 1.36; Mass (m / z): 221.1; 'HNMR (D6-DMSO): δ 8.32 (m, 4H), 7.76 (m, 2H), 7.46 (m, 1H), 6.60 (m, 1H), 4.49 (d, 2H).
2. Synthese von 1 -[(6-Chlorpyridin-3 -yl)methyl] -3 -(methoxycarbonyl)- 1 H-imidazo [ 1 ,2- a] pyrimidin-4 -ium-2 -olat 2. Synthesis of 1 - [(6-chloropyridin-3-yl) methyl] -3- (methoxycarbonyl) -1H-imidazo [1,2-a] pyrimidin-4-yl-2-olate
Eine Lösung von N-[(6-Chlorpyridin-3-yl)methyi]pyrimidin-2-amin (0,50 g, 2,3 mmol) in Dioxan, 4- Dimethylaminopyridin (1 Spatelspitze) und Triethylamin (0,46 g, 4,5 mmol) wurde bei 0 °C mit Methyl - 3-chlor-3-oxopropanoat (0,93 g, 6,8 mmol) versetzt und anschließend Übernacht bei 25 °C gerührt. Das Reaktionsgemisch wurde in eine Ammoniumchloridlösung gegossen und dann in Ethylacetat aufgenommen. Die organische Phase wurde über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Der Rückstand wurde auf Kieselgel adsorbiert, schnell chromatographiert und weiter umgesetzt. A solution of N - [(6-chloropyridin-3-yl) methyl] pyrimidin-2-amine (0.50 g, 2.3 mmol) in dioxane, 4-dimethylaminopyridine (1 spatula tip) and triethylamine (0.46 g , 4.5 mmol) at 0 ° C with methyl 3-chloro-3-oxopropanoate (0.93 g, 6.8 mmol) and then stirred overnight at 25 ° C. The reaction mixture was poured into an ammonium chloride solution and then taken up in ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was adsorbed on silica gel, rapidly chromatographed and reacted further.
Eine Lösung von Methyl-3 - { [(6-chlorpyridin-3 -yl)methyl](pyrimidin-2-yl)amino } -3 -oxopropanoat (0,29 g, 0,9 mmol) in Dioxan wurde bei 25 °C mit N-Bromsuccinimid (0,32 g, 1,8 mmol) versetzt und anschließend 2 Stunden bei 50 °C gerührt. Das Reaktionsgemisch wurde in eine Ammoniumchloridlösung gegossen und dann in Ethylacetat aufgenommen. Die organische Phase wurde über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Der Rückstand wurde auf Kieselgel adsorbiert und chromatographiert. Es wurden 97 mg (29 % d.Th.) l-[(6- Chlorpyridin-3 -yl)methyl] - -(methoxycarbonyl)- 1 H-imida/o [ 1 ,2-a]pyrimidin-4 -ium-2 -olat erhalten. HPLC-MS: iogP = 1,15; Masse (m/z): 319,0; 'HNMR (D6-DMSO): δ 9.62 (m, 1H), 8.55 (m, 1H), 8.45 (m, 1H), 7.83 (m, 1H), 7.49 (m, 2H), 5.18 (s, 2H), 3. 75 (s, 3H). Svnthesebeispiel Nr. 13 A solution of methyl 3 - {[(6-chloropyridin-3-yl) methyl] (pyrimidin-2-yl) amino} -3-oxopropanoate (0.29 g, 0.9 mmol) in dioxane became 25 ° C with N-bromosuccinimide (0.32 g, 1.8 mmol) and then stirred at 50 ° C for 2 hours. The reaction mixture was poured into an ammonium chloride solution and then taken up in ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was adsorbed onto silica gel and chromatographed. 97 mg (29% of theory) of l - [(6-chloropyridin-3-yl) methyl] - (methoxycarbonyl) -1 H -imidazo [1,2-a] pyrimidinium-4-ymium were obtained -2 -olate obtained. HPLC-MS: iogP = 1.15; Mass (m / z): 319.0; 'HNMR (D6-DMSO): δ 9.62 (m, 1H), 8.55 (m, 1H), 8.45 (m, 1H), 7.83 (m, 1H), 7.49 (m, 2H), 5.18 (s, 2H) , 3. 75 (s, 3H). Synthesis Example No. 13
5-(CMoraeetyl)-7-[(6-cMorpyridin^ 5- (CMoraeetyl) -7 - [(6-cMorpyridin ^
(Verbindung Nr. 1-5-001) (Compound No. 1-5-001)
Eine Lösung von N-[(2-Chlor-l,3-thiazol-5-yl)methyl]pyridin-2-amin [bekannt aus WO2009099929] (500 mg, 2,21 mmol) in Dioxan wurde mit Chloressigsäureanhydrid (757 mg, 4,43 mmol) und Chloressigsäure (418 mg, 4,43 mmol) versetzt und anschließend 40 Stunden unter Rückfluß erhitzt. Nach Abkühlen wurde das Reaktionsgemisch vorsichtig in 150 ml. 10% ige kalte Natriumcarbonatlö sung gegossen und mehrfach mit Dichlormethan extrahiert. Die organische Phase wurde über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Der Rückstand wurde auf Kieselgel adsorbiert und mit Di h 1 on riet ha n/2 - Propan o 1 (92:8) als Laufmittel chromatographiert. Es wurden 30,0 mg (3,76 % der Theorie) 5-(Chloracetyl)-7-[(6-chloφyridin-3- yl)methyl] -7H-imidazo[2, 1 -b] [ 1 ,3 ]thiazol-4-ium-6-olat erhalten. HPLC-MS: logP = 1 ,33; Masse (m/z): 341 ,9; 'HNMR (D6-DMSO): δ 4.65 (s, 2H), 5.17 (s, 2H ). 7.47, (m, 1H), 7.55 (m, 1H), 7.92 (m, 1H), 8.52 (m, 2H ). A solution of N - [(2-chloro-1,3-thiazol-5-yl) methyl] pyridin-2-amine [known from WO2009099929] (500 mg, 2.21 mmol) in dioxane was treated with chloroacetic anhydride (757 mg , 4.43 mmol) and chloroacetic acid (418 mg, 4.43 mmol) and then heated under reflux for 40 hours. After cooling, the reaction mixture was carefully poured into 150 ml. 10% Cold Natriumcarbonatlö solution and extracted several times with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was adsorbed on silica gel and chromatographed with Di h 1 on riet ha n / 2 - propane o 1 (92: 8) as the eluent. There were obtained 30.0 mg (3.76% of theory) of 5- (chloroacetyl) -7 - [(6-chloropyridin-3-yl) methyl] -7H-imidazo [2, 1 -b] [1, 3] thiazole-4-ium-6-olate obtained. HPLC-MS: logP = 1.33; Mass (m / z): 341, 9; 'HNMR (D 6 -DMSO): δ 4.65 (s, 2H), 5.17 (s, 2H). 7.47, (m, 1H), 7.55 (m, 1H), 7.92 (m, 1H), 8.52 (m, 2H).
Die in den folgenden Tabellen 1 -3 beschriebenen erfindungsgemäßen Verbindungen der Formel (1-1), (1-4) und (1-5) sind ebenfalls bevorzugte erfindungsgemäße Verbindungen der Formel (I), die man gemäß oder anal g zu den oben beschriebenen Synthesebeispielen erhält. Tabelle 1 The compounds of the formula (1-1), (1-4) and (1-5) according to the invention which are described in the following Tables 1-3 are likewise preferred compounds of the formula (I) according to the invention which are obtained according to or above the above obtained synthesis examples. Table 1
Tabelle 2 Table 2
Tabdle l Tabdle l
1 H-N.M R Daten b) der Verbindungen gemäfi Tabelien 1, 2 und 3 1 HN.MR data b) of the compounds according to Tables 1, 2 and 3
Beispiel 1-1-001 : 1H-NMR(601, 6 MHz, de-DMSO): δ= 9,855(2,1);9,844(2,1);8,517(2,5);8,514(2,5);7,894(1,0);7,892(1,0);7.882(1,3);7,880(2,3 );7,878(1,5);7,867(1,4);7,865(1 ,4);7,832(1 ,6);7,828(1,6);7,819(1 ,8);7,814(1 ,7);7,762(2,5);7,748(2,0);7,503(3,0);7,489(2,7);7,413(1 ,2);7,411 ( 1,2);7,400(2,2);7,390(1,2);7,388(1,2);5,262(8,5);4,807(16,0);3,320(17,8);2,523(0,4);2,520(0,4);2,511(5,8);2,508(11,4);2,505(15,2):2,502(11, 1);2.499(5,3) Example 1-1-001: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.855 (2.1); 9.844 (2.1); 8.517 (2.5); 8.514 (2.5 7.894 (1.0), 7.892 (1.0), 7.882 (1.3), 7.880 (2.3), 7.878 (1.5), 7.867 (1.4), 7.865 (1, 4) 7.832 (1, 6); 7.828 (1.6); 7.819 (1, 8); 7.814 (1, 7); 7.762 (2.5); 7.748 (2.0); 7.503 (3.0); 7.499 (2.7), 7.413 (1, 2), 7.411 (1.2), 7.400 (2.2), 7.399 (1.2), 7.388 (1.2), 5.262 (8.5), 4.807 (16.0) 3,320 (17.8); 2,523 (0.4); 2,520 (0.4); 2,511 (5.8); 2,508 (11.4); 2.505 (15.2) 2.502 ( 11, 1); 2,499 (5,3)
Beispiel 1-1-002: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,842(2.7);9.826(2,7):7,956(0,4);7,934(2,7);7,926(3,5);7,921(5,9):7,906(0,6);7,854(6.1Example 1-1-002: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.842 (2.7); 9,826 (2.7): 7.956 (0.4); 7.934 (2.7); 7,926 (3.5); 7,921 (5.9) 7,906 (0.6); 7,854 (6.1
);7,433(1,2);7,426(1,1);7,417(1,8);7.410(1,7);7,402(1,1);7,394(1,1);5,755(1 ,2);5,414(10,1);4,794(16,0);3,3^ 7.433 (1.2), 7.426 (1.1), 7.417 (1.8), 7.410 (1.7), 7.402 (1.1), 7.394 (1.1), 5.755 (1, 2) ; 5,414 (10.1); 4,794 (16.0); 3.3 ^
503(72,0);2,499(54,9);2,329(0,5);1,046(0,6);1,031(0,6);0,000(3,3)  503 (72.0); 2,499 (54.9); 2,329 (0.5); 1,046 (0.6); 1,031 (0.6); 0,000 (3.3)
Beispiel 1-1-003: 1H-NMR(601,6 MHz, de-DMSO): δ= 9,900(2,8);9,889(2,8);8,509(3,4);8,505(3,3);7,826(1,3);7,824(1,3);7,812(4,7);7,798(3,8Example 1-1-003: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9,900 (2.8), 9.889 (2.8), 8.509 (3.4), 8.055 (3.3 ); 7,826 (1.3); 7,824 (1.3); 7,812 (4.7); 7,798 (3.8
);7,719(3,2);7,704(2,5);7,495(3,8);7,481(3,4);7,373(1,6);7,361 (2,9);7,350(1 ,5);5,238(11,0):4,542(16,0);3,818(0,4);3,802(0,4);3,364(29,5);3^ 11(20,5);2,614(0,5);2,505(51 ,1);2,502(65,3);2,499(47,8);2,387(0,4);0,000(51,4) 7,719 (3,2); 7,704 (2.5); 7,495 (3,8); 7,481 (3,4); 7,373 (1,6); 7,361 (2,9); 7,350 (1, 5) 5.283 (11.0): 4.542 (16.0); 3.818 (0.4); 3.802 (0.4); 3.364 (29.5); 3 ^ 11 (20.5); 2.614 (0.5 2.555 (51, 1), 2.502 (65.3), 2.499 (47.8), 2.387 (0.4), 0.000 (51.4)
Beispiel 1-1-004: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,766(3,4);9,750(3,5);8,539(4,3);8,533(4,4);8,387(0,4);8,179(0,5);7,959(9,1);7,901 (0,5 );7,886(1,3);7,884(1,4);7,862(4,6);7,855(2J);7,846(2!5);7,841 (3,4);7,834(2,9);7J76(3,8);7,755(2,5);7,533(8,9);7!521(5,1);7,500(4,5);7!398( 1 ,8);7,395(1 ,9);7,379(3,3);7,363(1 ,6);7,360(1 ,6);5,548(0,6);5,497(16,0);5,289(11,5);5,259(0,5);4,806(0,7);3,320(147,5);2,891 (0,8);2, 732(0,7 );2,676(0,6);2,671(0,8);2,667(0,6);2,507(98,9);2,502(129,1);2,498(94,6);2,333(0,6);2,329(0,8);2,325(0,6);0,000(4,7) Example 1-1-004: 'H NMR (400.0 MHz, de-DMSO): δ = 9.766 (3.4); 9.750 (3.5); 8.539 (4.3); 8.533 (4.4 8.877 (0.4), 8.179 (0.5), 7.959 (9.1), 7.901 (0.5 7,886 (1,3); 7,884 (1,4); 7,862 (4,6); 7,855 (2J); 7,846 (2 ! 5); 7,841 (3,4); 7,834 (2,9); 7J76 (3,8); 7,755 (2,5); 7,533 (8,9); 7 ! 521 (5,1); 7,500 (4,5); 7 ! 398 (1, 8), 7,395 (1, 9), 7,379 (3,3), 7,363 (1,6), 7,360 (1,6), 5,548 (0,6), 5,497 (16,0), 5,289 (11.5); 5.259 (0.5); 4.806 (0.7); 3.320 (147.5); 2.891 (0.8); 2, 732 (0.7); 2.676 (0.6); 2,671 (0.8); 2,667 (0.6); 2,507 (98.9); 2.502 (129.1); 2,498 (94.6); 2,333 (0.6); 2,329 (0.8); 2,325 (0.6); 0,000 (4.7)
Beispiel 1-1-005: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,909(1,4);9,893(1,5);9,859(0,3);9,842(0,4);8,513(2.2);8,507(1,9);7,879(0,3);7,849(0,6 Example 1-1-005: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.909 (1.4); 9.893 (1.5); 9.859 (0.3); 9.842 (0.4 ); 8,513 (2.2); 8.507 (1.9); 7,879 (0.3); 7,849 (0.6
);7,846(0,6);7,827(1,7);7,824(2,0);7,817(1,3);7,809(1,4);7,803(1,5);7,797(1 ,2);7,765(0,5);7,740(1,8);7,719(1,1);7,506(2,5);7,485(2,2);7,407.846 (0.6), 7.827 (1.7), 7.824 (2.0), 7.817 (1.3), 7.809 (1.4), 7.803 (1.5), 7.797 (1, 2) ; 7,765 (0.5); 7,740 (1.8); 7,719 (1.1); 7,506 (2.5); 7,485 (2.2); 7.40
0,4);7,380(0,9);7,377(0,8);7,361(1,4);7,345(0,7);7,342(0,7);5,256(5,7);4,806(2,3);3,819(8,3);3,322(22,3);2,512(14,6);2,508(29,3);2,504(38,30.4); 7,380 (0.9); 7,377 (0.8); 7,361 (1.4); 7,345 (0.7); 7,342 (0.7); 5,256 (5.7); 4,806 (2 , 3); 3,819 (8.3); 3,322 (22.3); 2.512 (14.6); 2,508 (29.3); 2.504 (38.3
);2,499(27,8);2,495(13,5);2,335(0,4);2,143(16,0);1,047(0,3);0,008(0,5);0,000(14,5);-0,008(0,5) ); 2,499 (27.8); 2,495 (13.5); 2,335 (0.4); 2,143 (16.0); 1.047 (0.3) 0.008 (0.5); 0,000 (14.5) ; -0.008 (0.5)
Beispiel 1-1-006: 1H-NMR(400,0 MHz, de-DMSO): 5= 9,838(0,4);9,811(3,2);9,794(3,2);8,539(4,0);8,533(4.1);8,313(0.4);8,289(4,0);8,282(4,2Example 1-1-006: 1 H-NMR (400.0 MHz, de-DMSO): 5 = 9.838 (0.4); 9.811 (3.2); 9.794 (3.2); 8.539 (4.0 ); 8,533 (4.1); 8,313 (0.4); 8,289 (4.0); 8.282 (4.2
);8,151(3,0);8,148(3,3);8,141 (3,1);8,137(3,1);8,125(0,3);7,874(1,4);7,871(1 ,7);7,867(2,6);7,861 (2,5);7^ 8.151 (3.0), 8.148 (3.3), 8.141 (3.1), 8.137 (3.1), 8.125 (0.3), 7.874 (1.4), 7.871 (1, 7) 7,867 (2,6); 7,861 (2,5); 7 ^
2,3);7,831(2,1);7,763(3,7);7,742(2,4);7,523(4,6);7,502(4,1);7,389(1,7);7,388(1,7);7,370(3,1);7,354(1,6);7,351(1,5);7,336(0,7);7,332{1,0);7,^ 25(0,8);7,315(2,7);7,311(3,0);7,308(3,2);7,304(2,9);7,300(3,6);7,289(3,2);7,279(0,9):7,268(1,1);5,754(7,7);5,332(16,0);5,283(11,1);3,319 ,1);2,676(0,7):2,671(0,9);2,667(0,7):2,507(120,4);2,502(154,8):2,498(111,4):2,333(0,7);2,329(0,9);2,325(0,7);1,352(0,3);1,234(0,9):1,04 5);1,030(0,5);0,008(2,6);0,000(56,6);-0,009(2,0)  2.3); 7,831 (2.1); 7,763 (3.7); 7,742 (2.4); 7,523 (4.6); 7,502 (4.1); 7,389 (1.7); 7,388 (1 , 7); 7,370 (3,1); 7,354 (1,6); 7,351 (1,5); 7,336 (0.7); 7,332 {1,0); 7, 25 (0,8); 7,315 (2.7); 7,311 (3.0); 7,308 (3.2); 7,304 (2.9); 7,300 (3.6); 7,289 (3.2); 7,279 (0.9) 7,268 ( 1.1), 5.754 (7.7), 5.332 (16.0), 5.283 (11.1), 3.319, 1), 2.676 (0.7): 2.671 (0.9), 2.667 (0.7 ): 2.507 (120.4); 2.502 (154.8) 2.498 (111.4) 2.333 (0.7); 2,329 (0.9); 2,325 (0.7); 1,352 (0.3) 1.244 (0.9): 1.04 5); 1.030 (0.5); 0.008 (2.6); 0.000 (56.6); - 0.009 (2.0)
Beispiel 1-1-007: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,840(3.0);9,823(3,1);8,541(3,9);8,536(3.8);8.364(0,3);7,867(3,3);7,861(2.4);7,847(5,4 );7,840(29);7,828(2,1);7,825(2,0);7,761(3,7);7,739(2,3);7,522(4,5);7,501(4,0);7,456(0,4);7,435(0,4);7,391(1,6);7,388(1 ,6);7,372(3,0 0,4);7,356(1 ,6);7,353(1 ,5);7,286(0,4);7,279(3,4);7,273(1 ,0);7,260(4,9);7,257(4,5);7,247(0,9);7,239(4,0);7,232(0,4);6,931 (1 ,9):6,929(1 ,8);6,9 15(7,0);6,912(6,4);6,895(8,8);6,527(0,4);6,506(0,4);6,503(0,3);5,754(2,9);5,282(10,6);5,247(16,0);4,484(0,6);4,469(0,6);3,322(56,4);2,676P ,4);2,672(0,5);2,667(0,4);2,525(1 ,3);2,512(32,1);2,507(64,9);2,503(85,0);2,498(61,1);2,494(29,1);2,3M(0.4);2,330(0,5);2,32 Example 1-1-007: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.840 (3.0), 9.823 (3.1), 8.541 (3.9), 8.536 (3.8), 8.364 ( 0.3), 7.867 (3.3), 7.861 (2.4), 7.847 (5.4), 7.840 (29), 7.828 (2.1), 7.825 (2.0), 7.761 (3.7); 7.739 (2.3), 7.522 (4.5), 7.551 (4.0), 7.456 (0.4), 7.435 (0.4), 7.391 (1.6), 7.388 (1, 6), 7.372 (3.0), 7.356 (1, 6), 7.353 (1, 5), 7.286 (0.4), 7.279 (3.4), 7.273 (1, 0), 7.260 (4.9) 7.257 (4.5), 7.247 (0.9), 7.239 (4.0), 7.232 (0.4), 6.931 (1.9), 6.929 (1, 8), 6.915 (7, 0); 6,912 (6.4); 6,895 (8.8); 6,527 (0.4); 6,506 (0.4); 6,503 (0.3); 5,754 (2.9); 5,282 (10.6 5.247 (16.0); 4.484 (0.6); 4.469 (0.6); 3.322 (56.4); 2.676P, 4); 2.672 (0.5); 2.667 (0.4); 2.525 (1, 3), 2.512 (32.1), 2.507 (64.9), 2.503 (85.0), 2.498 (61.1), 2.494 (29.1), 2.3M (0.4), 2.330 (0.5) 2.32
);1,031(1,4);0,008(1,2);0,000(31, 7);-0,009(1,0) 1.031 (1.4), 0.008 (1.2), 0.000 (31, 7), - 0.009 (1.0)
Beispiel 1-1-008: 1H-NMR(601,6 MHz, de-DMSO): δ= 9,885(2,8);9,884(1,7);9,874(2,7);9,873(1,8);7,886(0,5);7,876(4,8);7,873(3,1);7,872(2,6 );7,866(2,4);7,864(2,2);7,852(0,5);7,850(0,6);7,844(6,7);7,396(0,4);7,388(1 ,3);7,384(1 ,2);7,378(1 ,9);7,374(2,0);7,367(1 ,3);7,363(1 ,4);5,753(Example 1-1-008: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.885 (2.8); 9.884 (1.7); 9.874 (2.7); 9.873 (1.8 7.886 (0.5), 7.876 (4.8), 7.873 (3.1), 7.872 (2.6), 7.866 (2.4), 7.864 (2.2), 7.852 (0.5) 7.850 (0.6), 7.844 (6.7), 7.396 (0.4), 7.388 (1, 3), 7.384 (1, 2), 7.378 (1, 9), 7.374 (2.0); 7.367 (1, 3), 7.363 (1, 4), 5.753 (
1,1);5,392{8,6):5,259(0,5);4,532(16,0);3,949(1,8);3,367(36,0);3,312(52,7);2,615(0,3);2,524(0,6);2,521(0,7):2,518(0,7);2,509(19,2):2,506(43, 3):2,503(61,1);2,500(43,7);2,497(19,6);2,387(0,3);2,185(0,3):1,357(2,8);0,097(0,4);0,005(3,5);0,000(127,8);-0,006(3,9);-0,100(0,5)1.1); 5,392 {8.6) 5,259 (0.5); 4,532 (16.0); 3,949 (1.8); 3,367 (36.0); 3,312 (52.7); 2.615 (0 , 3), 2.524 (0.6), 2.521 (0.7): 2.518 (0.7), 2.509 (19.2): 2.506 (43, 3): 2.503 (61.1), 2.500 (43, 7); 2.497 (19.6); 2,387 (0.3); 2,185 (0.3) 1,357 (2.8); 0.097 (0.4) 0.005 (3.5) 0.000 (127.8 ) - 0.006 (3.9) - 0.100 (0.5)
Beispiel 1-1-009: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,782(3,2);9,765(3,3);8,462(0,5);8,455(0,5);7,940(0,9);7,922(6,5);7,907(2,9);7,905(2,7Example 1-1-009: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.782 (3.2), 9.765 (3.3), 8.462 (0.5), 8.455 (0.5 ); 7,940 (0.9); 7.922 (6.5) 7.907 (2.9); 7,905 (2.7
):7,877(8,0);7,842(0,6);7,833(0,9);7,743(5,0);7,738(4,6):7,428(5,3);7,425(5,3);7,403(1 ,5);7,396(1,5):7,386(2,4);7,380(2,7):7,370(1,3):7,364( 1,4);6,616(0,4);6,609(0,4);6,605(0,4);6,273(3,5);6,268(5,8);6,263(3,5);5,544(1,7);5,522(16,0);5,466(1,3);5,449(10,8);3,321{49,3);2,892(0,3); 2,672(0,4);2,508(50,4);2,503(66,5);2,499(48,9);2,330(0,4);1,233(0,6); 1 ,047(0,4); 1 ,031 (0,4);0,008(1 , 1 );0,000(31 ,9);-0,008(1 ,3) ): 7.877 (8.0); 7,842 (0.6); 7,833 (0.9); 7,743 (5.0); 7,738 (4.6) 7.428 (5.3) 7.425 (5.3) 7.403 (1, 5); 7.396 (1.5): 7.386 (2.4); 7.380 (2.7): 7.370 (1.3): 7.644 (1.4); 6.616 (0.4); 6,609 (0.4); 6,605 (0.4); 6,273 (3.5); 6,268 (5.8); 6,263 (3.5); 5,544 (1.7); 5,522 (16.0); 5,466 (1.3); 5,449 (10.8); 3.321 {49,3); 2,892 (0.3); 2,672 (0.4); 2,508 (50.4); 2.503 (66.5); 2,499 (48.9); 2,330 (0.4); 1,233 (0.6); 1, 047 (0.4); 1, 031 (0.4), 0.008 (1, 1), 0.000 (31, 9), - 0.008 (1, 3)
Beispiel 1-1-010: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,752(3,5);9,735(3,5);7,964(9,1);7,944(0,7);7,929(7,0);7,923(4,0);7,916(3,2);7,891 (0,5Example 1-1-010: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.752 (3.5); 9.735 (3.5); 7.964 (9.1); 7.944 (0.7 7.929 (7.0), 7.923 (4.0), 7.916 (3.2), 7.891 (0.5
);7,872(8,3);7,534(8,9);7,412(1,5);7,404(1,4):7,396(2,1):7,389(2,1);7,380(1 ,3);7,373(1 ,4);5,487(16,0);5,445(11,3);4,342(0,5);4,331(0,5);3,327.872 (8.3); 7.534 (8.9); 7.412 (1.5); 7.404 (1.4): 7.396 (2.1): 7.389 (2.1); 7.380 (1, 3) 7.373 (1, 4), 5.487 (16.0), 5.445 (11.3), 4.342 (0.5), 4.331 (0.5), 3.32
2(43,1):2,893(0,8);2,733(0,7);2,673(0,3);2,508(43,7):2,504(57,2):2,499(41,4);2,331(0,3):1,047(4,3):1,031(4,3);0,008(1,1);0,000(28J);-2 (43.1) 2,893 (0.8); 2,733 (0.7); 2,673 (0.3); 2,508 (43.7) 2,504 (57.2) 2,499 (41.4); 2.331 (0.3) 1.047 (4.3) 1.031 (4.3) 0.008 (1.1) 0.000 (28J); -
0,008(1,0) 0.008 (1.0)
Beispiel 1-1-011 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,761(3,1);9,745(3.1);7,954(2,6);7,929(6,5);7,924(4,0);7,917(3.3);7,892(0,6);7,874(7.7 );7,818(5,5);7,812(5,4);7,771 (0,3);7,573(0,4);7,411(1,4);7,404(1,5);7,395(1 ,9);7,389(2,1);7,380(1,3);7,373(1,3);6,338{5,7):6,332(5,7);5,499( 0,5);5,478(14,4);5,445(10,5);5.421(0,5);5,414(0,4);4,583(0.3)A Example 1-1-011: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.761 (3.1); 9.745 (3.1); 7.954 (2.6); 7.929 (6.5); 7.924 (4.0); 7.917 (3.3); 7.892 (0.6); 7.874 (7.7); 7.818 (5.5); 7.812 (5.4); 7.771 (0.3); 7.573 (0.4 7.411 (1.4); 7.404 (1.5); 7.955 (1, 9); 7.389 (2.1); 7.380 (1.3); 7.373 (1.3); 6.338 {5.7) : 5.332 (5.7), 5.499 (0.5), 5.478 (14.4), 5.445 (10.5), 5,421 (0.5), 5.414 (0.4), 4.583 (0.3) A
3,2);2,504(70,4):2,499(52,1);2,330(0,4);2,326(0,4);1 ,338(0,4):1,226(0,5);0,008(0,5):0,000(11,7);-0,008(0,5)  3.2); 2.504 (70.4): 2.499 (52.1); 2.330 (0.4); 2.326 (0.4); 1.338 (0.4): 1.226 (0.5); 0.008 (0.5) 0.000 (11.7) - 0.008 (0.5)
Beispiel 1-1-012: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,790(2,0);9,773(2,2);9,754(0,3);8,313(0,4):7,934(0,7);7,918(4,5);7,903(2,0);7,901 (1,9 ):7,875(5,3);7,783(0,3);7,596(3,0);7,591 (2,9);7.402(0,9);7,395(1 ,0):7,386(1 ,4):7,379(1 ,7);7,370(0,8);7,363(1 ,0);7,281 (0,6);7.277(0,6);6,043( 0,6);6,026(3,0);6,021(3,1);5,443(7,1);5,410(9,3);3,325(29,0);2,891(0,3);2,676(0,4);2,671(0.6);2,667(0,4);2,524(1 ,4);2.511(36,6);2Example 1-1-012: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.790 (2.0), 9.773 (2.2), 9.754 (0.3), 8.313 (0.4 7.934 (0.7); 7.918 (4.5); 7.903 (2.0); 7.901 (1.9): 7.875 (5.3); 7.783 (0.3); 7.596 (3.0) 7.551 (2.9); 7,402 (0.9); 7,395 (1, 0): 7,386 (1, 4): 7,379 (1, 7); 7,370 (0.8); 7,363 (1, 0); 7.281 (0.6), 7.277 (0.6), 6.043 (0.6), 6.026 (3.0), 6.021 (3.1), 5.443 (7.1), 5.410 (9.3), 3.325 (29.0); 2.891 (0.3); 2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.524 (1, 4); 2.511 (36.6); 2
2,502(101,0):2,498(74,2):2,493(36,6);2,333(0,4):2,329(0,6);2,324(0,4):2,244(1,2):2,215(2,5);2,135(16,0);1,234(0,5):1,046(1,3);1,030(1,3):0, 008(1,7);0,000(50,3):-0,008(1,8) 2.502 (101.0) 2.498 (74.2) 2,493 (36.6); 2,333 (0.4) 2,329 (0.6); 2,324 (0.4) 2,244 (1.2): 2.215 (2.5); 2.135 (16.0); 1.234 (0.5): 1.046 (1.3); 1.030 (1.3): 0.008 (1.7); 0.000 (50.3): -0.008 (1.8)
Beispiel 1-1-013: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,785(1 ,4);9,768(1 ,4);7,936(0,4);7,921 (2,8);7,906(1 ,3);7,904(1 ,2);7,881 (0,3);7,872(3,5 );7,477(3,3);7,475(3,3);7,405(0,6);7,398(0,6);7,389(1,0);7,382(1,1);7,373(0,5);7,366(0,6);7.192(3,4);7,191(3.4);5,442(4,6);5,393^ 6,7);3,765(1,1);3,672(16,0);3,318(81,0);2,675(0,5);2,671(0,6);2,666(0,4);2,541(0,4);2,524(1,6);2,510(39,2);2,506(78,2);2,502(102,0);2,497( 73,7);2,493(35,6);2,333(0,4);2,328(0,6);2,324(0,4);1 ,045(0,7);1,030(0,7);0,008(1,9);0,000(48,3);-0,009(1,7) Example 1-1-013: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.785 (1, 4); 9.768 (1, 4); 7.936 (0.4); 7.921 (2.8 7.906 (1, 3), 7.904 (1.2), 7.881 (0.3), 7.872 (3.5), 7.477 (3.3), 7.475 (3.3), 7.405 (0.6) ; 7,398 (0.6); 7,389 (1.0); 7,382 (1.1); 7,373 (0.5); 7,366 (0.6); 7,192 (3.4); 7,191 (3.4); 5,442 ( 4.6), 5.363 ^ 6.7), 3.765 (1.1), 3.672 (16.0), 3.318 (81.0), 2.675 (0.5), 2.671 (0.6), 2.666 (0 , 4), 2.541 (0.4), 2.524 (1.6), 2.510 (39.2), 2.506 (78.2), 2.502 (102.0), 2.497 (73.7), 2.493 (35, 6); 2.333 (0.4); 2.328 (0.6); 2.324 (0.4); 1, 045 (0.7); 1.030 (0.7); 0.008 (1.9); 0.000 (48 , 3), - 0.009 (1.7)
Beispiel 1-1-014: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,743(3,6);9,726(3,5);8,518(10,5);7,960(10,9);7,952(0,8);7,938(6,6);7,936(7,0);7,930(3 ,9);7,925(3,5);7,922(3,1);7.903(0,5);7,900(0,5);7,877(8,7);7,412(1,5);7.404(1 ,5);7,398(1 ,7);7,396(1,9);7,390(1 ,9);7,388(1 ,9);7,381 (1 ,4);7,37 4(1,4);5,755(2,6);5,618(16,0);5,451(11,2);3,321(35,7);2,893(0,7);2,733(0,6);2,673{0,3);2,526(0,8);2,513(20,0):2,508(41,6);2,504(55,1);2,49 9(39,6):2,495(18,9);1,233(0,5);0,008(1,0);0,000(30,8);-0,009(1,1) Example 1-1-014: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.743 (3.6), 9.726 (3.5), 8.518 (10.5), 7.960 (10.9 7.952 (0.8), 7.938 (6.6), 7.936 (7.0), 7.930 (3.9), 7.925 (3.5), 7.922 (3.1), 7.903 (0.5) 7.900 (0.5); 7.877 (8.7); 7.412 (1.5); 7,404 (1, 5); 7,398 (1, 7); 7,396 (1,9); 7,390 (1, 9); 7.388 (1, 9), 7.381 (1, 4), 7.37 4 (1.4), 5.755 (2.6), 5.618 (16.0), 5.451 (11.2), 3.321 (35.7 ); 2,893 (0.7); 2,733 (0.6); 2.673 {0.3); 2,526 (0.8); 2,513 (20.0) 2,508 (41.6); 2.504 (55.1) 2.49 9 (39.6): 2.495 (18.9); 1.233 (0.5); 0.008 (1.0); 0.000 (30.8); -0.009 (1.1)
Beispiel 1-1-015: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,727(3.8);9,710(3,7);8,561(9,9);8,313(0,4);8,064(9,9);7,950(0,8);7,937(7,9);7,928(5,3Example 1-1-015: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.727 (3.8), 9.710 (3.7), 8.561 (9.9), 8.313 (0.4); 8,064 (9.9); 7,950 (0.8); 7,937 (7.9); 7,928 (5.3
);7,901(0,5);7,872(8,9);7,415(1,6);7,406(1,7);7,398(2,1);7,391 (2,1);7,385(1 ,5);7,377(1 ,4);5,602(16,0);5,446^ 7.901 (0.5), 7.872 (8.9), 7.415 (1.6), 7.406 (1.7), 7.398 (2.1), 7.391 (2.1), 7.385 (1, 5) 7.377 (1, 4), 5.602 (16.0), 5.446 ^
506(150,8);2,502(196,3);2,498(146,9);2,329(1,1);1,226(0,3);0,146(0,3);0,000(73,0);-0,150(0,3) 506 (150.8) 2.502 (196.3); 2.498 (146.9); 2,329 (1.1); 1,226 (0.3); 0,146 (0.3); 0,000 (73.0); - 0.150 (0.3)
Beispiel 1-1-016: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,953(0,4);9,936(0,4);9,914(1 ,6);9,898(1 ,7);8,511 (2,6);8,505(2,2);7,821 (1 ,6);7,815(1 ,6 );7,807(1,7);7,801 (2,0);7,794(1 ,9);7,788(1 ,4);7,719(1 ,9);7,706(0,6);7,698(1 ,3);7,500(2,9);7,480(2,6);7,373(0.9);7,371 (0,9);7,355(1 ,6);7,338(Example 1-1-016: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.953 (0.4), 9.936 (0.4), 9.914 (1.6), 9.898 (1.7 8,511 (2,6), 8,505 (2,2), 7,821 (1,6), 7,815 (1,6), 7,807 (1,7), 7,801 (2,0), 7,794 (1, 9) 7.788 (1, 4), 7.719 (1, 9), 7.706 (0.6), 7.698 (1, 3), 7.500 (2.9), 7.480 (2.6), 7.373 (0.9), 7.371 ( 0.9), 7.355 (1, 6), 7.338 (
0,8);7,336(0,8);5,754(4,1);5,250(1,8);5,239(5,9);4,589(8,8);3,709(0,4);3,694(1,1):3,679(1,5);3,664(1,1);3,649(0,5);3,319(59,5);2,672(0,5):2, 667(0,4);2,507(70,7);2,502(91,8);2,498(67,0);2,446(3,3):2,329(0,5);2,325(0,4);1,234(0,6);1,143(18,0);1 ,128(15,8);0,000(32,4);-0,008(1,3)0.8); 7,336 (0.8); 5,754 (4.1); 5,250 (1.8); 5,239 (5.9); 4,589 (8.8); 3,709 (0.4); 3,694 (1 , 1): 3.679 (1.5), 3.664 (1.1), 3.649 (0.5), 3.319 (59.5), 2.672 (0.5): 2, 667 (0.4), 2.507 ( 70.7) 2,502 (91.8); 2,498 (67.0); 2,446 (3.3) 2,329 (0.5); 2,325 (0.4); 1,234 (0.6); 1,143 (18 , 0); 1, 128 (15.8); 0.000 (32.4); - 0.008 (1.3)
Beispiel 1-1-017: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.826(3,3);9,810(3,3);7.955(0,5);7,933(0,7);7,916(6,5);7,901(3.1);7,873(8,0);7,531 (0,4 );7,406(1,4);7,400(1,4);7,390(2,4);7,384(2,5);7,374(1,3);7,368(1,4);7,331(0,4);7,310(0,3);7,286(0,4);7,280(3,4);7,274(1 ,1);7,259(4,9);7,25 4,7);7,246(1,1);7,239(4,0);6,933(1,9);6,917(8,0);6,914(6,6);6,896(9,3);6,880(0,3);5,755(0,5);5,439(10,9);5,331(0,5);5,239(16,0);5,21^ ,322(44,7);2,893(3,1);2,734(2.7);2,673(0.4);2,526(0,9);2,508(46.2);2,504(60.4);2,500(43,6);2,331(0,4);1 ,047(0,5):1,^ Example 1-1-017: 1 H NMR (400.0 MHz, de-DMSO): δ = 9,826 (3.3); 9.810 (3.3); 7,955 (0.5); 7,933 (0.7 7.916 (6.5), 7.901 (3.1), 7.873 (8.0), 7.531 (0.4), 7.406 (1.4), 7.400 (1.4), 7.399 (2.4), 7.384 (7,274 (2.5); 7.374 (1.3); 7,368 (1.4); 7,331 (0.4); 7,310 (0.3); 7,286 (0.4); 7,280 (3.4) 7.131), 7.259 (4.9), 7.25 (4.7), 7.246 (1.1), 7.239 (4.0), 6.933 (1.9), 6.917 (8.0), 6.914 ( 6.6); 6,896 (9.3); 6,880 (0.3); 5,755 (0.5); 5,439 (10.9); 5,331 (0.5); 5,239 (16.0); 5.21 ^, 322 (44,7); 2,893 (3,1); 2,734 (2.7); 2,673 (0.4); 2.526 (0.9); 2.508 (46.2); 2.504 (60.4); 2.500 (43.6); 2.331 (0.4); 1, 047 (0.5): 1, ^
0(22,9);-0,008(0,8) Beispiel 1-1-018: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.843(0,5);9,797(3,3);9,781(3,3);8,313(0,4);8,287(3,8);8,281(3,9);8,153(2,8);8,149(3,20 (22.9) - 0.008 (0.8) Example 1-1-018: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,843 (0.5), 9.797 (3.3), 9.781 (3.3), 8.313 (0.4 ); 8,287 (3.8); 8,281 (3.9); 8,153 (2.8); 8,149 (3.2
);8,142(2,9);8,138(3,0);8,126(0,5);8,119(0,4);7,934(0,6);7,919(6,5);7,914(3,8);7,906(3,0);7,903(2,7);7,884(0,7);7,881(0,6);7,869(8,0)); 8,142 (2.9); 8,138 (3.0); 8,126 (0.5); 8.119 (0.4); 7,934 (0.6); 7.919 (6.5) 7.914 (3.8) ; 7,906 (3.0); 7,903 (2.7); 7,884 (0.7); 7,881 (0.6); 7,869 (8.0)
1,4);7,396(1,4);7,388(2,0);7,381(2,1);7,372(1,3);7,365(1,4);7,337(0,7);7,333(0,9);7,330(0,7);7,326{0,8);7,316(2,5);7,312(2,8);7,309(3,0);7,31.4); 7,396 (1.4); 7,388 (2.0); 7,381 (2.1); 7,372 (1.3); 7,365 (1.4); 7,337 (0.7); 7,333 (0 , 9); 7,330 (0.7); 7.326 {0.8); 7,316 (2.5); 7,312 (2.8); 7,309 (3.0); 7.3
05(2,6);7,299(3,3);7,288(3,0);7,278(0,9);7,267(1 ,1);5,754(0,7);5,438(10,7);5,323(16,0);3,322(97,3);2,676(0,5);2,672(0,8);2,667(0,5);2,525(105 (2.6), 7.299 (3.3), 7.288 (3.0), 7.278 (0.9), 7.267 (1, 1), 5.754 (0.7), 5.438 (10.7), 5.323 (16.0) 3,322 (97.3); 2,676 (0.5); 2,672 (0.8); 2,667 (0.5); 2,525 (1
,9);2,511(47,8);2,507(96,1);2,503(125,7);2,498(90,9);2,494(44,2);2,334(0,6);2,329(0,8);2,325(0,6);1,352(0,3);1 ,234(1,0);0,008(1,8);0,000(4, 9); 2,511 (47.8); 2.507 (96.1); 2.503 (125.7); 2,498 (90.9); 2,494 (44.2); 2,334 (0.6); 2,329 (0, 8), 2.325 (0.6), 1.352 (0.3), 1, 234 (1.0), 0.008 (1.8), 0.000 (4
7,4);-0,009(1,7) 7.4) - 0.009 (1.7)
Beispiel 1-1-019: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,859(2,2);9,843(2,2);9,123(5,2);8,850(11.6);7,915(0,8);7,912(0,8);7,893(2,1);7.890(1, 6);7,875(1 ,7);7,872(1 ,7);7,841 (2,7);7,819(1 ,5);7,423(1 ,2);7,420(1 ,2);7,405(2,1);7,403(2,0);7,389(1 ,2);7,385(1 ,2);5,289(8,2);4,802(16,0);4,74 8(1,1);4,410(0,7):4,408(0,7);4,358(0,5);4,348(0,6);4,266(0,9);4.016(0,4);3,324(22,5);3,177(1,2);3.164(1,2);2,526(0.^ Example 1-1-019: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.859 (2.2); 9.843 (2.2); 9.123 (5.2); 8.850 (11.6); 7,915 (0.8), 7.912 (0.8), 7.893 (2.1), 7,890 (1, 6), 7,875 (1, 7), 7,872 (1, 7), 7,841 (2,7), 7,819 (1, 5); 7,423 (1,2), 7,420 (1,2), 7,405 (2,1), 7,403 (2,0), 7,389 (1,2), 7,385 (1,2), 5,289 (U.S. 8,2), 4,802 (16,0), 4,74 8 (1,1), 4,410 (0,7): 4,408 (0,7), 4,358 (0,5), 4,348 (0,6); 4,266 (0.9); 4,016 (0.4); 3,324 (22.5); 3,177 (1.2); 3,164 (1.2); 2,526 (0. ^
9);2,504(48,7);2,499(35,8);2,495(17,9);0,008(0,7);0,000(19,7);-0,009(0,8) 9); 2,504 (48.7); 2,499 (35.8); 2.495 (17.9) 0.008 (0.7); 0,000 (19.7) - 0.009 (0.8)
Beispiel 1-1-020: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,905(2,9);9,888(2,9);8,509(3,7);8,503(3,7);7,829(1,3);7,819(2,3);7,811(3,9);7.798(2,6 );7,792(4,1);7,720(3,4);7,698(2,2);7,498(4,3);7,478(3,8);7,376(1,6);7,359(2.8);7,343(1 ,3);7,M0(1,4);5,754(3,7);5,237(10,6);4,5^Example 1-1-020: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.905 (2.9), 9.888 (2.9), 8.509 (3.7), 8.503 (3.7 7.829 (1.3); 7.819 (2.3); 7.811 (3.9); 7.798 (2.6); 7.792 (4.1); 7.720 (3.4); 7.698 (2.2) 7,498 (4,3); 7,478 (3,8); 7,376 (1,6); 7,359 (2.8); 7,343 (1, 3); 7, M0 (1,4); 5,754 (3,7); 5,237 (10.6); 4.5 ^
3(2,2);3,565(7,0);3,548(7,1);3,530{2,2);3,320(139,8);2,671(0,7);2,667(0,5);2,507(84,5);2,502(112,3);2,498(84,1);2,329(0,7);2,325(0,5);1,17 4(7,1);1,156(14,4):1,139(6,9);0,000(12,0);-0,009(0.5) 3 (2.2); 3,565 (7.0); 3,548 (7.1); 3,530 {2,2); 3,320 (139.8); 2,671 (0.7); 2,667 (0.5); 2,507 (84.5); 2.502 (112.3); 2.498 (84.1); 2.329 (0.7); 2.325 (0.5); 1.17 4 (7.1); 1.156 (14.4) : 1.139 (6.9) 0.000 (12.0) - 0.009 (0.5)
Beispiel 1-1-021 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,777(3,9);9,760(3,9);8,324(0,9);8,002(1,2);7,980(7,3);7,964(3.1);7,962(3.0);7,942(1,0Example 1-1-021: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.777 (3.9), 9.760 (3.9), 8.324 (0.9), 8.002 (1.2 ); 7,980 (7.3); 7,964 (3.1); 7.962 (3.0); 7,942 (1.0
);7,940(1,0);7,874(9,9):7,858(0,4);7,472(1,7);7,467(1,7);7,456(3,1);7,450(3,2);7,439(1 ,6):7,434(1,6):5,434(12,3);5,407(0,4);4,350(0,6);4,341); 7,940 (1.0); 7,874 (9.9) 7,858 (0.4); 7,472 (1.7); 7,467 (1.7); 7,456 (3.1); 7,450 (3.2) 7.439 (1,6): 7,434 (1,6): 5,434 (12,3); 5,407 (0,4); 4,350 (0,6); 4,341
(0,6);4,274(14,6);4,094(0,3);3,780(0,9);3,769(0,3);3,753(0,3);3,449(0,6);3,412(0,4);3,326(51,1);3,173(2,2);3,164(2,1);3,037(1^ (3,412 (0.6); 4,274 (14.6); 4,094 (0.3); 3,780 (0.9); 3,769 (0.3); 3,753 (0.3); 3,449 (0.6) 0.4), 3.326 (51.1), 3.173 (2.2), 3.164 (2.1), 3.037 (1 ^
3,001(6,5);2,983(2,0);2,839(1,1):2,821{3,4);2,803(3,6);2,785(1,2);2,677(0,9);2,673(1,2);2,668(0,9);2,526(2,7);2,512(73,7);2,508(152,5);2,50 3,001 (6.5); 2,983 (2.0); 2,839 (1.1): 2.821 {3.4); 2,803 (3.6); 2,785 (1.2); 2,677 (0.9); 2,673 (1.2); 2,668 (0.9); 2,526 (2.7); 2,512 (73.7); 2,508 (152.5), 2.50
3(203,7);2,499(149,8);2,335(0,9);2,330(1 ,2);2,326(0,9); 1 ,352(0,5); 1 ,260(0,4); 1 ,243(7,7); 1 ,235(3,8); 1.225(16,0); 1 ,207(6,9); 1 ,166(3,7); 1 , 148(3 (203.7), 2.499 (149.8), 2.335 (0.9), 2.330 (1.2), 2.326 (0.9); 1, 352 (0.5); 1, 260 (0.4); 1, 243 (7, 7); 1, 235 (3,8); 1,225 (16.0); 1, 207 (6,9); 1, 166 (3,7); 1, 148 (
7,3);1.137(0,6);1,129(3,5);1,119(0,8);1,101(0,4);1,059(0,5);1,045(10,4);1,030(10,3);1,012(0,5);0,992(0,5);0,008(2,5);0,000(75,3):-7.3); 1,137 (0.6); 1,129 (3.5); 1,119 (0.8); 1,101 (0.4); 1,059 (0.5); 1,045 (10.4); 1.030 (10 , 3); 1,012 (0.5); 0.992 (0.5) 0.008 (2.5) 0.000 (75.3): -
0,008(2,8);-0,150(0,3) 0.008 (2.8) - 0.150 (0.3)
Beispiel 1-1-022: 1H-NMR(601,6 MHz, de-DMSO): δ= 9,868(1 ,4);9,857(1 ,5);8,516(1 ,6);8,512(1 ,7);7.893(0,7);7,891 (0,7);7,878(1 ,5);7,876(1 ,0Example 1-1-022: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.868 (1, 4), 9.857 (1.5), 8.516 (1, 6), 8.512 (1, 7 7.893 (0.7); 7.891 (0.7); 7.878 (1.5); 7.876 (1.0)
);7,866(0,9);7,864(0,9);7,833(1,1);7,829(1,1);7,819(1,2);7,815(1,2);7,766(1 ,7);7,751(1 ,3);7,505(2,1);7,491(1,^ 7.866 (0.9), 7.864 (0.9), 7.833 (1.1), 7.829 (1.1), 7.819 (1.2), 7.815 (1.2), 7.766 (1, 7) 7.751 (1, 3), 7.555 (2.1), 7.491 (1, ^
1,5);7,378(0,8);7,376(0,8);5,751(0,4);5,264(5,6);4,547(2,2);4,526(2,8);4,385(3,1);4,364(2,4);3,312(56,1);2,677(16,0);2,523(0,4):2,520(0,5):2 ,517(0,5);2,508(10,1);2,505(22,1);2,502(31,0);2,499(22,4);2,496(10,4);0,005(2,1);0,000(69,5);-0,006(2,3)  1.5); 7,378 (0.8); 7,376 (0.8); 5,751 (0.4); 5,264 (5.6); 4,547 (2.2); 4,526 (2.8); 4.385 (3 , 1), 4.364 (2.4), 3.312 (56.1), 2.677 (16.0), 2.523 (0.4): 2.520 (0.5): 2.517 (0.5), 2.508 ( (0.006 -; 10.1) 2,505 (22.1); 2.502 (31.0); 2,499 (22.4); 2.496 (10.4) 0.005 (2.1) 0.000 (69.5) 2.3)
Beispiel 1-1-023: 1H-NMR(601,6 MHz, de-DMSO): δ= 9,902(2,3);9,891(2,5);9,118(6,0);8,838(13,6);7,841(0,9);7,839(0,9);7,829(1,0);7,827(2, 3);7,825(1,9);7,815(2,0);7,813(2,0);7,794(2,8);7,780(1 ,3);7,378(1 ,3);7,376(1 ,3);7,366(2,0);7,365(1 ,9);7,355(1 ,3);7.353(1,3);5,752(0,5);5,266 (8,8);4,539(16,0);4,481(1,0);3,362(34,2);3,347(2,0^ Example 1-1-023: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.902 (2.3), 9.891 (2.5), 9.118 (6.0), 8.838 (13.6 7.841 (0.9), 7.839 (0.9), 7.829 (1.0), 7.827 (2.3), 7.825 (1.9), 7.815 (2.0), 7.813 (2.0) 7,794 (2,8); 7,780 (1,3); 7,378 (1,3); 7,376 (1,3); 7,366 (2,0); 7,365 (1,9); 7,355 (1, 3); 7,353 (1.3), 5.752 (0.5), 5.266 (8.8), 4.539 (16.0), 4.481 (1.0), 3.362 (34.2), 3.347 (2.0 ^
5);2,505(47,7);2,502(67,4);2,499(47,8);2,496(21,5);2,387(0,4);0,097(0,5);0,005(3,8);0,000(128,0);-0,006(3,9);-0,100(0,4)  5); 2,505 (47.7); 2.502 (67.4); 2,499 (47.8); 2,496 (21.5); 2,387 (0.4); 0.097 (0.5) 0.005 (3.8 ); 0.000 (128.0) - 0.006 (3.9) - 0.100 (0.4)
Beispiel 1-1-024: 'H-NMR(601,6 MHz, de-DMSO): δ= 9,785(3,1);9,776(2,3);9,774(3,2);9,772(2,2);8,638(0,4);8,518(3,7);8,515(3,7);7,931 (1,5 Example 1-1-024: 'H NMR (601.6 MHz, de-DMSO): δ = 9.785 (3.1); 9.776 (2.3); 9.774 (3.2); 9.772 (2.2 8.638 (0.4), 8.518 (3.7), 8.515 (3.7), 7.931 (1.5
);7,929(1,6);7,919(1,8);7,917(3,5);7,914(2,2);7,904(2,4);7,902(2,4);7,855(2,7):7,851(2,6);7,841 (2.9);7,837(3,0);7,832(3,8);7,817(2,8);7 4,6);7,504(4,2);7.455(1 ,9);7,453(1 ,9);7,442(3,2);7,431 (1 ,9);7,429(1 ,9);5.273(11 ,2);4,290(14,3);3,317(12,7);3,031 (1 ,8);3,019(6.2);3,007(6.3); 2,995(1,9);2,892(0,8);2,732(0,6);2,617(0,4);2,614(0,5);2,611(0,4);2,524(0,8);2,521(1,0);2,517(0,9);2,509(22,3);2,506(50,8);2,503(71,7);2,50 0(51,5);2,497(23,3);2,390(0,4);2,387(0,5);2,384(0,4);1,238(7,2);1,226(16,0);1,214(7,0);1,043(0,5);1,033(0,4);0,097(0,7);0,005(5,5);0,000(20); 7.929 (1.6) 7.919 (1.8); 7,917 (3.5); 7.914 (2.2); 7,904 (2.4); 7,902 (2.4); 7,855 (2.7) : 7.851 (2.6); 7.841 (2.9); 7.837 (3.0); 7.832 (3.8); 7.817 (2.8); 7 4.6); 7.504 (4.2); 7.455 (1 , 7,442 (1, 9), 7,429 (1, 9), 5,273 (11, 2), 4,290 (14,3), 3,317 (12, 9), 7), 3.031 (1, 8), 3.019 (6.2), 3.007 (6.3); 2,995 (1.9); 2,892 (0.8); 2,732 (0.6); 2,617 (0.4); 2,614 (0.5); 2,611 (0.4); 2,524 (0.8); 2,521 (1.0); 2.517 (0.9); 2.509 (22.3); 2.506 (50.8); 2.503 (71.7); 2.50 (51.5); 2.497 (23.3) ; 2,390 (0.4); 2,387 (0.5); 2,384 (0.4); 1,238 (7.2); 1,226 (16.0); 1,214 (7.0); 1,043 (0.5); 1,033 (0.4); 0.097 (0.7) 0.005 (5.5); 0,000 (20
0,9);-0,006(6,3);-0,100(0,7) 0.9) - 0.006 (6.3) - 0.100 (0.7)
Beispiel 1-1-025: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,848(2,9);9,831(2,9);7,925(0,6);7,909(5,6);7,894(2,5);7,891(2,4);7,872(0,6);7,869(0,7 Example 1-1-025: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.848 (2.9); 9.831 (2.9); 7.925 (0.6); 7.909 (5.6 ); 7,894 (2.5); 7,891 (2.4); 7,872 (0.6); 7,869 (0.7
);7,863(7,4);7,573(0,5);7,428(3,3);7,424(4,7);7,420(1,3);7,406(5,5);7,404(5,4);7,399(0,7);7,392(1,5);7,385(1,4);7,376(2,1);7,370(2,2);7,360( 1,2);7,354(1,3);7,296(3,4);7,291(1,1);7,277(5,9);7,261(1,4);7,257(3,5);7,175(1,2);7,172(2,1);7,169(1,2);7,158(1,0);7,154(3,1);7,138(0,7);7,1 35(1,2);5,755(0.4);5,429(9,7);4,584(0,4);4,569(0,4);4,417(16.0);3,326(29,4);3,321(33,1);2,673(0,4);2,526(0,9);2,521(1,3);2,513(2); 7,863 (7.4); 7.573 (0.5); 7.428 (3.3); 7,424 (4.7); 7,420 (1.3); 7,406 (5.5); 7,404 (5.4) 7.399 (0.7), 7.392 (1.5), 7.385 (1.4), 7.376 (2.1), 7.370 (2.2), 7.360 (1.2), 7.354 (1.3); 7,296 (3.4); 7,291 (1.1); 7,277 (5.9); 7,261 (1.4); 7,257 (3.5); 7,175 (1.2); 7,172 (2.1); 7,169 (1.2); 7.158 (1.0); 7.154 (3.1); 7.138 (0.7); 7.1.35 (1.2); 5.755 (0.4); 5.429 (9.7); 4.584 (0.4); 4,569 (0.4); 4,417 (16.0); 3,326 (29.4); 3.321 (33.1); 2,673 (0.4); 2,526 (0.9); 2,521 (1, 3); 2.513 (2
44,6);2,504(59,6);2,499(43,1);2,495(20,5);2,330(0,4);1,047(2,8);1 ,032(2,8);0,146(0,4);0,008(2,9);0,000(85,9);-0,009(2,9);-0,150(0,4)44.6), 2.504 (59.6), 2.499 (43.1), 2.495 (20.5), 2.330 (0.4), 1.047 (2.8), 1.032 (2.8), 0.146 (0.4) 0.008 (2.9) 0.000 (85.9) - 0.009 (2.9) - 0.150 (0.4)
Beispiel 1-1-026: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,901 (1 ,5);9,884(1 ,5);7,893(0,3);7,891 (0,3);7,877(2,7);7,875(2,7);7,871 (1 ,8);7,869(1 ,6Example 1-1-026: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.901 (1.5), 9.884 (1.5), 7.893 (0.3), 7.891 (0.3 7,877 (2,7), 7,875 (2,7), 7,871 (1, 8), 7,869 (1, 6
);7,862(1,4);7,859(1,3);7,849(3,8);7,840(0,3);7,390(0,7);7,384(0,7);7,374(1 ,0);7,368(1 ,0);7,358(0,6);7,352(0,7);5,756(0,8);5,395(4,6);4,579(7.862 (1.4), 7.859 (1.3), 7.849 (3.8), 7.840 (0.3), 7.390 (0.7), 7.384 (0.7), 7.374 (1, 0) 7.378 (1, 0); 7.358 (0.6); 7.352 (0.7); 5.756 (0.8); 5.395 (4.6); 4.579 (
8,3);3,715(0,4);3,700(1,1);3,684(1,5);3,669(1,1);3,654(0,4);3,326(14,6);3,323(14,8);2,523(0,5);2,515(7,7);2,510(16,2);2,506(21,7);2,501(8.3); 3,715 (0.4); 3,700 (1.1); 3,684 (1.5); 3,669 (1.1); 3,654 (0.4); 3,326 (14.6); 3,323 (14 (2.501;, 8); 2,523 (0.5); 2,515 (7.7); 2,510 (16.2); 2.506 (21.7)
7);2,496(7,6);1 ,233(0,4);1,147(16,0);1,132(15,7);0,008(1,3);0,000(36,5);-0,009(1,3) 7); 2.496 (7.6); 1, 233 (0.4); 1.147 (16.0); 1.132 (15.7); 0.008 (1.3); 0.000 (36.5); - 0.009 ( 1,3)
Beispiel 1-1-027: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,895(1,6);9,878(1,6);7,958(1,0);7,913(0.3);7,897(3,1);7.882(1,4);7,879(1.3);7,861 (4,1 );7,392(0,7);7,385(0,7);7,375(1,1);7,369(1,2);7,359(0,6);7,353(0,7);5,415(5,3);4,343(0,6);4,333(0,7);3,909(8,5);3,325(11,9);3,12^ (1,1);3,092(1,5);3,076(1,1);3,059(0,4);2,896(7,6);2,737(6.4);2.517(5,3);2,512(10,9);2.508(14,5);2,503(1^ Example 1-1-027: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.895 (1.6); 9.878 (1.6); 7.958 (1.0); 7.913 (0.3); 7,897 (3.1); 7,882 (1.4); 7,879 (1.3); 7,861 (4.1); 7,392 (0.7); 7,385 (0.7); 7,375 (1,1); 7,369 (1 , 2), 7,359 (0.6); 7,353 (0.7); 5,415 (5.3); 4,343 (0.6); 4,333 (0.7); 3,909 (8.5); 3,325 (11, 3); 3,12 ^ (1,1); 3,092 (1,5); 3,076 (1,1); 3,059 (0,4); 2,896 (7,6); 2,737 (6.4); 2,517 (5, 5); 3); 2.512 (10.9); 2,508 (14.5); 2.503 (1 →
,5); 1.049(5,1 ); 1 ,034(5, 1 );0,008(0,6);0,000(16,6);-0,009(0,6) , 5); 1,049 (5.1); 1, 034 (5, 1), 0.008 (0.6), 0.000 (16.6), - 0.009 (0.6)
Beispiel 1-1-028: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,891(3,1);9,875(3,1);7,956(1,4);7,911(0,6);7,895(5,6);7,879(2,7);7,869(1,7);7,858(7,3Example 1-1-028: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.891 (3.1); 9.875 (3.1); 7.956 (1.4); 7.911 (0.6 ); 7.895 (5.6); 7,879 (2.7); 7,869 (1.7); 7,858 (7.3
);7,392(1,1);7,386(1,2);7,377(2,0);7,370(2,1);7,360(1,2);7,354(1,2);5,412(9,9);5,388(1 ,7);4,341 (2,0);4,331^ ); 7,392 (1.1); 7,386 (1.2); 7,377 (2.0); 7,370 (2.1); 7,360 (1.2); 7,354 (1.2); 5,412 (9.9) 5.388 (1, 7); 4,341 (2,0); 4,331 ^
(0,7);3,780(0,8);3,770(0,8);3,765(0,7);3,755(0,6);3,321(28,3);3,165(0,9);3,147(1,0);3,129(0,3);2,894(8,3);2,735(8,0);2,645(2,1);2,627(6,6);2, 609(6,8);2,590(2,3);2,505(46,9);1,320(1,0);1,302(2,0);1 ,284{1,0);1,222(6,9);1,204(13,8);1,185(6,6);1,047{16,0);1,032(15,8);0,008(1,5);0,00 (3.147 (0.7); 3,780 (0.8); 3,770 (0.8); 3,765 (0.7); 3,755 (0.6); 3,321 (28.3); 3,165 (0.9) 1.0), 3.129 (0.3), 2.894 (8.3), 2.735 (8.0), 2.645 (2.1), 2.627 (6.6), 2.609 (6.8), 2.590 (2.3); 2.555 (46.9); 1.320 (1.0); 1.302 (2.0); 1, 284 {1.0); 1.222 (6.9); 1.204 (13.8); 1,185 (6.6); 1.047 {16.0) 1.032 (15.8) 0.008 (1.5); 0.00
1(30,0);0,000(36,7) 1 (30.0) 0.000 (36.7)
Beispiel 1-1-029: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,911(2,8);9,894(2,9);8,510(3,5);8,504(3,5);7,832(1,2);7,829(1,2);7,820(2,3);7,814(3,6Example 1-1-029: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.911 (2.8), 9.894 (2.9), 8.510 (3.5), 8.504 (3.5 ); 7,832 (1.2); 7,829 (1.2); 7,820 (2.3); 7,814 (3.6
):7,811(3,2);7,808(2,1);7,799(2,6);7,793(3,8);7,720(3,3);7,699(2.1);7,499(4,1);7,479(3,7);7,376 ): 7,811 (3.2); 7,808 (2.1); 7,799 (2.6); 7,793 (3.8); 7,720 (3.3); 7,699 (2.1); 7,499 (4.1); 7.479 (3.7); 7,376
1,3);5,239(10.1);4,585(16,0);3,482(4,6);3,465(9,6);3,449(4.8);3,318(28,6);2,672(0,4);2,512(22,1);2,508(44,1);2,503(57  1.3); 5,239 (10.1); 4,585 (16.0); 3,482 (4.6); 3,465 (9.6); 3,449 (4.8); 3,318 (28.6); 2,672 (0.4); 2,512 (22.1); 2,508 (44.1); 2,503 (57
(20,8);2,330(0,4);1 ,603(0,5);1,584(2,2);1,567(4,4);1,549(4,6);1,532(2,4);1 ,514(0,6);1,046(1,2);1,031(1,2)  (20.8); 2,330 (0.4); 1, 603 (0.5); 1.584 (2.2); 1.567 (4.4); 1.549 (4.6); 1.532 (2.4); 1, 514 (0.6); 1.046 (1.2); 1.031 (1.2)
0,008(2, 1 ); 0,000(53, 1 );-0,008(2, 1 ) 0.008 (2, 1); 0,000 (53, 1); - 0,008 (2, 1)
Beispiel 1-1-030: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,871(2,0);9,854(2,0);8,504(2,4);8,498(2,6);7,840(0.8):7,818(2.8);7,812(1,6);7,798(2,3 Example 1-1-030: 'H NMR (400.0 MHz, de-DMSO): δ = 9.871 (2.0); 9.854 (2.0); 8.504 (2.4); 8.498 (2.6 ); 7,840 (0.8) 7,818 (2.8); 7,812 (1.6); 7,798 (2.3
|);7,791(1,6);7,727(2,3);7,706(1,6);7,498(2,8);7,477(2,4);7,384(1,1);7,367(2,0);7,349(1 ,0);5,754(0,5);5,234(7,1);4,695(9 (16,0);3,316(31,7);2,671(0,4);2,502(62,7);2,328(0,4);0,000(36,7);-0,002(34,9) |); 7,791 (1.6); 7,727 (2.3); 7.706 (1.6); 7,498 (2.8); 7,477 (2.4); 7,384 (1.1); 7,367 (2.0 7,349 (1, 0); 5,754 (0.5); 5,234 (7,1); 4,695 (9 (16.0) 3,316 (31.7); 2,671 (0.4); 2,502 (62.7); 2,328 (0.4); 0,000 (36.7) - 0.002 (34.9)
Beispiel 1-1-031 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,832(3,0);9,816(3,1);8,537(3.8);8.531(3,8);7,870(1,3);7.867(1.6);7,863(2,5);7.857(2,5Example 1-1-031: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.832 (3.0); 9.816 (3.1); 8.537 (3.8); 8.531 (3.8); 7,870 (1.3); 7,867 (1.6); 7,863 (2.5); 7,857 (2.5
);7,851(1,8);7,848(3,1);7,843(3,2);7,836(2,8);7,830(2,2);7,827(2,1);7,761{3,6);7,739(2,3);7,521 (4,6);7,500(4,1);7,390(1 ,6);7,388(1,7);7 2,9);7,356(1 ,6);7,353(1 ,5);7, 105(3,6);7,099(1 ,2);7,094(0,5);7,088(1 ,6);7,083(6,5);7,072(0,7);7,067(1 ,4);7,061(4,8);7,051 (0,4);6,945(0,4);6,9 35(4,8);6,929(1,6);6,924(4,9);6,918(2,4);6,912(3,6);6,907(1,4);6,901(3,5);5,755(0,8);5,277(10,5);5,229(16,0);3,789(0,5);3,774(0,6);3,759 4);3,320(20,6);3,171(0,4);2,672(0,4);2,525(1,0);2,512(23,2);2,508(47,9);2,503(63,9);2,498(46,3);2,494(22,4);2,330(0,4);1,046(11,2);1P 1,1);0,008(2,0);0,000(57,0);-0,009(2,0) ); 7,851 (1.8); 7,848 (3.1); 7,843 (3.2); 7,836 (2.8); 7,830 (2.2); 7.827 (2.1), 7.761 {3.6) 7.739 (2.3), 7.521 (4.6), 7.500 (4.1), 7.390 (1.6), 7.388 (1.7), 7. 2.9), 7.356 (1, 6), 7.353 (1, 5); 7, 105 (3.6); 7.099 (1, 2); 7.094 (0.5); 7.088 (1, 6); 7.083 (6.5); 7.072 (0.7); 7,067 (1, 4), 7,061 (4,8), 7,051 (0,4), 6,945 (0,4), 6,9 35 (4,8), 6,929 (1,6), 6,924 (4,9 ); 6,918 (2.4); 6,912 (3.6); 6,907 (1.4); 6,901 (3.5); 5,755 (0.8); 5,277 (10.5); 5,229 (16.0) 3.789 (0.5), 3.774 (0.6), 3.759 4), 3.320 (20.6), 3.171 (0.4), 2.672 (0.4), 2.525 (1.0), 2.512 (23 , 2); 2,508 (47,9); 2,503 (63,9); 2,498 (46,3); 2,494 (22,4); 2,330 (0,4); 1,046 (11,2); 1P 1,1 ); 0,008 (2.0); 0,000 (57.0) - 0.009 (2.0)
Beispiel 1-1-032: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,890(2,9);9,873(2,9);7,891(0,4);7,889(0,5);7,877(5.3);7,875(5,6);7,870(3,0);7,868(2.9 );7,863(2,7);7,860(2,5);7,845(6,9);7,838(0,7);7,394(1,2);7,386(1 ,2);7,378(1 ,9);7,372(1 ,5);7,363(1,1);7,355(1 ,2);5,390(9,0);5,251 (0.5);4,569( 16,0);4,348(0,4);4,330(0,4);3,585(2,2);3,568(7,4);3,550(7,5);3,533(2,3);3,324(46,2);3,320(50,0);2,672(0,4);2,668(0,3);2 Example 1-1-032: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.890 (2.9), 9.873 (2.9), 7.891 (0.4), 7.889 (0.5 7.877 (5.3), 7.875 (5.6), 7.870 (3.0), 7.868 (2.9), 7.863 (2.7), 7.860 (2.5), 7.845 (6.9), 7.838 (0 , 7), 7,394 (1,2), 7,386 (1,2), 7,378 (1, 9), 7,372 (1, 5), 7,363 (1,1), 7,355 (1,2), 5,390 (9, 0), 5.251 (0.5), 4.569 (16.0), 4.348 (0.4), 4.330 (0.4), 3.585 (2.2), 3.568 (7.4), 3.550 (7.5); 3,533 (2.3); 3,324 (46.2); 3,320 (50.0); 2,672 (0.4); 2,668 (0.3); 2
2,512(25,9);2,508(54,0);2,503(72,2);2,499(52,2);2,494(25, 1);2,330(0,5);2,325(0,3); 1,316(0,4); 1 ,299(0,8); 1,281 (0,4); 1 , 176(7,4); 1,158(15,1);2.512 (25.9), 2.508 (54.0), 2.503 (72.2), 2.499 (52.2), 2.494 (25, 1), 2.330 (0.5), 2.325 (0.3); 1.316 (0.4); 1, 299 (0.8); 1,281 (0.4); 1, 176 (7,4); 1,158 (15.1);
1,141(7,2);1,046(1,0);1,031(1,0);0,146(0,5);0,008(3,6);0,000(108,7);-0,009(3,6);-0,150(0,5) 1,141 (7.2); 1,046 (1.0); 1,031 (1.0); 0.146 (0.5) 0.008 (3.6) 0.000 (108.7) - 0.009 (3.6); -0.150 (0.5)
Beispiel 1-1-033: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,897(3,1);9,895(1,9);9,881(3,0);9,878(1,9);7,894(0,5);7,892(0,5);7,880(5,3);7,877(5,6Example 1-1-033: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.897 (3.1), 9.895 (1.9), 9.881 (3.0), 9.878 (1.9 ); 7,894 (0.5); 7,892 (0.5); 7,880 (5.3); 7.877 (5.6
);7,873(3,1 );7,871 (2,9);7,865(2,7);7,862(2,5);7,848(7,2);7,840(0,7);7,393(1 ,3);7,386(1 ,3);7,377(1 ,8);7,370(1 ,7);7,362(1 ,2);7,355(1 ,2);5,394( 8,9);4,576(16,0);4,343(0,8);4,332(0,8);4,246(0,3);3,797(0,4);3,787(0,4);3,782(0,6);3,771(0,5);3,767(0,4);3,756(0,4);3,486(4,8);3,470(10,0) ,453(4,9);3,327(13,3);3,324(15,4);2,896(0,7);2,736(0,5);2,529(0,4);2,525(0,5);2,516(10,1):2,512(21 ,5);2,507(28,9);2,502(20,9);2,498(10,0); 1,606(0,5); 1,588(2,1); 1,571 (4,2); 1,552(4,5); 1,535(2^^ 7.873 (3.1), 7.871 (2.9), 7.865 (2.7), 7.862 (2.5), 7.848 (7.2), 7.840 (0.7), 7.393 (1, 3) 7,386 (1,3), 7,377 (1, 8), 7,370 (1,7), 7,362 (1,2), 7,355 (1,2), 5,394 (8,9), 4,576 (16,0); 4,343 (0.8); 4,332 (0.8); 4,246 (0.3); 3,797 (0.4); 3,787 (0.4); 3,782 (0.6); 3,771 (0.5); 3,767 (0.4); 3.756 (0.4); 3.486 (4.8); 3,470 (10.0), 453 (4.9), 3.327 (13.3), 3.324 (15.4), 2.896 ( 0.7), 2.736 (0.5), 2.529 (0.4), 2.525 (0.5), 2.516 (10.1): 2.512 (21, 5), 2.507 (28.9), 2.502 (20 , 9); 2,498 (10.0); 1,606 (0.5); 1,588 (2.1); 1,571 (4.2); 1.552 (4.5); 1.535 (2 ^ ^
6(0,6);0,880(7,2);0,008(1 ,7);0,000(55,4);-0,009(1 ,9) 6 (0.6), 0.880 (7.2), 0.008 (1, 7), 0.000 (55.4), - 0.009 (1, 9)
Beispiel 1-1-034: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,894(1,6);9,878(1,6);9,843(0,4);9,826(0,4);7,934(0.4);7,926(0,4);7,919(0.8);7,908(0,5Example 1-1-034: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.894 (1.6); 9.878 (1.6); 9.843 (0.4); 9.826 (0.4 ); 7,934 (0.4); 7,926 (0.4); 7.919 (0.8); 7,908 (0.5
);7,893(3,2);7,879(1,5);7,876(1,5);7,855(4,8);7,394(0,9);7,388(0,7);7,378(1 ,1);7,372(1 ,2);7,362(0,6);7,356(0,7);5,409(6,0);4,794(2,3);3,807 8,6);3,321(72,2);2,893(0,5);2,734(0,4);2,526(0,9);2,508(33,2);2,504(44,7);2,499(35,0);2,335(0,4);2,141 (16,0);1,047(0,6);1,032(0,6);0,008( 0);0,000(48,0);-0,008(2,4) 7.893 (3.2), 7.879 (1.5), 7.876 (1.5), 7.855 (4.8), 7.394 (0.9), 7.388 (0.7), 7.378 (1, 1) 7,372 (1,2), 7,362 (0,6), 7,356 (0,7), 5,409 (6,0), 4,794 (2,3), 3,807 8,6), 3,321 (72,2), 2,893 (0.5), 2.734 (0.4), 2.526 (0.9), 2.508 (33.2), 2.504 (44.7), 2.499 (35.0), 2.335 (0.4), 2.141 ( 16.0), 1.047 (0.6), 1.032 (0.6), 0.008 (0), 0.000 (48.0), - 0.008 (2.4)
Beispiel 1-1-035: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,847(6,4);9,830(6,8);7,968(1,1);7,965(1,2);7,946(5,0);7,943(5,7);7,928(13,8);7,911(1, 5);7,839(16,0);7,757(7,6);7,753(9,8);7,737(11,6);7,734(10,8);7,593(2,9);7,588(3,9);7,584(2,3);7,572(11,9);7,553(10,1);7,549(5,9);7,545(7,6) ;7,541 (4,6);7,535(2,2);7,527(4,7);7,518(0,9);7,513(0,9);7,509(1,3);7,441(2,9);7,435(2,7);7,425(5,0);7,419(4,8);7,409(2,8);7,402(2,7) ,7);5,441(0,7);5,398(16,0);5,355(0,7);4,564(6,8);4,532(11,8);4,459(11,9);4,426(6,9);3,321(77,8);3,178(0,3);2,678(0,5);2,673(0 Example 1-1-035: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.847 (6.4); 9.830 (6.8); 7.968 (1.1); 7.965 (1.2 7.946 (5.0), 7.943 (5.7), 7.928 (13.8), 7.911 (1.5), 7.839 (16.0), 7.757 (7.6), 7.753 (9.8) ; 7,737 (11.6); 7.734 (10.8); 7,593 (2.9); 7,588 (3.9); 7,584 (2.3); 7,572 (11.9); 7,553 (10.1); 7.549 (5.9), 7.545 (7.6), 7.541 (4.6), 7.535 (2.2), 7.527 (4.7), 7.518 (0.9), 7.513 (0.9), 7.509 (1.3), 7.441 (2.9), 7.435 (2.7), 7.425 (5.0), 7.419 (4.8), 7.409 (2.8), 7.402 (2.7), 7) ; 5,441 (0.7); 5,398 (16.0); 5,355 (0.7); 4,564 (6.8); 4,532 (11.8); 4,459 (11.9); 4,426 (6.9); 3,321 (77.8); 3,178 (0.3); 2,678 (0.5); 2,673 (0
2,526(2,0);2,513(38,1);2,509(76,5);2,504(101,1);2,500(76,3);2,495(39,7);2,335(0,5);2,331(0,6);2,326(0,5);1 ,232(0,5);1,047(1,0);1,032(1,0); 0,146(0,4);0,008(4,2);0,000(89,9);-0,008(4,8);-0,150(0,4)  2,526 (2.0); 2,513 (38.1); 2,509 (76.5); 2.504 (101.1); 2,500 (76.3); 2,495 (39.7); 2,335 (0.5); 2,331 (0.6); 2.326 (0.5); 1, 232 (0.5); 1.047 (1.0); 1.032 (1.0); 0.146 (0.4) 0.008 (4.2) 0.000 (89.9) - 0.008 (4.8) - 0.150 (0.4)
Beispiel 1-1-036: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,953(1 ,8);9,936(1 ,8);8,517(2,2);8,511 (2,3);7,821 (1 ,3);7,814(1 ,8);7,800(1 ,6);7,793(2,6Example 1-1-036: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.953 (1, 8); 9.936 (1, 8); 8.517 (2.2); 8.511 (2.3 7.821 (1, 3), 7.814 (1.8), 7.800 (1.6), 7.793 (2.6
);7,771(1,2);7,706(2,1);7,685(1,4);7,499(2,6);7,479(2.3);7,346(1,0);7,329(1 ,8);7,311(0,9);5,754(1P 7,771 (1,2); 7,706 (2,1); 7,685 (1,4); 7,499 (2,6); 7,479 (2.3); 7,346 (1,0); 7,329 (1, 8); 7,311 (0.9); 5,754 (1P
(0,4);2,507(52,3);2,502(69,0);2,498(52,6);2,447(16,0);2,329(0,4);0,008(2,2);0,000(48,6)  (0.000 (0.4) 2.507 (52.3); 2.502 (69.0); 2,498 (52.6); 2.447 (16.0); 2.329 (0.4) 0.008 (2.2) 48.6)
Beispiel 1-1-037: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,858(3.2);9,842(3,4);7,960(0,3);7,957(0.3);7,938(2,8);7,935(3,4);7,931(3,6);7,924(6,7Example 1-1-037: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.858 (3.2); 9.842 (3.4); 7.960 (0.3); 7.957 (0.3); 7.938 ( 2.8); 7,935 (3,4); 7,931 (3,6); 7.924 (6,7
);7,922(6,4);7,909(0,6);7,871 (0,6);7,858(7,7);7,422(1 ,3); 7,414(1 ,3);7,408(1 ,6);7,406(1 ,7);7,400(1 ,6);7,397(1 ,6);7,392(1 ,4);7,384(1 ,3);5,419(7.922 (6.4), 7.909 (0.6), 7.871 (0.6), 7.858 (7.7), 7.422 (1, 3); 7,414 (1,3), 7,408 (1,6), 7,406 (1, 7), 7,400 (1,6), 7,397 (1,6), 7,392 (1,4), 7,384 (1,3), 5,419 (
10,2);5,395(0J);4,490(3,8);4,458(6,0);4,364(6,2);4,340(0,4);4,332(4,0);4,094(0,4);4,081(0,4);3,319(79,6);3,177(1,9);3,168(0,6);3,164(1,8);310.2); 5.395 (0J); 4,490 (3.8); 4,458 (6.0); 4,364 (6.2); 4,340 (0.4); 4,332 (4.0); 4,094 (0.4 ); 4,081 (0.4); 3,319 (79.6); 3,177 (1.9); 3,168 (0.6); 3,164 (1.8); 3
,150(0,5);2,981(0,4);2,962(1,5);2,947(0,9);2,943(1,7);2,929(2,4);2,910(2,3);2,891 (0,8);2,824(0,7);2,805(2,3);2,787(2,5);2,772(1,7):2,769(1,1, 150 (0.5); 2,981 (0.4); 2,962 (1.5); 2,947 (0.9); 2,943 (1.7); 2,929 (2.4); 2,910 (2.3); 2.891 (0.8), 2.824 (0.7), 2.805 (2.3), 2.787 (2.5), 2.772 (1.7): 2.769 (1.1
);2,754(1,6);2,735(0,5);2,676(0,4);2,672(0,5);2,668(0,4);2,525(1,1);2,512(29,9);2,508(61,2);2,503(80,6);2,498(58,5);2,494(28,3);2,334(0,4);); 2,754 (1.6); 2,735 (0.5); 2,676 (0.4); 2,672 (0.5); 2,668 (0.4); 2,525 (1.1); 2,512 (29.9) ; 2,508 (61.2); 2.503 (80.6); 2,498 (58.5); 2,494 (28.3); 2,334 (0.4);
2,330(0,5);2,325(0,4);1,322(0,5);1,304(1,1);1,285(0,5);1 ,259(7,6);1,240(16,0);1,221(7,3);1,046(2,2);1,031(2,2);0,008(2,1);0,000(61,1);-2.330 (0.5), 2.325 (0.4), 1.322 (0.5), 1.304 (1.1), 1.285 (0.5), 1.259 (7.6), 1.240 (16.0) ; 1,221 (7.3); 1,046 (2.2); 1,031 (2.2); 0,008 (2.1); 0,000 (61.1); -
0,008(2,3) 0.008 (2.3)
Beispiel 1-1-038: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,870(2,9);9.854(3,0);7,957(0,4);7,935(3,2);7,930(3,5);7,923(6,3);7,922(6,3);7,909(0,5Example 1-1-038: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.870 (2.9), 9,854 (3.0), 7.957 (0.4), 7.935 (3.2 ); 7,930 (3.5); 7,923 (6.3); 7.922 (6.3); 7,909 (0.5
);7,857(7,4);7,424(1,2);7,416(1,2);7,408(1,6);7,402(1,5);7,394(1,2);7,386(1 ,2);5,419(9,5);4,390(2,7);4,358(6,1);4,317(5,7);4,285(2,4);4,093( 0,7);4,080(0,7);3,318(167,0);3,176(2,3);3,163(2,3);3,003(0,7);2,986(1,8);2,969(2,5);2,952(1,9);2,935{0,7);2,676{0,6);2,671(0,8);2,667(0,6);2 ,524(2,0);2,506(100,5);2,502(132,5);2,498(97,8);2,333(0,6);2,329(0,8);2,324(0,6);1,248(13,0);1,236(16,0);1,231(14,7);1,219(12,9);0,146(0,47.857 (7.4); 7.424 (1.2); 7.416 (1.2); 7.408 (1.6); 7.402 (1.5); 7.394 (1.2); 7.386 (1, 2) 5,419 (9.5); 4,390 (2,7); 4,358 (6,1); 4,317 (5,7); 4,285 (2,4); 4,093 (0.7); 4.080 (0.7); 3.318 (167.0); 3,176 (2.3); 3,163 (2.3); 3,003 (0.7); 2,986 (1.8); 2,969 (2.5); 2,952 (1.9); 2,935 {0.7); 2.676 {0.6); 2.671 (0.8); 2.667 (0.6); 2. 524 (2.0); 2.506 (100.5); 2.502 (132.5); 2,498 (97.8); 2,333 (0.6); 2,329 (0.8); 2,324 (0.6); 1,248 (13.0); 1.236 (16.0); 1,231 (14.7); 1,219 (12.9) 0.146 (0.4
);0,008(2,9);0,000(86,5);-0,008(3,8);-0,150(0,4) ); 0,008 (2.9); 0,000 (86.5) - 0.008 (3.8) - 0.150 (0.4)
Beispiel 1-1-039: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,855(1 ,9);9,839(2,0);7,937(3,8);7,927(4, 1);7,861 (5,0);7,833(0,4);7,814(0,4);7,422(1 ,0Example 1-1-039: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.855 (1, 9), 9.839 (2.0), 7.937 (3.8), 7.927 (4, 1 7.861 (5.0); 7.833 (0.4); 7.814 (0.4); 7.422 (1.0)
);7,411(1,4);7,406(1,1);7,401 (1,0);7,395(1,4);7,384(0,9);7,364(0,4);5,754(2,2);5,421(6,8);4,543(2,0);4,51 ^ 7.411 (1.4); 7.406 (1.1); 7.401 (1.0); 7.955 (1.4); 7.384 (0.9); 7.364 (0.4); 5.754 (2.2) 5,421 (6,8); 4,543 (2,0); 4,51 ^
60,4);3,175(0,5);3,163(0,5);2,771(0,3);2,679(16,0);2,541(0,7);2,506(95,8);2,502(128,9);2,498(105,6);2,329(0,7);1,235(5,6);0,854(0,5);0,146 (0,4);0,000(82,4);-0,150(0,4)  60.4) 3.175 (0.5); 3,163 (0.5); 2,771 (0.3); 2,679 (16.0); 2,541 (0.7); 2,506 (95.8); 2.502 (128 , 9), 2.498 (105.6), 2.329 (0.7), 1.235 (5.6), 0.854 (0.5), 0.146 (0.4), 0.000 (82.4), -0.150 (0 , 4)
Beispiel 1-1-040: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,859(2,0);9,842(2,1);9,833(1.7);9,816(1,7);7,920(0,4);7,907(4,8);7.899(2.8);7,896(2,6Example 1-1-040: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.859 (2.0); 9.842 (2.1); 9.833 (1.7); 9.816 (1.7); 7,920 (0.4); 7,907 (4.8); 7,899 (2.8); 7,896 (2.6
);7,893(2,3);7,885(2,3);7,880(2,9);7,860(9,6);7,841 (0,5);7,406(0,8);7,398(0,8);7,390(1 ,1);7,381 (1 ,6);7,376(1 ,5);7,364(1 ,5);7,359(1 ,4);7,347( 0,7);7,343(0,7);5,756(4,0);5,423(7,8);5,418(7,0);4,680(8,1);4,573(6,7);3,395(0,8);3,377(2,5);3,359(2,6);3,341(1,2);3,325(39,2);3,323(31,8);3 ,311(3,3);3,293(3,1);3,275(1,0);2,510(32,4);2,506(43,3);2,502(32,9);2,070(12,7);1,893(16,0);1,138{2,9);1,120(6,3);1 02(2,8);1,010(3,6);0,9 93(7,7);0,975(3,5);0,006(1 ,4);0,000(33,2);-0,008(1 ,6) 7.893 (2.3), 7.885 (2.3), 7.880 (2.9), 7.860 (9.6), 7.841 (0.5), 7.406 (0.8), 7.398 (0.8) 7.392 (1, 1), 7.381 (1, 6), 7.376 (1, 5), 7.364 (1, 5), 7.359 (1, 4), 7.377 (0.7), 7.343 (0.7); 5,756 (4.0); 5,423 (7.8); 5,418 (7.0); 4,680 (8.1); 4,573 (6.7); 3,395 (0.8); 3,377 (2.5); 3,359 (2.6); 3.341 (1.2); 3.325 (39.2); 3.323 (31.8); 3, 311 (3.3); 3.293 (3.1); 3.275 (1.0); 2,510 (32.4); 2,506 (43.3); 2.502 (32.9); 2.070 (12.7); 1,893 (16.0); 1.138 {2.9); 1,120 (6.3); 1 O 2 (2.8), 1.010 (3.6), 0.9 93 (7.7), 0.975 (3.5), 0.006 (1, 4), 0.000 (33.2), - 0.008 (1, 6)
Beispiel 1-1-041 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,909(3,5);9,893(3,4);7,938(0,5);7,935(0,6);7,921(0,6);7,918(0.8);7,912(0,6);7,905(0,5Example 1-1-041: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.909 (3.5), 9.893 (3.4), 7.938 (0.5), 7.935 (0.6 ); 7,921 (0.6); 7.918 (0.8); 7.912 (0.6); 7,905 (0.5
5;7,895(0,75;7,883(6,0);7,881 (6,5);7,875(3,6);7,873(3,7);7,870(3,7);7,867(3,1);7,855(0,8);7,843(8,8);7,438(0,4);7,433(0,4);7,420(0,8);7,416(5, 7.895 (0.75, 7.883 (6.0), 7.881 (6.5), 7.875 (3.6), 7.873 (3.7), 7.870 (3.7), 7.867 (3.1); (7,416; 7,855 (0.8); 7,843 (8.8); 7,438 (0.4); 7,433 (0.4); 7,420 (0.8)
1,0);7,401(4,3);7,394(4,1);7,385(7,9);7,381(7,8);7,378(7,8);7,359(6,4);7,354(2,3);7,339(2,5);7,321 (0,7);7,315(1,6);7,309(3,0);7,300(0,9);7,21.0); 7,401 (4.3); 7,394 (4.1); 7,385 (7.9); 7,381 (7.8); 7,378 (7.8); 7,359 (6.4); 7,354 (2 , 3), 7.399 (2.5), 7.321 (0.7), 7.315 (1.6), 7.309 (3.0), 7.300 (0.9), 7.2
93(2,1);7,286(0,6);7,280(0,5);7,276(0,8);7,271(0,4);5,754(4,0);5,412(0,5);5,387(10,1);5,374(1,1);5,018(0,9);5,013(0,9);4,794(0,4);4,657(16,93 (2.1); 7,286 (0.6); 7,280 (0.5); 7,276 (0.8); 7,271 (0.4); 5,754 (4.0); 5,412 (0.5); 5,387 (10,1); 5,374 (1.1); 5,018 (0.9); 5,013 (0.9); 4,794 (0.4); 4,657 (16,
0);4,617(14,5);4,498(0,5);4,484(0,5);4,146(0,8);4,142(0,8);3,331(87,0);3.324(72.7);2,677(0,6);2,672(0,8);2,668(0,6);2,525(1,8);^0); 4,617 (14.5); 4,498 (0.5); 4,484 (0.5); 4,146 (0.8); 4,142 (0.8); 3,331 (87.0); 3324 (72.7); 2,677 (0.6); 2,672 (0.8); 2,668 (0.6); 2,525 (1.8); ^
2,508(97,5);2,503(130,2);2,499(94,3);2,494(45,8);2,440(0,9);2,334(0,8);2,330(0,8);2,325(0,6);1,336(1,2);1,299(1,3);1,259{1,9);1,250(1,7);1,2,508 (97.5); 2.503 (130.2); 2,499 (94.3); 2,494 (45.8); 2,440 (0.9); 2,334 (0.8); 2,330 (0.8); 2,325 (0.6); 1,336 (1.2); 1,299 (1.3); 1.259 {1.9); 1,250 (1.7); 1,
233(1,7);0,146(0,4);0,008(2,8);0,000(87,3);-0,009(2,9);-0,150(0,4) 233 (1.7); 0.146 (0.4) 0.008 (2.8) 0.000 (87.3) - 0.009 (2.9) - 0.150 (0.4)
Beispiel 1-1-042: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,851(3,1);9,835(3,2);8,186(0,5);7,995(0,5);7,992(0,5);7,973(2,3);7,970(2,5);7,958(5,1 j);7,955(6,0);7,937(0,8);7,876(0,6);7,862(7,3);7,442(1,4);7,436(1,4);7,431(0,6);7,426(2,4);7,419(2,3);7,410(1,4);7,403(1 ,2);5,754 0J);5,427(9,6);5.403{0 ):4,931{12 );4J14(0,4);4,699(0,4);3,317(82,4);3 07(6,4);3,288(5,8):3,270(1,9):3 69(0,6);3,151(0,6);2,676(0,5);2 ,671(0,6);2,667(0,5);2,524(1,4);2,520(2.2);2,511 (36,6);2,507(76.4);2,502(102,4);2,498(73,9);2,493(35.5);2,333(0,4);2,329(0,6);2,324(0Example 1-1-042: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.851 (3.1); 9.835 (3.2); 8.186 (0.5); 7.995 (0.5 7.992 (0.5); 7.973 (2.3); 7.970 (2.5); 7.958 (5.1j); 7.955 (6.0); 7.937 (0.8); 7.876 (0.6 ); 7,862 (7.3); 7.442 (1.4); 7,436 (1.4); 7,431 (0.6); 7,426 (2.4); 7,419 (2.3); 7,410 (1.4) 7,403 (1, 2); 5,754 5J); 5,427 (9,6); 5,403 {0): 4,931 {12); 4J14 (0,4); 4,699 (0,4); 3,317 (82,4); 3,07 (6,4); 3,288 (5.8): 3.270 (1.9): 3 69 (0.6); 3.151 (0.6); 2.676 (0.5); 2.671 (0.6); 2.667 (0.5) 2.524 (1.4), 2.520 (2.2), 2.511 (36.6), 2.507 (76.4), 2.502 (102.4), 2.498 (73.9), 2.493 (35.5), 2.333 (0.4) ; 2,329 (0.6); 2,324 (0
322(0J);1,300(7,5);1,282(16,0);1,263(7,2);1,235(1,0);1 ,110(0,6);1,107(0,6);1,092{1,2);1,089(1,3);1,074(0,8);1,071(0,6);1,046(0,6);1,030(0,322 (0J), 1.300 (7.5), 1.282 (16.0), 1.263 (7.2), 1.235 (1.0), 1, 110 (0.6), 1.107 (0.6), 1.092 {1,2); 1,089 (1.3); 1,074 (0.8); 1,071 (0.6); 1,046 (0.6); 1,030 (0,
6);0,146(0,4);0,008(2,4);0,000(77,6);-0,008(2,8);-0,150(0,4) 6); 0.146 (0.4) 0.008 (2.4) 0.000 (77.6) - 0.008 (2.8) - 0.150 (0.4)
Beispiel 1-1-043: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,937(1, 6);9,920(1,6);7,881(0,4);7,880(0,4);7,862(2,8);7,859(3,3);7,854(4,2);7,846(1, 4Example 1-1-043: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.937 (1.6), 9.920 (1.6), 7.881 (0.4), 7.880 (0.4 7.862 (2.8), 7.859 (3.3), 7.854 (4.2), 7.846 (1, 4
);7,843(1,3);7,824(0,4):7,821 (0,3);7,573(0,4);7,364(0,7);7,358(0,7);7,348(1 ,3);7,342(1 ,4);7,331 (0,7);7,326(0,7);5,755(0,4);5,403(5,7):3,322( 21,4);2,528(0,4);2,523(0,6):2,514(8,6):2,510(18,0);2,505(24,1):2,501(17,2):2,496(8,2):2,441(16,0);0,008(0,3);0,000(10,0):-0,009(0,3)7.843 (1.3); 7.824 (0.4): 7.821 (0.3); 7.573 (0.4); 7.364 (0.7); 7.358 (0.7); 7.348 (1, 3) 7.342 (1, 4); 7.331 (0.7); 7.326 (0.7); 5.755 (0.4); 5.403 (5.7): 3.322 (21.4); 2.528 (0.4); 2,523 (0.6) 2,514 (8.6) 2,510 (18.0); 2.505 (24.1) 2.501 (17.2) 2.496 (8.2) 2.441 (16.0) 0.008 (0.3); 0,000 (10.0) - 0.009 (0.3)
Beispiel 1-1-044: 1H-NMR(400,0 MHz, de-DMSO): ö= 9,769(1 ,3);9,753(1 ,3):7,924(2,7);7,919(1 ,5);7,911 (1 ,2);7,908(1 ,1 );7,873(3,4);7,822(3,7 );7,479(3,1);7,478(3,6);7,405(0,65;7,398(0,6);7,389(0,8);7,382(0,9);7,374(0,5);7,367(0,6);5,478(6,1);5,443(4,2);3,318(37,7);2,671 (0,4);2,524 (1 ,0);2,511 (22,3);2,506(47,2);2,502(63,9);2,497(46,9);2,493(23,0);2,333(0,4);2,321 (16,0);2,298(0,5); 1 ,234(0,4); 1 ,045(0,5); 1 ,030(0,5);0,000(Example 1-1-044: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.769 (1, 3); 9.753 (1.3): 7.924 (2.7); 7.919 (1, 5) 7.911 (1, 2), 7.908 (1, 1), 7.873 (3.4), 7.822 (3.7), 7.479 (3.1), 7.478 (3.6), 7.405 (0.65; 7,398 (0.6); 7,389 (0.8); 7,382 (0.9); 7.374 (0.5); 7,367 (0.6); 5,478 (6.1); 5,443 (4.2); 3,318 (37.7), 2.671 (0.4), 2.524 (1.0), 2.511 (22.3), 2.506 (47.2), 2.502 (63.9), 2.497 (46.9), 2.493 ( 23.0); 2.333 (0.4); 2.321 (16.0); 2.298 (0.5); 1, 234 (0.4); 1, 045 (0.5); 1, 030 (0, 5); 0.000 (
4,0) 4.0)
Beispiel 1-1-045: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,747(3,8);9,731(3,8);8,377(6,6);7,950(0,7);7,935(7,7);7,930(4,2);7,923(3,5);7,921 (3,4Example 1-1-045: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.747 (3.8), 9.731 (3.8), 8.377 (6.6), 7.950 (0.7 7.935 (7.7), 7.930 (4.2), 7.923 (3.5), 7.921 (3.4
);7,899(0,7);7,886(8,1);7,876(9,6);7,411(1,6);7,404(1,6);7,395(2,2);7,388(2,2);7,380(1 ,4);7,373(1,5);5,585(16^ ); 7,899 (0.7); 7,886 (8.1); 7,876 (9.6); 7,411 (1.6); 7,404 (1.6); 7,395 (2.2); 7,388 (2.2) 7,380 (1, 4); 7,373 (1,5); 5,585 (16 ^
76(0,5);2,672(0,7);2,667(0,5);2,525(1,6);2,511(41,4);2,507(88,5);2,503(120,0);2,498(87,1);2,494(42,0);2,334(0,5);2,329(0,7);2,325(0 34(0,6); 1,046(0,8); 1,031 (0,8);0,000(8,3) 76 (0.5); 2,672 (0.7); 2,667 (0.5); 2,525 (1.6); 2,511 (41.4); 2.507 (88.5); 2.503 (120.0); 2,498 (87.1); 2.494 (42.0); 2.334 (0.5); 2.329 (0.7); 2.325 (0 34 (0.6); 1.046 (0.8); 1.031 (0.8) ; 0,000 (8.3)
Beispiel 1-1-046: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,739(3,7);9,723(3,6);7,947(0,7);7,934(6,6);7,932(6,9);7,928(4,0);7,920(3,4);7,917(3,1Example 1-1-046: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.739 (3.7), 9.723 (3.6), 7.947 (0.7), 7.934 (6.6 ); 7,932 (6.9); 7,928 (4.0); 7,920 (3.4); 7,917 (3.1
);7,898(0,7);7,895(0,6);7,874(8,9);7,413(1,7);7,406(1,7);7,397(2,2);7,390(2,3);7,382(1 ,5);7,375(1,6);7,295(7,2);7,291(7,3);6,894(7,4)i); 7,898 (0.7); 7.895 (0.6); 7,874 (8.9); 7,413 (1.7); 7,406 (1.7); 7,397 (2.2); 7,390 (2.3) 7,382 (1, 5); 7,375 (1,6); 7,295 (7,2); 7,291 (7,3); 6,894 (7,4) i
7,4);5,755(1,1);5,449(10,9);5,350(16,0):3,320(87,2);2,892(1,2);2,732(1,0);2,676(0,5);2,672(0,7);2,667(0,5);2,525(1,7);2,520(2,7);2,512(39,67.4); 5,755 (1.1); 5,449 (10.9); 5,350 (16.0) 3,320 (87.2); 2,892 (1.2); 2,732 (1.0); 2,676 (0 , 5); 2,672 (0.7); 2,667 (0.5); 2,525 (1.7); 2,520 (2.7); 2,512 (39.6
);2,507(83,6);2,503(112.2);2,498(80,9);2.494(38,6);2,334(0,5);2,330(0,6);2,325(0.5);1,235(0,8);0,000(8,2) ); 2,507 (83.6); 2.503 (112.2); 2,498 (80.9); 2494 (38.6); 2,334 (0.5); 2,330 (0.6); 2,325 (0.5); 1,235 (0 0.000 (8.2), 8)
Beispiel 1-1-047: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,728(3,5);9,711(3,7);9,698(0,3);8,046(7,2);8,040(7.3);7,952(0,6);7,940(7,2);7,938(7,7 );7,930(4,5);7.928(4,5);7,925(3,3);7,905(0,4);7,902(0,4);7,874(9,8);7,748(0,7);7,743(0,7);7,414(1 ,6);7,406(1 ,6);7,401 (1 ,7);7,398(1 ,8);7,393( 1 ,7);7,390(1,9);7,384(1,6);7,376(1,5);7,212(0,8);7,207(0,7);7,007(7,7);7,001 (7,7);5,754(5,5);5,719(1 ,5);5,677(0,5);5,653(16,0);5,449(11 ,4);3Example 1-1-047: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.728 (3.5), 9.711 (3.7), 9.698 (0.3), 8.046 (7.2 8.040 (7.3), 7.952 (0.6), 7.940 (7.2), 7.938 (7.7), 7.930 (4.5), 7.928 (4.5), 7.925 (3.3), 7.955 (0.4), 7.902 (0.4), 7.874 (9.8), 7.748 (0.7), 7.743 (0.7), 7.414 (1, 6), 7.406 (1, 6), 7.401 ( 1, 7), 7.398 (1, 8), 7.393 (1, 7), 7.399 (1.9), 7.384 (1.6), 7.376 (1.5), 7.212 (0.8), 7.207 (0 , 7); 7,007 (7,7); 7,001 (7,7); 5,754 (5,5); 5,719 (1, 5); 5,677 (0,5); 5,653 (16,0); 5,449 (11; 4); 3
,320(67,4);2,892(0,6);2,732(0,5);2,677(0,4);2,672(0,6):2,667(0,5);2,525(1,3);2,521(2,0);2,512(34,9);2,507(75,2);2,503(102,0);2,498(72,7);2, 494(34,1);2,334(0,4);2,330(0,6);2,325(0,4);1,234(0,4);1 ,046(0,7);1,031(0,7);0,000(8,5) , 320 (67.4); 2,892 (0.6); 2,732 (0.5); 2,677 (0.4); 2,672 (0.6) 2,667 (0.5); 2,525 (1.3); 2.521 (2.0), 2.512 (34.9), 2.507 (75.2), 2.503 (102.0), 2.498 (72.7), 2.494 (34.1), 2.344 (0.4) 2.330 (0.6), 2.325 (0.4), 1.234 (0.4), 1.046 (0.7), 1.031 (0.7), 0.000 (8.5)
Beispiel 1-1-048: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,762(3,9);9,745(3,9);8,313(0.6);8,002(2,2);7,990(2,1);7,979(0,8);7,953(0,8);7,936(7,5Example 1-1-048: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.762 (3.9); 9.745 (3.9); 8.313 (0.6); 8.002 (2.2); 7.990 (2.1); 7,979 (0.8); 7.953 (0.8); 7,936 (7.5
);7,921(3,3);7,919(3,1);7,900(0,8);7,897(0,8);7,879(10,2);7,814(7,5);7,809(7,7);7,412(1,7);7,406(1,7);7,396(2,8);7,390(3,0);7,380(1,5);7,374 (1,7);6,638(7,8);6,632(7,9);5,754(0,8);5,592(16,0);5,452(11,8);3,318(215,3);3,176{0,4);3,163(0,3);2,737(0,6);2,725(0,7);2,714(15,6);2,702(1 5,6);2,680(0,6);2,675(1,1);2,671(1,4);2,666(1,1);2,524(3,3);2,519(5,2);2,511(85,6);2,506(182,0);2,502(245,7);2,497(176,5);2,493(83,9);2,33 3(1,1);2,328(1,5);2,324(1,1);2,320(0,5);1,352(2,4);1,336(0,6);1.299(0,3);1 ,259{0,6);1,250{0,8);1,235(3,2);0,854(0,4);0,008(0,5);0,000(15,5);- 0,009(0,5) ); 7,921 (3.3); 7.919 (3.1); 7,900 (0.8); 7,897 (0.8); 7,879 (10.2); 7,814 (7.5); 7,809 (7.7) 7.412 (1.7), 7.406 (1.7), 7.396 (2.8), 7.390 (3.0), 7.380 (1.5), 7.374 (1.7), 6.638 (7.8); 6,632 (7.9); 5,754 (0.8); 5,592 (16.0); 5,452 (11.8); 3.318 (215.3); 3.176 {0.4); 3,163 (0.3); 2,737 (0.6), 2.725 (0.7), 2.714 (15.6), 2.702 (1.56), 2.680 (0.6), 2.675 (1.1), 2.671 (1.4), 2.666 (2,493 (1.1); 2,524 (3.3); 2,519 (5.2); 2,511 (85.6); 2.506 (182.0); 2.502 (245.7); 2.497 (176.5) 83.9), 2.33 3 (1.1), 2.328 (1.5), 2.324 (1.1), 2.320 (0.5), 1.352 (2.4), 1.336 (0.6); 1,299 (0.3); 1, 259 {0.6); 1.250 {0.8); 1.235 (3.2); 0.854 (0.4); 0.008 (0.5); 0.000 (15.5) - 0,009 (0,5)
Beispiel 1-1-049: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,779(2,5);9,762(2,5);8,313(0,4);7,932(0,6);7,917(4,5);7,913(3,0);7,903(2,2);7,900(2,0 );7,881 (0,6);7,872(6,4);7,489(4,9);7,403(1 ,2);7,396(1,2);7,387(1 ,7);7,380(1 ,9);7,371 (1 ,0);7,364(1 ,2);7,213(5,4);5,754(0,3);5,520(0,5);5,442(Example 1-1-049: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.779 (2.5), 9.762 (2.5), 8.313 (0.4), 7.932 (0.6 7.917 (4.5), 7.913 (3.0), 7.903 (2.2), 7.900 (2.0), 7.881 (0.6), 7.872 (6.4), 7.489 (4.9) 7.403 (1,2); 7,396 (1,2); 7,387 (1, 7); 7,380 (1,9); 7,371 (1, 0); 7,364 (1,2); 7,213 (5,4); (5,442; 5,754 (0.3); 5,520 (0.5)
7,9);5,421(12,4);3,317(133,0);2,675(0,7);2,671(0,9);2,666(0,7);2,662{0,3);2,524(2,1);2,519(3,2);2,511(54,0):2,506(118,0);2,502(161 ,4);2,497.9); 5,421 (12.4); 3,317 (133.0); 2,675 (0.7); 2,671 (0.9); 2,666 (0.7); 2,662 {0,3); 2.524 (2 , 1), 2.519 (3.2), 2.511 (54.0): 2.506 (118.0), 2.502 (161, 4), 2.49
7(116,7);2,492(55,4);2,333(0,7);2,328(1,0);2,324(0,7);2,074(0,7);2,029(16,0);1,235(0,7);1,045(0,4);1,030(0,4);0,000(1 ,3) 7 (116.7); 2.492 (55.4); 2,333 (0.7); 2,328 (1.0); 2,324 (0.7); 2,074 (0.7); 2,029 (16.0); 1.235 (0.7); 1.045 (0.4); 1.030 (0.4); 0.000 (1, 3)
Beispiel 1-1-050: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,784(3,6);9,768(3,6);7,944(0,9);7,926(7,7);7,911(3,5);7,889(0,9);7,872(8,5);7,643(0,3 );7,619(5,9);7,409(1,4);7,404(1,4);7,393(2,4);7,387i2,6);7,377(1,3);7,371(1 ,4);7,130(6,0);7,015(0,5);6,887(6,0);5,450(12,9);5,361 (16,0);3,32 3(27,6);3,175(0,8);3.164(0,8);2,671(0,5);2.503(81,9);2.328(0,5);1,352(2.4);1,336(0.6);1,299(0,3);1,257(0,6);1.249(0,8);1,232(3,5);0 ;0,000(4,1) Example 1-1-050: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.784 (3.6), 9.768 (3.6), 7.944 (0.9), 7.926 (7.7 7.911 (3.5); 7.889 (0.9); 7.872 (8.5); 7.643 (0.3); 7.619 (5.9); 7.409 (1.4); 7.404 (1.4) 7.393 (2.4); 7.387i2.6), 7.377 (1.3), 7.371 (1, 4), 7.130 (6.0), 7.015 (0.5), 6.887 (6.0), 5.450 (12.9); 5.361 (16.0); 3.32 3 (27.6); 3.175 (0.8); 3.164 (0.8); 2.671 (0.5); 2.503 (81.9) 2.328 (0.5); 1.352 (2.4); 1.336 (0.6); 1.299 (0.3); 1.257 (0.6); 1.249 (0.8); 1.232 (3.5); 0; 0.000 ( 4,1)
Beispiel 1-1-051 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,755(3,7);9,739(3,6);8,313(0,4);7,958(0,8);7.942(7,0);7,939(6,2);7.926(3,0);7,923(2.8 );7,904(0,7);7,901 (0,7);7,872(9,4);7,824(6.0);7,780(4,0);7,777(5,3);7,420(1 ,6);7,414(1 ,6);7,404(2,7);7,398(2,9);7,388(1 ,4);7,382(1 ,5);5,456( 12,3);5,448(16,0);3,319(110,8);2,675(0,8);2,671(1,1);2,667(0,8);2,662(0,4);2,524(2,7);2,520(4,2):2,511(65,7);2,507(138,3);2,502(184,8);2,4 97(132,4);2,493(62,7);2,338(0,4);2,333(0,8);2,329(1 , 1 );2,324(0,8);1 ,352(0,8): 1 ,250(0,3); 1 ,235(1 ,3); 1 ,046(0,3);0,008(0,3);0,000(12,2);- 0,008(0,4) Example 1-1-051: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.755 (3.7), 9.739 (3.6), 8.313 (0.4), 7.958 (0.8 7,942 (7.0), 7.939 (6.2), 7,926 (3.0), 7.923 (2.8), 7.904 (0.7), 7.901 (0.7), 7.872 (9.4), 7.824 (6.0); 7,780 (4.0); 7,777 (5,3); 7,420 (1, 6); 7,414 (1, 6); 7,404 (2,7); 7,398 (2,9); 7,388 (1); 4), 7.382 (1.5), 5.456 (12.3), 5.448 (16.0), 3.319 (110.8), 2.675 (0.8), 2.671 (1.1), 2.667 (0.8 2.662 (0.4), 2.524 (2.7), 2.520 (4.2): 2.511 (65.7), 2.507 (138.3), 2.502 (184.8), 2.497 (132 , 4); 2.493 (62.7); 2.338 (0.4); 2.333 (0.8); 2.329 (1, 1); 2.324 (0.8); 1, 352 (0.8): 1, 250 (0.3); 1, 235 (1, 3); 1, 046 (0.3), 0.008 (0.3), 0.000 (12.2), - 0.008 (0.4)
Beispiel 1-1-052: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,777(1 ,2);9,761 (1 ,2);7,924(2,1);7,922(2,3);7,917(1 ,2);7,909(1 ,1 );7,906(1 ,0);7,874(3,0Example 1-1-052: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.777 (1.2), 9.761 (1.2), 7.924 (2.1), 7.922 (2.3 7.917 (1, 2), 7.909 (1, 1), 7.906 (1, 0), 7.874 (3.0
);7,748(2,3);7,742(2,4);7,407(0,6);7,400(0,5);7,391(0,7);7,384(0,7);7,376(0,5);7,369(0,5);6,255(2,6);6,249(2,6);5,463(5,6);5,444(3,6);3,320 47,2);2,671 (0.4);2,529(0,5);2,524(1,0);2,520(1 ,4);2,511 (24,4);2,507(52,9);2,502(71 ,8);2.497(51 ,0);2,493(23,8);2,406(16,0);2,329(0,4);2,324 (0,3);0,000(0,6) ); 7,748 (2.3); 7,742 (2.4); 7,407 (0.6); 7,400 (0.5); 7,391 (0.7); 7,384 (0.7); 7,376 (0.5) 7.369 (0.5), 6.255 (2.6), 6.249 (2.6), 5.463 (5.6), 5.444 (3.6), 3.320 (47.2), 2.671 (0.4), 2.529 (0 , 5), 2.524 (1.0), 2.520 (1, 4), 2.511 (24.4), 2.507 (52.9), 2.502 (71, 8), 2.497 (51, 0), 2.493 (23, 8), 2.406 (16.0), 2.329 (0.4), 2.324 (0.3), 0.000 (0.6)
Beispiel 1-1-053: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,762(5,7);9,746(5,8);9,474(3,3);8,326(0.3);8,005(1,1);8,003(1,2);7,987(10,7);7,984(9,Example 1-1-053: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.762 (5.7), 9.746 (5.8), 9.474 (3.3), 8.326 (0.3); 8,005 (1.1); 8,003 (1.2); 7,987 (10.7); 7,984 (9,
0);7,972(4,7);7,969(4,5);7,950(1,2);7,947(1,2);7,869(15,2);7,577(5,5);7,571(5,0);7,557(8,0);7,553(7,3);7,499(0,4);7,477(2,8);7,471(2,7);7,460); 7,972 (4.7); 7,969 (4.5); 7,950 (1.2); 7,947 (1.2); 7,869 (15.2); 7,577 (5.5); 7,571 (5.0 ); 7.557 (8.0); 7,553 (7.3); 7,499 (0.4); 7,477 (2.8); 7,471 (2.7) 7.46
1(4,9);7,455(6,6);7,444(9,7);7,439(7,7);7,435(5,4);7,429(13,0);7,425(13,5);7,417(3,1);7,413(1,6);7,401(0,8);7,396(0,7);7,298(0,4);5,756(4,1)1 (4.9); 7,455 (6.6); 7,444 (9.7); 7,439 (7.7); 7,435 (5.4); 7.429 (13.0); 7,425 (13.5); 7,417 (3.1); 7,413 (1.6); 7,401 (0.8); 7,396 (0.7); 7,298 (0.4); 5,756 (4.1)
;5,424(16,0);4,295(6,0);4,251(5,9);4,024(0,4);4,010(0,4);3,360(46,0);2,970(0,7);2,678(0,5);2,673(0,7);2,669(0,5);2,526(1,6);2,522(2,4);2,51; 5,424 (16.0); 4,295 (6.0); 4,251 (5.9); 4,024 (0.4); 4,010 (0.4); 3,360 (46.0); 2,970 (0.7); 2,678 (0.5); 2,673 (0.7); 2,669 (0.5); 2,526 (1.6); 2,522 (2.4); 2.51
3(41 ,3);2,509(88,9);2,504(120, 1 );2,499(86,2);2,495(40,7):2,335P 3 (41, 3); 2.509 (88.9); 2.504 (120.1); 2.499 (86.2); 2.495 (40.7): 2.335P
0,009(4,5);-0,150(0,6)  0,009 (4.5) - 0.150 (0.6)
Beispiel 1-1-054: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,796(3,0);9,779(3,0);8,546(3,8);8,540(3,8);8,314(1 ,3);7,877(1 ,3);7.874(1 ,4);7,868(2,4Example 1-1-054: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.796 (3.0), 9.779 (3.0), 8.546 (3.8), 8.540 (3.8 8,314 (1, 3), 7,877 (1, 3), 7,874 (1, 4), 7,868 (2,4
);7,861(2,8);7,856(3,1);7,853(2,3);7,847(2,8);7,841(2,9);7,837(2,5);7,834(2,2);7,772(3,6);7,750(2,5);7,741(4,7);7,736(4,7);7,522(4,5);7,502( 4,1);7,429(4,8);7,426(4,7);7,387(1,6);7,384(1,7);7,368(3,0);7,352(1,5);7,349(1,5);6,275(3,3);6,269(5,4);6,264(3,2);5,533(16,0);5,296(10,4);3 ,329(37,4);2,527(0,5);2,513(11,6);2,509(23,8);2,505(31,6):2,500(22,9);2,496(11,1);0,008(0,6);0,000(17,9);-0,009(0,7) ); 7,861 (2.8); 7,856 (3.1); 7,853 (2.3); 7,847 (2.8); 7,841 (2.9); 7,837 (2.5); 7,834 (2.2) 7,772 (3.6); 7,750 (2.5); 7,741 (4,7); 7,736 (4,7); 7,522 (4,5); 7,502 (4,1); 7,429 (4,8); 7,426 (4.7); 7.387 (1.6); 7,384 (1.7); 7,368 (3.0); 7,352 (1.5); 7,349 (1.5); 6,275 (3.3); 6,269 (5.4); 6.264 (3.2); 5.533 (16.0); 5.296 (10.4); 3, 329 (37.4); 2.527 (0.5); 2.513 (11.6); 2,509 (23.8); 2,505 (31.6) 2,500 (22.9); 2.496 (11.1) 0.008 (0.6); 0,000 (17.9) - 0.009 (0.7)
Beispiel 1-1-055: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,820(3,3);9,803(3,2);7,932(0,6);7,930(0,7);7,917(5,9);7,915(6,2);7,911(3,7);7,909(3,4Example 1-1-055: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.820 (3.3); 9.803 (3.2); 7.932 (0.6); 7.930 (0.7 ); 7,917 (5.9); 7.915 (6.2); 7,911 (3.7); 7,909 (3.4
);7,902(2,9);7,899(2,8);7,880(0,6);7,877(0,7);7,868(8,2);7,855(0,4);7,573(0,7);7,406(1 ,6);7,399(1,5);7,390(2,2);7,383(2,3);7,374(1,3);7,368( 1 ,4);7,105(3,4);7,099(1 ,2);7,094(0,5);7,088(1 ,4);7,083(6,4);7,072(0,7);7,067(1 ,3);7,061 (4,6);7,051 (0,5);6,947(0,4);6,937(4,7);6,931 (1 ,5);6,9 26(4,8);6,920(2,3);6,914(3,6);6,909(1,4);6,903(3,5);6,522(0,4);6,501(0,3);5,433(10!2);5,416(0J);5!220(16,0);4,795(0,9);4,584(0,7);4,569(0,); 7,902 (2.9); 7,899 (2.8); 7,880 (0.6); 7.877 (0.7); 7,868 (8.2); 7,855 (0.4); 7.573 (0.7) 7,406 (1,6), 7,399 (1,5), 7,390 (2,2), 7,383 (2,3), 7,374 (1,3), 7,368 (1,4), 7,105 (3,4); 7,099 (1,2), 7,094 (0.5), 7,088 (1,4), 7,083 (6,4), 7,072 (0,7), 7,067 (1,3), 7,061 (4,6), 7,051 (0.5), 6.947 (0.4), 6.937 (4.7), 6.931 (1.5), 6.9 26 (4.8); 6,920 (2.3); 6,914 (3.6); 6,909 (1.4); 6,903 (3.5); 6,522 (0.4); 6,501 (0.3); 5,433 (10 ! 2); 5,416 (0J); 5 ! 220 (16.0); 4,795 (0.9); 4,584 (0.7); 4,569 (0,
6);4,040(0,4);4,022(0,4);3,322(33.9);2,673(0,3);2,527(07);2,522(1,1);2,513(18,9);2,509(40,4);2,5M(55,0);2,500 (2,509; 6); 4,040 (0.4); 4,022 (0.4); 3,322 (33.9); 2,673 (0.3); 2,527 (07); 2,522 (1.1); 2,513 (18.9) 40.4), 2.5 M (55.0); 2,500
3);1,990(1,7);1 ,232(0,4);1,195(0,5);1.177(0,9);1,159(0.5);0,008(2,0);0,000(60,8);-0,009(2,3)  3), 1.990 (1.7), 1, 232 (0.4), 1.195 (0.5), 1.177 (0.9), 1.159 (0.5), 0.008 (2.0), 0.000 (60.8 ) - 0.009 (2.3)
Beispiel 1-1-056: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,322(2,7);9,784(1 ,9);9,768(1 ,9);7,942(0,5);7,925(3,9);7.922(3,7);7,909(1 ,7);7,907(1 ,Example 1-1-056: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.322 (2.7), 9.784 (1.9), 9.768 (1.9), 7.942 (0.5 7,925 (3,9), 7,922 (3,7), 7,909 (1, 7), 7,907 (1,
7);7,888(0,6);7,885(0,6);7,875(5,2);7,604(2,9);7,598(2,9);7,407{0,9);7,401(0,9);7,390(1,5);7,385(1,7);7,374(0,8);7,368(0,9);6,472(3,1);6,466 (3,2);5,442(6,2);5,386(7,5);4,343(1,0);4,332(1,1);3J94(0,4);3,783(0,4);3,779(0,5);3,768(0,5);3,763(0,4);3,753(0,3);3,321(66,9);2,676(0,4);2, 672(0,5);2,667(0,4);2,525(1,3);2,520(2.0);2,511(30,0);2,507(63,4);2,502(85,6);2,498(62,4);2,494(30,5);2,334(0,4);2,329(0,^ 7); 7,888 (0.6); 7,885 (0.6); 7,875 (5.2); 7,604 (2.9); 7.598 (2.9); 7,407 {0.9); 7,401 (0.9 7,390 (1.5); 7,385 (1,7); 7,374 (0.8); 7,368 (0.9); 6,472 (3,1); 6,466 (3,2); 5,442 (6,2) ; 5,386 (7.5); 4,343 (1.0); 4,332 (1.1); 3J94 (0.4); 3,783 (0.4); 3,779 (0.5); 3,768 (0.5); 3.763 (0.4), 3.753 (0.3), 3.321 (66.9), 2.676 (0.4), 2.672 (0.5), 2.667 (0.4), 2.525 (1.3) ; 2,520 (2.0); 2,511 (30.0); 2.507 (63.4); 2.502 (85.6); 2,498 (62.4); 2,494 (30.5); 2,334 (0.4); 2,329 ( 0 ^
81(0,5);1,967(16,0);1,235(3,8);1,046(9,9);1,030(9,8);0,854(0,4);0,000(5,6) 81 (0.5); 1,967 (16.0); 1,235 (3.8); 1,046 (9.9); 1,030 (9.8); 0,854 (0.4); 0,000 (5.6)
Beispiel 1-1-057: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,753(3,9);9,737(3.9);7,985(4.1);7,982(4,3);7,949(0,6);7,935(7,9);7,927(4.3);7,924(4,0 );7,921 (3,5);7,902(0,5);7,899(0,5);7,876(9,6);7,411 (1 ,7); 7,403(1 ,6);7,397(1 ,8);7,395(2,0);7,389(1 ,9);7,387(2,0);7,380(1 ,5);7,373(1 ,6);6,747(Example 1-1-057: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.753 (3.9); 9.737 (3.9); 7.985 (4.1); 7.982 (4.3); 7.949 ( 0.6), 7.935 (7.9), 7.927 (4.3), 7.924 (4.0), 7.921 (3.5), 7.902 (0.5), 7.899 (0.5), 7.876 (9.6) 7,411 (1, 7); 7,403 (1,6), 7,397 (1,8), 7,395 (2,0), 7,389 (1, 9), 7,387 (2,0), 7,380 (1, 5), 7,373 (1,6), 6,747 (
4,8):6,742(4,9);5,659(0,5);5,633(16,0):5,453(12,2);3,320(65,3);2,677(0,4);2,872(0,6);2,668(0,4):2,525(1,4):2,521(2,0):2,512(33,8);2,508(72, 4);2,503(97,9);2.498(70,3);2,494(33,3):2,334(0,4);2,330(0,6);2,325(0,4);1 ,235(0,6);0,000(7,6) 4.8) 6,742 (4.9); 5,659 (0.5); 5,633 (16.0) 5,453 (12.2); 3,320 (65.3); 2,677 (0.4); 2,872 (0 , 6); 2.668 (0.4): 2.525 (1.4): 2.521 (2.0): 2.512 (33.8); 2.508 (72, 4); 2.503 (97.9); 2.498 (70, 3); 2,494 (33,3): 2,334 (0,4); 2,330 (0,6); 2,325 (0,4); 1, 235 (0,6); 0,000 (7,6)
Beispiel 1-1-058: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,757(1 ,9):9,740(1 ,9);8,009(0,5);7,987(3,4);7,985(3.3);7,971 (1 ,5);7,968(1 ,5);7,949(0,5Example 1-1-058: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.757 (1.9): 9.740 (1.9); 8.009 (0.5); 7.987 (3.4 7.985 (3.3), 7.971 (1, 5), 7.968 (1, 5), 7.949 (0.5
);7,946(0,6);7,875(4,8);7,861 (0,5);7,475(0,8);7,470(0,9);7,458(1,5);7,453(1 ,6);7,442(0,8);7,437(0,8);5,756(1,1);5,436(5,8);5,411 (0,5);4,3 7,5);3,324(23,6);2,673(0,4);2,668(0,4);2,653(16,0);2,528(0,9);2,521(1,2):2,513(18,3);2,508(38,8);2,504(52,2);2,499(37,8);2,495(18,2);2,356 (3,8):2,330(0,3); 1 ,046(3,5): 1 ,031 (3,5);0,008(1 ,4);0,000(45,5);-0,009(1 ,7) 7.946 (0.6), 7.875 (4.8), 7.861 (0.5), 7.475 (0.8), 7.470 (0.9), 7.458 (1.5), 7.453 (1, 6) 7.442 (0.8), 7.437 (0.8), 5.756 (1.1), 5.436 (5.8), 5.411 (0.5), 4.3 7.5), 3.324 (23.6) ; 2,673 (0.4); 2,668 (0.4); 2,653 (16.0); 2,528 (0.9); 2,521 (1.2) 2,513 (18.3); 2,508 (38.8); 2.504 (52.2); 2.499 (37.8); 2.495 (18.2); 2.356 (3.8): 2.330 (0.3); 1, 046 (3.5): 1, 031 (3.5); 0.008 (1, 4); 0.000 (45.5); - 0.009 (1, 7)
Beispiel 1-1-059: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,842(2,7);9,825(2,8);9,136(7.1);8,875(16,0);7,882(0,7);7,879(0,8);7,865(0,7);7,861(2, 1);7,858(2,1);7,843(2,4):7,840(2,6):7,832(2,9):7,830(3,2);7,828(2,8);7,811(1,1);7,396(1,4):7,392(1,4);7,379(2,5);7,375(2,5):7,362(1,4);7,358 (1.3);7.283(0.4);7,276(3.2);7,272(1,1);7,267(0,5);7,256(4,3);7,254(3,8);7,236(4,0);7.229(0,5);6,928(1.6);6,926(2.1);6,919(4,η Example 1-1-059: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.842 (2.7), 9.825 (2.8), 9.136 (7.1), 8.875 (16.0); 7.882 (0.7), 7.879 (0.8), 7.865 (0.7), 7.861 (2, 1), 7.858 (2.1), 7.843 (2.4): 7.840 (2.6): 7.832 (2.9) 7.830 (3.2); 7,828 (2.8); 7,811 (1.1); 7,396 (1.4) 7,392 (1.4); 7,379 (2.5); 7,375 ( 2.5): 7.362 (1.4), 7.358 (1.3), 7.283 (0.4), 7.276 (3.2), 7.272 (1.1), 7.267 (0.5), 7.256 (4.3), 7.254 ( 3.8); 7,236 (4.0); 7,229 (0.5); 6,928 (1.6); 6,926 (2.1); 6,919 (4, η
12(3,6);6,909(4,3);6,902(1,7);6,895(5,4);5,310(9,2);5,243(15,1);3,320(75,9);3,177(0,8);3,163 12 (3.6); 6,909 (4.3); 6,902 (1.7); 6,895 (5.4); 5,310 (9.2); 5,243 (15.1); 3,320 (75.9); 3,177 (0.8); 3,163
5);2,667(0,4);2,525(1,1);2,520(1,7):2,511(28,4):2,507(61,5);2,502(83,6);2,498(59,9):2,493(28,2);2,334(0,4):2,329(0,5);2,324(0,4);1,234ß ;0,008(0,4);0,000(16,8);-0,009(0,5)  5); 2,667 (0.4); 2,525 (1.1); 2,520 (1.7) 2,511 (28.4) 2,507 (61.5); 2.502 (83.6); 2.498 (59.9 2.433 (28.2); 2.344 (0.4): 2.329 (0.5); 2.324 (0.4); 1.234β; 0.008 (0.4); 0.000 (16.8); 0.5)
Beispiel 1-1-060: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,740(4,2);9,724(4,2);8,853(0,7);8,560(10,0);8,538(6,0);8,534(6,1);8,313(0,6);8,151(0,Example 1-1-060: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.740 (4.2); 9.724 (4.2); 8.853 (0.7); 8.560 (10.0 ); 8,538 (6.0); 8,534 (6.1); 8,313 (0.6); 8,151 (0,
7):8,063(9,9):7,952(0,8);7,895(1,9);7,876(4,1);7,857(5,9);7,842(3,7);7,836(3,6):7,784(5,1);7,762(3,5):7,522(5,2);7,501(4,8);7,399(2,5);7,3827): 8,063 (9.9) 7,952 (0.8); 7.895 (1.9); 7,876 (4.1); 7,857 (5.9); 7,842 (3.7); 7,836 (3.6 7,522 (5.2); 7,501 (4.8); 7,399 (2.5); 7,382:;:) 7.784 (5.1) 7.762 (3.5)
(4,2);7,364(2,3);6,570(0,7);5,612(16,0);5,290(13,8):3,318(265,9):2,891 (3,5);2,731(3,3):2,671(2,3);2,502(384,2):2,328(2,4);1,234(0,^(4,2); 7,364 (2,3); 6,570 (0,7); 5,612 (16,0); 5,290 (13,8): 3,318 (265,9): 2,891 (3,5); 2,731 ( 3.3) 2,671 (2.3); 2,502 (384.2) 2.328 (2.4) 1.234 (0, ^
0,6);0,000(127,2);-0,150(0,7) 0.6); 0.000 (127.2) - 0.150 (0.7)
Beispiel 1-1-061 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,913(2,6);9,897(2,7);9,120(7,1);9,042(0,4);8,851(0,7);8.841(15,6);8,750(0,9);7,849(0,Example 1-1-061: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.913 (2.6), 9.897 (2.7), 9.120 (7.1), 9.042 (0.4 ); 8,851 (0.7); 8,841 (15.6); 8,750 (0.9); 7,849 (0,
8);7,846(0,9);7,832(0,7j;7,828(2,2);7,824(2,2);7,810(2,55;7,807(2,6);7,800(2,9);7,798(3,2);7,796(2,8);7,778(1,0);7,383(1,4);7,378(1,4);7,366 (2,5):7,362(2.4);7,349(1,3);7,345(1,3);5,756(2,9);5,291i0,4):5,269(9,5):4,803(0,7);4,582(16,0);4,501(0,4);4,486(0,4):3,482(4,5):3,465(9,4);3, 449(4,6);3,337(23,8);3,329(19,1);2,528(0,4):2,523(0,7);2,515(11,9);2,510(25,7):2.506(34,9)i (0.9); 7,832 (0,7j; 7,828 (2.2);; 8) 7.846 7.824 (2.2); 7.810 (2.55; 7,807 (2.6); 7,800 (2.9); 7,798 (3,2), 7,796 (2,8), 7,778 (1,0), 7,383 (1,4), 7,378 (1,4), 7,366 (2,5): 7,362 (2.4), 7,349 (1 , 3); 7,345 (1.3); 5,756 (2.9); 5,291i0,4): 5,269 (9.5) 4,803 (0.7); 4,582 (16.0); 4,501 (0.4 4,486 (0,4): 3,482 (4,5): 3,465 (9.4); 3, 449 (4,6); 3,337 (23,8); 3,329 (19,1); 2,528 (0); 4): 2,523 (0.7); 2,515 (11.9); 2,510 (25.7) 2,506 (34.9) i
,566(4,2);1 ,548(4,4);1,531(2,2);1 ,513(0,6);1,354(0,8):1,232(1,1);1,226(1,0);0,912(7,7);0,894(15,4);0,875(6,9);0,000(9,9);-0,009(0,3) , 566 (4.2); 1.458 (4.4); 1.531 (2.2); 1.513 (0.6); 1.354 (0.8): 1.232 (1.1); 1.226 (1 , 0); 0.912 (7.7); 0.894 (15.4); 0,875 (6.9); 0,000 (9.9) - 0.009 (0.3)
Beispiel 1-1-062: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,818(1,9);9,802(1,9):7,900(0,6);7,895(0,6);7.891(0,4);7,878(3,6);7,875(3,7);7,859(7,0 );7,840(0,4);7,837(0,4);7,370(0,9);7,364(0,9);7,354(1,5);7,348(1,6);7,337(0,8);7,332(0,8);5,411 (6,3);4,641(0,6);4,574^ Example 1-1-062: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.818 (1.9); 9.802 (1.9): 7.900 (0.6); 7.895 (0.6 7.891 (0.4), 7.878 (3.6), 7.875 (3.7), 7.859 (7.0), 7.840 (0.4), 7.837 (0.4), 7.370 (0.9) 7.364 (0.9), 7.354 (1.5), 7.348 (1.6), 7.337 (0.8), 7.332 (0.8), 5.411 (6.3), 4.641 (0.6); 4.574 ^
0,5):3,319(54,1);2,892(0,4);2,886(0,6);2,879(0,7):2,869(1,2);2,859(0,7);2,853(0,6);2,672(0,4);2,525(0,8);2,521(1 ,2);2,512(19,9):2,508(42,5); 2,503(57,7);2,498(41,9):2,494(20,2);2,330(0,3);2,184(16,0):1,871(1,1);1,352(0,8);1,234(1,1);1,046(3,3);1,031(3,3):0,786(1 ,8);0,777(1,4);0,7 68(1 ,9);0,754(1 ,5);0,743(2,5);0,008(0,8);0,000(27,5);-0,009(1 ,0)  0.5) 3,319 (54.1); 2,892 (0.4); 2,886 (0.6); 2,879 (0.7) 2,869 (1.2); 2,859 (0.7); 2,853 (0 , 6), 2,672 (0.4), 2.525 (0.8), 2.521 (1.2), 2.512 (19.9): 2.508 (42.5); 2,503 (57.7); 2,498 (41.9) 2,494 (20.2); 2,330 (0.3); 2,184 (16.0) 1,871 (1.1); 1,352 (0.8); 1,234 (1,1); 1,046 (3,3); 1,031 (3,3): 0,786 (1, 8); 0,777 (1,4); 0,7 68 (1, 9); 0,754 (1, 5) 0.743 (2.5), 0.008 (0.8), 0.000 (27.5), - 0.009 (1, 0)
Beispiel 1-1-063: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,998(2,1);9,980(2.2);8,515(2,6);8.509(2,6);8,343(2,8);7,866(1.6);7,859(1,6);7,845(1,8Example 1-1-063: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.988 (2.1), 9.980 (2.2), 8.515 (2.6), 8.509 (2.6); 8,343 (2.8); 7,866 (1.6); 7,859 (1.6); 7,845 (1.8
);7,839(1,8);7,728(1,6);7,724(1,6);7,711(1,5);7,707(1,6);7,520(3,1);7,499(2,8);5,754(1 ,1);5,360(7,3):4,825(16,0);4,269(1,6);4,094(0,4);4,081 (0,5);3,568(0,8);3,320(62,5);3,176(2,7):3,163(2,6);2,671 (0,4);2,525(0,9):2,520(1,5);2,511(23,5);2,507(50,0);2,502(67,4);2,498(48,6);2,493(2 3.1);2,329(0,4);0.008(1 ,2);0,000(41 ,0);-0,009(1 ,5) ); 7.839 (1.8); 7,728 (1.6); 7,724 (1.6); 7.711 (1.5); 7,707 (1.6); 7,520 (3.1); 7,499 (2.8) 5.754 (1, 1); 5.360 (7.3): 4.825 (16.0); 4.269 (1.6); 4.094 (0.4); 4.081 (0.5); 3.568 (0.8); 3.326 (62.5), 3.176 (2.7): 3.163 (2.6), 2.671 (0.4), 2.525 (0.9): 2.520 (1.5), 2.511 (23.5), 2.507 (50.0); 2.502 (67.4); 2.498 (48.6); 2.493 (2 3.1); 2.329 (0.4); 0.008 (1, 2); 0.000 (41, 0); - 0.009 ( 1, 5)
Beispiel 1-1-064: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,734(3,2);9,718(3,2);8,110(6,9);8,109(7,5);7,956(0,6);7,941(6,5);7,936(3,6);7,929(3,0Example 1-1-064: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.734 (3.2), 9.718 (3.2), 8.110 (6.9), 8.109 (7.5 ); 7,956 (0.6); 7,941 (6.5); 7,936 (3.6); 7.929 (3.0
);7,926(2,8);7,907(0,5):7,904(0,5);7,880(8,0);7,755(6,8);7,753(7,2);7,416(1 ,4):7,408(1 ,4);7,400(1,9);7,393(2,0);7,385(1 ,3):7,378(1,4);5,812( 16,0);5,754(1,5);5,460(10,6);3,316(125,0);3,175(0,7);3,162(0,6);2,675(0,7);2,670(1,0);2,666(0,8);2,524(2,1);2,519(3,3);2,510(57,9);2,506(1 24,2);2,501 (168,8);2,497(123,4);2,492(59,9);2,337(0,3);2,332(0,7);2,328(1 ,0);2,323(0,8);1,234(0,6);-0,001(1,2) 7.926 (2.8), 7.907 (0.5): 7.904 (0.5), 7.880 (8.0), 7.755 (6.8), 7.753 (7.2), 7.416 (1, 4) : 7.408 (1, 4); 7,400 (1.9); 7,393 (2,0); 7,385 (1,3): 7,378 (1,4); 5,812 (16,0); 5,754 (1.5); 5,460 (10.6); 3.316 (125.0); 3,175 (0.7); 3,162 (0.6); 2,675 (0.7); 2,670 (1.0); 2,666 (0.8); 2,524 (2.1); 2.519 (3.3); 2.510 (57.9); 2.506 (1 24.2); 2.501 (168.8); 2.497 (123.4); 2.492 (59.9); 2.377 (0.3), 2.332 (0.7), 2.328 (1.0), 2.233 (0.8), 1.234 (0.6), - 0.001 (1.2)
Beispiel 1-1-065: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,742(2,9);9,726(2,9);9,135(7,1);8,875(16,0);8,855(1,4);8,557(8,0);8,313(0,6);8,183(0,Example 1-1-065: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.742 (2.9), 9.726 (2.9), 9.135 (7.1), 8.875 (16.0 ); 8,855 (1.4); 8,557 (8.0); 8,313 (0.6); 8,183 (0,
6);8,151(1,3);8,061(7,7);7,953(0,4);7,912(0,9);7,909(0,9);7,891(2,3);7,888(2,1);7,873(2,4):7,870(2,4):7,856(3,5):7,836(1,3):7,405(1,4)6); 8,151 (1.3); 8,061 (7.7); 7.953 (0.4) 7.912 (0.9); 7,909 (0.9); 7,891 (2.3); 7,888 (2.1 ); 7,873 (2.4) 7,870 (2.4) 7,856 (3.5) 7,836 (1.3) 7,405 (1.4)
(1 ,4);7,388(2,5);7,384(2,4);7,371 (1 ,3);7,367(1 ,3);6,573(1 ,4);5,611 (13.4);5,320(9,6);3.323(10,8);2,892(2.2):2,732(1 ,9);2,672(0,4);2,525(0,8);(1, 4); 7,388 (2,5); 7,384 (2,4); 7,371 (1,3); 7,367 (1, 3); 6,573 (1,4); 5,611 (13,4); 5,320 (9; 6), 3,323 (10.8), 2,892 (2.2): 2,732 (1, 9), 2,672 (0.4), 2.525 (0.8);
2,512(21,0):2,507(44,5);2,503(60,3);2,498(44,3):2,494(22,0);2,330(0,4);0,008(0,5);0,000(20,1);-0,009(1,0) 2,512 (21.0) 2,507 (44.5); 2.503 (60.3); 2,498 (44.3) 2,494 (22.0); 2,330 (0.4) 0.008 (0.5); 0,000 (20.1) - 0.009 (1.0)
Beispiel 1-1-066: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,797(2,8);9,781(2,9);9,136(7,2);8,877(16,0);8.313(5.6);7,892(0,7);7,889(0,8);7,870(2,Example 1-1-066: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.797 (2.8), 9.781 (2.9), 9.136 (7.2), 8.877 (16.0 ); 8,313 (5.6); 7,892 (0.7); 7,889 (0.8); 7,870 (2,
2);7,867(2,3);7,853(2,6);7,850(3,0);7,844(3,2);7,842(3,5);7,823(1,1);7,735(4,3);7,729(4,3);7,598(0,4);7,425(4,4);7,420(4,3):7,393(1,4);7,388 (1,4);7,376(2,6);7,371(2,5);7,359(1,3);7,355(1,3);6,271(3,2);6,265(5,3);6,260(3,2);6,252(0,6);6,247(0.3);5,527(15,7);5,323(9,9);3,322(37.9); 3,299(1,5);2,891(0,8):2,732{0,7);2,672(0,3);2,525(0,7):2,511(19,6);2,507(42,1);2,503(57,2):2,498(41,6);2,494(20,1);2,329(0,3);0,008{0,5);0,2); 7,867 (2.3); 7,853 (2.6); 7,850 (3.0); 7,844 (3.2); 7,842 (3.5); 7,823 (1.1); 7,735 (4.3 7.729 (4.3); 7.598 (0.4); 7.425 (4.4); 7.420 (4.3): 7.393 (1.4); 7.388 (1.4); 7.376 (2.6) ; 7,371 (2.5); 7,359 (1.3); 7,355 (1.3); 6,271 (3.2); 6,265 (5.3); 6,260 (3.2); 6,252 (0.6); 6,247 (0.3); 5,527 (15.7); 5,323 (9.9); 3,322 (37.9); 2.732 {0.7); 2,672 (0.3); 2,525 (0.7): 2,511 (19.6); 2.507 (42.1); 2.503; 3.299 (1.5) 2.891 (0.8) (57.2) 2,498 (41.6); 2,494 (20.1); 2.329 (0.3) 0.008 {0.5) 0,
000(18,1);-0,009(0,7) 000 (18.1) - 0.009 (0.7)
Beispiel 1-1-067: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,903(3,3);9,886(3.4);8,531(3,1);8,526(3,2);8,506(3,9);8,504(3,9);7,885(1,8);7,879(1,7 );7,864(2,0);7,858(2,0);7,771 (2,3);7,767(2,3);7,753(2,2);7,749(2,2);7,521(3,7);7,500(3,3);5,272(8,6);4,829(16,0);3,318(49,9);2,^Example 1-1-067: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.903 (3.3); 9.886 (3.4); 8.531 (3.1); 8.526 (3.2); 8.506 (3.9), 8.504 (3.9), 7.885 (1.8), 7.879 (1.7), 7.864 (2.0), 7.858 (2.0), 7.771 (2.3), 7.767 (3,318 (2.3); 7,753 (2.2); 7,749 (2.2); 7.521 (3.7); 7,500 (3.3); 5,272 (8.6); 4,829 (16.0) 49.9); 2, ^
7(47,0);2,502(61,6);2,498(44,8);2,329(0,4);0,008(0,5);0,000(13,3) 7 (47.0) 2,502 (61.6); 2,498 (44.8); 2.329 (0.4) 0.008 (0.5); 0,000 (13.3)
Beispiel 1-1-068: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,716(2.0);9,714(1,2);9,700(1.9);7,936(3,4);7,933(3,9);7,928(2,0);7,926(2,0);7,922(2,0Example 1-1-068: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.716 (2.0), 9.714 (1.2), 9.700 (1.9), 7.936 (3.4), 7.933 ( 3.9); 7,928 (2.0); 7,926 (2.0); 7.922 (2.0
);7,919(1,8);7,878(4,8);7,818(16,0);7,408(0,8);7,399(0,8);7,394(0,9);7,391(1,0);7,386(0,9);7,383(1,0);7,377(0,8);7,369(0,8);5,828(10,7):5,7^ 5(4,8);5,451(5,8);3,321 (27,6);2,526(0.4);2,521 (0,7);2,513(11,5);2,508(25,0);2,504(34,1);2,499(24,6):2,494(11 ,6): 1 ,353(0,6); 1 ,233(1 ,0);0,00 0(0,3) Beispiel 1-1-069: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,039(2,9);10.021(3,0);8,510(3,6);8,504(3,7);8,295(3,8):7,852(2,3);7.846(2,3);7,832(2 ,6);7,825(2,6);7,691(2,2);7,686(2,2);7,673(2,1);7,669(2,1);7,514(4,4)^ ); 7.919 (1.8); 7,878 (4.8); 7,818 (16.0); 7,408 (0.8); 7,399 (0.8); 7,394 (0.9); 7,391 (1.0) 7.386 (0.9), 7.383 (1.0), 7.377 (0.8), 7.369 (0.8), 5.828 (10.7): 5.7 ^ 5 (4.8), 5.451 (5 , 8), 3.321 (27.6), 2.526 (0.4), 2.521 (0.7), 2.513 (11.5), 2.508 (25.0), 2.504 (34.1), 2.499 (24.6) : 2,494 (11, 6): 1, 353 (0.6); 1, 233 (1, 0); 0.00 0 (0.3) Example 1-1-069: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.039 (2.9), 10,021 (3.0), 8.510 (3.6), 8.504 (3.7 8,295 (3,8): 7,852 (2,3); 7,846 (2,3); 7,832 (2, 6); 7,825 (2,6); 7,691 (2,2); 7,686 (2,2) ; 7,673 (2.1); 7.669 (2.1) 7.514 (4.4) ^
323(35,9);3,292(1,1);2,673(0,4);2,526(1,0);2,521(1,5);2,513(22,5);2,508(47,5);2,503(63,7);2,499(45,2);2,494(21,1);2,330(0,4);1 046(6,0);1,031(5,9);0,000(0,5)  323 (35.9); 3,292 (1.1); 2,673 (0.4); 2,526 (1.0); 2,521 (1.5); 2,513 (22.5); 2,508 (47.5); 2.503 (63.7); 2.499 (45.2); 2.494 (21.1); 2.330 (0.4); 1 046 (6.0); 1.031 (5.9); 0.000 (0.5)
Beispiel 1-1-070: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,868(2.8);9,853(3,3);9,842(2,3);8,530(5,9);8,321(0,5);7,864(1,3);7,853(2.3);7,845(4,7 );7,833(3.6);7,825(4,6);7,815(3,2);7,794(1.4);7,751(3,3);7,741 (2,8);7,730(2,3);7,719(1 ,6);7.523(4,3);7,502(3,9);7,387(1 ,5);7,370(2,9)Example 1-1-070: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.868 (2.8), 9.853 (3.3), 9.842 (2.3), 8.530 (5.9); 8,321 (0.5); 7,864 (1.3); 7,853 (2.3); 7,845 (4,7); 7,833 (3.6); 7,825 (4,6); 7,815 (3,2); 7,794 (1.4); 7.751 (3.3), 7.741 (2.8), 7.730 (2.3), 7.719 (1, 6), 7.523 (4.3), 7.502 (3.9), 7.387 (1, 5), 7.379 (2.9)
2,5);7,331(1,0);5,761(1,8);5,273(16,0);4,693(10,5);4,599(8,1);4,351(0,4);4,339(0,4):4,104(0,6);4,091(0,6);3,397(1,2);3,380(3,4);3,362 ,330(328,6);3,299(2,4);3,183(3,2);3,170(3,1):2,678(1,7);2,509(291 ,4):2,506(223,7);2,432(1,4);2,414(3,8):2,395(3,9):2,377(1,3);2,336(1,7):2, 203(1,5);2,185(4,8);2,166(4,9);2,148(1,6);1,359(0,4);1,242(1,1);1,131(3,6);1,114(7,6);1,09^ 2.5); 7,331 (1.0); 5,761 (1.8); 5,273 (16.0); 4,693 (10.5); 4,599 (8.1); 4,351 (0.4); 4,339 (0 , 4): 4.104 (0.6), 4.091 (0.6), 3.397 (1.2), 3.380 (3.4), 3.362, 330 (328.6), 3.299 (2.4), 3.183 ( 3.12); 3.170 (3.1): 2.678 (1.7); 2.509 (291, 4): 2.506 (223.7); 2.432 (1.4); 2.414 (3.8): 2.355 (3 , 9): 2,377 (1,3); 2,336 (1,7): 2, 203 (1,5); 2,185 (4,8); 2,166 (4,9); 2,148 (1,6); 1,359 ( 0.4); 1,242 (1.1); 1,131 (3.6); 1,114 (7.6); 1.09 ^
,3);0,982(4.9);0,966(5,4);0,948(10,6);0,929(4,9);0,007(1,0) , 3); 0.982 (4.9) 0.966 (5.4) 0.948 (10.6); 0.929 (4.9) 0.007 (1.0)
Beispiel 1-1-071 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,871 (1,6);9,855(1,7);9,845(1,4);9,829(1,3);8,526(3,3);8,520(3,4);8,311(0,4);7,863(0,7 );7,860(0,7);7,847(1,6);7,845(1 ,5);7,841 (2,9);7,838(2,2);7,830(1 ,8);7,826(2,3);7,822(1 ,9);7,819(2,8);7,816(1 ,6);7,809(2,2);7,805(1,1);7,790( 1 ,0);7,786(0,9);7,747(1 ,9);7, 734(1 ,7);7,726(1 ,4); 7,712(1 ,0);7,514(2,5); 7,507(2,1 );7,494(2,3);7,487(1 ,9);7,390(0,9);7.387(0,9);7,371 (1 ,6);7,3 65(0,9);7,362(0,8);7,355(1 ,0);7,352(1,0);7,346(1 ,3);7,330(0,7);7,327(0.6);5,752(1 ,2);5.268(6,8);4,685(7,0);4,585(5,5);4,522(0,4);3,391 (0,7); 3,373(2.2);3,356(2.7);3,328(116,3);3,309(3,3);3.291(2,7);3,273 Example 1-1-071: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.871 (1.6); 9.855 (1.7); 9.845 (1.4); 9.829 (1.3 8.526 (3.3), 8.520 (3.4), 8.311 (0.4), 7.863 (0.7), 7.860 (0.7), 7.847 (1.6), 7.845 (1, 5) 7.841 (2.9), 7.838 (2.2), 7.830 (1, 8), 7.826 (2.3), 7.822 (1.9), 7.819 (2.8), 7.816 (1, 6); 7.809 (2.2); 7.805 (1.1); 7.790 (1, 0); 7.786 (0.9); 7.747 (1, 9); 7, 734 (1, 7); 7.726 (1, 4) ; 7.712 (1, 0); 7.514 (2.5); 7.507 (2.1), 7.494 (2.3), 7.487 (1.9), 7.399 (0.9), 7.387 (0.9), 7.371 (1, 6), 7.3 65 (0.9 7.362 (0.8), 7.355 (1, 0), 7.352 (1.0), 7.346 (1.3), 7.330 (0.7), 7.327 (0.6), 5.752 (1.2), 5.268 (6.8); 4.685 (7.0); 4.585 (5.5); 4.522 (0.4); 3.391 (0.7); 3,373 (2.2); 3,356 (2.7); 3,328 (116.3); 3,309 (3.3); 3,291 (2.7); 3,273
8(63,4);2,504(85,2);2,499(60,6);2,495(28,4);2,335(0,4);2,331 (0,5);2,326(0,4):2,078(1 ,6);2,069(12,0); 1 ,891 (16,0);1 ,234(0,5); 1 ,134(2,5); 1,11 6(5,7);1,098(2,4);1 ,008(3,3);0,990(7,5);0,972(3,2);0,000(0,8)  8 (63.4), 2.504 (85.2), 2.499 (60.6), 2.495 (28.4), 2.335 (0.4), 2.331 (0.5), 2.326 (0.4): 2.078 (1,6), 2,069 (12,0); 1, 891 (16.0); 1, 234 (0.5); 1, 134 (2.5); 1.116 (5.7); 1.098 (2.4); 1.008 (3.3); 0.990 (7.5); 0.972 (3.2); 0.000 (0.8)
Beispiel 1-1-072: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,907(2,5);9,891(2,6);9,119(6,5);8,838(14,6);8,742(0,6);7,847(0,7);7,844(0,8);7,830(0,Example 1-1-072: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.907 (2.5); 9.891 (2.6); 9.119 (6.5); 8.838 (14.6 ); 8,742 (0.6); 7,847 (0.7); 7,844 (0.8); 7,830 (0,
7);7,826(2,0);7,822(2,0);7,808(2,3);7,805(2,3);7,796(2,7);7,794(3,0);7,792(2,6);7,774(1,0);7,383(1,3);7,379(1,3);7,366(2,4);7,362(2,3);7,349 (1,3);7,345(1,2);5,755(1,5);5,265(9,0);4,576(16,0);4,565(0,4);4,519(1,3);3,582(2,1);3,564(7,3);3,547(7,5);3,529(2,4);3,318(38,0);2,676(0,3); 2,672(0,5);2,667(0,4);2,525(1,0);2,520(1,5);2,512(27,6);2,507(59,4);2,503(80,6);2,498(57,4);2,493(26,9);2,334(0,3);2,329(0,5);2,325(0,3) 234(0,9);1,172(7,4);1,166(0,9);1,154(15,2);1,148(1,7);1,137(7,2);1 ,131(0,8);0,008(0,4);0,000(12,3);-0,009(0,4) 7); 7,826 (2.0); 7,822 (2.0); 7,808 (2.3); 7,805 (2.3); 7,796 (2.7); 7,794 (3.0); 7,792 (2.6 7.774 (1.0); 7.383 (1.3); 7.379 (1.3); 7.366 (2.4); 7.362 (2.3); 7.349 (1.3); 7.345 (1.2) ; 5,755 (1.5); 5,265 (9.0); 4,576 (16.0); 4,565 (0.4); 4,519 (1.3); 3,582 (2.1); 3,564 (7.3); 3,547 (7.5); 3,529 (2.4); 3,318 (38.0); 2,676 (0.3); 2,672 (0.5); 2,667 (0.4); 2,525 (1.0); 2,520 (1.5); 2,512 (27.6); 2.507 (59.4); 2.503 (80.6); 2,498 (57.4); 2.493 (26.9); 2.334 (0.3); 2.329 (0.5); 2.325 (0.3) 234 (0.9); 1.172 (7.4); 1.166 (0 , 9), 1.154 (15.2), 1.148 (1.7), 1.177 (7.2), 1, 131 (0.8), 0.008 (0.4), 0.000 (12.3), -0.009 (0.4)
Beispiel 1-1-073: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,805(3,4);9,788(3,4);7,936(0,8);7,921(7,2);7,906(3,0);7,884(0,7);7,882(0,7);7,870(8,5 );7,853(0,5);7,407(1,6);7,400(1 ,5);7,391 (2,4);7,384(2,5);7,375(1 ,3);7,368(1 ,4);7,301 (2,2);7,294(0,5);7,280(4,9);7.269(0,7);7,259(2.9);6,986( 6,6);6,981(5,3);6,976(3,6);6,971(3,1);6,908(2,3);6,903(2,1);6,888(2,1);6,882(1,9);5,755(0.5);5,437(11,4);5,414(0,7);5,276(16,0);4,7Example 1-1-073: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.805 (3.4), 9.788 (3.4), 7.936 (0.8), 7.921 (7.2 7.906 (3.0), 7.884 (0.7), 7.882 (0.7), 7.870 (8.5), 7.853 (0.5), 7.407 (1.6), 7.400 (1, 5) 7.391 (2,4); 7,384 (2,5); 7,375 (1,3); 7,368 (1,4); 7,301 (2,2); 7,294 (0.5); 7,280 (4,9); 7.269 (0.7), 7.259 (2.9), 6.986 (6.6), 6.981 (5.3), 6.976 (3.6), 6.971 (3.1), 6.908 (2.3), 6.903 (2 , 1); 6,888 (2.1); 6,882 (1.9); 5,755 (0.5); 5,437 (11.4); 5,414 (0.7); 5,276 (16.0); 4.7
,320(73,4);2,676(0,5);2,672(0,6);2,668(0,5);2,525(1,8);2,507(84,6);2,503(110,9);2,498(79,8);2,334(0,5);2,330(0,7);2,325(0,5):1,234(0,9);1,^ 46(1,3);1,031(1,3);0,146(0,6);0,008(5,2);0,000(128,3);-0,008(4,9);-0,150(0,6) , 320 (73.4); 2,676 (0.5); 2,672 (0.6); 2,668 (0.5); 2,525 (1.8); 2,507 (84.6); 2.503 (110.9); 2.498 (79.8), 2.334 (0.5), 2.330 (0.7), 2.325 (0.5): 1.234 (0.9), 1, 46 (1.3), 1.031 (1.3 ); 0.146 (0.6) 0.008 (5.2) 0.000 (128.3) - 0.008 (4.9) - 0.150 (0.6)
Beispiel 1-1-074: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,803(3,4);9,786(3,4);9,649(0,4);7,932(0,7);7,917(6,5);7,913(4,0);7,903(3,0);7,901 (2,8Example 1-1-074: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.803 (3.4) 9.786 (3.4); 9,649 (0.4); 7,932 (0.7 7.917 (6.5), 7.913 (4.0), 7.903 (3.0), 7.901 (2.8
);7,881(0,7);7,879(0,7);7,868(8,6);7,406(1,6);7,399(1,5);7,390(2,2);7,383(2,4);7,374(1 ,3);7,368(1,5);7,312(0,7);7,303(8,3);7,298(2,6);7,286( 2,7);7,281(9,5);7,272(0,9);7,197(0,4);7,175(0,4);6,950(0,9);6,942(9,1);6,936(2,8);8,925(2,5);6,919(8,1);6,910(0,7);6,773(0,4);6,751(0,4);5,7 55(10,0);5,433(10,8);5,244(16,0);3,320(51,2);2,676(0,4);2,672(0,6);2,667(0,5);2,525(1,5);2,512(37,6);2,507(78,5);2,503(104,9);2,498(75,2); 2,494(35,6);2,334(0,4);2,329(0,6);2,325(0,5); 1 ,234(0,8); 1 ,046(1 ,5); 1 ,031 (1 ,5);0, 146(0,6);0,008(5,5);0,000(151 ,9);-0,009(5,5);-0, 150(0,7)); 7,881 (0.7); 7,879 (0.7); 7,868 (8.6); 7,406 (1.6); 7,399 (1.5); 7,390 (2.2); 7,383 (2.4) 7.374 (1, 3), 7.368 (1.5), 7.312 (0.7), 7.303 (8.3), 7.298 (2.6), 7.286 (2.7), 7.281 (9.5); 7,272 (0.9); 7,197 (0.4); 7,175 (0.4); 6,950 (0.9); 6,942 (9.1); 6,936 (2.8); 8,925 (2.5); 6,919 (8.1); 6.910 (0.7); 6.773 (0.4); 6.751 (0.4); 5.7.55 (10.0); 5.433 (10.8); 5.244 (16.0) ; 3,320 (51.2); 2,676 (0.4); 2,672 (0.6); 2,667 (0.5); 2,525 (1.5); 2,512 (37.6); 2.507 (78.5); 2.503 (104.9); 2,498 (75.2); 2,494 (35.6); 2,334 (0.4); 2,329 (0.6); 2,325 (0.5); 1, 234 (0.8); 1, 046 (1, 5); 1, 031 (1, 5), 0, 146 (0.6), 0.008 (5.5), 0.000 (151, 9), - 0.009 (5.5), - 0, 150 (0.7)
Beispiel 1-1-075: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,858(1 ,7);9,841 (1 ,7);7,887(3,0);7,885(3,0);7,879(1 ,8);7,874(1 ,7);7.871 (1 ,5);7,853(0,3Example 1-1-075: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.858 (1, 7); 9.841 (1, 7); 7.877 (3.0); 7.885 (3.0 7,879 (1, 8), 7,874 (1, 7), 7,871 (1, 5), 7,853 (0.3
);7,842(3,9);7,402(0,7);7,394(0,7);7,388(0,8);7,386(0,8);7,380(0,9);7,372(0,7);7,364(0,9);5,390(5,1);4,991(0,5);4,764(0.4);4,711 (0,4) 8,1);4,401(0,4);4,285(9,1);3,694(0,8);3,671(16,0);3,322(27,0);2,527(0,5);2,522(0,7);2,513(11,8);2,509(25,0);2,504(33,7);2,500(24,2);2,495( 11 ,6);0,008(1 ,8);0,000(52,4);-0,009(1 ,9) ); 7,842 (3.9); 7,402 (0.7); 7,394 (0.7); 7,388 (0.8); 7,386 (0.8); 7,380 (0.9); 7,372 (0.7) 7.364 (0.9), 5.390 (5.1), 4.991 (0.5), 4.764 (0.4), 4.711 (0.4), 8.1), 4.401 (0.4), 4.285 (9.1 ); 3,694 (0.8); 3,671 (16.0); 3.322 (27.0); 2,527 (0.5); 2,522 (0.7); 2,513 (11.8); 2.509 (25.0) 2.504 (33.7), 2.500 (24.2), 2.495 (11, 6), 0.008 (1, 8), 0.000 (52.4), - 0.009 (1, 9)
Beispiel 1-1-076: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,851 (1 ,8);9,834(1 ,9);9,832(1 ,5);9,827(2,0);9,810(1 ,7);8,314(0,4);7,953(0.4);7,906(3,4Example 1-1-076: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.851 (1.8), 9.834 (1.9), 9.832 (1.5), 9.827 (2.0 9.810 (1, 7), 8.314 (0.4), 7.953 (0.4), 7.906 (3.4
);7,903(3,7);7,897(2,1);7,894(2,7);7,890(1,9);7,878(3,1);7,865(1,6);7,862(1 ,9);7,856(7,2);7,855(7,2);7,843(0,6);7,840(0,7);7,823(0,5);7,803( 0,4);7,407(0,8);7,398(0,9);7,394(0,8);7,390(0,9);7,384(1 ,6);7,381 (1 ,3); 7,378(1 ,4);7,368(2,1);7,362(1 ,8);7,356(1 ,4);7,351 (0,9);7,346(1,0);5,4 17(6,9);5,414(6,9);5,236(1 ,0);5,231 (1 ,0);4,671 (7,4);4,591 (7,6);3,318(101 ,6);3,022(15,8);2,994(0,6);2,952(9,3);2,891 (2,8);2,818(14,8);2,732( 2,3);2,680(0,4);2,678(0,8);2,671(1,1);2,667(0,8);2,662(0,4);2,525(2,7);2,520(4,1);2,511(64,6);2,507(137,1);2,502(184,3);2,498(131,2);2,493 (61,3);2,338(0,3);2,333(0,8);2,329(1,1);2,324(0,8);2,058(16,0);2,010(0,5);1,909(0,9);1,898(15,3);1 ,234(0,6);1,196(0,5);1,178(1,0);1,159(0 ;0,000(2,6) 7.903 (3.7), 7.897 (2.1), 7.894 (2.7), 7.890 (1.9), 7.878 (3.1), 7.865 (1.6), 7.862 (1, 9) 7.856 (7.2); 7.855 (7.2); 7.843 (0.6); 7.840 (0.7); 7.823 (0.5); 7.803 (0.4); 7.407 (0.8); 7.398 (0.9), 7.394 (0.8), 7.390 (0.9), 7.384 (1, 6), 7.381 (1, 3); 7.378 (1, 4), 7.368 (2.1), 7.362 (1, 8), 7.356 (1, 4), 7.351 (0.9), 7.346 (1.0), 5.4 (6.9 5.414 (6.9), 5.236 (1.0), 5.231 (1.0), 4.671 (7.4), 4.591 (7.6), 3.318 (101, 6), 3.022 (15.8) 2.994 (0.6), 2.952 (9.3), 2.891 (2.8), 2.818 (14.8), 2.732 (2.3), 2.680 (0.4), 2.678 (0.8); 2,671 (1.1); 2,667 (0.8); 2,662 (0.4); 2,525 (2.7); 2,520 (4.1); 2,511 (64.6); 2.507 (137.1); 2.502 (184.3); 2.498 (131.2); 2.493 (61.3); 2.348 (0.3); 2.333 (0.8); 2.329 (1.1); 2.324 (0.8); 2.058 ( 16.0), 2.010 (0.5), 1.909 (0.9), 1.898 (15.3), 1.234 (0.6), 1.196 (0.5), 1.178 (1.0), 1.159 (0; 0.000 (2.6)
Beispiel 1-1-077: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,910(1,3);9,893(1,3);9,122(3,3);8,843(7,3);7,865(0,4);7,862(0,4);7,848(0,4);7,844(1,0 );7,841 (1,0);7,826(1 ,2);7,823(1 ,3);7,817(1 ,4);7,814(1,5);7,795(0,5);7,385(0,7);7,381 (0,7);7,368(1 ,2);7,364(1 ,2);7,351 (0,6);7,347(0,6);5,757(Example 1-1-077: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.910 (1.3), 9.893 (1.3), 9.122 (3.3), 8.843 (7.3 7.865 (0.4), 7.862 (0.4), 7.848 (0.4), 7.844 (1.0), 7.841 (1.0), 7.826 (1.2), 7.823 (1, 3) 7.817 (1, 4); 7.814 (1.5); 7.795 (0.5); 7.385 (0.7); 7.381 (0.7); 7.368 (1, 2); 7.364 (1, 2); 7.351 (0.6); 7.377 (0.6); 5.577 (
0,5);5,283(4,7);3,814(8,0);3,325(18,9);2,526(0,4);2,521(0,6);2,513(9,2);2,508(19,5);2,504(26,2);2,499(18,5);2,495(8,5);2,140(16,0);1,235(0^0.5); 5,283 (4.7); 3,814 (8.0); 3,325 (18.9); 2,526 (0.4); 2,521 (0.6); 2,513 (9.2); 2,508 (19 , 5); 2,504 (26.2); 2,499 (18.5); 2,495 (8.5); 2,140 (16.0); 1.235 (0 ^
4);0,008(0,7);0,000(20,7);-0,009(0,6) 4) 0.008 (0.7); 0,000 (20.7) - 0.009 (0.6)
Beispiel 1-1-078: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,802(3,4);9,785(3,4);8,313(2,0);7,935(0,8);7,922(6.4);7,920(6,7);7,915(4,0);7,907(3,2Example 1-1-078: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.802 (3.4), 9.785 (3.4), 8.313 (2.0), 7.935 (0.8 ); 7.922 (6.4); 7,920 (6.7); 7.915 (4.0) 7.907 (3.2
);7,904(2,9);7,885(0,7);7,882(0,7);7,871(8,9);7,572(0,7);7,438(3,2);7,434(3,5);7,419(3,5);7,415(3,7);7,405(1,9);7,399(1 ,6);7,390(2,3);7,^); 7,904 (2.9); 7,885 (0.7); 7,882 (0.7); 7,871 (8.9); 7,572 (0.7); 7,438 (3.2); 7,434 (3.5) 7.419 (3.5); 7.415 (3.7); 7.405 (1.9); 7.399 (1, 6); 7.390 (2.3); 7, ^
2,4);7,374(1,4);7,367(1,6);7,228(1,5);7,224(1,4);7,207(2,5);7,188(2,1);7,184(1,9);6,989(2,9);6,986(3,4);6,968(2,6);6,965(2,7);6,950(2,0);6,92.4) 7.374 (1.4); 7,367 (1.6); 7,228 (1.5); 7,224 (1.4); 7,207 (2.5); 7,188 (2.1); 7,184 (1 , 9); 6,989 (2.9); 6,986 (3.4); 6,968 (2.6); 6,965 (2.7); 6,950 (2.0); 6.9
46(1,8);6,930(3,1);6,927(2,9);6,912(1,6);6,908(1 ,5);6,518(0,4);5,754(0,5);5,440(10,7);5,355(16,0);4,581(0,6);4,565(0,6);3,317(488,4)46 (1.8), 6.930 (3.1), 6.927 (2.9), 6.912 (1.6), 6.908 (1.5), 6.518 (0.4), 5.754 (0.5), 5.440 (10.7) 5,355 (16.0); 4,581 (0.6); 4,565 (0.6); 3,317 (488.4)
3,6);2,670(5,0);2,666(3,7);2,661(1,8);2,615(0,4);2,524(13,6);2,519(21,6);2,510(297,5);2,506(625,0);2,501(836,6);2,497(598,2);2,492(283,4);3.6); 2,670 (5.0); 2,666 (3.7); 2,661 (1.8); 2,615 (0.4); 2,524 (13.6); 2,519 (21.6); 2,510 (297 , 5); 2.506 (625.0); 2.501 (836.6); 2.497 (598.2); 2.492 (283.4);
2,337(1,6);2,332(3,5);2,328(4,9);2,323(3,4);1,236(2,4);1 ,045(0,9);1,030(0,8);0,854(0,3);0,146(4,7);0,137(0,4);0,008(40,6);0,000(1162,2);-2,337 (1,6), 2,332 (3,5), 2,328 (4,9), 2,323 (3,4), 1,236 (2,4), 1,045 (0,9), 1,030 (0,8) ; 0,854 (0.3); 0,146 (4.7); 0.137 (0.4) 0.008 (40.6); 0.000 (1162.2) -
0,009(44,3);-0,036(0,5);-0, 150(4,6) 0.009 (44.3); - 0.036 (0.5); - 0, 150 (4.6)
Beispiel 1-1-079: 1H-NMR(400,0 MHz. de-DMSO): δ= 10,040(2,7);10.022(2,8);8,508(3,5);8,502(3,6);8.290(3,7);7,850(2,1);7,844(2,1);7,830(2Example 1-1-079: 1 H-NMR (400.0 MHz de-DMSO): δ = 10.040 (2.7), 10.022 (2.8), 8.508 (3.5), 8.502 (3.6 ); 8,290 (3.7); 7,850 (2.1); 7,844 (2.1); 7,830 (2
,4);7,823(2,4);7,691(2,1);7,687(2,1);7,674(2,1);7,669(2,1);7,512(4,4);7,492(3,9);5,339(9,1);4,593(15,1);3,961(0,7);3,585(2,3);3 , 4); 7,823 (2.4); 7,691 (2.1); 7,687 (2.1); 7,674 (2.1); 7.669 (2.1) 7.512 (4.4); 7,492 (3, 9); 5,339 (9.1); 4,593 (15.1); 3,961 (0.7); 3,585 (2.3); 3
50(7,7);3,533(2,4);3,320(75,3);3,169(1,5);2,676(0,6);2,671(0,8);2,667(0,6);2,524(1,8);2,520(2,9);2,511(47,7);2,507(102,5);2,502(139,6^ 98(1(X).8);2,493(47,8);2,473(0,7);2.333(0,6);2,329(0,9);2,324(0,6);1,278(0.3);1,176(7,8);1, 159(16,0)1 50 (7.7); 3,533 (2.4); 3,320 (75.3); 3,169 (1.5); 2,676 (0.6); 2,671 (0.8); 2,667 (0.6); 2,524 (1.8); 2.520 (2.9); 2.511 (47.7); 2.507 (102.5); 2.502 (139.6 ^ 98 (1 (X) .8); 2.493 (47.8); 2.473 (0.7), 2.333 (0.6), 2.329 (0.9), 2.324 (0.6), 1.278 (0.3), 1.176 (7.8), 1.159 (16.0) 1
0,8);0,008(6,2);0,000(188,9);-0,009(6,5);-0,150(0,8)  0.8) 0.008 (6.2) 0.000 (188.9) - 0.009 (6.5) - 0.150 (0.8)
Beispiel 1-1-080: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,938(1,5);7,917(2,5);7,898(2,1);7,864(5,9);7,789(2,4);7,768(1,7);7,306(2,0);7,287(1,9 j);5,415(8,3);4,915(16,0);4,273(1,1);4,040(0,7);4,022(0,8);3,332(9,5);2,543(14,2);2,527(0,6);2,513(11,2);2,509(23,6);2,505(32,1) ;2,496(11 ,0); 1 ,991 (3,3); 1 , 195(0,9); 1 , 177(1 , 7); 1 , 159(0,8);0,008(0,8);0,000(23,5); -0,008(0,9) Example 1-1-080: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.938 (1.5); 7.917 (2.5); 7.898 (2.1); 7.864 (5.9 7.799 (2.4), 7.768 (1.7), 7.306 (2.0), 7.287 (1.9j), 5.415 (8.3), 4.915 (16.0), 4.273 (1.1 ); 4,040 (0.7); 4,022 (0.8); 3,332 (9.5); 2,543 (14.2); 2,527 (0.6); 2,513 (11.2); 2.509 (23.6) ; 2,505 (32.1) 2,496 (11, 0); 1, 991 (3,3); 1, 195 (0.9); 1, 177 (1, 7); 1, 159 (0.8); 0.008 (0.8); 0.000 (23.5); -0.008 (0.9)
Beispiel 1-1-081 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,873(1, 6);9,857(1,6);7,711(1,6);7,692(6,2);7,350(1,7);7,333(2,0);7,331(2,0);7,314(1, 5Example 1-1-081: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.873 (1.6), 9.857 (1.6), 7.711 (1.6), 7.692 (6.2 7,350 (1.7); 7,333 (2,0); 7,331 (2,0); 7,314 (1, 5
);5,538(5,9);5,536(5,9);4,830(16,0);4,762(0,8);3,569(2,5);3,321(29,9);2,672(0,4);2,668(0,4);2,641 (11,1);2,526(0,9);2,521(1 ,3);2,512(15 508(33,2);2,503(44,8);2,498(31,9);2,494(14,9);2,369(0,5);1,356(0,4);0,008(1,4);0,000(38,5);-0,009(1,3) ); 5,538 (5.9); 5,536 (5.9); 4,830 (16.0); 4,762 (0.8); 3,569 (2.5); 3,321 (29.9); 2,672 (0.4) 2,668 (0,4), 2,641 (11,1), 2,526 (0,9), 2,521 (1,3), 2,512 (15,508 (33,2), 2,503 (44,8), 2,498 (31, 9); 2,494 (14.9); 2,369 (0.5); 1.356 (0.4) 0.008 (1.4) 0.000 (38.5) - 0.009 (1.3)
Beispiel 1-1-082: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,919(2,5);9,902(2,5);7,681(5,8);7,648(2,3);7,629(2,5);7,311(2,3);7,301(0,4);7,293(3,0 );7,284(0,4);7.275(2.1);7,166(0,5);5,518(8,8);5,403(0,8);4,561 (15,9);3,958(2,6);3,372(49,4);3,363(42,8);3,359(46.4);3,354(44,3);3,^Example 1-1-082: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.919 (2.5); 9.902 (2.5); 7.681 (5.8); 7.648 (2.3 7.629 (2.5), 7.311 (2.3), 7.301 (0.4), 7.293 (3.0), 7.284 (0.4), 7.275 (2.1), 7.166 (0.5), 5.518 (8.8); 5.403 (0.8); 4.561 (15.9); 3.958 (2.6); 3.372 (49.4); 3.363 (42.8); 3.359 (46.4); 3.354 (44; 3); 3, ^
;3,343(36,8);3,339(37,7);2,674(0,4);2,666(1 ,6);2,636(16,0);2,528(0,6);2,523(0,9);2,514(17,1):2,510(36,9);2,505(50,1);2,501(36,1);2,496(17, 0);1.990(0,4);0,008(0,6);0,000(20,9);-0,008(0,7) 3.343 (36.8), 3.339 (37.7), 2.674 (0.4), 2.666 (1.6), 2.636 (16.0), 2.528 (0.6), 2.523 (0.9); 2.514 (17.1): 2.510 (36.9), 2.505 (50.1), 2.501 (36.1), 2.496 (17, 0), 1.990 (0.4), 0.008 (0.6), 0.000 (20.9) - 0.008 (0.7)
Beispiel 1-1-083: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,925(2,9);9,908(3,0);7.682(6,0);7.645(2,4);7,626(2,7);7,309(1,9);7,292(3,1);7,274(1,7Example 1-1-083: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.925 (2.9), 9.908 (3.0), 7.682 (6.0), 7.645 (2.4 ); 7,626 (2.7); 7,309 (1.9); 7,292 (3.1); 7,274 (1.7
);7,140(0,6);5,755(0,7);5,519(9,5);5,399(1,0);4,599(13,1);4,355(0,6);4,338(0,6);3,591(1,9);3,573(5,9);3,556(6,0);3,538(2,0);3,3); 7,140 (0.6); 5,755 (0.7); 5,519 (9.5); 5,399 (1.0); 4,599 (13.1); 4,355 (0.6); 4,338 (0.6) ; 3,591 (1.9); 3,573 (5.9); 3,556 (6.0); 3,538 (2.0); 3.3
4(1,8);2,636(16,0);2,507(49,4);2,504(53,9);2.331(0,3);2,039(0,3);1 ,327(0,6);1,309(1,2);1,292^ 4 (1.8), 2.636 (16.0), 2.507 (49.4), 2.504 (53.9), 2.331 (0.3), 2.039 (0.3), 1.327 (0.6) ; 1,309 (1.2); 1.292 ^
8,0);0,000(23,7)  8.0); 0.000 (23.7)
Beispiel 1-1-084: 'H-NMR(400,0 MHz, de-DMSO): δ= 9.776(3,5);9,760(3,4);8,112(4,7);8,104(4,7);7,935(0,6);7,922(6,2);7,920(6,9);7,914(3,8 Example 1-1-084: 'H-NMR (400.0 MHz, de-DMSO): δ = 9,776 (3.5), 9.760 (3.4), 8.112 (4.7), 8.104 (4.7 ); 7,935 (0.6); 7.922 (6.2); 7,920 (6.9); 7.914 (3.8
);7,908(3,3);7,905(3,1);7,886(0,5);7,883(0,5);7,864(8,3);7,450(2,0);7,442(1 ,8);7,428(4,3);7,420(4,4);7,404(1,6);7,391(7,5);7,380(2,1);7,370( 3,4);7,366(1,7);5,754(1,3);5,433(10,6);5,361(0,3);5,341(16,0);3,322(109,3);2,676(0,5);2,672(0,7);2,667(0,6);2,525(1,6);2,512(43,3);2,507(97.908 (3.3), 7.905 (3.1), 7.886 (0.5), 7.8383 (0.5), 7.864 (8.3), 7.450 (2.0), 7.442 (1, 8) 7.428 (4.3); 7.420 (4.4); 7.404 (1.6); 7.391 (7.5); 7.380 (2.1); 7.370 (3.4); 7.366 (1.7); 5,754 (1.3); 5,433 (10.6); 5,361 (0.3); 5,341 (16.0); 3.322 (109.3); 2,676 (0.5); 2,672 (0.7); 2,667 (0.6); 2,525 (1.6); 2,512 (43.3); 2.507 (9
3,4);2,503(128,0);2,498(92,9);2,494(44,6);2,334(0,5);2,330(0,7);2,325(0,6);1,046(0,7);1,031(0,7);0,008(2,2);0,000(71,5);-0,009(2,5)3.4); 2,503 (128.0); 2,498 (92.9); 2,494 (44.6); 2,334 (0.5); 2,330 (0.7); 2,325 (0.6); 1,046 (0 , 7); 1.031 (0.7) 0.008 (2.2) 0.000 (71.5) - 0.009 (2.5)
Beispiel 1-1-085: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,473(1 ,6);9,456(1 ,7);7,842(4,7);7,826(2,2);7.786(1 ,1)7,783(1 ,1 );7,768(1 ,3)7,765(1 ,6 );7,746(0,7)7,743(0,7)7,358(0,9)7,355(0,9);7,338(1,6);7,323(0,8);7,320(0,8);5,377(6,7);3,741 (16,0);3,326(19.9);2,515(8,0);2,511( 06(21 ,8):2,502(15,8);2,498(7,7); 1 ,048(1,0)1,033(1, 0)0,000(0,4) Example 1-1-085: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.473 (1, 6); 9.456 (1, 7); 7.842 (4.7); 7.826 (2.2 7,768 (1, 1) 7,783 (1, 1); 7,768 (1, 3) 7,765 (1,6); 7,746 (0,7) 7,743 (0,7) 7,358 (0,9) 7,355 (0); 9), 7.338 (1.6), 7.333 (0.8), 7.320 (0.8), 5.377 (6.7), 3.741 (16.0), 3.326 (19.9), 2.515 (8.0); 2.511 (06 (21, 8): 2.502 (15.8); 2.488 (7.7); 1.048 (1.0) 1.033 (1.0) 0.000 (0.4)
Beispiel 1-1-086: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,803(1,5);9,786(1,5);7,916(2,7);7,913(3,1);7,904(2,7);7,859(3,8);7,406(0,6);7,397(0,7Example 1-1-086: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.803 (1.5), 9.786 (1.5), 7.916 (2.7), 7.913 (3.1 ); 7,904 (2.7); 7,859 (3.8); 7,406 (0.6); 7,397 (0.7
);7,394(0,7);7,390(0,7);7,385(0,7);7,381(0,7);7,377(0,7);7,368(0,6);7,148(2,8);7,143(3,0);5,754(0,7);5,552(3,0);5,547(3,1);5,421 (4,9);5,260( 7,6);3,623(16,0);3,322(21,0);2,525(0,5);2,512(14,0);2,508(30,2);2,503(41,6);2,498(30,5);2,494(14,9);0,008(0,7);0,000(23,4);-0,008(0,9)); 7,394 (0.7); 7,390 (0.7); 7,385 (0.7); 7,381 (0.7); 7,377 (0.7); 7,368 (0.6); 7,148 (2.8) 7.143 (3.0), 5.754 (0.7), 5.552 (3.0), 5.547 (3.1), 5.421 (4.9), 5.260 (7.6), 3.623 (16.0); 3,322 (21.0); 2,525 (0.5); 2,512 (14.0); 2,508 (30.2); 2.503 (41.6); 2,498 (30.5); 2.494 (14.9) 0.008 (0.7); 0,000 (23.4) - 0.008 (0.9)
Beispiel 1-1-087: 1H-NMR(400.0 MHz, de-DMSO): δ= 9,885(3,1);9,868(3,1);7,892(0,6);7,879(5,6);7,877(6,0);7,871(3.4);7,865(2,9);7,862(2,7 );7,845(7,5);7,395(1, 3)7,387(1 ,3)7,379(2,0)7,372(1 ,8)7,364(1 ,3)7,356(1 ,3);5,754(0,6);5,392(9,8);5,256(0,3);4,608(16.0);3,667(3,9);3,656Example 1-1-087: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.885 (3.1); 9.868 (3.1); 7.892 (0.6); 7.879 (5.6); 7,877 (6.0); 7,871 (3.4); 7,865 (2.9); 7,862 (2.7); 7,845 (7.5); 7,395 (1, 3) 7,387 (1, 3) 7,379 (2.0 7.372 (1, 8) 7.364 (1, 3) 7.356 (1, 3), 5.754 (0.6), 5.392 (9.8), 5.256 (0.3), 4.608 (16.0), 3.667 (3, 9); 3,656
(5,4);3,651 (3,7);3,643(5,4);3,506(5,3);3,497(3,5);3,493(5,3);3,482(3,9);3,318(54,0);3,289(0,4);3,270(36,0);3,251(1,4);3,244(0,4);2,676(0,4); 2,672(0,6);2,667(0,5);2,525(1,3);2,511(36,8);2,507(78,2):2,503(105,6);2,498(76,9);2,494(37,3);2,334(0,5);2,329(0,6);2,325(0,5);1,233(0,5); 0,146(0,6);0,008(4,6);-0,001 (139,2);-0,009(5,4);-0,150(0,6) (5.4); 3.651 (3.7); 3.643 (5.4); 3.506 (5.3); 3.497 (3.5); 3.493 (5.3); 3.482 (3.9); 54.0) 3,289 (0.4); 3,270 (36.0); 3,251 (1.4); 3,244 (0.4); 2,676 (0.4); 2,672 (0.6); 2,667 (0.5); 2,525 (1.3); 2,511 (36.8); 2.507 (78.2) 2.503 (105.6); 2,498 (76.9); 2,494 (37.3) 2,334 (0.5); 2,329 (0.6); 2,325 (0.5); 1,233 (0.5); 0.146 (0.6), 0.008 (4.6), -0.001 (139.2), -0.009 (5.4), -0.150 (0.6)
Beispiel 1-1-088: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,751(3,7);9,734(3,8);7,941(1,2);7,919(4,9);7.915(5,2);7,897(3,4);7,895(3,4);7,880(9,4Example 1-1-088: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.751 (3.7), 9.734 (3.8), 7.941 (1.2), 7.919 (4.9 ); 7,915 (5.2); 7,897 (3.4); 7.895 (3.4); 7,880 (9.4
)7,847(0,4)7,634(2,8)7,630(3,0)7,617(3,0)7,613(2,9)7,469(1,6);7,464(1 ,6)7,452(1 ,9);7,447(2,9)7,441(1,8)7,429(2,0)7.425(1,7);7,416() 7.847 (0.4) 7.634 (2.8) 7.630 (3.0) 7.617 (3.0) 7.613 (2.9) 7.469 (1.6); 7.464 (1, 6) 7.452 (1, 9) ; 7.447 (2.9) 7.441 (1.8) 7.429 (2.0) 7,425 (1.7); 7,416 (
0,4)7,410(0,5)7,400(2,0)7,396(2,1)7.383(3,6);7,379(3,7)7,367(1,9);7,362(1,9);6,394(3,9);6,372(3,7);6,315(0,4);6,292(0,4);6,243(1,9);6,20.4) 7.410 (0.5) 7.400 (2.0) 7.396 (2.1) 7,383 (3.6); 7,379 (3.7) 7,367 (1.9); 7,362 (1.9); 6,394 (3.9); 6,372 (3.7); 6,315 (0.4); 6,292 (0.4); 6,243 (1.9); 6.2
26(3,7);6,210(1,9);5,451(12,1);5,401(0,6);5,267(0,5);5,235(16,0);4,514(0,4);3,382(170,8);3,374(135,6);3,365(143,8);3,359(121,7);3,350(18026 (3.7); 6,210 (1.9); 5,451 (12.1); 5,401 (0.6); 5,267 (0.5); 5,235 (16.0); 4,514 (0.4); 3,382 (170.8) 3.374 (135.6); 3.365 (143.8); 3,359 (121.7); 3,350 (180
,1);2,963(1 ,0);2,679(0,5);2,674(0,7);2,670(0,5);2,514(44,4);2,510(84,8);2,505(109,4);2,501(81,4);2,497(41,9);2,336(0,5);2,332(0,7);2,328(0,, 1), 2.963 (1, 0), 2.679 (0.5), 2.674 (0.7), 2.670 (0.5), 2.514 (44.4), 2.510 (84.8), 2.555 (109, 4); 2.501 (81.4); 2.497 (41.9); 2,336 (0.5); 2,332 (0.7); 2,328 (0,
6);0,000(8,4) 0,000 (8.4); 6)
Beispiel 1-1-089: 1H-NMR(601,6 MHz, de-DMSO): δ= 9,858(3,2);9,847(3,2);8,530(0,6);7,915(1, 5)7,901(3,9)7,892(2,7)7,890(2,7)7,880(2,6Example 1-1-089: 1 H-NMR (601.6 MHz, de-DMSO): δ = 9.858 (3.2); 9.847 (3.2); 8.530 (0.6); 7.915 (1.5 ) 7.901 (3.9) 7.892 (2.7) 7.890 (2.7) 7.880 (2.6
);7,878(2,8);7,875(1 ,1)7,866(1 ,2)7,864(1 ,2)7,855(7,7)7,411 (1 ,7)7,408(1 ,7)7,399(2,8)7,397(2,8)7,388(1 ,6)7,385(1 ,6);5,407(12,1)4,506 (16,0);3,405(0,3);3,330(11 ,9);3,255(0,3);3,170(1 ,3);3,094(0,5);3,086(0,6);3,082(1 ,5);3,074(1 ,5);3,070(1 ,5);3,062(1 ,5);3,058(0,6);3,050(0,5);7.878 (2.8); 7.875 (1, 1) 7.866 (1.2) 7.864 (1.2) 7.855 (7.7) 7.411 (1.7) 7.408 (1, 7) 7.399 (2.8 ) 7.397 (2.8) 7.388 (1, 6) 7.385 (1, 6), 5.407 (12.1) 4.506 (16.0), 3.405 (0.3), 3.330 (11, 9), 3.255 (0 , 3); 3.170 (1, 3); 3.094 (0.5); 3.086 (0.6); 3.082 (1.5); 3.074 (1.5); 3.070 (1.5); 3.062 (1); 5); 3,058 (0.6); 3,050 (0.5);
2,616(0,4);2,538(9,1);2,528(20,1);2,519(10,5);2,510(25,8);2,507(55,9);2,504(78,1);2,501(57,7);2.498(28,2);2,440(0,5);2,388(0,6);2,385(0,4) ; 1 ,233(0,7); 1 ,207(3,2); 1 , 195(6,7); 1 , 183(3.2);0,005(0,7);0,000(26,8);-0,006(1 ,3) 2,616 (0.4); 2,538 (9.1); 2,528 (20.1); 2,519 (10.5); 2,510 (25.8); 2.507 (55.9); 2,504 (78.1); 2.501 (57.7); 2.498 (28.2); 2.440 (0.5); 2.388 (0.6); 2.385 (0.4); 1, 233 (0.7); 1, 207 (3,2); 1, 195 (6,7); 1, 183 (3.2), 0.005 (0.7), 0.000 (26.8), - 0.006 (1, 3)
Beispiel 1-1-090: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,980(2,9);9,978(2,8);9,964(3,1);9,961(2,8);8.419(3,3);8,414(3,3);7,981(2,8);7,979(2,8 Example 1-1-090: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.980 (2.9), 9.978 (2.8), 9.964 (3.1), 9.961 (2.8 ); 8,419 (3.3); 8,414 (3.3); 7,981 (2.8); 7,979 (2.8
);7,961(3,1);7,959(2,9);7,778(1,7);7,771(1,8);7,757(2,1);7,751 (2,0);7,497(3,5);7,477(3,0);7,417(2,1);7,400(2,7);7,397(2,5);7,380(2,0);5,546( 9,2);4,844(16,0);3,322(64,8);2.671(0,3);2,506(46.4);2,502(57,7);2,498(44,3);2,329(0,3);1 ,989(0,4);0,000(6,2) 7.961 (3.1), 7.959 (2.9), 7.778 (1.7), 7.771 (1.8), 7.757 (2.1), 7.751 (2.0), 7.497 (3.5) 7.477 (3.0), 7.417 (2.1), 7,400 (2.7), 7.397 (2.5), 7.380 (2.0), 5.546 (9.2), 4.844 (16.0); 3.322 (64.8), 2.671 (0.3), 2.506 (46.4), 2.502 (57.7), 2.498 (44.3), 2.329 (0.3), 1.989 (0.4), 0.000 (6.2)
Beispiel 1-1-091 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,702(3,4);8,506(3,0);8,500(3,0);7,818(1 ,7)7,811 (17)7797(2.0)7,791 (2.0)7,767(1 ,3Example 1-1-091: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.702 (3.4), 8.506 (3.0), 8.500 (3.0), 7.818 (1.7 ) 7,811 (17) 7797 (2.0) 7,791 (2.0) 7,767 (1, 3
);7,763(1,3);7,744(2,3);7,741 (2,3);7,688(3,7);7,666(2,1);7,499(3,6);7,479(3,2);5,238(8,5);4,798(16,0);3,662(0,3);3,571(0,6);3,333(8,7);2,517 (5,1);2.513(10,6);2,508(14,2);2,504(10.3);2,500(4,9);2,373(14,4);0,000(6,1) 7.763 (1.3), 7.744 (2.3), 7.741 (2.3), 7.688 (3.7), 7.666 (2.1), 7.499 (3.6), 7.499 (3.2) 5,238 (8.5); 4,798 (16.0); 3,662 (0.3); 3,571 (0.6); 3,333 (8,7); 2,517 (5,1); 2,513 (10,6); 2,508 (14.2); 2,504 (10.3); 2,500 (4.9); 2,373 (14.4); 0,000 (6.1)
Beispiel 1-1-092: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,820(1,8);9,803(2,2);9,785(0,5);7,713(5,0);7,684(2.2);7,665(2,3);7,601(3,0);7,596(3,0Example 1-1-092: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.820 (1.8); 9.803 (2.2); 9.785 (0.5); 7.713 (5.0 ); 7,684 (2.2); 7,665 (2.3); 7,601 (3.0); 7,596 (3.0
)7,317(1,7)7,300(2,5)7,282(2,4);6,048(0,9);6,032(3,1);6,027(3,1);5,569(6,6);5,483(2,5);5,470(0,6);5,441(9,4);4,039(0,4);4,021 (0,4);3,32 70,2);2,699(0,8);2,671(0,7);2,653(13,8);2,524(1,1);2,507(56,1);2,502(73,5);2,498(52,9);2,334(0,3);2,329(0,4);2,325(0,3);2,248(0,8);2,217(3, 8);2, 140(16,0); 1 ,989(1 ,9); 1 ,299(0,4); 1 ,259(0,7); 1 ,235(1 ,3); 1 , 193(0,5); 1 , 175(1 ,0); 1 , 158(0,5)0,000(1,1) ) 7.317 (1.7) 7.300 (2.5) 7.282 (2.4); (5,483; 6,048 (0.9); 6,032 (3.1); 6,027 (3.1); 5,569 (6.6) 2.5), 5.470 (0.6), 5.441 (9.4), 4.039 (0.4), 4.021 (0.4), 3.32 (70.2), 2.699 (0.8), 2.671 ( 0.7); 2,653 (13.8); 2,524 (1.1); 2,507 (56.1); 2.502 (73.5); 2,498 (52.9); 2,334 (0.3); 2,329 (0 , 4); 2,325 (0.3); 2,248 (0.8); 2,217 (3,8); 2,140 (16,0); 1, 989 (1, 9); 1, 299 (0.4); 1, 259 (0.7); 1, 235 (1, 3); 1, 193 (0.5); 1, 175 (1, 0); 1, 158 (0.5) 0.000 (1.1)
Beispiel 1-1-093: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,789(2,5);9,772(2,5);7,831(0,4);7,822(5,8);7,816(5,9);7,711(6,9);7,698(2,5);7,679(2,7 Example 1-1-093: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.789 (2.5); 9.772 (2.5); 7.831 (0.4); 7.822 (5.8 ); 7.816 (5.9) 7.711 (6.9) 7.698 (2.5); 7,679 (2.7
);7,327(2,4);7,309(3,1);7,292(2,2);6,343(6,4);6,337(6,4);5,567(8,5);5,535(0,5);5,527(0,6);5,507(14,3);4,925(0,6);3,494(6,0);3,390(0,4);2,871); 7,327 (2.4); 7,309 (3.1); 7,292 (2.2); 6,343 (6.4); 6,337 (6.4); 5,567 (8.5); 5,535 (0.5) ; 5,527 (0.6); 5,507 (14.3); 4,925 (0.6); 3,494 (6.0); 3,390 (0.4); 2,871
(3,4);2,693(0,5);2,676(0,6);2,671 (0,8);2,667(0,8);2,651(16,0);2,547(0,4);2,532(0,4);2,524(1,3);2,511(33,5);2,507(70,6);2,502(95,2);2,498(69(3,4); 2,693 (0.5); 2,676 (0,6); 2,671 (0,8); 2,667 (0,8); 2,651 (16,0); 2,547 (0,4); 2,532 ( 0.4); 2,524 (1.3); 2,511 (33.5); 2.507 (70.6); 2.502 (95.2); 2,498 (69
,0);2,493(33,1);2,334(0,4);2,329(0,6);2,324(0,4);2,255(0,5);2,075(1,3);1,989(0,6);1,910(0,7);1,299(0,^ , 0); 2,493 (33.1); 2,334 (0.4); 2,329 (0.6); 2,324 (0.4); 2,255 (0.5); 2,075 (1.3); 1,989 (0, 6); 1,910 (0.7); 1,299 (0, ^
75(0,4);0,000(1,8)  75 (0.4); 0,000 (1.8)
Beispiel 1-1-094: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,813(1,2);9,797(1,2);7,712(3,0);7,687(1,2);7,668(1,2);7,491(0,3);7,483(3,1);7,481 (3,2 );7,320(1, 1 );7,302(1, 5)7,284(1 ,0)7, 198(3,4)7, 197(3,4)5,567 (3,9);5,427(0,5);5,406(6,3);4,056(0,5);4,038(1 ,5);4,021(1 ,5);4,003(0,5);3,771 ( 1,1);3,676(16,0);3,320(41,6);2.694(0,6);2,671(0.4);2,652(7,1);2,524(0,7);2,511(14,9);2,506(30.7);2,502(40,7);2,497(29,3);24 Example 1-1-094: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.813 (1.2), 9.797 (1.2), 7.712 (3.0), 7.687 (1.2 7.688 (1.2); 7.491 (0.3); 7.483 (3.1); 7.481 (3.2); 7.320 (1, 1); 7.302 (1.5) 7.284 (1, 0) 7 , 198 (3.4) 7, 197 (3.4) 5.567 (3.9), 5.427 (0.5), 5.406 (6.3), 4.056 (0.5), 4.038 (1.5); 4.021 (1.5), 4.003 (0.5), 3.771 (1.1), 3.676 (16.0), 3.320 (41.6), 2.694 (0.6), 2.671 (0.4), 2.652 (7 , 1); 2,524 (0.7); 2,511 (14.9); 2,506 (30.7); 2.502 (40.7); 2.497 (29.3); 24
(6,8); 1 ,259(0,4); 1 ,234(0,7); 1.193(1,8)1, 175(3,5); 1 , 157(1 ,7);0,000(0,8) (6.8); 1, 259 (0.4); 1, 234 (0.7); 1,193 (1.8) 1, 175 (3.5); 1, 157 (1, 7); 0.000 (0.8)
Beispie! 1-1-095: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,779(2,2);9,763(2,2);7.972(7,0);7,970(7,4);7,711(6,5);7,697(2,1);7,678(2.3);7,540(7,1 |);7,538(7,3)7,328(2,2)7,311 (2,6)7,310(2,7);7,293(2,0);5,5677,2);5,516(13,1);4,056(1,2);4,039(3,6);4,021(3,6);4,003(^ 76(0,5);2,671 (0,7);2,667(0,7);2.651 (14,0);2,525(1 ,3);2,520(2, 1);2,511 (30.3);2,507(65, 1);2,502(87,9);2,498(62.9);2,493(29,4);2.334(0,4);2.3 29(0,5);2,325(0,4);2,075(1 ,4);1 ,989(16,0);1 ,259(0,6);1 ,234(0,9);1 , 193(4,5); 1 ,175(9,0); 1 ,157(4,4);0,000(1 ,6) Step Example! 1-1-095: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.779 (2.2); 9.763 (2.2); 7.972 (7.0); 7.970 (7.4) 7.711 (6.5); 7.697 (2.1); 7.678 (2.3); 7.540 (7.1); 7.538 (7.3) 7.328 (2.2) 7.311 (2.6) 7.310 (2, 7); 7,293 (2.0); 5,5677,2); 5.516 (13.1); 4,056 (1.2); 4,039 (3.6); 4,021 (3.6); 4,003 (^ 76 (0.5), 2.671 (0.7), 2.667 (0.7), 2,651 (14.0), 2.525 (1, 3), 2.520 (2, 1), 2.511 (30.3), 2.507 (65 , 1), 2.502 (87.9), 2.498 (62.9), 2.493 (29.4), 2.334 (0.4), 2.3 29 (0.5), 2.325 (0.4), 2.075 (1, 4 1, 989 (16.0); 1, 259 (0.6); 1, 234 (0.9); 1, 193 (4.5); 1, 175 (9.0); 1, 157 (4,4); 0,000 (1, 6)
Beispiel 1-1-096: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,769(2,5);9,753(2.6);8,522(8,1);8,464(0,9)7,964(8,6)7,716(6,4)7,706(2.8)7,686(2,6Example 1-1-096: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,769 (2.5); 9,753 (2.6); 8,522 (8.1); 8,464 (0.9) 7,964 (8.6) 7.716 (6.4) 7.706 (2.8) 7.686 (2.6
);7,329(2,2);7,311 (3,0);7,293(2,0);5,646{13,0);5,573(8,5);5,496(0,7);4,039(0,8);4,021 (0,8);3,321 (72,6);2,676(0,5);2,671 {0,7);2,653(16,0);2,5 25( 1 ,2);2,511 (28,5);2,507(59, 1 ); 2,502(78,3);2,498(55.9);2,494(26,6); 2,334(0,3);2,329(0,5);2,325(0,3); 1 ,989(3,3); 1 ,336(0,5); 1 ,299(1 ,8); 1 ,257,329 (2,2); 7,311 (3,0); 7,293 (2,0); 5,646 {13,0); 5,573 (8,5); 5,496 (0.7); 4.039 (0.8) 4.021 (0.8), 3.321 (72.6), 2.676 (0.5), 2.671 {0.7), 2.653 (16.0), 2.5 25 (1, 2), 2.511 (28, 5); 2,507 (59, 1); 2,502 (78.3); 2,498 (55.9); 2,494 (26.6); 2,334 (0.3); 2,329 (0.5); 2,325 (0.3); 1, 989 (3,3); 1, 336 (0.5); 1, 299 (1, 8); 1, 25
9(3,0); 1 ,235(3,7); 1 , 193(1 , 1 ); 1 , 175(2, 1 ); 1 , 158(1 ,0);0,853(0,6);0,835(0,3);0,000(1 ,5) 9 (3.0); 1, 235 (3, 7); 1, 193 (1, 1); 1, 175 (2, 1); 1, 158 (1, 0), 0.853 (0.6), 0.835 (0.3), 0.000 (1, 5)
Beispiel 1-1-097: 1H-NMR(400,0 MHz, de-DMSO): 5= 9.927(2,9);9,911 (2,9)7,681 (5.8);7,644(2,2);7,625(2,4);7,307(1 ,9);7,288(3,0);7.278(0,7Example 1-1-097: 1 H-NMR (400.0 MHz, de-DMSO): 5 = 9,927 (2.9), 9.911 (2.9) 7.681 (5.8), 7.644 (2.2), 7.625 (2.4); 7.307 (1, 9); 7.288 (3.0); 7.278 (0.7
);7,271 (1,7);7,261 (0,4);7,141 (1 ,1 );5,518(8,7);5,414(0,4);5,399(1 ,5);4,602(15,0);4,269(0,9);4,252(1 ,9);4,236(0,9);3,489(4,5);3,472(9,2);3,4567.271 (1.7), 7.261 (0.4), 7.141 (1, 1), 5.518 (8.7), 5.414 (0.4), 5.399 (1.5), 4.602 (15.0) 4.269 (0.9), 4.252 (1, 9), 4.236 (0.9), 3.489 (4.5), 3.472 (9.2), 3.456
(4,6);3,348(216,8);3,345(191 ,8);3,341 (131 ,6);2,665(3,3);2,635(16,0);2,509(53,7);2,505(72,5);2,501 (53,7);2,463(0,9) (4,6); 3,348 (216,8); 3,345 (191,8); 3,341 (131,6); 2,665 (3,3); 2,635 (16,0); 2,509 (53,7); 2,505 ( 72.5), 2,501 (53.7), 2,463 (0.9)
,735(0,5); 1 ,718(1 ,0); 1 ,700(1 ,0); 1 ,683(0,5); 1 ,609(0,6); 1 ,590(2,4); 1 ,573(4,6); 1 ,555(4,9); 1 ,537(2,5); 1 ,520(0,6); 1 ,232(0,5); 1 , 194(0,4); 1 , 177(0,7 , 735 (0.5); 1, 718 (1, 0); 1, 700 (1, 0); 1, 683 (0.5); 1, 609 (0.6); 1, 590 (2,4); 1, 573 (4,6); 1, 555 (4.9); 1, 537 (2.5); 1, 520 (0.6); 1, 232 (0.5); 1, 194 (0.4); 1, 177 (0.7
);1 ,159(0,4);1 , 147(0,4);1 ,132(0,4);0,931 (1 ,7);0,919(8,0);0,913(4,0);0,900(15,4);0,882(7,1);0,008(0,4);0,000(12,2);-0,009(0,5) 1, 159 (0.4), 1, 147 (0.4), 1, 132 (0.4), 0.931 (1, 7), 0.919 (8.0), 0.913 (4.0); 0.900 (15.4); 0.882 (7.1) 0.008 (0.4) 0.000 (12.2) - 0.009 (0.5)
Beispiel 1-1-098: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,520(3,4);8,514(3,5);7,882(1 ,7)7,861 (3,0)7,842(2,2)7.828(1 ,9)7,822(1 ,9)7,807(2,1Example 1-1-098: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.520 (3.4); 8.514 (3.5); 7.882 (1.7) 7.861 (3.0) 7.842 (2.2) 7.828 (1.9) 7.822 (1.9) 7.807 (2.1
);7,801 (2,2);7,612(2,7);7,591 (2,3);7,504(3,9);7,483(3,4);7,290(2,6);7,271 (2,5);5,263(10,2);4,926(16,0);3,569(1 ,0);3,325(24,2);2,555(17,5);2, 509(21 ,5);2,505(28,9);2,501 (22,3);2,233(0,4);0,000(0,5) 7.801 (2.2), 7.612 (2.7), 7.551 (2.3), 7.504 (3.9), 7.483 (3.4), 7.290 (2.6), 7.271 (2.5) 5.263 (10.2), 4.926 (16.0), 3.569 (1, 0), 3.325 (24.2), 2.555 (17.5), 2.509 (21, 5), 2.505 (28.9 2.501 (22.3), 2.233 (0.4), 0.000 (0.5)
Beispiel 1-1-099: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,902(1 ,9);9,896(2,1);9,891 (2,2);9,885(1 ,9);8,506(3,5);8,500(3,5);8,019(0,9);8,013(0,9Example 1-1-099: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.902 (1, 9), 9.896 (2.1), 9.891 (2.2), 9.885 (1, 9 ); 8,506 (3.5); 8,500 (3.5); 8,019 (0.9); 8,013 (0.9
);7,995(1,8);7,990(1 ,5);7,975(1 ,3);7,969(1 ,2);7,860(2,1);7,848(2,2);7,837(3,1);7,824(1 ,7);7,818(2,3);7,811 (2,g 7,995 (1,8); 7,990 (1, 5); 7,975 (1, 3); 7,969 (1, 2); 7,860 (2,1); 7,848 (2,2); 7,837 (3,1) 7.824 (1, 7), 7.818 (2.3), 7.811 (2, g
0.5);5,272(10,2);4,808(16,0);4,343(0,4);3,362(0,9);3,172(2,1);2,806(0,4);2,609(0,4);2,506(16,6);0,000(4,6)  0.5); 5,272 (10.2); 4,808 (16.0); 4,343 (0.4); 3,362 (0.9); 3,172 (2.1); 2,806 (0.4); 2,609 (0.4 ); 2,506 (16.6); 0,000 (4.6)
Beispiel 1-1-100: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,740(3,3);9,724(3,3);8,430(3,7);8,366(0,4);7,887(1 ,6)7,866(1 ,9)7,859(2,0)7,837(1 ,8 Example 1-1-100: 'H NMR (400.0 MHz, de-DMSO): δ = 9.740 (3.3); 9.724 (3.3); 8.430 (3.7); 8.366 (0.4 7,887 (1,6) 7,866 (1,9) 7,859 (2,0) 7,837 (1, 8
);7,818(2,0);7,812(2,1);7,798(2,5);7,792(2,6);7,513(3,9);7,493(3,5);7,449(0,5);7,429(0.4);7,407(1 ,2);7,394(1 ,6);7,391 (1 ,8);7,386(1 ,7);7,378( 1 ,7);7,373(1 ,6);7,370(1 ,6);7,357(1 ,1);5,757(1 ,1);5,334(0,4);5,302(8,7);4,860(0,4);4,833(16,0);4,562(0,6);4,547(0,6);3,326(17,4);3,179(0,4);3 ,166(0,4);2,894(0,9);2,734(0,8);2,509(23,8);2,505(29,4);0,000(5,7) ); 7,818 (2.0); 7,812 (2.1); 7,798 (2.5); 7,792 (2.6); 7,513 (3.9); 7,493 (3.5); 7,449 (0.5) 7,429 (0.4); 7,407 (1,2), 7,394 (1,6), 7,391 (1,8), 7,386 (1, 7), 7,378 (1, 7), 7,373 (1,6), 7,370 ( 1, 6), 7.357 (1, 1), 5.757 (1, 1), 5.334 (0.4), 5.302 (8.7), 4.860 (0.4), 4.833 (16.0), 4.562 (0 , 6); 4.547 (0.6); 3.326 (17.4); 3.179 (0.4); 3, 166 (0.4); 2.894 (0.9); 2.734 (0.8); 2.509 ( 23.8) 2,505 (29.4); 0,000 (5.7)
Beispiel 1-1-101 : 1H-NMR(400,0 MHz, de-DMSO): 6= 9,483(1 ,6);9,467(1 ,7);8.498(2,1);8.492(2,2);7,800(1 ,2)7,794(1 ,3)7,780(1 ,4)7,773(1.4 );7,733(0,6);7,730(0,6);7,712(1 ,5);7,709(1 ,3);7,694(1 ,4);7,691 (1 ,4);7,666(2,1);7,646(0,9);7.489(2,5);7,468(2,2);7,343(0^ Example 1-1-101: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.483 (1, 6), 9.467 (1, 7), 8,498 (2.1), 8,492 (2.2 7,800 (1, 2) 7,794 (1, 3) 7,780 (1,4) 7,773 (1.4); 7,733 (0,6); 7,730 (0,6); 7,712 (1, 5); 7,709 (1); 3), 7.694 (1, 4), 7.691 (1, 4), 7.666 (2.1), 7.646 (0.9), 7.489 (2.5), 7.468 (2.2), 7.343 (0 ^
1 ,5);7,322(1 ,6):7,308(0,8);7,305(0,8);5,230(6,5);3,739(16,0);3,329(9,6);2,515(6,8);2,510(14,2);2,506(19,2);2,501 (14,2);2,497(7,1);0,000(0,3 )  1, 5); 7,322 (1,6): 7,308 (0.8); 7,305 (0,8); 5,230 (6,5); 3,739 (16,0); 3,329 (9,6); 2,515 (6 , 8), 2.510 (14.2), 2.506 (19.2), 2.501 (14.2), 2.497 (7.1), 0.000 (0.3)
Beispiel 1-1-102: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,929(3,3);9,911 (3,5);8,543(4,3);8,538(4,3);8,347(4,7);7,896(2,3);7,889(2,3);7,875(2,6Example 1-1-102: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.929 (3.3), 9.911 (3.5), 8.543 (4.3), 8.538 (4.3 ); 8,347 (4.7); 7,896 (2.3); 7,889 (2.3); 7,875 (2.6
);7,869(2,6);7,742(5,2);7,737(5,3);7,707(2,6);7,703(2,7);7,685(2,6);7,537(5,0);7,517(4,4);7,438(5,4);7,434(5,6);6,282(3,3);6,277(5,9);6,272( 3,4);5,546(16,0);5,393(11 ,1);4,341 (0,6);4,330(0,6);3,318(468,6);2,670(2,3);2,505(291 ,1);2,501 (387,6);2,497(291 ,6);2,328(2,2);1 ,351 (0,7);1 , 249(0,4);1 ,234(1 ,3);1 ,044(3,3);1 ,029(3,3);-0,001 (2,6) ); 7,869 (2.6); 7,742 (5.2); 7,737 (5.3); 7,707 (2.6); 7,703 (2.7); 7,685 (2.6); 7,537 (5.0) 7.517 (4.4), 7.438 (5.4), 7.434 (5.6), 6.282 (3.3), 6.277 (5.9), 6.272 (3.4), 5.546 (16.0); 5.393 (11, 1), 4.341 (0.6), 4.330 (0.6), 3.318 (468.6), 2.670 (2.3), 2.555 (291, 1), 2.501 (387.6), 2.497 (291, 6); 2,328 (2,2); 1, 351 (0,7); 1, 249 (0,4); 1, 234 (1,3); 1, 044 (3,3); 1 , 029 (3,3); - 0,001 (2,6)
Beispiel 1-1-103: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,542(3,8);8,536(3,9);7,858(4,1);7,852(2,4);7,838(5,8);7,831 (2,8);7,818(2,5);7,714(4,6Example 1-1-103: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.542 (3.8), 8.536 (3.9), 7.858 (4.1), 7.852 (2.4 7.838 (5.8), 7.831 (2.8), 7.818 (2.5), 7.714 (4.6
);7,709(4,7);7,609(3,0);7,588(2,5);7,521 (4.5);7,500(4.0);7,414(4,8);7,410(4,9);7.262(2,9);7,243(2,7);6,253(3,2);6,248(5,4);6,^ 7.709 (4.7), 7.609 (3.0), 7.588 (2.5), 7.521 (4.5), 7.500 (4.0), 7.414 (4.8), 7.410 (4.9), 7.262 (2 , 9); 7,243 (2.7); 6,253 (3.2); 6,248 (5.4); 6 ^
16,0);5,294(107);4,342(0,5);4,332(0,5);3,321 (78,6);2,676(0,4)£  16.0), 5.294 (107), 4.342 (0.5), 4.332 (0.5), 3.321 (78.6), 2.676 (0.4) pounds
(68,4);2.334(0,4);2,329(0,5);2,325(0,4); 1 ,046(4,3); 1 ,030(4,2);0,008(2, 1);0,000(51 ,5);-0,008(2,3)  (68.4) 2,334 (0.4); 2,329 (0.5); 2,325 (0.4); 1, 046 (4,3); 1, 030 (4,2), 0,008 (2, 1), 0,000 (51, 5), - 0,008 (2,3)
Beispiel 1-1-104: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,662(4,0);9,660(3,6);8,529(3,4);8,524(3,4);7,843(2,2);7,837(2,1 );7,822(2,4);7,816(2,4Example 1-1-104: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.662 (4.0), 9.660 (3.6), 8.529 (3.4), 8.524 (3.4 7.843 (2.2), 7.837 (2.1), 7.822 (2.4), 7.816 (2.4
5;7,743(1,3);7,739(1 ,4);7,733(4,2);7J32(4,3);7,728(4,4);7,726(4,4);7,721 (3,0);7,717(3,0);7,688(4,4);7,666(1 ,9);7,516(4,0);7,496(3,6);7,425( 4,1);7,424(4,3);7,420(4,5);7,419(4,2);6,269(3.4);6,264(5,3);6,259(3,4);5,520(14,8);5,268(9,0);3,729(0,5);3,334(51 ,6);2,672(0,^ 7,743 (4,4); 7,726 (4,4); 7,721 (3,0); 7.717 (3.0); 7.688 (4.4); 7.666 (1, 9); 7.516 (4.0); 7.496 (3.6); 7.425 (4.1); 7.424 (4.3); (4.5) 7,420; 7,419 (4.2); 6,269 (3.4); 6,264 (5.3); 6,259 (3.4); 5,520 (14.8); 5,268 (9.0); 3,729 (0 , 5); 3,334 (51, 6); 2,672 (0, ^
,520(1 ,4);2,512(18,9);2,507(40,2);2,503(56,5);2,498(42,1);2,494(19,8);2,335(16,0);0,008(1 ,6);0,000(48,1);-0,009(1 ,5)  , 520 (1, 4), 2.512 (18.9), 2.507 (40.2), 2.503 (56.5), 2.498 (42.1), 2.494 (19.8), 2.355 (16.0); 0.008 (1, 6); 0.000 (48.1); - 0.009 (1, 5)
Beispiel 1-1-105: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,673(4,2);9,656(4,4);8,452(4,5);7,859(2, 1);7,838(4,6);7,823(2,9);7,817(2,9);7,809(2,4Example 1-1-105: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.673 (4.2), 9.656 (4.4), 8.452 (4.5), 7.859 (2, 1 ); 7,838 (4.6); 7,823 (2.9); 7,817 (2.9); 7,809 (2.4
);7,772(0,5);7,745(5,4);7,742(5,4);7,528(4,8);7,507(4,3);7,436(5,9);7,434(6,4);7,375(1 ,3);7,360(2,0);7,346(1 ,9);7,324(1 ,2);6,276(5,5);5,572( 1 ,0);5,556(16,0);5,333(10,5);4,818(0,6);3,318(108,5);2,670(0,8);2,501 (134,8);2,328(0,8); 1 ,234(0,7);0,000(57,6);-0,002(48,8) ); 7,772 (0.5); 7,745 (5.4); 7,742 (5.4); 7,528 (4.8); 7,507 (4.3); 7,436 (5.9); 7,434 (6.4) 7,375 (1,3), 7,360 (2,0), 7,346 (1, 9), 7,324 (1,2), 6,276 (5,5), 5,572 (1, 0), 5,556 (16,0); 5.333 (10.5), 4.818 (0.6), 3.318 (108.5), 2.670 (0.8), 2.501 (134.8), 2.328 (0.8); 1, 234 (0.7), 0.000 (57.6), - 0.002 (48.8)
Beispiel 1-1-106: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.848(1 ,2);9,842(1 ,3);9,837(1 ,4);9,831 (1 ,2);8,531 (2,1);8,525(2.1 );7,991 (0.6)7,985(0,5Example 1-1-106: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,848 (1, 2), 9.842 (1, 3), 9.837 (1, 4), 9.831 (1, 2 8.531 (2.1), 8.525 (2.1), 7.991 (0.6) 7.985 (0.5
);7,967(1, 1)7,961 (0,8)7,947 (0,8)7,941 (0,7)7,866(1 , 3)7,859(2,4)7,846(2,4)7,839(1 ,6);7,823(0,9);7,739(2,6);7,734(2,6);7,528(2,5);7,508( 2,2);7,433(2,7);7,432(2,6);7,429(2,8);6,277(1 ,8);6,272(2,9);6,267(1 ,7);5,535(8,3);5,303(5,7);4,341 (2,2);4,331 (2,3);3,794(0,6);3,783(0,7);3,7 78(0,8);3,768(0,8);3,763(0,6);3,752(0,6);3,320(30,1);3,176(1 ,4);3, 163(1 ,4);2,506(30,6);2,502(38,8);2,498(27,5); 1 ,045(16,0);1 ,030(15,6);0,0 08(1 ,1);0,000(24,3);-0,009(0.9) 7.967 (1, 1) 7.961 (0.8) 7.947 (0.8) 7.941 (0.7) 7.866 (1.3) 7.859 (2.4) 7.846 (2.4) 7.839 (1, 6) 7.823 (0.9); 7.739 (2.6); 7.734 (2.6); 7.528 (2.5); 7.508 (2.2); 7.433 (2.7); 7.432 (2.6); 7,429 (2,8); 6,277 (1, 8); 6,272 (2,9); 6,267 (1, 7); 5,535 (8,3); 5,303 (5,7); 4,341 (2,2); 4,331 (2.3); 3.794 (0.6); 3.783 (0.7); 3.7.78 (0.8); 3.768 (0.8); 3.763 (0.6); 3.752 (0.6) 3,320 (30,1); 3,176 (1,4); 3,163 (1,4); 2,506 (30,6); 2,502 (38,8); 2,498 (27,5); 1, 045 (16.0), 1, 030 (15.6), 0.08 (1, 1), 0.000 (24.3), - 0.009 (0.9)
Beispiel 1-1-107: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.485(1 ,7);9,469(1 ,7);9,112(4,3);8.822(9,3);7,752(0,3);7,738(3.7);7,731 (2,1);7,724(1 ,8Example 1-1-107: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,485 (1, 7), 9.469 (1, 7), 9.112 (4.3), 8.822 (9.3 7.752 (0.3); 7.738 (3.7); 7.731 (2.1); 7.724 (1.8
);7,350(0,8);7,342(0,7);7,334(1 ,0);7,327(1 ,1 );7,319(0,7);7,311 (0,7);5,760(0,6);5,259(6,7);3,738(16,0);3,329(7^ 7,350 (0.8); 7,342 (0.7); 7,334 (1, 0); 7,327 (1, 1); 7,319 (0.7); 7,311 (0.7); 5,760 (0,6) 5.259 (6.7); 3.738 (16.0); 3.329 (7 ^
03(10,3);1 ,231 (0,4);1 ,048(1 , 1);1 , 033(1.1) 03 (10,3); 1, 231 (0,4); 1, 048 (1, 1); 1, 033 (1.1)
Beispiel 1-1-108: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,889(3,7);9,883(3,8);8,095(1 ,6);8,090(1 ,6);8,072(2,6);8,067(2.6);7,994(3,9);7,970(2,5Example 1-1-108: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.889 (3.7); 9.883 (3.8); 8.095 (1, 6); 8.090 (1, 6 ); 8,072 (2.6); 8,067 (2.6); 7,994 (3.9); 7,970 (2.5
);7,831 (5,8);5,424(8,5);4,791 (16,0);4,057(0,7);4,039(2,2);4,021 (2,2);4,003(0,8);3,321 (45,1 );2.525(0,6);2,512(14,5);2,507(30,2);2,503(40,6); 2,498(29,2);2,494(14,0); 1 ,990(9,4);1 , 194(2,4); 1 , 176(4,8); 1 , 158(2,4);0,007(0,5);0,000(16,4);-0,001 (15,3);-0,009(0,6) 7.831 (5.8), 5.444 (8.5), 4.791 (16.0), 4.057 (0.7), 4.039 (2.2), 4.021 (2.2), 4.003 (0.8) 3.321 (45.1), 2.525 (0.6), 2.512 (14.5), 2.507 (30.2), 2.503 (40.6); 2,498 (29.2); 2,494 (14.0); 1, 990 (9.4); 1, 194 (2,4); 1, 176 (4,8); 1, 158 (2.4), 0.007 (0.5), 0.000 (16.4), - 0.001 (15.3), - 0.009 (0.6)
Beispiel 1-1-109: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,909(2,9);9,892(3,0);8,600(4,2);8,596(4,4);8,567(4,1);8,561 (4,3);7,933(2,4);7,928(4,1 );7,923(2,5);7,842(1 ,0)7,840(1 ,1 );7,821 (2,6)7,802(1 ,9)7,799(1 ,9)7,743(3,5)7,721 (2,1)7,384(1 ,4)7,382(1 ,5)7,365(2,8)7,349(1 ,4);7,347( 1 ,4);5,256(10,5);4,548(16,0);3,369(30,0);3,320(29,7);2,509(27,7);2,505(38,9);2,500(29,8);0,008(1 ,5);0,000(45,2);-0,008(2,0) Example 1-1-109: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.909 (2.9); 9.892 (3.0); 8.600 (4.2); 8.596 (4.4 8.567 (4.1); 8.561 (4.3); 7.933 (2.4); 7.928 (4.1); 7.923 (2.5); 7.842 (1.0) 7.840 (1, 1); 7.821 (2.6) 7.802 (1.9) 7.799 (1.9) 7.743 (3.5) 7.721 (2.1) 7.384 (1, 4) 7.382 (1.5) 7.365 (2.8) 7.349 ( 1, 4), 7.347 (1, 4), 5.256 (10.5), 4.548 (16.0), 3.369 (30.0), 3.320 (29.7), 2.509 (27.7), 2.505 (38 , 9), 2,500 (29.8), 0.008 (1, 5), 0.000 (45.2), - 0.008 (2.0)
Beispiel 1-1-110: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,840(1 ,5);9,838(1 ,6);9,833(1 ,8);9,830(1 ,6);8,425(2,5);8.419(2,7);8,289(0,9);8,284(0,9 );8,267(1,0);8,261 (1 ,7);8,255(1 ,0);8,238(0,9);8,232(0,9);7,817(1 ,5);7,810(1 ,5);7,796(1 ,7);7,790(1 ,7);7,522(3,5);7,501 (3,0);5,755(0,9);5,290(Example 1-1-110: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.840 (1.5), 9.838 (1.6), 9.833 (1.8), 9.830 (1.6 8.425 (2.5), 8.419 (2.7), 8.289 (0.9), 8.284 (0.9), 8.267 (1.0), 8.261 (1, 7), 8.255 (1, 0) 8,238 (0,9); 8,232 (0,9); 7,817 (1, 5); 7,810 (1, 5); 7,796 (1, 7); 7,790 (1, 7); 7,522 (3,5); 7,501 (3.0); 5.755 (0.9); 5.290 (
6,4);4,834(16,0);3,320(28,6);2,524(0,5);2,510(1 1 ,6);2,506(25,5);2,502(36,7);2,497(28,2);2,493(14, 1);0,008(0,8);0,000(26,5);-0,008(1 ,0)4,434 (16,0); 3,320 (28,6); 2,524 (0.5); 2.510 (1 1, 6); 2,506 (25,5); 2,502 (36,7); 2,497 (6,4); 28.2), 2.493 (14, 1), 0.008 (0.8), 0.000 (26.5), - 0.008 (1, 0)
Beispiel 1-1-111 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,652(4,5);9,636(4,6);7,953(3,9);7,944(3,9);7,869(3,8);7,847(5,2);7,839(11 ,8)7,716(2, 3);7,713(26);7,697(2.8);7.694(4,2);7,675(2,0);7,673(2,2);7,344(2,2);7,342(2.5)7 Example 1-1-111: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.652 (4.5), 9.636 (4.6), 7.953 (3.9), 7.944 (3.9 7,869 (3.8), 7.847 (5.2), 7.839 (11, 8) 7.716 (2, 3); 7,713 (26); 7,697 (2.8); 7,694 (4.2); 7,675 (2.0); 7,673 (2.2); 7.344 (2.2); 7,342 (2.5) 7
2(93 );2797(0,4);2J88(1,2);2J79(1,8);2J70(2J);2J60(2J);2J52(1 ,8);2J43(1 ,3);2,733(0,6);2,677(0,4);2,673(0,6);2,669(0,4);2,526(1,4); 2,513(30,1);2,508(63,7);2,504(90,2);2,500(70,0);2,335(0,4);2,331(0,5);2,326(0,4);1,232(0,9);0,783(0,4);0,750(1,6);0,737(4,6);0,732(6,1);0,7 20(5,9);0,715(4,9);0,703(1,9);0,506(1,9);0,494(5,6);0,489(5,4);0,485(5.2);0,479(5,2);0,467(1,5);0,008(1,2);0,000(33,5);-0,008(1,2) 2 (93), 2797 (0.4), 2J88 (1.2), 2J79 (1.8), 2J70 (2J), 2J60 (2J), 2J52 (1, 8), 2J43 (1, 3); 2,733 (0.6); 2,677 (0.4); 2,673 (0.6); 2,669 (0.4); 2,526 (1.4); 2,513 (30.1); 2,508 (63.7); 2,504 (90.2); 2,500 (70.0); 2,335 (0.4); 2,331 (0.5); 2,326 (0.4); 1,232 (0.9); 0.783 (0.4); 0.750 (1.6); 0.737 (4.6); 0.732 (6.1); 0.7 20 (5.9); 0.715 (4.9) ; 0,703 (1.9); 0,506 (1.9); 0.494 (5.6) 0.489 (5.4) 0.485 (5.2) 0.479 (5.2) 0.467 (1.5) 0.008 ( 1.2); 0,000 (33.5) - 0.008 (1.2)
Beispiel 1-1-112: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,955(1 ,3):9,949(1 ,3);9,943(1 ,4);9,937(1 ,3);8,497(2,1);8,491 (2,2);7,954(2,2);7,942(0,7 );7,936(0,7);7,922(0,8);7,918(1 ,1 );7,916(0,9);7,912(1 ,0):7.898{1 ,0);7,892(0,9);7,820(1 ,4);7,814(1 ,4);7.808(1 ,4);7,800(1 ,8);7,794(2,1 );7,784( 1,0)7,772(0,9)7,505(2,6)7.484(2,3);5,246(5,9);4,580{10,2);3,583(1,5);3,565(5,0);3,548(5,1);3,530(1,6);3,321(32,5);2,892(16,0);2,732(13,6 );2,675(0,4);2,596(0,6);2,595(0,6);2,584(0,6);2,583(0,6);2,526(0,4);2,521(0,6);2,512(10,2);2,508(22,3);2,503(31,8);2,499(23 Example 1-1-112: 'H NMR (400.0 MHz, de-DMSO): δ = 9.955 (1.3): 9.949 (1.3); 9.943 (1.4); 9.937 (1.3 8.497 (2.1), 8.491 (2.2), 7.954 (2.2), 7.942 (0.7), 7.936 (0.7), 7.922 (0.8), 7.918 (1, 1) 7.916 (0.9); 7.912 (1, 0): 7.898 {1.0); 7.892 (0.9); 7.820 (1.4); 7.814 (1.4); 7.808 (1.4); 7.894 (1.8), 7.794 (2.1), 7.784 (1.0) 7.772 (0.9), 7.555 (2.6), 7.484 (2.3), 5.246 (5.9), 4.580 {10, 2); 3,583 (1.5); 3,565 (5.0); 3,548 (5.1); 3,530 (1.6); 3,321 (32.5); 2,892 (16.0); 2.732 (13.6 ); 2,675 (0.4); 2,596 (0.6); 2,595 (0.6); 2,584 (0.6); 2,583 (0.6); 2,526 (0.4); 2,521 (0.6) ; 2,512 (10.2); 2,508 (22.3); 2.503 (31.8); 2,499 (23
1 , 174(4,9); 1,156(10,1);!, 139(4,8); 1 ,046(0,5); 1,031 (0,5);0,008(0,5);0,000(18, 1 );-0,009(0,6) 1, 174 (4,9); 1,156 (10,1);!, 139 (4,8); 1, 046 (0.5); 1.031 (0.5), 0.008 (0.5), 0.000 (18, 1), - 0.009 (0.6)
Beispiel 1-1-113: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,761(3,9);9,759(3,6);8,495(3,4);8,489(3,4);7,797(2,1);7,791(2,0);7,776(2,4);7,770(2,4 );7,697(1.2);7,694(1,3);7,675(2,8);7,671(2,9);7.639(4,4);7,616(2,0);7,493(4,1);7,473(3,6);5,212(9,1);4,570(16,0);3,580(2.3);3,563(7,7Example 1-1-113: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.761 (3.9), 9.759 (3.6), 8.495 (3.4), 8.489 (3.4 7.797 (2.1), 7.791 (2.0), 7.776 (2.4), 7.770 (2.4), 7.697 (1.2), 7.694 (1.3), 7.675 (2.8), 7.671 (2.9); 7,639 (4.4); 7,616 (2.0); 7,493 (4.1); 7,473 (3.6); 5,212 (9.1); 4,570 (16.0); 3,580 ( 2.3); 3,563 (7.7
(7,8);3,528(2,4);3,322(38,2);2,893(0,6);2,733(0,5);2,527(0,6);2,522(1,0);2,513(14,1);2,509(30,4);2,504(43,1);2,499(32,2);2,495(15,4);2,361( 15,8); 1 , 171 (7,6); 1 , 154(15,6); 1 , 136(7,3); 1 ,047(0,5); 1 ,031 (0,5);0,008(0,6);0,000(19,6);-0,009(0,6) (7.8); 3,528 (2.4); 3,322 (38.2); 2,893 (0.6); 2,733 (0.5); 2,527 (0.6); 2,522 (1.0); 2,513 ( 14.1); 2.509 (30.4); 2.504 (43.1); 2.499 (32.2); 2.495 (15.4); 2.361 (15.8); 1, 171 (7,6); 1, 154 (15,6); 1, 136 (7,3); 1, 047 (0.5); 1, 031 (0.5), 0.008 (0.6), 0.000 (19.6), - 0.009 (0.6)
Beispiel 1-1-114: 1H-NMR(400,0 MHz, d6-DMSO): δ= 8,510(3,2);8,505(3,2);7,823(1,8);7,810(2,2);7,803(4,6);7,789(2,4);7,783(4.6);7,576(2,5Example 1-1-114: 1 H-NMR (400.0 MHz, d 6 -DMSO): δ = 8.510 (3.2); 8.055 (3.2); 7.823 (1.8); 7.810 (2, 2); 7,803 (4.6); 7.789 (2.4); 7,783 (4.6); 7,576 (2.5
);7,555(2,1);7,499(3,8);7,479(3,4);7,252(2,4);7,234(2,3);5758(1,1);5,248(9,0);4,666{16,0);3,560(2,2);3,542(7,5);3,525(77);3,507(2,3);3,322 (297);2,545(15,6);2,527(07);2,522(0,8);2,513(11,7);2,509(25,1);2,504(35,3);2,500(26,1);2,495(12,3);1,165(7,4):1,147(15,2);1,130(7,2);1,0 47(1, 1 ); 1 ,032(1 , 1 );0,008(0,7);0,000(20,9);-0,009(0,7) ); 7,555 (2.1); 7,499 (3.8); 7.479 (3.4); 7,252 (2.4); 7,234 (2.3); 5758 (1.1); 5,248 (9.0) 4.656 {16.0); 3.560 (2.2); 3.542 (7.5); 3.525 (77); 3.507 (2.3); 3.322 (297); 2.545 (15.6); 2.527 (07) ; 2,522 (0.8); 2,513 (11.7); 2,509 (25.1); 2,504 (35.3); 2,500 (26.1); 2,495 (12.3); 1.165 (7.4): 1.147 (15.2); 1.1130 (7.2); 1.0 47 (1, 1); 1, 032 (1, 1), 0.008 (0.7), 0.000 (20.9), - 0.009 (0.7)
Beispiel 1-1-115: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,584(3,9);9,568(3,9);8,375(3,8);8,369(3,9);7,722(2,1);7,716(2,0);7,702(2,4);7,695(2,3Example 1-1-115: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.584 (3.9), 9.568 (3.9), 8.375 (3.8), 8.369 (3.9 ); 7,722 (2.1); 7,716 (2.0); 7,702 (2.4); 7,695 (2.3
);7,483(4,8);7,462(4,0);7,416(2,9);7,395(3,9);7,280(27);7,263(2,8);7,259(2,4);7,242(2,1);5756(1,5);5,381(10,3);4,604(0,6);4,589(16,0);4,18); 7,483 (4.8); 7,462 (4.0); 7,416 (2.9); 7,395 (3.9); 7,280 (27); 7,263 (2.8); 7,259 (2.4); 7,242 (2.1), 5756 (1.5); 5,381 (10.3); 4,604 (0.6); 4,589 (16.0); 4.18
4(1,7);4,166(5,4);4,149(5,5);4,132(1,7);3,578(2,2);3,560(7,1);3,543(7,2);3,525{2,3);3,318(138,0);2,671(0,8);2,506(99,5);2,502(139,3);2,498(4 (1.7); 4,166 (5.4); 4,149 (5.5); 4,132 (1.7); 3,578 (2.2); 3,560 (7.1); 3,543 (7.2); 3,525 {2,3), (2,498; 3,318 (138.0); 2,671 (0.8); 2,506 (99.5); 2.502 (139.3)
106,3);2,453(0,3);2,329(0,8);1,230(5,8);1,212(11,9);1,195(5,5);1,172(7,2);1,155(14,6);1,137(7,0);1,045(1,3 106.3); 2,453 (0.3); 2,329 (0.8); 1,230 (5.8); 1,212 (11.9); 1,195 (5.5); 1,172 (7.2); 1,155 (14 , 6); 1,137 (7.0); 1,045 (1.3
8);-0,008(1,2)  8) - 0.008 (1.2)
Beispiel 1-1-116: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,030(3,2);10,028(3,3);10,013(3,4);10,011(3,3);8,406(3,4);8,400(3,5);7,912(3,0);7,91 0(3,2);7,892(3,4);7,890(3,3);7,753(1,9);7,746(1,9);7,732(2,3);7,726(2,3);7,490(4,3);7,469(3,8);7,378(2,7);7,362(2,9);7,358(2,8);7,342(2,6)i 755(0,5);5,526(9,5);4,609(16,0);3,589(2,3);3,571(7,6);3,554(7,7);3,536(2,4);3,319(145,5);2,671(0,8);2,524(1,6);2,510(44,6);2,506(96,3);2,5 01(136,3);2,497(101,8);2,493(49,2);2,328(0,8);1 ,179(7,5);1,161(15,3);1,144(7,3);1,045(0,5);1,030(0,5);0,008(1,1);0,000(36,0);-0,008(1,3)Example 1-1-116: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.030 (3.2); 10.028 (3.3); 10.013 (3.4); 10.011 (3.3 8.406 (3.4), 8.400 (3.5), 7.912 (3.0), 7.91 0 (3.2), 7.892 (3.4), 7.890 (3.3), 7.753 (1 , 9); 7.746 (1.9); 7,732 (2.3); 7,726 (2.3); 7,490 (4.3); 7.469 (3.8); 7,378 (2.7); 7,362 (2, 9), 7.358 (2.8), 7.342 (2.6), i 755 (0.5), 5.526 (9.5), 4.609 (16.0), 3.589 (2.3), 3.571 (7.6 ); 3,554 (7.7); 3,536 (2.4); 3,319 (145.5); 2,671 (0.8); 2,524 (1.6); 2,510 (44.6); 2.506 (96.3) 2.5 01 (136.3); 2.497 (101.8); 2.493 (49.2); 2.328 (0.8); 1, 179 (7.5); 1.161 (15.3); 1.144 ( 7.3); 1,045 (0.5); 1,030 (0.5) 0.008 (1.1) 0.000 (36.0) - 0.008 (1.3)
Beispiel 1-1-117: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,954(4,8);9,949(4,7);8,023(1,9);8,018(1,9);8,000(3,6);7,995(3,8);7,951(5,1);7,927(2,6Example 1-1-117: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.954 (4.8), 9.949 (4.7), 8.023 (1.9), 8.018 (1.9 ); 8,000 (3.6); 7,995 (3.8); 7,951 (5.1); 7.927 (2.6
);7,824(7,7);5,424(0,3);5,401 (10,0);4,569(16,0);3,967(0,4);3,483(47);3,466(9,9);3,449(4,9);3,322(16,5);2,526(075;2,513(17,3);2,508(377); 2,504(54, 1 );2,499(41 ,2);2,495(20,2);2,443(0,4);2,331 (0,3); 1 ,990(0,5); 1 ,603(0,6); 1 ,585(2,3); 1 ,567(4,3); 1 ,549(4,7); 1 ,532(2,3); 1 ,514(0,6);0,91 5(7,8);0,896(15,6);0,878(7,1);0,865(0,5);0,008(0,8);0,000(27,4);-0,008(1,0) 7.824 (7.7), 5.424 (0.3), 5.401 (10.0), 4.569 (16.0), 3.967 (0.4), 3.483 (47), 3.466 (9.9), 3.499 (4.9); 3.322 (16.5); 2.526 (075; 2.513 (17.3); 2.508 (377); 2.504 (54.1); 2.499 (41.2); 2.495 (20.2); 2,443 (0.4), 2.331 (0.3), 1.990 (0.5), 1.603 (0.6), 1.855 (2.3), 1.567 (4.3); 1, 549 (4,7); 1, 532 (2,3); 1, 514 (0,6); 0,91 5 (7,8); 0,896 (15,6); 0,878 (7,1) ; 0.865 (0.5) 0.008 (0.8); 0,000 (27.4) - 0.008 (1.0)
Beispiel 1-1-118: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,942(4,1);9,938(4,2);9,937(4,0);8,027(2.1);8,022(2,0);8,004(3,9);7,999(4,0);7,956(4,7Example 1-1-118: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.942 (4.1); 9.938 (4.2); 9.937 (4.0); 8.027 (2.1); 8,022 (2.0); 8,004 (3.9); 7,999 (4.0); 7,956 (4.7
);7,954(4,7);7,932(2,5);7,931 (2,4);7,825(7,7);5,403(9,3);4,528(16,0);4,058(0,9);4,040(2,7);4,022(2,7);4,005(0,9);3,368(35,5);3,324(30,η7.954 (4.7), 7.932 (2.5), 7.931 (2.4), 7.825 (7.7), 5.403 (9.3), 4.528 (16.0), 4.058 (0.9) ; 4,040 (2.7); 4,022 (2.7); 4,005 (0.9); 3,368 (35.5); 3,324 (30, η
28(0,5);2,523ί0,7);2,514(10,9);2,510(23,8);2,505(337);2,500(25,2);2,496(11,9);1,991(12,0);1,231(0,3);1,195(3,2);1,177(6,4);1,160(3,1);0,028 (0.5); 2,523ί0,7); 2,514 (10.9); 2,510 (23.8); 2.505 (337) 2.500 (25.2); 2,496 (11.9); 1,991 (12, 0); 1,231 (0.3); 1,195 (3.2); 1,177 (6.4); 1,160 (3.1); 0.0
08(0,6);0,000(21,3);-0,009(0,7) 08 (0.6); 0,000 (21.3) - 0.009 (0.7)
Beispiel 1-1-119: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,952(4,9);9,947(5,1);8,022(1,8);8,017(2,0);7,998(3.4);7,993(3,9);7,972(0,4);7,951 (5,5Example 1-1-119: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.952 (4.9), 9.947 (5.1), 8.022 (1.8), 8.017 (2.0 7,998 (3.4), 7,993 (3.9), 7,972 (0.4), 7,951 (5.5
);7,927(2,8);7,837(0,6);7,823(7,8);5,754(6,2);5,400(117);4,564{15,8):4,056(0,8);4,039(2,4);4,021 (2,4);4,003(0,8);3,584(2,1);3,566(6,9);3,54 9(7,0);3,531(2,3);3,319(59,0);2,672(0,6);2,503(94,2);2,499(80,6);2,444(0,6);2,329(0,6);1,989(10,0);1,397(0,6);1,299(0,4);1, 259(0,4); 1,249(0 ,3);1,232(1 ,3);1, 194(2,7);1, 175(11,3);1,158(16,0);1,140(6,7);0,008(1,5);0,000(46,2) ); 7.927 (2.8); 7,837 (0.6); 7,823 (7.8); 5,754 (6.2); 5,400 (117) 4,564 {15.8) 4,056 (0.8); 4,039 (2.4); 4.021 (2.4); 4.003 (0.8); 3.584 (2.1); 3.566 (6.9); 3.54 9 (7.0); 3.531 (2.3) ; 3,319 (59.0); 2,672 (0.6); 2,503 (94.2); 2,499 (80.6); 2,444 (0.6); 2,329 (0.6); 1,989 (10.0); 1.397 (0.6); 1.299 (0.4); 1.259 (0.4); 1,249 (0, 3), 1,232 (1,3), 1, 194 (2,7), 1, 175 (11,3), 1,158 (16,0), 1,140 (6,7), 0,008 (1, 0.000 (46.2), 5)
Beispiel 1-1-120: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,785(2.9);9,768(3,0);8,251(2,8);8,246(2,9);7,867(4,8);7,518(1,7);7,512(1,7);7,500(1,7Example 1-1-120: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.785 (2.9); 9.768 (3.0); 8.251 (2.8); 8.246 (2.9); 7,867 (4.8); 7,518 (1.7); 7,512 (1.7); 7,500 (1.7
);7,495(1,7);5,382(6,4);4771 (12,3);4,056(1,2);4,039(3,8);4,021(3,8);4,003(1,3);3,319(307);2,525(0,8);2,511(14,9);2,507(31,6);2,503(44,8); 2,498(33,6);2,494(16,3); 1 ,989(16,0); 1 , 194(4, 1 ); 1 , 176(8, 1 ); 1 , 158(4,0);0,000(5,7) 7.495 (1.7), 5.382 (6.4), 4771 (12.3), 4.056 (1.2), 4.039 (3.8), 4.021 (3.8), 4.003 (1.3) ; 3,319 (307) 2,525 (0.8); 2,511 (14.9); 2.507 (31.6); 2.503 (44.8); 2,498 (33.6); 2,494 (16.3); 1, 989 (16.0); 1, 194 (4, 1); 1, 176 (8, 1); 1, 158 (4.0); 0.000 (5.7)
Beispiel 1-1-121 : 1H-NMR(400,0 MHz, de-DMSO): δ= 7,852(5,2);7,836(2,7);7,799(2,0);7,779(2,6);7,758(1 ,2);7,500(2,3);7,481 (2,0);5,391 (7,5Example 1-1-121: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.852 (5.2), 7.836 (2.7), 7.799 (2.0), 7.779 (2.6 7.758 (1, 2), 7.500 (2.3), 7.481 (2.0), 5.391 (7.5
);4,057(0,9);4,039(27);4,021 (27);4,003(0,9);3,718(16,0);3,321(66,2);2,672{0,4);2,506(50,6);2,503(68,4);2,499(54,0);2,329(0,4);1,989(11,2) ; 1 ,909(0,7); 1 ,235(0,6); 1 , 193(2,8); 1 , 176(5,6); 1 , 158(2,8);-0,001 (5,4) 4.057 (0.9), 4.039 (27), 4.021 (27), 4.003 (0.9), 3.718 (16.0), 3.321 (66.2), 2.672 {0.4), 2.506 (50 , 6), 2.503 (68.4), 2.499 (54.0), 2.329 (0.4), 1.989 (11.2); 1, 909 (0.7); 1, 235 (0.6); 1, 193 (2,8); 1, 176 (5,6); 1, 158 (2,8); - 0,001 (5,4)
Beispiel 1-1-122: 1H-NMR(400,0 MHz, de-DMSO): δ= 7,849(4,3);7,782(0,8);7,760(1 ,9)7.742(1 ,9);7,715(2.0);7,694(0,9);7,220(1 ,5)7,202(1 ,4Example 1-1-122: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.849 (4.3); 7.782 (0.8); 7.760 (1.9) 7.742 (1, 9) 7.715 (2.0); 7.694 (0.9); 7.220 (1, 5) 7.202 (1, 4
);5,372(6,3);3,705(16,0);3,325i15,9);3,180(0,5);3,167(0,5);2,546{10,4);2,529(0,4);2,515(6,2);2,510(13,5);2,506(19,2);2,502(15,3);0,000{2,2)); 5,372 (6.3); 3,705 (16.0); 3,325i15,9); 3,180 (0.5); 3,167 (0.5); 2,546 {10.4); 2,529 (0.4); 2,515 (6.2); 2,510 (13.5); 2,506 (19.2); 2.502 (15.3); 0.000 {2.2)
Beispiel 1-1-123: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,668(3,1);9,649(3,2);7,864(5,1);7,468(2,8);7,461(3,0);7,070(1,7);7,063(1,7);7,051 (1,7 );7,044(1,7);5,373(7,0);4,725(12,6);3,998(16,0);3,323(40,2);2,509(24,1);2,504(33,2);2,500(26,0);1,990(0,4);0,000(1,4) Example 1-1-123: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.668 (3.1); 9.649 (3.2); 7.864 (5.1); 7.468 (2.8 7,461 (3,0); 7,070 (1,7); 7,063 (1,7); 7,051 (1,7); 7,044 (1,7); 5,373 (7,0); 4,725 (12,6) ; 3,998 (16.0); 3.323 (40.2); 2,509 (24.1); 2,504 (33.2); 2,500 (26.0); 1,990 (0.4); 0,000 (1.4)
Beispiel 1-1-124: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,715(3,0);9,697(3,1);7,857(5,1);7,429(2,7);7,423(2,7);7,038(1,8);7,031(1,7);7,019(1,7Example 1-1-124: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.715 (3.0), 9.697 (3.1), 7.857 (5.1), 7.429 (2.7 ); 7,423 (2.7); 7,038 (1.8); 7,031 (1.7); 7,019 (1.7
);7,012(1,7);5,349(6,4);4,471 (10,9);4,058(0,9);4,040(2,7);4,022(2,7);4,004(1,0);3,983(16,0);3,348(22,2);3,321(36,0);2,527(0,6);2,513(13,0); 2,509(26,6);2,504(36,4);2,500(26,9);2,496(12,8); 1 ,990(11 ,6); 1 , 195(3,0); 1 , 177(6, 1 ); 1 , 159(3,0);0,000(0,5) 7.012 (1.7), 5.349 (6.4), 4.471 (10.9), 4.058 (0.9), 4.040 (2.7), 4.022 (2.7), 4.004 (1.0) ; 3,983 (16.0); 3,348 (22.2); 3.321 (36.0); 2,527 (0.6); 2,513 (13.0); 2,509 (26.6); 2,504 (36.4); 2,500 (26.9); 2,496 (12.8); 1, 990 (11, 6); 1, 195 (3.0); 1, 177 (6, 1); 1, 159 (3.0); 0.000 (0.5)
Beispiel 1-1-125: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,696(3,3);7,859(1,2);7,845(6,2);7,838(4,3);7,823(2,9);7,820(2,8);7,801(0,8);7,797(0,8Example 1-1-125: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.696 (3.3); 7.859 (1.2); 7.845 (6.2); 7.838 (4.3 ); 7,823 (2.9); 7,820 (2.8); 7,801 (0.8); 7,797 (0.8
);5,393(8,1);4,789(16,0);3,328(35,1);2,532(0,5);2,518(11,4);2,514(23,4);2,510(32,0);2,505(23,7);2,501(11,4);2,384(13,5);1,996(0,4)); 5,393 (8.1); 4,789 (16.0); 3,328 (35.1); 2,532 (0.5); 2,518 (11.4); 2,514 (23.4); 2,510 (32.0) ; 2,505 (23.7); 2.501 (11.4); 2.384 (13.5); 1,996 (0.4)
Beispiel 1-1-126: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,699(3,2);9,682(3,3);7,869(6,3);7,786(3,8);7,279(2,1);7,264(2.0);7,262(2,0);5,357(9,1 );4,769(16,0);3,328(30,2);2,514(22,2);2,510(31,1);2,505(31,1);1,996(0,6);1, 182(0,3) Example 1-1-126: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.699 (3.2); 9.682 (3.3); 7.689 (6.3); 7.786 (3.8 7.279 (2.1), 7.264 (2.0), 7.262 (2.0), 5.357 (9.1), 4.769 (16.0), 3.328 (30.2), 2.514 (22.2), 2.510 (31.1); 2.555 (31.1); 1.996 (0.6); 1, 182 (0.3)
Beispiel 1-1-127: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,559(7.0);9,544(7,0);9,543(7,1);8,408(6,7);8,402(6.8);8,314(0,6);8,071(5,1);8,061 (5,1Example 1-1-127: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.599 (7.0); 9.544 (7.0); 9.543 (7.1); 8.408 (6.7); 8.402 (6.8), 8.314 (0.6), 8.071 (5.1), 8.061 (5.1
);7,767(3,9);7,761(3,8);7,746(4,5);7,740(4,4);7,629(3,0);7,608(3,6);7,602(3,3);7,581(3,4);7,494(8,5);7,473(7,2);7,309(2,4);7,296(3,0);7,2 767(0,4);3,763(0.4);3,752(0,3);3,317(213,9);2.814(0,6);2,805(1,7);2,796(2,5);2,787(3,8);2,778(3,9);2,769(2,6);2,760(1,8);2,750(0,7);2,675(1 ,4);2,671(2,0);2,666(1,4);2,524(5,1);2,510(111,2^^ ); 7,767 (3.9); 7,761 (3.8); 7.746 (4.5); 7,740 (4.4); 7,629 (3.0); 7,608 (3.6); 7,602 (3.3) ; 7,581 (3.4); 7,494 (8.5); 7,473 (7.2); 7,309 (2.4); 7,296 (3.0); 7.2 767 (0.4); 3,763 (0.4); 3,752 (0.3); 3,317 (213.9); 2,814 (0.6); 2,805 (1.7); 2,796 (2.5); 2,787 (3 , 2,778 (3.9); 2.769 (2.6); 2.760 (1.8); 2.750 (0.7); 2.675 (1.4); 2.671 (2.0); 2.666 (1, 4); 4); 2,524 (5.1); 2,510 (111.2 ^ ^
34(0,4);1,045(8,3);1,030(8,2);0J57(2,1);0J44(6,3);0J39(8,4);0J27(8,2);0J22(6,7);0,710(2,7);0,510(2,6);0,498(7,4);0,493(7,6);0,488(7,2); 0,484(7,2); 0,471 (2, 1 );0,000( 13,5)  34 (0.4); 1,045 (8.3); 1,030 (8.2); 0J57 (2,1); 0J44 (6,3); 0J39 (8.4); 0J27 (8.2), 0J22 (6.7); 0,710 (2.7); 0,510 (2.6); 0,498 (7.4); 0,493 (7.6); 0,488 (7.2); 0.484 (7.2); 0.471 (2, 1); 0.000 (13.5)
Beispiel 1-1-128: 'H-NMR(400,0 MHz, de-DMSO): ö= 9,683(3,9);9,666(4,0)7,868(3,5)7,850(12,3)7,828(2,2)7,816(0,8)7,699(2,1)7,697(2, Example 1-1-128: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.683 (3.9); 9.666 (4.0) 7.868 (3.5) 7.850 (12.3) 7.828 (2.2) 7.816 (0.8) 7.699 (2.1) 7.697 (2,
3)7,681(2,6)7,678(3,9)7,675(2,2)7,659(2,0)7,656(2,0)7,329(2,2)7,326(2,4)7,309(3,8)7,294(1, 9)7,291 (2,0);5,756(1,4);5,452(14,2);3,33 4(7,0);3,173(2,2);2,829(16,0);2,817(15,9);2,674(0,4);2,537(0,4);2,528(1,0);2,514(20,0);2,510(42,2);2,505(59,3);2,501(44,2);2,498(21,2);2,3 32(0,3); 1 ,357(0,4); 1 ,232(2,5):0,853(0,4);0,000(0,7) 3) 7.681 (2.6) 7.678 (3.9) 7.675 (2.2) 7.659 (2.0) 7.656 (2.0) 7.329 (2.2) (7.326 (2.4) 7.309 3.8) 7.294 (1.9) 7.291 (2.0), 5.756 (1.4), 5.452 (14.2), 3.33 4 (7.0), 3.173 (2.2), 2.829 (16.0) ; 2,817 (15.9); 2,674 (0.4); 2,537 (0.4); 2,528 (1.0); 2,514 (20.0); 2,510 (42.2); 2,505 (59.3); 2,501 (44.2); 2,498 (21,2); 2,3,32 (0,3); 1, 357 (0.4); 1, 232 (2.5): 0.853 (0.4); 0.000 (0.7)
Beispiel 1-1-129: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,675(3,5);9,658(3.6);8,002(1 ,4)7,988(2,8)7,973(1 ,4)7,866(3,1 );7,851 (9,5)7,845(4,3 );7,701 (1,9);7,699(2,0);7.683(2,3);7,680(3,3);7,661 (1 ,7)7,658(1 ,7)7,326(1 ,8)7,324(1 ,9)7,307(3,4)7,291 (1 ,7)7,289(1 ,7);5,450(12,4);3,324 (59,7);3,286(2,1);3,269(4,8);3,253(4,8);3,237(2,2);2,674(0,4);2,528(1,0);2,514(20,8);2,510(42,3);2,505(58,2);2,501(44,3);2,497(22,3);2,332( 0,3); 1 ,561 (0,5); 1 ,542(2,4); 1 ,524(4,7); 1 ,506(4,8); 1 ,488(2,6); 1 ,470(0,6); 1 ,231 (0,4);0,930(8,0);0,912(16,0);0,893(7,0);0,146(0,3);0,008(2,6);0, 000(71, 1 ); -0,008(3,0);-0, 150(0,3) Example 1-1-129: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.675 (3.5); 9.658 (3.6); 8.002 (1.4) 7.988 (2.8) 7.973 ( 1, 4), 7.866 (3.1), 7.851 (9.5), 7.845 (4.3), 7.701 (1.9), 7.699 (2.0), 7.683 (2.3), 7.680 (3.3 7.661 (1, 7) 7.658 (1, 7) 7.326 (1, 8) 7.324 (1.9) 7.307 (3.4) 7.291 (1, 7) 7.289 (1, 7); 5.450 (12.4); 3.324 (59.7), 3.286 (2.1), 3.269 (4.8), 3.253 (4.8), 3.237 (2.2), 2.674 (0.4), 2.528 (1.0) 2.514 (20.8), 2.510 (42.3), 2.505 (58.2), 2.501 (44.3), 2.497 (22.3), 2.332 (0.3); 1, 561 (0.5); 1, 542 (2,4); 1, 524 (4,7); 1, 506 (4,8); 1, 488 (2.6); 1, 470 (0.6); 1, 231 (0.4), 0.930 (8.0), 0.912 (16.0), 0.893 (7.0), 0.146 (0.3), 0.008 (2.6), 0.000 (71, 1 ); -0.008 (3.0); - 0, 150 (0.3)
Beispiel 1-1-130: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,596(2,6);9,579(2.7);8,375(3.2);7,806(2,6);7,786(2,7);7,706(1.7);7,690(2,0);7,476(3,0 );7,456(2,4);7,337(1,6);7,319(2,4);7,300(1,5);5,525(8,3);3,761 (16,0);3,320(149,8);2,671(1,1);2,598(0,4);2,502(163,1);2,328(1,0);0,146(0,6); 0.000(111.3);-0,150(0.6) Example 1-1-130: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.596 (2.6), 9.589 (2.7), 8.375 (3.2), 7.806 (2.6), 7.786 ( 2.7), 7.706 (1.7), 7.690 (2.0), 7.466 (3.0), 7.456 (2.4), 7.337 (1.6), 7.319 (2.4), 7.300 (1.5 5.525 (8.3), 3.761 (16.0), 3.320 (149.8), 2.671 (1.1), 2.598 (0.4), 2.502 (163.1), 2.328 (1.0) ; 0,146 (0.6); 0.000 (111.3) - 0.150 (0.6)
Beispiel 1-1-131 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,675(2,1);9,658(2.2);7,862(1,9);7,847(5,6);7,841(2,8);7,832(1,8);7,812(1,6);7,697(1,2Example 1-1-131: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.675 (2.1); 9.658 (2.2); 7.862 (1.9); 7.847 (5.6); 7,841 (2.8); 7,832 (1.8); 7,812 (1.6); 7,697 (1.2
);7,679(2,0);7,660(1 ,0)7,657(1 ,0)7,321 (1 ,2)7,304(2, 1 );7,286(1 ,0);5,437(7,6);4,092(0.7);4,076(1 ,0);4,058(1 , 1 );4,041 (0,7);3,322(66,0);2.673 (0,3);2,508(39,9);2,504(54,4);2,500(42,6);1,232(0,3);1,181(16,0);1 ,165(16,0);1,047(1,3);1,032(1,2);0,007(2,4);0,000(57,3):-0,008(2,8)7.679 (2.0); 7.660 (1, 0) 7.657 (1, 0) 7.321 (1, 2) 7.304 (2, 1); 7.286 (1, 0); 5.437 (7.6); 4.092 ( 4.076 (1, 0); 4.058 (1, 1); 4.041 (0.7); 3.322 (66.0); 2.673 (0.3); 2.508 (39.9); 2.504 (54.4 2.500 (42.6), 1.232 (0.3), 1.181 (16.0), 1, 165 (16.0), 1.047 (1.3), 1.032 (1.2), 0.007 (2, 4); 0.000 (57.3) - 0.008 (2.8)
Beispiel 1-1-132: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,621 (1 ,7);9,603(1 ,7);8.497(2,1);8,491 (2,2);8,218(2,3);7,829(1 ,3)7,822(1 ,3)7,808(1.5Example 1-1-132: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.621 (1, 7), 9.603 (1, 7), 8.497 (2.1), 8.491 (2.2 8,218 (2,3); 7,829 (1,3) 7,822 (1,3) 7,808 (1.5
);7,802(1,5);7,645(1 ,2)7,641 (1 ,3)7,627(1 ,2)7,623(1 ,3)7,498(2,6)7,477(2,3^ 7.802 (1.5), 7.645 (1.2) 7.641 (1.3) 7.627 (1.2) 7.623 (1.3) 7.498 (2.6) 7.477 (2.3)
9(18,0);2,504(25,4);2,500(19,1);2,496(9,3);1,047(2,0);1 ,032(1,9) 9 (18.0), 2.504 (25.4), 2.500 (19.1), 2.496 (9.3), 1.047 (2.0), 1.032 (1.9)
Beispiel 1-1-133: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,513(4,3);8,488(3,4);8,483(3,6);8,029(2,5);8,020(2,6);7,772(1,8);7,766(1,8);7,751 (2,0 );7,745(2,1);7,635(2,6);7,612(3,7);7,520(2,7);7,498(1,9);7,482(3,7);7,462(3,2);5,249(9,4);3,319(55,8);2,776(0,7);2767(1,1);2,758(1,^ Example 1-1-133: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.513 (4.3), 8.488 (3.4), 8.483 (3.6), 8.029 (2.5 8.020 (2.6); 7.772 (1.8); 7.766 (1.8); 7.751 (2.0); 7.745 (2.1); 7.635 (2.6); 7.612 (3.7) ; 7,520 (2.7); 7,498 (1.9); 7,482 (3.7); 7,462 (3.2); 5,249 (9.4); 3,319 (55.8); 2,776 (0.7); 2767 (1.1); 2.758 (1, ^
(1,5);2,741 (1,1);2,731(0,7);2,672(0,5);2,503(75,1);2,342(16,0);0,738(0,9);0,721(3,7);0,708(3,5);0,692(1,0);0,489(1,1);0,478(3,5);0,472(3,7); 0,463(3,4);0.451(0,9);0,000(2,2) (1.5); 2.741 (1.1); 2.731 (0.7); 2.672 (0.5); 2.503 (75.1); 2.342 (16.0); 0.738 (0.9); 0.721 (0.721). 3.7) 0.708 (3.5) 0.692 (1.0); 0.489 (1.1) 0.478 (3.5) 0.472 (3.7); 0.463 (3.4) 0.451 (0.9); 0,000 (2.2)
Beispiel 1-1-134: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,682(3,8);9,665(3,9);7,937(1,5);7.923(3,0);7,909(1,6);7,865(3,4);7,849(10,0);7,699(2,Example 1-1-134: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.682 (3.8), 9.665 (3.9), 7.937 (1.5), 7.923 (3.0 ); 7,909 (1.6); 7,865 (3.4); 7,849 (10.0); 7.699 (2,
0);7,697(2,0);7,678(3,5);7,659(1, 8)7,322(2,0)7,306(3,7)7,289(1, 8);5,755(4,0);5,445(13,9);3,353(1 ,2);3,335(4,3);3,321(60,4);3,302(4,3);3,2 84(1,2);2,673(0,5);2,508(59,9);2,504(82,6);2,500(65,7);2,331(0,5);1,233(0,3);1,143(7,7);1,125(16,0);1,107(7,5);0,000(0,7) 7.697 (2.0), 7.678 (3.5), 7.659 (1.8), 7.322 (2.0) 7.306 (3.7) 7.289 (1.8), 5.755 (4.0), 5.455 (13.9); 3.353 (1,2); 3,335 (4,3); 3,321 (60,4); 3,302 (4,3); 3,284 (1,2); 2,673 (0,5) ; 2,508 (59.9); 2,504 (82.6); 2,500 (65.7); 2,331 (0.5); 1,233 (0.3); 1,143 (7.7); 1,125 (16.0); 1,107 (7.5); 0,000 (0.7)
Beispiel 1-1-135: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,639(4,6);9,623(4,7);8,127(3,5);8,107(3,6);7,867(4,0);7,848(14,6);7,707(2,5);7,704(2,Example 1-1-135: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.639 (4.6), 9.623 (4.7), 8.127 (3.5), 8.107 (3.6 ); 7,867 (4.0); 7,848 (14.6); 7,707 (2.5); 7.704 (2,
5);7,689(3,1);7,686(4,3);7,667(2,2):7,664(2,1);7,324(2,4);7,321(2,5);7,305(4,5);7,289(2,2);7,286(2,2);5,444(16,0);4,457(1,1);4,436(2,2);4 5(2,2);4,395(1,2);4,342(0,5);4,331(0,5);3,320(144,5);2,677(0,6);2,672(0,9);2,668(0,6);2,526(2,6);2,512(51,4);2,508(103,8);2,503(141,4);2,4 99(105,6);2,494(51,3);2,335(0,6);2,330(0,8);2,326(0,6);2,303(0,8);2,295(1,2);2,284(1 ,9);2,277(2,9);2,266(2,5);2,255(3,0);2,248(2,2);2,237(^ ,4);2,230(1 , 1 ); 1 ,976(0,6); 1 ,970(0,5); 1 ,954(2, 1 ); 1 ,928(3,3); 1 ,922(2,8); 1 ,906(2,4); 1 ,899(2,4); 1 ,883(0,7); 1 ,877(0,8); 1 ,713(1 ,6); 1 ,704(1 ,7); 1 ,69 7(2,2); 1 ,689(2,2); 1 ,682(2,5); 1 ,671 (3,0); 1 ,661 (1 7.664 (2.1); 7,324 (2.4); 7,321 (2.5); 7,305 (4.5: 5); 7,689 (3.1);; 7.686 (4.3) 7.667 (2.2) 7,289 (2,2); 7,286 (2,2); 5,444 (16,0); 4,457 (1,1); 4,436 (2,2); 4 5 (2,2); 4,395 (1,2 ); 4,342 (0.5); 4,331 (0.5); 3,320 (144.5); 2,677 (0.6); 2,672 (0.9); 2,668 (0.6); 2,526 (2.6) 2.512 (51.4), 2.508 (103.8), 2.503 (141.4), 2.499 (105.6), 2.494 (51.3), 2.335 (0.6), 2.330 (0, 8), 2,326 (0,6), 2,303 (0,8), 2,295 (1,2), 2,284 (1, 9), 2,277 (2,9), 2,266 (2,5), 2,255 (3,0 2.248 (2.2), 2.237 (^, 4), 2.230 (1, 1); 1, 976 (0.6); 1, 970 (0.5); 1, 954 (2, 1); 1, 928 (3,3); 1, 922 (2,8); 1, 906 (2,4); 1, 899 (2,4); 1, 883 (0.7); 1, 877 (0.8); 1, 713 (1, 6); 1, 704 (1, 7); 1, 69 7 (2,2); 1, 689 (2, 2); 1, 682 (2.5); 1, 671 (3.0); 1, 661 (1
000(174,2);-0,008(6,6);-0, 150(0,8) 000 (174.2); - 0.008 (6.6); - 0, 150 (0.8)
Beispiel 1-1-136: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,567(2,2);9,551(2,1);8,622(3,7);8.615(2,8);8,104(2,0);8,098(1,6);8,083(2,2);8,076(1,7Example 1-1-136: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.567 (2.2); 9.551 (2.1); 8.622 (3.7); 8.615 (2.8 ); 8,104 (2.0); 8,098 (1.6); 8,083 (2.2); 8,076 (1.7
);7,815(3,1);7,794(2,7);7,726(1,1);7,707(2,1);7,687(1,3);7,430(1,4);7,413(2,6);7,400(3,1);7,379(2,1);57 ); 7,815 (3.1); 7,794 (2.7); 7,726 (1.1); 7,707 (2.1); 7,687 (1.3); 7,430 (1.4); 7,413 (2.6) ; 7,400 (3.1); 7,379 (2.1); 57
9(1,5);2,670(0,6);2,501(96,8);2,328(0,6);0,006(1 ,1);0,000(2,8) 9 (1.5), 2.670 (0.6), 2.501 (96.8), 2.328 (0.6), 0.006 (1, 1), 0.000 (2.8)
Beispiel 1-1-137: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,595(4.7);9,579(4.9);8,333(1,8);8,316(4,0);8,300(1,9);7.908(3,9);7,886(5.3);7,858(12,Example 1-1-137: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.595 (4.7), 9.589 (4.9), 8.333 (1.8), 8.316 (4.0), 8.300 ( 1.9); 7,908 (3.9); 7,886 (5.3); 7,858 (12,
9);7,775(2,7);7,772(2,8);7,756(3,3);7,753(4,6);7,750(2,5);7,735(2,3);7,731(2,3);7,370(2,5);7,367(2,6);7,351(4,5);7,335(2,4);7,332(2,3);5,756 (0,8);5,460(16,0);4,342(0.8);4,332(0,8);4,211(1,0);4,187(3,3):4,170(3,4);4,163(3,6);4,146(3,3);4,138(r 9); 7,775 (2.7); 7,772 (2.8); 7,756 (3.3); 7,753 (4.6); 7,750 (2.5); 7,735 (2.3); 7,731 (2.3 7.379 (2.5); 7.367 (2.6); 7.351 (4.5); 7.335 (2.4); 7.332 (2.3); 5.756 (0.8); 5.460 (16.0) ; 4,342 (0.8); 4,332 (0.8); 4,211 (1.0); 4,187 (3.3) 4,170 (3.4); 4,163 (3.6); 4,146 (3.3); 4,138 ( r
2,674(0,6);2,669(0,4);2,527(1,6);2,514(32,9);2,509(67,7);2,505(92,6);2,500(69,1);2,496(33,4);2,336(0,4);2,332(0,6);2,327(0,4);1,048(5,5);1, 032(5,4);0,146(0,5);0,008(3,7);0,000(105,0);-0,008(3,8);-0,150(0,4)  2,674 (0.6); 2,669 (0.4); 2,527 (1.6); 2,514 (32.9); 2,509 (67.7); 2,505 (92.6); 2,500 (69.1); 2,496 (33.4), 2.336 (0.4), 2.332 (0.6), 2.327 (0.4), 1.048 (5.5), 1.032 (5.4), 0.146 (0.5); 0.008 (3.7) 0.000 (105.0) - 0.008 (3.8) - 0.150 (0.4)
Beispiel 1-1-138: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,666(4,7);9,650(4,9);7,972(3.8);7,953(3,8);7,862(4,2);7,846(12,9);7,840(5,6);7,701(2,Example 1-1-138: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.666 (4.7); 9.650 (4.9); 7.972 (3.8); 7.953 (3.8); 7,862 (4.2); 7,846 (12.9); 7,840 (5.6); 7,701 (2,
6);7,698(2,6);7,682(3,3);7,679(4,5);7,660(2,3);7,657(2,2);7,326(2,5);7,324(2,5);7,308(4,5);7,291(2,3);7,289(2,2);5,440(16,0);4,344(0,6) 4(0,7);4,264(0,4);4,248(1,5);4,230(2,8);4,213(2,8);4,196(1,5);4,179(0,4);3,324(44,6);2,675(0,4);2,528(1,3);2,515(24,2);2,511(47,6);2,506(63 ,4);2,502(47, 1 );2,497(22,9);2,333(0,4); 1 ,965(0,8); 1 ,947(2,0); 1 ,934(2,9); 1 ,918(3, 1 ); 1 ,903(2,3); 1 ,887(1 ,2); 1 ,724(0,5); 1 ,705(1 ,7); 1 ,697(2,2); 1 , 685(3,2);1,667(2,6);1.642(1,3);1,634(1,0);1,628(1,4);1,619(0,8);1,602(2,5);1,595(2,2);1.585P 6); 7.698 (2.6); 7,682 (3.3); 7,679 (4.5); 7,660 (2.3); 7,657 (2.2); 7,326 (2.5); 7,324 (2.5 7.308 (4.5); 7.291 (2.3); 7.289 (2.2); 5.440 (16.0); 4.344 (0.6) 4 (0.7); 4.264 (0.4); 4,248 (1.5); 4,230 (2.8); 4,213 (2.8); 4,196 (1.5); 4,179 (0.4); 3,324 (44.6); 2,675 (0.4); 2,528 (1.3), 2.515 (24.2), 2.511 (47.6), 2.506 (63, 4), 2.502 (47, 1), 2.497 (22.9), 2.333 (0.4); 1, 965 (0.8); 1, 947 (2,0); 1, 934 (2,9); 1, 918 (3, 1); 1, 903 (2, 3); 1, 887 (1, 2); 1, 724 (0.5); 1, 705 (1, 7); 1, 697 (2, 2); 1, 685 (3.2); 1.667 (2.6); 1.642 (1.3); 1.634 (1.0); 1.628 (1.4); 1.619 (0.8); 1.602 (2.5) ; 1,595 (2.2); 1.585P
; 1 ,542(0,5); 1 ,535(0,4); 1 ,464(1 ,2); 1 ,448(2,5); 1 ,432(3,0); 1 ,418(2,8); 1 ,402(1 ,9); 1 ,383(0,7); 1 ,048(4,6); 1 ,033(4,6);0,008(2,2);0,000(50,3);- 0,008(1,9)  ; 1, 542 (0.5); 1, 535 (0.4); 1, 464 (1, 2); 1, 448 (2.5); 1, 432 (3.0); 1, 418 (2,8); 1, 402 (1, 9); 1, 383 (0.7); 1, 048 (4,6); 1, 033 (4,6); 0,008 (2,2); 0,000 (50,3); - 0,008 (1,9)
Beispiel 1-1-139: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,665(4,7);9,648(4,8);8,013(2,0);7,998(4,1);7,983(2,0);7,864(4,0);7,843(16,0);7,704(2,Example 1-1-139: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.665 (4.7); 9.648 (4.8); 8.013 (2.0); 7.998 (4.1 ); 7,983 (2.0); 7,864 (4.0); 7,843 (16.0); 7.704 (2,
5);7,702(2,5);7,683(4,2);7,664(2,2);7,662(2,1);7,358(6,8);7,337(14,5);7,325(2,9);7,323(2,8);7,300(13,6);7,290(3,3);7,287(3,4);7,279(6,4);7 53(0,8);7,232(0,5);5,755(4,7);5,438(15,6);3,560(2,1);3,543(5,3);3,527(5,4);3,510(2,3);3,322(59,5);3,307(0,7);2,838(4,2);2,820(7,8);2,803(3, 8);2,736(0,4);2,718(0,65;2,700(0,3);2,674(0,65;2,509(74,1);2,504(97,3);2,500(75,2);2,331(0,6);2,327(0,4);1,047(0,9);1,032(0,9);0,146(0,4);- 0,001 (87,4);-0, 150(0,4) 5); 7,702 (2.5); 7,683 (4.2); 7.664 (2.2); 7,662 (2.1); 7,358 (6.8); 7,337 (14.5); 7,325 (2.9 7,323 (2,8), 7,300 (13,6), 7,290 (3,3), 7,287 (3,4), 7,279 (6,4), 7 53 (0,8), 7,232 (0.5 ); 5,755 (4.7); 5,438 (15.6); 3,560 (2.1); 3,543 (5.3); 3,527 (5.4); 3,510 (2.3); 3,322 (59.5) 3.307 (0.7), 2.838 (4.2), 2.820 (7.8), 2.803 (3, 8), 2.736 (0.4), 2.718 (0.65, 2.700 (0.3), 2.674 (0.65; 2.509 (74.1); 2,504 (97.3); 2,500 (75.2); 2,331 (0.6); 2,327 (0.4); 1,047 (0.9); 1,032 (0 , 9), 0.146 (0.4), - 0.001 (87.4), - 0, 150 (0.4)
Beispiel 1-1-140: 1H-NMR(400,0 MHz, de-DMSO): ö= 9,808(5.6);9.794(5,4);9,792(5.6);8.392(5,7);8,386(5.7);8,313(0,5);8,142(4,3);8,133(4,2Example 1-1-140: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.808 (5.6); 9.794 (5.4); 9.792 (5.6); 8.392 (5.7); 8.386 ( 5.7); 8,313 (0.5); 8,142 (4.3); 8,133 (4.2
);7,733(5,4);7,713(8,4);7,706(3,3);7,691(3,7);7,685(3,7);7,477(7,0);7,456(5,9);7,324(4,3);7,307(4,7);7,304(4,7);7,287(3,9);5,754(6,5);5,56 16,0);3,318(255,2);2.819(0,4);2,809(1,3);2,800(2,0);2,791 (3,0);2,782(3,0);2,773(2,0);2,764(1 ,4);2754(0,5);2,675(1 ,1 );2,671 (1 ,5);2,667(1 ,2); 2,524(4,6);2.508(184,5);2,502(252,8);2,497(193,5);2,333(1,1);2,329(1,5);2,324(1 ,1);1 ,045(1,4);1,030(1,4);0,757(1,7);0,744(5,1);0,740(6,7); 0J27(6,6);0J22(5,3);0J10(2,1);0,509(2,1);0,497(6J);0,492(6,0);0,487(5J);0,482(5J);0,470(1J);0,146(1,2);0,008(9,4);0,000(245,3);- 0,008(10,4);-0,150(1,1) ); 7,733 (5.4); 7,713 (8.4); 7.706 (3.3); 7,691 (3.7); 7,685 (3.7); 7,477 (7.0); 7,456 (5.9) 7,324 (4,3); 7,307 (4,7); 7,304 (4,7); 7,287 (3,9); 5,754 (6,5); 5,56 16,0); 3,318 (255,2) 2.819 (0.4), 2.809 (1.3), 2.800 (2.0), 2.791 (3.0), 2.782 (3.0), 2.773 (2.0), 2.764 (1, 4); 2754 (0.5); 2.675 (1, 1); 2.671 (1.5); 2.667 (1, 2); 2.524 (4.6); 2.508 (184.5); 2.502 (252.8); 2.497 (193.5); 2.333 (1.1); 2.329 (1.5); 2.324 (1, 1); 1 , 045 (1.4); 1,030 (1.4); 0,757 (1.7); 0.744 (5.1) 0.740 (6.7); 0J27 (6.6); 0J22 (5,3); 0J10 (2.1), 0.509 (2.1) 0.497 (6J); 0.492 (6.0) 0.487 (5J); 0.482 (5J); 0.470 (1J); 0.146 (1.2); 0.008 (9.4); 0.000 (245.3); - 0.008 (10.4); - 0.150 (1.1)
Beispiel 1-1-141: 1H-NMR(400.0 MHz, de-DMSO): δ= 9,804(4.9);9,786(5,1);8,504(6.2);8,499(6,2);8,279(6,4);8,058(4,6);8,048(4,5);7,828(3,7Example 1-1-141: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.804 (4.9), 9.786 (5.1), 8.504 (6.2), 8.499 (6.2), 8.279 (6, 4); 8,058 (4.6); 8,048 (4.5); 7,828 (3.7
);7,822(3,6);7,807(4,2);7,801(4,2);7,639(3,7);7,635(3,7);7,622(3,6);7,618(3,6);7,500(7,0);7,479(6,3);5,755(6,4);5,382(16,0);4,341(0,4);^); 7,822 (3.6); 7,807 (4.2); 7,801 (4.2); 7,639 (3.7); 7,635 (3.7); 7,622 (3.6); 7,618 (3.6) ; 7,500 (7.0); 7.479 (6.3); 5,755 (6.4); 5,382 (16.0); 4,341 (0.4); ^
(0,4);3,320(89,8);2,825(0,5):2,816(1,4);2,807(2,0);2,798{3,1);2,788(3,1);2,780i2,0);2,770(1,4);2,761(0,5);2,677(0,5);2,673(0,6);2,668(0,5);2,2,816 (1.4); 2,807 (2.0); 2.798 {3.1); 2,788 (3.1); 2,780i2: (0.4); 3,320 (89.8) 2,825 (0.5) , 0); 2,770 (1.4); 2,761 (0.5); 2,677 (0.5); 2,673 (0.6); 2,668 (0.5); 2,
526(1,8);2,513(38,0);2,508(76,8);2,504(104,1):2,499(78,0);2,495(38,1);2,335(0,5):2,331(0,6);2,326(0,4):1,047(3,3);1,032(3,2);0,761(1,8);0,526 (1.8); 2,513 (38.0); 2,508 (76.8); 2.504 (104.1) 2.499 (78.0); 2,495 (38.1); 2,335 (0.5): 2.331 1,047 (3.3); 1,032 (3.2); 0.761 (1.8); 0: (0.6) 2.326 (0.4)
748(5.3);0,743(7,0);0,731(6,9);0,726(5,5);0,714(2,2);0,517(2,2);0,506(6,2);0,500(6,2);0,496(5,8);0.491(5,8);0,479(1.8);0,146^ 748 (5.3); 0,743 (7.0); 0.731 (6.9) 0.726 (5.5) 0.714 (2.2) 0.517 (2.2) 0.506 (6.2) 0.500 (6 2) 0.496 (5.8); 0,491 (5.8); 0,479 (1.8); 0.146 ^
;0,000(130, 1 );-0,008(5,2);-0, 150(0,6)  0.000 (130, 1); - 0.008 (5.2); - 0, 150 (0.6)
Beispiel 1-1-142: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,589(1,2);9,573(1,3);8,345(1,1):8,325(1,1);7,874(1,0);7,853(4,4);7,716(0,6);7,713(0,7 );7,694(1,1);7,676(0,6);7,673(0,6);7,392(16,0);7,319(0,6);7,316(0,7);7,300(1,2);7,284(0,6);7,2  Example 1-1-142: 'H NMR (400.0 MHz, de-DMSO): δ = 9.589 (1.2), 9.583 (1.3), 8.345 (1.1): 8.325 (1.1 7.874 (1.0), 7.853 (4.4), 7.716 (0.6), 7.713 (0.7), 7.694 (1.1), 7.676 (0.6), 7.673 (0.6) ; 7,392 (16.0); 7,319 (0.6); 7,316 (0.7); 7,300 (1.2); 7,284 (0.6); 7.2
(0,6);4,332(0,4);3, 774(0,4);3,321 (27,9);2,526(0,7);2,512(15,3);2,508(31 ,7);2,503(43,7);2,499(33,3);2,494(16,6); 1 ,474(3,7); 1 ,457(3,6); 1 ,047( (0.6); 4.332 (0.4); 3, 774 (0.4); 3.321 (27.9); 2.526 (0.7); 2.512 (15.3); 2.508 (31, 7); 2,503 (43.7); 2,499 (33.3); 2,494 (16.6); 1, 474 (3,7); 1, 457 (3,6); 1, 047 (
11 ,5);1 ,031 (11 ,4);0,008(1 ,7);0,000(48,9);-0,008(1 ,9) 11, 5), 1, 031 (11, 4), 0.008 (1, 7), 0.000 (48.9), - 0.008 (1, 9)
Beispiel 1-1-143: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,679(4.6);9,662(4,6);8,059(1,9);8,045(3,7);8,031(1,9);7,870(4,0);7,856(10,5);7,849(5,Example 1-1-143: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.679 (4.6), 9.662 (4.6), 8.059 (1.9), 8.045 (3.7); 8,031 (1.9); 7,870 (4.0); 7,856 (10.5); 7,849 (5,
6);7,704(2,6);7,685(3,9);7,683(3,9);7,664(2,3);7,326(2,6);7,308(4,5);7,291(2,3);5,755(0,4);5,452(16,0);3,325(85,8);3,199(4,9);3,183(8,5);3,1 67(4,9);2,674(0,5);2,505(86,5);2,332(0,5);1,357(0,6);1,234(0,4);1,186(0,5);1,035(0,8);1,023(1,4);1,01^ 6); 7.704 (2.6); 7,685 (3.9); 7,683 (3.9); 7.664 (2.3); 7,326 (2.6); 7,308 (4.5); 7,291 (2.3 5.755 (0.4), 5.452 (16.0), 3.325 (85.8), 3.199 (4.9), 3.183 (8.5), 3.167 (4.9), 2.674 (0 , 5); 2,505 (86.5); 2,332 (0.5); 1,357 (0.6); 1,234 (0.4); 1,186 (0.5); 1,035 (0.8); 1.023 (1, 4); 1.01 ^
;0,974(0,8);0,478(1,5);0,466(5,7):0,447(5,7);0,434(1,7);0,247(1,8);0,236(7,1);0,224(6,8);0,211(1,5);0,147(0,4);0,000(71,6);-0,149(0,4) 0.447 (5.7) 0.434 (1.7) 0.247 (1.8) 0.236 (7.1);:; 0,974 (0.8);; 0.478 (1.5) 0.466 (5.7) 0.224 (6.8); 0,211 (1.5); 0,147 (0.4); 0,000 (71.6) - 0.149 (0.4)
Beispiel 1-1-144: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,764(11,4);9,747(11,6);8.651(15,5);8,645(16,0);8,313(0,6);8,132(8,8);8,126(8,9);8,11Example 1-1-144: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.764 (11.4), 9.747 (11.6), 8.651 (15.5), 8.645 (16.0 ); 8,313 (0.6); 8,132 (8.8); 8,126 (8.9) 8.11
1(10,0);8,104(10,1):7,974(10,0);7,965(10,2);7,816(15,9);7,795(13,9);7,668(5,2);7,649(10,4);7,630(6,3);7,628(7,2);7,454(12,6);7,432(10,6);7 ,423(6,7);7,421(6,8);7,404(11,3);7,388(5,1);7,385(5,6);5,753(7,7);4,340(0,5);4,330(0,5);3,319(302,7);2,818(1,0);2,808(2,9);2,799(4,7);2,790 (6,6);2,781(6,7);2,772(4,7);2,763(3,1);2,753(1,1);2,671(2,1);2,585(0,3);2,506(262,8);2,502(352,0);2,498(293,9);2,329(2,0);1,508(0,6);1,234( 0,6);1,045(3,4);1,030(3.3);0,754(3,7);0,737(15,8);0,724(15,1);0,720(13,5);0,708(4,6);0,685(0,5);0,668(0,4):0,523(0,5);0,515(0,5^1 (10.0) 8,104 (10.1) 7,974 (10.0); 7,965 (10.2); 7.816 (15.9); 7,795 (13.9); 7.668 (5.2) 7.649 (10.4); 7.630 (6.3); 7.628 (7.2); 7.454 (12.6); 7.432 (10.6); 7, 423 (6.7); 7.421 (6.8); 7,404 (11.3); 7,388 (5.1); 7,385 (5.6); 5,753 (7.7); 4,340 (0.5); 4,330 (0.5); 3,319 (302.7); 2,818 (1.0); 2,808 (2.9); 2,799 (4,7); 2,790 (6,6); 2,781 (6,7); 2,772 (4,7); 2,763 (3,1); 2,753 ( 1.1); 2,671 (2.1); 2,585 (0.3); 2,506 (262.8); 2.502 (352.0); 2.498 (293.9); 2,329 (2.0); 1,508 (0 , 6), 1.234 (0.6), 1.045 (3.4), 1.030 (3.3), 0.754 (3.7), 0.737 (15.8), 0.724 (15.1), 0.720 (13.5) ; 0.708 (4.6) 0.685 (0.5); 0.668 (0.4) 0.523 (0.5); 0,515 (0.5 ^
0,473(15,0);0,468(15,5);0,464(15,2);0,459(14,4);0,446(3,9);0,146(1,4);0,000(291,8);-0,150(1,4) 0.473 (15.0); 0.468 (15.5); 0.464 (15.2); 0.459 (14.4); 0,446 (3.9); 0,146 (1.4); 0,000 (291.8) - 0.150 (1.4)
Beispiel 1-1-145: 'H-NMR(400,0 MHz, de-DMSO): 6= 10,190 (7,9);9,675(4,8);9,658(5,0);7,947(4,0);7,925(5,3);7,880(12,8);7,803(2,6);7,800(2 Example 1-1-145: 'H NMR (400.0 MHz, de-DMSO): 6 = 10.190 (7.9); 9.675 (4.8); 9.658 (5.0); 7.947 (4.0 ); 7,925 (5.3); 7,880 (12.8); 7,803 (2.6); 7,800 (2
,8);7,784(3,2);7,781(4,6);7,762(2,3);7,759(2,3);7,646(7,8);7,627(8,6);7,408(2,5);7,405(2,6);7,389(4,7);7,373(2,3);7,370(2,4);7,352(5,5) 3(8,3);7,312(5,6);7,054(2,8);7,036(4,9);7,017(2,3);5,756(0,5);5,511(16,0):3,322(91,2);2,678(0,5);2,673(0,7);2,669(0,5);2,526(1,9);2,513(38, 8);2,509(78,8);2,504(107,5);2,499(80,5);2,495(39,1);2,335(0,5);2,331(0,6);2,326(0,5);0,146(0,6);0,008(4,4);0,000(117,7);-0,008(4,3);- 0,150(0,5) , 8); 7,784 (3.2); 7.781 (4.6); 7,762 (2.3); 7.759 (2.3); 7,646 (7.8); 7.627 (8.6) 7.408 (2, 5); 7.405 (2.6); 7.389 (4.7); 7.373 (2.3); 7.370 (2.4); 7.352 (5.5) 3 (8.3); 7.312 (5.6) ; 7,054 (2.8); 7,036 (4.9); 7,017 (2.3); 5,756 (0.5); 5,511 (16.0) 3,322 (91.2); 2,678 (0.5); 2.653 (0.7), 2.669 (0.5), 2.526 (1.9), 2.513 (38, 8), 2.509 (78.8), 2.504 (107.5), 2.499 (80.5), 2.495 (39.1) 2,335 (0.5); 2,331 (0.6); 2,326 (0.5); 0.146 (0.6) 0.008 (4.4) 0.000 (117.7) - 0.008 (4,3) - 0,150 (0,5)
Beispiel 1-1-146: 'H-NMR(400,0 MHz, de-DMSO): 6= 10,280(8,7);9,617(5,0);9,600(5,1);8,697(7,2);8,690(7,2);8,313(0,9);8,205(4,2);8,198(4, Example 1-1-146: 'H-NMR (400.0 MHz, de-DMSO): 6 = 10.280 (8.7); 9.617 (5.0); 9.600 (5.1); 8.697 (7.2 ); 8,690 (7.2); 8,313 (0.9); 8,205 (4.2); 8,198 (4,
0);8,184(4,5);8,176(4,4);7,965(4,1);7,943(5,5);7,875(12,7);7,840(2,7);7,837(2,8):7,818(4,5);7,799(2,3);7,797(2,2);7,481(7,2);7,460(7,0);7,42 7(2,6);7,424(2,6);7,408(4,9);7,392(2,3);7,389(2,3);5,753(8,5);5,510(16,0);3,320(615,3);2,676(1,9);2,671(2,6);2,667(1,9);2,524(7,8);2,507(32 3,3);2,502(431,5);2,498(324,5);2,494(161,3);2,334(1,9);2,329(2,5);2,324(1,8);1,232(0,7);1,046(1,3);1,030(1,2);0,146(2,0);0,008(16,6);0,0000); 8,184 (4.5); 8,176 (4.4); 7,965 (4.1); 7,943 (5.5); 7,875 (12.7); 7,840 (2.7); 7,837 (2.8 7.818 (4.5), 7.799 (2.3), 7.797 (2.2), 7.481 (7.2), 7.460 (7.0), 7.42 7 (2.6), 7.424 (2 , 6); 7,408 (4.9); 7,392 (2.3); 7,389 (2.3); 5,753 (8.5); 5,510 (16.0); 3,320 (615.3); 2.676 (1, 9), 2.671 (2.6), 2.667 (1.9), 2.524 (7.8), 2.507 (32.3.3), 2.502 (431.5), 2.498 (324.5), 2.494 (161, 3); 2,334 (1.9); 2,329 (2.5); 2,324 (1.8); 1,232 (0.7); 1,046 (1.3); 1,030 (1.2); 0,146 (2.0 ); 0.008 (16.6); 0.000
(426,1);-0,008(17,3);-0,150(2,0) (426.1) - 0.008 (17.3) - 0.150 (2.0)
Beispiel 1-1-147: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,667(2,0);9,651(2,0);8,075(0,8);8,060(1,6);8,045(0,8);7,869(1,7);7,854(5,1);7.847(2,3Example 1-1-147: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.677 (2.0), 9.651 (2.0), 8.075 (0.8), 8.060 (1.6 ); 8,045 (0.8); 7,869 (1.7); 7,854 (5.1); 7,847 (2.3
);7,704(1,0);7,701(1,0);7,682(1,8);7,664(0,9);7,661(0,9);7,328(1,0);7,325(1,0);7,309(1,9);7,293(1,0);7,290(0,9);5,457(6,8);3,327(19,9);3,161); 7.704 (1.0); 7,701 (1.0); 7,682 (1.8); 7.664 (0.9); 7,661 (0.9); 7,328 (1.0); 7,325 (1.0) ; 7,309 (1.9); 7,293 (1.0); 7,290 (0.9); 5,457 (6.8); 3,327 (19.9); 3.161
(2,3);3,145(4,1);3,129(2,4);2,511(20,3);2,506(27,2);2,502(20,2);1,802(0,5);1,785(0,9);1,768(1,2);1,752(1,0^ (1.785; (2.3); 3,145 (4.1); 3,129 (2.4); 2,511 (20.3); 2,506 (27.2); 2.502 (20.2); 1,802 (0.5) 0.9); 1,768 (1.2); 1,752 (1.0 ^
,6);0,008(1,1);0,000(29,9);-0,008(1,2)  , 6); 0.008 (1.1) 0.000 (29.9) - 0.008 (1.2)
Beispiel 1-1-148: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,678(3,1);9,662(3,2);8,374(1,3);8,359(2,7);8.344(1,3);7.879(2,6);7,857(3,6);7,849(7,7 );7,720(1,7);7,701(2,8);7,681(1,4);7,342(16,0);7,331(15,1);7,322(4,2);7,305(1,7);7,279(0,4);7,269(1,2);7,258(1,9);7,248(2,0);7,237(1,2);7,22 7(0,5);5,448(10,7);4,530(6,3);4,515(6,2);4,345(0,3);4,334(0.3);3,325(66,7);2,673(0,4);2,504(59,1);2,332(0.4);1,048(2,3);1.033^ Example 1-1-148: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.678 (3.1), 9.662 (3.2), 8.374 (1.3), 8.359 (2.7 8,344 (1.3); 7,879 (2.6); 7,857 (3,6); 7,849 (7.7); 7,720 (1,7); 7,701 (2,8); 7,681 (1,4) ; 7,342 (16.0); 7,331 (15.1); 7,322 (4.2); 7,305 (1.7); 7,279 (0.4); 7,269 (1.2); 7,258 (1.9); 7.248 (2.0), 7.237 (1.2), 7.22 7 (0.5), 5.448 (10.7), 4.530 (6.3), 4.515 (6.2), 4.345 (0.3 1.033 ^); 4,334 (0.3); 3,325 (66.7); 2,673 (0.4); 2,504 (59.1); 2,332 (0.4); 1,048 (2.3)
,1)  ,1)
Beispiel 1-1-149: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,660(3,8);9,643(3,9);8,406(1,5);8,390(3,2);8,375(1,6);7,881(3,1);7,859(4,2);7,850(10, 0);7,724(2,0);7,721(2,1);7,706(2,5);7,703(3,5);7,700(2,1);7,684(1,8);7,681(1,8);7,399(3,5);7,394(1,8);7,384(2,7);7,378(16,0);7,364(13,3);7,3 48(1,5);7,342(3,3);7,337(2,5);7,334(2,3);7,317(3.6);7,302(1,9);7,299(2,1);7,275(0.4);5,449(12.4);4,515(6,8);4,500(6,8);4,343 Example 1-1-149: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.660 (3.8), 9.643 (3.9), 8.406 (1.5), 8.390 (3.2 8.375 (1.6), 7.881 (3.1), 7.859 (4.2), 7.850 (10, 0), 7.724 (2.0), 7.721 (2.1), 7.706 (2.5) ; 7,703 (3.5); 7,700 (2.1); 7,684 (1.8); 7,681 (1.8); 7,399 (3.5); 7,394 (1.8); 7,384 (2.7); 7.378 (16.0); 7.364 (13.3); 7.3 48 (1.5); 7.342 (3.3); 7.377 (2.5); 7.334 (2.3); 7.317 (3.6); 7,302 (1.9); 7,299 (2.1); 7,275 (0.4); 5,449 (12.4); 4,515 (6.8); 4,500 (6.8); 4,343
;4,294(0,5);4,279(0,5);3,323(62,4);2,678(0,4);2,673(0,5);2,669(0,4);2,527(1,3);2,513(30,1);2,509(63,7);2,504(89,4);2,500(67,3);2,495(32,6); 2,335(0,4);2,331(0,5);2,326(0,4);1,047(5,1);1,032(5,0);0,146(0,5);0,008(4,0);0,000(116,5);-0,008(4,2);-0,150(0,5)  ; 4,294 (0.5); 4,279 (0.5); 3,323 (62.4); 2,678 (0.4); 2,673 (0.5); 2,669 (0.4); 2,527 (1.3); 2,513 (30.1); 2,509 (63.7); 2,504 (89.4); 2,500 (67.3); 2,495 (32.6); 2,335 (0.4); 2,331 (0.5); 2,326 (0.4); 1,047 (5.1); 1,032 (5.0); 0.146 (0.5) 0.008 (4.0); 0,000 (116.5) - 0.008 (4.2) - 0.150 (0.5)
Beispiel 1-1-150: 'H-NMR(400,0 MHz, de-DMSO): δ= 10,244(8,6);9,639(5,0);9,623(5,2);7,951(4,1);7,929(5,5);7,874(13,2);7,814(2,8);7,811(2 Example 1-1-150: 'H NMR (400.0 MHz, de-DMSO): δ = 10.244 (8.6); 9.639 (5.0); 9.623 (5.2); 7.951 (4.1 ); 7.929 (5.5) 7.874 (13.2); 7,814 (2.8); 7,811 (2
,8);7,795(3,4);7,792(4,6);7,773(2,4);7,770(2,3);7,696(1,2);7,688(11,4);7,683(3,7);7,671(4,0);7,666(13,3);7,658(1,3);7,414(2,7);7,411(2,7);7, 395(5,1);7,382(14,0);7,377(6,2);7,365(3,8);7,360(11,7);7,352(1,1);5,755(1,3);5,507(16,0);3,322(87,7);2,678(0,6);2,673(0,8);2,668(0,6);2,52 6(2,3);2,513(47,4);2,508(94,8);2,504(127,6);2,499(94,5);2,495(45,6);2,335(0,6);2,331(0,7);2,326(0,5);0,146(0,7);0,008 , 8); 7,795 (3.4); 7,792 (4.6); 7,773 (2.4); 7,770 (2.3); 7,696 (1.2); 7.688 (11.4); 7,683 (3, 7), 7.671 (4.0), 7.666 (13.3), 7.658 (1.3), 7.414 (2.7), 7.411 (2.7), 7, 395 (5.1), 7.382 (14 , 0); 7,377 (6.2); 7,365 (3.8); 7,360 (11.7); 7,352 (1.1); 5,755 (1.3); 5,507 (16.0); 3,322 (87, 7); 2,678 (0,6); 2,673 (0,8); 2,668 (0,6); 2,52,6 (2,3); 2,513 (47,4); 2,508 (94,8); 2,504 ( 127.6); 2,499 (94.5); 2,495 (45.6); 2,335 (0.6); 2,331 (0.7); 2,326 (0.5); 0.146 (0.7) 0.008
0,008(5,3);-0,150(0,7)  0.008 (5.3) - 0.150 (0.7)
Beispiel 1-1-151: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,695(0,8);9,678(0,8);7,943(1.2);7,853(0,8);7,845(2,1);7,832(0,9);7,688(0,5);7,685(0,4 );7.670(0.6);7,667(0,8);7,648(0,4);7,645(0,4);7,302(0,4);7,299(0,4);7.283(0,7);7,267(0,4);7.264(0.4);5,756(0,6);5,435(2,7);3 Example 1-1-151: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.695 (0.8); 9.678 (0.8); 7.943 (1.2); 7.853 (0.8); 7.845 (2.1), 7.832 (0.9), 7.688 (0.5), 7.685 (0.4), 7.670 (0.6), 7.667 (0.8), 7.648 (0.4), 7.645 (0 , 4); 7,302 (0.4); 7,299 (0.4); 7,283 (0.7); 7,267 (0.4); 7,264 (0.4); 5,756 (0.6); 5,435 (2.7) ; 3
(0,4);2,513(6,8);2,509(13,5);2,504(17,9);2,500(13,2);2,495(6,3);1,387(16,0);1,233(0,3);0,008(0,9);0,000(21,8);-0,009(0,8)  (1.233 (0.4); 2,513 (6.8); 2,509 (13.5); 2,504 (17.9); 2,500 (13.2); 2,495 (6.3); 1,387 (16.0) 0.3) 0.008 (0.9); 0,000 (21.8) - 0.009 (0.8)
Beispiel 1-1-152: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,666(3,0);9,649(3,0);9,114(7.2);8,826(16,0);8,005(2,4);7,996(2,4);7,799(2,4);7,777(3, 3);7,678(1 ,6);7,675(1 ,6);7,660(2, 1);7,657(2,7);7,638(1 ,4);7,635(1 ,3);7,334(1 ,5);7,332(1 ,5);7,315(2,8);7,299(1 ,4);7,296(1 ,4);5,756(1 ,1 );5,306 (10,5);3,323(13,0);2,788(0,8);2,779(1,2);2,770(1,8);2,761(1,8);2,752(1,2);2,743(0,8);2,526(0,8);2,508(38,6);2,504(52,0);2,499(38,7);2,495(^ 8,9);1,047(3,4);1,032(3,3);0J41(1,1);0,728(3,2);0,724(4,0);0,711(4,1);0,706(3,2);0,694(1,3);0,496(1,3);0,485(3,7);0,480(3,6);0,475(3,4);0,4Example 1-1-152: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.666 (3.0); 9.649 (3.0); 9.114 (7.2); 8.826 (16.0); 8.005 (2.4); 7.996 (2.4); 7.799 (2.4); 7.777 (3, 3); 7.678 (1, 6); 7.675 (1, 6); 7.660 (2, 1); 7.657 (2.7); 7.638 (1, 4); 7.635 (1, 3); 7.334 (1, 5); 7.332 (1, 5); 7.315 (2.8); 7.299 (1, 4); 7.296 ( 1, 4), 5.756 (1, 1), 5.306 (10.5), 3.323 (13.0), 2.788 (0.8), 2.779 (1.2), 2.770 (1.8), 2.761 (1 , 8), 2.752 (1.2), 2.743 (0.8), 2.526 (0.8), 2.508 (38.6), 2.504 (52.0), 2.499 (38.7), 2.495 (^ 8 , 9); 1,047 (3.4); 1,032 (3.3); 0J41 (1.1); 0,728 (3.2); 0,724 (4.0); 0,711 (4.1); 0.706 (3, 2); 0.694 (1.3) 0.496 (1.3) 0.485 (3.7) 0.480 (3.6) 0.475 (3.4) 0.4
70(3,4);0,458(1 ,0);0,008(1 ,3);0,000(34,3);-0,008(1.3) 70 (3.4), 0.458 (1, 0), 0.008 (1, 3), 0.000 (34.3), - 0.008 (1.3)
Beispiel 1-1-153: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,692(8,8);9,629(4,9);9,613(5,1);8,341(7,1);8,334(7,2);8,314(0,4);8,275(6,6);8,252(7, |6);7,972(4,0);7,950(5,4);7,914(4,3);7,908(4,1);7,892(3,9);7,885(3,9);7,875(i2,4);7,848(2,7);7,827(4,3);7,808(2,2);7 2(2,6);7,415(4,9);7,399(2.3);5,755(4,4);5,508(16,0);3,318(84,1);2,676(0,9) ^ Example 1-1-153: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10,692 (8.8); 9,629 (4.9); 9,613 (5.1); 8,341 (7.1 8.344 (7.2), 8.344 (0.4), 8.275 (6.6), 8.252 (7, 6), 7.972 (4.0), 7.950 (5.4), 7.914 (4.3 ); 7,908 (4.1); 7,892 (3.9); 7,885 (3.9); 7,875 (i2,4); 7,848 (2.7); 7.827 (4.3); 7,808 (2.2) ; 7 2 (2.6), 7.415 (4.9), 7.399 (2.3), 5.755 (4.4), 5.508 (16.0), 3.318 (84.1), 2.676 (0.9) ^
9(151,6);2,334{0,9);2,330(1,2);2,325(0,9);0,146(0,6);0,008(5,0);0,000(124,9);-0,008(4,8);-0,150(0,6)  9 (151.6); 2.334 {0.9); 2,330 (1.2); 2,325 (0.9); 0.146 (0.6) 0.008 (5.0) 0.000 (124.9) - 0.008 (4.8) - 0.150 (0.6)
Beispiel 1-1-154: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,664(4,5);9,647(4,6);8,506(5,6);8,500(5.7);8,022(3,9);8,013(3,9);7,797(3,2);7,791 (3,2Example 1-1-154: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.664 (4.5), 9.647 (4.6), 8.506 (5.6), 8.500 (5.7); 8,022 (3.9), 8,013 (3.9), 7,797 (3.2), 7,791 (3
);7,777(3,7);7,770(3,6);7,724(3,0);7,702(5,4);7,662(2,8);7,660(2,9);7,644(3,3);7,641(4,0);7,622(1,8);7,619(1,7);7,489(6,^ ); 7,777 (3.7); 7,770 (3.6); 7,724 (3.0); 7,702 (5.4); 7,662 (2.8); 7,660 (2.9); 7.644 (3.3) ; 7,641 (4.0); 7,622 (1.8); 7,619 (1.7); 7,489 (6, ^
2,3);7,326(2,4);7,309(4,1);7,294(2,1);7,291(2,0);5,755(4,6);5,278(16,0);4,342(0,9);4,331(0,9)^  2.3); 7,326 (2.4); 7,309 (4.1); 7,294 (2.1); 7,291 (2.0); 5,755 (4.6); 5,278 (16.0); 4,342 (0 4,331 (0.9) ^;, 9)
,782(1,9);2,773(2,8);2,764(2,8);2,755(1,9);2,746(1,3):2,736(0,5);2,677(0,4);2,673(0,5);2,669(0,4);2,526(1,5):2,509(61,3);2,504(83,4);2,500( 63,3);2,335(0.4);2,331(0,5);2,327(0,4);1,233(0,5);1,047(5,9);1,032(5,8);0,745(1,6);0,732(4,8);0,727(6,3);0,715(6,2);0,710(5,0);0,69^ , 782 (1.9); 2,773 (2.8); 2,764 (2.8); 2,755 (1.9); 2,746 (1.3) 2,736 (0.5); 2,677 (0.4); 2.653 (0.5), 2.669 (0.4), 2.526 (1.5): 2.509 (61.3), 2.504 (83.4), 2.500 (63.3), 2.335 (0.4), 2.331 (0 , 5); 2,327 (0.4); 1,233 (0.5); 1,047 (5.9); 1,032 (5.8); 0,745 (1.6); 0.732 (4.8) 0.727 (6, 3); 0.715 (6.2) 0.710 (5.0); 0.69 ^
543(0,3);0,531(0,4);0,526(0,4);0,496(2,0);0,486(5,8);0,480(5,7);0,475(5,3);0,470(5,4);0,458(1,6);0,008(2,2);0,000(55,7);-0,008(2,3)543 (0.3); 0,531 (0.4); 0.526 (0.4) 0.496 (2.0) 0.486 (5.8) 0.480 (5.7) 0.475 (5.3) 0.470 (5.4); 0.458 (1.6) 0.008 (2.2) 0.000 (55.7) - 0.008 (2.3)
Beispiel 1-1-155: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,501 (1 ,3);9,495(1 ,4);9.489(1 ,5);9,483(1 ,3);8.482(2,4);8,477(2,4);7,827(0,6);7,821 (0,6Example 1-1-155: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.501 (1.3), 9.495 (1.4), 9.489 (1.5), 9.483 (1, 3) 8,482 (2.4), 8.477 (2.4), 7.827 (0.6), 7.821 (0.6
);7,803(1,4);7,797(2,4);7,791 (1,5);7,783(1,3);7,777(2,5);7,770(1,6):7,743(1 ,5);7,731(1 ,6);7,719(0,9);7,707(0,8);7,490(2,7);7,469(2,3);5,755 1,6);5,234(6,8):3,754(16,0);3,318(16,8);2,507(32,2);2,503(42,4);2,498(32,8);1,046(1,3);1 ,031(1,3);0,000(24,6) 7.807 (1.4), 7.797 (2.4), 7.791 (1.5), 7.783 (1.3), 7.777 (2.5), 7.770 (1.6): 7.743 (1, 5) 7.731 (1, 6); 7.719 (0.9); 7.707 (0.8); 7.490 (2.7); 7.469 (2.3); 5.755 1.6); 5.234 (6.8): 3.754 (16.0); 3.318 (16.8); 2.507 (32.2); 2.503 (42.4); 2.498 (32.8); 1.046 (1.3); 1, 031 (1.3); 0.000 (24.6)
Beispiel 1-1-156: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,441(1,0);9,438(1,1);9,436(1,1);9,432(1,1);9,430(1,1);9,427(1,0);8,389(1,7);8,383(1,7 );8,089(0,7);8.084(0,6):8,067(0,8);8,061 (1 ,2);8,055(0,7);8,038(0.7);8,032(0,6):7,772(1 ,0);7,766(1 ,0);7,752(1 ,2);7,745(1 ,2);7,501 (2,3);7,480( 2,0);5,754(3,0);5,260(4,2);3,775(16,0);3,317(23,4);2,524(0,7);2,511(^ Example 1-1-156: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.441 (1.0), 9.438 (1.1), 9.436 (1.1), 9.432 (1.1 9.430 (1.1); 9.427 (1.0); 8.389 (1.7); 8.383 (1.7); 8.089 (0.7); 8.084 (0.6): 8.067 (0.8) 8,061 (1,2), 8,055 (0,7), 8,038 (0.7), 8,032 (0,6): 7,772 (1, 0), 7,766 (1, 0), 7,752 (1, 2), 7,745 ( 1, 2); 7,501 (2,3); 7,480 (2,0); 5,754 (3,0); 5,260 (4,2); 3,775 (16,0); 3,317 (23,4); 2,524 (0 , 7); 2,511 (^
(29,6);-0,008(1,1) (29.6) - 0.008 (1.1)
Beispiel 1-1-157: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,497(2,6);8,492(2,7);7,793(1 ,4);7,788(1 ,4);7,773(1 ,6);7,767(1 ,6);7,722(1 ,2);7,702(2,3 );7,682(1,6);7,533(2,2);7,512(1,8);7,494(2,9);7,473(2,5);7,203(2,0);7,184(1 ,9);5.223(7,8);4,342(0,6);4,331(0,6);3,702(16,0);3,32^Example 1-1-157: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.497 (2.6); 8.492 (2.7); 7.793 (1, 4); 7.788 (1, 4 7.773 (1, 6); 7.767 (1, 6); 7.722 (1, 2); 7.702 (2.3); 7.682 (1.6); 7.533 (2.2); 7.512 (1.8) 7.494 (2.9), 7.473 (2.5), 7.203 (2.0), 7.184 (1, 9), 5.223 (7.8), 4.342 (0.6), 4.331 (0.6); 3,702 (16.0); 3.32 ^
4(12,8);2,503(47,5);1,046(4,0):1,031(4,0);0,000(23,0) 4 (12.8) 2,503 (47.5); 1,046 (4.0) 1,031 (4.0); 0,000 (23.0)
Beispiel 1-1-158: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,487(2,1);9,470(2,2);8,592(3,6);8,558(3,1);8,554(3,1);7,902(3,2);7,741(0,6);7,719(1,9 );7,701 (4,2);7,678(0,8);7,346(1 ,0);7,342(1 ,0);7,329(1,9);7,313(0,9);5,245(8,0);3,742(16,0);3,326(23,3);2,505(31 ,2); 1 ,048(1 ,4);1 ,032(1 ,3);0,0 00(21,7) Example 1-1-158: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.487 (2.1); 9.470 (2.2); 8.592 (3.6); 8.558 (3.1 8,554 (3.1); 7,902 (3,2); 7,741 (0.6); 7,719 (1.9); 7,701 (4,2); 7,678 (0.8); 7,346 (1, 0) 7.342 (1, 0), 7.329 (1.9), 7.313 (0.9), 5.245 (8.0), 3.742 (16.0), 3.326 (23.3), 2.555 (31, 2); 1, 048 (1, 4); 1, 032 (1, 3); 0.0 00 (21.7)
Beispiel 1-1-159: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,908(2,1);9,892(2.1);8,360(2.7);8,354(2,7);7,687(1,4);7,680(1,4);7,665(2.6);7,660(3,3Example 1-1-159: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.908 (2.1); 9.892 (2.1); 8.360 (2.7); 8.354 (2.7); 7.687 ( 1.4); 7,680 (1.4); 7,665 (2.6); 7,660 (3.3
);7,642(2,1);7,502(3,4);7,482(2,8);7,343(1,9);7,325(2,5);7,307(1,7);5,475(7,6);4,844(16,0);3,319(19,4);2,525(0,6);2,512(13,1);2,507(26,8);^ 503(36,9);2,498(27,5):2,494(13,2);2,432(13,3):0,008(0,5);0,000(13,2);-0,009(0,4) ); 7,642 (2.1); 7,502 (3.4); 7,482 (2.8); 7,343 (1.9); 7,325 (2.5); 7,307 (1.7); 5,475 (7.6) 4,844 (16,0); 3,319 (19,4); 2,525 (0,6); 2,512 (13,1); 2,507 (26,8); ^ 503 (36,9); 2,498 (27,5) : 2,494 (13.2); 2.432 (13.3) 0.008 (0.5); 0,000 (13.2) - 0.009 (0.4)
Beispiel 1-1-160: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,526(2,1);9,510(2,2);8,315(3,1);7,608(1,4);7,602(1,2);7,587(2,0);7,485(3,7);7.472(2,8 );7,464(2,6);7,261(1,5);7,244(2,4);7,226(1,3);5,452(7,4);4,341 (0,7);4,332(0,6);3,779(0,4);3,743(16,0);3,320(37,5);3,309(3,3);^ Example 1-1-160: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.526 (2.1), 9.510 (2.2), 8.315 (3.1), 7.608 (1.4 7.602 (1.2), 7.587 (2.0), 7.485 (3.7), 7.472 (2.8), 7.444 (2.6), 7.261 (1.5), 7.244 (2.4) 7.266 (1.3), 5.452 (7.4), 4.341 (0.7), 4.332 (0.6), 3.779 (0.4), 3.743 (16.0), 3.320 (37.5); 3,309 (3.3); ^
6(56,2);2,503(61,2);2,418(12,0);2,329(0,4):1,049(3,5):1 ,046(5,7):1,034(3,7);1,031(5,8);0,003(24,8);0,000(40,8)  6 (56.2); 2.503 (61.2); 2.418 (12.0); 2.329 (0.4): 1.049 (3.5): 1.046 (5.7): 1.034 (3.7) ; 1.031 (5.8) 0.003 (24.8); 0.000 (40.8)
Beispiel 1-1-161 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9.901 (2.3);9,885(2,4);8,501 (3,0):8,495(3,0);7,891 (1 ,6);7,885(1 ,6);7,870(1 ,8);7,864(1 ,8Example 1-1-161: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9901 (2.3); 9.885 (2.4); 8.051 (3.0): 8.495 (3.0); 7,891 (1,6); 7,885 (1, 6); 7,870 (1, 8); 7,864 (1, 8);
);7,833(1,0);7,831(1,0);7,812(2,2);7,793(1,4);7,790(1,3);7,595(2,4);7,573(2,0);7,513(3,5);7,492(3,2);7,405(1,3);7,403(1 ,3);7,386(2,^); 7,833 (1.0); 7,831 (1.0); 7,812 (2.2); 7,793 (1.4); 7,790 (1.3); 7,595 (2.4); 7.573 (2.0) 7.513 (3.5), 7.492 (3.2), 7.405 (1.3), 7.403 (1, 3), 7.386 (2, ^
1 ,2);6,040(0,5);6,022(1,6);6,004(1,7);5,986(0,5);4,795(16,0);3,320(33,5);2,512(16,8);2,508(33,5);2,503(45,3);2,499(33,7); 1 ,924(7,8); 1,906(1, 2), 6.040 (0.5), 6.022 (1.6), 6.004 (1.7), 5.986 (0.5), 4.795 (16.0), 3.320 (33.5), 2.512 (16 , 8); 2,508 (33.5); 2.503 (45.3); 2,499 (33.7); 1, 924 (7,8); (1,906
7,7):0,008(0,6);0,000(12,3);-0,008(0,5) 7.7) 0.008 (0.6); 0,000 (12.3) - 0.008 (0.5)
Beispiel 1-1-162: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,863(2,6);9,847(2,6);8,608(3,9);8,604(3,8);8,571(3,7);8,565(3,7);8,314(0,9);7,939(3,7Example 1-1-162: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.863 (2.6) 9.847 (2.6); 8,608 (3.9); 8,604 (3.8 ); 8,571 (3.7); 8,565 (3.7); 8,314 (0.9); 7.939 (3.7
);7,902(1,0);7,883(2,4);7,864(1,6);7,780(3,0);7,758(2,1);7,419(1.4);7,403(2,6);7,386(1.3);5,276(9,5);4,810(16,0);3,568(0,9);3,32^); 7,902 (1.0); 7,883 (2.4); 7,864 (1.6); 7,780 (3.0); 7.758 (2.1); 7,419 (1.4); 7,403 (2.6); 7,386 (1.3); 5,276 (9.5); 4,810 (16.0); 3,568 (0.9); 3.32 ^
2(0,6);2,507(69,7);2,503(90,2);2,498(68,9);2.329(0,5);0,146(0,4);0,000(74,5);-0,149(0,4) 2 (0.6); 2,507 (69.7); 2.503 (90.2); 2,498 (68.9); 2,329 (0.5); 0,146 (0.4); 0,000 (74.5); - 0.149 (0.4)
Beispiel 1-1-163: 1H-NMR(400.0 MHz, de-DMSO): δ= 9,874(2,9);9,857(3,0);8,854(4,0);8,315(0,5);8,024(1,8);8,004(2,4);7,906(1,3);7,887(6,3Example 1-1-163: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.874 (2.9), 9.857 (3.0), 8.854 (4.0), 8.315 (0.5); 8.024 (1.8); 8,004 (2.4); 7,906 (1.3); 7,887 (6.3
);7,867(4,7);7,783(3,3);7,762(2,3);7,429(1,6);7,412(2,9);7,395(1,5);5,386(9,4);4,810(16,0);3,570(1,2);3,326(11,7);2,506(33,3);0,000(23); 7,867 (4.7); 7,783 (3.3); 7,762 (2.3); 7.429 (1.6) 7.412 (2.9); 7,395 (1.5); 5,386 (9.4) ; 4,810 (16.0); 3,570 (1.2); 3,326 (11.7); 2,506 (33.3); 0.000 (23
Beispiel 1-1-164: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,026(4,3);10,010(4,5);8,406(5,2);7,913(4,1);7,893(4,5);7,752(2,7);7,747(2,3);7,731(3Example 1-1-164: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.026 (4.3); 10.010 (4.5); 8.406 (5.2); 7.913 (4.1 ); 7,893 (4.5); 7,752 (2.7); 7.747 (2.3); 7,731 (3
,2);7,727(2,7);7,488(4,7);7,467(4,2);7,380(2,4);7,379(2,5);7,362(3,7);7,343(2,4);5,754(1,0);5,528(12,8);4,571(16,0);3,372(28,0);3,371 3,318(51,9);2,672(0,6);2,502(100,2);2,328(0,6);0,000(54,3);-0,002(54,8);-0,016(2,7) , 2), 7,727 (2.7); 7,488 (4.7); 7,467 (4.2); 7,380 (2.4); 7,379 (2.5); 7,362 (3.7); 7,343 (2, 4), 5.754 (1.0), 5.528 (12.8), 4.571 (16.0), 3.372 (28.0), 3.371 3.318 (51.9), 2.672 (0.6), 2.502 (100, 2); 2,328 (0.6); 0,000 (54.3) - 0.002 (54.8) - 0.016 (2.7)
Beispiel 1-1-165: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,950(2,2);9,944(2,4);9,938(2,4);9,932(2, 1);8,497(3,8);8,491 (3,7);7,945(1 ,0);7,939(1 ,0Example 1-1-165: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.950 (2.2), 9.944 (2.4), 9.938 (2.4), 9.932 (2, 1 8.497 (3.8); 8.491 (3.7); 7.945 (1, 0); 7.939 (1.0)
);7,924(1,3);7,921(1,8);7,915(1,6);7,900(1,5);7,894(1,4):7,820(2,2):7,812(2,9);7,799(4,6);7,793(2,8);7,787(1,7);7,774(1 ,6);7,504(4,4);7,4 3,9);5,247(10,6);4,543(16,0);3,365(31,2);3,319(92.6);2,676(0,5);2,671(0,6);2,667(0,5);2,507(75,4);2,502(102,3);2,498(76,2);2,^); 7.924 (1.3) 7.921 (1.8) 7.915 (1.6); 7,900 (1.5); 7,894 (1.4) 7,820 (2.2) 7,812 (2.9) 7,799 (4,6); 7,793 (2,8); 7,787 (1,7); 7,774 (1, 6); 7,504 (4,4); 7,4 3,9); 5,247 (10,6) ; 4,543 (16.0); 3.365 (31.2); 3,319 (92.6); 2,676 (0.5); 2,671 (0.6); 2,667 (0.5); 2,507 (75.4); 2.502 ( 102.3); 2,498 (76.2); 2, ^
9(0,6);2,325(0,5);0,146(0,4);0,000(91,0);-0,008(3,5);-0,150(0,4) 9 (0.6); 2,325 (0.5); 0,146 (0.4); 0,000 (91.0) - 0.008 (3.5) - 0.150 (0.4)
Beispiel 1-1-166: 'H-NMR(400,0 MHz, de-DMSO): δ= 8,510(3,4);8,504(3,4);7,826(1,8);7,804(4,4);7,789(2,6);7,785(3,3);7,577(2,7);7,555(2,2 );7,498(4,1);7,477(3,6);7,255(2,5);7,236(2,4);5,754(8,4);5,246(9,8);4,620(16,0);3,806(0,5);3,338(31 ,1);3,320(114.8);2,676(0,4) Example 1-1-166: 'H NMR (400.0 MHz, de-DMSO): δ = 8.510 (3.4); 8.504 (3.4); 7.826 (1.8); 7.804 (4.4 7.799 (2.6); 7.785 (3.3); 7.577 (2.7); 7.555 (2.2); 7.498 (4.1); 7.477 (3.6); 7.255 (2.5) 7.236 (2.4), 5.754 (8.4), 5.246 (9.8), 4.620 (16.0), 3.806 (0.5), 3.338 (31, 1), 3.320 (114.8), 2.676 ( 0.4)
667(0,4);2,551(16,8);2,525(1 ,4);2,511(31,3);2,507(65,9);2,502(92,3);2,498(69,0);2,494(33,1);2,334(0,4);2,329(0,6);2,325(0,4);0,146(0,4);0 008(2,8):0,000(84,2);-0,008(2,8);-0,150(0,4) 667 (0.4), 2.551 (16.8), 2.525 (1, 4), 2.511 (31.3), 2.507 (65.9), 2.502 (92.3), 2.498 (69.0), 2.494 (33.1); 2.334 (0.4); 2.329 (0.6); 2.325 (0.4); 0.146 (0.4); 0 008 (2.8): 0.000 (84.2); - 0.008 (2.8) - 0.150 (0.4)
Beispiel 1-1-167: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,754(4.0);8,496(3,4);8,490(3,3);7,798(1,9);7,792(1.9):7.777(2.2);7,771(2,1);7,700(1.3 );7,697(1,3);7,678(2,8);7,674(2,8):7,642(4,2);7,620(1,9);7,492(3,8);7,472(3,4);5,213(9,4);4,532(14,3);3,363(28.3);3,321(55,5);2Example 1-1-167: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.754 (4.0); 8.496 (3.4); 8.490 (3.3); 7.798 (1.9); 7,792 (1.9): 7,777 (2.2); 7,771 (2.1); 7,700 (1.3); 7,697 (1.3); 7,678 (2,8); 7,674 (2,8): 7,642 (4,2); 7,620 (1.9); 7,492 (3.8); 7,472 (3.4); 5,213 (9.4); 4,532 (14.3); 3.363 (28.3); 3.321 (55.5), 2
08(43,4):2,503(57,3);2,499(43,1);2,365(16,0);2,330(0,4);0,000(48,8);-0,008(2,0) 08 (43.4) 2.503 (57.3); 2,499 (43.1); 2,365 (16.0); 2,330 (0.4); 0,000 (48.8) - 0.008 (2.0)
Beispiel 1-1-168: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,860(2,7):9,844(2,7);8.478(3,9);8,473(3,9);8,355(0,4);8,314(0,3);8,148(4.1);8,143(3,9 );8,034(0,4);8,030(0,3);7,903(1 ,1 );7,901 (1 ,1 );7,882(2,5);7,863(1 ,7);7,775(3,0);7,754(2,1);7,420(1 ,5);7,403(2,7);7,387(1 ,3);5,271 (9,9);4,805( 16,0);4,506(0,5);4,491(0,5);3,569(0,9);3,321(35,2);2,673(0,3);2,508(41,0):2,504(52,8);2,500(40,4);1,234(0,6);0,000(49,0)  Example 1-1-168: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.860 (2.7): 9.844 (2.7), 8.478 (3.9), 8.483 (3.9 8.355 (0.4), 8.344 (0.3), 8.148 (4.1), 8.143 (3.9), 8.034 (0.4), 8.030 (0.3), 7.903 (1, 1), 7.901 (1, 1); 7,882 (2.5); 7,863 (1, 7); 7,775 (3,0); 7,754 (2,1); 7,420 (1, 5); 7,403 (2,7); 7,387 ( 1, 3), 5.271 (9.9), 4.805 (16.0), 4.506 (0.5), 4.491 (0.5), 3.569 (0.9), 3.321 (35.2), 2.673 (0 , 3); 2,508 (41.0) 2,504 (52.8); 2,500 (40.4); 1,234 (0.6); 0,000 (49.0)
Beispiel 1-1-169: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,944(3,3);9,928(3,4);8,657(4,5);8.650(5,4);8,313(6,8);8,306(2,8);8,139(2,3);8,133(2,9Example 1-1-169: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.944 (3.3), 9.928 (3.4), 8.657 (4.5), 8.650 (5.4 ); 8,313 (6.8); 8,306 (2.8); 8,139 (2.3); 8,133 (2.9
);8,118(28);8.112(3.3);7,887(1,6);7,868(3,2);7,838(5,0);7.817(3,9);7,505(2,1);7,485(6,3);7.463(4,1);4,^ ); 8,118 (28); 8,112 (3.3); 7,887 (1.6); 7,868 (3.2); 7,838 (5.0); 7,817 (3.9); 7,505 (2.1); 7,485 (6 , 3); 7,463 (4.1); 4 ^
8(0,8);2,501 (126.5);2,500(126,5);2,328(0,8);0, 145(0,3);0,000(67,0);-0, 150(0,4)  8 (0.8), 2.501 (126.5), 2.500 (126.5), 2.328 (0.8), 0.145 (0.3), 0.000 (67.0), -0.150 (0.4 )
Beispiel 1-1-170: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,694(3,3);9,688(3,6);9,682(3,7);9,676(3,1);8,489(5,9);8,484(5,8):8,314(0,5);7,988(4,2 );7,979(4,2);7J95(4,6);7J88(3J);7J73(7!3);7J60(4J);7J43(2,6);7J37(2,4);7J22(3,0);7J18(2,8);7,699(1,2);7,693(1 ,1);7!492(6,4);7,471( 5,6);5,282(16,0);4,341 (0,7);4,330(0.7);3,318(276,0);2,800(0,4);2,791 (1 ,2);2,782(1 ,8);2,773(2,7);2,764(2,7);2,755(1 ,9);2,746(1 ,2);2,736(0,5);Example 1-1-170: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.694 (3.3); 9.688 (3.6); 9.682 (3.7); 9.676 (3.1 ); 8,489 (5.9); 8,484 (5.8) 8,314 (0.5); 7,988 (4.2 ); 7,979 (4.2); 7J95 (4,6); 7J88 (3J); 7J73 (7 3);! 7J60 (4J); 7J43 (2,6); 7J37 (2,4); 7J22 (3 , 0); 7J18 (2,8); 7,699 (1,2); 7,693 (1, 1); 7 ! 492 (6.4), 7.471 (5.6), 5.282 (16.0), 4.341 (0.7), 4.330 (0.7), 3.318 (276.0), 2.800 (0.4), 2.791 (1 , 2); 2,782 (1, 8); 2,773 (2,7); 2,764 (2,7); 2,755 (1,9); 2,746 (1,2); 2,736 (0,5);
2,671(2J);2,506(275,2);2,502(345,6);2,328(2,0);1,045(4J);1,030(4,1);0,752(1,5);0,734(6,1);0,722(6,3);0J17(5,0);0,705(1 ,8);0,505(1,9);0,4 94(6,1);0,488(6,1);0,479(5,5);0,466(1,5);0,147(0,7);0,000(146,4);-0,149(0,7) 2,671 (2J); 2.506 (275.2); 2.502 (345.6); 2,328 (2.0); 1,045 (4J); 1,030 (4.1); 0,752 (1.5); 0.734 (6.1 0.722 (6.3), 0J17 (5.0), 0.705 (1.8), 0.505 (1.9), 0.4 94 (6.1), 0.488 (6.1), 0.479 (5 , 5); 0.466 (1.5) 0.147 (0.7); 0,000 (146.4) - 0.149 (0.7)
Beispiel 1-1-171 : 'H-NMR(400,0 MHz, de-DMSO): δ= 8,504(4,6);8,498(4,5);8,081 (2,6);7,792(2,6);7,786(2,6);7,771 (2,9);7,765(2,7);7,653(1 ,4 );7,632(3,1);7,613(2,7);7,572(3,8):7,551(2.1);7,495(4,3);7,475(3,8);7,170(3,1);7,152(2.8);5,755(0,9);5.278^  Example 1-1-171: 'H NMR (400.0 MHz, de-DMSO): δ = 8.504 (4.6); 8.498 (4.5); 8.081 (2.6); 7.792 (2.6 7.786 (2.6); 7.771 (2.9); 7.765 (2.7); 7.653 (1, 4); 7.632 (3.1); 7.613 (2.7); 7.572 (3.8) : 7,551 (2.1); 7,495 (4.3); 7,475 (3.8); 7,170 (3.1); 7,152 (2.8); 5,755 (0.9); 5.278 ^
44(16,0);2,723(2,0);2,714(1,8);2,671(0,9);2,502(124,4);2,373(0,4);2,329(0,8);2,300(0,6);2,232(0,6);1,743(0,5);1, 356(1, 0);1, 234(0,6);0,702(1 ,2);0,689(4,1);0,685(4,7);0,673(4,8);0,668(4,0);0,656(1,5);0,635(0,4);0,617(0,4);0,487(1,7);0,476(5,1);0,470(5,4);0,461 (4,5)  44 (16.0); 2,723 (2.0); 2,714 (1.8); 2,671 (0.9); 2,502 (124.4); 2,373 (0.4); 2,329 (0.8); 2,300 (0.6); 2.232 (0.6); 1.743 (0.5); 1, 356 (1, 0); 1, 234 (0.6); 0.702 (1, 2); 0.689 (4.1 ); 0.685 (4.7) 0.673 (4.8) 0.668 (4.0) 0.656 (1.5) 0.635 (0.4) 0.617 (0.4) 0.487 (1.7) 0.476 (5.1); 0.470 (5.4); 0.461 (4.5)
0(46,0);-0,006(9,6)  0 (46.0) - 0.006 (9.6)
Beispiel 1-1-172: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,164(2,5);10,161(2,7);10,147(2,6);10,145(2,7);8,416(2,8);8,410(2,9);8,393(2,5);8,39 1 (2,6);8,374(2,7);8.371 (2,6);7,821(1,6);7,814(1,6);7,800(1 ,9);7,793(1,8);7,558(2,2);7,541 (2,6);7,538(2,8);7,532(3,6);7,521 (2,2);7,511 (3,0);5, 493(8,1);4,829(16,0);3,318(19,6);2,506(21,6);2,502(29,7);2,497(22,5);0,008(0,7);0,000(17,9);-0,008(0,7) Example 1-1-172: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.164 (2.5), 10.161 (2.7), 10.147 (2.6), 10.145 (2.7 8.416 (2.8), 8.410 (2.9), 8.393 (2.5), 8.391 (2.6), 8.374 (2.7), 8.371 (2.6), 7.821 (1 , 7,814 (1,6), 7,800 (1, 9), 7,793 (1,8), 7,558 (2,2), 7,541 (2,6), 7,538 (2,8), 7,532 (3, 6), 7.521 (2.2), 7.511 (3.0), 5.493 (8.1), 4.829 (16.0), 3.318 (19.6), 2.506 (21.6), 2.502 (29 , 7); 2.497 (22.5) 0.008 (0.7); 0,000 (17.9) - 0.008 (0.7)
Beispiel 1-1-173: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,737(2,2);7,765(0,5);7,743(3,0);7,735(2,3);7,732(2,1);7,713(0,4);7,709(0.4);7,382(3,8Example 1-1-173: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.737 (2.2); 7.765 (0.5); 7.743 (3.0); 7.735 (2.3 ); 7,732 (2.1); 7,713 (0.4); 7.709 (0.4); 7,382 (3.8
);7,311(0,3);5,256(0,5);5,231 (5,3);4,519(8,6);3,958(1,0);3,946(16,0);3,881(1,2);3,783(0,6);3,362^ 7,311 (0.3), 5.256 (0.5), 5.231 (5.3), 4.519 (8.6), 3.958 (1.0), 3.946 (16.0), 3.881 (1.2) ; 3,783 (0.6); 3.362 ^
6(0,5);2,513(12,1);2,508(25,8);2,504(36,1);2,499(26,9);2,495(13,0);2,367(9,1);2,268(0,7);0,000(10,0);-0,008(0,4)  6 (0.5); 2,513 (12.1); 2,508 (25.8); 2,504 (36.1); 2,499 (26.9); 2,495 (13.0); 2,367 (9.1); 2,268 (0.7); 0,000 (10.0) - 0.008 (0.4)
Beispiel 1-1-174: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.738(3,9);8,077(0,3);7,831(6,5);7,812(2,1);7,790(4,3);7,775(0,7);7,753(2.8):7,750(2.9Example 1-1-174: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,738 (3.9), 8.077 (0.3), 7.831 (6.5), 7.812 (2.1 ); 7,790 (4.3); 7,775 (0.7); 7,753 (2.8) 7,750 (2.9
);7,728(1,4);7,540(0,5);5,393(0,8);5,365(9,6);4,522(14,0);4,041(0,3);3,921(1,0);3,364(26,0);3,319(40,7);3,291(2,0);2,673(0,4);2,543(1,2) 08(48,4);2,504(67,7):2,500i53,3):2,371(16,0);2,331(0,5);2,304(1,2);2,212(0,8):2,076(0,8);0,146(0,3);0,007(2,9);0,000(68,8);-0,008(4,2);- 0,150(0,3) ); 7,728 (1.4); 7,540 (0.5); 5,393 (0.8); 5,365 (9.6); 4,522 (14.0); 4,041 (0.3); 3,921 (1.0) 3.364 (26.0), 3.319 (40.7), 3.291 (2.0), 2.673 (0.4), 2.543 (1.2) 08 (48.4), 2.504 (67.7): 2.500 i53,3): 2,371 (16.0); 2,331 (0.5); 2,304 (1.2); 2,212 (0.8) 2,076 (0.8); 0.146 (0.3) 0.007 (2 , 9), 0.000 (68.8), - 0.008 (4.2), - 0.150 (0.3)
Beispiel 1-1-175: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,747(4.3);7,831(6,6);7,809(2.1);7,787(4,2);7.749(2,9);7,746(2,9);7,727(1,5);5,364(9,4Example 1-1-175: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.747 (4.3); 7.831 (6.6); 7.809 (2.1); 7.787 (4.2); 7.749 ( 2.9) 7.746 (2.9); 7,727 (1.5); 5,364 (9.4
);4,559(13,7);3,963(0,6);3,583(1,8);3,565(6,0);3,548(6,1);3,530(2,0);3,320(20,9);2,544(1,1);2^ ); 4,559 (13.7); 3,963 (0.6); 3,583 (1.8); 3,565 (6.0); 3,548 (6.1); 3,530 (2.0); 3,320 (20.9) 2.544 (1.1); 2 ^
2,267(0,4); 1 , 174(5,9); 1 , 156(12, 1 ); 1 , 139(5,9); 1,115(0,5);0,000(44,7)  2,267 (0.4); 1, 174 (5.9); 1, 156 (12, 1); 1, 139 (5.9); 1,115 (0.5); 0,000 (44.7)
Beispiel 1-1-176: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,736(2,7);9,720(2,7);8,623(1,2);8,608(2,7);8,592(1,3);8,338(3,5);8,332(3,5);8,135(0,4 Example 1-1-176: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.736 (2.7), 9.720 (2.7), 8.623 (1.2), 8.608 (2.7 ); 8,592 (1.3); 8,338 (3.5); 8.332 (3.5); 8,135 (0.4
);7,622(1,8);7,615(1,8);7,601 (2,5);7,595(2,5);7,487(4.8);7,466(3,6);7,429(2,4);7,410(2,9);7,401 (2,5);7,395(1,4);7,386(1 ,8);7,379(14,8);7^ (12,3);7,363(1,8);7,354(1,0);7,347(2,1);7,295(0,6);7,273(0,4);7,239(2,7);7,221(3,5);7,203(2,2);5,510(8,8);4,522(5,7);4,507(5,7);4,340(1,2);4, 330(1,3);4,293(0,5);4,278(0,5);3,779(0,4);3,769(0,4);3,764(0,3);3,320(93,9);2,676(0,3);2,672(0,5);2,667(0,3);2,525(1,0);2,520(1,4);2,512(2^ ,6);2,507(55,9);2,503(79,2);2,498(57,8);2,494(26,8);2,446(0,6):2,430(16,0);2,334(0,3);2,329(0,5);2,325(0,4);1,046(8,4);1,031(8,3);0,146(0,4 );0,008(3, 1 );0,000(103,4);-0,009(3,2);-0, 150(0,5) 7.622 (1.8), 7.615 (1.8), 7.601 (2.5), 7.595 (2.5), 7.487 (4.8), 7.466 (3.6), 7.429 (2.4), 7.410 (2.9), 7.401 (2.5), 7.955 (1.4), 7.386 (1, 8), 7.379 (14.8), 7 ^ (12.3), 7.363 (1.8), 7.354 (5,510 (1.0); 7,347 (2.1); 7,295 (0.6); 7,273 (0.4); 7,239 (2.7); 7,221 (3.5); 7,203 (2.2) 4.5 (5.7), 4.457 (5.7), 4.340 (1.2), 4, 330 (1.3), 4.293 (0.5), 4.278 (0.5), 3.779 (2.525 (0.4); 3,769 (0.4); 3,764 (0.3); 3,320 (93.9); 2,676 (0.3); 2,672 (0.5); 2,667 (0.3) 2.520 (1.4), 2.512 (2 ^, 6), 2.507 (55.9), 2.503 (79.2), 2.498 (57.8), 2.494 (26.8), 2.446 ( 0.6) 2,430 (16.0); 2,334 (0.3); 2,329 (0.5); 2,325 (0.4); 1,046 (8.4); 1,031 (8.3); 0.146 (0 , 4); 0.008 (3, 1); 0.000 (103.4); - 0.009 (3.2); - 0, 150 (0.5)
Beispiel 1-1-177: 'H-NMR(400,0 MHz, de-DMSO): δ= 9.917(2,9);9,901(3,0);8,605(4,2);8,601(4,4);8,573(4,2);8,567(4,3);7,937(2,4);7,932(4,2 Example 1-1-177: 'H-NMR (400.0 MHz, de-DMSO): δ = 9,917 (2.9), 9.901 (3.0), 8.605 (4.2), 8.601 (4.4 ); 8.573 (4.2); 8,567 (4.3); 7,937 (2.4); 7,932 (4.2
);7,928(2,5);7,842(1,1);7,823(2,5);7,802(2,0);7,747(3,5);7,725(2,1);7,386(1 ,6);7,369(2,8);7,351 (1,4);5,761(0,4);5,260(10,4);4,591 (16,0);^ 4(2,1):3,577(6,8);3,559(6,9);3,542(2,2):3,325(60,7);2,679(0,4);2,674(0,4);2,531(1,0);2,514(52,1);2,510(73,8);2,505(56,6);2,336(0,4);1,240(0 ,4);1,182(6,9);1,165(13,9);1, 147(6,7) 7.928 (2.5), 7.842 (1.1), 7.823 (2.5), 7.802 (2.0), 7.747 (3.5), 7.725 (2.1), 7.386 (1, 6) 7,369 (2,8); 7,351 (1,4); 5,761 (0,4); 5,260 (10,4); 4,591 (16,0); ^ 4 (2,1): 3,577 (6,8) ; 3,542 (2.2); 3,559 (6.9) 3,325 (60.7); 2,679 (0.4); 2,674 (0.4); 2,531 (1.0); 2,514 (52.1); 2.510 (73.8), 2.505 (56.6), 2.336 (0.4), 1.240 (0, 4), 1.182 (6.9), 1.165 (13.9), 1, 147 (6.7)
Beispiel 1-1-178: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,943(4,6);9,927(4,6);8,491(5,7);8,485(6,1);8,313(0,6);8,265(0,4);8,260(0,5);7,873(3,2Example 1-1-178: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.943 (4.6); 9.927 (4.6); 8.491 (5.7); 8.485 (6.1 ); 8,313 (0.6); 8,265 (0.4); 8,260 (0.5); 7,873 (3.2
);7,867(3,2);7,852(3,6);7,846(3,5);7,765(1,8);7,762(2,1);7,744(4,3);7,725(2,6);7,722(3,0);7,547(4,6);7,525(3,8);7,506(7,2);7,485(6,4);7,362( 2,7);7,345(4,8);7,329(2,2);7,327(2,65;6,798{0,6);6,776{0,5);6,018(0,9);6,000(3,2);5,982(3,2);5,964(1,0);4,565(0,8);4,538(1,4);4,524(13,9);4, 520(14,5);4,478(0,7);3,828(3,7);3,361(5,6);3,356(51,8);3,316(212,7);2,676(1,0);2,671(1,4);2,667(1,0);2,524(2,8);2,506(160,9);2,502(230,4)^ 2,497(176,5):2,493(87,2);2,333(1,0);2,329(1,3):2,324(1,0);1,913(15,0);1,895(16,0);1,877(1,4);1,235(0,4):1,030(0,3);0,146(1,2);0,008(8,2);0, 000(266,6);-0,008(10,4);-0, 150(1,2) ); 7,867 (3.2); 7.852 (3.6); 7,846 (3.5); 7,765 (1.8); 7,762 (2.1); 7.744 (4.3); 7,725 (2.6) 7.722 (3.0); 7.547 (4.6); 7.525 (3.8); 7.506 (7.2); 7.485 (6.4); 7.362 (2.7); 7.345 (4.8); 7,329 (2.2); 7,327 (2.65; 6.798 {0.6); 6,776 {0.5); 6,018 (0.9); 6,000 (3.2); 5,982 (3.2); 5,964 ( 4.55 (0.8); 4.538 (1.4); 4.524 (13.9); 4.520 (14.5); 4.478 (0.7); 3.828 (3.7); 3.361) (2,506 (5.6); 3,356 (51.8); 3.316 (212.7); 2,676 (1.0); 2,671 (1.4); 2,667 (1.0); 2,524 (2.8) 2.502 (230.4) ^ 2.497 (176.5): 2.493 (87.2); 2.333 (1.0); 2.329 (1.3): 2.324 (1.0); 1.913 (15 , 0), 1.895 (16.0), 1.877 (1.4), 1.235 (0.4): 1.030 (0.3), 0.146 (1.2), 0.008 (8.2), 0.000 ( 266.6), - 0.008 (10.4), - 0, 150 (1.2)
Beispiel 1-1-179: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,905(2.7);9,888(2,9);8,468(4,1);8,462(4,2);8,137(4,4);8,132(4.3);7,841(1,1);7,838(1,1Example 1-1-179: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.905 (2.7), 9.888 (2.9), 8.468 (4.1), 8.462 (4.2); 8.137 (4.4); 8,132 (4.3); 7,841 (1.1); 7,838 (1.1
);7,819(2,7);7,816(1,9);7,800(1,9);7,797(1,8);7,738(3,2);7,716(2,0);7,385(1 ,4);7,382(1 ,4);7,366(2,6);7,350(^ 7,819 (2,7); 7,816 (1,9); 7,800 (1,9); 7,797 (1,8); 7,738 (3,2); 7,716 (2,0); 7,385 (1, 4) 7,382 (1, 4); 7,366 (2,6); 7,350 (^
(0,4);4,541 (16,0);3,910(1,3):3,366(33,3);3,321(57,4);2,527(0,7);2,522(1,0);2,513(18,0);2,509(38,4);2,504(53,8);2,500(39.4);2,495(18,5);0,0 (0.4); 4.541 (16.0); 3.910 (1.3): 3.366 (33.3); 3.321 (57.4); 2.527 (0.7); 2.522 (1.0); 2.513 ( 18.0) 2,509 (38.4); 2,504 (53.8); 2,500 (39.4); 2,495 (18.5); 0.0
08(2,1);0,000(67,5);-0,008(2,2) 08 (2.1); 0,000 (67.5) - 0.008 (2.2)
Beispiel 1-1-180: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,918(2,8);9,902(2,9);8,845(3,4);8,008(1,5);8,004(1,5);7,988(2.0);7,983(2.0);7,881 (4.1Example 1-1-180: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.918 (2.8), 9.902 (2.9), 8.845 (3.4), 8.008 (1.5 8.004 (1.5); 7.988 (2.0); 7.983 (2.0); 7.881 (4.1
);7,861(3,0);7,843(1,1);7,840(1,1);7,821(2,6);7,819(1,9);7,803(1,8);7,800(1 ,8);7,741(3,3);7,720(2,1);7,392(1,4);7,390(1 ,5);7,373(2,7);7,357^ 1,3);7,355(1,3);5,363(8,8);4,547(16,0);3,368(31,2);3,320(28,1);2,527(0,5);2,514(12,8);2,509(27,1);2,505(38,0);2,501(28,3);2,496(13,6);0,00 8(1,5);0,000(47,5);-0,008(1,7) 7.861 (3.0), 7.843 (1.1), 7.840 (1.1), 7.821 (2.6), 7.819 (1.9), 7.803 (1.8), 7.800 (1, 8) 7,741 (3,3); 7,720 (2,1); 7,392 (1,4); 7,390 (1, 5); 7,373 (2,7); 7,357 ^ 1,3); 7,355 (1,3); 5,363 (8.8); 4,547 (16.0); 3,368 (31.2); 3,320 (28.1); 2,527 (0.5); 2,514 (12.8); 2,509 (27.1); 2,505 (38.0); 2.501 (28.3); 2.496 (13.6); 0.008 (1.5); 0.000 (47.5); -0.008 (1.7)
Beispiel 1-1-181 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,732(2,7);9,716(2,7);8,322(3,4);8,316(3,4);8,190(2,5);8,180(2,5);7,598(1,6);7.592(1,6Example 1-1-181: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.732 (2.7), 9.716 (2.7), 8.322 (3.4), 8.316 (3.4 ); 8,190 (2.5); 8,180 (2.5); 7.598 (1.6) 7.592 (1.6
);7,578(2,2);7,571(2,3);7,482(4,6);7,461(3,2);7,420(2,2);7,401 (2,7);7,244(2,3);7,226(3,3);7,209(1,9);5,753(1,0);5,490(9,2);3,315(114,0);2,80 0(0,8);2,790(1 ,2);2,782(1 ,7);2,772(1 ,8);2,763(1 ,2);2,754(0,8);2,675(0,7);2,671 (1 ,0);2,666(0,8);2,523(2,2);2,506(119,9);2,501 (169,0);2,497(17.558 (2.2), 7.571 (2.3), 7.482 (4.6), 7.461 (3.2), 7.420 (2.2), 7.401 (2.7), 7.244 (2.3) 7,226 (3,3); 7,209 (1,9); 5,753 (1,0); 5,490 (9,2); 3,315 (114,0); 2,80 0 (0,8); 2,790 (1); 2,782 (1,7), 2,772 (1,8), 2,763 (1,2), 2,754 (0,8), 2,675 (0,7), 2,671 (1,0), 2,666 (0,8 2.523 (2.2), 2.506 (119.9), 2.501 (169.0), 2.497 (1
28,0);2,440(0,6);2,425(16,0);2,333(0,7);2,328(1,0);2,324(0,7);1,045(0,3);1 ,030(0,3);0,745(1,0);0,733(3,0);0,728(3,9);0,715(3,9);0,711P ,699(1,2);0,494(1,2);0,483(3,7);0,478(3,4);0,473(3,2);0,468(3,3);0,456(1,0);0,146(0,9);0,008(5,7);0,000(186,2);-0,008(6,9);-0,150(0,9)28.0), 2.440 (0.6), 2.425 (16.0), 2.333 (0.7), 2.328 (1.0), 2.324 (0.7), 1.045 (0.3), 1.030 (0.3); 0.745 (1.0); 0.733 (3.0); 0.728 (3.9); 0.715 (3.9); 0.711P, 699 (1.2); 0.494 (1.2) ; 0,483 (3.7); 0,478 (3.4); 0,473 (3.2); 0,468 (3.3); 0,456 (1.0); 0.146 (0.9) 0.008 (5.7); 0.000 (186.2) - 0.008 (6.9) - 0.150 (0.9)
Beispiel 1-1-182: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,960(2,6);9,944(2,7);8,345(3,4);8,339(3,5);7,657(1,8);7,650(1,7);7,636(2,3);7,629(2,2Example 1-1-182: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.960 (2.6); 9.944 (2.7); 8.345 (3.4); 8.339 (3.5 ); 7,657 (1.8); 7,650 (1.7); 7,636 (2.3); 7,629 (2.2
);7,593(2,3);7,574(2,6);7,495(4,4);7,474(3,5);7,301(2,3);7,283(3,2);7,266(2,0);5,457(9,0);4,609(15,4);3,589(2,1);3,571(6,9);3,554(7,0);3,536 (2,2);3,319(55,0);2,672(0,3);2,525(0,8);2,507(40,6);2,503(56,3);2,498(42,0);2,422(16,0);2,329(0,4);1,178(6,9);1,160(14,1);1, 143(6,8); 1 ,074(); 7,593 (2.3); 7,574 (2.6); 7,495 (4.4); 7,474 (3.5); 7,301 (2.3); 7.283 (3.2); 7,266 (2.0) 5.457 (9.0); 4.609 (15.4); 3.589 (2.1); 3.571 (6.9); 3.554 (7.0); 3.536 (2.2); 3.319 (55.0); 2,672 (0.3); 2,525 (0.8); 2,507 (40.6); 2.503 (56.3); 2,498 (42.0); 2,422 (16.0); 2,329 (0.4); 1,178 (6.9); 1.160 (14.1); 1, 143 (6.8); 1, 074 (
0,5);1,057(0,9);1,039(0,5);0,008(2,2);0,000(64,5);-0,008(2,5) 0.5); 1,057 (0.9); 1,039 (0.5) 0.008 (2.2) 0.000 (64.5) - 0.008 (2.5)
Beispiel 1-1-183: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,685(2,3);9,668(2,3);8,319(2,9);8,160(2,2);8,140(2,3);7,610(1,2);7,605(1,3);7,584(1,8 );7,487(2,9);7,466(2,1);7,114(1,5);7,094(2,2);7,077(1,5);5,752(9,4);5,634(6,6);3,854(0,5);3,843(0,5);3,823(0,6);3,776(1 ,0);3,742(16,0);3,691 (1 ,4);3,684(1 ,4);3,667(1 ,0);3,638(1 ,3);3,617(1 ,4);3,555(0,6);3,505(0,9);3,496(1,0);3,483(0,9);3,447(0,9);3,431 (0,6);3,418(0,6);3,391 (0,5);3,3 81 (0,6);3,316(241 ,8);2,670(2,5);2,501 (428,9);2,497(383,0);2,402(0,3);2,327(2,6); 1 ,235(0,8); 1 , 176(0,5); 1 , 158(0,5);1 , 138(0,4); 1,121 (0,6); 1 ,0 45(0,4);1,030(0,4);0,000(2,9) Beispiel 1-1-184: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,597(6,2);9,580(6,5);8,313(0,3);8,179(6,1);8,174(6,1);7,873(3,8);7.863(3,9);7,852(10, 9);7,438(3,7);7.433(3,7);7,420(3,6);7,415(3,7);5,4(X)(14,1);4,338(0,7);4,329(0,7);3,785(0,3);3,775(0,5);3,757(0,4);3,317(132,8);2^Example 1-1-183: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.685 (2.3), 9.668 (2.3), 8.319 (2.9), 8.160 (2.2 8,140 (2,3); 7,610 (1,2); 7,605 (1,3); 7,584 (1,8); 7,487 (2,9); 7,466 (2,1); 7,114 (1,5) ; 7,094 (2.2); 7,077 (1.5); 5,752 (9.4); 5,634 (6.6); 3,854 (0.5); 3,843 (0.5); 3,823 (0.6); 3.776 (1, 0); 3.742 (16.0); 3.691 (1, 4); 3.684 (1, 4); 3.667 (1, 0); 3.638 (1, 3); 3.617 (1, 4); 3.555 (0.6), 3.505 (0.9), 3.496 (1.0), 3.483 (0.9), 3.447 (0.9), 3.431 (0.6), 3.418 (0.6), 3.391 ( 0.5), 3.3 (0.6), 3.316 (241, 8), 2.670 (2.5), 2.501 (428.9), 2.497 (383.0), 2.402 (0.3); 2,327 (2.6); 1, 235 (0.8); 1, 176 (0.5); 1, 158 (0.5); 1, 138 (0.4); 1,121 (0.6); 1, 0 45 (0.4), 1.030 (0.4), 0.000 (2.9) Example 1-1-184: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.597 (6.2), 9.580 (6.5), 8.313 (0.3), 8.179 (6.1 8,174 (6.1); 7,873 (3.8); 7,863 (3.9); 7,852 (10,9); 7,438 (3,7); 7,433 (3,7); 7,420 (3,6) ; 7,415 (3.7); 5.4 (X) (14.1) 4,338 (0.7); 4,329 (0.7); 3,785 (0.3); 3,775 (0.5); 3,757 ( 0.4); 3,317 (132.8); 2 ^
782(1,1);2,773{1,7);2,764(2,4);2,755(2,5);2,746(1,7);2,737(1,1);2,727(0,4);2,676(0,7);2,671 (1,0);2,667(0,7);2,525(2,1);2,507(121,6);2,502(1 71,9);2,498(130,4);2,334(0J);2,329(1,0);2,325(0,8);1,046(16,0);1 ,031(15,8);0,749(1,4);0,736(4,3);0,731(5,6);0,719(5,5);0,714(4,4);0,702(1,782 (1.1); 2.773 {1.7); 2,764 (2.4); 2,755 (2.5); 2,746 (1.7); 2,737 (1.1); 2,727 (0.4); 2,676 (0.7); 2.671 (1.0); 2.667 (0.7); 2.525 (2.1); 2.507 (121.6); 2.502 (1 71.9); 2.498 (130.4); 2.334 (0J); 2.329 (1.0); 2.325 (0.8); 1.046 (16.0); 1, 031 (15.8); 0.749 (1.4); 0.736 (4.3); 0.731 ( 5.6) 0.719 (5.5) 0.714 (4.4) 0.702 (1,
7);0,505(1,7);0,494(5,2);0,488(5,0);0,484(4,7);0,478(4,7);0,466(1,4);0,146(0,8);0,008(5,9);0,000(183,1);-0,008(6,6);-0,150(0,9)7); 0,505 (1.7); 0.494 (5.2) 0.488 (5.0) 0.484 (4.7) 0.478 (4.7) 0.466 (1.4) 0.146 (0.8 ); 0,008 (5.9); 0,000 (183.1) - 0.008 (6.6) - 0.150 (0.9)
Beispiel 1-1-185: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,988(2,6);9,972(2,9);8,644(3,9);8,637(3,9);8,352(0,4);8,346(0,4);8,126(2,2);8,120(2,2Example 1-1-185: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.988 (2.6), 9.972 (2.9), 8.644 (3.9), 8.637 (3.9 ); 8,352 (0.4); 8.346 (0.4) 8.126 (2.2); 8,120 (2.2
);8,105(2,6);8,098(2,5);7,826(4,9j;7,805(4,7);7,790{1,5);7,787(1,5);7,469(1 ,6);7,453(6,4);7,433(3,4);7,417(0,3);7,074(0,4);7,052(0,4);4,532( 16,0):3,943(2,7):3,369(29,1);3,315(105,3);2,674(0,6);2,670(0,9);2,523(1,9);2,509(49,6);2,505(105,7):2,501(149,8):2,497(114,7);2,332(0,6);2 ,328(0,9);2,324(0,7);0,146(0,8);0,008(5,7);0,000(173.0);-0,008(6,8);-0,150(0,8) 8,105 (2,6); 8,098 (2.5); 7,826 (4,9j; 7,805 (4,7); 7,790 {1,5); 7,787 (1.5); 7,469 (1, 6); 7.453 (6.4), 7.433 (3.4), 7.417 (0.3), 7.074 (0.4), 7.052 (0.4), 4.532 (16.0): 3.943 (2.7): 3.369 (2.501: 2.505 (105.7) (29.1) 3.315 (105.3); 2,674 (0.6); 2,670 (0.9); 2,523 (1.9); 2,509 (49.6) 149.8): 2.497 (114.7); 2.332 (0.6); 2.328 (0.9); 2.324 (0.7); 0.146 (0.8); 0.008 (5.7); 0.000 (173.0) - 0.008 (6.8) - 0.150 (0.8)
Beispiel 1-1-186: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,948(2.8);9,932(2,9);8,492(3,7);8,486(3,7);7,874(1,9);7,868(1,9);7,853(2.2);7.846(2,1 );7,763(1.2);7,760(1,3);7,744(1 ,6);7,741 (2,7);7,738(1 ,8); 7, 722(1 ,7);7,719(1 ,7);7,545(2,8);7,523(2,4);7,506(4,5);7,485(4,0);7,364(1 ,6);7,361 ( 1 ,6);7,345(2,9);7,329(1 ,5);7,326(1 ,5);6,021 (0,6);6,003(2,0);5,985(2,0);5,967(0,6);5,755(5,0);4,605(0,5);4,564(9.4);4,561 (9,4);4,520(0,5);3,5Example 1-1-186: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.948 (2.8), 9.932 (2.9), 8.492 (3.7), 8.486 (3.7); 7,874 (1.9), 7.868 (1.9), 7.853 (2.2), 7.846 (2.1), 7.763 (1.2), 7.760 (1.3), 7.744 (1, 6), 7.741 (2.7 7,738 (1, 8); 7, 722 (1, 7); 7,719 (1, 7); 7,545 (2,8); 7,523 (2,4); 7,506 (4,5); 7,485 (4,0); 7,364 (1, 6) 7.361 (1, 6), 7.355 (2.9), 7.329 (1, 5), 7.326 (1, 5), 6.021 (0.6), 6.003 (2.0), 5.985 (2.0); 5.967 (0.6); 5.755 (5.0); 4.605 (0.5); 4.564 (9.4); 4.561 (9.4); 4.520 (0.5); 3.5
75(2,3):3,558(7,9);3,540(8,0);3,523(2,4);3,320(46,3);2,526(0,6);2,522(0,8):2,513(15,5);2,508(33,7);2,504(47,6):2,499(35,0);2,495(16,4);1^ 14(9,4);1,896(9,4);1,172(7,8);1,155(16,0);1,137(7,6):1,047(2,1):1,031(2,0);0,008{1,9);0,000(64,9):-0,009(2,1) 75 (2,3): 3,558 (7.9); 3,540 (8.0); 3,523 (2.4); 3,320 (46.3); 2,526 (0.6); 2,522 (0.8): 2.513 (15.5); 2.508 (33.7); 2.504 (47.6): 2.499 (35.0); 2.495 (16.4); 1 ^ 14 (9.4); 1.896 (9.4); 1,172 (7.8); 1,155 (16.0); 1.137 (7.6) 1.047 (2.1) 1.031 (2.0) 0.008 {1.9); 0.000 (64.9): - 0.009 (2.1)
Beispiel 1-1-187: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,517(5.3);9,710(2,8);9,693(2,9);8,379(3.6);8,373(3,7);8,313(0,5);8,283(0,5);8,278(0,Example 1-1-187: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.517 (5.3), 9.710 (2.8), 9.693 (2.9), 8.379 (3.6), 8.373 ( 3.7); 8,313 (0.5); 8,283 (0.5); 8,278 (0,
5):7,693(0,7);7,685(7 ;7,668(2,6);7,663(9,5):7,655(3,3);7,623(0,7);7,600(0,8):7,520(2,5);7,501(7,4);7,481(3,7);7,378{8,3):7,361 (2,9):7,356 (7,4);7,320(2,5);7,301(3,5);7,284(2,1);5,753(0,5);5,560(8,8);3,317(156,7);2,675(0,8):2,671(1,2);2,666(0,9);2,524(2,6);2,510(62,3);2,506(136 ,6);2,501(197,0);2,497(155,9);2,457(16,0);2,333(0,8);2,328(1,1);2,324(0,9);2,095(0,5);1,241(0,4);1,233(0,5);0,146(1,0);0,008(7,6);0,000(235): 7.693 (0.7); 7.685 (7.768 (2.6); 7.663 (9.5): 7.655 (3.3); 7.623 (0.7); 7.600 (0.8): 7.520 (2.5); 7.551 (7.4); 7.481 (3.7); 7.378 {8.3): 7.361 (2.9): 7.356 (7.4); 7.320 (2.5); 7.301 ( 3.5); 7,284 (2.1); 5,753 (0.5); 5,560 (8.8); 3,317 (156.7); 2,675 (0.8) 2,671 (1.2); 2,666 (0 , 9), 2.524 (2.6), 2.510 (62.3), 2.506 (136, 6), 2.501 (197.0), 2.497 (155.9), 2.457 (16.0), 2.333 (0, 8); 2,328 (1.1); 2,324 (0.9); 2,095 (0.5); 1,241 (0.4); 1,233 (0.5); 0.146 (1.0) 0.008 (7.6 ); 0.000 (23
3,7):-0,008(10,3);-0,150(1,0) 3.7) - 0.008 (10.3) - 0.150 (1.0)
Beispiel 1-1-188: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,920(2,7);9,904(2,7);8,847(3,1);8,843(3, 1);8,005(1 ,4);8,001 (1 ,4);7,985(1 ,8);7,980(1 ,9 );7,881 (3,8);7,860(2,8);7,839(1 ,0);7.836(1,1);7,817(2,5);7,814(1 ,8);7.798(1 ,8);7,795(1 ,8);7,737(3,1);7,715(1 ,9);7,390(1 ,4);7,387(1 ,4);7,372( 2,5);7,355(1,4);7,352(1,3);5,755(2,7);5,361(7,9);4,584(16,0):3,586(2,2);3,568(7,6);3,551(7,7);3,533(2,3);3,320(62,3);2,673(0,4);2,526(0,7);2 ,521(1,0);2,513(19,8);2,508(43,2);2,504(61,3);2,499(45,0);2,495(21,0);2,331(0,4);1,176(7,3);1,158(15,3);1,141(7,2) Example 1-1-188: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.920 (2.7), 9.904 (2.7), 8.847 (3.1), 8.843 (3, 1 8,005 (1,4), 8,001 (1,4), 7,985 (1,8), 7,980 (1,9), 7,881 (3,8), 7,860 (2,8), 7,839 (1, 0) 7.836 (1.1); 7.817 (2.5); 7.898 (1, 8); 7,798 (1, 8); 7,795 (1, 8); 7,737 (3,1); 7,715 (1,9); 7.398 (1, 4), 7.387 (1, 4), 7.372 (2.5), 7.355 (1.4), 7.352 (1.3), 5.755 (2.7), 5.361 (7.9), 4.584 (16.0) 3.586 (2.2); 3,568 (7.6); 3,551 (7.7); 3,533 (2.3); 3,320 (62.3); 2,673 (0.4); 2,526 ( 0.7); 2. 521 (1.0); 2.513 (19.8); 2.508 (43.2); 2.504 (61.3); 2.499 (45.0); 2.495 (21.0); 2.331 (0.4); 1,176 (7.3); 1,158 (15.3); 1,141 (7.2)
Beispiel 1-1-189: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.550(2,0);9,535(2,0);9,533(2,0);8,317(1,9);8,312(2,0);7,766(0,8);7,764(0,9);7,745(1,0Example 1-1-189: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,550 (2.0), 9.535 (2.0), 9.533 (2.0), 8.317 (1.9 ); 8,312 (2.0); 7,766 (0.8); 7.764 (0.9); 7,745 (1.0
);7,743(1,0);7,685(1,1);7,678(1,1);7,664(1,3);7,657(1,3);7,482(2,5);7,461(2,1);7,391(1 ,6);7,374(1,7);7,370(1,6);7 ); 7,743 (1.0); 7,685 (1.1); 7,678 (1.1); 7.664 (1.3); 7,657 (1.3); 7,482 (2.5); 7,461 (2.1) 7.391 (1,6); 7,374 (1,7); 7,370 (1,6); 7
16,0);3,320(13,3);2,513(5,7);2,509(12,5);2,504(17,9);2,500(13,5);2,496(6,5);1,990(0,6);1 , 177(0,3) 16.0) 3,320 (13.3); 2,513 (5.7); 2,509 (12.5); 2,504 (17.9); 2,500 (13.5); 2,496 (6.5); 1,990 (0 , 6); 1, 177 (0.3)
Beispiel 1-1-190: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,013(2,0);8,005(2,0);7,849(9,5);7,733(1,4);7,715(4,0);7,711(3,7);7,701(4,1);7,683(3,9Example 1-1-190: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.013 (2.0), 8.005 (2.0), 7.849 (9.5), 7.733 (1.4 ); 7,715 (4.0); 7.711 (3.7); 7,701 (4.1); 7,683 (3.9
);7,661(1,6):7,185(2,6);7,168(2.4);5,755(0,5);5,428(12,7);3,319(90.2);2,730(16,0);2.710(1,6);2,702(r ); 7,661 (1.6) 7,185 (2.6); 7,168 (2.4); 5,755 (0.5); 5,428 (12.7); 3,319 (90.2); 2,730 (16.0); 2710 (1 , 6); 2.702 (r
72(0,7);2667(0,5);2,525(1,2);2,520(1,8);2,512(32,4);2,507(70,4);2,503(99,6);2,498(73,0);2,494(34,1);2,334(0,4);2,330(0,6);^  72 (0.7); 2,667 (0.5); 2,525 (1.2); 2,520 (1.8); 2,512 (32.4); 2.507 (70.4); 2.503 (99.6); 2,498 (73.0) 2,494 (34.1); 2,334 (0.4); 2,330 (0.6); ^
6(1 ,3);1 ,031 (1 ,3);0,707(1 ,1 );0,695(3,4);0,690(4,4);0,677(4,3);0,672(3,5);0,660(1 ,4);0,496(1 ,7);0,486(4,7);0,480(4,3);0,475(4,0);0,470(4,2);0, 6 (1, 3); 1, 031 (1, 3); 0.707 (1, 1); 0.695 (3.4); 0.690 (4.4); 0.677 (4.3); 0.672 (3.5) 0.606 (1, 4), 0.496 (1, 7), 0.486 (4.7), 0.480 (4.3), 0.475 (4.0), 0.470 (4.2), 0,
458(1,3);0,146(0,5);0,008(3,4);0,000(116,6);-0,008(3,5):-0,149(0,5) 458 (1.3); 0.146 (0.5) 0.008 (3.4) 0.000 (116.6) - 0.008 (3.5) - 0.149 (0.5)
Beispiel 1-1-191 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,748(2,0);9,731(2,0);8,334(2,5);8,330(2,7);8,304(0,9);8,290(1,8);8,275(0,9);7,616(1,1 );7,610(1,2);7,595(1,6);7,589(1,7):7,493(3,0);7,472(2,2):7,407(1,7);7,388(2,1):7,226(1 ,5):7,208(2,4);7,191(1,3);5,754(0,5);5,517(6,7);3,318^ 23,8);3, 164(2,4);3, 148(4,3):3, 133(2,5);2,507(26,4);2,503(37,7);2,429(11 ,6); 1 ,800(0,5); 1 ,783(1 ,0); 1 , 766(1 ,2); 1 ,750(1 ,0); 1 ,733(0,5);0,920(16, 0);0,904(15,6);0,825(0,5);0,808(0,5);0,008(1,3);0,000(37,6);-0,002(23,1) Example 1-1-191: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.748 (2.0), 9.731 (2.0), 8.344 (2.5), 8.330 (2.7 8.304 (0.9), 8.290 (1.8), 8.275 (0.9), 7.616 (1.1), 7.610 (1.2), 7.595 (1.6), 7.589 (1.7) : 7.493 (3.0); 7.472 (2.2): 7.407 (1.7); 7.388 (2.1): 7.226 (1.5): 7.208 (2.4); 7.191 (1.3); 5.754 (0.5); 5.517 (6.7); 3.318 ^ 23.8); 3, 164 (2.4); 3, 148 (4.3): 3, 133 (2.5); 2.507 ( 26.4); 2.503 (37.7); 2.429 (11, 6); 1, 800 (0.5); 1, 783 (1, 0); 1, 766 (1, 2); 1, 750 (1, 0); 1, 733 (0.5), 0.920 (16, 0), 0.904 (15.6), 0.825 (0.5), 0.808 (0.5), 0.008 (1.3), 0.000 (37.6) ; -0.002 (23.1)
Beispiel 1-1-192: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,907(2,8);9,891(2,9);8,466(4.2);8,461(4,4);8,136(4,4);8,130(4,4);7,836(1,0);7,833(1,1Example 1-1-192: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.907 (2.8), 9.891 (2.9), 8.466 (4.2), 8.461 (4.4); 8,136 (4.4); 8,130 (4.4); 7,836 (1.0); 7,833 (1.1
);7,815(2,6);7,812(2,0);7,796(1,9);7,793(1,9);7,734(3,3);7,713(2,1);7,382(1 ,4);7,379(1 ,5);7,363(2,7);7,347(1,4);7,344(1 ,4);5,754(1,0);5,248( 10,1);4,577(16,0);3,585(2,2);3,568(7,2);3,550(7,4);3,533(2,3);3,317(69,8);2,677(0,4);2,672(0,5);2,667(0,4);2,525(1,1);2,512(28,1);2,507(59, 6);2,503(83,7);2,498(62,4);2.494(30,1);2.334(0,4);2,330(0,5);2,325(0,4);1 ,313(0,5);1,^ 7.815 (2.6), 7.812 (2.0), 7.796 (1.9), 7.793 (1.9), 7.734 (3.3), 7.713 (2.1), 7.382 (1, 4) 7.379 (1, 5); 7,363 (2,7); 7,347 (1,4); 7,344 (1, 4); 5,754 (1,0); 5,248 (10,1); 4,577 (16,0); 3,585 (2.2); 3,568 (7.2); 3,550 (7.4); 3,533 (2.3); 3,317 (69.8); 2,677 (0.4); 2,672 (0.5); 2,667 (0.4); 2.525 (1.1); 2.512 (28.1); 2.507 (59.6); 2.503 (83.7); 2.498 (62.4); 2.494 (30.1); 2.334 ( 0.4); 2.330 (0.5); 2.325 (0.4); 1, 313 (0.5); 1, ^
0,000(96,0);-0,008(3,6);-0, 150(0,4)  0,000 (96,0); - 0,008 (3,6); - 0, 150 (0,4)
Beispiel 1-1-193: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,956(2,5);9,940(2,6);8.345(3,3);8,338(3.4);8,313(0.4);7,657(1,7);7,650(1,7);7,636(2,2Example 1-1-193: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.956 (2.5), 9.940 (2.6), 8.345 (3.3), 8.338 (3.4); 8,313 (0.4); 7,657 (1.7); 7,650 (1.7); 7,636 (2.2
);7,629(2,2);7,596(2,3);7,577(2,5);7,494(4,5);7,473(3,5);7,303(2,3);7,285(3,2);7,267(2,1);5,753(0,7);5,456(9,1);4,570(15,75;3,369(32,1);3,31 6(178,3);2,675(0,7);2,671(1,0);2,666(0,7);2,524(1,9);2,510(52,7);2,506(115,6);2,501(166,4);2,497(126,6);2,493(61,9);2,421(16,0);2,333(0,7); 7,629 (2.2); 7,596 (2.3); 7,577 (2.5); 7,494 (4.5); 7,473 (3.5); 7,303 (2.3); 7,285 (3.2) 7.267 (2.1); 5.753 (0.7); 5.456 (9.1); 4.570 (15.75; 3.369 (32.1); 3.31 6 (178.3); 2.675 (0.7 ); 2,671 (1.0); 2,666 (0.7); 2,524 (1.9); 2,510 (52.7); 2.506 (115.6); 2.501 (166.4); 2.497 (126.6) ; 2,493 (61.9); 2,421 (16.0); 2,333 (0.7
);2,328(1,0);2,324(0,7);1,235(0,4);0,146(1,0);0,008(6,4);0,000(216,0);-0,008(8,1);-0,150(1,0) ); 2,328 (1.0); 2,324 (0.7); 1,235 (0.4); 0.146 (1.0) 0.008 (6.4) 0.000 (216.0) - 0.008 (8.1 ) - 0.150 (1.0)
Beispiel 1-1-194: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,525(1 ,9);9,509(1 ,9);8,336(2,2);8,331 (2,5);7,683(1 ,8);7,664(2,1 );7,652(1 ,3);7,646(1 ,3Example 1-1-194: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.525 (1, 9), 9.509 (1, 9), 8.366 (2.2), 8.31 L (2.5 7,683 (1, 8); 7,664 (2,1); 7,652 (1, 3); 7,646 (1, 3);
);7,631(1,4);7,625(1,6);7,465(2,5);7,444(2,0);7,345(1,3);7,326(1,8);7,309(1 ,2);5,599(6,1);4,336(0,5);3,857(0,5);3,830(0,5);3,805(0,9);3,789 1 ,3);3,773(1,7);3,745(14,6);3,720(1,0);3,712(1 ,0);3,701 (1 ,1);3,694(1 ,1 );3,685(1 ,0);3,669(1 ,0);3,651 (1 ,0);3,625(0,8);3,573(0,6);3,552(0,5);3, 535(0,6);3,505(0,7);3,490(0,8);3,472(0,7);3,440(0,6);3,369(0,4);3,322(10,9);3,170(1,0);3,095(0,3);3,089(0,4);3,077(0,3);2,541^7.631 (1.4), 7.625 (1.6), 7.465 (2.5), 7.444 (2.0), 7.345 (1.3), 7.366 (1.8), 7.309 (1, 2) 5,599 (6.1), 4.336 (0.5), 3.857 (0.5), 3.830 (0.5), 3.805 (0.9), 3.789 1, 3), 3.773 (1.7), 3.745 (14.6); 3.720 (1.0); 3.712 (1, 0); 3.701 (1, 1); 3.694 (1, 1); 3.685 (1, 0); 3.699 (1, 0); 3.651 ( 1, 0), 3.625 (0.8), 3.573 (0.6), 3.552 (0.5), 3.355 (0.6), 3.505 (0.7), 3.490 (0.8), 3.472 (0.7); 3,440 (0.6); 3,369 (0.4); 3,322 (10.9); 3,170 (1.0); 3,095 (0.3); 3,089 (0.4); 3,077 ( 0.3); 2.541 ^
,0);2,499(38,7);2,443(14,8);1 ,234(0,9);1,201(0,8);1,183(1,5);1,165(0,8);1,123(0,5);1,105(0,4);1,046(15,8);1,031(16,0);0,000(0,4), 0), 2,499 (38,7), 2,443 (14.8), 1, 234 (0.9), 1.201 (0.8), 1.183 (1.5), 1.165 (0.8), 1.123 ( 0.5); 1,105 (0.4); 1,046 (15.8); 1.031 (16.0); 0,000 (0.4)
Beispiel 1-1-195: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,668(4,5);9,651(4,6);8,589(6,6);8,584(6,9);8,563(6,5);8,557(6,7);8,014(3,8);8,005(3.9Example 1-1-195: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.688 (4.5), 9.651 (4.6), 8.589 (6.6), 8.584 (6.9 ); 8,563 (6.5); 8,557 (6.7); 8,014 (3.8); 8,005 (3.9
);7,912(3,7);7,906(6,4);7,901 (3,8);7,747(3,3);7,725(5,3);7,669(2,6);7,667(2,7);7,648(4,1);7,629(1,8);7,626(1,9);7,332(2,2);7,329(2,4);7,312( 4,3);7,297(2,0);7,294(2,1);5,292(16,0);3,317(111,2);2,802(0,4);2,792(1,2);2,783(1,9);2,774(2,7);2,765(2,8);2,756(1,9);2,747(1,3);2,737(0,4); 2,676(0,6);2,672(0,8);2,667(0,6);2,525(1,7);2,511(46,6);2,507(99,3);2,503(140,2);2,498(106,6);2,334(0,6);2,329(0,8);2,325(0,6);ί, 743(0,7);7.912 (3.7), 7.906 (6.4), 7.901 (3.8), 7.747 (3.3), 7.725 (5.3), 7.669 (2.6), 7.667 (2.7) 7.648 (4.1); 7.629 (1.8); 7.626 (1.9); 7.332 (2.2); 7.329 (2.4); 7.312 (4.3); 7.297 (2.0); 7,294 (2.1); 5,292 (16.0); 3,317 (111.2); 2,802 (0.4); 2,792 (1.2); 2,783 (1.9); 2,774 (2.7); 2,765 (2.8); 2,756 (1.9); 2,747 (1.3); 2,737 (0.4); 2,676 (0.6); 2,672 (0.8); 2,667 (0.6); 2,525 (1.7); 2,511 (46.6); 2.507 (99.3); 2.503 (140.2); 2,498 (106.6); 2.334 (0.6); 2.329 (0.8); 2.325 (0.6); ί, 743 (0.7);
1 ,234(0,3); 1 ,046(1 ,2);1 ,031 (1 ,2);0,743(1 ,6);0,731 (4,7);0,726(6,2);0,713(6, 1):0,708(4,9);0,696(2,0);0,503(2,0);0,492(5,7);0,486(5,5);0,482(5, 2);0,477(5,3);0,465(1,6);0,146(0,7);0,008(4,7);0,000(153,9);-0,008(6,6);-0,150(0,7) 1, 234 (0.3); 1, 046 (1, 2); 1, 031 (1, 2); 0.743 (1, 6); 0.731 (4.7); 0.726 (6.2); 0.713 (6, 1): 0.708 (4, 9), 0.696 (2.0), 0.503 (2.0), 0.492 (5.7), 0.486 (5.5), 0.482 (5, 2), 0.477 (5.3), 0.465 (1.6 ); 0.146 (0.7) 0.008 (4.7) 0.000 (153.9) - 0.008 (6.6) - 0.150 (0.7)
Beispiel 1-1-196: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,750(6.1);9,734(6,2);8,328(5,8);8,322(6,1);8,096(4,4);8.087(4.6);7,682(4,7);7,675(4,0Example 1-1-196: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.750 (6.1); 9.734 (6.2); 8.328 (5.8); 8.322 (6.1); 8,096 (4.4); 8,087 (4.6); 7,682 (4.7); 7,675 (4.0
);7,667(3,3);7,661(5,7);7,654(4,2);7,481(7,4);7,460(6,1);7,377(4,2);7,360(4,3);7,356(4,4);7,339(3,7);5,349(16,0);4,340(0,9);4,330(0,9);3,318 (55,5);2,829(0,4);2,820(1,2);2,811(2,0);2,802(2,8);2,793(2,9);2,784(2,0);2,775(1,3);2,765(0,5);2,672(0,5);2,668(0,4);2,525(1,0);2,508(57,5); 2,503(82,6);2,499(65,2);2,334(0,4);2,330(0,5);2,326(0,4);1,046(5,7);1,031(5,6);0,766(1,6);0,753(5,0);0,748(6,7);0,735(6,4);0,731 (5,4);0,718 (2,1);0,519(2,0);0,508(6,1);0,503(6,0);0,498(5,8);0,493(5,7);0,481(1,7);0,008(2,0);0,000(62,2);-0,008(2,8) Beispiel 1-1-197: 1H-NMR(400,0 MHz, de-DMSO): δ= 9.645(4,0);9,639(4,1);9,636(4,1);8,401 (6,4);8,396(6,5);8,314(0,4);8,222(0,4);8.039(4,9 );8,030(4,9);8,000(2,1);7,995(2,2);7,977(2,6);7,971 (3,9);7,965(2.4);7,948(2,2);7,942(2,0);7,773(3,6);7,767(3,5);7,753(4,^ ); 7,667 (3.3); 7,661 (5.7); 7,654 (4.2); 7,481 (7.4); 7,460 (6.1); 7,377 (4.2); 7,360 (4.3) 7.356 (4.4), 7.339 (3.7), 5.349 (16.0), 4.340 (0.9), 4.330 (0.9), 3.318 (55.5), 2.829 (0.4); 2,820 (1.2); 2,811 (2.0); 2,802 (2.8); 2,793 (2.9); 2,784 (2.0); 2,775 (1.3); 2,765 (0.5); 2,672 (0.5); 2,668 (0.4); 2,525 (1.0); 2,508 (57.5); 2,503 (82.6); 2,499 (65.2); 2,334 (0.4); 2,330 (0.5); 2,326 (0.4); 1,046 (5.7); 1,031 (5.6); 0.766 (1.6); 0.753 (5.0); 0.748 (6.7); 0.735 (6.4); 0.731 (5.4); 0.718 (2.1); 0.519 (2.0); 0.508 ( (0.008 -; 6.1); 0.503 (6.0) 0.498 (5.8) 0.493 (5.7) 0.481 (1.7) 0.008 (2.0) 0.000 (62.2) 2,8) Example 1-1-197: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,645 (4.0), 9.639 (4.1), 9.636 (4.1), 8.401 (6.4 8,396 (6.5); 8,314 (0.4); 8,222 (0.4); 8,039 (4.9); 8,030 (4.9); 8,000 (2,1); 7,995 (2,2) 7.977 (2.6), 7.971 (3.9), 7.965 (2.4), 7.948 (2.2), 7.942 (2.0), 7.773 (3.6), 7.767 (3.5), 7.753 ( 4 ^
7,8);7,483(6,9);5,754(16,0);5,347(0,4);5,302(15,5);4,340(0,8):4,330(0,8)^  7.8); 7,483 (6.9); 5,754 (16.0); 5,347 (0.4); 5,302 (15.5); 4,340 (0.8) 4,330 (0.8) ^
);2,788(3,3);2,779(3,3);2,771 (2,4);2,761 (1 ,6);2,752(0,6);2,671 (1 ,2);2,524(2,2);2,506(142,6);2,502(192,5);2,498(147,0);2,333(1,0);2,329(1 ,3) ;1 ,235(0,5);1 ,045(5,7);1 ,030(5,5);0,765(2,0);0,752(6,1);0,747(8,1 );0,735(7,9);0,730(6,8);0,718(2.5);0,696(0,4);0,680(0,4);0  2,788 (3,3), 2,779 (3,3), 2,771 (2,4), 2,761 (1,6), 2,752 (0,6), 2,671 (1,2), 2,524 (2,2) 2.506 (142.6); 2.502 (192.5); 2.498 (147.0); 2.333 (1.0); 2.329 (1, 3); 1, 235 (0.5); 1, 045 (5 , 7); 1, 030 (5.5); 0.765 (2.0); 0.752 (6.1); 0.747 (8.1); 0.735 (7.9); 0.730 (6.8); 0.718 ( 2.5) 0.696 (0.4) 0.680 (0.4) 0
,4);0,521 (2,4);0,510(7,3);0,504(7,6);0,500(7,2);0,495(7,2);0,482(2,2):0,146(0,6);0,008(5,4):0,000(139,5);-0,008(7,3);-0,149(0,6) , 4), 0.521 (2.4), 0.510 (7.3), 0.504 (7.6), 0.500 (7.2), 0.495 (7.2), 0.482 (2.2): 0.146 (0, 6) 0.008 (5.4) 0.000 (139.5) - 0.008 (7.3) - 0.149 (0.6)
Beispiel 1-1-198: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,515(1 ,8);9,499(1 ,9);8,465(2,4);8,459(2,5);7,843(1 ,3);7,837(1 ,3);7,822(1 ,5);7,817(1 ,5 );7,659(0,8);7,656(0,8);7,637(1 ,8):7,619{1 ,2):7,616(1 , 1 );7.495(2,7);7,474(4.0);7,451 (1 ,7);7,326(1 ,0):7,323(1 ,0);7.307(1 ,9);7,291 (1 ,0);7,288{ 0,9);6,024(0,4);6,(X)7(1 ,3);5,989(1 ,4);5,971 (0,5);5,754(0,9);3,726(16,0);3,333(50,5);2,509(25,0);2,504(32,6);2,500 Example 1-1-198: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.515 (1, 8), 9.499 (1, 9), 8.465 (2.4), 8.459 (2.5 7.843 (1, 3), 7.837 (1, 3), 7.822 (1.5), 7.817 (1.5), 7.659 (0.8), 7.656 (0.8), 7.637 (1, 8) : 7.619 {1, 2): 7.616 (1, 1); 7,495 (2.7); 7,474 (4.0); 7,451 (1, 7); 7,326 (1, 0): 7,323 (1, 0); 7,307 ( 1, 9), 7.291 (1, 0), 7.288 {0.9), 6.024 (0.4), 6, (X) 7 (1, 3), 5.989 (1, 4), 5.971 (0.5 ); 5,754 (0.9); 3,726 (16.0); 3.333 (50.5); 2,509 (25.0); 2,504 (32.6); 2,500
3); 1 ,881 (6,2); 1 ,047(1 , 1 ); 1 ,032(1 , 1 );0,000(29,6);-0,006(3,6) 3); 1, 881 (6,2); 1, 047 (1, 1); 1, 032 (1, 1), 0.000 (29.6), - 0.006 (3.6)
Beispiel 1-1-199: 1H-NMR(400,0 MHz, d6-DMSO): δ= 9,484(2,0);9,467(2.1);8.459(3,1);8,456(3,0);8, 113(3,3);8,109(3,0);7,741 (0.5);7,719(1 ,7Example 1-1-199: 1 H NMR (400.0 MHz, d 6 -DMSO): δ = 9.484 (2.0); 9.467 (2.1); 8.459 (3.1); 8.456 (3.0) ; 8, 113 (3,3); 8,109 (3,0); 7,741 (0.5); 7,719 (1, 7
);7,699(3,3);7,676(0,8);7,347(0,9);7,330(1 ,8);7,326(1 ,6);7,313(0,9);7,310(0,8);5,239(7,9);3,740(16,0);3,322(25,2);3,320(24,0);2,505 047(1 , 0);1 , 032(1 , 0);0,000(33,2) 7.699 (3.3); 7.676 (0.8); 7.347 (0.9); 7.330 (1, 8); 7.326 (1, 6); 7.313 (0.9); 7.310 (0.8) 3.329 (7.9), 3.740 (16.0), 3.322 (25.2), 3.320 (24.0), 2.505 047 (1, 0), 1, 032 (1, 0), 0.000 (33, 2)
Beispiel 1-1-200: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,677(5,4);9,661 (5,7);8,835(6,3);8,313(0,9);8,014(4.6);8,005(4,7);7,969(2,6);7,965(2,7Example 1-1-200: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.677 (5.4), 9.661 (5.7), 8.835 (6.3), 8.313 (0.9 ); 8,014 (4.6); 8,005 (4.7); 7,969 (2.6); 7,965 (2.7
);7,945(4,1 );7,869(7,9);7,849(5,2);7,737(3,8);7,715(6,4);7,667(3,^ 7.945 (4.1), 7.689 (7.9), 7.849 (5.2), 7.737 (3.8), 7.715 (6.4), 7.667 (3, ^
2,8);7,319(4,9):7,304(2,5):7,301 (2,6);5,398(16,0);3,568(2,1);3,351 (0,5);3,347(0,4);3,316(216,3):3,098(0,4);2,802(0,6);2,792(1 ,5):2,783(2,3); 2,774(3,4);2,765(3,2);2,756(2,3);2,747(1 ,7);2,737(0,6);2,675(1 ,7);2,671 (2,3);2.667(1 ,5);2,581 (0,4);2,524(5,3);2,520(7,6);2,511 (121 ,3);2,506 (259,2);2,502(364, 1 );2,497(270,6):2,493(128,5);2,333(1.4);2,329(2,2);2,324(1,5); 1.233(0,5); 1 , 197(0.4); 1 , 177(0,8); 1 , 160(0,5); 1,045(0.8); 1 ,0 30(0,8);0,744(2,0);0,732(5,8);0,727(7,3);0,714(7,4);0,709(5,7)  2.8), 7.329 (4.9): 7.304 (2.5): 7.301 (2.6), 5.398 (16.0), 3.568 (2.1), 3.351 (0.5), 3.347 (0 , 4); 3,316 (216,3): 3,098 (0.4); 2,802 (0,6); 2,792 (1,5): 2,783 (2,3); 2,774 (3,4); 2,765 (3,2); 2,756 (2,3); 2,747 (1, 7); 2,737 (0,6); 2,675 (1, 7); 2,671 (2,3); 2,667 (1, 5); 2.581 (0.4), 2.524 (5.3), 2.520 (7.6), 2.511 (121, 3), 2.506 (259.2), 2.502 (364, 1), 2.497 ( 270.6) 2.493 (128.5); 2,333 (1.4); 2,329 (2.2); 2,324 (1.5); 1,233 (0.5); 1, 197 (0.4); 1, 177 (0.8); 1, 160 (0.5); 1,045 (0.8); 1, 0 30 (0.8), 0.744 (2.0), 0.732 (5.8), 0.727 (7.3), 0.714 (7.4), 0.709 (5.7)
0,456(1 ,9);0,146(1 ,2):0,008(8,8);0,000(302,8);-0,009(10,5);-0,149(1 ,3)  0.456 (1, 9), 0.146 (1, 2): 0.008 (8.8), 0.000 (302.8), -0.009 (10.5), -0.149 (1, 3)
Beispiel 1-1-201 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,664(4,6);9,647(4,7);8,458(6,9);8,453(7, 1);8, 120(7,3);8,115(7,2);8,000(3,8);7,991 (3,9Example 1-1-201: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.664 (4.6), 9.647 (4.7), 8.458 (6.9), 8.453 (7, 1 8, 120 (7.3), 8.115 (7.2), 8,000 (3.8), 7.991 (3.9
):7,742(3,2);7,721 (5,3);7,668(2,7);7,665(2,9);7,650(3,2);7,647(4,2);7,644(2,0);7,628(2,0);7,625(1 ,9);7,332(2,3);7,329(2,5);7,312(4,1 );7,297( 2,1);7,294(2,1);5,755(3,9);5,286(16,0);3,319(67,2);2,799(0,4);2,789(1 ,2);2,780(1 ,9);2,772(2,8);2,762(2,9);2,753(1 ,9);2,744(1 ,3);2,735(0,5);2 ,677(0,5);2,672(0,7);2,668(0,5);2,526(1,5);2,521 (2,1 );2,512(36,4);2,508(78,1);2,503(1 10,1);2,499(81 ,4);2,494(38,3);2,335(0,5);2,330(0,6);2, 326(0,5);1 ,232(0,4);1 ,047(1 ,9);1 ,031 (1 ,9);0, 743(1 ,7);0,731 (4,7);0,726(6.2);0,714(6,2);0,708(4,8);0.697(2,0);0,499(2.1 );0,488(5,5);0,482(5,3)): 7.742 (3.2), 7.721 (5.3), 7.668 (2.7), 7.665 (2.9), 7.650 (3.2), 7.647 (4.2), 7.644 (2.0) 7.628 (2.0), 7.625 (1, 9), 7.332 (2.3), 7.329 (2.5), 7.312 (4.1), 7.297 (2.1), 7.294 (2.1); 5.755 (3.9), 5.286 (16.0), 3.319 (67.2), 2.799 (0.4), 2.789 (1,2), 2,780 (1, 9), 2,772 (2,8), 2,762 (2.9); 2.753 (1, 9); 2.744 (1, 3); 2.735 (0.5); 2.677 (0.5); 2.672 (0.7); 2.668 (0.5); 2.526 (1.5), 2.521 (2.1), 2.512 (36.4), 2.508 (78.1), 2.503 (1 10.1), 2.499 (81, 4), 2.494 (38.3); 2.335 (0.5); 2.330 (0.6); 2, 326 (0.5); 1, 232 (0.4); 1, 047 (1, 9); 1, 031 (1, 9); 0, 743 (1, 7), 0.731 (4.7), 0.726 (6.2), 0.714 (6.2), 0.708 (4.8), 0.697 (2.0), 0.499 (2.1), 0.488 (5 , 5); 0.482 (5.3)
;0,478(4,9);0,473(5,1);0,460(1 ,6);0,146(0,4);0,008(2,7);0,000(90,7);-0,008(2,9);-0,150(0,4) 0.478 (4.9); 0.473 (5.1); 0.460 (1, 6); 0.146 (0.4); 0.008 (2.7); 0.000 (90.7); -0.008 (2.9); ; -0.150 (0.4)
Beispiel 1-1-202: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,706(5,5);9,689(5,7);8,486(6,6);8,480(7.1);8,314(0,3);8,062(4,8);8,053(5,0);7,866(3,5Example 1-1-202: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.706 (5.5), 9.689 (5.7), 8.486 (6.6), 8.480 (7.1); 8.314 (0.3) 8.062 (4.8); 8,053 (5.0); 7,866 (3.5
);7,861 (3,6);7,845(3,9);7,839(3,9);7,613(0,5);7,590(8,2);7,579(11 ,6);7,498(7,4);7,477(6,7);7,315(2, 1);7,306(2,2);7,302(2,7);7,299(2,9);7,294 (2,7);7,290(2,7);7,286(2,6);7,277(1 ,9);6,027(1 ,1);6,009(3,7);5,991 (3,8);5,974(1 ,1);5,754(13,5);4,339(0,7);4,329(0,7);3,318(90,2);2,791 (0,4); 2,781 (1 ,4);2,772(2,1);2,763(3,0);2,754(3,1 );2,745(2,2);2,736(1 ,4);2,726(0,5);2,672(0,9);2,507(108,0);2,503(150,9);2,499(124,6);2,330(1 ,0); 1 ,927(16,0);1 ,909(16,0);1 ,234(0,3);1 ,046(4,6);1 ,031 {4,6);0,731 (1 ,6);0,715(7,3);0,702(6,8);0,697(6,3);0,685(2,0);0,487(2,2);0,476(6,8);0,4707.861 (3.6), 7.845 (3.9), 7.839 (3.9), 7.613 (0.5), 7.590 (8.2), 7.559 (11, 6), 7.498 (7.4) 7.477 (6.7), 7.315 (2, 1), 7.306 (2.2), 7.302 (2.7), 7.299 (2.9), 7.294 (2.7), 7.290 (2.7); 7,286 (2,6), 7,277 (1, 9), 6,027 (1, 1), 6,009 (3,7), 5,991 (3,8), 5,974 (1,1), 5,754 (13,5), 4,339 (0.7), 4.329 (0.7), 3.318 (90.2), 2.791 (0.4); 2,781 (1,4); 2,772 (2,1); 2,763 (3,0); 2,754 (3,1); 2,745 (2,2); 2,736 (1, 4); 2,726 (0,5); 2,672 (0.9); 2.507 (108.0); 2.503 (150.9); 2.499 (124.6); 2.330 (1.0); 1, 927 (16,0); 1, 909 (16,0); 1, 234 (0,3); 1, 046 (4,6); 1, 031 {4,6); 0,731 (1, 6 ); 0,715 (7.3); 0.702 (6.8); 0.697 (6.3) 0.685 (2.0) 0.487 (2.2) 0.476 (6.8); 0,470
(6,9);0,466(6,8);0,461 (6,6);0,449(1 ,8);0,145(0,4);0,000(90,8);-0,149(0,4) (6.9); 0.466 (6.8); 0.461 (6.6); 0.449 (1, 8); 0.145 (0.4); 0.000 (90.8); - 0.149 (0.4)
Beispiel 1-1-203: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,701 (2,6);9,685(2,6);8,121 (2,4);8,112(2,5);7,669(6,6);7,472(2,2);7,453(2.6);7,252(2.4Example 1-1-203: 1H-NMR (400.0 MHz, de-DMSO): δ = 9.701 (2.6); 9,685 (2.6); 8,121 (2.4); 8,112 (2.5 ); 7.669 (6.6); 7,472 (2.2); 7,453 (2.6); 7,252 (2.4
);7,234(3,3);7,216(2,0);5,754(0,5);5,554(9,0);3,318(58,5);2,796(0,8);2,787(1 ,2);2,778(1 ,8);2,768(1 ,8);2,760(1 ,2);2,751 (0,8);2,676(0,4);2,672 (0,6);2,667(0,4);2,633(16,0);2,525(1 ,3);2,511 (30,5);2,507(63,4);2,502(87,8);2,498(65,2);2,494(31 ,3);2,334(0,4);2,329(0,5);2,325(0,4);1 ,046( 0,5);1 ,031 (0,5);0,752(1 ,0);0,739(3,0);0,734(3,9);0,722(3,9);0,717(3,1);0,705(1 ,3);0,507(1 ,3);0,496(3,6);0,490(3,5);0,486(3,2);0,481 (3,3);0,47.234 (3.3), 7.216 (2.0), 5.754 (0.5), 5.554 (9.0), 3.318 (58.5), 2.796 (0.8), 2.787 (1, 2) 2,778 (1,8), 2,768 (1,8), 2,760 (1,2), 2,751 (0,8), 2,676 (0,4), 2,672 (0,6), 2,667 (0,4); 2.653 (16.0), 2.525 (1.3), 2.511 (30.5), 2.507 (63.4), 2.502 (87.8), 2.498 (65.2), 2.494 (31, 3), 2.344 (0.4); 2.329 (0.5); 2.325 (0.4); 1, 046 (0.5); 1, 031 (0.5); 0.752 (1.0); 0.739 (3.0 0.734 (3.9); 0.722 (3.9); 0.717 (3.1); 0.705 (1, 3); 0.507 (1, 3); 0.496 (3.6); 0.490 (3.5) 0.486 (3.2); 0.481 (3.3); 0.4
68(1 ,0);0,008(2,1);0,000(63.2);-0,009(2.2) 68 (1, 0), 0.008 (2.1), 0.000 (63.2), - 0.009 (2.2)
Beispiel 1-1-204: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,741 (2,1);9,724(2,1);8,349(2,2);8,343(2,3);8, 168(1 ,6);8,158(1 ,7);7,650(1 ,1);7,644(1 ,1Example 1-1-204: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.741 (2.1); 9.724 (2.1); 8.349 (2.2); 8.343 (2.3 8, 168 (1, 6), 8.158 (1, 7), 7.650 (1, 1), 7.644 (1, 1
);7,630(1,4);7,623(1 ,4);7,612(1 ,9);7,592(2,1 );7,465(2,8);7,444(2,3);7,331 (1 ,4);7,312(1 ,8);7,295(1 ,3);5,636(5,8);3,724(0,5);3,316(54,7)i7.630 (1.4); 7.623 (1, 4); 7.612 (1, 9); 7.592 (2.1); 7.465 (2.8); 7.444 (2.3); 7.331 (1, 4) 7,312 (1, 8), 7,295 (1,3), 5,636 (5,8), 3,724 (0,5), 3,316 (54,7) i
(0,5);2,789(0,7);2,780(1 ,1);2,771 (1 ,1 );2,762(0,8);2,753(0,5);2,671 (0,5);2,666(0,4);2,505(62,4);2,501 (88,0);2,497(69,4);2,454(16,0);2,328(0,(0.5); 2.789 (0.7); 2.780 (1, 1); 2.771 (1, 1); 2.762 (0.8); 2.753 (0.5); 2.671 (0.5); 2.666 ( 0.40), 2.505 (62.4), 2.501 (88.0), 2.497 (69.4), 2.454 (16.0), 2.328 (0),
5):1 ,234(0,3);1 ,045(0,6):1 ,030(0,6);0,746(0,6);0,733(1 ,9);0,728(2,5);0J16(2,45;0J11 (2,0);0,699(0,8);0,494(0,8);0,483(2,4):0,477(2,3);0,4735): 1, 234 (0.3); 1, 045 (0.6): 1, 030 (0.6); 0.746 (0.6); 0.733 (1, 9); 0.728 (2.5) ; 0J16 (2.45; 0J11 (2.0); 0.699 (0.8); 0.494 (0.8); 0.483 (2.4): 0.477 (2.3); 0.473
(2,2);0,468(2,2);0,455(0,7);0,007(1 ,8);0,000(50,8);-0,008(2,3) (2.2); 0.468 (2.2); 0.455 (0.7); 0.007 (1, 8); 0.000 (50.8); - 0.008 (2.3)
Beispiel 1-1-205: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,782(4,0);9,765(4,2);9,573(0,4);9,556(0.5);8,421 (5,0);7,817(1 ,9);7,796(4,9);7,775(3,6 );7,770(4,4);7,746(0,5);7,504(4,5);7,484(4,2);7,457(0,6);7,435(0,4);7,415(0,6);7,366(1 ,2);7,352(2, 1 );7,336(2,0);7,332(2,0);7,316(1 ,1 );7,292( 0,3);7,275(0,4);5,753(1 ,5);5,368(0,4);5,351 (1 ,4);5,281 (10,9);4,567(16,0);4,551 (2,5);3,906(2,9);3,371 (28,8);3,360(4,8);3,320(87,7);2,671 (0,7 );2,502(119,7);2,454(0,5);2,328(0,7); 1.234(1 ,3):0,146(0,4);0,000(69,8);-0, 150(0,4) Example 1-1-205: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.782 (4.0), 9.765 (4.2), 9.583 (0.4), 9.556 (0.5); 8.421 (5.0), 7.817 (1.9), 7.796 (4.9), 7.775 (3.6), 7.770 (4.4), 7.746 (0.5), 7.504 (4.5), 7.484 (4.2); 7.457 (0.6); 7.435 (0.4); 7.415 (0.6); 7.366 (1, 2); 7.352 (2, 1); 7.336 (2.0); 7.322 ( 7.416 (1, 1), 7.292 (0.3), 7.275 (0.4), 5.753 (1.5), 5.368 (0.4), 5.351 (1, 4), 5.281 (10 , 9), 4.567 (16.0), 4.551 (2.5), 3.906 (2.9), 3.371 (28.8), 3.360 (4.8), 3.320 (87.7), 2.671 (0, 7), 2.502 (119.7), 2.454 (0.5), 2.328 (0.7); 1,234 (1, 3): 0.146 (0.4); 0.000 (69.8); - 0, 150 (0.4)
Beispiel 1-1-206: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,490(1 ,5);9.474(1 ,5);7,676(3,8);7,544(1 ,3);7,525(1 ,5);7,268(1 ,4);7,250(2,0);7,232(1 ,2Example 1-1-206: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.490 (1.5), 9.474 (1.5), 7.676 (3.8), 7.544 (1.3 7.525 (1, 5); 7.268 (1, 4); 7.250 (2.0); 7.232 (1, 2);
);5,505(5,6);3,744(16,0);3,320(29,1);2,638(9,6);2,526(0,4);2,512(9,4);2,508(20,5);2,504(29,3);2,499(22,0);2,495(10,6);1 ,047(0,8); 1 ,031 (0,8) ;0,008(1 ,1);0,000(35,4);-0,008(1 ,2) ); 5,505 (5.6); 3,744 (16.0); 3,320 (29.1); 2,638 (9.6); 2,526 (0.4); 2,512 (9.4); 2,508 (20.5) 2.504 (29.3), 2.499 (22.0), 2.495 (10.6), 1.047 (0.8); 1, 031 (0.8), 0.008 (1, 1), 0.000 (35.4), - 0.008 (1, 2)
Beispiel 1-1-207: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,857(2.6);9,840(2,7);8,354(3,0);8,309(2,3);8,003(0,9);7.997(1 ,0);7,982(1 ,8);7.976(1 ,8 );7,962(1,1 );7,956(1 ,0);7,904(1 ,1 );7,885(2,4);7,867(1 ,6);7,864(1 ,7);7,790(3,0);7,769(2,0);7,418(1 ,4);7,401 (2,6);7,385(1 ,3);7,382(1 ,4);7,184( 1 ,9);7,177(1 ,9);7,163(1 ,8);7, 156(1 ,8);5,263(8,9);4,811 (16,0);3,683(0,5):3,572(2,2);3,383(102,9);2,516(14,9);2,512(20,3);2,507(16,1 );0,000( 2,5) Example 1-1-207: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.857 (2.6), 9.840 (2.7), 8.354 (3.0), 8.309 (2.3); 7.997 (1, 8), 7.962 (1.1), 7.956 (1, 0), 7.904 (1, 1), 7.855 (2.4); 7.867 (1, 6); 7.864 (1, 7); 7.790 (3.0); 7.769 (2.0); 7.418 (1, 4); 7.401 (2.6); 7.385 ( 1, 3), 7,382 (1,4), 7,184 (1, 9), 7,177 (1, 9), 7,163 (1, 8), 7, 156 (1, 8), 5,263 (8,9), 4,811 (16.0); 3.683 (0.5): 3.572 (2.2); 3.383 (102.9); 2.516 (14.9); 2.512 (20.3); 2.507 (16.1); 0.000 ( 2.5)
Beispiel 1-1-208: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,215(3,1 );9,716(1 ,6);9,700(1 ,7);7,706(3,8);7,571 (0.4);7,563(3,6);7,540(4,5);7,517(1 ,Example 1-1-208: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.215 (3.1), 9.716 (1.6), 9.700 (1, 7), 7.706 (3.8 7.571 (0.4), 7.563 (3.6), 7.540 (4.5), 7.517 (1,
7);7,302(1 ,3);7,285(2,0);7,267(1 , 1);6,934(0,4);6,925(3,8);6,903(3,7);5,756(5,6);5,626(5,0);3,741 (16,0);3,720(0,8);3,322(19, 1);2.659(9,1 );2,5 08(28, 1 );2,503(37,6);2,499(29, 1 j;0,000(1 ,3) 7); 7,302 (1,3), 7,285 (2,0), 7,267 (1,1), 6,934 (0,4), 6,925 (3,8), 6,903 (3,7), 5,756 (5,6 5.626 (5.0), 3.741 (16.0), 3.720 (0.8), 3.322 (19, 1), 2.659 (9.1), 2.5.08 (28, 1), 2.503 (37 , 6); 2,499 (29, 1 j, 0,000 (1, 3)
Beispiel 1-1-209: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,841 (2.1);9.825(2,1);8,310(1.0);7,939(0,7);7,937(0,7);7,918(1 ,8);7,899(1.5);7,897(1 ,4 );7,868(2,5);7,847(1 ,3);7,787(4,6);7,421 (1 ,0);7,418(1 ,0);7,403(1 ,9);7,387(1 ,0);7,383(0,9);5,389(7,4);4,809(0,4);4,795(12,6);3,570(1 ,7);3,355 (126,7);2,653(0,3);2,567(16,0);2,553(0,6);2,511 (21 ,0);2,507(28,0);2,502(21 ,8);0,000(5,1) Example 1-1-209: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.841 (2.1), 9.825 (2.1), 8.310 (1.0), 7.939 (0.7), 7.937 ( 7.918 (1, 8); 7.899 (1.5); 7.897 (1, 4); 7.868 (2.5); 7.847 (1.3); 7.787 (4.6); 7.421 (1.0) 7.418 (1, 0), 7.403 (1, 9), 7.387 (1, 0), 7.383 (0.9), 5.389 (7.4), 4.809 (0.4), 4.795 (12.6) 3.570 (1, 7), 3.355 (126.7), 2.653 (0.3), 2.567 (16.0), 2.553 (0.6), 2.511 (21, 0), 2.507 (28.0); 2,502 (21, 8); 0,000 (5,1)
Beispiel 1-1-210: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,634(0,6);9,617(0,6);8,520(0,6);8,500(0,6);7,681 (1 ,3);7,473(0,5);7,454(0,7);7,394(7,6 );7,373(0,5);7,340(0Λ);7,227(0,5);7,210(0,7);7,192(0,4);5,754(16,0);5,579(1 ,7);5, 128(0,4);3,750(1 ,4);3,377(1 ,3);3,318(10,6);2,632(3,2);2,50 7(18,7);2,503(25,3);2,498(19,5); 1 ,475(1,8);1 ,458(1 ,8);1 ,347(0,5);1 ,330(0,5);0,008(0,9);0,000(19,2) Example 1-1-210: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.634 (0.6), 9.617 (0.6), 8.520 (0.6), 8.500 (0.6 7.681 (1, 3), 7.473 (0.5), 7.454 (0.7), 7.394 (7.6) 7,373 (0.5); 7,340 (0Λ); 7,227 (0.5); 7,210 (0.7); 7,192 (0.4); 5,754 (16,0); 5,579 (1, 7); 5 , 128 (0.4), 3.750 (1, 4), 3.377 (1, 3), 3.318 (10.6), 2.632 (3.2), 2.50 7 (18.7), 2.503 (25, 3); 2,498 (19.5); 1, 475 (1.8); 1, 458 (1, 8); 1, 347 (0.5); 1, 330 (0.5); 0.008 (0.9); 0.000 (19.2)
Beispiel 1-1-211 : 1H-NMR(400,0 MHz, de-DMSO): δ= 10,375(4,7);9,717(2,6);9,700(2,6);8,313(0,6);8,266(0,6);8,261 (0,6);7,709(6,7);7,647(4, 7);7,628(5,3);7,587(0,7);7,560(2,4);7,541 (2,7);7,352(3,3);7,332(5,4);7,320(3,0);7,313(4,6);7,303(3,5);7,292(0,9);7.285(2,2) Example 1-1-211: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.375 (4.7), 9.717 (2.6), 9.700 (2.6), 8.313 (0.6 8,266 (0.6); 8,261 (0.6); 7,709 (6,7); 7,647 (4,7); 7,628 (5,3); 7,587 (0,7); 7,560 (2,4) 7.351 (2.7), 7.352 (3.3), 7.332 (5.4), 7.320 (3.0), 7.313 (4.6), 7.303 (3.5), 7.292 (0.9); 7,285 (2.2)
(0,5);7,0M(1 ,7);7,036(3,0);7,017(1 ,3);5,754{0,5);5,632(8,4);3,316(81 ,4);2,663(16,0);2,524(3,9);2,510(83,3);2,506(171 ,9);2,501 (236,9);2,49 7(178,9);2,493(88,2);2,333(1.0);2,328(1.4);2.324(1 ,0);1 ,474(0,5);0,008(0,6);0,000(16,8);-0,009(0,6) (0.5); 7.0M (1, 7); 7.036 (3.0); 7.017 (1, 3); 5.754 {0.5); 5.632 (8.4); 3.316 (81, 4); 2.653 (16.0), 2.524 (3.9), 2.510 (83.3), 2.506 (171, 9), 2.501 (236.9), 2.49 7 (178.9), 2.493 (88.2 2,333 (1.0); 2,328 (1.4); 2,324 (1, 0); 1, 474 (0.5); 0.008 (0.6); 0.000 (16.8); - 0.009 (0.6)
Beispiel 1-1-212: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,666(5,5);9,584(2,7);9,567(2,8);7.722(6,9);7.571 (2,4);7.552(2,8);7.384(0,4):7,368(1 ,0 );7,362(0,8);7,347(1 ,9);7,326(1 ,4);7,309(2,9);7,291 (3,3);7.273(2,2);7,220(0,7);7,211 (3.9);7.203(0^ Example 1-1-212: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.666 (5.5), 9.584 (2.7), 9.567 (2.8), 7.722 (6.9 7,571 (2.4); 7,552 (2.8); 7,384 (0.4): 7,368 (1, 0); 7,362 (0.8); 7,347 (1, 9); 7,326 (1, 4) 7.309 (2.9), 7.291 (3.3), 7.273 (2.2), 7.220 (0.7), 7.211 (3.9), 7.203 (0 ^
0,5);5,756(13,6);5,628(8,6);3,321 (19,1);3,178(0,5);3,165(0,5);2,664(16,0);2,526(1 ,1);2,513(21 ,3);2,^ 0.5), 5.656 (13.6), 5.628 (8.6), 3.321 (19.1), 3.178 (0.5), 3.165 (0.5), 2.664 (16.0), 2.526 (1 , 1); 2,513 (21, 3); 2, ^
(21 ,7);2,330(0,3);0,008(0,7);0,000(16,8);-0,008(0,7) (21, 7), 2.330 (0.3), 0.008 (0.7), 0.000 (16.8), - 0.008 (0.7)
Beispiel 1-1-213: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,744(0,8):9,727(0,8);8,115(1 ,3);7,666(1 ,8);7,444(0,7);7,427(0,8);7,209(0.6);7,191 (1 ,0Example 1-1-213: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.744 (0.8): 9.727 (0.8), 8.115 (1.3), 7.666 (1.8 7.444 (0.7), 7.427 (0.8), 7.209 (0.6), 7.191 (1.0
);7,173(0,5);5,560(2,6);3,319(24, 1):2,628(4,5):2,505(35,7):2,502(47,1);2,498(37,4);1 ,389(16,0);1 ,355(1 ,4); 1 ,330(0,5);1 ,308(0,6):1 ,297(1 ,0 1 ,272(0,4); 1 ,255(2, 1 ): 1 ,244(0,5); 1 ,228(1 ,5); 1 ,223(1 , 1 ); 1 , 187(1 ,5); 1 , 169(0,7) 7.173 (0.5); 5.560 (2.6); 3.319 (24, 1): 2.628 (4.5): 2.555 (35.7): 2.502 (47.1); 2.498 (37.4) ; 1, 389 (16,0); 1, 355 (1, 4); 1, 330 (0.5); 1, 308 (0.6): 1, 297 (1, 0 1, 272 (0.4); 1, 255 (2, 1): 1, 244 (0.5 1, 228 (1, 5); 1, 223 (1, 1); 1, 187 (1, 5); 1, 169 (0.7)
Beispiel 1-1-214: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,524(1 ,7);9,508(1 ,7);8,111 (2,1);7,770(0,6);7,764(0,6);7,750(1 ,1 );7,744(1 ,2);7,730(0,6Example 1-1-214: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.524 (1, 7), 9.508 (1, 7), 8.111 (2.1), 7.770 (0.6 7.764 (0.6), 7.750 (1, 1), 7.744 (1.2), 7.730 (0.6
);7,723(0,6);7,490(1 ,5);7,471 (1 ,8);7,258(1 ,4);7,240(2,2);7,223(1 ,2);7,163(1 ,3);7,157(1 ,4);7,142(1 ,2);7,135(1 ,3);5,451 (5,6);3,744(16,0);3,321 (14,1);2,508(21 ,0);2,503(29,4);2,499(23,7);2,433(10,8);1.233(0,5);0,000(0,4) 7,723 (0,6); 7,490 (1, 5); 7,471 (1, 8); 7,258 (1, 4); 7,240 (2,2); 7,223 (1, 2); 7,163 (1, 3) 7.157 (1, 4), 7.142 (1, 2), 7.135 (1, 3), 5.451 (5.6), 3.744 (16.0), 3.321 (14.1), 2.508 (21, 0); 2,503 (29.4); 2,499 (23.7); 2,433 (10.8); 1,233 (0.5); 0,000 (0.4)
Beispiel 1-1-215: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,486(1 ,8);9,469(1 ,8);8,591 (3,3);8,390(3,3);7,710(0.8);7,689(1 ,8);7,670(1 ,3);7,577(2,2Example 1-1-215: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.486 (1.8), 9.469 (1.8), 8.591 (3.3), 8.390 (3.3 7.710 (0.8), 7.689 (1, 8), 7.670 (1, 3), 7.577 (2.2
);7,555(1,5);7,335(1 ,0);7,317(1 ,8);7,300(0,9);5,334(6,9);3,721 (16,0);3,320(12,5);2,506(27,8);2,502(36,4);2,498(27,8);2,450(12,8);1 , 045(2,1) ; 1 ,030(2,1) 7.555 (1.5); 7.335 (1, 0); 7.317 (1, 8); 7,300 (0.9); 5,334 (6,9); 3,721 (16,0); 3,320 (12,5) 2.506 (27.8), 2.502 (36.4), 2.498 (27.8), 2.450 (12.8), 1.045 (2.1); 1, 030 (2,1)
Beispiel 1-1-216: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,584(5,4);9,687(2,7);9,670(2,8);8,280(3,8);7,713(8, 1);7,698(2,2);7,585(2,7);7,582(2,Example 1-1-216: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.584 (5.4), 9.687 (2.7), 9.670 (2.8), 8.280 (3.8 7.713 (8, 1); 7.698 (2.2); 7.585 (2.7); 7.582 (2,
6);7,566(3,2);7,561 (3,5);7,540(1 ,5);7,385(2,4);7,366(2,0);7,330(2,5);7,312(3,4);7,295(2,2);5,756(0,8);5,631 (8,5);3,322(33,4);2,662(16,0);2,5 26(1 ,4);2,513(24,9);2,508(50,4);2,504(68,7);2,499(51 ,8);2,495(25,7);2,331 (0,4);0,000(2,9) 6), 7.566 (3.2), 7.561 (3.5), 7.540 (1.5), 7.385 (2.4), 7.366 (2.0), 7.330 (2.5), 7.312 (3.4 7.295 (2.2), 5.756 (0.8), 5.631 (8.5), 3.322 (33.4), 2.662 (16.0), 2.5-26 (1, 4), 2.513 (24 , 9); 2,508 (50,4); 2,504 (68,7); 2,499 (51,8); 2,495 (25,7); 2,331 (0,4); 0,000 (2,9)
Beispiel 1-1-217: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,663(2.5);9,647(2,6);8,605(4,0);8,602(4.1);8,390(4,0);7,979(2,1 );7,970(2,1);7,623(3,8Example 1-1-217: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.663 (2.5); 9.647 (2.6); 8.605 (4.0); 8.602 (4.1); 8.390 ( 4.0), 7.979 (2.1), 7.970 (2.1), 7.623 (3.8
);7,614(5,4);7,612(5,2);7,601 (0,4);7,324(1 ,1 );7,^ 7.614 (5.4); 7.612 (5.2); 7.601 (0.4); 7.324 (1, 1); 7, ^
27,1);2,778(0,7);2,769(1 ,0);2,760(1 ,5);2,751 (1 ,5);2,742(1 ,0);2,733(0,7);2,508(30,2);2,503(40,7);2,499(30,8);2,450(16,0);1 ,046(0,4);1 ,0 27.1), 2.778 (0.7), 2.769 (1, 0), 2.760 (1.5), 2.751 (1.5), 2.742 (1.0), 2.733 (0.7), 2.508 (30 , 2), 2.503 (40.7), 2.499 (30.8), 2.450 (16.0), 1, 046 (0.4), 1, 0
4);0,731 (0,9);0,718(2,6);0,713(3,3);0,701 (3,3);0,696(2,6);0,684(1 ,0);0,473(1 ,1);0,462(3,1);0,457(3,0);0,452(2,8);0,447(2,8);0,435(0,9);^4), 0.731 (0.9), 0.718 (2.6), 0.713 (3.3), 0.701 (3.3), 0.696 (2.6), 0.684 (1, 0), 0.473 (1, 1 ); 0,462 (3.1); 0,457 (3.0); 0.452 (2.8) 0.447 (2.8) 0.435 (0.9); ^
(0,7) (0.7)
Beispiel 1-1-218: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,231 (8,3);9,689(5,2);9,672(5,5);8,665(8,1 );8,662(8,5);8.413(8,0);8,411 (8,0);7,740(0,Example 1-1-218: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.231 (8.3); 9.689 (5.2); 9.672 (5.5); 8.665 (8.1 8,662 (8.5), 8,413 (8.0), 8,411 (8,0), 7,740 (0,
6);7,738(0,6);7,718(4,4);7,715(5,2);7,709(5,9);7,704(10,9);7,702(10,9);7,689(0,9);7,623(8,1);7,604(9,0);7,392(2,3);7,385(2,2);7,378(2,^ 76(3,0);7,370(2,7);7,368(2,6);7,362(2,2);7,354(2,2);7,335i5,7);7,316(8,6);7,295(5,8);7,037(2,9);7,019(5, 1);7,000(2,3);5,465(16,0);4,343(0,5) ;4,333(0,5);3,322(74,7);2,676(0,5);2,672(0,7);2,667(0,5);2,525(2,4);2,512(42,1);2,507(85,0);2,503(116,0):2,498(87,3);2,494(43,2);2,462(32 4);2,334(0,4);2,329(0,7);2,325(0,5);1 ,232(0.3);1 ,046(4,0);1 ,031 (3,9);0.000(2,2) 6); 7,738 (0.6); 7,718 (4.4); 7,715 (5.2); 7.709 (5.9) 7.704 (10.9); 7,702 (10.9); 7.689 (0.9 7.623 (8.1), 7.604 (9.0), 7.392 (2.3), 7.385 (2.2), 7.378 (2, 76 (3.0), 7.370 (2.7), 7.368) (2.6); 7,362 (2.2); 7,354 (2.2); 7,335i5,7); 7,316 (8.6); 7,295 (5.8); 7,037 (2.9); 7,019 (5 , 1), 7,000 (2,3), 5,465 (16,0), 4,343 (0.5), 4,333 (0.5), 3,322 (74,7), 2,676 (0,5), 2,672 (0, 7); 2,667 (0.5); 2,525 (2.4); 2,512 (42.1); 2.507 (85.0); 2.503 (116.0) 2.498 (87.3); 2.494 (43.2 2.462 (32 4); 2.344 (0.4); 2.329 (0.7); 2.325 (0.5); 1, 232 (0.3); 1, 046 (4.0); 1, 031 (3 0.000 (2.2), 9)
Beispiel 1-1-219: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,441 (5.2);9,721 (2,8);9,705(2,8);8.380(3,6);8,374(3.6);7,681 (2.2);7,674(5,0);7,661 (5, 7);7,651 (4,9);7,644(1 ,6);7,638(3,7);7,630(0,4);7,504(6,1);7,488(3,2);7,484(4,6);7,310(2,5);7,293(3,4);7,275(2,1);7,192(0 Example 1-1-219: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.441 (5.2), 9.721 (2.8), 9.705 (2.8), 8.380 (3.6); 8.674 (3.6), 7.681 (2.2), 7.674 (5.0), 7.661 (5.7), 7.651 (4.9), 7.644 (1.6), 7.638 (3.7), 7.630 (0.4 ); 7.504 (6.1); 7,488 (3.2); 7,484 (4.6); 7,310 (2.5); 7,293 (3.4); 7,275 (2.1); 7,192 (0
(1 ,3);7,161 (6,6);7, 145(1 ,2);7,139(3,4);7,130{0,3);5,755(1 ,3);5,562(8,7);3,321 (41 ,0);2,677(0,3);2,672(0,4);2,668(0,3);2,512(26,1);2,507(52,7) ;2,503(72,2);2,498(54,7);2,494(27,4);2,457(16,0);2,330(0,4);2,325(0,3); 1 ,046(0,7); 1 ,031 (0,7);0,000(1 ,4)  (1, 3); 7,161 (6,6); 7,145 (1,2); 7,139 (3,4); 7,130 {0,3); 5,755 (1,3); 5,562 (8,7); 3.321 (41.0), 2.677 (0.3), 2.672 (0.4), 2.668 (0.3), 2.512 (26.1), 2.507 (52.7), 2.503 (72.2), 2.498 (54.7) 2,494 (27.4); 2,457 (16.0); 2,330 (0.4); 2,325 (0.3); 1, 046 (0.7); 1, 031 (0.7); 0.000 (1, 4)
Beispiel 1-1-220: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,927(1 ,9);9,911 (2,0);7,632(1 ,7);7,613(1 ,9);7,551 (4,4);7,302(1 ,6);7,284(2,3);7,266(1 ,4Example 1-1-220: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.927 (1, 9); 9.911 (2.0); 7.632 (1, 7); 7.613 (1, 9 7.551 (4.4); 7.302 (1, 6); 7.284 (2.3); 7.266 (1, 4);
);5,518(6,5);4,560(10,8);3,932(0,4);3,370(20,4);3,350(0,8);3,322(2,6);3,292(0,7);2,623(11 ,7);2,575(16,0);2,508(24,5);2,504(32,3);2,499(24, 7):2.456(0,5);0,000(12,5) ); 5,518 (6.5); 4,560 (10.8); 3,932 (0.4); 3,370 (20.4); 3,350 (0.8); 3,322 (2.6); 3,292 (0.7) 2.623 (11, 7), 2.575 (16.0), 2.508 (24.5), 2.504 (32.3), 2.499 (24, 7): 2.456 (0.5), 0.000 (12.5)
Beispiel 1-1-221 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,885(1 , 9);9,869(1 ,9);7,874(0,5);7,871 (0,5);7,852(1 ,5);7,849(1 ,4):7,835(1 ,7);7,832(1 , 8 );7,823(2,2);7,804(0,7);7,776(4,5);7,381 (0,9);7,377(0,9);7,364(1 ,7);7,360(1 ,6);7,348(0,9);7,343(0,8);5,366(6,4);4,531 (10,9);3,364(22,2);3,32 1 (16,1);2,563(16,0);2,526(0,8);2,513(15,0);2,508(30,5);2,504(41 ,7);2,499(31 ,1);2,495(15,2);0,008(0,7);0,000(17,7);-0,008(0,6) Example 1-1-221: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.885 (1.9), 9.689 (1.9), 7.874 (0.5), 7.871 (0.5 7,852 (1, 5); 7,849 (1, 4): 7,835 (1, 7); 7,832 (1, 8); 7,823 (2,2); 7,804 (0,7); 7,776 (4,5) 7.381 (0.9), 7.377 (0.9), 7.364 (1, 7), 7.360 (1, 6), 7.348 (0.9), 7.343 (0.8), 5.366 (6.4); 4.531 (10.9), 3.364 (22.2), 3.321 (16.1), 2.563 (16.0), 2.526 (0.8), 2.513 (15.0), 2.508 (30.5 2.504 (41, 7), 2.499 (31, 1), 2.495 (15.2), 0.008 (0.7), 0.000 (17.7), - 0.008 (0.6)
Beispiel 1-1-222: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,732(2,6);9,716(2,6);8,203(2,5);8,193(2,5);8, 123(2,9);8,119(3,0);7,763(0,9);7,757(0,9 );7,742(1,7);7,736(1 ,7);7,722(1 ,0);7,716(0,9);7,419(2,2);7,400(2,7);7,242(2,4);7,224(3,3);7,206(2,0);^ Example 1-1-222: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.732 (2.6), 9.716 (2.6), 8.203 (2.5), 8.193 (2.5 8, 123 (2.9), 8.119 (3.0), 7.763 (0.9), 7.757 (0.9), 7.742 (1.7), 7.736 (1, 7), 7.722 (1, 0); 7,716 (0.9); 7,419 (2.2); 7,400 (2.7); 7,242 (2.4); 7,224 (3.3); 7,206 (2.0); ^
1 ,9);5.490(7,9);3,318(45,7);2,801 (0,8);2, 792(1 ,2);2, 783(1 ,8);2,774(1 ,8);2,765(1 ,2);2,756(0,9);2,676(0,6);2,671 (0,7);2,667(0,5);2,524(2,4);2, 511 (43,3);2.507(87,6);2,502(120,2);2,498(91 ,2);2.493(45,8);2.441 (16,0);2,333(0,5);2,329(0,7);2,325(0,5);0,747(1 ,1);0,734  1, 9), 5,490 (7.9), 3,318 (45,7), 2,801 (0,8), 2, 792 (1, 2), 2, 783 (1, 8), 2,774 (1, 8) 2,765 (1,2), 2,756 (0,9), 2,676 (0,6), 2,671 (0,7), 2,667 (0,5), 2,524 (2,4), 2,511 (43,3 2.507 (87.6); 2.502 (120.2); 2.498 (91.2); 2.493 (45.8); 2.441 (16.0); 2.333 (0.5); 2.329 (0.7) 2.325 (0.5); 0.747 (1, 1); 0.734
,717(4,0);0,712(3,1);0,700(1 ,3);0,497(1,3);0,486(3,7);0,480(3,6);0,476(3,4);0,471 (3,4);0,459(1 ,1);0,008(1 ,8);0,000(43,8);-0,008(1 ,8) , 717 (4.0), 0.712 (3.1), 0.700 (1.3), 0.497 (1.3), 0.486 (3.7), 0.480 (3.6), 0.476 (3.4); 0.471 (3.4), 0.459 (1, 1), 0.008 (1, 8), 0.000 (43.8), - 0.008 (1, 8)
Beispiel 1-1-223: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,704(1 ,8);9,687(1 ,8);8,167(1 ,7);8,158(1 ,7);7,539(4,3);7,453(1 ,5);7,434(1 ,8);7,242(1 ,6Example 1-1-223: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.704 (1.8), 9.687 (1.8), 8.167 (1, 7), 8.158 (1, 7 7,539 (4,3); 7,453 (1, 5); 7,434 (1, 8); 7,242 (1, 6);
);7,224(2,2);7,206(1 ,4);5,553(6,0);3,319(19, 1);2,796(0,6);2,786(0,9);2,778(1 ,3);2,768(1 ,3);2,760(0,9);2,750(0,6);2,671 (0,4);2,667(0,37,224 (2,2), 7,206 (1,4), 5,553 (6,0), 3,319 (19, 1), 2,796 (0,6), 2,786 (0,9), 2,778 (1, 3) 2.768 (1, 3), 2.760 (0.9), 2.750 (0.6), 2.671 (0.4), 2.667 (0.3
(11 ,1);2,564(16,0);2,525(1 ,4);2,511 (23,0);2,507(46,1);2,502(62,8);2,498(47,3);2,494(23,6);2,329(0,4);0,749(0,7);0,736(2,1 );0,732(2,8);0,71(11, 1); 2.564 (16.0); 2.525 (1, 4); 2.511 (23.0); 2.507 (46.1); 2.502 (62.8); 2.498 (47.3); 2.494 ( 23.6), 2.329 (0.4), 0.749 (0.7), 0.736 (2.1), 0.732 (2.8), 0.71
9(2,7);0,714(2,2);0,702(0,9);0,503(0,9);0,492(2,5);0,486(2,4);0,482(2,3);0,477(2,3);0,464(0,7);0,008(1 ,0);0,000(22,9);-0,008(0,9) 9 (2.7); 0,714 (2.2); 0.702 (0.9); 0.503 (0.9); 0,492 (2.5); 0,486 (2.4); 0.482 (2.3) 0.477 (2,3); 0,464 (0,7); 0,008 (1, 0); 0,000 (22,9); - 0,008 (0,9)
Beispiel 1-1-224: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,908(2,4);9,892(2,4);8,631 (3,8);8,627(4, 1);8,400(3,9);8,398(3,9);7,819(1 ,0);7,816(1 ,2Example 1-1-224: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.908 (2.4), 9.892 (2.4), 8.631 (3.8), 8.627 (4, 1 8,400 (3.9), 8.398 (3.9), 7.819 (1, 0), 7.816 (1, 2
);7,800(1,3);7,797(2,4);7,794(1 ,7);7,779(1 ,5);7,776(1 ,5);7,638(2,6);7,617(2,1);7,377(1 ,3);7,374(1 ,4);7,358(2,3);7,342(1 ,2);7,339(1 ,2);5,755(7.800 (1.3); 7.797 (2.4); 7.794 (1, 7); 7.799 (1, 5); 7.776 (1.5); 7.638 (2.6); 7.617 (2.1) 7.377 (1, 3), 7.374 (1, 4), 7.358 (2.3), 7.342 (1, 2), 7.399 (1, 2), 5.755 (
0,6);5,352(8,3);4,506(13,9);3,931 (1 ,4);3,350(28,3);3,324(1 ,8);3,292(2,5);2,526(0,9);2,512(13,9);2,508(28,4);2,503(39, 1);2,499(30,0)i0.6), 5.352 (8.3), 4.506 (13.9), 3.931 (1, 4), 3.350 (28.3), 3.324 (1.8), 3.292 (2.5), 2.526 (0 , 9), 2.512 (13.9), 2.508 (28.4), 2.503 (39, 1), 2.499 (30.0) i
15,2);2,456(16,0);1 ,234(0,3);0,008(0,7);0,000(17,0);-0,009(0,7) 15.2), 2.456 (16.0), 1, 234 (0.3), 0.008 (0.7), 0.000 (17.0), - 0.009 (0.7)
Beispiel 1-1 -225: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,957(2,3);9,940(2,3);8,148(2,6);8,143(2,6);8,018(0,5);8,013(0,5);7,816(0,8);7,810(0,8Example 1-1-225: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.957 (2.3), 9.940 (2.3), 8.148 (2.6), 8.143 (2.6 ); 8,018 (0.5); 8,013 (0.5); 7.816 (0.8); 7,810 (0.8
);7,795(1,5);7,789(1 ,5);7,775(0,9);7,769(0,9);7,596(2,1);7,586(0,6);7,577(2,4);7,495(0,4);7,489(0,3);7,301 (2,2);7,283(2,8);7,271 (0,6);7,265( 2,0);7,254(0,4);7,175(1.8);7, 169(1 ,8);7,154(1 ,7);7,147(1 ,7);6,804(0,6);6,782(0,6);5,456(7.1);5.372 7.795 (1.5); 7.789 (1.5); 7.775 (0.9); 7.769 (0.9); 7.596 (2.1); 7.586 (0.6); 7.577 (2.4) 7.495 (0.4), 7.489 (0.3), 7.301 (2.2), 7.283 (2.8), 7.271 (0.6), 7.265 (2.0), 7.254 (0.4); 7,175 (1.8); 7, 169 (1, 8); 7,154 (1, 7); 7,147 (1, 7); 6,804 (0.6); 6,782 (0,6); 5,456 (7.1); 5,372
,320(21 ,7);3,177(1 ,1);3,163{1 ,1);2,672(0,4);2,525(1 ,3);2,512(23,7);2,507(48,3);2,503(66,1);2,498(49,6);2,494(24,2);2,472(2,6);2,437(14,6); 2,330(0,4); 1 ,046(0,5); 1 ,031 (0,5);0,008(1 ,0);0,000(26,0);-0,009(0,9) , 320 (21, 7), 3.177 (1, 1), 3.163 {1, 1), 2.672 (0.4), 2.525 (1.3), 2.512 (23.7), 2.507 (48.3); 2,503 (66.1); 2,498 (49.6); 2,494 (24.2); 2,472 (2.6); 2,437 (14.6); 2,330 (0.4); 1, 046 (0.5); 1, 031 (0.5), 0.008 (1, 0), 0.000 (26.0), - 0.009 (0.9)
Beispiel 1-1-226: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,901(2,4);9,884(2,6);9,873(0.7);8,350(2,5);8,346(2,6);8,293(0,7);8.287(0.7);7,986(0.9Example 1-1-226: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.901 (2.4); 9.884 (2.6); 9.873 (0.7); 8.350 (2.5); 8.346 (2.6) 8.293 (0.7); 8,287 (0.7); 7,986 (0.9
);7,980(0,9);7,965(1,6);7.959(1,6);7,945(0,9);7,939(0,9);7,839(0,8);7,837(1 ,0);7,828(0,4);7,818(2,2);7,815(1,9);7,799(1.6);7,79^7.980 (0.9), 7.965 (1.6), 7.959 (1.6), 7.945 (0.9), 7.939 (0.9), 7.839 (0.8), 7.837 (1, 0) ; 7,828 (0.4); 7,818 (2.2); 7,815 (1.9); 7,799 (1.6); 7.79 ^
0,6);7,788(0,5);7,749(2,8);7,737(0,8);7,727(1,7);7,715(0,5);7,703(0,5);7,697(0,5);7,681(0,5);7,675(0,5);7,378(1,2);7,375(1,3);7,360(2,4);^0.6); 7,788 (0.5); 7,749 (2.8); 7,737 (0.8); 7,727 (1.7); 7,715 (0.5); 7,703 (0.5); 7,697 (0 , 5); 7,681 (0.5); 7,675 (0.5); 7,378 (1.2); 7,375 (1.3); 7,360 (2.4); ^
58(2,4);7,343(1,6);7,340(1,4);7,176(1,7);7,169(1 ,7);7,154(1,7);7,147(1 ,6);6,795(0,8);6,773(0,8);5,237(8,1^ 58 (2.4), 7.343 (1.6), 7.340 (1.4), 7.176 (1.7), 7.169 (1, 7), 7.154 (1.7), 7.147 (1, 6), 6.795 (0.8); 6,773 (0.8); 5,237 (8.1 ^
;3,365(34,6);3,319(29,6);2,672(0,5);2,668(0,3);2,512(26,6);2,508(54,3);2,503(75,6);2,499(58,5);2,495(29,8);2,335(0,3);2,330(0,5);2,326(0,3 );0,008(0,9);0,000(24,7);-0.008(1 ,0)  ; 3,365 (34.6); 3,319 (29.6); 2,672 (0.5); 2,668 (0.3); 2,512 (26.6); 2,508 (54.3); 2.503 (75.6); 2.499 (58.5), 2.495 (29.8), 2.355 (0.3), 2.330 (0.5), 2.326 (0.3), 0.008 (0.9), 0.000 (24.7), - 0.008 (1, 0)
Beispiel 1-1-227: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,174(8,4);9,652(4,9);9,636(5,2);8,315(0.4);7,947(4,1);7.925(5.4);7,876(13,1);7,803(2Example 1-1-227: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.174 (8.4), 9.652 (4.9), 9.636 (5.2), 8.315 (0.4); 7,947 (4.1); 7,925 (5.4); 7,876 (13.1); 7,803 (2
,6);7,800(2,8);7,785(3,2);7,782(4,6);7,763(2,3);7,760(2,3);7,687(0,5);7,678(5,5);7,673(2,1);7,666(6,0);7,660(3,5);7,655(6.4);^ , 6); 7,800 (2.8); 7,785 (3.2); 7,782 (4.6); 7,763 (2.3); 7,760 (2.3); 7,687 (0.5); 7,678 (5, 5); 7,673 (2.1); 7,666 (6.0); 7,660 (3.5); 7.655 (6.4); ^
3(6,0);7,634(0,6);7,408(2.5);7,405(2,7);7,389(4,8);7,373(2,4);7,370(2,4);7,199(0,6);7,190(6,0);7,185(2,0);7,168(10,7);7,151 (1,^ 3 (6.0); 7,634 (0.6); 7,408 (2.5); 7,405 (2.7); 7,389 (4.8); 7,373 (2.4); 7,370 (2.4); 7,199 (0 , 6), 7.190 (6.0), 7.185 (2.0), 7.168 (10.7), 7.151 (1, ^
7,137(0,5);5,756(9,9);5,507(16,0);3,322(70,1):2,677(0,7);2,672(1,0):2,668(0,7):2,526(2,3);2,521(3,4);2,512(54,7);2,508(118,1);2,503(187,0) ;2.499(124,0);2.494(58,9):2,335(0,7);2.330(1,0);2,326(0,7);1,990(0,6);0,000(7,7) 7,137 (0.5); 5,756 (9.9); 5,507 (16.0); 3,322 (70.1) 2,677 (0.7); 2,672 (1.0) 2,668 (0.7): 2.526 (2.3); 2.521 (3.4); 2.512 (54.7); 2.508 (118.1); 2.503 (187.0); 2.499 (124.0); 2.494 (58.9): 2.335 ( 0.7); 2,330 (1.0); 2,326 (0.7); 1,990 (0.6); 0,000 (7.7)
Beispiel 1-1-228: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,735(3.6);9,718(3,7);8.503(4.3);8,496(4,4);8,050(1,3);8,036(2.8);8,021(1,4);7,882(2.3Example 1-1-228: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.735 (3.6), 9.718 (3.7), 8.503 (4.3), 8.496 (4.4), 8.050 ( 1.3); 8,036 (2.8); 8,021 (1.4); 7,882 (2.3
);7,875(2,3);7,861(2,6);7,854(2,5);7,580(6,6);7,570(7,0);7,506(5,1);7,485(4,6);7,299(1 ,5);7,288(2,6);7,282(1,7);7,277(1 ,6);7,271 (2,5);7,260(); 7,875 (2.3); 7,861 (2.6); 7,854 (2.5); 7,580 (6.6); 7,570 (7.0); 7,506 (5.1); 7,485 (4.6) 7.299 (1, 5), 7.288 (2.6), 7.282 (1.7), 7.277 (1, 6), 7.271 (2.5), 7.260 (
1,3);6,049{0,7);6,031(2,4);6,013{2,4);5,995(0,7);5,757(4,9);4,346(0,5);4,336(0,5);3,570(3,8);3,339(1,0);3,326(16,3);3,305(4,1);3,289(3,2);3,1.3); 6,049 {0.7); 6,031 (2.4); 6.013 {2.4); 5,995 (0.7); 5,757 (4.9); 4,346 (0.5); 4,336 (0 , 5); 3,570 (3.8); 3,339 (1.0); 3,326 (16.3); 3,305 (4.1); 3,289 (3.2); 3,
271(1,0):2,528(0.6);2,514(13,6);2,510(28,5);2.506(39,7);2,^ 271 (1,0): 2.528 (0.6); 2,514 (13.6); 2,510 (28.5); 2,506 (39.7); 2, ^
,048(3,8);1 ,033(3,8);0,000(2,2)  , 048 (3,8); 1, 033 (3,8); 0,000 (2,2)
Beispiel 1-1-229: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,312(9,1);9,729(5,4);9,712(5,7);8,539(6,8);8,532(6,9);8,315(0,4);7,929(3,6);7,923(3,Example 1-1-229: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.312 (9.1); 9.729 (5.4); 9.712 (5.7); 8.539 (6.8) ); 8.532 (6.9) 8.315 (0.4) 7.929 (3.6); 7,923 (3,
6);7,909(4,0);7,902(4,0):7,700{1,0);7,681(4,0);7,679(4,3);7,663(10,9):7,635(8,9);7,616(9,8);7,524(7,9);7,503(7,2):7,382(2,4);7,376(2,2);7,36 6(4,1);7,360(3,8);7,350(2,3);7,343(2,6);7,336(6,1);7,317(9,4);7,297(6,0);7,040(3,1);7,022(5,4);7,003(2,4);6,102(1,0);6,084i3,6);6,087(3,6);6, 049(1,0);5,755(2,0);4,828(0,4);3,373(0,3):3,320(66,2);2,676(0,9):2,671(1,2):2,667(0,9);2,525{2,9):2,511 (69,4);2,507(145,0):2,502{201,0);2, 498(149,9);2,333(0,9);2,329(1,1);2,325(0,8);1,983(16,0);1,965(15,9);1,046(0,7);1,030(0,6);0,008(0,4):0,000(9,6);-0,009(0,4) 6); 7,909 (4.0); 7,902 (4.0): 7.700 {1.0); 7,681 (4.0); 7,679 (4.3); 7,663 (10.9) 7,635 (8.9 7.616 (9.8), 7.524 (7.9), 7.503 (7.2): 7.382 (2.4), 7.376 (2.2), 7.366 (4.1), 7.360 (3 , 8); 7,350 (2.3); 7,343 (2.6); 7,336 (6.1); 7,317 (9.4); 7,297 (6.0); 7,040 (3.1); 7,022 (5, 4); 7,003 (2,4); 6,102 (1,0); 6,084i3,6); 6,087 (3,6); 6,049 (1,0); 5,755 (2,0); 4,828 (0); 4); 3.373 (0.3): 3.320 (66.2); 2.676 (0.9): 2.671 (1.2): 2.667 (0.9); 2.525 {2.9): 2.511 (69.4 2.507 (145.0): 2.502 {201.0); 2.498 (149.9); 2.333 (0.9); 2.329 (1.1); 2.325 (0.8); 1.983 (16); 0); 1,965 (15.9); 1,046 (0.7); 1,030 (0.6) 0.008 (0.4) 0.000 (9.6) - 0.009 (0.4)
Beispiel 1-1-230: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,366(8,9);9,643(5,0);9,627(5,2);7,984(5,3);7,962(4,1);7,940(5,5);7,879(13,2);7,831(2Example 1-1-230: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.366 (8.9); 9.643 (5.0); 9.627 (5.2); 7.984 (5.3 ); 7.962 (4.1); 7,940 (5.5); 7,879 (13.2); 7,831 (2
,7);7,828(2,8);7,812(3,4);7,809(4,6);7,790(2,3);7,787(2,3);7,471(2,3):7,450(6,6);7,431 (6,3):7,417(8,3):7,414(6,7);7,397(6,7);7,382(2,5^, 7); 7,828 (2.8); 7,812 (3.4); 7,809 (4.6); 7,790 (2.3); 7,787 (2.3); 7,471 (2.3) 7,450 (6, 6); 7.431 (6.3): 7.417 (8.3): 7.414 (6.7); 7.397 (6.7); 7.382 (2.5 ^
9(2,4);7,020(3,0):7,000(2,7):8,998(2,4);5,756(1,5);5,511 (16,0);3,323(75,1);2,678(0,8);2,673(0,8):2,669(0,6);2,527(2,0);2,522(3,0);2,513{46,9 (2.4); 7.020 (3.0): 7.000 (2.7): 8.998 (2.4); 5.756 (1.5); 5.511 (16.0); 3.323 (75.1); 2.678 2,669 (0.6); 2,527 (2.0); 2,522 (3.0); 2,513 {46: (0.8) 2,673 (0.8)
3);2,509(98,8);2,504(138,5);2,500(102,5);2,495(48,7);2,336(0,6);2,331(0,8);2,327(0,6):1,990(0,8);1,177(0,4);0,000(6,8) 3); 2,509 (98.8); 2.504 (138.5); 2,500 (102.5); 2,495 (48.7); 2,336 (0.6); 2,331 (0.8); 2,327 (0.6 ): 1,990 (0.8); 1,177 (0.4); 0,000 (6.8)
Beispiel 1-1-231 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,548(4,9);9,532(5,1);9,488(8,9);8,315(0,4);7,949(4,0);7,927(5,5);7,883(13,1);7,814(2,Example 1-1-231: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.548 (4.9), 9.532 (5.1), 9.488 (8.9), 8.315 (0.4 ); 7,949 (4.0); 7.927 (5.5); 7,883 (13.1); 7,814 (2,
6);7,811(2,8);7,796(3,2);7,793(4,6);7,774(2,3);7,771(2,3);7,397(2,5);7,394(2,7);7,378(4,9);7,368(1,8);7,362(3,6);7,352(1,2);7,347(3,1);7,342 (1,4);7,326(2,3);7,310(1,0);7,222(0.6);7,217(1,0);7,209(6,4);7,201(1,0):7,197(1,1);7,189(9,8);7,168(4,^ 6); 7,811 (2.8); 7,796 (3.2); 7,793 (4.6); 7,774 (2.3); 7,771 (2.3); 7,397 (2.5); 7,394 (2.7 7.378 (4.9); 7.688 (1.8); 7.362 (3.6); 7.352 (1.2); 7.347 (3.1); 7.342 (1.4); 7.326 (2.3) ; 7,310 (1.0); 7,222 (0.6); 7,217 (1.0); 7,209 (6.4); 7,201 (1.0) 7,197 (1.1); 7,189 (9.8); 7,168 ( 4 ^
039(0,4);4,022(0,4);3,322(95,0);2,677(0,7);2,673(0,9);2,668(0,7):2,526(2,1);2,521(3,1):2,512(50,3);2,508(109,0);2,503(155,1);2,4 2.495(56, 1 );2,335(0,6);2,330(0,9);2,326(0,7); 1 ,990(1,6); 1 , 194(0,4); 1 , 177(0,9); 1 , 159(0,4);0,000(7,3)  039 (0.4); 4,022 (0.4); 3,322 (95.0); 2,677 (0.7); 2,673 (0.9); 2,668 (0.7) 2,526 (2.1); 2,521 (3.1): 2.512 (50.3); 2.508 (109.0); 2.503 (155.1); 2.4 2.495 (56.1); 2.335 (0.6); 2.330 (0.9) ; 2,326 (0.7); 1, 990 (1.6); 1, 194 (0.4); 1, 177 (0.9); 1, 159 (0.4); 0.000 (7.3)
Beispiel 1-1-232: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,347(4.8);10,341(5,0);9,619(4,9);9.603(5,0);8,462(1 ,5);8,447(1 ,7);8,439(3,2);8,424(3Example 1-1-232: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.347 (4.8); 10.341 (5.0); 9.619 (4.9); 9.603 (5.0); 8.462 (1, 5), 8.447 (1, 7), 8.439 (3.2), 8.424 (3
,2);8,417(1 ,8);8,401(1,6);7,954(4,0);7,932(5,4);7,877(12,1);7,822{2,8);7,804(4,5);7,784(2,1);7,782(2,3);7,419(2,7);7,402(5,2);7,392(2,1);7,3 86(2,6);7,384(2,7);7,377(2,0);7,370(3,3);7,363(2,0);7,348(1,7);7,341(1 ,7);7,107(1 ,3);7,084(2,5);7,064(1,3);5,756(0,4);5,512(18,0);3,323(48, 5);2,678(0,5);2,674(0,7);2,526(1,7);2,509(87,6);2,504(124,7);2,500(99,4);2,331(0,7);2,327(0,6);1,990(0,4);0,008(0,4);0,000(10,4), 2), 8.417 (1, 8), 8.401 (1.6), 7.954 (4.0), 7.932 (5.4), 7.877 (12.1), 7.822 (2.8), 7.804 (4, 7,784 (2,1); 7,782 (2,3); 7,419 (2,7); 7,402 (5,2); 7,392 (2,1); 7,386 (2,6); 7,384 ( 2.7), 7.377 (2.0), 7.370 (3.3), 7.363 (2.0), 7.348 (1.7), 7.341 (1, 7), 7.107 (1, 3), 7,084 (2 , 5), 7,064 (1,3), 5,756 (0,4), 5,512 (18,0), 3,323 (48, 5), 2,678 (0,5), 2,674 (0,7), 2,526 (1, 7); 2,509 (87.6); 2.504 (124.7); 2,500 (99.4); 2,331 (0.7); 2,327 (0.6); 1,990 (0.4) 0.008 (0.4 ); 0.000 (10.4)
Beispiel 1-1-233: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,401 (8,5);9,655(4,9);9,639(5,0);8,315(0,5);8,285(6,3);7,967(4.0);7,945(5,3);7,881(12 ,1);7,832(2,7);7,813(4.3);7,793(2.2);7,791(2.2);7,722(2.7);7,701(3,5);7,581(2,5);7,561 (4,7);7,541(2,4);7,417(2,6);7,400(4,^ Example 1-1-233: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.401 (8.5), 9.655 (4.9), 9.639 (5.0), 8.315 (0.5 8,285 (6.3), 7.967 (4.0), 7.945 (5.3), 7.881 (12, 1), 7.832 (2.7), 7.813 (4.3), 7.793 (2.2), 7.791 (2.2); 7.722 (2.7), 7.701 (3.5), 7.581 (2.5), 7.561 (4.7), 7.541 (2.4), 7.417 (2.6), 7.400 (4, ^
6(3,2);5,756(1,0);5,514(16,0);3,321(75,9);2,672(1,3);2,668(0,9);2,525(3,1);2,507(152,8);2,503(210,8);2,499(160,4);2,330(1,2);2,326(0,9) 000(18,4)  6 (3.2); 5,756 (1.0); 5,514 (16.0); 3.321 (75.9); 2,672 (1.3); 2,668 (0.9); 2,525 (3.1); 2,507 (152.8); 2.503 (210.8); 2.499 (160.4); 2.330 (1.2); 2.236 (0.9) 000 (18.4)
Beispiel 1-1-234: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,595(8,6);9,669(4,8);9,652(5,0);8,584(4,0);8,581(4,5);8,563(4,4);8,560(4,6);7,943(3, 9);7,921(5,4);7,878(12.3):7,828(2,6);7,826(2,8);7,807(4,5);7,788(2,1);7,785(2,2);7,520(4,1):7,517(4,7);7,5(X)(4,7);7.497(5,0) Example 1-1-234: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.595 (8.6), 9.699 (4.8), 9.652 (5.0), 8.584 (4.0 8.581 (4.5), 8.563 (4.4), 8.560 (4.6), 7.943 (3.9), 7.921 (5.4), 7.878 (12.3): 7.828 (2.6), 7.826 (2.8); 7,807 (4.5); 7,788 (2.1); 7,785 (2.2); 7,520 (4.1) 7,517 (4.7); 7.5 (X) (4, 7); 7,497 (5.0)
1(2,6);7,405(4,7);7,389(2,3);7,386(2,3);7,353(2,0);7,349(2,1);7,331(4,0);7,313{2,3);7,310(2,3);7,078(2,5);7,072(2,7);7,056(3,9);7,053i4,1);7, 037(2,1);7,034(2,2);5,756(2,4);5,525(16,0);3,322(53,1);2,677(0,6);2,673(0,8);2,669(0,6);2,526(2,0);2,512(45,8);2,508(96,9);2,504(136,3);2, 499(104,4);2,335(0,6);2,330(0,8);2,326(0,6);1,990(0.4);0,008(0,4);0,000(11,0)  1 (2.6); 7,405 (4.7); 7,389 (2.3); 7,386 (2.3); 7,353 (2.0); 7,349 (2.1); 7,331 (4.0); 7,313 {2,3}; 7,310 (2,3); 7,078 (2.5); 7,072 (2,7); 7,056 (3,9); 7,053i4,1); 7,037 (2,1); 7,034 (2.2); 5,756 (2.4); 5,525 (16.0); 3.322 (53.1); 2,677 (0.6); 2,673 (0.8); 2,669 (0.6); 2,526 ( 2.0), 2.512 (45.8), 2.508 (96.9), 2.504 (136.3), 2.499 (104.4), 2.335 (0.6), 2.330 (0.8), 2.326 (0.6); 1,990 (0.4) 0.008 (0.4) 0.000 (11.0)
Beispiel 1-1-235: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,149(4,5);9,673(2,6);9,657(2,7);7,947(2,2);7,925(2,8);7,879(6,8);7,798(1,3);7,795(1,Example 1-1-235: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.149 (4.5); 9.673 (2.6); 9.657 (2.7); 7.947 (2.2 ); 7,925 (2.8); 7,879 (6.8); 7,798 (1.3); 7,795 (1,
4);7,779(1 ,7);7,777(2,4);7,758(1 ,2);7,755(1 ,2);7,457(5,9);7,440(2,0);7,402(1 ,3);7,400(1 ,4);7,383(2,5);7,367(1 ,2);7,365(1 ,3);7,227(1 ,3);7,2087,779 (1, 7); 7,777 (2,4); 7,758 (1,2); 7,755 (1,2); 7,457 (5,9); 7,440 (2,0); 7,402 (1, 3) 7,400 (1, 4), 7,383 (2,5), 7,367 (1,2), 7,365 (1,3), 7,227 (1,3), 7,208
(2,3);7,186(1.4);6,863(2,1);6,845(1,8);5,507(8,6);3,321(30,7);2,676(0,5);2,672(0,6);2,667(0,5);2,525(1,5);2,512(35,4);2,507(75,4);2,^(2.3); 7,186 (1.4); 6,863 (2.1); 6,845 (1.8); 5,507 (8.6); 3,321 (30.7); 2,676 (0.5); 2,672 (0, 6); 2.667 (0.5); 2,525 (1.5); 2,512 (35.4); 2.507 (75.4); 2, ^
,2);2,498(79,3);2,494(38,1);2,334(0,5);2,330(0,7);2,325(0,6);2,307(16,0);1 ,989(0,3);0,000(8,6) , 2); 2.498 (79.3); 2.494 (38.1); 2.344 (0.5); 2.330 (0.7); 2.325 (0.6); 2.307 (16.0); 1, 989 ( 0,000 (8.6); 0.3)
Beispiel 1-1-236: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,032(2.6);9,673(1 ,5);9,657(1 ,6);7.935(1 ,2);7,913(1 ,6);7,876(3,9);7,781 (0,8);7,778(0, 8);7,759(1 ,4);7,741 (0,7);7,738(0,7);7,561 (3,3);7,556(1 ,1);7,544(1 , 1);7,539(3,7);7,530(0,4);7,392(0,7);7,389(0,8);7,373(1 ,4);7,357(0,7);7,354 (0,7);6,925(3,5);6,920(1,1);8,908(1,0);6,902(3,4);5,756(0,8);5,504(4,7);3,741(16,0);3,321(21,2);2,672(0,4);2,525(0,8);2,520(1,3);2,512(19,4) ;2,507(41,6);2,503(58,6);2,498(43,5);2,494(20,7);2,330(0,3);0,000(5,0) Example 1-1-236: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.032 (2.6), 9.673 (1.5), 9.657 (1, 6), 7.935 (1.2); 7.913 (1, 6), 7.876 (3.9), 7.781 (0.8), 7.778 (0.8), 7.759 (1.4), 7.741 (0.7), 7.738 (0.7), 7.551 (3,3); 7,556 (1, 1); 7,544 (1, 1); 7,539 (3,7); 7,530 (0,4); 7,392 (0,7); 7,389 (0,8); 7,373 ( 1, 4), 7.357 (0.7), 7.354 (0.7), 6.925 (3.5), 6.920 (1.1), 8.908 (1.0), 6.902 (3.4), 5.756 (0 , 8); 5,504 (4.7); 3,741 (16.0); 3.321 (21.2); 2,672 (0.4); 2,525 (0.8); 2,520 (1.3); 2,512 (19, 4), 2.507 (41.6), 2.503 (58.6), 2.498 (43.5), 2.494 (20.7), 2.330 (0.3), 0.000 (5.0)
Beispiel 1-1-237: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,155(2,7);9,728(1,6);9,712(1,7);8,534(1,9);8,528(2,0);7,923(1,0);7,917(1,0);7,902(1, 1);7,896(1,1);7,858(2,0);7,648(3,1);7,560(0,3);7,552{3,4);7,547(1,2);7,535(1,2);7,529(3,7);7,521(2,6);7,500(2,1);7,366{0,7);7,358(0,6);7,353 (0,7);7,349(0,8);7,344(0,7);7,341 (0,7);7,337(0,7);7,328(0,6);6,919(0,4);6,911(3,6);6,905(1,2);6,^ Example 1-1-237: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.155 (2.7), 9.728 (1.6), 9.712 (1.7), 8.534 (1.9 8.828 (2.0), 7.923 (1.0), 7.917 (1.0), 7.902 (1, 1), 7.896 (1.1), 7.858 (2.0), 7.648 (3.1) ; 7,560 (0.3); 7.552 {3.4); 7,547 (1.2); 7,535 (1.2); 7,529 (3.7); 7.521 (2.6); 7,500 (2.1); 7.366 (0.7); 7.358 (0.6); 7.353 (0.7); 7.349 (0.8); 7.344 (0.7); 7.341 (0.7); 7.337 (0.7); 7.328 (0.6); 6,919 (0.4); 6,911 (3.6); 6,905 (1.2); 6 ^
60(1,0);3,734(18,0);3,323(34,0);2,525(0,9);2,512(18,3);2,507(37,5);2,503(51,7);2,498(38,5);2,494(18,7);1,989(1,5);1,979(4,5);1,961(4,4);1, 60 (1.0); 3,734 (18.0); 3.323 (34.0); 2,525 (0.9); 2,512 (18.3); 2.507 (37.5); 2.503 (51.7); 2,498 (38.5) 2,494 (18.7); 1,989 (1.5); 1,979 (4.5); 1,961 (4.4); 1,
176(0,6);0,008(2,5);0,000(63,6);-0,008(2,3) 176 (0.6) 0.008 (2.5) 0.000 (63.6) - 0.008 (2.3)
Beispiel 1-1-238: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,528(8,8);9,708(5,0);9,691(5,3);8,543(6,2);8,537(6,4);8,316(0,3);8,282(6,3);7,938(3,Example 1-1-238: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.528 (8.8), 9.708 (5.0), 9.691 (5.3), 8.543 (6.2 ); 8,537 (6.4); 8,316 (0.3); 8.282 (6.3) 7.938 (3,
4);7,932(3,3);7,918(3,7);7,911(3,7);7,738(0,9);7,715(4,1);7,700(12,0);7,682(4,6);7,562(2,5):7,542(4,8);7,528(7,7);7,507(6,7);7,396(2,2);7,39 0(2,0);7,379(4,0);7,373(6,6);7,364(3,1);7,357(3,0);7,352(3,3);6,102(0,9);6,085(3,3);6,067(3,4);6,049(0,9);5,756(1,2);4,057(0,4);4,039(1,1);4, 021(1 ,1);4,004(0,4);3,327(62,1);2,677(0,6);2,673(0!8);2!668(0,6);2,526(2,1);2,508(100,6);2,504(139,9);2!499(106,0);2!335(0,6);2,330(0,8);2 ,326(0,6);1 ,988(16,0);1,970{14,4);1 94(1,2);1 J76(2,4);1 59(1,2);0,146(0,5);0,008{3,8);0,000(107,4);-0,008(4,2);-0,150(0,5) 4); 7,932 (3.3); 7.918 (3.7); 7,911 (3.7); 7,738 (0.9); 7,715 (4.1); 7,700 (12.0); 7,682 (4.6 7.562 (2.5): 7.542 (4.8), 7.528 (7.7), 7.507 (6.7), 7.396 (2.2), 7.39 (2.0), 7.379 (4 , 0); 7,373 (6.6); 7,364 (3.1); 7,357 (3.0); 7,352 (3.3); 6,102 (0.9); 6,085 (3.3); 6,067 (3, 4); 6,049 (0.9); 5,756 (1.2); 4,057 (0.4); 4,039 (1.1); 4, 021 (1,1), 4,004 (0,4), 3,327 (62,1), 2,677 (0,6), 2,673 (0 ! 8), 2 ! 668 (0.6), 2.526 (2.1), 2.508 (100.6), 2.504 (139.9), 2 ! 499 (106,0); 2 ! 335 (0.6); 2.330 (0.8); 2, 326 (0.6); 1, 988 (16.0); 1.970 {14.4); 1 94 (1.2); 1 J76 ( 2.4), 1 59 (1.2), 0.146 (0.5), 0.008 {3.8), 0.000 (107.4), -0.008 (4.2), -0.150 (0.5)
Beispiel 1-1-239: 1H-NMR(400.0 MHz, de-DMSO): δ= 10,131 (4,1);9,695(2,5);9,679(2,6);8,334(2,4);8,315(2,6);7,939(2,1);7,918(2,8);7,879(6, 4);7,802(1 ,3);7,799(1 ,4);7,781 (2,3);7,762(1 ,2);7, 759(1 ,2);7,411 (1 ,3);7,409(1 ,4);7,392(2,5);7,376(1 ,2);7,374(1 ,2);7,241(1,9);7,222(2,1);7,202Example 1-1-239: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.131 (4.1); 9.695 (2.5); 9.679 (2.6); 8.344 (2.4); 8.915 (2.6), 7.939 (2.1), 7.918 (2.8), 7.879 (6, 4), 7.802 (1, 3), 7.799 (1.4), 7.781 (2.3), 7.762 (1,2); 7,759 (1,2); 7,411 (1,3); 7,409 (1,4); 7,392 (2,5); 7,376 (1,2); 7,374 (1, 2); 7,241 (1.9); 7,222 (2.1); 7,202
(1,0);7,182(1,9);7,163(1,1);6,976(1,4);6,957(2,3);6,939(1,0);5,532(8,5);3,324(70,1);2,672(0,5);2,668(0,4);2,508(61,9);2,503(85,9);2,499(65, 2);2,341 (16,0); 0,008(2, 1 );0,000(57,2);-0,008(2,4) (3,324 (1.0); 7.182 (1.9); 7,163 (1.1); 6,976 (1.4); 6,957 (2.3); 6,939 (1.0); 5,532 (8.5) 70.1); 2.672 (0.5); 2.668 (0.4); 2.508 (61.9); 2.503 (85.9); 2.499 (65.2); 2.341 (16.0); 0.008 (2, 1); 0.000 (57.2); - 0.008 (2.4)
Beispiel 1-1-240: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,338(2,3);9,336(2,3);9,322(2.4);8,315(0,3);8,059(1,8);8,050(1,8);7.690(5,4);7,320(1,6Example 1-1-240: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.338 (2.3); 9.366 (2.3); 9.322 (2.4); 8.315 (0.3); 8,059 (1.8); 8,050 (1.8); 7,690 (5.4); 7,320 (1.6
);7,300(2,8);7,253(2,1);7,236(2,1);7,232(1,4);7,216(1,2);5,513(7,3);4,047(16,0):3,319(41,8);2,777(0,6);2,768(0,8);2,759(1,2);2,750(1,2);2,74 1(0,9):2,732(0,6);2,671(0,8);2,507(101,9);2,502(137,6);2,498(103,4);2,333(0,6);2,329(0,8);2,325(0,6);1,045(0,6);1,030(0,6);0,742(0,7);0,72); 7,300 (2.8); 7,253 (2.1); 7,236 (2.1); 7,232 (1.4); 7,216 (1.2); 5,513 (7.3); 4,047 (16.0) 2.719 (41.8), 2.777 (0.6), 2.768 (0.8), 2.759 (1.2), 2.750 (1.2), 2.74 1 (0.9): 2.732 (0), 6); 2,671 (0.8); 2,507 (101.9); 2.502 (137.6); 2.498 (103.4); 2,333 (0.6); 2,329 (0.8); 2,325 (0.6 ); 1,045 (0.6); 1,030 (0.6); 0,742 (0.7); 0.72
9(2,2);0,724(2,8):0,712(2,8);0,707(2,2);0,695(0,9);0,494(0,9);0,483(2,6);0,477(2,5);0,468(2,4);0,456(0,7);0,146(0,4);0,008(3,7);0,000(94,7);^ 0,008(4,0);-0,150(0,4) 9 (2,2); 0.724 (2.8) 0.712 (2.8) 0.707 (2.2) 0.695 (0.9); 0.494 (0.9); 0,483 (2.6); 0.477 (2.5); 0.468 (2.4); 0.456 (0.7); 0.146 (0.4); 0.008 (3.7); 0.000 (94.7); 0.008 (4.0); 0.150 (0.4)
Beispiel 1-1-241 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,640(5,2);9,624(5,4);8,515(6,6);8,509(6,8);8.445(2,2);8,429(4.6);8,412(2,3);8,315(0,5Example 1-1-241: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.640 (5.2), 9.624 (5.4), 8.515 (6.6), 8.509 (6.8 ); 8,445 (2.2); 8,429 (4.6); 8.412 (2.3) 8.315 (0.5
);7,901(3,5);7,894(3,6):7,880(4,0);7,873(3,9):7,670(1,3):7,651 (3,8);7,648(3,9);7,630(6,6);7,624(6,4);7,605(1,7);7,510(7,7);7,489(7,0);7,342( 2,4);7,338(2,4);7,325(4,5);7,321(4,4);7,308(2,2);7,304(2,2);6,055(1,1);6,037(3,6);6,019(3,6);6,001 (1,1);5,755(6,8);4,334(0,3);4,169(2,6);4,1 62(2,2);4,153(2,3);4,145(3,8);4,138(2,4);4,128(2,2);4,121(2,6);4,104(0,8);4,097(0,8);3,321 (169,7);2,676(1,2);2,672(1,6);2,667(1,2);2,524(4, 5);2,507(192,0);2,502(265,0);2,498(203,0):2,333(1,1);2,329(1,5);1 ,950(16,0);1,932(15,9);1,045(2,0);1,030(2,0);0,146(0,8):0,008(6,8);0,000( 174,2);-0,008(7,8); -0, 150(0,8) 7.901 (3.5); 7.894 (3.6): 7.880 (4.0); 7.873 (3.9): 7.670 (1.3): 7.651 (3.8); 7.648 (3.9) 7.630 (6.6); 7.624 (6.4); 7.605 (1.7); 7.510 (7.7); 7.489 (7.0); 7.342 (2.4); 7.338 (2.4); 7,325 (4.5); 7,321 (4.4); 7,308 (2.2); 7,304 (2.2); 6,055 (1.1); 6,037 (3.6); 6,019 (3.6); 6,001 (1,1); 5,755 (6,8); 4,334 (0,3); 4,169 (2,6); 4,1,6 (2,2); 4,153 (2,3); 4,145 (3,8) 4.148 (2.4); 4.128 (2.2); 4.121 (2.6); 4.104 (0.8); 4.097 (0.8); 3.321 (169.7); 2.676 (1.2); 2,672 (1,6), 2,667 (1,2), 2,524 (4,5), 2,507 (192,0), 2,502 (265,0), 2,498 (203,0): 2,333 (1,1), 2,329 (1.5); 1, 950 (16.0); 1.932 (15.9); 1.045 (2.0); 1.030 (2.0); 0.146 (0.8): 0.008 (6.8); 0.000 (174.2); - 0.008 (7.8); -0, 150 (0.8)
Beispiel 1-1-242: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,605(2,5);9,588(2,6);8,641(3,9):8,638(4,1);8,397(4,0);8,355(1,0);8,338(2,1);8,321 (1,0 );7,706(0,6);7,703(0,6):7,684(1 ,8);7,681 (1 ,8);7,667(2,2);7,664(2,4);7,656(3,0);7.636(0,9);7,352(1 , 1 ):7,348(1 ,2);7,336(2,2);7,331 (2, 1);7,319( 1,1);7,314(1,0);5,755(0,5);5,416(8,1):4 93(0,5);4,168(1,7);4J52(1,8);4,144(1,9);4,127(1,7);4,120(0,8);4 03(0,6);3,320(11,3);2,676(0,4):2,Example 1-1-242: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.605 (2.5); 9.588 (2.6); 8.641 (3.9): 8.638 (4.1 8.397 (4.0), 8.355 (1.0), 8.338 (2.1), 8.321 (1.0), 7.706 (0.6), 7.703 (0.6): 7.684 (1, 8) 7.681 (1, 8); 7.667 (2.2); 7.664 (2.4); 7.656 (3.0); 7.636 (0.9); 7.352 (1, 1): 7.348 (1, 2); 7.366 (2.2); 7.331 (2, 1); 7.319 (1.1); 7.314 (1.0); 5.755 (0.5); 5.416 (8.1): 4 93 (0.5); 4.168 (1.7), 4J52 (1.8), 4.144 (1.9), 4.127 (1.7), 4.120 (0.8), 4 03 (0.6), 3.320 (11.3); 2.676 (0.4): 2,
671(0,5);2,667(0,4);2,525(1,2);2,511(27,1);2,507(57,6);2,502(80,8);2,498(60,7):2,494(29,5);2,454(16,0);2,333(0,3);2,329(0,5):2,325(0,3);0, 008(2,0):0,000(61,0);-0,008(2,2) 671 (0.5); 2,667 (0.4); 2,525 (1.2); 2,511 (27.1); 2.507 (57.6); 2.502 (80.8); 2.498 (60.7) 2.494 (29.5); 2.454 (16.0); 2.333 (0.3); 2.329 (0.5): 2.325 (0.3); 0.008 (2.0): 0.000 (61.0); -0.008 (2.2)
Beispiel 1-1-243: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,656(2,3);9,639(2,3);8,523(2,7);8,518(2,8);8,049(1,9);8,040(2.0);7.690(1,2);7,669(2,8 );7,646(1 ,5);7,644(1 ,6);7,629(1 ,7);7,626(2,0);7,608(1 ,9):7,604(2,4):7,589(1 ,7);7.584(1 ,8);7,315(1 , 1 ):7.312(1 , 1);7,298(1 ,9);7,295(2.0):7,281 (Example 1-1-243: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.656 (2.3), 9.639 (2.3), 8.523 (2.7), 8.518 (2.8 8.049 (1.9), 8.040 (2.0), 7.690 (1.2), 7.699 (2.8), 7.646 (1.5), 7.644 (1.6), 7.629 (1, 7), 7.626 (2.0); 7.608 (1, 9): 7.604 (2.4): 7.589 (1, 7); 7,584 (1, 8); 7,315 (1, 1): 7,312 (1, 1); 1, 9); 7.295 (2.0): 7.281 (
1,0);7,277(1,0);7,206(2,7):7,186(2,5):5,223(7,6):3,323(16,0);2,792(0,6):2,783(0,9);2,774(1,4);2,765(1,4);2,756(1 ,0);2,747(0,6);2,526(0,7):2, 512(17,1);2,508(35,8);2,504(49,9):2,499(37,9);2,414(16,0);0,745(0,8);0,732(2,4);0,727(3,1);0,715(3,1);0,710(2,5);0,698(1 ,0);0,500(1,0);0,41.0); 7,277 (1.0); 7,206 (2.7) 7,186 (2.5) 5,223 (7.6) 3,323 (16.0); 2,792 (0.6): 2.783 (0 2,774 (1,4); 2,765 (1,4); 2,756 (1, 0); 2,747 (0,6); 2,526 (0,7): 2, 512 (17,1); 2,508 ( 35.8) 2,504 (49.9) 2,499 (37.9); 2,414 (16.0); 0,745 (0.8); 0.732 (2.4) 0.727 (3.1) 0.715 (3 , 1), 0.710 (2.5), 0.698 (1.0), 0.500 (1.0), 0.4
89(2,9);0,484(2,8);0,479(2,6);0,474(2,7);0,462(0,8);0,008(1,4);0,000(42,0);-0,008(1,7) 89 (2.9); 0,484 (2.8); 0,479 (2.6); 0,474 (2.7); 0.462 (0.8) 0.008 (1.4) 0.000 (42.0); - 0.008 (1.7)
Beispiel 1-1-244: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,691(2,6);9,674(2,7);8,615(3,8);8,612(4,0);8,395(3,9);7,957(0,9);7,943(1,8);7,928(0,9Example 1-1-244: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.691 (2.6), 9.674 (2.7), 8.615 (3.8), 8.612 (4.0 ); 8,395 (3.9); 7,957 (0.9); 7,943 (1.8); 7,928 (0.9
);7,610(4,8);7,600(5,1);7,305(1,1);7,294(1,8);7,288(1,2);7,283(1,1);7,278(1 ,8);7,267(1 ,0);5,756(0,3);5,399(8,3);3,336(0,9);3,322{12,2);3,3047,610 (4,8); 7,600 (5,1); 7,305 (1,1); 7,294 (1,8); 7,288 (1,2); 7,283 (1,1); 7,278 (1, 8) 7.267 (1, 0), 5.756 (0.3), 5.399 (8.3), 3.336 (0.9), 3.322 {12.2), 3.304
(3,0);3,301 (3,1);3,286(2,7);3.268(0,8);2,672(0.4);2,525(0,9);2,511(20,1);2,507(41,7);2,503(57,9^ (3.0); 3.301 (3.1); 3.286 (2.7); 3.268 (0.8); 2.672 (0.4); 2.525 (0.9); 2.511 (20.1); 2.507 (41; 2.503 (57.9 ^; 7)
,5);1, 103(11,8);1,085(5,4);1,046(2,4);1,030(2,3);0,008(1,7);0,000(48,4);-0,008(1,8)  , 5), 1, 103 (11.8), 1.085 (5.4), 1.046 (2.4), 1.030 (2.3), 0.008 (1.7), 0.000 (48.4), - 0.008 (1.8)
Beispiel 1-1-245: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,691(2,5);9,675(2.6);8,610(3,8);8,607(4,0);8,392(3,9);7,864(0,5);7,853(1,4);7,841 (1,4Example 1-1-245: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.691 (2.5), 9.675 (2.6), 8.610 (3.8), 8.607 (4.0); 8.392 (3.9), 7.864 (0.5), 7.853 (1.4), 7.841 (1.4
);7,829(0,5);7,605(4,2);7,593(5,4);7,583(0,3);7,308(1,1);7,298(1,1);7,295(1 ,2);7,291(1 ,2);7,286(1,1);7,279(1,2);7,269(1 ,0);5,756(2,3);5,403(7.829 (0.5), 7.605 (4.2), 7.553 (5.4), 7.583 (0.3), 7.308 (1.1), 7.298 (1.1), 7.295 (1, 2) 7,291 (1,2), 7,286 (1,1), 7,279 (1,2), 7,269 (1,0), 5,756 (2,3), 5,403 (U.S.
8,5):3,321(24,9);2,810(10,0);2,798(10,0);2,671(0,4):2,511(20,9);2,507(43,1);2,502(60,3):2,498(46,0);2,494(22,9);2,450(16,0);2,329(0,4) 45(0,4); 1 ,030(0,4):0,008(2,0);0,000(54, 1 );-0,008(2,2) 8.5) 3.321 (24.9); 2,810 (10.0); 2,798 (10.0); 2,671 (0.4) 2,511 (20.9); 2.507 (43.1); 2,502 (60 , 3): 2.498 (46.0), 2.494 (22.9), 2.450 (16.0), 2.329 (0.4) 45 (0.4); 1, 030 (0.4): 0.008 (2.0); 0.000 (54, 1); - 0.008 (2.2)
Beispiel 1-1-246: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,732(4.1);9,716(4,3);8,497(4,7);8,490(4,9);7,961(0,8);7,950(2.3);7,938(2,3);7,926(0,8Example 1-1-246: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.732 (4.1), 9.716 (4.3), 8.497 (4.7), 8.490 (4.9); 7,961 (0.8); 7,950 (2.3); 7,938 (2.3); 7,926 (0.8
):7,873(2,5);7,867(2,5);7,853(2,8);7,846(2,8);7,575(6,9);7,566(7,8);7,563(7,7);7,503(5,6);7,482(5,1);7,301(1,8);7,290(2,1):7,285(2,0);7,280( 1,8);7,274(2,4);7,263(1.6);6,052(0,7);6,034(2,6);6,016(2,6);5,998(0,8);5,756(8,8);4,345(1,3);4,335(1,3);4,039(0,5);4,021(0,5);37): 7,873 (2.5); 7,867 (2.5); 7,853 (2.8); 7,846 (2.8); 7,575 (6.9); 7,566 (7.8); 7,563 (7.7) 7.503 (5.6); 7.482 (5.1); 7.301 (1.8); 7.290 (2.1): 7.285 (2.0); 7.280 (1.8); 7.274 (2.4); 7,263 (1.6); 6,052 (0.7); 6,034 (2.6); 6,016 (2.6); 5,998 (0.8); 5,756 (8.8); 4,345 (1.3); 4,335 (1 , 3); 4,039 (0.5); 4,021 (0.5); 37
84(0,4):3,779(0,6);3,768(0,5);3,764(0,4);3,753(0,4);3,323(34,9);2,812(15,8);2,800(16,0);2,677(0,4);2,673(0,5);2,668(0,5);2,526(1,1);2,521(1 ,7);2,512(25,4);2,508(54,6);2,503(77,2);2,499(58,1);2,495(28,0);2,330(0,4);2,326(0,3);1,990(2,2);1,943(12,3):1,925(12,3);1,233(0,4);1,194( 0,6);1,176(1,2);1,158(0,6);1,046(11,6);1,031(11,5);0,008(0,8);0,000(26,3);-0,008(0,9) 84 (0.4) 3,779 (0.6); 3,768 (0.5); 3,764 (0.4); 3,753 (0.4); 3,323 (34.9); 2,812 (15.8); 2,800 (16.0); 2.677 (0.4); 2.673 (0.5); 2.668 (0.5); 2.526 (1.1); 2.521 (1, 7); 2.512 (25.4); 2.508 ( 54.6) 2,503 (77.2); 2,499 (58.1); 2,495 (28.0); 2,330 (0.4); 2,326 (0.3); 1,990 (2.2); 1,943 (12 , 3): 1.925 (12.3), 1.233 (0.4), 1.194 (0.6), 1.176 (1.2), 1.158 (0.6), 1.046 (11.6), 1.031 (11, 11) 5) 0.008 (0.8); 0,000 (26.3) - 0.008 (0.9)
Beispiel 1-1-247: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,684(2,2);9,667(2,3);8,616(3,7);8,398(3,7);7,865(1,7);7,846(1,7);7,615(4,5);7,605(3,9Example 1-1-247: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.684 (2.2), 9.667 (2.3), 8.616 (3.7), 8.398 (3.7 ); 7,865 (1.7); 7,846 (1.7); 7.615 (4.5); 7,605 (3.9
);7,304(0,9);7,294(1,1);7,287(1,1);7,282(1,0);7,278(1,1);7,266(0,8);5,756(0,5);5,391(7,4);4,084(0,7);4,067(1,1);4,049(1 ,0);4,033(0,7);3,32 6,9);2,507(31,9);2,503(42,3);2,499(32,4);2,455(13,9);1,157(16,0);1,141(16,0);0,000(2,1) ); 7,304 (0.9); 7,294 (1.1); 7.287 (1.1) 7.282 (1.0); 7,278 (1.1); 7,266 (0.8); 5,756 (0.5) 5.391 (7.4), 4.084 (0.7), 4.067 (1.1), 4.049 (1.0), 4.033 (0.7), 3.32, 6.9), 2.507 (31.9) ; 2,503 (42.3); 2,499 (32.4); 2.455 (13.9); 1.157 (16.0); 1.141 (16.0); 0,000 (2.1)
Beispiel 1-1-248: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,725(1 ,8);9,709(1 ,8);8,004(1 ,5);7,985(1 ,6);7,677(4,6);7,458(1 ,6);7,439(1 ,9);7,231 (1 ,6Example 1-1-248: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.725 (1, 8), 9.709 (1, 8), 8.004 (1.5), 7.985 (1, 6 7.677 (4.6); 7.459 (1, 6); 7.439 (1, 9); 7.231 (1, 6);
);7,213(2,3);7,196(1,4);5,563(6,3);4,344(0,5);4,334(0,5):4,093(0,6);4,076(1 ,0):4,058(1 ,0);4,042(0,7);3,322(12,8);2,634(11,1):2,526(0,5);2,517.213 (2.3); 7.196 (1.4); 5.563 (6.3); 4.344 (0.5); 4.334 (0.5): 4.093 (0.6); 4.076 (1, 0) 4.058 (1.0), 3.322 (12.8), 2.634 (11.1): 2.526 (0.5), 2.51
2(12,9);2,508(28,0);2,504(40,0);2,499(30,8):1,185(15,9);1,169(18,0):1,046(4,3):1,031(4,3);1,011 (0 );0,994(0,6);0,008(0,4);0,000(12,3);-2 (12.9) 2,508 (28.0); 2,504 (40.0); 2,499 (30.8) 1,185 (15.9); 1.169 (18.0) 1.046 (4.3): 1.031 (4.3); 1.011 (0); 0.994 (0.6); 0.008 (0.4); 0.000 (12.3); -
0,008(0,5) 0.008 (0.5)
Beispiel 1-1-249: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,727(3,8);9,711 (4,0);8,501 (4,6);8,494(4,8);8, 109(1 ,5);8,095(3,0);8,080(1 ,5);7,877 (2,4Example 1-1-249: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.727 (3.8), 9.711 (4.0), 8.501 (4.6), 8.494 (4.8 8, 109 (1, 5), 8.095 (3.0), 8.080 (1.5), 7.877 (2.4
);7,871(2,4);7,856(2,7);7,850(2,7);7,598(0,3):7,572(5,4);7,563(7,8);7,550(0,6);7,506{5,2);7,485(4,7);7,296(1,5);7,288(1 ,6);7,283(1,8);7,280( 1 ,9);7,275(1 ,8);7,271 (1 ,7);7,267(1 ,7);7,258(1 ,4);6,050(0,7);6,033(2,5);6,015(2,6);5,997(0,8);3,569(1 ,9);3,321(44,7);3,272(1 ,5);3,269(1 ,5);3,7,572 (5.4); 7,563 (7.8); 7,550 (0.6);): 7,871 (2.4); 7,856 (2.7);; 7.850 (2.7) 7.598 (0.3) 7.506 {5.2); 7.455 (4.7); 7.296 (1.5); 7.288 (1, 6); 7.283 (1.8); 7.280 (1, 9); 7.275 (1, 8); 7.271 (1, 7), 7.267 (1, 7), 7.258 (1, 4), 6.050 (0.7), 6.033 (2.5), 6.015 (2.6), 5.997 (0.8), 3.569 (1, 9); 3,321 (44,7); 3,272 (1, 5); 3,269 (1, 5); 3,
254(4,1);3,236(4,2);3,222(1,6);2,677(0,5);2,672(0,7);2,668(0,5):2,507(83,4):2,503(115,0);2,499(88,9);2,330(0,7);2,325(0,5);1,942(11 ,2):1,9(4.1) 254; 3,236 (4.2); 3,222 (1.6); 2,677 (0.5); 2,672 (0.7); 2,668 (0.5) 2,507 (83.4) 2,503 (115.0); 2.499 (88.9); 2.330 (0.7); 2.325 (0.5); 1.942 (11, 2): 1.9
24(11,2);1,548(0,5);1,530(2,5);1,511(5,1);1,493(5,2);1,476(2,8);1,458(0,6);1,046(0,3);1,031 (0,3);0,9 24 (11.2); 1,548 (0.5); 1,530 (2.5); 1,511 (5.1); 1,493 (5.2); 1,476 (2.8); 1,458 (0.6); 1,046 (0.3); 1.031 (0.3); 0.9
3);0,008(1,5);0,000(40,1)  3) 0.008 (1.5) 0.000 (40.1)
Beispiel 1-1-250: 1H-NMR(400,0 MHz. de-DMSO): δ= 9,730(5,6);9,714(5,8);8.507(7,0);8,502(7,5);8,171(2,4);8,157(4.8);8.143(2,6);7,887(3,6 );7,881(3,8);7,866(4,0);7,860(4,2);7,583(10,9);7,573(11,7);7,509(7,3);7,488(6,6);7,309(0,3);7,297(2,1);7,287(3,6);7,281^ Example 1-1-250: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.730 (5.6), 9.714 (5.8), 8.507 (7.0), 8.502 (7.5 8,171 (2,4); 8,157 (4.8); 8,143 (2.6); 7,887 (3,6); 7,881 (3,8); 7,866 (4.0); 7,860 (4,2); 7,583 (10.9) 7.573 (11.7); 7,509 (7.3); 7,488 (6.6); 7,309 (0.3); 7,297 (2.1); 7.287 (3.6); 7,281 ^
0(3,7);7,260(2,0);6,051(1,2);6,033(3,9);6,015(3,9);5,997(1,3);5,756(4,9);4,346(1,4);4,335(1,5);3,795(0,5);3,780(0,6);3,769(0,6);3,753(0,4);3, 324(50,9):3,198(0,5);3,180(3,6);3,176(4,0);3,162(7,3):3,149(4,1);3,145(4,1);3,126(0,8);3,110(0,3);2,673(0,7):2,504(117,7):2,330(0,8);1,948( 0 (3.7); 7,260 (2.0); 6,051 (1.2); 6,033 (3.9); 6,015 (3.9); 5,997 (1.3); 5,756 (4.9); 4.346 (1.4); 4.335 (1.5); 3.795 (0.5); 3.780 (0.6); 3.769 (0.6); 3.753 (0.4); 3, 324 (50.9): 3,149 (4.1); 3,145 (4.1); 3,126 (0.8); 3,110: 3,198 (0.5); 3,180 (3.6);; 3.176 (4.0) 3.162 (7.3) (1,948; 2,330 (0.8) (0.3) 2,673 (0.7) 2,504 (117.7)
15,9); 1,930(16,0); 1,445(0,4); 1,429(0,4); 1,233(0,^ 15.9); 1,930 (16.0); 1.445 (0.4); 1,429 (0.4); 1,233 (0 ^
);0,469(1,9);0,455(7,3);0,444(3,9);0,435(7,0);0,425(2,5);0,408(0,4);0,233(2,3);0,221(8,8);0,208(8,5);0,197(2,2);0,000(4,7) Beispiel 1-1-251 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9.811(2,6);9,795(2,7);7,952(0,6);7,747(4,4);7,741(4,4);7,715(6,8);7,687(2,5);7,668(2,8 );7,431(4,5);7,428(4,5);7,318(2,4);7,300(3,2);7,282(2,2);6,276(3,1);6,271(5,2);6,266(3,2);5.574(8,8);5,551(15,2);3,321(50,2);2,^); 0.469 (1.9) 0.455 (7.3) 0.444 (3.9) 0.435 (7.0) 0.425 (2.5) 0.408 (0.4) 0.233 (2.3) ; 0,221 (8.8); 0,208 (8.5); 0,197 (2.2); 0,000 (4.7) Example 1-1-251: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9,811 (2.6), 9.795 (2.7), 7.952 (0.6), 7.747 (4.4 7.741 (4.4); 7.715 (6.8); 7.687 (2.5); 7.688 (2.8); 7.431 (4.5); 7.428 (4.5); 7.318 (2.4) ; 7,300 (3.2); 7.282 (2.2); 6,276 (3.1); 6,271 (5.2); 6,266 (3.2); 5,574 (8.8); 5,551 (15.2); 3,321 (50.2); 2, ^
2(3,1);2,671(1,0);2,655(16,0);2,525(1,5);2,511(33,2);2,507(70,5);2,502(99,3);2,498(75,9);2,494(38,0);2,334(0,4);2,329(0,6);2,325(0,4);0 6(0,4);0,008(2,8);0,000(84,6);-0,008(3,4);-0,150(0,4) 2 (3.1); 2,671 (1.0); 2,655 (16.0); 2,525 (1.5); 2,511 (33.2); 2.507 (70.5); 2.502 (99.3); 2,498 (75.9); 2.494 (38.0); 2.334 (0.4); 2.329 (0.6); 2.325 (0.4); 0 6 (0.4); 0.008 (2.8); 0.000 (84.6) - 0.008 (3.4) - 0.150 (0.4)
Beispiel 1-1-252: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,645(2,7);9,629(2,8);8,655(5,5);8.344(3,5);8,339(3,6);7,631(1,7);7,625(1.7);7,610(2,3 );7.604(2,3);7,495(2,5);7,487(4,9);7,476(2,9);7,467(3,6);7,292(2,3);7,274(3,3);7,256(2,0);5,494(8,9);4,039(0,8);4,021(0,8);3,32 Example 1-1-252: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.645 (2.7), 9.629 (2.8), 8.655 (5.5), 8.344 (3.5 8.399 (3.6), 7.631 (1.7), 7.625 (1.7), 7.610 (2.3), 7.604 (2.3), 7.495 (2.5), 7.487 (4.9), 7.466 (2.9); 7,467 (3.6); 7,292 (2.3); 7,274 (3.3); 7.256 (2.0); 5,494 (8.9); 4,039 (0.8); 4,021 ( 0.8), 3.32
(0,4);2,507(51,8);2,503(70,5);2,499(53,5);2,430(16,0);2,330(0,4); 1 ,990(3,3); 1 ,563(1 ,7); 1 ,549(4,5); 1 ,542(4,7); 1 ,529(2,0); 1 ,305(2,2); 1.291 (4, 5); 1 ,285(4,7); 1 ,270(1 ,7); 1 ,280(0,3); 1 ,234(0,4); 1 , 194(0,9); 1 , 176(1, 7);1,158(1,0);0,008(1,0);0,000(24,0) (0.4); 2,507 (51.8); 2.503 (70.5); 2,499 (53.5); 2,430 (16.0); 2,330 (0.4); 1, 990 (3,3); 1, 563 (1, 7); 1, 549 (4,5); 1, 542 (4,7); 1, 529 (2,0); 1, 305 (2, 2); 1,291 (4, 5); 1, 285 (4,7); 1, 270 (1, 7); 1, 280 (0.3); 1, 234 (0.4); 1, 194 (0.9); 1, 176 (1, 7); 1.158 (1.0); 0.008 (1.0); 0.000 (24.0)
Beispiel 1-1-253: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,745(2,7);9,729(2,8);8,338(3,6);8,333(3,7);8,214(2,0);8,194(2,1);7,614(1,8);7,607(1,8Example 1-1-253: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.745 (2.7), 9.729 (2.8), 8.338 (3.6), 8.333 (3.7 ); 8,214 (2.0); 8.194 (2.1); 7,614 (1.8); 7,607 (1.8
);7,593(2,5);7,587(2,5);7,492(4,6);7,471(3,3);7,405(2,3);7,386(2,8);7,226(2,4);7,208(3,4);7,190(2,1);5,505(8,7);4,039(0,45;4,021 (0,4);3,852); 7,593 (2.5); 7,587 (2.5); 7,492 (4.6); 7,471 (3.3); 7,405 (2.3); 7,386 (2.8); 7,226 (2.4) 7,208 (3.4), 7.190 (2.1), 5.055 (8.7), 4.039 (0.45, 4.021 (0.4), 3.852
0,3);3,829(0,9);3,818(0,8);3,808(0,9);3,785(0,3);3,323(19,2);2,526(0,8);2,513(16,1);2,508(33,7);2,504(47,0);2,499(35,8);2,426(16,0);1,990(0.3); 3,829 (0.9); 3,818 (0.8); 3,808 (0.9); 3,785 (0.3); 3,323 (19.2); 2,526 (0.8); 2,513 (16 , 1), (1,990; 2,508 (33.7); 2,504 (47.0); 2,499 (35.8); 2,426 (16.0)
1,8);1,860(1,6);1,847(1,4);1,837(1,6);1,829(1,6);1,689(1.4);1,678(1,3);1,666(1,6);1,656(1,7);1,563(0,7);1,554(0,7);1,532(0 1.8); 1,860 (1.6); 1,847 (1.4); 1,837 (1.6); 1,829 (1.6); 1,689 (1.4); 1,678 (1.3); 1,666 (1.6 ); 1,656 (1.7); 1,563 (0.7); 1,554 (0.7); 1,532 (0
97(0,5);1,379(1,5);1,352(1,7);1,320(1,1);1.295(1 ,0);1.288(1.2);1,265(2,3);1 ,240(2,1);1 ,217(1,0);1,194(  97 (0.5), 1.379 (1.5), 1.352 (1.7), 1.320 (1.1), 1.295 (1, 0), 1.288 (1.2), 1.265 (2.3), 1.228 (2.1); 1, 217 (1.0); 1.194 (
0,000(20,6);-0,008(0,8)  0,000 (20.6) - 0.008 (0.8)
Beispiel 1-1-254: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,703(3,7);9,686(3,8);8,007(3,2);7,998(3,3);7,804(8,7);7,803(8,5);7,755(2,4);7,733(3,9 );7,675(2,1 );7,672(2,2);7,656(2,6);7,653(3,3);7,634(1 ,6); 7,632(1 ,5);7,340(1 ,9);7.338(2,0);7,321 (3,6);7,305(1 ,8);7,303(1 ,7);6,222(0.8);6,204( 2,6);6,186(2,6);6,169(0,8);5,756(16,0);4,335(0,3);3,324(21,0);2,793(0,4);2,783(1,0);2,774(1,6);2,765(2,3);2,756(2,3);2,747(1,6);2,738(1,1);2 ,728(0,4);2,674(0,4);2,527(1,2);2,509(49,0);2,505(67,5);2,500(50,8);2,332(0,4);1,930(12,3);1,912(12,3);1,047(2,8);1,032(2,8);0,741 (1,4);0,7Example 1-1-254: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.703 (3.7), 9.686 (3.8), 8.007 (3.2), 7.998 (3.3 7.804 (8.7); 7.803 (8.5); 7.755 (2.4); 7.733 (3.9); 7.675 (2.1); 7.672 (2.2); 7.656 (2.6) 7.653 (3.3); 7.634 (1, 6); 7,632 (1, 5), 7,340 (1, 9), 7,338 (2,0), 7,321 (3,6), 7,305 (1, 8), 7,303 (1, 7), 6,222 (0.8), 6,204 (2 , 6); 6,186 (2.6); 6,169 (0.8); 5,756 (16.0); 4,335 (0.3); 3,324 (21.0); 2,793 (0.4); 2,783 (1, 2,774 (1,6); 2,765 (2,3); 2,756 (2,3); 2,747 (1,6); 2,738 (1,1); 2,728 (0,4); 2,674 (0 , 4); 2,527 (1.2); 2,509 (49.0); 2,505 (67.5); 2,500 (50.8); 2,332 (0.4); 1,930 (12.3); 1,912 (12, 3), 1.047 (2.8), 1.032 (2.8), 0.741 (1.4), 0.7
29(3,7);0,724(5,0);0,712(4,9);0,706(4,0);0,695(1 ,6);0,505(1,7);0,494(4,7);0,488(4,5);0,484(4,2);0,479(4,2);0,467(1,3);0,008(0,7);0,000(21^ ;-0,008(0,7) 29 (3.7); 0.724 (5.0); 0.712 (4.9); 0.706 (4.0); 0.695 (1, 6); 0.555 (1.7); 0.494 (4.7); 0.488 (4.5); 0.484 (4.2); 0.479 (4.2); 0.467 (1.3); 0.008 (0.7); 0.000 (21 ^; -0.008 (0.7)
Beispiel 1-1-255: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,745(2,7);9,728(2,8);8,333(3,9);8,328(3,7);8,284(1,3);8.269(2,6);8,255(1,3);7,615(1,8Example 1-1-255: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.745 (2.7), 9.728 (2.8), 8.333 (3.9), 8.328 (3.7 ); 8.284 (1.3); 8,269 (2.6); 8,255 (1.3); 7.615 (1.8
);7,608(1,7);7,594(2,6);7,588(2,4);7,493(4,5);7,472(3,2);7,405(2,4);7,386(2,9);7,224(2,3);7,207(3,3);7,189(2,0);5,513(9,0);3,323(27,8);3,177 (3,0);3,161 (5,4);3, 145(3,1 );2,673(0,3);2,508(46,9);2,504(60,0);2,499(45,3);2,427(16,0);2,331 (0,4); 1 ,990(1 ,3); 1 ,732(2,2); 1 ,702(4,5); 1 ,671 (2. 4); 1 ,634(1 ,3); 1 ,611 (1 ,0); 1 ,485(0,3); 1 ,468(0,^ ); 7,608 (1.7); 7,594 (2.6); 7,588 (2.4); 7,493 (4.5); 7,472 (3.2); 7,405 (2.4); 7,386 (2.9) 7.244 (2.3), 7.207 (3.3), 7.189 (2.0), 5.513 (9.0), 3.323 (27.8), 3.177 (3.0), 3.161 (5.4); 3.155 (3.1), 2.673 (0.3), 2.508 (46.9), 2.504 (60.0), 2.499 (45.3), 2.447 (16.0), 2.321 (0.4) ; 1, 990 (1, 3); 1, 732 (2, 2); 1, 702 (4,5); 1, 671 (2. 4); 1, 634 (1, 3); 1, 611 (1, 0); 1, 485 (0.3); 1, 468 (0, ^
(1,4);1,194(2,1);1.189(2,2);1,176(1.6);1, 162(2.7^ (1.4), 1.194 (2.1), 1.189 (2.2), 1.176 (1.6), 1.162 (2.7 ^
Beispiel 1-1-256: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,749(2,8);9,733(2,8);8,333(3,7);8,328(3,8);8,288(1,3);8,273(2,5);8,259(1,3);7,613(1,7Example 1-1-256: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.749 (2.8), 9.733 (2.8), 8.333 (3.7), 8.328 (3.8 ); 8,288 (1.3); 8,273 (2.5); 8,259 (1.3); 7,613 (1.7
);7,607(1,7);7,593(2,3);7,587(2,3);7,494(4,2);7,473(3,0);7,406(2,4);7,387(2,8);7,225(2,1);7,208(3,3);7,190(1,8);5,513(9,1);3,322(18,8);3,262 (3,1);3,246(5,0);3,230(3,2);2,673(0,4);2,503(67,2);2,428(16,0);2,330(0,4);2,094(0,5);2,076(1,3);2,057(1,8);2,039(1,4);2,020(0,6);1,990(1,2);); 7,607 (1.7); 7,593 (2.3); 7,587 (2.3); 7,494 (4.2); 7,473 (3.0); 7,406 (2.4); 7.387 (2.8) 7.225 (2.1); 7.208 (3.3); 7.190 (1.8); 5.513 (9.1); 3.322 (18.8); 3.262 (3.1); 3.246 (5.0); 3,230 (3.2); 2,673 (0.4); 2,503 (67.2); 2,428 (16.0); 2,330 (0.4); 2,094 (0.5); 2,076 (1.3); 2,057 (1.8); 2,039 (1.4); 2,020 (0.6); 1,990 (1.2);
1 ,744(0,6); 1 ,727(1 ,3); 1 ,715(1 ,8); 1 ,697(2,0); 1 ,685(1 ,5); 1, 744 (0.6); 1, 727 (1, 3); 1, 715 (1, 8); 1, 697 (2,0); 1, 685 (1, 5);
7);1,508(2,1);1 ,498(1,5);1,490(1,3);1 ,280(0,7);1,264(1,7);1,246(2,0);1,233(1,9);1,217(1,4):1,194(0,6);1,176(0,6);0,000(13,7)  7); 1.508 (2.1); 1.498 (1.5); 1.490 (1.3); 1, 280 (0.7); 1.264 (1.7); 1.246 (2.0); 1.233 1,194 (0.6); 1,176 (0.6); 0,000 (13.7) 1,217 (1.4) (1.9)
Beispiel 1-1-257: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,528(0,8);9,512(0,9);8,403(1 ,4);8,398(1 ,4);7,825(0,5);7,806(0,6);7,551 (0,9);7,532(1 ,0Example 1-1-257: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.528 (0.8); 9.512 (0.9); 8.403 (1, 4); 8.398 (1, 4 7.825 (0.5); 7.806 (0.6); 7.551 (0.9); 7.532 (1.0)
);7,471(1,7);7,451(1,5);7,268(0,9);7,250(1,4);7,232(0,8);4,343(1,3);4,335(1 ,3);3,792(0,6);3,785(0,6);3,776(0,8);3,770(0,8);3,762(0,6);3,755( 0,6);3,665(6,7);3,323(4,5);2,670(0,4);2,629(0,5);2,503(29,1);1 ,947(3,0);1,930(2,9);1,234(0,4);1,046(16,0);1,030(16,0);0,000(10,7)7.471 (1.7), 7.451 (1.5), 7.268 (0.9), 7.250 (1.4), 7.232 (0.8), 4.343 (1.3), 4.335 (1, 3) 3.792 (0.6), 3.785 (0.6), 3.776 (0.8), 3.770 (0.8), 3.762 (0.6), 3.755 (0.6), 3.665 (6.7); 3.323 (4.5), 2.670 (0.4), 2.629 (0.5), 2.503 (29.1), 1.947 (3.0), 1.930 (2.9), 1.234 (0.4) ; 1,046 (16.0); 1.030 (16.0); 0.000 (10.7)
Beispiel 1-1-258: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,786(2,5);9,769(2,6);8,432(4,2);8,426(4,3);8, 146(1.6)7,848(1 ,4);7,829(1 ,5);7,485(6,2Example 1-1-258: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.786 (2.5); 9.769 (2.6); 8.432 (4.2); 8.426 (4.3 8, 146 (1.6) 7.848 (1, 4), 7.829 (1.5), 7.455 (6.2
);7,464(8,2);7,445(3,3);7,231 (3,2);7,214(4,7);7,196(2,8);6,200(1,0);6,189(1 ,0);5,755(2,4);4,341 (0,7);4,331(0,7);3,319(19,5);3,274(0,4);3,25 (0,9);3,241 (1,8);3,224(2,6);3,208(2,2);3,191 (1,3);3,182(1,5);3,166(1,8);3,149(1,2);3,134(0,7);2,671( 7,464 (8,2); 7,445 (3,3); 7,231 (3,2); 7,214 (4,7); 7,196 (2,8); 6,200 (1,0); 6,189 (1, 0) 5.755 (2.4), 4.341 (0.7), 4.331 (0.7), 3.319 (19.5), 3.274 (0.4), 3.25 (0.9), 3.241 (1.8 3.244 (2.6); 3.208 (2.2); 3.191 (1.3); 3.182 (1.5); 3.166 (1.8); 3.149 (1.2); 3.134 (0.7); (2,671
25(1 ,4);2,511 (30,6);2,507(62,2);2,503(82,3);2,498(60,7);2,334(0,4):2,329(0,6);2,325(0,4);1 ,986(9, 7);1 ,969(9,6); 1 ,509(0,6); 1 ,491 (2,6);1 ,472( 5,3);1,454(5,5);1,436(2,9);1,418(0,7);1,046(4,9);1,031(4,8);0,884(8,1);0.866(16,0);0.847(7,2);0,008(0,6);0,000(18,1);-0,008(0,7) 25 (1,4), 2,511 (30,6), 2,507 (62,2), 2,503 (82,3), 2,498 (60,7), 2,334 (0,4): 2,329 (0,6), 2,325 (0.4); 1, 986 (9, 7); 1, 969 (9.6); 1, 509 (0.6); 1, 491 (2.6), 1.472 (5.3), 1.454 (5.5), 1.436 (2.9), 1.418 (0.7), 1.046 (4.9), 1.031 (4, 8); 0.884 (8.1) 0.866 (16.0); 0.847 (7.2) 0.008 (0.6); 0,000 (18.1) - 0.008 (0.7)
Beispiel 1-1-259: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,416(0,3);7,479(0,7);7,458(0,6);7,234(0,4);3,804(0,4);3,788(1,1);3,773(1,5);3,758(1.1Example 1-1-259: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.416 (0.3); 7.499 (0.7); 7.458 (0.6); 7.234 (0.4 ); 3,804 (0.4); 3,788 (1.1); 3,773 (1.5); 3,758 (1.1
);3,742(0,5);2,524(0,3);2,511 (7,3);2,507(14,4);2.502(18,4);2,498(12,6);2.493(5,7);1.966(0,8);1,^ 3.742 (0.5), 2.524 (0.3), 2.511 (7.3), 2.507 (14.4), 2.502 (18.4), 2.498 (12.6), 2.493 (5.7) ; 1,966 (0.8); 1 ^
1,024(0,3);0,675(0,4);0,662(0,4);0,436(0,4);0,431(0,4);0,426(0,4);0,421(0,3);0,000(4,1)  1,024 (0.3); 0,675 (0.4); 0,662 (0.4); 0.436 (0.4) 0.431 (0.4) 0.426 (0.4) 0.421 (0.3); 0,000 (4.1)
Beispiel 1-1-262: 'H-NMR(400.0 MHz, de-DMSO): δ= 9,508(1 ,7);9,492(1 ,8);7,797(4,2);7.737(0,5);7,718(1 ,4)7,700(1 ,6)7,698(1 ,6)7,688(2,0 Example 1-1-262: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.508 (1, 7), 9.492 (1.8), 7.797 (4.2), 7.737 (0.5); 7.718 (1, 4) 7.700 (1.6) 7.688 (1.6) 7.688 (2.0
);7,668(0,6);7,354(0,9);7,350(0,8);7,337(1,6);7,333(1,5);7,320(0,8);7,316(0,8);6,191(0,4);6,174(1,3);6,156( ); 7.668 (0.6); 7,354 (0.9); 7,350 (0.8); 7,337 (1.6); 7,333 (1.5); 7,320 (0.8); 7,316 (0.8) ; 6,191 (0.4); 6,174 (1.3); 6,156 (
16,0);3,352(4,5);2,509(24,9);2,504(34,0);2,500(25,4); 1 ,902(6,2); 1 ,884(6, 1 ); 1.047(0,5); 1,031 (0,5);0,000(3,8) 16.0) 3,352 (4.5); 2,509 (24.9); 2,504 (34.0); 2,500 (25.4); 1, 902 (6,2); 1, 884 (6, 1); 1,047 (0.5); 1.031 (0.5); 0.000 (3.8)
Beispiel 1-1-263: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,626(2,6);9,610(2,6);8,535(5,2);8,355(3,4);8,349(3,5);7,642(1,8);7,636(1,8);7,621 (2,3Example 1-1-263: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.626 (2.6); 9.610 (2.6); 8.535 (5.2); 8.355 (3.4 8.349 (3.5), 7.642 (1.8), 7.636 (1.8), 7.621 (2.3
);7,615(2,4);7,494(4,8);7,487(2,5);7,473(4,3);7,469(3,0);7,280(2,5);7,262(3,3);7,244(2,2);5,512(8,4);4,056(0,6);4,038(1 ,8);4,021 (1,8);4,003(); 7.615 (2.4); 7,494 (4.8); 7,487 (2.5); 7,473 (4.3); 7.469 (3.0); 7,280 (2.5); 7,262 (3.3) 7.244 (2.2); 5.512 (8.4); 4.056 (0.6); 4.038 (1, 8); 4.021 (1.8); 4.003 (
0,6);3,318(17,4);2,676(0,4);2,671(0,5);2,666(0,4);2,524(1,2);2,520(1,9);2,511(32,5);2,506(67,9);2,502(90,7);2,497(65,3);2,493(31,7);20.6); 3,318 (17.4); 2,676 (0.4); 2,671 (0.5); 2,666 (0.4); 2,524 (1.2); 2,520 (1.9); 2,511 (32 , 5); 2,506 (67.9); 2.502 (90.7); 2.497 (65.3); 2,493 (31.7); 2
16,0);2,333(0,5);2,329(0,7);2,324(0,6);2,299(1,3);2,269(1,5);1,989(7,9);1,881(1,0);1,857(1,7);1,832(1,0);1,683( 16.0) 2.333 (0.5); 2,329 (0.7); 2,324 (0.6); 2,299 (1.3); 2,269 (1.5); 1,989 (7.9); 1,881 (1 (1.683;, 0); 1,857 (1.7); 1,832 (1.0)
562(2,1);1,548(1,9):1,538(2,0);1,506(0,6);1,405(0,4);1,397(0,5);1,380(0,7);1,370(0,7);1,356(0,7);1,345(0,6);1,299(0,4);1,259(0,5);1,235(0,5) ; 1 , 193(2, 1 ); 1 , 175(4, 1 ); 1 , 157(2, 1 );0,000(9,2);-0,009(0,3)  562 (2.1); 1,548 (1.9) 1,538 (2.0); 1,506 (0.6); 1,405 (0.4); 1,397 (0.5); 1,380 (0.7); 1,370 (0.7); 1.356 (0.7); 1.345 (0.6); 1.299 (0.4); 1.259 (0.5); 1.235 (0.5); 1, 193 (2, 1); 1, 175 (4, 1); 1, 157 (2, 1); 0.000 (9.2); - 0.009 (0.3)
Beispiel 1-1-264: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,835(4,9);9,738(2,5);9,722(2,6);8,384(3,4);8,379(3.5);8,287(2.1);8,285(2.2);8,283(2,Example 1-1-264: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.835 (4.9), 9.738 (2.5), 9.722 (2.6), 8.384 (3.4 ) 8,379 (3.5) 8,287 (2.1); 8,285 (2.2); 8,283 (2,
0);8,275(2,3);8,273(2,1);8,271 (2,0);8,255(3,3);8,234(3,6);7,801 (1 ,2)7,796(1 ,2)7,779(2,0)7,762(1 ,2)7,757(1 ,2);7,695(1, 9)7,689(1 ,8)7,674 (2,3);7,668(2,3);7,536(2,3);7,517(2,8);7,507(4,4);7,486(3,4);7^ 8,275 (2,3); 8,255 (3,3); 8,234 (3,6); 7,801 (1, 2) 7,796 (1, 2) 7.799 (2.0) 7.762 (1, 2) 7.757 (1, 2); 7.695 (1.9) 7.689 (1, 8) 7.674 (2.3); 7.668 (2.3); 7.536 (2.3 7 ^); 7,517 (2.8); 7,507 (4.4); 7,486 (3.4)
49(1, 9)7,046(1, 8);7,037(1 ,7)7,034(1, 7);5,757(1 ,2);5,564(8,6);3,320(32,7);2,676(0,5);2,671 (0,6);2,667(0,5);2,525(1 ,6);2,511 (36,9);2,507(75 49 (1, 9) 7,046 (1, 8), 7,037 (1, 7) 7,034 (1, 7), 5,757 (1,2), 5,564 (8,6), 3,320 (32,7), 2,676 (0 , 5), 2.671 (0.6), 2.667 (0.5), 2.525 (1.6), 2.511 (36.9), 2.507 (75
,6);2,502(99,4);2,498(71,6);2,493(34,7);2,458(16,0);2,334(0,4);2,329(0,6);2,324(0,4);1,352(0,4);1.226(0,5);0,146(0,3);0,008(2,9);0,000(81,1 );-0,009(3,0);-0,150(0,3) , 6); 2.502 (99.4); 2,498 (71.6); 2,493 (34.7); 2.458 (16.0); 2,334 (0.4); 2,329 (0.6); 2,324 (0, 4), 1.352 (0.4), 1.226 (0.5), 0.146 (0.3), 0.008 (2.9), 0.000 (81.1), -0.009 (3.0), -0.150 (0 , 3)
Beispiel 1-1-265: 1H-NMR(400,0 MHz, de-DMSO): δ= 11,039(5,2);9,728(2,7);9,712(2,7);8.642(9,1);8,630(9,3);8.387(3,4);8,382(3,7);7,699(1,Example 1-1-265: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11.039 (5.2), 9.728 (2.7), 9.712 (2.7), 8.642 (9.1 ); 8,630 (9.3); 8,387 (3.4); 8,382 (3.7); 7,699 (1,
7)7,692(1, 9);7,678(2,1);7,672(2,3);7,554(2,3);7,535(2,8);7,507(4,1);7,486(3,3);7,355(2,1);7,337(3,2);7,319(1,8);7,144(2,6);7,132(4,8);7,1207) 7,692 (1, 9); 7,678 (2,1); 7,672 (2,3); 7,554 (2,3); 7,535 (2,8); 7,507 (4,1); 7,486 (3,3) ; 7,355 (2.1); 7,337 (3.2); 7,319 (1.8); 7,144 (2.6); 7,132 (4.8); 7,120
(2,5);5,757(5,5);5,560(8,8);3,319(44,3);2,671(0,8);2,506(101,9);2,502(137,2);2,498(110,7);2,459^ (2,498 (2.5); 5,757 (5.5); 5,560 (8.8); 3,319 (44.3); 2,671 (0.8); 2,506 (101.9); 2.502 (137.2) 110.7); 2,459 ^
30(0,5);0, 146(0,4);0,008(3,4);0,000(76,3);-0, 150(0,4) Beispiel 1-1-267: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,025(2,4);10,009(2,5);7,697(6,3):7.619(2,2);7.600(2,5);7,275(2,2);7,257(3,1);7,239(2 ,0);5,533(9,0);3,321(12,7);2,915(3,8);2,897(5,6);2,878(4,1);2,677(0,4);2,673(0,6);2,665(0,8);2,643(16,0);2,526(1 ,0);2,512(28,1);2 2,504(70,9);2,499(50,4);2,330(0,4);1,677(0,5);1,658(2,1);1,640(3,9);1,621(3,9);1, 603(2^ 30 (0.5); 0.146 (0.4); 0.008 (3.4); 0.000 (76.3); -0.150 (0.4) Example 1-1-267: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.025 (2.4); 10.009 (2.5); 7.697 (6.3): 7.619 (2.2 7,600 (2.5); 7.275 (2.2); 7.257 (3.1); 7.239 (2, 0); 5.533 (9.0); 3.321 (12.7); 2.915 (3.8) 2.887 (5.6); 2.878 (4.1); 2.677 (0.4); 2.673 (0.6); 2.665 (0.8); 2.643 (16.0); 2.526 (1.0); 2.512 (28.1), 2.504 (70.9), 2.499 (50.4), 2.330 (0.4), 1.677 (0.5), 1.658 (2.1), 1.640 (3.9); 1,621 (3,9); 1, 603 (2 ^
5(0,4);0,841 (0,5);0,822(0,4);0,803(0,5);0,008(1 ,0);0,000(25,8);-0,008(1 ,1 ) 5 (0.4), 0.841 (0.5), 0.822 (0.4), 0.803 (0.5), 0.008 (1, 0), 0.000 (25.8), - 0.008 (1, 1)
Beispiel 1-1-269: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,561(5,0);9,545(5,3);9,522(9.1):8,679(8,1);8,676(8,5);8,423(8,1);8,422(8,2);7,750(1,1Example 1-1-269: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.561 (5.0); 9.545 (5.3); 9.522 (9.1): 8.679 (8.1); 8,676 (8.5); 8,423 (8.1); 8,422 (8.2); 7,750 (1.1
);7,747(1,2);7,728(3,7);7,725(4,0);7,708(9,5);7,705(6,7);7,685(1,5);7,384(2,4);7,379(2,4);7,374(1,2);7,367(4,5);7,362(4,5);7,351 (3,4);7,345( 2,6);7,337(3,2);7,319(1,6);7,316(2,3);7,300(1,1);7,211(1,0);7,202(6,6);7,182(10,0);7,161(4,2);7,152(0,^ ); 7.747 (1.2); 7,728 (3.7); 7,725 (4.0); 7,708 (9.5); 7,705 (6.7); 7,685 (1.5); 7,384 (2.4) 7,379 (2,4); 7,374 (1,2); 7,367 (4,5); 7,362 (4,5); 7,351 (3,4); 7,345 (2,6); 7,337 (3,2); 7,319 (1.6); 7,316 (2.3); 7,300 (1.1); 7,211 (1.0); 7,202 (6.6); 7.182 (10.0); 7,161 (4.2); 7,152 (0 ^
,335(0,7);3,569(0,9);3,323(19,5);2,676(0,4);2,672(0,6);2,667(0,5);2,525(1,5);2,512(38,3):2,508(79,5):2,503(105,4);2,499(75,7);2,494(37,0); 2,467(32.9);2,334(0.4);2,330(0,6);2.325(0,5); 1 ,046(4,3); 1,031 (4.2);0,000(1,5)  , 335 (0.7); 3,569 (0.9); 3,323 (19.5); 2,676 (0.4); 2,672 (0.6); 2,667 (0.5); 2,525 (1.5); 2,512 (38.3) 2,508 (79.5) 2.503 (105.4); 2,499 (75.7); 2,494 (37.0); 2,467 (32.9); 2,334 (0.4); 2,330 (0.6); 2,325 (0.5); 1, 046 (4,3); 1.031 (4.2); 0.000 (1.5)
Beispiel 1-1-270: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,584(4,6);9,568(4,7);8.437(8,4);7,903(3,7);7,881 (5,2);7,841 (11 ,9);7,788(2.6);7,785(2,Example 1-1-270: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.584 (4.6), 9.568 (4.7), 8.437 (8.4), 7.903 (3.7 7,881 (5,2), 7,841 (11, 9), 7,788 (2.6), 7,785 (2,
7);7,769(3,1);7,766(4,3);7,747(2,1);7,745(2,1);7,387(2,4);7,384(2,5);7,368(4,5);7,352(2,2);7,349(2,2);5,758(10,5);5,438(16,0);3,569(0,6);3 28(14,5);2,677(0,6);2,672(0,9);2,668(0,6):2,526(2,2);2,512(53,6);2,508(110,6);2,503(146,5);2,499(105,7);2,495(51,8);2,335(0,6);2,330(0,9) 2,326(0,6): 1 ,562(2,8); 1 ,547(7,3); 1 ,540(7,7); 1 ,527(3,5); 1 ,487(0,3); 1 ,349(0,3); 1 ,309(3,6); 1 ,296(7,2); 1 ,289(7,7); 1 ,275(2,8); 1 ,235(0,7); 1 ,046(0, 4);1,031(0,4);0,008(0,4);0,000(12,1);-0,008(0,5) 7); 7,769 (3.1); 7,766 (4.3); 7.747 (2.1) 7.745 (2.1), 7.387 (2.4); 7,384 (2.5); 7,368 (4.5 7.352 (2.2), 7.349 (2.2), 5.758 (10.5), 5.438 (16.0), 3.569 (0.6), 3 28 (14.5), 2.677 (0.6 ); 2,672 (0.9); 2,668 (0.6) 2,526 (2.2); 2,512 (53.6); 2,508 (110.6); 2.503 (146.5); 2.499 (105.7) 2.495 (51.8); 2.335 (0.6); 2.330 (0.9) 2.326 (0.6): 1.562 (2.8); 1, 547 (7,3); 1, 540 (7,7); 1, 527 (3,5); 1, 487 (0.3); 1, 349 (0.3); 1, 309 (3,6); 1, 296 (7,2); 1, 289 (7, 7); 1, 275 (2,8); 1, 235 (0.7); 1, 046 (0, 4), 1.031 (0.4), 0.008 (0.4), 0.000 (12.1), - 0.008 (0.5)
Beispiel 1-1-271 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,630(0,8);9,613(0,8);8.538(1,4);8,498(1.0);8,492(1,0);7,879(0,5);7,873(0,5):7,858(0,6Example 1-1-271: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.630 (0.8); 9.613 (0.8); 8.538 (1.4); 8.498 (1.0); 8.492 (1.0); 7,879 (0.5); 7,873 (0.5) 7,858 (0.6
);7,852(0,6);7,666(0,6);7,648(0,7);7,633(1,0);7,613(0,4);7,503(1,1);7,482(1 ,0);7,358(0,4);7,341 (0,7);7,327(0,3);7,324(0,4);6,013(0,6);5,9 0,6);3,834(0,4);3,777(0,6);3,568(16,0);2,507(19,9);2,503(26,8);2,499(21,9);1,930(2,3);1,912(2,3);1, 543(0,5);1 ,529(1 ,2);1 ,523(1,4); 1 ,510(0,6 ); 1 ,290(0,6); 1,277(1,2); 1,270(1 ,3); 1,256(0,5) 7.852 (0.6), 7.666 (0.6), 7.648 (0.7), 7.633 (1.0), 7.613 (0.4), 7.503 (1.1), 7.482 (1, 0) 7.358 (0.4), 7.341 (0.7), 7.327 (0.3), 7.324 (0.4), 6.013 (0.6), 5.9 0.6), 3.834 (0.4) ; 3,777 (0.6); 3,568 (16.0); 2.507 (19.9); 2.503 (26.8); 2,499 (21.9); 1,930 (2.3); 1,912 (2.3); 1, 543 (0.5); 1, 529 (1, 2); 1, 523 (1.4); 1, 510 (0.6); 1, 290 (0.6); 1,277 (1.2); 1,270 (1, 3); 1.256 (0.5)
Beispiel 1-1-272: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,602(10,7);9,581(5,4);8,551(6,6);8,544(6,7);7,938(3,4);7,931(3,5);7,917(3,9);7.910(3, 8);7,711 (1 ,3);7,708(1 ,4);7,689(3,8);7,686(3,8);7,672(4,7);7,669(5, 1);7,661 (6,1);7,641 (1 ,8);7,528(7,7);7,507(7,0);7,370(2,6);7,366(2,5);7,353 (5,9);7,349(5,0);7,337(5,4);7,332(3,7);7,316(2,5);7,300(1,1);7.216(0,6);7.211(1,0);7,202(6.7);7,182(1^ Example 1-1-272: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.602 (10.7), 9.581 (5.4), 8.551 (6.6), 8.544 (6.7 7,938 (3, 4), 7,931 (3,5), 7,917 (3,9), 7,910 (3, 8), 7,711 (1, 3), 7,708 (1, 4), 7,689 (3,8) 7,686 (3,8); 7,672 (4,7); 7,669 (5,1); 7,661 (6,1); 7,641 (1, 8); 7,528 (7,7); 7,507 (7,0); 7.370 (2.6), 7.366 (2.5), 7.353 (5.9), 7.349 (5.0), 7.337 (5.4), 7.332 (3.7), 7.316 (2.5), 7.300 (1.1); 7,216 (0.6); 7,211 (1.0); 7,202 (6.7); 7.182 (1 →
100(1 ,1);6,082(3,5);6,064(3,6);6,046(1 ,0);5,757(2,2);3,321 (58,5);2,676(1 ,0);2,671 (1 ,4);2,667(1 ,0);2,525(3,5);2,511(88,1);2,507(181,7);2,50 2(239,7);2,498(172,1);2,493(83,1);2,333(1,1);2,329(1,4);1,982(16,0);1,965(15,9);1,232(0,3);1,045(0,6);1,030(0,7);0,000(5,4)  100 (1,1), 6,082 (3,5), 6,064 (3,6), 6,046 (1, 0), 5,757 (2,2), 3,321 (58,5), 2,676 (1, 0), 2,671 (1, 4); 2.667 (1, 0); 2.525 (3.5); 2.511 (88.1); 2.507 (181.7); 2.50 2 (239.7); 2.498 (172.1) ; 2,493 (83.1); 2,333 (1.1); 2,329 (1.4); 1,982 (16.0); 1,965 (15.9); 1,232 (0.3); 1,045 (0.6); 1,030 (0.7); 0,000 (5.4)
Beispiel 1-1-273: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,124(4,6);9,107(4,7);7,857(12,4);7,806(3,8);7,784(4,8);7,630(2,5);7,627(2,6);7,612(3,Example 1-1-273: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.124 (4.6), 9.107 (4.7), 7.857 (12.4), 7.806 (3.8 ); 7,784 (4.8); 7,630 (2.5); 7.627 (2.6) 7.612 (3,
1);7,609(4,4);7,606(2,5);7,590(2,3);7,587(2,3);7,227(2,4);7,224(2,5);7,208(4,2);7,207(4,2);7,192(2,3);7,188(2,2);5,758(7,3);5,400(16 ;3,70 5(0,8);3,491(0,8);3,323(44,3);2,677(0,5);2,673(0,7);2,668(0,5);2,526(1 ,7);2,521(2,6);2,513(41,3);2,508(86,0);2,504(114,1);2,499(80,5)i 5(37,8);2,335(0,5);2,330(0,7);2,326(0,5);1 ,853(4,7); 1 ,837(12,4);! ,820(4,6); 1 ,234(1 ,6);0,008(0,7);0,000(24,0);-0,009(0,8) 1); 7,609 (4.4); 7,606 (2.5); 7,590 (2.3); 7,587 (2.3); 7.227 (2.4); 7,224 (2.5); 7,208 (4.2 7,207 (4,2); 7,192 (2,3); 7,188 (2,2); 5,758 (7,3); 5,400 (16; 3,70 5 (0,8); 3,491 (0,8) 3.323 (44.3), 2.677 (0.5), 2.673 (0.7), 2.668 (0.5), 2.526 (1, 7), 2.521 (2.6), 2.513 (41.3); 2.508 (86.0), 2.504 (114.1), 2.499 (80.5), i5 (37.8), 2.355 (0.5), 2.330 (0.7), 2.326 (0.5), 1 , 853 (4,7); 1,837 (12,4);, 820 (4,6); 1, 234 (1,6); 0,008 (0,7); 0,000 (24,0); 0.009 (0.8)
Beispiel 1-1-274: 1H-NMR(400.0 MHz, de-DMSO): δ= 10,390(4,4);9,625(2,6);9,609(2,6);8,243(2,5);8,231 (2.6);7,806(1 ,3);7,784(1 ,9);7,760(1 ,Example 1-1-274: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.390 (4.4); 9.625 (2.6); 9.609 (2.6); 8.243 (2.5); 8,231 (2.6), 7.806 (1, 3), 7.784 (1, 9), 7.760 (1,
4);7,721(5,9);7,591(2,3);7,572(2,6);7,334(1,9);7,316(3,1);7,299(2,1);7,293(1,9);7,282(2,0);7,272(1,6);7,262(0,9);5,757(13,^ 4); 7.721 (5.9) 7.591 (2.3); 7,572 (2.6); 7,334 (1.9); 7,316 (3.1); 7,299 (2.1); 7,293 (1.9 ); 7.282 (2.0); 7,272 (1.6); 7,262 (0.9); 5,757 (13, ^
0(15,4);3, 175(0,6);3, 162(0,6);2,706(0,4);2,667(16,0);2,502(136,7);2,329(0,8);0, 146(0,4);0,000(81 ,6);-0, 150(0,4)  3, 175 (0.6), 2.706 (0.4), 2.667 (16.0), 2.502 (136.7), 2.329 (0, 8), 0, 146 (0.4), 0.000 (81, 6), - 0, 150 (0.4)
Beispiel 1-1-275: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,665(4,5);9,636(4,6);9,620(4,5);8,494(7,6);8,488(7,7);7,919(2,6);7,901(2,8);7,581 (4,8 );7,562(5,4);7,511(10,8);7,490(9,9);7,350(1,0);7,334(2.2);7,329(2,0);7,313(4,9);7,308(7,4);7,291^ Example 1-1-275: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.665 (4.5), 9.636 (4.6), 9.620 (4.5), 8.494 (7.6 8,488 (7.7); 7,919 (2,6); 7,901 (2,8); 7,581 (4,8); 7,562 (5,4); 7,511 (10,8); 7,490 (9,9) ; 7,350 (1.0); 7,334 (2.2); 7,329 (2.0); 7,313 (4.9); 7,308 (7.4); 7.291 ^
5(12,9);7,135(5,7);7,126(1,1);6,251(1,8);6,236(1 ,8);4,344(1,7);4,334(1 ,7);3,794(0,4);3,783(0,5);3,778(0,6);3,768(0,6);3,763(0,5);3 5 (12.9); 7.135 (5.7); 7.126 (1.1); 6.251 (1.8); 6.236 (1, 8); 4.344 (1.7); 4.334 (1, 7); 3.794 (0.4); 3,783 (0.5); 3,778 (0.6); 3,768 (0.6); 3,763 (0.5); 3
3,568(1,7);3,321(36,2);2,676(3,5);2,672(3,7);2,525(3,0);2,507(147,0);2,502(191,5);2,498(138,3);2,333(0,9);2,329(1,2);2,325(0,9);2,029(16,03,568 (1.7); 3,321 (36.2); 2,676 (3.5); 2,672 (3.7); 2,525 (3.0); 2,507 (147.0); 2.502 (191.5); 2,498 (138.3) 2.333 (0.9); 2,329 (1.2); 2,325 (0.9); 2,029 (16.0
);2,012(15,9);1 ,046(11,4);1,030(11,3);0,146(0,7);0,008(5,6);0,000(150,1);-0,008(6,1);-0,150(0,7) 2.012 (15.9), 1.046 (11.4), 1.030 (11.3), 0.146 (0.7), 0.008 (5.6), 0.000 (150.1), and 0.008 (6 , 1), - 0.150 (0.7)
Beispiel 1-1-276: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,815(5,6);9,576(2,6);9.560(2,6);7,729(6,5);7,572(2.3);7,554(2,6);7,440(1,3);7.437(1,3 );7,433(1,1);7.424(2,6);7.418(2,2);7,377(0,5);7,361(0,9);7,356(2,2);7,347(2,4);7,340(5,4);7,323(3,1);7,319(2,4);7,309(2,5);7,3 Example 1-1-276: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.815 (5.6); 9.576 (2.6); 9.560 (2.6); 7.729 (6.5 7,572 (2.3); 7,554 (2,6); 7,440 (1,3); 7,437 (1.3); 7,433 (1,1); 7,424 (2.6); 7,418 (2,2); 7,377 (7,309 (0.5); 7,361 (0.9); 7,356 (2.2); 7,347 (2.4); 7,340 (5.4); 7,323 (3.1); 7,319 (2.4) 2.5), 7.3
3,3);7,273(2,1);7,217(0,3);5,758(2,9);5,631(8,4);3,418(0,5);2,664(16,0);2,525(1,5);2,511(38,5);2,507(78,5);2,503(103,9);2,498(74,2);2,494( 3.3); 7,273 (2.1); 7,217 (0.3); 5,758 (2.9); 5,631 (8.4); 3,418 (0.5); 2,664 (16.0); 2.525 (1 (2,494;, 5); 2,511 (38.5); 2.507 (78.5); 2.503 (103.9); 2.498 (74.2)
35,6);2,334(0,4);2,329(0,6);2,325(0,4);1,046(3,0);1,030(2,9);0,008(2,0);0,000(56,8);-0,008(2,0) 35.6) 2,334 (0.4); 2,329 (0.6); 2,325 (0.4); 1,046 (3.0); 1,030 (2.9); 0,008 (2.0); 0,000 (56 , 8), - 0.008 (2.0)
Beispiel 1-1-277: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,875(5,3);9,571(2,6);9,555(2,6);7,735(6,2);7,583(7,9);7,563(10,2);7.550(2,6);7,369(2.Example 1-1-277: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.875 (5.3); 9.571 (2.6); 9.555 (2.6); 7.735 (6.2 ); 7,583 (7.9); 7,563 (10.2); 7,550 (2.6); 7,369 (. 2
6);7,349(3,6);7,329(1,9);7,304(2,1);7,287(3,1);7,269(1,8);5,757(3,3);5,631(8,2);3,320(14,3);2,666(16,0);2,506(128,3);2,502(166,8);2,498(12 2,1);2,329(1,0);2,325(0,7);1,045(1,0);1,030(1,0);0,146(0,3);0,008(2,6);0,000(72,7);-0,150(0,3) 6); 7,349 (3.6); 7,329 (1.9); 7,304 (2.1); 7.287 (3.1); 7,269 (1.8); 5,757 (3.3); 5,631 (8.2 3.322 (14.3), 2.666 (16.0), 2.506 (128.3), 2.502 (166.8), 2.498 (12 2.1), 2.329 (1.0), 2.325 (0.7 ); 1,045 (1.0); 1,030 (1.0); 0.146 (0.3) 0.008 (2.6) 0.000 (72.7) - 0.150 (0.3)
Beispiel 1-1-278: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,698(3,5);9,681(3,5);8,680(5,0);8,677(7,0);8,657(6,0);8,654(5,4);7,932(1,3);7,918(2,5Example 1-1-278: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.698 (3.5), 9.681 (3.5), 8.680 (5.0), 8.677 (7.0 ); 8.657 (6.0); 8,654 (5.4); 7,932 (1.3); 7.918 (2.5
);7,903(1,3);7,639(0,4);7,628(6,1);7,626(7,1);7,616(5,3);7,613(3,7);7,594(0,4);7,591(0,4);7,318(1,4);7 ); 7,903 (1.3); 7,639 (0.4); 7.628 (6.1); 7,626 (7.1); 7,616 (5.3); 7,613 (3.7); 7,594 (0.4) ; 7,591 (0.4); 7,318 (1.4); 7
1,6);7,293(1,7);7,289(1,4);7,280(1,3);5,757(3,3);5,471(13,1);3,335(1,1);3,320(16,8);3,302(4,1);3,299(4,3);3,284(3,7);3,266(1,1);2,676(0,4);2 ,671(0,6);2,667(0,4);2,525(1,2);2,511(32,2);2,507(68.6);2.502(93,0);2,498(68,3);2,493(33,9);2,333(0,4);2.329(0.6);2,324(0,4);1,2M 1.6); 7,293 (1.7); 7,289 (1.4); 7,280 (1.3); 5,757 (3.3); 5,471 (13.1); 3,335 (1.1); 3,320 (16 , 3,302 (4,1), 3,299 (4,3), 3,284 (3,7), 3,266 (1,1), 2,676 (0,4), 2, 671 (0,6), 2,667 (3) 0.4); 2,525 (1.2); 2,511 (32.2); 2.507 (68.6); 2,502 (93.0); 2,498 (68.3); 2,493 (33.9); 2,333 (0.4 ); 2,329 (0.6); 2,324 (0.4); 1.2M
18(7,5); 1 , 100(16,0); 1 ,082(7,4);0,008(0,5);0,000(18,3);-0,008(0,8) 18 (7.5); 1, 100 (16.0); 1, 082 (7.4), 0.008 (0.5), 0.000 (18.3), - 0.008 (0.8)
Beispiel 1-1-279: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,691 (3,5);9.675(3.5);8,681 (5,4);8.678(7, 1);8,659(6,3);7,999(1 ,3);7,984(2,6);7,969(1.3 );7,638(0,4);7,626(6,9);7,616(6,0);7,319(1,5);7,310(1,6);7,307(1,6);7,302(1 ,7);7,297(1 ,6);7,293(1.6);7,2  Example 1-1-279: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.691 (3.5), 9.675 (3.5), 8.681 (5.4), 8.678 (7, 1); 7.659 (6.3), 7.999 (1.3), 7.989 (2.6), 7.969 (1.3), 7.638 (0.4), 7.626 (6.9), 7.616 (6.0), 7.319 (1 , 7,310 (1,6); 7,302 (1, 7); 7,297 (1,6); 7,293 (1.6); 7,2);
13,0);3,321 (20,7);3,268(2,1);3,251(4,7);3,236(4,7);3,219(2,1);2,676(0,4);2,671(0,5);2,667(0,4);2,525(1,3);2,511(32,4);2,507(67,3);2,50 8);2,498(64,7);2,494(31 ,5);2,333(0,4);2,329(0,5);2,325(0,4); 1 ,536(0,5); 1 ,517(2,4); 1 ,499(4,7); 1 ,482(4,8); 1 ,464(2,6); 1 ,446(0,6);0,910(7,9);0,8 91(16,0);0,873(7,0);0,008(0,5);0,000(17,4);-0,008(0,7)  3,221 (20.7); 3,268 (2,1); 3,251 (4,7); 3,236 (4,7); 3,219 (2,1); 2,676 (0,4); 2,671 (0 , 5), 2.667 (0.4), 2.525 (1.3), 2.511 (32.4), 2.507 (67.3), 2.50 8), 2.498 (64.7), 2.494 (31, 5 ); 2,333 (0.4); 2,329 (0.5); 2,325 (0.4); 1, 536 (0.5); 1, 517 (2,4); 1,499 (4,7); 1, 482 (4,8); 1, 464 (2.6); 1, 446 (0.6), 0.910 (7.9), 0.8 91 (16.0), 0.873 (7.0), 0.008 (0.5), 0.000 (17.4), - 0.008 ( 0,7)
Beispiel 1-1-280: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,699(3,9);9,682(4,0);8.677(6,3);8,673(7,9);8,653(7,2);7,840(0,8);7,829(2,3);7,817(2,3Example 1-1-280: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.699 (3.9); 9.682 (4.0); 8.677 (6.3); 8.673 (7.9 ); 8.653 (7.2); 7,840 (0.8); 7,829 (2.3); 7,817 (2.3
);7,805(0,8);7,622(7,8);7,612(7,8);7,322(1,7);7,311(2,5);7,305(1,9);7,300(1 ,8);7,295(2,2);7,283(1,5);5,476(15,8);4,344(0,6);4,334(0,6);3,321 (28,2);2,809(16,0);2,797(15,9);2,676(0,5);2,671 (0,7);2,667(0,5);2,525(1,7);2,511 (42,4);2,507(85,4);2,502(111 ,7);2,498(80,3);2,334(0,5);2,3 29(0,7);2,325(0,5);1,045(4,4);1,030(4,4);0,008(0,6);0,000(16,4);-0,008(0,7) 7.805 (0.8), 7.622 (7.8), 7.612 (7.8), 7.322 (1.7), 7.311 (2.5), 7.305 (1.9), 7.300 (1, 8) 7.295 (2.2), 7.283 (1.5), 5.476 (15.8), 4.344 (0.6), 4.334 (0.6), 3.321 (28.2), 2.809 (16.0); 2.777 (15.9), 2.676 (0.5), 2.671 (0.7), 2.667 (0.5), 2.525 (1.7), 2.511 (42.4), 2.507 (85.4), 2.502 (111, 7); 2.498 (80.3); 2.344 (0.5); 2.3 29 (0.7); 2.325 (0.5); 1.045 (4.4); 1.030 (4.4) 0.008 (0.6); 0,000 (16.4) - 0.008 (0.7)
Beispiel 1-1-281 : 1H-NMR(400,0 MHz, de-DMSO): 6= 9,510(1,6);9,493(1,6);8,682(3,1);8,679(3,5);8,634(3,2);8,632(3,0);7,511(1,4);7,492(1,6 );7,265(1,4);7,247(2,1);7,229(1,3);5,601(7,0);3,715(16,0);3,320(7,4);2,506(34,2);2,502(44,8);^ Example 1-1-281: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.510 (1.6), 9.493 (1.6), 8.682 (3.1), 8.679 (3.5 8,634 (3,2); 8,632 (3,0); 7,511 (1,4); 7,492 (1,6); 7,265 (1,4); 7,247 (2,1); 7,229 (1,3) ; 5,601 (7.0); 3,715 (16.0); 3,320 (7.4); 2,506 (34.2); 2.502 (44.8); ^
;-0,008(1,3) Beispiel 1-1-282: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,703(8,8);9,540(4,7);9,523(4,8);7,954(3,9);7,932(5,1);7.893(11,4);7,813(2,5);7.811(2,; -0.008 (1.3) Example 1-1-282: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.703 (8.8), 9.540 (4.7), 9.523 (4.8), 7.954 (3.9 ); 7,932 (5.1); 7,893 (11.4); 7,813 (2.5); 7,811 (2,
6);7,792(4,2);7,773(2,2):7,582(12,9);7,561(15,8);7,392(2,6);7,375(5,1);7,370(5,3);7,359(2,9);7,350(6,1);7,329(3,1);5,513(15,5);4,345(2,3) 335(2,3);3,794(0,6);3,783(0,7);3,779(0,9);3,768(0,8);3,763(0,7);3,753(0,6);3,322(49,4):2,672(1,1);2,507(149,3);2,503(188,8);2,499(139,2):2 ,334(1 ,0);2.330(1 ,2);2.326(0,9);1 ,046(16,0);1 ,031 (15,9);0,000(15.2) 7,582 (12.9); 7,561 (15.8); 7,392 (2.6); 7,375 (5.1); 7,370 (5.3: 6);; 7.792 (4.2) 7.773 (2.2) 7.359 (2.9); 7.350 (6.1); 7.329 (3.1); 5.513 (15.5); 4.345 (2.3) 335 (2.3); 3.794 (0.6); 3,783 (0.7); 3,779 (0.9); 3,768 (0.8); 3,763 (0.7); 3,753 (0.6); 3,322 (49.4) 2,672 (1.1); 2,507 (149.3); 2.503 (188.8); 2.499 (139.2): 2.334 (1.0); 2.330 (1.2); 2.326 (0.9); 1.046 (16.0 ), 1, 031 (15.9), 0.000 (15.2)
Beispiel 1-1-283: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,640(9,0);9,544(4,7);9,527(5,0);7,953(3,9);7,931(5,3):7,888(11,6);7,815(2,7);7,796(4, 3);7,775(2,2);7,439(2,4);7,434(1,9);7,424(4,2);7,418(3,8);7,397(2,7);7,379(5,3);7,362(3,9);7,357(4,0);7,346(4,2);7,340(7,7) Example 1-1-283: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.640 (9.0), 9.544 (4.7), 9.527 (5.0), 7.953 (3.9 7.931 (5.3): 7.888 (11.6); 7.815 (2.7); 7.796 (4, 3); 7.775 (2.2); 7.439 (2.4); 7.434 (1.9) ; 7,424 (4.2); 7,418 (3.8); 7,397 (2.7); 7,379 (5.3); 7,362 (3.9); 7,357 (4.0); 7,346 (4.2); 7,340 (7.7)
(3,7);7,302(1,0);7,298(0,6);5,513(16,0):4,347(1,5);4,336(1,6);3,795(0,5);3,785(0,5);3,780(0,6);3,770(0,6);3,765(0,5);3,754(0,4);3,325(29,2); 2,674(0,7);2,509(88,6):2,505(115,2);2,501(87,0);2,341(0,6):2,331(0,7):1,047(13,2);1,032(13,1);0,000(9,7)  (3.7); 7,302 (1.0); 7,298 (0.6); 5,513 (16.0) 4,347 (1.5); 4,336 (1.6); 3,795 (0.5); 3,785 ( 0.5); 3,780 (0.6); 3,770 (0.6); 3,765 (0.5); 3,754 (0.4); 3,325 (29.2); 2,674 (0.7); 2,509 (88.6) 2.505 (115.2); 2.501 (87.0); 2,341 (0.6) 2,331 (0.7) 1,047 (13.2); 1.032 (13,1); 0,000 (9.7)
Beispiel 1-1-284: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,217(7,3);9,589(4,7);9,573(4,9);9,472(0,4);9,455(0,4);8,242(4,7);8,230(4,8);7,964(3,Example 1-1-284: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.217 (7.3), 9.589 (4.7), 9.583 (4.9), 9.472 (0.4 ); 9,455 (0.4); 8,242 (4.7); 8,230 (4.8); 7,964 (3,
9);7,943(5,3);7,885(12,1);7,840{1,5);7,835(2,8);7,832(2,8);7,814(4,7);7,810(4,1):7,806(2,7);7,795(2,6);7,792(2,9);7,789(3,0);7,784(3,6);7,77 9(2,6);7,762(2,7);7,759(2,5);7,422(2,5);7,420(2,6);7,404(4,7);7,387(2,3);7,385(2,3);7,337(0,4);7,303(2,3);7,294(3,0);7,283(4,1);7,273(2,6);7, 262(1,9);5,758(4,1):5,517(16,0);5,374(1,5);3,738(3,7);3,325(32,1);2,677(0,8);2,672(1 ,1);2,668{0,8);2,512(73,3);2,508(145,5);2,503(190,9);2 ,499(139,8);2,335(0,8):2.330(1 , 1 ):2,326(0,8);1 ,232(0,4); 1 ,046(1 ,3); 1 ,031 (1 ,2):0.008{0,8);0,000(18,0) 9); 7,943 (5.3); 7,885 (12.1); 7.840 {1.5); 7,835 (2.8); 7,832 (2.8); 7,814 (4.7); 7,810 (4.1 ): 7.806 (2.7); 7.795 (2.6); 7.792 (2.9); 7.789 (3.0); 7.784 (3.6); 7.77 9 (2.6); 7.762 (2 , 7); 7.759 (2.5); 7,422 (2.5); 7,420 (2.6); 7,404 (4.7); 7.387 (2.3); 7,385 (2.3); 7,337 (0, 4); 7,303 (2,3); 7,294 (3,0); 7,283 (4,1); 7,273 (2,6); 7,262 (1,9); 5,758 (4,1): 5,517 (16 , 0), 5.374 (1.5), 3.738 (3.7), 3.325 (32.1), 2.677 (0.8), 2.672 (1, 1), 2.668 (0.8), 2.512 (73, 3); 2,508 (145,5); 2,503 (190,9); 2,499 (139,8); 2,335 (0,8): 2,330 (1,1): 2,326 (0.8); 1, 232 (0.4); 1, 046 (1, 3); 1, 031 (1, 2): 0.008 {0.8); 0.000 (18.0)
Beispiel 1-1-285: 'H-NMR(400,0 MHz, de-DMSO): δ= 10,700(8,5);9,621(4,8);9,6O4(5,0);8,516(5,0);8,495(5,4);7,955(3,7);7,933(5,5);7,873(11 Example 1-1-285: 'H NMR (400.0 MHz, de-DMSO): δ = 10,700 (8.5), 9.621 (4.8), 9.6 O4 (5.0), 8.516 (5 , 0); 8,495 (5.4); 7,955 (3.7); 7,933 (5.5); 7,873 (11
,8);7,853(2,9);7,851(2,9);7,832(4,4);7,813(2,4);7,811(2,6);7,805(4,2);7,802(4,4);7,786(4,3);7,783(4,4);7,696(2,1);7,693(2,1);7,675(4,^, 8); 7,853 (2.9); 7,851 (2.9); 7,832 (4.4); 7,813 (2.4); 7,811 (2.6); 7,805 (4.2); 7,802 (4, 4); 7,786 (4.3); 7,783 (4.4); 7,696 (2.1); 7,693 (2.1); 7,675 (4, ^
6(2,2);7,653(2,1);7,436(2,6);7,419(4,8):7,403(2,4);7,401 (2,3);7,218(2,9);7,199(5,2);7,180(2,6):5,758(1,1);5,531(16,0);3,324(36,4);2,673(0,7)6 (2.2); 7.653 (2.1); 7.436 (2.6); 7.419 (4.8): 7.403 (2.4); 7.401 (2.3); 7.218 (2.9); 7.199 (5.2); 7,180 (2.6) 5,758 (1.1); 5,531 (16.0); 3,324 (36.4); 2,673 (0.7)
;2,509(95,4);2,504(123,1);2,500(91,3);2,331(0,7);1,047(0,5);1,031(0,5);0,000(2,4) ; 2,509 (95.4); 2.504 (123.1); 2,500 (91.3); 2,331 (0.7); 1,047 (0.5); 1,031 (0.5); 0,000 (2.4)
Beispiel 1-1-286: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,430(4,5);10,424(4,6);9,646(4,6);9,630(4.8);8,487(1 ,9);8,466(3,8);8.449(2,0);7,954(3Example 1-1-286: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.430 (4.5), 10.424 (4.6), 9.646 (4.6), 9.630 (4.8); 8.467 (1, 9), 8.466 (3.8), 8.449 (2.0), 7.954 (3
,8);7,932(5,2);7,881(11,0);7,824(2,7);7,805(4,3);7,784(2,2);7,421(2,6);7,404(4,7);7,386(2,3);7,318(2,0);7,298(2,6);7,292(2,3);7,269(2,3), 8); 7,932 (5.2); 7,881 (11.0); 7,824 (2.7); 7,805 (4.3); 7,784 (2.2); 7,421 (2.6); 7,404 (4, 7); 7,386 (2.3); 7,318 (2.0); 7,298 (2.6); 7,292 (2.3); 7,269 (2.3)
97(1,9);7,178(4,1);7,158(2,5);7,070(1,4);7,055(2,4);7,038(2,2);7,022(0,9);5,759(0,7);5,516(16,0);3,325(23,^ 97 (1.9); 7,178 (4.1); 7,158 (2.5); 7,070 (1.4); 7,055 (2.4); 7,038 (2.2); 7,022 (0.9); 5,759 (0.7); 5,516 (16.0); 3,325 (23, ^
0,6); 1 ,047(0,8); 1 ,032(0,8);0,000(1 ,8)  0.6); 1, 047 (0.8); 1, 032 (0.8); 0.000 (1, 8)
Beispiel 1-1-287: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,499(1, 1);9,482(1,1);7,755(2,5);7,574(1,7);7,555(1,9);7,273(1,3);7,255(2,0);7.237(1,1Example 1-1-287: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.499 (1, 1), 9.482 (1.1), 7.755 (2.5), 7.574 (1.7 ); 7,555 (1.9); 7,273 (1.3); 7,255 (2.0); 7,237 (1.1
);6,324(0,6);6,308(0,6);5,757(2,2);3,723(0,6);3,709(16,0);3,327(5,0);2,758(2,1);2,672(0,4);2,668(0,4);2,507(47,1);2,503(60,4);2,499(42,8) 329(0,4);1,942(4,7);1,925(4,6);1,234(0,5);1,046(1,0);1,030(1,0);0,146(0,3);0,008(2,5);0,000(67,9);-0,008(2,7);-0,150(0,3) ); 6,324 (0.6); 6,308 (0.6); 5,757 (2.2); 3,723 (0.6); 3,709 (16.0); 3,327 (5.0); 2,758 (2.1) 2.672 (0.4), 2.668 (0.4), 2.507 (47.1), 2.503 (60.4), 2.499 (42.8) 329 (0.4), 1.942 (4.7), 1.925 (4.6); 1,234 (0.5); 1,046 (1.0); 1,030 (1.0); 0.146 (0.3) 0.008 (2.5) 0.000 (67.9) - 0.008 (2.7) - 0.150 (0.3)
Beispiel 1-1-288: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,595(5,1);9,578(5,3);9,538(9,2);7,849(12,3);7,825(3.0);7,803(5,8);7,769(3.4);7,751(4.Example 1-1-288: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.595 (5.1), 9.588 (5.3), 9.538 (9.2), 7.849 (12.3 ); 7,825 (3.0); 7,803 (5.8); 7,769 (3.4); 7,751 (. 4
0);7,748(4,1);7,729(2,0);7,392(2,8);7,374(5,0);7,366(2,2);7,358(3,5);7,345(3,2);7,324(2,3);7,309(1,3);7,207(6,2);7,187(9,8);7,167(4,3);7,157 (1,1);6,292(1,0);6,275(3,6);6,257(3,7);6,240(1,1);5,757(0,8);3,321(40,0);2,672(1,2);2,507(166,8);2,503(203,1);2,498(144,9);2,329(1,2);1,980); 7,748 (4.1); 7,729 (2.0); 7,392 (2.8); 7.374 (5.0) 7.366 (2.2); 7,358 (3.5); 7,345 (3.2 7,324 (2,3); 7,309 (1,3); 7,207 (6,2); 7,187 (9,8); 7,167 (4,3); 7,157 (1,1); 6,292 (1,0) ; 6,275 (3.6); 6,257 (3.7); 6,240 (1.1); 5,757 (0.8); 3,321 (40.0); 2,672 (1.2); 2,507 (166.8); 2.503 (203.1); 2.498 (144.9); 2,329 (1.2) 1.98
7(16,0);1,969(15,9);1,046(2,1);1,031(2,1);0,146(0,4);0,000(96,6);-0,150(0,5) 7 (16.0) 1,969 (15.9); 1,046 (2.1); 1,031 (2.1); 0,146 (0.4); 0,000 (96.6) - 0.150 (0.5)
Beispiel 1-1-289: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,628(3,3);9,612(3,3);8,489(6,1);7,807(8,0);7,792(1,9);7,770(3,8);7,745(2,3);7,725(2,7Example 1-1-289: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.628 (3.3); 9.612 (3.3); 8.489 (6.1); 7.807 (8.0 ); 7,792 (1.9); 7,770 (3.8); 7,745 (2.3); 7,725 (2.7
);7,705(1,2);7,380(1,7);7,364(3,1);7,348(1,5);7,068(2,1);6,225(0,7);6,208(2,4);6,191(2,4);6,173(0,7);4,344(2,4);4,333(2,5);4,022(0,4);4); 7,705 (1.2); 7,380 (1.7); 7,364 (3.1); 7,348 (1.5); 7,068 (2.1); 6,225 (0.7); 6,208 (2.4) ; 6,191 (2.4); 6,173 (0.7); 4,344 (2.4); 4,333 (2.5); 4,022 (0.4); 4
0,4);4,006(0,4);3,998(0,4);3,829(0,8);3,821(0,8);3,793(0,8);3,782(0,7);3,778(0,9);3,767(0,9);3,763(0,7);3,752(0,6);3,320(37,0);3,209(0,8);3^0.4); 4,006 (0.4); 3,998 (0.4); 3,829 (0.8); 3,821 (0.8); 3,793 (0.8); 3,782 (0.7); 3,778 (0 , 9); 3,767 (0.9); 3,763 (0.7); 3,752 (0.6); 3,320 (37.0); 3,209 (0.8); 3 ^
186(6,2);2,671(0,9);2,506(126,5);2.502(161,7);2.498(121,6);2,329(0,9);2.301(0,5);1,932(10,4);1,91^ 186 (6.2); 2,671 (0.9); 2,506 (126.5); 2.502 (161.7); 2,498 (121.6); 2,329 (0.9); 2,301 (0.5); 1,932 (10.4); 1.91 ^
1,518(2,6);1.418(1,5);1,411(1,6);1,305(3,5);1.292(7,1);1 ,273(2,0);1,259(0.4);1.234(0,9);1,221(0,3^  1.518 (2.6), 1.418 (1.5), 1.411 (1.6), 1.305 (3.5), 1.292 (7.1), 1.273 (2.0), 1.259 (0.4), 1.234 (0.9); 1,221 (0.3 ^
4);1,167(0,4);1 ,102(0,3);1,093(0,3);1 ,088(0,4);1,079(0,5);1,063(0,4);1,045(16,0);1,030(15^ ^ 4), 1.167 (0.4), 1, 102 (0.3), 1.093 (0.3), 1.088 (0.4), 1.079 (0.5), 1.063 (0.4), 1.045 (16.0); 1.030 (15 ^ ^
57(0,5);0,946(0,6);0,937(0,4);0,928(0,4);0,919(0,4);0,146(0,4);0,000(75,6);-0,150(0,4)  57 (0.5); 0,946 (0.6); 0.937 (0.4) 0.928 (0.4) 0.919 (0.4) 0.146 (0.4) 0.000 (75.6); - 0.150 (0.4)
Beispiel 1-1-290: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,737(4,0);9,721(3,9);8,316(0,4);8,126(4,4);8,118(4,3);7,754(10.3);7.503(5.8);7,484(6, 7);7,257(4,6);7,239(7,2);7,221(3,9);6,375(2,9);6,358(2,8);5,757(3,0);3,728(0,3);3,320(67,2);2,758(10,6);2,750(11 ,9);2,741 (8,8);2,732(5,6);2, 722(3,5);2,713(1,7);2,671(2,5);2,667(2,0);2,630(0,4);2,506(282,8);2,502(370,6);2,498(273,0);2,329(2,1);1,969(16,0);1,952(15,9);1, 625(0,4); 1 ,423(0,9); 1 ,406(0,8); 1 ,235(0,5); 1 , 176(0.4); 1 , 163(0,6); 1 , 156(0,7); 1 ,006(0,6);0,997(0,5);0.725(2,2);0.714(7,2);0,709(8.9):0,697(8,7);0,692(7. 6);0.681(3,0);0,656(0.4);0,538(0,4);0,528(0,4);0,512(0,5);0,496( Example 1-1-290: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.737 (4.0), 9.721 (3.9), 8.316 (0.4), 8.126 (4.4 8,118 (4,3); 7,754 (10.3); 7,503 (5.8); 7,484 (6,7); 7,257 (4,6); 7,239 (7,2); 7,221 (3,9); 6,375 (2 , 9); 6,358 (2,8); 5,757 (3,0); 3,728 (0,3); 3,320 (67,2); 2,758 (10,6); 2,750 (11,9); 2,741 (8; 2,722 (3,5); 2,713 (1,7); 2,671 (2,5); 2,667 (2,0); 2,630 (0,4); 2,506 (282 , 8); 2,502 (370,6); 2,498 (273,0); 2,329 (2,1); 1,969 (16,0); 1,952 (15.9); 1, 625 (0.4); 1, 423 (0.9); 1, 406 (0.8); 1, 235 (0.5); 1, 176 (0.4); 1, 163 (0.6); 1, 156 (0.7); 1, 006 (0.6), 0.997 (0.5), 0.725 (2.2), 0.714 (7.2), 0.709 (8.9): 0.697 (8.7), 0.692 (7.6), 0.681 (3.0); 0.656 (0.4); 0,538 (0.4); 0,528 (0.4); 0,512 (0.5); 0,496 (
0,150(0,5) 0.150 (0.5)
Beispiel 1-1-291 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,669(7.5);9.633(0,6);9,611(4.2);9,596(4.1);8,317(0.4);7,806(10,7);7,602(6,4);7,583(7,Example 1-1-291: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.699 (7.5); 9.633 (0.6); 9.611 (4.2); 9.596 (4.1); 8.317 (0.4) ; 7,806 (10.7); 7,602 (6.4); 7,583 (7,
2);7,392(0,4);7.372(1,3);7,357(2,7);7,352(2,4);7,335(5,3);7,313(7,5);7,295(8,1);7,277(4,6);7,206(2,0);7,198(10,4);7,178(16,0);7^2); 7,392 (0.4); 7,372 (1.3); 7,357 (2.7); 7,352 (2.4); 7.335 (5.3); 7,313 (7.5); 7,295 (8.1 7 ^); 7,277 (4.6); 7,206 (2.0); 7,198 (10.4); 7,178 (16.0)
48(1,6);7,128(0,3);7,022(0,4);6,999(0,4);6,467(0,4);6,432(2,8);^ 48 (1.6); 7,128 (0.3); 7,022 (0.4); 6,999 (0.4); 6,467 (0.4); 6,432 (2.8); ^
;2,920(0,5);2,878(2,7);2,792(8,2);2,712(0,6);2,676(1,6);2,672(2,1);2,667(1,6);2,619(0,5);2,511 (121 ,5);2,507(241,5);2,503(315,8);2,498(224, 8);2,494(107,5);2,335(1,9);2,330(2,0);2,067(0,9);2,035(15,5);2,018(15,3);1,626(0,4);1 ,232(0,5);1^  ; 2,920 (0.5); 2,878 (2.7); 2,792 (8.2); 2,712 (0.6); 2,676 (1.6); 2,672 (2.1); 2,667 (1.6); 2,619 (0.5); 2,511 (121,5), 2,507 (241,5), 2,503 (315,8), 2,498 (224,8), 2,494 (107,5), 2,335 (1,9), 2,330 (2.0); 2.067 (0.9); 2.035 (15.5); 2.018 (15.3); 1.626 (0.4); 1, 232 (0.5); 1 ^
1,112(6,3);1,105(6,6);1,094(2,6);1,054(0,4);0,922(0,3);0,882(2,7);0,871(6,8);0,864(6,6);0,852(2,2);0,146(0,4);0,008(2,8);0,000(72,4);- 0,009(2,7);-0,150(0,3)  1,112 (6.3); 1,105 (6.6); 1,094 (2.6); 1,054 (0.4); 0,922 (0.3); 0,882 (2.7); 0,871 (6.8); 0,864 (6.6); 0.852 (2.2); 0.146 (0.4); 0.008 (2.8); 0.000 (72.4); - 0.009 (2.7); - 0.150 (0.3)
Beispiel 1-1-292: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,933(1 ,6);9,916(1 ,6);7,685(3,9);7,642(1 ,4);7,623(1 ,6);7,305(1 ,3);7,287(1 ,9);7,269(1 ,1 );5,520(5,6);4,607(8,7);3,716(0,4);3,701 (1 ,1 );3,685(1 ,5);3,670(1 ,1 );3,655(0,5);3,324(23,6);2,636(9,9);2,508(31 ,6);2,504(41,5);2.499(31 ,9);1 , 149(16,0);1,134(15,9);0,000(22,5) Example 1-1-292: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.933 (1.6), 9.916 (1.6), 7.685 (3.9), 7.642 (1, 4 7.623 (1, 6), 7.305 (1, 3), 7.287 (1, 9), 7.269 (1, 1), 5.520 (5.6), 4.607 (8.7), 3.716 (0.4) 3.701 (1, 1); 3.685 (1, 5); 3.670 (1, 1); 3.655 (0.5); 3.324 (23.6); 2.636 (9.9); 2.508 (31, 6); 2.504 (41.5); 2.499 (31, 9); 1, 149 (16.0); 1.134 (15.9); 0.000 (22.5)
Beispiel 1-1-293: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,944(1 ,8);9,928(1 ,9);7,686(4,3);7,641 (1 ,6);7,623(1 ,8);7,302(1 ,4);7,284(2,1);7,266(1 ,2Example 1-1-293: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.944 (1, 8), 9.928 (1, 9), 7.686 (4.3), 7.641 (1, 6 7,623 (1, 8); 7,302 (1, 4); 7,284 (2,1); 7,266 (1, 2);
);5,520(6,2);4,630(9,3);3,325(10,7);3,307(1,5);3,293(1,9);3,278(1,2);3,264(0,4);2,638(11,0);2,508(30,6);2,504(37,2);2,500(27,4);1,536(1 ,1); 1 ,517(3,9); 1 ,503(4,9); 1 ,499(4,7); 1 ,484(4,3); 1 ,466(1 ,4); 1 ,047(0,5); 1 ,031 (0,5);0,893(8, 1);0.875(16,0);0,856(7.2);0,000(20,0) ); 5,520 (6.2); 4,630 (9.3); 3,325 (10.7); 3,307 (1.5); 3,293 (1.9); 3,278 (1.2); 3,264 (0.4) 2.638 (11.0), 2.508 (30.6), 2.504 (37.2), 2.500 (27.4), 1.536 (1, 1); 1, 517 (3.9); 1, 503 (4,9); 1,499 (4,7); 1, 484 (4,3); 1, 466 (1, 4); 1, 047 (0.5); 1, 031 (0.5), 0.893 (8, 1), 0.875 (16.0), 0.856 (7.2), 0.000 (20.0)
Beispiel 1-1-294: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,935(2,6);9,919(2,7);7,686(6,5);7,641(2,4);7,622(2,7);7,301(2.1);7,284(3,1);7,266(1,9 );5,757(1,1);5.518(8,9);4,639(13,9);3,390(0,8);3.379(1,0);3,368(1.4);3,359(1,2);3.346(0,8);3,320(18,5);2,676(0,6);2,672(0,7);2,635(Example 1-1-294: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.935 (2.6), 9.919 (2.7), 7.686 (6.5), 7.641 (2.4 7,622 (2,7); 7,301 (2.1); 7,284 (3,1); 7,266 (1,9); 5,757 (1,1); 5,518 (8,9); 4,639 (13,9); 3,390 (0.8); 3,379 (1.0); 3,368 (1.4); 3,359 (1.2); 3,346 (0.8); 3,320 (18.5); 2,676 (0.6); 2,672 (0, 7); 2.635 (
07(85,9);2,503(107,3);2,498(78,6);2,330(0,6);1,915(1 );1,890(2,4);1,689(2,1);1,675(2,2);1,489(1,2);1,476(1,0);1,281(1,5);1,257(3,1);1,233^ 3,8);1,2O4(3,5);1,182(2,1);0,0O0(31,7) 07 (85.9), 2.503 (107.3), 2.498 (78.6), 2.330 (0.6), 1.915 (1), 1.890 (2.4), 1.689 (2.1), 1.675 (2 , 2); 1,489 (1,2); 1,476 (1,0); 1,281 (1,5); 1,257 (3,1); 1,233 ^ 3,8); 1,2O4 (3,5); 1,182 ( 0,0O0 (31.7), 2.1)
Beispiel 1-1-295: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,424(7,6);9.612(4,4);9,595(4.5);8,545(6,0);8,540(5,8);7,856(3,1);7,851(3,1);7,835(3, |8);7,829(4,3);7,802(6,1);7,790(4,0);7,771(4,3);7,755(15,6);7,752(16,0);7,514(5,6);7,493(5,0);7,413(2,2);7,395(4,0);7,379(2,0) 47(14,1);3,321(50,7);2,671(1 ,2);2,502(194,2);2,329{1,1);2,076(1,6);0,146(0,6);0,000(122,8);-0,150(0,6) Example 1-1-295: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.424 (7.6); 9.612 (4.4); 9.595 (4.5); 8.545 (6.0); 8.540 (5.8); 7.856 (3.1); 7.851 (3.1); 7.835 (3, | 8); 7.829 (4.3); 7.802 (6.1); 7.790 (4.0); 7,771 (4.3); 7,755 (15.6); 7.752 (16.0); 7,514 (5.6); 7,493 (5.0); 7,413 (2.2); 7,395 (4.0); 7,379 (2.0) 47 (14,1); 3,321 (50,7); 2,671 (1,2); 2,502 (194,2); 2,329 {1,1); 2,076 (1,6); 0,146 (0,6); 0,000 (122.8) - 0.150 (0.6)
Beispiel 1-1-296: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,939(0,5);9,923(0,5);7,687(1,3);7,638(0,5);7,619(0.5);7.306(0,4);7.289(0,6);7,271 (0,4 );5,528(1,8);5,503(0,6);5,494(0,6);5,490(0,7);5,483(0,8);4,572(3,0);3,899(0,4);3,329(3,7);2,939(0,8);2,936(0,8);2,933(0,5) Example 1-1-296: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.939 (0.5); 9.923 (0.5); 7.687 (1.3); 7.638 (0.5 7.619 (0.5), 7.306 (0.4), 7.289 (0.6), 7.271 (0.4), 5.528 (1.8), 5.503 (0.6), 5.494 (0.6), 5.490 (0.7); 5,483 (0.8); 4,572 (3.0); 3,899 (0.4); 3,329 (3.7); 2,939 (0.8); 2,936 (0.8); 2,933 ( 0.5)
3,1);2,508(13,6):2,503(17,6);2,499(12,8);1,645(1,9);1,633(1,4);1,188(16,0);1,135(1,8);0,008(1,2):0,000(20,5);-0,008(1,0)  3.1); 2,508 (13.6) 2,503 (17.6); 2,499 (12.8); 1,645 (1.9); 1,633 (1.4); 1,188 (16.0); 1.135 (1 , 8) 0.008 (1.2) 0.000 (20.5) - 0.008 (1.0)
Beispiel 1-1-297: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,881(2,6);9,864(2,7);7,679(6,4);7,652(2,7);7,330(1,9);7,312(3,0);7,294(1,8);5,522(9,1Example 1-1-297: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.881 (2.6); 9.864 (2.7); 7.679 (6.4); 7.652 (2.7 ); 7,330 (1.9); 7,312 (3.0); 7,294 (1.8); 5,522 (9.1
):4,809(11,8);4,261(1,7):4,237(5,2):4,213(5,3);4,190(1,9):3,707(0,3);3,321(56,1);2,672(0,9);2,636(16,0):2,502(142,2);2,450(0,3);2,329(0,8); 1 ,045(0,5); 1 ,030(0,5);0,000(63,4) ): 4,809 (11.8); 4,261 (1.7) 4,237 (5.2) 4,213 (5.3); 4,190 (1.9) 3,707 (0.3); 3,321 (56.1) ; 2,672 (0.9); 2,636 (16.0) 2.502 (142.2); 2,450 (0.3); 2,329 (0.8); 1, 045 (0.5); 1, 030 (0.5); 0.000 (63.4)
Beispiel 1-1-298: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,450(8,6);9,654(4,9);9,638(5,1);8,551(6,2);8,546(6,4);7,986(5,8);7,862(3,4);7,856(3,Example 1-1-298: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.450 (8.6), 9.654 (4.9), 9.638 (5.1), 8.551 (6.2 ); 8,546 (6.4); 7,986 (5.8); 7,862 (3.4); 7,856 (3,
4);7,841(3,9);7,835(3,9);7,818(2,6);7,797(6,1);7,776(3,6):7,758(4,1);7,737(1,7);7,514(7,0);7,493(6,3);7,463(2,1):7,443(6,1);7,423(5,5);74); 7,841 (3.9); 7,835 (3.9); 7,818 (2.6); 7,797 (6.1); 7,776 (3.6) 7.758 (4.1); 7,737 (1.7 ); 7,514 (7.0); 7,493 (6.3); 7,463 (2.1) 7,443 (6.1); 7,423 (5.5); 7
(7,0);7,385(6,5);7,367(2,2);7,012(3,2):6,993(2,9);5,354(16,0);3,326(92,6);2,673(0,8);2,508(112,1);2,504(147,1);2,330(0,8);2,076(1,7);0,146((7.0); 7,385 (6.5); 7,367 (2.2); 7,012 (3.2) 6,993 (2.9); 5,354 (16.0); 3,326 (92.6); 2,673 ( (0.146, 0.8); 2,508 (112.1); 2.504 (147.1); 2,330 (0.8); 2,076 (1.7)
0,7);0,008(6,5);0,000(134,7);-0,150(0,6) 0.7) 0.008 (6.5) 0.000 (134.7) - 0.150 (0.6)
Beispiel 1-1-299: 'H-NMR(400,0 MHz, de-DMSO): δ= 10,275(3,1 );9,685(1 ,8);9,668(1 ,9);8,550(2,3);8,544(2,3);7,857(1 ,3);7,851 (1 ,2);7,836(1 , 4);7,830(1 ,4);7,801(1,1);7,780(2,2);7,751 (1 ,2);7, 732(1 ,5);7,712(0,7);7,511 (2,5);7,490(2,3);7,388(3,4);7,371 (1 ,7);7,355(0,8);7,241 (1 ,1 );7,220 (2,5);7,200(1 ,6);7, 101 (1 ,5);7,079(1,1);6,621 (1 ,2);6,616(1 ,2);6,602(1,2);6,596(1,2);5,350(5,9);3,760(16,0);3.323(33,9);2.671 (0,5):2,507(71 ,2) ;2,502(92,0);2,498(68,8);2,329(0,5);0,146(0,4);0,008(4, 1 );0,000(86,9);-0,008(4,2):-0, 150(0,4)  Example 1-1-299: 'H-NMR (400.0 MHz, de-DMSO): δ = 10.275 (3.1); 9.685 (1.8); 9.688 (1.9); 8.550 (2.3 7,851 (1, 4); 7,830 (1,4); 7,801 (1,1); 7,780 (2,2); 7,751 (1,2), 7,732 (1,5), 7,712 (0,7), 7,511 (2,5), 7,490 (2,3), 7,388 (3,4), 7,371 (1, 7 7,355 (0.8), 7.241 (1, 1), 7.220 (2.5), 7.200 (1, 6), 7, 101 (1, 5), 7, 79 (1.1), 6.621 (1, 2), 6.616 (1.2), 6.602 (1.2), 6.596 (1.2), 5.350 (5.9), 3.760 (16.0), 3.323 (33.9), 2.671 (0.5 2.507 (71.2), 2.502 (92.0), 2.498 (68.8), 2.329 (0.5), 0.146 (0.4), 0.008 (4, 1), 0.000 (86.9) -0,008 (4,2): - 0, 150 (0,4)
Beispiel 1-1-300: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,231 (4,3);9,685(2,6);9,668(2,7);8,553(3,2);8,547(3,3);7.860(1,8);7,854(1,8);7,839(2, 0);7,833(2, 1);7,799(1 ,6);7,778(3, 1);7,743(1 ,7);7,725(2,2);7,705(1 ,0);7,511 (3,7);7,490(3,3);7,458(3,6);7,429(2,0);7,386(1,3);7,370(2,4);7,354Example 1-1-300: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.231 (4.3), 9.685 (2.6), 9.688 (2.7), 8.533 (3.2 8,547 (3,3); 7,860 (1,8); 7,854 (1,8); 7,839 (2, 0); 7,833 (2, 1); 7,799 (1, 6); 7,778 (3, 1) 7.743 (1, 7); 7.725 (2.2); 7.705 (1.0); 7.511 (3.7); 7.490 (3.3); 7.458 (3.6); 7.429 (2.0); 7,386 (1.3); 7,370 (2.4); 7,354
(1,2);7,220(1,7);7,200(3,2);7,181 (1,6);6,856(2,2);6,838(1,9);5,756(2,7);5,350(8,6);3,325(72,9);2,944(0,4);2,784(0,4);2,672(0,7);2,506(90,0)^ 2,502(118,3):2,498(91,2);2,329(0,8);2,325(0,6);2,301(16,0);2,086(1,8);2,075(1,0);1,957(0,3);1,232(0,7):0,146(0,5);0,007(4,6):0,000(101 ,6);- 0,008(6,7);-0,150(0,5) (1.2); 7.220 (1.7); 7.200 (3.2); 7.181 (1.6); 6.856 (2.2); 6.838 (1.9); 5.756 (2.7); 5.350 ( 8.6), 3.325 (72.9), 2.944 (0.4), 2.784 (0.4), 2.672 (0.7), 2.506 (90.0) ^ 2.502 (118.3): 2.498 (91 , 2), 2,329 (0.8); 2,325 (0.6); 2,301 (16.0); 2,086 (1.8); 2,075 (1.0); 1,957 (0.3); 1,232 (0, 7): 0.146 (0.5); 0.007 (4.6): 0.000 (101, 6); - 0.008 (6.7); - 0.150 (0.5)
Beispie! 1-1-301 : 1H-NMR(400,0 MHz, de-DMSO): δ= 10,601 (8.9);10,202(3,4);9,629(4,9);9,613(5,1);8,359(4,2);8,355(4,7);8,347(4,6);8,343(4 ,6);7,996(4,4);7,992(4.6);7,976(4,9);7,972(4,9);7,957(4,2);7,935(5,5);7.899(0,4);7,883(12,0);7,836(2.8);7,817(4,4);7,798(2,2);7,^Step Example! 1-1-301: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.601 (8.9); 10.202 (3.4); 9.629 (4.9); 9.613 (5.1); 8.359 (4.2), 8.355 (4.7), 8.347 (4.6), 8.343 (4, 6), 7.996 (4.4), 7.9292 (4.6), 7.976 (4.9), 7.972 (4, 9); 7,957 (4.2); 7,935 (5.5); 7,899 (0.4); 7,883 (12.0); 7,836 (2.8); 7,817 (4.4); 7,798 (2.2); 7 ^
32(2,7);7,416(4,9);7,399(2,4):7,205(4,4);7,193(4,3);7,185(4,2);7,174(4,1);5,757(2,7):5,520(16,0);5,223(0,4);3,324(42,5);2,672(1,2);2,668(0, 9);2,507(148,4);2,503(197,2):2,499(152,1);2,330(1,2);1,241(1,8);1 ,232(1,5);1.226(2,0):1,046(0,6);1,030(0,6);0,146(1,0);0,008(8,5);0,000(19 4.8);-0, 150(0.9) 32 (2.7); 7,416 (4.9); 7,399 (2.4) 7,205 (4.4); 7.193 (4.3); 7,185 (4.2); 7,174 (4.1); 5,757 (2.7): 5.520 (16.0), 5.223 (0.4), 3.324 (42.5), 2.672 (1.2), 2.668 (0.9), 2.507 (148.4), 2.503 ( 197.2): 2.499 (152.1); 2.330 (1.2); 1.241 (1.8); 1, 232 (1.5); 1.226 (2.0): 1.046 (0.6); 1.030 (0.6), 0.146 (1.0), 0.008 (8.5), 0.000 (19 4.8), - 0, 150 (0.9)
Beispiel 1-1-302: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,930(2,6);9,914(2,7);7,687(6,5);7,643(2,3);7,624(2,6);7,306(2,2);7,289(3,2);7,271 (2,0Example 1-1-302: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.930 (2.6); 9.914 (2.7); 7.687 (6.5); 7.643 (2.3 7.624 (2.6), 7.306 (2.2), 7.289 (3.2), 7.271 (2.0
);5,519(8,9);4,573(14,9);4,037(1,5):4,033(1,5);4,024(1,4):4,011(0,5):3,323(26,7);2,672(0,5);2,636(16,0):2,508(50,1):2,503(65,2):2,499(49,3) ;2,330(0,4); 1 ,698(1 ,0); 1 ,680(2,3); 1 ,666(5,4); 1 ,654(7,4); 1 ,638(3,4); 1 ,617(1 , 1 ); 1 ,598(0,4); 1 ,491 (2,2); 1 ,483(2,3); 1 ,475(1 ,9); 1 ,460(0,7); 1 ,231 (0 ,6);0,008(2,8);0.000(59,7) ); 5,519 (8.9); 4,573 (14.9); 4,037 (1.5) 4,033 (1.5); 4,024 (1.4) 4,011 (0.5) 3,323 (26.7) 2,672 (0.5); 2,636 (16,0): 2,508 (50,1): 2,503 (65,2): 2,499 (49,3); 2,330 (0,4); 1, 698 (1, 0); 1, 680 (2,3); 1, 666 (5.4); 1, 654 (7,4); 1, 638 (3,4); 1, 617 (1, 1); 1, 598 (0.4); 1,491 (2,2); 1, 483 (2, 3); 1, 475 (1, 9); 1, 460 (0.7); 1, 231 (0, 6), 0.008 (2.8), 0.000 (59.7)
Beispiel 1-1-303: 'H-NMR(400,0 MHz, de-DMSO): 6= 10,639(8,8);10,203(4,1);9,667(5,0);9,650(5,1);8,387(4,5);8,383(4,6);8,375(4,8);8,371(4 Example 1-1-303: 'H-NMR (400.0 MHz, de-DMSO): 6 = 10.639 (8.8), 10.203 (4.1), 9.667 (5.0), 9.650 (5.1 ); 8,387 (4.5); 8.383 (4.6) 8.375 (4.8) 8.371 (4
,3);7,940{4,4);7,930(5,2);7,926(5,8);7,919(7,1);7,911(6,0);7,907(5,0);7,876(11,4):7,827(3,0);7,806(4,4);7,787(2,4);7,428(3,1);7,411(5,2);7,3 94(2,6);7,150(3,9);7,138(4.2);7,131(3.9);7,119(3,7);6,527(0,4);6,514(0,4);6,103(0,5);5,503(16,^ , 3); 7.940 {4.4); 7,930 (5.2); 7,926 (5.8); 7.919 (7.1); 7,911 (6.0); 7,907 (5.0); 7,876 (11, 4): 7.827 (3.0), 7.806 (4.4), 7.877 (2.4), 7.428 (3.1), 7.411 (5.2), 7.3 94 (2.6), 7.150 ( 3.9); 7,138 (4.2); 7,131 (3.9); 7,119 (3.7); 6,527 (0.4); 6,514 (0.4); 6,103 (0.5); 5,503 (16, ^
, 1 );2,672(1 ,6);2,585(0,5);2,503(253,0);2,329(1 ,5); 1 ,543(0,5); 1 ,463(5,2); 1 ,233(2,2); 1 ,045(5,2); 1 ,030(5,2);0,000(22,6)  , 1), 2,672 (1,6), 2,585 (0,5), 2,503 (253,0), 2,329 (1,5); 1, 543 (0.5); 1, 463 (5,2); 1, 233 (2, 2); 1, 045 (5.2); 1, 030 (5.2); 0.000 (22.6)
Beispiel 1-1-304: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,647(4,3);9,579(2,5);9,563(2,5);7,943(2, 1);7,921 (2,7);7,890(6.2);7,791 (1 ,4);7,772(2,3Example 1-1-304: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.647 (4.3), 9.589 (2.5), 9.563 (2.5), 7.943 (2, 1 7.921 (2.7), 7.890 (6.2), 7.791 (1, 4), 7.772 (2.3
);7,753(1,1);7,750(1,1);7,393(2,0);7,374(2,6);7,365(2,6);7,346(1,2);7,286(1 ,4);7,268(2,6);7,233(2,6);7,213(3,2);7,194(1 ,2);5,757(5,8);5,515( 8,2);3,322(93,2);2,671(1,1);2,668(0,9);2,507(143,7);2,502(189,2);2,498(145,4);2,334(0,9);2,329(1,1);2,280(16,0);1,045(1,2);1,030(1,2);0,14 6(0,8):0,008(8,1);0,000(178,0);-0,150(0,8) 7,753 (1,1); 7,750 (1,1); 7,393 (2,0); 7,374 (2,6); 7,365 (2,6); 7,346 (1,2); 7,286 (1, 4) 7.268 (2.6), 7.233 (2.6), 7.213 (3.2), 7.194 (1, 2), 5.757 (5.8), 5.515 (8.2), 3.322 (93.2); 2,671 (1.1); 2,668 (0.9); 2,507 (143.7); 2.502 (189.2); 2.498 (145.4); 2,334 (0.9); 2,329 (1.1); 2,280 (16.0); 1.045 (1.2); 1.030 (1.2); 0.146 (0.8): 0.008 (8.1); 0.000 (178.0); - 0.150 (0.8 )
Beispiel 1-1-305: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,780(9,7);9,519(4,9);9,503(5,0);8,318(8,1);8,305(8.4);7.961(4,1);7,939(5,4);7,893(12, 6);7,825(2,8);7,807(4,4);7,788(2.4);7,785(2,3);7.730(9,0);7,716(8,7);7,396(2,6);7,379(4,8);7,363(2.3);7,361(2,3);5,757(12,3);5,511(16Example 1-1-305: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.780 (9.7), 9.519 (4.9), 9.503 (5.0), 8.318 (8.1 8,305 (8.4); 7,961 (4,1); 7,939 (5.4); 7,893 (12,6); 7,825 (2,8); 7,807 (4,4); 7,788 (2.4); 7,785 (2 , 3); 7,730 (9.0); 7,716 (8.7); 7,396 (2.6); 7,379 (4.8); 7,363 (2.3); 7,361 (2.3); 5,757 (12.3) ; 5,511 (16
76(0,4);3,324(139,3);2,892(2,4);2,732(2,1 );2,672(1 ,4);2,667(1 ,1 );2,507(178,8);2,503(236,3);2,498(175,8);2,334(1 ,0);2,330(1 ,4);2,325(1 ,0);2 ,087(0,5);1 ,234(1,0);1,046(3,2);1 ,030(3,1);0,146(1,0);0,008(8,9);0,000(228,9);-0,008(10,4);-0,150(1,1) 76 (0.4), 3.324 (139.3), 2.892 (2.4), 2.732 (2.1), 2.672 (1, 4), 2.667 (1, 1), 2.507 (178.8), 2.503 (236.3); 2.498 (175.8); 2.334 (1, 0); 2.330 (1, 4); 2.325 (1, 0); 2, 087 (0.5); 1, 234 (1.0 1.046 (3.2); 1.030 (3.1); 0.146 (1.0); 0.008 (8.9); 0.000 (228.9); - 0.008 (10.4); - 0.150 ( 1,1)
Beispiel 1-1-306: 1H-NMR(400,0 MHz. de-DMSO): δ= 10,563(3,9);10,559(4,0);9,607(4,7);9.591(4,8);8,345(1 ,6);8,337(1 ,7);8,330(1,8);8.321(1Example 1-1-306: 1 H-NMR (400.0 MHz de-DMSO): δ = 10.563 (3.9); 10.599 (4.0); 9.607 (4.7); 9.591 (4.8 8,345 (1,6), 8,337 (1, 7), 8,330 (1,8), 8,321 (1
,9);8,318(2,2);8,310(1,7);8,302(1 ,8);8,294(1 ,6);7,965(3,9);7,944(5,4);7,879(12,0);7,845(2,8);7,827(4,3);7,807(2,0);7,805(2,2);7,432(2 15(4,7);7,399(2,3);7,397(2,4);7,383(1,5);7,370(1 ,6):7,360(1,9);7,356(2,0);7,347(2,0);7,343(2,0);7,333(1,7);7,320(1,6);6,895(0,9);6,88 6,876(1 ,6);6,865(2.5);6,857(1 ,5);6,844(1 ,5);6,835(0,8);5,759(1 ,6);5,513(16,0);3,327(44,9);2,679(0,4);2,675(0,5);2,510(60,5);2,506(81 ,0);2,5 01(62,1);2,337(0,3);2,332(0,5);2,329(0,4);1,048(0,8);1,032(0,8);0,146(0,4);0,008(3,8);0,000(85,7);-0,008(4,6);-0,150(0,4) 8,318 (2,2), 8,310 (1,7), 8,302 (1,8), 8,294 (1,6), 7,965 (3,9), 7,944 (5,4), 7,879 (12), 7.845 (2.8), 7.827 (4.3), 7.807 (2.0), 7.805 (2.2), 7.432 (2 15 (4.7), 7.399 (2.3), 7.397 ( 2.4); 7.383 (1.5); 7.370 (1.6): 7.360 (1.9); 7.356 (2.0); 7.347 (2.0); 7.343 (2.0); 7.333 (1 , 7), 7,320 (1,6), 6,895 (0,9), 6,88 6,876 (1,6), 6,865 (2.5), 6,857 (1,5), 6,844 (1,5), 6,835 (0 , 8), 5.759 (1,6), 5,513 (16,0), 3,327 (44,9), 2,679 (0,4), 2,675 (0,5), 2,510 (60,5), 2,506 (81, 2.51 (62.1); 2.337 (0.3); 2.322 (0.5); 2.329 (0.4); 1.048 (0.8); 1.032 (0.8); 0.146 (0); 0.4) 0.008 (3.8) 0.000 (85.7) - 0.008 (4.6) - 0.150 (0.4)
Beispiel 1-1-307: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,994(8,8);9,542(4,8);9,526(4,9);8.033(0,4);8,022(0,4);7,970(4,0);7,948(5,5);7,891 (11 ,Example 1-1-307: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.994 (8.8), 9.542 (4.8), 9.526 (4.9), 8,033 (0.4 8,022 (0.4); 7,970 (4.0); 7,948 (5.5); 7,891 (11,
6);7,845(2,8);7,825(4,3);7,805(2,2);7,737(4,4);7,718(6,5);7,697(3,9);7,675(2,5);7,575(0,6);7,488(2,0);7,475(2,3);7,467(3,1);7,455(3,1);7,4476); 7.845 (2.8); 7,825 (4.3); 7,805 (2.2); 7,737 (4.4); 7,718 (6.5); 7,697 (3.9); 7,675 (2.5 ); 7,575 (0.6); 7,488 (2.0); 7,475 (2.3); 7,467 (3.1); 7,455 (3.1); 7,447
(1,7);7,434(1,5):7,420(2,8);7,403(5.0);7,386(2,5);7.204(0,3);6,520(0,4);6,500(0,6);6,475(0,5);5,757(1,0);5,516(16.0);4 (1.7); 7,434 (1.5) 7,420 (2.8); 7,403 (5.0); 7,386 (2.5); 7,204 (0.3); 6,520 (0.4); 6,500 (0, 6); 6,475 (0.5); 5,757 (1.0); 5,516 (16.0); 4
322(79,9);2,672(1,3);2,503(214,8);2,499(188,4);2,329(1,3);1,233(0,6);1,048(1,1);1,031(1,1);0,146{0,9);0,000{183,0):-0,149(0,9) 322 (79.9); 2,672 (1.3); 2,503 (214.8); 2,499 (188.4); 2,329 (1.3); 1,233 (0.6); 1,048 (1.1); 1,031 (1.1); 0.146 {0.9); 0.000 {183.0) - 0.149 (0.9)
Beispiel 1-1-308: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,651 (8,3);9,616(4,7);9,600(4,9);8,908(3,6);8,905(4,3);8,888(3,9);8,884(4,4);8,080(3,Example 1-1-308: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.651 (8.3), 9.616 (4.7), 9.600 (4.9), 8.908 (3.6 ); 8,905 (4.3); 8,888 (3.9); 8.884 (4.4); 8,080 (3,
8);8,077(4,5);8,069(4.4);8,066(4,6);7,958(3,7);7,937(5,4);7,880(11 ,1);7,851(2,9);7,832(4,2);7,811 (2,2);7,450(3,5);7,438(5,6);^ 8); 8.077 (4.5); 8.069 (4.4); 8.066 (4.6); 7.958 (3.7); 7.937 (5.4); 7.880 (11.1); 7.851 (2.9); 7.832 (4.2); 7.811 (2.2); 7.450 (3.5); 7.438 (5.6); ^
8(8,0);7,401(2,4);5,531(16,0);3,326(39,5);2,673(0,8);2,504(125,2);2,501(105,0);2,331(0,7);1,047(0,8);1 ,031(0,8);0,000(10,0)  8 (8.0); 7,401 (2.4); 5,531 (16.0); 3,326 (39.5); 2,673 (0.8); 2,504 (125.2); 2.501 (105.0); 2.331 (0.7); 1.047 (0.8); 1, 031 (0.8); 0.000 (10.0)
Beispiel 1-1-309: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,741(4,3);9,552(2,4);9,535(2,5);8,190(3,2);8,178(3,4);7,953(2,1);7,931(2,7);7,891 (5,6Example 1-1-309: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.741 (4.3), 9.552 (2.4), 9.535 (2.5), 8.190 (3.2 8.178 (3.4), 7.953 (2.1), 7.931 (2.7), 7.891 (5.6)
);7,812(1,4);7,791(2,2);7,772(1,2);7,579(0,5);7,509(0,4);7,498(0,4);7,390(4,2);7,376(4,4);7,357{1,3);5,758(1,5);5,517(8,0);5,237(0,6);4,588(); 7,812 (1.4); 7,791 (2.2); 7,772 (1.2); 7,579 (0.5); 7,509 (0.4); 7,498 (0.4); 7,390 (4.2) ; 7,376 (4.4); 7,357 {1,3); 5,758 (1.5); 5,517 (8.0); 5,237 (0.6); 4,588 (
0,5);4,573(0,4);3,327(9,2);2,672(0,6);2,503(87,2);2,499(68,8);2,317(16,0);2,229(1,4);2,206(0,4);2,152(1,8);2,075(0,4);1,233(1,1);0,000(7,7)0.5); 4,573 (0.4); 3,327 (9.2); 2,672 (0.6); 2,503 (87.2); 2,499 (68.8); 2.317 (16.0); 2.229 (1 , 4); 2,206 (0.4); 2,152 (1.8); 2,075 (0.4); 1,233 (1.1); 0,000 (7.7)
Beispiel 1-1-310: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,544(9,1);9,573(4,8);9,556(5,0);8,679(4,0);8,675(4,7);8,667(4,4);8,663(4,6);8,350(3,Example 1-1-310: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.544 (9.1), 9.583 (4.8), 9.556 (5.0), 8.679 (4.0 ); 8,675 (4.7); 8,667 (4.4); 8.663 (4.6); 8,350 (3,
9);8,345(4,3);8,330(4,2);8,326(4,3);7,985(3,9);7,963(5,5);7,888(12,0);7,871(3,1);7,852(4,4);7,830{2,3);7,449(2,7);7,433(4,8);7,415(2,6);7,40 5(4,3);7,393(4,1);7,386(4,2);7,374(4,0);5,757(0,4);5,521 (16,0)A 95,0);2,330(0,7);1,046(2,6);1 ,031(2,6);0,145(0,5);0,007(4,2);-0,001(101,3);-0,150(0,5) 9); 8.345 (4.3); 8,330 (4.2); 8,326 (4.3); 7,985 (3.9); 7,963 (5.5); 7,888 (12.0); 7,871 (3.1 7.852 (4.4), 7.830 {2.3), 7.499 (2.7), 7.433 (4.8), 7.415 (2.6), 7.40 5 (4.3), 7.393 (4 , 1); 7,386 (4,2); 7,374 (4,0); 5,757 (0,4); 5,521 (16,0) A 95.0); 2.330 (0.7); 1.046 (2.6); 1, 031 (2.6); 0.145 (0.5); 0.007 (4.2); - 0.001 (101.3); -0.150 (0.5)
Beispiel 1-1-311 : 1H-NMR(400,0 MHz, de-DMSO): δ= 10,455 (7,5);9,632(4,6);9,616(4,7):8.388(4.3);8,367(4,5);8,317(0,3):8,045(0,6);8.035(0. 6);7,940(3,9);7,918(5,5);7,870(11,5);7,829(2,8);7.810(4,4);7,788(2,1);7,721(4,0);7,702(4,3);7,677(2,0);7,657(3,8);7,638(2,1);7,575Example 1-1-311: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.455 (7.5); 9.632 (4.6); 9.616 (4.7): 8.388 (4.3); 8.367 (4.5), 8.317 (0.3): 8.045 (0.6), 8.035 (0.6), 7.940 (3.9), 7.918 (5.5), 7.870 (11.5), 7.829 (2.8); 7,810 (4.4); 7,788 (2.1); 7.721 (4.0); 7,702 (4.3); 7,677 (2.0); 7,657 (3.8); 7,638 ( 2.1); 7,575
8(2,7);7,402(4,9);7,385(2,5);7,283(2,4);7,264(4,2);7,245(2,1);7,207(0,4);6,576(0,5):6,560(0,6);6,547(0,5);6,522(0,8);6,501(0,8);5,757(2,1);58 (2.7); 7,402 (4.9); 7,385 (2.5); 7.283 (2.4); 7,264 (4.2); 7,245 (2.1); 7,207 (0.4); 6,576 (0.5) 6,560 (0.6); 6,547 (0.5); 6,522 (0.8); 6,501 (0.8); 5,757 (2.1); 5
519(16,0);4,583(1,5);4,568(1 ,6);3,323(82,2);2,672(1,4);2,507(184,9);2,5O3(240,7);2,499(192,5);2,330(1,4);1,352(1,1);1,3 519 (16.0); 4.583 (1.5); 4.568 (1, 6); 3.323 (82.2); 2.672 (1.4); 2.507 (184.9); 2.5O3 (240.7) ; 2,499 (192.5); 2,330 (1.4); 1,352 (1.1); 1.3
1 ,231 (2, 1 );0,146(0,9);0,000(172.0);-0, 150(0,9)  1, 231 (2, 1), 0.146 (0.9), 0.000 (172.0), - 0, 150 (0.9)
Beispiel 1-1-312: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,602(4,5);9,585(4,7);8,528(5,9);8,523(6,4);8,397(1,9);8.380(4,0);8,364(2,2);7,827(3,0Example 1-1-312: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.602 (4.5), 9.585 (4.7), 8.528 (5.9), 8.523 (6.4 ); 8,397 (1.9); 8,380 (4.0); 8,364 (2.2); 7.827 (3.0
);7,821(3,3);7,806(3,5);7,800(3,7);7,758(2,4);7,737(6,1);7,719(3,6);7,701(4,0);7,679(1 ,6);7,502(6,0):7,481(5,4);7,353(2,3);7,336(4,3);7 2,3);5,304(16,0);5,226(0,4);4,208(1 ,0);4, 184(3,4);4, 167(3,7);4,160(4, 1 );4, 143(3,4);4, 118(1 ,2);3,737(0,7);3,323(122,9);2,672(1 ,5);2,502(256, 5);2,330(1,5);2,301(0,7);1,235(0,5);0,146(0,9);0,000(175,6);-0,150(0,9) ); 7.821 (3.3) 7.806 (3.5); 7,800 (3.7); 7.758 (2.4); 7,737 (6.1); 7,719 (3.6); 7,701 (4.0) 7.679 (1,6); 7,502 (6,0): 7,481 (5,4); 7,353 (2,3); 7,336 (4,3); 7,3,3); 5,304 (16,0); 5,226 (0.4); 4.208 (1, 0); 4, 184 (3.4); 4, 167 (3.7); 4.160 (4, 1); 4, 143 (3.4); 4, 118 (1,2), 3,737 (0,7), 3,323 (122,9), 2,672 (1,5), 2,502 (256, 5), 2,330 (1,5), 2,301 (0,7), 1,235 ( 0.5); 0,146 (0.9); 0,000 (175.6) - 0.150 (0.9)
Beispiel 1-1-313: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,560(11 ,5);9,541 (5,2);8,560(6,0);8,554(6,2);7,868(3,4);7,861 (3,4);7,847(3,9);7,841 (3,Example 1-1-313: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.560 (11.5), 9.541 (5.2), 8.560 (6.0), 8.554 (6.2 7.868 (3.4), 7.861 (3.4), 7.847 (3.9), 7.841 (3,
9):7,800(2,5):7,779(6,0);7,760(3,4):7,758(3,5):7,743(3,7);7,740(4,0);7,721(1,6);7,718(1,7):7,520(6,8);7,500(6,1);7,383(2,5);7,380(3,1);7,363 (5,8):7,345(3,6):7,342(3,6):7,321 (2,3):7,305(1,0):7,215(1,1):7,207(6,0):7,187(9,3):7,166(4,0):7,158(0,9);5,350(16,0):3,323(122,6);2,676(0,9)9): 7,800 (2.5) 7,779 (6.0); 7,760 (3.4) 7.758 (3.5) 7,743 (3.7); 7,740 (4.0); 7.721 (1.6 7.718 (1.7): 7.520 (6.8); 7.500 (6.1); 7.833 (2.5); 7.380 (3.1); 7.363 (5.8): 7.345 (3.6) : 7.342 (3.6): 7.321 (2.3): 7.305 (1.0): 7.215 (1.1): 7.207 (6.0): 7.187 (9.3): 7.166 (4.0): 7,158 (0.9); 5,350 (16.0) 3.323 (122.6); 2,676 (0.9)
;2,672(1,3);2,668(0,9);2,507(166,4);2,503(217,9);2,498(163,9);2,334(1,0);2,329(1,2);2,325(1,0);0,146(0,9):0,008(7,9);0,000(200,1);- 0,008(10,0);-0,150(0,9) ; 2,672 (1.3); 2,668 (0.9); 2,507 (166.4); 2.503 (217.9); 2.498 (163.9); 2,334 (1.0); 2,329 (1.2); 2.325 (1.0); 0.146 (0.9): 0.008 (7.9); 0.000 (200.1); - 0.008 (10.0); - 0.150 (0.9)
Beispiel 1-1-314: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,768(8,8);9,551(4,6);9,534(4,7);8,568(5,9);8,562(6,0);7.881(3,3);7,875(3,3);7,860(3.8Example 1-1-314: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.768 (8.8), 9.551 (4.6), 9.534 (4.7), 8.568 (5.9 ) 8.562 (6.0); 7,881 (3.3); 7,875 (3.3); 7,860 (3.8
);7,854(3,8);7,812(2,8);7,791 (5,6);7,758(3,2);7,740(4,0);7,721 (1,7);7,718(1 ,7);7,578(13,0);7,558(16,0);7,533(6,6);7,512(5,8);7,380(2,4^7.854 (3.8), 7.812 (2.8), 7.791 (5.6), 7.758 (3.2), 7.740 (4.0), 7.721 (1.7), 7.718 (1, 7) ; 7,578 (13.0); 7,558 (16.0); 7,533 (6.6); 7,512 (5.8); 7,380 (2.4 ^
7(2,6):7,365(6,4);7,345(7,8);7,325(3,2);7,237(1,2):7,217(1,3);6,602(0,4);6,581(0,7);6,561(0,4);5,757(7,2);5,468(0,5):5,355(14,9):3,326(161,7 (2.6) 7.365 (6.4) 7.345 (7.8) 7.325 (3.2); 7,237 (1.2) 7,217 (1.3); 6,602 (0.4); 6,581 (0.7); 6,561 (0.4); 5,757 (7.2); 5,468 (0.5) 5,355 (14.9) 3,326 (161,
3);2,672(1,0);2,668(0,8);2,508(137,0);2,503(179,5):2,499(135,2);2,334(0,7):2,330(1,0);0,146(0,5);0,008(5,0);0,000(103,3);-0,150(0,5)3); 2,672 (1.0); 2,668 (0.8); 2,508 (137.0); 2.503 (179.5) 2.499 (135.2); 2,334 (0.7) 2,330 (1.0 ); 0.146 (0.5) 0.008 (5.0) 0.000 (103.3) - 0.150 (0.5)
Beispiel 1-1-315: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,688(8,7);9,644(5,0);9,627(5,1);8,555(6,3);8,549(6,4);8,353(4,4);8,350(4,9);8,342(4,Example 1-1-315: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.688 (8.7), 9.644 (5.0), 9.627 (5.1), 8.555 (6.3 ); 8,549 (6.4); 8,353 (4.4); 8,350 (4.9); 8,342 (4,
9);8,338(4,9);8,317(0,5);7,985(4,4);7,982(4,5);7,965(4,8);7,962(4,6);7,861(3,5);7,855(3,5);7,840(3,9);7,834(3,9);7,804(1,7);7,782(9,1);7,7639); 8,338 (4.9); 8,317 (0.5); 7,985 (4.4); 7,982 (4.5); 7,965 (4.8); 7.962 (4.6); 7,861 (3.5 ); 7,855 (3.5); 7,840 (3.9); 7,834 (3.9); 7,804 (1.7); 7,782 (9.1); 7,763
(4,0);7,741 (1,3);7,518(6,8);7,497(6,1);7,422(2,1);7,417(2,2);7,405(3,9);7,400(4,0);7,388(2,0);7,384(2,0);7,194(4,3);7,1^ (4.0); 7.741 (1.3); 7.518 (6.8); 7.497 (6.1); 7.422 (2.1); 7.417 (2.2); 7.405 (3.9); 7.400 ( 4.0); 7,388 (2.0); 7,384 (2.0); 7,194 (4.3); 7.1 ^
62(4,0):5,362(18,0);3,818(0,5);3,737(0,7);3,325(50,1);2,871(1 ,4);2,667(1,1);2,542(1,8);2,507(196,1);2,502{254,5);2,498(193,3);2,329(1,5);0 62 (4.0): 5.362 (18.0), 3.818 (0.5), 3.737 (0.7), 3.325 (50.1), 2.871 (1.4), 2.667 (1.1), 2.542 (1.8); 2,507 (196.1); 2.502 {254.5) 2.498 (193.3); 2,329 (1.5) 0
,146(0,8);0,000(178,4):-0,150(0,9) , 146 (0.8); 0,000 (178.4) - 0.150 (0.9)
Beispiel 1-1-316: 1H-NMR(400,0 MHz, de-DMSO): δ= 9,706(8,9);9,553(4.9);9,537(5,0);8,562(6,1);8,556(6,4);8.138(0,3);7,872(3.2);7,866(3,3Example 1-1-316: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.706 (8.9); 9.553 (4.9); 9.537 (5.0); 8.562 (6.1); 8,556 (6.4); 8,138 (0.3); 7,872 (3.2); 7,866 (3.3
);7,852(3,7);7,846(3,7);7,804(2,6);7,783(6,1);7,761(3,5);7,742(4,1);7,721(1 ,7);7,525(6,5);7,504(5,8):7,434(2,5);7,419(3,9);7,412(3,9);7,397^ 0,5);7,381(2,5);7,364(4,7);7,350(5,1);7,341(4,4);7,334(7,9);7,317(5,5);7,297(0,8);5,353(16,0);3,326(174,8):2,672(1,6);2,502(272,4);2,329(1, 6);2,075(1,5);0,146(0,8);-0,001 (152,5);-0,150(0,8) 7.852 (3.7), 7.846 (3.7), 7.804 (2.6), 7.783 (6.1), 7.761 (3.5), 7.742 (4.1), 7.721 (1, 7) 7.525 (6.5); 7.504 (5.8): 7.434 (2.5); 7.419 (3.9); 7.412 (3.9); 7.397 ^ 0.5); 7.381 (2.5); 7,364 (4.7); 7,350 (5.1); 7,341 (4.4); 7,334 (7.9); 7,317 (5.5); 7,297 (0.8); 5,353 (16.0); 3,326 (174.8): 2.672 (1.6); 2.502 (272.4); 2.329 (1, 6); 2.075 (1.5); 0.146 (0.8); - 0.001 (152.5); - 0.150 (0.8)
Beispiel 1-1-317: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,467(4,7):9,580(4,6);9,563(4,9);8,559(6,2);8,553(6.4);8,321(0,6);8,238(4,5);8,225(4, 7);7,873(5,4);7,867(4,3);7,852(6,5);7.846(6,6);7,828(3,0);7,811(6,0);7,801(4,0);7,781(4,0);7,761(1.5);7,519(7,0);7,498(6,4);7,^ Example 1-1-317: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.467 (4.7): 9.580 (4.6); 9.563 (4.9); 8.559 (6.2 8,553 (6.4), 8.321 (0.6), 8.238 (4.5), 8.225 (4. 7), 7.873 (5.4), 7.867 (4.3), 7.852 (6.5), 7.846 (6.6); 7,828 (3.0); 7,811 (6.0); 7,801 (4.0); 7.781 (4.0); 7,761 (1.5); 7,519 (7.0); 7,498 (6, 4); 7 ^
(2,4):7,410(3,9);7,406(4,3);7,393(2,1):7,389{2,1):7,319(2,1):7,309(2,8);7,298(3,8):7,289(2,5):7,277(2,0);5,364(16,0);4,063{14,1):3,821(0,6); 3,736(0,4);2,676(1,7);2,671 (2,4);2,667(1 ,8);2,542(1 ,7);2,507(310,3);2,502(412,3);2,498(309,6);2,334(1 ,7);2,329(2,4);2,325(1 ,8);0, 146(1 ,3); (2,4): 7.410 (3.9); 7,406 (4.3); 7,393 (2.1): 7.389 {2.1) 7,319 (2.1) 7,309 (2.8); 7,298 ( 3.8) 7,289 (2.5) 7,277 (2.0); 5,364 (16.0); {4.063 14.1) 3,821 (0.6); 3,736 (0.4), 2,676 (1,7), 2,671 (2,4), 2,667 (1,8), 2,542 (1, 7), 2,507 (310,3), 2,502 (412,3), 2,498 (309.6); 2.334 (1, 7); 2.329 (2.4); 2.325 (1, 8); 0.146 (1, 3);
0,007(11,3);0,000(269,9);-0,008(13,3);-0,150(1,3) 0.007 (11.3); 0.000 (269.9) - 0.008 (13.3) - 0.150 (1.3)
Beispiel 1-1-318: 'H-NMR(400,0 MHz, de-DMSO): δ= 11 ,334(7,4);9,551 (4,7);9,534(4,7);7,993(3,8);7,972(5.3);7,877(13,5);7,860(4.4);7,840(2 ,1);7,465{7,8);7,456(8,5);7,448(2,8);7,429(4,6);7,413(2,3);7,203(6,2);7,194{5,9);5,757(1,5);5,521(16,0);3,323(100,7);2,672(1,1);2,507(148,4 ):2,503(190,0);2,330(1,1);1,233(0,4);1,046(1,5);1,030(1,5);0,146(0,5);0,008(6,7):0,000(117,8);-0,150(0,5)  Example 1-1-318: 'H NMR (400.0 MHz, de-DMSO): δ = 11, 334 (7.4), 9.551 (4.7), 9.534 (4.7), 7.993 (3 , 8), 7.972 (5.3), 7.877 (13.5), 7.860 (4.4), 7.840 (2, 1), 7.465 (7.8), 7.456 (8.5), 7.448 (2.8), 7.429 (2.672; (4.6); 7,413 (2.3); 7,203 (6.2); 7,194 {5.9); 5,757 (1.5); 5,521 (16.0); 3.323 (100.7) 1.1), 2.507 (148.4): 2.503 (190.0), 2.330 (1.1), 1.233 (0.4), 1.046 (1.5), 1.030 (1.5), 0.146 (0 , 5); 0.008 (6.7) 0.000 (117.8) - 0.150 (0.5)
Beispiel 1-1-319: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,189(3,3);9,546(1,7);9,529(1,8);7,976(1,4);7,955(1,9);7,941(1,5);7,938(1,8);7,920(1, 6):7,917(1 ,9);7,897(4,4);7,888(1 ,7);7,886(1 ,7);7,869(1 ,8);7,866(1 ,7);7,852(1 ,0);7,833(1 ,6);7,811 (0,8);7,464(1 ,5):7,444(2,6):7,428(1 ,1 );7,425 (1,6);7,412(1,7);7,393(0,9);5,523(5,6);4,347(1,2);4,337(1,2);3,795(0,4);3,785(0,5);3,779(0,6);3,769(0,6);3,764(0,5);3,754(0,4);3,326(29,9);2, 509(33,1);2,504(44,0);2,500(33,2);1 ,047(16,0); 1 ,032(15,8);0,008(1 ,4);0,000(36,3);-0,009(1 ,9) Example 1-1-319: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10,189 (3.3); 9.546 (1.7) 9.529 (1.8); 7,976 (1.4 7.955 (1.9); 7.941 (1.5); 7.938 (1.8); 7.920 (1, 6): 7.917 (1.9); 7.897 (4.4); 7.888 (1, 7) 7,886 (1, 7), 7,869 (1, 8), 7,866 (1, 7), 7,852 (1, 0), 7,833 (1,6), 7,811 (0,8), 7,464 (1, 5): 7.444 (2.6): 7.428 (1, 1); 7.425 (1.6); 7.412 (1.7); 7.393 (0.9); 5.523 (5.6); 4.347 (1.2); 4.337 (3,326 (1.2); 3,795 (0.4); 3,785 (0.5); 3,779 (0.6); 3,769 (0.6); 3,764 (0.5); 3,754 (0.4) 29.9), 2.509 (33.1), 2.504 (44.0), 2.500 (33.2), 1.047 (16.0); 1, 032 (15.8), 0.008 (1, 4), 0.000 (36.3), - 0.009 (1, 9)
Beispiel 1-1-320: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,836(3,8);9,456(2,0);9,440(2,1);8,686(1,9);8,682(2,1);8,674(2,0);8,670(2.1);8,432(1, 8);8,428(1 ,9);8,412(1 ,9);8,408(1 ,9);7,981 (1,6);7,959(2.2);7,892(5,3);7,869(1,1);7,866(1,2);7,847(1,8);7,829(0,9);7,826(0,9);7,432(2,0);7,420Example 1-1-320: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.836 (3.8), 9.456 (2.0), 9.440 (2.1), 8.686 (1.9 8.682 (2.1), 8.674 (2.0), 8.670 (2.1), 8.432 (1, 8), 8.428 (1, 9), 8.412 (1, 9), 8.408 (1, 9), 7.981 (1.6); 7,959 (2.2); 7,892 (5.3); 7,869 (1.1); 7,866 (1.2); 7,847 (1.8); 7,829 (0.9); 7,826 (0, 9); 7,432 (2.0); 7,420
(2,0);7,411 (2,8);7,399(2,8);7,380(1,0):7,377(1,0):5,757(16,0);5,518(6,5);3,325(88,3);2,677(0,4);2,672(0,5);2,668(0,4):2,568(5,7);2,525(1,6);(2.0); 7.411 (2.8); 7.399 (2.8); 7.380 (1.0): 7.377 (1.0): 5.757 (16.0); 5.518 (6.5); 3.325 ( 88.3) 2,677 (0.4); 2,672 (0.5); 2,668 (0.4) 2,568 (5.7); 2,525 (1.6);
2,512(31,3);2,508(63,9);2,503(85,5);2,499(63,9);2,495(32,5):2,335(0,3);2,330(0,5);2,325(0,4);1,046(0,4);1,031(0,4);0,008(2,6);0,000 0,008(3,3);-0,150(0,3) 2,512 (31.3); 2,508 (63.9); 2.503 (85.5); 2,499 (63.9); 2,495 (32.5) 2,335 (0.3); 2,330 (0.5); 2,325 (0.4); 1.046 (0.4); 1.031 (0.4); 0.008 (2.6); 0.000 0.008 (3.3); - 0.150 (0.3)
Beispiel 1-1-321 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,616(1 ,2);9,600(1 ,2);9,496(1 ,9);7,932(1 ,0);7,910(1 ,3);7,892(2,9);7,767(0,7);7,748(1 ,1Example 1-1-321: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.616 (1.2), 9.600 (1.2), 9.496 (1.9), 7.932 (1.0 7.910 (1, 3), 7.892 (2.9), 7.767 (0.7), 7.748 (1, 1
);7,726(0,6);7,369(0,7);7,352(1,2);7,333(0,6);7,129(0,4);7,105(4,5);7,100(3,4):7,090(0,9);5,520(3,9);4,102(0,5);4,088(0,6);3,327); 7,726 (0.6); 7,369 (0.7); 7,352 (1.2); 7,333 (0.6); 7,129 (0.4); 7,105 (4.5); 7,100 (3.4) : 7,090 (0.9); 5,520 (3.9); 4,102 (0.5); 4,088 (0.6); 3,327
(2,7);3,165(2,7);2,509(27,1);2,504(34,7);2.500(26,5);2,228(16,0);0,000(20,5) (2.7); 3,165 (2.7); 2,509 (27.1); 2,504 (34.7); 2500 (26.5); 2,228 (16.0); 0.000 (20.5)
Beispiel 1-1-322: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,086(4,3);9,666(2,7);9,649(2,7);8,288(1 ,6);8,274(1 ,8);8,266(1 ,8);8,252(1 ,6);7,941 (2,Example 1-1-322: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.086 (4.3), 9.666 (2.7), 9.649 (2.7), 8.288 (1, 6 8.274 (1, 8), 8.266 (1, 8), 8.252 (1, 6), 7.941 (2,
2);7,919(2,9);7,878(5.8);7,801(1,5);7,781(2,4);7,761(1,3);7,409(1,5);7,391(2.7);7,374(1,4):7,134(1,6) (7.374, 2); 7.919 (2.9); 7,878 (5.8); 7,801 (1.5); 7.781 (2.4); 7,761 (1.3); 7,409 (1.5); 7,391 (2.7) 1.4) 7,134 (1.6)
(1,0);7,037(0,9);7,021(1,8);7,015(1,6);7,000(1,0);6,993(0,8);5,529(8,7);3,329(15,0);2,506(47,6)i  (3,329 (1.0); 7,037 (0.9); 7,021 (1.8); 7.015 (1.6); 7,000 (1.0); 6,993 (0.8); 5,529 (8.7) 2,506 (47.6) i; 15.0)
7)  7)
Beispiel 1-1-323: 'H-NMR(400,0 MHz, de-DMSO): δ= 9,586(2,0);9,570(2,0);9,277(3,6);7,931(1,6);7,909(2,2);7,883(5,0);7,783(1,1);7,764(1,8 );7,745(0,9);7,742(0,9);7,375(1.1);7,358(2,0);7,342(1,0);7,340(0,9);7,281 (0,6);7,264(0,8);7,260(1 ,4);7.244(1 ,4);7,239(0.9);7.223(0,7);6,948( 2.0);6,927(1.8);6,903(1.1);6,880(1,8);6,858(0,9);5,500(6,5);3,827(16,0);3,326(40,4);2,672(0,3);2.508(42,5);2,504(54  Example 1-1-323: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.586 (2.0); 9.570 (2.0); 9.277 (3.6); 7.931 (1.6 7.909 (2.2), 7.883 (5.0), 7.783 (1.1), 7.764 (1.8), 7.745 (0.9), 7.742 (0.9), 7.375 (1.1), 7.358 (2.0); 7.342 (1.0); 7.340 (0.9); 7.281 (0.6); 7.264 (0.8); 7.260 (1, 4); 7.244 (1, 4); 7.239 (7) 7.223 (0.7), 6.948 (2.0), 6.927 (1.8), 6.903 (1.1), 6.880 (1.8), 6.858 (0.9), 5.500 (6.5), 3.827 (16, 0); 3,326 (40.4); 2,672 (0.3); 2,508 (42.5); 2,504 (54
7);0,000(34,5):-0,008(1,6)  7); 0.000 (34.5) - 0.008 (1.6)
Beispiel 1-1-324: 1H-NMR(400,0 MHz, de-DMSO): δ= 11.408 (7,4);9,563(4.9);9,546(5,0);8,550(6.1);8,545(6,3);7,875(3,3);7,869(3,3);7,854(3,Example 1-1-324: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11,408 (7.4); 9.563 (4.9); 9.546 (5.0); 8.550 (6.1); 8.545 ( 6.3); 7,875 (3.3); 7,869 (3.3); 7,854 (3,
7);7,848(3,8);7,833(1,1);7,818(10,1);7,804(4,9);7,782(0,9);7,511(6,2);7,490(5,6);7,455(7,4);7,446(8,0);7,435(2,3);7,428(2,2);7,419(3,2^ 3(3,3);7,403(1,9);7,397(1,9);7,196(6,1);7,187(5,9);5,361 (16,0);3,326(207,9);2,671(1,8);2,506(245,7):2,502(303,8);2,329(1,7):0,145(0,7):- 0,001(138,4);-0,150(0,6) 7); 7,848 (3.8); 7,833 (1.1); 7,818 (10.1); 7,804 (4.9); 7,782 (0.9); 7,511 (6.2); 7,490 (5.6 7.455 (7.4), 7.446 (8.0), 7.435 (2.3), 7.428 (2.2), 7.419 (3.2 ^ 3 (3.3), 7.403 (1.9); 7.397 (1.9), 7.196 (6.1), 7.187 (5.9), 5.361 (16.0), 3.326 (207.9), 2.671 (1.8), 2.506 (245.7): 2.502 (303.8) 2.329 (1.7) 0.145 (0.7): - 0.001 (138.4) - 0.150 (0.6)
Beispiel 1-1-325: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,412(2,8);9,592(1 ,7);9,575(1 ,7);8,548(2,1 );8.542(2, 1):7,857(1 ,2);7.851 (1 ,2);7,836(1 , 4);7,830(1,4);7,816(0,8);7,796(2,1);7,780(1,2);7,778(1,2);7,762( Example 1-1-325: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.412 (2.8), 9.592 (1, 7), 9.575 (1, 7), 8.548 (2.1 8,542 (2, 1): 7,857 (1,2), 7,851 (1,2), 7,836 (1,4), 7,830 (1,4), 7,816 (0,8), 7,796 (2,1) (7,762;; 7,780 (1.2); 7,778 (1.2)
(0,8);7,390(1,4);7,387(1,5);7,373(0,8);7,370(0,7);7,327(2,8);7,322(2,9):6,374(3,0);6,370(3,0);5,366(5,5);3,734(16,0);3,325(40,4);2,507(39,6) ;2,503(52,0);2,498(38,4);0,008(2,2);0,000(51,8);-0,008(2,4)  (6,374: 7,322 (2.9) (0.8); 7,390 (1.4); 7.387 (1.5); 7,373 (0.8); 7,370 (0.7); 7,327 (2.8) 3.0), 6.370 (3.0), 5.366 (5.5), 3.734 (16.0), 3.325 (40.4), 2.507 (39.6), 2.503 (52.0), 2.448 (38 , 4) 0.008 (2.2) 0.000 (51.8) - 0.008 (2.4)
Beispiel 1-1-326: 'H-NMR(400,0 MHz, de-DMSO): δ= 10,512(3,2);9,735(1,9);9,718(2,0);8,543(2,3);8,537(2,3);8,474(1,6);8.470(1,7);8,455(1, 7);8,451 (1 ,7);7,835(1 ,3);7,829(1 ,3);7,814(1 ,5);7,808(1 ,5);7,751 (0,6);7,732(2,3);7,727(3,0);7,709(1 ,5);7, 707(1 ,5);7,688(0,5);7,685(0,5);7,510 Example 1-1-326: 'H NMR (400.0 MHz, de-DMSO): δ = 10.512 (3.2); 9.735 (1.9); 9.718 (2.0); 8.543 (2.3 8.377 (2.3), 8.474 (1.6), 8.470 (1.7), 8.455 (1, 7), 8.451 (1, 7), 7.835 (1, 3), 7.829 (1, 3) 7.814 (1, 5), 7.808 (1.5), 7.751 (0.6), 7.732 (2.3), 7.727 (3.0), 7.709 (1.5), 7.702 (1.5 ); 7.688 (0.5); 7,685 (0.5); 7,510
(2,7);7,489(2,5);7,380(0,9);7,376(0,9):7,363(1,6):7,359(1,7):7,347(0,8):7,342(0,8);7,308(0,3):7,059(1,0);7,055(1,2);7,038(2,0);7,035(2,1);7,0 05(0,9);7,001(1,0);6,986(1,5);6,982(1,6):6,966(0,9);6,962(0,9);6,937(1 ,1);6,933(1 ,1);6,917(1,4);6,914(1,5):6,899(0,6);6,895(0,6);5,757(0,5)^(2.7); 7,489 (2.5); 7,380 (0.9); 7,376 (0.9) 7,363 (1.6) 7,359 (1.7) 7,347 (0.8): (7,342 0.8), 7.308 (0.3): 7.059 (1.0), 7.055 (1.2), 7.038 (2.0), 7.035 (2.1), 7.0 05 (0.9); 7.001 (1.0), 6.986 (1.5), 6.982 (1.6): 6.966 (0.9), 6.962 (0.9), 6.937 (1, 1), 6.933 (1, 1), 6.917 6,899 (0.6); 6,895 (0.6); 5,757 (0.5) ^: 6,914 (1.5) (1.4)
5,358(6,0);3,877(16,0);3,684(0,3);3,324(112,7);2,676(0,5);2,671(0,7);2,667(0,5);2,524(2,5);2,511 (45,9);2,507(92,5);2,502(123,4);2,498(91,7 ):2,493(46,2);2,333(0,5);2,329(0,7):2,324(0,6);0,146(0,4);0,008(3,5):0,000(86,5);-0,008(3,9);-0,150(0,4) 5,358 (6.0); 3,877 (16.0); 3,684 (0.3); 3,324 (112.7); 2,676 (0.5); 2,671 (0.7); 2,667 (0.5); 2,524 (2.5); 2.511 (45.9); 2.507 (92.5); 2.502 (123.4); 2.498 (91.7): 2.493 (46.2); 2.333 (0.5); 2.329 ( 0.7) 2,324 (0.6); 0.146 (0.4) 0.008 (3.5) 0.000 (86.5) - 0.008 (3.9) - 0.150 (0.4)
Beispiel 1-1-327: 1H-NMR(400,0 MHz, de-DMSO): δ= 11,270(3,9);9,546(3,2);9,530(3,2);8,544(4,0);8,539(4,1);8,134(0,4);7,868(2,3);7,861(2, 2);7,847(2,6);7,841 (2,5);7,825(0,8);7,809(6,4);7,795(2,9);7,773(0,6):7,507(4,4);7,486(3,9);7,427(1,3);7,421 (1 ,4);7,411 (2,2);7,405(2,3);7,396Example 1-1-327: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11.270 (3.9); 9.546 (3.2); 9.530 (3.2); 8.544 (4.0 8,539 (4.1), 8.134 (0.4), 7.868 (2.3), 7.861 (2, 2), 7.847 (2.6), 7.841 (2.5), 7.825 (0.8) 7.809 (6.4); 7.795 (2.9); 7.773 (0.6): 7.507 (4.4); 7.486 (3.9); 7.427 (1.3); 7.421 (1, 4); 7.411 (2.2); 7.405 (2.3); 7.396
(1,2);7,389(1,3);7,120(4,8);7,117(4,9);5,353(10,2);3,388(81,2);2,676(0,7);2,672(1,0):2,542(1,2);2,507(133,0);2,503(172,1);2,499(128,4);2,3(2,672 (1.2); 7,389 (1.3); 7,120 (4.8); 7,117 (4.9); 5,353 (10.2); 3,388 (81.2); 2,676 (0.7) 1.0) 2,542 (1.2); 2,507 (133.0); 2.503 (172.1); 2,499 (128.4); 2.3
56(15,8);2,355(16,0);2,339(0,8);2,334(0,9);2,330(1,1);0,146(0,4);0,008(4,9);0,000(97,4);-0,008(4,9);-0,150(0,5) 56 (15.8); 2.355 (16.0); 2,339 (0.8); 2,334 (0.9); 2,330 (1.1); 0.146 (0.4) 0.008 (4.9); 0,000 (97.4) - 0.008 (4.9) - 0.150 (0.5)
Beispiel 1-1-328: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,202(3,9);9,710(2,5);9,694(2,5);8,550(3,1);8,544(3,1);8,353(2,2);8,333(2,3);8,137(8, 6);7,851 (1 ,8);7,844(1 ,7);7,830(2,0);7,824(2,0);7,785(1 ,1);7,764(2,9);7, 747(1 ,7);7, 745(1 ,8);7,730(1 ,8);7,727(2,0);7,708(0,8);7,705(0,8);7,515 (3,5);7,495(3,1);7,398(1,2);7,394(1,2);7,381 (2,1);7,377(2,2);7,364(1,1):7,360(1,1);7,233(1,8);7,214(2,1);^ Example 1-1-328: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.202 (3.9), 9.710 (2.5), 9.694 (2.5), 8.550 (3.1 8,544 (3,1); 8,353 (2,2); 8,333 (2,3); 8,137 (8,6); 7,851 (1, 8); 7,844 (1, 7); 7,830 (2,0) 7.724 (2.0); 7.785 (1, 1); 7.764 (2.9); 7, 747 (1, 7); 7, 745 (1, 8); 7,730 (1, 8); 7,727 (2 7.708 (3.5); 7.495 (3.1); 7.398 (1.2); 7.394 (1.2); 7.381 (2); 7,360 (1.1); 7,233 (1.8); 7,214 (2.1); ^: 1);; 7.377 (2.2) 7.364 (1.1)
69(1,4);6,953(2.2);6,950(2,3):6,932(1,0):5,375(8,0);3,324(18,1):2,676(0,6);2,671(0,9);2 (0,6);2,541(0.7);2,511(57,0);2,507(113,6):2,502( 69 (1.4); 6.953 (2.2); 6,950 (2.3) 6,932 (1.0) 5,375 (8.0); 3,324 (18.1) 2,676 (0.6); 2,671 (0 , 9), 2 (0.6), 2.541 (0.7), 2.511 (57.0), 2.507 (113.6): 2.502 (
150,3);2,498(111,0);2,494(55,9);2,325(16,0);0,146(0,6):0,008(5,6);0,000(143,5);-0,008(6,5);-0,150(0,7) (0.008 - 0.008 (5.6) 0.000 (143.5) 150.3) 2.498 (111.0); 2,494 (55.9);; 2.325 (16.0) 0.146 (0.6) 6.5) - 0.150 (0.7)
Beispiel 1-1-329: 1H-NMR(400,0 MHz, de-DMSO): δ= 12,740(0,5);10,455(3,6);9,623(2,1):9,607(2,3);8,544(2,9);8,539(3,0);8,133(2,0):8,017(2Example 1-1-329: 1 H-NMR (400.0 MHz, de-DMSO): δ = 12.740 (0.5); 10.455 (3.6); 9.623 (2.1): 9.607 (2.3 ); 8.544 (2.9); 8,539 (3.0); 8,133 (2.0): 8.017 (2
,8);8,003(2,9);7,855(1,6);7,849(1 ,6);7,834(1 ,8);7,828(2,0);7,798(3,8);7,779(2,0);7,757(0,7):7,510(3,1);7,489(2,8);7,414(1,1);7,397(r, 8), 8.003 (2.9), 7.855 (1.6), 7.849 (1.6), 7.834 (1.8), 7.828 (2.0), 7.798 (3.8), 7.779 (2, 0); 7.757 (0.7) 7,510 (3.1); 7,489 (2.8); 7,414 (1.1); 7,397 (r
4(1 ,0);7,234(3,6);7,231 (3,7);7,067(1 ,9);7,063(1 ,8);7,053(1 ,9);7,048(1,8);5,346(7,1);5,226(0,4);3,831(16,0);3,736(0.7);3,325(67,4);2,672(1,3)4 (1, 0), 7.234 (3.6), 7.231 (3.7), 7.067 (1, 9), 7.063 (1, 8), 7,053 (1, 9), 7,048 (1,8), 5,346 (7.1); 5,226 (0.4); 3,831 (16.0); 3,736 (0.7); 3,325 (67.4); 2,672 (1.3)
;2,502(231 ,8);2,329(1 ,3): 1 , 199(0,5): 1 , 180(1 ,0); 1 , 162(0,5);0, 146(0,9);0,000(173,4);-0, 150(0,8) 2.502 (231, 8); 2.329 (1, 3): 1, 199 (0.5): 1, 180 (1, 0); 1, 162 (0.5); 0.146 (0.9); 0.000 (173.4); - 0, 150 (0.8)
Beispiel 1-1-330: 1H-NMR(400,0 MHz, de-DMSO): δ= 10.323(3,6);9,579(2,1);9,562(2.2);7,962(1,8);7,940(2.4);7,876(4,8);7,831(1,2);7,812(1,Example 1-1-330: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10,323 (3.6), 9.589 (2.1), 9.562 (2.2), 7.962 (1.8); 7,940 (2.4); 7,876 (4.8); 7,831 (1.2); 7,812 (1,
9);7,791(1,0);7,418(1,2);7,401(2,1);7,383(1,1);7,331(3,4);7,327(3,6);6,367(3,5):6,363(3,7);5,524(7,1);3,744(16,0);3,327(26,3);2,505(43,1);0, 000(22,0) 9); 7,791 (1.0); 7,418 (1.2); 7,401 (2.1); 7,383 (1.1); 7,331 (3.4); 7,327 (3.6); 6,367 (3.5 : 6.363 (3.7), 5.524 (7.1), 3.744 (16.0), 3.327 (26.3), 2.555 (43.1), 0, 000 (22.0)
Beispiel 1-1-331 : 1H-NMR(400,0 MHz, de-DMSO): δ= 9,862(9,2);9,502(4,5);9,486(4,7);8,833(14,0);7.969(3,7);7,948(5,1);7,893(11,5);7,844(2Example 1-1-331: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.862 (9.2); 9.502 (4.5); 9.486 (4.7); 8.833 (14.0 ); 7,969 (3.7); 7,948 (5.1); 7,893 (11.5); 7,844 (2
,5);7,841(2,5);7,822(4,1);7,803(2,1);7,801(2,0);7,405(2,4);7,402(2,4);7,386(4,5):7,370(2,2);7,367(2,2);5,756(16,0);5,511(14,7);4,039(0,7);4, 021(0,7);3,323(93,4);2,677(0,7);2,672(1,0):2,668(0,7):2,508(128,0);2,503(166,2);2,499(124,6);2,330(1,0);2,326(0,7);1,990(3,0);1,299(0,4);1 ,259(0,6);1 ,234(1,0);1,194(0,9);1 ,176(1,7);1,158(0,8):0,146(0,9);0,008(9,0):0,000(191,5);-0,008(10,0):-0,150(0,9) , 5); 7,841 (2.5); 7,822 (4.1); 7,803 (2.1); 7,801 (2.0); 7,405 (2.4); 7,402 (2.4); 7,386 (4, 5): 7.379 (2.2), 7.367 (2.2), 5.756 (16.0), 5.511 (14.7), 4.039 (0.7), 4, 021 (0.7), 3.323 (93 , 4); 2,677 (0.7); 2,672 (1.0) 2,668 (0.7) 2,508 (128.0); 2.503 (166.2); 2,499 (124.6); 2.330 (1, 0); 2,326 (0,7); 1,990 (3,0); 1,299 (0,4); 1, 259 (0,6); 1, 234 (1,0); 1,194 (0,9); 1 , 176 (1.7); 1,158 (0.8): 0.146 (0.9) 0.008 (9.0) 0.000 (191.5) - 0.008 (10.0) - 0.150 (0.9 )
Beispiel 1-1-332: 1H-NMR(400,0 MHz, de-DMSO): 6= 9,562(3,8);9,515(2,0);9,498(2,0);7,961(1,6);7,939(2,2);7,883(4.9);7,838(1.2);7,819(1.8 );7,798(0,9);7,567(6,5);7.406(1,1);7,390(2,0);7.371(1,0):5,757(5.1);5,508(6,4);4,137(0,5);3,785(0,5);3,718(16,0);3,695(1,0) Example 1-1-332: 1 H-NMR (400.0 MHz, de-DMSO): 6 = 9.562 (3.8), 9.515 (2.0), 9.498 (2.0), 7.961 (1.6 7.939 (2.2), 7.883 (4.9), 7.838 (1.2), 7.819 (1.8), 7.798 (0.9), 7.567 (6.5), 7.406 (1.1), 7.390 (2.0 ); 7,371 (1.0) 5,757 (5.1); 5,508 (6.4); 4,137 (0.5); 3,785 (0.5); 3,718 (16.0); 3,695 (1.0)
(0,3);3,590(0,4);3,574(0,4);3,551 (0,3);3,485(0,4);3,325(25,7);2,673(0,3);2,508(39,7);2,503(53, 1 );2,499(41 ,3); 1 ,990(0,4); 1 ,233(0,5); 1 ,046(5, 1 ); 1 ,031 (5, 1 );0,008(2,7);0,000(61 ,3) (0.3), 3.590 (0.4), 3.574 (0.4), 3.551 (0.3), 3.485 (0.4), 3.325 (25.7), 2.673 (0.3), 2.508 ( 39.7), 2.503 (53, 1), 2.499 (41, 3); 1, 990 (0.4); 1, 233 (0.5); 1, 046 (5, 1); 1, 031 (5, 1), 0.008 (2.7), 0.000 (61, 3)
Beispiel 1-1-334: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,622(8,8);9,693(13,9);9,643(4,9);9,627(4,9);8,315(1 ,0);8,230(8,1);8,216(8,5);7,963(3Example 1-1-334: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.622 (8.8); 9.693 (13.9); 9.643 (4.9); 9.627 (4.9 8,315 (1, 0), 8,230 (8,1), 8,216 (8,5), 7,963 (3
,7);7,941(5,4);7,877(11,8);7,859(3,0);7,838(4,3);7,817(2,1);7,634(8,1);7,621(7,8);7,441(2,5);7,424(4,7);7,408(2,3);5,528(16,0);4,342(0,5);4,, 7); 7,941 (5.4); 7.877 (11.8); 7,859 (3.0); 7,838 (4.3); 7,817 (2.1); 7,634 (8.1); 7.621 (7, 8); 7,441 (2.5); 7,424 (4.7); 7,408 (2.3); 5,528 (16.0); 4,342 (0.5); 4,
331(0,6);3,318(416,8);2,693(0,4);2,675(3,5);2,671(4,7);2,667(3,6);2,644(0,4);2,506(566,5);2,502(768,0);2,497(585,7);2,333(3,4);2,328(4,5); 2,324(3,3);1,236(0,7);1,045(3,3);1,030(3,2);0,146(3,3);0,008(29,4);0,000(684,4);-0,149(3,2) 331 (0.6); 3,318 (416.8); 2,693 (0.4); 2,675 (3.5); 2,671 (4.7); 2,667 (3.6); 2,644 (0.4); 2,506 (566.5) 2.502 (768.0); 2.497 (585.7); 2,333 (3.4); 2,328 (4.5); 2,324 (3.3); 1,236 (0.7); 1,045 (3.3); 1,030 (3.2); 0.146 (3.3) 0.008 (29.4); 0.000 (684.4) - 0.149 (3.2)
Beispiel 1-1-335: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,527(9,5);9,635(5,0);9,619(5,1);8,394(4.5);8,390(5.0);8,382(4.8);8,378(5,0);8,136(4, 8);8,132(5,0);8,116(5,2);8,112(5,1);7,953(4,0);7,931(5,6);7,882(12,5);7,836(2,7);7,833(2,9);7,814(4,6);7,795(2,3);7,793(2,3);7,432(2,^Example 1-1-335: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.527 (9.5), 9.635 (5.0), 9.619 (5.1), 8.394 (4.5); 8.390 (5.0), 8.382 (4.8), 8.378 (5.0), 8.136 (4, 8), 8.132 (5.0), 8.116 (5.2), 8.112 (5.1), 7.953 (4.0 ); 7,931 (5.6); 7,882 (12.5); 7,836 (2.7); 7,833 (2.9); 7,814 (4.6); 7,795 (2.3); 7,793 (2.3) ; 7,432 (2 ^
9(2,7):7,413(4.8):7,397(2,4);7,394(2,4);7, 126(4,7);7, 115(4,6);7, 107(4,6);7,095(4,5);5,757(0,4);5,518(16,0);4,344(0,4);4,334(0,4);3,323(45,4) ;2,678(0,4);2,673(0,6);2,669(0,4);2,526(1 ,7);2,509(71 ,9);2,504(99,9); 2,500(77,0);2,336(0,4);2,331 (0,6);2,327(0,5); 1 ,243(0,4); 1 ,228(0,8); 1 ,0 47(4, 1 ); 1 ,032(4,0);0, 146(0,5);0,008(4,3);0,000(105,5);-0,008(5,0);-0, 150(0,5) 9 (2.7): 7.413 (4.8): 7.397 (2.4); 7.394 (2.4); 7, 126 (4.7); 7, 115 (4.6); 7, 107 (4, 6), 7.095 (4.5), 5.757 (0.4), 5.518 (16.0), 4.344 (0.4), 4.334 (0.4), 3.323 (45.4), 2.678 (0.4 2.673 (0.6), 2.669 (0.4), 2.526 (1, 7), 2.509 (71, 9), 2.504 (99.9); 2.500 (77.0), 2.336 (0.4), 2.331 (0.6), 2.327 (0.5); 1, 243 (0.4); 1, 228 (0.8); 1, 0 47 (4, 1); 1, 032 (4.0); 0.146 (0.5); 0.008 (4.3); 0.000 (105.5); - 0.008 (5.0); - 0.15 (0.5)
Beispiel 1-1-336: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,506(8,9);10,201(1.4);9.588(4.8);9,571(4,9);8,696(3,7);8,685(3,7);8,316(0,5);8,218(3 ,5);8,214(3,6);8,198(3,7);8,195(3,8);7,956(4,0);7,934(5,5);7,879(12,5);7,843(2,7);7,840(2,9);7,822(4,5);7,803(2,2);7,8M Example 1-1-336: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.506 (8.9); 10.201 (1.4); 9.588 (4.8); 9.571 (4.9); 8.696 ( 3.7), 8.685 (3.7), 8.316 (0.5), 8.218 (3.5), 8.214 (3.6), 8.198 (3.7), 8.195 (3.8), 7.956 (4 , 0); 7,934 (5.5); 7,879 (12.5); 7,843 (2.7); 7,840 (2.9); 7,822 (4.5); 7,803 (2.2); 7.8 m
12(6,2);7,404(3,3);7,395(5,0);7,384(2,7);5,756(4,0);5,516(16,0);3,324(316,1);2,676(1,4);2,672(1,8);2,507(240,3);2,503(317,9);2,498(240,0); 2,334(1,3);2,329(1,8);2.325(1,4);1.352(0,3);1,233(1,3);1 ,046(3,0);1,030(2,9);0,146(1,6);0,008(15,^  12 (6.2); 7,404 (3.3); 7,395 (5.0); 7,384 (2.7); 5,756 (4.0); 5,516 (16.0); 3.324 (316.1); 2.676 (1.4); 2,672 (1.8); 2,507 (240.3); 2.503 (317.9); 2.498 (240.0); 2.334 (1.3), 2.329 (1.8), 2.325 (1.4), 1.352 (0.3), 1.233 (1.3), 1.046 (3.0), 1.030 (2.9) ; 0,146 (1.6); 0,008 (15, ^
Beispiel 1-1-337: 1H-NMR(400,0 MHz, de-DMSO): δ= 10,199(1, 1);10,118(2,7);9,624(2,2);9,608(2,3);8,238(1 ,3);7,956(2,3);7,934(3,0);7,887(6Example 1-1-337: 1 H-NMR (400.0 MHz, de-DMSO): δ = 10.199 (1, 1), 10.118 (2.7), 9.624 (2.2), 9.608 (2.3 8,238 (1,3), 7,956 (2,3), 7,934 (3,0), 7,887 (6
,7);7,814(1 ,6);7,794(2,5);7,774(1 ,5);7,716(2,1);7,697(2,1);7,409(1,4);7,392(2,6);7,375(1,3);7,179(1,0);7,165(1,3);7,150(0,9);5,756(0,3);5,52 1(9,1);5,459(0,4);3,321(60,3);2,672(1,0);2,507(123,5);2,503(163,9);2,498(125,3);2,329(1,4);2,313(16,0);2,126(0,3);2,020(0,7);1,928(0,5);1,7.714 (1, 6), 7.794 (2.5), 7.744 (1.5), 7.716 (2.1), 7.697 (2.1), 7.409 (1.4), 7.392 (2, 7,375 (1,3); 7,179 (1,0); 7,165 (1,3); 7,150 (0.9); 5,756 (0.3); 5,52 1 (9,1); 5,459 (6); 0.4); 3,321 (60.3); 2,672 (1.0); 2,507 (123.5); 2.503 (163.9); 2.498 (125.3); 2,329 (1.4); 2,313 (16 , 0); 2,126 (0.3); 2,020 (0.7); 1,928 (0.5); 1,
234(0,9);1,046(0,6);1,031(0,6);0,146(0,7);0,008(6,8);0,000(142,6);-0,149(0,7) 234 (0.9); 1,046 (0.6); 1,031 (0.6); 0.146 (0.7) 0.008 (6.8); 0,000 (142.6) - 0.149 (0.7)
Beispiel 1-1-338: 1H-NMR(400,0 MHz, de-DMSO): δ= 11,672(8,0);9,478(4,6);9,462(4,7);8,440(16,0);8,027(3.4);8,005(5,4);7,945(2,7);7,943(2 ,8);7,924(4,1);7,905(1,9);7,903(2,0);7,876(11,3);7,484(2.3);7,482(2,4);7,465(4.5);7,449(2,2);7,447(2,2);5.528(15,6);3,319(53 Example 1-1-338: 1 H-NMR (400.0 MHz, de-DMSO): δ = 11.672 (8.0); 9.478 (4.6); 9.462 (4.7); 8.440 (16.0 8.027 (3.4), 8.005 (5.4), 7.945 (2.7), 7.943 (2.8), 7.924 (4.1), 7.905 (1.9), 7.903 (2.0), 7.876 (11.3) 7,484 (2.3); 7,482 (2.4); 7.465 (4.5); 7,449 (2.2); 7,447 (2.2); 5,528 (15.6); 3,319 (53
,672(1,0);2,667(0,7);2,525(3,1);2,507i118,7);2,503(163,4);2,498(125,1);2,333(0,7);2,329(1,0);2,325(0,7);1,989(0,8);1,176(0,4);0,146(0,7);0, , 672 (1.0); 2,667 (0.7); 2,525 (3.1); 2,507i118,7); 2.503 (163.4); 2.498 (125.1); 2,333 (0.7); 2,329 (1.0); 2,325 (0.7); 1,989 (0.8); 1,176 (0.4); 0,146 (0.7) 0,
008(5,2);0,000(132,2);-0,008(5,9);-0,150(0,6) 008 (5.2); 0,000 (132.2) - 0.008 (5.9) - 0.150 (0.6)
Beispiel 1-4-001 : 1H-NMR(400,0 MHz. de-DMSO): δ= 9,614(1 ,3);9,610(1 ,3);9,598(1 ,3);9,593(1 ,3);8,549(1 ,7);8,545(1 ,7);8,537(1 ,8);8,533(1 ,7 );8,445(1,8);8,439(1,8);7,830(1 ,2);7,824(1 ,2);7,810(1 ,3); 7,803(1 ,3);7,485(2,2);7,465(2,0);7,448(1 ,6);7,436(1 ,7);7,432(1 ,7);7,420(1 ,6);5,177(Example 1-4-001: 1 H-NMR (400.0 MHz de-DMSO): δ = 9.614 (1, 3), 9.610 (1.3), 9.588 (1.3), 9.593 (1, 3 8,549 (1, 7); 8.545 (1, 7); 8.537 (1, 8); 8.533 (1, 7); 8.445 (1.8); 8.439 (1.8); 7.830 (1, 2) 7.824 (1, 2); 7.810 (1, 3); 7.803 (1, 3), 7.485 (2.2), 7.465 (2.0), 7.448 (1, 6), 7.436 (1, 7), 7.432 (1, 7), 7.420 (1, 6), 5.177 (
5,7);3,773(0,3);3,749(16,0);3,735(1,7);3,710(0,7);3,584(0,5);3,570(0,6);3,559(0,7);3,537(0,5);3,522(0,6);3,336(3,4);2,525(0,5);2,512(13,5);2 ,507(27,8);2,503(38,3);2,498(28,7);2,494(14,0); 1 ,046(2,2); 1 ,030(2, 1 ) 5.7); 3,773 (0.3); 3,749 (16.0); 3,735 (1.7); 3,710 (0.7); 3,584 (0.5); 3,570 (0.6); 3,559 (0 , 7); 3,537 (0.5); 3,522 (0.6); 3,336 (3.4); 2,525 (0.5); 2,512 (13.5); 2 , 507 (27.8); 2.503 (38.3); 2,498 (28.7); 2,494 (14.0); 1, 046 (2, 2); 1, 030 (2, 1)
Beispiel 1-5-001 : 1H-NMR(400,0 MHz, de-DMSO): δ= 8,528(2,9);8,522(3,0);8.496(4,6);8,486(4,7);7,895(1 ,7);7,888(1 ,7);7,874(2,0);7,868(2,0Example 1-5-001: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.528 (2.9), 8.522 (3.0), 8.496 (4.6), 8.486 (4.7 7.895 (1, 7), 7.888 (1, 7), 7.874 (2.0), 7.868 (2.0
);7,563(3,3);7,542(3,0);7,473(4,6);7,463(4,6);5,176(9,4);4,837(0,4);4,655(16,0);4,612(0,5);3,323(17,5);3,170(0,3);2,512(13,9);2,508(28 503(39,0);2,499(30,2);2,494(15,6);0,000(2,8) ); 7,563 (3.3); 7,542 (3.0); 7,473 (4.6); 7,463 (4.6); 5,176 (9.4); 4,837 (0.4); 4,655 (16.0) 4.312 (0.5), 3.323 (17.5), 3.170 (0.3), 2.512 (13.9), 2.508 (28 503 (39.0), 2.499 (30.2), 2.494 (15), 0,000 (2.8); 6)
Beispiel i-5-002: 1H-NMR(400,0 MHz, de-DMSO): δ= 8,499(4.4);8,489(4,4);7,875(6,1);7,513(4,5);7,503(4,3);5,370(10, 1);4,645(16,0);3,464(0 ,4);3,388(1 ,6);3, 171 (1 ,8);2,508(33,2);2,504(45,6);2,499(35,3); 1 ,490(0,6); 1 ,353(1 ,4); 1 ,300(0,6); 1 ,259(0,8); 1 ,234(2,5);0,000(0,7) Example i-5-002: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.499 (4.4); 8.489 (4.4); 7.875 (6.1); 7.513 (4.5); 7.503 (4.3); 5.370 (10, 1); 4.645 (16.0); 3.344 (0.4); 3.388 (1, 6); 3, 171 (1, 8); 2.508 (33.2) ; 2,504 (45.6); 2,499 (35.3); 1,490 (0.6); 1, 353 (1, 4); 1, 300 (0.6); 1, 259 (0.8); 1, 234 (2.5); 0.000 (0.7)
a) Die Bestimmung des [M+H]+ mit der LC-MS im sauren Bereich erfolgte bei H 2,7 mit Acetonitril (enthält 0,1 % Ameisensäure) und Wasser als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril, Gerät: Agilent 1 100 LC -System, Agilen! MSD System, HTS a) The determination of [M + H] + with the LC-MS in the acidic range was carried out at H 2.7 with acetonitrile (contains 0.1% formic acid) and water as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile, device: Agilent 1 100 LC system, Agile! MSD system, HTS
PAL. PAL.
Die Bestimmung der in den vorangegangenen Tabellen und Hersteillingsbeispielen angegebenen logP-Werte erfolgte gemäß EEG Directive 79/831 Annex V.A8 durch I I PI ( High Performance Liquid Chromatography) an einer Phasen n mk ehrsän le (C18). Temperatur 43 °C. Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP Werte bekannt sind. b) Die Bestimmung der ! H-NMR-Daten erfolgte mit einem Bmker Avance 400 oder Bruker Avance I I I 600 ausgestattet mit einem Durchflusspi benkopf (60 μΐ Volumen), mit Tetramethylsilan als Referenz (0.0) und den Lösungsmitteln CD-CN. CDC13 oder D -DM SO. The determination of the logP values given in the preceding tables and examples of manufacture was carried out in accordance with EEG Directive 79/831 Annex V.A8 by means of II PI (High Performance Liquid Chromatography) on a phase NMR (C18). Temperature 43 ° C. The calibration is carried out with unbranched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known. b) The determination of ! H-NMR data were taken with a Bmker Avance 400 or Bruker Avance III 600 equipped with a flow head (60 μΐ volume), with tetramethylsilane as reference (0.0) and the solvents CD-CN. CDC1 3 or D-DM SO.
Die NMR-Daten ausgewählter Beispiele werden entweder in klassischer Form (δ-Werte, Multiplettaufspaltung, Anzahl der H-Atome) oder als NMR-Peak-Listen aufgeführt. The NMR data of selected examples are listed either in classical form (δ values, multiplet splitting, number of H atoms) or as NMR peak lists.
NMR-Peak-Listenyerfahren NMR peak Listenyerfahren
Die 'H-NMR-Daten ausgewählter Beispiele werden in Form von 'H-NMR-Peaklisten notiert. Zu jedem Si nal peak wird erst der δ -Werl in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die δ -Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. The 'H NMR data of selected examples are noted in terms of' H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in parentheses are listed. The δ value - signal intensity number pairs of different signal peaks are listed separated by semicolons.
Die Peakliste eines Beispieles hat daher die Form: δι (Intensitäti); δ2 (Intensität2); ; 5i (Intensität^; ; δη (Intensitätn) The peak list of an example therefore has the form: δι (intensity i); δ 2 (intensity 2 ); ; 5i (intensity ^;; δ η (intensity n )
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität imThe intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For wide signals, multiple peaks or the center of the signal and their relative intensity in the
Vergleich zum intensivsten Signal im Spektrum gezeigt werden. Zur Kalibrierung der chemischen Verschiebung von Ή -NMR- Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DM SO gemessen werden. Daher kann in NMR-Peakiisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der Ή-NMR-Peaks sind ähnlich den klassischen Ή-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Comparison to the most intense signal in the spectrum can be shown. To calibrate the chemical shift of Ή-NMR spectra, we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DM SO. Therefore, the peak of tetramethylsilane can occur in NMR peak lists, but it does not have to. The lists of the Ή-NMR peaks are similar to the classical Ή-NMR prints and thus usually contain all the peaks that are listed in a classical NMR interpretation.
Darüber hinaus können sie wie klassische Ή-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 'H-NMR-Peaks die gewöhnlichen Lö sungsmittelp eaks , zum Beispiel Peaks von DM SO in DMSO-De und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. In addition, they may, like classical Ή-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities. When indicating connection signals in the delta range of solvents and / or water, in our lists of 'H-NMR peaks the usual solvent peaks, for example peaks of DM SO in DMSO-De and the peak of water, are shown, which usually have a high intensity on average.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zi el Verbindungen (zum Beispiel mit einer Reinheit von >90%). The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the Zi el compounds (for example, with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein, ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von ' 'Neb enprodukt-Fingerabdrücken' ' zu erkennen. Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nachSuch stereoisomers and / or impurities may be typical of the particular manufacturing process, and their peaks may thus help to detect the reproduction of our manufacturing process from "near-end product fingerprints". An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expectation values) can, depending on
Bedarf die Peaks der Zieiverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 'H-NMR-Interpretation. Need to isolate the peaks of the Zieiverbindungen, where appropriate additional intensity filters are used. This isolation would be similar to peak picking in classical 'H NMR interpretation.
Weitere Details zu Ή-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Anwendun^sbeispiele Further details on Ή NMR peaks can be found in Research Disclosure Database Number 564025. Applicatio ^ sbeispiele
Die folgenden Beispiele zeigen die Insektizide und akarizide Wirkung der erfindungsgemäßen Verbindungen. Dabei beziehen sich die genannten erfindungsgemäßen Verbindungen auf die in den Tabellen Ibis 3 mit den entsprechenden Referenzzeichen (Nr.) aufgeführten Verbindungen: Ctenocephalides felis - in-vitro Kontakttests mit adullen Katzenflöhen The following examples show the insecticidal and acaricidal activity of the compounds of the invention. The compounds according to the invention refer to the compounds listed in Tables Ibis 3 with the corresponding reference signs (No.): Ctenocephalides felis - in vitro contact tests with adullen cat fleas
Für die Beschichtung der Teströhrchen werden zunächst 9 mg Wirkstoff in 1 ml Aceton p.a. gelöst und anschließend mit Aceton p.a. auf die gewünschte Konzentration verdünnt. 250 μΐ der Lösung werden durch Drehen und Kippen auf einem Rotationsschüttler (2 h S chaukelrotation bei 30 rpm) homogen auf den Innenwänden und dem Boden eines 25ml Glasröhrchens verteilt. Bei 900 ppm Wirkstofflösung und 44,7 cm2 Innenoberfläche wird bei homogener Verteilung eine Flächendosis von 5 μg/cm2 erreicht. For the coating of the test tubes, first 9 mg of active ingredient are dissolved in 1 ml of acetone pa and then diluted with acetone pa to the desired concentration. 250 μΐ of the solution are homogeneously distributed on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h S chaukelrotation at 30 rpm). At 900 ppm active ingredient solution and 44.7 cm 2 inner surface, a surface dose of 5 μg / cm 2 is achieved with homogeneous distribution.
Nach Abdampfen des Lösungsmittels werden die Gläschen mit 5-10 adulten KatzenflöhenAfter evaporation of the solvent, the vials with 5-10 adult cat fleas
(Ctenocephalides felis) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Gläschen aufrecht gestellt und die Flöhe auf den Boden des Gläschens geklopft. Flöhe, die unbeweglich auf dem Boden verbleiben oder sich unkoordiniert bewegen, gelten als tot bzw. angeschlagen. (Ctenocephalides felis) occupied, closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
Eine Substanz zeigt gute Wirkung gegen Ctenocephalides felis, wenn in diesem Test bei einer Aufwandmenge von 5 μg/cm2 mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Flöhe angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Flöhe geschädigt wurden. A substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 μg / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 5 μg/cm2: 1-1 -003, 1-1 -032, 1-1 -082, 1-1 -1 1 1, 1-1 -143, 1-1 -239, l- l - 240, 1- 1 -243 In this test, for example, the following compounds of the preparation examples showed an effect of 100% at an application rate of 5 μg / cm 2 : 1-1 -003, 1-1 -032, 1-1-082, 1-1 -1 1 , 1-1 -143, 1-1-239, 1-140, 1-1-243
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Hersteliungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 5 μ /cm2: 1- 1 -033 In this test, for example, the following compounds of Hersteliungsbeispiele showed an effect of 90% at a rate of 5 μ / cm 2 : 1-1 -033
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 5 μg/cm2: 1-1 -147 In this test, for example, the following compounds of the preparation examples showed an effect of 80% at an application rate of 5 μg / cm 2 : 1-1-147
Boophilus microplus --Injektionstest Boophilus microplus --Injection test
Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. 1 μΐ der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Solvent: Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration. 1 μΐ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet until larval hatching after about 42 days. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20 μ&'Ποπ 1-1-008, 1-1-009, 1-1-012, 1-1-016, 1-1-029, 1-1-054, 1- 1 - 165 In this test, the following compounds from the preparation examples showed an activity of 100% at an application rate of 20 μ &'Ποπ 1-1-008, 1-1-009, 1-1-012, 1-1-016, 1-1 -029, 1-1-054, 1-1 - 165
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkun von 80% bei einer Aufwandmenge von 20 μg/Tier: 1-1-003, 1-1-020, 1-1-033, 1-1 -034, 1-1-049, 1- 1 -152. 1- 1 - 202, 1-1-217, 1-1 -254 In this test, e.g. the following compounds of the preparation examples have an effect of 80% at an application rate of 20 μg / animal: 1-1-003, 1-1-020, 1-1-033, 1-1-034, 1-1-049, 1 - 1 -152. 1-1-202, 1-1-217, 1-1 -254
Ctenocephalides felis - Oraltest Lösungsmittel: Dimethylsulfoxid Ctenocephalides felis - Oraltest Solvent: Dimethylsulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit citri ertem Rinderblut erhält man die gewünschte Konzentration. For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
Ca. 20 nüchterne adulte Katzenflöhe (Ctenocephalides felis) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metallzylinder gestellt, dessen Unterseite mit Parafllm verschlossen ist. Der Zylinder enthält die Blut- Wirkstoff Zubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. On the chamber, a metal cylinder is placed, the underside of which is sealed with Parafllm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 95 % bei einer Aufwandmenge von lOOppm: 1-1-003 After 2 days the kill is determined in%. 100% means> that all fleas have been killed; 0% means that none of the fleas have been killed. In this test, e.g. the following compounds of the preparation examples an effect of 95% at a rate of lOOppm: 1-1-003
Lucilla cuprina - Test Lucilla cuprina - test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Ca. 20 LI -Larven der Australischen Schafgold fliege (Lucilla cuprlnä) werden in ein Testgefäß überfuhrt, welches gehacktes Pferdefleisch und die Wirkstoffzubereitung der gewünschten Konzentration enthält. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty LI larvae of the Australian Sheep Gold Fly (Lucilla cuprlnä) are transferred to a test vessel containing chopped horse meat and the active compound preparation of the desired concentration.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden. After 2 days the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Hersteillingsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: 1-1 -003, 1-1 -009, 1-1 -034, 1-1 -049, 1-1 -087, 1-1 -1 1 1, i- l - 145. 1- 1 -202. 1-1 -254 In this test, e.g. the following compounds of Hersteillingsbeispiele an effect of 100% at an application rate of 100 ppm: 1-1 -003, 1-1 -009, 1-1 -034, 1-1 -049, 1-1 -087, 1-1 -1 1 1, i- l - 145. 1- 1 -202. 1-1 -254
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Hersteillingsbeispiele eine Wirkung von 95 % bei einer Aufvvandmenge von 100 ppm: 1-1 -137, 1- 1 - 1 54 In this test, e.g. the following compounds of the Hersteillingsbeispiele an effect of 95% at a Aufvvandmenge of 100 ppm: 1-1 -137, 1- 1 - 1 54
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Hersteliungsbeispiele eine Wirkung von 90 % bei einer Aufwandmenge von 100 ppm: 1-1 -008, 1-1 -027, 1-1 -032, 1-1 -033, 1-1 -089 In this test, e.g. the following compounds of the preparation examples have an effect of 90% at an application rate of 100 ppm: 1-1 -008, 1-1-027, 1-1-032, 1-1-033, 1-1-089
Musca doniestica-Test Musca doniestica test
Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Solvent: dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Gefäße, die einen Schwamm enthalten, der mit Zuckerlösung und der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit 10 adulten Stubenfliegen (Musca domestlca) besetzt. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestlca). After 2 days the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100 ppm: 1-1 -008, 1-1 -032, 1-1 -033, 1-1 -1 11 In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 100 ppm: 1-1 -008, 1-1 -032, 1-1 -033, 1-1 -1 11
Bei diesem Test zeigten z.B. die folgenden Verbindungen der Hersteliungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100 ppm: 1-1 -003, 1-1 -034 In this test, e.g. the following compounds of the preparation examples an effect of 80% at an application rate of 100 ppm: 1-1 -003, 1-1 -034
Diahrotica halteata - Sprühtest Diahrotica halteata - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1 ,5 Gewichtsteile Dimethyl formamid  1, 5 parts by weight of dimethyl formamide
Emulgator: Alkylaryipoiyglykolether Zur Herstellung einer zweckmäßigen Wirksto ffzub ereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaitigem Wasser verdünnt. Vorgequollene Weizenkörner (Triticum aestivum) werden in einer mit Agar und etwas Wasser gefüllten Multiwell-Platte für einen Tag inkubiert (5 Saatkörner pro Kavität). Die gekeimten Weizenkörner werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Anschließend wird jede Kavität mit 10-20 Käferlarven von Diabrotica balteata infiziert. Emulsifier: Alkylaryipoiyglykolether To prepare a suitable Wirksto ffzub preparation is dissolved 1 part by weight of active compound with the specified parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Pre-swollen wheat grains (Triticum aestivum) are incubated in a multi-well plate filled with agar and a little water for one day (5 seeds per well). The germinated wheat grains are sprayed with an active compound preparation of the desired concentration. Each cavity is then infected with 10-20 beetle larvae of Diabrotica balteata.
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Weizenpflanzen wie in der unbehandelten, nicht infizierten Kontrolle gewachsen sind; 0 % bedeutet, dass keine Weizenpflanze gewachsen ist. After 7 days, the effect is determined in%. 100% means that all wheat plants have grown as in the untreated uninfected control; 0% means that no wheat plant has grown.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 160μg/weϊl: 1-1-004, 1-1-008, 1-1-020, 1-1-027, 1-1-028, 1-1-029, 1-1-032, 1-1-033, 1-1-034, 1-1-036, 1-1-082, 1-1-083, 1-1-087, 1-1-097, 1-1-111, 1-1-128, 1-1-129.1-1-137, 1-1-143, 1-1-145, 1-1-147, 1-1-148, 1-1-203, 1-1-216, 1-1-227, 1-1-230, 1-1-231.1-1-232.1-1-235.1-1-246.1-1-254. 1-1-267.1-1-276, 1-1-277.1-1-282, 1-1-283, 1-1-288, 1-1-290, 1-1-292 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 160μg / weϊl: 1-1-004, 1-1-008, 1-1-020, 1-1-027, 1-1-028, 1 -1-029, 1-1-032, 1-1-033, 1-1-034, 1-1-036, 1-1-082, 1-1-083, 1-1-087, 1-1 -097, 1-1-111, 1-1-128, 1-1-129.1-1-137, 1-1-143, 1-1-145, 1-1-147, 1-1-148, 1 -1-203, 1-1-216, 1-1-227, 1-1-230, 1-1-231.1-1-232.1-1-235.1-1-246.1-1-254. 1-1-267.1-1-276, 1-1-277.1-1-282, 1-1-283, 1-1-288, 1-1-290, 1-1-292
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80% bei einer Aufwandmenge von 160μg/weii: 1-1-041, 1-1-045, 1-1-135.1-1-154.1-1-202. i- 1-233.1-1-238, 1-1-258, 1-1-284, 1-1-287, 1-1-291 Phaedon Cochlea riae - Sprühtest In this test, z. For example, the following compounds of Preparation Examples have an effect of 80% at a dosage of 160 μg / ml: 1-1-041, 1-1-045, 1-1-135.1-1-154.1-1-202. i-1-233.1-1-238, 1-1-258, 1-1-284, 1-1-287, 1-1-291 Phaedon Cochlear riae - Spray Test
Lösungsmittel: 78,0 Gewichtsteile Aceton  Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirksto ffzub ereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis /um Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaitigem Wasser verdünnt. To prepare a suitable Wirksto ffzub preparation is dissolved 1 part by weight of active compound with the specified parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm to / to reach the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Käferlarven abgetötet wurden; 0 % bedeutet, dass keine Käferlarven abgetötet wurden. Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500 g/ha: 1-1-082, 1-1-083, 1-1-093, 1-1-094, 1-1-097, 1-1-154 After 7 days, the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 500 g / ha: 1-1-082, 1-1-083, 1-1-093, 1-1-094, 1-1-097, 1-1-154
1-1-198, 1-1-202, 1-1-203, 1-1-212, 1-1-216, 1-1-217, 1-1-240, 1-1-242, 1-1-243.1-1-244.1-1-246.1-1-254. 1-1-256.1-1-267.1-1-271, 1-1-274.1-1-276.1-1-297 Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 500 g/ha: 1-1-262, 1-1-277 1-1-198, 1-1-202, 1-1-203, 1-1-212, 1-1-216, 1-1-217, 1-1-240, 1-1-242, 1- 1-243.1-1-244.1-1-246.1-1-254. 1-1-256.1-1-267.1-1-271, 1-1-274.1-1-276.1-1-297 In this test, z. For example, the following compounds of the Preparation Examples have an effect of 83% at a rate of 500 g / ha: 1-1-262, 1-1-277
Meloidogyne ineognita- Test Meloidogyne ineognita test
Lösungsmittel: 125,0 Gewichtsteile Aceton  Solvent: 125.0 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße werden mit Sand, Wirkstofflösung, einer Ei-Larven-Suspension des südlichen Wurzelgallenälchens (Meloidogyne incognita) und Salatsamen gefüllt. Die Salatsamen keimen und die Pflänzchen entwickeln sich. An den Wurzeln entwickeln sich die Gallen. Nach 14 Tagen wird die nematizide Wirkung anhand der Gallenbildung in % bestimmt. Dabei bedeutet 100 %, dass keine Gallen gefunden wurden; 0 % bedeutet, dass die Zahl der Gallen an den behandelten Pflanzen der unbehandelten Kontrolle entspricht. Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots. After 14 days, the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Hersteilungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 20 ppm: 1-1-116, 1-1-143.1-1-147, 1-1-161, 1-1-176, 1-1-196, 1-1- 276, 1-1-277, 1-1-314.1-1-316.1-1-321.1-1-323 In this test, z. For example, the following compounds of Hersteilungsbeispiele effect of 90% at a rate of 20 ppm: 1-1-116, 1-1-143.1-1-147, 1-1-161, 1-1-176, 1-1- 196, 1-1-276, 1-1-277, 1-1-314.1-1-316.1-1-321.1-1-323
Tetranvchus urticae - Sprühtest, OP-resistent Tetranvchus urticae - spray test, surgical-resistant
Lösungsmittel: 78,0 GewichtsteileAceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator : Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe Bean leaf discs (Phaseolus vulgaris), which are common to all common spider mite species
(Tetranychus urticae) befallen sind, werden mit einer Wirksto ffzub er eitung der gewünschten (Tetranychus urticae) are treated with an active substance delivery of the desired
Konzentration gespritzt. Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. Concentration sprayed. After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 500 g/ha: 1-1-002, 1-1-009, 1-1-014, 1-1-017, 1-1-019, 1-1-137 1-1-139, 1-1-143, 1-1-158, 1-1-160, 1-1-166, 1-1-178, 1-1-271, 1-1-299.1-1-304. In this test, z. For example, the following compounds of Preparation Examples have an effect of 90% at a rate of 500 g / ha: 1-1-002, 1-1-009, 1-1-014, 1-1-017, 1-1-019 , 1-1-137 1-1-139, 1-1-143, 1-1-158, 1-1-160, 1-1-166, 1-1-178, 1-1-271, 1- 1-299.1-1-304.
Mvzus persicae - Sprühtest Mvzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolygiykolether Zur Hersteilung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Emulsifier: Alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 500g/ha: 1-1-004, 1-1-005, 1-1-009, 1-1-010, 1-1-012, 1-1-015, 1-1-020, 1-1- 028, 1-1-034, 1-1-036, 1-1-049, 1-1-056.1-1-083, 1-1-085, 1-1-092.1-1-097, 1-1-101, 1-1-106, 1-1-107, 1-1- 112, 1-1-122.1-1-152.1-1-165.1-1-178, 1-1-224.1-1-246.1-1-254, 1-1-267.1-1-274. [-1-276.1-1-279, 1-1- 282, 1-1-284, 1-1-292.1-1-296.1-1-297.1-1-303, 1-1-305, 1-1-307, 1-1-308, 1-1-310, 1-1- 13.1-1-319.1-1- 325,1-1-328 In this test, z. For example, the following compounds of the Preparation Examples have an effect of 90% at a rate of 500 g / ha: 1-1-004, 1-1-005, 1-1-009, 1-1-010, 1-1-012, 1 -1-015, 1-1-020, 1-1-028, 1-1-034, 1-1-036, 1-1-049, 1-1-056.1-1-083, 1-1-085 , 1-1-092.1-1-097, 1-1-101, 1-1-106, 1-1-107, 1-1-112, 1-1-122.1-1-152.1-1-165.1-1 -178, 1-1-224.1-1-246.1-1-254, 1-1-267.1-1-274. [-1-276.1-1-279, 1-1-282, 1-1-284, 1-1-292.1-1-296.1-1-297.1-1-303, 1-1-305, 1-1- 307, 1-1-308, 1-1-310, 1-1- 13.1-1-319.1-1- 325.1-1-328
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500g/ha: 1-1-003, 1-1-008, 1-1-016, 1-1-022.1-1-023, 1-1-026, 1-1- 027, 1-1-029, 1-1-043, 1-1-054, 1-1-061, 1-1-068, 1-1-070, 1-1-072, 1-1-076, 1-1-080, 1-1-081, 1-1-082, 1-1- 086, 1-1-087, 1-1-111, 1-1-210, 1-1-217, 1-1-220, 1-1-221.1-1-226.1-1-283, 1-1-293.1-1-314.1-1-301, 1-1- 304, 1-1-309, 1-1-311, 1-1-315.1-1-316 In this test, z. For example, the following compounds of Preparation Examples effect of 100% at a rate of 500g / ha: 1-1-003, 1-1-008, 1-1-016, 1-1-022.1-1-023, 1-1 -026, 1-1-027, 1-1-029, 1-1-043, 1-1-054, 1-1-061, 1-1-068, 1-1-070, 1-1-072 , 1-1-076, 1-1-080, 1-1-081, 1-1-082, 1-1-086, 1-1-087, 1-1-111, 1-1-210, 1 -1-217, 1-1-220, 1-1-221.1-1-226.1-1-283, 1-1-293.1-1-314.1-1-301, 1-1-304, 1-1-309 , 1-1-311, 1-1-315.1-1-316
Myzus persicae - Oraltest Myzus persicae - Oraltest
Lösungsmittel: 100 Gewichtsteile Aceton Zur Herstellung einer zweckmäßigen Wirksto ffzub ereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser bis zum Erreichen der gewünschten Konzentration auf. Solvent: 100 parts by weight of acetone To prepare a suitable Wirksto ffzub preparation is dissolved 1 part by weight of active compound with the specified parts by weight of solvent and filled with water until reaching the desired concentration.
50 μΐ der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150μ1 IPL41 Insektenmedium (33% + 15% Zucker) auf eine Endvolumen von 200 μΐ aufgefüllt. Anschließend werden die Platten mit Paratilm verschlossen, durch den eine gemischte Population der Grünen Pfirsichblattlaus (Myzus persicae), die sich in einer zweiten Mikrotiterplatte befindet, hindurchstechen und die Lösung aufnehmen kann. 50 μΐ of the active ingredient preparation are transferred into microtiter plates and filled with 150 μl IPL41 insect medium (33% + 15% sugar) to a final volume of 200 μΐ. The plates are then sealed with paratilm through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution.
Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Hersteilungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 20ppm : 1-1-001, 1-1-002, 1-1-003, 1-1-004, 1-1-005, 1-1-006, 1-1-008, I- 1-009, 1-1-010, 1-1-011, 1-1-012, 1-1-013, 1-1-014, 1-1-015, 1-1-016, 1-1-017, 1-1-018, 1-1-020, 1-1-022, I- 1-023, 1-1-025, 1-1-026, 1-1-027, 1-1-028, 1-1-029, 1-1-031, 1-1-032, 1-1-033, 1-1-034.1-1-035, 1-1-036, I- 1-037, 1-1-038, 1-1-039, 1-1-040, 1-1-041, 1-1-042, 1-1-043, I- 1-044.1-1-045.1-1-046, 1-1-047, 1-1-049, I- 1-051, 1-1-052, 1-1-054.1-1-055.1-1-059, 1-1-060, 1-1-061, 1-1-062, 1-1-064.1-1-065, 1-1-068, 1-1-070, I- 1-072, 1-1-075, 1-1-076, 1-1-077, 1-1-081, 1-1-082, 1-1-083, 1-1-084, 1-1-086, 1-1-087, 1-1-088, 1-1-089, I- 1-091, 1-1-092, 1-1-093, 1-1-096, 1-1-097, 1-1-098, 1-1-101, 1-1-103, 1-1-107, 1-1-108, 1-1-109, 1-1-110, I- 1-111,1-1-112, 1-1-113,1-1-114, 1-1-115,1-1-116, 1-1-117, 1-1-118,1-1-119, 1-1-121.1-1-122.1-1-124. I- 1-129, 1-1-131, 1-1-137, 1-1-138, 1-1-142.1-1-145.1-1-146, 1-1-147, 1-1-148, 1-1-151, 1-1-152.1-1-154. I- 1-155.1-1-157, 1-1-158, 1-1-159.1-1-160, 1-1-161, 1-1-165.1-1-166.1-1-167, 1-1-168, 1-1-169, 1-1-170, I- 1-171, 1-1-173, 1-1-174, 1-1-175.1-1-177, 1-1-178, 1-1-179, 1-1-180, 1-1-181, 1-1-182, 1-1-183, 1-1-185, I- 1-186, 1-1-188, 1-1-190, 1-1-192, 1-1-193, 1-1-198, 1-1-199, 1-1-201, 1-1-202, 1-1-203, 1-1-205, 1-1-206, I- 1-207, 1-1-208, 1-1-209, 1-1-210, 1-1-212, 1-1-213.1-1-214.1-1-215.1-1-216, 1-1-217, 1-1-218, 1-1-219, I- 1-220, 1-1-221. I- 1-222.1-1-223.1-1-224.1-1-225.1-1-226.1-1-227, 1-1-228, 1-1-229.1-1-231.1-1-234. I- 1-236, 1-1-239, 1-1-240.1-1-241.1-1-243.1-1-247.1-1-249.1-1-250.1-1-251.1-1-254.1-1-257, 1-1-269, I- 1-271, 1-1-272, 1-1-274, 1-1-275, i- 1-276.1-1-277, 1-1-278, 1-1-279.1-1-282, 1-1-283, 1-1-284, 1-1-285, I- 1-286, 1-1-287, 1-1-288, 1-1-289, 1-1-292, 1-1-293.1-1-296.1-1-297.1-1-299.1-1-301, 1-1-302, 1-1-304, I- 1-305, 1-1-306, 1-1-308, 1-1-309, 1-1-310, 1-1-311, I- 1-312.1-1-313.1-1-314.1-1-315.1-1-316, 1-1-317, 1- 1-319, 1-1-321.1-1-323, 1-1-325.1-1-326.1-1-328, 1-4-001, 1-5-001, 1-5-002 In this test, z. For example, the following compounds of Hersteilungsbeispiele effect of 100% at a rate of 20ppm: 1-1-001, 1-1-002, 1-1-003, 1-1-004, 1-1-005, 1-1 -006, 1-1-008, I-1-009, 1-1-010, 1-1-011, 1-1-012, 1-1-013, 1-1-014, 1-1-015 , 1-1-016, 1-1-017, 1-1-018, 1-1-020, 1-1-022, I-1-023, 1-1-025, 1-1-026, 1 -1-027, 1-1-028, 1-1-029, 1-1-031, 1-1-032, 1-1-033, 1-1-034.1-1-035, 1-1-036 , I-1-037, 1-1-038, 1-1-039, 1-1-040, 1-1-041, 1-1-042, 1-1-043, I-1-044.1-1 -045.1-1-046, 1-1-047, 1-1-049, I-1-051, 1-1-052, 1-1-054.1-1-055.1-1-059, 1-1-060 , 1-1-061, 1-1-062, 1-1-064.1-1-065, 1-1-068, 1-1-070, I-1-072, 1-1-075, 1-1 -076, 1-1-077, 1-1-081, 1-1-082, 1-1-083, 1-1-084, 1-1-086, 1-1-087, 1-1-088 , 1-1-089, 1-1-091, 1-1-092, 1-1-093, 1-1-096, 1-1-097, 1-1-098, 1-1-101, 1 -1-103, 1-1-107, 1-1-108, 1-1-109, 1-1-110, 1-111, 1-1112, 1-1-113, 1--1 -114, 1-1-115, 1-116, 1-1-117, 1-1-118, 1-119, 1-1-121, 1-122, 1-124. I-1-129, 1-1-131, 1-1-137, 1-1-138, 1-1-142.1-1-145.1-1-146, 1-1-147, 1-1-148, 1-1-151, 1-1-152.1-1-154. I-1-155.1-1-157, 1-1-158, 1-1-159.1-1-160, 1-1-161, 1-1-165.1-1-166.1-1-167, 1-1- 168, 1-1-169, 1-1-170, 1- 1-171, 1-1-173, 1-1-174, 1-1-175.1-1-177, 1-1-178, 1- 1-179, 1-1-180, 1-1-181, 1-1-182, 1-1-183, 1-1-185, 1- 1-186, 1-1-188, 1-1- 190, 1-1-192, 1-1-193, 1-1-198, 1-1-199, 1-1-201, 1-1-202, 1-1-203, 1-1-205, 1-1-206, 1-1207, 1-1-208, 1-1-209, 1-1-210, 1-1-212, 1-1-213.1-1-214.1-1-215.1- 1-216, 1-1-217, 1-1-218, 1-1-219, 1-2-220, 1-1-221. I-1-222.1-1-223.1-1-224.1-1-225.1-1-226.1-1-227, 1-1-228, 1-1-229.1-1-231.1-1-234. I-1-236, 1-1-239, 1-1-240.1-1-241.1-1-243.1-1-247.1-1-249.1-1-250.1-1-251.1-1-254.1-1-257, 1-1-269, I-1-271, 1-1-272, 1-1-274, 1-1-275, 1-276.1-1-277, 1-1-278, 1-1- 279.1-1-282, 1-1-283, 1-1-284, 1-1-285, 1-286, 1-1-287, 1-1-288, 1-1-289, 1- 1-292, 1-1-293.1-1-296.1-1-297.1-1-299.1-1-301, 1-1-302, 1-1-304, 1-305, 1-1-306, 1-1-308, 1-1-309, 1-1-310, 1-1-311, I-1-312.1-1-313.1-1-314.1-1-315.1-1-316, 1-1- 317, 1- 1-319, 1-1-321.1-1-323, 1-1-325.1-1-326.1-1-328, 1-4-001, 1-5-001, 1-5-002
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 2 Oppin: 1-1-053, 1-1-056.1-1-057, 1-1-066, 1-1-071, 1-1-078, 1-1-079, 1-1- 106, 1-1-125.1-1-126, 1-1-133.1-1-135.1-1-164, 1-1-172, 1-1-183, 1-1-191, 1-1-1 5.1-1-200, 1-1-211, 1-1- 232, 1-1-235.1-1-237.1-1-244.1-1-245.1-1-246.1-1-248, 1-1-252.1-1-259.1-1-265.1-1-294 Mv/us persicae - Sprühtest In this test, z. For example, the following compounds of the Preparation Examples Effect of 90% at an application rate of 2 Oppin: 1-1-053, 1-1-056.1-1-057, 1-1-066, 1-1-071, 1-1- 078, 1-1-079, 1-1-106, 1-1-125.1-1-126, 1-1-133.1-1-135.1-1-164, 1-1-172, 1-1-183, 1-1-191, 1-1-1 5.1-1-200, 1-1-211, 1-1-232, 1-1-235.1-1-237.1-1-244.1-1-245.1-1-246.1 -1-248, 1-1-252.1-1-259.1-1-265.1-1-294 Mv / us persicae - spray test
Lösungsmittel: 14 Gewichtsteile Dimethylformamid Solvent: 14 parts by weight of dimethylformamide
Emulgator: Alkyiarylpolyglykoiether  Emulsifier: Alkyiaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirksto ffzub ereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt. Paprikapflanzen (Capsic m annuum), die stark von der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt. To prepare a suitable Wirksto ffzub preparation is dissolved 1 part by weight of active compound with the specified parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution. Paprika plants (Capsic m annuum) which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.
Nach 6 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Läuse abgetötet wurden; 0 % bedeutet, dass keine Läuse abgetötet wurden. Bei diesem Test zeigten z. B. die folgenden Verbindungen der Hersteillingsbeispiele Wirkung von 100% bei einer Aufwandmenge von l OOppm: 1-1 -032, 1-1 -033, 1-1 -145, 1-1 -147, 1- 1 - 1 54. 1-1 -193 After 6 days the kill is determined in%. 100% means that all lice have been killed; 0% means that no lice have been killed. In this test, z. Example, the following compounds of Hersteillingsbeispiele effect of 100% at a rate of l OOppm: 1-1 -032, 1-1 -033, 1-1 -145, 1-1 -147, 1- 1 - 1 54. 1 -1 -193
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 99% bei einer Aufwandmenge von 1 OOppm: 1- 1 -227, 1- 1 -23 1 In this test, z. Example, the following compounds of the preparation examples effect of 99% at an application rate of 1 OOppm: 1- 1 -227, 1- 1 -23 1
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 95% bei einer Aufwandmenge von 1 OOppm: 1-1 -046, 1- 1 -045. 1-1 -062, 1-1 -113, 1-1 -137, 1-1 -179, 1- 1 -252 In this test, z. For example, the following compounds of the Preparation Examples effect of 95% at an application rate of 1 OOppm: 1-1 -046, 1-1 -045. 1-1 -062, 1-1-113, 1-1 -137, 1-1 -179, 1-1 -252
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 1 OOppm: 1-1 -002, 1- 1 -202 In this test, z. For example, the following compounds of the Preparation Examples have an effect of 90% at an application rate of 1 OOppm: 1-1 -002, 1-1 -202
Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 85%) bei einer Aufwandmenge von 1 OOppm: 1-1 -013, 1-1 -114 Bei diesem Test zeigten z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80%> bei einer Aufwandmenge von 1 OOppm: 1- 1 -044 In this test, z. Example, the following compounds of the preparation examples effect of 85%) at an application rate of 1 OOppm: 1-1 -013, 1-1 -114 In this test, z. Example, the following compounds of the preparation examples effect of 80%> at an application rate of 1 OOppm: 1- 1 -044

Claims

Patentansprüche: claims:
1. Verbindung der Formel (I) 1. Compound of formula (I)
worin  wherein
Q1 und Q2 zusammen für einen der Reste A- 1 bis A-5 stehen, die zusammen mit dem C- und N- Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q 1 and Q 2 together represent one of A-1 to A-5, which together with the C and N atoms to which they are attached form a 5- or 6-membered aromatic ring,
A-I A-2 A-3 A-4 A-5 A-1 A-2 A-3 A-4 A-5
T für R\ -OR6, -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und T is R 1 -OR 6 , -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
W für O steht, oder W stands for O, or
T für -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht und T is -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ) and
W für S steht, W stands for S,
G für eine Bindung, für -C(R9)(R10)- , oder für C(R9)(R10)C(R9a)(R10a) steht, G is a bond, -C (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
U für einen Cyclus der Reihe U-l bis U-28 steht ff)*? '« <*">»+: Ii Λ-F i U is a cycle of the series Ul to U-28 ff) *? '' <* "> » +: Ii Λ-F i
U-2 U-3 U-4 U-5 U-2 U-3 U-4 U-5
U-6 U-7 U-8  U-6 U-7 U-8
U-1 6 U-1 7 U-1 8 U-1 9 U-20 U-1 6 U-1 7 U-1 8 U-1 9 U-20
U-21 U-22 U-23 U-24 U-25  U-21 U-22 U-23 U-24 U-25
U-26 U-27 U-28  U-26 U-27 U-28
X" für Halogen, Nitro, OH. Cyano, SCN, SF5, CVC, -Alkyl, C3-C«-Cycloalkyl, G-C«- Halogenalkyl. G-Ce-Alkoxy, C i -C, -Halogenal koxy. Ca-Ce-Haiogencyeloalkyl, Ci-Ce- Alkoxy-C i -G -alkyl. G -C-Halogenalkoxy-C i -G -alkyl. C i -Ce-Aikoxy-G -G-alkyloxy, Cyano-Ci-Ce-alkyl, G-G-Cycloalkyl-G-G-alkyl, C:-( ,,-Alkenyl. G-G-Alkinyl, G-C6-X "for halogen, nitro, OH, cyano, SCN, SF 5 , CVC, -alkyl, C 3 -C" -cycloalkyl, GC "- haloalkyl, G-Ce-alkoxy, C i -C, -haloalkoxy C 1 -C 6 -alkyoxyalkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy alkyl, GG-cycloalkyl-GG-alkyl, C : - (,, - alkenyl, GG-alkynyl, GC 6 -
Alkylthio, G-G-Alkylcarbonyl, C3 -Ce -Cycloalkylcarbonyl, G-Ce-Alkenylcarbonyl, G- C. -Halogena!kylcarbony!. Ci-C6-Alkoxycarbonyl, C 1 -Cö-Alkoxyimino-C 1 -Ce -alkyl, Ci- G-Alkylsulfmyl, CrG-Alkylsulfonyl, Ci-Ce-Halogenalkylsulfonyl, C1 -G3- Alkylaminocarbonyl oder Di-(C 1 -C6)-alkylaminocarbonyl, Aryl, Hetaryl, Aryl-G -G- alkyl oder Hetaryl-C 1 -G -al ky I steht, wobei Aryl, Hetaryl, Aryl-C i -G -alkyl. und Hetaryl- Ci-Cö-alkyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-CVAlkyl, G- G-Haloalkyl. Ci-C4-Alkoxy oder ( i-Ci-Haloalkoxy substituiert sein können und wobei die Ring-N -Atome in U-17, U-18, U-19, U-26, U-27 und U-28 nicht durch Halogen, Nitro, OH. Cyano, SCN, SF5, Ci-Ce-Alkoxy, G-Ce-Halogenalkoxy, G-G-Alkylthio, G- G-Alkylsulfmyl oder C ι -CV Alkoxy-C ι -G-alkyloxy substituiert sind, n für 0, 1 , 2 oder 3 steht, Alkylthio, GG-alkylcarbonyl, C3-Ce-cycloalkylcarbonyl, G-Ce-alkenylcarbonyl, G-C-haloalkylcarbony! C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfmyl, C 1 -C 8 -alkylsulfonyl, C 1 -C -alkyl-haloalkylsulfonyl, C 1 -C 3 -alkylaminocarbonyl or di (C 1 -C 6) ) -alkylaminocarbonyl, aryl, hetaryl, aryl-G-alkyl or hetaryl-C 1 -G -al ky I, where aryl, hetaryl, aryl-C i -G alkyl. and hetaryl Ci-Cö-alkyl in each case up to three times by halogen, cyano, nitro, G-CValkyl, G-G-haloalkyl. Ci-C4-alkoxy or (i-Ci-haloalkoxy may be substituted and wherein the ring N atoms in U-17, U-18, U-19, U-26, U-27 and U-28 are not halogen , Nitro, OH, cyano, SCN, SF 5 , C 1 -C 6 -alkoxy, G-C 1 -haloalkoxy, GG-alkylthio, G-G-alkylsulfmyl or C 1 -C 4 -alkoxy-C 1 -G -alkyloxy, n is 0, 1, 2 or 3,
R1, R2, R \ R4 jeweils unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro, SF SCN, Amino, G-G-Alkylamino, Di-(G -G) -alkylamino, Hydroxy, COOH, G-G-Alkyl, G-G-Cycloalkyl, G-G -I lalogenalkyl. G-G-Alkoxy, G-G-Halogenalkoxy, G-G- Halogencycloalkyl, G-G-Halogencycloalkyl-G-G-alkyl, G-G-Alkoxy-G-G-aikyi, G-R 1 , R 2 , R \ R 4 are each independently hydrogen, halogen, cyano, nitro, SF SCN, amino, GG-alkylamino, di- (G-G) -alkylamino, hydroxy, COOH, GG-alkyl, GG -Cycloalkyl, GG -I lalogenalkyl. GG-alkoxy, GG-haloalkoxy, GG-halocycloalkyl, GG-halocycloalkyl-GG-alkyl, GG-alkoxy-GG-aikyi, G-
C -Halogenalkoxy-C > -G -alkyl , C -( , - Alkoxy- ·, -C, -alkyloxy, Cyano-C 1 -Cö-alkyl, C3-C6- Cycloalkyl-Ci-Ce-alkyl, C -C„-Alkenyl, C-Ct,-Alkenyloxy, C3-C6-Alkinyl, C3-C6- Alkinyloxy, SH, Ci-C6-Ailcylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C6- Halogenalkylsulfonyl, C 1 -Cö-Alkylcarbonyl, Cs-Ce-Cycloalkylcarbonyl, Ci-Ce- Halogenalkylcarbonyl, C' i-C. -Alkoxyiniino-C' i -C'. -a!kyl. Ci-Ce-Alkoxycarbonyl, Ci-Ce-C 1-haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkyloxy, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C -C "alkenyl, CC t, alkenyloxy, C 3 -C 6 alkynyl, C 3 -C 6 - alkynyloxy, SH, Ci-C 6 -Ailcylthio, Ci-C 6 alkylsulfinyl, Ci-C 6 alkylsulfonyl, C C6 - '. iC -Alkoxyiniino-C'. haloalkylsulfonyl, C 1 -Cö-alkylcarbonyl, Cs-Ce-cycloalkylcarbonyl, Ci-Ce haloalkylcarbonyl, C i -C -a alkyl Ci-Ce-alkoxycarbonyl,!. Ci-Ce
Alkylaminocarbonyl, Di-(Ci-C6)-aikyiaminocarbonyi, Aryl, Hetaryi, Aryl-C CV-alkyl oder Hetaryi-G-Ce-alkyi stehen, wobei Aryl, Hetaryi, Aryl-CVCValkyl und H etary I -C i -C » -alkyl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Ci-Ce- Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloaikyl, G-C6-Alkoxy, G-C6-Alkylaminocarbonyl, di- (Ci-C6) -aikyiaminocarbonyi, aryl, hetaryi, aryl-C-C-C-alkyl or Hetaryi-G-Ce-alkyi, where aryl, Hetaryi, aryl-CVCValkyl and H etary I -C i -C » alkyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 6 -C 12 -cycloalkyl, GC 6 - Alkoxy, GC 6 -
Halogenalkyl. G-Ce-Halogenalkoxy oder G-C6-Alkylthio substituiert sein können, oder Haloalkyl. G-Ce-haloalkoxy or G-C6-alkylthio may be substituted, or
R1 und R2 oder R 1 and R 2 or
R- und R3 oder R3 und R4 jeweils zusammen einen 5- oder 6 giiedrigen aliphatischen, aromatischen, heteroaromatischen oder heterocyclischen Ring bilden, welcher gegebenenfalls 1 bis 2 Atome aus der Reihe O, S und N enthalten kann und der gegebenenfalls ein- oder mehrfach durch Halogen oder durch G-C4-Alkyl substituiert sein kann, R and R 3 or R 3 and R 4 in each case together form a 5- or 6-membered aliphatic, aromatic, heteroaromatic or heterocyclic ring which may optionally contain 1 to 2 atoms from the series O, S and N and which may optionally contain one or more or may be substituted several times by halogen or by G-C4-alkyl,
R5 für Wasserstoff oder für G-Ce-Aikyl, C2-Ce-Alkenyl oder C2-Ce-Alkinyi steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis zu fünfach durch Halogen oder einfach durch Nitro, Cyano, C3-C6-Cycloalkyl, -O-R51, -S(0)p-R52, -N(R53)(R54), - C(=0)N( 53)(R54), -0-C(=0)-R55, -C(=0)-R55, O-SO2-R56, Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl substituiert sein können, wobei Aryl, Hetaryl, Heterocyclyl oder Oxoheterocyclyl wiederum jeweils einfach bis dreifach durch Halogen, Nitro, Cyano, G- ( Y-Alkyl, G-G-Cycloaikyi, G-G-Halogenaikyl, G-G-Alkoxy, G-G-Halogenalkoxy, G- G-Halogencycloalkyl, G-G-Aikoxy-G-G-alkyl, C ·, -C -Halogenal koxy-C 1 -G -alkyl , G- G-Alkoxy-G-G-alkyloxy, Cyano-Ci-C6-alkyl, G-G-Cycloalkyl-G-G -alkyl, G-G- Alkenyl, G-G-Aikinyl, G-G-Alkylthio, G-G-Alkylcarbonyl, C3-C6-Cycloalkylcarbonyl, G-G-Alkenylcarbonyl, G-G-Halogenalkylcarbonyl, C 1 -C6-Alkoxycarbonyl, G-G- Alkylsulfonyl, C 1 -G -Halogenalkylsulfonyl, Ci-C6-Alkylaminocarbonyl, Di-(G-G)- alkylamino carbonyl , C 1 -G - Alkyl carbonylamino , Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl wiederum gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G-Ce-Alkyl, C2-Ce-Alkenyi, C2-C6- Alkinyl, CVC -Alkoxy, Ci-Cö-Halogenalkyl, -( '„-Halogenalkoxy oder Ci-Ce-Alkylthio substituiert sein können, oder für C;-CV-Cycloalkyl oder C;-Ct,-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, Ci-Ce-Alkyi, Ci -Ce-Halogenalkyl, Ci-Cö-Alkoxy, C 1 -C, -Halogenalkoxy C3- Ce-Cycloalkyl, Ci-Ce-Alkylthio, Ci-Ce-Alkylsulfmyl, G-C6-Alkylsulfonyl, Aryl, Hetaryl, Aryl-Ci-Ce-alkyi oder substituiert sein können, wobei Aryl, Hetaryl, Aryl-Ci-Cö-alkyi und Hetaryl-G-Ce-alkyi jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, VCt-Alkyl, C i-Ci-Halogenal kyl , Cj -C4-Alkoxy oder C i-Ci-Haloalkoxy substituiert sein können, oder für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, C 1 -Ce-Alkylamino, Di-(Ci-Ce)- alkylamino, Hydroxy, COOH. (Ί -G- Alkyl, Cs-Ce-Cycloalkyl, C . -C -Halogenalkyl, G-C6- Alkoxy, C : -G -Halogenalkoxy. Cs-Ce-Haiogencycloalkyl, R 5 is hydrogen or G-Ce-Aikyl, C 2 -Ce-alkenyl or C 2 -Ce-Alkinyi, where the abovementioned radicals, where appropriate independently of one another, can be monosubstituted by halogen or simply by nitro, cyano, C 3 - C 6 -cycloalkyl, -OR 51 , -S (O) p -R 52 , -N (R 53 ) (R 54 ), C (= O) N ( 53 ) (R 54 ), -O-C (= O) -R 55 , -C (= O) -R 55 , O-SO 2 -R 56 , aryl, hetaryl, heterocyclyl or oxoheterocyclyl In turn, aryl, hetaryl, heterocyclyl or oxoheterocyclyl may be in each case monosubstituted to trisubstituted by halogen, nitro, cyano, G- (Y-alkyl, GG-cycloalkyl, GG-halogenoyl, GG-alkoxy, GG-haloalkoxy, G-G Halocycloalkyl, GG-aikoxy-GG-alkyl, C ·-, C-haloalkoxy-C 1 -G -alkyl, G-G-alkoxy-GG-alkyloxy, cyano-C 1 -C 6 -alkyl, GG-cycloalkyl- GG-alkyl, GG-alkenyl, GG-aikinyl, GG-alkylthio, GG-alkylcarbonyl, C3-C6-cycloalkylcarbonyl, GG-alkenylcarbonyl, GG-haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, GG-alkylsulfonyl, C 1 -G - Haloalkylsulfonyl, Ci-C6-alkylaminocarbonyl, di- (GG) - alkylamino carbonyl, C 1 -G - alkyl carbonylamino, aryl or hetaryl may be substituted, wherein aryl and hetaryl turn, optionally mono- or polysubstituted by identical or different halogen, cyano, Nitro, hydroxy, G-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl , C 1 -C 4 -alkoxy, C 1 -C 6 -haloalkyl, - ( ' "-haloalkoxy or C 1 -C 6 -alkylthio), or represents C 1 -C 4 -cycloalkyl or C 1 -C 4 -heterocyclyl, where the abovementioned radicals are, if appropriate independently of one another simply by trisubstituted by halogen, or simply by cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkylthio, Ci-Ce-alkylsulfmyl, GC 6 alkylsulfonyl, aryl, hetaryl, aryl-Ci-Ce-alkyi or Aryl, hetaryl, aryl-C 1 -C 6 -alkyl and hetaryl-G-C 1 -C 4 -alkyl may each be monosubstituted to trisubstituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 18 -haloalkyl, C 1 -C 4 Or aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, amino, cyano, SF 5 , SCN, C 1 -C 6 alkylamino, di (C 1 -C 6) alkylamino, hydroxy, COOH. (Ί-G-alkyl, Cs-Ce-cycloalkyl, C -C -haloalkyl, GC 6 -alkoxy, C: -G -haloalkoxy, Cs-Ce-halio-cetylalkyl,
alkyl. G-Ce-Aikoxy-G-Ce-allcyl, G-G-Halogenalkoxy-G-G-aikyl, G-C«-Alkoxy-G-C6- alkyloxy, Cyano-G-Ce-alkyl, Cs-Ce-Cycloalkyi-G-Ce-aikyi, G-G-Alkenyl, C-.-G -Alkinyl, Si l. G-G -Alkylthio. G-C6-Alkylcarbonyl, G-G-Cycloalkyicarbonyl, C2-C6- Alkenylcarbonyl, G-C6-Halogenalkylcarbonyl, G-C6-Alkoxycarbonyl, G-G- Alkylsulfonyl, C 1 -C« -Halogenalkylsulfonyl, G-G-Alkylaminocarbonyl, Di-(G-Ce)- alkylaminocarbonyl oder Tri-(G-G -alkyl )silyl, p für 0, 1 oder 2 steht, alkyl. G-Ce-Aikoxy-G-Ce-acyl, GG-haloalkoxy-GG-aikyl, GC "alkoxy-GC 6 -alkyloxy, cyano-G-Ce-alkyl, Cs-Ce-Cycloalkyi-G-Ce-aikyi, GG-alkenyl, C -.- G -alkynyl, Si l. GG alkylthio. GC 6 alkylcarbonyl, GG-cycloalkyicarbonyl, C 2 -C 6 alkenylcarbonyl, G-C 6 haloalkylcarbonyl, GC 6 alkoxycarbonyl, GG-alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, GG-alkylaminocarbonyl, di (G-Ce ) - alkylaminocarbonyl or tri- (GG-alkyl) silyl, p is 0, 1 or 2,
R51 für Wasserstoff oder für Ci-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl oder C3-C6-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Nitro, Cyano, C3-C6-Cycioalkyl, Cs -G -Alkoxy, G-Ce-Halogenalkoxy, G -G -Alkylthio, Ci-C6-Alkylsulfmyl, G-G-Alkylsuifonyl, G-G- Alkylcarbonyl, G-Ce-Alkoxyimino-G-G-alkyi, C3 -G-Cycloalkylcarbonyl, G-G- Alkenylcarbonyl, G-G-Halogenaikyl carbonyl, G -G-Alkoxycarbonyl, G-G- Alkylsulfonyl, C 1 -G -Halogenalkylsulfonyl, G-G-Alkylaminocarbonyl, Di-(G-G)- alkylamino carbonyl , Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-Ci-Alkyl, C > -C.i - I I a 1 oge n a I k y I . G -G-Alkoxy oder G-Gi-Hal alkoxy substituiert sein können, oder R 51 is hydrogen or C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 6 -C 12 -cycloalkyl or C 3 -C 6 -heterocyclyl, where the abovementioned radicals are, if desired, independently of one another monosubstituted to trisubstituted by halogen or simply by nitro, cyano, C 3 -C 6 -cycloalkyl, C 5 -G -alkoxy, G-C 1 -haloalkoxy, G -G-alkylthio, C 1 -C 6 -alkylsulfmyl, GG-alkylsulfonyl, GG-alkylcarbonyl , G-Ce-alkoxyimino-GG-alkyl, C 3 -G -cycloalkylcarbonyl, GG-alkenylcarbonyl, GG-haloalkylcarbonyl, G-G-alkoxycarbonyl, GG-alkylsulfonyl, C 1 -G -haloalkylsulfonyl, GG-alkylaminocarbonyl, di ( GG) - alkylamino carbonyl, aryl or hetaryl can be substituted, wherein aryl and hetaryl in each case monosubstituted to trisubstituted by halogen, cyano, nitro, G-Ci-alkyl, C> -Ci - II a 1 oge na I ky I. G -G alkoxy or G-Gi-Hal alkoxy may be substituted, or
R51 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, C 1 -C6-Alkylamino, Di-(G-G)- alkylamino, Hydroxy, COOH, G -G-Alkyl, G-G-Cycloalkyl, C . -C. -Halogenalkyl. Ci-C6- Alkoxy, G-Ce-Halogenalkoxy, C3-C6-Halogencycloalkyl, C3-C6-Halogencycloalkyl-Ci-C6- alkyl, Ci-C6-Alkoxy-Ci-C6-alkyl, t - , -Halogenalkoxy-C , -( -al ky l . i -G -Alkoxy-CVC„- alkyloxy, Cyano-G-C6-alkyl, Cs-Ce-Cycloalkyl-Ci-Ce-alkyl, C2-C6-Alkenyi, C3-C6-Alkinyl, Ci-Ce-Alkylthio, Ci-Ce-Alkylcarbonyl, Cs-Ce-Cycloaikylcarbonyl, C2-C6-Alkenylcarbonyl, C I -C, -Halogenalkylcarbonyl, Ci-Ce-Alkoxycarbonyi, C 1-Ce -Alkylsulfonyl, Ci-Ce- Halogenallcylsulfonyl, Ci-Ce-Alkylamino carbonyl, Di-(Ci-C6)-alkylaminocarbonyl oder Tri - (Ci-C6-alkyl)silyl, R 51 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF 5 , SCN, C 1 -C 6 -alkylamino, di- ( GG) -alkylamino, hydroxy, COOH, G-G-alkyl, GG-cycloalkyl, C. -C. -Haloalkyl. Ci-C 6 - alkoxy, G-Ce-haloalkoxy, C3-C6-halocycloalkyl, C3-C6-halocycloalkyl-Ci-C6 alkyl, Ci-C 6 alkoxy-C 6 alkyl, t -, haloalkoxy -C, - (-alkyl-i-G-alkoxy-CVC "- alkyloxy, cyano-GC 6 -alkyl, Cs-Ce-cycloalkyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -cycloacylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyi, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkylamino carbonyl, di- (C 1 -C 6 ) -alkylaminocarbonyl or tri (C 1 -C 6 -alkyl) silyl,
R52 für Ci-Ce-Alkyl, C2-C6-Alkenyi, C.-C, -Alkinyl. Cs-Ce-Cycloalkyl oder Cs-Ce-Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano , Cs-Ce-Cycloalkyi, G-Ce-Aikoxy, i -C. -Halogenalkoxy. Ci-Cö-Alkylthio, CI-CÖ- Alkylsulfinyl, Ci-Ce-Alkyisulfonyi, Ci-Ce-Alkylcarbonyl, Ci-Ce-Alkoxyimino-C 1-Cö-alkyl, C3-C6-Cycloalkylcarbonyl, C2-C6-Alkenylcarbonyl, G-Ce-Halogenalkylcarbonyi, CI-CÖ- Alkoxycarbonyl, C 1 -C6-Alkylsulfonyl, Ci-Cö-Halogenalkylsulfonyl, Ci-Ce- Alkylaminocarbonyl, Di-(C 1 -C6)-alkylaminocarbonyl, Aryl oder Hetaryl, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, CVC i-Alkyl, C1 -C4- Halogenalkyl, C i -C.;-Alkoxy oder ( VC i-Haloalkoxy substituiert sein können, oder für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Amino, Cyano, SF5, SCN, C i -Ce-Alkylamino, Di-(Ci-C«)- alkylamino, Hydroxy, COOK, CVC-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Haiogenalkyl, Ci-C6- Alkoxy. Ci-Cö-Halogenalkoxy, C3-C6-Halogencycloalkyl, Cs-Ce-Halogencycloalkyl-O-Ce- alkyl, Ci-Ce-Alkoxy-G-Ce-alkyi, G-Ce-Halogenalkoxy-G-Ce-alkyl, G-Ce-Alkoxy-G-Ce- alkyloxy, Cyano-Ci-C6-alkyl, C3-C6-Cycloalkyl-C i -C6-alkyl, C2-C6-Alkenyl, C3-C6-Alkinyl, Ci-Ce-Alkylthio, Ci-Cö-Alkylcarbonyl, Cs-Ce-Cycloalkylcarbonyi, C2-C6-Alkenylcarbonyl, Ci-Ce-Halogenalkylcarbonyl, G-Ce-Alkoxycarbonyl, C i -C« -Alkylsulfonyl, Ci-Ce- Halogenalkylsulfonyl, Ci-Ce - Alkylamino carbonyl , Di-(Ci-C6)-alkylaminocarbonyl oder Tri- (Ci-C6-alkyl)silyl, für Wasserstoff, Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, G-C4- Alkoxy, ( i -C 4-Alkoxy-C ; -C* -Alkyl, C i -Ce-Alkoxycarbonyl, Ci-Ce-Alkylcarbonyl, Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, CVCi-Alkyl, C - .·, - H a 1 og e n a I k y 1 , C i - 4-Alkoxy oder C i -C.i-Ha!oalkoxy substituiert sein können, für Wasserstoff oder für Ci-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl oder C3-C6-Cycloalkyl- Ct -Alkyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy. CVCY-Alkyl, Cs-Ce-Cycloalkyl, C i -d-Alkoxy. Ci-C4-Haloalkoxy, Ci-C4-Aikyithio, Ci-C4-Alkylsulfmyl, C i -C4-Alkylsulfonyl, G-Ce-Alkoxycarbonyi, i-Ct -Alkylcarbonyl oder C3-C6-Trialkylsilyl substituiert sein können, oder für Aryl, Hetaryl, Aryl-Ci-Ce-aikyl oder Heteroaryl-Ci-Ce-alkyl steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-Ce- Alkyl. Cs-Ce-Cycloalkyl, Cs-Ce-Cycloalkylamino, ( VC 4-Alkoxy, Ci-C4-Haloalkoxy, Ci-C4- Alkylthio. Ci-C -Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkylsulfimino, C2-C6- Alkoxycarbonyl oder C2-C6-Alkylcarbonyl, oder R53 und R54 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Atom aus der Reihe O.S oder N enthält und gegebenenfalls einfach bis vierfach mit CVC '-Alkyl, Halogen, Cyano, Amino oder G-C2-A!koxy substituiert sein kann, R 52 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkynyl. Cs-Ce-cycloalkyl or Cs-Ce-heterocyclyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, Cs-Ce-cycloalkyl, G-Ce-aoxoxy, i -C. -Haloalkoxy. Ci-COE-alkylthio, CI-C Ö - alkylsulfinyl, Ci-Ce-Alkyisulfonyi, Ci-Ce-alkylcarbonyl, Ci-Ce-alkoxyimino-C 1-COE-alkyl, C3-C6-cycloalkylcarbonyl, C 2 -C 6 alkenylcarbonyl , G-Ce-Halogenalkylcarbonyi, CI-C Ö - alkoxycarbonyl, C 1 -C 6 alkylsulfonyl, Ci-COE-haloalkylsulfonyl, Ci-Ce-alkylaminocarbonyl, di- (C 1 -C 6) alkylaminocarbonyl, aryl or hetaryl, wherein aryl and hetaryl can each be monosubstituted to trisubstituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or (C -C 1 -haloalkoxy) or aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, nitro, amino, cyano, SF 5 , SCN, C 1 -C 6 -alkylamino, di (Ci -C «) - alkylamino, hydroxy, COOK, CVC-alkyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -Haiogenalkyl, Ci-C 6 - alkoxy. C 1 -C 6 -haloalkoxy, C 3 -C 6 -halocycloalkyl, C 5 -C 12 -halocycloalkyl-O-C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-G-C 12 -alkyi, G-C 6 -haloalkoxy-G-C 12 -alkyl, C 1 -C 6 -cycloalkyloxy, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl , C 1 -C 6 -alkylthio, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -cycloalkylcarbonyi, C 2 -C 6 -alkenylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, G-C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl , Ci-Ce - alkylamino carbonyl, di- (Ci-C6) alkylaminocarbonyl or tri- (Ci-C 6 alkyl) silyl, represents hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, GC 4 -alkoxy, (i -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, aryl, Hetaryl, arylcarbonyl or hetarylcarbonyl, where aryl and hetaryl are in each case monosubstituted to trisubstituted by halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -, H-halogenoalkylene, C 1 -4 -alkoxy or C i -Ci-Ha! Oalkoxy can be substituted, for hydrogen od it is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkyl-C t -alkyl, where the abovementioned radicals optionally independently one to five times by halogen or simply by cyano, nitro, hydroxy. CVCY-alkyl, Cs-Ce-cycloalkyl, C i -d-alkoxy. Ci-C4-haloalkoxy, Ci-C 4 -Aikyithio, Ci-C 4 -Alkylsulfmyl, C i -C 4 alkylsulfonyl, G-Ce-Alkoxycarbonyi, i-Ct-alkylcarbonyl or C3-C6 trialkylsilyl may be substituted, or is aryl, hetaryl, aryl-Ci-Ce-aikyl or heteroaryl-C 1 -C 6 -alkyl, where the abovementioned radicals may optionally be substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, Ci -Ce- alkyl. Cs-Ce-cycloalkyl, Cs-Ce-cycloalkylamino, (VC-4 alkoxy, Ci-C4-haloalkoxy, Ci-C 4 -. Alkylthio Ci-C -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, Ci-C 4 - Alkylsulfimino, C 2 -C 6 - alkoxycarbonyl or C 2 -C 6 alkylcarbonyl, or R 53 and R 54 may be connected to each other via two to six carbon atoms and form a ring optionally additionally containing one further atom from the series OS or N and optionally monosubstituted to fourfold with CVC ' alkyl, halogen, cyano, amino or G -C 2 -alkoxy may be substituted,
R55 für Ci-Ce-Alkyl, C3-G,-Cycloalkyl, CVCY-Halogenalkyl. C3-C6-Halogencycloalkyl, C3-C6- Cycloalkyl-Ci-Ce-alkyl, C3-C6-Halogencycloalkyl-Ci-C6-alkyl, Cyano-Ci-C6-alkyl, G-C6- Alkoxy, C i -C-Halogenalkoxy. Ci -Ce-Alkoxy-G-Ce-alkyl, Ci-C, -Halogenalkoxy-C i -CY- alkyl, Aryl, Hetaryl. Aryl-C i-G -alkyl. oder II etary1-C > -C, -al kyI steht, wobei Aryl, Hetaryl. Aryl-C VCY-alky! und H etary1-C > -C,.-al ky1 gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, Ci-Ce-Alkyl, C3-Ce-Cycloalkyl, G-Ce- Halogenalkyl. CVC , -Alkoxy, G -Ce-Halogenalkoxy, C3-C6-Halogencycloalkyl oder G-Ce- Alkoxy-Ci-Cö -alkyl substituiert sein können, R 55 is Ci-Ce-alkyl, C 3 -G, -cycloalkyl, CVCY-haloalkyl. C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -halocycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, GC 6 -alkoxy , C i -C -haloalkoxy. C 1 -C 6 -alkoxy-G-C 1 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 6 -alkyl, aryl, hetaryl. Aryl-C iG-alkyl. or II etary1-C> -C, -alkyl, wherein aryl, hetaryl. Aryl-C VCY-alky! and H etary1-C> -C, -alky1 optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C -cycloalkyl, G-C 1 -haloalkyl. CVC, alkoxy, G -Ce-haloalkoxy, C3-C6-halocycloalkyl or G-Ce-alkoxy-Ci-Cö-alkyl may be substituted,
R56 für Ci-Ce-Alkyl, C3-C6-Cycloalkyl, Ci-C6-Halogenaikyl, C3-C6-Halogencycloalkyl, C3-C6- Cycloalkyl-Ci-Ce-alkyl, C3-C6-Halogencycloalkyl-Ci -C6-alkyl, Cyano-Ci-C6-alkyl, Ci-C6- Alkoxy, C i -C. -Halogenalkoxy. Ci -Ce-Alkoxy-Ci-Ce-aikyl, Ci-C'. -Halogenalkoxy-C'i-C.- alkyl. Aryl, Hetaryl oder Aryl-C i-Ce-aikyl steht, wobei Aryl, Hetaryl und Aryl-C i-C,. -alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, Ci-Ce-Alkyl, C3-C6-Cycloalkyl, C.-C, -Halogenalkyl. Ci-Ce-Aikoxy, Ci-C6- Halogenalkoxy, C3-Cö-Halogencycloalkyl oder C i-Ct,-Alkoxy-C ; -C, -alkyl substituiert sein können, R 56 for Ci-Ce alkyl, C 3 -C 6 cycloalkyl, C 6 -Halogenaikyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 - cycloalkyl-Ci-Ce-alkyl, C 3 -C 6 halocycloalkyl-Ci-C6 alkyl, cyano-Ci-C 6 alkyl, C 6 - alkoxy, C i -C. -Haloalkoxy. Ci-Ce-alkoxy-Ci-Ce-aikyl, Ci-C ' . Haloalkoxy-C ' iC-alkyl. Aryl, hetaryl or aryl-C i-Ce-aikyl, wherein aryl, hetaryl and aryl-C iC ,. alkyl optionally mono- or polysubstituted by identical or different halo, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl. Ci-Ce-alkoxy, Ci-C6 - haloalkoxy, C3-COE-halocycloalkyl or C iC t, alkoxy-C; -C, -alkyl may be substituted,
R' für Ci-Ce-Ailcyl, Cs-Ce-Cycloalkyl, Ci-C, -Halogenalkyl. Cs-Ce-Halogencycloalkyl, C3-C6- Cycloaikyl-G-Ce-aikyi, C3-C6-Halogencycloalkyl-C 1 -C6-alkyl, Cyano-Ci-C6-alkyl, Ci-C6- Alkoxy-Ci-G -alkyl, Ci-Ce-Halogenalkoxy-Ci -Ce-aikyl, Aryl, Hetaryl. Aryl-C i-Ce-alkyl oder Hetaryl-Ci-C, -alkyl steht, wobei Aryl, Hetaryl, Aryl-C i-Ce -alkyl und Hetaryl-G-Ce- alkyl gegebenenfalls einfach oder mehrfach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, Ci-Ce-Alkyl, C3-C6-Cycloalkyl, Ci-C, -Halogenalkyl. Ci-Ce-Alkoxy, Ci-C«- Halogenalkoxy, C:-C, -Halogencycloalkyl oder C ι -C,-Alkoxy-C ; -C( -alkyl substituiert sein können. R 'for Ci-Ce-Ailcyl, Cs-Ce-cycloalkyl, Ci-C, -haloalkyl. Cs-Ce-halocycloalkyl, C 3 -C 6 - Cycloaikyl-G-Ce-aikyi, C 3 -C 6 -halocycloalkyl-C 1 -C 6 alkyl, cyano-C 6 alkyl, C 6 - Alkoxy-Ci-G-alkyl, Ci-Ce-haloalkoxy-Ci-Ce-aikyl, aryl, hetaryl. Aryl-C i-Ce-alkyl or hetaryl-Ci-C, -alkyl, wherein aryl, hetaryl, aryl-C i-Ce-alkyl and hetaryl-G-Ce- alkyl optionally mono- or polysubstituted by identical or different halogen , Cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl. C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -halo-cycloalkyl or C 1 -C 4 -alkoxy-C; -C ( alkyl) may be substituted.
R für Wasserstoff, Ci-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1 -C4- Alkoxy, C VC Alkoxy-C' i -C' t - Alkyl, Ci -Ce-Alkoxycarbonyl oder Ci-Ce-Alkylcarbonyl steht, R is hydrogen, Ci-Ce-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C4- alkoxy, C VC alkoxy-C 'i -C 't - alkyl, Ci -Ce-alkoxycarbonyl or Ci-Ce-alkylcarbonyl,
R7a für Wasserstoff, CVCV, -Alkyl, C2-C6-Aikenyl, C:-C t,-Alkinyl, C3-C6-Cycloaikyl, C1-C4- Alkoxy-C ' -Alkyl, Ci-Ce-Alkoxycarbonyl oder C 1-Ce-Alkylcarbonyl steht, R 7a is hydrogen, CVCV alkyl, C 2 -C 6 -Aikenyl, C: -C t, alkynyl, C 3 -C 6 -Cycloaikyl, C1-C4 alkoxy-C 'alkyl, Ci-Ce- Alkoxycarbonyl or C 1 -C 6 -alkylcarbonyl,
R8 für Wasserstoff oder für C i-C -Alkyl, C;-G,-Alkenyl oder C:-C„-Alkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, Nitro, Hydroxy, G-Ce-Alkyi, C.' ;-C\,-C'yeloalkyl, G -CVAIkoxy, C1-C4- Haloaikoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkyisulfonyl, C1-C4- Alkylsulfimino, C i-CVAlkylsul fimino-C 1 -CValkyl, Ci-C4-Alkylsulfimino-C2-C5- alkylcarbonyl, Ci-C4-Alkyisulfoximino, Ci -C4-Alkylsulfoximino-C 1 -C4-alkyl, C1-C4- Alkylsulfoximino-C2-C5-alkylcarbonyl, C \ -G - A I koxycarbony I , G - -Alkylcarbonyl oder C3-C6-Trialkylsilyl substituiert sein können, oder R8 für Aryi-G-G-alkyl, Heteroaryl-G-G-alkyi, C3-Ci2-Cycloalkyl, C3 -C 12-Cy cloalkyl-C 1 -G-R 8 is hydrogen or represents C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl or C 1 -C 3 -alkynyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to five times by halogen or simply by cyano, nitro, hydroxy, G-C 1 -alkyl, C. '-C \ - C' yeloalkyl, G -CVAIkoxy, C1-C4 Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 -Alkyisulfonyl, C1-C4 Alkylsulfimino, C 1 -C -alkylsulfin-C 1 -C 12 -alkyl, C 1 -C 4 -alkylsulfimino-C 2 -C 5 -alkylcarbonyl, C 1 -C 4 -alkylsulfoximino, C 1 -C 4 -alkylsulfoximino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulfoximino-C 2 -C 4 -alkylsulfoximino-C 1 -C 4 -alkyl C5-alkylcarbonyl, C 1 -G -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl or C 3 -C 6 -trialkylsilyl, or R 8 for aryl-GG-alkyl, heteroaryl-GG-alkyl, C 3 -C 12 -cycloalkyl, C 3 -C 1 2 -Cy cloalkyl-C 1 -G-
Alkyl oder G-C 1.-Bicvcioalkyl steht, wobei die vorgenannten Reste gegebenenfalls substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, (VC, -Alk vi, G-G-Cycloa!kyl, G-G- Cycloalkylamino, G -C i-Alkoxy, VCi-Haloalkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfinyl, C 1 -C4-Alkylsulfonyl, C 1 -C4-Alkylsulfimino, C-C -Alkoxycarbonvl oder C2-C6-Alkyl or GC is 1.-Bicvcioalkyl, where the aforementioned radicals may optionally be substituted and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, (VC, -Alk vi, GG-Cycloalkyl, GG- cycloalkylamino, G i -C alkoxy, VCi-haloalkoxy, Ci-C4-alkylthio, Ci-C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 Alkylsulfimino, CC -Alkoxycarbonvl or C2-C6
Alkylcarbonyl, oder Alkylcarbonyl, or
R8 für einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituierten 5- oder 6-gliedrigen aromatischen oder heteroaromatischen Ring, einen 4- bis 6-giiedrigen teilweise gesättigten Ring oder gesättigten heterozyklischen Ring, oder einen gesättigten oder aromatischen hetero-bizyklischen Ring steht, welcher gegebenenfalls ein bis drei Heteroatome aus der Reihe O, S oder N enthalten kann und der gegebenenfalls ein- oder mehrfach substituiert sein kann, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, C i -C, -Alkyl, C—C, -Alkinvl, Ci-Ce-Haiogenalkyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkylammo, Ci-CVAikoxy, C1-C4-R 8 is an optionally mono- or polysubstituted, identically or differently substituted 5- or 6-membered aromatic or heteroaromatic ring, a 4- to 6-membered partially saturated ring or saturated heterocyclic ring, or a saturated or aromatic hetero-bicyclic ring, which may optionally contain one to three heteroatoms from the series O, S or N and which may optionally be mono- or polysubstituted, where the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, C i -C, Alkyl, C 1 -C 6 -alkynyl, C 1 -C 6 -halioalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylammo, C 1 -C 6 -alkoxy, C 1 -C 4 -alkyl
Haloalkoxy. Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C1-C4- Alkylsulfimino, C2-C6-Alkoxycarbonyl oder C2-C6 -Alkylcarbonyl, oder Haloalkoxy. C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfimino, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -alkylcarbonyl, or
R und R8 miteinander über zwei bis sechs Kohlenstoffatome verbunden sein können und einen Ring ausbilden, der gegebenenfalls zusätzlich ein weiteres Stickstoff-, Schwefel- oderR and R 8 may be connected to each other via two to six carbon atoms and form a ring, optionally in addition a further nitrogen, sulfur or
Sauerstoffatom enthält und gegebenenfalls einfach bis vierfach mit Ci -C -Alkyl, Halogen, Cyano, Amino oder C i-CVAlkoxy substituiert sein kann. Contains oxygen atom and may optionally be monosubstituted to four times with Ci -C alkyl, halogen, cyano, amino or Ci-CVAlkoxy substituted.
R9 für Wasserstoff, Fluor, Chlor. Ci-C4-Alkyl, C3-C6-Cycloalkyl oder G-C4-Haiogenalkyl steht, R9a für Wasserstoff, Fluor, Chlor, G-C4-Aikyl, C3-C6-Cycloalkyl oder CVCi-Halogenalkyl steht, R 9 is hydrogen, fluorine, chlorine. C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or GC 4 -Haiogenalkyl, R 9a is hydrogen, fluorine, chlorine, GC 4 -alkyl, C 3 -C 6 -cycloalkyl or CVCi-haloalkyl,
R10 für Wasserstoff, Fluor, Chlor oder C i -G-Alkyl steht, und R 10 is hydrogen, fluorine, chlorine or C i -G alkyl, and
R ioa fflr Wasserstoff, Fluor, Chlor oder VG-Alky! steht. R i o a for hydrogen, fluorine, chlorine or VG-alky! stands.
2. Verbindung nach Anspruch 1 , worin 2. A compound according to claim 1, wherein
Q! und Q2 zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N-Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q ! and Q 2 together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR6, -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, T R \ -OR 6, -N (R 7) (R 8) or -N (R 7a) -N (R 7) (R 8) group,
W für O steht, W stands for O,
G für eine Bindung, für -€(R9)(R10)-, oder für C(R9)(R10)C(R9a)(R10a) steht, G is a bond, - € (R 9 ) (R 10 ) -, or C (R 9 ) (R 10 ) C (R 9a ) (R 10a ),
U für einen Cyclus der Reihe U-l , U-2, U-5, U-6, U-9, U-l 0, U-20 oder U-23 steht, U is a cycle of the series U-1, U-2, U-5, U-6, U-9, U-10, U-20 or U-23,
Xa für Halogen, Nitro, Cyano, SF5, G -G-Alkyl, G-C4-Halogenalkyl, Ci-C4-Alkoxy, G-G- Halogenalkoxy. Ci-C -Aikoxy-Ci-C4-alkyi, Cyano-G-C4-alkyl, C2-C4-Alkenyi, G-G- Aikinyl, G-C4-Aikylthio, G-C4-Aikylcarbonyl, C i -C4-Alkoxycarbonyl, G-G-A!koxyimino- G-C4-alkyl, G-G-Alkylsulfmyl, G-C4-Alkylsulfonyl, G-C4-Halogenalkylsulfonyl, Phenyl, Pyridyl, Phenyl-G-C4-aikyl oder Pyridyl -C i -G-al ky 1 steht, wobei Phenyl, Pyridyl, Phenyl - G-C4-aikyl und Pyridyl-G-G-alky l jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, G-C4-Aikyl, G-C4-Halogenaikyl, G-C4-Alkoxy oder G-C4-Haloalkoxy substituiert sein können, n für 0, 1 , 2 oder 3 steht, X a is halogen, nitro, cyano, SF 5, G-G alkyl, GC 4 haloalkyl, Ci-C 4 alkoxy, haloalkoxy GG. Ci-C -alkoxy-Ci-C 4 -alkyi, cyano-GC 4 alkyl, C 2 -C 4 -Alkenyi, GG Aikinyl, GC 4 -Aikylthio, GC 4 -Aikylcarbonyl, C i -C 4 alkoxycarbonyl, GGA! Koxyimino-GC 4 -alkyl, GG-alkylsulfmyl, GC 4 -alkylsulfonyl, GC 4 -haloalkylsulfonyl, phenyl, pyridyl, phenyl-GC 4 -aikyl or pyridyl-C i -G -alkyl 1, wherein phenyl, pyridyl , Phenyl - GC 4 -acyl and pyridyl-GG-alkyl, each may be monosubstituted to trisubstituted by halogen, cyano, nitro, GC 4 -alkyl, GC 4 -haloalkyl, GC 4 -alkoxy or GC 4 -haloalkoxy, n for 0, 1, 2 or 3,
R1, R2, R3, R4 jeweils unabhängig voneinander für Wasserstoff, Halogen, Cyano, G-G- Alkyl, C3-C6-Cycloaikyl, G-C4-Halogenaikyl, G-C4-Alkoxy, G-G-Halogenalitoxy, G-C4- Alkoxy-C i-G-alkyl. C2-C4-Alkenyl, C2-C4-Alkenyloxy, C3-C4-Alkinyl, C3-C4-Alkinyloxy, G-C4-Alkyithio, G-C4-Alkylsulfmyl, G-C4-Alkyisulfonyl, Ci-C4-Alkoxyimino-Ci-C4-alkyl, C i -C4-Alkoxycarbonyl, Aryl oderHetaryl stehen, wobei Aryl und Hetaryl gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen, Cyano, G-C4-Alkyi, G-C4-Alkoxy, G-C4-Halogenalkyl, G-C4-Halogenalkoxy oder Ci -Ci-Alkylthio substituiert sein können, R5 für CH2Y steht, für Wasserstoff, Halogen, G -G-Alkyl, G -G -Halogenalkyl, -O-R51, -S(0)P R 1 , R 2 , R 3 , R 4 are each independently of one another hydrogen, halogen, cyano, GG-alkyl, C 3 -C 6 -cycloalkyl, GC 4 -haloalkyl, GC 4 -alkoxy, GG-haloalitoxy, GC 4 - Alkoxy-C iG-alkyl. C 2 -C 4 alkenyl, C 2 -C 4 alkenyloxy, C 3 -C 4 alkynyl, C 3 -C 4 alkynyloxy, GC 4 alkylthio, GC 4 alkylsulfmyl, GC 4 alkylsulfonyl, Ci-C 4 alkoxyimino-Ci-C 4 alkyl, C i -C 4 -alkoxycarbonyl, aryl oderHetaryl, where aryl and hetaryl which is optionally mono- to trisubstituted by identical or different halogen, cyano, GC 4 -Alkyi, GC 4 alkoxy, GC 4 -haloalkyl, GC 4 -haloalkoxy or Ci-Ci-alkylthio may be substituted, R 5 is CH 2 Y, is hydrogen, halogen, G-alkyl, G-haloalkyl, -OR 51 , -S (O) P
N(R53)(R54), 0-S02-R56 oder für einen der Reste Y-l bis Y-23 steht, N (R 53 ) (R 54 ), 0-S0 2 -R 56 or one of the radicals Yl to Y-23,
Y-1 3 Y-1 4 Y-1 5 Y-1 6 Y-1 7 Y-1 8  Y-1 3 Y-1 4 Y-1 5 Y-1 6 Y-1 7 Y-1 8
Y-1 9 Y-20 Y-21 Y-22 Y-23  Y-1 9 Y-20 Y-21 Y-22 Y-23
Xb für Halogen, Nitro, Cyano, G-G -Alkyl, C3-C6-Cycloalkyl, G-G -Halogenalkyl. G-Gs- Alkoxy, C i -G - Halogenalkoxy, C3-C6-Halogencycloalkyl, G -G-Alkoxy-C -G -alkyl, G-G- Halogenaikoxy-G -G-alkyl, C s -G -Alkoxy-C ι -G,-al kyloxy, Cyano-C i -Cö-alkyl, G-CÖ- Cycloalkyl-G -G-alkyl, C2-C6-Alkenyl, G-G-Alkinyi, G-G-Aikylthio, G-G- Alkylcarbonyl, G-G-Cycloalkylcarbonyi, C2-C6-Alkenylcarbonyl, G-G-X b is halogen, nitro, cyano, GG-alkyl, C 3 -C 6 -cycloalkyl, GG-haloalkyl. G-Gs alkoxy, C i -G - haloalkoxy, C3-C6-halocycloalkyl, G -G alkoxy-C -G alkyl, GG- Halogenaikoxy-G -G alkyl, C s -G alkoxy -C ι -G, -alkyloxy, cyano-C i -Cö-alkyl, GC Ö - cycloalkyl-G-alkyl, C 2 -C 6 -alkenyl, GG-Alkinyi, GG-Aikylthio, GG-alkylcarbonyl, GG-Cycloalkylcarbonyi , C 2 -C 6 -alkenylcarbonyl, GG-
Halogenalkylcarbonyi, C 1 -G -Alkoxy carbonyl, G-G-Alkylsulfonyl, G-Ce- Halogenalkylsulfonyl, G-Ce-Alkylaminocarbonyl, Di-(G-G)-aikylaminocarbonyi, G-G- Alkylcarbonylamino, Aryl oder Hetaryi stehen, wobei Aryl und Hetaryl gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, G- G-Alkyl, C2-C6-Alkenyl, C2-G-Alkinyl, G -G-Alkoxy, G -C -Halogenalkyl. G-G- Halogenaikoxy oder G-G-Alkyithio substituiert sein können und wobei die Ring- -Atome in Y-13, Y-14 und Y-16 nicht durch Halogen, Nitro, Cyano, C i -C.i-Alkoxy, C1-C4- Halogenalkoxy oder C ; -C V Alkoxy-C s -C Valky loxy substituiert sind, m für 0, 1 oder 2 steht, p für 0, 1 oder 2 steht, Halogenalkylcarbonyi, C 1 -G alkoxy carbonyl, GG-alkylsulfonyl, G-Ce- haloalkylsulfonyl, G-Ce-alkylaminocarbonyl, di- (GG) -aikylaminocarbonyi, GG- alkylcarbonylamino, aryl or hetaryi, where aryl and hetaryl optionally mono- or simply repeatedly, identically or differently, by halogen, cyano, nitro, hydroxy, G-G-alkyl, C 2 -C 6 -alkenyl, C 2 -G -alkynyl, G -G-alkoxy, G -C -haloalkyl. GG Halogenoikoxy or GG Alkyithio may be substituted and wherein the ring atoms in Y-13, Y-14 and Y-16 not by halogen, nitro, cyano, Ci-Ci-alkoxy, C1-C4-haloalkoxy or C; -CV alkoxy-C s -C Valky loxy substituted, m is 0, 1 or 2, p is 0, 1 or 2,
R für Wasserstoff oder für Ci-Ce-Alkyl, CVCVAIkenyl, C-d-Alkinyl. C3-C6-Cycloalkyl oder (■,-( , -Heterocyclyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano, Cs-Ce-Cycloaikyl, CVCVAlkoxy, C1-C4- Halogenaikoxy, Ci-C4-Alkyithio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C1-C4- Alkylcarbonyl, C 1 -C4-Alkoxyimino-C 1 -C4-alkyl, C ; -CV AI koxyearbon l, C1-C4- Alkylsulfonyl, C i - .·, - H a I o e n a 1 k y 1 s 111 f n y I . C 1 -C4-Alkylaminocarbonyl, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, CVCVAlkyl, C ; -C V H al gena 1 ky 1. CVCVAlkoxy oder CVCVHaloalkoxy substituiert sein können, oder R is hydrogen or Ci-Ce-alkyl, CVCVAIkenyl, Cd-alkynyl. C 3 -C 6 -cycloalkyl or (■, -,, -, heterocyclyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, Cs-Ce-cycloalkyl, C 1 -C -alkoxy, C 1 -C 4 -haloalkoxy, C i -Alkyithio -C 4, C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxyimino-C 1 -C 4 alkyl, C; -CV koxyearbon AI l, C1- C 1 -C 4 -alkylaminocarbonyl, aryl or hetaryl, where aryl and hetaryl are in each case monosubstituted to trisubstituted by halogen, cyano, C 1 -C 4 -alkylsulfonyl, C 1 -. Nitro, CVCValkyl, C; -CVH al gena 1 ky 1. CVCVAlkoxy or CVCVHaloalkoxy may be substituted, or
R51 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, Ci-C4-Alkyi, (VC-Halogenalkyl. G-C4-Alkoxy, C1-C4- Halogcnalkoxy. Ci-C4-Aikylthio oder C 1 -C4-Alkylsulfonyl, R 51 is aryl or hetaryl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, nitro, cyano, C 1 -C 4 -alkyl, (C-C-haloalkyl, C -C 4 -alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl,
R52 für Cs -C.;-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, Cs-Ce-Cycloalkyl oder C3-C6-Heterocyciyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano , C C 4-Alkoxy. C i - 4 - H a 1 o e n a I k x y . Ci- C4-Alkylthio, Ci-C4-Alkylsuifinyi, Ci-C4-Alkylsulfonyl, Ci-C4-Aikylcarbonyl, C1 -C4- Alkoxyimino-Ci -C4-alkyl, C ι -C4-Alkoxycarbony 1, C 1 -C4-Alkylsulfonyl, C1-C4- Halogenalkylsulfonyl, Ci-C4-Alkylaminocarbonyl, Aryl oder Hetaryl substituiert sein können, wobei Aryl und Hetaryl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, C1-C4- Alkyl, C ! -CVHaiogenal kyl. C i -( 4-Alkoxy oder C i -C i-Haloalkoxy substituiert sein können, oder R 52 is C s -C; alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Cs-Ce cycloalkyl or C 3 -C 6 heterocyciyl, where the abovementioned radicals are, where appropriate, independently of one another simply by trisubstituted by halogen or simply by cyano, CC 4-alkoxy. C i - 4 - H a 1 oena I kxy. Ci- C 4 alkylthio, Ci-C 4 -Alkylsuifinyi, Ci-C 4 alkylsulfonyl, Ci-C 4 -Aikylcarbonyl, C 1 -C4- alkoxyimino-Ci-C4-alkyl, C ι -C 4 -Alkoxycarbony 1, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 -alkylaminocarbonyl, aryl or hetaryl may be substituted, wherein aryl and hetaryl in each case simply up to three times by halogen, cyano, nitro, C 1 -C 4 -alkyl, C ! -CVHaiogenic kyl. C i - (4-alkoxy or C i -C i -haloalkoxy may be substituted, or
R52 für Aryl oder Hetaryl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Nitro, Cyano, CVCVAlkyl, Ci-C4-Halogena!kyl, G-C4-Alkoxy, G-C4- Halogenalkoxy, C ι -Ci-Alkylthio oder G- VAlkylsulfonyl, R53 für Wasserstoff, VC-Alkyl, C i -C4-Alkoxy carbonyl, Ci-C6-Alkylcarbonyl, Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl steht, wobei Aryl, Hetaryl, Arylcarbonyl oder Hetarylcarbonyl jeweils einfach bis dreifach durch Halogen, Cyano, Nitro, C i -O-Alky!, O- CVHalogenalkyl, Ci-C4-Alkoxy oder C i -CVHaloalkoxy substituiert sein können, R54 für Wasserstoff oder für Ci -Ct-Alky], C:- '.t-Alkenyl, C2-C4-Alkinyl oder C s-O-Cyeloalkyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis fünffach durch Halogen oder einfach durch Cyano, G -CVAlkyl. C3-C4-Cycloalkyl, CVCVAlkoxy, C1 -C4- Haloalkoxy. G -CVAlkylthio, C 1 -C4-Alkylsulfinyl, C 1 -C4-Alkylsulfonyl oder Phenyl substituiert sein können, R 52 is aryl or hetaryl, where the abovementioned radicals optionally may be mono- to trisubstituted and the substituents are independently selected from halo, nitro, cyano, CVCVAlkyl, Ci-C 4 -Halogena! Kyl, GC 4 alkoxy, GC 4 - haloalkoxy, C 1 -C -alkylthio or G-VA-alkylsulfonyl, R 53 represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, aryl, hetaryl, arylcarbonyl or hetarylcarbonyl, where aryl, hetaryl, arylcarbonyl or hetarylcarbonyl are in each case monosubstituted to trisubstituted by halogen, cyano , Nitro, C i -O-alkyl, O-CV haloalkyl, Ci-C4-alkoxy or C i -CVHaloalkoxy may be substituted, R 54 is hydrogen or Ci-Ct-Alky], C: - ' .t-alkenyl , C 2 -C 4 -alkynyl or C 5 -o-cyeloalkyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to five times by halogen or simply by cyano, C 1 -C 4 -alkyl. C 3 -C 4 cycloalkyl, C 2 -C 4 alkoxy, C 1 -C 4 haloalkoxy. C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or phenyl may be substituted,
R" für Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycioalkyi-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4- alkyl, Aryl -G -CValkyl oder H et ary 1 -C ; - .; -a 1 ky 1 steht, wobei Ar l-G -CValkyl und Hetaryl- ( j - .t-alkyl gegebenenfalls einfach bis dreifach, gleich oder unterschiedlich durch Halogen, Cyano, Nitro, G -Ct-Alkyl, G-G-Halogenalkyl. G -G-Alkoxy oder ( 1 -G-Halogena!koxy substituiert sein können, R "is C 4 alkyl, Ci-C4-haloalkyl, C3-C6-Cycioalkyi-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 4 - alkyl, aryl or -G -CValkyl H et ary 1 -C; -;; -a 1 ky 1, wherein Ar lG -CValkyl and hetaryl- (j - .t-alkyl optionally mono- to trisubstituted by identical or different halogen, cyano, nitro, G -Ct Alkyl, GG-haloalkyl, G-G-alkoxy or (1-G-haloalkoxy) may be substituted,
R7 für Wasserstoff, Ci-C4-Aikyl, C2-C4-Aikenyi, C2-C4-Aikinyl, C3-C6-Cycloalkyl, G-C4- Alkoxy, Ci-C4-Alkoxy-Ci-C4-Aikyl, C i -C - A I k x y c arbon y I oder Ci-C4-Alkyicarbonyl steht, R 7 is hydrogen, Ci-C 4 -alkyl, C 2 -C 4 -Aikenyi, C 2 -C 4 -Aikinyl, C 3 -C 6 cycloalkyl, GC 4 - alkoxy, Ci-C4-alkoxy-Ci-C4 -Aikyl, C i -C - Al kxyc arbon y I or Ci-C4-Alkyicarbonyl,
R7a für Wasserstoff, C i - VAlkyl, Ci-C4-Alkoxy carbonyl oder Ci-C4-Alkylcarbonyl steht, R 7a is hydrogen, C 1 -alkyl, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylcarbonyl,
R8 für Wasserstoff oder für Cj -C' -t-Alkyl, C^- -t-Alkeny! oder C;-C4-Alkiny! steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen, oder einfach durch Cyano, C VCVAIkoxy, C ; -C i-Haloalkoxy. C V -i-Alkylthio, Ci-C4-Alkylsulfmyl, C1 -C4- Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, oder Ci-C4-Alkylcarbonyi substituiert sein können, oder R8 für Phenylmethyl, Phenyiethyi, Pyridylmethyl, C3-C6-Cycloalkyl, C' ;-t ycloalkyl-C i -C^- alkyl oder ( V VBicycloalkvl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, -AlkvI, Ci- C4-Alkoxy, C i-Ci-Haloalkoxy. Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci-C4-Alkylsulfonyl, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl, oder R8 für Phenyl, Pyridyl, Pyrimidinyl, Thiazolyl, Thiadiazolyl Oxazolyl, Pyrazolyl, Thienyl oder Furanyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, G -Ci-Alkyl, C2-C4-Alkinyl, Ci-C4-Halogenaikyl, G-C4-Alkoxy, G-C4-Haloaikoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl oder Ci-C4-Alkylsulfonyl, C2-C6-Alkoxycarbonyi oder G-G-Alkylcarbonyl, oder R 8 is hydrogen or Cj -C ' t -alkyl, C ^ - t-alkeny! or C; -C 4 -alkyn! whereupon the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, or simply by cyano, C 1 -C 4 -alkoxy, C; -C 1 haloalkoxy. C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxycarbonyl, or C 1 -C 4 -alkylcarbonyi, or R 8 for phenylmethyl, phenylethyl, pyridylmethyl, C 3 -C 6 - Cycloalkyl, C ' ; -t ycloalkyl-C i -C ^ - alkyl or (V VBicycloalkvl, where the aforementioned radicals may optionally be mono- to trisubstituted by identical or different substituents and the substituents are independently selected from halogen, cyano, nitro, hydroxy, amino, -AlkvI, Ci- C 4 alkoxy, C i-C haloalkoxy. Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, Ci-C 4 alkylsulfonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C6- Alkylcarbonyl, or R 8 represents phenyl, pyridyl, pyrimidinyl, thiazolyl, thiadiazolyl, oxazolyl, pyrazolyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted, identically or differently, and the substituents are selected independently of one another from halogen, cyano, nitro, hydroxy, amino, -C G alkyl, C2-C4-alkynyl, Ci-C 4 -Halogenaikyl, GC 4 alkoxy, GC 4 -Haloaikoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl or C 4- alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl or GG-alkylcarbonyl, or
R7 und R8 zusammen für eine C .- VAlkylkette stehen, R9 für Wasserstoff, Fluor, Chlor oder Ci-C4-Alkyi steht, R9a für Wasserstoff, Fluor, Chlor oder Ci-C4-Alkyl, steht, R10 für Wasserstoff, Fluor, Chlor oder G-G-Alkyl steht, und R 7 and R 8 together represent a C 1 -C 4 -alkyl chain, R 9 is hydrogen, fluorine, chlorine or C 1 -C 4 -alkyl, R 9a is hydrogen, fluorine, chlorine or C 1 -C 4 -alkyl, R 2 10 is hydrogen, fluorine, chlorine or GG-alkyl, and
R10a für Wasserstoff, Fluor, Chlor oder Ci-C4-Aikyl steht. Verbindung nach Anspruch 1 oder 2, worin R 10a is hydrogen, fluorine, chlorine or C 1 -C 4 -acyl. A compound according to claim 1 or 2, wherein
Q1 und Q2 zusammen für einen der Reste A-l , A-4 oder A-5 stehen, die zusammen mit dem C- und N-Atom an das sie gebunden sind, einen 5- oder 6-giiedrigen aromatischen Ring bilden, Q 1 and Q 2 together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR* . -N(R7)(R8) oder -N(R7a)-N(R7)(R8) steht, T for R \ -OR * . -N (R 7 ) (R 8 ) or -N (R 7a ) -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für eine Bindung oder für -C(R9)(R10)- steht, G is a bond or -C (R 9 ) (R 10 ) -,
U für einen Cyclus der Reihe U-2, U-9, U- 10 oder U-2 steht, U is a cycle of the series U-2, U-9, U-10 or U-2,
Xa für Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl steht, n für 0, I oder 2 steht, X a is halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, n is 0, I or 2,
R1, R\ R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff, Halogen, Cyano, G-C4-Alkyi, Ci-C4-Halogenalkyl, G-C4-Alkoxy, G-C4-Halogena!koxy, G- C4-Alkoxy-G~C4-aikyi, C -G-Alkenyl, C2-C4-Alkenyloxy, G-G-Alkinyl, C3-C4-Alkinyloxy, G-C4-Alkylthio, G-C4-Alkylsulfmyl oder G-C4-Aikylsulfonyl stehen, R5 für CH - Y ste t R 1, R \ R 3, R 4 each, independently of one another represent a radical from the series hydrogen, halogen, cyano, GC 4 -Alkyi, Ci-C 4 haloalkyl, GC 4 alkoxy, GC koxy 4 -Halogena!, G C 4 alkoxy G C 4 alkyl, C 1 -G alkenyl, C 2 -C 4 alkenyloxy, GG alkynyl, C 3 -C 4 alkynyloxy, GC 4 alkylthio, GC 4 alkylsulfmyl or GC 4- alkylsulfonyl, R 5 is CH - Y
Y für Wasserstoff, Cl, Br, -O-R51, -S(0)P-R52, -N(R53)(R54) oder für einen der Reste Y-2, Y-3, Y-4. Y-5, Y-6 oder Y-7 steht, Y is hydrogen, Cl, Br, -OR 51 , -S (O) P -R 52 , -N (R 53 ) (R 54 ) or one of the radicals Y-2, Y-3, Y-4. Y-5, Y-6 or Y-7,
Xb für Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Methylamino carbonyl, Methyl carbonylamino , Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Ethylthio, Methylsulfinyl, Methylsulfonyl oder Methoxycarbonyl steht, m für 0, 1 oder 2 steht, p für 0, 1 oder 2 steht, X b is halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methylamino carbonyl, methyl carbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl, m is 0, 1 or 2, p is 0 , 1 or 2,
R51 für Wasserstoff oder für Cj -G -Alkyl, C2-C4-Aikenyl, C2-C4-Alkinyl oder G-Ce-Cycloaikyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen oder einfach durch Cyano, C3-C6-Cycloalkyl, G -Ct-Alkoxy, C d-Halogenalkoxy, Ci-C4-Alkylthio, G-C4- Alkylsulfmyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxy carbonyl oder G-Gj- Alkylsulfonyl substituiert sein können, oder einfach durch Phenyl, Thienyl, Pyridyl, Pyrimidinyl oder Pyrazolyl substituiert sein können, die wiederum jeweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder R 51 represents hydrogen or C j -G alkyl, C 2 -C 4 acyl, C 2 -C 4 alkynyl or G-Ce-cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, C 3 -C 6 -cycloalkyl, G -Ct-alkoxy, C d -haloalkoxy, C 1 -C 4 -alkylthio, GC 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy carbonyl or G May be substituted by phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, which in turn may each independently be monosubstituted to trisubstituted by halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy can, or
R51 für Phenyl, Thienyl, Pyridyl, Pyrimidinyl oder Pyrazolyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, R 51 is phenyl, thienyl, pyridyl, pyrimidinyl or pyrazolyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
R52 für Ci-C4-Aikyl oder C3-C6-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano , C1-C4- Alkoxy, Ci-C4-Halogenalkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, G-C4-Aikylsulfonyl, G-C4-Aikylearbonyl, G-Gt-Alkoxy carbonyl oder G-C4-Alkylsulfonyl sowie aus Phenyl, Thienyl, Pyridyl, Pyrimidinyl, Pyrazolyl, die jeweils unabhängig voneinander einfach bis dreifach durch Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy substituiert sein können, oder R52 für Phenyl, Thienyl, Pyridyl, Pyrimidinyl oder Pyra/olyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Trifluormethoxy, R 52 is C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl, where the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from halogen, cyano, C 1 -C 4 -alkoxy, C 4 haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, GC 4 -alkylsulfonyl, GC 4 -alkylcarbonyl, G-Gt-alkoxycarbonyl or C 1 -C 4 -alkylsulfonyl and also phenyl, thienyl, pyridyl, pyrimidinyl, Pyrazolyl, each of which may be substituted, independently of one another, monosubstituted to trisubstituted by halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy, or R 52 is phenyl, thienyl, pyridyl, pyrimidinyl or pyra / olyl, wherein the abovementioned radicals may optionally be monosubstituted to trisubstituted and the substituents are independently selected from halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy .
R53 für Wasserstoff, G-C4-Alkyl, G-C4-Aikoxycarbonyl oder Ci-Cö-Alkylcarbonyl steht, R 53 is hydrogen, GC 4 -alkyl, GC 4 -alkoxycarbonyl or Ci-Cö-alkylcarbonyl,
R54 für Wasserstoff oder für Ci-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl oder C3-C4-Cycloalkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach durch Halogen, oder einfach durch Cyano, Methyl, Ethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Phenyl substituiert sein können, R 54 is hydrogen or C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 -cycloalkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen, or may be readily substituted by cyano, methyl, ethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or phenyl,
R" für G-C4-Aiky!, Ci-C4-Halogenalkyi, C3-C6-Cycloalk> -Ci-C4-alkyl, Ci-C4-Aikoxy-G-C4- alkyl steht, R "for GC 4 -Aiky !, Ci-C 4 -Halogenalkyi, C 3 -C 6 -cycloalk> -C-C 4 alkyl, Ci-C 4 -alkoxy-GC 4 - alkyl,
R ' für Wasserstoff, Ci-C4-Alkyi, G-C4-Aikoxy, Ci-C4-Aikoxy-Ci-C4-Alkyi, Ci-C4-Alkoxycar- bonyl oder C i -C4-Alkylcarbonyl steht, R 'is hydrogen, Ci-C 4 -Alkyi, GC 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -Alkyi, Ci-C 4 carbonyl -Alkoxycar- or C i -C 4 alkylcarbonyl,
R7a für Wasserstoff, Ci-C4-Alkyl, C i -C4-Alkoxy carbonyl oder Ci-C4-Alkylcarbonyl steht, R 7a 4 alkyl, C i -C 4 alkoxy carbonyl, or Ci-C 4 alkylcarbonyl is hydrogen, Ci-C,
R8 für Wasserstoff oder für G-C4-Alkyl, CyCi-Alkenyl oder CVCVAIkinyl steht, wobei die vorgenannten Reste gegebenenfalls unabhängig voneinander einfach bis dreifach durch Halogen oder einfach durch Cyano, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy, Trifluorethoxy, Methylthio, Ethylthio, Methylsulfmyl, Ethylsulfmyl, Methylsulfonyl oder Ethylsulfonyl substituiert sein können, oder R 8 is hydrogen or GC 4 alkyl, CyCi alkenyl or CVCVAIkinyl, wherein the aforementioned radicals optionally independently of one another by halogen or simply by cyano, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, methylsulfmyl , Ethylsulfmyl, methylsulfonyl or ethylsulfonyl, or
R8 für Phenylmethyl, Phenyiethyl, Pyridylmethyl, Pyridylethyl, C3-C6-Cycloalkyl oder C3-C6- Cycloalkyl-Ci -C4-alkyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl, oder R 8 is phenylmethyl, Phenyiethyl, pyridylmethyl, pyridylethyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 - alkyl is cycloalkyl-Ci-C4, where the aforementioned radicals optionally may be mono- to trisubstituted and the substituents are independently are selected from among halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, or
R8 für Phenyl, Pyridyl, Pyrimidinyl, Thia/olyl, Thiadiazolyl, Oxazoiyl, Pyra/olyl, Thienyl oder Furanyl steht, wobei die vorgenannten Reste gegebenenfalls einfach bis dreifach gleich oder verschieden substituiert sein können und die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Methyl, Ethyl, Ethinyl, Trifluormethyl, Pentafluorethyl, Methoxy, Ethoxy, Trifluormethoxy, Methylthio, Methylsulfmyl, Methylsulfonyl oder Methoxycarbonyl, oder R 8 is phenyl, pyridyl, pyrimidinyl, thia / olyl, thiadiazolyl, oxazoiyl, pyra / olyl, thienyl or furanyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents independently of one another are selected from halogen, cyano, nitro, methyl, ethyl, ethynyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl, methylsulfonyl or methoxycarbonyl, or
R und R8 zusammen für eine Cs-Ce-Alkylkette stehen, R9 für Wasserstoff, Fluor, Chlor, Methyl oder Ethyl steht, und R and R 8 together represent a Cs-Ce-alkyl chain, R 9 is hydrogen, fluorine, chlorine, methyl or ethyl, and
R!0 für Wasserstoff, Fluor, Chlor Methyl oder Ethyl steht. Verbindung nach einem der Ansprüche 1 bis 3, worin R ! 0 is hydrogen, fluorine, chlorine, methyl or ethyl. A compound according to any one of claims 1 to 3, wherein
Q1 und Q2 zusammen für einen der Reste A-l, A-4 oder A-5 stehen, die zusammen mit dem C- und N-Atom an das sie gebunden sind, einen 5- oder 6-gliedrigen aromatischen Ring bilden, Q 1 and Q 2 together represent one of the radicals Al, A-4 or A-5 which, together with the C and N atoms to which they are attached, form a 5- or 6-membered aromatic ring,
T für R\ -OR" oder -N(R7)(R8) steht, T is R 1 -OR "or -N (R 7 ) (R 8 ),
W für O steht, W stands for O,
G für eine Bindung oder für -C(R9)(R!0)- steht, G is a bond or -C (R 9 ) (R ! 0 ) -,
U für U-2. U-9, U- 10 oder U-23 steht, U for U-2. U-9, U-10 or U-23,
Xa für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Trifluormethoxy oder Cyano steht, n für 0,1 oder 2 steht, X a is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy or cyano, n is 0.1 or 2,
R\ R -, R3, R4 jeweils unabhängig voneinander für einen Rest aus der Reihe Wasserstoff,R 1, R 3 , R 4 independently of one another are each a radical from the series of hydrogen,
Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, n- oder iso-Propyi, Methoxy, Ethoxy, n- oder iso-Propoxy, Methylthio, Ethylthio, Difluormethyl, Trifluormethyl, Trifluormethoxy oder Difluormethoxy stehen, Fluoro, chloro, bromo, iodo, cyano, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy,
R5 für CH2Y steht, R 5 is CH 2 Y,
Y für Wasserstoff, Chlor. 0-R\ -S(0)p-R52, -N(R53)(R ) oder für einen der Reste Y-2, Y-3, Y4, Y-5, Y-6 oder Y-7 steht, für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- und iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethyl, Trifiuormethyl, Methylaminocarbonyl oder Methyl carbonylamino steht, für 0 oderl steht, für 0,1 oder2 steht, für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pent-3-yl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, 2,2,2-Trifluorethyl, 2-Methoxyethyl, Methoxycarbonylmethyl, Phenyl, 2-Fiuor-Phenyl, 3-Fluor-Phenyl, 4-Fluor-Phenyl, 2-Chlor- Phenyl, 3-Chlor-Phenyl, 4-C hlor-Phenyl. Phenylmethyl, 4-Fluor-Phenylmethyl, 3-Fluor- Phenylmethyl, 2-Fluor-Phenylmethyl, Pyrid-3-yl, 6 - h I o - Py r i ii -3 -y 1 , Pyridyl-2-yl oder 1 - Methylpyrazol-5-yl steht, für Methyl, Ethyl, n- oder iso-Propyl, Phenyl oder Phenylmethyl steht, für Wasserstoff, Methyl, Ethyl. Methylcarbonyl oder Ethylcarbonyl steht, für Methyl, Ethyl, n- oder iso-Propyl, Cyclopropyl oder Phenylmethyl steht, für Methyl, Ethyl oder n- oder iso-Propyl steht, für Wasserstoff, Methyl oder Ethyl steht, für Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Trifluorethyl, Cyclopropyl, Fluorcyclopropyl, Chlorcyclopropyl, Cyanocyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanocyclohexyl, Cyclopropylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Methyl, Ethyl, Methoxy, Ethoxy, Trifiuormethyl, Pentafluorethyl, Trifluormethoxy, Cyano oder Nitro substituiertes Phenyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder hl r substituiertes Phenylmethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 1 -Phenvlethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 2- Phenylethyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor oder Methyl substituiertes Pyrid-3-νϊ, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Trifiuormethyl, Cyano, Nitro oder Ethinyl substituiertes Pyridyl-2-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fkior.Chlor oder Methoxy substituiertes Pyrid-4-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chlor substituiertes 1 ,3 -Pyrimidin-2-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor oder Chl r substituiertes l ,Y for hydrogen, chlorine. 0-R \ -S (0) p -R 52, -N (R 53) (R) or one of the radicals Y 2, Y 3, Y 4, Y 5, Y 6 or Y 7 represents . represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethyl, trifluoromethyl, methylaminocarbonyl or methylcarbonylamino, represents 0 or 1, represents 0.1 or 2, for hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pent-3-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2 , 2,2-trifluoroethyl, 2-methoxyethyl, methoxycarbonylmethyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl phenyl. Phenylmethyl, 4-fluoro-phenylmethyl, 3-fluoro-phenylmethyl, 2-fluoro-phenylmethyl, pyrid-3-yl, 6-h, o-pyric-3-yl, pyridyl-2-yl or 1-methylpyrazole -5-yl, is methyl, ethyl, n- or iso-propyl, phenyl or phenylmethyl, hydrogen, methyl, ethyl. Is methylcarbonyl or ethylcarbonyl, is methyl, ethyl, n- or isopropyl, cyclopropyl or phenylmethyl, is methyl, ethyl or n- or isopropyl, stands for hydrogen, methyl or ethyl, for methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, trifluoroethyl, cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, cyanocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyano-cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, optionally mono- or di-independent of each other by fluorine , Chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, cyano or nitro-substituted phenyl, optionally mono- to disubstituted independently of one another by fluorine or h r substituted phenylmethyl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 1 - Phenvlethyl, optionally mono- to disubstituted independently of one another by fluorine or chlorine 2-phenylethyl, optionally mono- to disubstituted independently of one another by fluorine, chlorine or methyl-substituted pyrid-3-νϊ, optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, trifluoromethyl, cyano, nitro or ethynyl-substituted pyridyl-2 yl, optionally mono- to disubstituted independently of one another by Fkior.Chlor or methoxy-substituted pyrid-4-yl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted 1, 3 -pyrimidin-2-yl, optionally mono- to disubstituted independently of one another by fluorine or chlorine-substituted L,
3-Pyrimidin-5-yl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor oder Methyl substituiertes Thia/o!-2-yl. 1 .2.3-pyrimidin-5-yl, optionally mono- to disubstituted independently of one another by fluorine, chlorine or methyl-substituted thia / o! -2-yl. 1 .2.
4 -T i ad i a/o 1 - - y I oder für gegebenenfalls durch Chlor. Brom oder Methyl substituiertes l -Methyl-Pyrazo!-5-yi steht, 4 -T i ad i a / o 1 - - y I or optionally chlorine. Bromine- or methyl-substituted 1-methyl-pyrazole! -5-yl,
R ' für Wasserstoff oder Methyl steht, und R 'is hydrogen or methyl, and
Ri0 für Wasserstoff steht. R i0 is hydrogen.
5. Verbindung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie eine Struktur gemäß Formel (1-1) aufweist 5. A compound according to any one of claims 1 to 4, characterized in that it has a structure according to formula (1-1)
in der G, U, T, R 1, R2, R3 und R4 die in Anspruch 1 definierten Bedeutungen oder die in Anspruch 2 definierten Bedeutungen oder die in Anspruch 3 definierten Bedeutungen oder die in Anspruch 4 definierten Bedeutungen haben. in which G, U, T, R 1 , R 2 , R 3 and R 4 have the meanings defined in claim 1 or the meanings defined in claim 2 or the meanings defined in claim 3 or the meanings defined in claim 4.
6. Verbindung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie eine Struktur gemäß Formel (1-4) aufweist 6. A compound according to any one of claims 1 to 4, characterized in that it has a structure according to formula (1-4)
in der G, U, T, R1, R2 und R ' die in Anspruch 1 definierten Bedeutungen oder die in Anspruch 2 definierten Bedeutungen oder die in Anspruch 3 definierten Bedeutungen oder die in Anspruch 4 definierten Bedeutungen haben. in which G, U, T, R 1 , R 2 and R 'have the meanings defined in claim 1 or the meanings defined in claim 2 or the meanings defined in claim 3 or the meanings defined in claim 4.
7. Verbindung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass sie eine Struktur gemäß Formel (1-5) aufweist 7. A compound according to any one of claims 1 to 4, characterized in that it has a structure according to formula (1-5)
in der G, U, T, R1 und R: die in Anspruch 1 definierten Bedeutungen oder die in Anspruch 2 definierten Bedeutungen oder die in Anspruch 3 definierten Bedeutungen oder die in Anspruch 4 definierten Bedeutungen haben. have the meanings defined in claim 1 or as defined in claim 2 or as defined in claim 3 or as defined in claim 4: wherein G, U, T, R 1 and R.
8 Formulierung, insbesondere agrochemische Formulierung, umfassend mindestens eine Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 7. A formulation, in particular an agrochemical formulation, comprising at least one compound of the formula (I) according to one of claims 1 to 7.
9. Formulierung nach Anspruch 8 ferner umfassend mindestens ein Streckmittel und/oder mindestens eine oberflächenaktive Substanz. 10. Formulierung nach Anspruch 8 oder 9, dadurch gekennzeichnet, dass die Verbindung der9. Formulation according to claim 8 further comprising at least one extender and / or at least one surface-active substance. 10. A formulation according to claim 8 or 9, characterized in that the compound of
Formel (I) in Mischung mit mindestens einem weiteren Wirkstoff vorliegt. Formula (I) is present in admixture with at least one further active ingredient.
Verfahren zur Bekämpfung von Schädlingen, insbesondere tierischen Schädlingen, dadurch gekennzeichnet, dass man eine Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 7 oder eine Formulierung gemäß einem der Ansprüche 8 bis 10 auf die Schädlinge und/oder ihren Lebensraum einwirken lässt. Method for controlling pests, in particular animal pests, characterized in that a compound of the formula (I) according to one of Claims 1 to 7 or a formulation according to one of Claims 8 to 10 is allowed to act on the pests and / or their habitat.
Verfahren nach Anspruch 11 , dadurch gekennzeichnet, dass der Schädling ein tierischer Schädling ist und ein Insekt, ein Spinnentier oder einen Nematoden umfasst, oder dass der Schädling ein Insekt, ein Spinnentier oder ein Nematode ist. A method according to claim 11, characterized in that the pest is an animal pest and comprises an insect, arachnid or a nematode, or that the pest is an insect, arachnid or a nematode.
Verwendung einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 7 oder einer Formulierung gemäß einem der Ansprüche 8 bis 10 zur Bekämpfung von tierischen Schädlingen. Use of a compound of the formula (I) according to any one of claims 1 to 7 or of a formulation according to any one of claims 8 to 10 for controlling animal pests.
Verwendung nach Anspruch 13, dadurch gekennzeichnet, dass der tierische Schädling ein Insekt, ein Spinnentier oder einen Nematoden umfasst, oder dass der tierische Schädling ein Insekt, ein Spinnentier oder ein Nematode ist. Use according to claim 13, characterized in that the animal pest comprises an insect, arachnid or a nematode, or that the animal pest is an insect, arachnid or a nematode.
Verwendung nach Anspruch 13 oder 14 im Pflanzenschutz. Use according to claim 13 or 14 in crop protection.
Verwendung nach Anspruch 13 oder 14 auf dem Gebiet der Tiergesundheit. Use according to claim 13 or 14 in the field of animal health.
Verfahren zum Schutz eines Saatgutes oder einer keimenden Pflanze vor Schädlingen, insbesondere tierischen Schädlingen, umfassend einen Verfahrensschritt, in welchem das Saatgut in Kontakt mit einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 7 oder mit einer Formulierung gemäß einem der Ansprüche 8 bis 10 gebracht wird. Method for protecting a seed or a germinating plant from pests, in particular animal pests, comprising a method step in which the Seed is brought into contact with a compound of formula (I) according to any one of claims 1 to 7 or with a formulation according to any one of claims 8 to 10.
18. Saatgut, erhalten durch ein Verfahren gemäß Anspruch 17.  18. Seed obtained by a method according to claim 17.
EP16801802.6A 2015-12-03 2016-11-29 Mesoionic halogenated 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olate derivatives and related compounds as insecticides Withdrawn EP3383874A1 (en)

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