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WO2015107133A1 - Quinoline derivatives as insecticides and acaricides - Google Patents

Quinoline derivatives as insecticides and acaricides Download PDF

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Publication number
WO2015107133A1
WO2015107133A1 PCT/EP2015/050732 EP2015050732W WO2015107133A1 WO 2015107133 A1 WO2015107133 A1 WO 2015107133A1 EP 2015050732 W EP2015050732 W EP 2015050732W WO 2015107133 A1 WO2015107133 A1 WO 2015107133A1
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WIPO (PCT)
Prior art keywords
spp
alkyl
stands
cyano
methyl
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PCT/EP2015/050732
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German (de)
French (fr)
Inventor
Markus Heil
Michael Maue
Eike Kevin Heilmann
Peter Jeschke
Ulrich Görgens
Kerstin Ilg
Arnd Voerste
Andreas Turberg
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Bayer Cropscience Ag
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Publication of WO2015107133A1 publication Critical patent/WO2015107133A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention relates to novel Quinolinderivate, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes.
  • Insecticidal indole or benzimidazolecarboxamides are already known, see WO-A-2011/054436 or WO-A-2012/119984.
  • certain novel quinoline derivatives e.g. Quiolin-2-carboxamides, strong insecticides and acaricidal properties with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility possess.
  • the novel compounds of the invention have not been disclosed.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity. It has now surprisingly been found that certain new quinoline derivatives and their N-oxides and salts have strong insecticidal and acaricidal properties with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility. The novel compounds of the invention have not been disclosed.
  • the present invention is therefore compounds of the general formula (I)
  • R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen-substituted Ci-Ce-alkyl, C 3 -C 6 -cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci -C 6 - alkylsulfonyl, Ci-Cö-alkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl or Ci-Cö-alkylsulfonyloxy, or
  • R 1 is an optionally 1 or 2 heteroatoms containing Ci-C i carbon chain which is bonded to two adjacent ring positions and forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring, which may be mono- or polysubstituted by Ci-Cö-alkyl or Halogen is then substituted, wherein n is then 1 and wherein the heteroatoms are selected from the group consisting of N, S and O, n is 1,2, 3, 4 or 5,
  • R 2 is hydrogen, halogen, cyano, hydroxyl or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy, where the substituents are independent are selected from fluorine, chlorine, bromine or iodine
  • R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C i-alkylcarbonyl or Ci-C i-alkoxycarbonyl, wherein the substituents independently of one another are selected from cyano, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
  • Q 1 is CR 4 or N
  • Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
  • R 4 is hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
  • R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, CI-C east - Alkoxy, (C 1 -C 6 -alkoxy) carbonyl, C 1 -C 6 -alkylamino, formyl, (C 1 -C 6 -alkyl) carbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -dialkylamino, (C 1 -C 6 alkylamino) carbonyl, (CI-COE dialkylamino) carbonyl, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl,
  • X is Ci-C6-haloalkyl, which may optionally additionally be monosubstituted to trisubstituted, where the substituents are independently selected from hydroxy, cyano or Ci-C i-alkoxy,
  • W stands for O or S
  • G stands for a free electron pair or for oxygen
  • R 13 , R 16 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl i-alkylcarbonyl, Ci-C i-alkoxycarbonyl or C2-C 4 alkenyl stand,
  • R 14 , R 15 independently of one another represent hydrogen or C 1 -C 4 -alkyl or R 14 , R 15 together form a 3-6-membered aliphatic ring,
  • Y is hydrogen or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 1 -C 12 -cycloalkenyl wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C 4 -Alkylaminothiocarbonyl, Ci-C 4 -Halogenalkylaminocarbonyl, di- (Ci-C 4 alkyl) aminocarbonyl, di- (Ci-C 4 alkyl) - aminothiocarbonyl, hydroxycarbonyl, Ci-C 4 alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci- C6
  • the respective number of substituents n in the formula (I) includes only the substituents which are different from hydrogen. For this reason, hydrogen is not included in the definition of R 1 either. Of course, the substituent is always hydrogen, if no substituent R 1 is present at the respective site.
  • the compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
  • the substituted quinolinecarboxylic acid amides are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below.
  • Preferred (embodiment 2-1) are the compounds of formula (I) in which
  • R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl or C 1 -C 4 - Alkylsulfonyl or Ci-C 4 alkylsulfonyloxy, n is 1, 2, 3, 4 or 5 stands
  • R 2 is hydrogen or optionally monosubstituted to trisubstituted Ci-Cö-alkyl, wherein the substituents are independently selected from fluorine, chlorine, bromine or iodine
  • R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C4-alkylcarbonyl or Ci-C4-alkoxycarbonyl, wherein the Substituents are independently selected from cyano, halogen or Ci- C4-alkoxy
  • Q 1 is CR 4 or N
  • Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
  • R 4 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
  • R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl , C 1 -C 4 alkoxy, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 4 alkyl) carbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, or C 1 -C 4 alkylsulfonyl, where the substituents are independent are selected from among halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
  • X is Ci-C4-haloalkyl
  • W is O
  • G is a lone pair of electrons or oxygen
  • R 13 is hydrogen, C 1 -C 4 -alkyl, cyanomethyl, C 1 -C 4 -alkoxymethyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or C 2 -C 4 -alkenyl stands, Y is hydrogen or or optionally mono- or polysubstituted by identical or different substituents Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl or C 3 -C 6 -cycloalkenyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C i-alkyl, Ci-C i-haloalkyl, C3-Cs-cycloalkyl, CI-C
  • Y is an optionally mono- or polysubstituted by identical or different substituent, phenyl, or an optionally monosubstituted or polysubstituted heterocycle selected from the group consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, 1,2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl,
  • Particularly preferred (embodiment 3-1) are the compounds of formula (I) in which R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by fluorine or chlorine-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkyl, C 4 -alkylsulfonyl or C 1 -C 4 -alkylsulfonyloxy, n is 1, 2, 3, 4 or 5, R 2 is hydrogen,
  • R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
  • Q 2 is CR 4
  • Q 3 is CR 4
  • R 4 is hydrogen, fluorine or chlorine
  • R 6 represents hydrogen, halogen, nitro, cyano, or represents optionally monosubstituted to trisubstituted by halogen C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, X represents trifluoromethyl, difluoromethyl or pentafluoroethyl,
  • G stands for a lone pair of electrons
  • R 13 is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl, optionally substituted once to three times, identically or differently substituted Ci-Cö Alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, or C 1 -C 6 -cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkyl Ci-C i-haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C 2 -C 4 - Alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alky
  • Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
  • R 2 is hydrogen
  • R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
  • Q is CR
  • Q is CR
  • X is trifluoromethyl, difluoromethyl or pentafluoroethyl
  • W is O
  • G stands for a free electron pair or for oxygen
  • R is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl
  • Y is optionally mono- to trisubstituted by identical or different substituents Ci-Cö Alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or Cs-Ce-cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-AlkyL-Ci-C4 haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkyl
  • Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
  • Very particularly preferred are the compounds of the formula (I) in which R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy or trifluoromethylsulfonyloxy, n is 1, 2 , 3, 4 or 5 stands
  • R is hydrogen, is hydrogen, CR 4 , CR 4 , CR 4 , CR 4 , hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl, trifluoromethyl
  • O stands for a lone pair of electrons
  • NR 13 - stands, wherein the former (left) attachment site on the ring and the second-mentioned (right) attachment site to Y, and wherein hydrogen or methyl is methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2-yl, 1-butyne 3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanomethyl, 2-cyanoprop-1-y
  • R 2 is hydrogen
  • R 3 is hydrogen, Q 1 is CR 4 ,
  • R 4 is hydrogen
  • R 6 is fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl
  • X is trifluoromethyl
  • G stands for a free electron pair or for oxygen
  • R 13 is hydrogen or methyl, methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2 yl, l-butyn-3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3 Cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyano-cyclopropyl, 2-cyanoprop-2-ene
  • R 1 , R 3 , R 4 ie R 4a and R 4b independently of one another have the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-1) describes a preferred embodiment of the erfindungeswashen compounds of formula (I).
  • R 2 is H
  • W is O
  • Q 1 and Q 2 are CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • A is - CO-NR 13 -.
  • G stands for a free Elektonenpar.
  • the invention relates to the compounds of the formula (I-2)
  • R 1 , R 3 , R 4 ie R 4a has the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those in embodiment (1 -1) or embodiment ( 2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-2) describes a preferred embodiment of the inventive compounds of the formula (I).
  • R 2 is H
  • W is O
  • Q 1 and Q 2 is CH
  • Q 3 is CR 4a
  • Q 4 is N
  • A is -CO- NR 13 -.
  • G stands for a free Elektonenpar.
  • the invention relates to the compounds of the formula (I-3)
  • R 1 , R 3 , R 4 ie R 4a and R 4b independently of one another have the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-3) describes a preferred embodiment of the inventive compounds of the formula (I).
  • R 2 is H
  • W is O
  • Q 1 is N
  • Q 2 is CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • G stands for a free Elektonenpar.
  • G is a lone electron pair and Q 1 , Q 2 , Q 3 and Q 4 are CR 4 , where all other groups, radicals and substituents are above in embodiment (1 -1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-2) have described meanings.
  • G is a free electron pair and R 2 is hydrogen and X is trifluoromethyl, where all other groups, radicals and substituents are those described above in the embodiment (1). 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • W is O
  • G is a lone electron pair
  • Q 1 , Q 2 , Q 3 and Q 4 are CR 4
  • A is -CO-NR 13 -, where all other groups, radicals and substituents are as defined above in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-5). 2) have described meanings.
  • preferred compounds according to the invention are the compounds of the general formula (I) or (1-1) shown in Table 1.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • the compounds of the formula (I) may also be present as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers in different compositions. Both the pure Stereoisomers as well as 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.
  • 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.
  • the present compounds of the general formula (I) may optionally have a chiral carbon atom.
  • these substituents may have both an (R) and an (S) configuration.
  • the present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
  • 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 12 -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 -heptyl, n-octyl, n-nonyl, n
  • alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having 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-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, preferred are C2-C6-alkenyl radicals and particularly preferred are C2-C4-alkenyl radicals.
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkynyl having at least one triple bond, for example, ethynyl, 1-propynyl C 3 -C 6 -alkynyl radicals are preferred and C 3 -C 4 -alkynyl radicals are particularly preferred.
  • the alkynyl radical may also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
  • aryl according to the invention is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl.
  • arylalkyl 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 being benzyl, phenylethyl or Methylbenzyl, with benzyl 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.
  • hetaryl is pyridinyl or pyrimidinyl.
  • 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, tetrahydrofuryl.
  • halo-substituted radicals for example “haloalkyl” are radicals which are mono- or polysubstituted to the maximum possible number of substituents halogenated radicals can be the same or different halogen atoms.
  • Halogen here stands for 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 “alkyl” having the meaning given above.
  • 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 pesticides, in particular pesticides.
  • pest control 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, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. 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 of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hi
  • Aulacorthum solani Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Plutella xylostella Plutella maculipennis
  • Prays spp. Prodenia spp.
  • Protoparce spp. Pseudaletia spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Eg Schoenobius bipunctifer, Scirpophaga spp.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests from the strain of Mollusca in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp , Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp.
  • Dracunculus spp. Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp , Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp.
  • Plant pests from the Nematoda strain ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata
  • Paratrichodorus spp. Eg Paratrichodorus minor, Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., Eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp , Scutellonema spp., Subanguina spp., Trichodorus spp., Eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., Eg Tylenchorhynchus annulatus, Tylenchulus spp., Eg Tylenchulus semipenetrans, Xiphinema spp., Eg Xiphinema
  • the compounds of the formula (I) may 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 agent against 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.
  • Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such.
  • 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.
  • adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • 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 promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • 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 the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol 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.
  • alcohols such as butanol or glycol 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 as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or 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.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride
  • Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers , Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: eg 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, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Particularly suitable are those extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons as well as 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 lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic 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 sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydroly
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • auxiliaries also adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like 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.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, 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 which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are 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 material mobility (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 soybean oil, fatty amine alkoxylates 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 forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application. mixtures
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators
  • suitable fungicides bactericides, acaricides, molluscicides, ne
  • 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.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • 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.
  • Suitable mixing partners are, for example, the following compounds: insecticides / acaricides / nematicides:
  • acetylcholinesterase (AChE) inhibitors such as carbamates, eg alanycarb, aldicarb, bendocarb, benfuracarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, Pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, eg acephates, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrif
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. 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, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], e
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfbxaflor.
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as Alkyl halides, eg methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and fenbutatin oxide or propargite or
  • Nicotinergic acetylcholine receptor antagonists 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 Bupro fezin.
  • Anti-skinning agents especially in dipterans, i.e., two-toed, such as Cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • Voltage-dependent sodium channel blockers eg indoxacarb or metaflumizone.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Dicofol, Diflovidazine, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazone, pyriminostrobin, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacill
  • inhibitors of ergosterol biosynthesis such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole cis, (1.21)
  • inhibitors of respiration such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS),
  • inhibitors of amino acid and protein biosynthesis such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin.
  • inhibitors of ATP production such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.
  • inhibitors of cell wall synthesis such as (9.1) benthia-valicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) Valifenalate and (9.10) Polyoxin B.
  • inhibitors of lipid and membrane synthesis such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8)
  • Isoprothiolane (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb ,, (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazenes and (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis such as (11.1) carpropamide, (11.2) diclocymet,
  • inhibitors of nucleic acid synthesis such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, ( 12.8) Hymexazole, (12.9) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid and (12.14) Octhilinone.
  • Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide.
  • decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap.
  • Other compounds such as (15.1) benthiazole, (15.2) betoxazine, (15.3) capsimycin,
  • the compounds of formula (I) may be combined with biological pesticides.
  • biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), 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, especially strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular 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-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. 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 especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • 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 armyworm
  • mNPV Spodoptera littoralis
  • Examples of plant extracts and products formed by microorganisms including proteins and secondary metabolites used as biological pest control agents can, are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) 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 are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts should be understood as meaning all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root.
  • leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, such as 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) takes place directly or by acting on their environment, habitat or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing on, injecting and in the case of propagation material , in particular in the case of seeds, continue to be coated in one or more layers.
  • all plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof 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 bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives 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 bottoms salt, increased flowering, easier harvesting, 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.
  • Such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, caused for example by toxins formed in the plants, in particular those caused by the genetic material from Bacillus Thuringiensis (eg 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 phytopathogenic fungi, bacteria and / or viruses, eg through systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and accordingly expressed proteins and toxins, as well as an increased tolerance of the plants against certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (SAR), systemin,
  • 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, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails. Plant protection - types of treatment
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched 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 can be, for example, by drenching, mixing in the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, ie the compounds of Formula (I) are introduced in solid form, (eg in the form of granules) in the location of the plants.
  • a solid application form eg as granules
  • 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 by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • 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.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers which contain a compound of the formula (I) and mixture partners may optionally be replaced by a Interlayer be separated.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent 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 one of the compounds of the formula (I) acts systemically is that the 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 the formula (I) can also be used in particular in the case of transgenic seed.
  • 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.
  • 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, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seed which contains at least one contains 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, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. 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 seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing 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 also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also 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 112 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 alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • 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-stryrylphenol 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 seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives 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. Examples include dichlorophen and Benzylalkoholhemiformal. 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 cellulose derivatives, 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, pp. 401-412).
  • 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, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing 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 pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • 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.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and 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 stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and crustaceans, eg in aquaculture and insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • control means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • the arthropods include: 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Omithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis;
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
  • Toxoplasmadidae for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum,
  • Theileria spec such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (eg, Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
  • Cestodes from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp ., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from 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.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or acaricide
  • an arthropodicide such as an insecticide or acaricide
  • 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 may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are:
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, especially the genera Aedes, Anopheles, eg A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, 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.
  • Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the application of the invention for the protection of wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • 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.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the compounds of formula (I) are used alone or in Combination with other active ingredients and / or excipients used.
  • 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.
  • 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.
  • the application is carried out, for example, in aerosols, pressureless sprays, eg pump and atomizer sprays, smoke machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven 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 compounds of the formula (I) can be prepared by the method described below.
  • the substituent eg, R 1, n, Q 1, etc.
  • R 1, n, Q 1, etc. have if not explicitly described otherwise the meanings described above.
  • the dicarboxylic acid of the general formula (II) can firstly be converted into an acid halide and then reacted in the presence of a base such as, for example, triethylamine or sodium hydroxide.
  • a base such as, for example, triethylamine or sodium hydroxide.
  • the carboxylic acid can also be carried out using coupling reagents such as dicyclohexylcarbodiimide and additives such as 1-hydroxybenzotriazole [Chem. Ber. 1970, 788].
  • coupling reagents such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, ⁇ , ⁇ -carbonyl-1H-imidazole, N- [(1H-benzotriazol-1-ylxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate , and similar compounds.
  • Suitable coupling reagents for carrying out the dartelling process are all those which are suitable for the preparation of an ester or amide bond (cf., for example, Bodansky et al. Peptide Synthesis, 2nd Ed., Wiley & Sons, New York, 1976; Gross, Meienhofer, The Peptides: Analysis, Synthesis, Biology (Academic Press, New York, 1979), use.
  • condensation reagent such as, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide or ⁇ , ⁇ -carbonyl-1H-imidazole, N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N- methylmethanaminiumhexafluorophosphat converted into compounds of general formula (1-1), wherein G then stands for a free electron pair.
  • a condensation reagent such as, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide or ⁇ , ⁇ -carbonyl-1H-imidazole, N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N- methylmethanaminiumhexafluorophosphat converted into compounds of general formula (1-1), wherein G then stands for a free electron pair.
  • the compounds of the formula (IV) can also be first converted into the corresponding acid chloride, for example by reaction with thionyl chloride or sulfuryl chloride, and then reacted with amines of the formula (VII) in the presence of a base such as triethylamine to give compounds of the formula (Ia) ,
  • R a , R, R 0 and R independently of one another have the meaning described above for R are partially known or can be obtained by hydrolysis of corresponding ester precursors (see, for example, quinoline-2,6-dicarboxylic acid: Journal of Heterocyclic Chemistry (1989 ), 26 (4), 929-31; 4-chloroquinoline-2,6-dicarboxylic acid: CAS registry number 902742-45-4; 2-methoxycarbonyl-4-methyl-quinoline-6-carboxylic acid: WO 9613485; methylquinoline-2,6-dicarboxylate: Bioorganic & Medicinal Chemistry (2006), 14 (13), 4600-4609).
  • Quinoline dicarboxylic acids of the formula (II-1a) are obtained here in analogy to known processes from nitriles of the formula (A-9) by alkaline hydrolysis, for example with LiOH in methanol.
  • Nitriles of the formula (A-9) can be obtained from quinoline N oxides of the formula (A-8) by reaction with a cyanide, for example trimethylsilyl cyanide in the presence of a base, for example triethylamine (cf., for example, WO-A-2011 / 9540).
  • Quinoline N-oxides of the formula (A-8) can be obtained by oxidation of a quinoline of the formula (A-7), for example with m-chloroperbenzoic acid (cf., for example, WO-A-2011/9540).
  • Quinolines of the formula (A-7) can be obtained in analogy to known processes by reacting an aniline of the formula (A-6) with glycerol in the presence of sulfuric acid (cf., for example, Heterocyles 29 (12) 2345-51, 1989).
  • Compounds of the formula (A-6) are commercially available, known from the literature or obtainable in analogy to processes known from the literature Quinazoline carboxylic acids of the formula ⁇ -2),
  • R a , R and R 0 independently of one another have the meaning described above for R are partially known or can be obtained by hydrolysis of corresponding ester precursors (cf., for example l, 8-naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92 (5), 959-966; 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047).
  • ester precursors cf., for example l, 8-naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92 (5), 959-966; 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047.
  • Quinazolinecarboxylic acids of the formula (II-2a) are hereby obtained in analogy to known processes from compounds of the formula (A-12) by oxidation of the methyl group, for example with potassium permanganate or selenium dioxide (cf., WO-A-2010/101949, J. Het 1989, 26, 929-31)
  • Compounds of the formula (A-12) can be obtained by halogenation of the corresponding hydroxy compounds of the formula (A-11), for example with phosphorus oxychloride or phosphorus oxybromide (cf., WO-A-2008/133753).
  • the compound of the formula (A-11) can be obtained by reacting 2-amino-6-methylpyridine with dimethyl 2- (methoxymethylene) propanedioate (see US2001 / 46989, J. Med. Chem. 1997, 40, 2674).
  • Quinazolinecarboxylic acids of the formula ⁇ -3) can be obtained by reacting 2-amino-6-methylpyridine with dimethyl 2- (methoxymethylene) propanedioate (see US2001 / 46989, J. Med. Chem. 1997, 40, 2674).
  • Quinazolinecarboxylic acids of the formula (II-3a) are hereby prepared in analogy to generally known processes from compounds of the formula (A-18) by hydrolysis of the cyano group, e.g. obtained with sodium hydroxide solution.
  • Nitriles of formula (A-18) can be obtained from the corresponding bromo compounds of formula (A-17) by reaction with cyanide (see WO-A-2012/177728, WO-A-2003/010146).
  • Quinazoline carboxylic acids of formula (A-17) may be e.g. by reaction of aminomethyl compounds of the formula (A-16) with ethyl 2-oxoacetates are obtained (see Bioorg., Med. Chem. 2009, 17, 8221-8233).
  • Compounds of the formula (A-16) can be obtained by generally known processes in a multistage synthesis from anilines of the formula (A-13) (see Organic Letters 15 (2013), 3766).
  • Amines of the general formula (III) are known from the literature or can be obtained analogously to processes known from the literature (cf., for example, WO-A-2011/054436, WO-A-2012/119984).
  • compounds of formula (I) and (II) can be prepared by the methods described above. If individual connections do not follow the procedure described above can be prepared, the synthesis by derivatization of other compounds of formulas (I) and (II) is possible or by individual modifications of the described methods. For example, it may be advantageous to prepare certain compounds of formulas (I) or (II) from other compounds of formulas (I) and (II), for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, olefination, halogenation, acylation , Alkylation and the like.
  • Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. 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.
  • chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane,
  • Octylcaprolactam 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, ⁇ , ⁇ '-diformyl-piperazine) and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
  • ketones e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
  • the process according to the invention is 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 and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature.
  • a protective gas atmosphere e.g., under nitrogen, argon or helium
  • 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, especially 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-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline , ⁇ -picoline, ⁇ -picoline, pyrimidine, acridine, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylenediamine, ⁇ ,
  • mineral acids for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic 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
  • hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids for example aluminum (III) chloride,
  • Step 2 Methyl 5-bromoquinolines-6-carbox late / methyl-7-bromoquinolines-6-carboxylates
  • Step 3 Methyl 5-bromo-1-oxido-quinoline-1 -ium-6-carboxylate / methyl-7-bromo-1-oxo-quinoline-l-ium-6-carboxylate
  • Methyl-5-bromo-2-cyano-quinoline-6-carboxylate (0.183 g, 0.629 mmol) was suspended in ethanol (25 mL) and sodium hydroxide solution (45%, 201 mg, 5.029 mmol) was added. The reaction mixture was stirred for 18 hours at 50 ° C and then stirred into 10 ml of ice water. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. There were obtained 0.128 g (68% of theory) of 5-bromoquinolines-2,6-dicarboxylic acid.
  • Step 6 5-Bromo-2 - [[2,2,2-trifluoro-1- (4-fluoro-3- (trifluoromethyl) phenyl] ethyl] cw
  • 5-Bromoquinolines-2,6-dicarboxylic acid 60 mg, 0.203 mmol was dissolved in N, N-dimethylformamide (1.0 mL) and sequentially 2,2,2-trifluoro-l- [4-fluoro-3- ( trifluoromethyl) phenyl] ethanamine (66.15 mg, 0.253 mmol), N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate (76.9 mg, 0.203 mmol); Methylmorpholine (81.99 mg, 0.811 mmol) was added.
  • Methyl 5-nitroquinoline-6-carboxylate 5-Nitroquinoline-6-carboxylic acid (6200 mg, 28.4 mmol) (eg known from WO9812180) was suspended in dichloromethane (125.0 mL) and treated at 0 ° C with oxalyl chloride ( 4328 mg, 34.1 mmol). The reaction mixture was first stirred for 1 h at room temperature and then for a further 1 h at reflux temperature. After distilling off the solvent, methanol (23 mL, 18211 mmol) was added and stirred at room temperature for 18 hours. The excess methanol was distilled off for the most part and the residue was mixed with 300 mL of water.
  • Methyl 5-aminoquinoline-6-carboxylate Methyl 5-nitroquinoline-6-carboxylate (600 mg, 25.8 mmol) was dissolved in methanol / THF (250.0 mL / 7.5 mL) and treated with Pd-C hydrogenated as catalyst (274 mg, 2.58 mmol) at 1 bar pressure. The reaction mixture was filtered through kieselguhr, washed with methanol and the solvent was distilled off under reduced pressure.
  • Methyl 5-iodoquinoline-6-carboxylate Methyl 5-aminoquinoline-6-carboxylate (4800 mg, 23.7 mmol) was slowly added at 100 ° C to a mixture of 3-methylbutyl nitrite (4449 mg, 37.9 mmol). and methylene diiodide (38.2 mL, 474 mmol). After stirring for 0.5 h at 100 ° C, the reaction mixture was mixed with water and extracted several times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and then concentrated.
  • 3-methylbutyl nitrite 4449 mg, 37.9 mmol
  • methylene diiodide 38.2 mL, 474 mmol
  • Methyl 5-iodoquinoline-6-carboxylate 1-oxide Methyl 5-aminoquinoline-6-carboxylate (2500 mg, 7.98 mmol) was initially charged in dichloromethane (15.0 mL) and hydrogen peroxide (50%, 1086 mg, 15.9 mmol) and methyltrioxorhenium (VII) (39.8 mg, 0.16 mmol). The reaction mixture was stirred for 18 h, then extracted repeatedly with water and the aqueous phase with ethyl acetate.
  • Methyl 2-cyano-5-iodoquinoline-6-carboxylate (600mg, 1.82mmol) was dissolved at 0 ° C in a solution of potassium cyanide (237mg, 3.64 mmol) in water (7.8 mL). To this was added benzoyl chloride (0.432 mL, 3.64 mmol) and stirred for 1 h under ice cooling. The aqueous phase was decanted off and the residue was stirred with 1M potassium carbonate solution. After addition of dichloromethane, the phases were separated, washed with water, dried over magnesium sulfate and the solvent removed in vacuo.
  • 5-iodoquinoline-2,6-dicarboxylic acid methyl 2-cyano-5-iodoquinoline-6-carboxylate (326 mg, 0.96 mmol) was suspended in ethanol (8.0 mL) and washed with sodium hydroxide solution (45%, 685 mg, 7.71 mmol). The reaction mixture was stirred for 18 hours at 50 ° C and then in 200 ml of ice water stirred. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. 243 mg (71% of theory) of 5-iodoquinoline-2,6-dicarboxylic acid were obtained.
  • R 2 is H
  • W is O
  • Q 1 and Q 2 are CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • A is -CO-NR 13 -
  • G is a free one Elektonenjo.
  • Example 1-1-01 1 H-NMR (400.0 MHz, de-DMSO): See Synthesis Example 1
  • Example 1-1-04 1 H-NMR (400.0 MHz, de-DMSO):
  • ⁇ 10.135 (2.0); 10.122 (2,1); 9.675 (2.5); 8,899 (10.1); 8.884 (10.9); 8,883 (10.3); 8,332 (10,2); 8,325 (15.4); 8,318 (11,6); 8,317 (11.0); 8,310 (16.0); 8,302 (10.9); 8,154 (5.8); 8,141 (6,2); 7,952 (14.8); 7,937 (14,3); 7,841 (5.5); 7,828 (7.0); 7,744 (5.1); 7,731 (8.7); 7,718 (3.9); 6.378 (2.6); 6,366 (1.9); 4,040 (0.6); 4.028 (0.6); 3,417 (0.4); 3,413 (0.3); 3,367 (653.8); 3,324 (0.4); 2,622 (0.4); 2,531 (0.7); 2,528 (0.9); 2,525 (0.9); 2,516 (23.7); 2,513 (49,7); 2,510 (67.9); 2,507 (49,7); 2,505 (23.8); 2,394 (0.4); 2,092 (10.2);
  • ⁇ 10.113 (1.9); 10,089 (2.0); 8.815 (2.4); 8,793 (2.6); 8,568 (2,1); 8,557 (2,1); 8.528 (1.1); 8,509 (1.9); 8.490 (1.1); 8.317 (0.5); 8,199 (3.8); 8,177 (3.7); 8.132 (2.3); 8.110 (2.5); 7.751 (3.5); 7,730 (3,1); 6,465 (0.8); 6.433 (1.1); 6,420 (0.8); 3,324 (95.7); 3.175 (1.1); 3.162 (1.0); 2,925 (0.6); 2,916 (0.9); 2.907 (1.3); 2,897 (1.3); 2,889 (0.8); 2,879 (0.6); 2,667 (16.0); 2,524 (4,6); 2,511 (51.5); 2,507 (100.9); 2,502 (131.4); 2,498 (94.5); 2,493 (45.9); 2.333 (0.6); 2,329 (0.9); 2.325 (0.6); 0.756 (0.9); 0.743 (2.5); 0.738 (3.3); 0.726 (3.0);
  • Example 1-1-16 1 H NMR (400.0 MHz, d 6 -DMSO):
  • ⁇ 10.147 (0.4); 10.131 (3.5); 10,106 (3,6); 8,884 (5.1); 8,862 (5.5); 8,861 (5.4); 8,650 (1.0); 8,640 (2.7); 8.628 (2.7); 8.617 (0.9); 8.366 (0.7); 8,307 (12,7); 8,299 (7.6); 8,285 (7.9); 8,277 (5.8); 8,155 (3,1); 8,136 (3,1); 7.921 (0.5); 7,908 (7,8); 7,899 (0.6); 7,886 (7.2); 7,840 (2.8); 7,821 (3.8); 7,744 (2.8); 7,724 (4.4); 7,705 (1.8); 6,421 (0.4); 6,399 (1.5); 6,377 (2,2); 6,354 (1.6); 6,333 (0.5); 3,619 (0.5); 3,608 (0.5); 3.602 (1.3); 3.596 (0.5); 3.586 (0.5); 3,331 (78.2); 2,850 (16.0); 2,838 (15,8); 2,698 (0.5); 2,686 (0.5); 2,677 (
  • ⁇ 10.135 (1.7); 10.111 (1.7); 8,879 (2,4); 8.857 (2.6); 8,593 (1.6); 8,574 (1.6); 8,308 (6,1); 8,297 (2.7); 8,286 (3.6); 8.275 (2.7); 8,159 (1.3); 8.140 (1.4); 7,881 (3.6); 7,859 (3.3); 7.841 (1.2); 7,821 (1.7); 7,745 (1.3); 7,726 (2.0); 7.706 (0.8); 6,399 (0.7); 6,377 (1.0); 6,354 (0.7); 5,759 (0.4); 4.147 (0.7); 4.113 (1.0); 4.112 (1.0); 4,095 (0.7); 4,039 (0.7); 4,021 (0.7); 3,334 (72.6); 2,673 (0.3); 2,526 (0.9); 2,512 (21.3); 2,508 (42.4); 2,504 (55.1); 2,499 (39.5); 2,495 (19.0); 2,331 (0.4); 1,990 (3.0); 1,208 (16,0); 1,191 (16.0); 1.176 (1.8);
  • ⁇ 10.122 (3.0); 10.098 (3.1); 9,784 (2.7); 9,222 (6.4); 8,972 (2.7); 8,871 (4,1); 8.849 (4.5); 8,323 (2,9); 8,300 (16.0); 8,278 (6.0); 8,268 (7.3); 8.246 (3.5); 8.157 (2.5); 8.138 (2.6); 7,843 (2.2); 7,823 (3,1); 7.746 (2.3); 7,727 (3.5); 7,707 (1.5); 6,421 (0.4); 6,400 (1.3); 6.379 (1.8); 6.356 (1.3); 6.334 (0.4); 3,337 (128.3); 2,678 (0.4); 2,674 (0.5); 2,670 (0.4);
  • ⁇ 10.163 (1.3); 10.139 (1.3); 8,882 (1.7); 8.860 (1.8); 8,693 (1.2); 8,673 (1.2); 8,407 (0.9); 8,392 (0.9); 8,308 (3.3); 8,289 (2,2); 8,286 (3,2); 8.260 (0.6); 7,893 (2,4); 7.871 (2.3); 7,680 (0.7); 7.655 (1.0); 7.632 (0.7); 6,435 (0.5); 6,413 (0.8); 6,391 (0.6); 4,210 (0.6); 4.191 (0.7); 4.174 (0.6); 4.056 (0.3); 4.038 (1.1); 4.021 (1.1); 4.003 (0.4); 3,326 (43.1); 2,729 (0.6); 2,712 (0.6); 2,696 (1.2); 2,678 (1.3); 2,668 (0.3); 2,642 (1.0); 2,625 (1.0); 2.609 (0.5); 2,592 (0.5); 2,525 (1.0); 2,512 (22.3); 2,507 (44.2); 2,503 (57.6); 2,498 (42.3);
  • ⁇ 10.205 (3.5); 10.181 (3.6); 9,571 (3.9); 9,552 (4.0); 8,925 (4,6); 8,924 (4,6); 8,903 (5.1); 8,902 (5.2); 8,513 (1.9); 8.494 (3,4); 8.475 (1.9); 8,349 (8.2); 8,343 (4,8); 8,341 (4,7); 8,326 (8.0); 8,321 (5,3); 8,320 (5.3); 7,957 (7.9); 7.935 (7.4); 6.491 (0.4); 6,470 (1.3); 6.449 (1.8); 6,426 (1.4); 6,404 (0.5); 5.758 (1.1); 5.104 (0.5); 5,086 (2.3); 5,068 (3.6); 5,050
  • Example 1-1-55 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-56 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-58 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-59 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-61 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-63 1 H-NMR (400.0 MHz, d6-DMSO):
  • ⁇ 10.170 (1.2); 10.145 (1.2); 9.496 (0.6); 9,482 (1.4); 9,468 (0.6); 8.861 (1.6); 8.839 (1.8); 8.408 (0.8); 8.391 (0.8); 8.365 (1.6); 8,343 (1.8); 8.322 (2.4); 8,300 (2,4); 8.275 (0.4); 8.269 (0.5); 8.261 (0.5); 8.254 (0.5); 8.248 (0.5); 7.905 (2.4); 7.884 (2.3); 7,682 (0.7); 7.656 (0.9); 7.633 (0.7); 6.442 (0.4); 6,420 (0.7); 6.397 (0.5); 5,759 (1.2); 4,440 (3,1); 4,426 (3,1); 4.057 (1.2); 4,039 (3.7); 4,021 (3.7); 4.004 (1.3); 3,336 (44.3); 2,528 (0.5); 2,514 (11,7); 2,510 (23.8); 2,505 (31.5); 2,501 (23.1); 2,496 (11.4); 1,991 (16.0); 1.338 (1.2);
  • Example 1-1-66 1 H-NMR (400.0 MHz, d6-DMSO):
  • NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists.
  • the 'H NMR data of selected examples are noted in terms of' H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in parentheses are listed. The ⁇ value - signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ 1 (intensity I); ⁇ 2 (intensity 2); ; ⁇ i (intensity i); ; ⁇ n (intensity n)
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 'H NMR interpretation.
  • Emulsifier alkylaryl polyglycol ether
  • 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.
  • 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).
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-1-01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1- 1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1- 25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1- 1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1- 50, 1-1-51, 1-1-52, 1-1- 53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-6
  • Emulsifier alkylaryl polyglycol ether
  • 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.
  • dilute with emulsifier-containing water Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z.
  • the following compounds of Preparation Examples have an effect of 90% at a rate of 100 g / ha: 1-1-01, 1-1-07, 1-1-11, 1-1-16, 1-1-32 , 1-1-56, 1-1-59
  • 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.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water 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.
  • SPODFR Spodoptera frugiperda - spray test
  • Emulsifier alkylaryl polyglycol ether
  • 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.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • active compound 10 mg are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
  • Tick nymphs Ambfyomma hebraeum
  • the ticks are put on filter paper in one
  • Petri dish transferred and stored in a climatic cabinet.
  • Boophilus microplus - Diptest BOOPMI Dip
  • Test animals Bovine tick (Boophilus microplus) strain Parkhurst, SP-resistant Solvent: Dimethylsulfoxide
  • the active ingredient 10 mg are dissolved in 0.5 ml of dimethyl sulfoxide.
  • the active compound solution is diluted with water to the particular desired concentration.
  • This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female bovine ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room.
  • 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 for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: 1-1-43, 1-1-47, 1-1-55, 1-1-56, 1-1- 62 90% at a rate of 100 ppm: 1-1-57
  • Boophilus microplus injection test (BOOPMI Inj)
  • 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.
  • CTECFE Ctenocephalides felis - Oral test
  • active compound 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.
  • 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, whose Bottom is closed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • Lucilla cuprina - test (LUCICU)
  • active compound 10 mg 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 Goldfinch ⁇ Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
  • 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 domestica).
  • the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed 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 uncoordinated are considered dead or struck.
  • a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / 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.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 5 ⁇ g / cm 2 : 1-1-01, 1-1-03, 1-1-14, 1-1-20, 1 -1-21, 1-1-25, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1 -35, 1-1-37, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50 , 1-1- 51.1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1 -1-59, 1-1-60, 1-1-61 Rhipicephalus sanguineus - in vitro contact tests with adults of brown dog tick
  • the vials are populated with 5-10 adult dog tick ⁇ Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated.
  • a substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.

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Abstract

The present invention relates to compounds of general formula (I), where R1 to R6, A, Y, X, G, Q1 to Q4 and n have the meanings cited in the description, and to a method for the preparation and use thereof as insecticides and acaricides.

Description

CHINOLINDERIVATE ALS INSEKTIZIDE UND AKARIZIDE  CHINOLINE DERIVATIVES AS INSECTICIDES AND ACARICIDES
Die vorliegende Erfindung betrifft neue Quinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen, vor allem von Arthropoden und insbesondere von Insekten, Spinnentieren und Nematoden. Insektizide Indol- bzw. Benzimidazolcarbonsäureamide sind bereits bekannt, siehe WO-A-2011/054436 oder WO-A-2012/119984. Es wurde nun überraschend gefunden, dass bestimmte neue Quinolinderivate wie z.B. Quiolin-2-carbonsäureamide, starke Insektizide und akarizide Eigenschaften bei gleichzeitig guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit besitzen. Die erfindungsgemäßen neuen Verbindungen wurden bislang nicht offenbart. 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 Kombinierbarkeit 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. The present invention relates to novel Quinolinderivate, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes. Insecticidal indole or benzimidazolecarboxamides are already known, see WO-A-2011/054436 or WO-A-2012/119984. It has now surprisingly been found that certain novel quinoline derivatives, e.g. Quiolin-2-carboxamides, strong insecticides and acaricidal properties with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility possess. The novel compounds of the invention have not been disclosed. 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 the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on 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 Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. Es wurde nun überraschend gefunden, dass bestimmte neue Quinolinderivate sowie deren N-Oxide und Salze starke Insektizide und akarizide Eigenschaften bei gleichzeitig guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit besitzen. Die erfindungsgemäßen neuen Verbindungen wurden bislang nicht offenbart. The object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity. It has now surprisingly been found that certain new quinoline derivatives and their N-oxides and salts have strong insecticidal and acaricidal properties with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility. The novel compounds of the invention have not been disclosed.
Gegenstand der vorliegenden Erfindung (Ausgestaltung 1-1) sind daher Verbindungen der allgemeinen Formel (I) The present invention (embodiment 1-1) is therefore compounds of the general formula (I)
Figure imgf000002_0001
Figure imgf000002_0001
wobei R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach durch Halogen substituiertes Ci-Ce-Alkyl, C3-C6-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Alkylthio, Ci-Ce-Alkylsulfinyl, Ci-C6- Alkylsulfonyl, Ci-Cö-Alkylcarbonyl, Ci-C6-Alkoxycarbonyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl oder Ci-Cö-Alkylsulfonyloxy steht, oder in which R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen-substituted Ci-Ce-alkyl, C 3 -C 6 -cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci -C 6 - alkylsulfonyl, Ci-Cö-alkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl or Ci-Cö-alkylsulfonyloxy, or
R1 für eine gegebenenfalls 1 oder 2 Heteroatome enthaltende Ci-C i-Kohlenstoffkette steht, die an zwei benachbarten Ringpositionen gebundenen ist und einen aliphatischen, aromatischen, heteroaromatischen oder heterocychschen Ring bildet, welcher gegebenenfalls ein-oder mehrfach durch Ci-Cö-Alkyl oder Halogen substituiert ist, wobei n dann gleich 1 ist und wobei die Heteroatome ausgewählt sind aus der Gruppe bestehend aus N, S und O, n für 1,2, 3, 4 oder 5 steht, R 1 is an optionally 1 or 2 heteroatoms containing Ci-C i carbon chain which is bonded to two adjacent ring positions and forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring, which may be mono- or polysubstituted by Ci-Cö-alkyl or Halogen is then substituted, wherein n is then 1 and wherein the heteroatoms are selected from the group consisting of N, S and O, n is 1,2, 3, 4 or 5,
R2 für Wasserstoff, Halogen, Cyano, Hydroxy oder für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder Ci-C6-Alkoxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Fluor, Chlor, Brom oder lod R 2 is hydrogen, halogen, cyano, hydroxyl or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy, where the substituents are independent are selected from fluorine, chlorine, bromine or iodine
R3 für Wasserstoff, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C i-Alkyl, C2-C4-Alkenyl, C3-C4-Alkinyl, Ci-C i-Alkylcarbonyl oder Ci-C i-Alkoxycarbonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Cyano, Halogen, C1-C4- Alkyl oder Ci-C4-Alkoxy R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C i-alkylcarbonyl or Ci-C i-alkoxycarbonyl, wherein the substituents independently of one another are selected from cyano, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
Q1 für C-R4 oder N steht, Q 1 is CR 4 or N,
Q2 für C-R4 steht, Q 2 is CR 4 ,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 oder N steht, wobei Q1 für C-R4 steht wenn Q4 für N steht und wobei Q4 für C-R4 steht wenn Q1 für N steht. Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
R4 für Wasserstoff, Halogen, Nitro, Cyano, Ci-C4-Alkyl, Ci-C4-Haloalkyl oder Ci-C4-Alkoxy steht, R 4 is hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
R6 für Wasserstoff, Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, CI-CÖ- Alkoxy, (Ci-C6-Alkoxy)carbonyl, Ci-C6-Alkylamino, Formyl, (Ci-C6-Alkyl)carbonyl, CI-CÖ- Alkoxyimino-Ci-C6-alkyl, Ci-C6-Dialkylamino, (Ci-C6-Alkylamino)carbonyl, (CI-CÖ- Dialkylamino)carbonyl, Ci-C6-Alkylthio, Ci-C6-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, CI-CÖ- Alkylaminosulfonyl oder Ci-C6-Alkylsulfonylamino steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-Cö-Alkyl, Ci-C6-Alkoxy, C3-C6-Cycloalkyl, Ci-C6-Halogenalkoxy oder Ci- Ce-Alkylthio, R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, CI-C east - Alkoxy, (C 1 -C 6 -alkoxy) carbonyl, C 1 -C 6 -alkylamino, formyl, (C 1 -C 6 -alkyl) carbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -dialkylamino, (C 1 -C 6 alkylamino) carbonyl, (CI-COE dialkylamino) carbonyl, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, CI-C Ö - alkylaminosulfonyl or Ci-C6-alkylsulfonylamino, where the substituents are independently are selected from among halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkoxy or C 1 -C 4 -alkylthio,
X für Ci-C6-Halogenalkyl steht, das gegebenenfalls zusätzlich einfach bis dreifach substituiert sein kann, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Hydroxy, Cyano oder Ci-C i-Alkoxy, X is Ci-C6-haloalkyl, which may optionally additionally be monosubstituted to trisubstituted, where the substituents are independently selected from hydroxy, cyano or Ci-C i-alkoxy,
W für O oder S steht, W stands for O or S,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a free electron pair or for oxygen,
A für eine bivalente chemische Gruppierung steht, die ausgewählt ist aus den Gruppierungen -C(=0)NR13-, -C(=S)NR13-, -C(=0)NR13-NR16-A is a bivalent chemical moiety selected from the groupings -C (= O) NR 13 -, -C (= S) NR 13 -, -C (= O) NR 13 -NR 16 -
, -C(=0)NR13C(R14)(R15)C(=0)NR16-, C(R14)(R15)NR13-C(=0)- , -CH=N-N(R13)-C(=W)-N(R16)-, - N(R13)-N(R16)-C(=0)- wobei die jeweils erstgenannte (linke) Anknüpf ngsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, , -C (= O) NR 13 C (R 14 ) (R 15 ) C (= O) NR 16 -, C (R 14 ) (R 15 ) NR 13 -C (= O) -, -CH = NN (R 13 ) -C (= W) -N (R 16 ) -, - N (R 13 ) -N (R 16 ) -C (= O) - wherein the first-mentioned (left) attachment site on the ring and the each second (right) attachment point is linked to Y,
R13, R16 unabhängig voneinander für Wasserstoff, für Ci-C i-Alkyl, Ci-C i-Alkoxy-Ci-C i-Alkyl, Cyano- Ci-C i-alkyl, C3-C6-Cycloalkyl, Ci-C i-Alkylcarbonyl, Ci-C i-Alkoxycarbonyl oder C2-C4-Alkenyl stehen, R 13 , R 16 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl i-alkylcarbonyl, Ci-C i-alkoxycarbonyl or C2-C 4 alkenyl stand,
R14, R15 unabhängig voneinander für Wasserstoff oder für Ci-C4-Alkyl stehen oder R14, R15 zusammen einen 3-6 gliedrigen aliphatischen Ring bilden, R 14 , R 15 independently of one another represent hydrogen or C 1 -C 4 -alkyl or R 14 , R 15 together form a 3-6-membered aliphatic ring,
Y für Wasserstoff oder für gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Ci-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl oder Cs-Ce-Cycloalkenyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-Alkylaminocarbonyl, Ci-C4-Alkylaminothiocarbonyl, Ci-C4-Halogenalkylaminocarbonyl, Di-(Ci-C4-Alkyl)-aminocarbonyl, Di-(Ci-C4-Alkyl)- aminothiocarbonyl, Hydroxycarbonyl, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci- C6-Alkyl-C3-C5-Cycloalkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-C6-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl, Ci-C4-Alkoxyimino-Ci-C4-Alkyl, Ci-Cö-Alkylthio, Ci-C6-Alkylsulfinyl, Ci-Cö-Alkylsulfonyl oder aus gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertem Aryl oder Hetaryl, wobei die Subsituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C i-Alkyl, Ci-C4-Halogenalkyl, Ci-C6-Alkoxy, oder CI-CÖ- Halogenalkoxy, oder Y für gegebenenfalls substituiertes Heterocyclyl, Aryl, Aryl-Ci-C4-alkyl, Hetaryl, Oxo-Heterocyclyl oder Hetaryl-Ci-C i-alkyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C i-Alkyl, Ci- C/t-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, CI-CÖ- Alkylsulfinyl oder Ci-C6-Alkylsulfonyl, sowie Salze und N-Oxide von Verbindungen der Formel (I) und deren Anwendung zur Bekämpfung von tierischen Schädlingen. Y is hydrogen or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 1 -C 12 -cycloalkenyl wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C 4 -Alkylaminothiocarbonyl, Ci-C 4 -Halogenalkylaminocarbonyl, di- (Ci-C 4 alkyl) aminocarbonyl, di- (Ci-C 4 alkyl) - aminothiocarbonyl, hydroxycarbonyl, Ci-C 4 alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci- C6-alkyl-C3-C 5 -cycloalkyl , C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl , Ci-Cö-alkylthio, Ci-C6-alkylsulfinyl, Ci-Cö-alkylsulfonyl or from optionally mono- or polysubstituted, the same or variously substituted aryl or hetaryl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C i-alkyl, Ci-C 4 -haloalkyl, Ci-C6-alkoxy, or CI-CÖ-haloalkoxy, or Y is optionally substituted heterocyclyl, aryl, aryl-C 1 -C 4 -alkyl, hetaryl, oxo-heterocyclyl or hetaryl-C 1 -C -alkyl, where the substituents are selected from halogen, nitro, cyano, hydroxy, C 1 -C 4 -alkyl, Alkyl, Ci-C / t-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy, Ci-C6-alkylthio, CI-CÖ-alkylsulfinyl or Ci-C6-alkylsulfonyl, and salts and N-oxides of compounds of Formula (I) and their use for controlling animal pests.
Die jeweilige Zahl der Substituenten n in der Formel (I) umfasst dabei nur die Substituenten, die von Wasserstoff verschieden sind. Aus diesem Grund ist Wasserstoff in der Definition von R1 auch nicht enthalten. Natürlich steht als Substituent immer Wasserstoff, wenn kein Substituent R1 an der jeweiligen Stelle vorhanden ist. The respective number of substituents n in the formula (I) includes only the substituents which are different from hydrogen. For this reason, hydrogen is not included in the definition of R 1 either. Of course, the substituent is always hydrogen, if no substituent R 1 is present at the respective site.
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. The compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
Die substituierten Quinolincarbonsäureamide sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formeln sind im Folgenden angegeben. The substituted quinolinecarboxylic acid amides are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below.
Bevorzugt (Ausgestaltung 2-1) sind die Verbindungen der Formel (I) in denen Preferred (embodiment 2-1) are the compounds of formula (I) in which
R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach durch Halogen substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl oder Ci-C4-Alkylsulfonyl oder Ci-C4-Alkylsulfonyloxy steht, n für 1 , 2, 3, 4 oder 5 steht R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl or C 1 -C 4 - Alkylsulfonyl or Ci-C 4 alkylsulfonyloxy, n is 1, 2, 3, 4 or 5 stands
R2 für Wasserstoff oder für gegebenenfalls einfach bis dreifach substituiertes Ci-Cö-Alkyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Fluor, Chlor, Brom oder Iod R3 für Wasserstoff, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C i-Alkyl, C2-C4-Alkenyl, C3-C4-Alkinyl, Ci-C4-Alkylcarbonyl oder Ci-C4-Alkoxycarbonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Cyano, Halogen oder Ci- C4-Alkoxy R 2 is hydrogen or optionally monosubstituted to trisubstituted Ci-Cö-alkyl, wherein the substituents are independently selected from fluorine, chlorine, bromine or iodine R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C4-alkylcarbonyl or Ci-C4-alkoxycarbonyl, wherein the Substituents are independently selected from cyano, halogen or Ci- C4-alkoxy
Q1 für C-R4 oder N steht, Q 1 is CR 4 or N,
Q2 für C-R4 steht, Q 2 is CR 4 ,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 oder N steht, wobei Q1 für C-R4 steht wenn Q4 für N steht und wobei Q4 für C-R4 steht wenn Q1 für N steht. Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
R4 für Wasserstoff, Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl oder Ci-C4-Alkoxy stehen, R 4 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
R6 für Wasserstoff, Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C4-Cycloalkyl , Ci- C4-Alkoxy, (Ci-C4-Alkoxy)carbonyl, (Ci-C4-Alkyl)carbonyl, Ci-C4-Alkylthio, C1-C4- Alkylsulfinyl, oder Ci-C4-Alkylsulfonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Ci-C4-Alkyl, Ci-C4-Alkoxy oder Ci-C4-Alkylthio, R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl , C 1 -C 4 alkoxy, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 4 alkyl) carbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, or C 1 -C 4 alkylsulfonyl, where the substituents are independent are selected from among halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
X für Ci-C4-Halogenalkyl steht, X is Ci-C4-haloalkyl,
W für O steht, G für ein freies Elektronenpaar oder für Sauerstoff steht, W is O, G is a lone pair of electrons or oxygen,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, A stands for the bivalent chemical group -C (= O) NR 13 -, whereby the respectively first mentioned (left) attachment site at the ring and the respectively second mentioned (right) attachment site at Y,
R13 für Wasserstoff, für Ci-C4-Alkyl, Cyanomethyl, Ci-C4-Alkoxymethyl, C3-C6-Cycloalkyl, C1-C4- Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder C2-C4-Alkenyl steht, Y für Wasserstoff oder oder für gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Ci-Ce-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl oder C3-C6- Cycloalkenyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C i-Alkyl, Ci-C i-Halogenalkyl, C3-Cs-Cycloalkyl, CI-CÖ- Alkyl-C3-C5-Cycloalkyl , C2-C4-Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, C1-C4- Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl oder C1-C4- Alkoxyimino-Ci-C4-Alkyl, oder aus gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertem Phenyl, Thienyl, Pyridinyl oder Pyrimidinyl, wobei die Subsituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy, oder R 13 is hydrogen, C 1 -C 4 -alkyl, cyanomethyl, C 1 -C 4 -alkoxymethyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or C 2 -C 4 -alkenyl stands, Y is hydrogen or or optionally mono- or polysubstituted by identical or different substituents Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl or C 3 -C 6 -cycloalkenyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C i-alkyl, Ci-C i-haloalkyl, C3-Cs-cycloalkyl, CI-C Ö - alkyl-C 3 -C 5 - cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, Ci-C4 alkylthio, C1-C4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 - Alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, or phenyl optionally monosubstituted or polysubstituted by identical or different substituents, thienyl, pyridinyl or pyrimidinyl, where the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy, or
Y für ein gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Phenyl, oder für einen gegebenenfalls einfach oder mehrfach substituierten Heterocyclus ausgewählt aus der Gruppe bestehend aus Thienyl, Furanyl, Pyrrolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1 ,2,4-Triazolyl, 1,2,3-Oxdiazolyl, 1 ,2,4-Oxdiazolyl, 1,3,4- Oxdiazolyl, 1,2,3-Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl, Tetrazolyl, Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1 ,2,4-Triazinyl, 1,3,5-Triazinyl, Pyrrolidinyl, Isoxazolidinyl, Pyrazolidinyl, Oxazolidinyl, Thiazolidinyl, Imidazolidinyl, 1 ,2,4-Oxadiazolidinyl, 1,2,4- Thiadiazolidinyl, 1 ,2,4-Triazolidinyl, 1,3,4-Oxadiazolidinyl, 1,3,4-Thiadiazolidinyl, 1,3,4- Triazolidinyl, Pyrrolinyl, Isoxazolinyl, 2,3-Dihydropyrazolyl, 3,4-Dihydropyrazolyl, 4,5- Dihydropyrazolyl, 2,3-Dihydrooxazolyl, 3,4-Dihydrooxazolyl, Piperidinyl, Tetrahydrothienyl, Piperazinyl, Morpholinyl, Thiomorpholinyl, Dihydropyranyl, Tetrahydropyranyl, Tetrahydrothienyl, 1 ,4-Dioxanyl, 1,3-Dioxanyl, Dioxolanyl, Dioxolyl, Tetrahydrofuranyl, Dihydrofuranyl, Oxetanyl, Thietanyl, Oxidothietanyl, Dioxidothietanyl, Oxiranyl, Azetidinyl, Oxazetidinyl, Oxaziridinyl, Oxazepanyl, Oxazinanyl, Azepanyl, Oxopyrrolidinyl, Dioxopyrrolidinyl, Oxomorpholinyl, Oxopiperidinyl, Oxopiperazinyl oder Oxotetrahydrofuranyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, CI-CÖ- Alkylsulfinyl oder Ci-C6-Alkylsulfonyl. Y is an optionally mono- or polysubstituted by identical or different substituent, phenyl, or an optionally monosubstituted or polysubstituted heterocycle selected from the group consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, 1,2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1, 2,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1, 2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,3,4-triazolidinyl, pyrrolinyl, Isoxazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl, piperidinyl, tetrahydrothienyl, piperazinyl, morpholinyl, thiomorpholinyl, Dihydropyranyl, tetrahydropyranyl, tetrahydrothienyl, 1,4-dioxanyl, 1,3-dioxanyl, dioxolanyl, dioxolyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, thietanyl, oxidothietanyl, dioxothietanyl, oxiranyl, azetidinyl, oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, Oxomorpholinyl, oxopiperidinyl, oxopiperazinyl or oxotetrahydrofuranyl, where the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C4 alkyl, Ci- C4-haloalkyl, Ci-C6 alkoxy, or Ci-C6 Haloalkoxy, Ci-C6-alkylthio, CI-CÖ-alkylsulfinyl or Ci-C 6 -alkylsulfonyl.
Besonders bevorzugt (Ausgestaltung 3-1) sind die Verbindungen der Formel (I) in denen R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, durch Fluor oder Chlor substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl oder Ci-C4-Alkylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht, R2 für Wasserstoff steht, Particularly preferred (embodiment 3-1) are the compounds of formula (I) in which R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by fluorine or chlorine-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkyl, C 4 -alkylsulfonyl or C 1 -C 4 -alkylsulfonyloxy, n is 1, 2, 3, 4 or 5, R 2 is hydrogen,
R3 für Wasserstoff, Methyl, Cyanomethyl, Ethyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl oder Ethoxycarbonyl steht, R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
Q1 für C-R4 steht, Q 1 is CR 4 ,
Q2 für C-R4 steht, Q3 für C-R4 steht, Q 2 is CR 4 , Q 3 is CR 4 ,
Q4 für C-R4 steht, Q 4 stands for CR 4 ,
R4 für Wasserstoff, Fluor oder Chlor steht, R 4 is hydrogen, fluorine or chlorine,
R6 für Wasserstoff, Halogen, Nitro, Cyano, oder für gegebenenfalls einfach bis dreifach durch Halogen substituiertes Ci-C4-Alkyl oder Ci-C4-Alkoxy steht, X für Trifluormethyl, Difluormethyl oder Pentafluorethyl steht, R 6 represents hydrogen, halogen, nitro, cyano, or represents optionally monosubstituted to trisubstituted by halogen C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, X represents trifluoromethyl, difluoromethyl or pentafluoroethyl,
W für O steht, W stands for O,
G für ein freies Elektronenpaar steht, G stands for a lone pair of electrons,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, und wobei A is the bivalent chemical group -C (= O) NR 13 -, wherein the first-mentioned attachment site at the ring and the second-mentioned (right-hand) attachment site to Y, and wherein
R13 für Wasserstoff, Methyl, Ethyl, Cyanomethyl, Methoxymethyl, Ethoxymethyl, Cyclopropyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl oder Prop-2-en-l-yl steht, für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Ci-Cö-Alkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, oder Cs-Ce-Cycloalkyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-AlkyL- Ci-C i-Halogenalkyl, C3-Cs-Cycloalkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl oder Ci-C4-Alkoxyimino-Ci-C4- Alkyl, Ci-Ce-Alkyl-Cs-Cs-Cycloalkyl, oder R 13 is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl, optionally substituted once to three times, identically or differently substituted Ci-Cö Alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, or C 1 -C 6 -cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkyl Ci-C i-haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C 2 -C 4 - Alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 4 -alkoxyimino-Ci -C 4 -alkyl, Ci-Ce-alkyl-Cs-Cs-cycloalkyl, or
Y für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Phenyl, Phenylmethyl, 3-Oxetan-l-yl, 3-Thietan-l-yl, 3-Oxidothietan-l-yl, 3,3-Dioxidothietan-l -yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyridin-2-yl-methyl, Pyridin-3-yl-methyl, Pyridin-4-yl-methyl, 1,3-Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
Pyrimidin-2-yl oder l,3-Pyrimidin-2-yl-methyl steht , wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy. Pyrimidin-2-yl or l, 3-pyrimidin-2-yl-methyl group, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C4 alkyl, Ci- C4-haloalkyl, Ci-C6 Alkoxy, or Ci-C6-haloalkoxy.
In einer weiteren Ausführungsform (Ausgestaltung 3-2) sind besonders bevorzugt die Verbindungen der Formel (I) in denen R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, durch Fluor oder Chlor substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl oder Ci-C4-Alkylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht, In a further embodiment (embodiment 3-2), particular preference is given to the compounds of the formula (I) in which R 1 is halogen, nitro, cyano, C 1 -C 4 -alkyl which is optionally monosubstituted or polysubstituted or substituted by fluorine or chlorine, -C 4 alkoxy, C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C1-C4 alkylsulfonyl or Ci-C is 4 alkylsulfonyloxy, n is 1, 2, 3, 4 or 5,
R2 für Wasserstoff steht, R3 für Wasserstoff, Methyl, Cyanomethyl, Ethyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl oder Ethoxycarbonyl steht, R 2 is hydrogen, R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
Q für C-R4 steht, Q stands for CR 4 ,
|2 | 2
Q für C-R steht,  Q stands for C-R,
Q für C-R steht, Q , für C-R steht, für Wasserstoff, Fluor oder Chlor steht, für Wasserstoff, Halogen, Nitro, Cyano, oder für gegebenenfalls einfach bis dreifach durch Halogen substituiertes Ci-C4-Alkyl oder Ci-C4-Alkoxy steht, X für Trifluormethyl, Difluormethyl oder Pentafluorethyl steht, W für O steht, Q is CR, Q is CR, is hydrogen, fluorine or chlorine, hydrogen, halogen, nitro, cyano, or optionally monosubstituted to trisubstituted by halogen Ci-C 4 alkyl or Ci-C 4 alkoxy stands, X is trifluoromethyl, difluoromethyl or pentafluoroethyl, W is O,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a free electron pair or for oxygen,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle anA is the bivalent chemical group -C (= O) NR 13 -, wherein the first-mentioned (left) attachment site on the ring and the second-mentioned (right) attachment site to
Y anknüpft, und wobei Y is connected, and where
R für Wasserstoff, Methyl, Ethyl, Cyanomethyl, Methoxymethyl, Ethoxymethyl, Cyclopropyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl oder Prop-2-en-l-yl steht, Y für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Ci-Cö-Alkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, oder Cs-Ce-Cycloalkyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-AlkyL- Ci-C4-Halogenalkyl, C3-Cs-Cycloalkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl oder Ci-C4-Alkoxyimino-Ci-C4-R is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl, Y is optionally mono- to trisubstituted by identical or different substituents Ci-Cö Alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or Cs-Ce-cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-AlkyL-Ci-C4 haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkylsulfmyl, C1-C4 alkylsulfonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 4 -alkoxyimino-C 1 -C 4
Alkyl, Ci-Ce-Alkyl-Cs-Cs-Cycloalkyl, oder Alkyl, Ci-Ce-alkyl-Cs-Cs-cycloalkyl, or
Y für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Phenyl, Phenylmethyl, 3-Oxetan-l-yl, 3-Thietan-l-yl, 3-Oxidothietan-l-yl, 3,3-Dioxidothietan-l -yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyridin-2-yl-methyl, Pyridin-3-yl-methyl, Pyridin-4-yl-methyl, 1,3-Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
Pyrimidin-2-yl oder l,3-Pyrimidin-2-yl-methyl steht , wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy. Pyrimidin-2-yl or l, 3-pyrimidin-2-yl-methyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy , or Ci-C6-haloalkoxy.
Ganz besonders bevorzugt (Ausgestaltung 4-1) sind die Verbindungen der Formel (I) in denen R1 für Cyano, Fluor, Chlor, Brom, Iod, Difluormethyl, Trifluormethyl, Pentafluorethyl, Difluormethoxy, Trifluormethoxy oder Trifluormethylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht Very particularly preferred (embodiment 4-1) are the compounds of the formula (I) in which R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy or trifluoromethylsulfonyloxy, n is 1, 2 , 3, 4 or 5 stands
R für Wasserstoff steht, für Wasserstoff steht, für C-R4 steht, für C-R4 steht, für C-R4 steht, für C-R4 steht, für Wasserstoff stehen, für Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder Trifluormethyl steht, für Trifluormethyl steht, für O steht, für ein freies Elektronenpaar steht, für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die erstgenannte (linke) Anknüpfungsstelle am Ring und die zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, und wobei für Wasserstoff oder Methyl steht, für Methyl, Ethyl, Propan-l-yl, Propan-2-yl, Butan- 1-yl, Butan-2-yl, 2-Methylpropan-l-yl, 2- Methylpropan-2-yl, l-Butin-3-yl, Cyclopropyl, Cyclobutyl, Cyanomethyl, 1- Methoxycarbonylmethyl, 1 -Cyanoethyl, 2-Cyanoethyl, 1 -Cyanoprop-l-yl, 2-Cyanoprop-l-yl, 3- Cyanoprop-l-yl, l-Cyanoprop-2-yl, 2-Cyanoprop-2-yl, 1 -Cyanocyclopropyl, 2-Cyanoprop-2-en-R is hydrogen, is hydrogen, CR 4 , CR 4 , CR 4 , CR 4 , hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl, trifluoromethyl, O stands for a lone pair of electrons, for the bivalent chemical group -C (= O) NR 13 - stands, wherein the former (left) attachment site on the ring and the second-mentioned (right) attachment site to Y, and wherein hydrogen or methyl is methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2-yl, 1-butyne 3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop -2-yl, 2-cyanoprop-2-yl, 1-cyano-cyclopropyl, 2-cyanoprop-2-ene
1- yl, 2-Cyanocyclopropyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 2- Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 1 -Fluorpropan-2-yl, 2,2-Difluorprop-l-yl, 1,3- Difluorpropan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 1 -Ethylcyclopropyl, 1- Ethinylcyclopropyl, 1 -Ethinylcyclobutyl, l-Methoxypropan-2-yl, 1 -Methoxycyclopropyl, 1- Ethoxycyclopropyl, 1 -Methoxycarbonylcyclopropyl, 1 -Ethoxycarbonyl-cyclopropyl, Cyclopropylmethyl, 1-Cyclopropyleth-l-yl, 1 -Trifluormethylcyclopropyl, Pyridin-2-yl, 5- Chlorpyridin-2-yl, 5-Fluorpyridin-2-yl, 1 -(Aminocarbonyl)cyclopropyl, 1- (Aminothiocarbonyl)cyclopropyl, l-Cyano-2-methylpropan-l -yl, l-Cyanobut-3-in-l-yl, 1-Cyano-1-yl, 2-cyanocyclopropyl, 1-cyano-cyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-fluoropropan-2-yl, 2,2- Difluoroprop-1-yl, 1,3-Difluoropropan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 1-ethylcyclopropyl, 1-ethynylcyclopropyl, 1-ethynylcyclobutyl, 1-methoxypropan-2-yl, 1-methoxycyclopropyl, 1 Ethoxycyclopropyl, 1-methoxycarbonylcyclopropyl, 1-ethoxycarbonyl-cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 1-trifluoromethylcyclopropyl, pyridin-2-yl, 5-chloropyridin-2-yl, 5-fluoropyridin-2-yl, 1 - (Aminocarbonyl) cyclopropyl, 1- (aminothiocarbonyl) cyclopropyl, 1-cyano-2-methylpropan-1-yl, 1-cyanobut-3-yn-1-yl, 1-cyano
2- methylpropan-l-yl, 1 -Cyano-propan-2-yl, 1-Cyano-l -cyclopropylethyl, 1-Cyano-l-ethylprop-l- yl, 1-Cyano-l-methylcyclopropyl-methyl, (2-R)-l-(Methylthio)propan-2-yl, (2-R)-l- (Methylsulfinyl)propan-2-yl, l,3-Dimethoxy-2-cyanopropan-2-yl, 3-Oxetan-l-yl, Pyridin-2- ylmethyl oder l,3-Pyrimidin-2-yl-methyl steht. 2-methylpropan-1-yl, 1-cyano-propan-2-yl, 1-cyano-1-cyclopropyl-ethyl, 1-cyano-1-ethyl-prop-1-yl, 1-cyano-1-methylcyclopropyl-methyl, (2 -R) -l- (methylthio) propan-2-yl, (2-R) -l- (Methylsulfinyl) propan-2-yl, l, 3-dimethoxy-2-cyanopropan-2-yl, 3-oxetan-1-yl, pyridin-2-ylmethyl or l, 3-pyrimidin-2-yl-methyl.
In einer weiteren Ausführungsform (Ausgestaltung 4-2) sind ganz besonders bevorzugt die Verbindungen der Formel (I) in denen R1 für Cyano, Fluor, Chlor, Brom, Iod, Difluormethyl, Trifluormethyl, Pentafluorethyl, Difluormethoxy, Trifluormethoxy oder Trifluormethylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht In a further embodiment (embodiment 4-2), very particular preference is given to the compounds of the formula (I) in which R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy or trifluoromethylsulfonyloxy, n stands for 1, 2, 3, 4 or 5
R2 für Wasserstoff steht, R 2 is hydrogen,
R3 für Wasserstoff steht, Q1 für C-R4 steht, R 3 is hydrogen, Q 1 is CR 4 ,
Q2 für C-R4 steht, Q 2 is CR 4 ,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 steht, Q 4 stands for CR 4 ,
R4 für Wasserstoff stehen, R6 für Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder Trifluormethyl steht, R 4 is hydrogen, R 6 is fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl,
X für Trifluormethyl steht, X is trifluoromethyl,
W für O steht, W stands for O,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a free electron pair or for oxygen,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die erstgenannte (linke) Anknüpfungsstelle am Ring und die zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, und wobei A is the bivalent chemical moiety -C (= O) NR 13 -, with the former (left) attachment site attached to the ring and the second-mentioned (right) attachment site attached to Y, and
R13 für Wasserstoff oder Methyl steht, für Methyl, Ethyl, Propan-l-yl, Propan-2-yl, Butan- 1-yl, Butan-2-yl, 2-Methylpropan-l-yl, 2 Methylpropan-2-yl, l-Butin-3-yl, Cyclopropyl, Cyclobutyl, Cyanomethyl, 1 Methoxycarbonylmethyl, 1 -Cyanoethyl, 2-Cyanoethyl, 1-Cyanoprop-l-yl, 2-Cyanoprop-l-yl, 3 Cyanoprop-l-yl, l-Cyanoprop-2-yl, 2-Cyanoprop-2-yl, 1 -Cyanocyclopropyl, 2-Cyanoprop-2-en-R 13 is hydrogen or methyl, methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2 yl, l-butyn-3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3 Cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyano-cyclopropyl, 2-cyanoprop-2-ene
1- yl, 2-Cyanocyclopropyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 2- Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 1 -Fluorpropan-2-yl, 2,2-Difluorprop-l-yl, 1,3- Difluorpropan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 1 -Ethylcyclopropyl, 1- Ethinylcyclopropyl, 1 -Ethinylcyclobutyl, l-Methoxypropan-2-yl, 1 -Methoxycyclopropyl, 1- Ethoxycyclopropyl, 1 -Methoxycarbonylcyclopropyl, 1 -Ethoxycarbonyl-cyclopropyl, Cyclopropylmethyl, 1-Cyclopropyleth-l-yl, 1 -Trifluormethylcyclopropyl, Pyridin-2-yl, 5- Chlorpyridin-2-yl, 5-Fluorpyridin-2-yl, 1 -(Aminocarbonyl)cyclopropyl, 1- (Aminothiocarbonyl)cyclopropyl, l-Cyano-2-methylpropan-l -yl, l-Cyanobut-3-in-l-yl, 1-Cyano-1-yl, 2-cyanocyclopropyl, 1-cyano-cyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-fluoropropan-2-yl, 2,2- Difluoroprop-1-yl, 1,3-Difluoropropan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 1-ethylcyclopropyl, 1-ethynylcyclopropyl, 1-ethynylcyclobutyl, 1-methoxypropan-2-yl, 1-methoxycyclopropyl, 1 Ethoxycyclopropyl, 1-methoxycarbonylcyclopropyl, 1-ethoxycarbonyl-cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 1-trifluoromethylcyclopropyl, pyridin-2-yl, 5-chloropyridin-2-yl, 5-fluoropyridin-2-yl, 1 - (Aminocarbonyl) cyclopropyl, 1- (aminothiocarbonyl) cyclopropyl, 1-cyano-2-methylpropan-1-yl, 1-cyanobut-3-yn-1-yl, 1-cyano
2- methylpropan-l-yl, 1 -Cyano-propan-2-yl, 1-Cyano-l -cyclopropylethyl, 1-Cyano-l-ethylprop-l- yl, 1-Cyano-l-methylcyclopropyl-methyl, (2-R)-l-(Methylthio)propan-2-yl, (2-R)-l- (Methylsulfinyl)propan-2-yl, l,3-Dimethoxy-2-cyanopropan-2-yl, 3-Oxetan-l-yl, Pyridin-2- ylmethyl oder l,3-Pyrimidin-2-yl-methyl steht. einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I- 2-methylpropan-1-yl, 1-cyano-propan-2-yl, 1-cyano-1-cyclopropyl-ethyl, 1-cyano-1-ethyl-prop-1-yl, 1-cyano-1-methylcyclopropyl-methyl, (2 -R) -l- (methylthio) propan-2-yl, (2-R) -1- (methylsulfinyl) propan-2-yl, 1,3-dimethoxy-2-cyanopropan-2-yl, 3-oxetane l-yl, pyridin-2-ylmethyl or l, 3-pyrimidin-2-yl-methyl. In a further preferred embodiment, the invention relates to the compounds of the formula (I-
Figure imgf000013_0001
Figure imgf000013_0001
wobei R1, R3, R4 (d.h. R4a und R4b haben unabhängig voneinander die oben für R4 beschriebene Bedeutung), R6, R13, Y und n die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. where R 1 , R 3 , R 4 (ie R 4a and R 4b independently of one another have the meaning described above for R 4 ), R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
Die Formel (1-1) beschreibt eine bevorzugte Ausführungsform der erfindungesgemäßen Verbindungen der Formel (I). Hier stehen R2 für H, W für O, Q1 und Q2 für CH, Q3 für C-R4a, Q4 für C-R4b und A für - CO-NR13-. G steht für ein freies Elektonenpaar. The formula (1-1) describes a preferred embodiment of the erfindungesgemäßen compounds of formula (I). Here R 2 is H, W is O, Q 1 and Q 2 are CH, Q 3 is CR 4a , Q 4 is CR 4b and A is - CO-NR 13 -. G stands for a free Elektonenpaar.
In einer weiteren bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I- 2)
Figure imgf000014_0001
In a further preferred embodiment, the invention relates to the compounds of the formula (I-2)
Figure imgf000014_0001
wobei R1, R3, R4 (d.h. R4a hat die oben für R4 beschriebene Bedeutung), R6, R13, Y und n die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1 -1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. wherein R 1 , R 3 , R 4 (ie R 4a has the meaning described above for R 4 ), R 6 , R 13 , Y and n have the meanings described above, in particular those in embodiment (1 -1) or embodiment ( 2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
Die Formel (1-2) beschreibt eine bevorzugte Ausführungsform der erfindungesgemäßen Verbindungen der Formel (I).Hier stehen R2 für H, W für O, Q1 und Q2 für CH, Q3 für C-R4a, Q4 für N und A für -CO- NR13-. G steht für ein freies Elektonenpaar. The formula (1-2) describes a preferred embodiment of the inventive compounds of the formula (I). Here R 2 is H, W is O, Q 1 and Q 2 is CH, Q 3 is CR 4a , Q 4 is N and A is -CO- NR 13 -. G stands for a free Elektonenpaar.
In einer weiteren bevorzugten Ausführungsform 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)
Figure imgf000014_0002
Figure imgf000014_0002
wobei R1, R3, R4 (d.h. R4a und R4b haben unabhängig voneinander die oben für R4 beschriebene Bedeutung), R6, R13, Y und n die oben beschriebenen Bedeutungen haben, insbesondere die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. where R 1 , R 3 , R 4 (ie R 4a and R 4b independently of one another have the meaning described above for R 4 ), R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
Die Formel (1-3) beschreibt eine bevorzugte Ausführungsform der erfindungesgemäßen Verbindungen der Formel (I).Hier stehen R2 für H, W für O, Q1 für N, Q2 für CH, Q3 für C-R4a, Q4 für C-R4b und A für -CO-NR13-. G steht für ein freies Elektonenpaar. The formula (1-3) describes a preferred embodiment of the inventive compounds of the formula (I). Here R 2 is H, W is O, Q 1 is N, Q 2 is CH, Q 3 is CR 4a , Q 4 is CR 4b and A for -CO-NR 13 -. G stands for a free Elektonenpaar.
In einer weiteren bevorzugten Ausführungsform der Erfindung steht in den Verbindungen der Formel (I) W für O, G für ein freies Elektronenpaar und Q1, Q2, Q3 und Q4 für C-R4, wobei alle anderen Gruppen, Reste und Substituenten die oben in Ausgestaltung (1 -1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. In einer weiteren bevorzugten Ausführungsform der Erfindung steht in den Verbindungen der Formel (I) W für O, G für ein freies Elektronenpaar und R2 für Wasserstoff und X für Trifluormethyl, wobei alle anderen Gruppen, Reste und Substituenten die oben in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. In a further preferred embodiment of the invention, in the compounds of the formula (I) W is O, G is a lone electron pair and Q 1 , Q 2 , Q 3 and Q 4 are CR 4 , where all other groups, radicals and substituents are above in embodiment (1 -1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-2) have described meanings. In a further preferred embodiment of the invention, in the compounds of the formula (I) W is O, G is a free electron pair and R 2 is hydrogen and X is trifluoromethyl, where all other groups, radicals and substituents are those described above in the embodiment (1). 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
In einer weiteren bevorzugten Ausführungsform der Erfindung steht in den Verbindungen der Formel (I) W für O, G für ein freies Elektronenpaar, Q1, Q2, Q3 und Q4 für C-R4 sowie A für -CO-NR13-, wobei alle anderen Gruppen, Reste und Substituenten die oben in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) beschriebenen Bedeutungen haben. In a further preferred embodiment of the invention, in the compounds of the formula (I) W is O, G is a lone electron pair, Q 1 , Q 2 , Q 3 and Q 4 are CR 4 and A is -CO-NR 13 -, where all other groups, radicals and substituents are as defined above in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-5). 2) have described meanings.
Ebenfalls bevorzugte erfindungsgemäße Verbindungen sind die in Tabelle 1 gezeigten Verbindungen der allgemeinen Formel (I) bzw. (1-1). Likewise preferred compounds according to the invention are the compounds of the general formula (I) or (1-1) shown in Table 1.
Die oben angegebenen einzelnen allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen für die Substituenten R1 bis R16, Q1 bis Q4, n, X, W, A, Y und G können erfindungsgemäß beliebig miteinander kombiniert werden. The above-mentioned individual general, preferred, particularly preferred and very particularly preferred meanings for the substituents R 1 to R 16 , Q 1 to Q 4 , n, X, W, A, Y and G can be combined with one another according to the invention.
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 oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder 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. Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Erfindungsgemäß besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. Particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.
Erfindungsgemäß ganz besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
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. Depending on the nature of the substituents, the compounds of the formula (I) may also be present as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers in different compositions. Both the pure Stereoisomers as well as 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 Polymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden. 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.
Die vorliegenden Verbindungen der allgemeinen Formel (I) können gegebenenfalls ein chirales Kohlenstoffatom aufweisen. The present compounds of the general formula (I) may optionally have a chiral carbon atom.
Gemäß den Regeln nach Cahn, Ingold und Prelog (CIP-Regeln) können diese Substituenten sowohl eine (R)- als auch eine (S)-Konfiguration aufweisen. Von der vorliegenden Erfindung werden Verbindungen der allgemeinen Formel (I) sowohl mit (S)- als auch mit (R)-Konfiguration an den jeweiligen chiralen Kohlenstoffatomen umfasst, d.h., dass die vorliegende Erfindung die Verbindungen der allgemeinen Formel (I) erfasst, in welchen die betreffenden Kohlenstoffatome jeweils unabhängig voneinander According to the rules of Cahn, Ingold and Prelog (CIP rules), these substituents may have both an (R) and an (S) configuration. The present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
(1) eine (R)-Konfiguration; oder (2) eine (S)-Konfiguration aufweisen. Wenn mehrere Chiralitätszentren in den Verbindungen der allgemeinen Formel (I) vorliegen, sind beliebige Kombinationen der Konfigurationen der Chiralitätszentren möglich, d.h. dass (1) an (R) configuration; or (2) have an (S) configuration. When multiple chiral centers are present in the compounds of general formula (I), any combinations of the configurations of the chiral centers are possible, i. that
(1) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration; (2) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (R)- Konfiguration; und (1) one chiral center the (R) configuration and the other chiral center the (S) configuration; (2) one chiral center the (R) configuration and the other chiral center the (R) configuration; and
(3) ein Chiralitätszentrum die (S)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration aufweisen kann. Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkyl, 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-Butyl, iso-Butyl, sek.-Butyl, tert.-Butyl, n- Pentyl, iso-Pentyl, Neopentyl, tert.-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 1 -Ethylpropyl, 1 ,2- Dimethylpropyl, Hexyl n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl und n-Dodecyl. Von diesen Alkylresten sind Ci-C6-Alkylreste besonders bevorzugt. Insbesondere bevorzugt sind Ci-C i-Alkylreste. (3) one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration. 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 12 -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 -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n Of these alkyl radicals, C 1 -C 6 -alkyl radicals are particularly preferred, C 1 -C -alkyl radicals being particularly preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkenyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-C12-Alkenylrest, welcher mindestens eine Doppelbindung aufweist, beispielsweise 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-Hexenyl, 4-Hexenyl, 5- Hexenyl und 1 ,4-Hexadienyl, verstanden. Bevorzugt hiervon sind C2-C6-Alkenylreste und besonders bevorzugt sind C2-C4-Alkenylreste. Unless otherwise defined elsewhere, the term "alkenyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having 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-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, preferred are C2-C6-alkenyl radicals and particularly preferred are C2-C4-alkenyl radicals.
Sofern nicht an 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-C12-Alkinylrest, welcher mindestens eine Dreifachbindung aufweist, beispielsweise Ethinyl, 1 -Propinyl und Propargyl, verstanden. Bevorzugt hiervon sind C3-C6-Alkinylreste und besonders bevorzugt sind C3-C4-Alkinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Unless otherwise defined elsewhere, the term "alkynyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkynyl having at least one triple bond, for example, ethynyl, 1-propynyl C 3 -C 6 -alkynyl radicals are preferred and C 3 -C 4 -alkynyl radicals are particularly preferred. The alkynyl radical may also have at least one double bond.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Cycloalkyl", 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-Cycloalkylreste. Unless otherwise defined elsewhere, the term "cycloalkyl", either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are 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, verstanden. Unless otherwise defined elsewhere, the term "aryl" according to the invention is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff„Arylalkyl" eine Kombination von erfindungsgemäß definierten Resten „Aryl" und „Alkyl" verstanden, wobei der Rest im Allgemeinen über die Alkylgrupe gebunden wird, Beispiele hierfür sind Benzyl, Phenylethyl oder a- Methylbenzyl, wobei Benzyl besonders bevorzugt ist. Unless otherwise defined elsewhere, the term "arylalkyl" 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 being benzyl, phenylethyl or Methylbenzyl, with benzyl 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. Bevorzugt steht Hetaryl für Pyridinyl oder Pyrimidinyl. 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. Preferably hetaryl is pyridinyl or pyrimidinyl.
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, Tetrahydrofuryl. 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, tetrahydrofuryl.
Sofern nicht an anderer Stelle anders definiert, bedeuten „Oxo-Heterocyclyl" 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 elsewhere, "oxo-heterocyclyl" or "dioxo-heterocyclyl" means a heterocyclyl which contains at at least one position in the ring a ring atom which is substituted by one or two (= 0) groups is. 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 „Halogenalkyl", 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. 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 the same or different halogen atoms. "Halogen" here stands for fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
Unter dem Begriff „Alkoxy", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkoxy, wird vorliegend ein Rest O-Alkyl verstanden, wobei der Begriff„Alkyl" die oben stehende Bedeutung aufweist. The term "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 "alkyl" having the meaning given above.
Verfahren und Verwendungen 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 Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel immer auch den Begriff Pflanzenschutzmittel. Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit 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, 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. Sie können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides. In the context of the present application, the term pest control 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, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. 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 gallinae, 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 coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus 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 Chilopoda 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, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Supella longipalpa; aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., 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 confinis, 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 ferrugineus, 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, Diloboderus spp., Epilachna spp., z.B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z.B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z.B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., 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., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z.B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z.B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, 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 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, Calliphora erythrocephala, Calliphora 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, Delia spp., z.B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z.B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., 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., Paralauterborniella subcincta, Pegomya spp., z.B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., z.B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis 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; aus der Ordnung der Hemiptera z.B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z.B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena 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, Aphanostigma 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, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z.B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis 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 stevensi, Eriosoma spp., z.B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla 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, 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, Nephotettix spp., z.B. Nephotettix cinetieeps,, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z.B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z.B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, 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, Psylla mali, Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., z.B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z.B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z.B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, 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. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunetus, 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, 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 hesperas, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., z.B. Nezara viridula, Oebalus spp., Piesma quadrata, Piezodoras spp., z.B. Piezodoras guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella 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., Diprion spp., z.B. Diprion similis, Hoplocampa spp., z.B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., z.B. Vespa crabro, Xeris spp.; aus der Ordnung der Isopoda z.B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z.B. Coptotermes spp., z.B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., z.B. Reticulitermes flavipes, Reticulitermes hesperas; 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., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z.B. Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphaloceras spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z.B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z.B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella 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 pranivora, Hedylepta spp., Helicoverpa spp., z.B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z.B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., 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 clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., z.B. Pectinophora gossypiella, Perileucoptera 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 (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z.B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia 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., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, 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, Hieroglyphus spp., Locusta spp., z.B. Locusta migratoria, Melanoplus spp., z.B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z.B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Ctenocephalides spp., z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z.B. Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, 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. Scutigerella spp., z.B. Scutigerella immaculata; Pests of the genus Arthropoda, in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hicoriae , Epitrimerus pyri, Eutetranychus spp., Eg Eutetranychus banksi, Eriophyes spp., Eg Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Eg Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp. , Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Eg Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pra tensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., eg 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., Eg Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., Eg Tetranychus cinnabaris, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the genus of Chilopoda, for example Geophilus spp., Scutigera spp .; from the order or class of Collembola eg Onychiurus armatus; Sminthurus viridis; from the class Diplopoda eg Blaniulus guttulatus; from the class of the Insecta, eg from the order of the Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Supella longipalpa; from the order of the Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., eg Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., eg Anthonomus grandis , Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Eg Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus eg Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., eg Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., eg Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., eg Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Eg Epilachna borealis, Epilachna varivestis, Epitrix spp., Eg Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator , Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Eg Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata , Leucoptera spp., Eg Leucoptera coffeella, Lissorhoptrus oryzop hilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., eg Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., eg Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, oryzae Oryzaphagus, Otiorhynchus spp., for example, Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri Phyllotreta spp., Eg Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., eg Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeam ais, Sphenophorus spp., Stegobium paniceum, Starchus spp., eg Starchus paludatus, Symphyletes spp., Tanymecus spp., eg Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., eg Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., eg Zabrus tenebrioides; from the order of the Diptera eg Aedes spp., eg Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., eg Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., eg Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., eg Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp Contarinia johnsoni, Contarina nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp. Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila sp p., eg, Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., eg Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., eg Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., eg Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp , Paralauterborniella subcincta, Pegomya spp., Eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., eg Tipula paludosa, Tipula simplex; from the order of the Hemiptera eg Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., eg Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Eg Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., Eg Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., Eg 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., Eg Aspidiotus nerii, Atanus spp. , Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp. , eg Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis , Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., Eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Mon ellia costalis, Monelliopsis pecanis, Myzus spp., eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae ,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp. Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Eg Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp. , Pyrilla spp., Quadraspidiotus spp., Eg, Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadr aspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum , Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., eg Eusystus heros, Euschistus servus, Eustistus tristigmus, Eushtistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocoris varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulinus, Lygus spp., Eg Lygus elisus, Lygus hesperas, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., Eg Nezara viridula, Oebalus spp., Piesma quadrata, Piezodoras spp. eg, Piezodoras guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Monomorium pharaonis, Sirex spp , Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., Eg Vespa crabro, Xeris spp .; from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera eg Coptotermes spp., eg Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., eg Reticulitermes flavipes, Reticulitermes hesperas; from the order of the Lepidoptera eg Achroia grisella, Acronica major, Adoxophyes spp., eg Adoxophyes orana, Aedia leucomelas, Agrotis spp., eg Agrotis segetum, Agrotis ipsilon, Alabama spp., eg Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., eg Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus pinarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp. eg Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphaloceras spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., eg Cydia nigricana, Cydia pomonella, Dalaca noctuides Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., Eg Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiph yas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., eg Grapholita molesta, Grapholita pranivora, Hedylepta spp Helicoverpa spp., Eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Eg Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp., eg Lymantria dispar, Lyonetia spp., eg Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., eg Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., eg Phthorimaea operculella, Phyllocnis citrella, Phyllonorycter spp., eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp. , Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Eg Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Eg Schoenobius bipunctifer, Scirpophaga spp. eg Scirpophaga innotata, Scotia segetum, Sesamia spp., eg Sesamia inferens, Sparganothis spp., Spodoptera spp., eg Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., Eg Trichoplusia ni, Tryporyza inc ertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria eg Acheta domesticus, Dichroplus spp., Gryllotalpa spp., eg Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., eg Locusta migratoria, Melanoplus spp., eg Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera eg Lepinotus spp., Liposcelis spp .; from the order of Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., eg Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus , Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., Eg Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, insbesondere 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.; Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp.; Pests from the strain of Mollusca, in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp . Animal and human parasites from the strains of Platyhelminthes and Nematoda, eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp , Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp. Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp , Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp. Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Op isthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp , Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp. Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria 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. Criconemella 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, Hoplolaimus spp., Longidorus spp., z.B. Longidorus africanus, Meloidogyne spp., z.B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., z.B. Paratrichodorus minor, Pratylenchus spp., z.B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z.B. Radopholus citrophilus, 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., z.B. Tylenchulus semipenetrans, Xiphinema spp., z.B. Xiphinema index. Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia z.B. Eimeria spp. bekämpfen. Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., Eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., Eg Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., Eg Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., Eg Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., eg Heterodera avenae, Heter ora glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., eg Longidorus africanus, Meloidogyne spp., eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp. , Paratrichodorus spp., Eg Paratrichodorus minor, Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., Eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp , Scutellonema spp., Subanguina spp., Trichodorus spp., Eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., Eg Tylenchorhynchus annulatus, Tylenchulus spp., Eg Tylenchulus semipenetrans, Xiphinema spp., Eg Xiphinema index. Furthermore, the order of the coccidia, eg Eimeria spp., Can be determined from the sub-region of the protozoa. fight.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstums-regulatoren 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. If appropriate, the compounds of the formula (I) may 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 agent against 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 Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsforderer, z. B. vegetative Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester vegetativer Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester 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 fordernde 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. Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides. B. drench, drip and spray liquors, comprising at least one compound of formula (I). Optionally, the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z. For example, vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such. Dioctylsulfosuccinate or hydroxypropyl-guar polymers and / or humectants, e.g. 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 Specifications, 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 einem oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Ver dicker 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 fördern. 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 Specifications, 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. Preferably, they are formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants. 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 promote 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 oberflächenaktive Stoffe. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z.B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen 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). As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as 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 infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasser-stoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol 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.
Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z.B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder aliphatische Kohlenwasserstoffe wie z.B. Chlorbenzol, Chlorethylen, oder Methylen- chlorid, aliphatische Kohlenwasserstoffe wie z.B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z.B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z.B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z.B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehl, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und /oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: 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. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or 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. In principle, all suitable carriers can be used. Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers , Mixtures of such carriers can also be used. Suitable carriers for granules are: eg 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, corn cobs and tobacco stems. Also, liquefied gaseous diluents or solvents can be used. Particularly suitable are those extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
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 Lignosulphonsäure, Salze von Phenolsulphonsäure oder Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen 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. 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 lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic 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 sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-sulphite liquors 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 Anwendungsformen 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. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. As further adjuvants, in the formulations and the applications derived therefrom, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen 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 vegetabile Öle sein. Furthermore, the formulations and their derived use forms as additional auxiliaries also adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like 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 Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Humectans, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar Polymere. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, 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 which reduce the dynamic 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 Betracht, 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 Stoffbeweglichkeit (Mobilität) 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 Sojaölmethylester, Fettamine Alkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Suitable penetration promoters in the present context are 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 material mobility (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 soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
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. 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 Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. Mischungen The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie. The application is done in a custom forms adapted to the application. mixtures
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbizide, Düngemitteln, Vogelrepellentien, 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. Desweiteren 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. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteerträge steigern, die Reife beeinflussen, die Qualität und/oder den Ernährungswert der Ernteprodukte 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, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the 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 Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
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 der Formel (I) in Mischungen mit Mitteln zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. Furthermore, 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 the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. In a particular embodiment of 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. Als Mischpartner kommen zum Beispiel die folgenden Verbindungen in Betracht: Insektizide / Akarizide / Nematizide: 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. Suitable mixing partners are, for example, the following compounds: 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). The active substances mentioned here with 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 ).
(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. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (1) acetylcholinesterase (AChE) inhibitors such as carbamates, eg alanycarb, aldicarb, bendocarb, benfuracarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, Pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, eg acephates, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoates, Dimethylvinphos, Disulfonot, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidone, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, thiometone, triazophos, triclorfone and vamidothion.
(2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B. Chlordane und Endosulfan oder Phenylpyrazole (Fiprole), z.B. Ethiprole und Fipronil. (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
(3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, 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, Cyphenothrin [(lR)-trans-Isomere], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomere), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(lR)-trans- Isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)- Isomere)], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (3) sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. 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, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, Flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(lR) -trans- isomer), prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) - isomer)], Tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Nikotinerge Acetylcholin-Rezeptor (nAChR) Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nikotin oder Sulfbxaflor. (5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispielsweise Spinosine, z.B. Spinetoram und Spinosad. (4) nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfbxaflor. (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
(6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) chloride channel activators, such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
(7) Juvenilhormon-Imitatoren, wie beispielsweise Juvenilhormon- Analoge, z.B. Hydroprene, Kinoprene und Methoprene oder Fenoxycarb oder Pyriproxyfen. (7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
(8) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise Alkylhalide, z.B. Methylbromid und andere Alkylhalide; oderChloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein. (8) agents with unknown or non-specific mechanisms of action, such as Alkyl halides, eg methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
(9) Selektive Fraßhemmer, z.B. Pymetrozine oder Flonicamid. (9) Selective feeding inhibitors, e.g. Pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox und Diflovidazin oder Etoxazole. (11) Mikrobielle Disruptoren der Insektendarmmembran, z.B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und BT Pflanzenproteine: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl . (10) mite growth inhibitors, e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole. (11) Insect intestinal membrane microbial disruptors, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
(12) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargite oder(12) oxidative phosphorylation inhibitors, ATP disruptors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and fenbutatin oxide or propargite or
Tetradifon. Tetradifon.
(13) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr, DNOC, and sulfluramide.
(14) Nikotinerge Acetylcholin-Rezeptor- Antagonisten, wie beispielsweise Bensultap, Cartap-hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Nicotinergic acetylcholine receptor antagonists 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 Bupro fezin. (17) Häutungshemmer (insbesondere bei Dipteren, d.h.Zweiflüglern), wie beispielsweise Cyromazine. (16) inhibitors of chitin biosynthesis, type 1, such as Bupro fezin. (17) Anti-skinning agents (especially in dipterans, i.e., two-toed), such as Cyromazine.
(18) Ecdyson-Rezeptor Agonisten, wie beispielsweise Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. (18) ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
(19) Oktopaminerge Agonisten, wie beispielsweise Amitraz. (19) Octopaminergic agonists, such as amitraz.
(20) Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (20) Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
(21) Komplex-I-Elektronentransportinhibitoren, beispielsweise METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenone (Derris). (21) complex I electron transport inhibitors, for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
(22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone. (23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat. (22) Voltage-dependent sodium channel blockers, eg indoxacarb or metaflumizone. (23) inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, eg spirodiclofen, spiromesifen and spirotetramat.
(24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanid. (25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen. (24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide. (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
(28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide, weitere Wirkstoffe wie beispielsweise Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Dicofol, Diflovidazin, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyrifluquinazon, Pyriminostrobin, Tetramethylfluthrin und Iodmethan; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) , sowie folgende Verbindungen:3- Brom-N- {2-brom-4-chlor-6- [( 1 -cyclopropylethyl)carbamoyl]phenyl} - 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol- 5-carboxamid (bekannt aus WO2005/077934) und l- {2-Fluor-4-methyl-5-[(2,2,2- trifluorethyl)sulfmyl]phenyl}-3-(trifluormethyl)-lH-l,2,4-triazol-5-arnin (bekannt aus WO2006/043635), {1 (2E)-3-(4-Ch^henyl)prop-2-en-l-yl]-5-fta (28) ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Dicofol, Diflovidazine, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazone, pyriminostrobin, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following compounds: 3-bromo-N- {2-bromo-4-chloro-6- [(1-cyclopropyl-ethyl) -carbamoyl] -phenyl} -1 - (3-chloropyridin-2-yl) -1 H -pyrazole-5-carboxamide (known from WO2005 / 077934) and 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfmyl] phenyl} -3- (trifluoromethyl) -1H-l, 2,4-triazole-5-arnine (known from WO2006 / 043635), {1 (2E) -3- (4-chloro-1-yl) prop-2 -en-l-yl] -5-fta
yl)methanon (bekannt aus WO2003/106457), 2-Chlor-N-[2-{l-[(2E)-3-(4-chlorphenyl)prop-2-en-l- yl]piperidin-4-yl}-4-(trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494), 3-(2,5- Dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009/049851), 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus WO2009/049851), 4-(But-2-in-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160), 4-(But-2-in-l-yloxy)-6-(3-chlorphenyl)pyrimidin (bekannt aus WO2003/076415), PF1364 (CAS-Reg.No. 1204776-60-2), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4,5-dihydro-l,2- oxazo 1-3 -yl]-2-methyl-N- {2-0X0-2- [(2,2,2-trifluorethyl)amino]ethyl}benzamid (bekannt ausyl) methanone (known from WO2003 / 106457), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) prop-2-en-1-yl] piperidin-4-yl } -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-ene 2-one (known from WO2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from WO2009 / 049851), 4- (but-2-yn-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160), 4- (but- 2-yn-1-yloxy) -6- (3-chlorophenyl) pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), 4- [5- (3,5-) Dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-l, 2-oxazo1,3-yl] -2-methyl-N- {2-0X0-2- [(2,2,2-trifluoroethyl) amino] ethyl} benzamide (known from
WO2005/085216), 4- {5-[3-Chlor-5-(trifluormethyl)phenyl]-5-(trifluormethyl)-4,5-dihydro-l,2-oxazol-3- yl}-N- {2-0X0-2- [(2,2,2-trifluorethyl)amino]ethyl}-l-naphthamid (bekannt aus WO2009/002809), Methyl- 2- [2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)-5-chlor-3 -methylbenzoyl] -2- methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2- yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2- [2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)-5- cyan-3 -methylbenzoyl] -2-methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[3,5- dibrom-2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)benzoyl] -2- ethylhydrazincarboxylat (bekannt aus WO2005/085216), l-(3-Chlorpyridin-2-yl)-N-[4-cyan-2-methyl-6- (methylcarbamoyl)phenyl] -3 - { [5-(trifluormethyl)-2H-tetrazol-2-yl]methyl} - 1 H-pyrazol-5-carboxamid (bekannt aus WO2010/069502), N- [2-(5-Amino- 1 ,3 ,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl] -3 -brom- 1 - (3-chlorpyridin-2-yl)-lH-pyrazol-5-carboxamid (bekannt aus CN102057925), 3-Chlor-N-(2-cyanpropan- 2-yl)-N- [4-( 1 , 1 , 1 ,2,3,3 ,3 -heptafluorpropan-2-yl)-2-methylphenyl]phthalamid (bekannt aus WO2012/034472), 8-Chlor-N-[(2-chlor-5-methoxyphenyl)sulfonyl]-6-(trifluormethyl)imidazo[l,2- a]pyridin-2-carboxamid (bekannt aus WO2010/129500), 4-[5-(3,5-Dich^henyl)-5-(trifluormethyl)-4,5- dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxidothietan-3-yl)benzamid (bekannt aus WO2009/080250), 4- [5-(3,5-Dichlo^henyl)-5-(trifluormethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l WO2005 / 085216), 4- {5- [3-chloro-5- (trifluoromethyl) phenyl] -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl} -N- {2 -0X0-2- [(2,2,2-trifluoroethyl) amino] ethyl} -l-naphthamide (known from WO2009 / 002809), methyl 2- [2- ({[3-bromo-1 - (3) chloropyridin-2-yl) -1 H -pyrazol-5-yl] carbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [2- ({ [3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), Methyl 2- [2- ({[3-bromo-1 - (3-chloropyridin-2-yl) -1 H -pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2 methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [3,5-dibromo-2- ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] ] carbonyl} amino) benzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), 1- (3-chloropyridin-2-yl) -N- [4-cyano-2-methyl-6-] (methylcarbamoyl) phenyl] -3 - {[5- (trifluoromethyl) -2H-tetrazol-2-yl] methyl} -1H-pyrazole-5-carboxamide (known from WO2010 / 069502), N- [2- (5 -Amino-1,3,3,4-thiadiazol-2-yl) -4-chloro-6-methylphenyl] -3-bromo-1 - (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide (known from CN102057925), 3-chloro-N- (2-cyanopropan-2-yl) -N- [4- (1,1,2,3,3,3-heptafluoropropan-2-yl) -2-methylphenyl ] Phthalamide (known from WO2012 / 034472), 8-chloro-N - [(2-chloro-5-methoxyphenyl) sulfonyl] -6- (trifluoromethyl) imidazo [l, 2-a] pyridine-2-carboxamide (known from WO2010 / 129500), 4- [5- (3,5-dichloro) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- ( 1-oxidothietan-3-yl) benzamide (known from WO2009 / 080250), 4- [5- (3,5-dichloro-1-yl-yl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazole 3-yl] -2-methyl-N- (l
yl)benzamid (bekannt aus WO2012/029672), l-[(2-Chlor-l,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H- pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus WO2009/099929), l-[(6-Chlorpyridin-3-yl)methyl]-4- oxo-3-phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus WO2009/099929), (5S,8R)-l-[(6- Chlo^yridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-lH-5,8-epoxyimidazo[l,2-a]azepin (bekannt aus WO2010/ 069266), (2E)- 1 - [(6-Chlorpyridin-3 -yl)methyl] -N'-nitro-2-pentylidenhydrazincarboximidamid (bekannt aus WO2010/060231), 4-(3-{2,6-Dichlor-4-[(3,3-dichloφrop-2-en-l-yl)oxy]phenoxy}propoxy)- 2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2-(tert-Butylcarbamoyl)-4-chlor- 6-methylphenyl] - 1 -(3 -chlorpyridin-2-yl)-3 -(fluormethoxy)- 1 H-pyrazol-5-carboxamid (bekannt aus WO2008/134969). yl) benzamide (known from WO2012 / 029672), 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-l-ium-2-olate (known from WO2009 / 099929), l - [(6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-l-ium-2-olate (known from WO2009 / 099929), (5S, 8R) -1 - [(6-chloro-3-yl) methyl] -9-nitro-2,3,5, 6,7,8-hexahydro-1H-5,8-epoxyimidazo [1,2-a] azepine (known from WO2010 / 069266), (2E) - 1 - [(6-chloropyridin-3-yl) methyl] - N'-nitro-2-pentylidenehydrazinecarboximidamide (known from WO2010 / 060231), 4- (3- {2,6-dichloro-4 - [(3,3-dichloφrop-2-en-1-yl) oxy] phenoxy} propoxy) -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN101337940), N- [2- (tert-butylcarbamoyl) -4-chloro-6-methylphenyl] -1- (3-chloropyridin-2-yl) 3 - (fluoromethoxy) -1 H -pyrazole-5-carboxamide (known from WO2008 / 134969).
Fungizide fungicides
Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides). The active ingredients specified here with their "common name" are known, for example, described in the "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides).
(1) Inhibitoren der Ergosterol-Biosynthese, wie beispielsweise (1.1) Aldimorph, (1.2) Azaconazol, (1.3) Bitertanol, (1.4) Bromuconazol, (1.5) Cyproconazol, (1.6) Diclobutrazol, (1.7) Difenoconazol, (1.8) Diniconazol, (1.9) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorph Acetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-Cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalil Sulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifm, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefurazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafin, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) l-(4-Ch^henyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanol, (1.61) Methyl- 1 -(2,2- dimethyl-2,3 -dihydro- 1 H-inden- 1 -yl)-l H-imidazol-5-carboxylat, ( 1.62) N'- {5-(Difluormethyl)-2-methyl-4- [3-(trimethylsilyl)propoxy]phenyl} -N-ethyl-N-methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'- {2- methyl-5-(trifluomethyl)-4-[3-(trimethy und (1.64) 0-[l-(4-(1) inhibitors of ergosterol biosynthesis, such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil Sulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifm, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) Penconazole, (1.38) piperalin, (1.39) prochlorazole, (1.40) propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) Tebuconazole, (1 .48) Terbinafine, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizole, (1.54) Triforin, (1.55) Triticonazole, (1.56) Uniconazole, (1.57) Uniconazole p, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1- (4-chloro-1-yl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, (1.61) methyl-1 - (2,2-dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylate, (1.62) N '- {5- (difluoromethyl) -2-methyl- 4- [3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N '- {2- methyl-5- (trifluoromethyl) -4- [3- (trimethyl and (1.64) 0- [1- (4-
Methoxyphenoxy)-3,3-dimethylbutan-2-yl]-lH-imidazol-l -carbothioat, (1.65) Pyrisoxazole. Methoxyphenoxy) -3,3-dimethylbutan-2-yl] -1H-imidazole-1-carbothioate, (1.65) pyrisoxazoles.
(2) Inhibitoren der Respiration (Atmungsketten-lnhibitoren), wie beispielsweise (2.1) Bixafen, (2.2) Boscalid, (2.3) Carboxin, (2.4) Diflumetorim, (2.5) Fenfuram, (2.6) Fluopyram, (2.7) Flutolanil, (2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mischung des syn-epimeren Razemates 1RS,4SR,9RS und des anti-empimeren Razemates 1RS,4SR,9SR, (2.12) Isopyrazam (anti- epimeres Razemat ), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti- epimeres Enantiomer 1S,4R,9R), (2.15) Isopyrazam (syn-epimeres Razemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxane, (2.23) Thifluzamid, (2.24) 1 -Methyl-N- [2-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] -3 -(trifluormethyl)- 1 H-pyrazol-4- carboxamid, (2.25) 3-(Difluormethyl)- 1 -methyl-N- [2-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] - 1 H-pyrazol-4- carboxamid, (2.26) 3 -(Difluormethyl)-N- [4-fluor-2-( 1 , 1 ,2,3,3,3-hexafluorpropoxy)phenyl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (2.27) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3-(difluormethyl)-l- methyl- lH-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4-{[4-(trifluormethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.29) Benzovindiflupyr, (2.30) N-[(lS,4R)-9-(Dichlormethylen)- l,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid und (2.31) N- [(1 R,4S)-9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3 -(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.32) 3 -(Difluormethyl)- 1 -methyl-N-(l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H- inden-4-yl)-lH-pyrazol-4-carboxamid, (2.33) l,3,5-Trimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl)-lH-pyrazol-4-carboxamid, (2.34) l-Methyl-3-(trifluomethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden- 4-yl)- 1 H-pyrazol-4-carboxamid, (2.35) 1 -Methyl-3 -(trifluormethyl)-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- lH-inden-4-yl]- lH-pyrazol-4-carboxamid, (2.36) 1 -Methyl-3-(trifluormethyl)-N-[(3S)- 1 , 1 ,3-trimethyl-2,3- dihydro-1 H-inden-4-yl]-l H-pyrazol-4-carboxamid, (2.37) 3-(Difluormethyl)- 1 -methyl-N- [(3 S)- 1,1,3- trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-l-methyl-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.39) 1 ,3,5-Trimethyl-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.40) 1 ,3,5-Trimethyl-N- [(3 S)- 1,1, 3 -trimethyl-2,3 -dihydro- lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2- Chlor-N-(l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)pyridine-3 -carboxamid, (2.43) Isofetamid (3) Inhibitoren der Respiration (Atmungsketten-lnhibitoren) am Komplex III der Atumungskette, wie beispielsweise (3.1) Ametoctradin, (3.2) Amisulbrom, (3.3) Azoxystrobin, (3.4) Cyazofamid, (3.5) Coumethoxystrobin, (3.6) Coumoxystrobin, (3.5) Dimoxystrobin, (3.8) Enestroburin, (3.9) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-Methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2- {[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylethanamid, (3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2- { [( {( 1 E)- 1 - [3 -(2) inhibitors of respiration (respiratory chain inhibitors) such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxine, (2.20) penflufen, (2.21) Penthiopyrad, (2.22) Sedaxanes, (2.23) Thifluzamide, (2.24) 1-Methyl-N- [2- (1, 1, 2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) -1 H -pyrazole-4 - carboxamide, (2.25) 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1 H -pyrazole ol-4-carboxamide, (2.26) 3 - (difluoromethyl) -N- [4-fluoro-2- (1,1,3,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole -4-carboxamide, (2.27) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.28 ) 5,8-Difluoro-N- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.29) benzovindiflupyr, ( 2.30) N - [(IS, 4R) -9- (dichloromethylene) -1,3,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -l-methyl-1H- pyrazole-4-carboxamide and (2.31) N- [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl ) - 1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3 - (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-indene) 4-yl) -1H-pyrazole-4-carboxamide, (2.33) l, 3,5-trimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) - 1H-pyrazole-4-carboxamide, (2.34) 1-methyl-3- (trifluoromethyl) -N- (1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1 H- pyrazole-4-carboxamide, (2.35) 1 -Met hyl-3 - (trifluoromethyl) -N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.36) 1 -Methyl-3- (trifluoromethyl) -N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, ( 2.37) 3- (Difluoromethyl) -1-methyl-N- [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide , (2.38) 3- (difluoromethyl) -1-methyl-N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1 H-pyrazole 4-carboxamide, (2.39) 1, 3,5-trimethyl-N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole 4-carboxamide, (2.40) 1, 3,5-trimethyl-N- [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole 4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, ( 2.43) isofetamide (3) inhibitors of respiration (respiratory chain inhibitors) at the complex III of the respiratory chain, such as (3.1) ametoctradine, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamide , (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.5) dimoxystrobin, (3.8) enestroburine, (3.9) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14 ) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) - 2- (2- {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N- methylethanamide, (3.24) (2E) -2- (methoxyimino) -N-methyl-2- (2- {[({(1 E) -1 - [3 -
(rrifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)ethanamid, (3.25) (2E)-2-(Methoxyimino)-N- methyl-2- {2- [(E)-( { 1 - [3 -(trifluormethyl)phenyl] ethoxy} imino)methyl]phenyl} ethanamid, (3.26) (2E)-2- {2- [({[(lE)-l-(3- {[(E)-l-Fluor-2-phenylethenyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylethanamid, (3.27) (2E)-2- {2- [( { [(2E,3E)-4-(2,6-Dichlorphenyl)but-3 -en-2- yliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamid, (3.28) 2-Chlor-N-(l,l,3- trimethyl-2,3 -dihydro- 1 H-inden-4-yl)pyridin-3 -carboxamid, (3.29) 5-Methoxy-2-methyl-4-(2- { [( {( 1 E)- 1 - [3-(trifluormethyl)phenyl]ethyliden}amino)o^ (3.30) Methyl-(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3- methoxyprop-2-enoat, (3.31) N-(3-Ethyl-3,5,5-rrimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamid, (3.32) 2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (4) Inhibitoren der Mitose und Zellteilung, wie beispielsweise (4.1) Benomyl, (4.2) Carbendazim, (4.3) Chlorfenazol, (4.4) Diethofencarb, (4.5) Ethaboxam, (4.6) Fluopicolid, (4.7) Fuberidazol, (4.8) Pencycuron, (4.9) Thiabendazol, (4.10) Thiophanat-Methyl, (4.11) Thiophanat, (4.12) Zoxamid, (4.13) 5-Chlor-7-(4-methylpiperidin-l-yl)-6- (2,4,6-trifluorphenyl)[l,2,4]triazolo[l,5-a]pyrimidin und (4.14) 3-Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4- (2,4,6-trifluoφhenyl)pyridazin. (rrifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) ethanamide, (3.25) (2E) -2- (methoxyimino) -N-methyl-2- {2- [(E) - ({1 - [3 - (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} ethanamide, (3.26) (2E) -2- {2- [({[(IE) -l- (3- {[(E) -l-fluoro -2-phenylethenyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethanamide, (3.27) (2E) -2- {2- [({[(2E, 3E ) -4- (2,6-dichlorophenyl) but-3 -ene-2-ylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethanamide, (3.28) 2-chloro-N- ( l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, (3.29) 5-methoxy-2-methyl-4- (2- {[({( 1E) - 1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) o (3.30) methyl (2E) -2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyprop-2-enoate, (3.31) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, (3.32) 2- {2- [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (4) Mitosis and cell division inhibitors such as (4. 1) Benomyl, (4.2) Carbendazim, (4.3) Chlorfenazole, (4.4) Diethofencarb, (4.5) Ethaboxam, (4.6) Fluopicolide, (4.7) Fuberidazole, (4.8) Pencycuron, (4.9) Thiabendazole, (4.10) Thiophanate-methyl , (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [ l, 5-a] pyrimidine and (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine.
(5) Verbindungen mit Multisite- Aktivität, wie beispielsweise (5.1) Bordeauxmischung, (5.2) Captafol, (5.3) Captan, (5.4) Chlorthalonil, (5.5) Kupferzubereitungen wie Kupferhydroxid, (5.6) Kupfernaphthenat, (5.7) Kupferoxid, (5.8) Kupferoxychlorid, (5.9) Kupfersulfat, (5.10) Dichlofluanid, (5.11) Dithianon, (5.12) Dodine, (5.13) Dodine freie Base, (5.14) Ferbam, (5.15) Fluorfolpet, (5.16) Folpet, (5.17) Guazatin, (5.18) Guazatinacetat, (5.19) Iminoctadin, (5.20) Iminoctadinalbesilat, (5.21) Iminoctadintriacetat, (5.22) Mankupfer, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Zinkmetiram, (5.27) Kupfer-Oxin, (5.28) Propamidin, (5.29) Propineb, (5.30) Schwefel und Schwefelzubereitungen wie beispielsweise Calciumpolysulfid, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram und (5,35) Anilazin. (6) Resistenzinduktoren, wie beispielsweise (6.1) Acibenzolar-S-Methyl, (6.2) Isotianil, (6.3) Probenazol, (6.4) Tiadinil und (6.5) Laminarin. (5) Compounds with multisite activity, such as (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper compounds such as copper hydroxide, (5.6) copper naphthenate, (5.7) copper oxide, (5.8 ) Copper oxychloride, (5.9) copper sulfate, (5.10) dichlorofluanide, (5.11) dithianone, (5.12) dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluoro folpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatinoacetate, (5.19) iminoctadine, (5.20) iminoctadinalesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zinc metiram, (5.27) copper Oxine, (5.28) propamidine, (5.29) propynol, (5.30) sulfur and sulfur compounds such as calcium polysulfide, (5.31) thiram, (5.32) tolylfluanide, (5.33) zineb, (5.34) ziram, and (5.35) anilazine. (6) resistance inducers such as (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil, and (6.5) laminarin.
(7) Inhibitoren der Aminosäure- und Protein-Biosynthese, wie beispielsweise (7.1) , (7.2) Blasticidin-S, (7.3) Cyprodinil, (7.4) Kasugamycin, (7.5) Kasugamycin Hydrochlorid Hydrat, (7.6) Mepanipyrim, (7.7) Pyrimethanil, (7.8) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolin und (7.9) Oxytetracyclin und (7.10) Streptomycin. (7) inhibitors of amino acid and protein biosynthesis, such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin.
(8) Inhibitoren der ATP Produktion, wie beispielsweise (8.1) Fentin Acetat, (8.2) Fentin Chlorid, (8.3) Fentin Hydroxid und (8.4) Silthiofam. (9) Inhibitoren der Zellwandsynthese, wie beispielsweise (9.1) Benthiavalicarb, (9.2) Dimethomorph, (9.3) Flumorph, (9.4) Iprovalicarb, (9.5) Mandipropamid, (9.6) Polyoxins, (9.7) Polyoxorim, (9.8) Validamycin A, (9.9) Valifenalat und (9.10) Polyoxin B. (8) inhibitors of ATP production, such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam. (9) inhibitors of cell wall synthesis, such as (9.1) benthia-valicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) Valifenalate and (9.10) Polyoxin B.
(10) Inhibitoren der Lipid- und Membran-Synthese, wie beispielsweise (10.1) Biphenyl, (10.2) Chlorneb, (10.3) Dicloran, (10.4) Edifenphos, (10.5) Etridiazol, (10.6) Iodocarb, (10.7) Iprobenfos, (10.8)(10) inhibitors of lipid and membrane synthesis, such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8)
Isoprothiolan, (10.9) Propamocarb, (10.10) Propamocarb Hydrochlorid, (10.11) Prothiocarb,, (10.12) Pyrazophos, (10.13) Quintozen, (10.14) Tecnazene und (10.15) Tolclofos-Methyl. Isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb ,, (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazenes and (10.15) tolclofos-methyl.
(11) Inhibitoren der Melanin-Biosynthese, wie beispielsweise (11.1) Carpropamid, (11.2) Diclocymet,(11) inhibitors of melanin biosynthesis, such as (11.1) carpropamide, (11.2) diclocymet,
(11.3) Fenoxanil, (11.4) Fthalid, (11.5) Pyroquilon, (11.6) Tricyclazol, und (11.7) 2,2,2-Trifluorethyl {3- methyl-1 -[(4-methylbenzoyl)amino]butan-2-yl}carbamat. (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilone, (11.6) tricyclazole, and (11.7) 2,2,2-trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butane-2 yl} carbamate.
(12) Inhibitoren der Nukleinsäuresynthese, wie beispielsweise (12.1) Benalaxyl, (12.2) Benalaxyl-M (Kiralaxyl), (12.3) Bupirimat, (12.4) Clozylacon, (12.5) Dimethirimol, (12.6) Ethirimol, (12.7) Furalaxyl, (12.8) Hymexazol, (12.9) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinsäure und (12.14) Octhilinon. (13) Inhibitoren der Signaltransduktion, wie beispielsweise (13.1) Chlozolinat, (13.2) Fenpiclonil, (13.3) Fludioxonil, (13.4) Iprodion, (13.5) Procymidon, (13.6) Quinoxyfen, (13.7) Vinclozolin und (13.8) Proquinazid. (12) inhibitors of nucleic acid synthesis, such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, ( 12.8) Hymexazole, (12.9) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid and (12.14) Octhilinone. (13) Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide.
(14) Entkoppler, wie beispielsweise (14.1) Binapacryl, (14.2) Dinocap, (14.3) Ferimzon, (14.4) Fluazinam und (14.5) Meptyldinocap. (15) Weitere Verbindungen, wie beispielsweise (15.1) Benthiazol, (15.2) Bethoxazin, (15.3) Capsimycin,(14) decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap. (15) Other compounds such as (15.1) benthiazole, (15.2) betoxazine, (15.3) capsimycin,
(15.4) Carvon, (15.5) Chinomethionat, (15.6) Pyriofenon (Chlazafenon), (15.7) Cufraneb, (15.8) Cyflufenamid, (15.9) Cymoxanil, (15.10) Cyprosulfamid, (15.11) Dazomet, (15.12) Debacarb, (15.13) Dichlorphen, (15.14) Diclomezin, (15.15) Difenzoquat, (15.16) Difenzoquat Methylsulphat, (15.17) Diphenylamin, (15.18) Ecomat, (15.19) Fenpyrazamin, (15.20) Flumetover, (15.21) Fluorimid, (15.22) Flusulfamid, (15.23) Flutianil, (15.24) Fosetyl-Aluminium, (15.25) Fosetyl-Calcium, (15.26) Fosetyl- Natrium, (15.27) Hexachlorbenzol, (15.28) Irumamycin, (15.29) Methasulfocarb, (15.30) Methylisothiocyanat, (15.31) Metrafenon, (15.32) Mildiomycin, (15.33) Natamycin, (15.34) Nickel Dimethyldithiocarbamat, (15.35) Nitrothal-Isopropyl, (15.36) Octhilinone, (15.37) Oxamocarb, (15.38) Oxyfenthiin, (15.39) Pentachlorphenol und dessen Salze, (15.40) Phenothrin, (15.41) Phosphorsäure und deren Salze, (15.42) Propamocarb-Fosetylat, (15.43) Propanosin-Natrium, (15.44) Pyrimorph, (15.45) (2E)- 3-(4-Tert-butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (15.46) (2Z)-3-(4-Tert- butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (15.47) Pyrrolnitrin, (15.48) Tebufloquin, (15.49) Tecloftalam, (15.50) Tolnifanide, (15.51) Triazoxid, (15.52) Trichlamid, (15.53) Zarilamid, (15.54) (3S,6S,7R,8R)-8-Benzyl-3-[( {3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl} carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl 2-methylpropanoat, (15.55) 1 -(4- {4-[(5R)-5- (2,6-Difluorphenyl)-4,5-dihydro- 1 ,2-oxazol-3-yl] - 1 ,3 -thiazol-2-yl} piperidin- 1 -yl)-2- [5-methyl-3 - (trifluormethyl)- lH-pyrazol- 1 -yl]ethanon, (15.56) 1 -(4- {4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-l ,2- oxazol-3 -yl] - 1 ,3 -thiazol-2-yl}piperidin- 1 -yl)-2- [5-methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] ethanon, (15.57) l-(4-{4-[5-(2,6-Difl^henyl)-4,5-dihydr^^^ (15.4) Carvone, (15.5) Quinomethionate, (15.6) Pyriofenone (Chlazafenone), (15.7) Cufraneb, (15.8) Cyflufenamid, (15.9) Cymoxanil, (15.10) Cyprosulfamide, (15.11) Dazomet, (15.12) Debacarb, (15.13 ) Dichlorophene, (15.14) diclomethine, (15.15) difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine, (15.18) ecomat, (15.19) fenpyrazamine, (15.20) flumetover, (15.21) fluorimimide, (15.22) flusulfamide, ( 15.23) flutianil, (15.24) fosetyl-aluminum, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium, (15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) methylisothiocyanate, (15.31) metrafenone, (15.32) Mildiomycin, (15.33) Natamycin, (15.34) Nickel Dimethyldithiocarbamate, (15.35) Nitrothal-isopropyl, (15.36) Octhilinone, (15.37) Oxamocarb, (15.38) Oxyfenthiine, (15.39) Pentachlorophenol and its salts, (15.40) Phenothrin , (15.41) Phosphoric acid and its salts, (15.42) Propamocarb-Fosetylate, (15.43) Propanosine sodium, (15.44) Pyrimorph, (15.45) (2E) - 3- (4-tert-butylphen yl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (15.46) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (15.47) pyrrole nitrate, (15.48) tebufloquine, (15.49) tecloftalam, (15.50) Tolnifanide, (15.51) Triazoxide, (15.52) Trichlamide, (15.53) Zarilamide, (15.54) (3 S, 6 S, 7 R, 8 R) -8-Benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl- 4,9-dioxo-1, 5-dioxonan-7-yl 2-methylpropanoate, (15.55) 1 - (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro 1, 2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3 - (trifluoromethyl) -1-pyrazol-1-yl] ethanone, (15.56) 1 - (4- {4 - [(5S) -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) -1-H-pyrazol-1-yl] ethanone, (15.57) 1- (4- {4- [5- (2,6-dIfL ^ -phenyl) -4,5-dihydr ^^^
methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1-yl] ethanon, (15.58) l-(4-Methoxyphenoxy)-3,3-dimethylbutan-2-yl lH-imidazole-l-carboxylat, (15.59) 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.60) 2,3-Dibutyl-6- chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.61) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole- l,3,5,7(2H,6H)-tetron, (15.62) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l-(4-{4-[(5R)-5-phenyl-methyl-3 - (trifluoromethyl) -1-H-pyrazol-1-yl] ethanone, (15.58) 1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate, (15.59) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (15.60) 2,3-dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 (3H) -one, (15.61) 2, 6-Dimethyl-1H, 5H- [1,4] dithiino [2,3-c: 5,6-c '] dipyrrole-1, 3,5,7 (2H, 6H) -tetrone, (15.62) 2- [5-methyl-3- (trifluoromethyl) -lH-pyrazol-l-yl] -l- (4- {4 - [(5R) -5-phenyl-
4.5- dihydro- 1 ,2-oxazol-3 -yl] - 1 ,3 -thiazol-2-yl} piperidin- 1 -yl)ethanon, ( 15.63) 2- [5-Methyl-3 - (trifluormethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5S)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2- yl} piperidin- l-yl)ethanon, (15.64) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l- {4-[4-(5-phenyl-4,5- dihydro-l,2-oxazol-3-yl)-l,3-thiazol-2-yl]piperidin-l-yl} ethanon, (15.65) 2-Butoxy-6-iodo-3-propyl-4H- chromen-4-οη, (15.66) 2-Chlor-5-[2-chlor-l-(2,6-difluor-4-methoxyphenyl)-4-methyl-lH-imidazol-5- yl]pyridin, (15.67) 2-Phenylphenol und Salze, (15.68) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4- dihydroisochinolin-l-yl)chinolin, (15.69) 3,4,5-Trichlorpyridine-2,6-dicarbonitril, (15.70) 3-Chlor-5-(4- chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.71) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.63) 2- [5-methyl-3- (trifluoromethyl) -1H pyrazol-1-yl] -1- (4- {4 - [(5S) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole-2-one yl} piperidin-1-yl) ethanone, (15.64) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- [4- [4- (5-phenyl-4, 5-dihydro-l, 2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin-1-yl} ethanone, (15.65) 2-butoxy-6-iodo-3-propyl-4H- chromen-4-one, (15.66) 2-Chloro-5- [2-chloro-1- (2,6-difluoro-4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl] pyridine, (15.67 ) 2-phenylphenol and salts, (15.68) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.69) 3,4,5-trichloropyridine- 2,6-dicarbonitrile, (15.70) 3-Chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, (15.71) 4- (4-chlorophenyl) -5- (2 , 6-difluorophenyl) -
3.6- dimethylpyridazin, (15.72) 5-Amino-l,3,4-thiadiazole-2-thiol, (15.73) 5-Chlor-N'-phenyl-N'-(prop-2- yn-l-yl)thiophene-2-sulfonohydrazid, (15.74) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.75) 5-3.6-dimethylpyridazine, (15.72) 5-Amino-l, 3,4-thiadiazole-2-thiol, (15.73) 5-Chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene -2-sulfonohydrazide, (15.74) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.75) 5-
Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.76) 5-Methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin- 7-amin, (15.77) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylat, (15.78) N'-(4- {[3-(4-Chlorbenzyl)-l,2,4- thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.79) N-(4-Chlorbenzyl)-3- [3 -methoxy-4-(prop-2-yn- 1 -yloxy)phenyl]propanamid, (15.80) N-[(4-Chlorphenyl)(cyano)methyl] -3 - [3 - methoxy-4-(prop-2-yn- 1 -yloxy)phenyl]propanamid, (15.81) N- [(5-Brom-3 -chlorpyridin-2-yl)methyl] -2,4- dichlornicotinamid, (15.82) N-[l-(5-Brom-3-chlorpyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.83) N-[l- (5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodonicotinamid, (15.84) N-{(E)-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.76) 5-methyl-6-octyl [l, 2,4] triazolo [l, 5-a] pyrimidine-7-amine, ( 15.77) Ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (15.78) N '- (4- {[3- (4-chlorobenzyl) -1,2,4-thiadiazol-5-yl] oxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.79) N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl ] propanamide, (15.80) N - [(4-Chlorophenyl) (cyano) methyl] -3 - [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl] propanamide, (15.81) N- [ (5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronotinamide, (15.82) N- [1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl] -2,4- Dichloromicotinamide, (15.83) N- [1- (5-Bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodonicotinamide, (15.84) N - {(E) -
[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.85) N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, (15.86) N'-{4-[(3-Tert-butyl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}-N-ethyl-N- methylimidoformamid, (15.87) N-Methyl-2-(l- {[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yl] acetyl} piperidin-4-yl)-N-( 1 ,2,3,4-tetrahydronaphthalen- 1 -yl)- 1 ,3 -thiazole-4-carboxamid, (15.88) N- Methyl-2-(l-{[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N-[(lR)-l,2,3,4- tetrahydronaphthalen-l-yl]-l,3-thiazole-4-carboxamid, (15.89) N-Methyl-2-(l- {[5-methyl-3- (trifluormethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [(1S)-1 ,2,3,4-tetrahydronaphthalen- 1 -yl]- 1 ,3- thiazole-4-carboxamid, (15.90) Pentyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamat, (15.91) Phenazine- 1 -carbonsäure, (15.92) Chinolin-8-ol, (15.93) Chinolin-8-ol sulfate (2:1), (15.94) Tert-butyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.95) l-Methyl-3-(trifluormethyl)-N- [2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (15.96) N-(4'-Chlorbiphenyl-2-yl)-3- (difluormethyl)-l -methyl- 1 H-pyrazol-4-carboxamid, (15.97) N-(2',4'-Dichlorbiphenyl-2-yl)-3- (difluormethyl)-l -methyl- lH-pyrazol-4-carboxamid, (15.98) 3-(Difluormethyl)-l-methyl-N-[4'- (trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (15.99) N-(2',5'-Difluorbiphenyl-2-yl)-l-methyl- 3-(trifluormethyl)-lH-pyrazol-4-carboxamid, (15.100) 3-(Difluormethyl)-l-methyl-N-[4'-(prop-l-yn-l- yl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, (15.101) 5-Fluor- 1 ,3-dimethyl-N-[4'-(prop- 1 -yn- 1 - yl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, ( 15.102) 2-Chlor-N-[4'-(prop- 1 -yn- 1 -yl)biphenyl-2- yl]nicotinamid, ( 15.103) 3 -(Difluormethyl)-N-[4'-(3,3-dimethylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (15.104) N-[4'-(3,3-dimethylbut- 1 -yn-1 -yl)biphenyl-2-yl]-5-fluor- 1 ,3-dimethyl- 1 H- pyrazol-4-carboxamid, ( 15.105) 3 -(Difluormethyl)-N-(4'-ethynylbiphenyl-2-yl)- 1 -methyl- 1 H-pyrazol-4- carboxamid, (15.106) N-(4'-Ethynylbiphenyl-2-yl)-5-fluor-l,3-dimethyl-lH-pyrazol-4-carboxamid, (15.107) 2-Chlor-N-(4'-ethynylbiphenyl-2-yl)nicotinamid, (15.108) 2-Chlor-N-[4'-(3,3-dimethylbut- 1 -yn- 1 - yl)biphenyl-2-yl]nicotinamid, ( 15.109) 4-(Difluormethyl)-2-methyl-N- [4'-(trifluormethyl)biphenyl-2-yl] - l,3-thiazole-5-carboxamid, (15.110) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l,3- dimethyl-lH-pyrazol-4-carboxamid, (15.111) 2-Chlor-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2- yl]nicotinamid, (15.112) 3-(Difluormethyl)-N-[4'-(3-methoxy-3-methylbut-l -yn-1 -yl)biphenyl-2-yl]-l - methyl- 1 H-pyrazol-4-carboxamid, (15.113) 5-Fluor-N- [4'-(3 -methoxy-3-methylbut- 1 -yn- 1 -yl)biphenyl-2- yl]-l,3-dimethyl-lH-pyrazol-4-carboxamid, (15.114) 2-Chlor-N-[4'-(3-methoxy-3-methylbut-l-yn-l- yl)biphenyl-2-yl]nicotinamid, (15.115) (5-Brom-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6- methylphenyl)methanon, (15.116) N- [2-(4- { [3-(4-Chlorphenyl)prop-2-yn- 1 -yl] oxy} -3 - methoxyphenyl)ethyl] -N2-(methylsulfonyl)valinamid, (15.117) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.118) But-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.119) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.120) Propyl 3,4,5-trihydroxybenzoat, (15.121) 1 ,3-Dimethyl-N-(l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, ( 15.122) 1,3- Dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (15.123) 1,3- Dimethyl-N-[(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, ( 15.124) [3 -(4- CWor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.125) (S)-[3-(4- Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.126) (R)-[3-(4- Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127) 2- {[3-(2- Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, (15.128) 1 - { [3 -(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol-5-yl thiocyanat, (15.129) 5- (Allylsulfanyl)- 1 - { [3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (15.130) 2-[l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, ( 15.131 ) 2- { [rel(2R,3 S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H- 1 ,2,4- triazol-3-thion, (15.132) 2- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4- dihydro-3H-l,2,4-triazol-3-thion, (15.133) l-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanat, (15.134) l- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanat, (15.135) 5-(Allylsulfanyl)-l- { [rel(2R,3 S)-3 -(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (15.136) 5- (Allylsulfanyl)- 1 - { [rel(2R,3R)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4- triazol, (15.137) 2-[(2S,4S,5S)-l-(2,4-Dichloφhenyl)-5-hydroxy-2,6,6-trimethylhe tan-4-yl]-2,4-dihydro- 3H- 1 ,2,4-triazol-3 -thion, ( 15.138) 2- [(2R,4S,5S)- 1 -(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (15.139) 2-[(2R,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, ( 15.140) 2- [(2S,4R,5R)- 1 -(2,4-Dichlorphenyl)-[(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (15.85) N - {(Z) - [(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2 , 3-difluorophenyl] methyl} -2-phenylacetamide, (15.86) N '- {4 - [(3-tert-butyl-4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro 5-methylphenyl} -N-ethyl-N-methylimidoformamide, (15.87) N -methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidine-4 -yl) -N- (1,2,3,4-tetrahydronaphthalen-1-yl) -1,3-thiazole-4-carboxamide, (15.88) N-methyl-2- (1 - {[5-methyl- 3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N - [(1R) -l, 2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazoles -4-carboxamide, (15.89) N-Methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1-H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -N- [ (1S) -1,2,3,4-tetrahydronaphthalene-1-yl] -1,3-thiazole-4-carboxamide, (15.90) pentyl {6 - [({[(1-methyl-1H-tetrazole-5 - yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) Quinolin-8-ol, (15.93) Quinolin-8-ol sulfate (2: 1), (15.94) Tert-butyl {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.95) 1-methyl-3- (trifluoromethyl) -N- [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4 carboxamide, (15.96) N- (4'-chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.97) N- (2 ', 4'- Dichlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.98) 3- (difluoromethyl) -1-methyl-N- [4'- (trifluoromethyl) biphenyl-2 -yl] -1H-pyrazole-4-carboxamide, (15.99) N- (2 ', 5'-difluorobiphenyl-2-yl) -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, ( 15,100) 3- (difluoromethyl) -1-methyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (15.101) 5- Fluoro-1,3-dimethyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (15.102) 2-chloro-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (15.103) 3- (difluoromethyl) -N- [4' - (3,3-dimethylbut-1-yn-1 -yl) biphenyl-2-yl] - 1 - methyl-1H-pyrazole-4-carboxamide, (15.104) N- [4 '- (3,3-dimethylbut-1 -yn-1-yl) biphenyl-2-yl] -5-fluoro-1, 3 dimethyl-1H-pyrazole-4-carboxamide, (15.105) 3- (difluoromethyl) -N- (4'-ethynyl-biphenyl-2-yl) -1-methyl-1H-pyrazole-4-carboxamide, (15.106) N - (4'-ethynyl-biphenyl-2-yl) -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.107) 2-chloro-N- (4'-ethynyl-biphenyl-2-yl) nicotinamide , (15.108) 2-Chloro-N- [4 '- (3,3-dimethylbut-1 -yn-1-yl) biphenyl-2-yl] nicotinamide, (15.109) 4- (difluoromethyl) -2-methyl- N- [4 '- (trifluoromethyl) biphenyl-2-yl] -1,3-thiazole-5-carboxamide, (15,110) 5-fluoro-N- [4' - (3-hydroxy-3-methylbut-1-one) yn-1-yl) biphenyl-2-yl] -l, 3-dimethyl-1H-pyrazole-4-carboxamide, (15.111) 2-chloro-N- [4 '- (3-hydroxy-3-methylbut-1 -yn-1-yl) biphenyl-2-yl] nicotinamide, (15.112) 3- (difluoromethyl) -N- [4 '- (3-methoxy-3-methylbut-1 -yn-1-yl) biphenyl-2 -yl] -1-methyl-1H-pyrazole-4-carboxamide, (15.113) 5-fluoro-N- [4 '- (3-methoxy-3-methylbut-1 -yn-1-yl) biphenyl-2 - yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, ( 15.114) 2-Chloro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (15.115) (5-bromo-2-methoxy-4 -methylpyridin-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (15.116) N- [2- (4- {[3- (4-chlorophenyl) prop-2-yn-1 - yl] oxy} -3-methoxyphenyl) ethyl] -N2- (methylsulfonyl) valinamide, (15.117) 4-oxo-4 - [(2-phenylethyl) amino] butanoic acid, (15,118) but-3-yn-1-yl {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.119) 4-amino 5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidine-2 (1H) -one), (15,120) propyl 3,4,5-trihydroxybenzoate, (15,121) 1, 3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (15,122) 1,3-dimethyl-N - [(3R) - 1, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (15.123) 1,3-dimethyl-N - [(3S) -1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-H-pyrazole-4-carboxamide, (15.124) [3- (4-C-nor-2-fluorophenyl) -5- ( 2,4-difluorophenyl) -l, 2-oxazol-4-yl] (pyridin-3- yl) methanol, (15.125) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl ) methanol, (15.126) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (15.127) 2- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole -3-thione, (15,128) 1 - {[3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole-5 -yl thiocyanate, (15.129) 5- (allylsulfanyl) -1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2, 4-triazole, (15,130) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4 -triazole-3-thione, (15,131) 2- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2, 4-dihydro-3H-1, 2,4- triazole-3-thione, (15,132) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4- dihydro-3H-l, 2,4-triazole-3-thione, (15.133) 1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2 - yl] methyl} -1H-l, 2,4-triazol-5-yl thiocyanate, (15.134) 1- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-) difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazol-5-yl thiocyanate, (15.135) 5- (allylsulfanyl) -l- {[rel (2R, 3S) -3 - ( 2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1,2,4-triazole, (15.136) 5- (allylsulfanyl) -1 - {[rel (2R , 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole, (15,137) 2 - [(2S, 4S, 5S) -l- (2,4-dichloro-phenyl) -5-hydroxy-2,6,6-trimethylhepan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3 -thione, (15,138) 2- [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro- 3H-l, 2,4-triazole-3-thione, (15,139) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane 4-yl] -2,4-dihydro-3H-1, 2,4-triazo l-3-thione, (15.140) 2- [(2S, 4R, 5R) -1- (2,4-dichlorophenyl) -
5- hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, ( 15.141 ) 2- [(2S,4S,5R)- 1 -(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (15.142) 2- [(2R,4S,5R)- 1 -(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 - thion, (15.143) 2-[(2R,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- 3H-l,2,4-triazol-3 -thion, (15.144) 2-[(2S,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3-thion, ( 15.145) 2-Fluor-6-(trifluormethyl)-N-( 1 , 1 ,3-trimethyl-2,3- dihydro-lH-inden-4-yl)benzamid, (15.146) 2-(6-Benzylpyridin-2-yl)quinazolin, (15.147) 2-[6-(3-Fluor-4- methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.148) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisochinolin-l-yl)chinolin, (15.149) Abscisinsäure, (15.150) 3-(Difluormethyl)-N-methoxy-l- methyl-N- [1 -(2,4,6-trichlorphenyl)propan-2-yl] - 1 H-pyrazol-4-carboxamid, (15.151) N'- [5-Brom-6-(2,3 - dihydro- 1 H-inden-2-yloxy)-2-methylpyridin-3 -yl] -N-ethyl-N-methylimidoformamid, ( 15.152) N'- {5-Brom-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (15,141) 2- [(2S, 4S, 5R) - 1 - (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (15,142 ) 2- [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2 , 4-triazole-3-thione, (15,143) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] - 2,4-dihydro-3H-l, 2,4-triazole-3-thione, (15.144) 2 - [(2S, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2, 6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.145) 2-Fluoro-6- (trifluoromethyl) -N- (1, 1 , 3-trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (15.146) 2- (6-benzylpyridin-2-yl) quinazoline, (15.147) 2- [6- (3-fluoro) 4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.148) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.149) abscisic acid, (15.150) 3- (Difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) propan-2-yl] -1 H -pyr azole-4-carboxamide, (15.151) N '- [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N -methylimidoformamide, (15.152) N '- {5-bromo-
6- [l-(3,5-difluoφhenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformam (15.153) N'- {5- Brom-6-[(lR)-l-(3,5-difluoφhenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformam6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformam (15.153) N '- {5-bromo-6 - [(IR) -l - (3,5-difluoφhenyl) ethoxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidoformam
(15.154) N'- {5-Brom-6-[(l S)- 1 -(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamid, (15.155) N'- {5-Brom-6- [(cis-4-isopropylcyclohexyl)oxy] -2-methylpyridin-3 -yl} -N- ethyl-N-methylimidoformamid, (15.156) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (15.157) N-Cyclopropyl-3-(difluormethyl)-5-fluor- N-(2-isopropylbenzyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.158) N-Cyclopropyl-N-(2- cyclopropylbenzyl)-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.159) N-(2-Tert- butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.160) N-(5- Chlor-2-ethylbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.161) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4- carboxamid, ( 15.162) N-Cyclopropyl-3 -(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor- 1 -methyl- 1 H- pyrazol-4-carboxamid, (15.163) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)- 1 - methyl- lH-pyrazol-4-carboxamid, (15.164) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor- 1 -methyl- lH-pyrazol-4-carboxamid, (15.165) N-(2-Cyclopentyl-5-fluorbenzyl)-N- cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.166) N-Cyclopropyl-3 - (difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxami (15.167) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxam (15.168) N-Cyclopropyl-3 -(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)- 1 -methyl- 1 H-pyrazol- 4-carboxamid, (15.169) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-l- methyl- lH-pyrazol-4-carboxamid, (15.170) N-(2-Tert-butyl-5-methylbenzyl)-N-cyclopropyl-3- (difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.171) N- [5 -Chlor-2-(15.154) N '- {5-Bromo-6 - [(1S) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.155 ) N'- {5-bromo-6- [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.156) N '- {5-bromo 6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.157) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- ( 2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.158) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H- pyrazole-4-carboxamide, (15.159) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.160) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.161) N- (5-chloro-2-isopropylbenzyl ) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3 - (difluoromethyl) -N- (2-ethyl-5 fluorobenzyl) -5-fluoro-1-methyl-1H- pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.164) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.165) N- (2-cyclopentyl-5- fluorobenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (15.167) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl -5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxy (15.168) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) - 1-methyl-1H-pyrazole-4-carboxamide, (15.169) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole 4-carboxamide, (15.170) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.171 ) N- [5 -chloro-2
(trifluormethyl)benzyl] -N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, ( 15.172) N-Cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl-N- [5-methyl-2-(trifluormethyl)benzyl] - 1 H- pyrazol-4-carboxamid, (15.173) N-[2-Chlor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5- fluor- 1 -methyl- lH-pyrazol-4-carboxamid, (15.174) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N- cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, ( 15.175) N-Cyclopropyl-3 - (difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, ( 15.176) N- Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carbothioamid, ( 15.177) 3-(Difluormethyl)-N-(7-fluor- 1 , 1 ,3 -trimethyl-2,3-dihydro- 1 H-inden-4-yl)- 1 -methyl- 1 H-pyrazol-4- carboxamid, (15.178) 3-(Difluormethyl)-N- [(3R)-7-fluor- 1 , 1 ,3 -trimethyl-2,3-dihydro- 1 H-inden-4-yl]- 1 - methyl- 1 H-pyrazol-4-carboxamid, ( 15.179) 3 -(Difluormethyl)-N- [(3 S)-7-fluor- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl]- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.180) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl- N-methylimidoformamid, ( 15.181 ) N'- {4- [(4,5-Dichlor- 1 ,3-thiazol-2-yl)oxy] -2,5-dimethylphenyl} -N-ethyl- N-methylimidoformamid, ( 15.182) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)- 1 ,3 -dimethyl- lH-pyrazol-5-amin. Alle genannten Mischpartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro 1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1 H -pyrazole-4-carboxamide, (15.173) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl 3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.174) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3 - (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5- fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.176) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4 carbothioamide, (15.177) 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole -4- carboxamide, (15.178) 3- (difluoromethyl) -N- [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1 - methyl-1H-pyrazole-4-carboxamide, (15.179) 3 - (di fluoromethyl) -N- [(3S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4- carboxamide, (15,180) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (15.181) N' - {4- [(4,5-dichloro-1,3-thiazole -2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (15.182) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl ) - 1, 3 -dimethyl-1H-pyrazole-5-amine. All of the above-mentioned mixing 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.
Biologische Schädlingsbekämpfungsmittel als Mischungspartner Biological pesticides as a mix partner
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte, und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. The compounds of formula (I) may be combined with biological pesticides. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that 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 231179), 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. NRRL 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 subspecies israelensis (serotype H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder 5. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD-1372), oder 5. 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 231179), 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, especially strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular 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-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. 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 HRO LEC 12, Lecanicillium lecanii, (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isaria fumosorosea), 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). Beauveria bassiana, especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), 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: Examples of viruses that can be used or used as biological pesticides are:
Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: 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 (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV. It also includes bacteria and fungi that are added as 'inoculant' plants or parts of plants 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 trifolü, 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: 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 trifolu, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp. Examples of plant extracts and products formed by microorganisms including proteins and secondary metabolites used as biological pest control agents can, 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/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Safener als Mischpartner 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, Regalia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (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). The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) 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).
Pflanzen und Pflanzenteile 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, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten 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 Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen 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 Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. Die erfindungsgemäße 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, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. Wie bereits oben erwähnt können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform 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 sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts should be understood as meaning all aboveground and subterranean parts and organs of 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 rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, such as 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) takes place directly or by acting on their environment, habitat or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing on, injecting and in the case of propagation material , in particular in the case of seeds, continue to be coated in one or more layers. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof 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 bred either 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, welches 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. Bodensalzgehalt, 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 Imidazolinonen, Sulfonylharnstoffen, Glyphosate 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, Zitrusfrüchten 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. Pflanzenschutz - Behandlungsarten The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives 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 bottoms salt, increased flowering, easier harvesting, 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, caused for example by toxins formed in the plants, in particular those caused by the genetic material from Bacillus Thuringiensis (eg 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 phytopathogenic fungi, bacteria and / or viruses, eg through systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and accordingly expressed proteins and toxins, as well as an increased tolerance of the plants against certain herbicidal active ingredients, 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, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails. Plant protection - types of treatment
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, (Ver-) Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-) Streuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, 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 Formel (I) selbst in den Boden zu injizieren. Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. The treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil. A preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
Bei systemisch wirksamen Verbindungen 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.h. die Verbindungen der Formel (I) werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein. In the case of systemically active compounds, 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 can be, for example, by drenching, mixing in the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, ie the compounds of Formula (I) are introduced in solid form, (eg in the form of granules) in the location of the plants. In water rice cultures, too by metering the compound of formula (I) in a solid application form (eg as granules) into a flooded paddy field.
Saatgutbehandlung seed treatment
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 Schädlingsbekämpfungsmitteln 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 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 eliminate or at least significantly reduce the additional application of pesticides 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 incorporate the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
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 Mischungspartner behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner 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 by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
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. 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.
Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut enthalten sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungspartner enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und Mischungspartner als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which contain a compound of the formula (I) and mixture partners may optionally be replaced by a Interlayer be separated. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent 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 der Verbindungen 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. One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the 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.
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. 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. 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. 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. 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, Baum-wolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z.B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln 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 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, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
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 Mikro- Organismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von trans-genem 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 be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed which contains at least one contains 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, Hülle, 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. 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, hull, 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 may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
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. Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. 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 seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing 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 also water.
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 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutyl-naphthalin-Sulfonate. 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-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglyko lether sowie Tri- stryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. 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 112 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 alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates. 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-stryrylphenol 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 Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Preservatives 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. Examples include dichlorophen and Benzylalkoholhemiformal. 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 cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
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 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 Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401- 412). Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen 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 Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. Gibberellins which may be present in the seed dressing formulations which can be used in accordance with the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412). 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 , Soy and beets or vegetable seed of various nature. The seed dressing 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-Formulierungen oder daraus 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 diskontinuierlichem oder kontinuierlichem Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen 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, all mixing devices which can usually be used for the dressing can be considered. Specifically, the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing 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-Formulierungen 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 animal Health
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 Endoparasiten umfasst insbesondere Helminthen und Protozoa wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten und Akariden. In the field of animal health, i. In the veterinary field, 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 and acarids.
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 Entwicklungsstadien 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; Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; Fische und Krustentiere, z.B. in der Aquakultur und auch Insekten wie Bienen. Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel, Reptilien, Amphibien und Aquariumfische. 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 stages of parasite development. Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and crustaceans, eg in aquaculture and insects such as bees. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. In a preferred embodiment, the compounds of formula (I) are administered to mammals.
Gemäß einer weiteren bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel und insbesondere Geflügel, verabreicht. According to a further preferred embodiment, the compounds of the formula (I) are administered to birds, namely caged birds and 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 erzielbar ist. 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.
In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen", 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 werden kann. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindung der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern kann. With regard to the field of animal health, the term "control" or "combat" means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, "combating" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
Zu den Arthropoden zählen: aus der Ordnung Anoplurida, zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina and Ischnocerina, zum Beispiel Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; aus der Ordnung Siphonapterida, zum Beispiel Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. The arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia Spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. , Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .; as well as pests and hygiene pests from the order Blattarida.
Weiterhin zählen zu den Arthropoden: 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; und aus der Ordnung Acaridida (Astigmata), zum Beispiel Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. Furthermore, the arthropods include: 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. , Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Zu parasitären Protozoen zählen: Parasitic protozoa include:
Mastigophora (Flagellata), wie zum Beispiel Trypanosomatidae, zum Beispiel Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Beispiel Trichomonadidae, zum Beispiel Giardia lamblia, G. canis; Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis;
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.; Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
Apicomplexa (Sporozoa), wie Eimeridae, zum Beispiel Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis,Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec, Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec, I. suis, Cystisospora spec, Cryptosporidium spec, insbesondere C. parvum; wieE. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis, Cystisospora spec , Cryptosporidium spec., Especially C. parvum; as
Toxoplasmadidae, zum Beispiel Toxoplasma gondii, Hammondia heydornii, Neospora caninum,Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum,
Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, wie Piroplasmea, zum Beispiel Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva,Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec., such as piroplasmea, for example Babesia argentina, B. bovis, B. canis, B. spec., Theileria parva,
Theileria spec, wie Adeleina, zum Beispiel Hepatozoon canis, H. spec. Zu pathogenen Endoparasiten, bei denen es sich um Helminthen handelt, zählen Plattwürmer (z.B. Monogenea, Cestodes und Trematodes), Rundwürmer, Acanthocephala und Pentastoma. Dazu zählen: Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec. Pathogenic endoparasites, which are helminths, include flatworms (eg, Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.; aus der Ordnung Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp. , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
Trematodes: aus der Klasse Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.; Rundwürmer: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.; aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Strongyloides spp.; aus der Ordnung Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.; aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; Trematodes: from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp. , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .; Roundworms: Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp ., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp.. Pentastoma: from 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 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. The administration can be prophylactic or therapeutic.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verwendung einer Verbindung der Formel (I) als Arzneimittel. Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
Ein weiterer Aspekt bezieht sich auf die Verwendung einer Verbindung der Formel (I) als Antiendoparasitikum, insbesondere als ein Helminthizid oder ein Mittel gegen Protozoen. Verbindungen der Formel (I) eignen sich für die Verwendung als Antiendoparasitikum, insbesondere als ein Helminthizid oder Mittel gegen Protozoen, beispielsweise in der Tierzucht, in der Tierhaltung, in Ställen und auf dem Hygienesektor. Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent. Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
Ein weiterer Aspekt wiederum betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder ein Akarizid Ein weiterer Aspekt betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder Akarizid, zum Beispiel in der Tierhaltung, in der Tierzucht, in Ställen oder auf dem Hygienesektor. Vektorkontrolle A further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide. Another aspect relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or acaricide For example, in animal husbandry, in animal husbandry, in stables or in the hygiene sector. vector control
Die Verbindungen der Formel (I) können auch in der Vektorkontrolle 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 may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., 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 Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms;
- Aedes: Gelbfieber, Dengue-Fieber, Filariasis, weitere virale Erkrankungen; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases;
- Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus; - Simulia: transmission of worms, in particular Onchocerca volvulus;
2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus); 3) Flöhe: Pest, endemisches Fleckfieber; 2) lice: skin infections, typhus (epidemic typhus); 3) Fleas: plague, endemic typhus fever;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, virale Hirnhautentzündung (FSME), Krim-Kongo-Fieber, Borreliose; 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
6) Zecken: Borelliosen wie Borrelia duttoni, Frühsommer-Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis). 6) Ticks: Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten wie 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 such as aphids, flies, cicadas or thrips, which 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, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Eine Vektorkontrolle 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, especially the genera Aedes, Anopheles, eg A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, 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 Krankheiten bzw. vor Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorkontrolle, 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 disease 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. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
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 der Ordnung Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order 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, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred. 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 einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d.h., es kann ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder als Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes. As further insecticides or as fungicides in particular the above-mentioned in 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 anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Surprisingly, 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 the formula (I) can be used alone or in combination with other active substances 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 Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen 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 protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins. To combat animal pests, the compounds of formula (I) are used alone or in Combination with other active ingredients and / or excipients used. 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, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. The application is carried out, for example, in aerosols, pressureless sprays, eg pump and atomizer sprays, smoke machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, Moth sacs and moth gels, as granules or dusts, in straw baits or bait stations.
Erläuterung der Verfahren und Zwischenprodukte Explanation of processes and intermediates
Die Verbindungen der Formel (I) können nach dem im Folgenden beschriebenen Verfahren hergestellt werden. Dabei sind exemplarisch die Verfahren zur Herstellung der Verbindungen der Formeln (Ia) herausgestellt, in denen A für -C(=0)NR13- , W für Sauerstoff und G für ein freies Elektronenpaar steht. Die Substituenten (z.B R1, n, Q1 etc.) haben sofern nicht explizit anders beschrieben die oben beschriebenen Bedeutungen. The compounds of the formula (I) can be prepared by the method described below. Here, by way of example, the processes for preparing the compounds of the formulas (Ia) are shown in which A is -C (= O) NR 13 -, W is oxygen and G is a free electron pair. The substituent (eg, R 1, n, Q 1, etc.) have if not explicitly described otherwise the meanings described above.
Die Verbindungen der allgemeinen Formel (Ia) The compounds of general formula (Ia)
Figure imgf000058_0001
Figure imgf000058_0001
können erhalten werden, in dem man Dicarbonsäuren der allgemeinen Formel (II) can be obtained by reacting dicarboxylic acids of the general formula (II)
Figure imgf000058_0002
Figure imgf000058_0002
zunächst mit Aminen der Formel (III) first with amines of the formula (III)
Figure imgf000058_0003
Figure imgf000058_0003
umsetzt. Hierbei kann die Dicarbonsäure der allgemeinen Formel (II) zum einen zunächst in ein Säurehalogenid überführt werden und anschließend in Gegenwart einer Base, wie z.B. Triethylamin oder Natriumhydroxid umgesetzt werden. Zum anderen kann die Carbonsäure aber auch unter der Verwendung von Kupplungsreagenzien wie z.B Dicyclohexylcarbodiimid und Additiven wie 1- Hydroxybenzotriazol durchgeführt werden [Chem. Ber. 1970, 788]. Verwendbar sind ferner Kupplungsreagenzien wie l-Ethyl-3-(3-dimethylaminopropyl)carbodiimid, Ι,Γ-Carbonyl-lH-imidazol, N- [( 1 H-Benzotriazol- 1 -yloxy)(dimethylamino)methylen] -N-methylmethanaminiumhexafluorophosphat, und ähnliche Verbindungen. Als Kupplungsreagenzien zur Durchführung des Dartellungsverfahrens finden alle, die zur Herstellung einer Ester- oder Amidbindung geeignet sind (vgl. z. B. Bodansky et al., Peptide Synthesis, 2nd ed., Wiley & Sons, New York, 1976; Gross, Meienhofer, The Peptide: Analysis, Synthesis, Biology (Academic Press, New York, 1979), Verwendung. implements. In this case, the dicarboxylic acid of the general formula (II) can firstly be converted into an acid halide and then reacted in the presence of a base such as, for example, triethylamine or sodium hydroxide. On the other hand, however, the carboxylic acid can also be carried out using coupling reagents such as dicyclohexylcarbodiimide and additives such as 1-hydroxybenzotriazole [Chem. Ber. 1970, 788]. It is also possible to use coupling reagents such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, Ι, Γ-carbonyl-1H-imidazole, N- [(1H-benzotriazol-1-ylxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate , and similar compounds. Suitable coupling reagents for carrying out the dartelling process are all those which are suitable for the preparation of an ester or amide bond (cf., for example, Bodansky et al. Peptide Synthesis, 2nd Ed., Wiley & Sons, New York, 1976; Gross, Meienhofer, The Peptides: Analysis, Synthesis, Biology (Academic Press, New York, 1979), use.
Die so erhaltenen Monocarbonsäuren der Formel (IV) The monocarboxylic acids of the formula (IV) thus obtained
Figure imgf000059_0001
Figure imgf000059_0001
werden anschließend mit Aminen der allgemeinen Formel (VII)
Figure imgf000059_0002
(VII) are subsequently reacted with amines of the general formula (VII)
Figure imgf000059_0002
(VII)
bevorzugt in Gegenwart eines Kondensationsreagenzes wie z.B. l-Ethyl-3-(3- dimethylaminopropyl)carbodiimid oder Ι,Γ-Carbonyl-lH-imidazol, N-[(lH-Benzotriazol-l- yloxy)(dimethylamino)methylen]-N-methylmethanaminiumhexafluorophosphat zu Verbindungen der allgemeinen Formel (1-1) umgesetzt, wobei G dann für ein freies Elektronenpaar steht. Alternativ können die Verbindungen der Formel (IV) auch zunächst z.B. durch Umsetzung mit Thionylchlorid oder Sulfurylchlorid in das entsprechende Säurechlorid überführt werden und anschließend mit Aminen der Formel (VII) in Gegenwart einer Base, wie z.B. Triethylamin zu Verbindungen der Formel (Ia) umgesetzt werden. Verbindungen der Formel (Ib) und (Ic) in denen A für die Gruppierungen -C(=0)NR13-NR16- und -C(=0)NR13C(R14)(R15)C(=0)NR16- steht können ebenfalls nach dem oben beschriebenen Verfahren erhalten werden, indem nach Syntheseschema 1 a Carbonsäurederivate der Formel (IV) mit Hydrazinen der Formel (Vlla) oder Aminosäureamiden der Formel (Vllb) umgesetzt werden. preferably in the presence of a condensation reagent such as, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide or Ι, Γ-carbonyl-1H-imidazole, N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N- methylmethanaminiumhexafluorophosphat converted into compounds of general formula (1-1), wherein G then stands for a free electron pair. Alternatively, the compounds of the formula (IV) can also be first converted into the corresponding acid chloride, for example by reaction with thionyl chloride or sulfuryl chloride, and then reacted with amines of the formula (VII) in the presence of a base such as triethylamine to give compounds of the formula (Ia) , Compounds of the formula (Ib) and (Ic) in which A is the grouping -C (= O) NR 13 -NR 16 - and -C (= O) NR 13 C (R 14 ) (R 15 ) C (= 0 ) NR 16 - can also be obtained by the process described above, by reacting according to synthesis scheme 1 a carboxylic acid derivatives of the formula (IV) with hydrazines of the formula (VIIa) or amino acid amides of the formula (VIIb).
Schema 1 a Scheme 1 a
Figure imgf000060_0001
Figure imgf000060_0001
Verbindungen der Formel (I-O), in denen W für O (Sauerstoffatom) und G für ein freies Elektronenpaar steht, können nach Syntheseschema lb mit einem Schwefelungsreagenz, wie z.B. Diphosphorpentasulfid oder Lawessons Reagenz (vgl. z.B. C. P. Dell in Comprehensive Organic Functional Group Transformations, Vol. 5, Hrsg.: A. R. Katrizky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, S. 565-628; M. Jesberger, T. P. Davis, L. Barner, Synthesis 2003, 13, 1929), zu Verbindungen der Formel (I-S), in denen W für S (Schwefelatom) steht, umgesetzt werden. Compounds of formula (I-O) in which W is O (oxygen atom) and G is a lone pair of electrons can be synthesized according to synthesis scheme Ib with a sulfurizing reagent, e.g. Diphosphorus pentasulfide or Lawesson's reagent (see, for example, CP Dell in Comprehensive Organic Functional Group Transformations, Vol. 5, eds .: AR Katrizky, O. Meth-Cohn, CW Rees, Pergamon, Oxford, 1995, pp. 565-628; Jesberger, TP Davis, L. Barner, Synthesis 2003, 13, 1929) to give compounds of formula (IS) wherein W is S (sulfur atom).
Schema lb Scheme Ib
Figure imgf000060_0002
Figure imgf000060_0002
(I-O) (I-S)  (I-O) (I-S)
Verbindungen der Formel (I-NO), in denen W für O (Sauerstoffatom) und G für O steht, können nach Syntheseschema lc aus Verbindungen der Formel (I-N) in denen G für ein freies Elektronenpaar steht, durch Umsetzung mit einem Oxidationsmittel wie z.B. meta-Perchlorbenzoesäure oder Wasserstoffperoxid in Essigsäure erhalten werden (vgl. z.B. WO-A-2011/9540) Schema lc Compounds of the formula (I-NO) in which W is O (oxygen atom) and G is O can, according to synthesis scheme Ic, from compounds of the formula (IN) in which G stands for a free electron pair, by reaction with an oxidizing agent such as meta-perchlorobenzoic acid or hydrogen peroxide in acetic acid are obtained (see for example WO-A-2011/9540) Scheme 1c
Figure imgf000061_0001
Figure imgf000061_0001
(I-N) (I-NO)  (I-N) (I-NO)
Verbindungen der Formel (Id bis Ig), in denen A für die Gruppierungen -C(R14)(R15)NR13-C(=0)-, - CH=N-N(R13)-C(=W)-N(R16)- oder -N(R13)-N(R16)-C(=0)- steht können nach Syntheseschema l d ausgehend von Verbindungen der Formel (IV) in Analogie zu allgemein bekannten Verfahren der organischen Chemie durch Derivatisierung der Carbonsäurefunktion zu Verbindungen mit Aminomethylfunktion (IVd), Hydrazinofunktion (IVg) oder Aldehydfunktion (IVb) und anschließender Umsetzung mit Säurechloriden der Formel (VIII) bzw. Semicarbazonen oder Thiosemicarbazonen der Formel (IX) erhalten werden (vgl. z.B. March's Advanced Organic Chemistry, 7th Edition, Wiley 2013). Compounds of the formula (Id to Ig) in which A represents the groupings -C (R 14 ) (R 15 ) NR 13 -C (= O) -, - CH = NN (R 13 ) -C (= W) - N (R 16 ) - or -N (R 13 ) -N (R 16 ) -C (= O) - can, according to synthesis scheme ld starting from compounds of formula (IV) in analogy to well-known methods of organic chemistry by derivatization the carboxylic acid function to compounds with aminomethyl (IVd), hydrazino (IVg) or aldehyde (IVb) and subsequent reaction with acid chlorides of the formula (VIII) or semicarbazones or thiosemicarbazones of the formula (IX) can be obtained (see, for example, March's Advanced Organic Chemistry, 7th Edition, Wiley 2013).
Schema ld Scheme ld
Figure imgf000061_0002
Figure imgf000061_0002
Figure imgf000061_0003
Figure imgf000061_0003
Figure imgf000061_0004
Quinolindicarbonsäuren der Formeln (II- 1 ),
Figure imgf000061_0004
Quinoline dicarboxylic acids of the formulas (II-1),
Figure imgf000062_0001
Figure imgf000062_0001
(wobei R a ,R , R 0 und R unabhängig voneinander die oben für R beschriebene Bedeutung haben) sind teilweise bekannt oder können durch Hydrolyse entsprechender Estervorstufen erhalten werden (vgl. z.B. Quinoline-2,6-dicarbonsäure: Journal of Heterocyclic Chemistry (1989), 26(4), 929-31 ; 4- Chlorquinoline-2,6-dicarbonsäure: CAS Registry Nummer 902742-45-4; 2-Methoxycarbonyl-4-methyl- quinolin-6-carbonsäure: WO 9613485; Dimethyl 8-methylquinolin-2,6-dicarboxylat: Bioorganic & Medicinal Chemistry (2006), 14(13), 4600-4609). Neue Quinolincarbonsäuren der Formel (Il-la mit R4a, R4b , R4c = H, R4d= H) können in Analogie zu bekannten Verfahren nach dem in Schema 2a beschriebenen Verfahren erhalten werden. (wherein R a , R, R 0 and R independently of one another have the meaning described above for R) are partially known or can be obtained by hydrolysis of corresponding ester precursors (see, for example, quinoline-2,6-dicarboxylic acid: Journal of Heterocyclic Chemistry (1989 ), 26 (4), 929-31; 4-chloroquinoline-2,6-dicarboxylic acid: CAS registry number 902742-45-4; 2-methoxycarbonyl-4-methyl-quinoline-6-carboxylic acid: WO 9613485; methylquinoline-2,6-dicarboxylate: Bioorganic & Medicinal Chemistry (2006), 14 (13), 4600-4609). New quinolinecarboxylic acids of the formula (II-1a with R 4a , R 4b , R 4c = H, R 4d = H) can be obtained in analogy to known processes by the process described in Scheme 2a.
Schema 2a Scheme 2a
Figure imgf000062_0002
Figure imgf000062_0002
(A-9) (11-1 a)  (A-9) (11-1a)
Quinolindicarbonsäuren der Formel (Il-la) werden hierbei in Analogie zu bekannten Verfahren aus Nitrilen der Formel (A-9) durch alkalische Hydrolyse, z.B. mit LiOH in Methanol erhalten. Nitrile der Formel (A-9) können aus Quinolin N-Oxiden der Formel (A-8) durch Umsetzung mit einem Cyanid, wie z.B. Trimethylsilylcyanid in Gegenwart einer Base, wie z.B. Trithylamin erhalten werden (vgl. z.B. WO-A-2011/9540). Quinolin N-Oxide der Formel (A-8) können durch Oxidation eines Quinolines der Formel (A-7) z.B. mit m-Chlor Perbenzoesäure erhalten werden (vgl. z.B. WO-A-2011/9540). Quinoline der Formel (A-7) können in Analogie zu bekannten Verfahren durch Umsetzung eines Anilins der Formel (A-6) mit Glycerin in Gegenwart von Schwefelsäure erhalten werden (vgl. z.B. Heterocyles 29(12) 2345-51, 1989). Verbindungen der Formel (A-6) sind kommerziell verfügbar, literaturbekannt oder in Analogie zu literaturbekannten Verfahren erhältlich Quinazolincarbonsäuren der Formel Π-2), Quinoline dicarboxylic acids of the formula (II-1a) are obtained here in analogy to known processes from nitriles of the formula (A-9) by alkaline hydrolysis, for example with LiOH in methanol. Nitriles of the formula (A-9) can be obtained from quinoline N oxides of the formula (A-8) by reaction with a cyanide, for example trimethylsilyl cyanide in the presence of a base, for example triethylamine (cf., for example, WO-A-2011 / 9540). Quinoline N-oxides of the formula (A-8) can be obtained by oxidation of a quinoline of the formula (A-7), for example with m-chloroperbenzoic acid (cf., for example, WO-A-2011/9540). Quinolines of the formula (A-7) can be obtained in analogy to known processes by reacting an aniline of the formula (A-6) with glycerol in the presence of sulfuric acid (cf., for example, Heterocyles 29 (12) 2345-51, 1989). Compounds of the formula (A-6) are commercially available, known from the literature or obtainable in analogy to processes known from the literature Quinazoline carboxylic acids of the formula Π-2),
Figure imgf000063_0001
Figure imgf000063_0001
(wobei R a ,R und R 0 unabhängig voneinander die oben für R beschriebene Bedeutung haben) sind teilweise bekannt oder können durch Hydrolyse entsprechender Estervorstufen erhalten werden (vgl. z.B. l,8-Naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92(5), 959-966; 5- hydroxy-l,8-Naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047). Neue(wherein R a , R and R 0 independently of one another have the meaning described above for R) are partially known or can be obtained by hydrolysis of corresponding ester precursors (cf., for example l, 8-naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92 (5), 959-966; 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047). New
Quinazolincarbonsäuren der Formel (II-2a) mit R4a, R4b, R4c = H; R6= Halogen) können z.B. in Analogie zu bekannten Verfahren nach der in Schema 4 beschriebenen Methode erhalten werden. Quinazolinecarboxylic acids of the formula (II-2a) with R 4a , R 4b , R 4c = H; R 6 = halogen) can be obtained, for example, in analogy to known methods according to the method described in Scheme 4.
Schema 4 Scheme 4
Figure imgf000063_0002
Figure imgf000063_0002
(ll-2a)  (II-2a)
Quinazolincarbonsäuren der Formel (II-2a) werden hierbei in Analogie zu bekannten Verfahren aus Verbindungen der Formel (A-12) durch Oxidation der Methylgruppe z.B. mit Kaliumpermanganat oder Selendioxid erhalten (vgl. WO-A-2010/101949; J. Het. Chem. 1989, 26, 929-31) Verbindungen der Formel (A-12) können durch Halogenierung der entsprechenden Hydroxyverbindungen der Formel (A- 11) z.B. mit Posphoroxychlorid oder Phosphoroxibromid erhalten werden (vgl. WO-A-2008/133753). Die Verbindung der Formel (A-11) kann durch Umsetzung von 2-Amino-6-methylpyridin mit Dimethyl 2-(methoxymethylene)propanedioat erhalten werden (vgl. US2001/46989; J. Med. Chem. 1997, 40, 2674) Quinazolincarbonsäuren der Formel Π-3), Quinazolinecarboxylic acids of the formula (II-2a) are hereby obtained in analogy to known processes from compounds of the formula (A-12) by oxidation of the methyl group, for example with potassium permanganate or selenium dioxide (cf., WO-A-2010/101949, J. Het 1989, 26, 929-31) Compounds of the formula (A-12) can be obtained by halogenation of the corresponding hydroxy compounds of the formula (A-11), for example with phosphorus oxychloride or phosphorus oxybromide (cf., WO-A-2008/133753). The compound of the formula (A-11) can be obtained by reacting 2-amino-6-methylpyridine with dimethyl 2- (methoxymethylene) propanedioate (see US2001 / 46989, J. Med. Chem. 1997, 40, 2674). Quinazolinecarboxylic acids of the formula Π-3),
Figure imgf000064_0001
Figure imgf000064_0001
(wobei R4b und R4c unabhängig voneinander die oben für R4 beschriebene Bedeutung haben) sind neu. Sie können beispielsweise in Analogie zu bekannten Verfahren nach der in Schema 5 beschriebenen Methode erhalten werden. (wherein R 4b and R 4c independently of one another have the meaning described above for R 4 ) are new. They can be obtained, for example, in analogy to known processes by the method described in Scheme 5.
Schema 5 Scheme 5
Figure imgf000064_0002
Figure imgf000064_0002
Quinazolincarbonsäuren der Formel (II-3a) werden hierbei in Analogie zu allgemein bekannten Verfahren aus Verbindungen der Formel (A-18) durch Hydrolyse der Cyanogruppe z.B. mit Natronlauge erhalten. Nitrile der Formel (A-18) können aus den entsprechenden Bromverbindungen der Formel (A-17) durch Umsetzung mit Cyanid ehalten werden (vgl. WO-A-2012/177728; WO-A- 2003/010146). Quinazolincarbonsäuren der Formel (A-17) können z.B. durch Umsetzung von Aminomethylverbindungen der Formel (A-16) mit Ethyl 2-Oxoacetate erhalten werden (vgl. Bioorg. Med. Chem. 2009, 17, 8221-8233). Verbindungen der Formel (A-16) können nach allgemein bekannten Verfahren in einer mehrstufigen Synthese aus Anilinen der Formel (A-13) erhalten werden (vgl. Organic Letters 15 (2013), 3766). Quinazolinecarboxylic acids of the formula (II-3a) are hereby prepared in analogy to generally known processes from compounds of the formula (A-18) by hydrolysis of the cyano group, e.g. obtained with sodium hydroxide solution. Nitriles of formula (A-18) can be obtained from the corresponding bromo compounds of formula (A-17) by reaction with cyanide (see WO-A-2012/177728, WO-A-2003/010146). Quinazoline carboxylic acids of formula (A-17) may be e.g. by reaction of aminomethyl compounds of the formula (A-16) with ethyl 2-oxoacetates are obtained (see Bioorg., Med. Chem. 2009, 17, 8221-8233). Compounds of the formula (A-16) can be obtained by generally known processes in a multistage synthesis from anilines of the formula (A-13) (see Organic Letters 15 (2013), 3766).
Amine der allgemeinen Formel (III) sind literaturbekannt oder können in Analogie zu literaturbekannten Verfahren erhalten werden (vgl. z.B. WO-A-2011/054436, WO-A-2012/119984). Amines of the general formula (III) are known from the literature or can be obtained analogously to processes known from the literature (cf., for example, WO-A-2011/054436, WO-A-2012/119984).
Verbindungen der Formeln (A-6), (A-10), (A-13), (VII), (VIII) und (IX) sind literaturbekannte Substanzen oder kommerziell erhältlich. Compounds of the formulas (A-6), (A-10), (A-13), (VII), (VIII) and (IX) are known from the literature or commercially available.
Im Allgemeinen können Verbindungen der Formel (I) und (II) 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) und (II) möglich oder durch individuelle Modifikationen der beschriebenen Verfahren. Zum Beispiel kann es Vorteile haben, gewisse Verbindungen der Formeln (I) oder (II) aus anderen Verbindungen der Formeln (I) und (II) herzustellen z.B. durch Hydrolyse, Verersterung, Amidbildung, Reduktion, Veretherung, Oxidation, Olefinierung, Halogenierung, Acylierung, Alkylierung und dergleichen. In general, compounds of formula (I) and (II) can be prepared by the methods described above. If individual connections do not follow the procedure described above can be prepared, the synthesis by derivatization of other compounds of formulas (I) and (II) is possible or by individual modifications of the described methods. For example, it may be advantageous to prepare certain compounds of formulas (I) or (II) from other compounds of formulas (I) and (II), for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, olefination, halogenation, acylation , Alkylation and the like.
Die erfindungsgemäßen Verfahren zur Herstellung der neuen Verbindungen der Formel (I) werden vorzugsweise unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren kommen neben Wasser alle inerten Lösungsmittel in Frage. Als Beispiele sind zu nennen:. Halogenkohlenwasserstoffe (z.B. Chlorkohlenwasserstoffe, wie Tetraethylen, Tetrachlorethan, Dichlorpropan, Methylenchlorid, Dichlorbutan, Chloroform, Tetrachlorkohlenstoff, Trichlorethan, Trichlorethylen, Pentachlorethan, Difluorbenzol, 1 ,2-Dichlorethan, Chlorbenzol, Brombenzol, Dichlorbenzol, Chlortoluol, Trichlorbenzol), Alkohole (z.B. Methanol, Ethanol, Isopropanol, Butanol), Ether (z.B. Ethylpropylether, Methyl-tert-butylether, Anisol, Phenetol, Cyclohexylmethylether, Dimethylether, Diethylether, Diproplether, Diisopropylether, Di-n-butylether, Diisobutylether, Diisoamylether, Ethylenglycoldimethylether, Tetrahydrofuran, 1,4-Dioxan, Dichlordiethylether und Polyether des Ethylenoxids und/oder Propylenoxids), Amine (z.B. Trimethyl-, Triethyl-, Tripropyl-, Tributylamin, N-Methylmorpholin, Pyridin und Tetramethylendiamin), Nitrokohlenwasserstoffe (z.B. Nitromethan, Nitroethan, Nitropropan, Nitrobenzol, Chlornitrobenzol, o- Nitrotoluol); Nitrile (wie z.B. Acetonitril, Propionitril, Butyronitril, Isobutyronitril, Benzonitril, m- Chlorbenzonitril), Tetrahydrothiophendioxid, Dimethylsulfoxid, Tetramethylensulfoxid, Dipropylsulfoxid, Benzylmethylsulfoxid, Diisobutylsulfoxid, Dibutylsulfoxid, Diisoamylsulfoxid, Sulfone (z.B. Dimethyl-, Diethyl-, Dipropyl-, Dibutyl-, Diphenyl-, Dihexyl-, Methylethyl-, 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 5 innerhalb eines Siedeinterwalles von 70°C bis 190°C, Cyclohexan, Methylcyclohexan, Petrolether, Ligroin, Octan, Benzol, Toluol, Chlorbenzol, 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,N-Dipropyl-formamid, Ν,Ν-Dibutyl-formamid, N-Methyl-pyrrolidin, N- Methyl-caprolactam, l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidin, Octylpyrrolidon,The processes according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. 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. Ethanol, isopropanol, butanol), ethers (eg ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4- Dioxane, dichloro diethyl ether and polyethers of ethylene oxide and / or propylene oxide), amines (eg trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine), nitrohydrocarbons (eg nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o - nitrotoluene); Nitriles (such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulfoxide, tetramethylene sulfoxide, dipropyl sulfoxide, benzylmethyl sulfoxide, diisobutyl sulfoxide, dibutyl sulfoxide, diisoamyl sulfoxide, sulfones (eg dimethyl, diethyl, dipropyl, dibutyl, Diphenyl, dihexyl, methylethyl, ethylpropyl, ethylisobutyl and pentamethylene sulfone), aliphatic, cycloaliphatic or aromatic hydrocarbons (eg pentane, hexane, heptane, octane, nonane and technical hydrocarbons), also known as "white spirits" with components having boiling points in the range of, for example, 40 ° C to 250 ° C, cymene, gasoline fractions 5 within a boiling rampart of 70 ° C to 190 ° C, cyclohexane, methylcyclohexane, petroleum ether, ligroin, octane, benzene, toluene, chlorobenzene, 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, N-dipropylformamide, Ν, Ν-dibutylformamide, N-methylpyrrolidine, N-methyl-caprolactam, l , 3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone,
Octylcaprolactam, l,3-Dimethyl-2-imidazolindion, N-Formyl-piperidin, Ν,Ν'-Diformyl-piperazin) und Ketone (z.B. Aceton, Acetophenon, Methylethylketon, Methylbutylketon). Octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, Ν, Ν'-diformyl-piperazine) and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
Selbstverständlich kann man das erfindungsgemäße Verfahren auch in Gemischen der genannten Lösungs- und Verdünnungsmittel durchführen. Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens 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. Of course, the process according to the invention can also be carried out in mixtures of the solvents and diluents mentioned. The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
Das erfindungsgemäße Verfahren wird 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. The process according to the invention is 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 and 15 bar.
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 einer 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 Herstellungsbeispiele). 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 a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature. The workup 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-Methyl- 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, Tricyclohexylamin, Triamylamin, Trihexylamin, N,N- Dimethylanilin, Ν,Ν-Dimethyl-toluidin, N,N-Dimethyl-p-aminopyridin, N-Methyl-pyrrolidin, N- Methyl-piperidin, N-Methyl-imidazol, N-Methyl-pyrazol, N-Methyl-morpholin, N-Methyl- hexamethylendiamin, Pyridin, 4-Pyrrolidinopyridin, 4-Dimethylamino-pyridin, Chinolin, α-Picolin, ß- Picolin, Pyrimidin, Acridin, Ν,Ν,Ν',Ν'-Tetramethylendiamin, Ν,Ν,Ν',Ν'-Tetraethylendiamin, Chinoxalin, N-Propyl-diisopropylamin, N-Ethyl-diisopropylamin, N,N'-Dimethyl-cyclohexylamin, 2,6- Lutidin, 2,4-Lutidin oder Triethyldiamin). Pentamethylpiperidine) and amines, especially 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-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline , α-picoline, β-picoline, pyrimidine, acridine, Ν, Ν, Ν ', Ν'-tetramethylenediamine, Ν, Ν, Ν', Ν'-tetraethylenediamine, quinoxaline, N-propyl-diisopropylamine, N-ethyl-diisopropylamine , N, N'-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 hydriodic 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) can be used.
Die folgenden Herstellungs- und Verwendungsbeispiele illustrieren die Erfindung ohne sie zu beschränken. The following examples of preparation and use illustrate the invention without limiting it.
Herstellungsbeispiele Preparation Examples
Synthesebeispiel Nr. 1 Synthesis Example No. 1
5-bromo-N6-(l-cyanocyclopropyl)-N2-[2,2,2-trifluoro-l-[4-fluoro-3-(trifluoromethyl) 5-bromo-N6- (l-cyanocyclopropyl) -N2- [2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl)
phenyl]ethyl]quinoline-2,6-dicarboxamide (Verbindung Nr. 1-1-01) Stufe 1 : Methyl-4-amino-2-bromo-benzoat phenyl] ethyl] quinolines-2,6-dicarboxamides (Compound No. 1-1-01) Step 1: Methyl 4-amino-2-bromo-benzoate
Figure imgf000068_0001
Figure imgf000068_0001
Eine Lösung von Methyl-2-bromo-4-nitrobenzoat (5,00 g, 19,2 mmol) in 2-Propanol / Wasser (45 ml; 20:80) wurde mit Amoniumchlorid (1,23 g, 23,07 mmol) und Eisenpulver (6,44 g, 115,4 mmol) versetzt und anschließend 30 Minuten unter Rückfluß erhitzt. Das Reaktionsgemisch wurde abgekühlt, über Kieselgur filtriert und mit Ethylacetat nachgewaschen. Die organische Phase wurde mit gesättigter Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Es wurden 3,75 g (82,2 % d.Th.) Methyl-4-amino-2-bromo-benzoat erhalten. HPLC-MS: logP = 1,64; Masse (m/z): 232,0 (M+H)+ A solution of methyl 2-bromo-4-nitrobenzoate (5.00 g, 19.2 mmol) in 2-propanol / water (45 mL, 20:80) was added with ammonium chloride (1.23 g, 23.07 mmol and iron powder (6.44 g, 115.4 mmol) and then heated at reflux for 30 minutes. The reaction mixture was cooled, filtered through kieselguhr and washed with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulfate and the solvent removed under reduced pressure. There were obtained 3.75 g (82.2% of theory) of methyl 4-amino-2-bromo-benzoate. HPLC-MS: log P = 1.64; Mass (m / z): 232.0 (M + H) +
Stufe 2: Methyl-5-bromoquinoline-6-carbox late / Methyl-7-bromoquinoline-6-carboxylate Step 2: Methyl 5-bromoquinolines-6-carbox late / methyl-7-bromoquinolines-6-carboxylates
Figure imgf000068_0002
Figure imgf000068_0002
Zu Methyl-4-amino-2-bromo-benzoat (3,45 g, 15,0 mmol) in Glycerin (6,90 g, 75,0 mmol) wurde zunächst Natrium-3-nitrobenzolsulfonat (6,75 g, 30,0 mmol) und anschließend 40 ml 75% ige Schwefelsäure gegeben und das Reaktionsgemisch 3 Stunden bei 100 °C gerührt. Es wurde auf 60°C abgekühlt und 40 ml Methanol zugesetzt. Dann wurde weitere 18 Stunden bei 60°C gerührt. Die abgekühlte Lösung wurde auf Eiswasser geschüttet, mit Ammoniumhydroxid basisch gestellt und anschließend mit Ethylacetat extrahiert. Die Organische Phase wurde über Magnesiumsulfat getrocknet, das Lösungsmittel unter vermindertem Druck abdestilliert und der Rückstand an Kieselgel chromatographiert (Eluens: Cyclohexan/Essigsäureetylester 1 : 1). Man erhielt 2,4 g (59 % der Theorie) eines Gemisches aus Methyl-5-bromoquinoline-6-carboxylate und Methyl-7-bromoquinoline-6- carboxylate im Verhältnis 60:40.  To methyl 4-amino-2-bromo-benzoate (3.45 g, 15.0 mmol) in glycerol (6.90 g, 75.0 mmol) was initially added sodium 3-nitrobenzenesulfonate (6.75 g, 30 , 0 mmol) and then added to 40 ml of 75% sulfuric acid and the reaction mixture was stirred at 100 ° C for 3 hours. It was cooled to 60 ° C and added to 40 ml of methanol. Then a further 18 hours at 60 ° C was stirred. The cooled solution was poured onto ice-water, basified with ammonium hydroxide and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel (eluant: cyclohexane / ethyl acetate 1: 1). This gave 2.4 g (59% of theory) of a mixture of methyl 5-bromoquinoline-6-carboxylate and methyl 7-bromoquinoline-6-carboxylates in the ratio 60:40.
Methyl-5-bromoquinoline-6-carboxylate Methyl-5-Bromoquinoline-6-carboxylate
HPLC-MS: logP = 2,09; Masse (m/z): 266,1 (M+H)+ Methyl-7-bromoquinoline-6-carboxylate HPLC-MS: logP = 2.09; Mass (m / z): 266.1 (M + H) + Methyl-7-Bromoquinoline-6-carboxylate
HPLC-MS: logP = 2,00; Masse (m/z): 266,1 (M+H)+ HPLC-MS: logP = 2.00; Mass (m / z): 266.1 (M + H) +
Stufe 3: Methyl- 5 -bromo-1 -oxido-quinolin-l -ium-6-carboxylat / Methyl-7 -bromo-1 -oxido-quinolin-l - ium-6-carboxylat Step 3: Methyl 5-bromo-1-oxido-quinoline-1 -ium-6-carboxylate / methyl-7-bromo-1-oxo-quinoline-l-ium-6-carboxylate
Figure imgf000069_0001
Figure imgf000069_0001
Ein Gemisch aus Methyl 5-bromoquinoline-6-carboxylate und Methyl-7-bromoquinoline-6-carboxylate im Verhältnis 60:40 (2,00 g, 7,52 mmol) wurde in Dichlormetan (200 mL) gelöst und m- Chlorbenzoesäure (70 %ig, 4,63 g, 18,8 mmol) zugesetzt. Das Reaktionsgemisch wurde 18 h bei Raumtem eratur gerührt, anschließend mit gesättigter Natriumhydrogencarbonatlösung sowie gesättigter Natriumchloridlösung gewaschen und über Magnesiumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck abdestilliert und der Rückstand an Kieselgel mit Ethylacetat chromatographiert (Eluens: Cyclohexan/Essigsäureetylester 1 : 1). Es wurden 1,10 g (51,7 % d.Th.) eines Gemisches aus Methyl-5-bromo-l-oxido-quinolin-l -ium-6-carboxylat und Methyl-7-bromoquinoline-6- carboxylate im Verhältnis 80:20 erhalten. A 60:40 (2.00 g, 7.52 mmol) mixture of methyl 5-bromoquinoline-6-carboxylate and methyl 7-bromoquinoline-6-carboxylate was dissolved in dichloromethane (200 mL) and m-chlorobenzoic acid ( 70%, 4.63 g, 18.8 mmol). The reaction mixture was stirred at room temperature for 18 h, then washed with saturated sodium bicarbonate solution and saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate (eluent: cyclohexane / ethyl acetate 1: 1). 1.10 g (51.7% of theory) of a mixture of methyl 5-bromo-1-oxido-quinoline-1 -ium-6-carboxylate and methyl 7-bromoquinoline-6-carboxylate were obtained 80:20 received.
Methyl- 5 -bromo-1 -oxido-quinolin-l -ium-6-carboxylat Methyl 5-bromo-1-oxo-quinoline-1 -ium-6-carboxylate
HPLC-MS: logP = 1,28; Masse (m/z): 281,9(M+H)+ HPLC-MS: logP = 1.28; Mass (m / z): 281.9 (M + H) +
Methyl-7 -bromo-1 -oxido-quinolin-l -ium-6-carboxylat Methyl 7-bromo-1-oxo-quinoline-1 -ium-6-carboxylate
HPLC-MS: logP = 1,21 ; Masse (m/z): 283,8(M+H)+ HPLC-MS: logP = 1.21; Mass (m / z): 283.8 (M + H) +
Stufe 4: Methyl-5-bromo-2-cyano-quinoline-6-carbox lat Step 4: Methyl 5-bromo-2-cyano-quinoline-6-carboxy late
Figure imgf000069_0002
Figure imgf000069_0002
Ein Gemisch aus Methyl-5-bromo-l-oxido-quinolin-l -ium-6-carboxylat und Methyl-7-bromo-l -oxido- quinolin-l -ium-6-carboxylat im Verhältnis 80:20 (0,350 g, 1,241 mmol) wurde bei 0 °C in einer Lösung aus Kaliumcyanid (0,162 g, 2,481 mmol) in Wasser (5 mL) vorgelegt. Hierzu wurde Benzoylchlorid (0,289 mL; 0,349 g, 2,48 mmol) gegeben und 1 h unter Eiskühlung nachgerührt. Die wässrige Phase wurde abdekantiert und der Rückstand mit IM Kaliumcarbonatlösung verrührt. Nach Zusatz von Dichlormethan wurden die Phasen getrennt, mit Wasser gewaschen, über Magnesiumsulfat getrocknet und das Lösungsmittel im Vakuum entfernt. Der Rückstand wurde an Kieselgel mit Cyclohexan/Ethylacetat (3/1) chromatographiert und ergab 0,23 g (61 % d. Th.) Methyl-5-bromo-2- cyano-quinoline-6-carboxylat. HPLC-MS: logP = 2,61 ; Masse (m/z): 292,9 (M+H)+; 'HNMR (D6- DMSO): δ 3.91 (s, 3H), 8.11 (m, 1H), 8.26 (m, 2H), 8.94 (m, 1H). A mixture of methyl 5-bromo-1-oxido-quinoline-1 -ium-6-carboxylate and methyl 7-bromo-1-oxide quinoline-1 -ium-6-carboxylate in the ratio 80:20 (0.350 g , 1.241 mmol) was initially charged at 0 ° C in a solution of potassium cyanide (0.162 g, 2.481 mmol) in water (5 mL). To this was added benzoyl chloride (0.289 mL, 0.349 g, 2.48 mmol) and stirred for 1 h while cooling with ice. The aqueous phase was decanted off and the residue was stirred with 1M potassium carbonate solution. After addition of dichloromethane, the phases were separated, washed with water, dried over magnesium sulfate and the solvent removed in vacuo. The residue was on silica gel with Cyclohexane / ethyl acetate (3/1) to give 0.23 g (61% of theory) of methyl 5-bromo-2-cyano-quinoline-6-carboxylate. HPLC-MS: logP = 2.61; Mass (m / z): 292.9 (M + H) + ; 'HNMR (D 6 -DMSO): δ 3.91 (s, 3H), 8.11 (m, 1H), 8.26 (m, 2H), 8.94 (m, 1H).
Stufe 5: 5-Bromoquinoline-2, 6-dicarbonsäure Step 5: 5-Bromoquinoline-2, 6-dicarboxylic acid
Figure imgf000070_0001
Figure imgf000070_0001
Methyl-5-bromo-2-cyano-quinoline-6-carboxylat. (0,183 g, 0,629 mmol) wurde in Ethanol (25 mL) suspendiert und mit Natronlauge (45%ig, 201 mg, 5,029 mmol) versetzt. Das Reaktionsgemisch wurde 18 Stunden bei 50°C nachgerührt und anschließend in 10 ml Eiswasser eingerührt. Nach Ansäuern mit 30%iger Salzsäure wurde der ausgefallene Feststoff abgesaugt und getrocknet. Es wurden 0,128 g (68 % d.Th.) 5-Bromoquinoline-2,6-dicarbonsäure erhalten. HPLC-MS: logP = 0,44; Masse (m/z): 295,9 (M+H)+; 'HNMR (D6-DMSO): δ 8.04 (d, 1H), 8.27 (d, 1H), 8.33 (d, 1H), 8.86 (d, 1H), 13.90 (br.s , 2H). Methyl-5-bromo-2-cyano-quinoline-6-carboxylate. (0.183 g, 0.629 mmol) was suspended in ethanol (25 mL) and sodium hydroxide solution (45%, 201 mg, 5.029 mmol) was added. The reaction mixture was stirred for 18 hours at 50 ° C and then stirred into 10 ml of ice water. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. There were obtained 0.128 g (68% of theory) of 5-bromoquinolines-2,6-dicarboxylic acid. HPLC-MS: log P = 0.44; Mass (m / z): 295.9 (M + H) + ; 'HNMR (D 6 -DMSO): δ 8.04 (d, 1H), 8.27 (d, 1H), 8.33 (d, 1H), 8.86 (d, 1H), 13.90 (br.s, 2H).
Stufe 6: 5-Bromo-2-[[2,2,2-trifluoro-l-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl]cw Step 6: 5-Bromo-2 - [[2,2,2-trifluoro-1- (4-fluoro-3- (trifluoromethyl) phenyl] ethyl] cw
6-carbonsäure 6-carboxylic acid
Figure imgf000070_0002
Figure imgf000070_0002
5-Bromoquinoline-2,6-dicarbonsäure (60 mg, 0,203 mmol) wurde in N,N-Dimethylformamid (1,0 mL) gelöst und nacheinander 2,2,2-Trifluor-l-[4-fluor-3-(trifluormethyl)phenyl]ethanamin (66,15 mg, 0,253 mmol), N-[(lH-Benzotriazol-l -yloxy)(dimethylamino)methylen]-N-methylmethanaminium- hexafluorophosphat (76,9 mg, 0,203 mmol) und 4-Methylmorpholin (81,99 mg, 0,811 mmol) zugegeben. Das Reaktionsgemisch wurde 18 h bei Raumtemperatur gerührt und anschließend Wasser zugegeben. Die wässrige Phase wurde dreimal mit Ethylacetat extrahiert, über Natriumsulfat getrocknet, auf Kieselgel adsorbiert und mit Cyclohexan/Ethylacetat (1 :1) chromatographiert. Es wurden 72,2 mg (66 % d.Th.) 5-Bromo-2-[[2,2,2-trifluoro-l-[4-fluoro-3 (trifluoromethyl)phenyl]ethyl]carbamoyl] quinoline-6-carbonsäureerhalten. HPLC-MS: logP = 3,63; Masse (m/z): 540,8 (M+H)+; 'HNMR (D6- DMSO): δ 6.41 (m, 1H), 7.65 (t, 1H), 7.95 (s, 1H), 8.08 (d, 1H), 8.25-8.40 (m, 4 H), 8.89 (d, 1H), 10.17 (s, 1H). Stufe 7: 5-bromo-N6-(l-cyanocyclopropyl)-N2-[2,2,2-trifluoro-l-[ 4-fluoro-3- (trifluoromethyl)phenyl] ethyl] quinoline-2, 6-dicarboxamid 5-Bromoquinolines-2,6-dicarboxylic acid (60 mg, 0.203 mmol) was dissolved in N, N-dimethylformamide (1.0 mL) and sequentially 2,2,2-trifluoro-l- [4-fluoro-3- ( trifluoromethyl) phenyl] ethanamine (66.15 mg, 0.253 mmol), N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate (76.9 mg, 0.203 mmol); Methylmorpholine (81.99 mg, 0.811 mmol) was added. The reaction mixture was stirred at room temperature for 18 h and then water was added. The aqueous phase was extracted three times with ethyl acetate, dried over sodium sulfate, adsorbed onto silica gel and chromatographed with cyclohexane / ethyl acetate (1: 1). 72.2 mg (66% of theory) of 5-bromo-2 - [[2,2,2-trifluoro-1- [4-fluoro-3 (trifluoromethyl) phenyl] ethyl] carbamoyl] quinoline-6 were obtained -carbonsäureerhalten. HPLC-MS: logP = 3.63; Mass (m / z): 540.8 (M + H) + ; 'HNMR (D 6 -DMSO): δ 6.41 (m, 1H), 7.65 (t, 1H), 7.95 (s, 1H), 8.08 (d, 1H), 8.25-8.40 (m, 4H), 8.89 ( d, 1H), 10.17 (s, 1H). Step 7: 5-bromo-N6- (1-cyanocyclopropyl) -N2- [2,2,2-trifluoro-1- (4-fluoro-3- (trifluoromethyl) phenyl] ethyl] quinoline-2,6-dicarboxamide
Figure imgf000071_0001
Figure imgf000071_0001
5-Bromo-2-[[2,2,2-trifluoro-l-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl]carbamoyl]quinoline-6- carbonsäure (67 mg, 0,124 mmol) wurde in DMF (2,0 mL) vorgelegt und zunächst N-[(1H- Benzotriazol-l -yloxy)(dimethylamino)methylen]-N-methylmethanaminium-hexafluorophosphat (58,9 mg, 0,155 mmol) und danach 4-Methylmorpholin (50,27 mg, 0,497 mmol) zugegeben. Das Reaktionsgemisch wurde 18 h bei Raumtemperatur gerührt und anschließend mit Wasser versetzt. Der ausgefallene Niederschlag wurde abfiltriert und an Kieselgel mit Cyclohexan/Essigsäureetylester als Eluens chromatographiert. Es wurden 30,0 mg (40 % der Theorie) 5-bromo-N6-(l-cyanocyclopropyl)- N2-[2,2,2-trifluoro-l -[4-fluoro-3-(trifluoromethyl)phenyl]ethyl]quinoline-2,6-dicarboxamide erhalten.  5-Bromo-2 - [[2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl] carbamoyl] quinoline-6-carboxylic acid (67mg, 0.124mmol) was dissolved in DMF ( 2.0 mL) and initially N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate (58.9 mg, 0.155 mmol) and then 4-methylmorpholine (50.27 mg , 0.497 mmol) was added. The reaction mixture was stirred for 18 h at room temperature and then treated with water. The precipitate was filtered off and chromatographed on silica gel with cyclohexane / Essigsäureetylester as the eluent. There were 30.0 mg (40% of theory) of 5-bromo-N6- (1-cyanocyclopropyl) -N2- [2,2,2-trifluoro-l - [4-fluoro-3- (trifluoromethyl) phenyl] ethyl ] Quinoline-2,6-dicarboxamides obtained.
HPLC-MS: logP = 3,69; Masse (m/z): 605,0; 'HNMR (D6-DMSO): δ 1.35 (m, 2H), 1.62 (m, 2H), 6.42, (m, 1H), 7.65 (t, 1H), 7.91 (s, 1H), 8.25-8.95 (m, 4 H), 8.85 (d, 1H), 9.65 (s, 1H), 10.13 (s, 1H). HPLC-MS: logP = 3.69; Mass (m / z): 605.0; 'HNMR (D 6 -DMSO): δ 1.35 (m, 2H), 1.62 (m, 2H), 6.42, (m, 1H), 7.65 (t, 1H), 7.91 (s, 1H), 8.25-8.95 ( m, 4H), 8.85 (d, 1H), 9.65 (s, 1H), 10.13 (s, 1H).
Synthesebeispiel Nr. 2 5-Chlor-N6-cyclopropyl-N2-[l-(3,5-dichlor-2,4-difluorphenyl)-2,2,2-trifluorethyl]chinolin-2,6- dicarboxamid-l-oxid (Verbindung Nr. I-la-1) Synthesis Example No. 2 5-Chloro-N6-cyclopropyl-N 2 - [1- (3,5-dichloro-2,4-difluorophenyl) -2,2,2-trifluoroethyl] quinoline-2,6-dicarboxamide 1-oxide (Compound No. I-1a-1)
Figure imgf000071_0002
Figure imgf000071_0002
5-Chlor-N6-cyclopropyl-N2-[l-(3,5-dichlor-2,4-difluo^henyl)-2,2,2-trifluorethyl]chinolin-2,6- dicarboxamid (300 mg, 0,54 mmol) (Verbindung Nr. 1-1-14) wurde in Trichlormethan (15,0 mL) vorgelegt und bei 0°C 3 -Chlorbenzoesäure (70 %ig, 400,1 mg, 1,62 mmol) zugesetzt. Das Reaktionsgemisch wurde unter Erwärmen auf Raumtemperatur 18 h gerührt, anschließend mit gesättigter Natriumhydrogencarbonatlösung versetzt und mit Wasser verdünnt. Die wässrige Phase wurde dreimal mit Ethylacetat extrahiert, über Natriumsulfat getrocknet, auf Kieselgel adsorbiert und mit Cyclohexan/Ethylacetat chromatographiert. Es wurden 37,0 mg (11 % der Theorie) 5-Chlor-N6- cyclopropyl-N2-[l-(3,5-dichlor-2,4-difluo^heny  5-chloro-N6-cyclopropyl-N2- [1- (3,5-dichloro-2,4-difluoroethylenel) -2,2,2-trifluoroethyl] quinoline-2,6-dicarboxamide (300 mg, 0; 54 mmol) (Compound No. 1-1-14) was initially charged in trichloromethane (15.0 mL) and at 0 ° C 3-chlorobenzoic acid (70%, 400.1 mg, 1.62 mmol) was added. The reaction mixture was stirred with warming to room temperature for 18 h, then treated with saturated sodium bicarbonate solution and diluted with water. The aqueous phase was extracted three times with ethyl acetate, dried over sodium sulfate, adsorbed onto silica gel and chromatographed with cyclohexane / ethyl acetate. 37.0 mg (11% of theory) of 5-chloro-N6-cyclopropyl-N2- [1- (3,5-dichloro-2,4-difluorobenzene
erhalten. HPLC-MS: logP = 4,23; Masse (m/z): 568,0; 'HNMR (D6-DMSO): δ 0.70 (m, 2H), 0.76 (m, 2H), 4.03, (m, 1H), 6.45 (m, 1H), 7.91 (d, 1H), 8.16-8.40 (m, 3 H), 8.74 (d, 1H), 8.81 (d, 1H). receive. HPLC-MS: log P = 4.23; Mass (m / z): 568.0; HNMR (D 6 -DMSO): δ 0.70 (m, 2H), 0.76 (m, 2H), 4.03, (m, 1H), 6.45 (m, 1H), 7.91 (d, 1H), 8.16-8.40 ( m, 3H), 8.74 (d, 1H), 8.81 (d, 1H).
Weitere neue Quinolin-2,6-dicarbonsäuren der Formel (IIa) wurden gemäß oder in Analogie zu den oben beschriebenen Synthesebeispielen erhalten: Further novel quinoline-2,6-dicarboxylic acids of the formula (IIa) were obtained according to or in analogy to the synthesis examples described above:
5-Chloroquinoline-2, 6-dicarbonsäure 5-chloroquinolines-2, 6-dicarboxylic acid
Figure imgf000072_0001
Figure imgf000072_0001
HPLC-MS: logP = 0,51 ; Masse (m/z): 251,9; 'HNMR (D6-DMSO): δ 8.11 (d, 1H), 8.21 (d, 2H), 8.30 (d, 1H), 9.01 (d, 1H), 13.90 (br.s , 2H). HPLC-MS: log P = 0.51; Mass (m / z): 251.9; 'HNMR (D 6 -DMSO): δ 8.11 (d, 1H), 8.21 (d, 2H), 8.30 (d, 1H), 9.01 (d, 1H), 13.90 (br.s, 2H).
5-Methylquinoline-2, 6-dicarbonsäure 5-methylquinoline-2, 6-dicarboxylic acid
Figure imgf000072_0002
Figure imgf000072_0002
HPLC-MS: logP = 0,30; Masse (m/z): 232,0; 'HNMR (D6-DMSO): δ 2.89 (s, 3H), 8.04 (m, 2H), 8.18 (d, 2H), 8.85 (d, 1H), 13.50 (br.s , 2H). HPLC-MS: log P = 0.30; Mass (m / z): 232.0; 'HNMR (D 6 -DMSO): δ 2.89 (s, 3H), 8.04 (m, 2H), 8.18 (d, 2H), 8.85 (d, 1H), 13.50 (br.s, 2H).
5-Iodquinoline-2, 6-dicarbonsäure 5-iodoquinoline-2, 6-dicarboxylic acid
Figure imgf000072_0003
Figure imgf000072_0003
Methyl-5-nitrochinolin-6-carboxylat: 5-Nitrochinolin-6-carbonsäure (6200 mg, 28,4 mmol) (z.B. bekannt aus WO9812180) wurde in Dichlormethan (125,0 mL) suspendiert und bei 0°C mit Oxalylchlorid (4328 mg, 34,1 mmol) versetzt. Das Reaktionsgemisch wurde zunächst 1 h bei Raumtemperatur und anschließend noch 1 h bei Rückflußtemperatur gerührt. Nach Ab destillieren des Lösungsmittels wurde Methanol (23 mL, 18211 mmol) zugesetzt und 18 Stunden bei Raumtemperatur gerührt. Das überschüssige Methanol wurde zum größten Teil abdestilliert und der Rückstand mit 300 mL Wasser versetzt. Der ausgefallene Niederschlag wurde abgesaugt und getrocknet, wobei 6,0 g (64% d. Th.) Methyl-5-nitrochinolin-6-carboxylat erhalten wurden. HPLC-MS: logP = 1,98; Masse (m/z): 233,1. Methyl-5-aminochinolin-6-carboxylat: Methyl-5-nitrochinolin-6-carboxylat (600 mg, 25,8 mmol) wurde in Methanol/THF (250,0 mL/7,5 mL) gelöst und mit Pd-C als Katalysator (274 mg, 2,58 mmol) bei 1 bar Druck hydriert. Das Reaktionsgemisch wurde über Kieselgur filtriert, mit Methanol nachgewaschen und das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wurde in Ethylacetat aufgenommen, mit Wasser gewaschen, über Magnesiumsulfat getrocknet, anschließend eingeengt, wobei 5,20 g (94,5 % d. Th.) Methyl-5-aminochinolin-6-carboxylat erhalten wurden. HPLC-MS: logP = 0,41 ; Masse (m/z): 203,0. Methyl 5-nitroquinoline-6-carboxylate: 5-Nitroquinoline-6-carboxylic acid (6200 mg, 28.4 mmol) (eg known from WO9812180) was suspended in dichloromethane (125.0 mL) and treated at 0 ° C with oxalyl chloride ( 4328 mg, 34.1 mmol). The reaction mixture was first stirred for 1 h at room temperature and then for a further 1 h at reflux temperature. After distilling off the solvent, methanol (23 mL, 18211 mmol) was added and stirred at room temperature for 18 hours. The excess methanol was distilled off for the most part and the residue was mixed with 300 mL of water. The resulting precipitate was filtered off with suction and dried to give 6.0 g (64% of theory) of methyl 5-nitroquinoline-6-carboxylate. HPLC-MS: log P = 1.98; Mass (m / z): 233.1. Methyl 5-aminoquinoline-6-carboxylate: Methyl 5-nitroquinoline-6-carboxylate (600 mg, 25.8 mmol) was dissolved in methanol / THF (250.0 mL / 7.5 mL) and treated with Pd-C hydrogenated as catalyst (274 mg, 2.58 mmol) at 1 bar pressure. The reaction mixture was filtered through kieselguhr, washed with methanol and the solvent was distilled off under reduced pressure. The residue was taken up in ethyl acetate, washed with water, dried over magnesium sulfate, then concentrated to give 5.20 g (94.5% of theory) of methyl 5-aminoquinoline-6-carboxylate. HPLC-MS: log P = 0.41; Mass (m / z): 203,0.
Methyl-5-iodchinolin-6-carboxylat: Methyl-5-aminochinolin-6-carboxylat (4800 mg, 23,7 mmol) wurde bei 100 °C langsam zu einem Gemisch aus 3-Methylbutylnitrit (4449 mg, 37,9 mmol) und Methylendiiodid (38,2 mL, 474 mmol) gegeben. Nachdem 0,5 h bei 100 °C nachgerührt wurde, versetzte man das Reaktionsgemisch mit Wasser und extrahierte mehrfach mit Ethylacetat. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, über Magnesiumsulfat getrocknet und anschließend eingeengt. Der Rückstand wurde auf Kieselgel adsorbiert und mit Cyclohexan/Ethylacetat chromatographiert. Es wurden wobei 3,14 g (39,3 % d. Th.) Methyl-5-iodchinolin-6-carboxylat erhalten. HPLC-MS: logP = 2,21 ; Masse (m/z): 314,0. Methyl 5-iodoquinoline-6-carboxylate: Methyl 5-aminoquinoline-6-carboxylate (4800 mg, 23.7 mmol) was slowly added at 100 ° C to a mixture of 3-methylbutyl nitrite (4449 mg, 37.9 mmol). and methylene diiodide (38.2 mL, 474 mmol). After stirring for 0.5 h at 100 ° C, the reaction mixture was mixed with water and extracted several times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and then concentrated. The residue was adsorbed onto silica gel and chromatographed with cyclohexane / ethyl acetate. There were obtained 3.14 g (39.3% of theory) of methyl 5-iodoquinoline-6-carboxylate. HPLC-MS: logP = 2.21; Mass (m / z): 314.0.
Methyl-5-iodchinolin-6-carboxylat-l-oxid: Methyl-5-aminochinolin-6-carboxylat (2500 mg, 7,98 mmol) wurde in Dichlormethan (15,0 mL) vorgelegt und Wasserstoffperoxid (50 %ig, 1086 mg, 15,9 mmol) sowie Methyltrioxorhenium (VII) (39,8 mg, 0,16 mmol) zugesetzt. Das Reaktionsgemisch wurde 18 h gerührt, anschließend mit Wasser und die wässrige Phase mehrfach mit Ethylacetat extrahiert. Nach Trocknen über Magnesiumsulfat wurde das Lösungsmittel unter vermindertem Druck abdestilliert, der Rückstand auf Kieselgel adsorbiert und mit Cyclohexan/Ethylacetat chromatographiert. Es wurden 0,61 g (23 % d. Th.) Methyl-5-iodchinolin-6-carboxylat-l-oxid erhalten. HPLC-MS: logP = 1,31; Masse (m/z): 330,0. Methyl 5-iodoquinoline-6-carboxylate 1-oxide: Methyl 5-aminoquinoline-6-carboxylate (2500 mg, 7.98 mmol) was initially charged in dichloromethane (15.0 mL) and hydrogen peroxide (50%, 1086 mg, 15.9 mmol) and methyltrioxorhenium (VII) (39.8 mg, 0.16 mmol). The reaction mixture was stirred for 18 h, then extracted repeatedly with water and the aqueous phase with ethyl acetate. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, the residue was adsorbed on silica gel and chromatographed with cyclohexane / ethyl acetate. There were obtained 0.61 g (23% of theory) of methyl 5-iodoquinoline-6-carboxylate 1-oxide. HPLC-MS: log P = 1.31; Mass (m / z): 330.0.
Methyl-2-cyan-5-iodchinolin-6-carboxylat: Methyl-5-iodchinolin-6-carboxylat- 1 -oxid (600 mg, 1,82 mmol) wurde bei 0 °C in einer Lösung aus Kaliumcyanid (237 mg, 3,64 mmol) in Wasser (7,8 mL) vorgelegt. Hierzu wurde Benzoylchlorid (0,432 mL, 3,64 mmol) gegeben und 1 h unter Eiskühlung nachgerührt. Die wässrigePhase wurde abdekantiert und der Rückstand mit IM Kaliumcarbonatlösung verrührt. Nach Zusatz von Dichlormethan wurden die Phasen getrennt, mit Wasser gewaschen, über Magnesiumsulfat getrocknet und das Lösungsmittel im Vakuum entfernt. Der Rückstand wurde an Kieselgel mit Cyclohexan/Ethylacetat chromatographiert und ergab 0,33 g (48 % d. Th.) Methyl-2- cyan-5-iodchinolin-6-carboxylat. HPLC-MS: logP = 2,66; Masse (m/z): 338,9. Methyl 2-cyano-5-iodoquinoline-6-carboxylate: Methyl 5-iodoquinoline-6-carboxylate-1-oxide (600mg, 1.82mmol) was dissolved at 0 ° C in a solution of potassium cyanide (237mg, 3.64 mmol) in water (7.8 mL). To this was added benzoyl chloride (0.432 mL, 3.64 mmol) and stirred for 1 h under ice cooling. The aqueous phase was decanted off and the residue was stirred with 1M potassium carbonate solution. After addition of dichloromethane, the phases were separated, washed with water, dried over magnesium sulfate and the solvent removed in vacuo. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate to give 0.33 g (48% of theory) of methyl 2-cyano-5-iodoquinoline-6-carboxylate. HPLC-MS: logP = 2.66; Mass (m / z): 338.9.
5-Iodchinolin-2, 6-dicarbonsäure: Methyl-2-cyan-5-iodchinolin-6-carboxylat (326 mg, 0,96 mmol) wurde in Ethanol (8,0 mL) suspendiert und mit Natronlauge (45%ig, 685mg, 7,71 mmol) versetzt. Das Reaktionsgemisch wurde 18 Stunden bei 50°C nachgerührt und anschließend in 200 ml Eiswasser eingerührt. Nach Ansäuern mit 30%iger Salzsäure wurde der ausgefallene Feststoff abgesaugt und getrocknet. Es wurden 243 m g (71 % d.Th.) 5-Iodchinolin-2,6-dicarbonsäure erhalten. HPLC-MS: logP = 0,6; Masse (m/z): 343,9 (M+H)+; 'HNMR (D6-DMSO): δ 7,95 (d, 1H), 8.19 (d, 1H), 8.23 (d, 1H), 8.77 (d, 1H), 13.90 (br.s , 2H). Die in der folgenden Tabelle 1 beschriebenen erfindungsgemäßen Verbindungen der Formel (1-1) sind ebenfalls bevorzugte erfindungsgemäße Verbindungen der Formel (I), die man gemäß oder analog zu den oben beschriebenen Synthesebeispielen erhält. Hier stehen in Formel (I) R2 für H, W für O, Q1 und Q2 für CH, Q3 für C-R4a, Q4 für C-R4b und A für -CO-NR13- , G steht für ein freies Elektonenpaar. 5-iodoquinoline-2,6-dicarboxylic acid: methyl 2-cyano-5-iodoquinoline-6-carboxylate (326 mg, 0.96 mmol) was suspended in ethanol (8.0 mL) and washed with sodium hydroxide solution (45%, 685 mg, 7.71 mmol). The reaction mixture was stirred for 18 hours at 50 ° C and then in 200 ml of ice water stirred. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. 243 mg (71% of theory) of 5-iodoquinoline-2,6-dicarboxylic acid were obtained. HPLC-MS: log P = 0.6; Mass (m / z): 343.9 (M + H) + ; 'HNMR (D 6 -DMSO): δ 7.95 (d, 1H), 8.19 (d, 1H), 8.23 (d, 1H), 8.77 (d, 1H), 13.90 (br.s, 2H). The compounds of the formula (1-1) according to the invention described in the following Table 1 are likewise preferred compounds of the formula (I) according to the invention, which are obtained according to or analogously to the synthesis examples described above. Here, in formula (I), R 2 is H, W is O, Q 1 and Q 2 are CH, Q 3 is CR 4a , Q 4 is CR 4b, and A is -CO-NR 13 -, G is a free one Elektonenpaar.
Tabelle 1 Table 1
Figure imgf000075_0001
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000079_0001
Figure imgf000080_0002
Figure imgf000080_0002
Anmerkung: Die in Synthesebeispiel 2 hergestellte Verbindung der Formel (I-la-1) gehört nicht zu den Verbindungen der Formel (I-l), da in der Verbindung der Formel (I-la-1) G für Sauerstoff steht: Note: The compound of the formula (I-1a) prepared in Synthesis Example 2 does not belong to the compounds of the formula (I-1) since in the compound of the formula (I-1a-1) G is oxygen:
Figure imgf000080_0001
(I-la-1).
Figure imgf000080_0001
(I-la-1).
1H-NMR Daten 1H NMR data
Beispiel 1-1-01: 1H-NMR (400,0 MHz, de-DMSO): Siehe Synthesebeispiel 1 Example 1-1-01: 1 H-NMR (400.0 MHz, de-DMSO): See Synthesis Example 1
Beispiel 1-1-02: 1H-NMR (400,0 MHz, CD3CN):  Example 1-1-02: 1H-NMR (400.0 MHz, CD3CN):
5=10,350 (0,3); 9,263 (3,1); 9,238 (3,2); 8,606 (7,6); 8,589 (7,6); 8,472 (8,5); 8,450 (10,3); 8,260 (10,3); 8,249 (0,7); 8,239 (8,5); 8,022 (8,6); 7,951 (4,6); 7,931 (5,3); 7,794 (4,3); 7,775 (16,0); 7,748 (10,4); 7,704 (5,0); 7,684 (7,3); 7,665 (3,0); 7,593 (0,4); 7,456 (0,4); 7,437 (0,5); 7,265 (2,2); 6,198 (1,0); 6,178 (3,5); 6,157 (4,1); 6,133 (3,5); 6,112 (1,1); 4,069 (0,9); 4,051 (0,9); 2,966 (0,6); 2,957 (1 ,8); 2,948 (2,9); 2,938 (4,1); 2,929 (4,1); 2,920 (2,9); 2,911 (1 ,8); 2,901 (0,7); 2,223 (1686,6); 2,123 (2,8); 2,117 (3,3); 2,110 (3,8); 2,104 (2,9); 2,098 (2,0); 1,974 (6,2); 1,967(21,1); 1,961 (18,1); 1,955(142,5); 1,949 (266,6); 1,943 (373,9); 1,937 (260,2); 1,931 (135,6); 1,804 (0,7); 1,795 (0,6); 1,784(1,2); 1,778(1,9); 1,771 (2,5); 1,765(1,8); 1,759(1,1); 1,437 (12,0); 1,372 (0,4); 1,271 (0,7); 1,222 (1,2); 1,205(2,2); 1,187 (1,2); 0,911 (0,5); 0,879 (0,4); 0,860 (0,4); 0,842 (2,9); 0,829 (8,2); 0,824 (10,9); 0,811 (11,4); 0,806 (8,3); 0,794 (3,9); 0,772 (0,7); 0,755 (0,9); 0,738 (0,4); 0,733 (0,4); 0,712 (0,6); 0,702 (0,6); 0,672 (3,8); 0,660 (9,6); 0,654 (10,0); 0,650 5 = 10.350 (0.3); 9,263 (3,1); 9.238 (3.2); 8,606 (7.6); 8,589 (7.6); 8,472 (8.5); 8,450 (10.3); 8.260 (10.3); 8.249 (0.7); 8,239 (8.5); 8.022 (8.6); 7.951 (4.6); 7,931 (5.3); 7,794 (4,3); 7,775 (16.0); 7,748 (10.4); 7,704 (5.0); 7,684 (7.3); 7.665 (3.0); 7,593 (0.4); 7.456 (0.4); 7.437 (0.5); 7.265 (2.2); 6.198 (1.0); 6.178 (3.5); 6,157 (4,1); 6.133 (3.5); 6.112 (1.1); 4,069 (0.9); 4,051 (0.9); 2.966 (0.6); 2.957 (1, 8); 2,948 (2.9); 2,938 (4,1); 2,929 (4,1); 2,920 (2.9); 2,911 (1, 8); 2,901 (0.7); 2,223 (1686,6); 2,123 (2,8); 2,117 (3,3); 2,110 (3.8); 2,104 (2,9); 2,098 (2.0); 1,974 (6.2); 1,967 (21.1); 1,961 (18,1); 1.955 (142.5); 1,949 (266.6); 1,943 (373.9); 1,937 (260,2); 1,931 (135.6); 1,804 (0.7); 1,795 (0.6); 1,784 (1.2); 1.778 (1.9); 1,771 (2.5); 1,765 (1.8); 1,759 (1.1); 1,437 (12.0); 1,372 (0.4); 1,271 (0.7); 1,222 (1,2); 1.205 (2.2); 1.187 (1.2); 0.911 (0.5); 0.879 (0.4); 0.860 (0.4); 0.842 (2.9); 0.829 (8.2); 0.824 (10.9); 0.811 (11.4); 0.806 (8.3); 0.794 (3.9); 0.772 (0.7); 0.755 (0.9); 0.738 (0.4); 0.733 (0.4); 0.712 (0.6); 0.702 (0.6); 0.672 (3.8); 0.660 (9.6); 0.654 (10.0); 0,650
(8,8); 0,645 (8,7); 0,632 (2,8); 0,600 (0,5); 0,595 (0,5); 0,000 (1 ,6) (8.8); 0.645 (8.7); 0.632 (2.8); 0.600 (0.5); 0.595 (0.5); 0,000 (1, 6)
Beispiel 1-1-03: 1H-NMR (400,0 MHz, CD3CN): Example 1-1-03: 1 H-NMR (400.0 MHz, CD3CN):
δ= 9,232 (1,9); 9,208 (1,9); 8,802 (4,2); 8,800 (4,6); 8,780 (4,4); 8,778 (4,9); 8,343 (0,3); 8,286 (0,3); 8,276 (7,3); 8,266 (0,4); 8,264 (0,4); 8,254 (6,7); 8,196 (4,3); 8,195 (4,6); 8,175 (4,7); 8,173 (5,0); 8,028 (4,5); 7,954 (2,4); 7,935 (2,8); 7,825 (0,4); 7,798 (2,3); 7,784 (8,3); 7,778 (3,4); 7,763 (6,7); 7,709 (2,7); 7,690 (3,9); 7,670 (1,5); 7,099 (1,8); 6,206 (0,5); 6,185 (1,8); 6,165 (2,1); 6,162 (2,0); 6,141 (1,8); 6,120 (0,6); 5,449 (16,0); 4,025 (0,5); 3,951 (0,5); 2,936 (0,4); 2,926 (1,2); 2,917 (1,8); 2,908 (2,7); 2,899 (2,8); 2,890 (1,8); 2,881 (1,3); 2,871 (0,4); 2,157 (8,7); 1,968 (0,6); 1,962 (0,7); 1,956 (6,0); 1,950 (11,1); 1,944(15,6); 1,937(10,7); 1,931 (5,5); 1,433 (2,9); 1,374 (1,2); 1,339 (0,4); 1,283 (0,5); 1,276 (1,3); 0,833 (1,6); 0,821 (4,3); 0,815 (5,9); 0,803 (6,1); 0,797 (4,3); 0,785 (2,1); 0,661 (2,1); 0,651 (4,9); 0,650 (4,9); 0,644 (5,2); 0,640 (4,5); 0,634 (4,5); 0,622 (1,5); 0,008 δ = 9.232 (1.9); 9,208 (1,9); 8,802 (4,2); 8,800 (4,6); 8,780 (4.4); 8,778 (4.9); 8,343 (0.3); 8,286 (0.3); 8.276 (7.3); 8.266 (0.4); 8.264 (0.4); 8,254 (6,7); 8,196 (4,3); 8,195 (4,6); 8,175 (4,7); 8,173 (5.0); 8.028 (4.5); 7.954 (2.4); 7,935 (2.8); 7.825 (0.4); 7,798 (2,3); 7,784 (8.3); 7,778 (3,4); 7,763 (6,7); 7,709 (2.7); 7.690 (3.9); 7,670 (1.5); 7,099 (1.8); 6,206 (0.5); 6.185 (1.8); 6,165 (2,1); 6.162 (2.0); 6.141 (1.8); 6.120 (0.6); 5,449 (16.0); 4.025 (0.5); 3.951 (0.5); 2,936 (0.4); 2,926 (1,2); 2.917 (1.8); 2,908 (2,7); 2,899 (2.8); 2,890 (1.8); 2,881 (1.3); 2,871 (0.4); 2,157 (8,7); 1,968 (0.6); 1,962 (0.7); 1,956 (6.0); 1,950 (11.1); 1,944 (15.6); 1,937 (10.7); 1,931 (5.5); 1,433 (2.9); 1.374 (1.2); 1,339 (0.4); 1.283 (0.5); 1.276 (1.3); 0.833 (1.6); 0.821 (4.3); 0.815 (5.9); 0.803 (6.1); 0.797 (4.3); 0.785 (2.1); 0.661 (2.1); 0.651 (4.9); 0.650 (4.9); 0.644 (5.2); 0.640 (4.5); 0.634 (4.5); 0.622 (1.5); 0,008
(0,5); 0,000 (13,1); -0,009 (0,5) (0.5); 0.000 (13.1); -0.009 (0.5)
Beispiel 1-1-04: 1H-NMR (400,0 MHz, de-DMSO): Example 1-1-04: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 10,047 (2,2); 10,022 (2,3); 9,471 (4,8); 8,831 (2,6); 8,809 (2,8); 8,296 (3,0); 8,199 (4,2); 8,177 (4,2); 8,167 (2,7); 8,146 (3,5); 8,132 (1,8); 7,838 (1,5); 7,819 (2,1); 7,789 (3,8); 7,767 (3,5); 7,743 (1,6); 7,723 (2,5); 7,704 (1,1); 6,384 (0,8); 6,363 (1,2); 6,340 (0,9); 4,348 (0,5); 4,338 (0,5); 3,325 (45,4); 3,086 (0,6); 2,690 (16,0); 2,677 (0,7); 2,672 (0,7); 2,667 (0,5); 2,617 (0,5); 2,576 (0,6); 2,525 (1,6); 2,512 (33,0); 2,507 (65,2); 2,503 (84,4); 2,498 (59,7); 2,494 (27,9); 2,334 (0,4); 2,329 (0,6); 2,325 (0,4); 1,626 (1,5); 1,611 (3,7); 1,604 (4,0); 1,592 (1,7); 1,353 (1,8); 1,340 (3,7); 1,333 (4,0); 1,319 (1,4); 1,046 (3,3); 1,030 (3,2); 0,146 (0,7); 0,024 (0,3); 0,008 (6,5); 0,000 (148,0); -0,009 (5,1); -0,150 (0,7) Beispiel 1-1-05: 1H-NMR (400,0 MHz, de-DMSO): δ = 10.047 (2.2); 10.022 (2.3); 9,471 (4,8); 8.831 (2.6); 8,809 (2.8); 8.296 (3.0); 8,199 (4.2); 8,177 (4,2); 8,167 (2,7); 8.146 (3.5); 8.132 (1.8); 7.838 (1.5); 7,819 (2,1); 7,789 (3.8); 7,767 (3.5); 7,743 (1.6); 7,723 (2.5); 7.704 (1.1); 6,384 (0.8); 6,363 (1,2); 6.340 (0.9); 4,348 (0.5); 4,338 (0.5); 3,325 (45.4); 3.086 (0.6); 2,690 (16.0); 2,677 (0.7); 2,672 (0.7); 2,667 (0.5); 2,617 (0.5); 2.576 (0.6); 2,525 (1.6); 2,512 (33.0); 2,507 (65,2); 2,503 (84,4); 2,498 (59.7); 2,494 (27.9); 2.334 (0.4); 2,329 (0.6); 2.325 (0.4); 1,626 (1.5); 1,611 (3.7); 1.604 (4.0); 1,592 (1.7); 1.353 (1.8); 1,340 (3.7); 1,333 (4.0); 1,319 (1.4); 1,046 (3.3); 1,030 (3.2); 0.146 (0.7); 0.024 (0.3); 0.008 (6.5); 0.000 (148.0); -0.009 (5.1); -0.150 (0.7) Example 1-1-05: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 10,027 (2,1); 10,002 (2,2); 8,962 (4,4); 8,811 (2,6); 8,789 (2,8); 8,317 (0,4); 8,294 (3,0); 8,176 (4,3); 8,154 (5,6); 8,139 (2,8); 8,118 (3,2); 8,025 (4,0); 8,003 (2,9); 7,840 (1,4); 7,820 (2,1); 7,745 (1,6); 7,725 (2,4); 7,706 (1,0); 7,215 (1,2); 7,166 (1,2); 6,385 (0,8); 6,363 (1,2); 6,340 (0,9); 4,348 (0,5); 4,337 (0,5); 3,324 (55,2); 2,689 (0,3); 2,664 (16,0); 2,542 (0,6); 2,525 (2,5); 2,511 (48,1); 2,507 (95,9); 2,502 (124,7); 2,498 (88,4); 2,493 (41,3); 2,334 (0,6); 2,329 (0,8); 2,325 (0,5); 1,384 (1,6); 1,373 (3,6); 1,365 (4,0); 1,355 (1,6); δ = 10.027 (2.1); 10.002 (2.2); 8,962 (4.4); 8,811 (2.6); 8,789 (2,8); 8.317 (0.4); 8.294 (3.0); 8,176 (4,3); 8,154 (5.6); 8.139 (2.8); 8.118 (3.2); 8.025 (4.0); 8.003 (2.9); 7,840 (1.4); 7,820 (2,1); 7,745 (1.6); 7.725 (2.4); 7.706 (1.0); 7.215 (1.2); 7.166 (1.2); 6.385 (0.8); 6,363 (1,2); 6.340 (0.9); 4,348 (0.5); 4,337 (0.5); 3,324 (55.2); 2.689 (0.3); 2,664 (16.0); 2,542 (0.6); 2,525 (2.5); 2,511 (48.1); 2,507 (95.9); 2,502 (124.7); 2,498 (88.4); 2,493 (41.3); 2.334 (0.6); 2.329 (0.8); 2.325 (0.5); 1.384 (1.6); 1.373 (3.6); 1,365 (4.0); 1.355 (1.6);
1,235 (0,6); 1,050 (1,9); 1,045 (5,9); 1,040 (4,0); 1,030 (7,1); 1,021 (1,5); 0,146 (1,1); 0,008 (10,7); 0,000 (257,5); -0,009 (9,1); -0,150 (1,1) 1.235 (0.6); 1,050 (1.9); 1.045 (5.9); 1,040 (4.0); 1,030 (7.1); 1.021 (1.5); 0.146 (1.1); 0.008 (10.7); 0,000 (257.5); -0.009 (9.1); -0.150 (1.1)
Beispiel 1-1-06: 1H-NMR (400,0 MHz, de-DMSO): Example 1-1-06: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 10,037 (2,1); 10,012 (2,2); 8,798 (2,6); 8,776 (2,8); 8,560 (2,3); 8,549 (2,3); 8,296 (3,3); 8,181 (3,6); 8,159 (3,8); 8,150 (2,1); 8,133 (4,2); 8,112 (2,8); 7,837 (1 ,7); 7,818 (2,3); 7,746 (4,1); 7,724 (5,1); 7,703 (1,1); 6,380 (0,9); 6,358 (1,4); 6,336 (1,0); 3,326 (28,8); 2,926 (0,6); 2,916 (1,0); 2,908 (1,4); 2,898 (1,4); 2,889 (1,0); 2,880 (0,7); 2,666 (16,0); 2,507 (53,9); 2,503 (66,5); 2,499 (51,2); 2,330 (0,4); 1,234 (0,7); 1,046 (1,5); 1,031 (1,5); 0,756 (0,9); 0,738 (3,5); 0,725 (3,3); 0,720 (2,8); 0,709 (1,1); 0,589 (1,2); 0,579 (3,7); δ = 10.037 (2.1); 10.012 (2.2); 8.798 (2.6); 8,776 (2.8); 8.560 (2.3); 8.549 (2.3); 8.296 (3.3); 8,181 (3.6); 8,159 (3,8); 8.150 (2.1); 8,133 (4,2); 8,112 (2,8); 7,837 (1, 7); 7.818 (2.3); 7,746 (4,1); 7,724 (5.1); 7,703 (1,1); 6,380 (0.9); 6.358 (1.4); 6.336 (1.0); 3,326 (28.8); 2,926 (0.6); 2.916 (1.0); 2.908 (1.4); 2,898 (1.4); 2,889 (1.0); 2,880 (0.7); 2,666 (16.0); 2,507 (53.9); 2,503 (66.5); 2,499 (51.2); 2,330 (0.4); 1,234 (0.7); 1.046 (1.5); 1.031 (1.5); 0.756 (0.9); 0.738 (3.5); 0.725 (3.3); 0.720 (2.8); 0.709 (1.1); 0.589 (1.2); 0.579 (3.7);
0,573 (3,6); 0,564 (3,0); 0,551 (0,9); 0,146 (0,5); 0,000 (93,6); -0,150 (0,5) 0.573 (3.6); 0.564 (3.0); 0.551 (0.9); 0.146 (0.5); 0,000 (93.6); -0.150 (0.5)
Beispiel 1-1-07: 1H-NMR (400,0 MHz, de-DMSO): Example 1-1-07: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 10,188 (3,7); 10,163 (3,9); 9,668 (8,5); 8,897 (4,8); 8,875 (5,3); 8,873 (5,3); 8,435 (4,9); 8,431 (4,9); 8,320 (10,6); 8,298 (10,1); 8,197 (2,4); 8,193 (2,3); 8,176 (2,7); 8,172 (2,6); 7,951 (7,8); 7,930 (7,2); 7,883 (5,1); 7,862 (4,5); 6,479 (0,4); 6,457 (1,4); 6,436 (2,0); 6,413 (1,5); 6,391 (0,4); 5,760 (0,4); 4,058 (1,2); 4,040 (3,6); 4,023 (3,7); 4,005 (1,2); 3,841 δ = 10.188 (3.7); 10.163 (3.9); 9,668 (8.5); 8,897 (4,8); 8,875 (5.3); 8,873 (5.3); 8,435 (4.9); 8,431 (4.9); 8,320 (10.6); 8,298 (10.1); 8,197 (2,4); 8,193 (2,3); 8.176 (2.7); 8,172 (2.6); 7.951 (7.8); 7,930 (7.2); 7,883 (5.1); 7,862 (4,5); 6,479 (0.4); 6.457 (1.4); 6,436 (2.0); 6.413 (1.5); 6,391 (0.4); 5,760 (0.4); 4.058 (1.2); 4,040 (3.6); 4,023 (3.7); 4.005 (1.2); 3,841
(0,7); 3,331 (40,5); 2,675 (0,4); 2,528 (1,0); 2,515 (25,6); 2,510 (50,3); 2,506 (64,3); 2,501 (44,9); 2,497 (20,7); 2,333 (0,4); 1,992 (16,0); 1,657 (2,7); 1,642 (6,5); 1,636 (6,9);(0.7); 3,331 (40.5); 2,675 (0.4); 2,528 (1.0); 2,515 (25,6); 2,510 (50.3); 2,506 (64,3); 2,501 (44.9); 2,497 (20.7); 2.333 (0.4); 1,992 (16.0); 1.657 (2.7); 1,642 (6.5); 1,636 (6.9);
1,623 (3,0); 1,359 (3,2); 1,345 (6,6); 1,338 (6,9); 1,324 (2,5); 1,195 (4,3); 1,177 (8,4); 1,159 (4,2); 0,008 (0,6); 0,000 (14,0); -0,009 (0,4) 1,623 (3.0); 1,359 (3.2); 1.345 (6.6); 1,338 (6.9); 1,324 (2.5); 1,195 (4.3); 1,177 (8.4); 1,159 (4,2); 0.008 (0.6); 0.000 (14.0); -0.009 (0.4)
Beispiel 1-1-08: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-08: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,104 (2,2); 10,080 (2,2); 9,474 (4,8); 8,831 (2,6); 8,809 (2,8); 8,430 (3,0); 8,427 (3,0); 8,196 (5,6); 8,174 (5,7); 8,163 (2,7); 8,141 (2,8); 7,881 (3,0); 7,860 (2,6); 7,791 (3,7); 7,769 (3,4); 6,442 (0,8); 6,420 (1,2); 6,398 (0,9); 5,759 (0,8); 4,040 (0,8); 4,022 (0,8); 3,330 (22,1); 2,692 (16,0); 2,674 (0,4); 2,527 (0,8); 2,514 (16,6); 2,510 (32,1); 2,505 (41,0); 2,501 (29,0); 2,496 (13,7); 1,991 (3,4); 1,629 (1,6); 1,615(3,9); 1,608(4,1); 1,595(1,7); 1,356 (1,9); 1,342 (3,9); 1,336 (4,1); 1,321 (1,4); 1,195 (0,9); 1,177(1,8); 1,159 (0,9);δ = 10.104 (2.2); 10.080 (2.2); 9,474 (4,8); 8.831 (2.6); 8,809 (2.8); 8,430 (3.0); 8,427 (3.0); 8.196 (5.6); 8,174 (5,7); 8,163 (2,7); 8,141 (2,8); 7.881 (3.0); 7.860 (2.6); 7,791 (3.7); 7,769 (3,4); 6.442 (0.8); 6.420 (1.2); 6,398 (0.9); 5,759 (0.8); 4,040 (0.8); 4.022 (0.8); 3,330 (22.1); 2,692 (16.0); 2,674 (0.4); 2,527 (0.8); 2,514 (16.6); 2,510 (32.1); 2,505 (41.0); 2,501 (29.0); 2,496 (13.7); 1,991 (3,4); 1,629 (1.6); 1,615 (3.9); 1,608 (4.1); 1,595 (1.7); 1.356 (1.9); 1,342 (3.9); 1,336 (4,1); 1,321 (1.4); 1,195 (0.9); 1,177 (1.8); 1,159 (0.9);
0,008 (0,8); 0,000 (16,3); -0,009 (0,6) 0.008 (0.8); 0,000 (16.3); -0.009 (0.6)
Beispiel 1-1-09: 1H-NMR (600,1 MHz, d6-DMSO): Example 1-1-09: 1 H NMR (600.1 MHz, d 6 -DMSO):
δ= 10,135 (2,0); 10,122 (2,1); 9,675 (2,5); 8,899 (10,1); 8,884 (10,9); 8,883 (10,3); 8,332 (10,2); 8,325 (15,4); 8,318 (11,6); 8,317 (11,0); 8,310 (16,0); 8,302 (10,9); 8,154 (5,8); 8,141 (6,2); 7,952 (14,8); 7,937 (14,3); 7,841 (5,5); 7,828 (7,0); 7,744 (5,1); 7,731 (8,7); 7,718 (3,9); 6,378 (2,6); 6,366 (1,9); 4,040 (0,6); 4,028 (0,6); 3,417 (0,4); 3,413 (0,3); 3,367 (653,8); 3,324 (0,4); 2,622 (0,4); 2,531 (0,7); 2,528 (0,9); 2,525 (0,9); 2,516 (23,7); 2,513 (49,7); 2,510 (67,9); 2,507 (49,7); 2,505 (23,8); 2,394 (0,4); 2,092 (10,2); 1,993 (2,6); 1,679 (0,3); 1,653 (5,7); 1,644(13,5); 1,639 (15,2); 1,630 (5,9); 1,604 (0,5); 1,387 (0,5); 1,360 (6,4); 1,351 (13,7); 1,346 (15,2); 1,337(5,3); 1,311 (0,4); 1,191 (0,7); 1,179δ = 10.135 (2.0); 10.122 (2,1); 9.675 (2.5); 8,899 (10.1); 8.884 (10.9); 8,883 (10.3); 8,332 (10,2); 8,325 (15.4); 8,318 (11,6); 8,317 (11.0); 8,310 (16.0); 8,302 (10.9); 8,154 (5.8); 8,141 (6,2); 7,952 (14.8); 7,937 (14,3); 7,841 (5.5); 7,828 (7.0); 7,744 (5.1); 7,731 (8.7); 7,718 (3.9); 6.378 (2.6); 6,366 (1.9); 4,040 (0.6); 4.028 (0.6); 3,417 (0.4); 3,413 (0.3); 3,367 (653.8); 3,324 (0.4); 2,622 (0.4); 2,531 (0.7); 2,528 (0.9); 2,525 (0.9); 2,516 (23.7); 2,513 (49,7); 2,510 (67.9); 2,507 (49,7); 2,505 (23.8); 2,394 (0.4); 2,092 (10.2); 1,993 (2.6); 1,679 (0.3); 1,653 (5.7); 1,644 (13.5); 1,639 (15.2); 1,630 (5.9); 1.604 (0.5); 1.387 (0.5); 1,360 (6.4); 1,351 (13.7); 1,346 (15,2); 1,337 (5.3); 1,311 (0.4); 1.191 (0.7); 1,179
(1,4); 1,167 (0,7); 0,000 (2,0) (1.4); 1.167 (0.7); 0,000 (2.0)
Beispiel 1-1-10: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-10: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,083 (6,2); 10,058 (6,4); 8,874 (8,6); 8,852 (9,5); 8,751 (6,6); 8,740 (6,6); 8,339 (0,4); 8,317 (1,2); 8,305 (13,2); 8,299 (8,7); 8,283 (12,7); 8,277 (9,7); 8,237 (16,0); 8,221 (16,0); 7,963 (0,4); 7,941 (0,4); 7,892 (12,2); 7,871 (11,3); 6,383 (0,6); 6,362 (2,3); 6,340 (3,3); 6,317 (2,5); 6,295 (0,8); 5,757 (0,4); 4,056 (0,4); 4,039 (1,2); 4,021 (1,2); 4,003 (0,4); 3,569 (3,5); 3,327 (193,6); 2,935 (0,6); 2,925 (1,8); 2,915 (2,5); 2,907 (3,9); 2,897 (4,0); 2,888 (2,5); 2,878 (1,9); 2,868 (0,7); 2,677 (1,0); 2,672 (1,4); 2,668 (1,1); 2,543 (0,8); 2,525 (3,5); 2,512 (82,3); 2,508 (163,6); 2,503 (213,4); 2,499 (154,1); 2,495 (74,6); 2,334 (1,0); 2,330 (1,4); 2,326 (1,0); 1,990 (5,1); 1,910 (0,6); 1,232 (0,4); 1,194 (1,3); 1,176 (2,6); 1,158 (1,3); 0,774 (2,4); 0,761 (7,3); 0,756 (9,8); 0,744 (9,0); 0,738 (7,7); 0,727 (3,0); 0,706 (0,4); 0,687 (0,3); 0,640 (0,3); 0,631 (0,3); 0,601 (3,1); 0,590 (9,6); 0,584 (9,0);δ = 10.083 (6.2); 10,058 (6.4); 8,874 (8.6); 8,852 (9.5); 8.751 (6.6); 8,740 (6.6); 8.399 (0.4); 8.317 (1.2); 8,305 (13.2); 8,299 (8.7); 8,283 (12,7); 8,277 (9.7); 8.237 (16.0); 8,221 (16,0); 7.963 (0.4); 7.941 (0.4); 7,892 (12.2); 7,871 (11.3); 6,383 (0.6); 6.362 (2.3); 6.340 (3.3); 6.317 (2.5); 6.295 (0.8); 5,757 (0.4); 4.056 (0.4); 4.039 (1.2); 4.021 (1.2); 4.003 (0.4); 3,569 (3.5); 3,327 (193.6); 2,935 (0.6); 2,925 (1.8); 2.915 (2.5); 2.907 (3.9); 2,897 (4.0); 2,888 (2.5); 2,878 (1.9); 2,868 (0.7); 2,677 (1.0); 2,672 (1.4); 2,668 (1.1); 2,543 (0.8); 2,525 (3.5); 2,512 (82,3); 2,508 (163,6); 2,503 (213.4); 2,499 (154.1); 2,495 (74.6); 2.334 (1.0); 2,330 (1.4); 2,326 (1.0); 1,990 (5.1); 1.910 (0.6); 1,232 (0.4); 1,194 (1.3); 1.176 (2.6); 1.158 (1.3); 0.774 (2.4); 0.761 (7.3); 0.756 (9.8); 0.744 (9.0); 0.738 (7.7); 0.727 (3.0); 0.706 (0.4); 0.687 (0.3); 0.640 (0.3); 0.631 (0.3); 0.601 (3.1); 0.590 (9.6); 0.584 (9.0);
0,580 (8,5); 0,574 (8,0); 0,562 (2,3); 0,465 (0,3); 0,457 (0,3); 0,146 (0,8); 0,008 (6,3); 0,000 (172,4); -0,008 (6,5); -0,150 (0,8) 0.580 (8.5); 0.574 (8.0); 0.562 (2.3); 0.465 (0.3); 0.457 (0.3); 0.146 (0.8); 0.008 (6.3); 0,000 (172.4); -0.008 (6.5); -0.150 (0.8)
Beispiel 1-1-11: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-11: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,090 (2,3); 10,065 (2,4); 9,671 (5,3); 8,896 (3,2); 8,874 (3,5); 8,336 (3,2); 8,323 (5,1); 8,315 (3,5); 8,314 (3,7); 8,301 (4,8); 8,237 (6,1); 8,221 (6,1); 7,953 (4,8); 7,931 (4,5); 6,366 (0,9); 6,345 (1,2); 6,322 (0,9); 3,328 (48,6); 2,673 (0,4); 2,513 (25,1); 2,509 (50,5); 2,504 (66,3); 2,500 (48,1); 2,495 (23,4); 2,331 (0,4); 2,088 (16,0); 1,655 (1,7); 1,641δ = 10.090 (2.3); 10.065 (2.4); 9,671 (5.3); 8.896 (3.2); 8.874 (3.5); 8.366 (3.2); 8,323 (5.1); 8.315 (3.5); 8,314 (3.7); 8,301 (4,8); 8,237 (6,1); 8,221 (6,1); 7,953 (4,8); 7.931 (4.5); 6.366 (0.9); 6,345 (1.2); 6,322 (0.9); 3,328 (48.6); 2,673 (0.4); 2,513 (25.1); 2,509 (50.5); 2,504 (66.3); 2,500 (48.1); 2,495 (23.4); 2,331 (0.4); 2,088 (16.0); 1.655 (1.7); 1.641
(4,2); 1,634 (4,5); 1,621 (1,9); 1,357 (2,0); 1,344 (4,2); 1,337 (4,5); 1,323 (1,6); 1,142 (0,5); 0,146 (0,4); 0,008 (4,2); 0,000 (95,6); -0,009 (3,5); -0,150 (0,4) (4.2); 1,634 (4.5); 1,621 (1.9); 1.357 (2.0); 1,344 (4,2); 1,337 (4,5); 1,323 (1.6); 1.142 (0.5); 0.146 (0.4); 0.008 (4.2); 0.000 (95.6); -0.009 (3.5); -0.150 (0.4)
Beispiel 1-1-12: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-12: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,121 (1,9); 10,096 (2,0); 9,482 (4,4); 8,849 (2,6); 8,827 (2,8); 8,524 (1,1); 8,505 (2,1); 8,486 (1,1); 8,219 (3,9); 8,197 (3,8); 8,168 (2,4); 8,146 (2,8); 7,797 (3,6); 7,775 (3,3); 6,467 (0,8); 6,446 (1,2); 6,423 (0,9); 4,039 (0,6); 4,021 (0,6); 3,328 (24,3); 2,694 (16,0); 2,673 (0,4); 2,509 (32,8); 2,504 (42,8); 2,500 (31,1); 2,088 (9,0); 1,991 (2,5); 1,628 (1,5); 1,614(3,9); 1,607 (4,1); 1,594 (1,7); 1,356(1,8); 1,343 (3,9); 1,336 (4,1); 1,321 (1,4); 1,194 (0,7); 1,177(1,3); 1,159 (0,7); 1,142 (0,4); 0,008 (2,5); 0,000 (63,2); -0,009 (2,2) Beispiel 1-1-13: 1H-NMR (400,0 MHz, d6-DMSO): δ = 10.121 (1.9); 10.096 (2.0); 9,482 (4,4); 8,849 (2.6); 8,827 (2,8); 8.524 (1.1); 8,505 (2.1); 8.486 (1.1); 8,219 (3.9); 8,197 (3,8); 8.168 (2.4); 8.146 (2.8); 7,797 (3.6); 7,775 (3.3); 6,467 (0.8); 6,446 (1,2); 6,423 (0.9); 4,039 (0.6); 4,021 (0.6); 3,328 (24.3); 2,694 (16.0); 2,673 (0.4); 2,509 (32,8); 2,504 (42.8); 2,500 (31.1); 2,088 (9.0); 1,991 (2.5); 1.628 (1.5); 1,614 (3.9); 1,607 (4.1); 1,594 (1.7); 1.356 (1.8); 1,343 (3.9); 1,336 (4,1); 1,321 (1.4); 1,194 (0.7); 1,177 (1.3); 1.159 (0.7); 1,142 (0.4); 0.008 (2.5); 0,000 (63.2); -0.009 (2.2) Example 1-1-13: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,113 (1,9); 10,089 (2,0); 8,815 (2,4); 8,793 (2,6); 8,568 (2,1); 8,557 (2,1); 8,528 (1,1); 8,509 (1,9); 8,490 (1,1); 8,317 (0,5); 8,199 (3,8); 8,177 (3,7); 8,132 (2,3); 8,110 (2,5); 7,751 (3,5); 7,730 (3,1); 6,465 (0,8); 6,443 (1,1); 6,420 (0,8); 3,324 (95,7); 3,175 (1,1); 3,162 (1,0); 2,925 (0,6); 2,916 (0,9); 2,907 (1,3); 2,897 (1,3); 2,889 (0,8); 2,879 (0,6); 2,667 (16,0); 2,524 (4,6); 2,511 (51,5); 2,507 (100,9); 2,502 (131,4); 2,498 (94,5); 2,493 (45,9); 2,333 (0,6); 2,329 (0,9); 2,325 (0,6); 0,756 (0,9); 0,743 (2,5); 0,738 (3,3); 0,726 (3,0);δ = 10.113 (1.9); 10,089 (2.0); 8.815 (2.4); 8,793 (2.6); 8,568 (2,1); 8,557 (2,1); 8.528 (1.1); 8,509 (1.9); 8.490 (1.1); 8.317 (0.5); 8,199 (3.8); 8,177 (3.7); 8.132 (2.3); 8.110 (2.5); 7.751 (3.5); 7,730 (3,1); 6,465 (0.8); 6.433 (1.1); 6,420 (0.8); 3,324 (95.7); 3.175 (1.1); 3.162 (1.0); 2,925 (0.6); 2,916 (0.9); 2.907 (1.3); 2,897 (1.3); 2,889 (0.8); 2,879 (0.6); 2,667 (16.0); 2,524 (4,6); 2,511 (51.5); 2,507 (100.9); 2,502 (131.4); 2,498 (94.5); 2,493 (45.9); 2.333 (0.6); 2,329 (0.9); 2.325 (0.6); 0.756 (0.9); 0.743 (2.5); 0.738 (3.3); 0.726 (3.0);
0,720 (2,6); 0,709 (1,1); 0,589 (1,1); 0,578 (3,2); 0,572 (2,9); 0,563 (2,7); 0,550 (0,8); 0,146 (1,0); 0,008 (10,4); 0,000 (231,7); -0,009 (10,1); -0,150 (1,1) 0.720 (2.6); 0.709 (1.1); 0.589 (1.1); 0.578 (3.2); 0.572 (2.9); 0.563 (2.7); 0,550 (0.8); 0.146 (1.0); 0.008 (10.4); 0.000 (231.7); -0.009 (10.1); -0.150 (1.1)
Beispiel 1-1-14: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-14: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,189 (5,8); 10,164 (6,0); 8,892 (9,4); 8,890 (9,1); 8,870 (10,3); 8,868 (10,2); 8,755 (7,3); 8,744 (7,4); 8,511 (3,6); 8,493 (6,5); 8,474 (3,6); 8,324 (16,0); 8,318 (2,4); 8,302 (15,7); 8,291 (9,1); 8,289 (8,8); 8,269 (10,1); 8,267 (10,1); 7,967 (0,5); 7,946 (0,5); 7,896 (15,0); 7,874 (14,0); 6,485 (0,7); 6,465 (2,4); 6,444 (3,5); 6,421 (2,6); 6,400 (0,8); 5,758 (0,7); 4,103 (0,7); 4,089 (0,7); 3,569 (0,4); 3,326 (141,8); 3,303 (0,7); 3,177 (3,1); 3,163 (3,0); 2,935 (0,7); 2,925 (2,1); 2,916 (2,8); 2,907 (4,5); 2,897 (4,6); 2,888 (2,8); 2,878 (2,2); 2,868 (0,8); 2,677 (1,1); 2,672 (1,4); 2,668 (1,1); 2,543 (0,8); 2,526 (3,4); 2,521 (5,5); 2,512 (81,7); 2,508 (168,0); 2,503 (221,4); 2,499 (157,1); 2,494 (73,9); 2,339 (0,6); 2,335 δ = 10.189 (5.8); 10.164 (6.0); 8,892 (9.4); 8,890 (9.1); 8,870 (10.3); 8,868 (10.2); 8,755 (7.3); 8,744 (7.4); 8,511 (3.6); 8,493 (6.5); 8.474 (3.6); 8,324 (16.0); 8.318 (2.4); 8,302 (15,7); 8,291 (9.1); 8,289 (8,8); 8.269 (10.1); 8,267 (10,1); 7.967 (0.5); 7.946 (0.5); 7,896 (15.0); 7,874 (14.0); 6.455 (0.7); 6,465 (2,4); 6.444 (3.5); 6,421 (2,6); 6,400 (0.8); 5,758 (0.7); 4.103 (0.7); 4,089 (0.7); 3,569 (0.4); 3,326 (141.8); 3.303 (0.7); 3,177 (3,1); 3.163 (3.0); 2,935 (0.7); 2,925 (2.1); 2,916 (2.8); 2,907 (4,5); 2,897 (4,6); 2,888 (2.8); 2,878 (2.2); 2,868 (0.8); 2,677 (1.1); 2,672 (1.4); 2,668 (1.1); 2,543 (0.8); 2,526 (3,4); 2,521 (5.5); 2,512 (81.7); 2,508 (168,0); 2,503 (221.4); 2,499 (157.1); 2,494 (73.9); 2,339 (0.6); 2,335
(1.0) ; 2,330 (1 ,4); 2,326 (1 ,0); 2,321 (0,5); 0,774 (3,0); 0,761 (8,1); 0,756 (11 ,5); 0,744 (10,6); 0,738 (8,9); 0,727 (3,7); 0,717 (0,4); 0,711 (0,4); 0,706 (0,5); 0,699 (0,3); 0,694 (0,4); 0,688 (0,5); 0,640 (0,4); 0,630 (0,4); 0,600 (3,7); 0,590 (10,9); 0,584 (10,1); 0,580 (9,4); 0,574 (9,2); 0,562 (2,9); 0,548 (0,5); 0,465 (0,4); 0,456 (0,4); 0,355 (0,3); 0,146 (2,0);(1.0); 2,330 (1, 4); 2,326 (1, 0); 2.321 (0.5); 0.774 (3.0); 0.761 (8.1); 0.756 (11, 5); 0.744 (10.6); 0.738 (8.9); 0.727 (3.7); 0.717 (0.4); 0.711 (0.4); 0.706 (0.5); 0.699 (0.3); 0.694 (0.4); 0.688 (0.5); 0.640 (0.4); 0.630 (0.4); 0.600 (3.7); 0.590 (10.9); 0.584 (10.1); 0.580 (9.4); 0.574 (9.2); 0.562 (2.9); 0.548 (0.5); 0.465 (0.4); 0.456 (0.4); 0.355 (0.3); 0.146 (2.0);
0,008 (16,5); 0,000 (454,5); -0,009 (17,0); -0,150 (2,0) 0.008 (16.5); 0,000 (454.5); -0.009 (17.0); -0.150 (2.0)
Beispiel 1-1-15: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-15: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,178 (7,4); 10,154 (7,6); 10,135 (0,4); 8,872 (10,3); 8,850 (11 ,3); 8,746 (7,9); 8,735 (8,0); 8,429 (10,3); 8,323 (0,5); 8,317 (0,9); 8,299 (15,9); 8,282 (10,7); 8,277 (16,0); 8,260 (11 ,0); 8,193 (4,9); 8,189 (4,9); 8,172 (5,5); 8,168 (5,5); 7,960 (0,6); 7,938 (0,5); 7,902 (0,5); 7,889 (15,7); 7,880 (11 ,0); 7,867 (14,7); 7,859 (9,5); 6,471 (0,7); 6,450 (2,8); 6,428 (4,2); 6,406 (3,0); 6,384 (0,9); 5,758 (2,1); 3,569 (3,3); 3,326 (248,5); 3,176 (0,3); 2,934 (0,8); 2,924 (2,2); 2,914 (3,0); 2,905 (4,7); 2,895 (4,8); 2,887 (3,0); 2,877 (2,2); 2,867 (0,8); 2,677 (1 ,4); 2,672 (2,0); 2,668 (1 ,4); 2,542 (1 ,0); 2,525 (4,8); 2,512 (114,9); 2,508 (233,3); 2,503 (307,1); 2,499 (220,6); 2,494 (105,7); 2,334 (1 ,4); 2,330 (1 ,9); 2,325 (1 ,4); 1 ,233 (0,6); 0,773 (3,0); 0,760 (8,6); 0,755 (11 ,9); 0,743 (10,9); 0,737 (9,3); 0,726 (3,7); 0,705 (0,5); 0,687 (0,4); 0,639 (0,4); 0,629 (0,4); 0,599 (3,8); 0,588 (11 ,5); 0,582 (10,6); 0,578δ = 10.178 (7.4); 10.154 (7.6); 10.135 (0.4); 8,872 (10.3); 8,850 (11, 3); 8.746 (7.9); 8,735 (8.0); 8,429 (10.3); 8.323 (0.5); 8.317 (0.9); 8,299 (15.9); 8,282 (10,7); 8,277 (16.0); 8,260 (11, 0); 8,193 (4,9); 8,189 (4,9); 8,172 (5.5); 8.168 (5.5); 7.960 (0.6); 7.938 (0.5); 7.902 (0.5); 7,889 (15.7); 7,880 (11, 0); 7,867 (14.7); 7,859 (9.5); 6,471 (0.7); 6,450 (2.8); 6,428 (4,2); 6,406 (3.0); 6,384 (0.9); 5,758 (2,1); 3,569 (3.3); 3,326 (248.5); 3.176 (0.3); 2,934 (0.8); 2.924 (2.2); 2,914 (3.0); 2,905 (4,7); 2,895 (4.8); 2,887 (3.0); 2,877 (2.2); 2,867 (0.8); 2,677 (1, 4); 2,672 (2.0); 2,668 (1, 4); 2,542 (1, 0); 2,525 (4,8); 2,512 (114.9); 2,508 (233,3); 2,503 (307,1); 2,499 (220.6); 2,494 (105.7); 2.334 (1, 4); 2,330 (1, 9); 2.325 (1, 4); 1, 233 (0.6); 0,773 (3.0); 0.760 (8.6); 0.755 (11, 9); 0.743 (10.9); 0.737 (9.3); 0.726 (3.7); 0.705 (0.5); 0.687 (0.4); 0.639 (0.4); 0.629 (0.4); 0.599 (3.8); 0.588 (11, 5); 0.582 (10.6); 0.578
(10,0); 0,573 (9,6); 0,560 (2,9); 0,464 (0,4); 0,456 (0,4); 0,355 (0,3); 0,341 (0,3); 0,146 (2,4); 0,008 (19,4); 0,000 (530,6); -0,009 (19,8); -0,034 (0,5); -0,150 (2,5) (10.0); 0.573 (9.6); 0.560 (2.9); 0.464 (0.4); 0.456 (0.4); 0.355 (0.3); 0.341 (0.3); 0.146 (2.4); 0.008 (19.4); 0.000 (530.6); -0.009 (19.8); -0.034 (0.5); -0.150 (2.5)
Beispiel 1-1-16: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-16: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,192 (6,8); 10,167 (7,0); 9,673 (16,0); 8,912 (9,5); 8,890 (10,5); 8,504 (3,8); 8,486 (6,9); 8,467 (3,7); 8,341 (15,0); 8,325 (9,9); 8,319 (15,0); 8,304 (10,7); 7,955 (14,7); 7,933 (13,5); 6,485 (0,7); 6,465 (2,6); 6,443 (3,7); 6,420 (2,8); 6,399 (0,9); 4,116 (0,8); 4,103 (2,5); 4,090 (2,6); 4,076 (0,9); 4,039 (0,9); 4,021 (0,9); 3,327 (170,9); 3,177 (10,1); 3,163 (9,8); 2,677 (1 ,0); 2,673 (1 ,4); 2,668 (1 ,0); 2,543 (0,7); 2,526 (3,8); 2,512 (84,2); 2,508 (168,9); 2,503 (221 ,5); 2,499 (158,4); 2,495 (75,2); 2,339 (0,5); 2,335 (1 ,0); 2,330 (1 ,4); 2,326 (1 ,1); 1 ,990 (4,0); 1 ,654 (5,2); 1 ,640 (12,6); 1 ,633 (13,5); 1 ,620 (5,8); 1 ,580 (0,5); 1 ,397 (0,5); 1 ,356 (6,0); 1 ,343 (12,6); 1 ,336 (13,2); 1 ,322 (4,8); 1 ,194 (1 ,1); 1 ,176 (2,1);δ = 10.192 (6.8); 10.167 (7.0); 9,673 (16.0); 8,912 (9.5); 8,890 (10.5); 8,504 (3,8); 8,486 (6,9); 8,467 (3,7); 8,341 (15.0); 8,325 (9.9); 8,319 (15.0); 8.304 (10.7); 7,955 (14.7); 7,933 (13.5); 6.455 (0.7); 6,465 (2.6); 6,443 (3.7); 6,420 (2,8); 6,399 (0.9); 4.116 (0.8); 4.103 (2.5); 4,090 (2.6); 4,076 (0.9); 4,039 (0.9); 4,021 (0.9); 3,327 (170.9); 3,177 (10.1); 3,163 (9.8); 2,677 (1, 0); 2,673 (1, 4); 2,668 (1, 0); 2,543 (0.7); 2,526 (3.8); 2,512 (84,2); 2,508 (168.9); 2,503 (221, 5); 2,499 (158.4); 2,495 (75.2); 2.399 (0.5); 2,335 (1, 0); 2,330 (1, 4); 2,326 (1, 1); 1, 990 (4.0); 1, 654 (5,2); 1, 640 (12,6); 1, 633 (13.5); 1, 620 (5.8); 1, 580 (0.5); 1, 397 (0.5); 1, 356 (6.0); 1, 343 (12,6); 1, 336 (13,2); 1, 322 (4,8); 1, 194 (1, 1); 1, 176 (2,1);
1 ,158 (1 ,1); 0,008 (1 ,5); 0,000 (40,5); -0,008 (1 ,4) 1, 158 (1, 1); 0.008 (1, 5); 0,000 (40.5); -0.008 (1, 4)
Beispiel 1-1-17: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-17: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,153 (6,9); 10,128 (7,2); 10,109 (0,4); 8,888 (0,3); 8,875 (9,0); 8,873 (9,4); 8,853 (9,8); 8,851 (10,6); 8,748 (7,4); 8,738 (7,5); 8,404 (4,6); 8,387 (4,4); 8,327 (0,6); 8,318 (0,8); 8,305 (15,4); 8,289 (9,3); 8,287 (10,1); 8,283 (16,0); 8,267 (12,3); 8,265 (13,0); 8,259 (3,7); 8,250 (2,9); 8,244 (2,8); 7,962 (0,5); 7,940 (0,5); 7,892 (14,6); 7,870 (13,6); 7,679δ = 10.153 (6.9); 10.128 (7.2); 10,109 (0.4); 8,888 (0.3); 8,875 (9.0); 8,873 (9.4); 8,853 (9.8); 8.851 (10.6); 8,748 (7.4); 8,738 (7.5); 8,404 (4,6); 8,387 (4,4); 8,327 (0.6); 8,318 (0.8); 8,305 (15.4); 8,289 (9.3); 8,287 (10.1); 8,283 (16.0); 8,267 (12.3); 8,265 (13.0); 8,259 (3,7); 8.250 (2.9); 8,244 (2,8); 7.962 (0.5); 7.940 (0.5); 7,892 (14.6); 7,870 (13.6); 7,679
(4.1) ; 7,653 (5,3); 7,630 (3,9); 6,455 (0,7); 6,434 (2,6); 6,412 (3,8); 6,389 (2,8); 6,367 (0,8); 4,058 (0,9); 4,040 (2,8); 4,022 (2,8); 4,005 (0,9); 3,330 (121 ,4); 3,313 (0,5); 2,937 (0,7); 2,927 (2,0); 2,917 (2,7); 2,909 (4,3); 2,899 (4,4); 2,890 (2,7); 2,881 (2,1); 2,870 (0,8); 2,679 (0,5); 2,675 (0,7); 2,670 (0,5); 2,528 (1 ,4); 2,514 (38,1); 2,510 (77,8); 2,506 (103,6); 2,501 (76,1); 2,497 (37,0); 2,337 (0,5); 2,332 (0,7); 2,328 (0,5); 1 ,991 (12,4); 1 ,233 (0,7); 1 ,195 (3,4); 1 ,177 (6,8); 1 ,159 (3,3); 0,776 (2,8); 0,763 (7,8); 0,758 (11 ,0); 0,746 (10,1); 0,740 (8,7); 0,728 (3,5); 0,707 (0,4); 0,689 (0,4); 0,642 (0,4); 0,632 (0,4); 0,602 (3,6); 0,592 (10,6); 0,586 (9,8); 0,582 (9,3); 0,576 (8,9); 0,564 (2,8); 0,467 (0,4); 0,459 (0,4); 0,146(4.1); 7,653 (5.3); 7,630 (3.9); 6.455 (0.7); 6,434 (2.6); 6.412 (3.8); 6,389 (2,8); 6,367 (0.8); 4,058 (0.9); 4,040 (2.8); 4.022 (2.8); 4.005 (0.9); 3,330 (121, 4); 3,313 (0.5); 2.937 (0.7); 2,927 (2.0); 2,917 (2.7); 2,909 (4,3); 2,899 (4.4); 2,890 (2.7); 2,881 (2,1); 2,870 (0.8); 2,679 (0.5); 2.675 (0.7); 2,670 (0.5); 2.528 (1, 4); 2,514 (38.1); 2,510 (77.8); 2,506 (103.6); 2,501 (76.1); 2,497 (37.0); 2.377 (0.5); 2.332 (0.7); 2.328 (0.5); 1, 991 (12,4); 1, 233 (0.7); 1, 195 (3,4); 1, 177 (6,8); 1, 159 (3,3); 0.776 (2.8); 0.763 (7.8); 0.758 (11, 0); 0.746 (10.1); 0.740 (8.7); 0.728 (3.5); 0.707 (0.4); 0.689 (0.4); 0.642 (0.4); 0.632 (0.4); 0.602 (3.6); 0.592 (10.6); 0.586 (9.8); 0.582 (9.3); 0.576 (8.9); 0.564 (2.8); 0.467 (0.4); 0.459 (0.4); 0.146
(0,4); 0,008 (3,4); 0,000 (95,6); -0,008 (3,4); -0,150 (0,4) (0.4); 0.008 (3.4); 0.000 (95.6); -0.008 (3.4); -0.150 (0.4)
Beispiel 1-1-18: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-18: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,159 (5,5); 10,134 (5,6); 9,666 (12,3); 8,894 (7,3); 8,872 (8,0); 8,402 (3,8); 8,389 (3,7); 8,341 (0,4); 8,320 (16,0); 8,298 (15,4); 8,271 (2,1); 8,265 (2,3); 8,257 (2,6); 8,250 (2,4); 8,244 (2,3); 7,949 (10,9); 7,927 (10,0); 7,680 (3,3); 7,655 (4,3); 7,632 (3,1); 6,458 (0,6); 6,437 (2,1); 6,415 (3,1); 6,392 (2,3); 6,371 (0,7); 5,758 (1 ,5); 4,039 (0,6); 4,021 (0,7); 3,328 (72,2); 2,677 (0,6); 2,673 (0,9); 2,668 (0,6); 2,543 (0,6); 2,513 (55,8); 2,508 (104,8); 2,504 (132,9); 2,499 (94,3); 2,495 (44,8); 2,335 (0,7); 2,331 (0,8); 2,326 (0,6); 1 ,990 (2,7); 1 ,655 (4,1); 1 ,640 (10,2); 1 ,633 (10,7); 1 ,620 (4,4); 1 ,580 (0,4); 1 ,397 (0,4); 1 ,356 (4,9); 1 ,343 (10,4); 1 ,336 (10,7); 1 ,321 (3,8); 1 ,232 (1 ,3); 1 ,194 (0,8); 1 ,176 (1 ,5); 1 ,158δ = 10.159 (5.5); 10.134 (5.6); 9,666 (12.3); 8,894 (7.3); 8,872 (8.0); 8,402 (3,8); 8,389 (3.7); 8,341 (0.4); 8,320 (16,0); 8,298 (15.4); 8,271 (2,1); 8.265 (2.3); 8.257 (2.6); 8.250 (2.4); 8.244 (2.3); 7.949 (10.9); 7,927 (10.0); 7,680 (3.3); 7,655 (4.3); 7,632 (3,1); 6.458 (0.6); 6,437 (2,1); 6,415 (3,1); 6,392 (2,3); 6,371 (0.7); 5,758 (1, 5); 4,039 (0.6); 4,021 (0.7); 3,328 (72.2); 2,677 (0.6); 2,673 (0.9); 2,668 (0.6); 2,543 (0.6); 2,513 (55.8); 2,508 (104.8); 2,504 (132.9); 2,499 (94.3); 2,495 (44.8); 2.335 (0.7); 2.331 (0.8); 2,326 (0.6); 1, 990 (2,7); 1, 655 (4,1); 1, 640 (10,2); 1, 633 (10,7); 1, 620 (4,4); 1, 580 (0.4); 1, 397 (0.4); 1, 356 (4,9); 1, 343 (10.4); 1, 336 (10,7); 1, 321 (3,8); 1, 232 (1, 3); 1, 194 (0.8); 1, 176 (1, 5); 1, 158
(0,7); 0,007 (2,7); -0,001 (48,3); -0,009 (1 ,7) (0.7); 0.007 (2.7); -0.001 (48.3); -0.009 (1, 7)
Beispiel 1-1-19: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-19: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,092 (2,1); 10,067 (2,1 ); 8,794 (2,5); 8,772 (2,7); 8,558 (2,2); 8,547 (2,2); 8,424 (2,8); 8,187 (1 ,4); 8,174 (4,6); 8,152 (3,8); 8,126 (2,3); 8,104 (2,6); 7,877 (2,9); 7,856 (2,6); 7,744 (3,5); 7,722 (3,2); 6,434 (0,8); 6,413 (1 ,2); 6,390 (0,9); 3,325 (95,7); 2,925 (0,6); 2,915 (0,9); 2,907 (1 ,3); 2,897 (1 ,3); 2,888 (0,9); 2,877 (1 ,1); 2,665 (16,0); 2,557 (0,3); 2,541 (0,5); 2,511 (48,4); 2,507 (92,1); 2,503 (118,1); 2,498 (84,0); 2,494 (40,1); 2,334 (0,6); 2,329 (0,7); 2,325 (0,5); 1 ,373 (0,4); 1 ,234 (3,1); 1 ,045 (1 ,3); 1 ,030 (1 ,3); 0,854 (0,5); 0,755 (0,9); 0,742 (2,5); 0,737 (3,3); 0,725 (3,0); 0,719 (2,6); 0,708 (1 ,0); 0,588 (1 ,1); 0,577 (3,5); 0,572 (3,0); 0,568 (2,9); 0,562 (2,7); 0,550 (0,8); 0,008 (1 ,0); 0,000 (20,7); -0,008δ = 10.092 (2.1); 10.067 (2.1); 8,794 (2.5); 8,772 (2.7); 8.558 (2.2); 8.547 (2.2); 8,424 (2.8); 8,187 (1, 4); 8,174 (4,6); 8,152 (3,8); 8.126 (2.3); 8,104 (2,6); 7,877 (2.9); 7.856 (2.6); 7.744 (3.5); 7,722 (3,2); 6,434 (0.8); 6.413 (1, 2); 6,390 (0.9); 3,325 (95.7); 2,925 (0.6); 2,915 (0.9); 2,907 (1, 3); 2,897 (1, 3); 2,888 (0.9); 2,877 (1, 1); 2,665 (16.0); 2,557 (0.3); 2,541 (0.5); 2,511 (48.4); 2,507 (92,1); 2,503 (118,1); 2,498 (84.0); 2,494 (40.1); 2.334 (0.6); 2,329 (0.7); 2.325 (0.5); 1, 373 (0.4); 1, 234 (3,1); 1, 045 (1, 3); 1, 030 (1, 3); 0.854 (0.5); 0.755 (0.9); 0.742 (2.5); 0.737 (3.3); 0.725 (3.0); 0.719 (2.6); 0.708 (1, 0); 0.588 (1, 1); 0.577 (3.5); 0.572 (3.0); 0.568 (2.9); 0.562 (2.7); 0,550 (0.8); 0.008 (1, 0); 0.000 (20.7); -0,008
(0J) (0J)
Beispiel 1-1-20: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-20: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,069 (2,0); 10,044 (2,1); 8,795 (2,6); 8,773 (2,8); 8,561 (2,2); 8,550 (2,2); 8,400 (1 ,4); 8,384 (1 ,4); 8,264 (0,9); 8,255 (1 ,0); 8,244 (0,9); 8,179 (3,8); 8,157 (3,6); 8,131 (2,3); δ = 10.069 (2.0); 10.044 (2.1); 8.795 (2.6); 8,773 (2.8); 8.561 (2.2); 8.550 (2.2); 8,400 (1, 4); 8.384 (1, 4); 8.264 (0.9); 8,255 (1, 0); 8,244 (0.9); 8,179 (3,8); 8,157 (3,6); 8.131 (2.3);
8,109 (2,6); 7,746 (3,4); 7,724 (3,1); 7,676 (1,3); 7,651 (1,7); 7,628 (1,2); 6,419 (0,8); 6,396 (1,2); 6,374 (0,9); 3,329 (55,2); 2,927 (0,6); 2,917 (0,9); 2,908 (1,3); 2,898 (1,3); 2,889 (0,9); 2,880 (0,7); 2,666 (16,0); 2,508 (40,5); 2,504 (52,9); 2,499 (38,8); 1,990 (1,3); 1,234 (2,7); 1,194 (0,4); 1,176 (0,8); 1,158 (0,4); 0,854 (0,4); 0,757 (0,8); 0,743 (2,5); 0,7398.109 (2.6); 7,746 (3,4); 7,724 (3,1); 7.676 (1.3); 7.651 (1.7); 7.628 (1.2); 6,419 (0.8); 6.396 (1.2); 6,374 (0.9); 3,329 (55.2); 2,927 (0.6); 2,917 (0.9); 2,908 (1,3); 2,898 (1.3); 2,889 (0.9); 2,880 (0.7); 2,666 (16.0); 2,508 (40.5); 2,504 (52.9); 2,499 (38.8); 1,990 (1.3); 1,234 (2.7); 1,194 (0.4); 1.176 (0.8); 1.158 (0.4); 0,854 (0.4); 0.757 (0.8); 0.743 (2.5); 0.739
(3,3); 0,726 (3,0); 0,721 (2,6); 0,709 (1,0); 0,590 (1,1); 0,579 (3,4); 0,573 (3,1); 0,569 (3,0); 0,564 (2,8); 0,551 (0,8); 0,008 (1,8); 0,000 (43,2); -0,008 (1,7) (3.3); 0.726 (3.0); 0.721 (2.6); 0.709 (1.0); 0.590 (1.1); 0.579 (3.4); 0.573 (3.1); 0.569 (3.0); 0.564 (2.8); 0.551 (0.8); 0.008 (1.8); 0.000 (43.2); -0.008 (1.7)
Beispiel 1-1-21: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-21: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,077 (2,1); 10,052 (2,2); 9,472 (4,7); 8,829 (2,5); 8,807 (2,7); 8,399 (1,4); 8,385 (1,4); 8,272 (0,8); 8,266 (0,8); 8,258 (1,0); 8,250 (0,9); 8,244 (0,8); 8,197 (4,1); 8,175 (4,0); 8,164 (2,4); 8,142 (2,7); 7,789 (3,6); 7,767 (3,3); 7,678 (1,2); 7,652 (1,6); 7,629 (1,2); 6,422 (0,8); 6,401 (1,2); 6,378 (0,8); 4,039 (0,8); 4,021 (0,9); 3,327 (35,2); 2,691 (16,0);δ = 10.077 (2.1); 10.052 (2.2); 9,472 (4,7); 8.829 (2.5); 8,807 (2.7); 8,399 (1.4); 8.385 (1.4); 8,272 (0.8); 8.266 (0.8); 8.258 (1.0); 8,250 (0.9); 8,244 (0.8); 8,197 (4,1); 8.175 (4.0); 8.164 (2.4); 8,142 (2,7); 7,789 (3.6); 7,767 (3.3); 7.678 (1.2); 7.652 (1.6); 7.629 (1.2); 6,422 (0.8); 6,401 (1,2); 6,378 (0.8); 4,039 (0.8); 4,021 (0.9); 3,327 (35,2); 2,691 (16.0);
2.673 (0,5); 2,669 (0,4); 2,526 (1,2); 2,513 (21,3); 2,508 (42,7); 2,504 (55,9); 2,499 (39,9); 2,495 (19,0); 2,331 (0,3); 1,990 (3,7); 1,627 (1,5); 1,613 (3,7); 1,606 (4,0); 1,593 (1,7);2,673 (0.5); 2,669 (0.4); 2.526 (1.2); 2,513 (21,3); 2,508 (42,7); 2,504 (55.9); 2,499 (39.9); 2,495 (19.0); 2.331 (0.3); 1,990 (3.7); 1,627 (1.5); 1,613 (3.7); 1.606 (4.0); 1,593 (1.7);
1,354 (1,8); 1,341 (3,8); 1,334 (4,0); 1,319(1,4); 1,194(1,0); 1,176 (2,0); 1,158 (1,0); 0,008 (0,8); 0,000 (22,0); -0,009 (0,8) 1.354 (1.8); 1,341 (3.8); 1,334 (4.0); 1,319 (1.4); 1,194 (1.0); 1.176 (2.0); 1.158 (1.0); 0.008 (0.8); 0,000 (22,0); -0.009 (0.8)
Beispiel 1-1-22: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-22: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,147 (0,4); 10,131 (3,5); 10,106 (3,6); 8,884 (5,1); 8,862 (5,5); 8,861 (5,4); 8,650 (1,0); 8,640 (2,7); 8,628 (2,7); 8,617 (0,9); 8,336 (0,7); 8,307 (12,7); 8,299 (7,6); 8,285 (7,9); 8,277 (5,8); 8,155 (3,1); 8,136 (3,1); 7,921 (0,5); 7,908 (7,8); 7,899 (0,6); 7,886 (7,2); 7,840 (2,8); 7,821 (3,8); 7,744 (2,8); 7,724 (4,4); 7,705 (1,8); 6,421 (0,4); 6,399 (1,5); 6,377 (2,2); 6,354 (1,6); 6,333 (0,5); 3,619 (0,5); 3,608 (0,5); 3,602 (1,3); 3,596 (0,5); 3,586 (0,5); 3,331 (78,2); 2,850 (16,0); 2,838 (15,8); 2,698 (0,5); 2,686 (0,5); 2,677 (0,6); 2,673 (0,7); 2,669 (0,5); 2,554 (0,3); 2,543 (0,4); 2,526 (2,3); 2,513 (41,0); 2,509 (81,3); 2,504 (105,6); 2,500 (75,3); 2,495 (35,9); 2,335 (0,5); 2,331 (0,7); 2,326 (0,5); 1,777 (0,6); 1,769δ = 10.147 (0.4); 10.131 (3.5); 10,106 (3,6); 8,884 (5.1); 8,862 (5.5); 8,861 (5.4); 8,650 (1.0); 8,640 (2.7); 8.628 (2.7); 8.617 (0.9); 8.366 (0.7); 8,307 (12,7); 8,299 (7.6); 8,285 (7.9); 8,277 (5.8); 8,155 (3,1); 8,136 (3,1); 7.921 (0.5); 7,908 (7,8); 7,899 (0.6); 7,886 (7.2); 7,840 (2.8); 7,821 (3.8); 7,744 (2.8); 7,724 (4.4); 7,705 (1.8); 6,421 (0.4); 6,399 (1.5); 6,377 (2,2); 6,354 (1.6); 6,333 (0.5); 3,619 (0.5); 3,608 (0.5); 3.602 (1.3); 3.596 (0.5); 3.586 (0.5); 3,331 (78.2); 2,850 (16.0); 2,838 (15,8); 2,698 (0.5); 2,686 (0.5); 2,677 (0.6); 2,673 (0.7); 2,669 (0.5); 2,554 (0.3); 2,543 (0.4); 2.526 (2.3); 2,513 (41.0); 2,509 (81.3); 2,504 (105.6); 2,500 (75.3); 2,495 (35.9); 2.335 (0.5); 2.331 (0.7); 2,326 (0.5); 1,777 (0.6); 1,769
(0,6); 1 ,760 (1 ,5); 1 ,752 (0,6); 1 ,744 (0,5); 1 ,357 (1 ,3); 0,008 (1 ,5); 0,000 (37,4); -0,009 (1 ,3) (0.6); 1, 760 (1, 5); 1, 752 (0.6); 1, 744 (0.5); 1, 357 (1, 3); 0.008 (1, 5); 0,000 (37.4); -0.009 (1, 3)
Beispiel 1-1-23: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-23: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,145 (1,3); 10,120 (1,4); 8,886 (1,8); 8,864 (1,9); 8,699 (1,2); 8,679 (1,2); 8,317 (2,4); 8,312 (4,3); 8,296 (2,2); 8,290 (2,6); 8,160 (1,1); 8,140 (1,2); 7,908 (0,4); 7,896 (2,5); 7,886 (0,4); 7,874 (2,4); 7,841 (1,0); 7,822 (1,4); 7,745 (1,0); 7,726 (1,6); 7,706 (0,7); 6,401 (0,6); 6,379 (0,8); 6,356 (0,6); 4,212 (0,6); 4,195 (0,7); 4,175 (0,6); 4,039 (0,5); 4,021 (0,5); 3,334 (34,1); 2,730 (0,6); 2,713 (0,6); 2,697 (1,3); 2,680 (1,3); 2,643 (1,1); 2,626 (1,1); 2,610 (0,6); 2,593 (0,5); 2,513 (13,5); 2,509 (26,7); 2,504 (34,6); 2,500 (25,2); 2,496δ = 10.145 (1.3); 10.120 (1.4); 8,886 (1.8); 8,864 (1.9); 8,699 (1.2); 8.679 (1.2); 8.317 (2.4); 8,312 (4,3); 8.296 (2.2); 8,290 (2.6); 8.160 (1.1); 8.140 (1.2); 7.908 (0.4); 7,896 (2.5); 7,886 (0.4); 7.874 (2.4); 7,841 (1.0); 7.822 (1.4); 7,745 (1.0); 7,726 (1.6); 7.706 (0.7); 6,401 (0.6); 6,379 (0.8); 6.356 (0.6); 4,212 (0.6); 4.195 (0.7); 4.175 (0.6); 4.039 (0.5); 4,021 (0.5); 3,334 (34.1); 2,730 (0.6); 2,713 (0.6); 2,697 (1.3); 2,680 (1.3); 2,643 (1.1); 2.626 (1.1); 2,610 (0.6); 2,593 (0.5); 2,513 (13.5); 2,509 (26.7); 2,504 (34.6); 2,500 (25.2); 2,496
(12.6) ; 2,146 (16,0); 2,118 (1,9); 1,991 (2,2); 1,302 (0,7); 1,284 (0,9); 1,274 (5,2); 1,257 (5,1); 1,194 (0,6); 1,176(1,2); 1,158 (0,6); 0,008 (0,3); 0,000 (9,3); -0,008 (0,5) (12.6); 2.146 (16.0); 2,118 (1.9); 1,991 (2.2); 1,302 (0.7); 1,284 (0.9); 1,274 (5.2); 1.257 (5.1); 1,194 (0.6); 1,176 (1.2); 1.158 (0.6); 0.008 (0.3); 0.000 (9.3); -0.008 (0.5)
Beispiel 1-1-24: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-24: 1 H-NMR (400.0 MHz, d 6 -DMSO):
δ= 10,147 (1,8); 10,123 (1,8); 9,518 (0,9); 9,504 (1,9); 9,490 (0,9); 8,907 (2,5); 8,885 (2,8); 8,339 (2,6); 8,325 (3,8); 8,317 (3,3); 8,303 (5,8); 8,157 (1,5); 8,138 (1,6); 7,947 (3,6); 7,926 (3,3); 7,842 (1,3); 7,823 (1,9); 7,746 (1,4); 7,726 (2,2); 7,707 (0,9); 6,404 (0,7); 6,382 (1,1); 6,359 (0,8); 5,759 (0,6); 4,444 (4,7); 4,430 (4,6); 4,057 (1,2); 4,039 (3,7); 4,021δ = 10.147 (1.8); 10.123 (1.8); 9.518 (0.9); 9,504 (1.9); 9,490 (0.9); 8,907 (2.5); 8,885 (2.8); 8.399 (2.6); 8,325 (3.8); 8,317 (3.3); 8,303 (5,8); 8.157 (1.5); 8.138 (1.6); 7,947 (3.6); 7,926 (3.3); 7,842 (1.3); 7,823 (1.9); 7.746 (1.4); 7,726 (2,2); 7,707 (0.9); 6.404 (0.7); 6,382 (1,1); 6,359 (0.8); 5,759 (0.6); 4,444 (4,7); 4,430 (4,6); 4.057 (1.2); 4,039 (3.7); 4,021
(3,8); 4,003 (1,3); 3,337 (106,1); 2,674 (0,3); 2,509 (40,6); 2,504 (51,6); 2,500 (37,1); 1,991 (16,0); 1,194 (4,2); 1,176 (8,3); 1,158 (4,1); 0,000 (22,5); -0,008 (0,9) (3.8); 4.003 (1.3); 3,337 (106,1); 2,674 (0.3); 2,509 (40.6); 2,504 (51.6); 2,500 (37.1); 1,991 (16.0); 1,194 (4,2); 1.176 (8.3); 1,158 (4,1); 0,000 (22.5); -0.008 (0.9)
Beispiel 1-1-25: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-25: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,139 (1,2); 10,115 (1,2); 8,880 (1,6); 8,858 (1,8); 8,857 (1,8); 8,632 (1,1); 8,611 (1,1); 8,308 (4,4); 8,303 (2,7); 8,286 (2,7); 8,281 (1,9); 8,159 (0,9); 8,140 (1,0); 7,870 (2,3); 7,849 (2,4); 7,842 (0,9); 7,822 (1,2); 7,745 (0,9); 7,726 (1,4); 7,706 (0,6); 6,399 (0,5); 6,377 (0,7); 6,355 (0,5); 5,760 (0,3); 4,226 (0,6); 4,209 (0,7); 4,207 (0,6); 4,190 (0,6); 4,056 (1,2); 4,039 (3,8); 4,021 (3,8); 4,003 (1,3); 3,461 (0,9); 3,445 (0,9); 3,437 (1,2); 3,422 (1,1); 3,333 (35,1); 3,314 (15,5); 3,296 (0,9); 2,513 (14,6); 2,508 (27,5); 2,504 (35,0); 2,499δ = 10.139 (1.2); 10.115 (1.2); 8,880 (1.6); 8,858 (1.8); 8.857 (1.8); 8.632 (1.1); 8.611 (1.1); 8,308 (4.4); 8,303 (2,7); 8,286 (2,7); 8,281 (1.9); 8,159 (0.9); 8.140 (1.0); 7.870 (2.3); 7.849 (2.4); 7,842 (0.9); 7.822 (1.2); 7,745 (0.9); 7,726 (1.4); 7.706 (0.6); 6,399 (0.5); 6,377 (0.7); 6.355 (0.5); 5,760 (0.3); 4,226 (0.6); 4,209 (0.7); 4,207 (0.6); 4.190 (0.6); 4.056 (1.2); 4,039 (3.8); 4,021 (3.8); 4.003 (1.3); 3,461 (0.9); 3,445 (0.9); 3,437 (1,2); 3.422 (1.1); 3,333 (35.1); 3,314 (15.5); 3.296 (0.9); 2,513 (14.6); 2,508 (27.5); 2,504 (35.0); 2,499
(24.7) ; 2,495 (11,7); 1,990 (16,0); 1,193 (4,9); 1,185 (5,7); 1,176 (9,6); 1,168 (5,6); 1,158 (4,6); 0,008 (0,5); 0,000 (9,1); -0,009 (0,3) (24.7); 2,495 (11.7); 1,990 (16.0); 1,193 (4.9); 1.185 (5.7); 1.176 (9.6); 1.168 (5.6); 1,158 (4,6); 0.008 (0.5); 0.000 (9.1); -0.009 (0.3)
Beispiel 1-1-26: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-26: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,146 (5,5); 10,122 (5,6); 9,508 (5,7); 9,492 (5,7); 8,900 (7,3); 8,877 (8,1); 8,326 (9,1); 8,322 (13,1); 8,306 (14,4); 8,300 (13,3); 8,160 (4,2); 8,141 (4,6); 7,959 (11,3); 7,937 (10,4); 7,843 (3,8); 7,824 (5,4); 7,747 (4,0); 7,727 (6,3); 7,708 (2,6); 6,426 (0,6); 6,404 (2,2); 6,382 (3,2); 6,360 (2,3); 6,338 (0,7); 5,102 (0,4); 5,085 (1,8); 5,067 (3,8); 5,050 (4,1); 5,032 (2,4); 5,016 (0,7); 4,856 (8,4); 4,840 (13,3); 4,822 (7,8); 4,600 (8,4); 4,584 (16,0); 4,568 (7,5); 4,057 (0,8); 4,039 (2,3); 4,021 (2,4); 4,004 (0,8); 3,336 (143,8); 2,678 (0,5);δ = 10.146 (5.5); 10.122 (5.6); 9,508 (5,7); 9,492 (5.7); 8,900 (7.3); 8,877 (8.1); 8,326 (9.1); 8,322 (13.1); 8,306 (14.4); 8,300 (13.3); 8,160 (4,2); 8,141 (4,6); 7,959 (11.3); 7.937 (10.4); 7,843 (3.8); 7,824 (5.4); 7.747 (4.0); 7,727 (6.3); 7,708 (2.6); 6,426 (0.6); 6,404 (2,2); 6,382 (3,2); 6.360 (2.3); 6.338 (0.7); 5.102 (0.4); 5,085 (1.8); 5,067 (3.8); 5,050 (4.1); 5,032 (2,4); 5,016 (0.7); 4,856 (8,4); 4,840 (13.3); 4,822 (7,8); 4,600 (8.4); 4,584 (16,0); 4,568 (7.5); 4.057 (0.8); 4.039 (2.3); 4.021 (2.4); 4.004 (0.8); 3,336 (143.8); 2,678 (0.5);
2.674 (0,7); 2,669 (0,5); 2,527 (1,8); 2,514 (40,2); 2,509 (80,1); 2,505 (104,3); 2,500 (74,8); 2,496 (35,8); 2,336 (0,5); 2,331 (0,6); 2,327 (0,5); 1,991 (10,4); 1,194 (2,8); 1,1762,674 (0.7); 2,669 (0.5); 2,527 (1.8); 2,514 (40,2); 2,509 (80.1); 2,505 (104.3); 2,500 (74.8); 2,496 (35.8); 2.336 (0.5); 2.331 (0.6); 2,327 (0.5); 1,991 (10.4); 1,194 (2.8); 1,176
(5,5); 1,158 (2,7); 0,008 (1,2); 0,000 (30,9); -0,009 (1,1) (5.5); 1,158 (2,7); 0.008 (1.2); 0.000 (30.9); -0.009 (1.1)
Beispiel 1-1-27: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-27: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,136 (3,0); 10,112 (3,0); 8,883 (4,1); 8,861 (4,5); 8,707 (1,5); 8,693 (2,9); 8,679 (1,4); 8,307 (10,4); 8,302 (7,2); 8,285 (6,1); 8,280 (4,7); 8,156 (2,4); 8,137 (2,5); 7,893 (5,8); 7,872 (5,4); 7,841 (2,1); 7,821 (3,0); 7,744 (2,2); 7,724 (3,4); 7,705 (1,4); 6,420 (0,3); 6,398 (1,2); 6,376 (1,8); 6,354 (1,3); 6,331 (0,4); 3,332 (308,7); 3,297 (2,2); 3,280 (4,7); 3,265 (4,7); 3,248 (2,0); 2,676 (1,1); 2,672 (1,5); 2,667 (1,1); 2,507 (180,8); 2,503 (229,7); 2,498 (165,6); 2,334 (1,1); 2,329 (1,4); 2,325 (1,0); 1,621 (0,5); 1,603 (2,4); 1,585 (4,9); δ = 10.136 (3.0); 10.112 (3.0); 8,883 (4,1); 8,861 (4,5); 8,707 (1.5); 8,693 (2.9); 8.679 (1.4); 8,307 (10.4); 8,302 (7.2); 8,285 (6,1); 8,280 (4,7); 8,156 (2,4); 8.137 (2.5); 7,893 (5.8); 7,872 (5.4); 7,841 (2.1); 7,821 (3.0); 7.744 (2.2); 7,724 (3,4); 7,705 (1.4); 6,420 (0.3); 6,398 (1.2); 6.376 (1.8); 6,354 (1.3); 6,331 (0.4); 3,332 (308.7); 3.297 (2.2); 3,280 (4,7); 3,265 (4,7); 3,248 (2.0); 2,676 (1.1); 2,672 (1.5); 2,667 (1,1); 2,507 (180,8); 2,503 (229,7); 2,498 (165.6); 2.334 (1.1); 2,329 (1.4); 2.325 (1.0); 1,621 (0.5); 1.603 (2.4); 1,585 (4.9);
1,567 (5,0); 1,549 (2,6); 1,532 (0,6); 0,979 (7,9); 0,960 (16,0); 0,942 (7,0); 0,008 (2,0); 0,000 (47,1); -0,008 (1,9) 1,567 (5.0); 1,549 (2.6); 1,532 (0.6); 0.979 (7.9); 0.960 (16.0); 0.942 (7.0); 0.008 (2.0); 0,000 (47.1); -0.008 (1,9)
Beispiel 1-1-28: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-28: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,137 (4,9); 10,113 (5,1); 8,958 (4,8); 8,939 (4,9); 8,883 (6,8); 8,861 (7,5); 8,331 (0,4); 8,311 (16,0); 8,297 (8,1); 8,289 (9,8); 8,275 (7,6); 8,158 (4,0); 8,139 (4,4); 7,894 (9,3); 7,872 (8,6); 7,841 (3,7); 7,822 (5,2); 7,745 (3,8); 7,726 (5,9); 7,706 (2,5); 6,421 (0,5); 6,400 (2,0); 6,378 (3,0); 6,355 (2,2); 6,333 (0,7); 4,490 (0,4); 4,469 (1,6); 4,449 (3,2); 4,429 (3,2); 4,409 (1,7); 4,389 (0,4); 4,057 (0,6); 4,039 (1,8); 4,021 (1,8); 4,003 (0,6); 3,337 (236,3); 2,674 (0,8); 2,509 (95,4); 2,504 (122,6); 2,500 (90,9); 2,331 (0,9); 2,326 (1,0); 2,321 (1,2); 2,304 (2,3); 2,293 (3,6); 2,286 (4,0); 2,278 (3,9); 2,266 (3,4); 2,246 (1,3); 2,091 (1,0); 2,068 (3,2); 2,044 (4,6); 2,039 (4,4); 2,021 (3,2); 2,015 (3,4); 1,991 (8,5); 1,748 (1,9);δ = 10.137 (4.9); 10,113 (5,1); 8,958 (4,8); 8,939 (4.9); 8,883 (6.8); 8,861 (7.5); 8,331 (0.4); 8,311 (16.0); 8,297 (8,1); 8,289 (9.8); 8.275 (7.6); 8.158 (4.0); 8,139 (4,4); 7,894 (9.3); 7,872 (8.6); 7,841 (3.7); 7,822 (5.2); 7,745 (3.8); 7,726 (5.9); 7.706 (2.5); 6,421 (0.5); 6,400 (2.0); 6,378 (3.0); 6,355 (2,2); 6,333 (0.7); 4,490 (0.4); 4.469 (1.6); 4,449 (3.2); 4,429 (3,2); 4.409 (1.7); 4.389 (0.4); 4.057 (0.6); 4,039 (1.8); 4,021 (1.8); 4.003 (0.6); 3,337 (236,3); 2,674 (0.8); 2,509 (95.4); 2,504 (122.6); 2,500 (90.9); 2.331 (0.9); 2,326 (1.0); 2.321 (1.2); 2.344 (2.3); 2,293 (3.6); 2,286 (4.0); 2,278 (3.9); 2,266 (3,4); 2.246 (1.3); 2.091 (1.0); 2,068 (3.2); 2.044 (4.6); 2,039 (4.4); 2.021 (3.2); 2.015 (3.4); 1,991 (8.5); 1,748 (1.9);
1,735 (3,6); 1,724 (4,3); 1,710(5,9); 1,701 (3,0); 1,693 (2,3); 1,685 (2,3); 1,667 (0,8); 1,232 (0,4); 1,194 (2,0); 1,176 (3,9); 1,158 (1,9); 0,000 (48,8) 1,735 (3.6); 1,724 (4.3); 1,710 (5.9); 1,701 (3.0); 1,693 (2.3); 1.685 (2.3); 1,667 (0.8); 1,232 (0.4); 1,194 (2.0); 1.176 (3.9); 1,158 (1.9); 0,000 (48.8)
Beispiel 1-1-29: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-29: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,146 (5,3); 10,121 (5,4); 9,168 (2,8); 9,153 (5,7); 9,138 (2,8); 8,897 (7,2); 8,875 (7,8); 8,329 (7,5); 8,317 (11,2); 8,307 (16,0); 8,295 (10,7); 8,157 (4,6); 8,137 (5,0); 7,913 (9,2); 7,891 (8,5); 7,842 (4,1); 7,822 (5,9); 7,746 (4,0); 7,726 (6,3); 7,707 (2,6); 6,422 (0,7); 6,400 (2,3); 6,378 (3,4); 6,355 (2,6); 6,337 (2,3); 6,208 (2,0); 6,198 (4,0); 6,189 (2,0); 6,068 (1,0); 6,059 (2,0); 6,050 (1,0); 5,758 (2,3); 4,056 (0,5); 4,039 (1,3); 4,021 (1,3); 4,003 (0,5); 3,807 (1,7); 3,798 (2,3); 3,783 (2,0); 3,768 (3,7); 3,758 (4,4); 3,754 (4,4); 3,744 (3,5); 3,728 (2,0); 3,718 (2,3); 3,714 (2,3); 3,704 (1,7); 3,479 (0,3); 3,351 (798,8); 3,273 (0,3); 2,674 (1,1); 2,505 (167,7); 2,332 (1,0); 1,990 (5,4); 1,234 (0,4); 1,194 (1,4); 1,176δ = 10.146 (5.3); 10.121 (5.4); 9.168 (2.8); 9.153 (5.7); 9.138 (2.8); 8,897 (7.2); 8,875 (7.8); 8.329 (7.5); 8,317 (11,2); 8,307 (16.0); 8.295 (10.7); 8,157 (4,6); 8.137 (5.0); 7,913 (9,2); 7,891 (8.5); 7,842 (4.1); 7,822 (5.9); 7.746 (4.0); 7,726 (6.3); 7,707 (2.6); 6,422 (0.7); 6,400 (2.3); 6,378 (3,4); 6.355 (2.6); 6.337 (2.3); 6.208 (2.0); 6.198 (4.0); 6.189 (2.0); 6.068 (1.0); 6,059 (2.0); 6.050 (1.0); 5.758 (2.3); 4.056 (0.5); 4,039 (1.3); 4,021 (1.3); 4.003 (0.5); 3,807 (1.7); 3,798 (2,3); 3,783 (2.0); 3,768 (3.7); 3,758 (4.4); 3,754 (4.4); 3,744 (3.5); 3,728 (2.0); 3.718 (2.3); 3.714 (2.3); 3,704 (1.7); 3,479 (0.3); 3,351 (798,8); 3,273 (0.3); 2,674 (1.1); 2,505 (167,7); 2.332 (1.0); 1,990 (5.4); 1,234 (0.4); 1,194 (1.4); 1,176
(2,8); 1,158 (1,4); 0,000 (63,6) (2.8); 1.158 (1.4); 0,000 (63.6)
Beispiel 1-1-30: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-30: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,148 (3,1); 10,123 (3,2); 9,359 (1 ,6); 9,344 (3,3); 9,328 (1,5); 8,904 (4,0); 8,882 (4,4); 8,560 (2,7); 8,549 (2,7); 8,338 (4,1); 8,319 (8,3); 8,310 (4,8); 8,298 (5,8); 8,160 (2,4); 8,141 (2,6); 7,995 (5,7); 7,973 (5,2); 7,865 (1,6); 7,861 (1,5); 7,846 (4,8); 7,842 (4,9); 7,826 (4,1); 7,823 (4,6); 7,747 (2,2); 7,727 (3,4); 7,708 (1,4); 7,525 (3,7); 7,505 (3,2); 7,333δ = 10.148 (3.1); 10.123 (3,2); 9,359 (1,6); 9,344 (3.3); 9.328 (1.5); 8.904 (4.0); 8,882 (4,4); 8,560 (2.7); 8,549 (2.7); 8,338 (4,1); 8,319 (8,3); 8,310 (4,8); 8,298 (5.8); 8.160 (2.4); 8.141 (2.6); 7.995 (5.7); 7,973 (5.2); 7.865 (1.6); 7.861 (1.5); 7,846 (4.8); 7,842 (4.9); 7,826 (4,1); 7,823 (4,6); 7.747 (2.2); 7,727 (3,4); 7,708 (1.4); 7,525 (3.7); 7,505 (3.2); 7.333
(2.0) ; 7,320 (2,2); 7,315 (2,0); 7,303 (1,8); 6,405 (1,2); 6,383 (1,8); 6,360 (1,3); 6,338 (0,4); 5,760 (2,5); 4,640 (6,4); 4,625 (6,2); 4,057 (1,2); 4,039 (3,7); 4,021 (3,7); 4,003 (1,2); 3,335 (92,7); 2,677 (0,4); 2,673 (0,5); 2,509 (61,2); 2,504 (75,1); 2,500 (53,0); 2,336 (0,4); 2,331 (0,5); 1,991 (16,0); 1,194 (4,2); 1,176 (8,4); 1,158 (4,1); 0,000 (19,0); -0,008 (0,7) Beispiel 1-1-31: 1H-NMR (400,0 MHz, d6-DMSO): (2.0); 7,320 (2,2); 7.315 (2.0); 7,303 (1,8); 6.405 (1.2); 6,383 (1.8); 6.360 (1.3); 6.338 (0.4); 5,760 (2.5); 4,640 (6.4); 4,625 (6.2); 4.057 (1.2); 4,039 (3.7); 4,021 (3.7); 4,003 (1,2); 3,335 (92.7); 2,677 (0.4); 2,673 (0.5); 2,509 (61.2); 2,504 (75.1); 2,500 (53.0); 2.336 (0.4); 2.331 (0.5); 1,991 (16.0); 1,194 (4,2); 1.176 (8.4); 1,158 (4,1); 0.000 (19.0); -0.008 (0.7) Example 1-1-31: 1 H-NMR (400.0 MHz, d 6 -DMSO):
δ= 10,140 (3,8); 10,115 (3,9); 9,214 (3,9); 9,194 (4,0); 8,886 (5,3); 8,864 (5,8); 8,318 (3,7); 8,312 (14,6); 8,290 (12,1); 8,158 (3,0); 8,139 (3,3); 7,887 (7,4); 7,865 (6,9); 7,842 (2,8); 7,822 (3,9); 7,745 (2,8); 7,725 (4,4); 7,706 (1,8); 6,421 (0,4); 6,400 (1,5); 6,378 (2,3); 6,355 (1,6); 6,334 (0,5); 5,759 (1,8); 4,901 (0,4); 4,895 (0,4); 4,883 (1,5); 4,877 (1,6); 4,864δ = 10.140 (3.8); 10.115 (3.9); 9.214 (3.9); 9.194 (4.0); 8,886 (5.3); 8,864 (5.8); 8,318 (3.7); 8,312 (14.6); 8,290 (12.1); 8.158 (3.0); 8.139 (3.3); 7,887 (7.4); 7,865 (6.9); 7,842 (2.8); 7,822 (3.9); 7,745 (2.8); 7,725 (4.4); 7.706 (1.8); 6,421 (0.4); 6,400 (1.5); 6.378 (2.3); 6.355 (1.6); 6.334 (0.5); 5,759 (1.8); 4.901 (0.4); 4,895 (0.4); 4,883 (1.5); 4,877 (1.6); 4,864
(2.1) ; 4,860 (2,1); 4,846 (1,6); 4,840 (1,5); 4,828 (0,4); 4,823 (0,4); 4,056 (0,5); 4,038 (1,4); 4,020 (1,4); 4,003 (0,5); 3,336 (349,9); 3,313 (1,9); 3,297 (0,4); 3,275 (7,2); 3,269 (7,1); 2,677 (0,8); 2,673 (1,0); 2,668 (0,8); 2,508 (128,7); 2,504 (163,4); 2,499 (117,0); 2,335 (0,8); 2,330 (1,0); 2,326 (0,7); 1,990 (6,2); 1,442 (16,0); 1,424 (15,9); 1,193 (1,6); 1,175(2.1); 4,860 (2,1); 4,846 (1.6); 4,840 (1.5); 4.828 (0.4); 4,823 (0.4); 4.056 (0.5); 4,038 (1.4); 4,020 (1.4); 4.003 (0.5); 3,336 (349.9); 3,313 (1.9); 3,297 (0.4); 3,275 (7.2); 3,269 (7.1); 2,677 (0.8); 2,673 (1.0); 2,668 (0.8); 2,508 (128,7); 2,504 (163.4); 2,499 (117.0); 2.335 (0.8); 2,330 (1.0); 2,326 (0.7); 1,990 (6.2); 1,442 (16.0); 1,424 (15.9); 1.193 (1.6); 1,175
(3.2) ; 1 ,158 (1,6); 0,008 (3,1); 0,000 (69,2); -0,008 (2,8) (3.2); 1, 158 (1.6); 0.008 (3.1); 0,000 (69.2); -0.008 (2.8)
Beispiel 1-1-32: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-32: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,135 (1,7); 10,111 (1,7); 8,879 (2,4); 8,857 (2,6); 8,593 (1,6); 8,574 (1,6); 8,308 (6,1); 8,297 (2,7); 8,286 (3,6); 8,275 (2,7); 8,159 (1,3); 8,140 (1,4); 7,881 (3,6); 7,859 (3,3); 7,841 (1,2); 7,821 (1,7); 7,745 (1,3); 7,726 (2,0); 7,706 (0,8); 6,399 (0,7); 6,377 (1,0); 6,354 (0,7); 5,759 (0,4); 4,147 (0,7); 4,131 (1,0); 4,112 (1,0); 4,095 (0,7); 4,039 (0,7); 4,021 (0,7); 3,334 (72,6); 2,673 (0,3); 2,526 (0,9); 2,512 (21,3); 2,508 (42,4); 2,504 (55,1); 2,499 (39,5); 2,495 (19,0); 2,331 (0,4); 1,990 (3,0); 1,208 (16,0); 1,191 (16,0); 1,176 (1,8);δ = 10.135 (1.7); 10.111 (1.7); 8,879 (2,4); 8.857 (2.6); 8,593 (1.6); 8,574 (1.6); 8,308 (6,1); 8,297 (2.7); 8,286 (3.6); 8.275 (2.7); 8,159 (1.3); 8.140 (1.4); 7,881 (3.6); 7,859 (3.3); 7.841 (1.2); 7,821 (1.7); 7,745 (1.3); 7,726 (2.0); 7.706 (0.8); 6,399 (0.7); 6,377 (1.0); 6,354 (0.7); 5,759 (0.4); 4.147 (0.7); 4.113 (1.0); 4.112 (1.0); 4,095 (0.7); 4,039 (0.7); 4,021 (0.7); 3,334 (72.6); 2,673 (0.3); 2,526 (0.9); 2,512 (21.3); 2,508 (42.4); 2,504 (55.1); 2,499 (39.5); 2,495 (19.0); 2,331 (0.4); 1,990 (3.0); 1,208 (16,0); 1,191 (16.0); 1.176 (1.8);
1,158 (0,8); 0,008 (1,0); 0,000 (25,6); -0,009 (0,9) 1.158 (0.8); 0.008 (1.0); 0.000 (25.6); -0.009 (0.9)
Beispiel 1-1-33: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-33: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,134 (2,8); 10,109 (2,8); 8,883 (3,8); 8,861 (4,1); 8,860 (4,0); 8,708 (1,4); 8,694 (2,7); 8,680 (1,4); 8,335 (0,5); 8,308 (9,9); 8,301 (5,8); 8,286 (6,0); 8,279 (4,4); 8,277 (4,2); 8,157 (2,4); 8,138 (2,3); 7,898 (5,9); 7,877 (5,3); 7,841 (2,1); 7,821 (2,9); 7,744 (2,2); 7,725 (3,3); 7,705 (1,4); 6,400 (1,1); 6,378 (1,7); 6,355 (1,2); 6,332 (0,4); 4,056 (0,4); 4,038δ = 10.134 (2.8); 10,109 (2,8); 8,883 (3.8); 8,861 (4,1); 8.860 (4.0); 8,708 (1.4); 8,694 (2.7); 8,680 (1.4); 8.335 (0.5); 8,308 (9.9); 8,301 (5.8); 8,286 (6.0); 8,279 (4,4); 8,277 (4,2); 8,157 (2,4); 8.138 (2.3); 7,898 (5.9); 7,877 (5.3); 7,841 (2.1); 7,821 (2.9); 7.744 (2.2); 7,725 (3.3); 7,705 (1.4); 6,400 (1.1); 6.378 (1.7); 6.355 (1.2); 6.332 (0.4); 4.056 (0.4); 4,038
(1.3) ; 4,021 (1,3); 4,003 (0,4); 3,370 (1,1); 3,352 (3,6); 3,333 (112,3); 3,320 (4,3); 3,302 (1,1); 2,677 (0,5); 2,673 (0,7); 2,668 (0,5); 2,526 (1,6); 2,512 (38,9); 2,508 (77,4); 2,504 (99,8); 2,499 (71,5); 2,495 (34,3); 2,335 (0,5); 2,330 (0,6); 2,326 (0,5); 1,990 (5,6); 1,236 (0,5); 1,193 (2,7); 1,189 (7,6); 1,175 (5,0); 1,170 (16,0); 1,157 (2,8); 1,152 (7,3); 1,058(1.3); 4,021 (1.3); 4.003 (0.4); 3,370 (1,1); 3,352 (3.6); 3,333 (112.3); 3,320 (4.3); 3.302 (1.1); 2,677 (0.5); 2,673 (0.7); 2,668 (0.5); 2,526 (1.6); 2,512 (38.9); 2,508 (77.4); 2,504 (99.8); 2,499 (71.5); 2,495 (34.3); 2.335 (0.5); 2,330 (0.6); 2,326 (0.5); 1,990 (5.6); 1,236 (0.5); 1,193 (2.7); 1.199 (7.6); 1,175 (5.0); 1,170 (16.0); 1.157 (2.8); 1,152 (7.3); 1,058
(0,4); 0,008 (1,0); 0,000 (26,6); -0,008 (1,0) (0.4); 0.008 (1.0); 0,000 (26.6); -0.008 (1.0)
Beispiel 1-1-34: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-34: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,122 (3,0); 10,098 (3,1); 9,784 (2,7); 9,222 (6,4); 8,972 (2,7); 8,871 (4,1); 8,849 (4,5); 8,323 (2,9); 8,300 (16,0); 8,278 (6,0); 8,268 (7,3); 8,246 (3,5); 8,157 (2,5); 8,138 (2,6); 7,843 (2,2); 7,823 (3,1); 7,746 (2,3); 7,727 (3,5); 7,707 (1,5); 6,421 (0,4); 6,400 (1,3); 6,379 (1,8); 6,356 (1,3); 6,334 (0,4); 3,337 (128,3); 2,678 (0,4); 2,674 (0,5); 2,670 (0,4); δ = 10.122 (3.0); 10.098 (3.1); 9,784 (2.7); 9,222 (6.4); 8,972 (2.7); 8,871 (4,1); 8.849 (4.5); 8,323 (2,9); 8,300 (16.0); 8,278 (6.0); 8,268 (7.3); 8.246 (3.5); 8.157 (2.5); 8.138 (2.6); 7,843 (2.2); 7,823 (3,1); 7.746 (2.3); 7,727 (3.5); 7,707 (1.5); 6,421 (0.4); 6,400 (1.3); 6.379 (1.8); 6.356 (1.3); 6.334 (0.4); 3,337 (128.3); 2,678 (0.4); 2,674 (0.5); 2,670 (0.4);
2,509 (55,8); 2,505 (70,1); 2,501 (50,2); 2,336 (0,3); 2,331 (0,4); 1,901 (2,3); 1,892 (4,8); 1,883 (5,3); 1,874 (2,2); 1,331 (2,5); 1,322 (5,3); 1,313 (5,2); 1,303 (2,0); 1,233 (0,4);2,509 (55.8); 2,505 (70.1); 2,501 (50,2); 2.336 (0.3); 2,331 (0.4); 1,901 (2,3); 1,892 (4.8); 1,883 (5.3); 1,874 (2.2); 1,331 (2.5); 1,322 (5.3); 1,313 (5.2); 1.303 (2.0); 1,233 (0.4);
0,008 (1,8); 0,000 (31,2); -0,008 (1,3) 0.008 (1.8); 0,000 (31.2); -0.008 (1.3)
Beispiel 1-1-35: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-35: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,140 (3,9); 10,115 (4,1); 8,883 (5,5); 8,861 (6,0); 8,650 (3,8); 8,629 (3,8); 8,310 (14,2); 8,307 (11,3); 8,288 (8,6); 8,284 (6,9); 8,161 (3,2); 8,141 (3,5); 7,871 (7,7); 7,849 (7,7); 7,842 (3,1); 7,822 (4,1); 7,746 (3,0); 7,726 (4,7); 7,707 (1,9); 6,421 (0,5); 6,399 (1,6); 6,377 (2,4); 6,354 (1,7); 6,333 (0,5); 4,056 (1,0); 4,038 (3,2); 4,021 (3,2); 4,003 (1,1); 3,607 (1,2); 3,588 (2,3); 3,571 (2,3); 3,551 (1,3); 3,534 (0,3); 3,334 (220,4); 2,677 (0,7); 2,673 (0,9); 2,668 (0,7); 2,508 (110,1); 2,504 (143,8); 2,499 (105,4); 2,335 (0,6); 2,330 (0,9); 2,326 (0,7); 1,990 (13,8); 1,259 (16,0); 1,243 (15,8); 1,193 (3,7); 1,176 (7,3); 1,158 (3,6); 1,000 (0,4); 0,987 (0,8); 0,980 (1,2); 0,967 (2,2); 0,960 (1,5); 0,955 (1,6); 0,947 (2,3); 0,935 (1,3); 0,927 (0,9); 0,915 (0,5); 0,516 (0,5); 0,503 (0,8); 0,494 (1,8); 0,486 (1,7); 0,481 (2,0); 0,473 (2,5); 0,460 (1,4); 0,452 (2,2); 0,440 (1,7); 0,429 (1,9); 0,421 (2,2); 0,409δ = 10.140 (3.9); 10,115 (4,1); 8,883 (5.5); 8,861 (6.0); 8,650 (3.8); 8,629 (3.8); 8,310 (14.2); 8,307 (11.3); 8,288 (8,6); 8,284 (6.9); 8,161 (3,2); 8,141 (3,5); 7,871 (7.7); 7,849 (7.7); 7,842 (3.1); 7,822 (4,1); 7.746 (3.0); 7,726 (4,7); 7,707 (1.9); 6,421 (0.5); 6,399 (1.6); 6,377 (2,4); 6,354 (1.7); 6,333 (0.5); 4.056 (1.0); 4,038 (3.2); 4,021 (3.2); 4.003 (1.1); 3.607 (1.2); 3,588 (2,3); 3.571 (2.3); 3,551 (1.3); 3,534 (0.3); 3,334 (220.4); 2,677 (0.7); 2,673 (0.9); 2,668 (0.7); 2,508 (110.1); 2,504 (143.8); 2,499 (105.4); 2.335 (0.6); 2,330 (0.9); 2,326 (0.7); 1,990 (13.8); 1,259 (16,0); 1,243 (15,8); 1,193 (3.7); 1.176 (7.3); 1.158 (3.6); 1,000 (0.4); 0.987 (0.8); 0.980 (1.2); 0.967 (2.2); 0.960 (1.5); 0.955 (1.6); 0.947 (2.3); 0.935 (1.3); 0.927 (0.9); 0.915 (0.5); 0.516 (0.5); 0.503 (0.8); 0.494 (1.8); 0.486 (1.7); 0.481 (2.0); 0.473 (2.5); 0.460 (1.4); 0.452 (2.2); 0.440 (1.7); 0.429 (1.9); 0.421 (2.2); 0.409
(2.6) ; 0,398 (2,2); 0,388 (2,9); 0,376 (2,8); 0,365 (2,0); 0,353 (0,8); 0,325 (1,2); 0,313 (2,1); 0,303 (2,6); 0,291 (2,2); 0,281 (1,3); 0,268 (0,5); 0,008 (2,4); 0,000 (59,7); -0,008 (2,6) Beispiel 1-1-36: 1H-NMR (400,0 MHz, d6-DMSO): (2.6); 0.398 (2.2); 0.388 (2.9); 0.376 (2.8); 0.365 (2.0); 0.353 (0.8); 0.325 (1.2); 0.313 (2.1); 0.303 (2.6); 0.291 (2.2); 0.281 (1.3); 0.268 (0.5); 0.008 (2.4); 0.000 (59.7); -0.008 (2.6) Example 1-1-36: 1 H-NMR (400.0 MHz, d 6 -DMSO):
δ= 10,150 (2,4); 10,126 (2,5); 9,565 (2,6); 9,547 (2,6); 8,907 (3,3); 8,885 (3,7); 8,341 (3,3); 8,327 (5,0); 8,319 (4,3); 8,305 (7,9); 8,286 (0,4); 8,158 (2,0); 8,139 (2,2); 7,951 (4,7); 7,930 (4,3); 7,842 (1,9); 7,822 (2,6); 7,745 (1,9); 7,726 (3,0); 7,706 (1,3); 6,402 (1,0); 6,380 (1,5); 6,358 (1,1); 6,336 (0,3); 5,102 (0,4); 5,084 (1,8); 5,066 (2,8); 5,048 (1,8); 5,030 (0,4); 4,498 (1,2); 4,481 (4,1); 4,463 (4,2); 4,445 (1,2); 4,056 (0,4); 4,038 (1,1); 4,020 (1,1); 4,003 (0,4); 3,331 (169,2); 2,677 (0,8); 2,672 (1,0); 2,668 (0,7); 2,507 (122,8); 2,503 (155,5); 2,499 (111,7); 2,334 (0,8); 2,330 (1,0); 2,326 (0,7); 1,990 (4,8); 1,565 (10,3); 1,547(10,2); 1,406 (16,0); 1,388 (15,9); 1,365 (1,9); 1,348(1,8); 1,233 (0,7); 1,225 (0,6);δ = 10.150 (2.4); 10.126 (2.5); 9.565 (2.6); 9.547 (2.6); 8,907 (3.3); 8,885 (3.7); 8,341 (3.3); 8,327 (5.0); 8,319 (4,3); 8,305 (7.9); 8,286 (0.4); 8.158 (2.0); 8.139 (2.2); 7,951 (4,7); 7,930 (4.3); 7,842 (1.9); 7.822 (2.6); 7,745 (1.9); 7,726 (3.0); 7.706 (1.3); 6,402 (1.0); 6,380 (1.5); 6.358 (1.1); 6.336 (0.3); 5.102 (0.4); 5,084 (1.8); 5,066 (2.8); 5,048 (1.8); 5,030 (0.4); 4,498 (1,2); 4,481 (4,1); 4,463 (4,2); 4,445 (1,2); 4.056 (0.4); 4.038 (1.1); 4.020 (1.1); 4.003 (0.4); 3,331 (169,2); 2,677 (0.8); 2,672 (1.0); 2,668 (0.7); 2,507 (122,8); 2,503 (155.5); 2,499 (111.7); 2.334 (0.8); 2,330 (1.0); 2,326 (0.7); 1,990 (4.8); 1,565 (10.3); 1,547 (10.2); 1,406 (16,0); 1.388 (15.9); 1,365 (1.9); 1,348 (1.8); 1,233 (0.7); 1.225 (0.6);
1,193 (1,3); 1,175 (2,6); 1,158 (1,3); 0,961 (0,4); 0,008 (2,9); 0,000 (64,6); -0,008 (2,8) 1.193 (1.3); 1,175 (2.6); 1.158 (1.3); 0.961 (0.4); 0.008 (2.9); 0,000 (64.6); -0.008 (2.8)
Beispiel 1-1-37: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-37: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,166 (4,7); 10,141 (4,9); 9,503 (4,8); 9,486 (4,9); 8,899 (6,0); 8,898 (6,1); 8,877 (6,5); 8,876 (6,8); 8,408 (3,1); 8,391 (3,0); 8,320 (16,0); 8,298 (16,0); 8,281 (1,6); 8,276 (1,7); 8,270 (1,8); 8,261 (2,1); 8,254 (1,9); 8,248 (1,9); 7,957 (9,8); 7,935 (9,0); 7,682 (2,8); 7,657 (3,6); 7,634 (2,6); 6,462 (0,5); 6,440 (1,8); 6,418 (2,6); 6,395 (1,9); 6,373 (0,6); 5,101 (0,4); 5,084 (1,5); 5,066 (3,2); 5,050 (3,5); 5,032 (2,1); 5,015 (0,6); 4,856 (7,3); 4,839 (11,4); 4,821 (6,8); 4,600 (7,4); 4,584 (14,1); 4,568 (6,6); 4,057 (0,6); 4,040 (1,9); 4,022 (1,9); 4,004 (0,6); 3,329 (78,2); 2,678 (0,5); 2,674 (0,6); 2,669 (0,5); 2,527 (1,4); 2,513 (33,8); 2,509 (68,6); 2,505 (90,1); 2,500 (65,1); 2,496 (31,1); 2,336 (0,4); 2,331 (0,6); 2,327 (0,4);δ = 10.166 (4.7); 10.141 (4.9); 9,503 (4,8); 9,486 (4.9); 8,899 (6.0); 8,898 (6,1); 8,877 (6.5); 8,876 (6.8); 8,408 (3,1); 8.391 (3.0); 8,320 (16,0); 8,298 (16.0); 8,281 (1.6); 8.276 (1.7); 8,270 (1.8); 8,261 (2,1); 8.254 (1.9); 8,248 (1.9); 7,957 (9.8); 7,935 (9.0); 7,682 (2.8); 7.657 (3.6); 7.634 (2.6); 6,462 (0.5); 6,440 (1.8); 6.418 (2.6); 6,395 (1.9); 6,373 (0.6); 5.101 (0.4); 5,084 (1.5); 5,066 (3.2); 5,050 (3.5); 5,032 (2.1); 5,015 (0.6); 4,856 (7.3); 4,839 (11,4); 4,821 (6.8); 4,600 (7.4); 4,584 (14.1); 4,568 (6.6); 4.057 (0.6); 4,040 (1.9); 4,022 (1.9); 4.004 (0.6); 3,329 (78.2); 2,678 (0.5); 2,674 (0.6); 2,669 (0.5); 2,527 (1.4); 2,513 (33,8); 2,509 (68.6); 2,505 (90.1); 2,500 (65.1); 2,496 (31.1); 2.336 (0.4); 2.331 (0.6); 2,327 (0.4);
1,991 (8,3); 1,234 (0,9); 1,194 (2,3); 1,176 (4,5); 1,159 (2,2); 0,000 (8,9) 1,991 (8.3); 1,234 (0.9); 1,194 (2,3); 1.176 (4.5); 1.159 (2.2); 0,000 (8.9)
Beispiel 1-1-38: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-38: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,168 (6,1); 10,144 (6,2); 9,515 (3,2); 9,501 (6,8); 9,487 (3,2); 8,907 (8,3); 8,884 (9,1); 8,406 (4,4); 8,391 (4,3); 8,346 (0,5); 8,335 (8,5); 8,325 (11,9); 8,313 (9,6); 8,303 (11,0); 8,274 (2,4); 8,268 (2,6); 8,259 (3,0); 8,253 (2,7); 8,246 (2,6); 7,948 (11,3); 7,926 (10,3); 7,682 (3,7); 7,656 (4,9); 7,633 (3,5); 6,463 (0,7); 6,441 (2,4); 6,419 (3,6); 6,397 (2,6); 6,375 (0,8); 5,759 (4,4); 4,445 (16,0); 4,431 (15,9); 4,058 (0,8); 4,040 (2,4); 4,022 (2,5); 4,004 (0,8); 3,333 (142,1); 2,675 (0,6); 2,510 (71,1); 2,506 (91,5); 2,502 (68,0); 2,337δ = 10.168 (6.1); 10.144 (6.2); 9.515 (3.2); 9.501 (6.8); 9,487 (3,2); 8,907 (8,3); 8,884 (9.1); 8,406 (4.4); 8,391 (4,3); 8.346 (0.5); 8,335 (8.5); 8.325 (11.9); 8,313 (9.6); 8,303 (11,0); 8.274 (2.4); 8.268 (2.6); 8.259 (3.0); 8,253 (2,7); 8.246 (2.6); 7,948 (11.3); 7,926 (10.3); 7,682 (3.7); 7.656 (4.9); 7.633 (3.5); 6,463 (0.7); 6,441 (2,4); 6,419 (3.6); 6.397 (2.6); 6.375 (0.8); 5,759 (4.4); 4,445 (16.0); 4,431 (15,9); 4.058 (0.8); 4.040 (2.4); 4.022 (2.5); 4.004 (0.8); 3,333 (142.1); 2,675 (0.6); 2,510 (71.1); 2,506 (91.5); 2,502 (68.0); 2,337
(0,4); 2,333 (0,6); 2,328 (0,5); 1,991 (10,2); 1,232 (0,5); 1,195 (2,7); 1,177 (5,3); 1,159 (2,6); 0,000 (7,3) (0.4); 2.333 (0.6); 2.328 (0.5); 1,991 (10.2); 1,232 (0.5); 1,195 (2.7); 1,177 (5.3); 1.159 (2.6); 0,000 (7.3)
Beispiel 1-1-39: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-39: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,165 (7,1); 10,140 (7,3); 9,165 (3,4); 9,150 (7,4); 9,135 (3,5); 8,896 (9,0); 8,895 (9,0); 8,874 (9,8); 8,873 (10,0); 8,407 (4,5); 8,393 (4,5); 8,339 (0,5); 8,326 (9,3); 8,325 (9,3); 8,317 (16,0); 8,305 (10,4); 8,303 (10,5); 8,295 (15,1); 8,280 (2,3); 8,276 (2,5); 8,269 (2,7); 8,261 (3,1); 8,254 (2,8); 8,248 (2,8); 7,914 (14,7); 7,892 (13,8); 7,682 (4,1); 7,656 (5,2); 7,633 (3,8); 6,462 (0,7); 6,440 (2,6); 6,418 (3,8); 6,395 (2,8); 6,373 (0,9); 6,349 (1,3); 6,339 (2,6); 6,330 (1,2); 6,210 (2,6); 6,200 (5,7); 6,191 (2,6); 6,070 (1,3); 6,061 (2,8); 6,052 (1,4); 5,759 (5,0); 4,040 (0,5); 4,022 (0,5); 3,810 (1,9); 3,800 (2,5); 3,795 (2,3); 3,786 (2,2); 3,770 (4,3); 3,761 (4,9); 3,756 (4,8); 3,746 (4,1); 3,731 (2,3); 3,721 (2,4); 3,716 (2,5); 3,706 (2,0); 3,332 (154,6); 3,307 (0,3); 2,679 (0,5); 2,675 (0,7); 2,670 (0,5); 2,528 (1,5); 2,515 (38,1); 2,510 (77,5); 2,506 (102,0); 2,501 (73,3); 2,497 (34,8); 2,337 (0,5); 2,333δ = 10.165 (7.1); 10.140 (7.3); 9.165 (3.4); 9.150 (7.4); 9.135 (3.5); 8,896 (9.0); 8,895 (9.0); 8,874 (9.8); 8,873 (10.0); 8,407 (4,5); 8,393 (4,5); 8.399 (0.5); 8,326 (9.3); 8,325 (9.3); 8,317 (16.0); 8,305 (10.4); 8,303 (10.5); 8,295 (15: 1); 8,280 (2.3); 8.276 (2.5); 8.269 (2.7); 8,261 (3,1); 8.254 (2.8); 8.248 (2.8); 7.914 (14.7); 7,892 (13.8); 7,682 (4,1); 7.656 (5.2); 7.633 (3.8); 6,462 (0.7); 6,440 (2.6); 6,418 (3.8); 6,395 (2.8); 6,373 (0.9); 6.349 (1.3); 6,339 (2,6); 6.330 (1.2); 6.210 (2.6); 6,200 (5.7); 6,191 (2,6); 6.070 (1.3); 6,061 (2.8); 6,052 (1.4); 5,759 (5.0); 4,040 (0.5); 4.022 (0.5); 3,810 (1.9); 3,800 (2.5); 3,795 (2.3); 3,786 (2.2); 3,770 (4,3); 3,761 (4.9); 3,756 (4,8); 3,746 (4,1); 3,731 (2,3); 3,721 (2,4); 3,716 (2.5); 3,706 (2.0); 3,332 (154.6); 3.307 (0.3); 2,679 (0.5); 2.675 (0.7); 2,670 (0.5); 2,528 (1.5); 2,515 (38.1); 2,510 (77.5); 2,506 (102,0); 2,501 (73.3); 2,497 (34.8); 2.377 (0.5); 2,333
(0,7); 2,328 (0,5); 1,991 (2,1); 1,231 (0,5); 1,195 (0,6); 1,177 (1,2); 1,159 (0,6); 0,008 (0,3); 0,000 (10,5); -0,009 (0,3) (0.7); 2.328 (0.5); 1,991 (2.1); 1.231 (0.5); 1,195 (0.6); 1.177 (1.2); 1.159 (0.6); 0.008 (0.3); 0.000 (10.5); -0.009 (0.3)
Beispiel 1-1-40: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-40: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,166 (0,5); 10,143 (6,0); 10,118 (5,9); 9,779 (5,2); 9,218 (11,9); 8,966 (5,2); 8,897 (0,4); 8,884 (0,8); 8,869 (7,5); 8,847 (8,0); 8,400 (4,6); 8,386 (4,5); 8,316 (5,6); 8,297 (16,0); 8,275 (13,0); 8,264 (15,7); 8,243 (8,4); 8,154 (0,4); 7,956 (0,4); 7,934 (0,4); 7,922 (0,6); 7,900 (0,7); 7,680 (3,7); 7,655 (5,1); 7,632 (3,5); 6,457 (0,7); 6,436 (2,5); 6,414δ = 10.166 (0.5); 10.143 (6.0); 10.118 (5.9); 9,779 (5.2); 9.218 (11.9); 8.966 (5.2); 8.897 (0.4); 8.884 (0.8); 8,869 (7.5); 8,847 (8.0); 8,400 (4,6); 8,386 (4,5); 8.316 (5.6); 8,297 (16.0); 8.275 (13.0); 8,264 (15,7); 8,243 (8.4); 8.154 (0.4); 7.956 (0.4); 7,934 (0.4); 7.922 (0.6); 7,900 (0.7); 7,680 (3.7); 7,655 (5.1); 7.632 (3.5); 6.457 (0.7); 6,436 (2.5); 6,414
(3.7) ; 6,391 (2,6); 6,369 (0,8); 5,757 (5,6); 4,838 (0,4); 4,817 (0,4); 4,583 (0,4); 4,039 (0,4); 4,021 (0,5); 3,333 (58,5); 2,677 (0,9); 2,673 (1,2); 2,508 (126,6); 2,504 (157,8); 2,500 (117,0); 2,335 (0,8); 2,331 (1,0); 1,990 (1,8); 1,900 (4,6); 1,891 (8,9); 1,882 (9,9); 1,874 (4,5); 1,372 (0,4); 1,330 (4,8); 1,321 (10,2); 1,312 (10,0); 1,303 (4,2); 1,259 (0,8); 1,234 (3.7); 6.391 (2.6); 6,369 (0.8); 5,757 (5.6); 4,838 (0.4); 4,817 (0.4); 4,583 (0.4); 4,039 (0.4); 4,021 (0.5); 3,333 (58.5); 2,677 (0.9); 2,673 (1.2); 2,508 (126.6); 2,504 (157.8); 2,500 (117.0); 2.335 (0.8); 2.331 (1.0); 1,990 (1.8); 1,900 (4,6); 1,891 (8.9); 1,882 (9.9); 1,874 (4.5); 1,372 (0.4); 1,330 (4,8); 1,321 (10,2); 1,312 (10,0); 1,303 (4,2); 1,259 (0.8); 1,234
(2,6); 1,194 (0,7); 1,176 (1,1); 1,158 (0,6); 0,917 (3,2); 0,853 (0,5); 0,109 (2,1); 0,095 (0,8); 0,000 (4,1) (2,6); 1,194 (0.7); 1.176 (1.1); 1.158 (0.6); 0.917 (3.2); 0.853 (0.5); 0,109 (2,1); 0.095 (0.8); 0,000 (4.1)
Beispiel 1-1-41: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-41: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,167 (1,4); 10,143 (1,5); 9,361 (0,7); 9,346 (1,5); 9,331 (0,7); 8,902 (1,9); 8,880 (2,1); 8,569 (1,2); 8,557 (1,2); 8,408 (1,0); 8,391 (0,9); 8,334 (1,9); 8,319 (2,8); 8,312 (2,3); 8,297 (2,5); 8,276 (0,5); 8,270 (0,6); 8,262 (0,7); 8,254 (0,6); 8,248 (0,6); 7,995 (2,6); 7,973 (2,3); 7,884 (0,6); 7,880 (0,6); 7,865 (1,2); 7,861 (1,3); 7,846 (0,7); 7,842 (0,7); 7,682 (0,8); 7,656 (1,1); 7,633 (0,8); 7,539 (1,6); 7,520 (1,5); 7,350 (0,9); 7,337 (0,9); 7,332 (0,9); 7,319 (0,8); 6,441 (0,5); 6,419 (0,8); 6,396 (0,6); 5,758 (0,8); 4,647 (3,0); 4,632 (2,9); 4,057 (1,3); 4,040 (3,8); 4,022 (3,9); 4,004 (1,3); 3,367 (2,4); 2,893 (0,3); 2,691 (0,8); 2,509 (21,5); 2,505 (28,7); 2,500 (21,6); 1,991 (16,0); 1,194 (4,3); 1,176 (8,4); 1,159 (4,2);δ = 10.167 (1.4); 10.143 (1.5); 9.361 (0.7); 9.346 (1.5); 9,331 (0.7); 8,902 (1.9); 8,880 (2.1); 8,569 (1.2); 8,557 (1.2); 8.408 (1.0); 8.391 (0.9); 8,334 (1.9); 8,319 (2.8); 8.312 (2.3); 8.297 (2.5); 8.276 (0.5); 8.270 (0.6); 8.262 (0.7); 8.254 (0.6); 8.248 (0.6); 7.995 (2.6); 7.973 (2.3); 7.884 (0.6); 7,880 (0.6); 7.865 (1.2); 7.861 (1.3); 7.846 (0.7); 7,842 (0.7); 7.682 (0.8); 7.656 (1.1); 7.633 (0.8); 7,539 (1.6); 7,520 (1.5); 7,350 (0.9); 7,337 (0.9); 7.332 (0.9); 7,319 (0.8); 6.441 (0.5); 6,419 (0.8); 6.396 (0.6); 5,758 (0.8); 4,647 (3.0); 4,632 (2,9); 4.057 (1.3); 4,040 (3.8); 4,022 (3.9); 4.004 (1.3); 3.367 (2.4); 2,893 (0.3); 2,691 (0.8); 2,509 (21.5); 2,505 (28.7); 2,500 (21.6); 1,991 (16.0); 1,194 (4,3); 1.176 (8.4); 1,159 (4,2);
0,000 (2,4) 0,000 (2,4)
Beispiel 1-1-42: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-42: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,154 (1,7); 10,130 (1,7); 8,877 (2,2); 8,876 (2,2); 8,855 (2,4); 8,854 (2,5); 8,588 (1,6); 8,569 (1,6); 8,406 (1,1); 8,393 (1,1); 8,305 (3,7); 8,292 (2,3); 8,290 (2,4); 8,283 (3,9); 8,270 (3,1); 8,268 (3,2); 8,247 (0,7); 7,878 (3,5); 7,857 (3,3); 7,680 (1,0); 7,655 (1,3); 7,631 (0,9); 6,434 (0,6); 6,412 (0,9); 6,389 (0,7); 4,147 (0,6); 4,130 (1,0); 4,111 (1,0); 4,095 (0,7); 3,326 (58,7); 2,677 (0,4); 2,672 (0,5); 2,667 (0,4); 2,525 (1,2); 2,512 (28,5); 2,507 (56,2); 2,503 (72,7); 2,498 (52,5); 2,494 (25,3); 2,334 (0,4); 2,330 (0,5); 2,325 (0,4); 1,990δ = 10.154 (1.7); 10.130 (1.7); 8.877 (2.2); 8.876 (2.2); 8.855 (2.4); 8.854 (2.5); 8,588 (1.6); 8,569 (1.6); 8.406 (1.1); 8.393 (1.1); 8,305 (3.7); 8.292 (2.3); 8.290 (2.4); 8,283 (3.9); 8,270 (3,1); 8,268 (3,2); 8.247 (0.7); 7,878 (3.5); 7,857 (3.3); 7,680 (1.0); 7.655 (1.3); 7,631 (0.9); 6,434 (0.6); 6.412 (0.9); 6,389 (0.7); 4.147 (0.6); 4.130 (1.0); 4.111 (1.0); 4,095 (0.7); 3,326 (58.7); 2,677 (0.4); 2,672 (0.5); 2,667 (0.4); 2.525 (1.2); 2,512 (28.5); 2,507 (56,2); 2,503 (72,7); 2,498 (52.5); 2,494 (25.3); 2.334 (0.4); 2.330 (0.5); 2.325 (0.4); 1,990
(0,6); 1,207 (16,0); 1,191 (15,9); 1,176 (0,5); 0,000 (1,5) (0.6); 1,207 (16,0); 1,191 (15.9); 1.176 (0.5); 0,000 (1.5)
Beispiel 1-1-43: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-43: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,157 (4,1); 10,133 (4,2); 8,953 (4,0); 8,934 (4,0); 8,881 (5,4); 8,859 (6,0); 8,407 (2,8); 8,394 (2,8); 8,318 (0,7); 8,309 (8,5); 8,291 (6,3); 8,287 (8,9); 8,270 (7,6); 8,262 (2,3);δ = 10.157 (4.1); 10.133 (4.2); 8,953 (4.0); 8.934 (4.0); 8,881 (5.4); 8,859 (6.0); 8,407 (2,8); 8,394 (2.8); 8.318 (0.7); 8,309 (8.5); 8,291 (6,3); 8,287 (8.9); 8,270 (7.6); 8.262 (2.3);
8.254 (1,8); 8,247 (1,7); 7,892 (8,1); 7,871 (7,5); 7,681 (2,5); 7,655 (3,2); 7,632 (2,3); 6,458 (0,4); 6,437 (1,6); 6,414 (2,3); 6,392 (1,7); 6,370 (0,5); 4,490 (0,3); 4,469 (1,3); 4,449 (2,6); 4,429 (2,6); 4,409 (1,3); 4,057 (1,2); 4,039 (3,6); 4,022 (3,6); 4,004 (1,2); 3,329 (77,7); 2,678 (0,5); 2,673 (0,6); 2,669 (0,4); 2,513 (36,0); 2,509 (67,9); 2,504 (86,7); 2,500 (62,3); 2,336 (0,5); 2,331 (0,7); 2,326 (0,8); 2,322 (1,0); 2,312 (1,3); 2,305 (1,9); 2,293 (2,9); 2,286 (3,2); 2,279 (3,1); 2,266 (2,7); 2,247 (1,1); 2,092 (0,8); 2,086 (0,7); 2,069 (2,6); 2,045 (3,8); 2,039 (3,5); 2,022 (2,6); 2,016 (2,7); 1,991 (16,0); 1,749 (1,6); 1,736 (3,0); 1,725(3,5); 1,711 (4,8); 1,701 (2,4); 1,693 (1,8); 1,686(1,8); 1,668 (0,7); 1,194(4,1); 1,1768,254 (1.8); 8.247 (1.7); 7,892 (8,1); 7,871 (7.5); 7.681 (2.5); 7.655 (3.2); 7.632 (2.3); 6.458 (0.4); 6.437 (1.6); 6,414 (2,3); 6,392 (1.7); 6,370 (0.5); 4,490 (0.3); 4.469 (1.3); 4,449 (2.6); 4,429 (2,6); 4.409 (1.3); 4.057 (1.2); 4,039 (3.6); 4,022 (3.6); 4.004 (1.2); 3,329 (77.7); 2,678 (0.5); 2,673 (0.6); 2,669 (0.4); 2,513 (36.0); 2,509 (67.9); 2,504 (86.7); 2,500 (62.3); 2.336 (0.5); 2.331 (0.7); 2,326 (0.8); 2,322 (1.0); 2,312 (1,3); 2.305 (1.9); 2,293 (2.9); 2.286 (3.2); 2,279 (3,1); 2,266 (2.7); 2.247 (1.1); 2,092 (0.8); 2.086 (0.7); 2.069 (2.6); 2.045 (3.8); 2.039 (3.5); 2.022 (2.6); 2.016 (2.7); 1,991 (16.0); 1,749 (1.6); 1,736 (3.0); 1.725 (3.5); 1,711 (4,8); 1,701 (2,4); 1,693 (1.8); 1,686 (1.8); 1,668 (0.7); 1,194 (4.1); 1,176
(8.1) ; 1,159 (4,0); 0,000 (1,8) (8.1); 1,159 (4.0); 0,000 (1.8)
Beispiel 1-1-44: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-44: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,155 (2,9); 10,131 (3,0); 8,882 (3,8); 8,860 (4,2); 8,704 (1,4); 8,691 (2,9); 8,677 (1,4); 8,406 (2,0); 8,393 (1,9); 8,308 (6,0); 8,296 (3,9); 8,286 (6,0); 8,274 (5,3); 8,261 (1,4); 8,253 (1,2); 8,247 (1,2); 7,898 (5,7); 7,876 (5,2); 7,680 (1,7); 7,655 (2,2); 7,632 (1,6); 6,437 (1,1); 6,415 (1,6); 6,392 (1,2); 6,370 (0,4); 5,759 (0,7); 4,057 (0,7); 4,040 (2,1); 4,022δ = 10.155 (2.9); 10.131 (3.0); 8,882 (3,8); 8,860 (4.2); 8,704 (1.4); 8,691 (2.9); 8.677 (1.4); 8,406 (2.0); 8,393 (1.9); 8,308 (6.0); 8.296 (3.9); 8,286 (6.0); 8.274 (5.3); 8.261 (1.4); 8.253 (1.2); 8.247 (1.2); 7,898 (5.7); 7,876 (5.2); 7,680 (1.7); 7.655 (2.2); 7.632 (1.6); 6.437 (1.1); 6,415 (1.6); 6,392 (1.2); 6,370 (0.4); 5,759 (0.7); 4.057 (0.7); 4,040 (2.1); 4,022
(2.2) ; 4,004 (0,7); 3,372 (1,0); 3,354 (3,4); 3,330 (43,9); 3,322 (4,4); 3,304 (1,1); 2,674 (0,3); 2,513 (21,5); 2,509 (41,2); 2,505 (52,8); 2,500 (38,3); 2,332 (0,3); 1,991 (9,3); 1,194(2.2); 4.004 (0.7); 3,372 (1.0); 3.354 (3.4); 3,330 (43.9); 3,322 (4.4); 3.304 (1.1); 2,674 (0.3); 2,513 (21.5); 2,509 (41.2); 2,505 (52,8); 2,500 (38.3); 2.332 (0.3); 1,991 (9.3); 1,194
(3,9); 1,190 (7,7); 1,176 (7,2); 1,172 (16,0); 1,159 (3,7); 1,154 (7,4); 0,000 (1,2) (3.9); 1,190 (7.7); 1.176 (7.2); 1,172 (16.0); 1,159 (3.7); 1.144 (7.4); 0,000 (1.2)
Beispiel 1-1-45: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-45: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,154 (3,8); 10,129 (3,9); 8,883 (5,1); 8,861 (5,6); 8,647 (1,1); 8,637 (3,0); 8,625 (3,0); 8,614 (1,0); 8,405 (2,6); 8,391 (2,6); 8,318 (0,4); 8,305 (7,9); 8,294 (5,3); 8,283 (7,9); 8,272 (7,1); 8,258 (1,9); 8,250 (1,7); 8,244 (1,6); 7,907 (7,6); 7,885 (7,0); 7,680 (2,3); 7,654 (3,0); 7,631 (2,1); 6,458 (0,4); 6,436 (1,5); 6,414 (2,2); 6,392 (1,6); 6,370 (0,5); 4,057 (0,4); 4,039 (1,1); 4,022 (1,1); 4,004 (0,4); 3,329 (78,2); 2,850 (16,0); 2,839 (15,8); 2,678 (0,5); 2,673 (0,6); 2,669 (0,5); 2,526 (1,6); 2,513 (35,3); 2,509 (67,4); 2,504 (85,6); 2,500δ = 10.154 (3.8); 10.129 (3.9); 8,883 (5.1); 8,861 (5,6); 8.647 (1.1); 8.637 (3.0); 8.625 (3.0); 8.614 (1.0); 8.405 (2.6); 8.391 (2.6); 8.318 (0.4); 8,305 (7.9); 8.294 (5.3); 8,283 (7.9); 8,272 (7.1); 8,258 (1.9); 8,250 (1.7); 8,244 (1.6); 7.907 (7.6); 7,885 (7.0); 7.680 (2.3); 7.654 (3.0); 7,631 (2.1); 6.458 (0.4); 6,436 (1.5); 6.414 (2.2); 6,392 (1.6); 6,370 (0.5); 4.057 (0.4); 4.039 (1.1); 4.022 (1.1); 4.004 (0.4); 3,329 (78.2); 2,850 (16.0); 2,839 (15,8); 2,678 (0.5); 2,673 (0.6); 2,669 (0.5); 2,526 (1.6); 2,513 (35.3); 2,509 (67.4); 2,504 (85.6); 2,500
(61,6); 2,336 (0,4); 2,331 (0,5); 2,327 (0,4); 1,991 (4,8); 1,194(1,3); 1,176 (2,5); 1,158 (1,2); 0,000 (1,9) (61.6); 2.336 (0.4); 2.331 (0.5); 2,327 (0.4); 1,991 (4,8); 1,194 (1.3); 1.176 (2.5); 1.158 (1.2); 0,000 (1,9)
Beispiel 1-1-46: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-46: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,160 (3,7); 10,135 (3,9); 9,210 (3,9); 9,190 (4,0); 8,885 (5,1); 8,863 (5,6); 8,407 (2,6); 8,392 (2,5); 8,311 (7,9); 8,306 (5,6); 8,289 (7,6); 8,284 (6,7); 8,269 (1,6); 8,261 (1,8); 8,247 (1,6); 7,886 (7,2); 7,864 (6,6); 7,681 (2,3); 7,656 (3,0); 7,633 (2,1); 6,458 (0,4); 6,437 (1,5); 6,415 (2,1); 6,392 (1,6); 6,371 (0,5); 4,901 (0,4); 4,896 (0,4); 4,884 (1,4); 4,879 (1,6); 4,865 (2,0); 4,861 (2,1); 4,847 (1,6); 4,842 (1,4); 4,829 (0,4); 4,824 (0,4); 4,057 (0,3); 4,039 (1,0); 4,021 (1,0); 4,003 (0,3); 3,327 (82,1); 3,273 (6,7); 3,267 (6,7); 2,678 (0,5); 2,673 (0,7); 2,669 (0,5); 2,508 (80,5); 2,504 (104,6); 2,500 (76,5); 2,335 (0,5); 2,330 (0,7); 2,327 (0,5); 1,990 (4,2); 1,443 (16,0); 1,425 (15,9); 1,194 (1,1); 1,176 (2,2); 1,158 (1,1);δ = 10.160 (3.7); 10.135 (3.9); 9.210 (3.9); 9.190 (4.0); 8,885 (5.1); 8,863 (5,6); 8.407 (2.6); 8,392 (2.5); 8,311 (7.9); 8,306 (5.6); 8,289 (7,6); 8,284 (6,7); 8.269 (1.6); 8.261 (1.8); 8.247 (1.6); 7,886 (7.2); 7,864 (6.6); 7.681 (2.3); 7.656 (3.0); 7.633 (2.1); 6.458 (0.4); 6.437 (1.5); 6,415 (2,1); 6,392 (1.6); 6,371 (0.5); 4.901 (0.4); 4,896 (0.4); 4,884 (1.4); 4,879 (1.6); 4.865 (2.0); 4,861 (2,1); 4,847 (1.6); 4,842 (1.4); 4,829 (0.4); 4,824 (0.4); 4.057 (0.3); 4,039 (1.0); 4,021 (1.0); 4.003 (0.3); 3,327 (82,1); 3,273 (6.7); 3,267 (6,7); 2,678 (0.5); 2,673 (0.7); 2,669 (0.5); 2,508 (80.5); 2,504 (104.6); 2,500 (76.5); 2.335 (0.5); 2,330 (0.7); 2,327 (0.5); 1,990 (4.2); 1,443 (16.0); 1.425 (15.9); 1,194 (1,1); 1.176 (2.2); 1.158 (1.1);
0,000 (2,0) 0,000 (2.0)
Beispiel 1-1-47: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-47: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,159 (4,0); 10,135 (4,1); 8,881 (5,2); 8,859 (5,6); 8,646 (3,8); 8,625 (3,9); 8,409 (2,8); 8,395 (2,8); 8,317 (0,8); 8,309 (8,2); 8,301 (5,6); 8,287 (8,4); 8,279 (7,4); 8,263 (2,1);δ = 10.159 (4.0); 10,135 (4,1); 8,881 (5.2); 8,859 (5,6); 8,646 (3.8); 8.625 (3.9); 8,409 (2.8); 8,395 (2.8); 8.317 (0.8); 8,309 (8.2); 8,301 (5.6); 8,287 (8.4); 8,279 (7.4); 8,263 (2,1);
8.255 (1,8); 8,250 (1,8); 7,870 (7,4); 7,848 (6,9); 7,681 (2,4); 7,656 (3,2); 7,633 (2,2); 6,458 (0,4); 6,436 (1,6); 6,414 (2,3); 6,391 (1,7); 6,369 (0,5); 4,057 (0,7); 4,039 (2,1); 4,021 8,255 (1.8); 8,250 (1.8); 7,870 (7.4); 7,848 (6.9); 7.681 (2.4); 7.656 (3.2); 7.633 (2.2); 6.458 (0.4); 6,436 (1.6); 6,414 (2,3); 6.391 (1.7); 6,369 (0.5); 4.057 (0.7); 4,039 (2.1); 4,021
(2.1) ; 4,003 (0,7); 3,609 (1,2); 3,589 (2,3); 3,572 (2,4); 3,552 (1,3); 3,328 (80,8); 2,677 (0,5); 2,673 (0,7); 2,669 (0,5); 2,508 (78,8); 2,504 (101,0); 2,499 (74,6); 2,335 (0,5); 2,331 (0,7); 2,327 (0,5); 1,990 (8,8); 1,260 (16,0); 1,243 (15,9); 1,194 (2,5); 1,176 (4,8); 1,158 (2,4); 1,000 (0,3); 0,988 (0,8); 0,981 (1,2); 0,968 (2,2); 0,961 (1,5); 0,956 (1,6); 0,948 (2,3); 0,936 (1,4); 0,928 (1,1); 0,916 (0,5); 0,516 (0,5); 0,503 (0,8); 0,495 (1,8); 0,487 (1,7); 0,482 (2,1); 0,473 (2,6); 0,461 (1,5); 0,452 (2,2); 0,442 (1,7); 0,429 (1,9); 0,422 (2,2); 0,409(2.1); 4.003 (0.7); 3,609 (1.2); 3,589 (2,3); 3,572 (2,4); 3,552 (1.3); 3,328 (80.8); 2,677 (0.5); 2,673 (0.7); 2,669 (0.5); 2,508 (78.8); 2,504 (101.0); 2,499 (74.6); 2.335 (0.5); 2.331 (0.7); 2,327 (0.5); 1,990 (8.8); 1,260 (16,0); 1,243 (15.9); 1.194 (2.5); 1.176 (4.8); 1.158 (2.4); 1,000 (0.3); 0.988 (0.8); 0.981 (1.2); 0.968 (2.2); 0.961 (1.5); 0.956 (1.6); 0.948 (2.3); 0.936 (1.4); 0.928 (1.1); 0.916 (0.5); 0.516 (0.5); 0.503 (0.8); 0.495 (1.8); 0.487 (1.7); 0.482 (2.1); 0.473 (2.6); 0.461 (1.5); 0.452 (2.2); 0.442 (1.7); 0.429 (1.9); 0.422 (2.2); 0.409
(2,6); 0,398 (2,2); 0,389 (2,9); 0,376 (2,8); 0,366 (2,0); 0,353 (0,8); 0,326 (1,2); 0,313 (2,1); 0,304 (2,6); 0,291 (2,2); 0,281 (1,3); 0,268 (0,6); 0,000 (2,1) (2,6); 0.398 (2.2); 0.389 (2.9); 0.376 (2.8); 0.366 (2.0); 0.353 (0.8); 0.326 (1.2); 0.313 (2.1); 0.304 (2.6); 0.291 (2.2); 0.281 (1.3); 0.268 (0.6); 0,000 (2,1)
Beispiel 1-1-48: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-48: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,163 (1,3); 10,139 (1,3); 8,882 (1,7); 8,860 (1,8); 8,693 (1,2); 8,673 (1,2); 8,407 (0,9); 8,392 (0,9); 8,308 (3,3); 8,289 (2,2); 8,286 (3,2); 8,260 (0,6); 7,893 (2,4); 7,871 (2,3); 7,680 (0,7); 7,655 (1,0); 7,632 (0,7); 6,435 (0,5); 6,413 (0,8); 6,391 (0,6); 4,210 (0,6); 4,191 (0,7); 4,174 (0,6); 4,056 (0,3); 4,038 (1,1); 4,021 (1,1); 4,003 (0,4); 3,326 (43,1); 2,729 (0,6); 2,712 (0,6); 2,696 (1,2); 2,678 (1,3); 2,668 (0,3); 2,642 (1,0); 2,625 (1,0); 2,609 (0,5); 2,592 (0,5); 2,525 (1,0); 2,512 (22,3); 2,507 (44,2); 2,503 (57,6); 2,498 (42,3); 2,494δ = 10.163 (1.3); 10.139 (1.3); 8,882 (1.7); 8.860 (1.8); 8,693 (1.2); 8,673 (1.2); 8,407 (0.9); 8,392 (0.9); 8,308 (3.3); 8,289 (2,2); 8,286 (3,2); 8.260 (0.6); 7,893 (2,4); 7.871 (2.3); 7,680 (0.7); 7.655 (1.0); 7.632 (0.7); 6,435 (0.5); 6,413 (0.8); 6,391 (0.6); 4,210 (0.6); 4.191 (0.7); 4.174 (0.6); 4.056 (0.3); 4.038 (1.1); 4.021 (1.1); 4.003 (0.4); 3,326 (43.1); 2,729 (0.6); 2,712 (0.6); 2,696 (1.2); 2,678 (1.3); 2,668 (0.3); 2,642 (1.0); 2,625 (1.0); 2.609 (0.5); 2,592 (0.5); 2,525 (1.0); 2,512 (22.3); 2,507 (44.2); 2,503 (57.6); 2,498 (42.3); 2,494
(20,9); 2,330 (0,4); 2,144 (16,0); 2,117 (1,4); 1,990 (4,5); 1,300 (0,6); 1,283 (0,7); 1,273 (5,2); 1,256 (5,1); 1,193(1,3); 1,176 (2,5); 1,158 (1,2); 0,000 (1,2) (20.9); 2,330 (0.4); 2,144 (16,0); 2,117 (1.4); 1,990 (4.5); 1,300 (0.6); 1.283 (0.7); 1,273 (5.2); 1.256 (5.1); 1.193 (1.3); 1.176 (2.5); 1.158 (1.2); 0,000 (1.2)
Beispiel 1-1-49: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-49: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,158 (3,2); 10,134 (3,2); 8,882 (4,1); 8,860 (4,4); 8,704 (1,8); 8,691 (3,3); 8,677 (1,7); 8,407 (2,5); 8,393 (2,4); 8,308 (6,2); 8,298 (4,7); 8,286 (6,4); 8,276 (6,1); 8,261 (2,0); 7,894 (5,6); 7,872 (5,2); 7,680 (1 ,9); 7,655 (2,7); 7,632 (1 ,8); 6,458 (0,4); 6,437 (1 ,3); 6,414 (2,0); 6,392 (1 ,4); 6,370 (0,4); 5,758 (1 ,0); 4,057 (0,5); 4,039 (1 ,3); 4,022 (1 ,4); 4,004 (0,5); 3,330 (54,3); 3,299 (2,5); 3,282 (5,3); 3,267 (5,3); 3,251 (2,3); 2,674 (0,4); 2,509 (53,0); 2,505 (65,5); 2,500 (50,5); 2,331 (0,4); 1,991 (5,6); 1,624 (0,6); 1,606 (2,7); 1,588δ = 10.158 (3.2); 10.134 (3.2); 8,882 (4,1); 8,860 (4.4); 8,704 (1.8); 8,691 (3.3); 8.677 (1.7); 8,407 (2.5); 8.393 (2.4); 8,308 (6.2); 8,298 (4,7); 8,286 (6.4); 8,276 (6,1); 8.261 (2.0); 7,894 (5.6); 7,872 (5.2); 7,680 (1, 9); 7.655 (2.7); 7,632 (1, 8); 6.458 (0.4); 6,437 (1, 3); 6.414 (2.0); 6,392 (1, 4); 6,370 (0.4); 5,758 (1, 0); 4.057 (0.5); 4.039 (1, 3); 4.022 (1, 4); 4.004 (0.5); 3,330 (54.3); 3,299 (2.5); 3,282 (5.3); 3,267 (5.3); 3.251 (2.3); 2,674 (0.4); 2,509 (53.0); 2,505 (65.5); 2,500 (50.5); 2,331 (0.4); 1,991 (5.6); 1,624 (0.6); 1.666 (2.7); 1,588
(5.2) ; 1,570 (5,3); 1,552 (2,8); 1,534 (0,7); 1,194 (1,6); 1,176 (3,0); 1,159 (1,5); 0,981 (8,1); 0,962 (16,0); 0,944 (7,2); 0,925 (0,3); 0,000 (54,3) (5.2); 1,570 (5.3); 1,552 (2.8); 1,534 (0.7); 1,194 (1.6); 1.176 (3.0); 1.159 (1.5); 0.981 (8.1); 0.962 (16.0); 0.944 (7.2); 0.925 (0.3); 0,000 (54.3)
Beispiel 1-1-50: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-50: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,171 (3,5); 10,146 (3,6); 9,562 (3,9); 9,544 (4,0); 8,905 (4,7); 8,883 (5,2); 8,406 (2,4); 8,390 (2,4); 8,347 (0,4); 8,337 (4,8); 8,326 (7,8); 8,315 (5,6); 8,304 (7,4); 8,274 (1,4); 8,268 (1,5); 8,260 (1,7); 8,252 (1,5); 8,247 (1,5); 7,950 (7,4); 7,928 (6,8); 7,681 (2,2); 7,655 (2,8); 7,633 (2,0); 6,461 (0,4); 6,439 (1,4); 6,417 (2,0); 6,394 (1,5); 6,373 (0,4); 5,757 (0,4); 5,102 (0,6); 5,084 (2,7); 5,066 (4,2); 5,048 (2,8); 5,030 (0,6); 4,057 (0,6); 4,039 (1,8); 4,021 (1,8); 4,003 (0,6); 3,329 (186,1); 2,677 (0,7); 2,673 (1,0); 2,668 (0,7); 2,526 (3,1); 2,512 (54,4); 2,508 (106,6); 2,504 (138,6); 2,499 (100,2); 2,495 (48,4); 2,335 (0,6); 2,330 (0,8); 2,326 (0,6); 1,990 (7,9); 1,566 (16,0); 1,548 (15,8); 1,243 (0,4); 1,233 (0,5); 1,225δ = 10.171 (3.5); 10.146 (3.6); 9.562 (3.9); 9.544 (4.0); 8,905 (4,7); 8,883 (5.2); 8,406 (2,4); 8.390 (2.4); 8.377 (0.4); 8,337 (4,8); 8,326 (7,8); 8.315 (5.6); 8,304 (7.4); 8.274 (1.4); 8.268 (1.5); 8.260 (1.7); 8.252 (1.5); 8.247 (1.5); 7.950 (7.4); 7.928 (6.8); 7.681 (2.2); 7.655 (2.8); 7.633 (2.0); 6,461 (0.4); 6,439 (1.4); 6.417 (2.0); 6,394 (1.5); 6,373 (0.4); 5,757 (0.4); 5.102 (0.6); 5,084 (2.7); 5,066 (4.2); 5,048 (2.8); 5,030 (0.6); 4.057 (0.6); 4,039 (1.8); 4,021 (1.8); 4.003 (0.6); 3,329 (186,1); 2,677 (0.7); 2,673 (1.0); 2,668 (0.7); 2,526 (3,1); 2,512 (54.4); 2,508 (106.6); 2,504 (138.6); 2,499 (100.2); 2,495 (48.4); 2.335 (0.6); 2,330 (0.8); 2,326 (0.6); 1,990 (7.9); 1,566 (16.0); 1,548 (15.8); 1,243 (0.4); 1,233 (0.5); 1,225
(0,5); 1,194 (2,1); 1,176 (4,2); 1,158 (2,1); 0,146 (0,7); 0,008 (6,7); 0,000 (159,3); -0,009 (6,1); -0,150 (0,7) (0.5); 1,194 (2,1); 1.176 (4.2); 1,158 (2,1); 0.146 (0.7); 0.008 (6.7); 0.000 (159.3); -0.009 (6.1); -0.150 (0.7)
Beispiel 1-1-51: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-51: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,199 (3,7); 10,174 (3,8); 9,563 (4,1); 9,545 (4,2); 8,907 (4,8); 8,905 (4,7); 8,885 (5,2); 8,883 (5,3); 8,434 (4,8); 8,335 (4,7); 8,324 (8,0); 8,314 (5,4); 8,302 (7,7); 8,199 (2,3); 8,195 (2,3); 8,178 (2,6); 8,174 (2,6); 7,951 (7,9); 7,929 (7,3); 7,884 (5,1); 7,863 (4,5); 6,480 (0,4); 6,459 (1,4); 6,437 (2,0); 6,414 (1,5); 6,392 (0,4); 5,758 (1,5); 5,104 (0,6); 5,086 (2,8); 5,068 (4,4); 5,050 (2,8); 5,032 (0,6); 4,057 (0,9); 4,039 (2,8); 4,022 (2,9); 4,004 (1,0); 3,329 (89,2); 2,678 (0,4); 2,674 (0,6); 2,669 (0,4); 2,527 (1,4); 2,514 (32,7); 2,509 (65,9); 2,505 (86,3); 2,500 (61,5); 2,496 (28,9); 2,336 (0,4); 2,331 (0,6); 2,327 (0,4); 1,991 (12,7); 1,568 (16,0); 1,550 (15,9); 1,232 (0,4); 1,226 (0,4); 1,194 (3,4); 1,177 (6,7);δ = 10.199 (3.7); 10.174 (3.8); 9,563 (4,1); 9,545 (4.2); 8,907 (4,8); 8,905 (4,7); 8,885 (5.2); 8,883 (5.3); 8,434 (4,8); 8,335 (4,7); 8,324 (8.0); 8,314 (5.4); 8,302 (7.7); 8.199 (2.3); 8.195 (2.3); 8.178 (2.6); 8.174 (2.6); 7.951 (7.9); 7,929 (7.3); 7,884 (5.1); 7,863 (4,5); 6,480 (0.4); 6.459 (1.4); 6.437 (2.0); 6,414 (1.5); 6,392 (0.4); 5,758 (1.5); 5.104 (0.6); 5,086 (2.8); 5,068 (4.4); 5,050 (2.8); 5,032 (0.6); 4.057 (0.9); 4,039 (2.8); 4.022 (2.9); 4.004 (1.0); 3,329 (89.2); 2,678 (0.4); 2,674 (0.6); 2,669 (0.4); 2,527 (1.4); 2,514 (32,7); 2,509 (65.9); 2,505 (86.3); 2,500 (61.5); 2,496 (28.9); 2.336 (0.4); 2.331 (0.6); 2,327 (0.4); 1,991 (12.7); 1,568 (16,0); 1,550 (15.9); 1,232 (0.4); 1,226 (0.4); 1,194 (3,4); 1,177 (6.7);
1,159 (3,3); 0,146 (0,6); 0,008 (4,9); 0,000 (126,9); -0,009 (4,4); -0,150 (0,6) 1,159 (3.3); 0.146 (0.6); 0.008 (4.9); 0.000 (126.9); -0.009 (4.4); -0.150 (0.6)
Beispiel 1-1-52: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-52: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,100 (3,6); 10,075 (3,8); 9,566 (4,1); 9,548 (4,2); 8,947 (0,5); 8,907 (5,0); 8,885 (5,4); 8,351 (4,9); 8,329 (12,7); 8,317 (0,8); 8,307 (7,1); 8,240 (9,5); 8,224 (9,5); 8,153 (0,5); 8,080 (0,4); 7,953 (7,1); 7,931 (6,6); 7,002 (0,5); 6,390 (0,4); 6,369 (1,4); 6,347 (2,1); 6,324 (1,5); 6,303 (0,5); 5,757 (4,2); 5,103 (0,6); 5,086 (2,7); 5,068 (4,2); 5,050 (2,7); 5,032 (0,6); 3,748 (1,2); 3,328 (103,5); 2,677 (0,6); 2,673 (0,8); 2,668 (0,6); 2,508 (92,4); 2,504 (118,5); 2,499 (87,1); 2,335 (0,6); 2,330 (0,8); 2,326 (0,6); 1,990 (1,1); 1,568 (16,0);δ = 10,100 (3.6); 10.075 (3.8); 9,566 (4,1); 9,548 (4.2); 8.947 (0.5); 8,907 (5.0); 8,885 (5.4); 8.351 (4.9); 8,329 (12,7); 8.317 (0.8); 8,307 (7.1); 8.240 (9.5); 8.224 (9.5); 8,153 (0.5); 8,080 (0.4); 7,953 (7.1); 7.931 (6.6); 7.002 (0.5); 6,390 (0.4); 6.369 (1.4); 6,347 (2,1); 6,324 (1.5); 6,303 (0.5); 5,757 (4,2); 5.103 (0.6); 5,086 (2.7); 5,068 (4.2); 5,050 (2.7); 5,032 (0.6); 3.748 (1.2); 3,328 (103.5); 2,677 (0.6); 2,673 (0.8); 2,668 (0.6); 2,508 (92.4); 2,504 (118.5); 2,499 (87.1); 2.335 (0.6); 2,330 (0.8); 2,326 (0.6); 1,990 (1.1); 1,568 (16,0);
1,550 (15,8); 1,377 (0,4); 1,243 (0,4); 1,232 (0,6); 1,227 (0,6); 1,194 (0,4); 1,176 (0,6); 0,146 (0,7); 0,007 (8,5); 0,000 (148,6); -0,008 (7,0); -0,150 (0,7) 1,550 (15.8); 1.377 (0.4); 1,243 (0.4); 1,232 (0.6); 1,227 (0.6); 1,194 (0.4); 1.176 (0.6); 0.146 (0.7); 0.007 (8.5); 0.000 (148.6); -0.008 (7.0); -0.150 (0.7)
Beispiel 1-1-53: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-53: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,205 (3,5); 10,181 (3,6); 9,571 (3,9); 9,552 (4,0); 8,925 (4,6); 8,924 (4,6); 8,903 (5,1); 8,902 (5,2); 8,513 (1,9); 8,494 (3,4); 8,475 (1,9); 8,349 (8,2); 8,343 (4,8); 8,341 (4,7); 8,326 (8,0); 8,321 (5,3); 8,320 (5,3); 7,957 (7,9); 7,935 (7,4); 6,491 (0,4); 6,470 (1,3); 6,449 (1,8); 6,426 (1,4); 6,404 (0,5); 5,758 (1,1); 5,104 (0,5); 5,086 (2,3); 5,068 (3,6); 5,050δ = 10.205 (3.5); 10.181 (3.6); 9,571 (3.9); 9,552 (4.0); 8,925 (4,6); 8,924 (4,6); 8,903 (5.1); 8,902 (5.2); 8,513 (1.9); 8.494 (3,4); 8.475 (1.9); 8,349 (8.2); 8,343 (4,8); 8,341 (4,7); 8,326 (8.0); 8,321 (5,3); 8,320 (5.3); 7,957 (7.9); 7.935 (7.4); 6.491 (0.4); 6,470 (1.3); 6.449 (1.8); 6,426 (1.4); 6,404 (0.5); 5.758 (1.1); 5.104 (0.5); 5,086 (2.3); 5,068 (3.6); 5,050
(2.3) ; 5,032 (0,5); 4,057 (0,5); 4,039 (1,6); 4,021 (1,6); 4,004 (0,5); 3,327 (48,1); 2,678 (0,4); 2,673 (0,5); 2,669 (0,4); 2,527 (1,5); 2,513 (29,3); 2,509 (58,3); 2,504 (76,3); 2,500 (54,3); 2,495 (25,4); 2,336 (0,4); 2,331 (0,5); 2,326 (0,3); 1,990 (7,0); 1,568 (16,0); 1,550 (15,8); 1,194 (1,9); 1,177 (3,7); 1,159 (1,8); 0,146 (0,5); 0,017 (0,5); 0,008 (4,8); 0,000(2.3); 5,032 (0.5); 4.057 (0.5); 4,039 (1.6); 4,021 (1.6); 4.004 (0.5); 3,327 (48.1); 2,678 (0.4); 2,673 (0.5); 2,669 (0.4); 2,527 (1.5); 2,513 (29.3); 2,509 (58.3); 2,504 (76.3); 2,500 (54.3); 2,495 (25.4); 2.336 (0.4); 2.331 (0.5); 2,326 (0.3); 1,990 (7.0); 1,568 (16,0); 1,550 (15.8); 1,194 (1.9); 1,177 (3.7); 1,159 (1.8); 0.146 (0.5); 0.017 (0.5); 0.008 (4.8); 0,000
(127,2); -0,009 (4,4); -0,150 (0,5) (127.2); -0.009 (4.4); -0.150 (0.5)
Beispiel 1-1-54: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-54: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,156 (2,0); 10,131 (2,1); 8,839 (2,6); 8,817 (3,0); 8,563 (1,9); 8,544 (2,0); 8,409 (1,4); 8,393 (1,4); 8,324 (2,7); 8,304 (5,7); 8,282 (4,1); 8,272 (0,9); 8,264 (1,0); 8,256 (0,9); 8,251 (0,9); 7,846 (3,6); 7,824 (3,3); 7,682 (1,2); 7,656 (1,6); 7,633 (1,1); 6,437 (0,8); 6,415 (1,1); 6,392 (0,8); 4,145 (0,7); 4,128 (1,1); 4,110 (1,1); 4,093 (0,7); 4,039 (0,4); 4,021δ = 10.156 (2.0); 10,131 (2,1); 8.839 (2.6); 8,817 (3.0); 8,563 (1.9); 8,544 (2.0); 8,409 (1.4); 8,393 (1.4); 8,324 (2.7); 8,304 (5.7); 8,282 (4,1); 8,272 (0.9); 8.264 (1.0); 8.256 (0.9); 8.251 (0.9); 7,846 (3.6); 7,824 (3.3); 7,682 (1.2); 7.656 (1.6); 7.633 (1.1); 6.437 (0.8); 6.415 (1.1); 6,392 (0.8); 4,145 (0.7); 4,128 (1,1); 4.110 (1.1); 4,093 (0.7); 4,039 (0.4); 4,021
(0,4); 3,330 (28,3); 2,508 (36,8); 2,504 (48,0); 2,500 (37,1); 1,991 (1,6); 1,213 (16,0); 1,196 (16,0); 1,176 (1,1); 1,158 (0,5); 1,115 (1,6); 1,099 (1,5); 0,000 (0,4) (0.4); 3,330 (28.3); 2,508 (36,8); 2,504 (48.0); 2,500 (37.1); 1,991 (1.6); 1,213 (16,0); 1,196 (16.0); 1.176 (1.1); 1.158 (0.5); 1,115 (1.6); 1.099 (1.5); 0,000 (0.4)
Beispiel 1-1-55: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-55:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,155 (2,8); 10,130 (2,8); 8,843 (3,7); 8,821 (4,3); 8,676 (1,3); 8,663 (2,7); 8,649 (1,3); 8,407 (1,8); 8,391 (1,8); 8,326 (3,9); 8,304 (10,5); 8,282 (6,8); 8,270 (1,1); 8,261 (1,3); 8,254 (1,1); 8,248 (1,1); 7,862 (6,0); 7,841 (5,7); 7,681 (1,7); 7,656 (2,2); 7,633 (1,6); 6,437 (1,0); 6,415 (1,5); 6,392 (1,1); 6,370 (0,3); 5,759 (0,9); 3,367 (1,0); 3,349 (3,3); 3,330 (45,2); 3,317 (3,5); 3,299 (1,0); 3,088 (0,5); 2,678 (0,4); 2,673 (0,5); 2,669 (0,4); 2,527 (1,3); 2,522 (2,0); 2,513 (28,1); 2,509 (58,2); 2,504 (78,0); 2,500 (57,5); 2,495 (28,4); 2,336δ = 10.155 (2.8); 10.130 (2.8); 8,843 (3.7); 8,821 (4.3); 8.676 (1.3); 8,663 (2.7); 8.649 (1.3); 8.407 (1.8); 8.391 (1.8); 8,326 (3.9); 8.304 (10.5); 8,282 (6,8); 8.270 (1.1); 8.261 (1.3); 8.254 (1.1); 8.248 (1.1); 7,862 (6.0); 7,841 (5.7); 7.681 (1.7); 7.656 (2.2); 7.633 (1.6); 6.437 (1.0); 6,415 (1.5); 6,392 (1,1); 6,370 (0.3); 5,759 (0.9); 3.367 (1.0); 3,349 (3.3); 3,330 (45.2); 3,317 (3.5); 3,299 (1.0); 3.088 (0.5); 2,678 (0.4); 2,673 (0.5); 2,669 (0.4); 2,527 (1,3); 2,522 (2.0); 2,513 (28.1); 2,509 (58.2); 2,504 (78.0); 2,500 (57.5); 2,495 (28.4); 2,336
(0,4); 2,331 (0,5); 2,327 (0,4); 2,088 (4,0); 1,991 (0,6); 1,195 (7,6); 1,176 (16,0); 1,158 (7,3); 1,142 (0,4); 0,000 (0,8) (0.4); 2.331 (0.5); 2,327 (0.4); 2,088 (4.0); 1,991 (0.6); 1,195 (7.6); 1.176 (16.0); 1,158 (7.3); 1,142 (0.4); 0,000 (0.8)
Beispiel 1-1-56: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-56:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,159 (3,9); 10,135 (4,0); 8,843 (5,3); 8,821 (6,0); 8,631 (3,7); 8,610 (3,8); 8,410 (2,6); 8,394 (2,6); 8,334 (5,4); 8,312 (6,3); 8,307 (8,8); 8,285 (9,5); 8,274 (1,6); 8,265 (1,8); 8,259 (1,6); 8,253 (1,6); 7,835 (8,1); 7,814 (7,7); 7,682 (2,4); 7,657 (3,1); 7,634 (2,2); 6,459 (0,4); 6,438 (1,5); 6,415 (2,2); 6,393 (1,6); 6,371 (0,5); 4,057 (0,4); 4,039 (1,1); 4,021 (1,1); 4,004 (0,4); 3,587 (1,2); 3,568 (2,3); 3,551 (2,3); 3,531 (1,2); 3,329 (37,6); 2,678 (0,4); 2,673 (0,6); 2,669 (0,5); 2,526 (1,5); 2,513 (35,0); 2,509 (72,1); 2,504 (96,1); 2,500δ = 10.159 (3.9); 10.135 (4.0); 8,843 (5.3); 8,821 (6.0); 8,631 (3.7); 8,610 (3.8); 8.410 (2.6); 8.394 (2.6); 8,334 (5.4); 8,312 (6.3); 8,307 (8.8); 8,285 (9.5); 8.274 (1.6); 8.265 (1.8); 8.259 (1.6); 8,253 (1.6); 7,835 (8,1); 7,814 (7,7); 7,682 (2,4); 7,657 (3,1); 7.634 (2.2); 6,459 (0.4); 6.438 (1.5); 6.415 (2.2); 6,393 (1.6); 6,371 (0.5); 4.057 (0.4); 4.039 (1.1); 4.021 (1.1); 4.004 (0.4); 3,587 (1.2); 3.568 (2.3); 3.551 (2.3); 3.531 (1.2); 3,329 (37.6); 2,678 (0.4); 2,673 (0.6); 2,669 (0.5); 2.526 (1.5); 2,513 (35.0); 2,509 (72.1); 2,504 (96.1); 2,500
(70.4) ; 2,495 (34,4); 2,335 (0,4); 2,331 (0,6); 2,326 (0,4); 2,088 (0,7); 1,991 (4,9); 1,265 (16,0); 1,249 (15,8); 1,194 (1,3); 1,176 (2,6); 1,159 (1,3); 1,001 (0,3); 0,988 (0,8); 0,980 (1,1); 0,968 (2,1); 0,960 (1,3); 0,956 (1,5); 0,948 (2,2); 0,941 (0,7); 0,935 (1,3); 0,928 (0,9); 0,915 (0,5); 0,517 (0,4); 0,508 (0,6); 0,503 (0,7); 0,495 (1,6); 0,488 (1,4); 0,482 (1,9); 0,474 (2,5); 0,461 (2,3); 0,452 (2,4); 0,438 (1,9); 0,431 (2,1); 0,427 (2,1); 0,417 (2,6); 0,412 (2,3); 0,403 (2,2); 0,396 (1,9); 0,390 (2,7); 0,380 (1,7); 0,366 (0,7); 0,332 (1,0); 0,319(70.4); 2,495 (34.4); 2.335 (0.4); 2.331 (0.6); 2,326 (0.4); 2.088 (0.7); 1,991 (4.9); 1,265 (16.0); 1,249 (15.8); 1,194 (1.3); 1.176 (2.6); 1,159 (1.3); 1,001 (0.3); 0.988 (0.8); 0.980 (1.1); 0.968 (2.1); 0.960 (1.3); 0.956 (1.5); 0.948 (2.2); 0.941 (0.7); 0.935 (1.3); 0.928 (0.9); 0.915 (0.5); 0.517 (0.4); 0.508 (0.6); 0.503 (0.7); 0.495 (1.6); 0.488 (1.4); 0.482 (1.9); 0.474 (2.5); 0.461 (2.3); 0.452 (2.4); 0.438 (1.9); 0.431 (2.1); 0.427 (2.1); 0.417 (2.6); 0.412 (2.3); 0.403 (2.2); 0.396 (1.9); 0.390 (2.7); 0.380 (1.7); 0.366 (0.7); 0.332 (1.0); 0.319
(1,7); 0,310 (2,3); 0,298 (2,0); 0,288 (1,2); 0,276 (0,5); 0,146 (0,8); 0,008 (5,4); 0,000 (155,2); -0,009 (5,9); -0,150 (0,8) (1.7); 0.310 (2.3); 0.298 (2.0); 0.288 (1.2); 0.276 (0.5); 0.146 (0.8); 0.008 (5.4); 0.000 (155.2); -0.009 (5.9); -0.150 (0.8)
Beispiel 1-1-57: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-57: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,176 (3,7); 10,151 (3,8); 9,546 (4,2); 9,528 (4,3); 8,863 (5,0); 8,841 (5,6); 8,411 (2,7); 8,396 (2,7); 8,371 (5,1); 8,349 (5,7); 8,326 (7,2); 8,304 (7,0); 8,279 (1,5); 8,273 (1,7); 8,265 (1,9); 8,258 (1,7); 8,252 (1,7); 7,916 (7,0); 7,895 (6,6); 7,684 (2,3); 7,658 (3,1); 7,635 (2,1); 6,464 (0,4); 6,443 (1,5); 6,421 (2,2); 6,398 (1,6); 6,377 (0,5); 5,105 (0,6); 5,087 (2,7); 5,069 (4,2); 5,051 (2,7); 5,034 (0,6); 4,057 (0,9); 4,040 (2,7); 4,022 (2,7); 4,004 (0,9); 3,337 (88,5); 2,675 (0,5); 2,671 (0,4); 2,510 (62,6); 2,506 (80,0); 2,501 (59,3); 2,337 (0,4); 2,333 (0,5); 2,328 (0,4); 1,992 (11,3); 1,570 (16,0); 1,552 (15,8); 1,351 (0,3); 1,338(1,6); 1,300 (0,3); 1,260 (0,5); 1,250 (2,0); 1,234 (0,7); 1,195 (3,1); 1,177 (6,0); 1,159δ = 10.176 (3.7); 10.151 (3.8); 9.546 (4.2); 9.528 (4.3); 8,863 (5.0); 8,841 (5.6); 8,411 (2.7); 8.396 (2.7); 8,371 (5.1); 8,349 (5.7); 8,326 (7.2); 8,304 (7.0); 8.279 (1.5); 8,273 (1.7); 8.265 (1.9); 8.258 (1.7); 8.252 (1.7); 7.916 (7.0); 7,895 (6.6); 7.684 (2.3); 7,658 (3,1); 7,635 (2.1); 6,464 (0.4); 6,443 (1.5); 6,421 (2,2); 6,398 (1.6); 6,377 (0.5); 5.105 (0.6); 5,087 (2.7); 5,069 (4.2); 5,051 (2.7); 5,034 (0.6); 4.057 (0.9); 4,040 (2.7); 4.022 (2.7); 4.004 (0.9); 3,337 (88.5); 2,675 (0.5); 2,671 (0.4); 2,510 (62.6); 2,506 (80.0); 2,501 (59,3); 2.377 (0.4); 2.333 (0.5); 2,328 (0.4); 1,992 (11.3); 1,570 (16.0); 1,552 (15.8); 1.351 (0.3); 1,338 (1.6); 1,300 (0.3); 1,260 (0.5); 1,250 (2.0); 1,234 (0.7); 1,195 (3,1); 1,177 (6.0); 1,159
(3.0) ; 0,000 (8,1); -0,008 (0,4) (3.0); 0,000 (8,1); -0.008 (0.4)
Beispiel 1-1-58: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-58:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,165 (5,3); 10,141 (5,5); 9,477 (5,5); 9,461 (5,6); 8,857 (7,2); 8,835 (8,0); 8,408 (3,6); 8,393 (3,5); 8,350 (7,4); 8,329 (8,4); 8,316 (11 ,0); 8,294 (10,6); 8,277 (2,0); 8,270δ = 10.165 (5.3); 10.141 (5.5); 9,477 (5.5); 9.461 (5.6); 8,857 (7.2); 8,835 (8.0); 8,408 (3.6); 8,393 (3.5); 8,350 (7.4); 8,329 (8.4); 8,316 (11, 0); 8.294 (10.6); 8.277 (2.0); 8,270
(2.1) ; 8,263 (2,5); 8,255 (2,2); 8,249 (2,1); 7,921 (10,8); 7,899 (10,1); 7,682 (3,2); 7,657 (4,2); 7,634 (3,1); 6,461 (0,5); 6,440 (2,1); 6,417 (3,0); 6,395 (2,2); 6,373 (0,7); 5,089 (0,4); 5,072 (1,7); 5,055 (3,6); 5,038 (4,0); 5,020 (2,3); 5,004 (0,7); 4,855 (8,1); 4,838 (12,9); 4,820 (7,6); 4,612 (8,4); 4,596 (16,0); 4,580 (7,5); 4,057 (0,7); 4,039 (2,2); 4,021 (2,2); 4,003 (0,8); 3,328 (87,2); 2,677 (0,9); 2,673 (1,2); 2,669 (0,9); 2,526 (3,0); 2,512 (69,5); 2,508 (140,7); 2,504 (186,5); 2,499 (137,3); 2,495 (68,2); 2,335 (0,9); 2,330 (1,2); 2,326(2.1); 8.263 (2.5); 8.255 (2.2); 8.249 (2.1); 7.921 (10.8); 7,899 (10.1); 7,682 (3,2); 7,657 (4,2); 7,634 (3,1); 6,461 (0.5); 6,440 (2,1); 6.417 (3.0); 6,395 (2.2); 6,373 (0.7); 5,089 (0.4); 5,072 (1.7); 5,055 (3.6); 5,038 (4.0); 5,020 (2,3); 5.004 (0.7); 4,855 (8,1); 4,838 (12.9); 4,820 (7.6); 4,612 (8.4); 4,596 (16,0); 4,580 (7.5); 4.057 (0.7); 4.039 (2.2); 4.021 (2.2); 4.003 (0.8); 3,328 (87.2); 2,677 (0.9); 2,673 (1.2); 2,669 (0.9); 2.526 (3.0); 2,512 (69.5); 2,508 (140.7); 2,504 (186.5); 2,499 (137.3); 2,495 (68.2); 2.335 (0.9); 2,330 (1.2); 2,326
(0,8); 1,990 (9,5); 1,234 (0,5); 1,194 (2,6); 1,176 (5,1); 1,158 (2,5); 1,142 (0,4); 0,146 (1,4); 0,030 (0,5); 0,008 (10,4); 0,000 (275,5); -0,009 (10,5); -0,150 (1,3) (0.8); 1,990 (9.5); 1.234 (0.5); 1.194 (2.6); 1.176 (5.1); 1.158 (2.5); 1,142 (0.4); 0.146 (1.4); 0.030 (0.5); 0.008 (10.4); 0,000 (275.5); -0.009 (10.5); -0.150 (1.3)
Beispiel 1-1-59: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-59:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,163 (8,4); 10,139 (8,7); 9,153 (4,2); 9,138 (8,9); 9,123 (4,2); 8,852 (11,2); 8,830 (12,5); 8,407 (5,7); 8,393 (5,6); 8,390 (5,6); 8,356 (11,5); 8,335 (12,8); 8,313 (16,0); 8,291δ = 10.163 (8.4); 10.139 (8.7); 9,153 (4,2); 9.138 (8.9); 9,123 (4,2); 8,852 (11,2); 8,830 (12.5); 8,407 (5.7); 8,393 (5.6); 8,390 (5.6); 8,356 (11.5); 8,335 (12.8); 8,313 (16,0); 8,291
(15.5) ; 8,281 (3,1); 8,276 (3,1); 8,269 (3,3); 8,261 (3,9); 8,254 (3,5); 8,248 (3,4); 7,888 (0,4); 7,876 (15,8); 7,854 (14,9); 7,682 (5,0); 7,656 (6,6); 7,633 (4,7); 6,460 (0,9); 6,439(15.5); 8,281 (3,1); 8,276 (3,1); 8.269 (3.3); 8,261 (3,9); 8.254 (3.5); 8.248 (3.4); 7,888 (0.4); 7.876 (15.8); 7,854 (14.9); 7,682 (5.0); 7.656 (6.6); 7.633 (4.7); 6,460 (0.9); 6,439
(3.2) ; 6,417 (4,7); 6,394 (3,5); 6,372 (1,0); 6,348 (1,5); 6,339 (2,9); 6,329 (1,4); 6,209 (3,0); 6,200 (6,3); 6,190 (3,0); 6,070 (1,4); 6,060 (3,1); 6,051 (1,6); 4,057 (0,6); 4,039 (1,7); 4,021 (1,7); 4,004 (0,6); 3,801 (2,3); 3,791 (2,9); 3,787 (2,8); 3,777 (2,6); 3,762 (4,9); 3,752 (5,8); 3,747 (5,8); 3,737 (4,8); 3,722 (2,6); 3,712 (2,8); 3,707 (3,0); 3,698 (2,3); 3,334 (128,7); 3,330 (117,9); 2,678 (1,1); 2,673 (1,5); 2,669 (1,2); 2,526 (4,2); 2,509 (168,9); 2,504 (224,3); 2,500 (169,9); 2,335 (1,0); 2,331 (1,4); 2,327 (1,1); 1,991 (7,2); 1,362 (0,4);(3.2); 6,417 (4,7); 6,394 (3.5); 6,372 (1.0); 6.348 (1.5); 6,339 (2.9); 6,329 (1.4); 6.209 (3.0); 6,200 (6.3); 6.190 (3.0); 6.070 (1.4); 6.060 (3.1); 6.051 (1.6); 4.057 (0.6); 4,039 (1.7); 4,021 (1.7); 4.004 (0.6); 3.801 (2.3); 3,791 (2.9); 3,787 (2.8); 3,777 (2.6); 3,762 (4.9); 3,752 (5.8); 3,747 (5.8); 3,737 (4,8); 3,722 (2.6); 3,712 (2.8); 3,707 (3.0); 3,698 (2.3); 3,334 (128,7); 3,330 (117.9); 2,678 (1,1); 2,673 (1.5); 2,669 (1.2); 2,526 (4,2); 2,509 (168,9); 2,504 (224.3); 2,500 (169.9); 2.335 (1.0); 2.331 (1.4); 2,327 (1,1); 1,991 (7.2); 1.362 (0.4);
1,338 (2,3); 1,286 (0,4); 1,226 (3,1); 1,194 (2,0); 1,176 (3,7); 1,158 (1,9); 0,000 (1,9) 1.338 (2.3); 1,286 (0.4); 1,226 (3,1); 1,194 (2.0); 1.176 (3.7); 1,158 (1.9); 0,000 (1,9)
Beispiel 1-1-60: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-60: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,157 (2,8); 10,133 (2,9); 8,843 (3,9); 8,821 (4,4); 8,681 (1,4); 8,667 (2,9); 8,653 (1,4); 8,408 (1,9); 8,391 (1,8); 8,328 (4,0); 8,319 (0,3); 8,305 (8,4); 8,282 (6,7); 8,270 (1,1); 8,261 (1,3); 8,254 (1,2); 8,248 (1,1); 7,858 (6,1); 7,836 (5,7); 7,681 (1,8); 7,655 (2,2); 7,633 (1,7); 6,437 (1,1); 6,415 (1,6); 6,392 (1,2); 6,370 (0,4); 4,039 (0,5); 4,021 (0,5); 3,329 δ = 10.157 (2.8); 10.133 (2.9); 8,843 (3.9); 8,821 (4.4); 8.681 (1.4); 8,667 (2.9); 8,653 (1.4); 8,408 (1.9); 8.391 (1.8); 8,328 (4.0); 8.319 (0.3); 8,305 (8.4); 8,282 (6,7); 8.270 (1.1); 8.261 (1.3); 8.254 (1.2); 8.248 (1.1); 7,858 (6.1); 7,836 (5.7); 7.681 (1.8); 7.655 (2.2); 7.633 (1.7); 6.437 (1.1); 6,415 (1.6); 6,392 (1.2); 6,370 (0.4); 4.039 (0.5); 4,021 (0.5); 3,329
(53,2); 3,292 (1,8); 3,275 (4,2); 3,260 (4,2); 3,243 (1,9); 2,678 (0,4); 2,673 (0,6); 2,669 (0,4); 2,526 (1,4); 2,513 (33,1); 2,509 (67,7); 2,504 (90,0); 2,499 (66,0); 2,495 (32,6); 2,335 (0,4); 2,331 (0,6); 2,326 (0,4); 2,088 (0,6); 1,991 (2,1); 1,630 (0,5); 1,612 (2,3); 1,594 (4,6); 1,576 (4,7); 1,558 (2,5); 1,540 (0,6); 1,194 (0,6); 1,176 (1,1); 1,158 (0,5); 0,986 (7,9);(53.2); 3,292 (1.8); 3,275 (4,2); 3,260 (4,2); 3,243 (1.9); 2,678 (0.4); 2,673 (0.6); 2,669 (0.4); 2,526 (1.4); 2,513 (33.1); 2,509 (67.7); 2,504 (90.0); 2,499 (66.0); 2,495 (32.6); 2.335 (0.4); 2.331 (0.6); 2,326 (0.4); 2.088 (0.6); 1,991 (2.1); 1,630 (0.5); 1,612 (2,3); 1,594 (4,6); 1,576 (4,7); 1,558 (2.5); 1,540 (0.6); 1,194 (0.6); 1.176 (1.1); 1.158 (0.5); 0.986 (7.9);
0,968 (16,0); 0,949 (7,0); 0,000 (0,9) 0.968 (16.0); 0.949 (7.0); 0,000 (0.9)
Beispiel 1-1-61: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-61:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,155 (7,5); 10,130 (7,9); 8,836 (9,0); 8,814 (10,1); 8,789 (0,5); 8,720 (8,2); 8,710 (8,6); 8,584 (0,4); 8,407 (6,5); 8,391 (6,5); 8,362 (0,8); 8,340 (1,0); 8,320 (9,4); 8,299 (16,0); 8,281 (13,9); 8,262 (5,2); 7,935 (0,4); 7,913 (0,4); 7,861 (10,8); 7,839 (10,4); 7,818 (0,6); 7,681 (4,5); 7,656 (7,1); 7,633 (4,3); 6,457 (0,9); 6,435 (3,3); 6,414 (4,9); 6,391δ = 10.155 (7.5); 10.130 (7.9); 8,836 (9.0); 8,814 (10.1); 8,789 (0.5); 8,720 (8,2); 8,710 (8.6); 8,584 (0.4); 8,407 (6.5); 8,391 (6.5); 8.362 (0.8); 8.340 (1.0); 8,320 (9.4); 8,299 (16.0); 8,281 (13.9); 8.262 (5.2); 7.935 (0.4); 7.913 (0.4); 7.861 (10.8); 7,839 (10.4); 7.818 (0.6); 7,681 (4,5); 7,656 (7.1); 7.633 (4.3); 6.457 (0.9); 6,435 (3.3); 6,414 (4,9); 6,391
(3.5) ; 6,369 (1,1); 4,058 (0,6); 4,041 (1,6); 4,023 (1,6); 4,005 (0,6); 3,332 (50,7); 3,090 (1,6); 2,913 (2,2); 2,904 (3,4); 2,895 (4,9); 2,885 (4,9); 2,877 (3,7); 2,868 (2,5); 2,818 (0,8); 2,805 (0,8); 2,675 (1,0); 2,506 (138,3); 2,333 (1,0); 1,992 (6,6); 1,232 (0,7); 1,214 (0,4); 1,195 (2,1); 1,177 (3,7); 1,160 (1,9); 0,810 (0,4); 0,774 (2,9); 0,756 (12,2); 0,743 (11,2); 0,739 (10,9); 0,727 (4,2); 0,706 (0,7); 0,688 (0,5); 0,654 (0,5); 0,644 (0,5); 0,614 (4,0); 0,596 (13,3); 0,590 (11,8); 0,577 (3,6); 0,485 (0,5); 0,356 (0,4); 0,344 (0,4); 0,000 (1,7) Beispiel 1-1-62: : 1H-NMR (400,0 MHz, d6-DMSO): (3.5); 6.369 (1.1); 4.058 (0.6); 4,041 (1.6); 4.023 (1.6); 4.005 (0.6); 3,332 (50,7); 3,090 (1.6); 2,913 (2,2); 2.904 (3.4); 2,895 (4.9); 2,885 (4.9); 2,877 (3.7); 2,868 (2.5); 2.818 (0.8); 2,805 (0.8); 2,675 (1.0); 2,506 (138.3); 2.333 (1.0); 1,992 (6.6); 1,232 (0.7); 1.214 (0.4); 1,195 (2.1); 1,177 (3.7); 1,160 (1.9); 0.810 (0.4); 0.774 (2.9); 0.756 (12.2); 0.743 (11.2); 0.739 (10.9); 0.727 (4.2); 0.706 (0.7); 0.688 (0.5); 0.654 (0.5); 0.644 (0.5); 0.614 (4.0); 0.596 (13.3); 0.590 (11.8); 0.577 (3.6); 0.485 (0.5); 0.356 (0.4); 0.344 (0.4); 0.000 (1.7) Example 1-1-62:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,160 (3,9); 10,136 (4,0); 9,188 (3,8); 9,168 (3,9); 8,846 (5,2); 8,824 (5,8); 8,409 (2,6); 8,394 (2,6); 8,339 (5,3); 8,318 (6,1); 8,310 (7,7); 8,288 (7,7); 8,271 (1,6); 8,264 (1,8); 8,256 (1 ,6); 8,250 (1 ,6); 7,851 (7,5); 7,830 (7,1); 7,682 (2,3); 7,657 (3,1); 7,634 (2,2); 6,460 (0,4); 6,439 (1 ,5); 6,417 (2,2); 6,394 (1 ,6); 6,372 (0,5); 4,901 (0,4); 4,896 (0,4); 4,884 (1,4); 4,878 (1,6); 4,864 (2,0); 4,860 (2,1); 4,847 (1,6); 4,841 (1,5); 4,829 (0,4); 4,823 (0,4); 4,039 (1,0); 4,022 (1,0); 4,004 (0,3); 3,331 (59,6); 3,272 (6,8); 3,267 (6,7); 2,678 (0,5); 2,674 (0,7); 2,669 (0,5); 2,527 (1,8); 2,513 (39,5); 2,509 (77,8); 2,505 (100,9); 2,500 (74,2); 2,336 (0,5); 2,332 (0,7); 2,327 (0,5); 1,991 (4,1); 1,449 (16,0); 1,432 (15,9); 1,221δ = 10.160 (3.9); 10.136 (4.0); 9.188 (3.8); 9.168 (3.9); 8,846 (5.2); 8,824 (5.8); 8,409 (2.6); 8.394 (2.6); 8,339 (5.3); 8,318 (6,1); 8.310 (7.7); 8,288 (7,7); 8.271 (1.6); 8,264 (1.8); 8,256 (1, 6); 8.250 (1, 6); 7.851 (7.5); 7,830 (7.1); 7.682 (2.3); 7,657 (3,1); 7.634 (2.2); 6,460 (0.4); 6,439 (1, 5); 6.417 (2.2); 6,394 (1, 6); 6,372 (0.5); 4.901 (0.4); 4,896 (0.4); 4,884 (1.4); 4,878 (1.6); 4,864 (2.0); 4,860 (2,1); 4,847 (1.6); 4,841 (1.5); 4,829 (0.4); 4,823 (0.4); 4,039 (1.0); 4.022 (1.0); 4.004 (0.3); 3,331 (59.6); 3,272 (6.8); 3,267 (6,7); 2,678 (0.5); 2,674 (0.7); 2,669 (0.5); 2,527 (1.8); 2,513 (39.5); 2,509 (77.8); 2,505 (100.9); 2,500 (74.2); 2.336 (0.5); 2.332 (0.7); 2,327 (0.5); 1,991 (4.1); 1,449 (16.0); 1,432 (15.9); 1,221
(0,5); 1,204 (0,5); 1,194(1,2); 1,176 (2,2); 1,159 (1,1); 0,000 (1,0) (0.5); 1.204 (0.5); 1,194 (1.2); 1.176 (2.2); 1.159 (1.1); 0,000 (1.0)
Beispiel 1-1-63: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-63:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,170 (1,2); 10,145 (1,2); 9,496 (0,6); 9,482 (1,4); 9,468 (0,6); 8,861 (1,6); 8,839 (1,8); 8,408 (0,8); 8,391 (0,8); 8,365 (1,6); 8,343 (1,8); 8,322 (2,4); 8,300 (2,4); 8,275 (0,4); 8,269 (0,5); 8,261 (0,5); 8,254 (0,5); 8,248 (0,5); 7,905 (2,4); 7,884 (2,3); 7,682 (0,7); 7,656 (0,9); 7,633 (0,7); 6,442 (0,4); 6,420 (0,7); 6,397 (0,5); 5,759 (1,2); 4,440 (3,1); 4,426 (3,1); 4,057 (1,2); 4,039 (3,7); 4,021 (3,7); 4,004 (1,3); 3,336 (44,3); 2,528 (0,5); 2,514 (11,7); 2,510 (23,8); 2,505 (31,5); 2,501 (23,1); 2,496 (11,4); 1,991 (16,0); 1,338 (1,2);δ = 10.170 (1.2); 10.145 (1.2); 9.496 (0.6); 9,482 (1.4); 9,468 (0.6); 8.861 (1.6); 8.839 (1.8); 8.408 (0.8); 8.391 (0.8); 8.365 (1.6); 8,343 (1.8); 8.322 (2.4); 8,300 (2,4); 8.275 (0.4); 8.269 (0.5); 8.261 (0.5); 8.254 (0.5); 8.248 (0.5); 7.905 (2.4); 7.884 (2.3); 7,682 (0.7); 7.656 (0.9); 7.633 (0.7); 6.442 (0.4); 6,420 (0.7); 6.397 (0.5); 5,759 (1.2); 4,440 (3,1); 4,426 (3,1); 4.057 (1.2); 4,039 (3.7); 4,021 (3.7); 4.004 (1.3); 3,336 (44.3); 2,528 (0.5); 2,514 (11,7); 2,510 (23.8); 2,505 (31.5); 2,501 (23.1); 2,496 (11.4); 1,991 (16.0); 1.338 (1.2);
1,250(1,4); 1,194(4,3); 1,177 (8,5); 1,159 (4,2); 0,000 (3,7) 1,250 (1.4); 1,194 (4.3); 1,177 (8.5); 1,159 (4,2); 0,000 (3,7)
Beispiel 1-1-64: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-64: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,176 (0,5); 10,143 (6,0); 10,118 (5,9); 9,779 (5,2); 9,238 (11,9); 8,966 (5,2); 8,897 (0,4); 8,884 (0,8); 8,869 (7,5); 8,847 (8,0); 8,400 (4,6); 8,386 (4,5); 8,316 (5,6); 8,297 (16,0); 8,275 (13,0); 8,264 (15,7); 8,243 (8,4); 8,154 (0,4); 7,956 (0,4); 7,934 (0,4); 7,922 (0,6); 7,900 (0,7); 7,680 (3,7); 7,655 (5,1); 7,632 (3,5); 6,457 (0,7); 6,436 (2,5); 6,414 (3,7); 6,391 (2,6); 6,359 (0,8); 5,757 (5,6); 4,838 (0,4); 4,837 (0,4); 4,583 (0,4); 4,039 (0,4); 4,021 (0,5); 3,333 (58,5); 2,677 (0,9); 2,673 (1,2); 2,508 (126,6); 2,514 (157,8); 2,500 (117,0); 2,335 (0,8); 2,331 (1,0); 1,990 (1,8); 1,900 (4,6); 1,891 (8,9); 1,882 (9,9); 1,874 (4,5); 1,372 (0,4); 1,330 (4,8); 1,351 (10,2); 1,312(10,0); 1,303 (4,2); 1,259 (0,8); 1,234δ = 10.176 (0.5); 10.143 (6.0); 10.118 (5.9); 9,779 (5.2); 9.238 (11.9); 8.966 (5.2); 8.897 (0.4); 8.884 (0.8); 8,869 (7.5); 8,847 (8.0); 8,400 (4,6); 8,386 (4,5); 8.316 (5.6); 8,297 (16.0); 8.275 (13.0); 8,264 (15,7); 8,243 (8.4); 8.154 (0.4); 7.956 (0.4); 7,934 (0.4); 7.922 (0.6); 7,900 (0.7); 7,680 (3.7); 7,655 (5.1); 7.632 (3.5); 6.457 (0.7); 6,436 (2.5); 6,414 (3.7); 6.391 (2.6); 6,359 (0.8); 5,757 (5.6); 4,838 (0.4); 4,837 (0.4); 4,583 (0.4); 4,039 (0.4); 4,021 (0.5); 3,333 (58.5); 2,677 (0.9); 2,673 (1.2); 2,508 (126.6); 2,514 (157.8); 2,500 (117.0); 2.335 (0.8); 2.331 (1.0); 1,990 (1.8); 1,900 (4,6); 1,891 (8.9); 1,882 (9.9); 1,874 (4.5); 1,372 (0.4); 1,330 (4,8); 1,351 (10.2); 1,312 (10.0); 1,303 (4,2); 1,259 (0.8); 1,234
(2.6) ; 1,194 (0,7); 1,176 (1,1); 1,158 (0,6); 0,917 (3,2); 0,873 (0,5); 0,109 (2,1); 0,095 (0,8); 0,000 (4,1) (2.6); 1,194 (0.7); 1.176 (1.1); 1.158 (0.6); 0.917 (3.2); 0.873 (0.5); 0,109 (2,1); 0.095 (0.8); 0,000 (4.1)
Beispiel 1-1-65: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-65: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 10,159 (5,5); 10,134 (5,6); 9,666 (12,3); 8,894 (7,3); 8,872 (8,0); 8,402 (3,8); 8,389 (3,7); 8,341 (0,4); 8,320 (16,0); 8,298 (15,4); 8,271 (2,1); 8,265 (2,3); 8,257 (2,6); 8,250δ = 10.159 (5.5); 10.134 (5.6); 9,666 (12.3); 8,894 (7.3); 8,872 (8.0); 8,402 (3,8); 8,389 (3.7); 8,341 (0.4); 8,320 (16,0); 8,298 (15.4); 8,271 (2,1); 8.265 (2.3); 8.257 (2.6); 8,250
(2.4) ; 8,244 (2,3); 7,949 (10,9); 7,927 (10,0); 7,680 (3,3); 7,655 (4,3); 7,632 (3,1); 6,458 (0,6); 6,437 (2,1); 6,415 (3,1); 6,392 (2,3); 6,371 (0,7); 5,758 (1,5); 4,039 (0,6); 4,021 (0,7); 3,328 (72,2); 2,677 (0,6); 2,673 (0,9); 2,668 (0,6); 2,543 (0,6); 2,513 (55,8); 2,508 (104,8); 2,504 (132,9); 2,499 (94,3); 2,495 (44,8); 2,335 (0,7); 2,331 (0,8); 2,326 (0,6); 1,990(2.4); 8.244 (2.3); 7.949 (10.9); 7,927 (10.0); 7,680 (3.3); 7,655 (4.3); 7,632 (3,1); 6.458 (0.6); 6,437 (2,1); 6,415 (3,1); 6,392 (2,3); 6,371 (0.7); 5,758 (1.5); 4,039 (0.6); 4,021 (0.7); 3,328 (72.2); 2,677 (0.6); 2,673 (0.9); 2,668 (0.6); 2,543 (0.6); 2,513 (55.8); 2,508 (104.8); 2,504 (132.9); 2,499 (94.3); 2,495 (44.8); 2.335 (0.7); 2.331 (0.8); 2,326 (0.6); 1,990
(2.7) ; 1,655 (4,1); 1,640 (10,2); 1,633 (10,7); 1,620 (4,4); 1,580 (0,4); 1,397 (0,4); 1,356 (4,9); 1,343 (10,4); 1,336 (10,7); 1,321 (3,8); 1,232 (1,3); 1,194 (0,8); 1,176 (1,5); 1,158(2.7); 1,655 (4.1); 1,640 (10.2); 1,633 (10.7); 1,620 (4.4); 1,580 (0.4); 1.397 (0.4); 1,356 (4.9); 1,343 (10.4); 1.336 (10.7); 1,321 (3.8); 1,232 (1,3); 1,194 (0.8); 1.176 (1.5); 1,158
(0,7); 0,007 (2,7); -0,001 (48,3); -0,009 (1,7) (0.7); 0.007 (2.7); -0.001 (48.3); -0.009 (1.7)
Beispiel 1-1-66: : 1H-NMR (400,0 MHz, d6-DMSO): Example 1-1-66:: 1 H-NMR (400.0 MHz, d6-DMSO):
δ= 10,155 (7,5); 10,130 (7,9); 8,836 (9,0); 8,814 (10,1); 8,789 (0,5); 8,720 (8,2); 8,710 (8,6); 8,584 (0,4); 8,407 (6,5); 8,391 (6,5); 8,362 (0,8); 8,340 (1,0); 8,320 (9,4); 8,299 (16,0); 8,281 (13,9); 8,262 (5,2); 7,935 (0,4); 7,913 (0,4); 7,861 (10,8); 7,839 (10,4); 7,818 (0,6); 7,681 (4,5); 7,656 (7,1); 7,633 (4,3); 6,457 (0,9); 6,435 (3,3); 6,414 (4,9); 6,391δ = 10.155 (7.5); 10.130 (7.9); 8,836 (9.0); 8,814 (10.1); 8,789 (0.5); 8,720 (8,2); 8,710 (8.6); 8,584 (0.4); 8,407 (6.5); 8,391 (6.5); 8.362 (0.8); 8.340 (1.0); 8,320 (9.4); 8,299 (16.0); 8,281 (13.9); 8.262 (5.2); 7.935 (0.4); 7.913 (0.4); 7.861 (10.8); 7,839 (10.4); 7.818 (0.6); 7,681 (4,5); 7,656 (7.1); 7.633 (4.3); 6.457 (0.9); 6,435 (3.3); 6,414 (4,9); 6,391
(3.5) ; 6,369 (1,1); 4,058 (0,6); 4,041 (1,6); 4,023 (1,6); 4,005 (0,6); 3,332 (50,7); 3,090 (1,6); 2,913 (2,2); 2,904 (3,4); 2,895 (4,9); 2,885 (4,9); 2,877 (3,7); 2,868 (2,5); 2,818 (0,8); 2,805 (0,8); 2,675 (1,0); 2,506 (138,3); 2,333 (1,0); 1,992 (6,6); 1,232 (0,7); 1,214 (0,4); 1,195 (2,1); 1,177 (3,7); 1,160 (1,9); 0,810 (0,4); 0,774 (2,9); 0,756 (12,2); 0,743 (11,2); 0,739 (10,9); 0,727 (4,2); 0,706 (0,7); 0,688 (0,5); 0,654 (0,5); 0,644 (0,5); 0,614 (4,0); 0,596 (13,3); 0,590 (11,8); 0,577 (3,6); 0,485 (0,5); 0,356 (0,4); 0,344 (0,4); 0,000 (1,7) (3.5); 6.369 (1.1); 4.058 (0.6); 4,041 (1.6); 4.023 (1.6); 4.005 (0.6); 3,332 (50,7); 3,090 (1.6); 2,913 (2,2); 2.904 (3.4); 2,895 (4.9); 2,885 (4.9); 2,877 (3.7); 2,868 (2.5); 2.818 (0.8); 2,805 (0.8); 2,675 (1.0); 2,506 (138.3); 2.333 (1.0); 1,992 (6.6); 1,232 (0.7); 1.214 (0.4); 1,195 (2.1); 1,177 (3.7); 1,160 (1.9); 0.810 (0.4); 0.774 (2.9); 0.756 (12.2); 0.743 (11.2); 0.739 (10.9); 0.727 (4.2); 0.706 (0.7); 0.688 (0.5); 0.654 (0.5); 0.644 (0.5); 0.614 (4.0); 0.596 (13.3); 0.590 (11.8); 0.577 (3.6); 0.485 (0.5); 0.356 (0.4); 0.344 (0.4); 0,000 (1.7)
a) Die Bestimmung des M+ mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 Acetonitril (enthält 0,1% Ameisensäure) und Wasser als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril Gerät: Agilent 1100 LC-System, Agilent MSD System, HTS PAL. a) The determination of M + with the LC-MS in the acidic range is carried out at pH 2.7 acetonitrile (contains 0.1% formic acid) and water as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile Device: Agilent 1100 LC system, Agilent MSD system, HTS PAL.
Die Bestimmung der in den vorangegangenen Tabellen und Herstellungsbeispielen angegebenen logP-Werte erfolgte gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (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 erfolgt mit einem Bruker Avance 400 ausgestattet mit einem Durchflussprobenkopf (60 μΐ Volumen), mit Tetramethylsilan als Referenz (0.0) und den Lösungsmitteln CD3CN, CDCI3 oder D6-DMSO. The determination of the logP values given in the preceding tables and preparation examples was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (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) Determination of the 'H NMR data is carried out on a Bruker Avance 400 equipped with a 60 μΐ volume flow head, with tetramethylsilane as reference (0.0) and the solvents CD 3 CN, CDCl 3 or D 6 -DMSO.
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-Listenverfahren NMR peak list procedures
Die 'H-NMR-Daten ausgewählter Beispiele werden in Form von 'H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der δ -Wert 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: δ 1 (Intensitätl); δ 2 (Intensität2); ; δ i (Intensitäti); ; δ n (Intensitätn) The peak list of an example therefore has the form: δ 1 (intensity I); δ 2 (intensity 2); ; δ i (intensity i); ; δ n (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 im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von 'H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. To calibrate the chemical shift of 'H NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
Die Listen der 'H-NMR-Peaks sind ähnlich den klassischen 'H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. The lists of the 'H NMR peaks are similar to the classical' H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
Darüber hinaus können sie wie klassische 'H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. In addition, they can, like classic 'H-NMR prints solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 'H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. When indicating compound signals in the delta range of solvents and / or water, our lists of 'H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D6 and the peak of water, which are usually in the Average high intensity.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (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 target 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 "Nebenprodukt-Fingerabdrucken" zu erkennen. Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints."
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD-Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 'H-NMR-Interpretation. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 'H NMR interpretation.
Weitere Details zu 'H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on 'H NMR peaks can be found in Research Disclosure Database Number 564025.
Anwendungsbeispiele applications
Die folgenden Beispiele zeigen die Insektizide und akarizide Wirkung der erfindungsgemäßen Verbindungen. Dabei beziehen sich die genannten erfindungsgemäßen Verbindungen auf die in der Tabelle 1 mit den entsprechenden Referenzzeichen (Nr.) aufgeführten Verbindungen: Phaedon cochleariae - Sprühtest (PHAECO) The following examples show the insecticidal and acaricidal activity of the compounds of the invention. In this case, the abovementioned compounds according to the invention relate to the compounds listed in Table 1 with the corresponding reference signs (No.): Phaedon cochleariae spray test (PHAECO)
Lösungsmittel: Gewichtsteile Aceton Solvent: parts by weight of acetone
Gewichtsteile Dimethylformamid  Parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
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. 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.
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. 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.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 100 g/ha: 1-1-01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1-1- 11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1- 25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1- 39, 1-1-40, 1-1-41, 1-1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1-50, 1-1-51, 1-1-52, 1-1- 53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-1-63, 1-la-1 In this test, z. For example, the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-1-01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1- 1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1- 25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1- 1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1- 50, 1-1-51, 1-1-52, 1-1- 53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-1-63, 1-la-1
100 % bei einer Aufwandmenge von 500 g/ha: 1-1 -02, 1-1-03, 1-1-04 Tetranychus urticae - Sprühtest, OP-resistent (TETRUR) 100% at a rate of 500 g / ha: 1-1 -02, 1-1-03, 1-1-04 Tetranychus urticae - spray test, OP-resistant (TETRUR)
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 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. Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. 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. Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90 % bei einer Aufwandmenge von 100 g/ha: 1-1-01, 1-1-07, 1-1-11, 1-1-16, 1-1-32, 1-1-56, 1-1-59 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. In this test, z. For example, the following compounds of Preparation Examples have an effect of 90% at a rate of 100 g / ha: 1-1-01, 1-1-07, 1-1-11, 1-1-16, 1-1-32 , 1-1-56, 1-1-59
100 % bei einer Aufwandmenge von 100 g/ha: 1-1-05, 1-1-15, 1-1-17, 1-1-18, 1-1-20, 1-1 -21, 1-1-23, 1-1- 24, 1-1-25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31, 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1- 40, 1-1-41, 1-1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1- 54, 1-1-55, 1-1-57, 1-1-58, 1-1-60, 1-1-61, 1-1-62, 1-1-63, 1-la-1 100% at a rate of 100 g / ha: 1-1-05, 1-1-15, 1-1-17, 1-1-18, 1-1-20, 1-1 -21, 1-1 -23, 1-1-24, 1-1-25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31 , 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1 -1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1 -50, 1-1-51, 1-1-52, 1-1-53, 1-1- 54, 1-1-55, 1-1-57, 1-1-58, 1-1-60 , 1-1-61, 1-1-62, 1-1-63, 1-la-1
100 % bei einer Aufwandmenge von 500 g/ha: 1-1 -03, 1-1-04 100% at a rate of 500 g / ha: 1-1 -03, 1-1-04
Myzus persicae - Sprühtest (MYZUPE) Myzus persicae - spray test (MYZUPE)
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid Emulgator: Alkylarylpolyglykolether  1, 5 parts by weight of dimethylformamide emulsifier: 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. Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus {Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. 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. 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. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 20 g/ha: 1-1-60 After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. In this test, z. Example, the following compounds of the preparation examples effect of 90% at an application rate of 20 g / ha: 1-1-60
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90%> bei einer Aufwandmenge von 100 g/ha: 1-1-01 , 1-1-25, 1-1-27, 1-1-28, 1-1-30, 1-1-39, 1-1-42, 1-1-46, 1-1- 48, 1-1-55, 1-1-56, 1-1-57, 1-1-59, 1-1-61 In this test, z. For example, the following compounds of the Preparation Examples Effect of 90%> at an application rate of 100 g / ha: 1-1-01, 1-1-25, 1-1-27, 1-1-28, 1-1-30 , 1-1-39, 1-1-42, 1-1-46, 1-1-48, 1-1-55, 1-1-56, 1-1-57, 1-1-59, 1 -1-61
100% bei einer Aufwandmenge von 100 g/ha: 1-1-17, 1-1-37, 1-1-40, 1-1-41, 1-1-44, 1-1-49, 1-1-54, 1-1- 62 100% at a rate of 100 g / ha: 1-1-17, 1-1-37, 1-1-40, 1-1-41, 1-1-44, 1-1-49, 1-1 -54, 1-1-62
90%) bei einer Aufwandmenge von 500 g/ha: 1-1-03, 1-1-04 90%) at a rate of 500 g / ha: 1-1-03, 1-1-04
Spodoptera frugiperda - Sprühtest (SPODFR) Lösungsmittel: 78,0 Gewichtsteile Aceton Spodoptera frugiperda - spray test (SPODFR) 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 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. 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.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms {Spodoptera frugiperda) besetzt. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm {Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in %> bestimmt. Dabei bedeutet 100 %>, dass alle Raupen abgetötet wurden; 0 %> bedeutet, dass keine Raupe abgetötet wurde. After 7 days the effect is determined in%>. 100% means> that all caterpillars have been killed; 0%> means that no caterpillar has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83 %> bei einer Aufwandmenge von 20 g/ha: 1-1-32 In this test, z. Example, the following compounds of the preparation examples effect of 83%> at a rate of 20 g / ha: 1-1-32
83 % bei einer Aufwandmenge von 100 g/ha: 1-1-09, 1-1-12, 1-1-35, 1-1-47, 1-1-56 83% at a rate of 100 g / ha: 1-1-09, 1-1-12, 1-1-35, 1-1-47, 1-1-56
100 % bei einer Aufwandmenge von 100 g/ha: 1-1 -01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-10, 1-1-11, 1-1- 13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-33, 1-1- 34, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1-1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-48, 1-1-49, 1-1- 50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-1-63, 1-la-1 100% at a rate of 100 g / ha: 1-1 -01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-10, 1-1 -11, 1-1- 13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20 , 1-1-21, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-33, 1-1-34, 1-1-36, 1 1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1-1-42, 1-1-43, 1-1-44, 1-1 -45, 1-1-46, 1-1-48, 1-1-49, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54 , 1-1-55, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-1-63, 1 la-1
100 % bei einer Aufwandmenge von 500 g/ha: 1-1 -03, 1-1-04 Amblyomma hebaraeum -Test 100% at a rate of 500 g / ha: 1-1 -03, 1-1-04 Amblyomma hebaraeum 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. Zeckennymphen (Ambfyomma hebraeum) werden in perforierte Plastikbecher gesetzt und in der gewünschten Konzentration eine Minute getaucht. Die Zecken werden auf Filterpapier in eine 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. Tick nymphs (Ambfyomma hebraeum) are placed in perforated plastic cups and dipped for one minute at the desired concentration. The ticks are put on filter paper in one
Petrischale überführt und in einem Klimaschrank gelagert. Petri dish transferred and stored in a climatic cabinet.
Nach 42 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Zecken abgetötet wurden; 0 % bedeutet, dass keine der Zecken abgetötet wurde. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von lOOppm: 1-1-47 After 42 days the kill is determined in%. 100% means that all ticks have been killed; 0% means that none of the ticks have been killed. In this test, z. For example, the following compounds of Preparation Examples an effect of 80% at a rate of lOOppm: 1-1-47
100% bei einer Aufwandmenge von lOOppm: 1-1-43, 1-1-56, 1-1-60, 1-1-62 100% at an application rate of 100 ppm: 1-1-43, 1-1-56, 1-1-60, 1-1-62
Boophilus microplus - Diptest (BOOPMI Dip) Boophilus microplus - Diptest (BOOPMI Dip)
Testtiere: Rinderzecken (Boophilus microplus) Stamm Parkhurst, SP-resistent Lösungsmittel: Dimethylsulfoxid Test animals: Bovine tick (Boophilus microplus) strain Parkhurst, SP-resistant Solvent: Dimethylsulfoxide
10 mg Wirkstoff werden in 0,5 ml Dimethylsulfoxid gelöst. Zwecks Herstellung einer geeigneten Formulierung verdünnt man die Wirkstofflösung mit Wasser auf die jeweils gewünschte Konzentration. 10 mg of active ingredient are dissolved in 0.5 ml of dimethyl sulfoxide. In order to prepare a suitable formulation, the active compound solution is diluted with water to the particular desired concentration.
Diese Wirkstoffzubereitung wird in Röhrchen pipettiert. 8-10 gesogene, adulte, weibliche Rinderzecken (Boophilus microplus) werden in ein weiteres Röhrchen mit Löchern überführt. Das Röhrchen wird in die Wirkstoffzubereitung getaucht wobei alle Zecken vollständig benetzt werden. Nach Ablaufen der Flüssigkeit werden die Zecken auf Filterscheiben in Kunststoffschalen überführt und in einem klimatisierten Raum aufbewahrt. This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female bovine ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored 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 for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80 % bei einer Aufwandmenge von 100 ppm: 1-1-43, 1-1-47, 1-1-55, 1-1-56, 1-1-62 90 % bei einer Aufwandmenge von 100 ppm: 1-1-57 In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: 1-1-43, 1-1-47, 1-1-55, 1-1-56, 1-1- 62 90% at a rate of 100 ppm: 1-1-57
95 % bei einer Aufwandmenge von 100 ppm: 1-1-60 Boophilus microplus -Injektionstest (BOOPMI Inj) 95% at an application rate of 100 ppm: 1-1-60 Boophilus microplus injection test (BOOPMI Inj)
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. 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 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. 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. 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. 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 for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90 % bei einer Aufwandmenge von 20 μg/Tier: I- 1 -24 In this test, e.g. the following compounds of the Preparation Examples an effect of 90% at an application rate of 20 ug / animal: I-1 -24
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 20 μg/Tier: 1-1-01 , 1-1-03, 1-1-04, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1- 1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1- 1-25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-37, 1-1-40, 1-1-42, 1-1-43, 1- 1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1- 1-60, 1-1-61, 1-1-62, 1-la-1 In this test, e.g. the following compounds of the Preparation Examples have an effect of 100% at an application rate of 20 μg / animal: 1-1-01, 1-1-03, 1-1-04, 1-1-06, 1-1-07, 1 -1-08, 1-1-09, 1- 1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1 -16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1- 1-25 , 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1 -1-35, 1-1-37, 1-1-40, 1-1-42, 1-1-43, 1- 1-45, 1-1-46, 1-1-47, 1-1 -48, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57 , 1-1-58, 1-1-59, 1- 1-60, 1-1-61, 1-1-62, 1-la-1
Ctenocephalides felis - Oraltest (CTECFE) Ctenocephalides felis - Oral test (CTECFE)
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit citriertem 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 Parafilm verschlossen ist. Der Zylinder enthält die Blut- Wirkstoffzubereitung, 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, whose Bottom is closed with parafilm. 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 zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: 1-1 -01, 1-1-03, 1-1-04, 1-1-06, 1-1 -07, 1-1-08, 1-1-09, 1-1- 10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1- 24, 1-1-25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-37, 1-1-40, 1-1-42, 1-1- 43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1- 59, 1-1-60, 1-1-61, 1-1-62, 1-la-1 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 Preparation Examples an effect of 100% at a rate of 100 ppm: 1-1 -01, 1-1-03, 1-1-04, 1-1-06, 1-1 -07, 1-1 -08, 1-1-09, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16 , 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1 -1-25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1 -34, 1-1-35, 1-1-37, 1-1-40, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47 , 1-1-48, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1 -1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-la-1
Lucilla cuprina - Test (LUCICU) Lucilla cuprina - test (LUCICU)
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 Schafgoldfliege {Lucilla cuprina) werden in ein Testgefäß überführt, 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 Goldfinch {Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound 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. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: After 2 days the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed. In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 100 ppm:
1-1-01, 1-1-03, 1-1-04, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-37, 1-1-40, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50, 1-1-51, 1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1-la-1 1-1-01, 1-1-03, 1-1-04, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1- 1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1-1-17, 1-1-18, 1-1- 19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-37, 1-1-40, 1-1-42, 1- 1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50, 1-1-51, 1-1-52, 1-1- 53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-59, 1-1-60, 1-1-61, 1-1-62, 1 la-1
90 % bei einer Aufwandmenge von 100 ppm: 1-1-58 90% at a rate of 100 ppm: 1-1-58
80 % bei einer Aufwandmenge von 100 ppm: 1-1-25 80% at a rate of 100 ppm: 1-1-25
Musca domestica-Test (MUSCDO) Lösungsmittel: Dimethylsulfoxid Musca domestica test (MUSCDO) 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. 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 domestica) besetzt. 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 domestica).
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. 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 zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80 % bei einer Aufwandmenge von 100 ppm: 1-1-12, 1-1-13, 1-1-19, 1-1-46, 1-1-51, 1-1-62 In this test, e.g. the following compounds of the Preparation Examples have an effect of 80% at an application rate of 100 ppm: 1-1-12, 1-1-13, 1-1-19, 1-1-46, 1-1-51, 1-1 -62
90 % bei einer Aufwandmenge von 100 ppm: 1-1-06, 1-1-08, 1-1-21, 1-1-24, 1-1-47, 1-1-48, 1-1-56 90% at a rate of 100 ppm: 1-1-06, 1-1-08, 1-1-21, 1-1-24, 1-1-47, 1-1-48, 1-1-56
100 % bei einer Aufwandmenge von 100 ppm: 1-1 -01, 1-1-03, 1-1-07, 1-1-11, 1-1 -14, 1-1-15, 1-1-16, 1-1- 17, 1-1-18, 1-1-20, 1-1-29, 1-1-34, 1-1-40, 1-1-43, 1-1-45, 1-1-50, 1-1-52, 1-1-53, 1-1-61, 1-1-60, 1-1-55, 1-1- 57, 1-1-59 Ctenocephalides felis - in-vitro Kontakttests mit adulten Katzenflöhen 100% at a rate of 100 ppm: 1-1 -01, 1-1-03, 1-1-07, 1-1-11, 1-1 -14, 1-1-15, 1-1-16 , 1-1-17, 1-1-18, 1-1-20, 1-1-29, 1-1-34, 1-1-40, 1-1-43, 1-1-45, 1 -1-50, 1-1-52, 1-1-53, 1-1-61, 1-1-60, 1-1-55, 1-1-57, 1-1-59 Ctenocephalides felis - in -vitro contact tests with adult 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 Schaukelrotation 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 swing rotation 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 Katzenflöhen (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. After evaporation of the solvent, the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed 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 uncoordinated 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. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 5 μg/cm2: 1-1-01 , 1-1-03, 1-1-14, 1-1-20, 1-1-21, 1-1-25, 1-1-27, 1-1- 28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1-35, 1-1-37, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50, 1-1- 51,1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-61 Rhipicephalus sanguineus - in-vitro Kontakttests mit Adulten der braunen Hundezecke 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. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 5 μg / cm 2 : 1-1-01, 1-1-03, 1-1-14, 1-1-20, 1 -1-21, 1-1-25, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1 -35, 1-1-37, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50 , 1-1- 51.1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1 -1-59, 1-1-60, 1-1-61 Rhipicephalus sanguineus - in vitro contact tests with adults of brown dog tick
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 Schaukelrotation 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 swing rotation 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 Hundezecken {Rhipicephalus sanguineus) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend im Dunkeln bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Zecken auf den Boden des Gläschens geklopft und auf einer Wärmeplatte bei 45-50°C maximal 5 min. inkubiert. After evaporation of the solvent, the vials are populated with 5-10 adult dog tick {Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated.
Zecken, die unbeweglich auf dem Boden verbleiben oder sich so unkoordiniert bewegen, dass sie nicht gezielt der Wärme durch nach oben klettern ausweichen können, gelten als tot bzw. angeschlagen. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
Eine Substanz zeigt gute Wirkung gegen Rhipicephalus sanguineus, wenn in diesem Test bei einer Aufwandmenge von 5 μg/cm2 mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Zecken angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Zecken geschädigt wurden. A substance shows good activity against Rhipicephalus sanguineus, 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 ticks were struck or dead. 0% effect means that no ticks have been damaged.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100%) bei einer Aufwandmenge von 5 μg/cm2: 1-1-56, 1-1-61 In this test, for example, the following compounds of the preparation examples show an effect of 100%) at an application rate of 5 μg / cm 2 : 1-1-56, 1-1-61
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%) bei einer Aufwandmenge von 1 μg/cm2: 1-1-43, 1-1-50 In this test, for example, the following compounds of the preparation examples show an effect of 80%) at an application rate of 1 μg / cm 2 : 1-1-43, 1-1-50
80% bei einer Aufwandmenge von 5 μg/cm2: 1-1-14, 1-1-35, 1-1-52, 1-1-54, 1-1-55, 1-1-57, 1-1-59, 1-1-60 80% at a rate of 5 μg / cm 2 : 1-1-14, 1-1-35, 1-1-52, 1-1-54, 1-1-55, 1-1-57, 1- 1-59, 1-1-60

Claims

Patentansprüche: Patent claims:
1. Verbindungen der allgemeinen Formel (I) 1. Compounds of the general formula (I)
Figure imgf000101_0001
Figure imgf000101_0001
wobei where
R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach durch Halogen substituiertes Ci-Ce-Alkyl, Cs-Ce-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Ce-Alkylthio, Ci-Ce- Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C6-Alkylcarbonyl, Ci-C6-Alkoxycarbonyl, CI-CÖ- Alkoxyimino-Ci-C6-alkyl oder Ci-Cö-Alkylsulfonyloxy steht, oder R 1 for halogen, nitro, cyano, for Ci-Ce-alkyl, Cs-Ce-cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-C6, which may be mono or polysubstituted by halogen -Alkylsulfonyl, Ci-C6-alkylcarbonyl, Ci-C6-alkoxycarbonyl, CI-C O -alkoxyimino-Ci-C 6 -alkyl or Ci-Cö-alkylsulfonyloxy, or
R1 für eine gegebenenfalls 1 oder 2 Heteroatome enthaltende Ci-C i-Kohlenstoffkette steht, die an zwei benachbarten Ringpositionen gebundenen ist und einen aliphatischen, aromatischen, heteroaromatischen oder heterocyclischen Ring bildet, welcher gegebenenfalls ein-oder mehrfach durch Ci-Cö-Alkyl oder Halogen substituiert ist, wobei n dann gleich 1 ist und wobei die Heteroatome ausgewählt sind aus der Gruppe bestehend aus N, S und O, n für 1,2, 3, 4 oder 5 steht, or Halogen is substituted, where n is then equal to 1 and where the heteroatoms are selected from the group consisting of N, S and O, n is 1,2, 3, 4 or 5,
R2 für Wasserstoff, Halogen, Cyano, Hydroxy oder für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder Ci- Cö-Alkoxy steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Fluor, Chlor, Brom oder lod R 2 represents hydrogen, halogen, cyano, hydroxy or is optionally mono- or polysubstituted, identically or differently substituted Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-Cö-alkoxy, where the substituents are independent are selected from one another from fluorine, chlorine, bromine or iodine
R3 für Wasserstoff, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C i-Alkyl, C2-C4-Alkenyl, C3-C4-Alkinyl, Ci-C4-Alkylcarbonyl oder C1-C4- Alkoxycarbonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Cyano, Halogen, C1-C4- Alkyl oder Ci-C4-Alkoxy Q1 für C-R4 oder N steht, R 3 represents hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C2-C4-alkenyl, C3-C4-alkynyl, Ci-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl, where the substituents are independently selected from cyano, halogen, C1-C4-alkyl or Ci-C4-alkoxy Q 1 stands for CR 4 or N,
Q2 für C-R steht, Q2 stands for CR,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 oder N steht, wobei Q1 für C-R4 steht wenn Q4 für N steht und wobei Q4 für C-R4 steht wenn Q1 für N steht. Q 4 stands for CR 4 or N, where Q 1 stands for CR 4 if Q 4 stands for N and where Q 4 stands for CR 4 if Q 1 stands for N.
R4 für Wasserstoff, Halogen, Nitro, Cyano, Ci-C i-Alkyl, Ci-C i-Haloalkyl oder Ci-C i-Alkoxy steht, R 4 represents hydrogen, halogen, nitro, cyano, Ci-C i-alkyl, Ci-C i-haloalkyl or Ci-C i-alkoxy,
R6 für Wasserstof, Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-Cö-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6- Cycloalkyl , Ci-C6-Alkoxy, (Ci-C6-Alkoxy)carbonyl, Ci-C6-Alkylamino, Formyl, (CI-CÖ- Alkyl)carbonyl, Ci-C6-Alkoxyimino-Ci-C6-alkyl, Ci-C6-Dialkylamino, (CI-CÖ- Alkylamino)carbonyl, (Ci-C6-Dialkylamino)carbonyl, Ci-C6-Alkylthio, CI-CÖ- Alkylsulfinyl, Ci-Cö-Alkylsulfonyl, Ci-C6-Alkylaminosulfonyl oder CI-CÖ- Alkylsulfonylamino steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Hydroxy, Amino, Ci-Cö-Alkyl, Ci-C6-Alkoxy, C3-C6-Cycloalkyl, Ci-C6-Halogenalkoxy oder Ci- Ce-Alkylthio, R 6 for hydrogen, halogen, nitro, cyano, for optionally mono- or polysubstituted, identically or differently substituted Ci-Cö-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C3-C6-cycloalkyl, Ci-C6 -Alkoxy, (Ci-C6-alkoxy)carbonyl, Ci-C6-alkylamino, formyl, (CI-CÖ-alkyl)carbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl, Ci-C6-dialkylamino, (CI- CÖ-alkylamino)carbonyl, (Ci-C6-dialkylamino)carbonyl, Ci-C6-alkylthio, CI-CÖ-alkylsulfinyl, Ci-Cö-alkylsulfonyl, Ci-C6-alkylaminosulfonyl or CI-CÖ-alkylsulfonylamino, where the substituents are independent are selected from each other from halogen, cyano, nitro, hydroxy, amino, Ci-Cö-alkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, Ci-C6-haloalkoxy or Ci-Ce-alkylthio,
X für Ci-Cö-Halogenalkyl steht, das gegebenenfalls zusätzlich einfach bis dreifach substituiert sein kann, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Hydroxy, Cyano oder Ci-C i-Alkoxy, X For CI-CÖ-HALOGENALKYL, which may also be simply substituted up to three times, whereby the substituents are selected independently of one another from hydroxy, cyano or ci-c i-alkoxy,
W für O oder S steht, W stands for O or S,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a lone pair of electrons or oxygen,
A für eine bivalente chemische Gruppierung steht, die ausgewählt ist aus den Gruppierungen -C(=0)NR13-, -C(=S)NR13-, -C(=0)NR13-NR16-A represents a bivalent chemical group which is selected from the groups -C(=0)NR 13 -, -C(=S)NR 13 -, -C(=0)NR 13 -NR 16 -
, -C(=0)NR13C(R14)(R15)C(=0)NR16-, C(R14)(R15)NR13-C(=0)- , -CH=N-N(R13)-C(=W)- N(R16)-, -N(R13)-N(R16)-C(=0)- wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, R13, R16 unabhängig voneinander für Wasserstoff, für Ci-C i-Alkyl, Ci-C4-Alkoxy-Ci-C4-Alkyl, Cyano-Ci-C4-alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkylcarbonyl, Ci-C4-Alkoxycarbonyl oder C2-C4- Alkenyl stehen, , -C(=0)NR 13 C(R 14 )(R 15 )C(=0)NR 16 -, C(R 14 )(R 15 )NR 13 -C(=0)- , -CH=NN (R 13 )-C(=W)- N(R 16 )-, -N(R 13 )-N(R 16 )-C(=0)- where the first mentioned (left) connection point on the ring and the respective second-mentioned (right-hand) connection point connects to Y, R 13 , R 16 independently of each other for hydrogen, for Ci-C i-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, cyano-Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl or C2- C4-alkenyl,
R14, R15 unabhängig voneinander für Wasserstoff oder für Ci-C4-Alkyl stehen oder R14, R15 zusammen einen 3-6 gliedrigen aliphatischen Ring bilden, R 14 , R 15 independently represent hydrogen or Ci-C4-alkyl or R 14 , R 15 together form a 3-6 membered aliphatic ring,
Y für Wasserstoff oder für gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Ci-Ce-Alkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl oder C3-C6- Cycloalkenyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-Alkylaminocarbonyl, Ci-C4-Alkylaminothiocarbonyl, Ci-C4-Halogenalkylaminocarbonyl, Di-(Ci-C4-Alkyl)-aminocarbonyl, Di-(Ci-C4-Alkyl)- aminothiocarbonyl, Hydroxycarbonyl, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-C6-Cycloalkyl, Ci- C4-Alkyl-C3-C4-Cycloalkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Ci-Ce-Alkoxy, Ci-Ce-Halogenalkoxy, Ci-C6-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl, Ci-C4-Alkoxyimino-Ci-C4-Alkyl, Ci-Cö-Alkylthio, Ci-C6-Alkylsulfinyl, Ci-Cö-Alkylsulfonyl oder aus gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertem Aryl oder Hetaryl, wobei die Subsituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C6-Alkoxy, oder CI-CÖ- Halogenalkoxy, oder Y represents hydrogen or optionally mono- or polysubstituted, identically or differently substituted Ci-Ce-alkyl, C 2 -Ce-alkenyl, C 2 -C6-alkynyl, Cs-Ce-cycloalkyl or C3-C6-cycloalkenyl, where the Substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-alkylaminothiocarbonyl, Ci-C4-haloalkylaminocarbonyl, di-(Ci-C4-alkyl)-aminocarbonyl, di-(Ci -C4-alkyl)- aminothiocarbonyl, hydroxycarbonyl, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci-C4-alkyl-C3-C4-cycloalkyl, C 2 -Ce-alkenyl, C 2 - C6-alkynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-C6-alkoxycarbonyl, Ci-Cö-alkylcarbonyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, Ci-Cö-alkylthio, Ci-C6- Alkylsulfinyl, Ci-Cö-alkylsulfonyl or from aryl or hetaryl which is optionally substituted once or more, identically or differently, the substituents being selected from halogen, nitro, cyano, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci -C6-alkoxy, or CI-CÖ- haloalkoxy, or
Y für gegebenenfalls substituiertes Heterocyclyl, Aryl, Aryl-Ci-C4-alkyl, Hetaryl, Oxo- Heterocyclyl oder Hetaryl-Ci-C4-alkyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, CI-CÖ- Alkylsulfinyl oder Ci-C6-Alkylsulfonyl, sowie Salze und N-Oxide von Verbindungen der Formel (I). Y represents optionally substituted heterocyclyl, aryl, aryl-Ci-C4-alkyl, hetaryl, oxo-heterocyclyl or hetaryl-Ci- C4 -alkyl, the substituents being selected from halogen, nitro, cyano, hydroxy, Ci-C4- Alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy, Ci-C6-alkylthio, CI-CÖ-alkylsulfinyl or Ci-C6-alkylsulfonyl, as well as salts and N-oxides of compounds of the formula ( I).
Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 , wobei für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach durch Halogen substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl oder Ci- C4-Alkylsulfonyl oder Ci-C4-Alkylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht Compounds of the general formula (I) according to claim 1, wherein for halogen, nitro, cyano, for optionally mono- or polysubstituted by halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfmyl or Ci-C 4 -alkylsulfonyl or Ci-C 4 -alkylsulfonyloxy, n stands for 1, 2, 3, 4 or 5
R für Wasserstoff oder für gegebenenfalls einfach bis dreifach substituiertes Ci-Cö-Alkyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Fluor, Chlor, Brom oder lodR represents hydrogen or optionally mono- to tri-substituted Ci-Cö-alkyl, the substituents being independently selected from fluorine, chlorine, bromine or iodine
R3 für Wasserstoff, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C i-Alkyl, C2-C4-Alkenyl, C3-C4-Alkinyl, Ci-C i-Alkylcarbonyl oder C1-C4- Alkoxycarbonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Cyano, Halogen oder Ci- C4-Alkoxy R 3 for hydrogen, for optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 alkenyl, C3-C 4 alkynyl, Ci-C i-alkylcarbonyl or C 1 -C 4 - Alkoxycarbonyl stands, the substituents being independently selected from cyano, halogen or Ci-C4-alkoxy
Q1 für C-R4 oder N steht, Q 1 stands for CR 4 or N,
Q2 für C-R4 steht, Q 2 stands for CR 4 ,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 oder N steht, wobei Q1 für C-R4 steht wenn Q4 für N steht und wobei Q4 für C-R4 steht wenn Q1 für N steht. Q 4 stands for CR 4 or N, where Q 1 stands for CR 4 if Q 4 stands for N and where Q 4 stands for CR 4 if Q 1 stands for N.
R4 für Wasserstoff, Halogen, Ci-C4-Alkyl, Ci-C4-Haloalkyl oder Ci-C4-Alkoxy stehen, R 4 represents hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl or Ci-C 4 alkoxy,
R6 für Wasserstoff, Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Ci-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C4- Cycloalkyl , Ci-C4-Alkoxy, (Ci-C4-Alkoxy)carbonyl, (Ci-C4-Alkyl)carbonyl, C1-C4- Alkylthio, Ci-C4-Alkylsulfmyl, oder Ci-C4-Alkylsulfonyl steht, wobei die Substituenten unabhängig voneinander ausgewählt sind aus Halogen, Cyano, Nitro, Ci- C4-Alkyl, Ci-C4-Alkoxy oder Ci-C4-Alkylthio, R 6 for hydrogen, halogen, nitro, cyano, for optionally mono- or polysubstituted, identically or differently substituted Ci-C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C3-C 4 -cycloalkyl , Ci-C 4 -alkoxy, (Ci-C 4 -alkoxy)carbonyl, (Ci-C 4 -alkyl)carbonyl, C 1 -C 4 -alkylthio, Ci-C 4 -alkylsulfmyl, or Ci-C 4 -alkylsulfonyl stands, the substituents being independently selected from halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 alkoxy or Ci-C 4 alkylthio,
X für Ci-C4-Halogenalkyl steht, X represents Ci-C 4 -haloalkyl,
W für O steht, W stands for O,
G für ein freies Elektronenpaar oder für Sauerstoff steht, A für die bivalente chemische Gruppierung -C(=0)NR - steht, wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, G stands for a lone pair of electrons or oxygen, A stands for the bivalent chemical group -C(=0)NR -, where the first-mentioned (left) attachment point is attached to the ring and the second-mentioned (right) attachment point is attached to Y,
R13 für Wasserstoff, für Ci-C i-Alkyl, Cyanomethyl, Ci-C i-Alkoxymethyl, Cs-Ce-Cycloalkyl, Ci-C i-Alkylcarbonyl, Ci-C i-Alkoxycarbonyl oder C2-C4-Alkenyl steht, R 13 is hydrogen, Ci-C i-alkyl, cyanomethyl, Ci-C i-alkoxymethyl, Cs-Ce-cycloalkyl, Ci-C i-alkylcarbonyl, Ci-C i-alkoxycarbonyl or C2-C4-alkenyl,
Y für Wasserstoff oder oder für gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Ci-Ce-Alkyl, C2-Ce-Alkenyl, C2-C6-Alkinyl, Cs-Ce-Cycloalkyl oder C3-C6- Cycloalkenyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C3-Cs-Cycloalkyl, C1-C4- Alkyl-C3-C4-Cycloalkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, C1-C4- Alkylsulfinyl, Ci-C4-Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl oder C1-C4- Alkoxyimino-Ci-C4-Alkyl, oder aus gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertem Phenyl, Thienyl, Pyridinyl oder Pyrimidinyl, wobei die Subsituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C6-Alkoxy oder Ci-C6-Halogenalkoxy, oder Y represents hydrogen or or optionally mono- or multiple-, identically or differently substituted Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6-alkynyl, Cs-Ce-cycloalkyl or C3-C6-cycloalkenyl, where the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-Cs-cycloalkyl, C1-C4-alkyl-C 3 -C 4 -cycloalkyl, C 2 - C 4 alkenyl, C 2 -C 4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C1-C4 alkylsulfinyl, Ci-C4 alkylsulfonyl, Ci-C4 alkoxycarbonyl, Ci-Cö alkylcarbonyl or C1-C4-alkoxyimino-Ci-C4-alkyl, or from phenyl, thienyl, pyridinyl or pyrimidinyl which is optionally mono- or polysubstituted, identically or differently substituted, the substituents being selected from halogen, nitro, cyano, hydroxy, Ci-C4 -Alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy, or
Y für ein gegebenenfalls ein- oder mehrfach, gleich oder verschieden substituiertes Phenyl, oder für einen gegebenenfalls einfach oder mehrfach substituierten Heterocyclus ausgewählt aus der Gruppe bestehend aus Thienyl, Furanyl, Pyrrolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, 1,2,3-Triazolyl, 1 ,2,4-Triazolyl, 1,2,3- Oxdiazolyl, 1 ,2,4-Oxdiazolyl, 1,3,4-Oxdiazolyl, 1,2,3-Thiadiazolyl, 1 ,2,4-Thiadiazolyl, 1,3,4-Thiadiazolyl, Tetrazolyl, Pyridinyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,4- Triazinyl, 1,3,5-Triazinyl, Pyrrolidinyl, Isoxazolidinyl, Pyrazolidinyl, Oxazolidinyl, Thiazolidinyl, Imidazolidinyl, 1 ,2,4-Oxadiazolidinyl, 1 ,2,4-Thiadiazolidinyl, 1,2,4- Triazolidinyl, 1,3,4-Oxadiazolidinyl, 1,3,4-Thiadiazolidinyl, 1,3,4-Triazolidinyl, Pyrrolinyl, Isoxazolinyl, 2,3-Dihydropyrazolyl, 3,4-Dihydropyrazolyl, 4,5-Dihydropyrazolyl, 2,3- Dihydrooxazolyl, 3,4-Dihydrooxazolyl, Piperidinyl, Tetrahydrothienyl, Piperazinyl, Morpholinyl, Thiomorpholinyl, Dihydropyranyl, Tetrahydropyranyl, Tetrahydrothienyl, 1 ,4-Dioxanyl, 1,3-Dioxanyl, Dioxolanyl, Dioxolyl, Tetrahydrofuranyl, Dihydrofuranyl, Oxetanyl, Thietanyl, Oxidothietanyl, Dioxidothietanyl, Oxiranyl, Azetidinyl, Oxazetidinyl, Oxaziridinyl, Oxazepanyl, Oxazinanyl, Azepanyl, Oxopyrrolidinyl, Dioxopyrrolidinyl, Oxomorpholinyl, Oxopiperidinyl, Oxopiperazinyl oder Oxotetrahydrofuranyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C i-Alkyl, Ci- C i-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy, Ci-C6-Alkylthio, CI-CÖ- Alkylsulfinyl oder Ci-C6-Alkylsulfonyl. Y is an optionally mono- or polysubstituted, identically or differently substituted phenyl, or for an optionally mono- or polysubstituted heterocycle selected from the group consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1,2,4-triazolyl, 1,2,3-oxdiazolyl, 1,2,4-oxdiazolyl, 1,3,4-oxdiazolyl, 1,2,3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, isoxazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1,3,4-oxadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,3,4-triazolidinyl, pyrrolinyl, Isoxazolinyl, 2,3-Dihydropyrazolyl, 3,4-Dihydropyrazolyl, 4,5-Dihydropyrazolyl, 2,3-Dihydrooxazolyl, 3,4-Dihydrooxazolyl, Piperidinyl, Tetrahydrothienyl, Piperazinyl, Morpholinyl, Thiomorpholinyl, Dihydropyranyl, Tetrahydropyranyl, Tetrahydrothienyl, 1 , 4-Dioxanyl, 1,3-Dioxanyl, Dioxolanyl, Dioxolyl, Tetrahydrofuranyl, Dihydrofuranyl, Oxetanyl, Thietanyl, Oxidothietanyl, Dioxidothietanyl, Oxiranyl, Azetidinyl, Oxazetidinyl, Oxaziridinyl, Oxazepanyl, Oxazinanyl, Azepanyl, Oxopyrrolidinyl, Dioxopyrrolidinyl, Ox omorpholinyl, oxopiperidinyl, oxopiperazinyl or Oxotetrahydrofuranyl stands, where the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C i-alkyl, Ci-C i-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy, Ci-C6-alkylthio, CI-CÖ - Alkylsulfinyl or Ci-C6-alkylsulfonyl.
Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 oder 2, wobei Compounds of the general formula (I) according to claim 1 or 2, wherein
R1 für Halogen, Nitro, Cyano, für gegebenenfalls einfach oder mehrfach, durch Fluor oder Chlor substituiertes Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, Ci- C4-Alkylsulfonyl oder Ci-C4-Alkylsulfonyloxy steht, n für 1 , R 1 for halogen, nitro, cyano, for Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, Ci-C 4 -alkylsulfmyl, Ci- C 4 -alkylsulfonyl or Ci-C 4 -alkylsulfonyloxy, n is 1,
2, 3, 4 oder 5 steht, 2, 3, 4 or 5 stands,
R2 für Wasserstoff steht, R 2 stands for hydrogen,
R3 für Wasserstoff, Methyl, Cyanomethyl, Ethyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl oder Ethoxycarbonyl steht, R 3 represents hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
Q1 für C-R4 steht, Q 1 stands for CR 4 ,
Q2 für C-R4 steht, Q 2 stands for CR 4 ,
Q3 für C-R4 steht, Q 3 stands for CR 4 ,
Q4 für C-R4 steht, Q 4 stands for CR 4 ,
R4 für Wasserstoff, Fluor oder Chlor steht, R 4 represents hydrogen, fluorine or chlorine,
R6 für Wasserstoff, Halogen, Nitro, Cyano, oder für gegebenenfalls einfach bis dreifach durch Halogen substituiertes Ci-C4-Alkyl oder Ci-C4-Alkoxy steht, R 6 represents hydrogen, halogen, nitro, cyano, or Ci-C 4 -alkyl or Ci-C 4 -alkoxy which is optionally substituted one to three times by halogen,
X für Trifluormethyl, Difluormethyl oder Pentafluorethyl steht, X represents trifluoromethyl, difluoromethyl or pentafluoroethyl,
W für O steht, W stands for O,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a lone pair of electrons or oxygen,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die jeweils erstgenannte (linke) Anknüpfungsstelle am Ring und die jeweils zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, und wobei R für Wasserstoff, Methyl, Ethyl, Cyanomethyl, Methoxymethyl, Ethoxymethyl, Cyclopropyl, Methylcarbonyl, Ethylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl oder Prop-2-en-l-yl steht, A stands for the bivalent chemical group -C(=0)NR 13 -, where the first-mentioned (left) attachment point is attached to the ring and the second-mentioned (right) attachment point is attached to Y, and where R represents hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl,
Y für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Ci-C6-Alkyl, C2- C i-Alkenyl, C2-C4-Alkinyl, oder Cs-Ce-Cycloalkyl steht, wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Aminothiocarbonyl, Aminocarbonyl, Ci-C4-AlkyL- Ci-C4-Halogenalkyl, C3-Cs-Cycloalkyl, C2-C4- Alkenyl, C2-C4-Alkinyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-Alkylsulfmyl, C1-C4- Alkylsulfonyl, Ci-C4-Alkoxycarbonyl, Ci-Cö-Alkylcarbonyl oder Ci-C4-Alkoxyimino-Ci-C4- Alkyl, Ci-Ce-Alkyl-Cs-Cs-Cycloalkyl, oder Y represents optionally mono- to tri-substituted, identically or differently substituted C-C6-alkyl, C2-C i-alkenyl, C2-C4-alkynyl, or Cs-Ce-cycloalkyl, the substituents being selected from halogen, nitro, cyano , hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkyL-Ci-C4-haloalkyl, C3-Cs-cycloalkyl, C2-C4-alkenyl, C 2 -C 4 alkynyl, Ci-C 4 -alkoxy, Ci-C 4 -Alkylthio, Ci-C 4 -alkylsulfmyl, C1-C4-alkylsulfonyl, Ci-C4-alkoxycarbonyl, Ci-Cö-alkylcarbonyl or Ci-C4-alkoxyimino-Ci-C4-alkyl, Ci-Ce-alkyl-Cs-Cs- Cycloalkyl, or
Y für gegebenenfalls ein- bis dreifach, gleich oder verschieden substituiertes Phenyl, Phenylmethyl, 3-Oxetan-l-yl, 3-Thietan-l-yl, 3-Oxidothietan-l-yl, 3,3-Dioxidothietan-l-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyridin-2-yl-methyl, Pyridin-3-yl-methyl, Pyridin- 4-yl-methyl, l,3-Pyrimidin-2-yl oder l,Y is optionally mono- to tri-substituted, identically or differently substituted phenyl, phenylmethyl, 3-oxetan-l-yl, 3-thietan-l-yl, 3-oxidothietan-l-yl, 3,3-dioxidothietan-l-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyridin-2-yl-methyl, Pyridin-3-yl-methyl, Pyridin-4-yl-methyl, l,3-Pyrimidin-2- yl or l,
3-Pyrimidin-2-yl-methyl steht , wobei die Substituenten ausgewählt sind aus Halogen, Nitro, Cyano, Hydroxy, Ci-C4-Alkyl, Ci- C4-Halogenalkyl, Ci-C6-Alkoxy, oder Ci-C6-Halogenalkoxy. 3-Pyrimidin-2-yl-methyl is where the substituents are selected from halogen, nitro, cyano, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy.
4. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1, 2 oder 3, wobei 4. Compounds of the general formula (I) according to claim 1, 2 or 3, wherein
R1 für Cyano, Fluor, Chlor, Brom, Iod, Difluormethyl, Trifluormethyl, Pentafluorethyl, Difluormethoxy, Trifluormethoxy oder Trifluormethylsulfonyloxy steht, n für 1, 2, 3, 4 oder 5 steht R 1 represents cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy or trifluoromethylsulfonyloxy, n represents 1, 2, 3, 4 or 5
R2 für Wasserstoff steht, R 2 stands for hydrogen,
R3 für Wasserstoff steht, R 3 stands for hydrogen,
Q1 für C-R4 steht, Q 1 stands for CR 4 ,
Q2 für C-R steht, für C-R steht, Q4 für C-R4 steht, Q 2 stands for CR, stands for CR, Q 4 stands for CR 4 ,
R4 für Wasserstoff stehen, R 4 represents hydrogen,
R6 für Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder Trifluormethyl steht, X für Trifluormethyl steht, W für O steht, R 6 is fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl, X is trifluoromethyl, W is O,
G für ein freies Elektronenpaar oder für Sauerstoff steht, G stands for a lone pair of electrons or oxygen,
A für die bivalente chemische Gruppierung -C(=0)NR13- steht, wobei die erstgenannte (linke) Anknüpfungsstelle am Ring und die zweitgenannte (rechte) Anknüpfungsstelle an Y anknüpft, und wobei A stands for the bivalent chemical group -C(=0)NR 13 -, where the first-mentioned (left) attachment point is attached to the ring and the second-mentioned (right) attachment point is attached to Y, and where
R13 für Wasserstoff oder Methyl steht, R 13 represents hydrogen or methyl,
Y für Methyl, Ethyl, Propan-l-yl, Propan-2-yl, Butan- 1-yl, Butan-2-yl, 2-Methylpropan-l-yl, 2-Methylpropan-2-yl, l-Butin-3-yl, Cyclopropyl, Cyclobutyl, Cyanomethyl, 1- Methoxycarbonylmethyl, 1 -Cyanoethyl, 2-Cyanoethyl, 1-Cyanoprop-l-yl, 2-Cyanoprop-l- yl, 3-Cyanoprop-l-yl, 1 -Cyanoprop-2-yl, 2-Cyanoprop-2-yl, 1 -Cyanocyclopropyl, 2- Cyanoprop-2-en-l-yl, 2-Cyanocyclopropyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3- Cyanocyclobutyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 1 -Fluorpropan-2-yl, 2,2-Difluorprop-l-yl, l,3-Difluorpropan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Ethinylcyclopropyl, 1 -Ethinylcyclobutyl, 1 -Methoxypropan-2-yl, 1 - Methoxycyclopropyl, 1 -Ethoxycyclopropyl, 1 -Methoxycarbonylcyclopropyl, 1 - Ethoxycarbonyl-cyclopropyl, Cyclopropylmethyl, 1-Cyclopropyleth-l -yl, 1- Trifluormethylcyclopropyl, Pyridin-2-yl, 5-Chlorpyridin-2-yl, 5-Fluorpyridin-2-yl, 1- (Aminocarbonyl)cyclopropyl, 1 -(Aminothiocarbonyl)cyclopropyl, 1 -Cyano-2- methylpropan-l-yl, l-Cyanobut-3-in-l-yl, l-Cyano-2-methylpropan-l-yl, 1 -Cyano-propan- 2-yl, 1-Cyano-l-cyclopropylethyl, 1-Cyano-l-ethylprop-l-yl, 1-Cyano-l - methylcyclopropyl-methyl, (2-R)- 1 -(Methylthio)propan-2-yl, (2-R)- 1 -Y for methyl, ethyl, propan-l-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-l-yl, 2-methylpropan-2-yl, l-butyn- 3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-l-yl, 1-cyanoprop- 2-yl, 2-cyanoprop-2-yl, 1-cyanocyclopropyl, 2-cyanoprop-2-en-l-yl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 2-fluoroethyl, 2, 2-Difluoroethyl, 2,2,2-Trifluoroethyl, 1 -Fluoropropan-2-yl, 2,2-Difluoroprop-l-yl, l,3-Difluoropropan-2-yl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 1 - Ethylcyclopropyl, 1 -Ethynylcyclopropyl, 1 -Ethynylcyclobutyl, 1 -Methoxypropan-2-yl, 1 - Methoxycyclopropyl, 1 -Ethoxycyclopropyl, 1 -Methoxycarbonylcyclopropyl, 1 - Ethoxycarbonylcyclopropyl, Cyclopropylmethyl, 1-Cyclopropyleth-l -yl, 1-Trifluoromethylcyclopropyl, Pyridin-2-yl, 5-chloropyridin-2-yl, 5-fluoropyridin-2-yl, 1-(aminocarbonyl)cyclopropyl, 1-(aminothiocarbonyl)cyclopropyl, 1-cyano-2-methylpropan-l-yl, l- Cyanobut-3-yn-l-yl, l-cyano-2-methylpropan-l-yl, 1-cyano-propan-2-yl, 1-cyano-l-cyclopropylethyl, 1-cyano-l-ethylprop-l- yl, 1-Cyano-l - methylcyclopropyl-methyl, (2-R)- 1 -(Methylthio)propan-2-yl, (2-R)- 1 -
(Methylsulfinyl)propan-2-yl, l,3-Dimethoxy-2-cyanopropan-2-yl, 3-Oxetan-l-yl, Pyridin- 2-ylmethyl oder l,3-Pyrimidin-2-yl-methyl steht. (Methylsulfinyl)propan-2-yl, l,3-dimethoxy-2-cyanopropan-2-yl, 3-oxetan-l-yl, pyridin-2-ylmethyl or l,3-pyrimidin-2-yl-methyl.
5. Agrochemische Formulierung enthaltend Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 4 in biologisch wirksamen Gehalten von zwischen 0,00000001 und 98 Gew.-%, bezogen auf das Gewicht der agrochemischen Formulierung, sowie Streckmittel und/oder oberflächenaktive Stoffe. 5. Agrochemical formulation containing compounds of the general formula (I) and / or their salts according to one of claims 1 to 4 in biologically effective levels of between 0.00000001 and 98% by weight, based on the weight of the agrochemical formulation, as well as extenders and/or surface-active substances.
Agrochemische Formulierung gemäß Anspruch 5 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. Agrochemical formulation according to claim 5 additionally containing a further agrochemical active ingredient.
Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 4 auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt, wobei Verfahren zur Behandlung des menschlichen oder tierischen Körpers ausgeschlossen sind. Process for combating animal pests, in which compounds of the general formula (I) and / or their salts according to one of claims 1 to 4 are allowed to act on animal pests and / or their habitat, processes for treating the human or animal body being excluded are.
Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4 zur Bekämpfung von tierischen Schädlingen. Use of compounds of the general formula (I) according to one of claims 1 to 4 for combating animal pests.
Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4 zum Schutz des Vermehrungsmaterials von Pflanzen. Use of compounds of the general formula (I) according to one of claims 1 to 4 for protecting the propagating material of plants.
Quinolincarbonsäuren der Formel (II-l) Quinolinecarboxylic acids of the formula (II-l)
Figure imgf000109_0001
Figure imgf000109_0001
wobei where
R a , R , R 0 und R unabhängig voneinander die in Anspruch 4 für R beschriebene Bedeutung haben und R a , R , R 0 and R independently of one another have the meaning described for R in claim 4 and
R6 die in Anspruch 4 angegebene Bedeutung hat. R 6 has the meaning given in claim 4.
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