EP3414236A1 - Substituierted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents - Google Patents

Substituierted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents

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Publication number
EP3414236A1
EP3414236A1 EP17702147.4A EP17702147A EP3414236A1 EP 3414236 A1 EP3414236 A1 EP 3414236A1 EP 17702147 A EP17702147 A EP 17702147A EP 3414236 A1 EP3414236 A1 EP 3414236A1
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EP
European Patent Office
Prior art keywords
spp
methyl
phenyl
cyano
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17702147.4A
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German (de)
French (fr)
Inventor
Johannes-Rudolf Jansen
Markus Heil
Reiner Fischer
David WILCKE
Matthieu WILLOT
Kerstin Ilg
Sascha EILMUS
Peter Lösel
Wolfram Andersch
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP3414236A1 publication Critical patent/EP3414236A1/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present application relates to novel heterocyclic compounds, intermediates for their preparation and their use for controlling animal pests.
  • WO 2011/009804 A2 heterocyclic compounds, inter alia, imidazolyl carboxamides are described which can be used as insecticides. However, no imidazolylcarboxamides are described which are directly substituted on the imidazolyl radical by aryls or hetaryl. The imidazolylcarboxamides listed in WO 2011/009804 A2 show clear weaknesses in their insecticidal activity.
  • Modern insecticides must meet many requirements, for example, in terms of the amount, duration and breadth of their effect and possible use. Issues related to toxicity, beneficial and pollinator protection, environmental properties, application rates, the ability to be combined with other active substances or formulation auxiliaries, as well as the amount of effort required to synthesize an active substance, and resistance may arise. just to name a few paramenter. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties compared with the known compounds, at least with regard to individual aspects.
  • the object of the present invention was to provide compounds which complement the spectrum of pesticides in various aspects.
  • the problem is solved, as well as other tasks not explicitly mentioned, which can be deduced or deduced from the relationships discussed herein, by the provision of compounds of the formula (I)
  • V is a radical selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
  • W is a radical selected from among hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
  • X is a radical selected from the group optionally substituted aryl or hetaryl
  • Y is a radical selected from hydrogen, cyano, optionally substituted alkyl, alkenyl, or alkynyl, optionally interrupted by heteroatoms and optionally substituted cycloalkyl and optionally interrupted by heteroatoms and optionally substituted cycloalkylalkyl , Arylalkyl or hetarylalkyl,
  • A is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl or alkynyl and optionally interrupted by heteroatoms and optionally substituted cycloalkyl or cycloalkylalkyl,
  • T is oxygen or a pair of electrons, and their salts.
  • substituted aryl or hetaryl also encompasses those radicals which have bonded to two adjacent ring positions of the aryl or hetaryl ring a chain consisting of one to two heteroatoms from the series S, N or O and / or one to five carbon atoms and this thus forms an optionally partially unsaturated aliphatic, aromatic, heteroaromatic or optionally partially unsaturated heterocyclic ring, such that a bicyclic cycle results for X together with the aryl or hetaryl radical.
  • Q is oxygen or sulfur
  • V is a radical from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
  • W is a radical from the series consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
  • X is a radical from the series, optionally mono- or polysubstituted independently of one another by halogen, NL 1 ! , Nitro, cyano or optionally substituted alkyl, halo genalkyl, alkoxy, alkyl-S (0) m -, haloalkoxy, haloalkyl-S (0) m -, carboxy, aryl or hetaryl-substituted aryl or hetaryl, where a radical from the series hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, is a radical from the series hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or
  • L 1 and L 2 together with N represents an optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms bonded via N,
  • Y is a radical selected from hydrogen, methyl, cyano, optionally mono- or polysubstituted independently of one another by halogen, C 1 -C 4 - alkoxy, Ci-C 4 alkyl-S (0) m - or cyano-substituted C COE Alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally monosubstituted to disubstituted by halogen, C 1 -C 4 -
  • Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano-substituted Cs-Cs-cycloalkyl, optionally mono- or disubstituted independently of one another by O, S (0) m, CO or NR 2 is interrupted and is optionally mono- to tetrasubstituted independently of one another by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano substitution jewes, straight or branched C 3 -C 8 cycloalkyl-Ci-C4-alkyl, and is optionally mono- to trisubstituted independently of one another by halogen, C 1 -C 4 - alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S (0) m -, C 4 haloalkoxy, C C4-haloalkyl-S
  • A represents a radical selected from hydrogen, methyl, which is optionally monosubstituted to polysubstituted independently of one another by halogen, C 1 -C 4 - alkoxy, Ci-C4-alkyl-S (0) m - or cyano-substituted CI-COE alkyl, C3 -C 6 alkenyl or C 3 -C 6 alkynyl and optionally mono- to disubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or cyano-substituted C 3 -C 6 -cycloalkyl and optionally monosubstituted or disubstituted independently of one another by halogen, C 1 - C4 alkyl, Ci-C4-haloalkyl, Ci-
  • R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
  • T is oxygen or a pair of electrons, and their salts.
  • radicals Q, V, W, Y, m, A, R 2 and T are defined as in the preferred range (1-1) and
  • X is a radical from the series, optionally mono- to polysubstituted independently of one another
  • L is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
  • Alkynyl or cycloalkyl a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or
  • L 1 and L 2 together with N is an N-bonded, optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms.
  • V is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano
  • W is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine , Methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano
  • X is a radical from the series which is optionally monosubstituted to polysubstituted independently of one another by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S (0) m - , GC 4 -
  • L 1 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkyl,
  • L 2 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -C -alkenyl, C 2 -C -alkynyl or C 3 -C 6 -cycloalkyl, or
  • L 1 and L 2 together with N represents an optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms bonded via N,
  • cyano which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci-C4 alkyl, C3-C4 alkenyl, or C 3 -C 4 -alkynyl, optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C 6 -cycloalkyl and optionally mono- to disubstituted independently of one another by O, S (0) m , CO or NR 2 interrupted, optionally monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl
  • A represents a radical selected from hydrogen, methyl, which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci- -alkyl, C 3 -C 6 alkenyl or C 3 -C 6 -alkynyl optionally mono- or disubstituted independently by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C6- Cycloalkyl and optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted, straight-chain or branched C 3 -
  • R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
  • T is oxygen or a pair of electrons, and their salts.
  • radicals Q, V, W, Y, m, A, R 2 and T are defined as in the preferred range (2-1) and is a radical from the series, optionally mono- to polysubstituted independently of one another
  • L is a radical selected from hydrogen, optionally substituted Ci-C 4 alkyl, C 2 - C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 cycloalkyl,
  • L 2 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -
  • L 1 and L 2 together with N is an N-bonded, optionally substituted, saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms.
  • Methyl, ethyl and cyano represents a radical from the series optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluorofhyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro -2H-pyran-4-yloxy) methyl, dimethylsulfamoyl,
  • T stands for oxygen or an electron pair. Taking into account the position of the carboxamide group on the imidazole radical, formula (I) gives the very particularly preferred structure (II) and salts thereof. Very particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (3-2),
  • radicals Q, V, W, Y, m, A and T are defined as in the preferred range (3-1) and X is a radical from the series, where appropriate, monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, Ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, Difluorofhyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoe
  • V is hydrogen and fluorine
  • W is a radical from the series hydrogen, chlorine, bromine and methyl
  • X is a radical from the series optionally simply to three times independently by
  • Y is a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and benzyl, m is a number 0, 1 or 2,
  • A is a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl,
  • T is oxygen or a pair of electrons and their salts. Taking into account the position of the carboxamide group on the imidazole radical, formula (I) gives the particularly preferred structure (II) and salts thereof. Particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (4-2), The radicals Q, V, W, Y, m, A and T are defined as in the preferred range (4-1) and
  • X is a radical from the series, if appropriate, simply to three times independently
  • Q is oxygen or sulfur and preferably oxygen, stands for hydrogen
  • radicals Q, V, W, Y, A and T are defined as in the preferred range (5-1) and
  • X is a radical from the series 3 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3 (Methylsulfanyl) phenyl, pyrimidin-2-yl, 3 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4 -Chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3
  • 6-methoxypyridin-3-yl 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2 Methoxyphenyl, 1,3-benzodioxole
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine,
  • Hetaryl (equivalent to heteroaryl, also as part of a larger unit such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl , Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4 Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl , Benz
  • halogen is fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine,
  • Hetaryl also as part of a larger moiety, such as hetarylalkyl
  • pyridyl pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, benzyl, pyridinylmethyl and thiazolylmethyl and
  • Heterocyclyl (also as part of a larger unit such as heterocyclylalkyl) for a saturated or unsaturated 3-, 4- or 5-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, but not 2 nitrogen atoms directly to be adjacent, for example 1- or 2-aziridinyl, 2-oxiranyl, 2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2 yl, 1-, 2- or 3-pyrrolidinyl.
  • 3-1 or (3-2) unless stated otherwise,
  • Halogen for fluorine, chlorine, bromine and iodine preferably fluorine, chlorine and bromine and
  • Heterocyclyl (also as part of a larger unit, such as heterocyclylalkyl) for a saturated or unsaturated 3- or 4-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, but not two nitrogen atoms to be directly adjacent for example, 1- or 2-aziridinyl, 2-oxiranyl, 2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl or 1,3-dioxetan-2-yl
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • T in the compounds of the formula (I) is oxygen
  • these compounds are present as NT oxides.
  • T in the compounds of the formula (I) is an electron pair
  • these compounds are present as pyridines.
  • the invention relates to the compounds of the formula (I) or of the formula (II) where the radicals Q, V, W, Y, m, A, R 2 and T are as defined in the preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or Preferred range (5-1) or preferred range (5-2) and X has the meanings described in embodiment (0).
  • the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or preferred range ( 5-2) and
  • X and L 1 and L 2 have the meanings described in the preferred range (1-1) or (1-2).
  • the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or Preferred range (5-2) and
  • X and L 1 and L 2 have the meanings described in the preferred range (2-1) or (2-2).
  • the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or preferred range ( 5-2) and X has the meanings described in the preferred range (3-1) or (3-2).
  • the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (5-1) or Preferred range (5-2) and
  • X has the meanings described in the preferred range (4-1) or the preferred range (4-2).
  • the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range ( 4-2) and
  • X has the meanings described in the preferred range (5-1) or the preferred range (5-2).
  • Another object of the invention are the intermediates of the formulas (Xa-Xd)
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus encompasses both pure stereoisomers and any desired mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs against 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, in particular nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, Ceramic, plastic or even metal (s) to ensure that they are free of hygienic pests and / or their excretions.
  • measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, Ceramic, plastic or even metal (s) to ensure that they are free of hygienic pests and / or their excretions Priormarily excluded from the scope of the invention in this regard are surgical or therapeutic, on the human body or the body of Animals to be applied and diagnostic regulations that are carried out on the human body or the bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications where these hygiene measures, rules and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, Hotels, hospitals, stables, animal husbandry, etc.
  • the term "hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
  • hygiene pests include the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as 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 from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp , Steneotarsonemus spinki, Tarsonemus spp., Z. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • B. Blaniulus guttulatus from the class of the Insecta, z. B. from the order of Blattodea z.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica unde- cimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • 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 b Camillus, Hypera postica, Hypomeces squamosus , Hypothenemus spp., E.g.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., E.g.
  • Melanotus longulus oregonensis Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoce- ros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prosthanus truncatus, Psylliodes spp., E.g.
  • Tanymecus spp. E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B.
  • Delia antiqua Delia coarctata, Delia florilega, Delia platura, Delia radicum, Derma- tobia hominis, Drosophila spp., e.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurotrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteys facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Moneliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncome topia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. Phylloxera devastatrix, Phyloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Trioza spp. Z. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. Helicoverpa armigera, Helicoverpa zea, Helioses spp., E.g. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
  • Leucoptera coffeella Lithocolletis spp., Z. B. Lithocoletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
  • Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudotelia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera z. B.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
  • Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., Eg.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
  • the compounds of the formula (I) may also be used in certain concentrations or as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) 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 further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain further pesticides and / or effect-improving adjuvants such as penetration promoters. those, z.
  • vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates ( CS); 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 FAOAVHO 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.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example 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.
  • formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties.
  • Suitable extenders z As water, polar and nonpolar organic chemical liquids such. 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, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the 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 ester
  • 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, eg.
  • Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated - te aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such.
  • acetone methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strong polar solvents such as dimethyl sulfoxide and water.
  • all suitable carriers can be used.
  • carriers are in particular question: z.
  • ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals 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: z.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, eg.
  • alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when used in water.
  • auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg. Example, iron oxide, titanium oxide, Ferrocy blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and / or physical stability can also be present. It may also contain foam-forming agents or defoamers.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional 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, sequestering agents, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • Retention promoters are all those substances which reduce the dynamic surface tension, such as, for example, dioctyl sulfosuccinate or which increase the viscoelasticity, such as, for example, hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are customarily used in order to prevent the penetration of agrochemical active ingredients into To improve plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or 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 are used to such.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or Plant growth regulators are used to such.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytot
  • flowering and fruiting behavior it is also possible to improve flowering and fruiting behavior, to optimize germination and rooting, to facilitate harvest and to increase crop yield, to influence ripeness, to increase the quality and / or nutritional value of harvested produce, to extend shelf life and / or to improve the workability of harvested produce improve.
  • the compounds of the formula (I) may be mixed 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 formula (I) can be used to improve plant properties such as 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.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, Triazamates, trimethacarb, XMC and xylylcarb or organophosphates, e.g.
  • carbamates e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosul
  • sodium channel modulators 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 isomer], deltamethrin, empenthrin [(EZ) (lR) isomer], es
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • allosteric modulators of the nicotinic acetylcholine receptor (nAChR) such as spinosyn, e.g. B. spinetoram and spinosad.
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinop- ren and methoprene or fenoxycarb or pyriproxyfen.
  • Non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
  • alkyl halides e.g. Methyl bromide and other alkyl halides
  • chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and diflovidazine or otoxazole.
  • Microbial disruptors of insect intestinal membrane such.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors such as diafliuron or organotin compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, i.e., two-wingers, such as cyromazine.
  • ecdysone receptor agonists such as chroma- tozide, halofenozide, methoxyfenocide and tebufenozide.
  • octopamine receptor agonists such as amitraz.
  • Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Roenton (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Roenton (Derris).
  • inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
  • inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
  • ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole, cyanotiliprole and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiazole, benzoximat, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fludexafon, fluopyram, fluralan, flux
  • All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
  • All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenocynazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole , (1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochloraz, (1,017) propiconazole, (1,018) Prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) t
  • inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) Fluxapyroxad, (2.008) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,
  • 3) respiratory chain inhibitors on complex III for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) Enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin , (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(E)
  • inhibitors of mitosis and cell division for example, (4,001) carbendazim, (4,002) diethyenebarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008 ) Zoxamide,, (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-Chloro-5- (4-chlorophenyl) -4- (2,6 -difluorophenyl) -6-methylpyridazine, (4.011)
  • inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil,
  • inhibitors of cell wall synthesis for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
  • inhibitors of melanin biosynthesis for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl carbamate.
  • inhibitors of signal transduction for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • compounds which may act as decouplers for example (14.001) fluazinam, (14.002) meptyldinocap.
  • the compounds of formula (I) may be combined with biological pesticides.
  • Bio 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 I-1582) or Bacillus pumilus, in particular strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thurin giensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp , aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrison strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • B. thuringiensis subspecies israelensis serotype H-14
  • strain AM65-52 Accession No. ATCC 1276
  • B. thuringiensis subsp aizawai, in particular strain ABTS-1857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-1 or B. thuringiens
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain 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 (new: Isaria fumosoroseus) , in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • 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
  • bacteria and fungi which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • plant extracts and products formed by microorganisms including proteins and secondary metabolites, which are or can be used as biological pest control agents are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, flurazoles, fluxofenim, furilazoles, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-mefhoxy-N - (4-
  • plants are understood as meaning all plants and plant populations, such as desirable and undesired wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potatoes, sugar beets, sugar cane , Tomatoes, peppers, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, Pears, citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soy, potatoes, sugar beets, sugar cane , Tomatoes, peppers, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, oilseed
  • Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and technological methods or combinations of these methods, including the transgenic plants and including plant varieties that can be protected or not protected by plant variety rights. Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes .
  • the plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B.
  • plants and their parts can be treated.
  • 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.
  • PV plants are understood as meaning plants with new properties (“traits”) have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • 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").
  • traits 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, causes z.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), Cryl-IA, CrylllA, CryIIIB2 , Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • PAT phosphinotricin
  • 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 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, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the application form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, ie the compounds of formula (I) are applied to the foliage, the frequency of treatment and the rate should be adjusted to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of the formula (I) on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, i. H. the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops, this can also be done by dosing the compound of formula (I) in a solid application form (eg as granules) into a flooded paddy field.
  • seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention.
  • the invention also relates to seed which has been treated at the same time with a compound of formula (I) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component.
  • the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • 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.
  • 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. 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 the formula (I) can also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia, mycorrhizal and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation.
  • symbionts such as rhizobia, mycorrhizal and / or endophytic bacteria or fungi
  • 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, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seeds may be used that have been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, for example customary diluents and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, Glue, gibberelline and also water.
  • customary additives for example customary diluents and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, Glue, gibberelline 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 under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • 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. Preference is given to using alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • 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 application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of formula (I), which have favorable toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual 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; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of formula (I) are administered to birds, namely caged birds or, in particular, poultry.
  • control or “combat” in the present context means that the compounds of formula (I) are effective in their occurrence of the particular parasite in an animal infected with such parasites to a harmless extent. More specifically, “combating” in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomy
  • Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Idagia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp.
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephal
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as: Metamonada: from the order Vaccinonadida, for example Giardia spp., Spironucleus spp.
  • Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
  • Euglenozoa from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
  • Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B.
  • Leucocytozoon spp. Plasmodium spp .; from the order Piroplasmida z. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtonella spp.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • Acute helixes pathogenic to humans or animals include, for example, acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., monogenea, cestodes, and trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea z.
  • Dactylogyrus spp. Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
  • Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeu- xiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp.
  • Fischoederius spp. Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp , Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
  • Nematodes from the order Trichinellida, for example: Capillaria spp., Trichinella spp., Trichomosides spp., Trichuris spp.
  • Aelurostrongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp.
  • Cyclococercus spp. Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastropogylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Obeli
  • Skjrabi- nema spp. Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp., From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphyl actinic or therapeutic.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
  • Another aspect relates to the compounds of formula (I) for use as anti-parasitic agents.
  • Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
  • Another aspect relates to the compounds of the formula (I) for use as anti-topazarasitic kum, in particular an arthropodicide, very particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg, solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg, surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, especially with pharmaceutically acceptable ones conventionally used in veterinary formulations Excipients and / or adjuvants conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
  • Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a nonhuman animal that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, that requires it.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of the formula (I) with other active substances, in particular with endo- and ectoparasiticides, are provided hereby for the veterinary field.
  • blending not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are used all active substances should be formulated in a common formulation or all active substances should be formulated in separate formulations; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as a mixing partner include, but are not limited to, the insecticides and acaricides detailed above.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoup
  • Active substances with unknown or non-specific mechanisms of action eg. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
  • Organochlorine compounds e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetone, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner;
  • Pyrethroids e.g. Eg, (cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU 15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis Permethrin, clocythrin, cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs), neonicotinoids, e.g. B. Nithiazine
  • Dicloromezotiaz, triflumezopyrim, macrocyclic lactones e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
  • Triphene Epofenonan, Diofenolan; Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, codemon or neem components
  • Dinitrophenols e.g. Dinocap, dinobuton, binapacryl
  • Benzoylureas eg. Fluazuron, penfluron,
  • Amidine derivatives e.g. Chormorman, cymiazole, demiditraz hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestocidal agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, Milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
  • all said mixing partners can optionally form salts with suitable bases or acids.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachidoid, which is able to attack pathogens such as.
  • pathogens such as.
  • viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stabbing flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are: 1) mosquitoes
  • Anopheles malaria, filariasis
  • - Culex Japanese encephalitis, filariasis, other viral diseases, transmission of other worms
  • - Aedes yellow fever, dengue fever, other viral diseases, filariasis
  • mites acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;
  • Ticks Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example 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, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control.
  • Fung, z. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials.
  • the compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • 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, i. h., They can be applied to the appropriate material without further changes.
  • insecticides or fungicides in particular those mentioned above come into question.
  • the compounds of the formula (I) can be used to protect against fouling of objects, in particular of hulls, sieves, nets, structures, wharfs 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, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • 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 of the orders Scorpiones, Araneae and Opiliones, of the classes Chilopoda and Diplopoda, of the class Insecta the order Blattodea, of 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, non-pressurized sprays, z.
  • the compounds of formula (I) can be synthesized, for example, by methods A to E as illustrated in the following schemes.
  • the metal organyls required for process A eg aryl / hetarylboronic acid ester, etc.
  • the aryl / hetaryl bromides required for process B are mostly purchased products or can be prepared by processes generally known in organic chemistry.
  • nitrile oxides required for process C or their precursors are largely purchased products or can be prepared by processes generally known in organic chemistry.
  • the ortho-iodophenols required for the process D are largely purchased products or can be prepared by processes generally known in organic chemistry.
  • amidation reactions are carried out in the presence of a condensing agent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent.
  • Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples include activating reagents such as phosgene, phosphorus trichloride, phosphorus oxychloride, oxalyl chloride, oxalyl bromide or thionyl chloride; Carbodiimides, such as '-dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (EDCI), or other customary condensation agents, such as phosphorus pentoxide, polyphosphoric acid,' -carbonyldiimidazole, 2-chloropyridine 1 Methoiodide (Mukaiyamas reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrol
  • Bis (tetramethylene) cloruronium tetrafluoroborate 0- (1H-benzotriazol-1-yl) -N, ⁇ , ⁇ ', ⁇ '-tetramethyluronium hexafluorophosphate (HBTU), 0- (7i7-benzotriazol-1-yl) - N, N, N ', N'-bis (tetramethylene) uronium hexafluorophosphate, 0- (1H-benzotriazol-1-yl) -N, ⁇ , ⁇ ', ⁇ '-tetramethyluronium tetrafluoroborate (TBTU), 0- (1H-Benzotriazol-1-yl) -N, N, ⁇ ', ⁇ '-bis (tetramethylene) uronium tetrafluoroborate, 0- (7-azabenzotriazol-1-yl) - / V, / V, / V'
  • Suitable acid acceptors are all customary inorganic or organic bases, for example organic amines such as triethylamine, diisopropylethylamine, methylmorpholine, pyridine or dimethylimidopyridine, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate or cesium carbonate; Alkalihydrogencarbonate such as sodium bicarbonate or potassium bicarbonate.
  • the amidation reaction in the processes according to the invention is optionally carried out in the presence of a suitable reaction auxiliary, for example N, N-dimethylformamide or -dimethylaminopyridine.
  • Suitable solvents are all interten organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene, cyclohexane), halogenated hydrocarbons (such as chlorotoluene, dichlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1,2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, propionitrile, butyronitrile, benzonitrile), amides (such as dimethylformamide, N, N). Dimethylacetamide, / V-methylformanilide, -methylpyrrolidone,
  • chloroformates may be used, e.g. Methyl chloroformate, ethyl chloroformate, isobutyl chloroformate and isopropyl chloroformate. Also, diethyl acetyl chloride, trimethylacetyl chloride and the like can be used therefor.
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the NMR spectra were determined with a Bruker Avance 400 equipped with a flow through probe head (60 ⁇ volume). In individual cases the NMR spectra were measured with a Bruker Avance II 600.
  • the NMR data of selected examples are listed in classical form ( ⁇ values, multiplet splitting, number of H atoms). The splitting of the signals was described as follows: s (singlet), d (doublet), t (triplet), q (quartet), quint (quintuplet), m (multiplet), br (for broad signals).
  • the solvents used were CD 3 CN, CDCl 3 or D6-DMSO, tetramethylsilane (0.00 ppm) being used as reference.
  • Step 1 (4.565 mmol) of 1-methyl-2-bromo-imidazole-5-carboxylic acid methyl ester (ABCR) was dissolved in 10 ml of ethanol, treated with 5.48 ml of 1 N NaOH (aq.) And stirred at room temperature for 60 min.
  • the batch was concentrated to dryness and suspended in 6 ml of water in an ultrasound bath. The white crystals were filtered off and washed with 2mL of water. The mother liquor was concentrated almost to dryness. The crystals were filtered off with suction and washed with a little water. The combined crystals were dried in an oil pump vacuum. Yield: 890 mg (95% of theory). logP [a]: 0.31;
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity 1); 82 (intensity 2); ; ⁇ (intensity i); ; ⁇ (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 1 H NMR interpretation.
  • Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control.
  • 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 the desired concentration is reached. 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.
  • 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 the desired concentration is reached. 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.
  • IPL41 insect medium (33% + 15% sugar) to a final volume of 200 ⁇ filled. Subsequently, the plates are sealed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Myzus persicae green peach aphid
  • Emulsifier Alkylary polyglycol ether
  • 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 the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Paprika plants Capsicum annuum which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.
  • Emulsifier alkylaryl polyglycol ether
  • 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 the desired concentration is reached.
  • emulsifier concentration 1000 ppm
  • 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.

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Abstract

The present invention relates to compounds of the general formula (I), wherein Q, V, T, W, X, Y and A have the meanings given in the description, and to the use thereof for controlling animal pests.

Description

Substituierte 2-(Het)aryl-imidazolyl-carboxyamide als Schädlingsbekämpfungsmittel  Substituted 2- (het) aryl-imidazolyl-carboxyamides as pesticides
Die vorliegende Anmeldung betrifft neue heterocyclische Verbindungen, Zwischenprodukte zu Ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen. The present application relates to novel heterocyclic compounds, intermediates for their preparation and their use for controlling animal pests.
In WO 2011/009804 A2 sind heterocyclische Verbindungen unter anderem auch Imidazolyl- carboxamide beschrieben, die als Insektizide verwendet werden können. Es werden jedoch keine Imidazolylcarboxamide beschrieben, die direkt am Imidazolylrest durch Aryle oder Hetaryle substituiert sind. Die in der WO 2011/009804 A2 aufgeführten Imidazolylcarboxamide zeigen dabei deutliche Schwächen in ihrer Insektiziden Wirkung. In WO 2011/009804 A2 heterocyclic compounds, inter alia, imidazolyl carboxamides are described which can be used as insecticides. However, no imidazolylcarboxamides are described which are directly substituted on the imidazolyl radical by aryls or hetaryl. The imidazolylcarboxamides listed in WO 2011/009804 A2 show clear weaknesses in their insecticidal activity.
Moderne Insektizide müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Nützling- und Bestäuberschonung, der Umwelteigenschaften, der Aufwandmengen, der Kombinier - barkeit 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, um nur einige Paramenter zu nennen. Schon aus all diesen Gründen kann die Suche nach neu- en Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern insecticides must meet many requirements, for example, in terms of the amount, duration and breadth of their effect and possible use. Issues related to toxicity, beneficial and pollinator protection, environmental properties, application rates, the ability to be combined with other active substances or formulation auxiliaries, as well as the amount of effort required to synthesize an active substance, and resistance may arise. just to name a few paramenter. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties compared with the known compounds, at least with regard to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten ergänzt wird. Gelöst wird die Aufgabe, sowie weitere nicht explizit genannte Aufgaben, die aus den hierin diskutierten Zusammenhängen ableitbar oder erschließbar sind, durch die Bereitstellung von Verbindungen der Formel (I) The object of the present invention was to provide compounds which complement the spectrum of pesticides in various aspects. The problem is solved, as well as other tasks not explicitly mentioned, which can be deduced or deduced from the relationships discussed herein, by the provision of compounds of the formula (I)
(i)  (I)
in welcher (Ausführung (0)) in which (version (0))
Q für Sauerstoff oder Schwefel steht, V für einen Rest aus der Reihe Wasserstoff, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halo- genalkoxy und Cyano steht, Q stands for oxygen or sulfur, V is a radical selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
W für einen Rest aus der Reihe Wasserstoff, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halo- genalkoxy und Cyano steht, W is a radical selected from among hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
X für einen Rest aus der Reihe gegebenenfalls substituiertes Aryl oder Hetaryl steht,Y für einen Rest aus der Reihe Wasserstoff, Cyano, gegebenenfalls substituiertes Alkyl, Alkenyl, oderAlkinyl, gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkyl und gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkylalkyl, Arylalkyl oder Hetarylal- kyl steht, X is a radical selected from the group optionally substituted aryl or hetaryl, Y is a radical selected from hydrogen, cyano, optionally substituted alkyl, alkenyl, or alkynyl, optionally interrupted by heteroatoms and optionally substituted cycloalkyl and optionally interrupted by heteroatoms and optionally substituted cycloalkylalkyl , Arylalkyl or hetarylalkyl,
A für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl oder Alkinyl und gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkyl oder Cycloalkylalkyl steht, A is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl or alkynyl and optionally interrupted by heteroatoms and optionally substituted cycloalkyl or cycloalkylalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
Hierbei umfasst für den Rest X der Begriff substituiertes Aryl oder Hetaryl auch solche Reste, die an zwei benachbarten Ringpositionen des Aryl oder Hetarylrings eine aus ein bis zwei Heteroatomen aus der Reihe S, N oder O und/oder ein bis fünf Kohlenstoffatomen bestehende Kette gebunden haben und diese somit einen gegebenenfalls teilweise ungesättigten aliphatischen, aromatischen, hete- roaromatischen oder gegebenenfalls teilweise ungesättigten heterocychschen Ring bildet, so dass sich für X zusammen mit dem Aryl oder Hetarylrest ein Bizyklus ergibt. Here, for the radical X, the term substituted aryl or hetaryl also encompasses those radicals which have bonded to two adjacent ring positions of the aryl or hetaryl ring a chain consisting of one to two heteroatoms from the series S, N or O and / or one to five carbon atoms and this thus forms an optionally partially unsaturated aliphatic, aromatic, heteroaromatic or optionally partially unsaturated heterocyclic ring, such that a bicyclic cycle results for X together with the aryl or hetaryl radical.
Bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (1-1). Preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Their combination forms the preferred range (1-1).
Q für Sauerstoff oder Schwefel steht, V für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C/t-Alkyl, Ci-C/t-Halogenalkyl, Q is oxygen or sulfur, V is a radical from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
Ci-C/t-Alkoxy, Ci-C/t-Halogenalkoxy und Cyano steht,  Ci-C / t-alkoxy, Ci-C / t-haloalkoxy and cyano,
W für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C/t-Alkyl, Ci-C t-Halogenalkyl, W is a radical from the series consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
Ci-C/t-Alkoxy, Ci-C/t-Halogenalkoxy und Cyano steht,  Ci-C / t-alkoxy, Ci-C / t-haloalkoxy and cyano,
X für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinan- der durch Halogen, NL1! , Nitro, Cyano oder gegebenenfalls substituiertes Alkyl, Halo- genalkyl, Alkoxy, Alkyl-S(0)m-, Halogenalkoxy, Halogenalkyl-S(0)m-, Carboxy, Aryl oder Hetarylsubstituiertes Aryl oder Hetaryl steht, wobei für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, oder X is a radical from the series, optionally mono- or polysubstituted independently of one another by halogen, NL 1 ! , Nitro, cyano or optionally substituted alkyl, halo genalkyl, alkoxy, alkyl-S (0) m -, haloalkoxy, haloalkyl-S (0) m -, carboxy, aryl or hetaryl-substituted aryl or hetaryl, where a radical from the series hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, is a radical from the series hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättig- ten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht, L 1 and L 2 together with N represents an optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms bonded via N,
Y für einen Rest aus der Reihe Wasserstoff, Methyl, Cyano, gegebenenfalls einfach bis mehrfach unabhängig voneinander durch Halogen, C1-C4- Alkoxy, Ci-C4-Alkyl-S(0)m- oder Cyano substituiertes Ci-Cö-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4-Y is a radical selected from hydrogen, methyl, cyano, optionally mono- or polysubstituted independently of one another by halogen, C 1 -C 4 - alkoxy, Ci-C 4 alkyl-S (0) m - or cyano-substituted C COE Alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally monosubstituted to disubstituted by halogen, C 1 -C 4 -
Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes Cs-Cs-Cycloalkyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch O, S(0)m, CO oder NR2 unterbrochenes und gegebenenfalls einfach bis vierfach unabhängig voneinander durch Halogen, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substitu- iertes, geradkettiges oder verzweigtes C3-C8-Cycloalkyl-Ci-C4-alkyl und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, Ci-C4-Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Nitro oder Cyano substituiertes Arylalkyl oder Hetarylalkyl steht, m für eine Zahl 0, 1 oder 2 steht, Alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano-substituted Cs-Cs-cycloalkyl, optionally mono- or disubstituted independently of one another by O, S (0) m, CO or NR 2 is interrupted and is optionally mono- to tetrasubstituted independently of one another by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano substitution iertes, straight or branched C 3 -C 8 cycloalkyl-Ci-C4-alkyl, and is optionally mono- to trisubstituted independently of one another by halogen, C 1 -C 4 - alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S (0) m -, C 4 haloalkoxy, C C4-haloalkyl-S (0) m -, nitro or cyano substituted arylalkyl or hetarylalkyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, gegebenenfalls einfach bis mehrfach unabhängig voneinander durch Halogen, C1-C4- Alkoxy, Ci-C4-Alkyl-S(0)m- oder Cyano substituiertes CI-CÖ- Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C t-Alkoxy oder Cyano substituiertes C3-C6-Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C8-Cycloalkyl-Ci-C4-alkyl steht, A represents a radical selected from hydrogen, methyl, which is optionally monosubstituted to polysubstituted independently of one another by halogen, C 1 -C 4 - alkoxy, Ci-C4-alkyl-S (0) m - or cyano-substituted CI-COE alkyl, C3 -C 6 alkenyl or C 3 -C 6 alkynyl and optionally mono- to disubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or cyano-substituted C 3 -C 6 -cycloalkyl and optionally monosubstituted or disubstituted independently of one another by halogen, C 1 - C4 alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy or cyano, straight or branched C3-C8-cycloalkyl-Ci-C 4 alkyl,
R2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
Alkinyl oder Cycloalkyl steht,  Alkynyl or cycloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
Weiterhin bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (1-2). Further preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Their combination forms the preferred range (1-2).
Dabei sind die Reste Q, V, W, Y, m, A, R2 und T definiert wie in Vorzugsbereich (1-1) und The radicals Q, V, W, Y, m, A, R 2 and T are defined as in the preferred range (1-1) and
X steht für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinander durch X is a radical from the series, optionally mono- to polysubstituted independently of one another
Halogen, NLlL2, Nitro, Cyano oder gegebenenfalls substituiertes Alkyl, Halogenalkyl, Alkoxy, Alkyl-S(0)m-, Halogenalkoxy, Halogenalkyl-S(0)m-, Carboxy, Aryl oder Heta- ryl substituiertes Aryl oder Hetaryl oder für einen Aryl oder Hetarylring, welcher an zwei benachbarten Ringpositionen eine aus einem bis zwei Heteroatomen aus der Reihe N, S oder O und/oder einem bis fünf Kohlenstoffatomen bestehnde Kette gebunden hat und diese dabei einen gegenenefalls teilweise ungesättigten aliphatischen, aromatischen, heteroaromatischen oder gegebenenfalls teilweise ungesättigten heterocyclischen Ring bildet, wobei Halogen, NL l L 2 , nitro, cyano or optionally substituted alkyl, haloalkyl, alkoxy, alkyl-S (0) m -, haloalkoxy, haloalkyl-S (0) m -, carboxy, aryl or hetero-substituted aryl or hetaryl or an aryl or hetaryl ring which has attached to two adjacent ring positions a chain consisting of one to two heteroatoms from the series N, S or O and / or one to five carbon atoms and which hereby has a partially unsaturated aliphatic, aromatic, heteroaromatic or optionally forming partially unsaturated heterocyclic ring, wherein
L für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, L is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
Alkinyl oder Cycloalkyl steht, für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, oder Alkynyl or cycloalkyl, a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättigten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht. L 1 and L 2 together with N is an N-bonded, optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms.
Besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufge- führten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (2-1). Particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Their combination forms the preferred range (2-1).
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
V für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluor- methyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy und Cyano steht, W für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluor- methyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy und Cyano steht, V is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano, W is a radical from the series consisting of hydrogen, fluorine, chlorine, bromine , Methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano,
X für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinander durch Halogen, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, G-C4-X is a radical from the series which is optionally monosubstituted to polysubstituted independently of one another by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S (0) m - , GC 4 -
Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Ci-C4-Carboxy, NI^L2, Nitro, Cyano oder einfach bis dreifach unabhängig voneinander durch Halogen, Ci-C4-Alkyl, Ci-C4- Halogenalkyl, Ci-C -Alkoxy, Ci-C -Alkyl-S(0)m-, Ci-C -Halogenalkoxy, Ci-C - Halogenalkyl-S(0)m-, Nitro oder Cyano substituiertes Aryl oder Hetaryl substituiertes Aryl oder Hetaryl steht, wobei Haloalkoxy, Ci-C 4 -haloalkyl-S (0) m -, Ci-C 4 -Carboxy, NI ^ L 2 , nitro, cyano or monosubstituted to trisubstituted independently by halogen, Ci-C 4 alkyl, Ci-C 4 - haloalkyl, Ci-C-alkoxy, Ci-C-alkyl-S (0) m -, Ci-C-haloalkoxy, Ci-C - haloalkyl-S (0) m -, substituted nitro or cyano substituted aryl or hetaryl Aryl or hetaryl stands, where
L1 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2-L 1 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkyl,
C4-Alkenyl, C2-C4-Alkinyl oder C3-C6-Cycloalkyl steht, C 4 alkenyl, C 2 -C 4 alkynyl or C 3 -C 6 cycloalkyl,
L2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2- C -Alkenyl, C2-C -Alkinyl oder C3-C6-Cycloalkyl steht, oder L 2 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -C -alkenyl, C 2 -C -alkynyl or C 3 -C 6 -cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättigten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht, L 1 and L 2 together with N represents an optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms bonded via N,
Y für einen Rest aus der Reihe Wasserstoff, Cyano, gegebenenfalls einfach bis fünffach unabhängig voneinander durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m- oderCyano substituiertes Ci-C4-Alkyl, C3-C4-Alkenyl oder C3-C4-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes C3-C6- Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch O, S(0)m, CO oder NR2 unterbrochenes und gegebenenfalls einfach bis vierfach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C6-Cycloalkyl-Ci-C2-alkyl steht, m für eine Zahl 0, 1 oder 2 steht, Y for a remainder of the series hydrogen, cyano, which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci-C4 alkyl, C3-C4 alkenyl, or C 3 -C 4 -alkynyl, optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C 6 -cycloalkyl and optionally mono- to disubstituted independently of one another by O, S (0) m , CO or NR 2 interrupted, optionally monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano, straight-chain or branched C 3 -C 6 cycloalkyl-Ci-C 2- alkyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, gegebenenfalls einfach bis fünffach unabhängig voneinander durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m- oder Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes C3-C6- Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C6-Cycloalkyl-Ci-C2-alkyl steht, A represents a radical selected from hydrogen, methyl, which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci- -alkyl, C 3 -C 6 alkenyl or C 3 -C 6 -alkynyl optionally mono- or disubstituted independently by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C6- Cycloalkyl and optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted, straight-chain or branched C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl,
R2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl,
Alkinyl oder Cycloalkyl steht,  Alkynyl or cycloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
Weiterhin besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich Furthermore, particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Their combination is the preferred area
Dabei sind die Reste Q, V, W, Y, m, A, R2 und T definiert wie in Vorzugsbereich (2-1) und steht für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinander durch The radicals Q, V, W, Y, m, A, R 2 and T are defined as in the preferred range (2-1) and is a radical from the series, optionally mono- to polysubstituted independently of one another
Halogen, Ci-C4-Alkyl, Ci-C -Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, C1-C4- Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Ci-C4-Carboxy, NL1! , Nitro, Cyano oder gegebenenfalls einfach bis dreifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, Ci-C4-Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Nitro oder Cyano substituiertes Aryl oder Hetaryl substituiertes Aryl oder Hetaryl oder für einenAryl oder Hetarylring , welcher an zwei benachbarten Ringpositionen eine aus einem oder zwei Heteroatomen aus der Reihe N, S oder O und einem oder zwei Kohlenstoffatomen bestehende Kette gebunden hat und diese dabei einen heteroaromatischen oder gegebenefalls teilweise ungesättigten heterocyclischen Ring bildet, wobei Halogen, C 1 -C 4 -alkyl, C 1 -C -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl-S (O) m -, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl-S ( 0) m -, Ci-C4-carboxy, NL 1 ! , Nitro, cyano or optionally mono- to trisubstituted independently of one another by halogen, C 1 -C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S (0) m -, C C 4 haloalkoxy, Ci-C4-haloalkyl-S (0) m -, nitro or cyano substituted aryl or hetaryl substituted aryl or hetaryl or for an aryl or hetaryl ring, which at two adjacent ring positions one from one or two heteroatoms from the series N, S or O and one or two carbon atoms connected chain and this forms a heteroaromatic or optionally partially unsaturated heterocyclic ring, wherein
L für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2- C4-Alkenyl, C2-C4-Alkinyl oder C3-C6-Cycloalkyl steht, L is a radical selected from hydrogen, optionally substituted Ci-C 4 alkyl, C 2 - C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 cycloalkyl,
L2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2-L 2 is a radical selected from the group consisting of hydrogen, optionally substituted C 1 -C 4 -alkyl, C 2 -
C4-Alkenyl, C2-C4-Alkinyl oder C3-C6-Cycloalkyl steht, oder C 4 alkenyl, C 2 -C 4 alkynyl or C 3 -C 6 cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättig- ten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht. L 1 and L 2 together with N is an N-bonded, optionally substituted, saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms.
Ganz besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufgeführten Reste werden im Folgenden erläutert. Unter Berücksichtigung der Position der Carbo- xamidgruppe am Imidazolrest ergibt sich die ganz besonders bevorzugte Struktur (II). Ihre Kombination bildet den Vorzugsbereich (3-1). Very particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Taking into account the position of the carboxamide group on the imidazole radical, the most preferred structure (II) results. Their combination forms the preferential range (3-1).
für Sauerstoff oder Schwefel steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Methyl und Cyano steht, für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom. Methyl, Ethyl und Cyano steht, für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Trifluormethyl-S(0)m-, Difluorefhyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4- yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethylamino, Diethylamino, Ethylmethylami- no, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Trifluormethyl- S(0)m-, Difluorethyl-S(0)m-, Trifluorefhyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropy- lcarbonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothia- zolyl, Pyrazolyl, Imidazolyl, Oxadiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4- yi substituiertes Aryl oder Hetaryl steht, für einen Rest aus der Reihe Wasserstoff, Benzyl, gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Methoxy, Ethoxy oder Cyano substituiertes Methyl, Ethyl, Propyl, Allyl oder Propargyl steht, für eine Zahl 0, 1 oder 2 steht, A für einen Rest aus der Reihe Wasserstoff, gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Methoxy, Ethoxy oder Cyano substituiertes Methyl, Ethyl, Propyl, Allyl, Propargyl, Cylopropyl oder Cyclopropylmethyl steht und is oxygen or sulfur, is a radical from the series hydrogen, fluorine, chlorine, methyl and cyano, is a radical from the series hydrogen, fluorine, chlorine, bromine. Methyl, ethyl and cyano, represents a radical from the series optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluorofhyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro -2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano and optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) m -, Difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0) m-, trifluorofhyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-Etho xy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl or cyano-substituted phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl , Imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or l, 2,3-triazole-4-yi substituted aryl or hetaryl, is a radical from the series hydrogen, benzyl, optionally mono- to trisubstituted independently of one another by fluorine, methoxy , Ethoxy or cyano is substituted methyl, ethyl, propyl, allyl or propargyl, a number is 0, 1 or 2, A is a radical selected from the group consisting of hydrogen, optionally monosubstituted to trisubstituted independently of one another by fluorine, methoxy, ethoxy or cyano, methyl, ethyl, propyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl and
T für Sauerstoff oder ein Elektronenpaar steht. Aus Formel (I) ergibt sich unter Berücksichtigung der Position der Carboxamidgruppe am Imidazol- rest die ganz besonders bevorzugte Struktur (II) und deren Salze. Ganz besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (II) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (3-2), T stands for oxygen or an electron pair. Taking into account the position of the carboxamide group on the imidazole radical, formula (I) gives the very particularly preferred structure (II) and salts thereof. Very particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (3-2),
Dabei sind die Reste Q, V, W, Y, m, A und T definiert wie in Vorzugsbereich (3-1) und X steht für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Trifluormethyl-S(0)m-, Difluorefhyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4- yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethylamino, Diethylamino, Ethylmethylami- no, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Trifluormethyl- S(0)m-, Difluorethyl-S(0)m-, Trifluorefhyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropy- lcarbonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothia- zolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl substituiertes Aryl oder Hetaryl oder für einen Aryl oder Hetarylring, welcher an zwei benachbarten Ringpositionen eine aus einem oder zwei Sauerstoffatomen und einem oder zwei Kohlenstoffatomen bestehende Kette gebunden hat und diese dabei einen heteroaromatischen oder gegebenefalls teilweise ungesättigten heterocyclischen Ring bildet. Insbesonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (I) aufgeführten Reste werden im Folgenden erläutert. Unter Berücksichtigung der Position der Carboxamid- gruppe am Imidazolrest ergibt sich die insbesonders bevorzugte Struktur (II). Ihre Kombination mit den insbesonders bevorzugten Substituenten bildet den Vorzugsbereich (4-1). The radicals Q, V, W, Y, m, A and T are defined as in the preferred range (3-1) and X is a radical from the series, where appropriate, monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, Ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, Difluorofhyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano and optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0) m -, trifluorofhyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) m ethyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl or cyano-substituted phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl , Isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxdiazolyl, thiadiazolyl, benzofuran-2-yl or l, 2,3-triazol-4-yl substituted aryl or hetaryl or for an aryl or hetaryl ring which is present at two adjacent ring positions has attached a chain consisting of one or two oxygen atoms and one or two carbon atoms and this forms a heteroaromatic or optionally partially unsaturated heterocyclic ring. Particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (I) are explained below. Taking into account the position of the carboxamide Group on Imidazolrest results in the particularly preferred structure (II). Their combination with the particularly preferred substituents forms the preferred range (4-1).
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
V für Wasserstoff und Fluor steht, V is hydrogen and fluorine,
W für einen Rest aus der Reihe Wasserstoff, Chlor, Brom und Methyl steht, W is a radical from the series hydrogen, chlorine, bromine and methyl,
X für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch X is a radical from the series optionally simply to three times independently by
Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl- S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Triflu- ormethyl-S(0)m-, Difluorefhyl-S(0)m-, Trifluorefhyl-S(0)m-, (Tetrahydro-2H-pyran-4- yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethylamino, Diethylamino, Ethylmethylami- no, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)n-, Difluormethoxy, Trifluormethoxy, Trifluormethyl- S(0)m-, Difluorethyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropy- lcarbonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothia- zolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl steht, Fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) m -, difluoromethoxy, trifluoromethoxy , Trifluoromethyl-S (0) m -, difluorofhyl-S (0) m -, trifluorofhyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2 Ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano and optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy , Ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) n -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0 ) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholine-4 -yl or cyano-substituted phenyl, naphthyl, pyridyl, pyrimidyl, Pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxdiazolyl, thiadiazolyl, benzofuran-2-yl or l, 2,3-triazol-4-yl substituted phenyl, naphthyl, Pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or 1,2,3-triazol-4-yl,
Y für einen Rest aus der Reihe Wasserstoff, Methyl, Ethyl, Propyl, Difluorethyl, Trifluorethyl, Methoxymethyl, Ethoxymethyl, Cyanomethyl und Benzyl steht, m für eine Zahl 0, 1 oder 2 steht, Y is a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and benzyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, Ethyl, Propyl, Difluorethyl, Trifluorethyl, Methoxymethyl, Ethoxymethyl, Cyanomethyl, Allyl, Propargyl, Cylopropyl oder Cyclopropyl- methyl steht, A is a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl,
T für Sauerstoff oder ein Elektronenpaar steht und deren Salze. Aus Formel (I) ergibt sich unter Berücksichtigung der Position der Carboxamidgruppe am Imidazol- rest die insbesonders bevorzugte Struktur (II) und deren Salze. Insbesonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (II) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (4-2), Dabei sind die Reste Q, V, W, Y, m, A und T definiert wie in Vorzugsbereich (4-1) und T is oxygen or a pair of electrons and their salts. Taking into account the position of the carboxamide group on the imidazole radical, formula (I) gives the particularly preferred structure (II) and salts thereof. Particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (4-2), The radicals Q, V, W, Y, m, A and T are defined as in the preferred range (4-1) and
X steht für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch X is a radical from the series, if appropriate, simply to three times independently
Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl- S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Triflu- ormefhyl-S(0)m-, Difluorefhyl-S(0)m-, Trifluorefhyl-S(0)m-, (Tetrahydro-2H-pyran-4- yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethylamino, Diethylamino, Ethylmethylami- no, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)n-, Difluormethoxy, Trifluormethoxy, Trifluormethyl-Fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) m -, difluoromethoxy, trifluoromethoxy , Trifluoromethyl-S (0) m -, difluorofhyl-S (0) m -, trifluorofhyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2 Ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano and optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy , Ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) n -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-
S(0)m-, Difluorethyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropy- lcarbonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothia- zolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl oder für ein Phenyl, welches an zwei benachbarten Ringpositionen eine aus einem oder zwei Sauerstoffatomen und einem oder zwei Kohlenstoffatomen bestehende Kette gebunden hat und diese dabei einen gegebenenfalls teilweise ungesättigten heterocyclischen Ring bildet. S (0) m -, difluoroethyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2- oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl or cyano-substituted phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxdiazolyl , Thiadiazolyl, benzofuran-2-yl or l, 2,3-triazol-4-yl substituted phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl , Oxdiazolyl, thiadiazolyl, benzofuran-2-yl or l, 2,3-triazol-4-yl or a phenyl which has bonded to two adjacent ring positions a chain consisting of one or two oxygen atoms and one or two carbon atoms and these forms an optionally partially unsaturated heterocyclic ring.
Ganz besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (II) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (5- 1). Very particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (5-1).
Q für Sauerstoff oder Schwefel und bevorzugt für Sauerstoff steht, für Wasserstoff steht, Q is oxygen or sulfur and preferably oxygen, stands for hydrogen,
für einen Rest aus der Reihe Wasserstoff, Chlor und Brom und bevorzugt für Wasserstoff steht, is a radical from the series hydrogen, chlorine and bromine and is preferably hydrogen,
für einen Rest aus der Reihe 3-[(2,2,2-Trifluorethyl)sulfanyl]phenyl, 2-Fluor-4-methyl-5- [(2,2,2-trifluorethyl)sulfanyl]phenyl, 3-(Methylsulfanyl)phenyl, Pyrimidin-2-yl, 3-[(2,2,2- Trifluorethyl)sulfinyl]phenyl, Phenyl, Pyridin-3-yl, 3,5-Dimethylphenyl, 2-Chlorphenyl, 3- Chlorphenyl, 4-Chlorphenyl, 2,4-Dichlorphenyl, 3,4-Dichlorphenyl, l-Methyl-lH-pyrrol-2-yl, 3-Furyl, 2,5-Dimethyl-3-thienyl, 3-[(Trifluormethyl)sulfanyl]phenyl, 3-a radical from the series 3 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 2-fluoro-4-methyl-5- [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3- (methylsulfanyl ) phenyl, pyrimidin-2-yl, 3 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl , 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3 - [(trifluoromethyl) sulfanyl] -phenyl, 3 -
[(Cyclopropylmethyl)sulfanyl]phenyl, 3-(Methoxymethyl)phenyl, 3-[(Tetrahydro-2H-pyran-4- yloxy)methyl] phenyl, 3-(Dimethylsulfamoyl)phenyl, 3-(Methylsulfonyl)phenyl, 4-Methyl-3- (methylsulfanyl)phenyl, l-(2-Cyanphenyl)-lH-pyrazol-4-yl, l-(4-Fluorphenyl)-lH-pyrazol-4- yl, l-Phenyl-lH-pyrazol-4-yl, 1-Naphthyl, 5-(Methoxycarbonyl)-l-naphthyl, 4-Fluor-2- (methoxycarbonyl)phenyl, 4-Fluor-l-naphthyl, 4-Chlor-3-(ethoxycarbonyl)phenyl, 2- (Methoxycarbonyl)phenyl, Pyridin-4-yl, 6-(Ethoxycarbonyl)pyridin-2-yl, 3- (Ethoxycarbonyl)phenyl, 2-Naphthyl, 4-Methoxy-3-(methoxycarbonyl)phenyl, 4-Chlor-2- (methoxycarbonyl)phenyl, 3-Thienyl, 3-(2-Ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2- Ethoxy-2-oxoethoxy)phenyl, 3-(2-Ethoxy-2-oxoethoxy)-4,5-difluorphenyl, 3-(2-Ethoxy-2- oxoethoxy)-4-fluorphenyl, 3-(Ethoxycarbonyl)-4-fluorphenyl, (3-[(Cyclopropylmethyl) sulfanyl] phenyl, 3- (methoxymethyl) phenyl, 3 - [(tetrahydro-2H-pyran-4-yloxy) methyl] phenyl, 3- (dimethylsulfamoyl) phenyl, 3- (methylsulfonyl) phenyl, 4-methyl -3- (methylsulfanyl) phenyl, 1- (2-cyanophenyl) -1H-pyrazol-4-yl, 1- (4-fluorophenyl) -1H-pyrazol-4-yl, 1-phenyl-1H-pyrazole-4 yl, 1-naphthyl, 5- (methoxycarbonyl) -1-naphthyl, 4-fluoro-2- (methoxycarbonyl) phenyl, 4-fluoro-1-naphthyl, 4-chloro-3- (ethoxycarbonyl) phenyl, 2- (methoxycarbonyl ) phenyl, pyridin-4-yl, 6- (ethoxycarbonyl) pyridin-2-yl, 3- (ethoxycarbonyl) phenyl, 2-naphthyl, 4-methoxy-3- (methoxycarbonyl) phenyl, 4-chloro-2- (methoxycarbonyl ) phenyl, 3-thienyl, 3- (2-ethoxy-2-oxoethoxy) -4-methylphenyl, 3- (2-ethoxy-2-oxoethoxy) phenyl, 3- (2-ethoxy-2-oxoethoxy) -4, 5-difluorophenyl, 3- (2-ethoxy-2-oxoethoxy) -4-fluorophenyl, 3- (ethoxycarbonyl) -4-fluorophenyl, (3
{ [(Cyclopropylcarbonyl)oxy]methyl}phenyl, 3-{ [(Cyclopropylcarbonyl)oxy]methyl}-4- fluorphenyl, Pyridin-2-yl, 3-(Difluormethyl)phenyl, 3-[(Trifluormethyl)sulfinyl]phenyl, 4- Fluor-3-(trifluormethyl)phenyl, 3-Chlor-5-(trifluormethyl)phenyl, 3-(Trifluormethyl)phenyl, 3,5-Bis(trifluormethyl)phenyl, 3-Fluor-5-(trifluormethyl)phenyl, 4-Cyan-3-{[(Cyclopropylcarbonyl) oxy] methyl} phenyl, 3- {[(cyclopropylcarbonyl) oxy] methyl} -4-fluorophenyl, pyridin-2-yl, 3- (difluoromethyl) phenyl, 3 - [(trifluoromethyl) sulfinyl] phenyl, 4-fluoro-3- (trifluoromethyl) phenyl, 3-chloro-5- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-fluoro-5- (trifluoromethyl) phenyl, 4-cyano-3-
(trifluormethyl)phenyl, 3-(2,2,2-Trifluorethyl)phenyl, 3-(Pentafluorethyl)phenyl, 3- Cyanphenyl, 4-Chlor-3-cyanphenyl, 3-Cyan-5-fluorphenyl, 3-Cyan-5-(trifluormethyl)phenyl, 5-Cyan-2-methoxyphenyl, 3-Cyan-4-fluorphenyl, 5-Cyanpyridin-3-yl, 5-Cyan-6- (dimethylamino)pyridin-3-yl, 5-Cyan-6-(morpholin-4-yl)pyridin-3-yl, 5-Cyan-6- ethoxypyridin-3-yl, 5-Cyan-6-methoxypyridin-3-yl, 3-Chlor-5-cyanphenyl, l-Benzofuran-2-yl,(trifluoromethyl) phenyl, 3- (2,2,2-trifluoroethyl) phenyl, 3- (pentafluoroethyl) phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5 - (trifluoromethyl) phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6- (dimethylamino) pyridin-3-yl, 5-cyano-6 - (morpholin-4-yl) pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran 2-yl,
3- Phenyl- 1 ,2-oxazol-5-yl, 3-(Ethoxycarbonyl)- 1 ,2-oxazol-5-yl, 1-Isopropyl- 1H- 1,2,3-triazol-3-phenyl-1,2-oxazol-5-yl, 3- (ethoxycarbonyl) -1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazole
4- yl, l-Methyl-lH-l,2,3-triazol-4-yl oder 5-Cyan-6-methoxypyridin-3-yl, für Methyl steht, 4-yl, 1-methyl-1H-1,2,3-triazol-4-yl or 5-cyano-6-methoxypyridin-3-yl, is methyl,
für einen Rest aus der Reihe Wasserstoff, Methyl und Ethyl und bevorzugt für Methyl und Ethyl steht und is a radical selected from the group of hydrogen, methyl and ethyl and is preferably methyl and ethyl and
für ein Elektronenpaar steht. Weiterhin ganz besonders bevorzugte Substituenten bzw. Bereiche der in den Verbindungen der Formel (II) aufgeführten Reste werden im Folgenden erläutert. Ihre Kombination bildet den Vorzugsbereich (5-2) für die Verbindungen der Formel (Π) und deren Salze. stands for an electron pair. Furthermore, very particularly preferred substituents or ranges of the radicals listed in the compounds of the formula (II) are explained below. Their combination forms the preferred range (5-2) for the compounds of formula (Π) and their salts.
Dabei sind die Reste Q, V, W, Y, A und T definiert wie in Vorzugsbereich (5-1) und The radicals Q, V, W, Y, A and T are defined as in the preferred range (5-1) and
X steht für einen Rest aus der Reihe 3-[(2,2,2-Trifluorethyl)sulfanyl]phenyl, 2-Fluor-4- methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl, 3-(Methylsulfanyl)phenyl, Pyrimidin-2- yl, 3-[(2,2,2-Trifluorethyl)sulfinyl]phenyl, Phenyl, Pyridin-3-yl, 3,5-Dimethylphenyl, 2- Chlorphenyl, 3-Chlorphenyl, 4-Chlorphenyl, 2,4-Dichlorphenyl, 3,4-Dichlorphenyl, 1- Methyl-lH-pyrrol-2-yl, 3-Furyl, 2,5-Dimethyl-3-thienyl, 3-X is a radical from the series 3 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3 (Methylsulfanyl) phenyl, pyrimidin-2-yl, 3 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4 -Chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3
[(Trifluormethyl)sulfanyl]phenyl, 3-[(Cyclopropylmethyl)sulfanyl]phenyl, 3- (Methoxymethyl)phenyl, 3-[(Tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3- (Dimethylsulfamoyl)phenyl, 3-(Methylsulfonyl)phenyl, 4-Methyl-3-[(Trifluoromethyl) sulfanyl] phenyl, 3 - [(cyclopropylmethyl) sulfanyl] phenyl, 3- (methoxymethyl) phenyl, 3 - [(tetrahydro-2H-pyran-4-yloxy) methyl] phenyl, 3- (dimethylsulfamoyl) phenyl, 3- (methylsulfonyl) phenyl, 4-methyl-3-
(methylsulfanyl)phenyl, 1 -(2-Cyanphenyl)- lH-pyrazol-4-yl, 1 -(4-Fluorphenyl)- 1H- pyrazol-4-yl, 1 -Phenyl- lH-pyrazol-4-yl, 1-Naphthyl, 5-(Methoxycarbonyl)-l-naphthyl,(methylsulfanyl) phenyl, 1- (2-cyanophenyl) -1H-pyrazol-4-yl, 1- (4-fluorophenyl) -1H-pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1 -Naphthyl, 5- (methoxycarbonyl) -l-naphthyl,
4- Fluor-2-(methoxycarbonyl)phenyl, 4-Fluor- 1 -naphthyl, 4-Chlor-3- (ethoxycarbonyl)phenyl, 2-(Methoxycarbonyl)phenyl, Pyridin-4-yl, 6- (Ethoxycarbonyl)pyridin-2-yl, 3-(Ethoxycarbonyl)phenyl, 2-Naphthyl, 4-Methoxy-3- (methoxycarbonyl)phenyl, 4-Chlor-2-(methoxycarbonyl)phenyl, 3-Thienyl, 3-(2- Ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-Ethoxy-2-oxoethoxy)phenyl, 3-(2-Ethoxy- 2-oxoethoxy)-4,5-difluorphenyl, 3-(2-Ethoxy-2-oxoethoxy)-4-fluorphenyl, 3- (Ethoxycarbonyl)-4-fluorphenyl, (3-{ [(Cyclopropylcarbonyl)oxy]methyl}phenyl, 3- { [(Cyclopropylcarbonyl)oxy]methyl}-4-fluorphenyl, Pyridin-2-yl, 3- (Difluormethyl)phenyl, 3- [(Trifluormethyl)sulfinyl]phenyl, 4-Fluor-3- (trifluormethyl)phenyl, 3-Chlor-5-(trifluormethyl)phenyl, 3-(Trifluormethyl)phenyl, 3,5- Bis(trifluormethyl)phenyl, 3-Fluor-5-(trifluormethyl)phenyl, 4-Cyan-3- (trifluormethyl)phenyl, 3-(2,2,2-Trifluorethyl)phenyl, 3-(Pentafluorethyl)phenyl, 3- Cyanphenyl, 4-Chlor-3-cyanphenyl, 3-Cyan-5-fluorphenyl, 3-Cyan-5- (trifluormethyl)phenyl, 5-Cyan-2-methoxyphenyl, 3-Cyan-4-fluorphenyl, 5- Cyanpyridin-3-yl, 5-Cyan-6-(dimethylamino)pyridin-3-yl, 5-Cyan-6-(morpholin-4- yl)pyridin-3-yl, 5-Cyan-6-ethoxypyridin-3-yl, 5-Cyan-6-methoxypyridin-3-yl, 3-Chlor-4-fluoro-2- (methoxycarbonyl) phenyl, 4-fluoro-1-naphthyl, 4-chloro-3- (ethoxycarbonyl) phenyl, 2- (methoxycarbonyl) phenyl, pyridin-4-yl, 6- (ethoxycarbonyl) pyridine 2-yl, 3- (ethoxycarbonyl) phenyl, 2-naphthyl, 4-methoxy-3- (methoxycarbonyl) phenyl, 4-chloro-2- (methoxycarbonyl) phenyl, 3-thienyl, 3- (2-ethoxy-2- oxoethoxy) -4-methylphenyl, 3- (2-ethoxy-2-oxoethoxy) phenyl, 3- (2-ethoxy-2-oxoethoxy) -4,5-difluorophenyl, 3- (2-ethoxy-2-oxoethoxy) - 4-fluorophenyl, 3- (ethoxycarbonyl) -4-fluorophenyl, (3- {[(cyclopropylcarbonyl) oxy] methyl} phenyl, 3- {[(cyclopropylcarbonyl) oxy] methyl} -4-fluorophenyl, pyridin-2-yl, 3- (Difluoromethyl) phenyl, 3- [(trifluoromethyl) sulfinyl] phenyl, 4-fluoro-3- (trifluoromethyl) phenyl, 3-chloro-5- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 3.5- Bis (trifluoromethyl) phenyl, 3-fluoro-5- (trifluoromethyl) phenyl, 4-cyano-3- (trifluoromethyl) phenyl, 3- (2,2,2-trifluoroethyl) phenyl, 3- (pentafluoroethyl) phenyl, 3 Cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5- (trifluoromethyl) ph enyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6- (dimethylamino) pyridin-3-yl, 5-cyano-6 (morpholine) 4-yl) pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro
5- cyanphenyl, l-Benzofuran-2-yl, 3-Phenyl-l,2-oxazol-5-yl, 3-(Ethoxycarbonyl)-l,2- oxazol-5-yl, l-Isopropyl-lH-l,2,3-triazol-4-yl, 1 -Methyl- lH-l,2,3-triazol-4-yl, 5-Cyan-5-cyano-phenyl, 1-benzofuran-2-yl, 3-phenyl-1,2-oxazol-5-yl, 3- (ethoxycarbonyl) -l, 2-oxazol-5-yl, 1-isopropyl-1H-1, 2,3-triazol-4-yl, 1-methyl-1H-1,2,3-triazol-4-yl, 5-cyano
6- methoxypyridin-3-yl, 6-Methoxypyridin-2-yl, 2,3-Dihydro-l-benzofuran-7-yl, 1- Benzofuran-7-yl, 2,6-Dimethoxypyridin-3-yl, 2-Methoxyphenyl, 1,3-Benzodioxol-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran-7-yl, 2,6-dimethoxypyridin-3-yl, 2 Methoxyphenyl, 1,3-benzodioxole
4- yl, 2,4-Dimethoxyphenyl, 2,5-Dimethoxyphenyl, 6-(Trifluormethyl)pyridin-2-yl,4-yl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 6- (trifluoromethyl) pyridin-2-yl,
5- Chlor-2-methoxypyridin-3-yl, 2-Methoxypyridin-3-yl, 6-Ethoxypyridin-3-yl, 5- Chlor-6-methoxypyridin-3-yl, 2-(Methylsulfanyl)pyridin-3-yl, 2-Ethoxypyridin-3-yl, 5,6-Dimethoxypyridin-3-yl, 2-Methoxypyridin-4-yl, 6-Mefhoxy-5- (trifluormethyl)pyridin-3-yl, 6-Methoxy-5-nitropyridin-3-yl, 2,6-Dimefhoxypyridin- 4-yl, 2- (Methylsulf anyl)phenyl, 2-Methoxy-6-(trifluormethyl)-pyridin-4-yl, 3- Cyan-5-methoxypheriyl, 5-Fluor-2-methoxypyridin-3-yl, 6-Isopropoxypyridin-3- yl, 6-Methoxypyridin-3-yl, 2-(2-Amino-2-oxoethoxy)phenyl, 3-Cyan-4- isopropoxyphenyl oder 3-Chlorpyridin-2-yl. 5-chloro-2-methoxypyridin-3-yl, 2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5- Chloro-6-methoxypyridin-3-yl, 2- (methylsulfanyl) pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy -5- (trifluoromethyl) pyridin-3-yl, 6-methoxy-5-nitropyridin-3-yl, 2,6-dimefoxypyridin-4-yl, 2- (methylsulfinyl) phenyl, 2-methoxy-6- (trifluoromethyl ) -pyridin-4-yl, 3-cyano-5-methoxypheriyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl, 6-methoxypyridin-3-yl, 2- (2-amino 2-oxoethoxy) phenyl, 3-cyano-4-isopropoxyphenyl or 3-chloropyridin-2-yl.
Im Vorzugsbereich (1-1) oder (1-2) ist, sofern nichts anderes angegeben ist, In the preferred range (1-1) or (1-2), unless otherwise stated,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und lod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine,
Hetaryl (gleichbedeutend mit Heteroaryl, auch als Teil einer größeren Einheit, wie beispielsweise Hetarylalkyl) ausgewählt aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, 1,2,3- Triazolyl, 1,2,4-Triazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1,2,3-Oxadiazolyl, 1,2,4- Oxadiazolyl, 1,3,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,3,4- Thiadiazolyl, 1,2,5-Thiadiazolyl, Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, 1,2,3-Triazinyl, 1,2,4- Triazinyl, 1,3,5-Triazinyl, Benzofuryl, Benzisofuryl, Benzothienyl, Benzisothienyl, Indolyl, Isoin- dolyl, Indazolyl, Benzothiazolyl, Benzisothiazolyl, Benzoxazolyl, Benzisoxazolyl, Benzimidazolyl, 2,1,3-Benzoxadiazole, Chinolinyl, Isochinolinyl, Cinnolinyl, Phthalazinyl, Chinazolinyl, Chinoxali- nyl, Naphthyridinyl, Benzotriazinyl, Purinyl, Pteridinyl und Indolizinyl, Heterocyclyl für einen gesättigten 3-, 4-, 5- oder 6-Ring, der 1 oder 2 Stickstoffatome und/oder ein Sauerstoffatom und/oder ein Schwefelatom enthält, wobei jedoch nicht 2 Stickstoffatome direkt benachbart sein sollen, beispielsweise für Aziridinyl, Azetidinyl, Azolidinyl, Azinanyl, Oxiranyl, O- xetanyl, Oxolanyl, Oxanyl, Dioxanyl, Thiiranyl, Thietanyl, Thiolanyl, Thianyl, Tetrahydrofuryl. Hetaryl (equivalent to heteroaryl, also as part of a larger unit such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl , Thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4 Thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl , Benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazoles, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl , Benzotriazinyl, purinyl, pteridinyl and indolizinyl, heterocyclyl for a saturated 3-, 4-, 5- or 6-membered ring containing 1 or 2 nitrogen atoms and / or one oxygen atom and / or ei but not 2 nitrogen atoms to be directly adjacent, for example, aziridinyl, azetidinyl, azolidinyl, azinanyl, oxiranyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiiranyl, thietanyl, thiolanyl, thianyl, tetrahydrofuryl.
Im Vorzugsbereich (2-1) oder (2-2) steht, sofern nichts anderes angegeben ist, Halogen für Fluor, Chlor, Brom und lod, bevorzugt für Fluor, Chlor und Brom, In the preferred range (2-1) or (2-2), unless otherwise stated, halogen is fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine,
Hetaryl (auch als Teil einer größeren Einheit, wie Hetarylalkyl) für Pyridyl, Pyrimidyl, Thiazolyl, Oxazolyl, Pyrazolyl, Thienyl, Furanyl, Benzyl, Pyridinylmethyl und Thiazolylmethyl sowie Hetaryl (also as part of a larger moiety, such as hetarylalkyl) for pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl, benzyl, pyridinylmethyl and thiazolylmethyl and
Heterocyclyl (auch als Teil einer größeren Einheit, wie Heterocyclylalkyl) für einen gesättigten oder ungesättigten 3-, 4- oder 5-Ring, der 1 oder 2 Stickstoffatome und/oder ein Sauerstoffatom und/oder ein Schwefelatom enthält, wobei jedoch nicht 2 Stickstoffatome direkt benachbart sein sollen, beispielsweise für 1- oder 2- Aziridinyl, 2-Oxiranyl, 2-Thiiranyl, 1- oder 2- Azetidinyl, 2- oder 3- Oxetanyl, 2- oder 3-Thietanyl, l,3-Dioxetan-2-yl, 1-, 2- oder 3-Pyrrolidinyl. Im Vorzugsbereich (3-1) oder (3-2) steht, sofern nichts anderes angegeben ist, Heterocyclyl (also as part of a larger unit such as heterocyclylalkyl) for a saturated or unsaturated 3-, 4- or 5-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, but not 2 nitrogen atoms directly to be adjacent, for example 1- or 2-aziridinyl, 2-oxiranyl, 2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2 yl, 1-, 2- or 3-pyrrolidinyl. In the preferred range (3-1) or (3-2), unless stated otherwise,
Halogen für Fluor, Chlor, Brom und lod, bevorzugt für Fluor, Chlor und Brom und Halogen for fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine and
Heterocyclyl (auch als Teil einer größeren Einheit, wie Heterocyclylalkyl) für einen gesättigten oder ungesättigten 3- oder 4-Ring, der 1 oder 2 Stickstoffatome und/oder ein Sauerstoffatom und/oder ein Schwefelatom enthält, wobei jedoch nicht 2 Stickstoffatome direkt benachbart sein sollen, beispielsweise für 1- oder 2-Aziridinyl, 2-Oxiranyl, 2-Thiiranyl, 1- oder 2-Azetidinyl, 2- oder 3-Oxetanyl, 2- oder 3-Thietanyl oder l,3-Dioxetan-2-yl.Durch Halogen substituierte Reste, z.B. Halogenalkyl (= Haloalkyl), sind, sofern nichts anderes gesagt ist, einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder lod, insbesondere für Fluor, Chlor oder Brom. Heterocyclyl (also as part of a larger unit, such as heterocyclylalkyl) for a saturated or unsaturated 3- or 4-membered ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, but not two nitrogen atoms to be directly adjacent for example, 1- or 2-aziridinyl, 2-oxiranyl, 2-thiiranyl, 1- or 2-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl or 1,3-dioxetan-2-yl Halogen substituted radicals, eg Halogenoalkyl (= haloalkyl) are, unless stated otherwise, halogenated one or more times up to the maximum possible number of substituents. For multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein. Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
Gegebenenfalls substituierte Reste können, wenn nichts anderes erwähnt ist, einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Unless otherwise specified, optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
Wenn T in den Verbindungen der Formel (I) für Sauerstoff steht, liegen diese Verbindungen als NT- Oxide vor. When T in the compounds of the formula (I) is oxygen, these compounds are present as NT oxides.
Wenn T in den Verbindungen der Formel (I) für ein Elektronenpaar steht, liegen diese Verbindungen als Pyridine vor. When T in the compounds of the formula (I) is an electron pair, these compounds are present as pyridines.
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. Erfindungsgemäß bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (1-1) oder Vorzugsbereich (1-2)). 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. Preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferred range (1-1) or preferred range (1-2)).
Erfindungsgemäß besonders bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vor- zugsbereich (2-1) oder Vorzugsbereich (2-2)). Erfindungsgemäß ganz besonders bevorzugt verwendet werden Verbindungen der Formel (II), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (3-1) oder Vorzugsbereich (3-2)). Particular preference is given according to the invention to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present (preferred range (2-1) or preferred range (2-2)). Very particularly preferably used according to the invention are compounds of the formula (II) in which a combination of the meanings listed above as being very particularly preferred is present (preferred range (3-1) or preferred range (3-2)).
Erfindungsgemäß insbesondere bevorzugt verwendet werden Verbindungen der Formel (II), in wel- chen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (4-1) oder Vorzugsbereich (4-2)). Particular preference is given according to the invention to compounds of the formula (II) in which a combination of the meanings given above as very particularly preferred is present (preferred range (4-1) or preferred range (4-2)).
Erfindungsgemäß noch weiter bevorzugt verwendet werden Verbindungen der Formel (II), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt (Vorzugsbereich (5-1) oder Vorzugsbereich (5-2)). In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Vorzugsbereich (1- 1) oder Vorzugsbereich (1-2) oder Vorzugsbereich (2-1) oder Vorzugsbereich (2-2) oder Vorzugsbereich (3-1) oder Vorzugsbereich (3-2) oder Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) oder Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) und X die in Ausführungsform (0) beschriebenen Bedeutungen hat. Even more preferably used according to the invention are compounds of the formula (II) in which a combination of the meanings given above as very particularly preferred is present (preferred range (5-1) or preferred range (5-2)). In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) where the radicals Q, V, W, Y, m, A, R 2 and T are as defined in the preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or Preferred range (5-1) or preferred range (5-2) and X has the meanings described in embodiment (0).
In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Ausführungsform (0) oder Vorzugsbereich (2-1) oder Vorzugsbereich (2-2) oder Vorzugsbereich (3-1) oder Vorzugsbereich (3-2) oder Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) oder Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) und In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or preferred range ( 5-2) and
X und L1 und L2 die in Vorzugsbereich (1-1) oder (1-2) beschriebenen Bedeutungen haben. X and L 1 and L 2 have the meanings described in the preferred range (1-1) or (1-2).
In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Ausführungsform (0) oder Vorzugsbereich (1-1) oder Vorzugsbereich (1-2) oder Vorzugsbereich (3-1) oder Vorzugsbe- reich (3-2) oder Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) oder Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) und In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or Preferred range (5-2) and
X und L1 und L2 die in Vorzugsbereich (2-1) oder (2-2) beschriebenen Bedeutungen haben. X and L 1 and L 2 have the meanings described in the preferred range (2-1) or (2-2).
In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Ausführungsform (0) oder Vorzugsbereich (1-1) oder Vorzugsbereich (1-2) oder Vorzugsbereich (2-1) oder Vorzugsbereich (2-2) oder Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) oder Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) und X die in Vorzugsbereich (3-1) oder (3-2) beschriebenen Bedeutungen hat. In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (4-1) or preferred range (4-2) or preferred range (5-1) or preferred range ( 5-2) and X has the meanings described in the preferred range (3-1) or (3-2).
In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Ausführungsform (0) oder Vorzugsbereich (1-1) oder Vorzugsbereich (1-2) oder Vorzugsbereich (2-1) oder Vorzugsbe- reich (2-2) oder Vorzugsbereich (3-1) oder Vorzugsbereich (3-2) oder Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) und In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (5-1) or Preferred range (5-2) and
X die in Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) beschriebenen Bedeutungen hat. X has the meanings described in the preferred range (4-1) or the preferred range (4-2).
In einer bevorzugten Ausführungsform betrifft die Erfindung die Verbindungen der Formel (I) oder der Formel (II), wobei die Reste Q, V, W, Y, m, A, R2 und T definiert sind wie in Ausführungsform (0) oder Vorzugsbereich (1-1) oder Vorzugsbereich (1-2) oder Vorzugsbereich (2-1) oder Vorzugsbereich (2-2) oder Vorzugsbereich (3-1) oder Vorzugsbereich (3-2) oder Vorzugsbereich (4-1) oder Vorzugsbereich (4-2) und In a preferred embodiment, the invention relates to the compounds of the formula (I) or of the formula (II) wherein the radicals Q, V, W, Y, m, A, R 2 and T are defined as in embodiment (0) or preferred range (1-1) or preferred range (1-2) or preferred range (2-1) or preferred range (2-2) or preferred range (3-1) or preferred range (3-2) or preferred range (4-1) or preferred range ( 4-2) and
X die in Vorzugsbereich (5-1) oder Vorzugsbereich (5-2) beschriebenen Bedeutungen hat. Ein weiterer Gegenstand der Erfindung sind die Zwischenprodukte der Formeln (Xa-Xd) X has the meanings described in the preferred range (5-1) or the preferred range (5-2). Another object of the invention are the intermediates of the formulas (Xa-Xd)
(Xb), (Xb)
(Xd), wobei die vorhandenen Reste die Bedeutungen gemäß der oben genannten erfindungsgemäßen Ausführungsformen der Verbindung nach Formel (I) oder (II) oder bevorzugt gemäß einem der Vorzugsbereiche (1-1), (1-2), (2-1), (2-2), (3-1), (3-2), (4-1), (4-2), (5-1) oder (5-2) und besonders bevorzugt gemäß dem Vorzugsbereich (5-1) oder (5-2) haben. (Xd), where the radicals present are the meanings according to the abovementioned embodiments of the invention of the compound of the formula (I) or (II) or preferably according to one of the preferred ranges (1-1), (1-2), (2-1), (2- 2), (3-1), (3-2), (4-1), (4-2), (5-1) or (5-2) and particularly preferably according to the preferred range (5-1) or (5-2).
Isomere isomers
Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereo- mere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit sowohl reine Stereo- isomere als auch beliebige Gemische dieser Isomere. Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus encompasses both pure stereoisomers and any desired mixtures of these isomers.
Verfahren und Verwendungen Methods and uses
Im Folgenden betreffen die Ausführungen zu den Verbindungen der Formel (I) selbstverständlich auch die Verbindungen der Formel (II), welche in Formel (I) umfasst sind. In the following, the statements relating to the compounds of the formula (I) of course also relate to the compounds of the formula (II) which are included in formula (I).
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. Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. 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.
Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. In the context of the present application, the term pest control always always includes the term pesticides.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblü- tertoxizität 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, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Im Rahmen der vorliegenden Patentanmeldung ist der Begriff„Hygiene" so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauber- keit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder thera- peutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. The compounds of the formula (I) are suitable for plant protection, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs against 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, in particular nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, Ceramic, plastic or even metal (s) to ensure that they are free of hygienic pests and / or their excretions.Primarily excluded from the scope of the invention in this regard are surgical or therapeutic, on the human body or the body of Animals to be applied and diagnostic regulations that are carried out on the human body or the bodies of animals.
Der Begriff„Hygienesektor" deckt alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen wichtig sind, zum Bei- spiel im Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. The term "hygiene sector" covers all areas, technical fields and industrial applications where these hygiene measures, rules and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, Hotels, hospitals, stables, animal husbandry, etc.
Der Begriff„Hygieneschädling" ist daher so zu verstehen, dass damit ein oder mehrere Tierschädlinge gemeint sind, deren Gegenwart im Hygienesektor problematisch ist, insbesondere aus Gesundheitsgründen. Es ist daher ein Hauptziel, das Vorhandensein von Hygieneschädlingen und/oder das Ausgesetztsein ihnen gegenüber im Hygienesektor zu vermeiden oder auf ein Mindestmaß zu begrenzen. Dies lässt sich insbesondere durch die Anwendung eines Pestizids erreichen, das sich sowohl zum Verhindern eines Befalls als auch zum Verhindern eines bereits vorhandenen Befalls einsetzen lässt. Man kann auch Zubereitungen verwenden, die eine Exposition gegenüber Schädlingen verhindern oder reduzieren. Hygieneschädlinge schließen zum Beispiel die unten erwähnten Orga- nismen ein. The term "hygiene pest" should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests For example, hygiene pests include the organisms mentioned below.
Der Begriff „Hygieneschutz" deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen aufrechterhalten und/oder verbessert werden. The term 'hygiene protection' thus covers all activities which maintain and / or improve those hygiene measures, rules and procedures.
Die Verbindungen der Formel (I) können vorzugsweise als 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 compounds of the formula (I) 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., Boo- philus 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, Glycy- phagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus coffeae, Oli- gonychus 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, Polyphagotarso- nemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z. B. Tarsonemus confusus, Tar- sonemus pallidus, Tetranychus spp., z. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetra- nychus 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 asahi- nai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z. B. Periplaneta americana, Periplaneta australasi- ae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., z. B. Agriotes linneatus, Agriotes mancus, Alphitobi- us diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z. B. Atoma- ria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z. B. Ceutor- rhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conode- rus spp., Cosmopolites spp., z. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Cur- culio spp., z. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindroco- pturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica unde- cimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus 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 unda- Iis, 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, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomor- pha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoce- ros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z. B. Otiorhynchus cri- bricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon coch- leariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z. B. Phyllotreta armoraciae, Phyllot- reta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Proste - phanus truncatus, Psylliodes spp., z. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punc- tulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z. B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z. B. Zabrus tenebrioides; aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; aus der Ordnung der Diptera z. B. Aedes spp., z. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z. B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, 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, Cu- licoides 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, Derma- tobia hominis, Drosophila spp., z. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., z. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z. B. Musca domestica, Musca domestica vicina, O- estrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya oder Pegomy- ia spp., z. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., z. B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rha- goletis 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, To- xotrypana curvicauda; aus der Ordnung der Hemiptera z. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia unca- toides, Acrida turrita, Acyrthosipon spp., z. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleuro- thrixus floccosus, Allocaridara malayensis, Amrasca spp., z. B. Amrasca bigutulla, Amrasca devas- tans, Anuraphis cardui, Aonidiella spp., z. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inor- nata, Aphanostigma piri, Aphis spp., z. B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis for- besi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytai- nilla 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, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chroma- phis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z. B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chitten- deni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Hete- ropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z. B. Le- canium corni (=Parthenolecanium corni), Lepidosaphes spp., z. B. Lepidosaphes ulmi, Lipaphis ery- simi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z. B. Macrosiphum euphor- biae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monel- liopsis pecanis, Myzus spp., z. B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z. B. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncome- topia 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, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madei- rensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phy- lloxera 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, Ptero- malus spp., Pulvinaria 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, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, To- maspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporario- rum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z. B. Cimex adjunc- tus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoco- risa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z. B. Lygocoris pabulinus, Lygus spp., z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., 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., Camponotus spp., Dolichovespula spp., Diprion spp., z. B. Diprion similis, Hoplocampa spp., z. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes flavipes, Reticu- litermes hesperus; aus der Ordnung der Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., z. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z. B. Ephestia elutella, Ephestia kuehni- ella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudoci- ma spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z. B. Euproctis chrysorrhoea, Euxoa spp., Felda spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z. B. Grapholita molesta, Grapho- lita prunivora, Hedylepta spp., Helicoverpa spp., z. B. Helicoverpa armigera, Helicoverpa zea, Helio- this spp., z. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocol- letis 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., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pec- tinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthori- maea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyl- lonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseuda- letia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B. Scirpophaga innotata, Sco- tia segetum, Sesamia spp., z. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z. B. Spodop- tera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Tricho- phaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Vira- chola 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, Mela- noplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pedi- culus 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. Ctenocepha- lides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetana- phothrips leeuweni, Drepanothrips reuteri, Enneothrips Hävens, Frankliniella spp., z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella immaculata; Pests from the strain of Arthropoda, in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Z. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Z. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp , Steneotarsonemus spinki, Tarsonemus spp., Z. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of Chilopoda z. Geophilus spp., Scutigera spp .; from the order or class of Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of Diplopoda z. B. Blaniulus guttulatus; from the class of the Insecta, z. B. from the order of Blattodea z. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., E.g. B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Z. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. Ceutorhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conradus spp., Cosmopolites spp., E.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curiculio spp., E.g. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocpturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., E.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica unde- cimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., e.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. 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., E.g. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., E.g. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoce- ros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prosthanus truncatus, Psylliodes spp., E.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctullata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., E.g. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemus spp., E.g. Starchus paludatus, Symphyletes spp., Tanymecus spp., E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera z. B. Aedes spp., Z. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., E.g. Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Derma- tobia hominis, Drosophila spp., e.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., E.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., E.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., E.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Ragoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., E. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., Z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of Hemiptera z. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncadoides, Acrida turrita, Acyrthosipon spp., E.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurotrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp. Aonidiella aurantii, Aonidiella citrina, Aonidiella inor- nata, Aphanostigma piri, Aphis spp., E.g. 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, Arytai - nilla spp., Aspidiella spp., Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chrysophis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurode chittheni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp ., Drosicha spp., Dysaphis spp., Z. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. Empaasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Hetereopsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Z. B. Lepidosaphes ulmi, Lipaphis ery- simi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteys facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Moneliopsis pecanis, Myzus spp., E.g. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncome topia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. Phylloxera devastatrix, Phyloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., E.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Toaspis spp., Toxoptera spp., e.g. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporario- rum, Trioza spp., Z. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. Eustistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocoris varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp. , z. Lygocoris pabulinus, Lygus spp., E.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., Z. B. Diprion similis, Hoplocampa spp., Z. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of Isoptera z. B. Coptotermes spp., Z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of Lepidoptera z. Achroia grisella, Acronica major, Adoxophyes spp., E.g. Adoxophytes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., Z. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata , Chilo spp., Z. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., E.g. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g. Ephestia elutella, Ephestia kuehnillella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., E.g. Euproctis chrysorrhoea, Euxoa spp., Felda spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. Helicoverpa armigera, Helicoverpa zea, Helioses spp., E.g. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B. Lithocoletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. 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., Omphisa spp., Operophtera spp., Oria spp. Orthaga spp., Ostrinia spp. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. B. Phthori maea operculella, Phyllocnis citrella, Phyllonorycter spp., e.g. B. Phyllonorycter blancardella, Phyl- lonorycter crataegella, Pieris spp., Z. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudotelia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g. Scirpophaga innotata, scotia segetum, sesamia spp., E.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., Z. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera z. Lepinotus spp., Liposcelis spp .; from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephalides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetana-phothrips leeuweni, Drepanothrips reuteri, Enneothrips hevens, Frankliniella spp., Z. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp , B. Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.; sowie aus der Klasse der Gastropoda z. B. Arion spp., z. B. Arion ater rufus, Biomphalaria spp., Bu- linus spp., Deroceras spp., z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Buillus spp., Deroceras spp., Z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d. h. pflanzenparasitäre Nematoden, insbeson- dere Aglenchus spp., z. B. Aglenchus agricola, Anguina spp., z. B. Anguina tritici, Aphelenchoides spp., z. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z. B. Be- lonolaimus 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 pal- lida, Globodera rostochiensis, Helicotylenchus spp., z. B. Helicotylenchus dihystera, Hemicrico- nemoides spp., Hemicycliophora spp., Heterodera spp., z. B. Heterodera avenae, Heterodera glyci- nes, Heterodera schachtii, Hirschmaniella spp., 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., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z. B. Paratrichodorus minor, Paratylenchus spp., Praty- lenchus 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, Ty- lenchulus spp., z. B. Tylenchulus semipenetrans, Xiphinema spp., z. B. Xiphinema index. Plant pests from the strain of Nematoda, d. H. plant parasitic nematodes, in particular Aglenchus spp. Aglenchus agricola, Anguina spp., E.g. Anguina tritici, Aphelenchoides spp., E.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. B. lonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. Globodera palida, Globodera rostochiensis, Helicotylenchus spp., E.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., E.g. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., Eg. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Auf- wandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykoti- ka, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Myco- plasma-like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. Formulierungen If appropriate, the compounds of the formula (I) may also be used in certain concentrations or as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) 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
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 Penetrationsför- derer, z. B. pflanzliche Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester pflanzlicher 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 Ammo- niumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fördernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar-Polymere und/oder Humectants wie z. B. Glycerin und/oder Dünger wie beispielsweise Ammonium, Kalium oder Phosphor enthaltende Dünger. The present invention further relates to formulations and application forms prepared therefrom as pesticides such. B. drench, drip and spray liquors, comprising at least one compound of formula (I). If appropriate, the use forms contain further pesticides and / or effect-improving adjuvants such as penetration promoters. those, z. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg. As organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such. As dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such. As glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser disper- gierbare 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 Produc- tion and Protection Papers - 173, prepared by the FAOAVHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einer oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates ( CS); These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAOAVHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. They are preferably formulations or use forms which contain auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example 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 oberflächenaktiven Stoffen. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants. The preparation of the formulations is carried out either in suitable systems or before or during use.
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 imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties.
Als Streckmittel eignen sich z. B. Wasser, polare und unpolare organische chemische Flüssigkeiten z. B. aus den Klassen der aromatischen und nicht-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). 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: Aro- maten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe 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, Methyl - ethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. Suitable extenders z. As water, polar and nonpolar organic chemical liquids such. 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, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide). In the case of using water as an extender z. As well as organic solvents can be used as an auxiliary solvent. 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, eg. As 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, strong 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, chlorier - te aromatische oder chlorierte aliphatische Kohlenwasserstoffe wie z. B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z. B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z. B. Methanol, Ethanol, iso-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 Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und/oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwen- det 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. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated - te aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water. In principle, all suitable carriers can be used. As carriers are in particular question: z. For example, ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals 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: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corncobs and tobacco stems.
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. Also, liquefied gaseous diluents or solvents can be used. In particular, are such extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for. As aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulfonsäure, Salze von Phenolsulfonsäure oder Naph- thalinsulfonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulfobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von po- lyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulfate, Sulfonate 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 Anwen- dung 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 lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, eg. As alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen 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 used in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocy anblau 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, Oxida- tionsschutzmittel, Lichtschutzmittel oder andere die chemische und/oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. As further auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg. Example, iron oxide, titanium oxide, Ferrocy blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and / or physical stability can 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, kör- nige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und pflanzliche Öle sein. Furthermore, the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.
Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsför- derer, Stabilisatoren, Sequestiermittel, Komplexbildner, Feuchthaltemittel, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welcher für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. 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, sequestering agents, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflä- chenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar-Polymere. Retention promoters are all those substances which reduce the dynamic surface tension, such as, for example, dioctyl sulfosuccinate or which increase the viscoelasticity, such as, for example, 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 Beweglichkeit der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Me- thode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Al- koholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettaminalkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium- Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. Suitable penetration promoters in the present context are all those substances which are customarily used in order to prevent the penetration of agrochemical active ingredients into To improve plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or 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.
Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwen- dungsformen (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, Herbiziden, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semi- ochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z. B. das Wirkungs- spektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repel- lenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Des Weiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfä- higkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteertrag steigern, die Reife beeinflussen, die Qualität und/oder der 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 are used to such. For example, to widen the range of action, to extend the duration of action, to increase the speed of action, to prevent repellency or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. It is also possible to improve flowering and fruiting behavior, to optimize germination and rooting, to facilitate harvest and to increase crop yield, to influence ripeness, to increase the quality and / or nutritional value of harvested produce, to extend shelf life and / or to improve the workability of harvested produce improve.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Se- miochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. In addition, the compounds of the formula (I) may be mixed 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 formula (I) can be used to improve plant properties such as 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. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids.
Insektizide/Akarizide/Nematizide Insecticides / acaricides / nematicides
Die hier mit ihrem„Common Name" genannten Wirkstoffe sind bekannt und beispielsweise im Pes- tizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z. B. http://www.alanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen IRAC Mode of Action Classification Scheme. The active substances mentioned here by their "common name" are known and described, for example, in the Pesticides Handbook ("The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: // www. alanwood.net/pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.
(1) Acetylcholinesterase(AChE)-Inhibitoren, wie beispielsweise Carbamate, z. B. Alanycarb, Aldi- carb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Me- tolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder Organophosphate, z. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlore thoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoat, Dimethyl- vinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0-(methoxyaminothio- phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothio- fos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetra- chlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Blocker, wie beispielsweise Cyclodien-organochlorine, z. B. Chlordan und Endosulfan oder Phenylpyrazole (Fiprole), z. B. Ethiprol und Fipronil. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, Triazamates, trimethacarb, XMC and xylylcarb or organophosphates, e.g. Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinone, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos , Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0- (methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoate, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiotos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachloro-phosphine, thiometone, triazophos, triclorfone and vamidothion. (2) GABA-controlled chloride channel blockers, such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
(3) Natrium-Kanal-Modulatoren, wie beispielsweise Pyrethroide, z. B. Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans- Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bio- resmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Hal- fenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Pral- lethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(lR)-Isomer], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (3) sodium channel modulators, 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 isomer], deltamethrin, empenthrin [(EZ) (lR) isomer], esfenvalerate, Etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR) -trans-isomer], prompethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, Tefluthrin, tetramethrin, tetramethrin [(lR) isomer], tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Neonicotinoide, z. B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nicotin oder Sulfoxaflor oder Flupyradifurone. (5) Allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Spinosyne, z. B. Spinetoram und Spinosad. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone. (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as spinosyn, e.g. B. spinetoram and spinosad.
(6) Allosterische Modulatoren des Glutamat- abhängigen Chloridkanals(GluCl), wie beispielsweise Avermectine/Milbemycine, z. B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl), such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
(7) Juvenilhormon-Mimetika, wie beispielsweise Juvenilhormon-Analoge, z. B. Hydropren, Kinop- ren und Methopren oder Fenoxycarb oder Pyriproxyfen. (7) Juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinop- ren and methoprene or fenoxycarb or pyriproxyfen.
(8) Verschiedene nicht spezifische (multi-site) Inhibitoren, wie beispielsweise Alkylhalogenide, z. B. Methylbromid und andere Alkylhalogenide; oder Chloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein oder Methylisocyanaterzeuger, z. B. Diazomet und Metam. (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
(9) Modulatoren chordotonaler Organe, z. B. Pymetrozin oder Flonicamid. (10) Milbenwachstumsinhibitoren, wie z. B. Clofentezin, Hexythiazox und Diflovidazin oder Eto- xazol. (9) modulators of chordotonic organs, e.g. As pymetrozine or flonicamide. (10) mite growth inhibitors, such as. Clofentezine, hexythiazox and diflovidazine or otoxazole.
(11) Mikrobielle Disruptoren der Insektendarmmembran, wie z. B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und fi.i.-Pflanzenproteine: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab 1/35 Abi. (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren, wie beispielsweise Diaf- enthiuron oder Organozinnverbindungen, z. B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargit oder Tetradifon. (11) Microbial disruptors of insect intestinal membrane such. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and fi.i. plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab 1/35 Abi. (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors such as diafliuron or organotin compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
(13) Entkoppler der oxidativen Phoshorylierung durch Störung des Protonengradienten, wie bei- spielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by disruption of the proton gradient, such as, for example, chlorfenapyr, DNOC, and sulfluramide.
(14) Blocker des nicotinischen Acetylcholinrezeptorkanals, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Blockers of the nicotinic acetylcholine receptor channel, such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin.
(17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern), wie beispielsweise Cyroma- zin. (17) Skinning disruptor (especially in dipterans, i.e., two-wingers), such as cyromazine.
(18) Ecdyson-Rezeptor-Agonisten, wie beispielsweise Chromafenozid, Halofenozid, Methoxyfeno- zid und Tebufenozid. (18) ecdysone receptor agonists, such as chroma- tozide, halofenozide, methoxyfenocide and tebufenozide.
(19) Oktopamin- Rezeptor- Agonisten, wie beispielsweise Amitraz. (19) octopamine receptor agonists, such as amitraz.
(20) Mitochondriale Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethyl- non oder Acequinocyl oder Fluacrypyrim. (20) Mitochondrial Complex III Electron Transport Inhibitors, such as, for example, hydramethylnono- or acequinocyl or fluacrypyrim.
(21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, wie beispielsweise METI-Akarizide, z. B. Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Ro- tenon (Derris). (21) Mitochondrial Complex I Electron Transport Inhibitors, such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Roenton (Derris).
(22) Blocker des spannungsabhängigen Natriumkanals, wie z. B. Indoxacarb oder Metaflumizone. (22) blocker of the voltage-dependent sodium channel, such. Indoxacarb or metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z. B. Spirodiclofen, Spiromesifen und Spirotetramat. (24) Inhibitoren des mitochondrialen Komplex-IV-Elektronentransports, wie beispielsweise Phosphi- ne, z. B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanide, Calci- umcyanid, Kaliumcyanid und Natriumcyanid. (25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, wie beispielsweise beta- Ketonitrilderivate, z. B. Cyenopyrafen und Cyflumetofen und Carboxanilide, wie beispielsweise Pyflubumid. (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat. (24) inhibitors of mitochondrial complex IV electron transport, such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide. (25) inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
(28) Ryanodinrezeptor-Modulatoren, wie beispielsweise Diamide, z. B. Chlorantraniliprol, Cyantra- niliprol und Flubendiamid, weitere Wirkstoffe wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzo- ximat, Bifenazat, Broflanilid, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclani- liprol, Cycloxaprid, Cyhalodiamid, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizin, Fluensulfon, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tioxazafen, Thiofluoximat, Triflumezopyrim und lodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo), sowie folgende Verbindungen: 1 -{ 2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl } -3-(trifluormethyl)- 1H- 1 ,2,4-triazol-5- amin (bekannt aus WO2006/043635) (CAS 885026-50-6), { l'-[(2E)-3-(4-Chlorphenyl)prop-2-en-l- yl] -5-fluorspiro [indol-3,4'-piperidin] - 1 (2H)-yl } (2-chlorpyridin-4-yl)methanon (bekannt aus WO2003/106457) (CAS 637360-23-7), 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) (CAS 872999-66-1), 3-(4-Chlor-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2- on (bekannt aus WO 2010052161) (CAS 1225292-17-0), 3-(4-Chlor-2, 6-dimethylphenyl)-8- methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS-1440516-42-6), 4-(But-2-in- l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160) (CAS 792914-58-0), PF1364 (bekannt aus JP2010/018586) (CAS- Reg.No. 1204776-60-2), N-[(2E)-l-[(6-Chlorpyridin-3-yl)methyl]pyridin-2(lH)-yliden]-2,2,2- trifluoracetamid (bekannt aus WO2012/029672) (CAS 1363400-41-2), (3E)-3-[l-[(6-Chlor-3- pyridyl)methyl]-2-pyridyliden]- l,l,l-trifluorpropan-2-on (bekannt aus WO2013/144213) (CAS 1461743- 15-6), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-l-methyl-3-(pentafluorethyl)-4- (trifluormethyl)-lH-pyrazol-5-carboxamid (bekannt aus WO2010/051926) (CAS 1226889-14-0), 5- Brom-4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazol-3- carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorphenyl)-4,5- dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid, 4-[5-(3,5- Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(trans-l-oxido-3- thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]- 2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid (bekannt aus WO 2013/050317 AI) (CAS 1332628- 83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- trifluorpropyl)sulfinyl]propanamid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yi]-N- ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013/162715 AI, WO 2013/162716 A2, US 2014/0213448 AI) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l- yl] amino] - 1 - [2,6-dichlor-4-(trifluormethyl)phenyl] -4- [(trifluormethyl)sulfinyl] - 1 H-pyrazol-3- carbonitrile (bekannt aus CN 101337937 A) (CAS 1105672-77-2), 3-Brom-N-[4-chlor-2-mefhyl-6- [(methylamino)thioxomethyl]phenyl] - 1 -(3-chlor-2-pyridinyl)- lH-pyrazol-5-carboxamid, (Liudaiben- jiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(l,l- dimethylethyl)amino]carbonyl] -6-methylphenyl] - 1 -(3-chlor-2-pyridinyl)-3-(fluormethoxy)- 1H- pyrazol-5-carboxamid (bekannt aus WO 2012/034403 AI) (CAS 1268277-22-0), N-[2-(5-Amino- l,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom- l-(3-chlor-2-pyridinyl)-lH-pyrazol-5- carboxamid (bekannt aus WO 2011/085575 AI) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3- dichlor-2-propen-l-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1108184-52-6); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l-[3- (trifluormethyl)phenyl]ethyliden]-N-[4-(difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9); Cyclopropancarbonsäure-3-(2,2-dichlorefhenyl)-2,2- dimethyl-4-(lH-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46- 4); (4aS)-7-Chlor-2,5-dihydro-2-[[(methoxycarbonyl)[4- [(trifluormethyl)thio]phenyl] amino] carbonyl] indeno [ 1 ,2-e] [ 1 ,3,4]oxadiazin-4a(3H)- carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-0-ethyl- 2,4-di-O-methyl- 1 - [N- [4- [ 1 - [4-( 1 , 1 ,2,2,2-pentafluorethoxy)phenyl] - 1H- 1 ,2,4-triazol-3- yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014/0275503 AI) (CAS 1181213-14-8); 8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmefhoxy-4- trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2. l]octan (CAS 933798- 27-7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3- yl)-3-azabicyclo[3.2.1]octan (bekannt aus WO 2007040280 AI, WO 2007040282 AI) (CAS 934001- 66-8) und N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)thio]- propanamid (bekannt aus WO 2015/058021 AI, WO 2015/058028 AI) (CAS 1477919-27-9). Fungizide (28) ryanodine receptor modulators, such as diamides, e.g. B. chlorantraniliprole, cyanotiliprole and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiazole, benzoximat, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fludexafon, fluopyram, fluralan, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilan, meperfluthrin, Paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, spirobudiclofen, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following compounds: 1 - {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} - 3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {1 '- [(2E) -3- (4-chlorophenyl ) prop-2-en-1-yl] -5-fluorospiro [indole-3,4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457) (CAS 637360-23-7), 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) (CAS 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-l, 8- diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2-oxo l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), 4- (but-2-yl-yloxy) -6 - (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 ( known from JP2010 / 018586) (CAS Reg.No. No. 1204776-60-2), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridin-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3E) -3- [l - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1-trifluoropropan-2-one ( known from WO2013 / 144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5 carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6- (methylcarbamoyl) phenyl] -2- (3 chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) - 3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) -benzamide, 4- [5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3 -isoxazolyl] -2-methyl-N- (trans-1-oxido-3-thietanyl) benzamide and 4 - [(5S) -5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl ) -3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) benzamide (known from WO 2013/050317 A1) (CAS 1332628-83-7 ), N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-) trifluoropropyl) sulfinyl] propanamide, (+) - N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfinyl] propanamide and (-) - N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide (known from WO 2013/162715 A1, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5 - [[(2E) -3-chloro-2-propen-1-yl ] amino] - 1 - [2,6-dichloro-4- (trifluoromethyl) phenyl] -4- [(trifluoromethyl) sulfinyl] -1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77 -2), 3-bromo-N- [4-chloro-2-methyl-6- [(methylamino) thioxomethyl] phenyl] -1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(1,1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazole 5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N- [2- (5-amino, 3,4-thiadiazol-2-yl) -4-chloro-6 methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4- [3- [ 2,6-dichloro-4 - [(3,3-dichloro-2-propen-1-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4- (difluoromethoxy) phenyl] hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3- (2,2-dichloro-phenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS) -7-chloro-2,5-dihydro-2 - [[(methoxycarbonyl) [4- [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1, 2-e] [1, 3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-Deoxy-3-O-ethyl-2,4-di-O-methyl-1 - [N- [4- [1 - [4- (1,1,2,2-pentafluoroethoxy) -phenyl] - 1H-1, 2,4-triazol-3-yl] phenyl] carbamate] -AL-mannopyranose (known from US 2014/0275503 Al) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-anti) -8- (2-Cyclopropylmethylthio-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2. 1-octane (CAS 933798-27-7), (8-syn) -8- (2-cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) and N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoropropyl) thio] propanamide (known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9). fungicides
Die hier mit ihrem "Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im "Pesticide Manual" (16. Aufl. British Crop Protection Council) oder im Internet recherchierbar (beispielsweise: http://www.alanwood.net/pesticides) beschrieben. The active ingredients specified here by their "common name" are known and described, for example, in the "Pesticide Manual" (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides).
Alle genannten Mischungspartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktio- nellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Alle genannten fungiziden Mischungspartner der Klassen (1) bis (15) können gegebenenfalls tauto- mere Formen einschließen. All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids. All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoco- nazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.011) Imazalil Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triti- conazol, (1.026) (lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (1.027) (lS,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, ( 1.028) (2R)-2-( 1 -Chlorcyclopropyl)-4- [( 1 R)-2,2- dichlorcyclopropyl] - 1 -( 1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol ( 1.029) (2R)-2-( 1 -Chlorcyclopropyl)-4- [( 1 S)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.030) (2R)-2- [4-(4-1) inhibitors of ergosterol biosynthesis, for example, (1,001) cyproconazole, (1,002) difenocynazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole , (1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochloraz, (1,017) propiconazole, (1,018) Prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (1R, 2S, 5S) - 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1.027) (IS, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) - 4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol (1.029) (2R) -2- (1-chlorocyclopropyl ) -4- [(1S) -2,2-dichloro cyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1030) (2R) -2- [4- (4-
Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.031) (2S)-2-( 1 - Chlorcyclopropyl)-4- [( 1 R)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.032) (2S)- 2-( 1 -Chlorcyclopropyl)-4- [( 1 S)-2,2-dichlorcyclopropyl] - 1 -( 1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.033) (2S)-2- [4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.034) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, ( 1.037) 1 -( { (2R,4S)-2- [2-Chlor-4-(4-chlorphenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2-yl Jmethyl)- 1 H- 1 ,2,4-triazol, (1.038) 1 -( { (2S,4S)-2- [2-Chlor-4-(4-chlorphenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2- yl}methyl)-lH-l,2,4-triazol, (1.039) l-{ [3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl] methyl } - 1H- 1 ,2,4-triazol-5-yl-thiocy anat, ( 1.040) 1 - { [rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl-thiocyanat, (1.041) l-{ [rel(2R,3S)-3-(2- Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl } - 1 H- 1 ,2,4-triazol-5-yl-thiocy anat, ( 1.042) 2- [(2R,4R,5R)- 1 -(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4- triazol-3-thion, (1.043) 2-[(2R,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H- 1 ,2,4-triazol-3-thion, ( 1.044) 2- [(2R,4S,5R)- l-(2,4-Dichlorophenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.045) 2-[(2R,4S,5S)-l-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazol-3-thion, (1.047) 2-[(2S,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.048) 2-[(2S,4S,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.049) 2-[(2S,4S,5S)-l-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.050) 2-[l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3- thion, ( 1.051) 2- [2-Chlor-4-(2,4-dichlorophenoxy)phenyl] - 1 -( 1H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.052) 2- [2-Chlor-4-(4-chlorphenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.053) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.054) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol, ( 1.055) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.056) 2-{ [3-(2- Chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl}-^^ Chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1031) (2S) -2- (1-chlorocyclopropyl) - 4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.032) (2S) -2- (1 -Chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1033) (2S) -2 [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1034) (R) - [ 3- (4-Chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -l, 2-oxazol-4-yl] (pyridin-3-yl) -methanol, (1035) (S) - [3 - (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (1.036) [3- (4-chloro -2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (1.037) 1 - ({(2R, 4S) -2- [2-Chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl-methyl) -1 H -1, 2,4-triazole, (1038) 1 - ({ 2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl} methyl) -1H-l, 2,4-triazole, ( 1.039) l- {[3- (2-Chl orphenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl-thiocyanate, (1040) 1 - {[rel (2R, 3R ) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazol-5-yl thiocyanate, (1041) 1 { [rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl-thiocy anate, (1.042) 2- [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H - 1, 2,4-triazole-3-thione, (1043) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4 -yl] - 2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2- [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5- hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.045) 2 - [(2R, 4S, 5S) -l - (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.046) 2 - [(2S, 4R, 5R) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4-dihydro-3H-l, 2,4 triazole-3-thione, (1,047) 2 - [(2S, 4R, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1048) 2 - [(2S, 4S, 5R ) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, 1.049) 2 - [(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1050) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H -l, 2,4-triazol-3- thione, (1.051) 2- [2-Chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.052) 2- [2-Chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1, 2,4-triazol-1-yl) butan-2-ol, (1.053) 2- [4- ( 4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.054) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) pentan-2-ol, (1.055) 2- [4- (4-chlorophenoxy) -2- ( trifluoromethyl) phenyl] -1- (1H-l, 2,4-triazol-1-yl) propan-2-ol, (1.056) 2- {[3- (2-chlorophenyl) -2- (2,4,6-triazol-1-yl) propan-2-ol] difluorophenyl) oxiran-2-yl] methyl} - ^ ^
(1.057) 2-{ [rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-dirluoφhenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H- l,2,4-triazol-3-thion, (1.058) 2-{ [rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-dirluoφhenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2- methyl-l-(lH-l,2,4-triazol-l-ylmethyl)cyclopentanol, (1.060) 5-(Allylsulfanyl)-l-{ [3-(2- chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl } - 1 H- 1 ,2,4-triazol, ( 1.061 ) 5-( Allylsulf anyl) - 1 - { [rel(2R,3R)-3-(2-ch^henyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.062) 5-(Allylsulfanyl)-l-{ [rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH- 1,2,4-triazol, (1.063) N'-(2,5-Dimethyl-4-{ [3-(l,l,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4-{ [3-(2,2,2- trifluorethoxy)phenyl] sulfanyl }phenyl)-N-ethyl-N-methylimidoformamid, ( 1.065) N'-(2,5-Dimethyl- 4-{ [3-(2,2,3,3-tetrarluoφropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.066) N'-(2,5-Dimethyl-4- { [3-(pentafluorethoxy)phenyl] sulfanyl }phenyl)-N-efhyl-N- methylimidoformamid, (1.067) N'-(2,5-Dimethyl-4-{3-[(l, 1,2,2- tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.068) N'-(2,5- Dimethyl-4-{3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.069) N,-(2,5-Dimethyl-4-{3-[(2,2,3,3-tetrafluoφropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamid, (1.070) N'-(2,5-Dimethyl-4- { 3- [(pentafluorethyl) sulfanyl] phenoxy Jphenyl)- N-ethyl-N-methylimidoformamid, (1.071) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N- methylimidoformamid, (1.072) N'-(4-{ [3-(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N- ethyl-N-methylimidoformamid, ( 1.073) N'-(4- { 3-[(Difluormethyl)sulfanyl]phenoxy } -2,5- dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.074) N'-[5-Brom-6-(2,3-dihydro-lH-inden-2- yloxy)-2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamid, ( 1.075) N'- { 4- [(4,5 -Dichlor- 1 ,3- thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamid, (1.076) N'-{5-Brom-6- [( 1R)- l-(3,5-difluorophenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamid,(1.057) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-dirloo-phenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.058) 2- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-dirloo-phenyl) -oxiran-2-yl] -methyl} - 2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1, 2, 4-triazol-1-ylmethyl) cyclopentanol, (1.060) 5- (allylsulfanyl) -1- [[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole, (1061) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3- (2-chloro-1-yl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazole, (1.062) 5- (allylsulfanyl) -l- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- ( 2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (1.063) N '- (2,5-dimethyl-4- {[3- (1, 1, 2 , 2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.064) N '- (2,5-dimethyl-4- {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.065) N '- (2,5-dimethyl-4- {[3- (2,2,3,3-tetrarluoropropoxy) phenyl] sulfa nyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.066) N '- (2,5-dimethyl-4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.067) N '- (2,5-Dimethyl-4- {3 - [(1, 1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.068) N' - (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.069) N , - (2,5-dimethyl -4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.070) N '- (2,5-dimethyl-4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy jphenyl) - N -ethyl-N-methylimidoformamide, (1.071) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1.072) N' - (4- {[3- (Difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1.073) N '- (4- {3 - [(Difluoromethyl) sulfanyl] phenoxy } -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1.074) N '- [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridine 3-yl] -N-ethyl-N-methylimidoformamide, (1.0 75) N'- {4- [(4,5-dichloro-1, 3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (1.076) N'- {5-bromo-6- [(1R) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide,
( 1.077) N- { 5 -Brom-6- [( 1 S) - 1 -(3,5-difluoφhenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N- methylimidoformamid, (1.078) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3- yl } -N-ethyl-N-methylimidoformamid, ( 1.079) N- { 5-Brom-6- [(trans-4-isopropylcyclohexyl)oxy] -2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (1.080) N-{5-Bromo-6-[l-(3,5- difΊuoφhenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamid. (1.077) N- {5-Bromo-6- [(1S) -1- (3,5-difluoro-phenyl) -ethoxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.078) N '- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.079) N- {5-bromo-6- [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1080) N- {5-bromo-6- [1- (3,5-difΊuo-phenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide.
2) Inhibitoren der Atmungskette am Komplex I oder II beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimeres Enan- tiomer 1R,4S,9S), (2.011) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.012) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.013) Isopyrazam (Mischung des syn-epimeren Razemates 1RS,4SR,9RS und des anti-epimeren Razemates 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) l,3-Dimethyl-N-(l,l,3-trimethyl- 2,3-dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.023) 1 ,3-Dimethyl-N- [(3R)- 1,1,3- trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.024) 1,3-Dimethyl-N-[(3S)- l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.025) l-Methyl-3- (trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.026) 2-Fluor-6- (trifluoromethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)benzamid, (2.027) 3-2) inhibitors of the respiratory chain on complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) Fluxapyroxad, (2.008) furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.016) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, ( 2.019) pydiflumetofen, (2.020) pyrazolium, (2.021) sedaxanes, (2.022) l, 3-dimethyl-N- (l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) - 1 H-pyrazole-4-carboxamide, (2.023) 1, 3-dimethyl-N- [(3R) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -LH- pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4 carboxamide, (2.025) 1-methyl-3- (trifluoromethyl) -N- [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide d, (2.026) 2-Fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -benzamide, (2.027) 3-
(Difluormethyl)- 1 -methyl-N-( 1 ,1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl)- lH-pyrazol-4-carboxamid, (2.028) 3-(Difluormethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl]-lH-pyrazol-4-carboxamid, (2.030) 3-(Difluormethyl)-N-(7-fluor-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazol-4-carboxamid, (2.031) 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, (2.032) 3- (Difluoromethyl)-N-[(3S)-7-fluor- 1 , l,3-trimethyl-2,3-dihydro- lH-inden-4-yl]- 1 -methyl- lH-pyrazol- 4-carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4-{ [4-(trifluormethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5-iluorbenzyl)-N-cyclopropyl-3- (difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.035) N-(2-tert-Butyl-5- methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-rluor-l -methyl- lH-pyrazol-4-carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(diiluormethyl)-5-iluor-l -methyl- lH-pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(diiluormethyl)-5-iluor-l- methyl-lH-pyrazol-4-carboxamid, (2.039) N-[(lR,4S)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4- methanonaphthalen-5-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.040) N-[(1S,4R)- 9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl]-3-(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.041) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3-(Difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.028) 3- (difluoromethyl) -l-methyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.029) 3- (difluoromethyl ) -l-methyl-N - [(3S) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.030) 3- ( Difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3- (Difluoromethyl) -N - [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4 carboxamide, (2.032) 3- (difluoromethyl) -N - [(3S) -7-fluoro-1,1,3,1-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N- [2- (2-fluoro-4- {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazoline-4 amine, (2.034) N- (2-Cyclopentyl-5-iluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N- ( 2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-r Luoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (diisoromethyl) -5 -ilor-1-methyl-1H-pyrazole-4 carboxamide, (2.037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N- ( 5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (diisoromethyl) -5 -ilor-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N - [(IR, 4S) -9- ( Dichloromethylene) -l, 2,3,4-tetrahydro-l, 4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.040) N - [(1S , 4R) - 9- (Dichloromethylene) - 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, ( 2.041) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3-
(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.042) N-[2-Chlor-6-(trifluormethyl)benzyl]- N-cyclopropyl-3-(diiluormethyl)-5-iluor-l -methyl- lH-pyrazol-4-carboxamid, (2.043) N-[3-Chlor-2- iluor-6-(triiluormethyl)benzyl] -N-cyclopropyl-3-(diiluormethyl)-5-iluor- 1 -methyl- lH-pyrazol-4- carboxamid, (2.044) N-[5-Chlor-2-(triiluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-rluor- 1 -methyl- lH-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3-(difluormethyl)-5-rluor-l-methyl-N- [5-methyl-2-(trifluormethyl)benzyl]-lH-pyrazol-4-carboxamid, (2.046) N-Cyclopropyl-3- (diiluormethyl)-5-fluor-N-(2-rluor-6-isopropylbenzyl)-l -methyl- lH-pyrazol-4-carboxamid, (2.047) N-Cyclopropyl-3-(diiluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-l -methyl- lH-pyrazol-4- carboxamid, (2.048) N-Cyclopropyl-3-(diiluormethyl)-5-iluor-N-(2-isopropylbenzyl)-l-methyl-lH- pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3-(difluoromethyl)-5-fluor-N-(2-isopropyibenzyl)-(difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.042) N- [2-chloro-6- (trifluoromethyl) benzyl] - N -cyclopropyl-3- (di-silo-methyl) -5-iluor-1 L - methyl-1H-pyrazole-4-carboxamide, (2.043) N- [3-chloro-2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (di-silo-methyl) -5-iluor-1-methyl- 1H-pyrazole-4-carboxamide, (2.044) N- [5-chloro-2- (tri-methyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4 carboxamide, (2.045) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1H-pyrazole-4-carboxamide, (2.046) N -Cyclopropyl-3- (diisormethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-Cyclopropyl-3- (di-silo-methyl) - 5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4 carboxamide, (2.048) N-cyclopropyl-3- (diisormethyl) -5-iluor-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3- (difluoromethyl ) -5-fluoro-N- (2-isopropyibenzyl) -
1- methyl-lH-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2- isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.051) N-Cyclopropyl-3-(difluormethyl)-N- (2-ethyl-4,5-dimethylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.052) N-Cyclopropyl-3- (difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.053) N- Cyclopropyl-3-(diiluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-iluor-l-methyl-lH-pyrazole-4- carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3-(diiluormethyl)-5-fluor-l- methyl-lH-pyrazole-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3- (difluormethyl)-5-fluor-l-methyl-lH-pyrazole-4-carboxamid, (2.056) N-Cyclopropyl-N-(2- cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazole-4-carboxamid. 1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -l-methyl-1H-pyrazole-4 -carboxamide, (2.051) N-Cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N -Cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-Cyclopropyl-3- (di-silo-methyl) - N- (2-ethyl-5-methylbenzyl) -5-iluor-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- ( dichloromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-one methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.
3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Ami- sulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostro- bin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[({ [(lE)-l-(3-{ [(E)-l-Fluor-2- phenylvinyl]oxy}phenyl)ethyliden] amino}oxy)methyl]phenyl}-2-(methoxyimino)-N- methylacetamid, (3.022) (2E,3Z)-5-{ [l-(4-Chlorphenyl)-lH-pyrazol-3-yl]oxy }-2-(methoxyimino)- N,3-dimethylpent-3-enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy- N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N- methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4- methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-yl-2-methylpropanoat, (3.026) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.027) N-(3- Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{ [l-(4-Chlor-3) respiratory chain inhibitors on complex III, for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) Enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin , (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin (3.021) (2E) -2- {2 - [({[(E) -l- (3- {[(E) -l-fluoro- 2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5- {[1- (4-chlorophenyl) - lH-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl } -2-methoxy-N-methylacetamide, (3.024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.025) (3S, 6S , 7R, 8R) -8-benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-l, 5-dioxonan-7-yl-2-methylpropanoate, (3.026) 2- {2 - [( 2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3.028) ( 2E, 3Z) -5- {[l- (4-chloro
2- fluorphenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid. 2-fluorophenyl) -1H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide.
4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofen- carb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, , (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5- phenylpyridazin, (4.010) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (4.011)4) inhibitors of mitosis and cell division, for example, (4,001) carbendazim, (4,002) diethyenebarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008 ) Zoxamide,, (4.009) 3-Chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-Chloro-5- (4-chlorophenyl) -4- (2,6 -difluorophenyl) -6-methylpyridazine, (4.011)
3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.012) 4-(2-Brom-4- fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.013) 4-(2-Brom-4- fluorphenyl)-N-(2-brom-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.014) 4-(2-Brom-4- fluorphenyl)-N-(2-bromphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.015) 4-(2-Brom-4-fluorphenyl)- N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)- l,3-dimethyl-lH-pyrazol-5-amin, (4.018) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-l,3- dimethyl-lH-pyrazol-5-amin, (4.019) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l,3- dimethyl-lH-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl- lH-pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol- 5-amin, (4.022) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.023) N-(2-Brom- 6-fluoφhenyl)-4-(2-chlor-4-rluoφhenyl)-1 -dimethyl-lH-pyrazol-5-amirl, (4.024) N-(2- Bromphenyl)-4-(2-chlor-4-fluorphenyl)-13-dimethyl-lH-pyrazol-5-amin, (4.025) N-(4-Chlor-2,6- dirluo henyl)-4-(2-chlor-4-rΊuo henyl)-1 -dimethyl-lH-pyrazol-5-amirl. 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4,012) 4- (2-bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -l , 3-dimethyl-1H-pyrazol-5-amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.015) 4- (2-Bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4- (2-Bromo 4-fluorophenyl) -N- (2-chlorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.017) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) - l, 3-dimethyl-1H-pyrazol-5-amine, (4.018) 4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5 amine, (4.019) 4- (2-chloro-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,020) 4- (2-chloro-4-fluorophenyl) 2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2 -fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4,023) N- (2-bromo-6-fluoro-phenyl) -4- (2-chloro-4-fluoro-phenyl) -1-dimethyl-1H-pyrazole-5-amyl, (4.024) N- (2-bromophenyl) -4- (2 chloro-4-fluorophenyl) -13-dimethyl-1H-pyrazol-5-amine, (4.025) N- (4-chloro-2,6-dirloo-benzyl) -4- (2-chloro-4-rΊuo-henyl) - 1-dimethyl-1H-pyrazole-5-amyl.
5) Verbindungen mit Befähigung zu Multisite-Aktivität, beispielsweise (5.001) Bordeauxmischung, (5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006) Kup- fernaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinkmetiram, (5.017) Kupfer-Oxin, (5.018) Propineb, (5.019) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Verbindungen, die zum Auslösen einer Wirtsabwehr befähigt sind, beispielsweise (6.001) Aciben- zolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. 5) Compounds capable of multisite activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008 ) Copper oxychloride, (5.009) copper (2 +) sulfate, (5.010) dithianone, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, ( 5,017) copper-oxine, (5,018) propineb, (5,019) sulfur and sulfur preparations including calcium polysulfide, (5,020) thiram, (5,021) zineb, (5,022) ziram. 6) Compounds capable of inducing host defense, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
7) Inhibitoren der Aminosäure- und/oder Protein-Biosynthese, beispielsweise (7.001) Cyprodinil,7) inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil,
(7.002) Kasugamycin, (7.003) Kasugamycinhydrochlorid-hydrat, (7.004) Oxytetracyclin (7.005) Pyrimefhanil, (7.006) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolin. (8) Inhibitoren der ATP- Produktion, beispielsweise (8.001) Silthiofam. (7.002) Kasugamycin, (7.003) Kasugamycin Hydrochloride Hydrate, (7.004) Oxytetracycline (7.005) Pyrimefhanil, (7.006) 3- (5-Fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl ) quinoline. (8) inhibitors of ATP production, for example, (8,001) silthiofam.
9) Inhibitoren der Zellwandsynthese, beispielsweise (9.001) Benthiavalicarb, (9.002) Dimethomorph,9) inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
(9.003) (9.007) Vali- fenalat, (9.008) (2E)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(moφholin-4-yl)prop-2-en-l- on, (9.009) (2Z)-3-(4-tert.-Butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(moφholin-4-yl)prop-2-en-l-on. 10) Inhibitoren der Lipid- und Membran-Synthese, beispielsweise (10.001) Propamocarb, (10.002) Propamocarbhydrochlorid, (10.003) Tolclofos-Methyl. (9.003) (9.007) Valiphenate, (9.008) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (4-fluoro-4-yl) prop-2- en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (4-methyl-4-yl) prop-2-ene -l-on. 10) Inhibitors of lipid and membrane synthesis, for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tricyclazol, (11.002) 2,2,2- Trifluorethyl- { 3-methyl- 1- [(4-methylbenzoyl)amino]butan-2-yl Jcarbamat. 11) inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl carbamate.
12) Inhibitoren der Nukleinsäuresynthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam). 12) inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
13) Inhibitoren der Signaltransduktion, beispielsweise (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 14) Verbindungen, die als Entkoppler wirken können, beispielsweise (14.001) Fluazinam, (14.002) Meptyldinocap. 13) inhibitors of signal transduction, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin. 14) compounds which may act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Weitere Verbindungen, beispielsweise (15.001) Abscisinsäure, (15.002) Benthiazol, (15.003) Bethoxazin, (15.004) Capsimycin, (15.005) Carvon, (15.006) Chinomethionat, (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Flutianil, (15.012) Fosetyl-Aluminium, (15.013) Fosetyl-Calcium, (15.014) Fosetyl-Natrium, (15.015) Methylisothio- cyanat, (15.016) Metrafenon, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel- Dimethyldithiocarbamat, (15.020) Nitrothal-Isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapipro- lin, (15.023) Oxyfenthiin, (15.024) Pentachlorphenol und Salze, (15.025) Phosphonsäure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pyriofenone (Chlazafenone) (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) l-(4-{4-[(5R)-5-(2,6-Difluorphenyl)-4,5- dihydro- 1 ,2-oxazol-3-yl]- 1 ,3-thiazol-2-yl Jpiperidin- 1 -yl)-2-[5-methyl-3-(trifluormethyl)- lH-pyrazol- 1 -yljethanon, ( 15.032) 1 -(4- { 4- [(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro- 1 ,2-oxazol-3-yl] - 1 ,3-thiazol- 2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]ethanon, (15.033) 2-(6- Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrol- 1, 3,5,7 (2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2- in- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3-yl } - l,3-thiazol-2-yl)piperidin- l-yl]ethanon, (15.036) 2- [3,5-Bis(difluormethyl)- lH-pyrazol- 1 -yl] - 1 -[4-(4- { 5-[2-chlor-6-(prop-2-in- 1 -yloxy)phenyl] -4,5- dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l -yljethanon, (15.037) 2-[3,5- Bis(difluormethyl)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- { 5- [2-fluor-6-(prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3-yl } - 1 ,3-thiazol-2-yl)piperidin- 1 -yl] ethanon, ( 15.038) 2- [6-(3-Fluor-4-methoxyphenyl)- 5-methylpyridin-2-yl] quinazolin, ( 15.039) 2- { (5R)-3- [2-( 1 - { [3,5-Bis(difluormethyl)- 1 H-pyrazol- 1 - yl]acetyl }piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5-dihydro- l,2-oxazol-5-yl } -3-chlorphenyl 15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) Cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil , (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (15.013) Fosetyl-calcium, (15.014) Fosetyl-sodium, (15.015) Methylisothiocyanate, (15.016) Metrafenone, (15.017) Mildiomycin, ( 15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal isopropyl, (15.021) oxamocarb, (15.022) oxathiapipro- lin, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15,026) propamocarb-fosetylate, (15,027) pyriofenone (Chlazafenone) (15,028) tebufloquine, (15,029) tecloftalam, (15,030) tolnifanide, (15,031) 1- (4- {4 - [(5R) -5- (2, 6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl] piperidine-1-yl) -2- [5-methyl-3- (trifluoromethyl) lH-pyrazole-1-yl-ylanone, (15.032) 1 - (4- {4- [(5S) -5- (2,6-Difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2 - [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2,6-dimethyl-1H, 5H - [l, 4] dithiino [2,3-c: 5,6-c '] dipyrrole-1, 3,5,7 (2H, 6H) -tetrone, (15,035) 2- [3,5-bis ( difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {4- [2- (prop-2-yl-1-ynyloxy) phenyl] -4,5-dihydro-1, 2- oxazol-3-yl} - l, 3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.036) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] - 1 [4- (4- {5- [2-chloro-6- (prop-2-yn-1-ynyloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1, 3-thiazol-2-yl) piperidin-1-yl-ylanone, (15.037) 2- [3,5-bis (difluoromethyl) -1 H -pyrazol-1-yl] -1- [4- (4- [5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine 1 -yl] ethanone, (15.038) 2- [6- (3-fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.039) 2- {(5R) -3- [2- (5-O) 1 - {[3,5-bis (difluoromethyl) -1 H -pyrazol-1-yl] ac ethyl] piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenyl
methanesulfonat, (15.040) 2-{(5S)-3-[2-(l-{ [3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]acetyl }piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5-dihydro- l,2-oxazol-5-yl } -3-chlorphenyl methanesulfonate, (15.040) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -1, 3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenyl
methanesulfonat, ( 15.041 ) 2- { 2- [(7,8-Difluor-2-methylquinolin-3-yl)oxy] -6-fluorphenyl }propan-2- ol, (15.042) 2-{2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 2-{3-[2- ( 1 - { [3,5-Bis(difluormethyl)- 1 H-pyrazol- 1 -yl] acetyl } piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5-dihydro- 1 ,2-oxazol-5-yl } -3-chlorphenyl-methansulfonat, ( 15.044) 2- { 3- [2-( 1 - { [3,5-Bis(difluormethyl)- 1 H- pyrazol- 1 -yl] acetyl }piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5-dihydro- 1 ,2-oxazol-5-yl Jphenyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-(4,4,5-Trifluor-3,3-dimefhyl- 3,4-dihydroisoquinolin-l-yl)quinolin, (15.047) 3-(4,4-Difluor-3,3-dimethyl-3,4-dihydroisoquinolin- l-yl)quinolin, (15.048) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino-5- fluorpyrimidin-2(lH)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino- l,3,4-thiadiazol-2-thiol, (15.051) 5-Chlor-N'-phenyl-N'-(prop-2-yn-l-yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4- methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fluor-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro- 1,4-benzoxazepin, (15.055) But-3-yn-l-yl {6-[({ [(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylen]amino }oxy)methyl]pyridin-2-yl }carbamat, (15.056) Ethyl (2Z)-3-amino-2- cyano-3-phenylacrylat, (15.057) Phenazin-1 -carbonsäure, (15.058) Propyl 3,4,5-trihydroxybenzoat, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfat (2: 1), (15.061) tert-Butyl {6-[({ [(l-mefhyl-lH- tetrazol-5-yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamat. methanesulfonate, (15.041) 2- {2- [(7,8-difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} -propan-2-ol, (15.042) 2- {2-fluoro-6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15.043) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) - 1 H -pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (15.044) 2- {3- [2- (1 - {[3,5-Bis (difluoromethyl) -1 H -pyrazol-1-yl] -acetyl} -piperidin-4-yl) -1,3-thiazole 4-yl] -4,5-dihydro-1,2-oxazol-5-yl-phenylmethylsulfonate, (15.045) 2-phenylphenol and its salts, (15.046) 3- (4,4,5-trifluoro-3, 3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.047) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolinyl-1-yl) quinoline, (15.048) 4 -Amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidine-2 (1H) -one), (15.049) 4-oxo-4 - [(2-phenylethyl) amino] butyric acid, ( 15,050) 5-amino-l, 3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.052) 5-Fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.053) 5-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.054) 9 fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro- 1,4-benzoxazepine, (15,055) but-3-yn-1-yl {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy ) methyl] pyridin-2-yl} carbamate, (15.056) ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5- trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2: 1), (15.061) tert-butyl {6 - [({[(1-methyl-1H-tetrazole-5- yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate.
Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Biological pesticides as mixture components
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. The compounds of formula (I) may be combined with biological pesticides.
Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflan- zenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. 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 I- 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 thurin- giensis, insbesondere B. thuringiensis Subspezies israelensis (Serotyp H-14), Stamm AM65-52 (Ac- cession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS-1857 (SD- 1372), oder B. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebri- onis 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 I-1582) or Bacillus pumilus, in particular strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421), Bacillus thurin giensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp , aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrison 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 (neu: Isaria fumosoro- sea), insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Pae- cilomyces 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, in particular 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 (new: Isaria fumosoroseus) , in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Peckilomyces 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, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. ver- wendet 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.  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.
Es sind auch Bakterien und Pilze umfasst, die als Jnokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: It also includes bacteria and fungi, which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobi- um spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp..  Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., Especially 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., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungs- mittel eingesetzt werden bzw. verwendet werden können, sind:  Examples of plant extracts and products formed by microorganisms, including proteins and secondary metabolites, which are or can be used as biological pest control agents are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum ar- vense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Py- rethrum/Pyrethrine, 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.  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 / Pyrethrin, 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, Brassicaceae extract, in particular rapeseed or mustard powder.
Safener als Mischungskomponenten  Safener as a mixture component
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Beno- xacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Mefhoxy-N-({4-The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, flurazoles, fluxofenim, furilazoles, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-mefhoxy-N - (4-
[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloracetyl)-l-oxa- 4-azaspiro[4.5]decan (CAS 71526-07-3), 2,2,5-Trimethyl-3-(dichloracetyl)-l,3-oxazolidin (CAS 52836-31-4). [(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) -1,3-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), beispielswei- se Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika, Gurke, Melone, Möhre, Wassermelone, Zwiebel, Salat, Spinat, Porree, Bohnen, Brassica oleracea (z. B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gen technologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sorten- schutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien wie Saatgut, Stecklinge, junge (unausgereifte) Pflanzen bis hin zu ausgereiften Pflanzen verstanden werden. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Or- gane 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 gehören auch geerntete Pflanzen oder geerntete Pflanzenteile 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 der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, Spritzen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. 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 durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desirable and undesired wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potatoes, sugar beets, sugar cane , Tomatoes, peppers, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) 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 that can be obtained by conventional breeding and optimization methods or by biotechnological and technological methods or combinations of these methods, including the transgenic plants and including plant varieties that can be protected or not protected by plant variety rights. Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants. Plant parts are to be understood as meaning all aboveground and underground parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes , The plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping. As already mentioned above, according to the invention all plants and their parts can be treated. 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, optionally in combination with conventional methods (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, 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), Cryl- IA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z. B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinone, Sulfonylharnstoffe, Glyphosat oder Phosphinotricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. 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, causes z. By toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), Cryl-IA, CrylllA, CryIIIB2 , Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z. For example, systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with 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.
Pflanzenschutz - Behandlungsarten Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei 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. die Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. 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, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the application form or the compound of the formula (I) itself into the soil. A preferred direct treatment of the plants is foliar application, ie the compounds of formula (I) are applied to the foliage, the frequency of treatment and the rate should be adjusted to the infestation pressure of the respective pest.
Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Ver- bindungen 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 erfindungsgemäßen Verbindungen der Formel (I) werden in fester Form (z. B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasser- reiskulturen 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 substances, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of the formula (I) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, i. H. the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops, this can also be done by dosing 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 Be- handlung 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 auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. The control of animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, the treatment of seeds presents a number of problems 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 include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort. The present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I). The method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Be- handlung 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 erfindungsgemäßen Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und einer Mi- schungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention. The invention also relates to seed which has been treated at the same time with a compound of formula (I) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component. For seeds which have been treated at different times with a compound of formula (I) and a mixture component, the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Ver- bindung der Formel (I) einem Filmcoating- Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmit- telbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. One of the advantages that occurs when a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
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. Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt 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. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophy tischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of the formula (I) can also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia, mycorrhizal and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation.
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baumwolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z. B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, 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, Gemüse und Reis zu. Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseu- domonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. 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, soybean, cotton, canola, oilseed rape, vegetables and rice. 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 originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufge- bracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu ei- nem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage"), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. 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 Aufwand- mengen phytotoxische Effekte zeigen können. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp. For example, seeds may be used that have been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example, in water to a certain stage of the rice embryo ("Pigeon Breast Stage"), which stimulates germination and a more uniform emergence. 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 should be taken into account, in particular, for active substances which may show phytotoxic effects in certain quantities.
Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt wer- den, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. 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, as well as ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lö- sungs- 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 the compounds of the formula (I) with customary additives, for example customary diluents and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, Glue, gibberelline 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. 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 under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
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 Alkylnaphthalinsulfonate, wie Diisopro- pyl- oder Diisobutylnaphthalinsulfonate. 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. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfo- nat-Formaldehydkondensate. 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. 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. Preference is given to using alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are 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.
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. 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.
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. 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 infra- ge, be-sonders 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). Gibberellins which may be present in the seed dressing formulations which can be used according to the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, and gibberellic acid is particularly preferably used. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 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. 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 dem daraus durch Zugabe von Wasser hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im Einzelnen geht man bei der Bei- zung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichen oder kontinuierlichen 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. Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann innerhalb 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. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water, all mixing devices which can usually be used for the dressing can be considered. More specifically, in the case of the addition, the seed is placed in a mixer in discontinuous or continuous operation, which adds in each case the desired amount of seed dressing formulations, either as such or after prior dilution with water, and until uniform distribution of the seed dressing Formulation on the seed mixes. Optionally, 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.
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 Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. In the field of animal health, d. H. 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 or 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; oder Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; oder Fische oder Krustentiere, z. B. in der Aquakultur, oder gegebenenfalls Insekten wie Bienen. 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; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel; Reptilien, Amphibien oder Aquariumfische. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
Gemäß einer bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. In a particular embodiment, the compounds of formula (I) are administered to mammals.
Gemäß einer weiteren bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. According to another specific embodiment, the compounds of formula (I) are administered to birds, namely caged birds or, in particular, poultry.
Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions (in meat, milk, wool, hides, eggs, honey and the like) are to 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" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern. Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., O- dagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; aus der Ordnung Siphonapterida, zum Beispiel Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Panstrongylus spp., Rhodnius spp., Tri- atoma spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. With regard to the field of animal health, the term "control" or "combat" in the present context means that the compounds of formula (I) are effective in their occurrence of the particular parasite in an animal infected with such parasites to a harmless extent. More specifically, "combating" in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication. For example, the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium Spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., Idagia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp. , Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Tritoma spp .; as well as pests and hygiene pests from the order Blattarida.
Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: Further, in arthropods, by way of example and not limitation, the following Akari may be mentioned:
Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Ornithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicepha- lus (Boophilus) spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Rail- lietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp.; aus der Ordnung Actinedida (Prostigma- ta), zum Beispiel Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; und aus der Ordung der Acaridida (Astigmata), zum Beispiel Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp .; from the order Actidida (Prostigma), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites Spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
Zu Beispielen für parasitäre Protozoen zählen, ohne hierauf beschränkt zu sein: Examples of parasitic protozoa include, but are not limited to:
Mastigophora (Flagellata), wie: Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. Mastigophora (Flagellata), such as: Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp.
Parabasala: aus der Ordnung Trichomonadida zum Beispiel Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Parabasala: from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
Euglenozoa: aus der Ordnung Trypanosomatida zum Beispiel Leishmania spp., Trypanosoma spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba spp., Centramoebidae, zum Beispiel Acanthamoeba sp., Euamoebidae, z. B. Hartmanella sp. Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtonella spp. Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida z. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtonella spp.
Microspora wie Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., und außerdem z. B. Myxozoa spp. Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
Zu den für Menschen oder Tiere pathogenen Helminthen zählen zum Beispiel Acanthocephala, Ne- matoden, Pentastoma und Platyhelminthen (z.B. Monogenea, Cestodes und Trematodes). Acute helixes pathogenic to humans or animals include, for example, acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., monogenea, cestodes, and trematodes).
Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Exemplary helminths include, but are not limited to:
Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Monogenea: z. For example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Cestodes: from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeu- xiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. For example, from the order Cyclophyllida: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeu- xiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
Trematodes: aus der Klasse Digenea zum Beispiel: Austrobilharzia spp., Brachylaima spp., Calico- phoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echino- stoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Trematodes: from the genus Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyricum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp. Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp , Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
Nematoden: aus der Ordnung Trichinellida zum Beispiel: Capillaria spp., Trichinella spp., Trichomo- soides spp., Trichuris spp. Nematodes: from the order Trichinellida, for example: Capillaria spp., Trichinella spp., Trichomosides spp., Trichuris spp.
Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp. For example, from the order Tylenchida: Micronema spp., Parastrangyloides spp., Strongyloides spp.
Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastro- ngylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Orni- thostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroi- des spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Telador- sagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. From the order Rhabditina for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp. , Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastropogylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroid spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp , Stephanurus spp., Strongylus spp., Syngamus spp., Telador sagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
Aus der Ordnung Spirurida zum Beispiel: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomo- soides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabi- nema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. For example, from the order Spirurida: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp. Skjrabi- nema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp., Aus der Ordnung Polymorphida zum Beispiel: Filicollis 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 Moniliformida for example: Moniliformis spp., From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Pentastoma: from the order Porocephalida for example Linguatula spp.
Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphyl aktisch oder therapeutisch erfolgen. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphyl actinic or therapeutic.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) zur Verwendung als Arzneimittel. Thus, one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) zur Verwendung als Antiendo- parasitikum. Another aspect relates to the compounds of formula (I) for use as anti-parasitic agents.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwendung als Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platymelminthizid, Acanthocephalizid oder Pentastomizid. Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) zur Verwen- dung als Antiprotozoikum. Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung als Antiektoparasiti- kum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Another aspect relates to the compounds of the formula (I) for use as anti-topazarasitic kum, in particular an arthropodicide, very particularly an insecticide or an acaricide.
Weitere Aspekte der Erfindung sind veterinärmedizinische Formulierungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizinischen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharma- zeutisch unbedenklichen Exzipienten und/oder herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten Hilfsmitteln umfasst. Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations. A related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, especially with pharmaceutically acceptable ones conventionally used in veterinary formulations Excipients and / or adjuvants conventionally used in veterinary formulations.
Ein anderer spezieller Aspekt der Erfindung sind veterinärmedizinische Formulierungen ausgewählt aus der Gruppe ektoparasitizider und endoparasitizider Formulierungen, insbesondere ausgewählt aus der Gruppe anthelmintischer, antiprotozolischer und arthropodizider Formulierungen, ganz besonders ausgewählt aus der Gruppe nematizider, platyhelminthizider, acanthocephalizider, pentastomizider, insektizider und akkarizider Formulierungen, gemäß den erwähnten Aspekten, sowie Verfahren zu ihrer Herstellung. Another specific aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ekto- parasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method of treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a nonhuman animal that needs it.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ekto- parasiten und Endoparasiten, durch Anwendung einer wie hier definierten veterinärmedizinischen Formulierung bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal, that requires it.
Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung" die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal. In the present veterinary or veterinary context, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment.
Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das vete- rinärmedizinische Gebiet bereitgestellt. In a particular embodiment, mixtures of at least one compound of the formula (I) with other active substances, in particular with endo- and ectoparasiticides, are provided hereby for the veterinary field.
Auf dem Gebiet der Tiergesundheit bedeutet„Mischung" nicht nur, dass zwei (oder mehr) verschiedene Wirkstoffe in einer gemeinsamen Formulierung formuliert werden und entsprechend zusammen angewendet werden, sondern bezieht sich auch auf Produkte, die für jeden Wirkstoff getrennte Formulierungen umfassen. Dementsprechend können, wenn mehr als zwei Wirkstoffe angewendet wer- den sollen, alle Wirkstoffe in einer gemeinsamen Formulierung formuliert werden oder alle Wirkstoffe in getrennten Formulierungen formuliert werden; ebenfalls denkbar sind gemischte Formen, bei denen einige der Wirkstoffe gemeinsam formuliert und einige der Wirkstoffe getrennt formuliert sind. Getrennte Formulierungen erlauben die getrennte oder aufeinanderfolgende Anwendung der in Rede stehenden Wirkstoffe. In the animal health field, "blending" not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are used all active substances should be formulated in a common formulation or all active substances should be formulated in separate formulations; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the separate or sequential use of the active substances in question.
Die hier mit ihrem„Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im „Pesticide Manual" (siehe oben) beschrieben oder im Internet recherchierbar (z.B. The active ingredients specified here by their "common name" are known and described, for example, in the "Pesticide Manual" (see above) or searchable on the Internet (e.g.
Beispielhafte Wirkstoffe aus der Gruppe der Ektoparasitizide als Mischungspartner schließen, ohne dass dies eine Einschränkung darstellen soll, die oben ausführlich aufgelisteten Insektizide und Ak- karizide ein. Weitere verwendbare Wirkstoffe sind unten gemäß der oben erwähnten Klassifikation, die auf dem aktuellen IRAC Mode of Action Classification Scheme beruht, aufgeführt: (1) Acetyl- cholinesterase (AChE)-Inhibitoren; (2) GABA-gesteuerte Chlorid-Kanal-Blocker; (3) Natrium- Kanal-Modulatoren; (4) kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (5) allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (6) allosterische Modulatoren des Glutamat- abhängigen Chloridkanals (GluCl); (7) Juvenilhormon- Mimetika; (8) verschiedene nichtspezifische (Multi-Site) Inhibitoren; (9) Modulatoren Chordotonaler Organe; (10) Milbenwachstumsinhibitoren; (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren; (13) Entkoppler der oxidativen Phosphorylierung durch Störung des Protonengra- dienten; (14) Blocker des nicotinischen Acetylcholinrezeptorkanals; (15) Inhibitoren der Chitinbiosynthese, Typ 0; (16) Inhibitoren der Chitinbiosynthese, Typ 1; (17) Häutungsdisruptor (insbesondere bei Dipteren, d.h. Zweiflüglern); (18) Ecdyson-Rezeptor-Agonisten; (19) Octopamin-Rezeptor- Agonisten; (21) mitochondriale Komplex- I-Elektronentransportinhibitoren; (25) mitochondriale Komplex-II-Elektronentransportinhibitoren; (20) mitochondriale Komplex-III- Elektronentransportinhibitoren; (22) Blocker des spannungsabhängigen Natriumkanals; (23) Inhibitoren der Acetyl-CoA-Carboxylase; (28) Ryanodinrezeptor-Modulatoren; Exemplary agents from the group of ectoparasiticides as a mixing partner include, but are not limited to, the insecticides and acaricides detailed above. Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of oxidative phosphorylation by disrupting the proton gradient; (14) blocker of the nicotinic acetylcholine receptor channel; (15) inhibitors of chitin biosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1; (17) molting disruptor (especially in dipterans, i.e., two-winged); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) blocker of the voltage-dependent sodium channel; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators;
Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, z. B. Fentrifanil, Feno- xacrim, Cyclopren, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quino- methionat, Triarathen, Clothiazoben, Tetrasul, Kaliumoleat, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Brompropylat, Cryolit; Active substances with unknown or non-specific mechanisms of action, eg. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Piri- miphos(-ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Sulprofos, Propa- phos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton-S-methylsulfon, Isazofos, Cyanofen- phos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpy- rifos(-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensul- fothion, Etrimfos; Compounds from other classes, for example butacarb, dimetilane, cloethocarb, phosphocarb, pirimiphos (-ethyl), parathion (-ethyl), methacrifos, isopropyl-o-salicylate, trichlorofon, sulprofos, propaphos, sebufos, pyridathion, prothoate, Dichlorofenthione, demeton-S-methylsulfone, isazofos, cyanofephos, dialifos, carbophenothione, autothiofos, aromfenvinfos (-methyl), azinphos (-ethyl), chlorophenyl rifos (-ethyl), fosmethilane, iodofenofen, dioxabenzofos, formothion, fonofos, flupyrazofos, fensulfothion, etrimfos;
Organochlorverbindungen, z. B. Camphechlor, Lindan, Heptachlor; oder Phenylpyrazole, z. B. Ace- toprol, Pyrafluprol, Pyriprol, Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Organochlorine compounds, e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetone, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner;
Pyrethroide, z. B. (eis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU 15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bio- ethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalot- hrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs), Neonicotinoide, z. B. Nithiazin Pyrethroids, e.g. Eg, (cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU 15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis Permethrin, clocythrin, cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs), neonicotinoids, e.g. B. Nithiazine
Dicloromezotiaz, Triflumezopyrim makroeyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprino- mectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Dicloromezotiaz, triflumezopyrim, macrocyclic lactones, e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
Tripren, Epofenonan, Diofenolan; Biologicals, Hormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Cod- lemon oder Neem-Komponenten Triphene, Epofenonan, Diofenolan; Biologicals, hormones or pheromones, for example natural products, e.g. Thuringiensin, codemon or neem components
Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Dinitrophenols, e.g. Dinocap, dinobuton, binapacryl;
Benzoylharnstoffe, z. B. Fluazuron, Penfluron, Benzoylureas, eg. Fluazuron, penfluron,
Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Bienenstockvarroa-Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Amidine derivatives, e.g. Chormorman, cymiazole, demiditraz hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid.
Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Exemplary agents from the group of endoparasiticides, as a mixture partner, include, but are not limited to, anthelmintic agents and antiprotozoal agents.
Zu den anthelmintischen Wirkstoffen zählen, ohne hierauf beschränkt zu sein, die folgenden nemati- ziden, trematiziden und/oder cestoziden Wirkstoffe: aus der Klasse der makrocyclischen Lactone zum Beispiel: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; aus der Klasse der Benzimidazole und Probenzimidazole zum Beispiel: Oxibendazol, Mebendazol, Triclabendazol, Thiophanat, Parbendazol, Oxfendazol, Netobimin, Fenbendazol, Febantel, Thiabendazol, Cyclobendazol, Cambendazol, Albendazol-sulfoxid, Albendazol, Flubendazol; aus der Klasse der Depsipeptide, vorzugsweise cyclischen Depsipetide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Levamisol, Tetramisol; aus der Klasse der Aminophenylamidine zum Beispiel: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Aminoacetonitrile zum Beispiel: Monepantel; aus der Klasse der Paraherquamide zum Beispiel: Paraherquamid, Derquantel; aus der Klasse der Salicylanilide zum Beispiel: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; aus der Klasse der substituierten Phenole zum Beispiel: Nitroxynil, Bithionol, Disophenol, Hexachlo- rophen, Niclofolan, Meniclopholan; aus der Klasse der Organophosphate zum Beispiel: Trichlorfon, Naphthalofos, Dichlor vo s/DD VP, Crufomat, Coumaphos, Haloxon; aus der Klasse der Piperazinone/Chinoline zum Beispiel: Praziquantel, Epsiprantel; aus der Klasse der Piperazine zum Beispiel: Piperazin, Hydroxyzin; aus der Klasse der Tetracycline zum Beispiel: Tetracyclin, Chlorotetracyclin, Doxycyclin, Oxytetracyclin, Rolitetracyclin; aus diversen anderen Klassen zum Beispiel: Bunamidin, Niridazol, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon. Antiprotozoische Wirkstoffe, darunter, ohne hierauf beschränkt zu sein, die folgenden Wirkstoffe: aus der Klasse der Triazine zum Beispiel: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; aus der Klasse Polyletherionophor zum Beispiel: Monensin, Salinomycin, Maduramicin, Narasin; aus der Klasse der makrocyclischen Lactone zum Beispiel: Milbemycin, Erythromycin; aus der Klasse der Chinolone zum Beispiel: Enrofloxacin, Pradofloxacin; aus der Klasse der Chinine zum Beispiel: Chloroquin; aus der Klasse der Pyrimidine zum Beispiel: Pyrimethamin; aus der Klasse der Sulfonamide zum Beispiel: Sulfachinoxalin, Trimethoprim, Sulfaclozin; aus der Klasse der Thiamine zum Beispiel: Amprolium; aus der Klasse der Lincosamide zum Beispiel: Clindamycin; aus der Klasse der Carbanilide zum Beispiel: Imidocarb; aus der Klasse der Nitrofurane zum Beispiel: Nifurtimox; aus der Klasse der Chinazolinonalkaloide zum Beispiel: Halofuginon; aus diversen anderen Klassen zum Beispiel: Oxamniquin, Paromomycin; aus der Klasse der Vakzine oder Antigene aus Mikroorganismen zum Beispiel: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus. The anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestocidal agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, Milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipetides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines for example: Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amide shell, deacylated amide shell (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: Monepantel; from the class of Paraherquamide, for example: Paraherquamid, Derquantel; from the class of salicylanilides for example: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, nicolofolane, meniclopholan; from the class of organophosphates, for example: trichlorofon, naphthalofos, dichloro / DD VP, crufomat, coumaphos, haloxone; from the class of piperazinones / quinolines for example: praziquantel, epsiprantel; from the class of piperazines for example: piperazine, hydroxyzine; from the class of tetracyclines for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetoline, emetine, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon. Antiprotozoal agents, including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofurans, for example: nifurtimox; from the class of quinazolinone alkaloids, for example: halofuginone; from various other classes for example: oxamniquine, paromomycin; from the class of vaccines or antigens from microorganisms for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus ,
Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids.
Vektorbekämpfung Die Verbindungen der Formel (I) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arach- nide, 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. Vector Control 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 arachidoid, which is able to attack pathogens such as. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens can be transferred to a host either mechanically (eg, trachoma by non-stabbing flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: 1) Mücken Examples of vectors and their transmitted diseases or pathogens are: 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von anderen Würmern; - Aedes: Gelbfieber, Dengue-Fieber, weitere virale Erkrankungen, Filariasis; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis;
- Simulien: Übertragung von Würmern, insbesondere Onchocerca volvulus; - Simulia: transmission of worms, in particular Onchocerca volvulus;
- Psychodidae: Übertragung von Leishmaniose - Psychodidae: transmission of leishmaniasis
2) Läuse: Hautinfektionen, epidemisches Fleckfieber; 2) lice: skin infections, epidemic typhus;
3) Flöhe: Pest, endemisches Fleckfieber, Bandwürmer; 4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 3) fleas: plague, endemic typhus, tapeworms; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, epidemisches Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis- Enzephalitis, Frühsommer-Meningoenzephalitis (FSME), Krim-Kongo-Fieber, Borreliose; 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;
6) Zecken: Borelliosen wie Borrelia bungdorferi sensu lato., Borrelia duttoni, Frühsommer- Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis), Ehrlichiose. Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten, zum Beispiel Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. 6) Ticks: Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis. Examples of vectors for the purposes of the present invention are insects, for example 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, Psychodide wie Phlebotomus, Lutzomyia, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) Resistenzbrechend sind. Vector control is also possible when the compounds of formula (I) are resistive.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorbekämp- fung, z. B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorrats- und Materialschutz. Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control. Fung, z. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and 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 den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepi- doptera, Psocoptera und Zygentoma. The compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. 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 einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. 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., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, i. h., They can be applied to the appropriate material without further changes. As further insecticides or fungicides, in particular those mentioned above come into question.
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet wer- den 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 fouling of objects, in particular of hulls, sieves, nets, structures, wharfs 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 ver- wendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen, Tierzuchtanlagen 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. 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, Heter- optera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. 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, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development. These pests include for example pests of the class Arachnida, of the orders Scorpiones, Araneae and Opiliones, of the classes Chilopoda and Diplopoda, of the class Insecta the order Blattodea, of 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 Verdampfer- plättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapie- ren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. The application is carried out for example in aerosols, non-pressurized sprays, z. As pump and Zerstäubersprays, foggers, Foggern, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators propeller driven evaporators, energy-less or passive evaporation systems, moth papers, mantle bags 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 beispielsweise nach Verfahren A bis E wie in den folgenden Schemata dargestellt synthetisiert werden. The compounds of formula (I) can be synthesized, for example, by methods A to E as illustrated in the following schemes.
Verfahren A Method A
10 Verfahren E 10 Method E
Die für das Verfahren A benötigten Metallorganyle (z. B. Aryl/Hetaryl-boronsäure/ester, etc.), sowie die benötigten Katalysatoren sind größtenteils Kaufprodukte oder lassen sich nach allgemein in der organischen Chemie bekannten Verfahren herstellen. Die für das Verfahren B benötigten Aryl/Hetaryl-bromide sind größtenteils Kaufprodukte oder lassen sich nach allgemein in der organischen Chemie bekannten Verfahren herstellen. The metal organyls required for process A (eg aryl / hetarylboronic acid ester, etc.), as well as the required catalysts, are mostly purchased products or can be prepared by processes generally known in organic chemistry. The aryl / hetaryl bromides required for process B are mostly purchased products or can be prepared by processes generally known in organic chemistry.
Die für das Verfahren C benötigten Nitriloxide, bzw. deren Vorstufen sind größtenteils Kaufprodukte oder lassen sich nach allgemein in der organischen Chemie bekannten Verfahren herstellen. The nitrile oxides required for process C or their precursors are largely purchased products or can be prepared by processes generally known in organic chemistry.
Die für das Verfahren D benötigten ortho-Iodphenole sind größtenteils Kaufprodukte oder lassen sich nach allgemein in der organischen Chemie bekannten Verfahren herstellen. The ortho-iodophenols required for the process D are largely purchased products or can be prepared by processes generally known in organic chemistry.
Die für das Verfahren F benötigten 3-Amino-pyridine der Formel (X) sind kommerziell erhältlich oder können beispielweise nach literaturbekannten Verfahren hergestellt werden, z. B., Liu, Zhen- Jiang; Vors, Jean-Pierre; Gesing, Ernst R. F.; Bolm, Carsten, Advanced Synthesis and Catalysis, 2010 , 352, 3158 - 3162, BAYER CROPSCIENCE AG Patent: US2010/305124 AI, 2010, Shafir, Alexandr; Buchwald, Stephen L., Journal of the American Chemical Society, 2006 , 128, 8742 - 8743. The required for the process F 3-aminopyridines of the formula (X) are commercially available or can be prepared, for example, by literature methods, for. B., Liu, Zhen-Jiang; Vors, Jean-Pierre; Gesing, Ernst R. F .; Bolm, Carsten, Advanced Synthesis and Catalysis, 2010, 352, 3158-3162, BAYER CROPSCIENCE AG Patent: US2010 / 305124 AI, 2010, Shafir, Alexandr; Buchwald, Stephen L., Journal of the American Chemical Society, 2006, 128, 8742-8743.
Amidierunssv erfahren Amidierunssv experienced
Die Intermediate der Formel (IX) in dem erfindungsgemäßen Verfahren F lassen sich mit Hilfe von literaturbekannten Methoden oder analog den explizit genannten Beispielen synthetisieren. The intermediates of the formula (IX) in the process F according to the invention can be determined with the aid of synthesize literature methods or analogously to the examples explicitly mentioned.
Für den Amidierungsschritt sind zahlreiche Reaktionsbedingungen beschrieben worden, z.B. G. Benz in Comprehensive Organic Synthesis, Ist Ed., Pergamon Press, Oxford, 1991, Vol. 6, S. 381-417; P.D. Bailey et al. in Comprehensive Organic Functional Group Transformation, Ist Ed., Elsevier Sci- ence Ltd., Oxford, 1995, Vol. 5, S. 257-308 und R.C. Larock in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York, Weinheim, 1999, S. 1929-1994. Einige dieser Reaktionen verlaufen über intermediäre Carbonsäurechloride, die isoliert oder in situ erzeugt eingesetzt werden können. Numerous reaction conditions have been described for the amidation step, eg G. Benz in Comprehensive Organic Synthesis, Ist Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp. 381-417; PD Bailey et al. in Comprehensive Organic Functional Group Transformation, I st Ed., Elsevier sci ence Ltd., Oxford, 1995, Vol. 5, pp 257-308 and Larock RC in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH, New York , Weinheim, 1999, p. 1929-1994. Some of these reactions proceed via intermediate carboxylic acid chlorides, which can be used in isolation or generated in situ.
Die Amidierungsreaktionen erfolgen gegebenenfalls in Gegenwart eines Kondensationsmittels, ge- geben enfalls in Gegenwart eines Säureakzeptors und gegebenenfalls in Gegenwart eines Lösungsmittels. If appropriate, the amidation reactions are carried out in the presence of a condensing agent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a solvent.
Als Kondensationsmittel kommen alle üblicherweise für derartige Amidierungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Aktivierungsreagenzien wie Phosgen, Phosphortrichlorid, Phosphoroxychlorid, Oxalylchlorid, Oxalylbromid oder Thionylchlorid; Car- bodiimide, wie '-Dicyclohexylcarbodiimid (DCC) und l-(3-Dimethylaminopropyl)-3-ethyl- carbodiimid (EDCI), oder andere übliche Kondensationsmittel, wie Phosphorpentoxid, Polyphos- phorsäure, '-Carbonyldiimidazol, 2-Chlorpyridin 1-Methoiodid (Mukaiyamas Reagenz), 2- Ethoxy-N-ethoxycarbonyl- 1 ,2-dihydrochinolin (EEDQ), Triphenylphosphin/Tetrachlorkohlenstoff, Brom-tripyrrolidino-phosphonium-hexafluorphosphat (BROP), 0-(7i7-Benzotriazol- 1 - yloxy)tris(dimethylamino)phosphonium-hexafluorphosphat (BOP), Ν,Ν,Ν',Ν'-Suitable condensing agents are all condensing agents customarily used for such amidation reactions. Examples include activating reagents such as phosgene, phosphorus trichloride, phosphorus oxychloride, oxalyl chloride, oxalyl bromide or thionyl chloride; Carbodiimides, such as '-dicyclohexylcarbodiimide (DCC) and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide (EDCI), or other customary condensation agents, such as phosphorus pentoxide, polyphosphoric acid,' -carbonyldiimidazole, 2-chloropyridine 1 Methoiodide (Mukaiyamas reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidinophosphonium hexafluorophosphate (BROP), 0- (7i-benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (BOP), Ν, Ν, Ν ', Ν'-
Bis(tetramethylen)cloruronium-tetrafluorborat, 0-(l H-Benzotriazol-l-yl)-N, Ν,Ν',Ν'- tetramethyluronium-hexafluorphosphat (HBTU), 0-(7i7-Benzotriazol- l-yl)-N,N,N',N'- bis(tetramethylen)uronium-hexafluorphosphat, 0-(l H-Benzotriazol-l-yl)-N, Ν,Ν',Ν'- tetramethyluronium-tetrafluorborat (TBTU), 0-(l H-Benzotriazol-l-yl)-N,N, Ν',Ν'- bis(tetramethylen)uronium-tetrafluorborat, 0-(7-Azabenzotriazol-l-yl)-/V,/V,/V',/V'- tetramethyluronium-hexafluorphosphat (HATU), 1-Hydroxybenzotriazol (HOBt) und 4-(4,6- Dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholiniumsalz (DMT.MM), meistens als Chlorid verfügbar. Diese Reagenzien können separat oder in Kombination eingesetzt werden. Bis (tetramethylene) cloruronium tetrafluoroborate, 0- (1H-benzotriazol-1-yl) -N, Ν, Ν ', Ν'-tetramethyluronium hexafluorophosphate (HBTU), 0- (7i7-benzotriazol-1-yl) - N, N, N ', N'-bis (tetramethylene) uronium hexafluorophosphate, 0- (1H-benzotriazol-1-yl) -N, Ν, Ν', Ν'-tetramethyluronium tetrafluoroborate (TBTU), 0- (1H-Benzotriazol-1-yl) -N, N, Ν ', Ν'-bis (tetramethylene) uronium tetrafluoroborate, 0- (7-azabenzotriazol-1-yl) - / V, / V, / V' , / V'-tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and 4- (4,6-dimethoxy-l, 3,5-triazin-2-yl) -4-methylmorpholinium salt (DMT.MM), mostly available as chloride. These reagents can be used separately or in combination.
Als Säureakzeptor kommen alle üblichen anorganischen oder organischen Basen infrage, beispiels- weise organische Amine wie Triethylamin, Diisopropylethylamin, -Mefhylmorpholin, Pyridin oder -Dimefhylaminopyridin, Alkali- und Erdalkalicarbonate wie Lithiumcarbonat Natriumcarbonat, Kaliumcarbonat oder Caesiumcarbonat; Alkalyhydrogencarbonate wie Natrumhydrogencarbonat oder Kaliumhydrogencarbonat. Die Amidierungsreaktion in den erfindungsgemäßen Verfahren wird gegebenenfalls in Gegenwart eines geeigneten Reaktionshilfstoffes wie beispielsweise N,N- Dimethylformamid oder -Dimethylaminopyridin durchgeführt. Als Lösungs- oder Verdün- nungsmittel kommen alle interten organischen Lösungsmittel in Betracht, beispielsweise aliphatische oder aromatische Kohlenwasserstoffe (wie Petrolether, Toluol, Cyclohexan), halogenierte Kohlenwasserstoffe (wie Chlortoluol, Dichlorbenzol, Dichlormethan, Chloroform, 1,2-Dichlorethan), Ether (wie Diethylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan), Ester (wie Essigsäureefhylester- oder -methylester), Nitrokohlenwasserstoffe (wie Nitromethan, Nitroethan, Nitrobenzol), Nitrile (wie Acetonitril, Propionitril, Butyronitril. Benzonitril), Amide (wie -Dimefhylformamid, N,N- Dimethylacetamide, /V-Methylformanilid, -Mefhylpyrrolidon, Hexamethylphosphorsäuretriamid) sowie Dimethylsulfoxid, Sulfolan oder Wasser oder Gemische der genannten Lösungsmittel. Suitable acid acceptors are all customary inorganic or organic bases, for example organic amines such as triethylamine, diisopropylethylamine, methylmorpholine, pyridine or dimethylimidopyridine, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate or cesium carbonate; Alkalihydrogencarbonate such as sodium bicarbonate or potassium bicarbonate. The amidation reaction in the processes according to the invention is optionally carried out in the presence of a suitable reaction auxiliary, for example N, N-dimethylformamide or -dimethylaminopyridine. As a solution or dilution Suitable solvents are all interten organic solvents, for example aliphatic or aromatic hydrocarbons (such as petroleum ether, toluene, cyclohexane), halogenated hydrocarbons (such as chlorotoluene, dichlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane), ethers (such as diethyl ether, dioxane, tetrahydrofuran , 1,2-dimethoxyethane), esters (such as ethyl acetate or methyl ester), nitrohydrocarbons (such as nitromethane, nitroethane, nitrobenzene), nitriles (such as acetonitrile, propionitrile, butyronitrile, benzonitrile), amides (such as dimethylformamide, N, N). Dimethylacetamide, / V-methylformanilide, -methylpyrrolidone, hexamethylphosphoric triamide) and also dimethyl sulfoxide, sulfolane or water or mixtures of the solvents mentioned.
Es können auch gemischte Anhydride zur Darstellung von Verbindungen der Formel (II) verwendet werden (vgl. J. Am. Chem. Soc. 1967, 5012). Bei diesem Verfahren können Chlorameisensäureester zum Einsatz kommen, wie z.B. Chlorameisensäuremethylester, Chlorameisensäureethylester, Chlo- rameisensäureisobutylester und Chlorameisensäureisopropylester. Ebenfalls können dafür Diethyl- acetylchlorid, Trimethylacetylchlorid und ähnliche Verbindungen verwendet werden. It is also possible to use mixed anhydrides for the preparation of compounds of the formula (II) (compare J. Am. Chem. Soc. 1967, 5012). In this process, chloroformates may be used, e.g. Methyl chloroformate, ethyl chloroformate, isobutyl chloroformate and isopropyl chloroformate. Also, diethyl acetyl chloride, trimethylacetyl chloride and the like can be used therefor.
Die Verfahren A bis F sind grundsätzlich im Stand der Technik bekannt, daher werden nachfolgend lediglich bespielhaft für weniger beaknnte Varianten Literaturhinweise gegeben: The methods A to F are known in principle in the prior art, therefore, below are given as examples only for less suitable variants references:
Für das Verfahren B sei auf: Bellina, Fabio; Guazzelli, Nicola; Lessi, Marco; Manzini, Chiara; Tetrahedron, 2015 , vol. 71, 2298 verwiesen. Darin wird die B: Pd/Cu cokatalysierte C-H- (Het)arylierung beschrieben. For method B, see: Bellina, Fabio; Guazzelli, Nicola; Lessi, Marco; Manzini, Chiara; Tetrahedron, 2015, vol. 71, 2298. It describes the B: Pd / Cu cocatalyzed C-H (Het) arylation.
Für das Verfahren D sei auf Vito Fiandanese et al., Tetrahedron 2008, 64, 53-60 verwiesen. Darin wird die Tandem Sonogashira-Oxocyclisierung von Alkinen und ortho-Iod-Phenolen beschrieben. For method D, see Vito Fiandanese et al., Tetrahedron 2008, 64, 53-60. It describes the tandem Sonogashira oxocyclization of alkynes and ortho-iodo-phenols.
Herstellungsbeispiele Preparation Examples
Die folgenden Herstellungs- und Verwendungsbeispiele illustrieren die Erfindung, ohne sie zu beschränken. Die Produkte wurden mittels 1H-NMR Spektroskopie und/oder LC/MS (Liquid Chromatography Mass Spectrometry) charakterisiert. Die Bestimmung der logP Werte erfolgte gemäß OECD Guideline 117 (EC Directive 92/69/EEC) durch HPLC (High Performance Liquid Chromatography) an reversed-phase (RP) Säulen (C18), mit nachfolgenden Methoden: The following examples of preparation and use illustrate the invention without limiting it. The products were characterized by 1H NMR spectroscopy and / or LC / MS (Liquid Chromatography Mass Spectrometry). The determination of the logP values was carried out according to OECD Guideline 117 (EC Directive 92/69 / EEC) by HPLC (High Performance Liquid Chromatography) on reversed-phase (RP) columns (C18), using the following methods:
[a] Die Bestimmung mit der LC-MS im sauren Bereich erfolgte bei pH 2,7 mit 0,1 % wässriger Ameisensäure und Acetonitril (enthält 0,1% Ameisensäure) als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril. [b] Die Bestimmung mit der LC-MS im neutralen Bereich erfolgte bei pH 7.8 mit 0,001 molarer wässriger Ammoniumhydrogencarbonat-Lösung und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril. [a] The determination with the LC-MS in the acidic range was carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. [b] The determination with the LC-MS in the neutral range was carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
Die Eichung erfolgte mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP- Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinander folgenden Alkanonen). The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
Die NMR-Spektren wurden mit einem Bruker Avance 400, ausgestattet mit einem Durchflusspro- benkopf (60 μΐ Volumen), bestimmt. In Einzelfällen wurden die NMR Spektren mit einem Bruker Avance II 600 gemessen. Die NMR-Daten ausgewählter Beispiele werden in klassischer Form (δ-Werte, Multiplettaufspal- tung, Anzahl der H-Atome) aufgeführt. Die Aufspaltung der Signale wurde wie folgt beschrieben: s (Singulett), d (Duplett), t (Triplett), q (Quartett), quint (Quintuplett), m (Multiplett), br (für breite Signale). Als Lösungsmittel wurden CD3CN, CDCI3 oder D6-DMSO verwendet, wobei als Referenz Tetramethylsilan (0.00 ppm) eingesetzt wurde. Verfahren A The NMR spectra were determined with a Bruker Avance 400 equipped with a flow through probe head (60 μΐ volume). In individual cases the NMR spectra were measured with a Bruker Avance II 600. The NMR data of selected examples are listed in classical form (δ values, multiplet splitting, number of H atoms). The splitting of the signals was described as follows: s (singlet), d (doublet), t (triplet), q (quartet), quint (quintuplet), m (multiplet), br (for broad signals). The solvents used were CD 3 CN, CDCl 3 or D6-DMSO, tetramethylsilane (0.00 ppm) being used as reference. Method A
Beispiel (50) Example (50)
1 1 '-Bis di hen l hos hino 1 1 '-bis di hen l hos hino
Herstellung der Verbindung (XI) Preparation of compound (XI)
Schritt 1 lg (4.565 mmol) l-Methyl-2-brom-imidazol-5-carbonsäuremethylester (ABCR) wurden in 10ml Ethanol gelöst, mit 5.48ml 1 N NaOH(aq.) versetzt und 60 Min bei Raumtemperatur gerührt. Nach Zugabe von 5.5mL IN HCl(aq.) (auf pH ~ 3 eingestellt), entsteht ein weißer Niederschlag. Der Ansatz wurde bis zur Trockene eingeengt und im Ultraschallbad in 6mL Wasser suspendiert. Die weißen Kristalle wurden abfiltriert und mit 2mL Wasser gewaschen. Die Mutterlauge wurde fast bis zur Trockenen eingeengt. Die Kristalle wurden abgesaugt und mit wenig Wasser gewaschen. Die vereinigten Kristalle wurden im Ölpumpenvakuum getrocknet. Ausbeute: 890mg (95% d. Theorie). logP[a] :0.31; Step 1 (4.565 mmol) of 1-methyl-2-bromo-imidazole-5-carboxylic acid methyl ester (ABCR) was dissolved in 10 ml of ethanol, treated with 5.48 ml of 1 N NaOH (aq.) And stirred at room temperature for 60 min. To Addition of 5.5 mL IN HCl (aq.) (Adjusted to pH ~ 3) gives a white precipitate. The batch was concentrated to dryness and suspended in 6 ml of water in an ultrasound bath. The white crystals were filtered off and washed with 2mL of water. The mother liquor was concentrated almost to dryness. The crystals were filtered off with suction and washed with a little water. The combined crystals were dried in an oil pump vacuum. Yield: 890 mg (95% of theory). logP [a]: 0.31;
Ή-NMR (de-DMSO, 400MHz); δ = 3.82 (s, 3H), 7.60 (s, 1H), 13.15 (s, 1H) ppm. Schritt 2 Ή-NMR (de-DMSO, 400MHz); δ = 3.82 (s, 3H), 7.60 (s, 1H), 13.15 (s, 1H) ppm. step 2
Eine Suspension von 890mg (4.341 mmol) l-Methyl-2-brom— imidazol-5-carbonsäure (IX-1) in 15 ml Dichlormethan, wurde mit ca. 60 mg DMF aus einer Spritzenkanüle versetzt. Bei Raumtemperatur wurden 940mg (4.341 mmol) Oxalylbromid hinzugefügt, wobei eine intensive Gasentwicklung einsetzte. Am nächsten Tag wurden weitere 10 ml Dichlormethan und 140 mg Oxalylbromid hinzugegeben. Nach lh Rühren bei Raumtemperatur erfolgte eine weitere Zugabe von 110mg Oxalylbromid und 30 mg DMF und es wurde weitere Stunde bei Raumtemperatur nachgerührt, LC MS -Kontrolle zeigte 96% Umsatz. Die Suspension wurde ohne weitere Aufarbeitung zur Synthese der Verbindung (XI- 1) eingesetzt. A suspension of 890 mg (4,341 mmol) of 1-methyl-2-bromo-imidazole-5-carboxylic acid (IX-1) in 15 ml of dichloromethane was admixed with about 60 mg of DMF from a syringe cannula. At room temperature, 940 mg (4,341 mmol) of oxalyl bromide were added, with intense gas evolution. The next day, an additional 10 ml of dichloromethane and 140 mg of oxalyl bromide were added. After stirring for 1 h at room temperature, a further addition of 110 mg of oxalyl bromide and 30 mg of DMF was carried out and stirring was continued for a further hour at room temperature, LC MS control showed 96% conversion. The suspension was used without further work-up for the synthesis of the compound (XI-1).
Schritt 3 Herstellung der Verbindung (XI) Step 3 Preparation of Compound (XI)
14.02g (40.19 mmol) l-Methyl-2-brom-imidazol-5-carbonsäurebromid (X-l) wurden in 80ml Dichlormethan suspendiert und auf 0°C abgekühlt. Eine Lösung aus 4.35g (40.19 mmol) 3- Methylamino-pyridin (V-1) und 41 ml (241.2 mmol) Hünig-Base gelöst in 40ml Dichlormethan wurden bei 0°C zugeben. Es wurde lh bei Raumttemperatur nachgerührt, anschließend 4h unter Rückfluss gekocht und über Nacht bei RT stehen gelassen. Der Ansatz wurde im Vakkum eingeengt Der Rückstand wurde in 500mL Dichlormethan aufgenommen und 3x mit insgesamt 400 ml Wasser gewaschen (2 x ca. 200ml und lx ca. 100ml). Die vereinigten wässrigen Phasen wurden mit ca. 50ml Dichlormethan extrahiert und die organischen Phasen vereinigt. Die vereinigten organischen Phasen wurden 2x mit einer wässrigen NaHC03-Lsg. gewaschen (3,5g NaHC03 in 150ml Wasser). Die vereinigten wässrigen Phasen wurden mit ca. 50ml Dichlormethan extrahiert, die organischen Phasen vereinigt, getrocknet und im Vakkum eingeengt. Ausbeute: 10.45g (81.9% d. Theorie) braunes, zähes Öl in einer Reinheit LC/MS 93%. logP[a] : 0.65; logP[n] : 0.93 14.02 g (40.19 mmol) of 1-methyl-2-bromo-imidazole-5-carboxylic acid bromide (X-1) were suspended in 80 ml of dichloromethane and cooled to 0 ° C. A solution of 4.35 g (40.19 mmol) of 3-methylaminopyridine (V-1) and 41 mL (241.2 mmol) of Hünig base dissolved in 40 mL of dichloromethane was added at 0 ° C. The mixture was stirred at room temperature for 1 h, then refluxed for 4 h and allowed to stand overnight at RT. The mixture was concentrated in vacuo. The residue was taken up in 500 ml of dichloromethane and washed 3 × with a total of 400 ml of water (2 × approx. 200 ml and 1 × approx. 100 ml). The combined aqueous phases were extracted with about 50 ml of dichloromethane and the organic phases were combined. The combined organic phases were washed twice with an aqueous NaHCO 3 solution. washed (3.5g NaHCO3 in 150ml water). The combined aqueous phases were extracted with about 50 ml of dichloromethane, the organic phases combined, dried and concentrated in vacuo. Yield: 10.45 g (81.9% of theory) brown, viscous oil in a purity LC / MS 93%. logP [a]: 0.65; logP [n]: 0.93
XH-NMR (de-DMSO, 400MHz); δ = 3.37 (s, 3H), 3.75 (s, 3H), 6.25 (s, 1H), 7.43-7.47 (m, 1H), 7.84- 7.87 (m, 1H), 8.48-8.49 (m, 1H), 8.52 (m, 1H) ppm. X H NMR (de-DMSO, 400MHz); δ = 3.37 (s, 3H), 3.75 (s, 3H), 6.25 (s, 1H), 7.43-7.47 (m, 1H), 7.84-7.87 (m, 1H), 8.48-8.49 (m, 1H), 8.52 (m, 1H) ppm.
Herstellung der Verbindung (50) Eine Mischung aus 200 mg (0.67 mmol) Bromid (XI), 141 mg (0.67 mmol) [4-Fluor-3- (trifluormethyl)phenyl]borsäure, 3.8 Äquivalenten Natriumcarbonat, 0.05 Eq. 1,1'- Bis(diphenylphosphino)ferrocenpalladium(II)chlorid, 0.05 Eq. 1 , l'-Bis(diphenylphosphino)ferrocen, 2 ml 1,2-Dimethoxyethan und 0.5 ml Wasser wurde mit Argon gespült und anschliessend in der Mikrowelle unter Rühren für 30 Minuten auf 140°C erhitzt. Der Ansatz wurde eingedampft und zwischen DichlormethanA asser verteilt. Die organische Phase wurde mit Magnesiumsulfat getrocknet, filtiert und das Filtrat zur Trockene eingedampft. Der so erhaltene Rückstand wird mittels. HPLC aufgerei- nigt. Ausbeute 138 mg (51% d. Theorie). Preparation of Compound (50) A mixture of 200 mg (0.67 mmol) bromide (XI), 141 mg (0.67 mmol) of [4-fluoro-3- (trifluoromethyl) phenyl] boric acid, 3.8 equivalents of sodium carbonate, 0.05 eq '- Bis (diphenylphosphino) ferrocenepalladium (II) chloride, 0.05 Eq. 1, l'-bis (diphenylphosphino) ferrocene, 2 ml of 1,2-dimethoxyethane and 0.5 ml of water was purged with argon and then in the microwave with stirring for 30 Heated to 140 ° C for a few minutes. The reaction was evaporated and partitioned between dichloromethane and water. The organic phase was dried with magnesium sulfate, filtered and the filtrate evaporated to dryness. The residue thus obtained is. HPLC purified. Yield 138 mg (51% of theory).
Ή-NMR (CD3CN 400MHz); δ = 3.43 (s, 3H), 3.83 (s, 3H), 6.39 (s, 1H), 7.37-7-45 (m, 2H), 7.71- 7.74 (m, 1H), 7.86- 7.90 (m, 2H), 8.46-8.49 (m, 2H). Beispiel (7) Ή-NMR (CD 3 CN 400 MHz); δ = 3.43 (s, 3H), 3.83 (s, 3H), 6.39 (s, 1H), 7.37-7-45 (m, 2H), 7.71-7.74 (m, 1H), 7.86-7.90 (m, 2H ), 8.46-8.49 (m, 2H). Example (7)
Herstellung der Verbindung (7) Preparation of compound (7)
100 mg (0,33 mmol) Bromid (XI), 41,6 mg (0,33 mmol) Pyridin-3-ylborsäure und 25 mg (0,03 mmol) Bis(tricyclohexylphosphin)palladium(II)chlorid wurden in einem Gemisch aus entgastem Dioxan (2 mL) und entgaster Natriumcarbonatlösung (2M, 1 mL) vorgelegt und in der Mikrowelle 30 min auf 120 °C erhitzt. Anschließend wurde auf Raumtemperatur abgekühlt und das Reaktionsgemisch wurde über eine Mischung aus Kieselgel und Extrelut® NT filtriert. Das Filtrat wurde zur Trockne eingeengt. Der Rückstand wurde durch RP-HPLC mit einem Wasser / Acetonitril- Gradienten als Laufmittel gereinigt. 1H-NMR(400 MHz, D6-DMSO) δ ppm: 3,42 (s, 3H), 3,87 (s, 3H), 6,42 (s, 1H), 7,46-7,49 (m, 1H), 7,51-7,54 (m, 1H), 7,88-7,91 (m, 1H), 8,06-8,09 (m, 1H), 8,49-8,51 (m, 1H), 8,54-8,55 (m, 1H), 8,65-8,67 (m, IH), 8,83-8,84 (m, IH) Beispiel (6) 100 mg (0.33 mmol) of bromide (XI), 41.6 mg (0.33 mmol) of pyridin-3-ylboronic acid and 25 mg (0.03 mmol) of bis (tricyclohexylphosphine) palladium (II) chloride were added in a mixture from degassed dioxane (2 mL) and degassed sodium carbonate solution (2M, 1 mL) and heated in the microwave at 120 ° C for 30 min. It was then cooled to room temperature and the reaction mixture was filtered through a mixture of silica gel and Extrelut® NT. The filtrate was concentrated to dryness. The residue was purified by RP-HPLC with a water / acetonitrile gradient as eluent. 1 H NMR (400 MHz, D 6 -DMSO) δ ppm: 3.42 (s, 3H), 3.87 (s, 3H), 6.42 (s, 1H), 7.46-7.49 (m, 1H), 7.51-7.54 (m, 1H), 7.88-7.91 (m, 1H), 8.06-8.09 (m, 1H), 8.49-8 , 51 (m, 1H), 8.54-8.55 (m, 1H), 8.65-8.67 (m, IH), 8.83-8.84 (m, IH) Example (6)
Herstellung der Verbindung (6) 100 mg (0,33 mmol Bromid (XI), 41,3 mg (0,33 mmol) Phenylborsäure und 25 mg (0,03 mmol) Bis(tricyclohexylphosphin)palladium(II)chlorid wurden in einem Gemisch aus entgastem Dioxan (2 mL) und entgaster Natriumcarbonatlösung (2M, 1 mL) vorgelegt und in der Mikrowelle 30 min auf 120 °C erhitzt. Anschließend wurde auf Raumtemperatur abgekühlt und das Reaktionsgemisch wurde über eine Mischung aus Kieselgel und Extrelut® NT filtriert. Das Filtrat wurde zur Trockne ein- geengt. Der Rückstand wurde durch RP-HPLC mit einem Wasser / Acetonitril-Gradienten als Laufmittel gereinigt. Preparation of Compound (6) 100 mg (0.33 mmol bromide (XI), 41.3 mg (0.33 mmol) phenylboronic acid and 25 mg (0.03 mmol) bis (tricyclohexylphosphine) palladium (II) chloride were added in a A mixture of degassed dioxane (2 mL) and degassed sodium carbonate solution (2M, 1 mL) was added and heated in the microwave for 30 minutes at 120 ° C. It was then cooled to room temperature and the reaction mixture was filtered through a mixture of silica gel and Extrelut® NT. The filtrate was concentrated to dryness and the residue was purified by RP-HPLC eluting with a water / acetonitrile gradient.
1H-NMR(400 MHz, D6-DMSO) δ ppm: 3,41 (s, 3H), 3,83 (s, 3H), 6,37 (s, IH), 7,46-7,51 (m, 4H), 7,62-7,64 (m, 2H), 7,87-7,90 (m, IH), 8,49-8,50 (m, IH), 8,54-8,55 (m, IH). 1 H NMR (400 MHz, D 6 -DMSO) δ ppm: 3.41 (s, 3H), 3.83 (s, 3H), 6.37 (s, IH), 7.46-7.51 (m, 4H), 7.62-7.64 (m, 2H), 7.87-7.90 (m, IH), 8.49-8.50 (m, IH), 8.54-8 , 55 (m, IH).
Beispiel (14) Example (14)
Herstellung der Verbindung (14) Preparation of the compound (14)
100 mg (0,33 mmol) Bromid (XI), 70,2 mg (0,33 mmol) l-Methyl-2-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrrol und 25 mg (0,03 mmol) Bis(tricyclohexylphosphin)palladium(II)- chlorid wurden in einem Gemisch aus entgastem Dioxan (2 mL) und entgaster Natrium- carbonatlösung (2M, 1 mL) vorgelegt und in der Mikrowelle 30 min auf 120 °C erhitzt. Anschließend wurde auf Raumtemperatur abgekühlt und das Reaktionsgemisch wurde über eine Mischung aus Kieselgel und Extrelut® NT filtriert. Das Filtrat wurde zur Trockne eingeengt. Der Rückstand wurde durch RP-HPLC mit einem Wasser / Acetonitril-Gradienten als Laufmittel gereinigt. 100 mg (0.33 mmol) bromide (XI), 70.2 mg (0.33 mmol) 1-methyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 yl) -IH-pyrrole and 25 mg (0.03 mmol) of bis (tricyclohexylphosphine) palladium (II) chloride were initially introduced into a mixture of degassed dioxane (2 ml) and degassed sodium carbonate solution (2M, 1 ml) and poured into the microwave heated for 30 min at 120 ° C. It was then cooled to room temperature and the reaction mixture was filtered through a mixture of silica gel and Extrelut® NT. The filtrate was concentrated to dryness. The residue was purified by RP-HPLC with a water / acetonitrile gradient as eluent.
1H-NMR(400 MHz, D6-DMSO) δ ppm: 3,40 (s, 3H), 3,63 (s, 3H), 3,79 (s, 3H), 6,12-6,14 (m, IH), 6,37 (s, IH), 6,43-6,44 (m, IH), 6,93-6,94 (m, IH), 7,44-7,48 (m, IH), 7,85-7,88 (m, IH), 8,48-8,49 (m, IH), 8,52-8,53 (m, IH). Beispiel (33) 1 H-NMR (400 MHz, D 6 -DMSO) δ ppm: 3.40 (s, 3H), 3.63 (s, 3H), 3.79 (s, 3H), 6, 12-6, 14 (m, IH), 6.37 (s, IH), 6.43-6.44 (m, IH), 6.93-6.94 (m, IH), 7.44-7.48 (m , IH), 7.85-7.88 (m, IH), 8.48-8.49 (m, IH), 8.52-8.53 (m, IH). Example (33)
Herstellung der Verbindung (33) Preparation of the compound (33)
210 mg (0,71 mmol) Bromid (XI), 87 mg, (0,71 mmol) Pyridin-4-ylborsäure und 82 mg (0,07 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Dioxan (4,3 mL) und entgaster Natriumcarbonatlösung (2M, 3,2 mL) vorgelegt und 14 h bei 92 °C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt und das Reaktionsgemisch wurde über Celite® filtriert. Das Filtrat wurde zur Trockne eingeengt. Der Rückstand wurde in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt. Die organische Phase wurde über Magnesiumsulfat getrock- net und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert. Der Rückstand wurde durch RP- HPLC mit einem Wasser / Acetonitril-Gradienten als Laufmittel gereinigt. 210 mg (0.71 mmol) of bromide (XI), 87 mg, (0.71 mmol) of pyridin-4-ylboronic acid and 82 mg (0.07 mmol) of tetrakis (triphenylphosphine) palladium (0) were dissolved in a mixture of degassed Dioxane (4.3 mL) and degassed sodium carbonate solution (2M, 3.2 mL) and stirred at 92 ° C for 14 h. It was then cooled to room temperature and the reaction mixture was filtered through Celite®. The filtrate was concentrated to dryness. The residue was taken up in dichloromethane and water. The phases were separated. The organic phase was dried over magnesium sulphate and filtered. The solvent was distilled off in vacuo. The residue was purified by RP-HPLC with a water / acetonitrile gradient as eluent.
1H-NMR(400 MHz, D6-DMSO) δ ppm: 3,42 (s, 3H), 3,92 (s, 3H), 6,46 (s, 1H), 7,45-7,48 (m, 1H), 7,67-7,69 (m, 2H), 7,88-7,90 (m, 1H), 8,48-8,54 (m, 2H), 8,68-8,70 (m, 2H). 1 H NMR (400 MHz, D 6 -DMSO) δ ppm: 3.42 (s, 3H), 3.92 (s, 3H), 6.46 (s, 1H), 7.45-7.48 (m, 1H), 7.67-7.69 (m, 2H), 7.88-7.90 (m, 1H), 8.48-8.54 (m, 2H), 8.68-8 , 70 (m, 2H).
Beispiel (47) Example (47)
Herstellung der Verbindung (47) Preparation of compound (47)
120 mg (0,40 mmol) Bromid (XI), 225 mg (0,61 mmol) 2-(Tributylstannyl)pyridin, 52 mg (1,22 mmol) Lithiumchlorid und 7,7 mg (0,04 mmol) Kupfer(I)iodid wurden in entgastem Dioxan (2,4 mL) vorgelegt und mit 94 mg (0,08 mmol) Tetrakis(triphenylphosphin)palladium(0) versetzt. Unter einer Argonatmosphäre wurde die Mischung in der Mikrowelle 60 min auf 150 °C erhitzt. Anschließend wurde auf Raumtemperatur abgekühlt und das Reaktionsgemisch wurde über Celite® filtriert. Das Filtrat wurde zur Trockne eingeengt. Der Rückstand wurde durch säulenchromatographische Reinigung mit einem Wasser / Acetonitril-Gradienten als Laufmittel gereinigt. 120 mg (0.40 mmol) bromide (XI), 225 mg (0.61 mmol) 2- (tributylstannyl) pyridine, 52 mg (1.22 mmol) lithium chloride and 7.7 mg (0.04 mmol) copper ( I) iodide were initially charged in degassed dioxane (2.4 mL) and treated with 94 mg (0.08 mmol) of tetrakis (triphenylphosphine) palladium (0). Under an argon atmosphere, the mixture was heated in the microwave at 150 ° C for 60 minutes. It was then cooled to room temperature and the reaction mixture was filtered through Celite®. The filtrate was concentrated to dryness. The residue was purified by column chromatography with a water / acetonitrile gradient as eluent.
1H-NMR(400 MHz, D6-DMSO) δ ppm: 3,42 (s, 3H), 4,17 (s, 3H), 6,46 (s, 1H), 7,41-7,46 (m, 2H), 7,86-7,92 (m, 2H), 7,96-7,98 (m, 1H), 8,43-8,53 (m, 2H), 8,65-8,66 (m, 1H). Beispiel (65) 1 H NMR (400 MHz, D 6 -DMSO) δ ppm: 3.42 (s, 3H), 4.17 (s, 3H), 6.46 (s, 1H), 7.41-7.46 (m, 2H), 7.86-7.92 (m, 2H), 7.96-7.98 (m, 1H), 8.43-8.53 (m, 2H), 8.65-8 , 66 (m, 1H). Example (65)
(XI) Mikrowelle 140V (XI) Microwave 140V
Herstellung der Verbindung (65) Preparation of the compound (65)
Eine Mischung aus 200 mg (0.67 mmol) Bromid (XI), 222 mg (0.81 mmol) 2-(Dimethylamino)-5- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitril, 2 Äquivalenten Kaliumcarbonat, 0.06 Eq. l,l'-Bis(diphenylphosphino)ferrocenpalladium(II)chlorid, 0.8 ml Acetonitril und 0.2 ml Wasser wurde mit Argon gespült und anschliessend in der Mikrowelle unter Rühren für 20 Minuten auf 140°C erhitzt. Der Ansatz wurde mit Essigester versetzt, filtriert und eingedampft. Der Rückstand wurde an Kieselgel mit Dichlormethan/Methanol und via HPLC aufgereinigt. Ausbeute 26 mg (10% d. Theorie) . A mixture of 200 mg (0.67 mmol) bromide (XI), 222 mg (0.81 mmol) 2- (dimethylamino) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) nicotinonitrile, 2 equivalents of potassium carbonate, 0.06 eq. l, l'-bis (diphenylphosphino) ferrocenpalladium (II) chloride, 0.8 ml of acetonitrile and 0.2 ml of water was purged with argon and then in the microwave with stirring for 20 minutes at 140 ° C. heated. The mixture was treated with ethyl acetate, filtered and evaporated. The residue was purified on silica gel with dichloromethane / methanol and via HPLC. Yield 26 mg (10% of theory).
^-NMR (CD3CN 400MHz); δ = 3.30 (s, 6H), 3.42 (s, 3H), 3.80 (s, 3H), 6.35 (s, 1H), 7.37-7-40 (m, 1H), 7.70-7.73 (m, 1H), 8.00-8.02 (m, 1H), 8.44-8.49 (m, 3H). ^ -NMR (CD 3 CN 400MHz); δ = 3.30 (s, 6H), 3.42 (s, 3H), 3.80 (s, 3H), 6.35 (s, 1H), 7.37-7-40 (m, 1H), 7.70-7.73 (m, 1H), 8.00-8.02 (m, 1H), 8.44-8.49 (m, 3H).
Beispiel (75) Example (75)
Herstellung der Verbindung (VII-Ethyl) Preparation of the compound (VII-ethyl)
Eine Mischung 29.2 g (161 mmol) l-Methyl-lH-imidazol-5-carbonylchlorid Hydrochlorid (Burm et al., Heterocycles, 2001 , vol. 55, # 3 p. 495 - 503), 19.7 g (161 mol) N-Ethylpyridin-3-amin und 300 ml Pyridin wurde für 15 Stunden bei 100°C unter Argon gerührt. Nach Abkühlen auf Raumtemperatur wurde filtriert und das Filtrat eingeengt, mit 250 mmol Natriumhydrogencarbonat versetzt und in 1000 ml Essigsäureethylester für 2 Stunden gerührt. Es wurde erneut filtriert, das Filtrat eingedampft und der Rückstand wurde an Kieselgel mit Essigsäureethylester/Methanol chromatogra- phiert. Ausbeute 29.0 g (77% d. Th.) logP[n]: 0.78. A mixture of 29.2 g (161 mmol) of 1-methyl-1H-imidazole-5-carbonyl chloride hydrochloride (Burm et al., Heterocycles, 2001, vol. 55, # 3 pp 495-503), 19.7 g (161 mol) N -Ethylpyridin-3-amine and 300 ml of pyridine were stirred for 15 hours at 100 ° C under argon. After cooling to room temperature was filtered and the filtrate was concentrated, treated with 250 mmol of sodium bicarbonate and stirred in 1000 ml of ethyl acetate for 2 hours. It was filtered again, the filtrate was evaporated and the residue was chromatographed on silica gel with ethyl acetate / methanol. Yield 29.0 g (77% of theory) logP [n]: 0.78.
'H-NMR (CD3CN, 400MHz); δ = 1.15 (t, 3H), 3.80 (s, 3H), 3.88 (q, 2H), 6.10 (s, 1H), 7.36-7.40 (m, 2H), 7.65-7.68 (m, 1H), 8.38 (m, 1H), 8.49 (m, 1H). 'H-NMR (CD 3 CN, 400 MHz); δ = 1.15 (t, 3H), 3.80 (s, 3H), 3.88 (q, 2H), 6.10 (s, 1H), 7.36-7.40 (m, 2H), 7.65-7.68 (m, 1H), 8.38 ( m, 1H), 8.49 (m, 1H).
Herstellung der Verbindung (XI-Ethyl) Preparation of the compound (XI-ethyl)
(VII-Ethyl) (XI-Ethyl)  (VII-ethyl) (XI-ethyl)
Zu einer Lösung von 5.00 g (21.7 mmol) VII-Ethyl in 150 wasserfreiem Tetrahydrofuran tropfte man bei -90°C unter Argon 9.1 ml einer 2.5 molaren Lösung von n-Butyllithium in Hexan innerhalb von 15 Minuten zu. Die Innentemperatur wurde zwischen -85 und -90°C gehalten und nach beendeter Zugabe liess man noch 10 Minuten in diesem Temperaturbereich weiterrühren. Nun wurde bei einer Temperatur zwischen -90 und -95°C eine Lösung von einem Äquivalent l,2-Dibrom-l,l,2,2- tetrachlorethan in 50 ml Tetrahydrofuran über einen Zeitraum von 10 Minuten unter Rühren zugetropft. Nach weiteren 30 Minuten bei -80°C und weiteren 45 Minuten bei -70°C liess man innerhalb von einer Stunde auf Raumtemperatur erwärmen. Durch Zugabe von Ammoniumchlorid wurde ein pH- Wert von 7 eingestellt, filtriert und das Filtrag eindampft. Chromatographie an Kieselgel mit Dichlormethan/Methanol ergab 4.90 g (71 % d. Th.) XI-Ethyl. Ή-NMR (CD3CN 400MHz); δ = 1.15 (t, 3H), 3.76 (s, 3H), 3.88 (q, 2H), 6.17 (s, 1H), 7.36-7-39 (m, 1H), 7.65-7.68 (m, 1H), 8.38 (m, 1H), 8.49 (m, 1H). To a solution of 5.00 g (21.7 mmol) of VII-ethyl in 150 anhydrous tetrahydrofuran was added dropwise at -90 ° C under argon 9.1 ml of a 2.5 molar solution of n-butyllithium in hexane within 15 minutes. The internal temperature was maintained between -85 and -90 ° C and after completion of the addition was allowed to continue stirring for 10 minutes in this temperature range. Now at a temperature between -90 and -95 ° C, a solution of one equivalent of l, 2-dibromo-l, l, 2,2-tetrachloroethane in 50 ml of tetrahydrofuran was added dropwise over a period of 10 minutes with stirring. After a further 30 minutes at -80 ° C and another 45 minutes at -70 ° C was allowed within from one hour to room temperature. By addition of ammonium chloride, a pH of 7 was set, filtered and the Filtrag evaporated. Chromatography on silica gel with dichloromethane / methanol gave 4.90 g (71% of theory) of XI-ethyl. Ή-NMR (CD 3 CN 400MHz); δ = 1.15 (t, 3H), 3.76 (s, 3H), 3.88 (q, 2H), 6.17 (s, 1H), 7.36-7-39 (m, 1H), 7.65-7.68 (m, 1H), 8.38 (m, 1H), 8.49 (m, 1H).
Herstellung der Verbindung (75) Preparation of the compound (75)
Eine Mischung aus 115 mg (0.372 mmol) Bromid (XI-Ethyl), 101 mg (0.391 mmol) 2-Mefhoxy-5- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitril, 2 Äquivalenten Kaliumcarbonat, 0.05 Äquivalenten l,l'-Bis(diphenylphosphino)ferrocenpalladium(II)chlorid, 0.8 ml Acetonitril und 0.2 ml Wasser wurde mit Argon gespült und anschliessend in der Mikrowelle unter Rühren für 20 Minuten auf 140°C erhitzt. Der Ansatz wurde mit Dichlormethan versetzt, filtriert und eingedampft. Der Rückstand wurde an Kieselgel mit Dichlormethan/Methanol auf gereinigt. Ausbeute 65 mg (47% d. Theorie) . A mixture of 115 mg (0.372 mmol) bromide (XI-ethyl), 101 mg (0.391 mmol) 2-mehoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) nicotinonitrile, 2 equivalents of potassium carbonate, 0.05 equivalents of 1,1'-bis (diphenylphosphino) ferrocene palladium (II) chloride, 0.8 ml of acetonitrile and 0.2 ml of water was purged with argon and then heated in the microwave with stirring for 20 minutes at 140 ° C. , The batch was treated with dichloromethane, filtered and evaporated. The residue was purified on silica gel with dichloromethane / methanol. Yield 65 mg (47% of theory).
XH-NMR (CD3CN 400MHz); δ = 1.18 (t, 3H), 3.81 (s, 3H), 3.92 (q, 2H), 4.07 (s, 3H), 6.34 (s, 1H), 7.39-7-42 (m, 1H), 7.70-7.73 (m, 1H), 8.23 (m, 1H), 8.40 (m, 1H), 8.49 (m, 1H), 8.59 (m, 1H). X H NMR (CD 3 CN 400MHz); δ = 1.18 (t, 3H), 3.81 (s, 3H), 3.92 (q, 2H), 4.07 (s, 3H), 6.34 (s, 1H), 7.39-7-42 (m, 1H), 7.70- 7.73 (m, 1H), 8.23 (m, 1H), 8.40 (m, 1H), 8.49 (m, 1H), 8.59 (m, 1H).
Verfahren B Beispiel (20) Method B Example (20)
Herstellung der Verbindung (XII) Preparation of the compound (XII)
Eine Suspension von 12g (95.2 mmol) l-Methyl-imidazol-5-carbonsäure in 72 ml Toluol wurde mit 12.71g (104.7 mmol) Thionylchlorid versetzt und über Nacht unter Rückfluss gerührt. Das Reaktionsgemisch wurde im Vakuum eingeengt. Der Rückstand wurde mit einer Lösung von 10.3g (95.2 mmol) 3-Methylamino-pyridin (V-l) in 72ml Pyridin versetzt und die resultierende Reaktionsmischung 4h auf 115°C erwärmt. Anschließend wurde erneut im Vakuum eingeengt und der Rückstand an Kieselgel säulenchromatographisch mit Acetonitril/ Methanol 3: 1 als Laufmittel gereinigt. Es wurden 8.1g (39.3 % d. Theorie) der Titelverbindung (XV-1) erhalten. logP[n]: 0.42 A suspension of 12 g (95.2 mmol) of 1-methylimidazole-5-carboxylic acid in 72 ml of toluene was treated with 12.71 g (104.7 mmol) of thionyl chloride and stirred overnight under reflux. The Reaction mixture was concentrated in vacuo. The residue was admixed with a solution of 10.3 g (95.2 mmol) of 3-methylaminopyridine (VI) in 72 ml of pyridine and the resulting reaction mixture was heated to 115 ° C. for 4 h. It was then concentrated again in vacuo and the residue was purified on silica gel by column chromatography with acetonitrile / methanol 3: 1 as eluent. There were obtained 8.1 g (39.3% of theory) of the title compound (XV-1). logP [n]: 0.42
Ή-NMR (CD3CN, 400MHz); δ = 3.39 (s, 3H), 3.81 (s, 3H), 6.17 (s, 1H), 7.36-7.40 (m, 2H), 7.67- 7.70 (m, 1H), 8.41 (m, 1 H) 8.47 (m, 1H) ppm. Ή-NMR (CD 3 CN, 400MHz); δ = 3.39 (s, 3H), 3.81 (s, 3H), 6.17 (s, 1H), 7.36-7.40 (m, 2H), 7.67-7.70 (m, 1H), 8.41 (m, 1H) 8.47 ( m, 1H) ppm.
Herstellung der Verbindung (20) Eine Mischung aus 150 mg (0.69 mmol) Imidazol (XII), 376 mg (1.38 mmol) 4-[(3- Brombenzyl)oxy]tetrahydro-2H-pyran, 0.05 Äquivalenten Palladium(II)acetat, 2 Äquivalenten. Kupfer(I)iodid und 4.5 ml Ν,Ν-Dimethylacetamid wurde mit Argon gespült und anschliessend in der Mikrowelle unter Rühren für 20 Minuten auf 160°C erhitzt. Der Ansatz wurde auf 15 ml Dichlorme- than und 12 ml lOproz. Natriumthiosulfatlösung gegeben und 3 mal mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, f Udert und eingedampft. Den so erhaltenen Rückstand chromatographierte man an Kieselgel mit Essigsäureethyles- ter/Methanol. Ausbeute 110 mg (38% d. Theorie). Preparation of compound (20) A mixture of 150 mg (0.69 mmol) imidazole (XII), 376 mg (1.38 mmol) 4 - [(3-bromobenzyl) oxy] tetrahydro-2H-pyran, 0.05 equivalents of palladium (II) acetate, 2 equivalents. Copper (I) iodide and 4.5 ml of Ν, Ν-dimethylacetamide was purged with argon and then heated in the microwave with stirring for 20 minutes at 160 ° C. The batch was diluted to 15 ml dichloromethane and 12 ml 10%. Sodium thiosulfate solution and extracted 3 times with dichloromethane. The combined organic phases were dried over magnesium sulfate, evaporated and evaporated. The residue thus obtained was chromatographed on silica gel with ethyl acetate / methanol. Yield 110 mg (38% of theory).
Ή-NMR (CD3CN, 400MHz); δ = 1.48-1.57 (m, 2H), 1.89-1.97 (m, 2H, vom Lösungsmittelsignal überlagert), 3.35- 3.41 (m, 2H) 3.42 (s, 3H), 3.60 (m, 1H), 3.82 (s, 3H), 3.82-3.88 (m, 2H), 4.60 (s, 2H), 6.37 (s, 1H), 7.37- 7.51 (m, 4H), 7.56 (s, 1H), 7.71-7.74 (m, 1H), 8.46-8.49 (m, 2H). Ή-NMR (CD 3 CN, 400MHz); δ = 1.48-1.57 (m, 2H), 1.89-1.97 (m, 2H, superimposed by the solvent signal), 3.35-3.41 (m, 2H) 3.42 (s, 3H), 3.60 (m, 1H), 3.82 (s, 3H), 3.82-3.88 (m, 2H), 4.60 (s, 2H), 6.37 (s, 1H), 7.37-7.51 (m, 4H), 7.56 (s, 1H), 7.71-7.74 (m, 1H) , 8.46-8.49 (m, 2H).
Verfahren C Method C
Beispiel (71) Example (71)
Herstellung der Verbindung (XIII) Preparation of the compound (XIII)
(XII) (XIII) 5.00 g (23.1 mmol) des Imidazols (XII) wurden in 150 mL THF gelöst und auf -90 °C abgekühlt. Die Temperatur wurde während der Reaktion zwischen -85 °C und -90 °C gehalten. 9.68 mL (24.2 mmol) 2.5 molare n-BuLi-Lösung in «-Hexan wurden innerhalb von 30 Minuten bei -90 °C zugetropft und 5 Minuten nachgerührt. Anschließend wurden innerhalb von 20 Minuten 0.242 g (69.4 mmol) lod, in 50 mL THF gelöst, zugetropft. Es wurden weitere 30 Minuten bei -80 °C nachgerührt und dann innerhalb von 1 h auf Raumtemperatur erwärmt. Der Ansatz wurde mit halbkonzentrierter Natriumhydrogencarbonatlösung/Dichlormethan extrahiert. Die wässrige Phase wurde nochmals dreimal mit Dichlormethan extrahiert. Die organischen Phasen wurden vereinigt, mit wenig Wasser gewaschen, mit Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wurde an Kieselgel durch MPLC mit Essigsäureethylester/Methanol als Laufmittel gereinigt. Nach Aufreinigung wurden 4.35 g (55.0% d. Theorie) erhalten. logP[a] : 0.66; logP[n] : 0.97; (XII) (XIII) 5.00 g (23.1 mmol) of the imidazole (XII) were dissolved in 150 mL of THF and cooled to -90 ° C. The temperature was maintained between -85 ° C and -90 ° C during the reaction. 9.68 mL (24.2 mmol) of 2.5 molar n-BuLi solution in hexane were added dropwise within 30 minutes at -90 ° C and stirred for 5 minutes. Subsequently, 0.242 g (69.4 mmol) of iodine dissolved in 50 ml of THF were added dropwise within 20 minutes. The mixture was stirred for a further 30 minutes at -80 ° C and then warmed to room temperature within 1 h. The reaction was extracted with half-concentrated sodium bicarbonate solution / dichloromethane. The aqueous phase was extracted again three times with dichloromethane. The organic phases were combined, washed with a little water, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC with ethyl acetate / methanol as eluent. After purification, 4.35 g (55.0% of theory) were obtained. logP [a]: 0.66; logP [n]: 0.97;
Ή-NMR (de-DMSO, 400MHz); δ = 3.37 (s, 3H), 3.74 (s, 3H), 6.27 (s, 1H), 7.42-7.45 (m, 1H), 7.82- 7.85 (m, 1H), 8.465-8.495 (m, 2H) ppm. Ή-NMR (de-DMSO, 400MHz); δ = 3.37 (s, 3H), 3.74 (s, 3H), 6.27 (s, 1H), 7.42-7.45 (m, 1H), 7.82-7.85 (m, 1H), 8.465-8.495 (m, 2H) ppm ,
Herstellung der Verbindung (XIV) Preparation of compound (XIV)
(XIV)  (XIV)
(XIII) Eine Lösung von 2.31 g (6.75 mmol) des Imidazols (XIII) und 2.34 mL (8.11 mmol) Tri- butyl(ethinyl)stannan in 67 mL Toluol wurde mit Argon entgast. 0.403 g (0.349 mmol) Palladium- tetrakis(triphenylphosphin) wurden hinzugefügt und die Lösung wurde 2.5 h unter Rückfluß gerührt. Der Ansatz wurde eingeengt und mit konzentrierter Natriumchloridlösung/Essigsäureethylester extrahiert. Die organische Phase wurde mit Natriumsulfat getrocknet, filtriert und eingeengt. Der Rück- stand wurde an Kieselgel durch MPLC mit Essigsäureethylester/Methanol als Laufmittel gereinigt. Nach Aufreinigung wurden 750 mg (45.8% d. Theorie) erhalten. logP[a] : 0.53; logP[n] : 0.87;  (XIII) A solution of 2.31 g (6.75 mmol) of imidazole (XIII) and 2.34 mL (8.11 mmol) of tri-butyl (ethynyl) stannane in 67 mL toluene was degassed with argon. 0.403 g (0.349 mmol) of palladium tetrakis (triphenylphosphine) was added and the solution was stirred at reflux for 2.5 h. The reaction was concentrated and extracted with concentrated sodium chloride solution / ethyl acetate. The organic phase was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC with ethyl acetate / methanol as eluent. After purification, 750 mg (45.8% of theory) were obtained. logP [a]: 0.53; logP [n]: 0.87;
Ή-NMR (CD3CN, 400MHz); δ = 3.395 (s, 3H), 3.74 (s, 1H), 3.86 (s, 3H), 6.22 (s, 1H), 7.35-7.38 (m, 1H), 7.66-7.69 (m, 1H), 8.412-8.417 (m, 1H), 8.46-8.48 (m, 1H) ppm. Herstellung der Verbindung (71) Ή-NMR (CD 3 CN, 400MHz); δ = 3.395 (s, 3H), 3.74 (s, 1H), 3.86 (s, 3H), 6.22 (s, 1H), 7.35-7.38 (m, 1H), 7.66-7.69 (m, 1H), 8.412- 8.417 (m, 1H), 8.46-8.48 (m, 1H) ppm. Preparation of the compound (71)
Eine Suspension von 120 mg (0.499 mmol) des Imidazols (XIV), 85.8 mg (0.549 mmol) N- Hydroxybenzolcarboximidoylchlorid und 75.9 mg (0.549 mmol) Kaliumcarbonat in 5.5 mL Dich- lormethan wurde 16 h bei Raumtemperatur gerührt. Der Ansatz wurde mit Wasser gequencht und mit Dichlormethan extrahiert. Die organischen Phasen wurden vereinigt, mit Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wurde an Kieselgel durch MPLC mit Essigsäureefhyles- ter/Methanol als Laufmittel gereinigt. Nach Aufreinigung wurden 750 mg (45.8% d. Theorie) erhalten. logP[a] : 1.90; logP[n] : 2.37; A suspension of 120 mg (0.499 mmol) of imidazole (XIV), 85.8 mg (0.549 mmol) of N-hydroxybenzenecarboximidoyl chloride and 75.9 mg (0.549 mmol) of potassium carbonate in 5.5 mL dichloromethane was stirred at room temperature for 16 h. The reaction was quenched with water and extracted with dichloromethane. The organic phases were combined, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC using ethyl acetate / methanol as eluent. After purification, 750 mg (45.8% of theory) were obtained. logP [a]: 1.90; logP [n]: 2.37;
^-NMR (de-DMSO, 400MHz); δ = 3.43 (s, 3H), 4.06 (s, 3H), 6.55 (s, 1H), 7.44-7.48 (m, 1H), 7.53- 7.57 (m, 3H), 7.60 (s, 1H), 7.87-7.91 (m, 1H), 7.96-7.98 (m, 2H), 8.48-8.50 (m, 1H), 8.55-8.56 (m, 1H) ppm. ^ -NMR (de-DMSO, 400MHz); δ = 3.43 (s, 3H), 4.06 (s, 3H), 6.55 (s, 1H), 7.44-7.48 (m, 1H), 7.53-7.57 (m, 3H), 7.60 (s, 1H), 7.87- 7.91 (m, 1H), 7.96-7.98 (m, 2H), 8.48-8.50 (m, 1H), 8.55-8.56 (m, 1H) ppm.
Herstellung der Verbindung (74) Preparation of the compound (74)
(XIV) (74)  (XIV) (74)
Eine Lösung von 244 mg (3.75 mmol) Natriumazid, 31.2 mg (0.125 mmol) Kupfer(II)-sulfat- Pentahydrat, 58.1 mg (0.293 mmol) Natrium-L-Ascorbat und 0.058 mL (0.936 mmol) Methyliodid in 9 mL Dimethylsulfoxid und 1 mL Wasser wurde 10 Min bei Raumtemperatur gerührt. 150 mg (0.624 mmol) 2-Ethinyl-N,l-dimethyl-N-(pyridin-3-yl)-lH-imidazol-5-carboxamid (C) wurden hinzugefügt und die Lösung wurde 16 h bei Raumtemperatur gerührt. Der Ansatz wurde mit Wasser verdünnt, mit konzentrierter Natriumhydrogencarbonatlösung basisch (pH = 8) gestellt und dreimal mit Essig- säureethylester extrahiert. Die organischen Phasen wurden vereinigt, dreimal mit Wasser gewaschen, mit Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wurde über RP18 durch HPLC mit Acetonitril/Wasser als Laufmittel gereinigt. Nach Aufreinigung wurden 38.0 mg (20.5% d. Theorie) erhalten. logP[a] : 0.27; logP[n] : 0.76; A solution of 244 mg (3.75 mmol) of sodium azide, 31.2 mg (0.125 mmol) of copper (II) sulfate pentahydrate, 58.1 mg (0.293 mmol) of sodium L-ascorbate and 0.058 mL (0.936 mmol) of methyl iodide in 9 mL of dimethylsulfoxide and 1 mL of water was stirred for 10 min at room temperature. 150 mg (0.624 mmol) of 2-ethynyl-N, 1-dimethyl-N- (pyridin-3-yl) -1H-imidazole-5-carboxamide (C) were added and the solution was stirred at room temperature for 16 h. The reaction was diluted with water, basified (pH = 8) with concentrated sodium bicarbonate solution and washed three times with acetic acid. acid ethyl ester extracted. The organic phases were combined, washed three times with water, dried with sodium sulfate, filtered and concentrated. The residue was purified via RP18 by HPLC with acetonitrile / water as eluent. After purification, 38.0 mg (20.5% of theory) were obtained. logP [a]: 0.27; logP [n]: 0.76;
Ή-NMR (de-DMSO, 400MHz); δ = 3.41 (s, 3H), 4.09 (s, 3H), 4.10 (s, 3H), 6.36 (s, IH), 7.43-7.46 (m, IH), 7.85-7.88 (m, IH), 8.46-8.48 (m, 2H), 8.53-8.54 (m, IH) ppm. Ή-NMR (de-DMSO, 400MHz); δ = 3.41 (s, 3H), 4.09 (s, 3H), 4.10 (s, 3H), 6.36 (s, IH), 7.43-7.46 (m, IH), 7.85-7.88 (m, IH), 8.46- 8.48 (m, 2H), 8.53-8.54 (m, IH) ppm.
Verfahren D Method D
Herstellung der Verbindung (70) Preparation of compound (70)
Eine Lösung von 100 mg (0.416 mmol) des Imidazols (XIV) und 45.8 mg (0.208 mmol) 2-Iodphenol in 1 mL THF und 2 mL Triethylamin wurde mit Argon entgast. 7.3 mg (0.010 mmol) Dichloro- bis(triphenylphosphin)palladium und 3.4 mg (0.021 mmol) Kupferiodid wurden hinzugefügt und die Lösung wurde 6 h bei 50 °C gerührt. Der Ansatz wurde mit konzentrierter Ammoniumchloridlö- sung/Essigsäureethylester extrahiert. Die wässrige Phase wurde nochmals zweimal mit Essigsäureet- hylester extrahiert. Die organischen Phasen wurden vereinigt, dreimal mit Wasser gewaschen, mit Natriumsulfat getrocknet, filtriert und eingeengt. Der Rückstand wurde an Kieselgel durch MPLC mit Essigsäureethylester/Methanol als Laufmittel gereinigt. Nach Aufreinigung wurden 13.0 mg (9.4% d. Theorie) erhalten. logP[a] : 1.63; logP[n] : 1.87; A solution of 100 mg (0.416 mmol) of the imidazole (XIV) and 45.8 mg (0.208 mmol) of 2-iodophenol in 1 mL THF and 2 mL triethylamine was degassed with argon. 7.3 mg (0.010 mmol) of dichloro-bis (triphenylphosphine) palladium and 3.4 mg (0.021 mmol) of copper iodide were added and the solution was stirred at 50 ° C for 6 h. The batch was extracted with concentrated ammonium chloride solution / ethyl acetate. The aqueous phase was extracted twice more with ethyl acetate. The organic phases were combined, washed three times with water, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel by MPLC with ethyl acetate / methanol as eluent. After purification, 13.0 mg (9.4% of theory) were obtained. logP [a]: 1.63; logP [n]: 1.87;
Ή-NMR (de-DMSO, 400MHz); δ = 3.43 (s, 3H), 4.07 (s, 3H), 6.48 (s, IH), 7.30-7.34 (m, IH), 7.38- 7.42 (m, 2H), 7.44-7.48 (m, IH), 7.65-7.67 (m, IH), 7.72-7.74 (m, IH), 7.87-7.90 (m, IH), 8.48-8.49 (m, IH), 8.54-8.55 (m, IH) ppm. Verfahren E Beispiel (2) Ή-NMR (de-DMSO, 400MHz); δ = 3.43 (s, 3H), 4.07 (s, 3H), 6.48 (s, IH), 7.30-7.34 (m, IH), 7.38-7.42 (m, 2H), 7.44-7.48 (m, IH), 7.65-7.67 (m, IH), 7.72-7.74 (m, IH), 7.87-7.90 (m, IH), 8.48-8.49 (m, IH), 8.54-8.55 (m, IH) ppm. Method E Example (2)
Herstellung der Verbindung (XVI) Preparation of the compound (XVI)
2 g (6,59 mmol) 5-Brom-4-fluor-2-methylphenyl-2,2,2-trifluorethylsulfid (US2015/344499 AI, S. 64), 1,76 g (6,92 mmol) Bis(pinacolato)diboron, 162 mg (0,19 mmol) [l,r-Bis(diphenylphosphino)- ferrocen]palladium(II)chlorid, 110 mg (0,19 mmol) l, -Bis(diphenylphosphino)ferrocen und 1,94 g (19,7 mmol) Kaliumacetat wurden in entgastem Dioxan (29 mL) vorgelegt und 6 h zum Sieden erhitzt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan aufgenommen. Die organische Phase wurde mit Wasser gewaschen, über Magnesiumsulfat getrocknet und filtriert. Das Gemisch wurde in Ethylacetat gelöst, über Kieselgel filtriert und das Lösungsmittel wurde im Vakuum abdestilliert. Der Rückstand wurde durch säulenchromatographische Reinigung mit einem Cyclohexan / Aceton- Gradienten als Laufmittel gereinigt. logP (sauer/neutral): 4,89/4,80; MH+: 351; 1H-NMR(400 MHz, D6-DMSO) δ ppm: 1,29 (s, 12H), 2,46 (s, 3H), 3,79 (q, 2H), 7,17 (d, 1H), 7,77 (d, 1H). 2 g (6.59 mmol) of 5-bromo-4-fluoro-2-methylphenyl-2,2,2-trifluoroethylsulfide (US2015 / 344499 Al, p. 64), 1.76 g (6.92 mmol) of bis ( pinacolato) diboron, 162 mg (0.19 mmol) of [1, r-bis (diphenylphosphino) ferrocene] palladium (II) chloride, 110 mg (0.19 mmol) of 1-bis (diphenylphosphino) ferrocene and 1.94 g (19.7 mmol) of potassium acetate were placed in degassed dioxane (29 mL) and heated to boiling for 6 h. It was then cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane. The organic phase was washed with water, dried over magnesium sulfate and filtered. The mixture was dissolved in ethyl acetate, filtered through silica gel, and the solvent was distilled off in vacuo. The residue was purified by column chromatography with a cyclohexane / acetone gradient as eluent. logP (acid / neutral): 4.89 / 4.80; MH + : 351; 1 H-NMR (400 MHz, D 6 -DMSO) δ ppm: 1.29 (s, 12H), 2.46 (s, 3H), 3.79 (q, 2H), 7.17 (d, 1H ), 7.77 (d, 1H).
Herstellung der Verbindung (XVIII) Preparation of the compound (XVIII)
250 mg (1,14 mmol) des Bromids (ABCR), 400 mg (1,14 mmol) 2-{2-Fluor-4-mefhyl-5-[(2,2,2- trifluorethyl)sulfanyl]phenyl}-4,4,5,5-tetramethyl-l,3,2-dioxaborolan und 39 mg (0,03 mmol) Tetrakis(triphenylphosphin)palladium(0) wurden in einem Gemisch aus entgastem Acetonitril (4 mL) und entgaster Natriumcarbonatlösung (IM, 5 mL) vorgelegt und 14 h bei 72 °C gerührt. Anschließend wurde auf Raumtemperatur abgekühlt, das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Dichlormethan aufgenommen. Die organische Phase wurde mit Wasser gewaschen, über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Cyclohe- xan / Aceton-Gradienten als Laufmittel gereinigt. logP (sauer/neutral): 3,09/3,19; MH+: 363; 1H-NMR(400 MHz, D6-DMSO) δ ρρηι: 2,46 (s, 3H), 3,71 (s, 3H), 3,83 (s, 3H), 3,99 (q, 2H), 7,42 (d, 1H), 7,75 (d, 1H), 7,81 (s, 1H). 250 mg (1.14 mmol) of the bromide (ABCR), 400 mg (1.14 mmol) of 2- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} - 4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 39 mg (0.03 mmol) tetrakis (triphenylphosphine) palladium (0) were dissolved in a mixture of degassed acetonitrile (4 mL) and degassed sodium carbonate solution (I.M. , 5 mL) and stirred at 72 ° C for 14 h. It was then cooled to room temperature, the reaction mixture was concentrated in vacuo and the residue was taken up in dichloromethane. The organic phase was washed with water, dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography with a cyclohexane / acetone gradient as eluent. logP (acid / neutral): 3.09 / 3.19; MH + : 363; 1 H NMR (400 MHz, D 6 -DMSO) δρρηι: 2.46 (s, 3H), 3.71 (s, 3H), 3.83 (s, 3H), 3.99 (q, 2H ), 7.42 (d, 1H), 7.75 (d, 1H), 7.81 (s, 1H).
Herstellung der Verbindung (XIX) Preparation of the compound (XIX)
50,5 mg (0,13 mmol) Methyl-2-{2-fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl}-l-methyl- lH-imidazol-5-carboxylat wurden in einem Gemisch aus Tetrahydrofuran (0,8 mL) und Wasser (0,8 mL) vorgelegt und die Lösung wurde auf 0 °C gekühlt. Anschließend wurden 6,7 mg (0,27 mmol) Lithiumhydroxid zugegeben und es wurde 14 h bei Raumtemperatur gerührt. Das organische Lösungsmittel wurde im Vakuum abdestilliert und die wässrige Lösung wurde mit IN HCl auf pH = 3 eingestellt. Das Produkt fiel als Feststoff aus. Dieser wurde abgesaugt und getrocknet. logP (sauer/neutral): 1,83/0,95; MH+: 349; 1H-NMR(400 MHz, D6-DMSO) δ ρριη: 2,47 (s, 3H), 3,69 (s, 3H), 4,00 (q, 2H), 7,41 (d, 1H), 7,73-7,75 (m, 2H). 50.5 mg (0.13 mmol) of methyl 2- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl} -1-methyl-1H-imidazole-5 Carboxylate was placed in a mixture of tetrahydrofuran (0.8 mL) and water (0.8 mL) and the solution was cooled to 0 ° C. Subsequently, 6.7 mg (0.27 mmol) of lithium hydroxide were added and it was stirred for 14 h at room temperature. The organic solvent was distilled off in vacuo and the aqueous solution was adjusted to pH = 3 with 1N HCl set. The product precipitated as a solid. This was filtered off with suction and dried. logP (acid / neutral): 1.83 / 0.95; MH + : 349; 1 H-NMR (400 MHz, D 6 -DMSO) δρριη: 2.47 (s, 3H), 3.69 (s, 3H), 4.00 (q, 2H), 7.41 (d, 1H ), 7.73-7.75 (m, 2H).
Beispiel (2) Example (2)
Herstellung der Verbindung (2) Preparation of compound (2)
28 mg (0,08 mmol) der Carbonsäure (XIX) wurden in Dioxan (0,5 mL) vorgelegt und mit 18,5 mg (0,09 mmol) EDCI versetzt. Die Mischung wurde eine 1 h bei Raumtemperatur gerührt. Dann wurden 8,7 mg (0,08 mmol) N-Methylpyridin-3-amin (XX), gelöst in Dioxan (0,5 mL), zugegeben und es wurde 14 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde im Vakuum eingeengt und der Rückstand wurde in Wasser und Ethylacetat aufgenommen. Die Phasen wurden getrennt, die wässrige Phase wurde zweimal mit Essigester extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet und filtriert. Der Rückstand wurde durch säulenchromatographi- sche Reinigung mit einem Cyclohexan / Ethylacetat-Gradienten als Laufmittel gereinigt. logP (sauer/neutral): 2,23/2,48; MH+: 439; 1H-NMR(400 MHz, D6-DMSO) δ ppm: 2,45 (s, 3H), 3,41 (s, 3H), 3,65 (s, 3H), 3,98 (q, 2H), 6,39 (s, 1H), 7,37 (d, 1H), 7,47-7,50 (m, 1H), 7,66 (d, 1H), 7,89- 7,92 (m, 1H), 8,50-8,56 (m, 2H) 28 mg (0.08 mmol) of the carboxylic acid (XIX) were initially charged in dioxane (0.5 mL) and treated with 18.5 mg (0.09 mmol) of EDCI. The mixture was stirred for 1 h at room temperature. Then, 8.7 mg (0.08 mmol) of N-methylpyridin-3-amine (XX) dissolved in dioxane (0.5 mL) was added and stirred at room temperature for 14 h. The reaction mixture was concentrated in vacuo and the residue was taken up in water and ethyl acetate. The phases were separated, the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and filtered. The residue was purified by column chromatography with a cyclohexane / ethyl acetate gradient as eluent. logP (acid / neutral): 2.23 / 2.48; MH + : 439; 1 H NMR (400 MHz, D 6 -DMSO) δ ppm: 2.45 (s, 3H), 3.41 (s, 3H), 3.65 (s, 3H), 3.98 (q, 2H ), 6.39 (s, 1H), 7.37 (d, 1H), 7.47-7.50 (m, 1H), 7.66 (d, 1H), 7.89-7.92 ( m, 1H), 8.50-8.56 (m, 2H)
Tabelle 1 Table 1
Verbindungen der Formel (II) Compounds of the formula (II)
in welcher die Substituenten, die in der Tabelle angegebenen Bedeutungen haben (Y = Methyl, W= V = Wasserstoff, Q=0, T=Elektronenpaar): Die Abkürzung "na" bedeutet, dass keine entsprechenden Werte vorliegen. in which the substituents have the meanings given in the table (Y = methyl, W = V = hydrogen, Q = 0, T = electron pair): The abbreviation "na" means that there are no corresponding values.
logp- logp-logp-logp
Beispielnr. X A Example No.. X A
neutral sauer  neutral sour
1 Methyl 2,21 1,721 methyl 2.21 1.72
2 'XX Methyl 2,48 2,23 2 ' XX methyl 2.48 2.23
3 Methyl 1,75 1,24 3 methyl, 1.75, 1.24
CK  CK
4 Methyl 0,73 0,35  4 methyl, 0.73, 0.35
5 Methyl 1,43 1,07 5 methyl 1.43 1.07
6 Methyl na 0,58 6 methyl 0.58
7 Methyl na 0,18 7 methyl on 0.18
8 Methyl na 1,168 methylene 1,16
9 oc Methyl na 1,10  9 oc methyl to 1,10
10 Methyl na 1,2910 methyl on 1,29
logp- logp- logp-logp
Beispielnr. X A Example No.. X A
neutral sauer neutral sour
11 Xk Methyl na 1,23 11 Xk methyl to 1,23
12 Methyl na 1,66 12 methyl, 1.66
13 CA Methyl na 1,79 13 C A methyl to 1.79
14 Methyl na 0,6214 methyl, 0.62
15 Methyl na 0,29 15 methyl, 0.29
16 Methyl na 0,99 16 methyl, 0.99
17 Methyl 2,28 2,00 17 methyl 2,28 2,00
CK  CK
18 Methyl 2,36 1,87 18 methyl 2.36 1.87
19 Methyl 1,43 0,8619 methyl 1.43 0.86
20 Methyl 1,57 1,11 logp- logp-20 methyl 1.57 1.11 logp-logp
Beispielnr. X A Example No.. X A
neutral sauer neutral sour
22 Methyl 1,08 0,75 22 Methyl 1.08 0.75
23 Methyl 2,03 1,43 23 methyl 2.03 1.43
24 Methyl 1,49 1,07 24 Methyl 1.49 1.07
25 Methyl 1,68 1,21 25 methyl 1.68 1.21
26 Methyl 1,70 1,19 26 methyl 1,70 1,19
27 Methyl 1,89 1,35 27 Methyl 1.89 1.35
28 Methyl 1,95 1,56 28 methyl 1.95 1.56
29 Methyl 1,55 1,04 29 Methyl 1.55 1.04
30 Methyl 2,05 1,57 logp- logp-30 methyl 2.05 1.57 logp-logp
Beispielnr. X A Example No.. X A
neutral sauer  neutral sour
31 Methyl 2,08 1,77 31 methyl 2.08 1.77
33
32 Methyl na 0,81  32 methyl, 0.81
33 'CK Methyl 0,86 0,03 33 ' CK methyl 0.86 0.03
34 Methyl 1,45 34 methyl 1,45
35 Methyl 1,77 1,42 35 Methyl 1.77 1.42
36 Methyl 1,96 1,41 36 methyl 1.96 1.41
37 Methyl 1,38 0,96 37 methyl 1,38 0.96
38 Methyl na 1,36 38 methyl on 1.36
39 Methyl 1,27 0,51 39 methyl 1,27 0,51
40 Methyl 2,14 1,53 logp- logp-40 methyl 2,14 1,53 logp-logp
Beispielnr. X A Example No.. X A
neutral sauer neutral sour
51 >A Methyl 2,43 2,17 51> A methyl 2.43 2.17
52 Methyl 1,99 1,64 52 methyl 1.99 1.64
53 Methyl 2,63 2,4353 methyl 2,63 2,43
54 Methyl 2,14 1,90 54 methyl 2,14 1,90
55 Methyl 1,92 1,72 55 Methyl 1.92 1.72
56 Methyl 1,96 na 56 methyl 1,96 na
57 Methyl 2,40 2,09 57 methyl 2,40 2,09
^^^^^  ^^^^^
58 Methyl 1,33 0,91 58, methyl, 1.33, 0.91
59 Methyl 1,69 1,42 59 methyl 1.69 1.42
60 Methyl 1,52 1,2160 methyl 1,52 1,21
logp- logp- logp-logp
Beispielnr. X A Example No.. X A
neutral sauer neutral sour
61 Methyl 1,96 1,85 61 methyl 1.96 1.85
62 Methyl 1,37 0,78 62 methyl, 1.37, 0.78
63 Methyl 1,52 1,1563 methyl 1,52 1,15
64 Methyl 0,98 0,75  64 methyl 0.98 0.75
65 Methyl 1,50 1,10 65 methyl 1,50 1,10
66 Methyl 1,45 1,16 66 methyl 1,45 1,16
67 Methyl 1,73 1,50 67 Methyl 1.73 1.50
68 Methyl 1,44 1,20 68 methyl 1.44 1.20
69 Methyl 1,74 1,52 69 methyl 1,74 1,52
70 Methyl 1,87 1,63 LogP- LogP-70 methyl, 1.87, 1.63 LogP- LogP-
Beispielnr. X A Example No.. X A
neutral sauer  neutral sour
71 X^o Methyl 1,99 1,9 71 X ^ o Methyl 1.99 1.9
72 Methyl 1,51 1,42 72 methyl 1.51 1.42
73 Methyl 1,24 0,88 73 methyl 1.24 0.88
74 Methyl 0,76 0,27 74 methyl 0.76 0.27
75 Ethyl 1,65 1,46 75 ethyl 1.65 1.46
76 Ethyl 1,95 1,69 76 ethyl 1.95 1.69
77 A Ethyl 1,39 0,97 77 A Ethyl 1.39 0.97
78 Methyl 1,6 1,2378 methyl 1,6 1,23
79 Methyl 0,7 79 methyl 0.7
80 <£ Methyl 1,62 0,97 LogP- LogP-80 <£ methyl 1.62 0.97 LogP- LogP-
Beispielnr. X A Example No.. X A
neutral sauer  neutral sour
81 Methyl 1,69 0,89 81 methyl 1.69 0.89
82 Methyl 1,45 0,6582 methyl 1,45 0,65
83 Methyl 1,44 0,9 83 methyl 1,44 0.9
84 Methyl 1,54 0,8 84 methyl 1.54 0.8
85 Methyl 0,9 85 methyl 0.9
86 Methyl 2,04 1,91 86 methyl 2.04 1.91
87 Methyl 1,64 1,35 87 methyl 1.64 1.35
88 Methyl 1,16 0,5388 methyl 1,16 0,53
89 Methyl 1,53 0,93 89 methyl 1.53 0.93
90 Methyl 1,68 1,2890 methyl 1,68 1,28
LogP- LogP- LogP- LogP-
Beispielnr. X A Example No.. X A
neutral sauer neutral sour
CH3 CH 3
101 Methyl 1,38 0,91  101 methyl 1,38 0.91
F-O F -O
102 Methyl 1,79 1,21 102 methyl 1,79 1,21
103 Methyl 1,25 0,58 103 methyl 1,25 0,58
104 Methyl 1,03 0,23 104 methyl 1.03 0.23
105 Methyl 1,87 1,55105 methyl 1,87 1,55
106 Methyl 1,1 0,75 106 methyl 1,1.75
Tabelle 2 Table 2
NMR-Daten ausgewählter Beispiele NMR-Peak-Listenverfahren  NMR data of selected examples NMR peak list method
Die 1H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-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 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets 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: δΐ (Intensität 1); 82 (Intensität 2); ; δί (Intensität i); ; δη (Intensität 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 peak list of an example therefore has the form: δΐ (intensity 1); 82 (intensity 2); ; δί (intensity i); ; δη (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.
Zur Kalibrierung der chemischen Verschiebung von 1H-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 1H NMR spectra, we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. Darüber hinaus können sie wie klassische 1H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. The lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, like classical 1H NMR prints, they can show solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-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 1H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a 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%). 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. 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."
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 1 H-NMR-Interpretation. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected 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 1 H NMR interpretation.
Weitere Details zu IH-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on IH NMR peaks can be found in Research Disclosure Database Number 564025.
Tabelle 2: Analytische NMR-Daten zu den in der Tabelle 1 angegebenen Verbindungen: Table 2: Analytical NMR data for the compounds indicated in Table 1:
1 1H-NM (400,0 MHz, DMSO): δ= 8,544(2,6); 8,538(2,6); 8,504(1,7); 8,500(1,9); 8,492(1,9); 1 1H-NM (400.0 MHz, DMSO): δ = 8.544 (2.6); 8,538 (2.6); 8,504 (1.7); 8,500 (1.9); 8.492 (1.9);
8,489(1,9); 7,926(0,5); 7,919(0,5); 7,908(1,0); 7,905(1,2); 7,902( 1,2); 7,898(1,0); 7,888(1,1); 7,884(1,3); 7,882(1,3); 7,878(1,1); 7,755(0,4); 7,740(3,1); 7,600(1,3); 7,580(1,7); 7,539(1,2); 7,519(2,3); 7,489(3,5); 7,477(1,6); 7,469(3,7); 7,456(1,4); 7,450( 1,0); 6,374(3,6); 5,758(1,5); 4,139(1,0); 4,113(3,1); 4,087(3,2); 4,061(1,1); 3,878(0,4); 3,833( 16,0); 3,412(15,3); 3,333(29,7); 2,687(1,9); 2,674(2,0); 2,507(26,6); 2,503(34,4); 2,499(26,4); 1,352(1,0); 1,337(0,4); 1,259(0,4); 1,249(0,6); 1,234(1,4); 0,000(5,7)  8,489 (1.9); 7,926 (0.5); 7.919 (0.5); 7.908 (1.0); 7,905 (1.2); 7.902 (1.2); 7,898 (1.0); 7,888 (1.1); 7,884 (1.3); 7,882 (1.3); 7,878 (1.1); 7,755 (0.4); 7,740 (3.1); 7,600 (1.3); 7,580 (1.7); 7,539 (1.2); 7,519 (2.3); 7,489 (3.5); 7,477 (1.6); 7.469 (3.7); 7,456 (1.4); 7,450 (1.0); 6,374 (3.6); 5,758 (1.5); 4,139 (1.0); 4,113 (3.1); 4,087 (3.2); 4,061 (1.1); 3,878 (0.4); 3,833 (16.0); 3,412 (15.3); 3.333 (29.7); 2,687 (1.9); 2,674 (2.0); 2,507 (26.6); 2,503 (34.4); 2,499 (26.4); 1,352 (1.0); 1,337 (0.4); 1,259 (0.4); 1,249 (0.6); 1,234 (1.4); 0.000 (5.7)
2 1H-NMR(400,0 MHz, DMSO): δ= 8,559(3,2); 8,552(3,2); 8,517(2,2); 8,514(2,3); 8,505(2,3);  2 1 H-NMR (400.0 MHz, DMSO): δ = 8.559 (3.2); 8,552 (3.2); 8,517 (2.2); 8,514 (2.3); 8,505 (2.3);
8,502(2,2); 8,317(0,5); 7,920(1,3); 7,916(1,6); 7,910(1,2); 7,899( 1,4); 7,896(1,6); 7,890(1,3); 7,673(3,0); 7,655(2,9); 7,502(1,8); 7,490(1,8); 7,481(1,7); 7,470( 1,6); 7,388(2,7); 7,361(2,6); 6,896(0,8); 6,718(0,5); 6,390(4,0); 4,014(1,2); 3,988(3,9); 3,974(0,8); 3,962(4,0); 3,936(1,4); 3,653(11,3); 3,649( 11,0); 3,407(20,0); 3,374(0,4); 3,329(196,1); 2,735(0,3); 2,676(1,2);  8,502 (2.2); 8,317 (0.5); 7,920 (1.3); 7,916 (1.6); 7.910 (1.2); 7,899 (1.4); 7,896 (1.6); 7,890 (1.3); 7,673 (3.0); 7.655 (2.9); 7,502 (1.8); 7,490 (1.8); 7,481 (1.7); 7,470 (1.6); 7,388 (2.7); 7,361 (2.6); 6,896 (0.8); 6,718 (0.5); 6,390 (4.0); 4,014 (1.2); 3,988 (3.9); 3,974 (0.8); 3,962 (4.0); 3,936 (1.4); 3,653 (11.3); 3,649 (11.0); 3,407 (20.0); 3,374 (0.4); 3,329 (196.1); 2,735 (0.3); 2,676 (1.2);
2,672(1,5); 2,667(1,2); 2,556(0,6); 2,507(170,2); 2,502(215,1); 2,498(160,2); 2,449(16,0); 2,334(1,1); 2,329(1,4); 2,325(1,1); 1,351(7,3); 1,336(2,9); 1,314(0,5); 1,298(1,4); 1,259(2,4); 1,250(4,4); 1,230(9,2); 1,140(0,5); 0,868(0,6); 0,852(1,2); 0,836(0,7); 0,000(10,9)  2,672 (1.5); 2,667 (1.2); 2,556 (0.6); 2.507 (170.2); 2.502 (215.1); 2.498 (160.2); 2,449 (16.0); 2,334 (1.1); 2,329 (1.4); 2,325 (1.1); 1,351 (7.3); 1.336 (2.9); 1,314 (0.5); 1.298 (1.4); 1,259 (2.4); 1,250 (4.4); 1,230 (9.2); 1,140 (0.5); 0.868 (0.6); 0.852 (1.2); 0.836 (0.7); 0.000 (10.9)
3 1H-NMR(400,0 MHz, CD3CN ): δ= 8,484(1,3); 8,481(1,3); 8,472(1,4); 8,469(1,4); 8,460(1,9); 3 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.484 (1.3); 8.481 (1.3); 8,472 (1.4); 8.469 (1.4); 8,460 (1.9);
8,454(1,9); 7,739(0,8); 7,735(0,9); 7,733(0,9); 7,729(0,7); 7,718(0,9); 7,715(1,0); 7,712(1,0); 7,708(0,8); 7,440(2,3); 7,419(0,6); 7,408(1,2); 7,399(1,6); 7,387( 1,2); 7,381(2,2); 7,376(1,1); 7,360(2,1); 7,355(2,1); 7,349(2,0); 7,344(1,2); 7,339(1,0); 7,335(0,9); 7,331(1,0); 7,328(0,7); 6,371(3,3); 3,945(0,3); 3,820(15,3); 3,425( 15,6); 2,958(15,3); 2,827(12,7); 2,503(16,0);  8,454 (1.9); 7,739 (0.8); 7,735 (0.9); 7,733 (0.9); 7,729 (0.7); 7,718 (0.9); 7.715 (1.0); 7,712 (1.0); 7,708 (0.8); 7,440 (2.3); 7,419 (0.6); 7,408 (1.2); 7,399 (1.6); 7.387 (1.2); 7,381 (2.2); 7,376 (1.1); 7,360 (2.1); 7,355 (2.1); 7,349 (2.0); 7.344 (1.2); 7,339 (1.0); 7.335 (0.9); 7,331 (1.0); 7,328 (0.7); 6,371 (3.3); 3,945 (0.3); 3,820 (15.3); 3,425 (15.6); 2,958 (15.3); 2,827 (12.7); 2,503 (16.0);
2,174(45,5); 1,973( 13,8); 1,964(1,2); 1,957(2,3); 1,952(11,7); 1,946(17,6); 1,940(23,3);  2,174 (45.5); 1,973 (13.8); 1,964 (1.2); 1,957 (2.3); 1,952 (11.7); 1,946 (17.6); 1,940 (23.3);
1,934(16,1); 1,927(8,4); 1,821(0,3); 1,270(0,6); 0,007(2,2); 0,000(46,8); -0,008(2,2)  1,934 (16.1); 1,927 (8.4); 1,821 (0.3); 1.270 (0.6); 0.007 (2.2); 0,000 (46.8); -0.008 (2.2)
4 1H-NMR(400,0 MHz, DMSO): δ= 8,939(5,8); 8,927(5,9); 8,537(1,9); 8,532(2,0); 8,482(1,4);  4 1 H-NMR (400.0 MHz, DMSO): δ = 8.939 (5.8); 8,927 (5.9); 8,537 (1.9); 8.532 (2.0); 8,482 (1.4);
8,478(1,6); 8,470(1,5); 8,466(1,6); 7,898(0,8); 7,894(0,9); 7,892(0,9); 7,888(0,8); 7,878(0,9); 7,874(1,0); 7,871(1,0); 7,868(0,8); 7,549(1,6); 7,536(3,1); 7,524( 1,5); 7,470(1,0); 7,468(1,0); 7,458(1,1); 7,456(1,0); 7,449(1,0); 7,448(1,0); 7,437(0,9); 7,436(0,9); 6,501(1,9); 5,757(0,4); 4,086(16,0); 3,427( 15,1); 3,411(0,6); 3,345(44,0); 2,672(0,4); 2,668(0,3); 2,526(1,1); 2,521(1,7); 2,512(25,0); 2,508(52,2); 2,503(69,3); 2,499(50,5); 2,494(24,9); 2,330(0,4); 2,325(0,3);  8.478 (1.6); 8,470 (1.5); 8,466 (1.6); 7,898 (0.8); 7,894 (0.9); 7,892 (0.9); 7,888 (0.8); 7,878 (0.9); 7,874 (1.0); 7,871 (1.0); 7,868 (0.8); 7,549 (1.6); 7,536 (3.1); 7,524 (1.5); 7.470 (1.0); 7,468 (1.0); 7,458 (1.1); 7,456 (1.0); 7,449 (1.0); 7,448 (1.0); 7,437 (0.9); 7,436 (0.9); 6,501 (1.9); 5,757 (0.4); 4,086 (16.0); 3,427 (15,1); 3,411 (0.6); 3,345 (44.0); 2,672 (0.4); 2,668 (0.3); 2,526 (1.1); 2,521 (1.7); 2,512 (25.0); 2,508 (52.2); 2,503 (69.3); 2,499 (50.5); 2,494 (24.9); 2,330 (0.4); 2,325 (0.3);
0,146(0,4); 0,008(3,3); 0,000(97,7); -0,009(3,9); -0,150(0,4)  0.146 (0.4); 0.008 (3.3); 0,000 (97.7); -0.009 (3.9); -0.150 (0.4)
5 1H-NMR(400,0 MHz, DMSO): δ= 8,549(3,2); 8,545(3,2); 8,500(2,2); 8,497(2,2); 8,489(2,4);  5 1 H NMR (400.0 MHz, DMSO): δ = 8.549 (3.2); 8,545 (3.2); 8,500 (2.2); 8,497 (2.2); 8,489 (2.4);
8,485(2,0); 8,141(3,6); 8,026(3,9); 7,907(1,8); 7,903(1,8); 7,888(3,9); 7,877(3,2); 7,873(2,8); 7,868(2,8); 7,772(1,8); 7,752(2,5); 7,733(1,0); 7,488(1,5); 7,476( 1,6); 7,468(1,6); 7,456(1,3); 6,411(3,8); 5,754(1,7); 4,277(0,6); 4,268(0,5); 4,241(1,3); 4,214( 1,5); 4,192(1,4); 4,166(1,4); ,140(0,5); 4,130(0,6); 3,878(16,0); 3,419(15,5); 3,388(0,7); 3,319(13,1); 2,671(1,0);8,485 (2.0); 8,141 (3.6); 8.026 (3.9); 7,907 (1.8); 7,903 (1.8); 7,888 (3.9); 7.877 (3.2); 7,873 (2.8); 7,868 (2.8); 7.772 (1.8); 7,752 (2.5); 7,733 (1.0); 7,488 (1.5); 7.466 (1.6); 7,468 (1.6); 7,456 (1.3); 6,411 (3.8); 5,754 (1.7); 4,277 (0.6); 4,268 (0.5); 4,241 (1.3); 4,214 (1.5); 4,192 (1.4); 4,166 (1.4); , 140 (0.5); 4,130 (0.6); 3,878 (16.0); 3,419 (15.5); 3,388 (0.7); 3,319 (13.1); 2,671 (1.0);
,506(133,1); 2,502(151,4); 2,328(1,0); 0,146(0,4); 0,000(86,6); -0,150(0,5), 506 (133.1); 2.502 (151.4); 2,328 (1.0); 0.146 (0.4); 0,000 (86.6); -0.150 (0.5)
H-NM (400,0 MHz, DMSO): δ= 8,547(1,8); 8,546(1,9); 8,541(2,0); 8,502(1,4); 8,498(1,5);,490(1,6); 8,487(1,5); 7,904(0,8); 7,900(1,0); 7,897(0,9); 7,894(0,9); 7,884(1,0); 7,880(1,1);,877(1,1); 7,873(0,9); 7,641(1,8); 7,634(1,4); 7,630(1,2); 7,621(2,6); 7,617(2,3); 7,509(0,7);,505(0,6); 7,497(2,3); 7,492(1,7); 7,489(2,2); 7,483(3,9); 7,479(4,3); 7,471(1,1); 7,468(1,4);,467(1,4); 7,456(1,1); 7,455(1,0); 6,366(3,2); 3,831(16,0); 3,411(15,0); 3,359(0,4);H-NM (400.0 MHz, DMSO): δ = 8.547 (1.8); 8,546 (1.9); 8,541 (2.0); 8,502 (1.4); 8,498 (1.5) ;, 490 (1.6); 8,487 (1.5); 7,904 (0.8); 7,900 (1.0); 7,897 (0.9); 7,894 (0.9); 7,884 (1.0); 7,880 (1.1) ;, 877 (1.1); 7,873 (0.9); 7,641 (1.8); 7,634 (1.4); 7,630 (1.2); 7.621 (2.6); 7,617 (2.3); 7,509 (0.7) ;, 505 (0.6); 7,497 (2.3); 7,492 (1.7); 7,489 (2.2); 7,483 (3.9); 7.479 (4.3); 7,471 (1.1); 7,468 (1.4) ;, 467 (1.4); 7,456 (1.1); 7.455 (1.0); 6,366 (3.2); 3,831 (16.0); 3,411 (15.0); 3,359 (0.4);
,327(134,9); 3,301(0,4); 2,671(0,3); 2,541(21,9); 2,524(0,8); 2,519(1,2); 2,511(19,4);, 327 (134.9); 3,301 (0.4); 2,671 (0.3); 2,541 (21.9); 2,524 (0.8); 2,519 (1.2); 2,511 (19.4);
,506(40,1); 2,502(53,5); 2,497(40,0); 2,493(20,2); 2,328(0,4); 0,000(1,0), 506 (40.1); 2,502 (53.5); 2,497 (40.0); 2,493 (20.2); 2,328 (0.4); 0.000 (1.0)
H-NMR(400,0 MHz, DMSO): δ= 20,010(0,4); 8,839(1,7); 8,835(1,7); 8,666(1,2); 8,662(1,4);,654(1,4); 8,650(1,4); 8,548(1,7); 8,542(1,9); 8,505(1,3); 8,501(1,6); 8,493(1,5); 8,490(1,5);,089(0,7); 8,084(1,1); 8,079(0,8); 8,069(0,9); 8,064(1,2); 8,059(0,9); 7,910(0,7); 7,906(0,9);,900(0,8); 7,889(0,9); 7,886(1,0); 7,883(1,1); 7,879(0,9); 7,539(1,0); 7,527(1,0); 7,520(1,0);,507(0,9); 7,489(1,1); 7,477(1,1); 7,468(1,1); 7,456(1,0); 6,418(2,6); 3,865(16,0); 3,415(14,7);,370(1,3); 3,326(1758,5); 3,240(1,0); 2,675(3,3); 2,670(4,5); 2,666(3,4); 2,541(9,4);H NMR (400.0 MHz, DMSO): δ = 20.010 (0.4); 8,839 (1.7); 8,835 (1.7); 8,666 (1.2); 8,662 (1.4) ;, 654 (1.4); 8,650 (1.4); 8,548 (1.7); 8,542 (1.9); 8,505 (1.3); 8,501 (1.6); 8,493 (1.5); 8,490 (1.5) ;, 089 (0.7); 8,084 (1.1); 8.079 (0.8); 8,069 (0.9); 8,064 (1.2); 8,059 (0.9); 7.910 (0.7); 7,906 (0.9) ;, 900 (0.8); 7,889 (0.9); 7,886 (1.0); 7,883 (1.1); 7,879 (0.9); 7,539 (1.0); 7,527 (1.0); 7,520 (1.0) ;, 507 (0.9); 7,489 (1.1); 7,477 (1.1); 7,468 (1.1); 7,456 (1.0); 6,418 (2.6); 3,865 (16.0); 3,415 (14.7) ;, 370 (1.3); 3.326 (1758.5); 3,240 (1.0); 2,675 (3.3); 2,670 (4.5); 2,666 (3.4); 2,541 (9.4);
,524(11,3); 2,519(16,9); 2,510(240,7); 2,506(501,5); 2,501(671,4); 2,497(490,9); 2,492(236,5);,333(3,1); 2,328(4,3); 2,324(3,2); 2,289(0,4); 1,236(0,5); 0,000(13,4), 524 (11.3); 2,519 (16.9); 2,510 (240.7); 2.506 (501.5); 2.501 (671.4); 2.497 (490.9); 2.492 (236.5) ;, 333 (3.1); 2,328 (4.3); 2,324 (3.2); 2,289 (0.4); 1.236 (0.5); 0.000 (13.4)
H-NMR(400,0 MHz, DMSO): δ= 8,531(1,5); 8,525(1,6); 8,497(1,1); 8,493(1,2); 8,485(1,2);,481(1,2); 7,892(0,7); 7,889(0,8); 7,886(0,8); 7,882(0,7); 7,872(0,8); 7,868(0,9); 7,866(0,9);,862(0,7); 7,483(0,9); 7,481(0,9); 7,471(0,9); 7,469(0,9); 7,462(0,8); 7,461(0,8); 7,450(0,8);,449(0,8); 7,216(3,6); 7,101(1,6); 6,333(2,8); 3,810(12,3); 3,404(11,6); 3,342(0,6);H NMR (400.0 MHz, DMSO): δ = 8.531 (1.5); 8,525 (1.6); 8,497 (1.1); 8,493 (1.2); 8.485 (1.2) ;, 481 (1.2); 7,892 (0.7); 7,889 (0.8); 7,886 (0.8); 7,882 (0.7); 7,872 (0.8); 7,868 (0.9); 7,866 (0.9) ;, 862 (0.7); 7,483 (0.9); 7,481 (0.9); 7,471 (0.9); 7.469 (0.9); 7,462 (0.8); 7,461 (0.8); 7,450 (0.8) ;, 449 (0.8); 7,216 (3.6); 7,101 (1.6); 6,333 (2.8); 3,810 (12.3); 3,404 (11.6); 3,342 (0.6);
,323(109,8); 2,670(0,4); 2,541(21,6); 2,524(0,9); 2,510(22,1); 2,506(44,1); 2,501(57,7);, 323 (109.8); 2,670 (0.4); 2,541 (21.6); 2,524 (0.9); 2,510 (22.1); 2,506 (44.1); 2,501 (57.7);
,497(42,5); 2,492(21,1); 2,333(0,4); 2,316(16,0); 0,000(1,1), 497 (42.5); 2,492 (21.1); 2,333 (0.4); 2,316 (16.0); 0.000 (1.1)
H-NMR(400,0 MHz, DMSO): δ= 8,544(2,2); 8,539(2,2); 8,509(1,6); 8,506(1,7); 8,497(1,7);,494(1,6); 7,891(0,9); 7,887(1,1); 7,885(1,0); 7,881(0,9); 7,871(1,0); 7,867(1,2); 7,864(1,2);,861(1,0); 7,633(1,2); 7,614(2,3); 7,580(0,8); 7,574(0,9); 7,564(1,2); 7,558(1,3); 7,553(0,6);,544(0,7); 7,537(0,8); 7,490(1,6); 7,478(1,6); 7,474(2,2); 7,471(3,0); 7,462(3,0); 7,456(4,0);,444(0,6); 6,393(2,7); 3,565(16,0); 3,410(15,2); 3,384(0,8); 3,324(662,6); 3,269(0,7);H NMR (400.0 MHz, DMSO): δ = 8.544 (2.2); 8,539 (2.2); 8,509 (1.6); 8,506 (1.7); 8,497 (1.7) ;, 494 (1.6); 7,891 (0.9); 7,887 (1.1); 7,885 (1.0); 7,881 (0.9); 7,871 (1.0); 7,867 (1.2); 7,864 (1.2) ;, 861 (1.0); 7,633 (1.2); 7,614 (2.3); 7,580 (0.8); 7,574 (0.9); 7,564 (1.2); 7,558 (1.3); 7,553 (0.6) ;, 544 (0.7); 7,537 (0.8); 7,490 (1.6); 7,478 (1.6); 7,474 (2.2); 7,471 (3.0); 7,462 (3.0); 7,456 (4.0) ;, 444 (0.6); 6,393 (2.7); 3,565 (16.0); 3,410 (15.2); 3,384 (0.8); 3.324 (662.6); 3,269 (0.7);
,252(0,5); 2,994(0,3); 2,675(1,7); 2,670(2,3); 2,666(1,8); 2,541(60,2); 2,510(144,7);, 252 (0.5); 2,994 (0.3); 2,675 (1.7); 2,670 (2.3); 2,666 (1.8); 2,541 (60.2); 2,510 (144.7);
,506(273,9); 2,501(355,6); 2,497(273,5); 2,493(150,3); 2,367(0,3); 2,332(1,7); 2,328(2,3);,324(1,8); 0,000(6,2), 506 (273.9); 2.501 (355.6); 2.497 (273.5); 2,493 (150.3); 2,367 (0.3); 2,332 (1.7); 2,328 (2.3) ;, 324 (1.8); 0.000 (6.2)
H-NMR(400,0 MHz, DMSO): δ= 8,537(1,9); 8,532(2,0); 8,500(1,5); 8,496(1,6); 8,488(1,6);,484(1,5); 7,899(0,8); 7,895(1,0); 7,892(0,9); 7,888(0,9); 7,878(0,9); 7,875(1,0); 7,872(1,0);,868(0,9); 7,692(2,2); 7,687(1,5); 7,633(0,7); 7,629(1,2); 7,624(0,7); 7,616(1,0); 7,612(1,5);,607(1,0); 7,560(0,6); 7,555(0,4); 7,544(1,7); 7,540(3,2); 7,538(2,7); 7,536(2,6); 7,519(1,5);,500(0,4); 7,484(1,1); 7,482(1,1); 7,472(1,1); 7,471(1,1); 7,464(1,0); 7,462(1,0); 7,452(1,0);,450(1,0); 6,392(2,9); 3,851(16,0); 3,411(14,8); 3,325(238,3); 3,301(0,6); 2,675(0,5);H-NMR (400.0 MHz, DMSO): δ = 8.537 (1.9); 8.532 (2.0); 8,500 (1.5); 8,496 (1.6); 8.488 (1.6) ;, 484 (1.5); 7,899 (0.8); 7.895 (1.0); 7,892 (0.9); 7,888 (0.9); 7,878 (0.9); 7,875 (1.0); 7,872 (1.0) ;, 868 (0.9); 7,692 (2.2); 7,687 (1.5); 7,633 (0.7); 7,629 (1.2); 7,624 (0.7); 7,616 (1.0); 7.612 (1.5) ;, 607 (1.0); 7,560 (0.6); 7,555 (0.4); 7,544 (1.7); 7,540 (3.2); 7,538 (2.7); 7,536 (2.6); 7,519 (1.5) ;, 500 (0.4); 7,484 (1.1); 7,482 (1.1); 7,472 (1.1); 7,471 (1.1); 7,464 (1.0); 7,462 (1.0); 7,452 (1.0) ;, 450 (1.0); 6,392 (2.9); 3,851 (16.0); 3,411 (14.8); 3.325 (238.3); 3,301 (0.6); 2,675 (0.5);
,671(0,6); 2,666(0,5); 2,541(35,4); 2,524(1,5); 2,519(2,4); 2,511(36,5); 2,506(75,8);, 671 (0.6); 2,666 (0.5); 2,541 (35.4); 2,524 (1.5); 2,519 (2.4); 2,511 (36.5); 2,506 (75.8);
,501(101,6); 2,497(74,6); 2,492(36,3); 2,473(0,4); 2,333(0,5); 2,328(0,7); 2,324(0,5);, 501 (101.6); 2,497 (74.6); 2,492 (36.3); 2.473 (0.4); 2,333 (0.5); 2,328 (0.7); 2,324 (0.5);
,000(2,2), 000 (2,2)
H-NMR(400,0 MHz, DMSO): δ= 8,541(1,9); 8,535(2,0); 8,498(1,5); 8,494(1,6); 8,486(1,6);,482(1,5); 7,899(0,8); 7,896(0,9); 7,893(0,9); 7,889(0,8); 7,879(0,9); 7,875(1,0); 7,872(1,0);,869(0,9); 7,689(0,4); 7,682(3,2); 7,677(1,2); 7,666(1,4); 7,661(4,7); 7,655(0,7); 7,569(0,6);,563(4,7); 7,558(1,4); 7,546(1,1); 7,541(3,2); 7,483(1,1); 7,482(1,1); 7,471(1,1); 7,470(1,1);,463(1,0); 7,462(1,0); 7,451(1,0); 7,450(1,0); 6,377(3,2); 3,834(16,0); 3,408(15,1); 3,365(0,5);,325(446,9); 3,291(0,6); 2,679(0,5); 2,675(1,0); 2,670(1,4); 2,666(1,0); 2,662(0,5); 2,541(41,6);,524(3,2); 2,519(4,9); 2,510(76,1); 2,506(156,4); 2,501(207,5); 2,497(152,7); 2,492(74,8);,337(0,5); 2,333(0,9); 2,328(1,3); 2,324(1,0); 0,000(2,6)H-NMR (400.0 MHz, DMSO): δ = 8.541 (1.9); 8,535 (2.0); 8,498 (1.5); 8,494 (1.6); 8.486 (1.6) ;, 482 (1.5); 7,899 (0.8); 7,896 (0.9); 7,893 (0.9); 7,889 (0.8); 7,879 (0.9); 7,875 (1.0); 7,872 (1.0) ;, 869 (0.9); 7.689 (0.4); 7,682 (3.2); 7,677 (1.2); 7,666 (1.4); 7,661 (4.7); 7.655 (0.7); 7,569 (0.6) ;, 563 (4.7); 7,558 (1.4); 7,546 (1.1); 7,541 (3.2); 7,483 (1.1); 7,482 (1.1); 7,471 (1.1); 7.470 (1.1) ;, 463 (1.0); 7,462 (1.0); 7,451 (1.0); 7,450 (1.0); 6,377 (3.2); 3,834 (16.0); 3,408 (15.1); 3.365 (0.5) ;, 325 (446.9); 3,291 (0.6); 2,679 (0.5); 2,675 (1.0); 2,670 (1.4); 2,666 (1.0); 2,662 (0.5); 2,541 (41.6) ;, 524 (3.2); 2,519 (4.9); 2,510 (76.1); 2.506 (156.4); 2.501 (207.5); 2.497 (152.7); 2.492 (74.8) ;, 337 (0.5); 2,333 (0.9); 2,328 (1.3); 2,324 (1.0); 0,000 (2.6)
H-NMR(400,0 MHz, DMSO): δ= 20,009(0,6); 8,539(1,9); 8,533(2,0); 8,501(1,5); 8,492(1,6);,489(1,6); 7,879(1,0); 7,865(1,0); 7,861(1,1); 7,855(1,0); 7,827(2,7); 7,821(2,9); 7,576(1,2);,571(1,2); 7,555(2,1); 7,550(2,2); 7,505(3,6); 7,484(3,1); 7,472(1,2); 7,464(1,1); 7,452(1,1);,407(2,5); 3,834(0,4); 3,571(16,0); 3,408(15,0); 3,371(1,1); 3,324(2480,1); 3,228(1,3); ,187(0,8); 2,994(0,5); 2,675(5,0); 2,670(6,8); 2,666(5,0); 2,541(36,7); 2,524(17,1);H NMR (400.0 MHz, DMSO): δ = 20.009 (0.6); 8,539 (1.9); 8,533 (2.0); 8,501 (1.5); 8.492 (1.6) ;, 489 (1.6); 7,879 (1.0); 7,865 (1.0); 7,861 (1.1); 7,855 (1.0); 7.827 (2.7); 7.821 (2.9); 7,576 (1.2) ;, 571 (1.2); 7,555 (2.1); 7,550 (2.2); 7,505 (3.6); 7,484 (3.1); 7,472 (1.2); 7,464 (1.1); 7,452 (1.1) ;, 407 (2.5); 3,834 (0.4); 3.571 (16.0); 3,408 (15.0); 3,371 (1.1); 3.324 (2480.1); 3,228 (1.3); , 187 (0.8); 2,994 (0.5); 2,675 (5.0); 2,670 (6.8); 2,666 (5.0); 2,541 (36.7); 2,524 (17.1);
,510(384,4); 2,506(771,9); 2,501(1012,5); 2,497(743,1); 2,492(363,2); 2,332(4,7); 2,328(6,5);,323(4,8); 2,288(0,5); 1,235(0,8); 0,000(17,7), 510 (384.4); 2.506 (771.9); 2.501 (1012.5); 2.497 (743.1); 2.492 (363.2); 2,332 (4.7); 2,328 (6.5) ;, 323 (4.8); 2,288 (0.5); 1,235 (0.8); 0.000 (17.7)
H-NM (400,0 MHz, DMSO): δ= 8,536(2,5); 8,530(2,6); 8,497(1,8); 8,494(1,8); 8,486(1,8);,483(1,8); 7,909(3,1); 7,905(3,2); 7,898(1,2); 7,894(1,3); 7,888(1,0); 7,877(1,1); 7,873(1,3);,868(1,0); 7,765(2,3); 7,744(3,5); 7,665(2,1); 7,660(2,0); 7,644(1,4); 7,639(1,4); 7,481(1,4);,469(1,4); 7,461(1,3); 7,449(1,3); 6,403(3,4); 3,862(16,0); 3,410(15,3); 3,325(107,4);H-NM (400.0 MHz, DMSO): δ = 8.536 (2.5); 8,530 (2.6); 8,497 (1.8); 8,494 (1.8); 8.486 (1.8) ;, 483 (1.8); 7,909 (3.1); 7,905 (3.2); 7,898 (1.2); 7,894 (1.3); 7,888 (1.0); 7.877 (1.1); 7,873 (1.3) ;, 868 (1.0); 7,765 (2.3); 7.744 (3.5); 7,665 (2.1); 7,660 (2.0); 7.644 (1.4); 7,639 (1.4); 7,481 (1.4) ;, 469 (1.4); 7,461 (1.3); 7,449 (1.3); 6,403 (3.4); 3,862 (16.0); 3,410 (15.3); 3.325 (107.4);
,286(0,4); 2,671(0,4); 2,541(13,6); 2,506(46,9); 2,502(58,1); 2,329(0,3); 0,000(0,9), 286 (0.4); 2,671 (0.4); 2,541 (13.6); 2,506 (46.9); 2,502 (58.1); 2,329 (0.3); 0.000 (0.9)
H-NMR(400,0 MHz, DMSO): δ= 8,530(1,9); 8,525(1,9); 8,491(1,4); 8,488(1,5); 8,480(1,5);,476(1,5); 7,884(0,8); 7,880(0,9); 7,877(0,9); 7,874(0,8); 7,864(0,9); 7,860(1,0); 7,857(1,0);,853(0,9); 7,477(1,0); 7,476(1,1); 7,465(1,0); 7,464(1,1); 7,457(1,0); 7,455(1,0); 7,445(1,0);,443(1,0); 6,936(1,3); 6,931(1,7); 6,930(1,7); 6,925(1,4); 6,442(1,5); 6,438(1,6); 6,433(1,8);,428(1,7); 6,373(3,6); 6,139(1,7); 6,132(1,9); 6,129(1,8); 6,123(1,6); 3,789(16,0); 3,629(15,1);,401(15,3); 3,381(0,4); 3,371(0,4); 3,325(392,9); 3,286(0,5); 2,675(0,9); 2,670(1,2); 2,666(0,9);,661(0,5); 2,541(42,4); 2,524(3,1); 2,519(4,8); 2,510(66,5); 2,506(137,3); 2,501(183,9);H NMR (400.0 MHz, DMSO): δ = 8.530 (1.9); 8,525 (1.9); 8,491 (1.4); 8.488 (1.5); 8,480 (1.5) ;, 476 (1.5); 7,884 (0.8); 7,880 (0.9); 7.877 (0.9); 7,874 (0.8); 7,864 (0.9); 7,860 (1.0); 7,857 (1.0) ;, 853 (0.9); 7,477 (1.0); 7,476 (1.1); 7.465 (1.0); 7,464 (1.1); 7.457 (1.0); 7.455 (1.0); 7,445 (1.0) ;, 443 (1.0); 6,936 (1.3); 6,931 (1.7); 6,930 (1.7); 6,925 (1.4); 6,442 (1.5); 6,438 (1.6); 6,433 (1.8) ;, 428 (1.7); 6,373 (3.6); 6,139 (1.7); 6,132 (1.9); 6,129 (1.8); 6,123 (1.6); 3,789 (16.0); 3.629 (15.1) ;, 401 (15.3); 3,381 (0.4); 3,371 (0.4); 3.325 (392.9); 3,286 (0.5); 2,675 (0.9); 2,670 (1.2); 2.666 (0.9) ;, 661 (0.5); 2,541 (42.4); 2,524 (3.1); 2,519 (4.8); 2,510 (66.5); 2.506 (137.3); 2.501 (183.9);
,497(137,6); 2,492(70,3); 2,337(0,4); 2,333(0,9); 2,328(1,2); 2,324(0,9); 2,319(0,4); 0,000(3,2)H-NMR(400,0 MHz, DMSO): δ= 8,518(1,9); 8,512(2,0); 8,478(1,4); 8,474(1,5); 8,466(1,5);,462(1,5); 8,216(2,0); 8,214(2,5); 8,212(2,5); 8,210(2,0); 7,877(0,8); 7,873(0,9); 7,870(0,9);,866(0,8); 7,856(0,9); 7,852(1,0); 7,850(1,0); 7,846(0,9); 7,805(1,8); 7,800(2,8); 7,796(1,7);,464(1,1); 7,462(1,1); 7,452(1,1); 7,450(1,0); 7,443(1,0); 7,431(1,0); 6,848(2,0); 6,846(2,2);,844(2,2); 6,842(2,1); 6,310(3,4); 3,855(16,0); 3,396(15,1); 3,360(0,4); 3,326(206,1);, 497 (137.6); 2,492 (70.3); 2,337 (0.4); 2,333 (0.9); 2,328 (1.2); 2,324 (0.9); 2,319 (0.4); 0.000 (3.2) H-NMR (400.0 MHz, DMSO): δ = 8.518 (1.9); 8,512 (2.0); 8.478 (1.4); 8.474 (1.5); 8,466 (1.5) ;, 462 (1.5); 8,216 (2.0); 8,214 (2.5); 8,212 (2.5); 8.210 (2.0); 7.877 (0.8); 7,873 (0.9); 7,870 (0.9) ;, 866 (0.8); 7,856 (0.9); 7.852 (1.0); 7,850 (1.0); 7,846 (0.9); 7,805 (1.8); 7,800 (2.8); 7,796 (1.7) ;, 464 (1.1); 7,462 (1.1); 7,452 (1.1); 7,450 (1.0); 7,443 (1.0); 7,431 (1.0); 6,848 (2.0); 6.846 (2.2) ;, 844 (2.2); 6,842 (2.1); 6,310 (3.4); 3,855 (16.0); 3,396 (15.1); 3,360 (0.4); 3,326 (206.1);
,675(0,4); 2,670(0,5); 2,666(0,4); 2,541(39,8); 2,524(1,2); 2,510(32,1); 2,506(65,9);, 675 (0.4); 2,670 (0.5); 2,666 (0.4); 2,541 (39.8); 2,524 (1.2); 2,510 (32.1); 2,506 (65.9);
,501(87,8); 2,497(64,8); 2,492(32,0); 2,333(0,4); 2,328(0,6); 2,324(0,4); 0,000(1,5), 501 (87.8); 2,497 (64.8); 2,492 (32.0); 2,333 (0.4); 2,328 (0.6); 2,324 (0.4); 0.000 (1.5)
H-NMR(400,0 MHz, DMSO): δ= 8,527(1,9); 8,521(2,0); 8,495(1,4); 8,492(1,6); 8,483(1,5);,480(1,6); 7,881(0,8); 7,877(0,9); 7,874(0,9); 7,871(0,9); 7,860(0,9); 7,857(1,0); 7,854(1,1);,850(1,0); 7,478(1,1); 7,466(1,1); 7,458(1,1); 7,446(1,0); 6,814(2,4); 6,812(2,5); 6,333(3,4);,674(16,0); 3,397(15,2); 3,381(0,4); 3,357(0,8); 3,327(636,7); 3,278(0,7); 3,256(0,4);H-NMR (400.0 MHz, DMSO): δ = 8.527 (1.9); 8.521 (2.0); 8,495 (1.4); 8.492 (1.6); 8,483 (1.5) ;, 480 (1.6); 7,881 (0.8); 7.877 (0.9); 7,874 (0.9); 7,871 (0.9); 7,860 (0.9); 7,857 (1.0); 7,854 (1.1) ;, 850 (1.0); 7,478 (1.1); 7.466 (1.1); 7,458 (1.1); 7,446 (1.0); 6,814 (2.4); 6,812 (2.5); 6,333 (3.4) ;, 674 (16.0); 3,397 (15.2); 3,381 (0.4); 3,357 (0.8); 3.327 (636.7); 3,278 (0.7); 3,256 (0.4);
,994(0,3); 2,675(1,0); 2,671(1,4); 2,666(1,1); 2,541(44,3); 2,524(3,3); 2,519(5,0); 2,511(77,2);,506(160,7); 2,502(216,1); 2,497(159,8); 2,492(79,3); 2,402(8,3); 2,333(1,0); 2,328(1,4);,324(1,0); 2,271(10,6); 0,000(4,2), 994 (0.3); 2,675 (1.0); 2,671 (1.4); 2,666 (1.1); 2,541 (44.3); 2,524 (3.3); 2,519 (5.0); 2,511 (77.2) ;, 506 (160.7); 2.502 (216.1); 2.497 (159.8); 2,492 (79.3); 2.402 (8.3); 2,333 (1.0); 2,328 (1.4) ;, 324 (1.0); 2.271 (10.6) 0.000 (4.2)
H-NMR(400,0 MHz, DMSO): δ= 8,549(2,3); 8,544(2,2); 8,504(1,6); 8,500(1,7); 8,492(1,7);,488(1,7); 7,972(2,4); 7,909(1,8); 7,906(2,4); 7,889(2,3); 7,885(2,7); 7,883(2,3); 7,879(1,3);,838(1,1); 7,819(1,4); 7,691(1,6); 7,671(2,6); 7,652(1,1); 7,488(1,2); 7,477(1,2); 7,468(1,2);,456(1,1); 6,429(2,6); 3,864(16,0); 3,418(15,4); 3,360(5,3); 2,944(0,8); 2,784(0,6); 2,675(0,5);,670(0,6); 2,666(0,5); 2,510(39,0); 2,506(73,9); 2,501(95,5); 2,497(70,5); 2,493(35,5);H NMR (400.0 MHz, DMSO): δ = 8.549 (2.3); 8.544 (2.2); 8,504 (1.6); 8,500 (1.7); 8.492 (1.7) ;, 488 (1.7); 7,972 (2.4); 7,909 (1.8); 7,906 (2.4); 7,889 (2.3); 7,885 (2.7); 7,883 (2.3); 7,879 (1.3) ;, 838 (1.1); 7,819 (1.4); 7,691 (1.6); 7,671 (2.6); 7,652 (1.1); 7,488 (1.2); 7,477 (1.2); 7,468 (1.2) ;, 456 (1.1); 6,429 (2.6); 3,864 (16.0); 3,418 (15.4); 3,360 (5.3); 2,944 (0.8); 2,784 (0.6); 2,675 (0.5) ;, 670 (0.6); 2,666 (0.5); 2,510 (39.0); 2,506 (73.9); 2,501 (95.5); 2,497 (70.5); 2,493 (35.5);
,332(0,5); 2,328(0,6); 2,324(0,5); 1,988(0,8); 1,957(0,6); 1,175(0,4); 0,000(1,1), 332 (0.5); 2,328 (0.6); 2,324 (0.5); 1,988 (0.8); 1,957 (0.6); 1.175 (0.4); 0.000 (1.1)
H-NMR(400,0 MHz, DMSO): δ= 8,540(2,0); 8,534(2,1); 8,501(1,4); 8,498(1,5); 8,489(1,6);,486(1,6); 7,901(0,9); 7,897(1,0); 7,895(1,0); 7,891(0,9); 7,881(1,0); 7,877(1,2); 7,874(1,2);,871(1,0); 7,520(2,5); 7,485(1,3); 7,473(1,3); 7,465(1,2); 7,454(1,1); 7,453(1,2); 7,417(8,2);,414(9,8); 6,366(3,4); 5,754(4,7); 4,355(0,3); 4,342(0,7); 4,329(0,4); 3,831(16,0); 3,783(1,0);,456(0,6); 3,443(0,6); 3,439(0,7); 3,426(0,7); 3,421(0,5); 3,409(15,4); 3,398(1,2); 3,318(21,5);,984(4,8); 2,966(4,9); 2,944(0,7); 2,906(0,3); 2,888(0,3); 2,784(0,5); 2,524(0,7); 2,511(13,1);,506(26,7); 2,502(35,6); 2,497(26,4); 2,493(13,3); 1,988(0,6); 1,957(0,5); 1,175(0,3);H NMR (400.0 MHz, DMSO): δ = 8.540 (2.0); 8,534 (2.1); 8,501 (1.4); 8,498 (1.5); 8,489 (1.6) ;, 486 (1.6); 7.901 (0.9); 7,897 (1.0); 7.895 (1.0); 7,891 (0.9); 7,881 (1.0); 7.877 (1.2); 7.874 (1.2) ;, 871 (1.0); 7,520 (2.5); 7,485 (1.3); 7,473 (1.3); 7.465 (1.2); 7,454 (1.1); 7,453 (1.2); 7,417 (8.2) ;, 414 (9.8); 6,366 (3.4); 5,754 (4.7); 4,355 (0.3); 4,342 (0.7); 4,329 (0.4); 3,831 (16.0); 3.783 (1.0) ;, 456 (0.6); 3,443 (0.6); 3,439 (0.7); 3,426 (0.7); 3,421 (0.5); 3,409 (15.4); 3,398 (1.2); 3,318 (21.5) ;, 984 (4.8); 2,966 (4.9); 2,944 (0.7); 2,906 (0.3); 2,888 (0.3); 2,784 (0.5); 2,524 (0.7); 2,511 (13.1) ;, 506 (26.7); 2,502 (35.6); 2,497 (26.4); 2,493 (13.3); 1,988 (0.6); 1,957 (0.5); 1.175 (0.3);
,074(1,1); 1,056(2,3); 1,039(1,4); 1,025(0,5); 1,019(0,5); 1,015(0,4); 1,007(0,9); 0,999(0,4);,995(0,5); 0,987(0,6); 0,545(0,8); 0,534(2,2); 0,530(2,3); 0,525(1,1); 0,520(1,1); 0,514(2,2);,510(2,1); 0,500(0,9); 0,277(0,9); 0,266(2,4); 0,263(2,5); 0,255(2,2); 0,251(2,6); 0,240(0,7);,008(2,0); 0,000(53,3); -0,009(2,3), 074 (1.1); 1,056 (2.3); 1,039 (1.4); 1.025 (0.5); 1,019 (0.5); 1,015 (0.4); 1,007 (0.9); 0.999 (0.4) ;, 995 (0.5); 0.987 (0.6); 0.545 (0.8); 0.534 (2.2); 0.530 (2.3) 0.525 (1.1); 0.520 (1.1); 0.514 (2.2) ;, 510 (2.1); 0,500 (0.9); 0.277 (0.9); 0.266 (2.4); 0.263 (2.5); 0,255 (2.2); 0.251 (2.6); 0.240 (0.7) ;, 008 (2.0); 0,000 (53.3); -0.009 (2.3)
H-NMR(400,0 MHz, CD3CN): δ= 8,483(1,0); 8,480(1,1); 8,471(1,2); 8,468(1,3); 8,463(1,6);,457(1,5); 7,738(0,8); 7,735(0,9); 7,732(0,8); 7,728(0,7); 7,718(0,9); 7,714(1,0); 7,712(0,9);,708(0,8); 7,536(1,9); 7,521(0,5); 7,517(0,7); 7,502(0,9); 7,498(1,5); 7,479(0,9); 7,460(1,8);,442(1,1); 7,434(1,0); 7,430(1,5); 7,411(0,7); 7,407(1,2); 7,395(0,9); 7,393(0,9); 7,386(0,8);,374(0,8); 6,372(2,8); 5,447(4,3); 4,479(6,7); 3,823(15,5); 3,427(15,4); 3,348(16,0); 2,958(0,4); ,191(38,7); 1,972(0,5); 1,958(0,8); 1,952(4,2); 1,946(7,5); 1,940(10,1); 1,934(6,9); 1,928(3,5);,008(0,4); 0,000(11,5); -0,009(0,4)H NMR (400.0 MHz, CD 3 CN): δ = 8.483 (1.0); 8,480 (1.1); 8,471 (1.2); 8,468 (1.3); 8.463 (1.6) ;, 457 (1.5); 7,738 (0.8); 7,735 (0.9); 7,732 (0.8); 7,728 (0.7); 7,718 (0.9); 7,714 (1.0); 7,712 (0.9) ;, 708 (0.8); 7,536 (1.9); 7.521 (0.5); 7,517 (0.7); 7,502 (0.9); 7,498 (1.5); 7.479 (0.9); 7,460 (1.8) ;, 442 (1.1); 7,434 (1.0); 7,430 (1.5); 7,411 (0.7); 7,407 (1.2); 7,395 (0.9); 7,393 (0.9); 7,386 (0.8) ;, 374 (0.8); 6,372 (2.8); 5,447 (4.3); 4,479 (6.7); 3,823 (15.5); 3,427 (15.4); 3,348 (16.0); 2,958 (0.4); , 191 (38.7); 1,972 (0.5); 1,958 (0.8); 1,952 (4.2); 1,946 (7.5); 1,940 (10.1); 1,934 (6.9); 1,928 (3.5) ;, 008 (0.4); 0,000 (11.5); -0.009 (0.4)
H-NM (400,0 MHz, CD3CN): δ= 8,484(1,4); 8,480(1,6); 8,472(1,8); 8,468(1,8); 8,463(2,2);,456(2,1); 7,738(0,8); 7,734(1,0); 7,731(1,0); 7,727(0,9); 7,717(1,0); 7,714(1,1); 7,711(1,1);,707(1,0); 7,561(2,1); 7,510(0,5); 7,506(0,5); 7,501(0,8); 7,498(1,0); 7,488(1,3); 7,483(1,1);,473(0,8); 7,454(2,4); 7,453(2,6); 7,446(2,0); 7,441(2,7); 7,438(2,6); 7,405(1,1); 7,404(1,1);,393(1,2); 7,392(1,2); 7,385(1,1); 7,383(1,1); 7,373(1,0); 7,371(1,0); 6,371(3,5); 5,446(7,4);,438(0,8); 4,591(7,2); 3,877(0,9); 3,867(1,8); 3,856(1,2); 3,848(1,3); 3,837(2,3); 3,823(16,0);,816(2,0); 3,631(0,6); 3,619(0,7); 3,608(1,1); 3,598(0,8); 3,586(0,6); 3,576(0,3); 3,426(15,5);,418(2,0); 3,407(1,5); 3,400(1,4); 3,382(1,5); 3,376(2,0); 3,353(1,1); 3,346(1,2); 2,167(1,7);,155(0,8); 1,971(0,8); 1,963(0,9); 1,957(1,8); 1,951(6,2); 1,945(10,9); 1,939(14,3); 1,933(11,0);,926(6,6); 1,901(1,4); 1,897(1,3); 1,891(1,4); 1,568(0,6); 1,558(0,6); 1,544(1,0); 1,535(1,4);,525(0,9); 1,521(0,9); 1,511(1,3); 1,501(0,9); 1,488(0,5); 1,478(0,5); 0,008(2,6); 0,000(27,9); -,009(3,6)H-NM (400.0 MHz, CD 3 CN): δ = 8.484 (1.4); 8,480 (1.6); 8,472 (1.8); 8,468 (1.8); 8.463 (2.2) ;, 456 (2.1); 7,738 (0.8); 7.734 (1.0); 7,731 (1.0); 7,727 (0.9); 7,717 (1.0); 7,714 (1.1); 7.711 (1.1) ;, 707 (1.0); 7,561 (2.1); 7,510 (0.5); 7,506 (0.5); 7,501 (0.8); 7,498 (1.0); 7,488 (1.3); 7,483 (1.1) ;, 473 (0.8); 7,454 (2.4); 7,453 (2.6); 7,446 (2.0); 7,441 (2.7); 7,438 (2.6); 7,405 (1.1); 7,404 (1.1) ;, 393 (1.2); 7,392 (1.2); 7,385 (1.1); 7,383 (1.1); 7,373 (1.0); 7,371 (1.0); 6,371 (3.5); 5,446 (7.4) ;, 438 (0.8); 4,591 (7.2); 3,877 (0.9); 3,867 (1.8); 3,856 (1.2); 3,848 (1.3); 3,837 (2.3); 3,823 (16.0) ;, 816 (2.0); 3,631 (0.6); 3,619 (0.7); 3,608 (1.1); 3,598 (0.8); 3.586 (0.6); 3,576 (0.3); 3,426 (15.5) ;, 418 (2.0); 3,407 (1.5); 3,400 (1.4); 3.382 (1.5); 3,376 (2.0); 3,353 (1.1); 3,346 (1.2); 2.167 (1.7) ;, 155 (0.8); 1,971 (0.8); 1,963 (0.9); 1,957 (1.8); 1,951 (6.2); 1,945 (10.9); 1,939 (14.3); 1,933 (11.0) ;, 926 (6.6); 1,901 (1.4); 1,897 (1.3); 1,891 (1.4); 1,568 (0.6); 1.558 (0.6); 1.544 (1.0); 1.535 (1.4) ;, 525 (0.9); 1,521 (0.9); 1.511 (1.3); 1,501 (0.9); 1,488 (0.5); 1,478 (0.5); 0.008 (2.6); 0,000 (27.9); -, 009 (3.6)
H-NMR(400,0 MHz, CD3CN): δ= 8,486(1,6); 8,482(1,6); 8,474(1,8); 8,470(2,1); 8,466(2,4);,460(2,1); 8,127(1,6); 8,122(2,6); 8,119(1,6); 7,997(1,2); 7,994(0,9); 7,977(1,4); 7,974(1,1);,943(1,3); 7,927(1,2); 7,924(1,5); 7,742(2,3); 7,736(1,2); 7,732(1,1); 7,722(3,3); 7,712(1,0);,702(1,1); 7,405(1,2); 7,394(1,2); 7,385(1,1); 7,373(1,0); 6,416(3,3); 5,446(12,4); 4,068(0,5);,050(0,5); 3,869(16,0); 3,434(15,9); 3,091(15,8); 2,146(5,8); 1,971(2,3); 1,963(0,9); 1,957(1,9);,952(6,6); 1,945(11,2); 1,939(14,2); 1,933(10,0); 1,927(5,2); 1,221(0,5); 1,203(1,1); 1,186(0,5);,000(30,3)H NMR (400.0 MHz, CD 3 CN): δ = 8.486 (1.6); 8,482 (1.6); 8.474 (1.8); 8,470 (2.1); 8,466 (2.4) ;, 460 (2.1); 8,127 (1.6); 8,122 (2.6); 8.119 (1.6); 7,997 (1.2); 7,994 (0.9); 7.977 (1.4); 7,974 (1.1) ;, 943 (1.3); 7.927 (1.2); 7.924 (1.5); 7,742 (2.3); 7,736 (1.2); 7,732 (1.1); 7,722 (3.3); 7,712 (1.0) ;, 702 (1.1); 7,405 (1.2); 7,394 (1.2); 7,385 (1.1); 7,373 (1.0); 6,416 (3.3); 5,446 (12.4); 4.068 (0.5) ;, 050 (0.5); 3,869 (16.0); 3,434 (15.9); 3,091 (15.8); 2,146 (5.8); 1,971 (2.3); 1,963 (0.9); 1,957 (1.9) ;, 952 (6.6); 1,945 (11.2); 1,939 (14.2); 1,933 (10.0); 1,927 (5.2); 1,221 (0.5); 1,203 (1.1); 1,186 (0.5) ;, 000 (30.3)
H-NMR(400,0 MHz, CD3CN): δ= 8,483(1,5); 8,480(1,7); 8,471(1,7); 8,468(1,9); 8,460(2,2);,454(2,2); 7,740(0,9); 7,736(1,0); 7,734(1,1); 7,730(0,9); 7,720(1,0); 7,716(1,1); 7,713(1,2);,710(1,0); 7,406(1,2); 7,394(1,2); 7,386(1,1); 7,374(1,1); 7,357(3,0); 7,259(6,6); 6,363(3,7);,447(1,1); 3,823(15,9); 3,542(1,0); 3,527(0,9); 3,424(16,0); 2,957(0,7); 2,826(0,5); 2,483(15,1);,331(13,5); 2,167(12,2); 1,971(1,1); 1,963(1,2); 1,957(2,5); 1,952(7,3); 1,945(12,0);H NMR (400.0 MHz, CD 3 CN): δ = 8.483 (1.5); 8,480 (1.7); 8,471 (1.7); 8,468 (1.9); 8,460 (2.2) ;, 454 (2.2); 7,740 (0.9); 7,736 (1.0); 7.734 (1.1); 7,730 (0.9); 7,720 (1.0); 7,716 (1.1); 7,713 (1.2) ;, 710 (1.0); 7,406 (1.2); 7,394 (1.2); 7,386 (1.1); 7.374 (1.1); 7,357 (3.0); 7,259 (6.6); 6,363 (3.7) ;, 447 (1.1); 3,823 (15.9); 3,542 (1.0); 3,527 (0.9); 3,424 (16.0); 2,957 (0.7); 2,826 (0.5); 2.483 (15.1) ;, 331 (13.5); 2,167 (12.2); 1,971 (1.1); 1,963 (1.2); 1,957 (2.5); 1,952 (7.3); 1,945 (12.0);
,939(15,1); 1,933(10,8); 1,927(5,7); 1,130(2,9); 1,113(5,7); 1,095(2,8); 0,000(28,4), 939 (15.1); 1,933 (10.8); 1,927 (5.7); 1,130 (2.9); 1,113 (5.7); 1,095 (2.8); 0.000 (28.4)
H-NMR(400,0 MHz, DMSO): δ= 8,883(4,9); 8,692(1,4); 8,608(0,9); 8,564(0,4); 8,540(2,4);,487(1,8); 8,477(2,1); 8,419(0,4); 8,413(0,4); 8,242(4,9); 8,065(2,2); 8,046(2,9); 8,028(1,1);,015(2,0); 7,999(0,6); 7,971(0,8); 7,934(1,0); 7,917(4,7); 7,914(4,7); 7,900(2,9); 7,897(3,1);,891(2,5); 7,888(2,4); 7,884(2,2); 7,880(2,2); 7,874(2,6); 7,870(2,8); 7,864(2,4); 7,849(0,9);,845(0,9); 7,825(1,3); 7,804(0,8); 7,797(0,7); 7,657(1,2); 7,652(1,2); 7,636(1,9); 7,633(1,7);,623(1,5); 7,616(1,3); 7,609(1,0); 7,599(0,5); 7,591(0,5); 7,580(0,4); 7,559(0,3); 7,475(1,4);,463(1,7); 7,454(1,7); 7,443(1,6); 6,636(0,4); 6,352(3,4); 4,208(1,1); 4,056(0,6); 4,038(1,8);,021(1,9); 4,003(0,8); 3,940(16,0); 3,799(0,3); 3,413(15,5); 3,365(0,6); 3,321(16,8); 2,945(0,3);,671(0,6); 2,502(79,9); 2,498(64,9); 2,329(0,5); 1,989(7,4); 1,958(0,5); 1,259(0,4); 1,235(2,4);,193(2,1); 1,175(4,2); 1,158(2,2); 0,146(0,4); 0,000(86,1); -0,150(0,5)H-NMR (400.0 MHz, DMSO): δ = 8.883 (4.9); 8.692 (1.4); 8,608 (0.9); 8,564 (0.4); 8,540 (2.4) ;, 487 (1.8); 8,477 (2.1); 8.419 (0.4); 8.413 (0.4); 8,242 (4.9); 8,065 (2.2); 8,046 (2.9); 8,028 (1.1) ;, 015 (2.0); 7,999 (0.6); 7,971 (0.8); 7,934 (1.0); 7,917 (4.7); 7.914 (4.7); 7,900 (2.9); 7,897 (3.1) ;, 891 (2.5); 7,888 (2.4); 7,884 (2.2); 7,880 (2.2); 7,874 (2.6); 7,870 (2.8); 7,864 (2.4); 7,849 (0.9) ;, 845 (0.9); 7,825 (1.3); 7,804 (0.8); 7,797 (0.7); 7,657 (1.2); 7,652 (1.2); 7,636 (1.9); 7,633 (1.7) ;, 623 (1.5); 7,616 (1.3); 7,609 (1.0); 7,599 (0.5); 7,591 (0.5); 7,580 (0.4); 7,559 (0.3); 7.475 (1.4) ;, 463 (1.7); 7,454 (1.7); 7,443 (1.6); 6,636 (0.4); 6,352 (3.4); 4,208 (1.1); 4,056 (0.6); 4.038 (1.8) ;, 021 (1.9); 4,003 (0.8); 3,940 (16.0); 3,799 (0.3); 3,413 (15.5); 3,365 (0.6); 3,321 (16.8); 2.945 (0.3) ;, 671 (0.6); 2,502 (79.9); 2,498 (64.9); 2,329 (0.5); 1,989 (7.4); 1,958 (0.5); 1,259 (0.4); 1.235 (2.4) ;, 193 (2.1); 1.175 (4.2); 1,158 (2.2); 0.146 (0.4); 0,000 (86.1); -0.150 (0.5)
H-NMR(400,0 MHz, DMSO): δ= 8,638(2,7); 8,633(2,8); 8,535(2,1); 8,529(2,2); 8,486(1,6);,476(1,6); 8,180(5,0); 7,890(0,9); 7,886(1,2); 7,870(1,1); 7,866(1,4); 7,860(1,1); 7,856(0,9);,833(1,7); 7,813(0,9); 7,536(0,4); 7,520(1,3); 7,515(1,7); 7,496(2,7); 7,489(1,8); 7,482(1,2);,474(1,8); 7,462(1,6); 7,454(1,4); 7,442(1,3); 7,416(1,0); 7,410(1,0); 7,395(1,3); 7,381(0,5);,374(0,6); 6,331(3,9); 5,754(0,8); 4,163(0,4); 3,919(16,0); 3,418(0,9); 3,408(15,2); 3,365(0,4);,322(5,3); 2,507(28,0); 2,502(36,5); 2,498(27,9); 1,235(0,7); 0,008(1,8); 0,000(41,5)H-NMR (400.0 MHz, DMSO): δ = 8.638 (2.7); 8.633 (2.8); 8,535 (2.1); 8,529 (2.2); 8.486 (1.6) ;, 476 (1.6); 8,180 (5.0); 7,890 (0.9); 7,886 (1.2); 7,870 (1.1); 7,866 (1.4); 7,860 (1.1); 7,856 (0.9) ;, 833 (1.7); 7,813 (0.9); 7,536 (0.4); 7,520 (1.3); 7,515 (1.7); 7,496 (2.7); 7,489 (1.8); 7,482 (1.2) ;, 474 (1.8); 7,462 (1.6); 7,454 (1.4); 7.442 (1.3); 7,416 (1.0); 7.410 (1.0); 7,395 (1.3); 7,381 (0.5) ;, 374 (0.6); 6,331 (3.9); 5,754 (0.8); 4,163 (0.4); 3,919 (16.0); 3,418 (0.9); 3,408 (15.2); 3.365 (0.4) ;, 322 (5.3); 2,507 (28.0); 2,502 (36.5); 2,498 (27.9); 1,235 (0.7); 0.008 (1.8); 0.000 (41.5)
H-NMR(400,0 MHz, DMSO): δ= 8,936(5,1); 8,539(2,5); 8,533(2,5); 8,488(1,6); 8,485(1,8);,476(1,7); 8,473(1,8); 8,127(5,1); 7,939(3,2); 7,919(3,5); 7,893(0,9); 7,887(1,2); 7,883(1,0);,873(1,0); 7,867(1,3); 7,863(1,0); 7,554(1,9); 7,535(3,3); 7,515(2,2); 7,474(1,4); 7,462(1,4);,454(1,4); 7,442(1,3); 7,378(1,2); 7,360(2,0); 7,341(0,8); 6,331(4,1); 4,203(0,4); 3,944(16,0);,422(0,6); 3,411(15,1); 3,320(16,5); 2,944(1,0); 2,784(0,8); 2,532(0,4); 2,506(32,6);H-NMR (400.0 MHz, DMSO): δ = 8.936 (5.1); 8,539 (2.5); 8,533 (2.5); 8.488 (1.6); 8.485 (1.8) ;, 476 (1.7); 8.473 (1.8); 8,127 (5.1); 7.939 (3.2); 7.919 (3.5); 7,893 (0.9); 7,887 (1.2); 7,883 (1.0) ;, 873 (1.0); 7,867 (1.3); 7,863 (1.0); 7,554 (1.9); 7,535 (3.3); 7,515 (2.2); 7,474 (1.4); 7,462 (1.4) ;, 454 (1.4); 7.442 (1.3); 7,378 (1.2); 7,360 (2.0); 7,341 (0.8); 6,331 (4.1); 4,203 (0.4); 3,944 (16.0) ;, 422 (0.6); 3,411 (15.1); 3,320 (16.5); 2,944 (1.0); 2,784 (0.8); 2,532 (0.4); 2,506 (32.6);
,502(43,5); 2,497(33,2); 1,957(0,9); 1,901(1,0); 1,235(0,9); 0,008(1,6); 0,000(41,6); -0,008(2,0)H-NMR(400,0 MHz, CD3CN): δ= 8,532(2,3); 8,528(3,2); 8,519(1,4); 8,516(1,4); 8,055(1,3);,034(1,4); 7,995(1,2); 7,976(1,4); 7,789(0,7); 7,785(0,9); 7,782(0,8); 7,779(0,8); 7,768(0,8);,764(1,0); 7,762(1,0); 7,758(0,9); 7,616(1,0); 7,598(1,7); 7,578(2,0); 7,565(1,1); 7,562(1,3); ,545(1,0); 7,541(1,2); 7,535(2,5); 7,519(1,4); 7,515(1,9); 7,511( 1,4); 7,497(0,7); 7,494(0,7);,450(2,3); 7,440(1,2); 7,430(1,6); 7,419(1,0); 6,510(3,5); 4,068(0,7); 4,050(0,7); 3,922(0,8);,551(16,0); 3,462( 15,8); 3,446(0,9); 2,956(0,7); 2,826(0,6); 2,155(12,8); 1,971(3,7); 1,964(0,8);,957(1,7); 1,951(8,8); 1,945(16,1); 1,939(21,8); 1,933(15,6); 1,927(8,3); 1,221(0,8); 1,203(1,6);,186(0,8); 0,008(1,8); 0,000(46,5), 502 (43.5); 2,497 (33.2); 1,957 (0.9); 1,901 (1.0); 1,235 (0.9); 0.008 (1.6); 0,000 (41.6); -0.008 (2.0) H-NMR (400.0 MHz, CD3CN): δ = 8.532 (2.3); 8.528 (3.2); 8,519 (1.4); 8,516 (1.4); 8,055 (1.3) ;, 034 (1.4); 7,995 (1.2); 7,976 (1.4); 7.789 (0.7); 7,785 (0.9); 7,782 (0.8); 7,779 (0.8); 7.768 (0.8) ;, 764 (1.0); 7,762 (1.0); 7.758 (0.9); 7,616 (1.0); 7.598 (1.7); 7,578 (2.0); 7,565 (1.1); 7,562 (1.3); , 545 (1.0); 7,541 (1.2); 7,535 (2.5); 7,519 (1.4); 7,515 (1.9); 7,511 (1.4); 7,497 (0.7); 7,494 (0.7) ;, 450 (2.3); 7,440 (1.2); 7,430 (1.6); 7,419 (1.0); 6.510 (3.5); 4,068 (0.7); 4,050 (0.7); 3.922 (0.8) ;, 551 (16.0); 3,462 (15.8); 3,446 (0.9); 2,956 (0.7); 2,826 (0.6); 2,155 (12.8); 1,971 (3.7); 1.964 (0.8) ;, 957 (1.7); 1,951 (8.8); 1,945 (16.1); 1,939 (21.8); 1,933 (15.6); 1,927 (8.3); 1,221 (0.8); 1.203 (1.6) ;, 186 (0.8); 0.008 (1.8); 0.000 (46.5)
H-NM (400,0 MHz, CD3CN ): δ= 8,689(2,3); 8,685(2,3); 8,537(2,2); 8,531(3,1); 8,522(1,5);,519(1,4); 8,204(1,0); 8,199(1,0); 8,185(1,0); 8,181(1,1); 8,028( 1,4); 8,024(1,3); 8,006(1,5);,002(1,5); 7,787(0,8); 7,783(0,9); 7,781(0,9); 7,777(0,8); 7,767(0,9); 7,763(1,0); 7,760(1,1);,757(0,9); 7,707(0,6); 7,689(2,1); 7,671(3,5); 7,668(3,0); 7,656(0,7); 7,588(1,9); 7,566(1,7);,452(1,1); 7,440(1,1); 7,431(1,0); 7,419(0,9); 6,519(3,4); 3,938( 16,0); 3,574(15,8); 3,464(15,8);,956(0,8); 2,825(0,7); 2,153(1,2); 1,970(1,0); 1,964(0,4); 1,958(1,0); 1,952(5,1); 1,946(9,3);,940(12,6); 1,933(8,8); 1,927(4,6); 0,008( 1,1); 0,000(27,8); -0,008(1,4)H-NM (400.0 MHz, CD 3 CN): δ = 8.689 (2.3); 8.685 (2.3); 8,537 (2.2); 8,531 (3.1); 8,522 (1.5) ;, 519 (1.4); 8,204 (1.0); 8,199 (1.0); 8.185 (1.0); 8,181 (1.1); 8,028 (1.4); 8.024 (1.3); 8,006 (1.5) ;, 002 (1.5); 7.787 (0.8); 7,783 (0.9); 7.781 (0.9); 7,777 (0.8); 7,767 (0.9); 7,763 (1.0); 7,760 (1.1) ;, 757 (0.9); 7,707 (0.6); 7.689 (2.1); 7,671 (3.5); 7.668 (3.0); 7,656 (0.7); 7,588 (1.9); 7,566 (1.7) ;, 452 (1.1); 7,440 (1.1); 7,431 (1.0); 7,419 (0.9); 6,519 (3.4); 3,938 (16.0); 3,574 (15.8); 3,464 (15.8) ;, 956 (0.8); 2,825 (0.7); 2,153 (1.2); 1,970 (1.0); 1,964 (0.4); 1,958 (1.0); 1,952 (5.1); 1.946 (9.3) ;, 940 (12.6); 1,933 (8.8); 1,927 (4.6); 0.008 (1.1); 0,000 (27.8); -0.008 (1.4)
H-NMR(400,0 MHz, CD3CN ): δ= 8,486(1,5); 8,483(1,5); 8,468(2,4); 8,461(2,1); 7,751(0,8);,748(1,0); 7,745(1,0); 7,741(0,8); 7,731(1,0); 7,727(1,1); 7,725( 1,1); 7,721(0,9); 7,706(1,2);,701(1,2); 7,683(1,1); 7,677(1,2); 7,479(0,6); 7,465(0,8); 7,458( 1,6); 7,444(1,6); 7,435(1,1);,429(1,0); 7,417(1,7); 7,415(1,7); 7,408(2,2); 7,399(1,2); 7,387( 1,4); 6,300(3,5); 5,446(0,7);,068(0,4); 4,050(0,5); 3,806(0,3); 3,717(0,6); 3,665(0,7); 3,649(16,0); 3,556(15,5); 3,441(0,7);,426(15,7); 3,320(0,6); 3,292(0,5); 2,957(0,7); 2,826(0,6); 2,140(4,1); 1,971(2,5); 1,963(0,7);,951(8,1); 1,945(14,4); 1,939(19,0); 1,933(13,2); 1,927(6,9); 1,270(0,8); 1,221(0,5); 1,204(1,0);,186(0,5); 0,000(40,2)H NMR (400.0 MHz, CD 3 CN): δ = 8.486 (1.5); 8,483 (1.5); 8,468 (2.4); 8.461 (2.1); 7,751 (0.8) ;, 748 (1.0); 7,745 (1.0); 7.741 (0.8); 7,731 (1.0); 7,727 (1.1); 7.725 (1.1); 7.721 (0.9); 7.706 (1.2) ;, 701 (1.2); 7,683 (1.1); 7,677 (1.2); 7.479 (0.6); 7.465 (0.8); 7.458 (1.6); 7,444 (1.6); 7.435 (1.1) ;, 429 (1.0); 7,417 (1.7); 7,415 (1.7); 7,408 (2.2); 7,399 (1.2); 7,387 (1.4); 6,300 (3.5); 5,446 (0.7) ;, 068 (0.4); 4,050 (0.5); 3,806 (0.3); 3,717 (0.6); 3,665 (0.7); 3,649 (16.0); 3.556 (15.5); 3,441 (0.7) ;, 426 (15.7); 3,320 (0.6); 3,292 (0.5); 2,957 (0.7); 2,826 (0.6); 2,140 (4.1); 1,971 (2.5); 1,963 (0.7) ;, 951 (8.1); 1,945 (14.4); 1,939 (19.0); 1,933 (13.2); 1,927 (6.9); 1.270 (0.8); 1,221 (0.5); 1.204 (1.0) ;, 186 (0.5); 0.000 (40.2)
H-NMR(400,0 MHz, CD3CN ): δ= 8,530(3,1); 8,526(2,6); 8,524(2,5); 8,518(1,7); 8,514(1,5);,192(1,3); 8,172(1,4); 7,784(0,8); 7,780(0,9); 7,778(0,9); 7,774(0,8); 7,764(0,9); 7,760(1,1);,758(1,2); 7,754(1,0); 7,674(0,6); 7,672(0,6); 7,655(1,3); 7,637(1,0); 7,634(0,9); 7,621(0,9);,618(0,9); 7,600(1,4); 7,597(1,2); 7,583(0,7); 7,580(0,6); 7,530( 1,1); 7,517(1,2); 7,511(1,4);,497(1,6); 7,490(1,3); 7,469(1,0); 7,449(1,1); 7,447(1,1); 7,435( 1,1); 7,429(1,0); 7,427(1,0);,417(0,9); 7,415(1,0); 7,341(1,3); 7,321(1,1); 7,315(1,4); 7,295( 1,1); 6,503(3,4); 4,068(0,7);,050(0,7); 3,553(16,0); 3,460(16,0); 3,447(0,4); 2,956(1,7); 2,826(1,4); 2,138(7,5); 1,971(4,4);,964(0,7); 1,957(1,5); 1,952(7,5); 1,945(13,6); 1,939(18,2); 1,933(12,7); 1,927(6,7); 1,221(0,8);,204(1,6); 1,186(0,8); 0,008(1,6); 0,000(39,1); -0,008(2,0)H NMR (400.0 MHz, CD 3 CN): δ = 8.530 (3.1); 8,526 (2.6); 8,524 (2.5); 8.518 (1.7); 8,514 (1.5) ;, 192 (1.3); 8,172 (1.4); 7,784 (0.8); 7,780 (0.9); 7,778 (0.9); 7,774 (0.8); 7.764 (0.9); 7,760 (1.1) ;, 758 (1.2); 7,754 (1.0); 7,674 (0.6); 7,672 (0.6); 7.655 (1.3); 7,637 (1.0); 7,634 (0.9); 7.621 (0.9) ;, 618 (0.9); 7,600 (1.4); 7,597 (1.2); 7,583 (0.7); 7,580 (0.6); 7,530 (1,1); 7,517 (1.2); 7,511 (1.4) ;, 497 (1.6); 7,490 (1.3); 7.469 (1.0); 7,449 (1.1); 7,447 (1.1); 7.435 (1.1); 7.429 (1.0); 7,427 (1.0) ;, 417 (0.9); 7,415 (1.0); 7,341 (1.3); 7,321 (1.1); 7,315 (1.4); 7.295 (1.1); 6,503 (3.4); 4.068 (0.7) ;, 050 (0.7); 3,553 (16.0); 3,460 (16.0); 3,447 (0.4); 2,956 (1.7); 2,826 (1.4); 2,138 (7.5); 1,971 (4.4) ;, 964 (0.7); 1,957 (1.5); 1,952 (7.5); 1,945 (13.6); 1,939 (18.2); 1,933 (12.7); 1,927 (6.7); 1.221 (0.8) ;, 204 (1.6); 1,186 (0.8); 0.008 (1.6); 0,000 (39.1); -0.008 (2.0)
H-NMR(400,0 MHz, CD3CN ): δ= 8,480(1,6); 8,471(1,6); 8,456(1,9); 8,450(1,9); 8,011(2,3);,006(2,4); 7,731(2,1); 7,725(1,9); 7,710(2,7); 7,705(2,4); 7,606(2,7); 7,585(1,9); 7,402(1,2);,390(1,2); 7,382(1,1); 7,370(1,0); 6,391(3,4); 5,446(1,0); 4,387( 1,3); 4,369(4,0); 4,351(4,0);,333(1,4); 3,839(16,0); 3,563(0,6); 3,426( 15,7); 2,957(3,3); 2,826(2,9); 2,143(5,4); 1,971(3,2);,958(1,2); 1,952(5,9); 1,946(10,8); 1,940( 14,6); 1,933(10,2); 1,927(5,3); 1,378(0,5); 1,371(3,9);,360(1,1); 1,353(7,8); 1,342(0,7); 1,336(3,9); 1,095(0,3); 0,008( 1,2); 0,000(31,4)H NMR (400.0 MHz, CD 3 CN): δ = 8.480 (1.6); 8,471 (1.6); 8.456 (1.9); 8,450 (1.9); 8.011 (2.3) ;, 006 (2.4); 7,731 (2.1); 7,725 (1.9); 7.710 (2.7); 7,705 (2.4); 7,606 (2.7); 7,585 (1.9); 7,402 (1.2) ;, 390 (1.2); 7,382 (1.1); 7,370 (1.0); 6,391 (3.4); 5,446 (1.0); 4.387 (1.3); 4,369 (4.0); 4,351 (4.0) ;, 333 (1.4); 3,839 (16.0); 3,563 (0.6); 3,426 (15.7); 2,957 (3.3); 2,826 (2.9); 2.143 (5.4); 1,971 (3.2) ;, 958 (1.2); 1,952 (5.9); 1,946 (10.8); 1,940 (14.6); 1,933 (10.2); 1,927 (5.3); 1,378 (0.5); 1.371 (3.9) ;, 360 (1.1); 1,353 (7.8); 1,342 (0.7); 1.336 (3.9); 1,095 (0.3); 0.008 (1.2); 0.000 (31.4)
H-NMR(400,0 MHz, CD3CN ): δ= 8,490(1,3); 8,486(1,4); 8,474(3,1); 8,468(1,9); 7,978(1,2);,975(1,2); 7,959(1,3); 7,956(1,3); 7,756(0,7); 7,752(0,8); 7,749(0,8); 7,745(0,7); 7,735(0,8);,731(0,9); 7,729(1,0); 7,725(0,8); 7,688(0,4); 7,684(0,5); 7,669( 1,3); 7,665(1,3); 7,650(1,1);,646(1,0); 7,635(1,0); 7,631(1,2); 7,616(1,3); 7,612(1,4); 7,597(0,5); 7,593(0,5); 7,435(1,4);,431(1,5); 7,421(1,2); 7,416(1,3); 7,412(1,7); 7,401(1,0); 7,389(0,9); 6,310(3,3); 5,446(2,2);,877(0,4); 3,638(16,0); 3,560(15,5); 3,429(15,5); 2,957(0,4); 1,971(1,3); 1,963(0,6); 1,957(1,3);,951(7,2); 1,945(13,2); 1,939(17,7); 1,933(12,3); 1,927(6,4); 1,203(0,5); 0,008(1,4);H NMR (400.0 MHz, CD 3 CN): δ = 8.490 (1.3); 8.486 (1.4); 8.474 (3.1); 8,468 (1.9); 7,978 (1.2) ;, 975 (1.2); 7,959 (1.3); 7,956 (1.3); 7,756 (0.7); 7,752 (0.8); 7,749 (0.8); 7,745 (0.7); 7,735 (0.8) ;, 731 (0.9); 7,729 (1.0); 7,725 (0.8); 7.688 (0.4); 7,684 (0.5); 7.699 (1.3); 7,665 (1.3); 7,650 (1.1) ;, 646 (1.0); 7,635 (1.0); 7,631 (1.2); 7,616 (1.3); 7.612 (1.4); 7,597 (0.5); 7,593 (0.5); 7.435 (1.4) ;, 431 (1.5); 7,421 (1.2); 7,416 (1.3); 7,412 (1.7); 7,401 (1.0); 7,389 (0.9); 6,310 (3.3); 5,446 (2.2) ;, 877 (0.4); 3,638 (16.0); 3,560 (15.5); 3,429 (15.5); 2,957 (0.4); 1,971 (1.3); 1,963 (0.6); 1,957 (1.3) ;, 951 (7.2); 1,945 (13.2); 1,939 (17.7); 1,933 (12.3); 1,927 (6.4); 1,203 (0.5); 0.008 (1.4);
,000(37,4); -0,009(1,8), 000 (37.4); -0.009 (1.8)
H-NMR(400,0 MHz, DMSO): δ= 8,697(3,4); 8,682(3,6); 8,544(2,4); 8,538(2,5); 8,496(1,8);,486(1,9); 8,484(1,9); 7,980(0,4); 7,974(0,6); 7,946(0,3); 7,934(0,4); 7,902(1,1); 7,897(0,9);,881(1,3); 7,687(4,0); 7,672(4,0); 7,482(1,4); 7,471(1,5); 7,462( 1,5); 7,450(1,4); 6,458(3,0);,936(1,1); 3,915(16,0); 3,893(1,2); 3,418( 15,7); 3,404(2,4); 3,369(1,4); 3,330(2,4); 3,241(0,4);,756(2,1); 2,670(0,6); 2,505(67,3); 2,501(87,1); 2,497(67,4); 2,328(0,6); 0,146(0,4); 0,007(2,9);,000(72,0); -0,150(0,4)H-NMR (400.0 MHz, DMSO): δ = 8.697 (3.4); 8.682 (3.6); 8.544 (2.4); 8,538 (2.5); 8,496 (1.8) ;, 486 (1.9); 8,484 (1.9); 7,980 (0.4); 7,974 (0.6); 7,946 (0.3); 7,934 (0.4); 7,902 (1.1); 7,897 (0.9) ;, 881 (1.3); 7,687 (4.0); 7,672 (4.0); 7,482 (1.4); 7,471 (1.5); 7.462 (1.5); 7,450 (1.4); 6,458 (3.0) ;, 936 (1.1); 3,915 (16.0); 3,893 (1.2); 3,418 (15.7); 3,404 (2.4); 3,369 (1.4); 3,330 (2.4); 3,241 (0.4) ;, 756 (2.1); 2,670 (0.6); 2,505 (67.3); 2,501 (87.1); 2,497 (67.4); 2,328 (0.6); 0.146 (0.4); 0.007 (2.9) ;, 000 (72.0); -0.150 (0.4)
H-NMR(400,0 MHz, CD3CN ): δ= 8,481(0,9); 8,203(2,1); 8,082(1,3); 8,062(1,4); 7,840(1,0);,821(1,2); 7,737(0,9); 7,716(1,0); 7,614(1,2); 7,595(2,1); 7,575( 1,0); 7,411(0,6); 7,399(0,6);,392(0,6); 7,380(0,5); 6,403(1,0); 5,446(1,5); 4,380(1,3); 4,362(4,0); 4,344(4,0); 4,327(1,4); ,847(15,5); 3,433( 16,0); 2,151(2,0); 1,964(0,4); 1,958(1,1); 1,952(5,8); 1,946(10,5);H NMR (400.0 MHz, CD 3 CN): δ = 8.481 (0.9); 8,203 (2.1); 8,082 (1.3); 8.062 (1.4); 7,840 (1.0) ;, 821 (1.2); 7,737 (0.9); 7,716 (1.0); 7,614 (1.2); 7,595 (2.1); 7,575 (1.0); 7,411 (0.6); 7,399 (0.6) ;, 392 (0.6); 7,380 (0.5); 6,403 (1.0); 5,446 (1.5); 4,380 (1.3); 4,362 (4.0); 4,344 (4.0); 4,327 (1.4); , 847 (15.5); 3,433 (16.0); 2,151 (2.0); 1,964 (0.4); 1,958 (1.1); 1,952 (5.8); 1,946 (10.5);
,939(14,0); 1,933(9,7); 1,927(5,0); 1,378(4,2); 1,361(8,3); 1,343(4,1); 0,008(1,3); 0,000(30,0); -,008(1,3), 939 (14.0); 1,933 (9.7); 1,927 (5.0); 1,378 (4.2); 1.361 (8.3) 1,343 (4.1); 0.008 (1.3); 0,000 (30.0); -, 008 (1.3)
H-NM (400,0 MHz, CD3CN ): δ= 8,493(1,5); 8,485(2,8); 8,481(2,9); 8,121(2,3); 7,981(2,4);,971(1,1); 7,961(3,1); 7,954(1,3); 7,945(0,9); 7,930(1,1); 7,759(0,8); 7,755(1,0); 7,745(1,6);,741(1,7); 7,734(1,2); 7,728(1,1); 7,724(1,3); 7,720(1,2); 7,598(0,4); 7,588(2,7); 7,581(1,5);,579(1,6); 7,574(1,5); 7,571(1,4); 7,564(2,3); 7,418(1,1); 7,406( 1,1); 7,398(1,0); 7,386(1,0);,429(3,0); 4,068(0,5); 4,050(0,5); 3,921(15,6); 3,445(16,0); 2,158(0,9); 1,971(2,3); 1,963(0,4);,957(0,8); 1,951(4,3); 1,945(7,8); 1,939(10,4); 1,933(7,2); 1,927(3,7); 1,221(0,6); 1,203(1,2);,185(0,6); 0,008(0,8); 0,000(17,5); -0,008(0,7)H-NM (400.0 MHz, CD 3 CN): δ = 8.493 (1.5); 8,485 (2.8); 8.481 (2.9); 8,121 (2.3); 7,981 (2.4) ;, 971 (1.1); 7,961 (3.1); 7,954 (1.3); 7,945 (0.9); 7,930 (1.1); 7.759 (0.8); 7,755 (1.0); 7,745 (1.6) ;, 741 (1.7); 7.734 (1.2); 7,728 (1.1); 7,724 (1.3); 7,720 (1.2); 7.598 (0.4); 7,588 (2.7); 7,581 (1.5) ;, 579 (1.6); 7,574 (1.5); 7,571 (1.4); 7,564 (2.3); 7,418 (1.1); 7.406 (1.1); 7,398 (1.0); 7,386 (1.0) ;, 429 (3.0); 4,068 (0.5); 4,050 (0.5); 3,921 (15.6); 3,445 (16.0); 2,158 (0.9); 1,971 (2.3); 1,963 (0.4) ;, 957 (0.8); 1,951 (4.3); 1,945 (7.8); 1,939 (10.4); 1,933 (7.2); 1,927 (3.7); 1,221 (0.6); 1.203 (1.2) ;, 185 (0.6); 0.008 (0.8); 0,000 (17.5); -0.008 (0.7)
H-NMR(400,0 MHz, CD3CN ): δ= 8,479(1,6); 8,476(1,7); 8,467(1,8); 8,464(1,8); 8,456(2,1);,450(2,1); 8,415(0,4); 8,409(0,4); 7,908(2,3); 7,903(2,5); 7,747( 1,3); 7,741(1,2); 7,725(2,4);,719(2,1); 7,708(1,0); 7,705(1,1); 7,702(1,1); 7,699(0,9); 7,399( 1,3); 7,388(1,4); 7,379(1,1);,368(1,2); 7,186(2,2); 7,164(2,1); 6,348(3,5); 6,164(0,4); 5,446(4,8); 3,898(13,8); 3,822(16,0);,816(15,6); 3,806(2,9); 3,422(14,2); 3,385(2,7); 2,143(5,2); 1,971(1,3); 1,963(0,6); 1,952(6,0);,945(10,6); 1,939( 13,9); 1,933(9,8); 1,927(5,1); 1,221(0,3); 1,203(0,6); 0,000(22,4)H-NMR (400.0 MHz, CD 3 CN): δ = 8.469 (1.6); 8,476 (1.7); 8,467 (1.8); 8,464 (1.8); 8.456 (2.1) ;, 450 (2.1); 8,415 (0.4); 8,409 (0.4); 7.908 (2.3); 7,903 (2.5); 7,747 (1.3); 7.741 (1.2); 7,725 (2.4) ;, 719 (2.1); 7,708 (1.0); 7,705 (1.1); 7,702 (1.1); 7,699 (0.9); 7,399 (1.3); 7,388 (1.4); 7,379 (1.1) ;, 368 (1.2); 7,186 (2.2); 7,164 (2.1); 6,348 (3.5); 6,164 (0.4); 5,446 (4.8); 3,898 (13.8); 3,822 (16.0) ;, 816 (15.6); 3,806 (2.9); 3,422 (14.2); 3,385 (2.7); 2.143 (5.2); 1,971 (1.3); 1,963 (0.6); 1,952 (6.0) ;, 945 (10.6); 1,939 (13.9); 1,933 (9.8); 1,927 (5.1); 1,221 (0.3); 1,203 (0.6); 0.000 (22.4)
H-NMR(400,0 MHz, DMSO): δ= 8,527(2,2); 8,521(2,3); 8,485(1,5); 8,482(1,6); 8,473(1,6);,470(1,6); 8,183(4,5); 7,962(1,7); 7,959(1,8); 7,955(2,0); 7,952( 1,8); 7,886(0,8); 7,882(1,0);,880(1,0); 7,876(0,9); 7,866(0,9); 7,862(1,1); 7,859(1,1); 7,856(0,9); 7,683(1,5); 7,676(1,6);,670(1,8); 7,663(1,6); 7,471(1,3); 7,457(2,6); 7,454(2,3); 7,444( 1,8); 7,441(2,3); 6,324(3,6);,891(16,0); 3,403( 15,2); 2,891(0,6); 2,732(0,5); 2,528(0,9); 2,524(1,0); 2,510(18,2);H-NMR (400.0 MHz, DMSO): δ = 8.527 (2.2); 8.521 (2.3); 8,485 (1.5); 8,482 (1.6); 8.473 (1.6) ;, 470 (1.6); 8,183 (4.5); 7.962 (1.7); 7,959 (1.8); 7,955 (2.0); 7.952 (1.8); 7,886 (0.8); 7,882 (1.0) ;, 880 (1.0); 7,876 (0.9); 7,866 (0.9); 7,862 (1.1); 7,859 (1.1); 7,856 (0.9); 7,683 (1.5); 7.676 (1.6) ;, 670 (1.8); 7,663 (1.6); 7,471 (1.3); 7.457 (2.6); 7,454 (2.3); 7.444 (1.8); 7,441 (2.3); 6,324 (3.6) ;, 891 (16.0); 3,403 (15,2); 2,891 (0.6); 2,732 (0.5); 2,528 (0.9); 2,524 (1.0); 2,510 (18.2);
,506(36,5); 2,502(48,2); 2,497(35,9); 0,008(1,8); 0,000(47,1), 506 (36.5); 2.502 (48.2) 2,497 (35.9); 0.008 (1.8); 0.000 (47.1)
H-NMR(400,0 MHz, CD3CN ): δ= 8,479(1,3); 8,476(1,4); 8,467(1,4); 8,464(1,5); 8,452(2,0);,446(2,0); 7,732(0,7); 7,728(0,9); 7,726(0,9); 7,722(0,8); 7,711(0,8); 7,707(1,0); 7,705(1,0);,701(0,9); 7,401(1,2); 7,389(1,2); 7,380(1,1); 7,368(1,0); 7,275( 1,5); 7,256(1,9); 7,115(1,4);,112(1,6); 7,096(1,1); 7,093(1,2); 6,980(2,6); 6,978(2,5); 6,343(3,6); 4,721(9,6); 4,215(1,3);,197(3,8); 4,179(3,8); 4,162(1,3); 3,794(16,0); 3,418(15,8); 2,956(0,4); 2,283(11,7); 2,150(2,2);,971(1,6); 1,963(0,5); 1,957(1,3); 1,951(7,1); 1,945(12,9); 1,939(17,4); 1,933(12,0); 1,926(6,2);,269(0,5); 1,245(4,3); 1,228(8,5); 1,210(4,2); 1,203(0,8); 1,185(0,3); 0,008(2,1); 0,000(53,1); -,008(2,3)H NMR (400.0 MHz, CD 3 CN): δ = 8.479 (1.3); 8,476 (1.4); 8,467 (1.4); 8,464 (1.5); 8.452 (2.0) ;, 446 (2.0); 7,732 (0.7); 7,728 (0.9); 7,726 (0.9); 7,722 (0.8); 7.711 (0.8); 7,707 (1.0); 7,705 (1.0) ;, 701 (0.9); 7,401 (1.2); 7,389 (1.2); 7,380 (1.1); 7,368 (1.0); 7.275 (1.5); 7.256 (1.9); 7,115 (1.4) ;, 112 (1.6); 7,096 (1.1); 7,093 (1.2); 6,980 (2.6); 6,978 (2.5); 6,343 (3.6); 4,721 (9.6); 4.215 (1.3) ;, 197 (3.8); 4,179 (3.8); 4,162 (1.3); 3,794 (16.0); 3,418 (15.8); 2,956 (0.4); 2,283 (11.7); 2,150 (2.2) ;, 971 (1.6); 1,963 (0.5); 1,957 (1.3); 1,951 (7.1); 1,945 (12.9); 1,939 (17.4); 1,933 (12.0); 1.926 (6.2) ;, 269 (0.5); 1.245 (4.3); 1.228 (8.5); 1,210 (4.2); 1,203 (0.8); 1,185 (0.3); 0.008 (2.1); 0,000 (53.1); -, 008 (2.3)
H-NMR(400,0 MHz, CD3CN ): δ= 8,483(1,4); 8,480(1,4); 8,471(1,5); 8,468(1,4); 8,459(2,0);,453(1,9); 7,735(0,8); 7,731(0,9); 7,729(0,9); 7,725(0,8); 7,715(0,9); 7,711(1,0); 7,709(1,0);,705(0,8); 7,417(1,1); 7,404(1,2); 7,396(2,3); 7,384(1,1); 7,376( 1,6); 7,373(1,1); 7,208(1,5);,189(1,3); 7,102(1,4); 7,096(1,9); 7,093(1,5); 7,021(1,1); 7,020(1,1); 7,015(1,0); 7,001(1,0);,999(1,0); 6,994(0,9); 6,363(3,5); 5,447(8,7); 4,703(9,4); 4,227( 1,3); 4,209(3,8); 4,191(3,8);,174(1,3); 4,068(0,5); 4,050(0,5); 3,814(15,9); 3,423(16,0); 2,175(10,6); 1,971(2,2); 1,963(0,5);,957(1,2); 1,951(5,9); 1,945(10,6); 1,939( 14,1); 1,933(9,7); 1,927(5,0); 1,256(4,4); 1,238(8,5);,221(4,7); 1,203(1,1); 1,185(0,5); 0,008(3,1); 0,000(61,5); -0,009(3,1); -0,150(0,3)H-NMR (400.0 MHz, CD 3 CN): δ = 8.483 (1.4); 8,480 (1.4); 8,471 (1.5); 8,468 (1.4); 8.459 (2.0) ;, 453 (1.9); 7,735 (0.8); 7,731 (0.9); 7,729 (0.9); 7,725 (0.8); 7.715 (0.9); 7.711 (1.0); 7.709 (1.0) ;, 705 (0.8); 7,417 (1.1); 7,404 (1.2); 7,396 (2.3); 7,384 (1.1); 7.376 (1.6); 7,373 (1.1); 7,208 (1.5) ;, 189 (1.3); 7,102 (1.4); 7,096 (1.9); 7,093 (1.5); 7,021 (1.1); 7,020 (1.1); 7.015 (1.0); 7,001 (1.0) ;, 999 (1.0); 6,994 (0.9); 6,363 (3.5); 5,447 (8.7); 4,703 (9.4); 4,227 (1,3); 4,209 (3.8); 4.191 (3.8) ;, 174 (1.3); 4,068 (0.5); 4,050 (0.5); 3,814 (15.9); 3,423 (16.0); 2,175 (10.6); 1,971 (2.2); 1,963 (0.5) ;, 957 (1.2); 1,951 (5.9); 1,945 (10.6); 1,939 (14,1); 1,933 (9.7); 1,927 (5.0); 1,256 (4.4); 1.238 (8.5) ;, 221 (4.7); 1,203 (1.1); 1,185 (0.5); 0.008 (3.1); 0,000 (61.5); -0.009 (3.1); -0.150 (0.3)
H-NMR(400,0 MHz, CD3CN ): δ= 8,480(1,5); 8,477(1,5); 8,468(1,6); 8,465(1,5); 8,445(2,2);,439(2,2); 7,731(0,8); 7,727(1,1); 7,725(1,0); 7,721(0,8); 7,710( 1,0); 7,707(1,2); 7,704(1,1);,701(0,9); 7,401(1,3); 7,390(1,3); 7,381(1,2); 7,369(1,1); 7,159(0,7); 7,154(0,7); 7,142(0,7);,137(0,8); 7,132(0,8); 7,127(0,8); 7,115(0,7); 7,110(0,7); 7,042(1,4); 7,024(1,4); 6,350(3,6);,798(9,8); 4,231(1,3); 4,213(3,9); 4,196(4,0); 4,178(1,3); 4,068(0,9); 4,050(0,9); 3,800(16,0);,418(15,9); 2,957(0,4); 2,826(0,4); 2,143(6,8); 1,971(4,2); 1,957(1,2); 1,951(5,3); 1,945(9,4);,939(12,5); 1,933(8,8); 1,927(4,6); 1,253(4,3); 1,235(8,5); 1,217(4,3); 1,203(2,0); 1,185(1,0);,007(2,6); 0,000(47,7)H NMR (400.0 MHz, CD 3 CN): δ = 8.480 (1.5); 8,477 (1.5); 8,468 (1.6); 8,465 (1.5); 8,445 (2.2) ;, 439 (2.2); 7,731 (0.8); 7,727 (1.1); 7,725 (1.0); 7.721 (0.8); 7.710 (1.0); 7,707 (1.2); 7.704 (1.1) ;, 701 (0.9); 7,401 (1.3); 7,390 (1.3); 7,381 (1.2); 7,369 (1.1); 7,159 (0.7); 7,154 (0.7); 7,142 (0.7) ;, 137 (0.8); 7,132 (0.8); 7.127 (0.8); 7,115 (0.7); 7.110 (0.7); 7,042 (1.4); 7,024 (1.4); 6.350 (3.6) ;, 798 (9.8); 4,231 (1.3); 4,213 (3.9); 4,196 (4.0); 4,178 (1.3); 4,068 (0.9); 4,050 (0.9); 3,800 (16.0) ;, 418 (15.9); 2,957 (0.4); 2,826 (0.4); 2.143 (6.8); 1,971 (4.2); 1,957 (1.2); 1,951 (5.3); 1.945 (9.4) ;, 939 (12.5); 1,933 (8.8); 1,927 (4.6); 1,253 (4.3); 1,235 (8.5); 1,217 (4.3); 1,203 (2.0); 1.185 (1.0) ;, 007 (2.6); 0.000 (47.7)
H-NMR(400,0 MHz, CD3CN ): δ= 8,480(1,5); 8,478(1,6); 8,469(1,5); 8,466(1,6); 8,451(2,2);,445(2,2); 7,733(0,8); 7,729(1,0); 7,727(1,0); 7,724(0,8); 7,713(0,9); 7,709(1,1); 7,707(1,1);,402(1,2); 7,390(1,2); 7,382(1,1); 7,370(1,0); 7,270(0,9); 7,249( 1,6); 7,242(0,8); 7,221(1,6);,214(1,3); 7,209(1,7); 7,198(1,3); 7,193(1,7); 7,187(2,5); 7,178(0,7); 7,173(0,5); 7,166(0,6);,161(0,4); 6,345(3,8); 5,447(4,4); 4,769(9,5); 4,226(1,3); 4,208(3,9); 4,190(3,9); 4,172(1,3);,085(0,5); 4,068(1,5); 4,050(1,5); 4,032(0,5); 3,790(15,8); 3,419(16,0); 2,956(0,8); 2,825(0,7); ,171(13,4); 1,971(6,8); 1,957(1,0); 1,952(4,5); 1,946(8,1); 1,939(10,7); 1,933(7,5); 1,927(3,9);,249(4,3); 1,231(8,4); 1,221(1,9); 1,214(4,2); 1,203(3,3); 1,185( 1,6); 0,008(2,0); 0,000(41,7)H-NM (400,0 MHz, CD3CN ): δ= 8,484(1,4); 8,481(1,4); 8,472(1,5); 8,469(1,5); 8,461(2,0);,455(2,0); 8,115(1,2); 8,109(1,3); 8,097(1,3); 8,092(1,2); 7,829(0,7); 7,823(0,7); 7,818(0,8);,812(0,8); 7,808(0,8); 7,802(0,8); 7,796(0,8); 7,791(0,7); 7,735(0,8); 7,731(1,0); 7,729(1,0);,725(0,8); 7,715(1,0); 7,711(1,1); 7,708(1,1); 7,705(0,9); 7,403( 1,2); 7,392(1,2); 7,383(1,1);,371(1,0); 7,337(1,3); 7,315(1,4); 7,310(1,4); 7,288(1,2); 6,380(3,6); 5,446(2,4); 4,383(1,3);,365(4,0); 4,347(4,0); 4,329(1,4); 3,827(15,5); 3,428(16,0); 2,957(8,5); 2,826(7,3); 2,159(10,2);,971(8,6); 1,957(1,2); 1,951(5,4); 1,945(9,6); 1,939(12,7); 1,933(8,7); 1,927(4,5); 1,368(4,1);,350(8,1); 1,332(4,0); 1,203(0,4); 0,000(11,1)H NMR (400.0 MHz, CD 3 CN): δ = 8.480 (1.5); 8.478 (1.6); 8.469 (1.5); 8,466 (1.6); 8.451 (2.2) ;, 445 (2.2); 7,733 (0.8); 7,729 (1.0); 7,727 (1.0); 7,724 (0.8); 7,713 (0.9); 7.709 (1.1); 7,707 (1.1) ;, 402 (1.2); 7,390 (1.2); 7,382 (1.1); 7,370 (1.0); 7,270 (0.9); 7.249 (1.6); 7,242 (0.8); 7,221 (1.6) ;, 214 (1.3); 7,209 (1.7); 7,198 (1.3); 7.193 (1.7); 7.187 (2.5); 7,178 (0.7); 7,173 (0.5); 7,166 (0.6) ;, 161 (0.4); 6,345 (3.8); 5,447 (4.4); 4,769 (9.5); 4,226 (1.3); 4,208 (3.9); 4,190 (3.9); 4,172 (1.3) ;, 085 (0.5); 4,068 (1.5); 4,050 (1.5); 4,032 (0.5); 3,790 (15.8); 3,419 (16.0); 2,956 (0.8); 2,825 (0.7); , 171 (13.4); 1,971 (6.8); 1,957 (1.0); 1,952 (4.5); 1,946 (8.1); 1,939 (10.7); 1,933 (7.5); 1,927 (3.9) ;, 249 (4.3); 1,231 (8.4); 1,221 (1.9); 1,214 (4.2); 1,203 (3.3); 1.185 (1.6); 0.008 (2.0); 0.000 (41.7) H-NM (400.0 MHz, CD 3 CN): δ = 8.484 (1.4); 8.481 (1.4); 8,472 (1.5); 8.469 (1.5); 8.461 (2.0) ;, 455 (2.0); 8,115 (1.2); 8,109 (1.3); 8,097 (1.3); 8,092 (1.2); 7,829 (0.7); 7,823 (0.7); 7,818 (0.8) ;, 812 (0.8); 7,808 (0.8); 7,802 (0.8); 7,796 (0.8); 7,791 (0.7); 7,735 (0.8); 7,731 (1.0); 7,729 (1.0) ;, 725 (0.8); 7.715 (1.0); 7.711 (1.1); 7,708 (1.1); 7,705 (0.9); 7,403 (1,2); 7,392 (1.2); 7,383 (1.1) ;, 371 (1.0); 7,337 (1.3); 7,315 (1.4); 7.310 (1.4); 7,288 (1.2); 6,380 (3.6); 5,446 (2.4); 4,383 (1.3) ;, 365 (4.0); 4,347 (4.0); 4,329 (1.4); 3.827 (15.5); 3.428 (16.0); 2,957 (8.5); 2,826 (7.3); 2.159 (10.2) ;, 971 (8.6); 1,957 (1.2); 1,951 (5.4); 1,945 (9.6); 1,939 (12.7); 1,933 (8.7); 1,927 (4.5); 1,368 (4.1) ;, 350 (8.1); 1.332 (4.0); 1,203 (0.4); 0.000 (11.1)
H-NMR(400,0 MHz, CD3CN ): δ= 8,474(0,7); 7,738(0,5); 7,735(0,6); 7,729(0,5); 7,718(0,6);,714(0,7); 7,709(0,5); 7,588(1,5); 7,562(0,6); 7,544(1,0); 7,503(0,5); 7,484(1,3); 7,465(1,7);,462(1,4); 7,443(0,3); 7,406(0,6); 7,394(0,6); 7,386(0,6); 7,374(0,5); 6,384(1,3); 5,447(1,5);,142(5,1); 3,867(0,5); 3,827(10,0); 3,428( 10,1); 2,956(16,0); 2,826(13,7); 2,183(3,7);H NMR (400.0 MHz, CD 3 CN): δ = 8.474 (0.7); 7,738 (0.5); 7,735 (0.6); 7,729 (0.5); 7,718 (0.6) ;, 714 (0.7); 7.709 (0.5); 7,588 (1.5); 7,562 (0.6); 7,544 (1.0); 7,503 (0.5); 7,484 (1.3); 7.465 (1.7) ;, 462 (1.4); 7,443 (0.3); 7,406 (0.6); 7,394 (0.6); 7,386 (0.6); 7.374 (0.5); 6,384 (1.3); 5,447 (1.5) ;, 142 (5.1); 3,867 (0.5); 3.827 (10.0); 3,428 (10.1); 2,956 (16.0); 2,826 (13.7); 2,183 (3.7);
,970(15,0); 1,957(0,7); 1,951(2,7); 1,945(4,8); 1,939(6,3); 1,932(4,4); 1,926(2,3); 1,674(0,4);,667(0,4); 1,655(0,8); 1,643(0,4); 1,636(0,4); 0,915(0,7); 0,908(2,2); 0,904(1,8); 0,895(3,3);,887(0,9); 0,879(1,0); 0,874(1,9); 0,867(0,7); 0,000(5,8), 970 (15.0); 1,957 (0.7); 1,951 (2.7); 1,945 (4.8); 1,939 (6.3); 1,932 (4.4) 1,926 (2.3); 1.674 (0.4) ;, 667 (0.4); 1,655 (0.8); 1,643 (0.4); 1.636 (0.4); 0.915 (0.7); 0.908 (2.2); 0.904 (1.8); 0.895 (3.3) ;, 887 (0.9); 0.879 (1.0); 0.874 (1.9); 0.867 (0.7); 0,000 (5.8)
H-NMR(400,0 MHz, CD3CN ): δ= 8,460(1,8); 7,732(1,2); 7,730(1,1); 7,726(0,9); 7,715(1,1);,711(1,3); 7,709(1,3); 7,550(1,3); 7,532(1,3); 7,519(0,8); 7,514(0,7); 7,506(0,9); 7,499(1,1);,493(0,8); 7,485(0,9); 7,402(1,0); 7,390(1,2); 7,382(1,1); 7,370(1,0); 7,202(1,3); 7,180(1,6);,178(1,7); 7,156(1,2); 7,100(0,7); 6,359(2,0); 5,447(4,0); 4,425(3,6); 4,410(3,6); 3,794(16,0);,422(16,0); 3,384( 1,7); 2,955(8,1); 2,824(7,1); 2,179(11,6); 1,970(7,8); 1,957(1,2); 1,952(4,2);,946(7,4); 1,940(9,5); 1,933(6,7); 1,927(3,4); 1,531(0,3); 1,520(0,7); 1,512(0,8); 1,500(1,3);,488(0,9); 1,481(0,8); 1,469(0,4); 1,269(0,4); 0,770(0,7); 0,758(2,0); 0,751(2,9); 0,747(2,5);,740(2,8); 0,733(1,2); 0,724(0,5); 0,710(1,4); 0,703(2,7); 0,696( 1,7); 0,690(1,5); 0,683(2,8);,676(1,4); 0,668(0,6); 0,665(0,6); 0,000(4,1)H NMR (400.0 MHz, CD 3 CN): δ = 8.460 (1.8); 7,732 (1.2); 7,730 (1.1); 7,726 (0.9); 7.715 (1.1) ;, 711 (1.3); 7.709 (1.3); 7,550 (1.3); 7,532 (1.3); 7,519 (0.8); 7,514 (0.7); 7,506 (0.9); 7,499 (1.1) ;, 493 (0.8); 7,485 (0.9); 7,402 (1.0); 7,390 (1.2); 7,382 (1.1); 7,370 (1.0); 7,202 (1.3); 7,180 (1.6) ;, 178 (1.7); 7,156 (1.2); 7,100 (0.7); 6,359 (2.0); 5,447 (4.0); 4,425 (3.6); 4,410 (3.6); 3.794 (16.0) ;, 422 (16.0); 3.384 (1.7); 2,955 (8.1); 2,824 (7.1); 2,179 (11.6); 1,970 (7.8); 1,957 (1.2); 1,952 (4.2) ;, 946 (7.4); 1,940 (9.5); 1,933 (6.7); 1,927 (3.4); 1,531 (0.3); 1,520 (0.7); 1,512 (0.8); 1,500 (1.3) ;, 488 (0.9); 1,481 (0.8); 1,469 (0.4); 1,269 (0.4); 0,770 (0.7); 0.758 (2.0); 0.751 (2.9); 0.747 (2.5) ;, 740 (2.8); 0.733 (1.2); 0.724 (0.5); 0.710 (1.4); 0.703 (2.7); 0.696 (1.7); 0,690 (1.5); 0.683 (2.8) ;, 676 (1.4); 0.668 (0.6); 0.665 (0.6); 0.000 (4.1)
H-NMR(400,0 MHz, DMSO): δ= 8,663(1,4); 8,653(1,4); 8,531(2,2); 8,525(2,3); 8,475(1,8);,471(2,0); 8,463(2,1); 8,460(2,3); 8,433(6,4); 8,317(0,9); 7,979( 1,3); 7,959(2,2); 7,917(1,0);,913(1,1); 7,898(1,4); 7,894(1,5); 7,887(0,9); 7,879(1,5); 7,866(0,9); 7,863(1,1); 7,860(1,1);,856(0,9); 7,463(1,2); 7,450(1,2); 7,442(2,0); 7,430(1,9); 7,423( 1,1); 7,420(1,0); 7,411(0,8);,408(0,9); 6,462(3,0); 4,172(16,0); 4,015(0,4); 3,993(0,5); 3,979(0,4); 3,936(0,7); 3,916(0,5);,893(0,6); 3,864(0,7); 3,552(7,4); 3,420(17,4); 3,242(0,7); 3,121(0,4); 3,105(0,3); 2,675(1,3);,671(1,8); 2,667(1,4); 2,541(0,9); 2,506(206,9); 2,502(276,0); 2,498(215,5); 2,333(1,3);H NMR (400.0 MHz, DMSO): δ = 8.663 (1.4); 8.653 (1.4); 8,531 (2.2); 8,525 (2.3); 8,475 (1.8) ;, 471 (2.0); 8.463 (2.1); 8,460 (2.3); 8.433 (6.4); 8,317 (0.9); 7.979 (1.3); 7,959 (2.2); 7,917 (1.0) ;, 913 (1.1); 7,898 (1.4); 7,894 (1.5); 7,887 (0.9); 7,879 (1.5); 7,866 (0.9); 7,863 (1.1); 7,860 (1.1) ;, 856 (0.9); 7,463 (1.2); 7,450 (1.2); 7.442 (2.0); 7,430 (1.9); 7.423 (1.1); 7,420 (1.0); 7.411 (0.8) ;, 408 (0.9); 6,462 (3.0); 4,172 (16.0); 4,015 (0.4); 3,993 (0.5); 3,979 (0.4); 3,936 (0.7); 3,916 (0.5) ;, 893 (0.6); 3,864 (0.7); 3,552 (7.4); 3,420 (17.4); 3,242 (0.7); 3,121 (0.4); 3,105 (0.3); 2,675 (1.3) ;, 671 (1.8); 2,667 (1.4); 2,541 (0.9); 2.506 (206.9); 2.502 (276.0); 2.498 (215.5); 2,333 (1.3);
,329(1,8); 2,324(1,4); 0,008(1,0); 0,000(32,4), 329 (1.8); 2,324 (1.4); 0.008 (1.0); 0.000 (32.4)
H-NMR(400,0 MHz, CD3CN ): δ= 8,484(1,7); 8,471(2,0); 8,465(2,5); 8,459(2,3); 7,767(3,8);,746(1,7); 7,741(1,6); 7,716(1,3); 7,660(0,7); 7,641(2,0); 7,628( 1,8); 7,609(1,6); 7,590(0,5);,407(1,2); 7,395(1,3); 7,387(1,2); 7,375(1,1); 6,983(1,2); 6,843(2,3); 6,703(1,2); 6,398(3,6);,844(15,8); 3,431( 16,0); 2,151(4,4); 1,963(2,1); 1,951(8,9); 1,945(15,9); 1,939(21,2);H NMR (400.0 MHz, CD 3 CN): δ = 8.484 (1.7); 8,471 (2.0); 8,465 (2.5); 8.459 (2.3); 7,767 (3.8) ;, 746 (1.7); 7.741 (1.6); 7,716 (1.3); 7,660 (0.7); 7,641 (2.0); 7.628 (1.8); 7,609 (1.6); 7,590 (0.5) ;, 407 (1.2); 7,395 (1.3); 7.387 (1.2); 7,375 (1.1); 6,983 (1.2); 6,843 (2.3); 6,703 (1.2); 6,398 (3.6) ;, 844 (15.8); 3,431 (16.0); 2,151 (4.4); 1,963 (2.1); 1,951 (8.9); 1,945 (15.9); 1,939 (21.2);
,933(15,2); 1,927(8,0); 1,842(0,4); 1,270(0,3); 0,000(58,7), 933 (15.2); 1,927 (8.0); 1,842 (0.4); 1.270 (0.3); 0.000 (58.7)
H-NMR(600,1 MHz, CD3CN ): δ= 8,486(1,1); 8,484(1,1); 8,478(1,2); 8,476(1,2); 8,470(1,4);,466(1,5); 8,044(1,4); 8,037(1,6); 7,971(0,7); 7,969(0,9); 7,968(0,9); 7,966(0,7); 7,958(0,8);,956(1,1); 7,955(1,0); 7,953(0,8); 7,923(0,7); 7,909(0,8); 7,796( 1,1); 7,783(1,9); 7,770(0,8);,747(0,6); 7,745(0,7); 7,743(0,7); 7,741(0,6); 7,734(0,7); 7,731(0,8); 7,730(0,8); 7,727(0,7);,409(0,8); 7,408(0,8); 7,401(0,8); 7,400(0,8); 7,395(0,8); 7,394(0,7); 7,387(0,7); 7,386(0,7);,437(1,7); 3,858(16,0); 3,436(15,6); 3,275(0,3); 1,956(0,7); 1,951(0,8); 1,948(4,4); 1,944(7,8);,939(11,4); 1,935(7,7); 1,931(3,9); 1,135( 1,4); 0,000(1,9)H-NMR (600.1 MHz, CD 3 CN): δ = 8.486 (1.1); 8,484 (1.1); 8.478 (1.2); 8,476 (1.2); 8,470 (1.4) ;, 466 (1.5); 8.044 (1.4); 8,037 (1.6); 7,971 (0.7); 7,969 (0.9); 7,968 (0.9); 7.966 (0.7); 7,958 (0.8) ;, 956 (1.1); 7,955 (1.0); 7.953 (0.8); 7,923 (0.7); 7,909 (0.8); 7.796 (1.1); 7,783 (1.9); 7,770 (0.8) ;, 747 (0.6); 7,745 (0.7); 7,743 (0.7); 7.741 (0.6); 7.734 (0.7); 7,731 (0.8); 7,730 (0.8); 7,727 (0.7) ;, 409 (0.8); 7,408 (0.8); 7,401 (0.8); 7,400 (0.8); 7,395 (0.8); 7,394 (0.7); 7.387 (0.7); 7,386 (0.7) ;, 437 (1.7); 3,858 (16.0); 3,436 (15.6); 3,275 (0.3); 1,956 (0.7); 1,951 (0.8); 1,948 (4.4); 1,944 (7.8) ;, 939 (11.4); 1,935 (7.7); 1,931 (3.9); 1,135 (1.4); 0.000 (1.9)
H-NMR(400,0 MHz, CD3CN ): δ= 8,486(1,3); 8,482(1,3); 8,474(1,4); 8,470(1,4); 8,462(1,8);,455(1,7); 7,903(1,2); 7,887(1,9); 7,879(0,7); 7,873(0,5); 7,866(0,6); 7,861(0,4); 7,742(0,7);,738(0,8); 7,736(0,8); 7,732(0,7); 7,722(0,8); 7,718(0,9); 7,715(0,9); 7,712(0,8); 7,453(0,8);,432(0,9); 7,406(1,7); 7,394(1,1); 7,393(1,0); 7,386(1,0); 7,374(0,9); 6,391(2,9); 5,447(6,5);,827(15,5); 3,763(0,4); 3,428(16,0); 3,388(0,4); 2,167(8,3); 1,958(0,7); 1,952(3,7); 1,946(6,7);,940(9,1); 1,934(6,2); 1,928(3,2); 0,008(1,1); 0,000(24,6); -0,009(0,9) 1H-NM (400,0 MHz, CD3CN): δ= 8,485(1,4); 8,482(1,4); 8,473(1,5); 8,470(1,5); 8,455(2,0); 8,449(2,0); 7,881(2,1); 7,842(2,2); 7,808(2,0); 7,738(0,8); 7,734(1,0); 7,731(0,9); 7,727(0,8); 7,717(0,9); 7,713(1,0); 7,711(1,0); 7,707(0,8); 7,406(1,2); 7,394(1,2); 7,385(1,1); 7,374(1,0); 6,412(3,0); 5,447(4,9); 3,898(0,6); 3,860(16,0); 3,441(0,7); 3,430(15,9); 2,156(22,2); 1,964(0,5); 1,958(1,0); 1,952(6,0); 1,946(10,9); 1,940(14,8); 1,933(10,1); 1,927(5,2); 0,008(1,5); H NMR (400.0 MHz, CD 3 CN): δ = 8.486 (1.3); 8,482 (1.3); 8.474 (1.4); 8,470 (1.4); 8,462 (1.8) ;, 455 (1.7); 7,903 (1.2); 7,887 (1.9); 7,879 (0.7); 7,873 (0.5); 7,866 (0.6); 7,861 (0.4); 7,742 (0.7) ;, 738 (0.8); 7,736 (0.8); 7,732 (0.7); 7,722 (0.8); 7,718 (0.9); 7.715 (0.9); 7,712 (0.8); 7,453 (0.8) ;, 432 (0.9); 7,406 (1.7); 7,394 (1.1); 7,393 (1.0); 7,386 (1.0); 7.374 (0.9); 6,391 (2.9); 5,447 (6.5) ;, 827 (15.5); 3,763 (0.4); 3.428 (16.0); 3,388 (0.4); 2,167 (8.3); 1,958 (0.7); 1,952 (3.7); 1.946 (6.7) ;, 940 (9.1); 1,934 (6.2); 1,928 (3.2); 0.008 (1.1); 0,000 (24.6); -0.009 (0.9) 1H-NM (400.0 MHz, CD 3 CN): δ = 8.485 (1.4); 8,482 (1.4); 8.473 (1.5); 8,470 (1.5); 8.455 (2.0); 8,449 (2.0); 7,881 (2.1); 7,842 (2.2); 7,808 (2.0); 7,738 (0.8); 7.734 (1.0); 7,731 (0.9); 7,727 (0.8); 7,717 (0.9); 7,713 (1.0); 7.711 (1.0); 7,707 (0.8); 7,406 (1.2); 7,394 (1.2); 7,385 (1.1); 7.374 (1.0); 6,412 (3.0); 5,447 (4.9); 3,898 (0.6); 3,860 (16.0); 3,441 (0.7); 3,430 (15.9); 2,156 (22.2); 1,964 (0.5); 1,958 (1.0); 1,952 (6.0); 1,946 (10.9); 1,940 (14.8); 1,933 (10.1); 1,927 (5.2); 0.008 (1.5);
0,000(37,5); -0,009(1,6) 0,000 (37.5); -0.009 (1.6)
1H-NMR(400,0 MHz, DMSO): δ= 8,559(1,0);8,514(0,8);8,364(0,5);7,988(1,3);7,965(2,6);7,904( 1 H NMR (400.0 MHz, DMSO): δ = 8.559 (1.0), 8.514 (0.8), 8.364 (0.5), 7.988 (1.3), 7.965 (2.6), 7.904 (
1,0);7,884(1,1);7,857(1,0);7,837(1,5);7,761(1,2);7,742(1,8);7,722(0,7);7,494(0,8);7,483(0,8);7,41.0); 7,884 (1.1); 7,857 (1.0); 7,837 (1.5); 7,761 (1.2); 7,742 (1.8); 7,722 (0.7); 7,494 (0 , 8); 7,483 (0.8); 7.4
74(0,8);7,462(0,7);6,422(3,1);3,903(6,1);3,875(16,0);3,419(14,8);3,331(95,2);2,676(0,4);2,672(74 (0.8); 7,462 (0.7); 6,422 (3.1); 3,903 (6.1); 3,875 (16.0); 3,419 (14.8); 3,331 (95.2); 2.676 (2.672 (0.4)
0,6);2,667(0,4);2,525(1,5);2,507(70,9);2,503(99,3);2,498(76,3);2,334(0,4);2,329(0,5);2,325(0,4)0.6); 2,667 (0.4); 2,525 (1.5); 2,507 (70.9); 2.503 (99.3); 2,498 (76.3); 2,334 (0.4); 2,329 (0 2,325 (0.4);, 5)
;1,236(0,4);0,000(4,5) ; 1,236 (0.4); 0,000 (4.5)
1H-NMR(400,0 MHz, CD3CN): δ= 8,488(1,4); 8,484(1,4); 8,476(1,5); 8,472(1,4); 8,462(2,0); 8,455(2,0); 8,164(4,5); 8,078(1,9); 7,746(0,8); 7,742(0,9); 7,740(0,9); 7,736(0,7); 7,726(0,9); 7,722(1,0); 7,719(1,0); 7,716(0,8); 7,410(1,1); 7,398(1,1); 7,390(1,0); 7,378(1,0); 6,438(3,0); 5,447(7,6); 3,880(16,0); 3,437(15,7); 2,170(23,1); 1,958(0,7); 1,953(4,1); 1,947(7,4); 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.488 (1.4); 8,484 (1.4); 8,476 (1.5); 8,472 (1.4); 8,462 (2.0); 8.455 (2.0); 8,164 (4.5); 8.078 (1.9); 7.746 (0.8); 7,742 (0.9); 7,740 (0.9); 7,736 (0.7); 7,726 (0.9); 7,722 (1.0); 7,719 (1.0); 7,716 (0.8); 7.410 (1.1); 7,398 (1.1); 7,390 (1.0); 7,378 (1.0); 6,438 (3.0); 5,447 (7.6); 3,880 (16.0); 3,437 (15.7); 2,170 (23.1); 1,958 (0.7); 1,953 (4.1); 1,947 (7.4);
1,940(10,0); 1,934(6,8); 1,928(3,5); 0,008(0,8); 0,000(19,4); -0,009(0,7) 1,940 (10.0); 1,934 (6.8); 1,928 (3.5) 0.008 (0.8); 0,000 (19.4); -0.009 (0.7)
1H-NMR(400,0 MHz, CD3CN): δ= 8,485(1,5); 8,481(1,4); 8,473(1,5); 8,469(1,5); 8,457(2,0); 8,451(2,0); 7,757(2,3); 7,742(0,9); 7,738(1,0); 7,735(0,9); 7,732(0,8); 7,721(0,9); 7,718(1,1); 7,715(1,0); 7,711(0,8); 7,653(1,0); 7,629(0,9); 7,566(0,9); 7,544(1,0); 7,407(1,1); 7,395(1,1); 7,387(1,0); 7,375(1,0); 6,415(3,1); 3,868(16,0); 3,431(15,9); 2,188(24,5); 1,959(0,5); 1,953(2,6); 1,947(4,8); 1,941(6,4); 1,935(4,4); 1,928(2,2); 0,000(7,3) 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.485 (1.5); 8.481 (1.4); 8.473 (1.5); 8.469 (1.5); 8.457 (2.0); 8.451 (2.0); 7.757 (2.3); 7,742 (0.9); 7,738 (1.0); 7,735 (0.9); 7,732 (0.8); 7.721 (0.9); 7,718 (1.1); 7.715 (1.0); 7.711 (0.8); 7,653 (1.0); 7,629 (0.9); 7,566 (0.9); 7,544 (1.0); 7,407 (1.1); 7,395 (1.1); 7.387 (1.0); 7,375 (1.0); 6.415 (3.1); 3,868 (16.0); 3,431 (15.9); 2,188 (24.5); 1,959 (0.5); 1,953 (2.6); 1,947 (4.8); 1,941 (6.4); 1,935 (4.4); 1,928 (2.2); 0,000 (7.3)
1H-NMR(400,0 MHz, CD3CN): δ= 8,483(1,3); 8,480(1,4); 8,471(1,4); 8,468(1,4); 8,453(1,8); 8,447(1,8); 8,126(2,6); 8,067(0,6); 8,046(3,3); 8,040(2,6); 8,037(2,3); 8,019(0,4); 8,016(0,4); 7,740(0,8); 7,736(1,0); 7,734(0,9); 7,730(0,8); 7,720(0,9); 7,716(1,1); 7,713(1,1); 7,710(0,9); 7,404(1,1); 7,392(1,1); 7,383(1,0); 7,372(1,0); 6,458(2,8); 5,447(0,3); 3,891(16,0); 3,434(15,8); 2,166(22,0); 1,958(0,7); 1,952(3,9); 1,946(7,2); 1,940(9,7); 1,934(6,7); 1,928(3,4); 0,008(1,0); 0,000(22,3); -0,008(1,0)  1 H NMR (400.0 MHz, CD 3 CN): δ = 8.483 (1.3); 8,480 (1.4); 8,471 (1.4); 8,468 (1.4); 8,453 (1.8); 8,447 (1.8); 8,126 (2.6); 8,067 (0.6); 8,046 (3.3); 8,040 (2.6); 8,037 (2.3); 8,019 (0.4); 8.016 (0.4); 7,740 (0.8); 7,736 (1.0); 7.734 (0,9); 7,730 (0.8); 7,720 (0.9); 7,716 (1.1); 7,713 (1.1); 7.710 (0.9); 7,404 (1.1); 7,392 (1.1); 7,383 (1.0); 7,372 (1.0); 6,458 (2.8); 5,447 (0.3); 3,891 (16.0); 3,434 (15.8); 2,166 (22.0); 1,958 (0.7); 1,952 (3.9); 1,946 (7.2); 1,940 (9.7); 1,934 (6.7); 1,928 (3.4); 0.008 (1.0) 0,000 (22.3); -0.008 (1.0)
1H-NMR(400,0 MHz, CD3CN): δ= 8,484(1,0); 8,470(1,2); 8,462(1,4); 8,021(0,4); 7,741(0,7); 7,738(0,9); 7,735(0,8); 7,731(0,7); 7,721(0,8); 7,717(1,0); 7,715(1,0); 7,711(0,8); 7,597(1,0); 7,581(3,3); 7,516(0,9); 7,497(1,8); 7,477(1,2); 7,456(1,4); 7,437(0,7); 7,408(0,9); 7,396(0,9); 7,388(0,9); 7,376(0,8); 6,382(2,5); 5,446(1,7); 3,826(16,0); 3,613(0,9); 3,585(2,7); 3,557(2,7); 3,528(0,9); 3,429(16,0); 2,151(1,8); 2,106(0,7); 1,963(0,8); 1,957(1,8); 1,951(10,1); 1,945(18,3); 1,939(24,7); 1,933(16,8); 1,926(8,6); 1,270(0,3); 0,146(0,3); 0,008(2,9); 0,000(68,2); - 0,009(2,5); -0,150(0,3) 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.484 (1.0); 8,470 (1.2); 8,462 (1.4); 8,021 (0.4); 7.741 (0.7); 7,738 (0.9); 7,735 (0.8); 7,731 (0.7); 7.721 (0.8); 7,717 (1.0); 7.715 (1.0); 7.711 (0.8); 7,597 (1.0); 7,581 (3.3); 7,516 (0.9); 7,497 (1.8); 7,477 (1.2); 7,456 (1.4); 7,437 (0.7); 7,408 (0.9); 7,396 (0.9); 7,388 (0.9); 7,376 (0.8); 6,382 (2.5); 5,446 (1.7); 3,826 (16.0); 3,613 (0.9); 3,585 (2.7); 3,557 (2.7); 3,528 (0.9); 3,429 (16.0); 2,151 (1.8); 2,106 (0.7); 1,963 (0.8); 1,957 (1.8); 1,951 (10.1); 1,945 (18.3); 1,939 (24.7); 1,933 (16.8); 1,926 (8.6); 1.270 (0.3); 0.146 (0.3); 0.008 (2.9); 0,000 (68.2); - 0.009 (2.5); -0.150 (0.3)
1H-NMR(400,0 MHz, CD3CN): δ= 8,484(0,9); 8,470(1,4); 8,030(0,7); 7,894(1,0); 7,872(2,9); 7,764(0,7); 7,745(2,2); 7,728(0,8); 7,725(1,0); 7,722(1,0); 7,718(1,3); 7,716(1,3); 7,696(1,3); 7,677(0,5); 7,412(0,8); 7,400(0,8); 7,392(0,8); 7,380(0,7); 6,411(2,4); 5,447(1,7); 3,839(16,0); 3,433(15,9); 2,959(1,3); 2,829(1,0); 2,190(0,4); 1,974(1,2); 1,964(0,5); 1,958(1,1); 1,952(5,8); 1,946(10,6); 1,940(14,3); 1,933(9,8); 1,927(5,0); 0,008(1,8); 0,000(40,7); -0,009(1,5) 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.484 (0.9); 8,470 (1.4); 8,030 (0.7); 7,894 (1.0); 7,872 (2.9); 7.764 (0.7); 7,745 (2.2); 7,728 (0.8); 7,725 (1.0); 7,722 (1.0); 7,718 (1.3); 7,716 (1.3); 7,696 (1.3); 7,677 (0.5); 7,412 (0.8); 7,400 (0.8); 7,392 (0.8); 7,380 (0.7); 6,411 (2.4); 5,447 (1.7); 3,839 (16.0); 3,433 (15.9); 2,959 (1.3); 2,829 (1.0); 2,190 (0.4); 1,974 (1.2); 1,964 (0.5); 1,958 (1.1); 1,952 (5.8); 1,946 (10.6); 1,940 (14.3); 1,933 (9.8); 1,927 (5.0); 0.008 (1.8); 0,000 (40.7); -0.009 (1.5)
1H-NMR(400,0 MHz, CD3CN): δ= 8,486(1,0); 8,475(1,1); 8,461(1,3); 7,958(2,3); 7,954(1,6); 7,907(0,9); 7,904(1,2); 7,900(0,8); 7,887(1,0); 7,884(1,4); 7,880(0,9); 7,816(0,8); 7,813(1,2); 7,809(0,8); 7,796(1,1); 7,793(1,5); 7,790(0,9); 7,745(0,7); 7,742(0,9); 7,739(0,8); 7,736(0,7); 7,725(0,8); 7,721(1,0); 7,719(0,9); 7,715(0,7); 7,656(1,3); 7,636(2,2); 7,617(0,9); 7,411(0,8); 7,399(0,8); 7,391(0,8); 7,379(0,7); 6,410(2,9); 5,448(2,1); 3,841(15,8); 3,430(16,0); 2,205(14,1); 1,959(0,7); 1,953(3,8); 1,947(7,0); 1,940(9,5); 1,934(6,5); 1,928(3,4); 0,008(0,4); 0,000(10,4); - 0,009(0,4) 1 H NMR (400.0 MHz, CD 3 CN): δ = 8.486 (1.0); 8,475 (1.1); 8.461 (1.3); 7,958 (2.3); 7,954 (1.6); 7,907 (0.9); 7,904 (1.2); 7,900 (0.8); 7,887 (1.0); 7,884 (1.4); 7,880 (0.9); 7.816 (0.8); 7,813 (1.2); 7,809 (0.8); 7,796 (1.1); 7,793 (1.5); 7,790 (0.9); 7,745 (0.7); 7,742 (0.9); 7,739 (0.8); 7,736 (0.7); 7,725 (0.8); 7.721 (1.0); 7,719 (0.9); 7.715 (0.7); 7,656 (1.3); 7,636 (2.2); 7,617 (0.9); 7,411 (0.8); 7,399 (0.8); 7,391 (0.8); 7,379 (0.7); 6,410 (2.9); 5,448 (2.1); 3,841 (15.8); 3,430 (16.0); 2.205 (14.1); 1,959 (0.7); 1,953 (3.8); 1,947 (7.0); 1,940 (9.5); 1,934 (6.5); 1,928 (3.4); 0.008 (0.4); 0,000 (10.4); - 0.009 (0.4)
1H-NMR(400,0 MHz, CD3CN): δ= 8,482(1,6); 8,479(1,5); 8,471(1,7); 8,467(1,5); 8,450(2,1); 8,444(2,2); 8,018(2,5); 8,013(2,8); 7,876(1,4); 7,870(1,3); 7,854(1,7); 7,849(1,7); 7,736(0,9); 7,733(1,1); 7,730(1,0); 7,726(0,8); 7,716(1,1); 7,707(3,6); 7,685(2,1); 7,404(1,2); 7,392(1,2); 7,383(1,1); 7,371(1,0); 6,399(3,2); 3,838(16,0); 3,425(16,0); 2,152(11,4); 1,964(0,4); 1,958(1,1); ,952(4,8); 1,946(8,6); 1,940(11,2); 1,934(7,9); 1,927(4,1); 0,000(11,5)1 H NMR (400.0 MHz, CD 3 CN): δ = 8.482 (1.6); 8.479 (1.5); 8,471 (1.7); 8,467 (1.5); 8,450 (2.1); 8,444 (2.2); 8,018 (2.5); 8,013 (2.8); 7,876 (1.4); 7,870 (1.3); 7,854 (1.7); 7,849 (1.7); 7,736 (0.9); 7,733 (1.1); 7,730 (1.0); 7,726 (0.8); 7,716 (1.1); 7,707 (3.6); 7,685 (2.1); 7,404 (1.2); 7,392 (1.2); 7,383 (1.1); 7,371 (1.0); 6,399 (3.2); 3,838 (16.0); 3,425 (16.0); 2,152 (11.4); 1,964 (0.4); 1,958 (1.1); , 952 (4.8); 1,946 (8.6); 1,940 (11.2); 1,934 (7.9); 1,927 (4.1); 0.000 (11.5)
H-NM (400,0 MHz, DMSO): δ= 8,536(2,4); 8,530(2,5); 8,500(1,7); 8,497(1,8); 8,488(1,8);,485(1,7); 8,003(3,5); 8,000(2,4); 7,996(1,3); 7,989(1,2); 7,974(1,0); 7,971(1,0); 7,968(1,1);,914(1,0); 7,910(1,1); 7,902(1,2); 7,897(1,2); 7,895(1,2); 7,891(1,5); 7,885(1,3); 7,881(1,7);,871(1,0); 7,482(1,3); 7,470(1,3); 7,462(1,3); 7,450(1,2); 6,440(2,9); 5,755(0,5); 3,893(16,0);,414(15,1); 3,325(93,2); 2,671(0,3); 2,510(21,8); 2,506(42,8); 2,502(55,6); 2,497(40,8);H-NM (400.0 MHz, DMSO): δ = 8.536 (2.4); 8,530 (2.5); 8,500 (1.7); 8,497 (1.8); 8.488 (1.8) ;, 485 (1.7); 8,003 (3.5); 8,000 (2.4); 7,996 (1.3); 7,989 (1.2); 7,974 (1.0); 7,971 (1.0); 7,968 (1.1) ;, 914 (1.0); 7.910 (1.1); 7,902 (1.2); 7,897 (1.2); 7.895 (1.2); 7,891 (1.5); 7,885 (1.3); 7,881 (1.7) ;, 871 (1.0); 7,482 (1.3); 7.470 (1.3); 7,462 (1.3); 7,450 (1.2); 6,440 (2.9); 5,755 (0.5); 3,893 (16.0) ;, 414 (15.1); 3,325 (93.2); 2,671 (0.3); 2,510 (21.8); 2,506 (42.8); 2,502 (55.6); 2,497 (40.8);
,329(0,3); 0,000(1,5), 329 (0.3); 0.000 (1.5)
H-NMR(400,0 MHz, CD3CN): δ= 8,517(1,8); 8,514(1,6); 8,505(1,8); 8,485(2,6); 8,479(2,3);,238(2,9); 8,201(2,7); 8,178(2,6); 7,778(1,0); 7,773(1,2); 7,758(1,1); 7,752(1,3); 7,442(1,3);,430(1,4); 7,422(1,2); 7,410(1,1); 6,469(3,2); 5,481(0,5); 5,477(1,3); 3,900(16,0); 3,468(6,3);,464(15,9); 2,242(103,2); 2,201(0,9); 1,994(1,1); 1,987(3,5); 1,982(9,2); 1,976(14,9);H NMR (400.0 MHz, CD 3 CN): δ = 8.517 (1.8); 8,514 (1.6); 8,505 (1.8); 8,485 (2.6); 8.479 (2.3) ;, 238 (2.9); 8,201 (2.7); 8.178 (2.6); 7,778 (1.0); 7,773 (1.2); 7.758 (1.1); 7,752 (1.3); 7.442 (1.3) ;, 430 (1.4); 7,422 (1.2); 7.410 (1.1); 6,469 (3.2); 5,481 (0.5); 5,477 (1.3); 3,900 (16.0); 3.468 (6.3) ;, 464 (15.9); 2.242 (103.2); 2,201 (0.9); 1,994 (1.1); 1,987 (3.5); 1,982 (9.2); 1,976 (14.9);
,971(18,5); 1,965(12,7); 1,959(6,5), 971 (18.5); 1,965 (12.7); 1,959 (6.5)
H-NMR(400,0 MHz, CD3CN): δ= 8,498(1,3); 8,495(1,3); 8,486(1,4); 8,483(1,4); 8,459(1,7);,452(1,8); 7,855(1,2); 7,850(1,3); 7,833(1,4); 7,828(1,5); 7,734(0,7); 7,730(0,8); 7,727(0,8);,724(0,7); 7,714(0,8); 7,710(0,9); 7,707(0,9); 7,703(0,8); 7,641(2,5); 7,636(2,4); 7,418(1,0);,406(1,0); 7,404(0,9); 7,397(0,9); 7,385(0,9); 7,384(0,9); 7,230(2,2); 7,208(2,0); 6,381(3,0);,222(0,4); 5,446(0,5); 3,883(14,3); 3,763(2,6); 3,564(16,0); 3,422(15,9); 3,387(2,8); 2,764(0,6);,751(0,6); 2,144(31,5); 1,963(0,6); 1,957(1,2); 1,951(7,8); 1,945(14,5); 1,939(19,9);H NMR (400.0 MHz, CD 3 CN): δ = 8.498 (1.3); 8,495 (1.3); 8.486 (1.4); 8,483 (1.4); 8.459 (1.7) ;, 452 (1.8); 7,855 (1.2); 7,850 (1.3); 7,833 (1.4); 7,828 (1.5); 7.734 (0.7); 7,730 (0.8); 7,727 (0.8) ;, 724 (0.7); 7,714 (0.8); 7.710 (0.9); 7,707 (0.9); 7,703 (0.8); 7,641 (2.5); 7,636 (2.4); 7,418 (1.0) ;, 406 (1.0); 7,404 (0.9); 7,397 (0.9); 7,385 (0.9); 7,384 (0.9); 7,230 (2.2); 7,208 (2.0); 6,381 (3.0) ;, 222 (0.4); 5,446 (0.5); 3,883 (14.3); 3,763 (2.6); 3,564 (16.0); 3,422 (15.9); 3,387 (2.8); 2,764 (0.6) ;, 751 (0.6); 2,144 (31.5); 1,963 (0.6); 1,957 (1.2); 1,951 (7.8); 1,945 (14.5); 1,939 (19.9);
,933(13,8); 1,927(7,2); 0,008(0,4); 0,000(12,7); -0,009(0,5), 933 (13.8); 1,927 (7.2); 0.008 (0.4); 0,000 (12.7); -0.009 (0.5)
H-NMR(400,0 MHz, CD3CN): δ= 8,484(1,1); 8,481(1,2); 8,472(1,2); 8,469(1,2); 8,452(1,4);,446(1,5); 7,982(0,9); 7,976(1,2); 7,967(1,0); 7,961(1,2); 7,942(0,8); 7,936(0,6); 7,929(0,8);,923(0,6); 7,920(0,9); 7,914(0,7); 7,907(0,8); 7,901(0,7); 7,739(0,7); 7,735(0,8); 7,732(0,8);,728(0,7); 7,718(0,8); 7,714(0,9); 7,712(0,9); 7,708(0,8); 7,453(1,1); 7,430(2,0); 7,407(1,5);,405(1,0); 7,394(0,9); 7,393(0,9); 7,386(0,9); 7,384(0,8); 7,374(0,8); 7,372(0,8); 6,384(2,6);,822(16,0); 3,425(16,0); 2,178(1,0); 1,964(0,4); 1,958(0,8); 1,952(4,4); 1,946(8,1); 1,940(11,1);,933(7,7); 1,927(4,0); 0,000(3,2)H NMR (400.0 MHz, CD 3 CN): δ = 8.484 (1.1); 8.481 (1.2); 8,472 (1.2); 8.469 (1.2); 8.452 (1.4) ;, 446 (1.5); 7,982 (0.9); 7,976 (1.2); 7.967 (1.0); 7,961 (1.2); 7,942 (0.8); 7,936 (0.6); 7.929 (0.8) ;, 923 (0.6); 7,920 (0.9); 7.914 (0.7); 7,907 (0.8); 7.901 (0.7); 7,739 (0.7); 7,735 (0.8); 7,732 (0.8) ;, 728 (0.7); 7,718 (0.8); 7,714 (0.9); 7,712 (0.9); 7,708 (0.8); 7,453 (1.1); 7,430 (2.0); 7,407 (1.5) ;, 405 (1.0); 7,394 (0.9); 7,393 (0.9); 7,386 (0.9); 7,384 (0.8); 7.374 (0.8); 7,372 (0.8); 6,384 (2.6) ;, 822 (16.0); 3,425 (16.0); 2,178 (1.0); 1,964 (0.4); 1,958 (0.8); 1,952 (4.4); 1,946 (8.1); 1,940 (11.1) ;, 933 (7.7); 1,927 (4.0); 0.000 (3.2)
H-NMR(400,0 MHz, CD3CN): δ= 9,035(2,4); 9,030(2,4); 8,931(2,5); 8,926(2,4); 8,488(1,4);,484(1,3); 8,476(1,5); 8,472(1,4); 8,456(1,9); 8,450(1,9); 8,330(1,6); 8,325(2,9); 8,320(1,5);,748(0,8); 7,744(0,9); 7,742(0,9); 7,738(0,7); 7,728(0,9); 7,724(1,0); 7,721(1,0); 7,717(0,8);,411(1,1); 7,399(1,1); 7,390(1,0); 7,378(1,0); 6,446(2,7); 3,871(16,0); 3,763(0,8); 3,433(15,7);,387(0,9); 2,207(0,7); 1,964(0,5); 1,958(1,0); 1,952(4,7); 1,946(8,5); 1,940(11,5); 1,934(7,9);,928(3,9); 0,008(0,3); 0,000(7,4)H NMR (400.0 MHz, CD 3 CN): δ = 9.035 (2.4); 9,030 (2.4); 8.931 (2.5); 8,926 (2.4); 8.488 (1.4) ;, 484 (1.3); 8,476 (1.5); 8,472 (1.4); 8.456 (1.9); 8,450 (1.9); 8,330 (1.6); 8,325 (2.9); 8,320 (1.5) ;, 748 (0.8); 7.744 (0.9); 7,742 (0.9); 7,738 (0.7); 7,728 (0.9); 7,724 (1.0); 7.721 (1.0); 7,717 (0.8) ;, 411 (1.1); 7,399 (1.1); 7,390 (1.0); 7,378 (1.0); 6,446 (2.7); 3,871 (16.0); 3,763 (0.8); 3,433 (15.7) ;, 387 (0.9); 2,207 (0.7); 1,964 (0.5); 1,958 (1.0); 1,952 (4.7); 1,946 (8.5); 1,940 (11.5); 1.934 (7.9) ;, 928 (3.9); 0.008 (0.3); 0.000 (7.4)
H-NMR(400,0 MHz, CD3CN): δ= 8,494(1,8); 8,488(1,7); 8,479(1,3); 8,467(1,2); 8,444(1,6);,017(1,1); 8,013(1,9); 8,007(1,6); 7,728(0,8); 7,708(0,9); 7,403(0,7); 7,391(0,8); 7,382(0,7);,370(0,6); 6,346(2,0); 5,451(1,3); 5,447(1,9); 3,808(5,6); 3,804(7,9); 3,420(5,6); 3,416(7,8);,307(11,3); 3,303(16,0); 2,197(1,1); 1,956(3,4); 1,950(6,6); 1,945(9,2); 1,944(9,3); 1,939(10,6);,933(7,5); 0,004(1,7); 0,000(2,4)H-NMR (400.0 MHz, CD 3 CN): δ = 8.494 (1.8); 8.488 (1.7); 8.479 (1.3); 8,467 (1.2); 8,444 (1.6) ;, 017 (1.1); 8,013 (1.9); 8,007 (1.6); 7,728 (0.8); 7,708 (0.9); 7,403 (0.7); 7,391 (0.8); 7.382 (0.7) ;, 370 (0.6); 6,346 (2.0); 5,451 (1.3); 5,447 (1.9); 3,808 (5.6); 3,804 (7.9); 3,420 (5.6); 3,416 (7.8) ;, 307 (11.3); 3,303 (16.0); 2,197 (1.1); 1,956 (3.4); 1,950 (6.6); 1,945 (9.2); 1,944 (9.3); 1,939 (10.6) ;, 933 (7.5); 0.004 (1.7); 0.000 (2.4)
H-NMR(400,0 MHz, CD3CN): δ= 8,565(1,6); 8,559(1,6); 8,480(1,0); 8,477(1,0); 8,468(1,1);,465(0,9); 8,446(1,4); 8,440(1,5); 8,096(1,7); 8,090(1,7); 7,734(0,6); 7,731(0,7); 7,728(0,7);,714(0,7); 7,710(0,8); 7,708(0,7); 7,404(0,7); 7,392(0,7); 7,384(0,7); 7,372(0,6); 6,363(2,1);,446(3,7); 3,817(8,5); 3,762(16,0); 3,419(8,4); 2,145(27,4); 2,143(28,0); 1,963(1,6);H NMR (400.0 MHz, CD 3 CN): δ = 8.565 (1.6); 8,559 (1.6); 8,480 (1.0); 8,477 (1.0); 8,468 (1.1) ;, 465 (0.9); 8.446 (1.4); 8,440 (1.5); 8,096 (1.7); 8,090 (1.7); 7.734 (0.6); 7,731 (0.7); 7,728 (0.7) ;, 714 (0.7); 7.710 (0.8); 7,708 (0.7); 7,404 (0.7); 7,392 (0.7); 7,384 (0.7); 7,372 (0.6); 6,363 (2.1) ;, 446 (3.7); 3,817 (8.5); 3,762 (16.0); 3,419 (8.4); 2,145 (27.4); 2.143 (28.0); 1,963 (1.6);
,951(15,1); 1,945(26,4); 1,939(34,0); 1,933(24,5); 1,929(12,7); 1,927(12,6); 1,135(0,9);, 951 (15.1); 1,945 (26.4); 1,939 (34.0); 1,933 (24.5); 1.929 (12.7); 1,927 (12.6); 1.135 (0.9);
,000(7,9), 000 (7.9)
H-NMR(400,0 MHz, CD3CN): δ= 8,576(4,2); 8,483(2,6); 8,480(2,5); 8,472(2,8); 8,450(4,0);,230(4,4); 8,039(1,4); 7,737(1,9); 7,720(2,1); 7,716(2,1); 7,407(1,6); 7,395(2,0); 7,388(1,7);,376(1,4); 6,385(4,2); 5,448(8,4); 4,560(1,5); 4,543(4,2); 4,525(4,2); 4,508(1,5); 3,820(16,0);,423(15,9); 2,467(0,4); 2,188(4,9); 1,951(17,0); 1,946(25,2); 1,940(26,9); 1,934(19,6);H NMR (400.0 MHz, CD 3 CN): δ = 8.576 (4.2); 8,483 (2.6); 8,480 (2.5); 8,472 (2.8); 8,450 (4.0) ;, 230 (4.4); 8,039 (1.4); 7,737 (1.9); 7,720 (2.1); 7,716 (2.1); 7,407 (1.6); 7,395 (2.0); 7,388 (1.7) ;, 376 (1.4); 6,385 (4.2); 5,448 (8.4); 4,560 (1.5); 4,543 (4.2); 4,525 (4.2); 4,508 (1.5); 3,820 (16.0) ;, 423 (15.9); 2,467 (0.4); 2,188 (4.9); 1,951 (17.0); 1,946 (25.2); 1,940 (26.9); 1,934 (19.6);
,438(4,5); 1,420(8,4); 1,403(4,3); 1,203(0,4); 1,134(0,6); 0,000(4,5), 438 (4.5); 1,420 (8.4); 1,403 (4.3); 1,203 (0.4); 1,134 (0.6); 0,000 (4.5)
H-NMR(400,0 MHz, CD3CN): δ= 8,602(2,6); 8,596(2,7); 8,484(1,4); 8,481(1,5); 8,473(1,5);,469(1,5); 8,450(2,1); 8,444(2,0); 8,240(2,9); 8,234(2,8); 8,048(0,9); 7,742(0,8); 7,738(0,9);,736(0,9); 7,732(0,8); 7,722(0,9); 7,718(1,0); 7,715(1,0); 7,712(0,9); 7,407(1,1); 7,395(1,1);,387(1,1); 7,375(1,0); 6,387(3,0); 5,447(2,7); 4,077(16,0); 3,820(15,6); 3,424(15,3); 2,252(0,7); 2,208(0,6); 2,171(0,4); 2,114(0,3); 2,107(0,3); 1,964(0,9); 1,958(1,8); 1,952(7,6); 1,946(13,4); 1,940(17,8); 1,934(12,4); 1,927(6,3); 0,000(1,9) H NMR (400.0 MHz, CD 3 CN): δ = 8.602 (2.6); 8.596 (2.7); 8,484 (1.4); 8.481 (1.5); 8.473 (1.5) ;, 469 (1.5); 8,450 (2.1); 8,444 (2.0); 8,240 (2.9); 8,234 (2.8); 8,048 (0.9); 7,742 (0.8); 7,738 (0.9) ;, 736 (0.9); 7,732 (0.8); 7,722 (0.9); 7,718 (1.0); 7.715 (1.0); 7,712 (0.9); 7,407 (1.1); 7,395 (1.1) ;, 387 (1.1); 7,375 (1.0); 6,387 (3.0); 5,447 (2.7); 4,077 (16.0); 3,820 (15.6); 3,424 (15.3); 2,252 (0.7); 2.208 (0.6); 2,171 (0.4); 2,114 (0.3); 2,107 (0.3); 1,964 (0.9); 1,958 (1.8); 1,952 (7.6); 1,946 (13.4); 1,940 (17.8); 1,934 (12.4); 1,927 (6.3); 0.000 (1.9)
1H-NM (400,0 MHz, CD3CN): δ= 8,486(0,9); 8,474(0,9); 8,450(1,1); 8,444(1,1); 7,916(0,9); 7,912(2,3); 7,907(3,8); 7,903(3,2); 7,899(1,0); 7,854(1,7); 7,850(2,2); 7,846(1,3); 7,738(0,7); 7,734(0,8); 7,731(0,8); 7,728(0,7); 7,717(0,8); 7,714(0,9); 7,711(0,8); 7,707(0,8); 7,406(0,9); 7,394(0,9); 7,386(0,8); 7,374(0,8); 6,411(2,4); 5,447(0,3); 3,852(16,0); 3,427(15,9); 3,388(1,2); 3,303(1,3); 2,464(0,4); 2,162(60,6); 2,119(0,4); 2,113(0,5); 2,107(0,5); 2,101(0,4); 1,964(2,2); 1,958(4,1); 1,952(26,6); 1,946(49,4); 1,939(68,6); 1,933(47,5); 1,927(24,2); 1,914(0,3); 1H-NM (400.0 MHz, CD 3 CN): δ = 8.486 (0.9); 8.474 (0.9); 8,450 (1.1); 8,444 (1.1); 7,916 (0.9); 7.912 (2.3); 7,907 (3.8); 7,903 (3.2); 7,899 (1.0); 7,854 (1.7); 7,850 (2.2); 7,846 (1.3); 7,738 (0.7); 7.734 (0.8); 7,731 (0.8); 7,728 (0.7); 7,717 (0.8); 7,714 (0.9); 7.711 (0.8); 7,707 (0.8); 7,406 (0.9); 7,394 (0.9); 7,386 (0.8); 7.374 (0.8); 6,411 (2.4); 5,447 (0.3); 3,852 (16.0); 3,427 (15.9); 3,388 (1.2); 3,303 (1.3); 2.464 (0.4); 2,162 (60.6); 2,119 (0.4); 2,113 (0.5); 2,107 (0.5); 2,101 (0.4); 1,964 (2.2); 1,958 (4.1); 1,952 (26.6); 1,946 (49.4); 1,939 (68.6); 1,933 (47.5); 1,927 (24.2); 1,914 (0.3);
1,768(0,4); 0,000(0,6) 1,768 (0.4); 0.000 (0.6)
1H-NMR(400,0 MHz, DMSO): δ= 8,551(2,0); 8,545(2,1); 8,491(1,5); 8,488(1,5); 8,479(1,5); 8,476(1,4); 8,313(0,4); 7,903(0,9); 7,900(1,0); 7,897(1,0); 7,893(0,9); 7,883(1,0); 7,879(1,1); 7,876(1,1); 7,873(0,9); 7,737(1,5); 7,718(1,6); 7,674(1,5); 7,653(1,8); 7,476(1,2); 7,463(1,2); 7,455(1,2); 7,443(1,1); 7,419(1,0); 7,414(4,3); 7,412(4,0); 7,401(1,4); 7,398(1,6); 7,380(1,1); 7,377(1,0); 7,338(1,3); 7,336(1,2); 7,319(1,7); 7,300(0,8); 7,298(0,7); 6,478(2,9); 5,753(0,4); ,067(16,0); 3,427(14,9); 3,319(168,6); 2,676(0,6); 2,671(0,7); 2,666(0,6); 2,524(1,8);  1 H NMR (400.0 MHz, DMSO): δ = 8.551 (2.0); 8,545 (2.1); 8,491 (1.5); 8.488 (1.5); 8.479 (1.5); 8,476 (1.4); 8,313 (0.4); 7,903 (0.9); 7,900 (1.0); 7,897 (1.0); 7,893 (0.9); 7,883 (1.0); 7,879 (1.1); 7,876 (1.1); 7,873 (0.9); 7,737 (1.5); 7,718 (1.6); 7,674 (1.5); 7,653 (1.8); 7,476 (1.2); 7,463 (1.2); 7.455 (1.2); 7,443 (1.1); 7,419 (1.0); 7,414 (4.3); 7,412 (4.0); 7,401 (1.4); 7,398 (1.6); 7,380 (1.1); 7,377 (1.0); 7,338 (1.3); 7,336 (1.2); 7,319 (1.7); 7,300 (0.8); 7,298 (0.7); 6.478 (2.9); 5,753 (0.4); , 067 (16.0); 3,427 (14.9); 3.319 (168.6); 2,676 (0.6); 2,671 (0.7); 2,666 (0.6); 2,524 (1.8);
2,511(43,7); 2,506(91,4); 2,502(126,3); 2,497(92,5); 2,493(43,2); 2,333(0,5); 2,329(0,7); 2,511 (43.7); 2,506 (91.4); 2.502 (126.3); 2,497 (92.5); 2,493 (43.2); 2,333 (0.5); 2.329 (0.7);
2,324(0,5); 1,988(0,5); 0,146(0,4); 0,008(2,9); 0,000(93,6); -0,009(3,0); -0,149(0,4) 2,324 (0.5); 1,988 (0.5); 0.146 (0.4); 0.008 (2.9); 0,000 (93.6); -0.009 (3.0); -0.149 (0.4)
1H-NMR(400,0 MHz, DMSO): δ= 8,556(2,2); 8,550(2,3); 8,496(1,7); 8,492(1,7); 8,484(1,8); 8,480(1,7); 7,984(1,8); 7,974(2,1); 7,965(2,4); 7,960(2,1); 7,906(0,9); 7,902(1,0); 7,899(1,0); 7,896(0,9); 7,886(1,0); 7,882(1,1); 7,879(1,1); 7,875(1,0); 7,597(6,6); 7,565(0,8); 7,556(2,8); 7,553(2,7); 7,545(4,4); 7,539(4,6); 7,530(0,5); 7,475(1,3); 7,463(1,3); 7,455(1,2); 7,443(1,2); 6,551(1,8); 5,753(1,3); 4,058(16,0); 3,435(14,5); 3,319(102,3); 2,675(0,4); 2,671(0,5);  1 H NMR (400.0 MHz, DMSO): δ = 8.556 (2.2); 8,550 (2.3); 8,496 (1.7); 8.492 (1.7); 8,484 (1.8); 8,480 (1.7); 7,984 (1.8); 7,974 (2.1); 7,965 (2.4); 7,960 (2.1); 7,906 (0.9); 7,902 (1.0); 7,899 (1.0); 7,896 (0.9); 7,886 (1.0); 7,882 (1.1); 7,879 (1.1); 7,875 (1.0); 7,597 (6.6); 7,565 (0.8); 7,556 (2.8); 7,553 (2.7); 7,545 (4.4); 7,539 (4.6); 7,530 (0.5); 7,475 (1.3); 7,463 (1.3); 7.455 (1.2); 7,443 (1.2); 6,551 (1.8); 5,753 (1.3); 4,058 (16.0); 3,435 (14.5); 3.319 (102.3); 2,675 (0.4); 2,671 (0.5);
2,666(0,4); 2,524(1,1); 2,519(1,7); 2,511(27,9); 2,506(58,4); 2,502(81,1); 2,497(59,8); 2,666 (0.4); 2,524 (1.1); 2,519 (1.7); 2,511 (27.9); 2,506 (58.4); 2,502 (81.1); 2,497 (59.8);
2,493(28,3); 2,333(0,4); 2,329(0,5); 2,324(0,3); 1,236(0,6); 0,008(1,9); 0,000(61,1); -0,008(2,1)2,493 (28.3); 2,333 (0.4); 2,329 (0.5); 2,324 (0.3); 1,236 (0.6); 0.008 (1.9); 0,000 (61.1); -0.008 (2.1)
1H-NMR(400,0 MHz, DMSO): δ= 8,538(2,0); 8,532(2,1); 8,491(1,5); 8,488(1,6); 8,479(1,5); 8,476(1,6); 7,898(0,8); 7,894(1,0); 7,892(1,0); 7,888(0,9); 7,878(1,0); 7,874(1,1); 7,872(1,1); 7,868(0,9); 7,468(1,3); 7,456(1,3); 7,448(1,2); 7,436(1,1); 7,350(6,5); 6,556(1,6); 5,754(2,6); ,431(1,2); 4,413(4,0); 4,395(4,0); 4,378(1,3); 4,010(16,0); 3,423(14,7); 3,320(36,8); 2,524(0,7); 2,511(14,6); 2,507(30,3); 2,502(42,3); 2,498(32,2); 1,359(4,3); 1,341(8,9); 1,323(4,2);1 H NMR (400.0 MHz, DMSO): δ = 8.538 (2.0); 8.532 (2.1); 8,491 (1.5); 8.488 (1.6); 8.479 (1.5); 8,476 (1.6); 7,898 (0.8); 7,894 (1.0); 7,892 (1.0); 7,888 (0.9); 7,878 (1.0); 7,874 (1.1); 7,872 (1.1); 7,868 (0.9); 7,468 (1.3); 7,456 (1.3); 7,448 (1.2); 7,436 (1.1); 7,350 (6.5); 6,556 (1.6); 5,754 (2.6); , 431 (1.2); 4,413 (4.0); 4,395 (4.0); 4,378 (1.3); 4,010 (16.0); 3,423 (14.7); 3,320 (36.8); 2,524 (0.7); 2,511 (14.6); 2,507 (30.3); 2,502 (42.3); 2,498 (32.2); 1,359 (4.3); 1,341 (8.9); 1.323 (4.2);
,008(1,9); 0,000(52,8); -0,008(1,9)  , 008 (1.9); 0,000 (52.8); -0.008 (1.9)
1H-NMR(400,0 MHz, DMSO): δ= 8,600(5,3); 8,530(1,4); 8,525(1,4); 8,472(1,1); 8,461(1,1); 8,315(0,8); 7,875(0,8); 7,872(1,0); 7,869(1,0); 7,865(0,8); 7,855(0,9); 7,851(1,0); 7,849(1,1); 7,845(0,9); 7,456(1,1); 7,445(1,1); 7,436(1,0); 7,424(0,9); 6,364(3,2); 5,754(0,5); 4,917(0,4); ,901(1,0); 4,884(1,4); 4,867(1,0); 4,850(0,4); 4,099(16,0); 3,408(14,3); 3,318(18,8); 3,295(0,3); 2,671(0,4); 2,510(22,7); 2,506(45,5); 2,502(62,2); 2,497(47,1); 2,493(23,5); 2,328(0,4);  1 H NMR (400.0 MHz, DMSO): δ = 8.600 (5.3); 8,530 (1.4); 8,525 (1.4); 8,472 (1.1); 8.461 (1.1); 8.315 (0.8); 7,875 (0.8); 7,872 (1.0); 7,869 (1.0); 7,865 (0.8); 7,855 (0.9); 7,851 (1.0); 7,849 (1.1); 7.845 (0.9); 7,456 (1.1); 7,445 (1.1); 7,436 (1.0); 7,424 (0.9); 6,364 (3.2); 5,754 (0.5); 4.917 (0.4); , 901 (1.0); 4,884 (1.4); 4,867 (1.0); 4,850 (0.4); 4,099 (16.0); 3,408 (14.3); 3,318 (18.8); 3,295 (0.3); 2,671 (0.4); 2,510 (22.7); 2,506 (45.5); 2,502 (62.2); 2,497 (47.1); 2,493 (23.5); 2,328 (0.4);
1,529(14,8); 1,512(14,8); 1,235(0,5); 0,008(1,0); 0,000(22,8); -0,008(0,9) 1,529 (14.8); 1.512 (14.8); 1,235 (0.5); 0.008 (1.0) 0,000 (22.8); -0.008 (0.9)
1H-NMR(400,0 MHz, DMSO): δ= 8,537(2,0); 8,531(2,1); 8,478(1,6); 8,470(5,2); 8,463(1,7); 7,884(0,8); 7,880(1,0); 7,877(1,0); 7,874(0,9); 7,863(0,9); 7,859(1,1); 7,857(1,1); 7,853(0,9); 7,462(1,1); 7,451(1,2); 7,442(1,1); 7,430(1,0); 6,360(3,0); 5,754(0,9); 4,102(13,9); 4,094(16,0); 3,406(14,1); 3,319(53,3); 2,675(0,4); 2,671(0,6); 2,666(0,4); 2,541(0,5); 2,506(71,2);  1 H NMR (400.0 MHz, DMSO): δ = 8.537 (2.0); 8,531 (2.1); 8.478 (1.6); 8,470 (5.2); 8.463 (1.7); 7,884 (0.8); 7,880 (1.0); 7.877 (1.0); 7,874 (0.9); 7,863 (0.9); 7,859 (1.1); 7,857 (1.1); 7,853 (0.9); 7,462 (1.1); 7,451 (1.2); 7.442 (1.1); 7,430 (1.0); 6,360 (3.0); 5,754 (0.9); 4,102 (13.9); 4,094 (16.0); 3,406 (14.1); 3,319 (53.3); 2,675 (0.4); 2,671 (0.6); 2,666 (0.4); 2,541 (0.5); 2,506 (71.2);
2,502(95,1); 2,497(73,3); 2,333(0,4); 2,328(0,6); 2,324(0,4); 0,008(0,7); 0,000(15,1)2,502 (95.1); 2,497 (73.3); 2,333 (0.4); 2,328 (0.6); 2,324 (0.4); 0.008 (0.7); 0.000 (15.1)
H-NMR(400,0 MHz, CD3CN): δ= 8,592(2,3);8,586(2,4);8,505(1,2);8,501(1,3);8,493(1,3);H NMR (400.0 MHz, CD3CN): δ = 8.592 (2.3), 8.586 (2.4), 8.055 (1.2), 8.501 (1.3), 8.493 (1.3);
,489(1,3);8,415(1,7);8,409(1,7);8,231(2,6);8,225(2,6);8,052(0,7);7,729(0,7);7,725(0,8);, 489 (1.3); 8,415 (1.7); 8,409 (1.7); 8,231 (2.6); 8,225 (2.6); 8,052 (0.7); 7,729 (0.7); 7,725 (0.8);
,723(0,8);7,719(0,7);7,709(0,8);7,705(0,9);7,702(0,9);7,698(0,8);7,421(0,9);7,420(1,0);, 723 (0.8); 7,719 (0.7); 7.709 (0.8); 7,705 (0.9); 7,702 (0.9); 7.698 (0.8); 7,421 (0.9); 7,420 (1.0);
,409(0,9);7,408(1,0);7,401(0,8);7,399(0,9);7,389(0,8);7,387(0,8);6,337(2,5);5,448(7,0);, 409 (0.9); 7,408 (1.0); 7,401 (0.8); 7,399 (0.9); 7,389 (0.8); 7.387 (0.8); 6,337 (2.5); 5,448 (7.0);
,074(16,0);3,945(1,0);3,927(3,1);3,909(3,1);3,891(1,0);3,817(15,3);1,965(0,3);1,958(0,6);,953(4,3);1,946(8,0);1,940(11,2);1,934(7,7);1,928(3,9);1,195(3,3);1,177(7,1);1,159(3,3);, 074 (16.0); 3,945 (1.0); 3,927 (3.1); 3,909 (3.1); 3,891 (1.0); 3,817 (15.3); 1,965 (0.3); 1,958 (0.6) ;, 953 (4.3); 1,946 (8.0); 1,940 (11.2); 1,934 (7.7); 1,928 (3.9); 1,195 (3.3); 1,177 (7.1); 1,159 (3.3);
,008(1,3);0,000(44,8);-0,008(1,6), 008 (1.3); 0,000 (44.8) - 0.008 (1.6)
H-NMR(400,0 MHz, CD3CN): δ= 8,567(2,4);8,561(2,6);8,504(1,0);8,493(1,0);8,412(1,3);H-NMR (400.0 MHz, CD3CN): δ = 8.567 (2.4), 8.561 (2.6), 8.504 (1.0), 8.493 (1.0), 8.412 (1.3);
,219(2,6);8,214(2,6);7,722(1,0);7,706(0,9);7,702(1,1);7,420(1,0);7,408(1,0);7,399(1,0);, 219 (2.6); 8,214 (2.6); 7,722 (1.0); 7.706 (0.9); 7,702 (1.1); 7,420 (1.0); 7,408 (1.0); 7,399 (1.0);
,387(0,9);6,334(2,1);5,446(4,0);4,557(1,3);4,539(4,1);4,521(4,2);4,504(1,4);3,944(1,1); 3,926(3,5);3,908(3,6);3,890(1,2);3,816(16,0);1,964(0,5);1,958(0,9);1,952(6,0);1,946(11,4); 1,940(16,1);1,934(11,3);1,927(5,9);1,436(4,2);1,418(8,5);1,401(4,2);1,355(0,5);1,194(3,8); 1,177(8,0);1,159(3,8);0,008(1,8);0,000(59,4) , 387 (0.9); 6,334 (2.1); 5,446 (4.0); 4,557 (1.3); 4,539 (4.1); 4,521 (4.2); 4,504 (1.4); 3,944 (1.1); 3,926 (3.5); 3,908 (3.6); 3,890 (1.2); 3,816 (16.0); 1,964 (0.5); 1,958 (0.9); 1,952 (6.0); 1,946 (11.4); 1,940 (16.1); 1,934 (11.3); 1,927 (5.9); 1,436 (4.2); 1,418 (8.5); 1,401 (4.2); 1,355 (0.5); 1,194 (3.8); 1,177 (8.0); 1,159 (3.8); 0,008 (1.8); 0,000 (59.4)
77 1H-NM (400,0 MHz, CD3CN): δ= 8,619(1,1);8,617(1,1);8,607(1,1);8,605(1,1);8,475(1,3); 77 1 H-NM (400.0 MHz, CD3CN): δ = 8.619 (1.1), 8.617 (1.1), 8.607 (1.1), 8.605 (1.1), 8.475 (1.3) ,
8,471(1,4);8,463(1,4);8,459(1,4);8,411(1,9);8,406(1,9);7,986(1,4);7,966(1,8);7,827(0,8); 7,823(0,8);7,808(1,2);7,804(1,2);7,788(0,7);7,784(0,7);7,700(0,7);7,697(0,9);7,694(0,8); 7,690(0,7);7,680(0,8);7,676(1,0);7,674(0,9);7,670(0,8);7,387(1,0);7,375(1,0);7,367(0,9); 7,355(0,9);7,349(0,9);7,347(0,9);7,337(0,8);7,335(0,9);7,331(0,9);7,328(0,8);7,318(0,8); 8,471 (1.4); 8.463 (1.4) 8.459 (1.4); 8,411 (1.9); 8,406 (1.9); 7,986 (1.4); 7.966 (1.8) 7.827 (0.8); 7,823 (0.8); 7,808 (1.2); 7,804 (1.2); 7,788 (0.7); 7,784 (0.7); 7,700 (0.7); 7,697 (0.9); 7,694 (0.8); 7,690 (0.7); 7,680 (0.8); 7.676 (1.0); 7,674 (0.9); 7,670 (0.8); 7.387 (1.0); 7,375 (1.0); 7,367 (0.9); 7,355 (0.9); 7,349 (0.9); 7,347 (0.9); 7,337 (0.8); 7.335 (0.9); 7,331 (0.9); 7,328 (0.8); 7,318 (0.8);
7,316(0,7);6,415(3,2);5,447(0,7);4,188(16,0);3,961(1,1);3,943(3,4);3,925(3,5);3,907(1,1);7,316 (0.7); 6.415 (3.2); 5,447 (0.7); 4,188 (16.0); 3,961 (1.1); 3,943 (3.4); 3,925 (3.5); 3,907 (1,1);
2,161(3,9);1,958(0,4);1,952(2,8);1,946(5,1);1,940(7,2);1,934(5,0);1,928(2,5);1,200(3,6);2,161 (3.9); 1,958 (0.4); 1,952 (2.8); 1,946 (5.1); 1,940 (7.2); 1,934 (5.0); 1,928 (2.5); 1,200 (3.6);
1,182(7,4);1,165(3,5);0,008(1,2);0,000(28,9);-0,008(1,2) 1,182 (7.4); 1.165 (3.5) 0.008 (1.2) 0.000 (28.9) - 0.008 (1.2)
78 1H-NM (400,0 MHz, CD3CN): δ= 8,454(1,0);8,441(1,9);7,721(1,1);7,715(0,8);7,712(0,9); 78 1 H-NM (400.0 MHz, CD3CN): δ = 8.454 (1.0); 8.441 (1.9); 7.721 (1.1); 7.715 (0.8); 7.712 (0.9) ;
7,709(0,9);7,702(2,2);7,695(0,9);7,691(1,0);7,689(1,0);7,682(1,8);7,607(2,1);7,588(1,5); (0.9) 7.709; 7,702 (2.2); 7,695 (0.9); 7,691 (1.0); 7,689 (1.0); 7,682 (1.8); 7,607 (2.1); 7,588 (1.5);
7,379(0,9);7,368(0,9);7,359(0,8);7,347(0,8);6,785(1,8);6,764(1,7);6,445(2,0);5,447(1,1);7,379 (0.9); 7,368 (0.9); 7,359 (0.8); 7,347 (0.8); 6,785 (1.8); 6,764 (1.7); 6,445 (2.0); 5,447 (1,1);
4,225(15,9);3,960(16,0);3,437(15,7);2,183(0,7);1,958(0,5);1,952(3,5);1,946(6,6);1,940(9,0);4,225 (15.9); 3,960 (16.0); 3,437 (15.7); 2,183 (0.7); 1,958 (0.5); 1,952 (3.5); 1,946 (6.6); 1,940 (9.0);
1,934(6,2);1,928(3,1);0,000(7,3) 1,934 (6.2); 1,928 (3.1); 0,000 (7.3)
79 1H-NMR(400,0 MHz, CD3CN): δ= 8,489(0,6);8,486(0,6);8,477(0,6);8,474(0,6);8,451(0,8); 79 1 H-NMR (400.0 MHz, CD3CN): δ = 8.489 (0.6), 8.486 (0.6), 8.477 (0.6), 8.474 (0.6), 8.451 (0.8) ;
8,445(0,9);7,733(0,4);7,731(0,4);7,727(0,3);7,716(0,4);7,713(0,4);7,710(0,4);7,706(0,4); 7,412(0,5);7,400(0,5);7,391(0,4);7,379(0,4);7,346(0,5);7,343(0,5);7,327(0,6);7,324(0,6); 7,147(0,5);7,128(0,6);6,934(0,7);6,915(1,0);6,896(0,5);6,351(1,6);5,446(2,4);4,620(1,1); 4,598(2,1);4,576(1,2);3,661(7,8);3,417(7,7);3,285(0,7);3,263(1,2);3,241(0,6);2,626(1,0); 2,147(4,5);1,957(0,4);1,951(3,3);1,945(6,2);1,939(8,6);1,933(5,9);1,927(3,0);1,200(0,5); 1,134(16,0);0,000(4,1)  8,445 (0.9); 7,733 (0.4); 7,731 (0.4); 7,727 (0.3); 7,716 (0.4); 7,713 (0.4); 7,710 (0.4); 7.706 (0.4); 7,412 (0.5); 7,400 (0.5); 7,391 (0.4); 7,379 (0.4); 7,346 (0.5); 7,343 (0.5); 7,327 (0.6); 7,324 (0.6); 7,147 (0.5); 7,128 (0.6); 6,934 (0.7); 6,915 (1.0); 6,896 (0.5); 6,351 (1.6); 5,446 (2.4); 4,620 (1,1); 4,598 (2.1); 4,576 (1.2); 3,661 (7.8); 3,417 (7.7); 3,285 (0.7); 3,263 (1.2); 3,241 (0.6); 2,626 (1.0); (4.5) 2,147; 1,957 (0.4); 1,951 (3.3); 1,945 (6.2); 1,939 (8.6); 1,933 (5.9); 1,927 (3.0); 1,200 (0.5); 1,134 (16.0); 0,000 (4.1)
80 1H-NMR(400,0 MHz, CD3CN): δ= 8,511(0,5);8,508(0,6);8,494(0,9);8,487(0,8);7,801(1,0); 80 1 H-NMR (400.0 MHz, CD3CN): δ = 8.511 (0.5), 8.508 (0.6), 8.494 (0.9), 8.487 (0.8), 7.801 (1.0) ;
7,795(1,2);7,789(0,6);7,773(0,8);7,770(0,9);7,762(0,3);7,751(0,4);7,748(0,4);7,745(0,4); 7,433(0,4);7,420(0,7);7,416(0,6);7,401(1,1);7,378(0,7);7,359(0,9);6,959(1,1);6,954(1,0); 6,448(1,2);5,447(1,3);3,711(5,8);3,454(0,7);3,445(5,7);3,285(0,7);2,627(1,6);2,149(4,6); 1,952(2,5);1,945(4,6);1,939(6,1);1,933(4,2);1,927(2,1);1,199(0,5);1,134(16,0);0,000(2,9) 7,795 (1.2); 7.789 (0.6); 7,773 (0.8); 7,770 (0.9); 7,762 (0.3); 7,751 (0.4); 7,748 (0.4); 7,745 (0.4); 7,433 (0.4); 7,420 (0.7); 7,416 (0.6); 7,401 (1.1); 7,378 (0.7); 7,359 (0.9); 6,959 (1.1); 6,954 (1.0); 6.448 (1.2); 5,447 (1.3); 3,711 (5.8); 3,454 (0.7); 3,445 (5.7); 3,285 (0.7); 2,627 (1.6); 2,149 (4.6); 1,952 (2.5); 1,945 (4.6); 1,939 (6.1); 1,933 (4.2); 1,927 (2.1); 1,199 (0.5); 1,134 (16.0); 0.000 (2.9)
81 1H-NMR(400,0 MHz, CD3CN): δ= 8,492(1,2);8,488(1,3);8,480(1,3);8,476(1,3);8,454(1,7); 81 1 H-NMR (400.0 MHz, CD3CN): δ = 8.492 (1.2), 8.488 (1.3), 8.480 (1.3), 8.466 (1.3), 8.454 (1.7) ;
8,449(1,8);8,043(0,4);7,735(0,7);7,731(0,8);7,728(0,8);7,725(0,7);7,714(0,8);7,711(1,0); 8,449 (1.8); 8,043 (0.4); 7,735 (0.7); 7,731 (0.8); 7,728 (0.8); 7,725 (0.7); 7,714 (0.8); 7.711 (1.0);
7,708(0,9);7,704(0,8);7,586(2,4);7,565(2,5);7,414(1,0);7,402(1,0);7,394(0,9);7,382(0,9);7,708 (0.9); 7.704 (0.8); 7,586 (2.4); 7,565 (2.5); 7,414 (1.0); 7,402 (1.0); 7,394 (0.9); 7,382 (0.9);
6,431(2,7);6,411(2,6);6,352(3,0);5,447(2,4);3,954(16,0);3,943(15,4);3,584(15,5);3,417(15,3);6,431 (2.7); 6,411 (2.6); 6,352 (3.0); 5,447 (2.4); 3,954 (16.0); 3,943 (15.4); 3,584 (15.5); 3,417 (15.3);
1,963(0,4);1,957(0,9);1,952(5,6);1,945(10,4);1,939(14,2);1,933(9,7);1,927(4,9);0,000(6,1)1,963 (0.4); 1,957 (0.9); 1,952 (5.6); 1,945 (10.4); 1,939 (14.2); 1,933 (9.7); 1,927 (4.9); 0,000 (6.1)
82 1H-NMR(400,0 MHz, CD3CN): δ= 8,498(0,4);8,487(0,4);8,466(0,5);8,462(0,5);7,733(0,3); 82 1 H-NMR (400.0 MHz, CD3CN): δ = 8.498 (0.4), 8.487 (0.4), 8.466 (0.5), 8.462 (0.5), 7.733 (0.3) ;
7,712(0,4);7,710(0,4);7,485(0,4);7,418(0,4);7,406(0,4);7,398(0,3);7,386(0,3);7,279(0,4); 7,276(0,4);7,260(0,4);7,257(0,4);7,107(0,6);7,086(0,6);7,053(0,3);7,034(0,6);6,352(0,4); 5,446(2,0);3,806(5,2);3,566(3,5);3,421(5,5);2,626(1,4);2,146(2,4);1,951(2,4);1,945(4,5); 1,939(6,0);1,933(4,2);1,927(2,1);1,134(16,0);0,000(3,3)  7,712 (0.4); 7,710 (0.4); 7,485 (0.4); 7,418 (0.4); 7,406 (0.4); 7,398 (0.3); 7,386 (0.3); 7,279 (0.4); 7,276 (0.4); 7,260 (0.4); 7,257 (0.4); 7,107 (0.6); 7,086 (0.6); 7,053 (0.3); 7,034 (0.6); 6,352 (0.4); 5,446 (2.0); 3,806 (5.2); 3,566 (3.5); 3,421 (5.5); 2,626 (1.4); 2,146 (2.4); 1,951 (2.4); 1,945 (4.5); 1,939 (6.0); 1,933 (4.2); 1,927 (2.1); 1,134 (16.0); 0,000 (3.3)
83 1H-NMR(400,0 MHz, CD3CN): δ= 8,491(1,6);8,488(1,5);8,479(1,6);8,476(1,6);8,455(2,2); 83 1 H NMR (400.0 MHz, CD3CN): δ = 8.491 (1.6), 8.488 (1.5), 8.479 (1.6), 8.466 (1.6), 8.455 (2.2) ;
8,449(2,2);8,029(1,1);7,743(0,9);7,739(1,1);7,736(1,0);7,733(0,8);7,722(1,0);7,718(1,2); 8,449 (2.2); 8,029 (1.1); 7,743 (0.9); 7,739 (1.1); 7,736 (1.0); 7,733 (0.8); 7,722 (1.0); 7,718 (1.2)
7,413(1,2);7,401(1,2);7,393(1,1);7,381(1,0);6,972(0,5);6,961(1,2);6,959(1,3);6,948(2,8);7,413 (1.2); 7,401 (1.2); 7,393 (1.1); 7,381 (1.0); 6,972 (0.5); 6,961 (1.2); 6,959 (1.3); 6,948 (2.8);
6,939(1,0);6,929(4,3);6,927(3,7);6,916(3,3);6,383(3,5);6,024(10,7);5,447(3,3);3,730(16,0);6.939 (1.0); 6,929 (4.3); 6,927 (3.7); 6,916 (3.3); 6,383 (3.5); 6,024 (10.7); 5,447 (3.3); 3,730 (16.0);
3,421(15,8);1,963(0,4);1,951(5,0);1,945(9,2);1,939(12,2);1,933(8,5);1,927(4,3);0,000(3,7)3,421 (15.8); 1,963 (0.4); 1,951 (5.0); 1,945 (9.2); 1,939 (12.2); 1,933 (8.5); 1,927 (4.3); 0,000 (3.7)
84 1H-NMR(400,0 MHz, CD3CN): δ= 8,490(1,5);8,486(1,5);8,478(1,5);8,475(1,4);8,453(2,0); 84 1 H-NMR (400.0 MHz, CD3CN): δ = 8.490 (1.5); 8.486 (1.5); 8.478 (1.5); 8.475 (1.4); 8.453 (2.0) ;
8,447(2,0);7,728(0,9);7,725(1,0);7,722(0,9);7,718(0,8);7,708(1,0);7,704(1,1);7,702(1,1); 8,447 (2.0); 7,728 (0.9); 7,725 (1.0); 7,722 (0.9); 7,718 (0.8); 7,708 (1.0); 7.704 (1.1); 7,702 (1,1);
7,698(0,8);7,411(1,1);7,400(1,1);7,391(1,0);7,379(0,9);7,192(2,3);7,171(2,5);6,625(2,1);7.698 (0.8); 7,411 (1.1); 7,400 (1.1); 7,391 (1.0); 7,379 (0.9); 7,192 (2.3); 7,171 (2.5); 6.625 (2.1);
6,619(2,8);6,603(1,8);6,598(1,1);6,582(1,5);6,577(1,1);6,321(3,7);3,836(15,8);3,793(15,0);6,619 (2.8); 6,603 (1.8); 6,598 (1.1); 6,582 (1.5); 6,577 (1.1); 6,321 (3.7); 3,836 (15.8); 3.793 (15.0);
3,548(16,0);3,414(16,0);2,763(0,5);2,750(0,5);2,144(8,7);1,963(0,6);1,951(7,4);1,945(13,3); 1,939(17,6); 1,933(12,0);1,927(6,1);1,199(2,4);1,134(1,4);0,000( 1,9) 3,548 (16.0); 3.414 (16.0); 2,763 (0.5); 2,750 (0.5); 2,144 (8.7); 1,963 (0.6); 1,951 (7.4); 1,945 (13.3); 1,939 (17.6); 1,933 (12.0), 1.927 (6.1), 1.199 (2.4), 1.144 (1.4), 0.000 (1.9)
85 1H-NM (400,0 M Hz, CD3CN): δ= 8,492(0,9);8,481(1,0);8,458(1,3);8,452(1,3);7,728(0,7); 85 1 H-NM (400.0 M Hz, CD3CN): δ = 8.492 (0.9), 8.481 (1.0), 8.458 (1.3), 8.452 (1.3), 7.728 (0.7 );
7,726(0,6);7,712(0,6);7,708(0,7);7,414(0,7);7,403(0,7);7,394(0,7);7,382(0,6);7,030(1,8); 7,726 (0.6); 7,712 (0.6); 7,708 (0.7); 7,414 (0.7); 7,403 (0.7); 7,394 (0.7); 7,382 (0.6); 7,030 (1.8);
7,025(3,4);6,835(1,4);6,829(1,2);6,349(2,1);5,447(2,1);5,445(2,0);3,742(16,0);3,571(8,1);7,025 (3.4); 6,835 (1.4); 6,829 (1.2); 6,349 (2.1); 5,447 (2.1); 5,445 (2.0); 3,742 (16.0); 3.571 (8.1);
3,570(7,8);3,419(8,1);3,418(7,7);2,763(0,4);2,750(0,4);2,632(0,8);2,151(6,3);1,950(3,8);3,570 (7.8); 3,419 (8.1); 3,418 (7.7); 2,763 (0.4); 2,750 (0.4); 2,632 (0.8); 2,151 (6.3); 1,950 (3.8);
1,945(6,2);1,944(6,7);1,939(8,3);1,938(8,3); 1,933(5,8);1,931(5,6);1,927(3,0);1,199(1,3); l,134(8,9);l,132(8,3);0,000(0,9);-0,002(0,9) 1,945 (6.2); 1,944 (6.7); 1,939 (8.3); 1,938 (8.3); 1,933 (5.8); 1,931 (5.6); 1,927 (3.0); 1,199 (1.3); l, 134 (8.9); l, 132 (8.3); 0,000 (0.9) - 0.002 (0.9)
86 1H-NM (400,0 M Hz, CD3CN): δ= 8,457(1,6);8,454(1,6);8,443(3,5);8,437(2,2);8,263(1,6); 86 1 H-NM (400.0 M Hz, CD3CN): δ = 8.457 (1.6), 8.454 (1.6), 8.433 (3.5), 8.437 (2.2), 8.263 (1.6 );
8,243(1,9);8,058(1,0);8,038(1,8);8,018(0,9);7,766(2,0);7,747(1,7);7,718(0,9);7,714(1,0); 8,243 (1.9); 8,058 (1.0); 8,038 (1.8); 8,018 (0.9); 7,766 (2.0); 7.747 (1.7); 7,718 (0.9); 7,714 (1.0);
7,712(1,0);7,708(0,8);7,698(1,0);7,694( 1,1);7,691(1,1);7,688(0,8);7,378(1,2);7,366(1,2);7.712 (1.0), 7.708 (0.8), 7.688 (1.0), 7.694 (1.1), 7.691 (1.1), 7.688 (0.8), 7.378 (1.2), 7.366 (1,2);
7,358(1,1);7,346(1,0);6,504(3,0);4,212( 16,0);3,444(15,9);2,163(4,5); 1,964(0,5);1,952(6,3);7.358 (1.1), 7.346 (1.0), 6.504 (3.0), 4.212 (16.0), 3.444 (15.9), 2.163 (4.5); 1,964 (0.5); 1,952 (6.3);
1,946(11,3); 1,940(14,8);1,934(10,1);1,928(5,1);0,000(1,3) 1,946 (11.3); 1,940 (14.8); 1,934 (10.1); 1,928 (5.1); 0,000 (1.3)
87 1H-NM R(400,0 M Hz, CD3CN): δ= 8,497(1,3);8,493(1,3);8,485(1,4);8,481(1,2);8,454(1,8); 87 1 H-NM R (400.0 M Hz, CD3CN): δ = 8.497 (1.3), 8.493 (1.3), 8.485 (1.4), 8.481 (1.2), 8.454 (1, 8th);
8,449(1,8);8,276(2,6);8,269(2,6);7,735(0,8);7,732(0,9);7,729(0,9);7,725(0,8);7,714(3,6); 8,449 (1.8); 8.276 (2.6); 8,269 (2.6); 7,735 (0.8); 7,732 (0.9); 7,729 (0.9); 7,725 (0.8); 7,714 (3.6);
7,708(3,4);7,417(1,0);7,405(1,0);7,396(0,9);7,384(0,9);6,391(2,7);5,447(4,0);3,923(16,0);7,708 (3.4); 7,417 (1.0); 7,405 (1.0); 7,396 (0.9); 7,384 (0.9); 6,391 (2.7); 5,447 (4.0); 3,923 (16.0);
3,606(15,7);3,422(15,6);1,964(0,6);1,957(1,4);1,952(6,5);1,946( 11,6);1,940( 15,3);1,933(10,3);3.606 (15.7), 3.422 (15.6), 1.964 (0.6), 1.957 (1.4), 1.952 (6.5), 1.946 (11.6), 1.940 (15.3), 1.933 (10.3);
1,927(5,1);0,000(1,4) 1,927 (5.1); 0,000 (1.4)
88 1H-NM R(400,0 M Hz, CD3CN): δ= 8,497(1,4);8,494(1,4);8,485(1,5);8,482(1,5);8,461(2,0); 88 1 H-NM R (400.0 M Hz, CD 3 CN): δ = 8.497 (1.4), 8.494 (1.4), 8.485 (1.5), 8.482 (1.5), 8.461 (2, 0);
8,455(2,0);8,295(1,3);8,290(1,4);8,283( 1,4);8,278(1,4);8,033(1,6);7,742(0,8);7,738(1,0); 8.455 (2.0), 8.295 (1.3), 8.290 (1.4), 8.283 (1.4), 8.278 (1.4), 8.033 (1.6), 7.742 (0.8), 7.738 (1.0);
7,736(1,0);7,732(0,8);7,722(0,9);7,718( 1,1);7,716(1,1);7,712(0,9);7,694(1,4);7,689(1,5);7.736 (1.0), 7.732 (0.8), 7.722 (0.9), 7.718 (1.1), 7.716 (1.1), 7.712 (0.9), 7.694 (1.4), 7.689 (1.5);
7,676(1,6);7,671(1,5);7,418(1,1);7,406( 1,1);7,398(1,0);7,386(0,9);7,063(1,4);7,050(1,5);7.676 (1.6), 7.671 (1.5), 7.418 (1.1), 7.406 (1.1), 7.398 (1.0), 7.386 (0.9), 7.063 (1.4), 7.050 (1.5);
7,044(1,4);7,032(1,3);6,381(3,1);5,447(2,2);3,927(16,0);3,594(15,6);3,424(15,6);2,761(1,5);7,044 (1.4); 7,032 (1.3); 6,381 (3.1); 5,447 (2.2); 3,927 (16.0); 3,594 (15.6); 3,424 (15.6); 2,761 (1.5);
1,964(0,5);1,952(5,8);1,946(10,8);1,939(14,7);1,933(10,2);1,927(5,3); 1,199(1,1); 1,134(2,1);1,964 (0.5); 1,952 (5.8); 1,946 (10.8); 1,939 (14.7); 1,933 (10.2); 1,927 (5.3); 1,199 (1.1); 1,134 (2.1);
0,000(6,8) 0,000 (6.8)
89 1H-NM R(400,0 M Hz, CD3CN): δ= 8,482(1,4);8,478(1,4);8,470(1,5);8,466(1,4);8,456(2,0); 89 1 H-NM R (400.0 M Hz, CD 3 CN): δ = 8.482 (1.4), 8.478 (1.4), 8.470 (1.5), 8.466 (1.4), 8.456 (2, 0);
8,450(2,0);8,347(1,9);8,340(2,0);7,854( 1,4);7,848(1,4);7,832(1,6);7,826(1,5);7,736(0,8); 8.450 (2.0), 8.347 (1.9), 8.340 (2.0), 7.854 (1.4), 7.848 (1.4), 7.832 (1.6), 7.826 (1.5), 7.736 (0.8);
7,733(0,9);7,730(0,8);7,726(0,7);7,716(0,9);7,712(1,0);7,706(0,8);7,404(1,1);7,393(1,1);7,733 (0.9); 7,730 (0.8); 7,726 (0.7); 7,716 (0.9); 7,712 (1.0); 7.706 (0.8); 7,404 (1.1); 7,393 (1,1);
7,384(1,0);7,372(1,0);6,824(2,2);6,803(2,1);6,361(3,5);4,406(1,2);4,388(3,9);4,370(3,9);7,384 (1.0); 7,372 (1.0); 6,824 (2.2); 6,803 (2.1); 6,361 (3.5); 4,406 (1.2); 4,388 (3.9); 4,370 (3.9);
4,361(0,4);4,353(1,3);3,813(16,0);3,421(15,7);2,764(1,1);2,751( 1,1);2,625(1,0);2,147(8,7);4.361 (0.4), 4.353 (1.3), 3.813 (16.0), 3.421 (15.7), 2.764 (1.1), 2.751 (1.1), 2.625 (1.0), 2.147 (8.7);
1,964(0,5);1,958(1,2);1,952(7,5);1,946( 13,8);1,940(18,7);1,933( 12,7);1,927(6,5); 1,380(4,1);1.964 (0.5), 1.958 (1.2), 1.952 (7.5), 1.946 (13.8), 1.940 (18.7), 1.933 (12.7), 1.927 (6.5); 1,380 (4.1);
1,362(8,1);1,345(4,0);1,322(0,3);1,312(3,8); 1,201(1,2);1,134(11,8) 1,362 (8.1); 1,345 (4.0); 1,322 (0.3); 1,312 (3.8); 1,134 (11.8); 1,201 (1.2)
90 1H-NM R(400,0 M Hz, CD3CN): δ= 8,481(1,2);8,469(1,2);8,453(1,6);8,448(1,7);8,302(2,4); 90 1 H-NM R (400.0 M Hz, CD 3 CN): δ = 8.481 (1.2), 8.469 (1.2), 8.453 (1.6), 8.448 (1.7), 8.302 (2, 4);
8,297(2,6);7,962(2,8);7,957(2,9);7,740(0,7);7,736(0,9);7,733(0,9);7,730(0,8);7,719(0,8); 8,297 (2.6); 7.962 (2.8); 7,957 (2.9); 7,740 (0.7); 7,736 (0.9); 7,733 (0.9); 7,730 (0.8); 7,719 (0.8);
7,716(1,0);7,713(1,0);7,709(0,9);7,407( 1,0);7,395(1,0);7,387(0,9);7,375(0,9);6,376(2,8);7.716 (1.0); 7.713 (1.0); 7.709 (0.9); 7.407 (1.0); 7.955 (1.0); 7.387 (0.9); 7.375 (0.9); 6.376 (2.8);
5,447(7,0);4,024(16,0);3,826(15,7);3,422(15,4);1,964(0,5);1,958(0,9); 1,952(5,8); 1,946(10,9);5,447 (7.0); 4,024 (16.0); 3.826 (15.7); 3,422 (15.4); 1,964 (0.5); 1,958 (0.9); 1,952 (5.8); 1,946 (10.9);
1,940(15,1); 1,934(10,4);1,928(5,4) 1,940 (15.1); 1,934 (10.4); 1,928 (5.4)
91 1H-NM R(400,0 M Hz, CD3CN): δ= 8,552(1,3);8,547(1,4);8,539(1,4);8,535(1,4);8,501(1,0); 91 1 H-NM R (400.0 M Hz, CD3CN): δ = 8.552 (1.3), 8.547 (1.4), 8.539 (1.4), 8.535 (1.4), 8.501 (1, 0);
8,490(1,1);8,469(1,3);7,735(0,8);7,731(0,9);7,729(0,9);7,725(0,7);7,715(0,9);7,711(1,0); 8,490 (1.1); 8.469 (1.3); 7,735 (0.8); 7,731 (0.9); 7,729 (0.9); 7,725 (0.7); 7,715 (0.9); 7.711 (1.0);
7,709(1,0);7,705(0,8);7,556(1,1);7,552( 1,1);7,537(1,2);7,533(1,2);7,416(0,9);7,405(1,0);7.709 (1.0), 7.705 (0.8), 7.556 (1.1), 7.552 (1.1), 7.537 (1.2), 7.533 (1.2), 7.416 (0.9), 7.405 (1.0);
7,396(0,9);7,384(0,8);7,179(1,3);7,167( 1,3);7,160(1,2);7,148(1,1);6,416(1,1);5,447(3,1);7.396 (0.9), 7.384 (0.8), 7.179 (1.3), 7.167 (1.3), 7.160 (1.2), 7.148 (1.1), 6.416 (1.1), 5.447 (3.1);
3,590(12,7);3,429(15,8);2,765(0,5);2,752(0,5);2,622(0,7);2,483( 16,0);2,145( 19,4);1,964(0,6);3.590 (12.7), 3.429 (15.8), 2.765 (0.5), 2.752 (0.5), 2.622 (0.7), 2.483 (16.0), 2.145 (19.4), 1.964 (0.6);
1,952(8,2);1,946(15,1);1,939(20,4);1,933(14,1);1,927(7,3);1,332(0,4); 1,201(0,8); 1,134(8,5)1,952 (8.2); 1,946 (15.1); 1,939 (20.4); 1,933 (14.1); 1,927 (7.3); 1,332 (0.4); 1,201 (0.8); 1.134 (8.5)
92 1H-NM R(400,0 M Hz, CD3CN): δ= 8,488(1,9);8,477(2,0);8,452(2,5);8,447(2,5);8,264(1,6); 92 1 H-NMR (400.0 M Hz, CD3CN): δ = 8.488 (1.9), 8.477 (2.0), 8.452 (2.5), 8.447 (2.5), 8.264 (1, 6);
8,260(1,6);8,252(1,7);7,728(1,3);7,708( 1,5);7,685(1,6);7,667(1,7);7,410(1,3);7,399(1,4); 8.260 (1.6), 8.252 (1.7), 7.728 (1.3), 7.708 (1.5), 7.685 (1.6), 7.677 (1.7), 7.410 (1.3), 7.399 (1.4);
7,390(1,2);7,378(1,2);7,038(1,4);7,026( 1,6);7,020(1,5);7,008(1,3);6,366(3,7);5,447(1,4);7,390 (1,2), 7,378 (1,2), 7,038 (1,4), 7,026 (1,6), 7,020 (1,5), 7,008 (1,3), 6,366 (3,7), 5,447 (1.4);
4,431(1,3);4,413(3,9);4,396(4,0);4,378( 1,3);3,616(15,8);3,423(16,0);3,020(0,4);2,149(11,9);4.431 (1.3), 4.413 (3.9), 4.396 (4.0), 4.378 (1.3), 3.616 (15.8), 3.423 (16.0), 3.020 (0.4), 2.149 (11.9);
1,951(6,0);1,945(10,7);1,939(13,9);1,933(9,7);1,927(5,0);1,332(4,1); 1,315(8,1);1,297(4,1);1,951 (6.0); 1,945 (10.7); 1,939 (13.9); 1,933 (9.7); 1,927 (5.0); 1,332 (4.1); 1,315 (8.1); 1,297 (4.1);
1,270(0,3) 93 1H-NM (400,0 MHz, CD3CN): δ= 8,482(1,2);8,480(1,2);8,471(1,2);8,468(1,2);8,456(1,8); 8,450(1,7);7,892(2,2);7,888(2,1);7,737(0,8);7,716(0,9);7,408(1,0);7,396(1,0);7,387(0,9); 7,375(0,8);7,343(2,2);7,338(2,1);6,366(2,9);5,447(2,8);3,961(12,8);3,836(16,0);3,424(12,4); 2,151(16,4);1,964(0,5);1,952(7,2);1,946(13,1);1,940(17,7);1,934(12,1);1,928(6,2) 1.270 (0.3) 93 1 H-NM (400.0 MHz, CD3CN): δ = 8.482 (1.2), 8.480 (1.2), 8.471 (1.2), 8.468 (1.2), 8.456 (1.8) ; 8,450 (1.7); 7,892 (2.2); 7,888 (2.1); 7,737 (0.8); 7,716 (0.9); 7,408 (1.0); 7,396 (1.0); 7.387 (0.9); 7,375 (0.8); 7,343 (2.2); 7,338 (2.1); 6,366 (2.9); 5,447 (2.8); 3,961 (12.8); 3.836 (16.0); 3,424 (12.4); 2,151 (16.4); 1,964 (0.5); 1,952 (7.2); 1,946 (13.1); 1,940 (17.7); 1,934 (12.1); 1,928 (6.2)
94 1H-NM (400,0 MHz, CD3CN): δ= 8,481(1,4);8,478(1,4);8,469(1,5);8,466(1,4);8,448(2,0); 94 1 H-NM (400.0 MHz, CD3CN): δ = 8.481 (1.4), 8.478 (1.4), 8.469 (1.5), 8.466 (1.4), 8.448 (2.0) ;
8,442(2,0);8,231(2,0);8,218(2,1);8,032(0,4);7,732(0,8);7,728(0,9);7,726(0,9);7,722(0,7); 8.442 (2.0); 8,231 (2.0); 8,218 (2.1); 8,032 (0.4); 7,732 (0.8); 7,728 (0.9); 7,726 (0.9); 7,722 (0.7);
7,712(0,9);7,708(1,1);7,705(1,0);7,702(0,8);7,400(1,1);7,389(1,1);7,380(1,0);7,368(1,0);7,712 (0.9); 7,708 (1.1); 7,705 (1.0); 7,702 (0.8); 7,400 (1.1); 7,389 (1.1); 7,380 (1.0); 7,368 (1.0);
7,171(1,7);7,168(1,6);7,158(1,6);7,155(1,6);6,968(3,0);6,411(3,1);5,447(0,5);3,924(15,6);7,171 (1.7); 7,168 (1.6); 7,158 (1.6); 7,155 (1.6); 6,968 (3.0); 6,411 (3.1); 5,447 (0.5); 3,924 (15.6);
3,872(16,0);3,425(15,6);1,964(0,4);1,958(0,9);1,952(5,6);1,946(10,3);1,940(14,2);1,934(9,7);3,872 (16.0); 3.425 (15.6); 1,964 (0.4); 1,958 (0.9); 1,952 (5.6); 1,946 (10.3); 1,940 (14.2); 1.934 (9.7);
1,927(5,0);0,000(6,2) 1,927 (5.0); 0,000 (6.2)
95 1H-NMR(400,0 MHz, CD3CN): δ= 8,583(1,6);8,579(1,6);8,485(1,2);8,481(1,3);8,473(1,3); 95 1 H-NMR (400.0 MHz, CD3CN): δ = 8,583 (1.6), 8.579 (1.6), 8.485 (1.2), 8.481 (1.3), 8.473 (1.3) ;
8,469(1,3);8,456(1,7);8,450(1,8);8,162(1,6);8,157(1,6);8,032(1,0);7,744(0,7);7,740(0,8); (1.3) 8.469; 8.456 (1.7); 8,450 (1.8); 8.162 (1.6); 8,157 (1.6); 8,032 (1.0); 7.744 (0.7); 7,740 (0.8);
7,738(0,8);7,734(0,7);7,723(0,8);7,720(0,9);7,717(0,9);7,713(0,8);7,409(1,0);7,397(1,0);7,738 (0.8); 7.734 (0.7); 7,723 (0.8); 7,720 (0.9); 7,717 (0.9); 7,713 (0.8); 7,409 (1.0); 7,397 (1.0);
7,389(0,9);7,377(0,9);6,393(3,0);5,448(10,1);4,059(16,0);3,836(15,4);3,427(15,2);1,958(0,5);7,389 (0.9); 7,377 (0.9); 6,393 (3.0); 5,448 (10.1); 4,059 (16.0); 3.836 (15.4); 3.427 (15.2); 1,958 (0.5);
1,953(3,7);1,946(6,9);1,940(9,5);1,934(6,4);1,928(3,3);0,000(3,8) 1,953 (3.7); 1,946 (6.9); 1,940 (9.5); 1,934 (6.4); 1,928 (3.3); 0,000 (3.8)
96 1H-NMR(400,0 MHz, CD3CN): δ= 8,653(2,6);8,648(2,8);8,496(2,9);8,491(3,1);8,475(1,8); 96 1 H-NMR (400.0 MHz, CD3CN): δ = 8.653 (2.6), 8.648 (2.8), 8.496 (2.9), 8.491 (3.1), 8.475 (1.8) ;
8,472(1,7);8,459(2,3);8,453(2,3);8,024(5,7);7,747(0,9);7,742(1,1);7,738(0,8);7,727(1,0); 8,472 (1.7); 8.459 (2.3); 8,453 (2.3); 8.024 (5.7) 7.747 (0.9); 7,742 (1.1); 7,738 (0.8); 7,727 (1.0);
7,721(1,2);7,718(0,9);7,412(1,2);7,400(1,2);7,391(1,1);7,380(1,0);6,409(3,3);5,447(6,5);7.721 (1.2); 7,718 (0.9); 7,412 (1.2); 7,400 (1.2); 7,391 (1.1); 7,380 (1.0); 6,409 (3.3); 5,447 (6.5);
4,112(16,0);3,857(15,6);3,430(15,4);2,158(0,8);2,153(0,8);2,119(0,7);2,113(0,7);2,107(0,7);4,112 (16.0); 3,857 (15.6); 3,430 (15.4); 2,158 (0.8); 2,153 (0.8); 2,119 (0.7); 2,113 (0.7); 2,107 (0.7);
2,101(0,7);1,964(1,0);1,952(12,1);1,946(22,2);1,940(30,0);1,934(21,2);1,927(11,4);0,000(0,4)2,101 (0.7); 1,964 (1.0); 1,952 (12.1); 1,946 (22.2); 1,940 (30.0); 1,934 (21.2); 1,927 (11.4); 0.000 (0.4)
97 1H-NMR(400,0 MHz, CD3CN): δ= 8,479(0,5);8,468(0,5);8,441(0,7);7,727(0,4);7,723(0,5); 97 1 H-NMR (400.0 MHz, CD3CN): δ = 8.479 (0.5), 8.468 (0.5), 8.441 (0.7), 7.727 (0.4), 7.723 (0.5) ;
7,721(0,5);7,717(0,4);7,707(0,5);7,703(0,5);7,700(0,5);7,697(0,4);7,400(0,5);7,388(0,5); 7,379(0,4);7,367(0,4);6,524(5,3);6,385(1,3);5,447(1,2);3,922(16,0);3,877(0,5);3,849(8,2); 3,419(8,1);2,152(0,9);1,952(2,9);1,946(5,3);1,940(7,2);1,934(5,0);1,927(2,6);0,000(1,2) 7.721 (0.5); 7,717 (0.4); 7,707 (0.5); 7,703 (0.5); 7,700 (0.5); 7,697 (0.4); 7,400 (0.5); 7,388 (0.5); 7,379 (0.4); 7,367 (0.4); 6.524 (5.3); 6,385 (1.3); 5,447 (1.2); 3,922 (16.0); 3,877 (0.5); 3,849 (8.2); 3,419 (8.1); 2,152 (0.9); 1,952 (2.9); 1,946 (5.3); 1,940 (7.2); 1,934 (5.0); 1,927 (2.6); 0,000 (1,2)
98 1H-NMR(400,0 MHz, CD3CN): δ= 8,491(0,3);8,488(0,4);8,479(0,4);8,476(0,4);8,463(0,5); 98 1 H-NMR (400.0 MHz, CD3CN): δ = 8.491 (0.3), 8.488 (0.4), 8.479 (0.4), 8.466 (0.4), 8.463 (0.5) ;
8,457(0,5);7,396(0,6);7,376(0,5);7,251(0,4);7,248(0,4);7,233(0,8);7,229(0,6);6,374(0,8); 5,447(0,8);3,559(3,9);3,425(3,9);2,629(1,2);2,382(3,7);2,150(2,3);1,952(1,8);1,945(3,3); 1,939(4,6);1,933(3,2);1,927(1,7);1,134(16,0);0,000(1,0)  8.457 (0.5); 7,396 (0.6); 7,376 (0.5); 7,251 (0.4); 7,248 (0.4); 7,233 (0.8); 7,229 (0.6); 6,374 (0.8); 5,447 (0.8); 3,559 (3.9); 3,425 (3.9); 2,629 (1.2); 2,382 (3.7); 2,150 (2.3); 1,952 (1.8); 1,945 (3.3); 1,939 (4.6); 1,933 (3.2); 1,927 (1.7); 1,134 (16.0); 0,000 (1.0)
99 1H-NMR(400,0 MHz, CD3CN): δ= 8,481(1,3);8,478(1,3);8,470(1,4);8,467(1,3);8,446(1,9); 99 1 H NMR (400.0 MHz, CD3CN): δ = 8.481 (1.3); 8.478 (1.3); 8.470 (1.4); 8.467 (1.3); 8.446 (1.9) ;
8,440(1,9);7,734(0,8);7,730(1,0);7,728(0,9);7,724(0,8);7,714(0,9);7,710(1,1);7,707(1,1); 8,440 (1.9); 7.734 (0.8); 7,730 (1.0); 7,728 (0.9); 7,724 (0.8); 7,714 (0.9); 7,710 (1.1); 7,707 (1,1);
7,704(0,9);7,604(3,1);7,401(1,1);7,389(1,1);7,380(1,0);7,368(1,0);7,219(3,0);6,447(2,7);7.704 (0.9); 7,604 (3.1); 7,401 (1.1); 7,389 (1.1); 7,380 (1.0); 7,368 (1.0); 7,219 (3.0); 6,447 (2.7);
5,447(2,1);3,979(15,7);3,904(16,0);3,430(15,7);2,138(5,8);1,964(0,6);1,952(8,2);1,946(15,1);5,447 (2.1); 3,979 (15.7); 3,904 (16.0); 3,430 (15.7); 2,138 (5.8); 1,964 (0.6); 1,952 (8.2); 1,946 (15,1);
1,940(20,1);1,934(13,8);1,927(7,1);0,000(4,5) 1,940 (20.1); 1,934 (13.8); 1,927 (7.1); 0,000 (4.5)
100 1H-NMR(400,0 MHz, CD3CN): δ= 8,485(1,4);8,482(1,5);8,473(1,5);8,470(1,6);8,453(2,1); 100 1 H-NMR (400.0 MHz, CD3CN): δ = 8.485 (1.4), 8.482 (1.5), 8.473 (1.5), 8.470 (1.6), 8.453 (2.1) ;
8,447(2,2);8,028(0,7);7,740(0,8);7,736(1,0);7,734(1,0);7,730(0,9);7,720(1,0);7,714(1,2); 8,447 (2.2); 8,028 (0.7); 7,740 (0.8); 7,736 (1.0); 7.734 (1.0); 7,730 (0.9); 7,720 (1.0); 7,714 (1,2);
7,710(1,0);7,517(3,2);7,406(2,8);7,399(2,3);7,387(1,2);7,375(1,1);7,363(2,0);7,360(2,2);7.710 (1.0); 7,517 (3.2); 7,406 (2.8); 7,399 (2.3); 7.387 (1.2) 7.375 (1.1); 7,363 (2.0); 7,360 (2,2);
7,354(1,7);6,392(3,3);5,447(5,3);3,861(15,8);3,839(16,0);3,426(15,9);2,151(0,4);2,135(0,3);7,354 (1.7); 6,392 (3.3); 5,447 (5.3); 3,861 (15.8); 3,839 (16.0); 3,426 (15.9); 2,151 (0.4); 2,135 (0.3);
2,113(0,3);2,107(0,3);1,964(0,5);1,952(6,2);1,946(11,6);1,940(15,8);1,934(11,2);1,927(5,9);2,113 (0.3); 2,107 (0.3); 1,964 (0.5); 1,952 (6.2); 1,946 (11.6); 1,940 (15.8); 1,934 (11.2); 1,927 (5.9);
0,000(3,1) 0.000 (3.1)
101 1H-NMR(400,0 MHz, CD3CN): δ= 8,496(1,4);8,493(1,4);8,485(1,5);8,481(1,4);8,455(1,9); 101 1 H-NMR (400.0 MHz, CD3CN): δ = 8.496 (1.4), 8.493 (1.4), 8.485 (1.5), 8.481 (1.4), 8.455 (1.9) ;
8,449(1,9);8,180(2,4);8,172(2,4);7,738(0,8);7,734(0,9);7,731(0,9);7,728(0,8);7,718(0,9); 8,449 (1.9); 8,180 (2.4); 8,172 (2.4); 7,738 (0.8); 7.734 (0.9); 7,731 (0.9); 7,728 (0.8); 7,718 (0.9);
7,714(1,1);7,711(1,0);7,707(0,8);7,562(1,3);7,554(1,3);7,541(1,4);7,534(1,3);7,417(1,1);7,714 (1.1); 7.711 (1.0); 7,707 (0.8); 7,562 (1.3); 7,554 (1.3); 7,541 (1.4); 7,534 (1.3); 7,417 (1,1);
7,405(1,1);7,396(1,0);7,384(1,0);6,387(2,9);5,447(5,1);3,914(16,0);3,611(15,9);3,423(15,6);7,405 (1.1); 7,396 (1.0); 7,384 (1.0); 6,387 (2.9); 5,447 (5.1); 3,914 (16.0); 3,611 (15.9); 3.423 (15.6);
2,166(0,4);2,156(0,4);1,964(0,6);1,952(6,0);1,946(10,9);1,939(14,7);1,933(10,1);1,927(5,3);2,166 (0.4); 2,156 (0.4); 1,964 (0.6); 1,952 (6.0); 1,946 (10.9); 1,939 (14.7); 1,933 (10.1); 1,927 (5.3);
0,000(2,0) 0.000 (2.0)
102 1H-NMR(400,0 MHz, d5-DMSO): δ= 8,541(2,1);8,535(2,2);8,501(1,5);8,498(1,6);8,489(1,7); 102 1 H NMR (400.0 MHz, d 5 -DMSO): δ = 8.541 (2.1), 8.535 (2.2), 8.501 (1.5), 8.498 (1.6), 8.489 (1 , 7);
8,486(1,6);8,416(2,3);8,411(2,4);8,138(2,1);7,948(1,5);7,942(1,4);7,927(1,6);7,921(1,5); 8.486 (1.6) 8.416 (2.3); 8,411 (2.4); 8,138 (2.1); 7,948 (1.5); 7,942 (1.4); 7.927 (1.6); 7,921 (1.5);
7,901(0,9);7,898(1,1);7,895(1,0);7,891(0,9);7,881(1,0);7,877(1,1);7,875(1,1);7,871(0,9); 7,487(1,1);7,475(1,2);7,466(1,1);7,454(1,0);6,852(2,2);6,830(2,2);6,356(3,5);5,757(5,6);7.901 (0.9); 7,898 (1.1); 7.895 (1.0); 7,891 (0.9); 7,881 (1.0); 7.877 (1.1); 7,875 (1.1); 7,871 (0.9); 7,487 (1.1); 7,475 (1.2); 7,466 (1.1); 7,454 (1.0); 6,852 (2.2); 6,830 (2.2); 6,356 (3.5); 5,757 (5,6);
5,331(0,4);5,315(1,2);5,300(1,6);5,284(1,2);5,269(0,5);3,826(14,7);3,405(13,9);3,323(1,3);5,331 (0.4); 5,315 (1.2); 5,300 (1.6); 5,284 (1.2); 5,269 (0.5); 3,826 (14.7); 3.405 (13.9); 3.323 (1,3);
2,507(33,2);2,502(42,2);2,498(31,1);1,321(16,0);1,306(15,9);1,285(0,9);1,270(0,6);0,000(0,9)2,507 (33.2); 2.502 (42.2); 2,498 (31.1); 1.321 (16.0); 1.306 (15.9); 1,285 (0.9); 1,270 (0.6); 0,000 (0.9)
103 1H-NM (400,0 MHz, CD3CN): δ= 8,482(1,4);8,479(1,4);8,470(1,5);8,467(1,4);8,457(2,0); 103 1 H-NM (400.0 MHz, CD3CN): δ = 8.482 (1.4), 8.479 (1.4), 8.470 (1.5), 8.467 (1.4), 8.457 (2.0) ;
8,451(2,0);8,370(1,9);8,365(2,0);7,865(1,4);7,859(1,3);7,844(1,4);7,838(1,4);7,738(0,8); 7,734(0,9);7,732(0,9);7,728(0,7);7,718(0,9);7,714(1,0);7,711(1,0);7,708(0,8);7,406(1,0); 7,394(1,1);7,385(1,0);7,373(0,9);6,865(2,0);6,843(1,9);6,364(3,4);3,936(16,0);3,815(15,5); 8.451 (2.0); 8,370 (1.9); 8.365 (2.0); 7,865 (1.4); 7,859 (1.3); 7,844 (1.4); 7,838 (1.4); 7,738 (0.8); (0.9) 7.734; 7,732 (0.9); 7,728 (0.7); 7,718 (0.9); 7,714 (1.0); 7.711 (1.0); 7,708 (0.8); 7,406 (1.0); 7,394 (1.1); 7,385 (1.0); 7,373 (0.9); 6,865 (2.0); 6,843 (1.9); 6,364 (3.4); 3,936 (16.0); 3,815 (15.5);
3,422(15,2);2,156(8,4);1,964(0,6);1,952(7,0);1,946(12,8);1,940(17,1);1,934(11,9);1,927(6,1); 0,000(0,7) 3,422 (15.2); 2,156 (8.4); 1,964 (0.6); 1,952 (7.0); 1,946 (12.8); 1,940 (17.1); 1,934 (11.9); 1,927 (6.1); 0.000 (0.7)
104 1H-NM (400,0 MHz, CD3CN): δ= 8,496(1,4);8,486(1,5);8,468(2,1);8,462(2,1);8,030(0,4); 104 1 H-NM (400.0 MHz, CD3CN): δ = 8.496 (1.4), 8.486 (1.5), 8.468 (2.1), 8.462 (2.1), 8.030 (0.4) ;
7,747(1,0);7,726(1,2);7,507(0,7);7,503(0,7);7,484(1,4);7,467(0,9);7,463(0,9);7,420(1,2); 7.747 (1.0); 7,726 (1.2); 7,507 (0.7); 7,503 (0.7); 7,484 (1.4); 7,467 (0.9); 7,463 (0.9); 7,420 (1,2);
7,408(1,2);7,400(1,1);7,388(1,0);7,367(1,4);7,364(1,4);7,348(1,7);7,345(1,6);7,298(0,4);7,408 (1.2); 7,400 (1.1); 7,388 (1.0); 7,367 (1.4); 7,364 (1.4); 7,348 (1.7); 7,345 (1.6); 7,298 (0.4);
7,136(1,1);7,117(1,9);7,102(2,4);7,082(1,8);6,451(0,3);6,388(2,7);5,897(0,4);4,498(9,6);7,136 (1.1); 7,117 (1.9); 7,102 (2.4); 7,082 (1.8); 6,451 (0.3); 6,388 (2.7); 5,897 (0.4); 4,498 (9.6);
3,946(1,6);3,686(14,2);3,430(16,0);3,417(1,9);2,298(0,5);2,183(1,0);2,179(1,0);2,113(0,6);3,946 (1.6); 3,686 (14.2); 3,430 (16.0); 3,417 (1.9); 2,298 (0.5); 2,183 (1.0); 2,179 (1.0); 2,113 (0.6);
2,107(0,6);2,101(0,5);1,964(9,7);1,952(8,6);1,946(15,3);1,939(20,5);1,933(14,5);1,927(7,7);2,107 (0.6); 2,101 (0.5); 1,964 (9.7); 1,952 (8.6); 1,946 (15.3); 1,939 (20.5); 1,933 (14.5); 1,927 (7.7);
1,134(2,1);0,000(0,5) 1,134 (2.1); 0,000 (0.5)
105 1H-NMR(400,0 MHz, CD3CN): δ= 8,481(1,5);8,477(1,4);8,469(1,6);8,465(1,4);8,451(2,0); 105 1 H-NMR (400.0 MHz, CD3CN): δ = 8.481 (1.5); 8.477 (1.4); 8.469 (1.6); 8.465 (1.4); 8.451 (2.0) ;
8,445(2,0);7,826(2,0);7,821(2,9);7,807(1,7);7,801(1,0);7,785(1,6);7,779(1,2);7,732(0,9); 8,445 (2.0); 7,826 (2.0); 7.821 (2.9); 7,807 (1.7); 7,801 (1.0); 7,785 (1.6); 7,779 (1.2); 7,732 (0.9);
7,729(1,0);7,726(0,9);7,722(0,7);7,712(1,0);7,708(1,1);7,705(1,1);7,702(0,8);7,403(1,1);7,729 (1.0); 7,726 (0.9); 7,722 (0.7); 7,712 (1.0); 7,708 (1.1); 7,705 (1.1); 7,702 (0.8); 7,403 (1,1);
7,391(1,1);7,382(1,0);7,370(1,0);7,217(2,1);7,195(2,0);6,349(3,5);5,447(3,6);4,842(0,4);(1.1) 7,391; 7,382 (1.0); 7,370 (1.0); 7,217 (2.1); 7,195 (2.0); 6,349 (3.5); 5,447 (3.6); 4,842 (0.4);
4,827(1,0);4,812(1,3);4,797(1,0);4,782(0,4);3,811(16,0);3,420(15,7);2,148(7,5);1,952(4,8);4,827 (1.0); 4,812 (1.3); 4,797 (1.0); 4,782 (0.4); 3,811 (16.0); 3.420 (15.7); 2,148 (7.5); 1,952 (4.8);
1,946(9,0);1,940(12,3);1,934(8,4);1,927(4,2);1,390(15,6);1,375(15,4);1,312(0,5);1,297(0,5);1,946 (9.0); 1,940 (12.3); 1,934 (8.4); 1,927 (4.2); 1,390 (15.6); 1.375 (15.4); 1,312 (0.5); 1,297 (0.5);
0,008( 1,5 );0,000(36,5 );-0,009( 1,4) 0.008 (1.5); 0.000 (36.5); - 0.009 (1.4)
106 1H-NMR(400,0 MHz, d5-DMSO): δ= 8,670(1,6);8,667(2,0);8,658(1,8);8,655(2,0);8,565(2,5); 106 1 H NMR (400.0 MHz, d 5 -DMSO): δ = 8.670 (1.6), 8.667 (2.0), 8.658 (1.8), 8.655 (2.0), 8.565 (2 , 5);
8,559(2,6);8,508(1,5);8,504(1,9);8,496(1,7);8,493(1,9);8,135(1,7);8,132(2,0);8,114(1,9); 8,559 (2.6); 8,508 (1.5); 8,504 (1.9); 8,496 (1.7); 8,493 (1.9); 8,135 (1.7); 8,132 (2.0); 8,114 (1.9);
8,111(2,1);7,911(0,8);7,908(1,1);7,905(1,2);7,902(1,0);7,891(1,0);7,887(1,2);7,885(1,3);8,111 (2.1); 7,911 (0.8); 7,908 (1.1); 7,905 (1.2); 7,902 (1.0); 7,891 (1.0); 7,887 (1.2); 7,885 (1,3);
7,881(1,1);7,596(1,7);7,585(1,6);7,576(1,6);7,564(1,5);7,489(1,3);7,478(1,4);7,469(1,3);7,881 (1.1); 7,596 (1.7); 7,585 (1.6); 7,576 (1.6); 7,564 (1.5); 7,489 (1.3); 7,478 (1.4); 7.469 (1,3);
7,457(1,2);6,424(2,7);3,701(16,0);3,419(15,0);3,322(10,9);2,956(0,4);2,671(0,4);2,506(42,3);7.457 (1.2); 6,424 (2.7); 3,701 (16.0); 3,419 (15.0); 3.322 (10.9); 2,956 (0.4); 2,671 (0.4); 2,506 (42.3);
2,502(57,2);2,497(45,9);2,328(0,3);0,007(2,1);0,000(49,3) 2,502 (57.2); 2.497 (45.9); 2.328 (0.3) 0.007 (2.1) 0.000 (49.3)
Anwendungsbeispiele applications
Meloidogyne incognita- Test Meloidogyne incognita test
Lösungsmittel: 125,0 Gewichtsteile Aceton  Solvent: 125.0 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße werden mit Sand, Wirkstofflösung, einer Ei-Larven-Suspension des südlichen Wurzelgallen- älchens (Meloidogyne incognita) und Salatsamen gefüllt. Die Salatsamen keimen und die Pflänzchen entwickeln sich. An den Wurzeln entwickeln sich die Gallen. Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.
Nach 14 Tagen wird die nematizide Wirkung anhand der Gallenbildung in % bestimmt. Dabei bedeutet 100 %, dass keine Gallen gefunden wurden; 0 % bedeutet, dass die Zahl der Gallen an den behandelten Pflanzen der unbehandelten Kontrolle entspricht. After 14 days, the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20ppm: 83 Tetranychus urticae - Sprühtest, OP-resistent  In this test, z. For example, the following compounds of the Preparation Examples Effect of 100% at an application rate of 20 ppm: 83 Tetranychus urticae - spray test, OP-resistant
Lösungsmittel: 78,0 GewichtsteileAceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator : Alkylarylpolyglykolether 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 Emulgatorkon- zentration 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 the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. 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. After 6 days, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 500g/ha: 105 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 500g/ha: 52, 57, 72 Myzus persicae - Sprühtest In this test, z. Example, the following compounds of the preparation examples an effect of 100% at a rate of 500g / ha: 105 In this test, for. For example, the following compounds of the Preparation Examples have an effect of 90% at a rate of 500g / ha: 52, 57, 72 Myzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: 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 Emulgatorkon- zentration 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 the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 6 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung vonIn this test, z. B. the following compounds of the preparation of the effect of
100% bei einer Aufwandmenge von 500g/ha: 1, 6, 9, 16, 21, 22, 23, 33, 38, 48, 52, 57, 58, 61, 62, 65, 67, 68, 69, 71, 73, 74, 75, 77, 79, 80, 81, 82, 84, 87, 95, 97, 101, 103, 104 100% at an application rate of 500 g / ha: 1, 6, 9, 16, 21, 22, 23, 33, 38, 48, 52, 57, 58, 61, 62, 65, 67, 68, 69, 71, 73, 74, 75, 77, 79, 80, 81, 82, 84, 87, 95, 97, 101, 103, 104
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung vonIn this test, z. B. the following compounds of the preparation of the effect of
90% bei einer Aufwandmenge von 500g/ha: 2, 3, 4, 5, 7, 10, 11, 13, 14, 15, 17, 18, 19, 20, 24, 25, 26, 27, 28, 29, 30, 31, 32, 35, 36, 37, 39, 40, 44, 45, 47, 53, 54, 55, 56, 59, 60, 63, 64, 66, 76, 78, 83, 86, 88, 89, 90, 91, 92, 93, 94, 99, 100, 102, 105, 106 90% at a rate of 500g / ha: 2, 3, 4, 5, 7, 10, 11, 13, 14, 15, 17, 18, 19, 20, 24, 25, 26, 27, 28, 29, 30, 31, 32, 35, 36, 37, 39, 40, 44, 45, 47, 53, 54, 55, 56, 59, 60, 63, 64, 66, 76, 78, 83, 86, 88, 89, 90, 91, 92, 93, 94, 99, 100, 102, 105, 106
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 100g ha: 8 In this test, z. Example, the following compounds of the preparation examples effect of 90% at a rate of 100g ha: 8
Myzus persicae - Oraltest Myzus persicae - Oraltest
Lösungsmittel: 100 Gewichtsteile Aceton  Solvent: 100 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser bis zum Erreichen der gewünschten Konzentration auf. 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 until the desired concentration is reached.
50 μΐ der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150μ1 50 μΐ of the active ingredient preparation are transferred into microtiter plates and with 150μ1
IPL41 Insektenmedium (33% + 15% Zucker) auf eine Endvolumen von 200 μΐ aufgefüllt. Anschließend werden die Platten mit Parafilm verschlossen, durch den eine gemischte Population der Grünen Pfirsichblattlaus (Myzus persicae), die sich in einer zweiten Mikrotiterplatte befindet, hindurchstechen und die Lösung aufnehmen kann. Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. IPL41 insect medium (33% + 15% sugar) to a final volume of 200 μΐ filled. Subsequently, the plates are sealed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 33, 36, 38, 39, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 20 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 , 18, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 33, 36, 38, 39, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55 , 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80 , 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 20ppm: 19, 32, 35, 37, 44, 45, 106 Myzus persicae - Sprühtest In this test, z. For example, the following compounds of the Preparation Examples Effect of 90% at a rate of 20ppm: 19, 32, 35, 37, 44, 45, 106 Myzus persicae - spray test
Lösungsmittel: 14 Gewichtsteile Dimethylformamid Solvent: 14 parts by weight of dimethylformamide
Emulgator : Alkylary lpolyglykolether  Emulsifier: Alkylary polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkon- zentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt. 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 the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
Paprikapflanzen (Capsicum annuum), die stark von der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt. Paprika plants (Capsicum annuum) which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.
Nach 6 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Läuse abgetötet wurden; 0 % bedeutet, dass keine Läuse abgetötet wurden. After 6 days the kill is determined in%. 100% means that all lice have been killed; 0% means that no lice have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20ppm: 12, 49, 50, 51, 77 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 20 ppm: 12, 49, 50, 51, 77
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 95% bei einer Aufwandmenge von 20ppm: 46, 70 Absetzbeispiele In this test, z. Example, the following compounds of the preparation examples effect of 95% at a rate of 20 ppm: 46, 70th Absetzbeispiele
Myzus persicae - Sprühtest (MYZUPE)  Myzus persicae - spray test (MYZUPE)
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkon- zentration 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 the desired concentration is reached. 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 der gewünschten Zeit 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 überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 3 After the desired time, 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. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 3
Myzus persicae - Oraltest (MYZUPE O) Myzus persicae - Oral test (MYZUPE O)
Lösungsmittel: 100 Gewichtsteile Aceton Solvent: 100 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser bis zum Erreichen der gewünschten Konzentration auf. 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 until the desired concentration is reached.
50 μΐ der Wirkstoffzubereitung werden in Mikro titerplatten überführt und mit 150μ1 IPL41 Insektenmedium (33% + 15% Zucker) auf eine Endvolumen von 200 μΐ aufgefüllt. Anschließend werden die Platten mit Parafilm verschlossen, durch den eine gemischte Population der Grünen Pfirsichblattlaus (Myzus persicae), die sich in einer zweiten Mikrotiterplatte befindet, hindurchstechen und die Lösung aufnehmen kann. 50 μΐ of the active ingredient preparation are transferred to microtiter plates and filled with 150 μl IPL41 insect medium (33% + 15% sugar) to a final volume of 200 μΐ. Subsequently, the plates are sealed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution.
Nach 5 oder 6 Tagen (dat) wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 5 or 6 days (dat), the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 3 In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 3
Tabelle 3: Substanz Struktur Tierart Konzentration % Wirkung datTable 3: Substance structure species concentration% effect dat
Vergleichsbsp.1 0 MYZUPE 100gai/ha 0 5/6 dat WO2011/009804 MYZUPEO 4 ppm 0 5 dat Comparative 1 0 MYZUPE 100gai / ha 0 5/6 dat WO2011 / 009804 MYZUPEO 4 ppm 0 5 dat
Vergleichsbsp.2 0 MYZUPE 100gai/ha 0 6 dat WO2011/009804 MYZUPEO 4 ppm 0 5 dat Comparative spec.2 0 MYZUPE 100gai / ha 0 6 dat WO2011 / 009804 MYZUPEO 4 ppm 0 5 dat
Bsp. Nr.1 MYZUPEO 4 ppm 100 5 dat Erfindungsgemäß Ex. No. 1 MYZUPEO 4 ppm 100 5 dat According to the invention
Bsp. Nr.4 MYZUPE 100gai/ha 90 6 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Example No. 4 MYZUPE 100gai / ha 90 6 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp. Nr.6 MYZUPE 100gai/ha 90 6 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Example No. 6 MYZUPE 100gai / ha 90 6 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp.Nr.11 MYZUPE 100gai/ha 90 6 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Ex.11 MYZUPE 100gai / ha 90 6 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp.Nr.16 MYZUPE 100gai/ha 90 6 dat Erfindungsgemäß (TT i r MYZUPEO 4 ppm 100 5 dat Ex.16 MYZUPE 100gai / ha 90 6 dat According to the invention (TT i r MYZUPEO 4 ppm 100 5 dat
Bsp.Nr.55 MYZUPE 100gai/ha 90 6 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Ex.55 MYZUPE 100gai / ha 90 6 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp.Nr.64 MYZUPE 100gai/ha 90 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat 64 MYZUPE 100gai / ha 90 5 dat Inventive MYZUPEO 4 ppm 100 5 dat
Bsp.Nr.65 MYZUPE 100gai/ha 90 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Bsp. Nr.68 MYZUPE 100gai/ha 100 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Example No.65 MYZUPE 100gai / ha 90 5 dat According to the invention MYZUPEO 4 ppm 100 5 dat Example No. 68 MYZUPE 100gai / ha 100 5 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp. Nr.78 MYZUPE 100gai/ha 70 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Ex. No. 78 MYZUPE 100gai / ha 70 5 dat According to the invention MYZUPEO 4 ppm 100 5 dat
Bsp. Nr.81 MYZUPE 100gai/ha 70 5 dat Erfindungsgemäß MYZUPEO 4 ppm 70 5 dat Ex. No. 81 MYZUPE 100gai / ha 70 5 dat According to the invention MYZUPEO 4 ppm 70 5 dat
Bsp. Nr.87 MYZUPE 100gai/ha 90 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Ex. No. 87 MYZUPE 100gai / ha 90 5 dat According to the invention MYZUPEO 4 ppm 100 5 dat
\  \
Bsp. Nr.99 MYZUPE 100gai/ha 70 5 dat Erfindungsgemäß MYZUPEO 4 ppm 100 5 dat Ex. No. 99 MYZUPE 100gai / ha 70 5 dat According to the invention MYZUPEO 4 ppm 100 5 dat

Claims

Patentansprüche claims
in welcher  in which
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
V für einen Rest aus der Reihe Wasserstoff, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halo- genalkoxy und Cyano steht, V is a radical selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
W für einen Rest aus der Reihe Wasserstoff, Halogen, Alkyl, Halogenalkyl, Alkoxy, Halo- genalkoxy und Cyano steht, W is a radical selected from among hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and cyano,
X für einen Rest aus der Reihe gegebenenfalls substituiertes Aryl oder Hetaryl steht, X is a radical from the series optionally substituted aryl or hetaryl,
Y für einen Rest aus der Reihe Wasserstoff, Cyano, gegebenenfalls substituiertes Alkyl, Alkenyl, oderAlkinyl, gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkyl und gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkylalkyl, Arylalkyl oder Hetarylalkyl steht, Y is a radical selected from the group consisting of hydrogen, cyano, optionally substituted alkyl, alkenyl, or alkynyl, optionally interrupted by heteroatoms and optionally substituted cycloalkyl and optionally interrupted by heteroatoms and optionally substituted cycloalkylalkyl, arylalkyl or hetarylalkyl,
A für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl oder Alkinyl und gegebenenfalls durch Heteroatome unterbrochenes und gegebenenfalls substituiertes Cycloalkyl oder Cycloalkylalkyl steht, A is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl or alkynyl and optionally interrupted by heteroatoms and optionally substituted cycloalkyl or cycloalkylalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
2. Verbindung nach Anspruch 1, bei der Q für Sauerstoff oder Schwefel steht, V für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C t-Alkyl, Ci-C t-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy und Cyano steht, A compound according to claim 1, wherein Q is oxygen or sulfur, V is a radical selected from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and cyano,
W für einen Rest aus der Reihe Wasserstoff, Halogen, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Halogenalkoxy und Cyano steht, W 4 haloalkoxy and cyano represents a radical from the series hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C,
X für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinander durch X is a radical from the series optionally mono- to polysubstituted independently of one another
Halogen, NI^L2, Nitro, Cyano oder gegebenenfalls substituiertes Alkyl, Halogenalkyl, Alkoxy, Alkyl-S(0)m-, Halogenalkoxy, Halogenalkyl-S(0)m-, Carboxy, Aryl oder Heta- ryl substituiertes Aryl oder Hetaryl steht oder für einenen Aryl oder Hetarylring steht, welcher an zwei benachbarten Ringpositionen eine aus einem bis zwei Heteroatomen aus der Reihe N, S oder O und/oder einem bis fünf Kohlenstoffatomen bestehnde Kette gebunden hat und diese dabei einen gegen- enefalls teilweise ungesättigten aliphatischen, aromatischen, heteroaromatischen oder gegebenenfalls teilweise ungesättigten heterocyclischen Ring bildet, wobei Halogen, NI ^ L 2 , nitro, cyano or optionally substituted alkyl, haloalkyl, alkoxy, alkyl-S (0) m -, haloalkoxy, haloalkyl-S (0) m -, carboxy, aryl or hetero-substituted aryl or hetaryl or stands for an aryl or hetaryl ring which has attached to two adjacent ring positions a chain which consists of one or two heteroatoms from the series N, S or O and / or one to five carbon atoms and which thereby has an oppositely partially unsaturated aliphatic, forms aromatic, heteroaromatic or optionally partially unsaturated heterocyclic ring, wherein
L1 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, L 1 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl,
L2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, oder L 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättigten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht, L 1 and L 2 together with N represents an optionally substituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms bonded via N,
Y für einen Rest aus der Reihe Wasserstoff, Methyl, Cyano, gegebenenfalls einfach bis mehrfach unabhängig voneinander durch Halogen, C1-C4- Alkoxy, Ci-C4-Alkyl-S(0)m- oder Cyano substituiertes Ci-Cö-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes Cs-Cs-Cycloalkyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch O, S(0)m, CO oder NR2 unterbrochenes und gegebenenfalls einfach bis vierfach unabhängig voneinander durch Halogen, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C8-Cycloalkyl-Ci-C4-alkyl und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, Ci-C4-Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Nitro oder Cyano substituiertes Arylalkyl oder Hetarylalkyl steht, m für eine Zahl 0, 1 oder 2 steht, Y is a radical selected from hydrogen, methyl, cyano, optionally mono- or polysubstituted independently of one another by halogen, C 1 -C4- alkoxy, Ci-C 4 alkyl-S (0) m - or cyano-substituted C-alkyl COE , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally mono- or disubstituted independently of one another by halogen, C 1 -C4- alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano-substituted Cs-Cs-cycloalkyl, optionally mono- or disubstituted independently of one another by O, S (0 ) m, CO or NR 2 is interrupted and is optionally mono- to tetrasubstituted independently of one another by halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy or cyano, straight or branched C 3 -C 8 cycloalkyl-Ci-C4-alkyl and which is optionally mono- to trisubstituted independently of one another by halogen, C 1 -C 4 - alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 alkyl-S ( 0) m -, Ci-C4-haloalkoxy, Ci-C4-haloalkyl-S (0) m -, nitro or cyano substituted arylalkyl or hetarylalkyl, m represents a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, gegebenenfalls einfach bis mehrfach unabhängig voneinander durch Halogen, C1-C4- Alkoxy, Ci-C4-Alkyl-S(0)m- oder Cyano substituiertes Ci-Cö-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes C3-C6-Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C8-Cycloalkyl-Ci-C4-alkyl steht, A represents a radical selected from hydrogen, methyl, which is optionally monosubstituted to polysubstituted independently of one another by halogen, C 1 -C 4 - 4 alkyl-S alkoxy, Ci-C (0) m - or cyano-substituted Ci-COE-alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl and optionally mono- or disubstituted independently of one another by halogen, C 1 -C 4 - alkyl, Ci-C4-haloalkyl, Ci-C 4 alkoxy or cyano-substituted C 3 - C6 cycloalkyl, and optionally mono- or disubstituted independently of one another by halogen, C 1 -C4- alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy or cyano, straight or branched C 3 -C 8 cycloalkyl-Ci- C 4 alkyl,
R2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
3. Verbindung nach Anspruch 1, bei der Q für Sauerstoff oder Schwefel steht, V für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluor- methyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy und Cyano steht, A compound according to claim 1, wherein Q is oxygen or sulfur, V is a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano,
W für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluor- methyl, Trifluormethyl, Methoxy, Ethoxy, Difluormethoxy, Trifluormethoxy und Cyano steht, W is a radical selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy and cyano,
X für einen Rest aus der Reihe gegebenenfalls einfach bis mehrfach unabhängig voneinander durch X is a radical from the series optionally mono- to polysubstituted independently of one another
Halogen, Ci-C4-Alkyl, Ci-C -Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, C1-C4- Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Ci-C4-Carboxy, NI^L2, Nitro, Cyano oder gegebenenfalls einfach bis dreifach unabhängig voneinander durch Halogen, C1-C4- Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy, Ci-C4-Alkyl-S(0)m-, Ci-C4-Halogenalkoxy, Ci-C4-Halogenalkyl-S(0)m-, Nitro oder Cyano substituiertes Aryl oder Hetaryl substituiertes Aryl oder Hetaryl steht oder für einenen Aryl oder Hetarylring steht, welcher an zwei benachbarten Ringpositionen eine aus einem oder zwei Heteroatomen aus der Reihe N, S oder O und einem oder zwei Kohlenstoffatomen bestehende Kette gebunden hat und diese dabei einen heteroaromatischen oder gegebenefalls teilweise ungesättigten heterocyclischen Ring bildet, wobei Halogen, C 1 -C 4 -alkyl, C 1 -C -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl-S (O) m -, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl-S ( 0) m -, Ci-C 4 -Carboxy, NI ^ L 2 , nitro, cyano or optionally monosubstituted to trisubstituted independently by halogen, C 1 -C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy , Ci-C 4 alkyl-S (0) m -, C 4 haloalkoxy, Ci-C 4 haloalkyl-S (0) m -, nitro or cyano-substituted aryl or hetaryl substituted aryl or hetaryl or is an aryl or hetaryl ring which has bonded to two adjacent ring positions a consisting of one or two heteroatoms from the series N, S or O and one or two carbon atoms, thereby forming a heteroaromatic or optionally partially unsaturated heterocyclic ring, wherein
L1 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2- C4-Alkenyl, C2-C4-Alkinyl oder C3-C6-Cycloalkyl steht, L 1 is a radical selected from hydrogen, optionally substituted Ci-C 4 alkyl, C 2 - C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 cycloalkyl,
L2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Ci-C4-Alkyl, C2- C4-Alkenyl, C2-C4-Alkinyl oder C3-C6-Cycloalkyl steht, oder L 2 is a radical selected from hydrogen, optionally substituted Ci-C 4 alkyl, C 2 C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 cycloalkyl, or
L1 und L2 zusammen mit N für einen über N gebundenen, gegebenenfalls substituierten gesättigten, teilweise gesättigten oder aromatischen Heterocyclus mit 3 bis 7 Ringatomen steht, für einen Rest aus der Reihe Wasserstoff, Cy; gegebenenfalls einfach bis fünffach unabhängig voneinander durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m- oderCyano substituiertes Ci-C4-Alkyl, C3-C4-Alkenyl oder C3-C4-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes C3-C6- Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch O, S(0)m, CO oder NR2 unterbrochenes und gegebenenfalls einfach bis vierfach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C6-Cycloalkyl-Ci-C2-alkyl steht, m für eine Zahl 0, 1 oder 2 steht, L 1 and L 2 together with N represents an optionally substituted unsubstituted saturated, partially saturated or aromatic heterocycle having 3 to 7 ring atoms, a radical selected from the group consisting of hydrogen, Cy; which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci-C4 alkyl, C3-C4 alkenyl, or C 3 -C 4 -alkynyl, optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C 6 -cycloalkyl and optionally mono- to disubstituted independently of one another by O, S (0) m , CO or NR 2 interrupted, optionally monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano, straight-chain or branched C 3 -C 6 cycloalkyl-Ci-C 2- alkyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, gegebenenfalls einfach bis fünffach unabhängig voneinander durch Fluor, Chlor, Brom, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m- oder Cyano substituiertes Ci-Ce-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl, gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes C3-C6- Cycloalkyl und gegebenenfalls einfach bis zweifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Methoxy, Ethoxy oder Cyano substituiertes, geradkettiges oder verzweigtes C3-C6-Cycloalkyl-Ci-C2-alkyl steht, A represents a radical selected from hydrogen, methyl, which is optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, bromine, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m - or cyano-substituted Ci- -alkyl, C 3 -C 6 alkenyl or C 3 -C 6 -alkynyl optionally mono- or disubstituted independently by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted C 3 -C6- Cycloalkyl and optionally mono- to disubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or cyano-substituted, straight-chain or branched C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl,
R2 für einen Rest aus der Reihe Wasserstoff, gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Cycloalkyl steht, R 2 is a radical selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl,
T für Sauerstoff oder ein Elektronenpaar steht, und deren Salze. T is oxygen or a pair of electrons, and their salts.
4. Verbindung nach Anspruch 1 gemäß der Formel (II), bei der 4. A compound according to claim 1 according to the formula (II), wherein
(II),  (II)
Q für Sauerstoff oder Schwefel steht, Q stands for oxygen or sulfur,
V für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Methyl und Cyano steht, V is a radical from the series hydrogen, fluorine, chlorine, methyl and cyano,
W für einen Rest aus der Reihe Wasserstoff, Fluor, Chlor, Brom. Methyl, Ethyl und Cyano steht, W is a radical from the series hydrogen, fluorine, chlorine, bromine. Methyl, ethyl and cyano,
X für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Me- thoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluorme- thoxy, Trifluormethoxy, Trifluormethyl-S(0)m-, Difluorethyl-S(0)m-, Trifluorefhyl- S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethylamino, Diethylamino, Ethylmethylamino, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopro- pyl-methyl-S(0)m-, Difluormethoxy, Trifluormethoxy, Trifluormethyl-S(0)m-, Difluo- rethyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropy- lcarbonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Py- rimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran- 2-yl oder l,2,3-Triazol-4-yl substituiertes Aryl oder Hetaryl steht oder für einenen Aryl oder Hetarylring steht, welcher an zwei benachbarten Ringpositionen eine aus einem oder zwei Sauerstoffatomen und einem oder zwei Kohlenstoffatomen bestehende Kette gebunden hat und diese dabei einen heteroaromatischen oder gege- benefalls teilweise ungesättigten heterocyclischen Ring bildet, X is a radical from the series, where appropriate, monosubstituted to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) m -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0) m -, trifluoro-ethyl-S (0) m -, (tetrahydro-2H -pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano, and optionally mono- to trisubstituted independently of one another by fluorine , Chloro, bromo, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl-S (0) m -, difluoromethoxy, Trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclo propylcarbonyl) oxy, morpholin-4-yl or cyano-substituted phenyl, naphthyl, pyridyl, pyrimididyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxdiazolyl, thiadiazolyl, Benzofuran-2-yl or l, 2,3-triazol-4-yl substituted aryl or hetaryl or is an aryl or hetaryl ring, which at two adjacent ring positions one of one or two oxygen atoms and one or two carbon atoms has bound an existing chain and forms a heteroaromatic or, preferably, partially unsaturated heterocyclic ring,
Y für einen Rest aus der Reihe Wasserstoff, Benzyl, gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Methoxy, Ethoxy oder Cyano substituiertes Methyl, Ethyl, Propyl, Allyl oder Propargyl steht, m für eine Zahl 0, 1 oder 2 steht, Y is a radical from the group consisting of hydrogen, benzyl, optionally monosubstituted to trisubstituted independently of one another by fluorine, methoxy, ethoxy or cyano, methyl, ethyl, propyl, allyl or propargyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Methoxy, Ethoxy oder Cyano substituiertes Methyl, Ethyl, Propyl, Allyl, Propargyl, Cylopropyl oder Cyclopropylmethyl steht, A is a radical selected from the group consisting of hydrogen, optionally monosubstituted to trisubstituted independently of one another by fluorine, methoxy, ethoxy or cyano, methyl, ethyl, propyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl,
T für Sauerstoff oder ein Elektronenpaar steht und deren Salze. T is oxygen or a pair of electrons and their salts.
5. Verbindung nach Anspruch 4, bei der 5. A compound according to claim 4, wherein
Q für Sauerstoff oder Schwefel steht, V für Wasserstoff und Fluor steht, Q is oxygen or sulfur, V is hydrogen and fluorine,
W für einen Rest aus der Reihe Wasserstoff, Chlor, Brom und Methyl steht, W is a radical from the series hydrogen, chlorine, bromine and methyl,
X für einen Rest aus der Reihe gegebenenfalls einfach bis dreifach unabhängig voneinander durch X is a radical from the series optionally simply to three times independently by
Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl-S(0)m-, Difluormethoxy, Trifluor- methoxy, Trifluormethyl-S(0)m-, Difluorethyl-S(0)m-, Trifluorethyl-S(0)m-, (Tetra- hydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycar- bonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcarbonyl)oxy, Morpholin-4-yl, Dimethyl- amino, Diethylamino, Ethylmethylamino, Cyano und gegebenenfalls einfach bis dreifach unabhängig voneinander durch Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Methoxy, Ethoxy, Methyl-S(0)m-, Ethyl-S(0)m-, Cyclopropyl-methyl- S(0)n-, Difluormethoxy, Trifluormethoxy, Trifluormethyl-S(0)m-, Difluorethyl-S(0)m- , Trifluorethyl-S(0)m-, (Tetrahydro-2H-pyran-4-yloxy)methyl, Dimethylsulfamoyl, Methoxycarbonyl, Ethoxycarbonyl, 2-Ethoxy-2-oxoethoxy, (Cyclopropylcar- bonyl)oxy, Morpholin-4-yl oder Cyano substituiertes Phenyl, Naphtyl, Pyridyl, Pyri- midyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thia- zolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl substituiertes Phenyl, Naphtyl, Pyridyl, Pyrimidyl, Pyridazinyl, Pyrazinyl, Triazinyl, Furanyl, Thienyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Pyrazolyl, Imidazolyl, Oxdiazolyl, Thiadiazolyl, Benzofuran-2-yl oder l,2,3-Triazol-4-yl steht oder für ein Phenyl, welches an zwei benachbarten Ringpositionen eine aus einem oder zwei Sauerstoffatomen und einem oder zwei Kohlenstoffatomeen bestehende Kette gebunden hat und diese dabei einen gegebenenfalls teilweise ungesättigten heterocyc- lischen Ring bildet, Fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropyl-methyl-S (0) m -, difluoromethoxy, trifluoro - methoxy, trifluoromethyl-S (0) m -, difluoroethyl-S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycar - Bonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy, morpholin-4-yl, dimethylamino, diethylamino, ethylmethylamino, cyano and optionally mono- to trisubstituted independently of one another by fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl , Trifluoromethyl, methoxy, ethoxy, methyl-S (0) m -, ethyl-S (0) m -, cyclopropylmethyl- S (0) n -, difluoromethoxy, trifluoromethoxy, trifluoromethyl-S (0) m -, difluoroethyl -S (0) m -, trifluoroethyl-S (0) m -, (tetrahydro-2H-pyran-4-yloxy) methyl, dimethylsulfamoyl, methoxycarbonyl, ethoxycarbonyl, 2-ethoxy-2-oxoethoxy, (cyclopropylcarbonyl) oxy , Morpholin-4-yl or cyano-substituted phenyl, naphthyl, pyridyl, pyridine midyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxdiazolyl, thiadiazolyl, benzofuran-2-yl or 1,2,3-triazol-4-yl substituted phenyl, Naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, benzofuran-2-yl or 1,2,3-triazol-4-yl or a phenyl which has a chain of one or two oxygen atoms and one or two carbon atoms attached to two adjacent ring positions and forms an optionally partially unsaturated heterocyclic ring,
Y für einen Rest aus der Reihe Wasserstoff, Methyl, Ethyl, Propyl, Difluorethyl, Trifluo- rethyl, Methoxymethyl, Ethoxymethyl, Cyanomethyl und Benzyl steht, m für eine Zahl 0, 1 oder 2 steht, Y is a radical selected from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl and benzyl, m is a number 0, 1 or 2,
A für einen Rest aus der Reihe Wasserstoff, Methyl, Ethyl, Propyl, Difluorethyl, Trifluo- rethyl, Methoxymethyl, Ethoxymethyl, Cyanomethyl, Allyl, Propargyl, Cylopropyl oder Cyclopropyl-methyl steht, A is a radical from the group consisting of hydrogen, methyl, ethyl, propyl, difluoroethyl, trifluoroethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl, cyclopropyl or cyclopropylmethyl,
T für Sauerstoff oder ein Elektronenpaar steht und deren Salze. T is oxygen or a pair of electrons and their salts.
6. Verbindung nach Anspruch 4, bei der 6. A compound according to claim 4, wherein
Q für Sauerstoff oder Schwefel und bevorzugt für Sauerstoff steht, V für Wasserstoff steht, Q is oxygen or sulfur and preferably oxygen, V is hydrogen,
W für einen Rest aus der Reihe Wasserstoff, Chlor und Brom und bevorzugt für Wasserstoff steht,  W is a radical from the series hydrogen, chlorine and bromine and is preferably hydrogen,
X für einen Rest aus der Reihe 3-[(2,2,2-Trifluorethyl)sulfanyl]phenyl, 2-Fluor-4- methyl-5-[(2,2,2-trifluorethyl)sulfanyl]phenyl, 3-(Methylsulfanyl)phenyl, Pyrimidin-2- yl, 3-[(2,2,2-Trifluorethyl)sulfinyl]phenyl, Phenyl, Pyridin-3-yl, 3,5-Dimethylphenyl, 2-Chlorphenyl, 3-Chlorphenyl, 4-Chlorphenyl, 2,4-Dichlorphenyl, 3,4-Dichlorphenyl, 1 - Methyl- lH-pyrrol-2-yl, 3-Furyl, 2,5-Dimethyl-3-thienyl, 3- [(Trifluormethyl) sulf anyl]pheny 1, 3 - [(Cyclopropylmethyl) sulf anyl] pheny 1, 3 - (Methoxymethyl)phenyl, 3-[(Tetrahydro-2H-pyran-4-yloxy)methyl]phenyl, 3- (Dimethylsulfamoyl)phenyl, 3-(Methylsulfonyl)phenyl, 4-Methyl-3- (methylsulfanyl)phenyl, 1 -(2-Cyanphenyl)- 1 H-pyrazol-4-yl, 1 -(4-Fluorphenyl)- 1 H- pyrazol-4-yl, l-Phenyl-lH-pyrazol-4-yl, 1-Naphthyl, 5-(Methoxycarboriyl)-l- naphthyl, 4-Fluor-2-(methoxycarbonyl)phenyl, 4-Fluor-l-naphthyl, 4-Chlor-3- (ethoxycarbonyl)phenyl, 2-(Methoxycarbonyl)phenyl, Pyridin-4-yl, 6- (Ethoxycarbonyl)pyridin-2-yl, 3-(Ethoxycarbonyl)phenyl, 2-Naphthyl, 4-Methoxy-3- (methoxycarbonyl)phenyl, 4-Chlor-2-(methoxycarbonyl)phenyl, 3-Thienyl, 3-(2- Ethoxy-2-oxoethoxy)-4-methylphenyl, 3-(2-Ethoxy-2-oxoethoxy)phenyl, 3-(2-Ethoxy-X is a radical from the series 3 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfanyl] phenyl, 3- ( Methylsulfanyl) phenyl, pyrimidin-2-yl, 3 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4- Chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1-methyl-1H-pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3- [(trifluoromethyl) sulfinyl] phenyl 1, 3 - [(cyclopropylmethyl) sulfinyl] phenyl 1, 3 - (methoxymethyl) phenyl, 3 - [(tetrahydro-2H-pyran-4-yloxy) methyl] phenyl, 3- (dimethylsulfamoyl) phenyl, 3- (methylsulfonyl) phenyl, 4-methyl-3- (methylsulfanyl) phenyl, 1 - (2-cyanophenyl) -1 H -pyrazol-4-yl, 1- (4-fluorophenyl) -1 H -pyrazol-4-yl, 1-phenyl-1H-pyrazol-4-yl, 1-naphthyl, 5- (methoxycarboryl) -l-naphthyl, 4-fluoro-2- (methoxycarbonyl) -phenyl, 4-fluoro-1-naphthyl, 4-chloro-3- (ethoxycarbonyl) -phenyl, 2- (methoxycarbonyl) -phenyl, pyridine-4 -yl, 6- (ethoxycarbonyl) pyridin-2-yl, 3- (ethoxycarbonyl) phenyl, 2-naphthyl, 4-methoxy-3- (methoxycarbonyl) phenyl, 4-chloro-2- (methoxycarbonyl) phenyl, 3-thienyl , 3- (2-ethoxy-2-oxoethoxy) -4-methylphenyl, 3- (2-ethoxy-2-oxoethoxy) phenyl, 3- (2-ethoxy)
2- oxoethoxy)-4,5-difluorphenyl, 3-(2-Ethoxy-2-oxoethoxy)-4-fluorphenyl, 3- (Ethoxycarbonyl)-4-fluorphenyl, (3-{ [(Cyclopropylcarbonyl)oxy]methyl}phenyl, 3- { [(Cyclopropylcarbonyl)oxy]methyl}-4-fluorphenyl, Pyridin-2-yl, 3- (Difluormethyl)phenyl, 3 - [(Trifluormethyl) sulfinyl] phenyl, 4-Fluor-3 - (trifluormethyl)phenyl, 3-Chlor-5-(trifluormethyl)phenyl, 3-(Trifluormethyl)phenyl, 3,5-Bis(trifluormethyl)phenyl, 3-Fluor-5-(trifluormethyl)phenyl, 4-Cyan-3- (trifluormethyl)phenyl, 3-(2,2,2-Trifluorethyl)phenyl, 3-(Pentafluorethyl)phenyl, 3- Cyanphenyl, 4-Chlor-3-cyanphenyl, 3-Cyan-5-fluorphenyl, 3-Cyan-5- (trifluormethyl)phenyl, 5-Cyan-2-methoxyphenyl, 3-Cyan-4-fluorphenyl, 5- Cyanpyridin-3-yl, 5-Cyan-6-(dimethylamino)pyridin-3-yl, 5-Cyan-6-(morpholin-4- yl)pyridin-3-yl, 5-Cyan-6-ethoxypyridin-3-yl, 5-Cyan-6-methoxypyridin-3-yl, 3- Chlor-5-cyanphenyl, l-Benzofuran-2-yl, 3-Phenyl-l,2-oxazol-5-yl, 3- (Ethoxycarbonyl)- 1 ,2-oxazol-5-yl, 1 -Isopropyl- 1 H- 1 ,2,3-triazol-4-yl, 1 -Methyl- 1 H- l,2,3-triazol-4-yl, 5-Cyan-6-methoxypyridin-3-yl, 6-Methoxypyridin-2-yl, 2,3- Dihydro-l-benzofuran-7-yl, l-Benzofuran-7-yl, 2,6-Dimethoxypyridin-3-yl,2-oxoethoxy) -4,5-difluorophenyl, 3- (2-ethoxy-2-oxoethoxy) -4-fluorophenyl, 3- (ethoxycarbonyl) -4-fluorophenyl, (3- {[(cyclopropylcarbonyl) oxy] methyl} phenyl , 3- {[(Cyclopropylcarbonyl) oxy] methyl} -4-fluorophenyl, pyridin-2-yl, 3- (difluoromethyl) phenyl, 3 - [(trifluoromethyl) sulfinyl] phenyl, 4-fluoro-3 - (trifluoromethyl) phenyl , 3-chloro-5- (trifluoromethyl) phenyl, 3- (trifluoromethyl) phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-fluoro-5- (trifluoromethyl) phenyl, 4-cyano-3- (trifluoromethyl) phenyl , 3- (2,2,2-Trifluoroethyl) phenyl, 3- (pentafluoroethyl) phenyl, 3-cyanophenyl, 4-chloro-3-cyanophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5- (trifluoromethyl) phenyl, 5-cyano-2-methoxyphenyl, 3-cyano-4-fluorophenyl, 5-cyanopyridin-3-yl, 5-cyano-6- (dimethylamino) pyridin-3-yl, 5-cyano-6-morpholine 4-yl) pyridin-3-yl, 5-cyano-6-ethoxypyridin-3-yl, 5-cyano-6-methoxypyridin-3-yl, 3-chloro-5-cyanophenyl, 1-benzofuran-2-yl, 3-phenyl-1, 2-oxazol-5-yl, 3- (ethoxycarbonyl) -1,2-oxazol-5-yl, 1-isopropyl-1H-1,2,3-triazol-4-yl, 1 -Methyl- 1H- 1, 2,3-triazol-4-yl, 5-cyano-6-methoxypyridin-3-yl, 6-methoxypyridin-2-yl, 2,3-dihydro-1-benzofuran-7-yl, 1-benzofuran. 7-yl, 2,6-dimethoxypyridin-3-yl,
2-Methoxyphenyl, l,3-Benzodioxol-4-yl, 2,4-Dimethoxyphenyl, 2,5- Dimethoxyphenyl, 6-(Trifluormethyl)pyridin-2-yl, 5-Chlor-2-methoxypyridin-3-yl,2-methoxyphenyl, 1,3-benzodioxol-4-yl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 6- (trifluoromethyl) pyridin-2-yl, 5-chloro-2-methoxypyridin-3-yl,
2-Methoxypyridin-3-yl, 6-Ethoxypyridin-3-yl, 5-Chlor-6-methoxypyridin-3-yl,2-methoxypyridin-3-yl, 6-ethoxypyridin-3-yl, 5-chloro-6-methoxypyridin-3-yl,
2-(Methylsulfanyl)pyridin-3-yl, 2-Ethoxypyridin-3-yl, 5,6-Dimethoxypyridin-3- yl, 2-Methoxypyridin-4-yl, 6-Methoxy-5-(trifluormethyl)pyridin-3-yl, 6- Methoxy-5-nitropyridin-3-yl, 2,6-Dimethoxypyridin-4-yl, 2- (Methylsulfanyl)phenyl, 2-Methoxy-6-(trifluormethyl)-pyridin-4-yl, 3-Cyan-5- methoxyphenyl, 5-Fluor-2-methoxypyridin-3-yl, 6-Isopropoxypyridin-3-yl,2- (methylsulfanyl) pyridin-3-yl, 2-ethoxypyridin-3-yl, 5,6-dimethoxypyridin-3-yl, 2-methoxypyridin-4-yl, 6-methoxy-5- (trifluoromethyl) pyridine-3 yl, 6-methoxy-5-nitropyridin-3-yl, 2,6-dimethoxypyridin-4-yl, 2- (methylsulfanyl) phenyl, 2-methoxy-6- (trifluoromethyl) -pyridin-4-yl, 3-cyano -5-methoxyphenyl, 5-fluoro-2-methoxypyridin-3-yl, 6-isopropoxypyridin-3-yl,
6-Methoxypyridin-3-yl, 2-(2-Amino-2-oxoethoxy)phenyl, 3-Cyan-4- isopropoxyphenyl oder3-Chlorpyridin-2-yl steht, 6-methoxypyridin-3-yl, 2- (2-amino-2-oxoethoxy) phenyl, 3-cyano-4-isopropoxyphenyl or 3-chloropyridin-2-yl,
Y für Methyl steht, A für einen Rest aus der Reihe Wasserstoff, Methyl und Ethyl und bevorzugt für Methyl und Ethyl steht, Y is methyl, A is a radical from the series consisting of hydrogen, methyl and ethyl and is preferably methyl and ethyl,
T für ein Elektronenpaar steht  T stands for an electron pair
und deren Salze.  and their salts.
7. Mittel, mit einem Gehalt von mindestens einer Verbindung gemäß einem der Ansprüche 1 bis 6 und üblichen Streckmitteln und/oder oberflächenaktiven Substanzen insbesondere zur Bekämpfung von tierischen Schädlingen. 7. A composition containing at least one compound according to any one of claims 1 to 6 and conventional extenders and / or surface-active substances, in particular for controlling animal pests.
8. Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man wenigstens eine Verbindung gemäß einem der Ansprüche 1 bis 6 oder ein Mittel gemäß Anspruch 7 auf die tierischen Schädlinge und/oder ihren Lebensraum einwirken lässt. 8. A method for controlling animal pests, which comprises allowing at least one compound according to any one of claims 1 to 6 or an agent according to claim 7 to act on the animal pests and / or their habitat.
Verwendung wenigstens einer Verbindung gemäß einem der Ansprüche 1 bis 6 oder eines Mittels gemäß Anspruch 7 zur Bekämpfung von tierischen Schädlingen. Use of at least one compound according to any one of claims 1 to 6 or an agent according to claim 7 for controlling animal pests.
Verfahren gemäß Anspruch 8 oder Verwendung gemäß Anspruch 9, bei dem die chirurgische, therapeutische und diagnostische Behandlung des menschlichen oder tierischen Körpers ausgeschlossen ist. A method according to claim 8 or use according to claim 9, wherein the surgical, therapeutic and diagnostic treatment of the human or animal body is excluded.
11. Verwendung wenigstens einer Verbindung gemäß einem der Ansprüche 1 bis 6 zum Schutz des Vermehrungsmaterials von Pflanzen. 11. Use of at least one compound according to any one of claims 1 to 6 for the protection of the propagation material of plants.
Agrochemische Formulierung enthaltend wenigstens eine Verbindung gemäß einem der Ansprüche 1 bis 6 in biologisch wirksamen Gehalten von zwischen 0,00000001 und 98 Gew.-%, bezogen auf das Gewicht der agrochemischen Formulierung, sowie Streckmittel und/oder oberflächenaktive Stoffe. An agrochemical formulation comprising at least one compound according to any one of claims 1 to 6 in biologically active contents of between 0.00000001 and 98% by weight, based on the weight of the agrochemical formulation, as well as diluents and / or surface-active substances.
Agrochemische Formulierung gemäß Anspruch 12 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. Agrochemical formulation according to claim 12 additionally containing a further agrochemical active ingredient.
14. Zwischenprodukte der Formeln (Xa-Xd) 14. Intermediates of Formulas (Xa-Xd)
(Xb), (Xb)
(Xc), (Xd),  (Xc), (Xd),
wobei die vorhandenen Reste die Bedeutungen gemäß einem der Ansprüche 1 bis 6 und besonders bevorzugt die Bedeutung gemäß Anspruch 6 haben.  where the radicals present have the meanings according to one of claims 1 to 6 and particularly preferably the meaning according to claim 6.
EP17702147.4A 2016-02-11 2017-02-06 Substituierted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents Withdrawn EP3414236A1 (en)

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