WO2018177993A1 - Pyrazoles for controlling arthropods - Google Patents

Pyrazoles for controlling arthropods Download PDF

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Publication number
WO2018177993A1
WO2018177993A1 PCT/EP2018/057612 EP2018057612W WO2018177993A1 WO 2018177993 A1 WO2018177993 A1 WO 2018177993A1 EP 2018057612 W EP2018057612 W EP 2018057612W WO 2018177993 A1 WO2018177993 A1 WO 2018177993A1
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spp
methyl
alkyl
compounds
formula
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PCT/EP2018/057612
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German (de)
French (fr)
Inventor
Tobias HARSCHNECK
Alexander ARLT
Robert Velten
Michael Maue
Kerstin Ilg
Ulrich Görgens
Andreas Turberg
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Bayer Cropscience Aktiengesellschaft
Bayer Aktiengesellschaft
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Publication of WO2018177993A1 publication Critical patent/WO2018177993A1/en

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    • 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
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid

Definitions

  • the present application relates to novel compounds, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes.
  • WO 2011/113756 discloses triazole derivatives which have insecticidal activity.
  • the object of the present invention was to provide compounds by which the spectrum of pesticides widened under various aspects and / or their activity is improved.
  • One aspect of the present invention relates to novel insecticidal, acaricidal and / or parasiticidal halogen-substituted compounds of the general formula (I) - -
  • R 1 is H, in each case optionally with one or more substituents selected independently from amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C 4 -alkyl, Alkyl, C 3 -C 10 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkyl-amino, N, N-di-C 1 -C 4 -alkylamino, N -C 1 -C 4 alkanoylamino, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 4 cycl
  • an oxo group As methylidene or ethylidene), an oxo group, an imino group substituted Ci-C6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C 7 -Cvcloalkyl, C6-.Cio-.Ci4-aryl (Ci-C3 ) -alkyl 3. 4, 5. 6. 7. 8.
  • thietanyl such as thiethanyl-3-yl oxidothiethane, such as 1-oxo-thietan-3-yl or dioxothiethane, such as 1, l-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci-CsValkyl, preferably represents optionally substituted by halogen or cyano-substituted C3-C7-cycloalkyl;
  • thietanyl such as thiethanyl-3-yl oxidothiethane, such as 1-oxo-thietan-3-yl or dioxothiethane, such as 1, l-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci-CsValkyl, preferably represents optionally substituted by halogen or cyano-substituted C3
  • R 2 is H or C 1 -C 6 alkyl
  • Ai, A2 and A3 are each independently N, O, CR 3, S, or NR 4, wherein Ai, A2, A3, Z and the C-atom of the ring form an aromatic system;
  • Each R 3 is independently H, Cl, F, I, Br or optionally halogenated C 1 -C 4 alkyl;
  • Each R 4 is independently H or optionally halogenated C 1 -C 4 alkyl; Q is O or S;
  • Z is C or N, particularly preferably C
  • T is one of the 5-membered heteroaromatics T1-T8 listed below, wherein the
  • Binding to is marked with a rhombus #
  • R 5 is optionally halogenated (C 1 -C 6) -alkyl, optionally halogenated (C 1 -C 6) -alkoxy, -S (O) o-2 (C 1 -C 2) -alkyl or NO 2, preferably perhalogenated (C 1 -C 4 ) -Alkyl, perhalogenated (C 1 -C 4 ) -alkoxy or -S (O) o- ( 2 -C (Ci-C 2 ) -alkyl, more preferably perfluorinated (Ci-C 4 ) -alkyl, perfluorinated (Ci-C 4) alkoxy or -S (0) o-2 - (Ci-C 2) alkyl, more preferably is CF3;
  • R 6 represents optionally halogenated (C 3 -C 6 ) -cycloalkyl, optionally halogenated (C 1 -C 6) -alkoxy or optionally halogenated (C 1 -C 6) -alkyl, preferably perhalogenated (C 1 -C 4 ) -alkyl or perhalogenated (C 1 -C 4 ) -alkyl; C 4) alkoxy, more preferably perfluorinated (C 1 -C 4) -alkyl or perfluorinated (C 1 -C 4) -alkoxy, even more preferably C 2 F 5; - - As well as salts, N-oxides and tautomeric forms of the compounds of formula (I).
  • a preferred embodiment of the present invention is directed to compounds according to paragraph [0009], wherein R 2 is H or methyl.
  • a further preferred embodiment is directed to compounds according to one of the paragraphs [0009] or [0010], where T is for Tl, T4 or T5.
  • T stands for T2, T3, T4, T5, T6, T7 or T8, particularly preferably for T4 or T5.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0011], wherein R 1 is cyclopropyl or 1 -CN-cyclopropyl.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0013], wherein Q is O.
  • a further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0014], wherein A 3 is S.
  • a further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0015], wherein Z is C and A 2 is C-Hal, wherein Hal preferably represents I, Br or Cl, more preferably Br or I and especially preferably represents Br stand.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0016], wherein A3 is S, Z is C and A2 is C-Hal, wherein Hal is preferably Br, I or Cl, more preferably represents Cl, and Ai is CH or N.
  • a further preferred embodiment is directed to compounds of the formula (Ia),
  • a further preferred embodiment is directed to compounds of the formula (Ib) wonn Q, R 1 , R 2 , R 5 and R 6 and Ai as for compounds of formula (I) or a preferred embodiment of compounds of formula ( I) or a preferred embodiment of compounds of formula (I) are defined herein and Hai is preferably I, Br or Cl.
  • a further preferred embodiment is directed to compounds of the formula (Ic) Wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined for compounds of the formula (I) herein and Hai is preferably I, Br or Cl stands.
  • a further preferred embodiment is directed to compounds of the formula (Ia) wherein Q is O, Ai is N or CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally substituted by CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • a further preferred embodiment is directed to compounds according to formula (Ib) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • a further preferred embodiment is directed to compounds according to formula (Ic) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • Another aspect relates to an insecticidal composition
  • an insecticidal composition comprising at least one compound of the formula (I) according to any one of paragraphs [0009] to [0023] and an extender and / or a surface-active substance.
  • Another aspect relates to a process for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound according to any of paragraphs [0009] to [0023] is treated.
  • Another aspect relates to the use of compounds according to any one of paragraphs [0009] to [0023], or of a insecticidal agent according to paragraph [0024] for controlling pests.
  • Another aspect relates to seeds containing a compound according to any one of paragraphs [0009] to [0023] as part of a casing applied to the seed, or as a further layer in addition to a coating on the seed is applied.
  • Another aspect relates to a method for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound of formula (I) or derived from formula (I) Formula is treated as described herein.
  • Yet another aspect relates to the use of compounds of formula (I) or a formula derived from formula (I) as described herein or of a insecticidal agent as described herein for controlling pests.
  • Another aspect relates to the use of compounds of formula (I) or of a formula derived from formula (I) as described herein in the vector control.
  • Yet another aspect relates to seed in which a compound of formula (I) or a formula derived from formula (I) as described herein is applied to the seed in addition to a casing as part of a casing or as a further layer or layers is.
  • a further aspect relates to a process for applying a coating comprising at least one compound of formula (I) or a formula derived from formula (I) as described herein or for applying a compound of formula (I) or one of formula ( I) derived formula as herein described, applied as a layer or further layers in addition to a casing on seed, comprising the steps of a) mixing seeds with a coating material consisting of or comprising a compound of formula (I) or one of formula (I) derived formula as described herein, b) enriching the obtained coated seed mass, c) drying the resulting enriched seed mass, d) degumming (disagglomerating or deagglomerating) the obtained dried seed mass.
  • the compounds of the formula (I) described herein or of a formula derived from formula (I) may optionally be present in different composition depending on the nature of the substituents as geometric and / or as optically active isomers or corresponding isomer mixtures.
  • the invention relates to both the pure isomers and the isomer mixtures.
  • the compounds of the invention may also be present as metal complexes.
  • Definitions It will be understood by those skilled in the art, unless expressly stated, that the terms “a,” “an,” or “an” as used in this application, “depending on the situation,” “a (1)”, “ may mean one (1) or more or at least one (1).
  • C atoms Structures with a variable number of possible carbon atoms (C atoms) can be referred to in the present application as Cuntere limit C atoms ⁇ Cobere boundary C atoms ⁇ structures (C U GC 0 G structures), the more determined to become.
  • An alkyl group may consist of 3 to 10 C atoms and then corresponds to C3-Cio-alkyl.
  • Ring structures of C atoms and heteroatoms may be referred to as "uG to oG-membered" structures
  • An example of a 6-membered ring structure is toluene (a 6-membered ring structure substituted with a methyl group).
  • Halogen refers to the elements of the 7th main group, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine.
  • alkyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s Butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 2-dimethylpropyl, 1,3-dimethylbutyl, 1, 4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3 Dimethylbutyl
  • alkyls having 1 to 4 carbon atoms such as methyl, ethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl, among others.
  • the alkyls according to the invention may be substituted by one or more, identical or different radicals.
  • alkenyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl , 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2 -butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl 2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl
  • alkenyls having 2 to 4 carbon atoms such as 2-propenyl, 2-butenyl or 1-methyl-2-propenyl, among others.
  • the alkenyls according to the invention may be substituted by one or more identical or different radicals. - -
  • alkynyl alone or as part of a chemical group - is straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one triple bond such as 2-propynyl, 2-butynyl, 3-butynyl, 1 - Methyl 2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1, 1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 2-methyl-4-pent
  • alkynyls having 2 to 4 carbon atoms such as, inter alia, ethynyl, 2-propynyl or 2-butynyl-2-propenyl.
  • the alkynyls according to the invention may be substituted by one or more, identical or different radicals.
  • cycloalkyl alone or as part of a chemical group - for mono-, bi- or tricyclic hydrocarbons, preferably having 3 to 10 carbons such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1] heptyl, bicyclo [2.2.2] octyl or adamantyl. Also preferred are cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms, such as, inter alia, cyclopropyl or cyclobutyl.
  • the cycloalkyls of the invention may be substituted by one or more, identical or different radicals.
  • alkylcycloalkyl is mono-, bi- or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Further preferred are alkylcycloalkyls having 4, 5 or 7 carbon atoms, such as, for example, ethylcyclopropyl or 4-methylcyclohexyl.
  • the alkylcycloalkyls of the invention may be substituted by one or more, identical or different radicals.
  • cycloalkylalkyl is mono-, bi- or tricyclic cycloalkylalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Also preferred are cycloalkylalkyl having 4, 5 or 7 carbon atoms, such as cyclopropylmethyl or cyclobutylmethyl.
  • the cycloalkylalkyls of the invention may be substituted by one or more, identical or different radicals.
  • hydroxyalkyl is straight-chain or branched alcohol, preferably having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. Further preferred are hydroxyalkyl groups having 1 to 4 carbon atoms.
  • the hydroxyalkyl groups according to the invention may be substituted by one or more identical or different radicals - -
  • alkoxy represents straight-chain or branched O-alkyl, preferably having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Further preferred are alkoxy groups having 1 to 4 carbon atoms.
  • the alkoxy groups according to the invention may be substituted by one or more identical or different radicals.
  • alkylsulfanyl is straight-chain or branched S-alkyl, preferably having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio and t-butylthio. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms.
  • the Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
  • alkylsulfinyl represents straight-chain or branched alkylsulfinyl, preferably having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl and t-butylsulfinyl. Further preferred are alkylsulfinyl groups having 1 to 4 carbon atoms.
  • the alkylsulfinylgrappen invention can be substituted with one or more, identical or different radicals.
  • alkylsulfonyl represents straight-chain or branched alkylsulfonyl, preferably having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl and t-butylsulfonyl. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms.
  • the Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
  • the alkylcarbonyls according to the invention may be substituted by one or more identical or different radicals.
  • cycloalkylcarbonyl represents straight-chain or branched cycloalkylcarbonyl, preferably having 3 to 10 carbon atoms in the cycloalkyl moiety, such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptyl, bycyclo [2.2.2] octylcarbonyl and adamantylcarbonyl. Also preferred are cycloalkylcarbonyl having 3, 5 or 7 carbon atoms in the cycloalkyl moiety.
  • the Cycloalkylcarbonylgrappen invention can be substituted with one or more, identical or different radicals. - -
  • alkoxycarbonyl alone or as part of a chemical group - is straight-chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl.
  • the alkoxycarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
  • alkylaminocarbonyl means straight-chain or branched alkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl.
  • the alkylammocarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
  • N-dialkylamino-carbonyl is straight-chain or branched NN-dialkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as NN-dimethylamino-carbonyl, ⁇ . ⁇ -diethylamino-carbonyl, NN Di (n-propylamino) carbonyl, N, N'-di (isopropylamino) carbonyl and N, N'-di (s-butylamino) carbonyl.
  • the N, N-dialkylaminocarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • aryl is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl.
  • aryl also represents polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, where the binding site is on the aromatic system.
  • the aryl groups according to the invention may be substituted by one or more, identical or different radicals.
  • substituted aryls are the arylalkyls, which may likewise be substituted by one or more identical or different radicals in the C 1 -C -alkyl- and / or C 6 -C 4 -aryl moiety.
  • arylalkyls include benzyl and 1-phenylethyl.
  • heterocycle means a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S. , P, B, Si, Se and which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in - - Heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent.
  • the heterocyclic rings usually contain not more than 4 nitrogen atoms, and / or not more than 2 oxygen atoms and / or not more than 2 sulfur atoms.
  • the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • the invention also includes polycyclic systems, for example 8-azabicyclo [3.2.1] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • the invention also includes spirocyclic systems, for example 1-oxa-5-aza-spiro [2.3] hexyl.
  • Heterocyclyl groups according to the invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl , Oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholin
  • heteroarylene ie heteroaromatic systems.
  • heteroaryl means heteroaromatic compounds, that is, fully unsaturated aromatic heterocyclic compounds which fall under the above deficient heterocycles.
  • heteroaryls are furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2 , 4- and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3-triazinyl, 1,2, 4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, oxepinyl, thiepinyl, 1, 2,4-triazolonyl and 1,2,4-diazepinyl.
  • the heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals.
  • substituents such as a substituted alkyl, alkenyl, alkynyl, alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl, represent, for example, a substituted radical derived from the unsubstituted body, wherein the substituents are, for example, one (1) substituent or more substituents, preferably 1, 2, 3, 4, 5, 6, or 7, selected from a group consisting of amino , Hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C 4 -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C -alkyl, C 3 -C -cycloalkyl, C 2 -C -alken
  • an oxo group As methylidene or ethylidene), an oxo group, an imino group and a substituted imino group.
  • Particularly preferred substituted groups are halogenated groups. These may have one or more halogen substituents, but these groups still have at least one CH bond, or be perhalogenated.
  • the exemplified substituents (“first substituent level"), if they contain hydrocarbon-containing moieties, optionally further substituted there (“second substituent plane"), for example by one or more of the substituents each independently selected from halogen, hydroxy, amino , Nitro, cyano, isocyano, azido, acylamino, an oxo group and an imino group.
  • the term "(optionally) substituted" group includes only one or two substituent levels.
  • halogen-substituted chemical groups or halogenated groups are monosubstituted or polysubstituted by halogen up to the maximum possible number of substituents.
  • groups are also referred to as halo groups (such as, for example, haloalkyl).
  • the halogen atoms may be the same or different and may all be bonded to one or more carbon atoms.
  • halogen is in particular fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferably fluorine or Cl.
  • halogen-substituted groups are monohalocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl or 1-fluorocyclobutyl, monohaloalkyl, such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroalkyl ethyl, chloromethyl, or fluoromethyl; Perhaloalkyl such as trichloromethyl or trifluoromethyl or CF 2 CF 3, polyhaloalkyl such as difluoromethyl, 2-fluoro-2-chloro-ethyl, dichloromethyl, 1, 1, 2,2-tetrafluoroethyl, or 2,2,2-trifluoroethyl.
  • monohaloalkyl such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroalkyl ethyl, chloromethyl,
  • haloalkyls are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2 , 2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl and pentafluoro-t-butyl.
  • haloalkyls having 1 to 4 carbon atoms and 1 to 9, preferably 1 to 5 identical or different halogen atoms, which are selected from fluorine, chlorine or bromine.
  • halogenoalkyls having 1 or 2 carbon atoms and having 1 to 5 identical or different halogen atoms, which are selected from fluorine or chlorine, such as, inter alia, difluoromethyl, trifluoromethyl or 2,2-difluoroethyl.
  • halogen-substituted compounds are haloalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 , OCH 2 CHF 2 and 0CH 2 CH 2 C1, haloalkylsulfanyls such as difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio , 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkylsulfinyls such as difluoromethylsulfinyl, trifluoromethylsulfinyl , Trichloromethylsulfin
  • radicals with C atoms those having 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred.
  • Preferred are usually substituents selected from the group halogen, e.g. Fluorine and chlorine, (Ci-C i) alkyl, preferably methyl or ethyl, (Ci-C i) haloalkyl, preferably trifluoromethyl, (Ci-C4) alkoxy, preferably methoxy or ethoxy, (Ci-C i) haloalkoxy, nitro and cyano.
  • Particularly preferred are the substituents methyl, methoxy, fluorine and chlorine.
  • Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals, which are N-substituted for example by one or two identical or different radicals from the group alkyl, hydroxy, amino, alkoxy, acyl and aryl ; preferably N-mono- and N, N-dialkylamino, (eg methylamino, ethylamino, N, N-dimethylamino, N, N-diethylamino, N, N-propylamino, N, N-diisopropylamino or N, N-dibutylamino), N-mono- or N, N-dialkoxyalkylamino groups ( for example, N-methoxymethylamino, N-methoxyethylamino, N, N'-di (methoxymethyl) amino or N, N'-di (methoxyethyl) amino), N-mono- and
  • cyclic amino groups heteroaromatic or aliphatic ring systems having one or more nitrogen atoms.
  • the heterocycles are saturated or unsaturated, consist of one or more, optionally fused ring systems and Optionally contain further heteroatoms, such as one or two nitrogen, oxygen and / or sulfur atoms.
  • the term also includes such groups having a spiro or bridged ring system.
  • the number of atoms that form the cyclic amino group is arbitrary and may, for example, in the case of a single-ring system of 3 to 8 ring atoms and in the case of a two-ring system of 7 to 1 1 atoms.
  • Examples of cyclic amino groups with saturated and unsaturated monocyclic groups having a nitrogen atom as a heteroatom are 1-azetinyl, pyrrolidino, 2-pyrrolidin-1-yl, 1 - pyrrolyl, piperidino, 1, 4-dihydropyrazine-1-yl, 1 2,5,6-tetrahydropyrazine-1-yl, 1,4-dihydropyridin-1-yl, 1, 2,5,6-tetrahydropyridin-1-yl, called homopiperidinyl;
  • Exemplary of cyclic amino groups with saturated and unsaturated monocyclic groups having two or more nitrogen atoms as heteroatoms are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 1, 2- Dihydro-piperazine-1-yl, 1,2-dihydro-pyrimidin-1-
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 haloalkyl, Ci-C4 .Halogenalkoxy, Ci-C 4 .Alkylsulfanyl, Ci-C.
  • Haloalkylsulfanyl, cyano, isocyano and nitro for example, o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4 Trifluoromethyl- and trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl, 4-heptafluorophenyl.
  • Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group - -
  • Halogen, cyano, C 1 -C -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 Haloalkoxy is substituted, in particular by one or two Ci-C4-Alkylreste substituted.
  • Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 haloalkoxy groups, nitro, and oxo, in particular mono- or polysubstituted by radicals from the is especially substituted by one or two Ci-C 4 alkyl group halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4 haloalkyl, and oxo.
  • alkyl substituted heteroaryls are furylmethyl, thienylmethyl, pyrazolylmethyl, imidazolylmethyl, 1,2,3- and 1,2,4-triazolylmethyl, isoxazolylmethyl, thiazolylmethyl, isothiazolylmethyl, 1,2,3-, 1,3,4 , 1,2,4- and 1,2,5-oxadiazolylmethyl, azepinylmethyl, pyrrolylmethyl, pyridylmethyl, pyridazinylmethyl, pyrimidinylmethyl, pyrazinylmethyl, 1,3,5-, 1,2,4- and 1,2,3- Triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinylmethyl, oxepinylmethyl, thiepinylmethyl and 1,2,4-diazepinylmethyl.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. ?
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always includes the term pesticides.
  • the compounds of formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the crop and to control animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are 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 understood to mean the entirety of all measures, methods and behaviors with the goal of avoiding diseases - in particular infectious diseases - and the health of humans, animals and / or the environment Serve and / or maintain the cleanliness.
  • This includes according to the invention in particular measures for cleaning, disinfection and sterilization, for example, textiles or hard surfaces, mainly glass, wood, concrete, porcelain, ceramic, plastic or metal (s), and their
  • measures for cleaning, disinfection and sterilization for example, textiles or hard surfaces, mainly glass, wood, concrete, porcelain, ceramic, plastic or metal (s), and their
  • methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are carried out on the human or animal body are excluded.
  • honeygiene sector therefore encompasses all areas, technical areas and commercial uses in which such measures, processes and hygiene behaviors are of importance, such as hygiene in kitchens, bakeries, airports, spas, swimming pools, shopping centers, Hotels, hospitals, stables, etc.
  • the term “hygiene pest” is understood to mean one or more animal pests (e) whose presence in the hygiene sector is problematical, in particular for health reasons, and it is therefore the primary aim to prevent or treat hygiene pests in the hygiene sector This can be done, in particular, by the use of a pest control agent, which can be used both prophylactically and only when infested to control the pest It is also possible to use agents that cause a contact is avoided or reduced with the pest etc. For example, the following organisms may be considered as hygiene pests.
  • the term “hygiene protection” therefore includes all actions for the maintenance and / or improvement of such measures, procedures and behaviors for hygiene.
  • 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 the Arthropoda in particular from the class of the Arachnida eg Acarus spp., For example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp.
  • Acarus siro Ac
  • Curculio spp. Eg Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., Eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgi fera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.
  • Contarinia spp. Eg Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., Eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp , Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg, Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophil a spp., eg Drosophila melanogaster, Drosophila suzukii, E
  • Diaphorina citri Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantagmea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna , Empoasca solana, Empoasca stevensi, Eriosoma spp., Eg Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geo
  • Nephotettix spp. Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon
  • Toxoptera spp. Eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops, Tri
  • Cydia spp. Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Egg dana saccharina, Ephestia spp., eg, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea , Euxoa spp., Felt
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests of the Mollusca strain in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., E.g.
  • Echinococcus spp. E.g. Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., E.g.
  • Enterobius vermicularis Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp. , eg Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., E.g.
  • Loa Loa Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodiras spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp.
  • Opisthorchis spp. Onchocerca volvulus, Opisthorchis spp., Osleras spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp.
  • Schistosoma spp. Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Eg Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., E.g. Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., E.g.
  • Trichinella spiralis Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., E.g. Trichuris trichuria, Uncinaria spp., Wuchereria spp., E.g. Wuchereria bancrofti;
  • Ditylenchus spp. E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., E.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmanieila spp., Hoplolaimus spp., Longidorus 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., E.g.
  • 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, Tylenchulus spp., E.g. Tylenchulus semipenetrans, Xiphinema spp., E.g. Xiphinema index.
  • nematodes in the present context includes all species of the strain Nematoda and in particular species, the plants or fungi (for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others) or even humans and animals (for example species of Trichinellida, Tylenchida, Rhabditida and Spirurida) parasites or causing damage to these animals, as well as other parasitic helminths.
  • the plants or fungi for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others
  • humans and animals for example species of Trichinellida, Tylenchida, Rhabditida and Spirurida
  • a nematocide in crop protection as described herein has the ability to control nematodes.
  • controlling nematodes means killing the nematodes or preventing or aggravating their development or growth, or preventing or hindering their penetration into or their sucking on the plant tissue.
  • the efficacy of the compounds is compared by a comparison of mortality, bile formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes between one treated with the compound of formula (I) Plant, plant part or the treated soil and an untreated plant, plant part or untreated soil (100%) determined.
  • a reduction of 25-50% compared to an untreated plant, plant part or untreated soil more preferably a reduction of 51-79%, and most preferably complete suppression or complete prevention of development and growth of the nematodes by reduction achieved by 80 to 100%.
  • Nematodes as described herein also include control of nematode proliferation (development of cysts and / or eggs).
  • Compounds of formula (I) may also be used to maintain healthy plants or animals and may be used for curative, preventive or systemic control of nematode control. Methods are known to those skilled in the art, such as mortality, bile formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes.
  • the use of a compound of formula (I) can keep the plant healthy and also includes a reduction in the damage caused by nematodes as well as an increase in the amount of harvest.
  • nematodes refers to plant nematodes, which include all nematodes that cause damage to plants
  • Plant nematodes include plant parasitic nematodes and soil-borne nematodes
  • Plant parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp semi-parasites such as Tylenchulus spp; migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonema spp .; localized parasites such as Heterodera spp., Globodera spp., and Meloidogyne spp., and stalk and leaf endoparasites such as Ditylenchus spp
  • Particularly harmful root parasitic soil nematodes are, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and / or root-k
  • nematodes to combat which a compound of formula (I) can be used include nematodes of the genus Meloidogyne such as the Southern Root-Knot Nematode (Meloidogyne incognita), the Javanese Root-Knot Nematode (Meloidogyne Javavanica, Northern Root-knot nematode (Meloidogyne hapla) and the peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as potato scabies (Ditylenchus destructor) and cane and stemlets (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as Cob root Nematode (Pratylenchus penetrans), the Chrysanthemum Root-Lesion Nematode (Pratylenchus fallax), the Coffee Rooted
  • the plants for the protection of which a compound of the formula (I) can be used include plants such as cereals (for example rice, barley, wheat, rye, oats, corn and the like), beans (soybean, azuki bean, Bean, broad beans, peas, peanuts and the like), fruit trees / fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries and the like), vegetables (cabbage, tomato, spinach, Broccoli, lettuce, onion, tubeworm, pepper and the like), root crops (carrot, potato, sweet potato, radish, lotus root, rutabaga and the like), plants for industrial raw materials (cotton, hemp, paper mulberry, mitsumata, rape, turnip, hops, sugar cane , Sugar beet, olive, gum, palm, coffee, tobacco, tea and the like), cucurbits (squash, cucumber, watermelon, melon and the like),
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of coffee, in particular Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. and from Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. and Scutellonema spp.
  • the compounds of formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci and Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodor
  • the compounds of formula (I) are particularly suitable for controlling tomato nematodes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus , Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of cucurbits, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei.
  • the compounds of the formula (I) are particularly suitable for controlling cotton nematodes, in particular Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.
  • the compounds of the formula (I) are particularly suitable for combating nematodes of maize, in particular Belonolaimus longicaudatus, Paratrichodorus minor and Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, arenaria, Meloidogyne, Meloidogyne arenaria thamesi, graminis Meloidogyne, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, naasi Meloidogyne, Heterodera avenae, Heterodera oryzae,
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of soybean, in particular of Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus and Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus colum
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of the tobacco, in particular Meloidogyne incognita, Meloidogyne javanica and Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatus, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp.,
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of citrus plants, in particular Pratylenchus coffeae and Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita , Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans.
  • the compounds of the formula (I) are particularly suitable for controlling banana nematodes, in particular Pratylenchus coffeae, Radopholus similis and Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp. - -
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of the pineapple, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyuras, Pratylenchus goodeyi., Meloidogyne spp., Rotylenchulus reniformis and Longidoras elongatus, Longidoras laevicapitatus, Trichodoras primitivus, Trichodoras minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopho
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of grapes, in particular Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus Pratylenchus brachyuras, Pratylenchus thornei and Tylenchulus semipenetrans.
  • Pratylenchus vulnus Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus Praty
  • the compounds of the formula (I) are particularly suitable for combating nematodes of tree crops - pome fruit, in particular Pratylenchus penetrans and Pratylenchus vulnus, Longidoras elongatus, Meloidogyne incognita and Meloidogyne hapla.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of tree crops - stone fruits, in particular Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyuras, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyuram and Hoplolaimus galeatus.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops, sugarcane and rice, in particular Trichodoras spp., Criconemella spp. and from Pratylenchus spp. , Paratrichodoras spp., Meloidogyne spp. , Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp. Heterodera spp, Xiphinema spp. and Cacopauras pestis.
  • the term "nematodes" in the present context refers to nematodes that harm humans or animals.
  • Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.
  • Strongylus spp. Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp.
  • Neostrongylus spp. Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp , Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp.
  • Ollulanus spp. For example, from the spout of Spirurida: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa s
  • the present invention also relates to the use of the compounds of formula (I) as anthelmintic drugs.
  • Pathogenic endoparasitic helminths include platyhelmintha (e.g., Monogenea, Cestodes, and Trematodes), Acanthocephala, and Pentastoma. The following helminths are to be mentioned as preferred:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.
  • Cestodes from the order of Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.
  • Trematodes from the class of Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp.
  • Echinoparyphium spp. Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis
  • Acanthocephala from the order of Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order of Polymorphida for example: Filicollis spp .; from the order of Moniliformida for example: Moniliformis spp., From the order of Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
  • Pentastoma from the order of the Porocephalida for example Linguatula spp.
  • the compounds of formula (I) are administered in a known manner, directly or enterally, parenterally, dermally or nasally in the form of suitable forms of application.
  • the administration can be prophylactic or therapeutic.
  • the compounds of formula (I) may optionally also in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents 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.
  • 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 other pesticides and / or effect-improving Adjuvants such as penetration enhancers, e.g.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rape oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention promoting agents such.
  • dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as 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 FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • extenders e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g.
  • Cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters
  • ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strong polar solvents such as dimethyl sulfoxide and water.
  • Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: e.g.
  • Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foam-producing agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability, may furthermore 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-like 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, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers. ?
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
  • the formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), more preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly preferably between 0 , 5 and 90 wt .-% 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 pest control agents) 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.
  • 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 or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt.
  • the compounds of formula (I) may be present in admixture with other active ingredients or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos,
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, - -
  • Bioallethrin S-cyclopentenyl isomer bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) - trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, momfluoroth
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • nAChR nicotinergic acetylcholine receptor
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as
  • Alkyl halides e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • Bacillus thuringiensis subspecies israelensis Bacillus sphaericus
  • Bacillus thuringiensis subspecies aizawai Bacillus thuringiensis subspecies kurstaki
  • Bacillus thuringiensis subspecies tenebrionis and BT plant proteins CrylAb, CrylAc, CrylFa, Cry2Ab, mCry
  • inhibitors of oxidative phosphorylation, ATP disruptors such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • ATP disruptors such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Decoupling of oxidative phosphorylation by interruption of the H proton gradient such as chlorfenapyr, DNOC, and sul
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Anti-skinning agents especially in dipterans, i.e., two-wingers, such as cyromazines.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • voltage dependent sodium channel blockers e.g. Indoxacarb or metaflumizone.
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
  • agents with unknown or ambiguous mechanism of action such as afidopyropene, afoxolans, azadirachtin, benclothiaz, benzoximate, bifenazates, broflanilides, bromopropylates, quinomethionate, cryolites, cyclaniliproles, cycloxapride, cyhalodiamides, dicloromethzotiaz, dicofol, diflovidazine, flometoquine, fluazaindolizines, fluensulfones, flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Lotilaner, Meperfluthrin, Paichongding, Pyflubumide,
  • the drugs specified herein with their "common name” are known, for example as described in the "Pesticide Manual” or on the Internet (for example: http://www.alanwood.net/pesticides). All of the listed five-component mixed partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. In addition, tautomeric forms are also included for the listed ficcidial mixed partners of classes (1) to (15), provided that tautomerism is possible.
  • inhibitors of ergosterol biosynthesis for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis,
  • inhibitors of mitosis and cell division for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6- trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6 trifluorophenyl) pyridazine.
  • inhibitors of amino acid and / or protein biosynthesis for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) mepanipyrim, (7.07) Pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
  • inhibitors of ATP production for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
  • Validamycin A (9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4 -yl) prop-2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4- yl) prop-2-ene-1-one.
  • inhibitors of lipid and membrane synthesis for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08)
  • Isoprothiolane (10.09) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene, (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis for example (11.01) carpropamide, (11.02) diclocymet, (1 1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl ⁇ 3-methyl-l - carbamate [(4-methylbenzoyl) amino] butan-2-yl ⁇ .
  • inhibitors of signal mediation for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
  • the compounds of formula (I) may be combined with biological pesticides. 5
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are: - 5 -
  • 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
  • NPV Africann Cotton worm
  • bacteria and fungi which are added as 'inoculant' plants or plant parts or plant organs and, by virtue of their particular properties, promote plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and products formed by microorganisms including proteins and secondary metabolites, which can be used as biological pest control agents are:
  • the compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) - 1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant parts
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired ones 5
  • Wild plants or crops for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peppers and chilli, cucumbers, melons, carrots, watermelons, Onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plants are to be understood as meaning all stages of development of the plants, for example seeds, cuttings and young (immature) plants through to mature plants.
  • Plant parts are understood to mean all aboveground and subterranean 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 crops (harvested plants or 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 acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
  • plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes. 5
  • 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 Abwehr ability of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes, for example.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) in the plants are produced, furthermore an increased from defensive ability of the plants against plant-pathogenic mushrooms, bacteria and / or viruses, causes eg systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as increased tolerance of the plants to certain herbicidal agents, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g., "PAT" gene).
  • SAR systemically acquired resistance
  • systemin phytoalexins
  • elicitors elicitors
  • 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, rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape.
  • Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • 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 by dipping, (spraying) spraying, (spraying), Sprinkling, vaporizing, spraying, misting, sprinkling, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layered Enveloping, etc. It is also possible, the compounds of formula (I) according to the ultra-low-volume method or to inject the use form or compound of formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site.
  • this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from infestation by pests by treating the seeds with one of the compounds of formula (I).
  • the method according to the invention for protecting seed and germinating plants from infestation by pests further comprises a method in which the seed is cultivated simultaneously or sequentially with a compound of the formula (I) and Mixing partner is treated. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • a compound of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation comes. 5?
  • the compounds of the formula (I) are suitable for the protection of seeds 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 formula (I) is of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly 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, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coatings, and ULV formulations.
  • formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
  • Suitable 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.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • 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.
  • 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. 5
  • all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention.
  • examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed-dressing formulations of the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates at The compound of the formula (I) is generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I) which are of low toxicity to warm-blooded animals are useful in the control of parasites used in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals occur. They are effective against all or individual stages of parasite development.
  • farm animals include mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
  • Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians, and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • controlling means that by the compounds of the formula (I), the occurrence of the respective parasite in an animal infected with such parasites to a harmless extent is effective , can be reduced. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication. - -
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • arthropods include:
  • 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G.
  • Trypanosomatidae for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
  • Eimeridae for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E.
  • gallopavonis E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. sitesdai E. suis, E. tenella, E.
  • S. suihominis such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
  • Cestodes from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle
  • Plagiorchis spp. Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
  • Roundworms Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp.
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia s
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the compounds of formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • Another aspect in turn relates to the use of a compound of formula (I) as an anti-parasitic, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of formula (I) as an anti-topazarasitic, in particular an arthropodicide such as Insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
  • an arthropodicide such as Insecticide or acaricide
  • Anthelminthic agents including trematicide and cestocide agents: from the class of macrocyclic lactones, e.g. Such as: abamectin, doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin, nemadectin, selamectin; from the class of benzimidazoles and sample zimidazoles, e.g.
  • albendazole albendazole, albendazole sulfoxide, cambendazole, cyclobendazole, febantel, fenbendazole, flubendazole, mebendazole, netobimine, oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate, triclabendazole; from the class of cyclooctadepsipeptides, e.g. B: emodepside, PF1022; from the class of aminoacetonitrile derivatives, e.g. For example: Monepantel; from the class of tetrahydropyrimidines, e.g.
  • B . Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, e.g. B .: butamisole, levamisole, tetramisole; from the class of salicylanilides, e.g. For example: bromoxanide, breadanide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide, tribromomalan; from the class of Paraherquamide, z.
  • B . Derquantel, paraherquamide; - 5 - from the class of Aminophenylamidine, z.
  • amidantel deacylated amide shell (dAMD), tribendimidine
  • organophosphates e.g. B .: Coumaphos, Crufomat, Dichlorvos, Haloxon, Naphthalofos, Trichlorfon
  • substituted phenols e.g. Bithionol, disophenol, hexachlorophene, nicolofolan, meniclopholan, nitroxynil
  • piperazinones e.g. B .: praziquantel, epsiprantel; from other diverse classes, eg.
  • amoscanate bephenium, bunamidine, clonazepam, clorsulone, diamfenetide, dichlorophen, diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, miracil, mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz, omphalotin, oxamniquine, paromomycin, piperazine, resorantel ,
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • - Culex Japanese encephalitis, filariasis, other viral diseases, transmission of worms
  • - Aedes yellow fever, dengue fever, filariasis, other viral diseases
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors for the purposes of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vector control is also possible when the compounds of formula (I) are resistive.
  • Compounds of formula (I) are suitable for use in the prevention of diseases or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials. Protection of technical materials
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • 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, ie, it may be readily available n
  • the compounds of formula (I) can be used to protect against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water , Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera , Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out, for example, in aerosols, pressureless sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • aerosols pressureless sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Another aspect of the invention is the use of a compound of formula (I) as a herbicide.
  • reaction Scheme 1 shows a general method for the preparation of the compounds ( ⁇ ') according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • Ei, E2 and E3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to Tl, T2, T3 and T6.
  • U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide.
  • U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate.
  • X stands for F or Cl.
  • a preferred embodiment of compounds of the general structure ⁇ according to the invention are compounds of the general structure Ia according to the invention.
  • Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such.
  • suitable bases such as aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as.
  • dioxane or THF can be obtained.
  • Intermediates of general structure 6 can be obtained by reaction of intermediates of general structure 5 with halogenating agents.
  • halogenating agents for example, N-halosuccinimides are used [see, for example, WO 2009/112845, WO 2012/137181].
  • Compounds of general structure 5 can be prepared by palladium catalyzed reactions from reactants 3 and 4 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocydes 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.].
  • the compounds of general structure 4 are either commercially available or can be prepared by methods known to those skilled in the art [see, e.g. WO2016 / 066697; Eur. J. Med. Chem.
  • the compounds of general structure 3 can be prepared by literature methods from reaction partners of the general structure 1 and 2 [see, for example. WO2014 / 122083; WO 2014/135439; WO2016 / 020441].
  • the compounds of general structure 2 are commercially available.
  • Compounds of general structure 1 can be prepared by methods known to those skilled in the art [see, e.g. WO 2015/181139; WO2016 / 020441].
  • Reaction scheme 1b shows a further process for the preparation of the compounds ( ⁇ ') according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • Ei, E 2 and E 3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to T 1, T 2 , T 3 and T 6.
  • U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide.
  • U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate.
  • X stands for F or Cl. Shark stands for Cl, I or 7
  • a preferred embodiment of compounds of the general structure ⁇ according to the invention are compounds of the general structure Ia according to the invention.
  • Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such as. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF can be obtained.
  • Compounds of general structure 6 can be prepared by palladium catalyzed reactions from reactants 3 and 16 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocycles 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.].
  • the compounds of general structure 16 are either commercially available or can be prepared by methods known to those skilled in the art.
  • Compounds of general structure 3 can be prepared analogously to the methods described above.
  • Reaction Scheme 2 shows a general method for the preparation of the compounds (Ib) according to the invention.
  • Alk is a C 1 -C 4 alkyl.
  • Q stands for O.
  • X stands for F or Cl.
  • Intermediates of the general structure 13 may be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Lett., 2009, 50, 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 12 and acetylenes of general structure 10 can be obtained.
  • Compounds of general structure 10 can be obtained by reaction of intermediates of general structure 1 and trimethylsilylacetylene under conditions known from the literature (see, for example, WO2015 / 193218).
  • Scheme 3 depicts a general method for the preparation of the compounds (Ic) according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q is O.
  • X 1 is F or Cl, X 2 is Br or I.
  • Intermediates of the general structure 20 can be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Letl, 2009, 50 , 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 17 and acetylenes of general structure 19 can be obtained. Intermediates of general structure 17 can be obtained in analogy to processes known from the literature starting from halides of general structure 1 by reaction with sodium azide (for example US2017 / 112129 A1, WO2012 / 80376 Al). Halides of general structure 1 are commercially available or can be prepared by methods known to the person skilled in the art.
  • Reaction Scheme 4 depicts a general method for the preparation of the compounds (Id) according to the invention. Reaction scheme 3
  • oximes 24 are first treated with suitable halogenating agents, e.g. N-halosuccinimides and then reacted with acetylenes 10 in the presence of a suitable base, e.g. Triethylamine (e.g., WO2015 / 150442).
  • suitable halogenating agents e.g. N-halosuccinimides
  • acetylenes 10 in the presence of a suitable base, e.g. Triethylamine (e.g., WO2015 / 150442).
  • Oximes of the general structure 24 are known or can be prepared from aldehydes of the general structure 23 analogously to literature methods (eg Bull. Chem. Soc., 1985, 58, 352-360; J. Chem. Soc., Perk. Trans 1 1980, 4, 1029-1037). Aldehydes of general structure 23 are commercially available or can be prepared by methods known to those skilled in the art. ?
  • Reaction Scheme 5 depicts another general method for the preparation of the compounds (Id) and (Ie) according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • X stands for I, Br or Cl.
  • the regioisomeric intermediates of general structure 31 or 31 ' can be prepared analogously to processes known from the literature by condensation of intermediates of general structure 30 Hydroxylamine or its hydrochloride are obtained (eg Eur. J. Med. Chem. 2016, 117, 85-98, WO2009 / 029632).
  • Intermediates of general structure 29 can be prepared after deprotonation with a suitable base, e.g. NaH or NaOMe can be converted to intermediates of general structure 30 by reaction with intermediates of general structure 28 (eg Eur. J. Med. Chem. 2016, 117, 85-98; Adv. Synth. Catal. 2016, 358, 2811-2816 ).
  • Intermediates of general structure 28 and 29 are either commercially available or can be prepared by methods known to the person skilled in the art or known from the literature.
  • Step 1 Preparation of 2 , -methyl-5 , - (pentafluoroethyl -4- (4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl-4 , - (trifluoromethyl-2 , H -L3 , -bipyrazole
  • Step 2 Preparation of methyl 5- , 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H-L3 , - bipyrazol-4-yl-thiophene-3-carboxylate
  • N-iodosuccinimide (159 mg) is added and the mixture is stirred overnight at 50 ° C.
  • the reaction mixture is cooled to room temperature, diluted with EtOAc and washed successively with saturated aqueous NaHSO 3 solution, water, saturated aqueous NaHCO 3 solution and saturated aqueous NaCl solution.
  • the solvent is removed under reduced pressure and the residue is purified by HPLC (gradient: H 2 O / acetonitrile).
  • Step 4 Preparation of 2-iodo-5- ⁇ 2 , -methyl-5 , - (entafluoroethyl) -4 , - (trifluoromethyl) -2 , H, 3 , -bipyrazol-4-yl-thiophene-3-carboxylic acid.
  • reaction mixture is stirred at 60 ° C for 1.5 h.
  • the reaction solution is cooled to room temperature, diluted with EtOAc and washed with aqueous HCl (IM) and saturated aqueous NaCl solution.
  • IM aqueous HCl
  • the organic phase is dried over MgSC and the solvent removed under reduced pressure.
  • 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H, 1,3'-bipyrazol-4-yl] thiophene-3-carboxylic acid becomes a yellow solid received (217 mg) and used without further purification in the subsequent reaction.
  • the reaction mixture is diluted with CH 2 CI 2 and washed with HCl (IN).
  • the organic phase is dried over MgSC and the solvent is removed under reduced pressure.
  • the residue is purified by HPLC (gradient: H 2 O / acetonitrile) and N-cyclopropyl-2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4'- (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxamide (Ia-1) is obtained as a colorless solid (80 mg).
  • Step 1 Preparation of 5-azido-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
  • Methyl 5-bromothiophene-3-carboxylate (1 g) is placed under argon in argon-saturated N, N-dimethylformamide (7 mL) and triethylamine (5.08 g).
  • bis (triphenylphosphine) palladium (II) dichloride 143 mg
  • copper (I) iodide (19 mg) are added and the reaction mixture is stirred at 80 ° C for 4 h.
  • the reaction solution is added after cooling with ethyl acetate and washed with HCl solution (5%) and aqueous saturated sodium chloride solution.
  • the organic phase is dried and freed from the solvent under reduced pressure.
  • Step 3 Preparation of methyl 5- ⁇ 1-ri-methyl-3- (pentafluoroethyl-4-trifluoromethyl-1H-pyrazol-5-yl-1H-1,2,3-triazol-4-yl ⁇ thiophene 3-carboxylate
  • the reaction solution from step 1 is diluted with water (3.5 mL). Methyl-5-ethynylthiophene-3-carboxylate (861 mg), copper (II) sulfate pentahydrate (90.5 mg), sodium ascorbate (71.8 mg) and tris [(1-benzyl-1H-1,2,3-triazole-4 -yl) methyl] amine (19.2 mg) is added and it is stirred at room temperature until the product from step 1 is completely reacted. The reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and freed from the solvent under reduced pressure.
  • Step 4 Preparation of methyl 2-chloro-5- ⁇ 1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole 4-yl ⁇ thiophene-3-carboxylate
  • Methyl 5- ⁇ 1- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl ⁇ thiophene-3 carboxylate (302 mg) is charged in acetic acid, N-chlorosuccinimide (127 mg) is added and the mixture is stirred for 4 h at room temperature. It is then heated to a bath temperature of 50 ° C and stirred overnight. The reaction mixture is diluted with ethyl acetate and washed with aqueous sodium thiosulfate solution and aqueous saturated sodium chloride solution.
  • Step 5 Preparation of 2-chloro-5- ⁇ 1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-4-yl ⁇ thiophene-3-carboxylic acid methyl 2-chloro-5- ⁇ 1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -LH-l, 2,3- Triazol-4-yl ⁇ thiophene-3-carboxylate (128 mg) is initially charged in tetrahydrofuran, an aqueous solution of lithium hydroxide (0.72 mL, 1M) is added dropwise and it is left overnight at room temperature touched.
  • lithium hydroxide (0.72 mL, 1M
  • Step 6 Preparation of 2-chloro-N-cyclopropyl-5- ⁇ 1 -ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazole 4-yl ⁇ thiophene-3-carboxamide (Ib-4)
  • Step 1 Preparation of 5-ethynyl-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
  • Ethinyl (trimethyl) silane 750 mg is placed under argon in tetrahydrofuran (12 mL) and cooled to -78 ° C.
  • n-Butyllithium (3.58 mL, 1.6M) is added dropwise and it is stirred for 5 minutes at -78 ° C.
  • 5-fluoro-l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (1.09 g) is added dropwise and stirred for 30 minutes at 0 ° C and 60 minutes at room temperature. The reaction is cooled again to -78 ° C and terminated by adding water.
  • Step 3 Preparation of methyl 5- ⁇ 4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-1-yl ⁇ thiophene -3-carboxylate
  • Methyl 5-azidothiophene-3-carboxylate (426 mg) is initially charged in dimethyl sulfoxide (4 mL) and water (2 mL), 5-ethynyl-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -H-OH.
  • pyrazole (815 mg)
  • Step 4 Preparation of methyl 2-chloro-5- ⁇ 4 1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole-1 -yl ⁇ thiophene-3-carboxylate
  • reaction mixture is heated to 50 ° C bath temperature and stirred for a further 5 h.
  • N-chlorosuccinimide 37 mg
  • N-chlorosuccinimide 74 mg
  • 80 ° C for 6 h 80 ° C for 6 h.
  • N-chlorosuccinimide 74 mg
  • the reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution.
  • the organic phase is dried, filtered and evaporated from the solvent under reduced pressure.
  • the residue is purified by means of pHPLC (gradient: acetonitrile / water).
  • Step 5 Preparation of 2-chloro-5- ⁇ 4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazole 1 -yl ⁇ thiophene-3-carboxylic acid
  • 3-Ethylcarbodiimide hydrochloride (94 mg) are introduced into dichloromethane (5 mL) and N, N-dimethylformamide (0.5 mL) and stirred for 15 minutes at room temperature. Then cyclopropylamine (28 ⁇ .) was added and stirred overnight at room temperature. The reaction mixture is diluted with dichloromethane and washed with HCl solution (I.M.). The organic phase is dried and removed from the solvent under reduced pressure.
  • Step 1 Preparation of ethyl 5-chloro-2- ⁇ 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H- ⁇ L3 , - bipyrazol-4-yl-L3-thiazole-4 carboxylate
  • reaction vail is then sealed and stirred overnight at room temperature.
  • the reaction mixture is filtered through silica gel and rinsed with ethyl acetate.
  • the filtrate is diluted with ethyl acetate and washed with water and aqueous saturated sodium chloride solution.
  • the organic phase is dried, filtered and freed from the solvent under reduced pressure.
  • the residue is purified by flash chromatography (gradient: c-hexane / ethyl acetate).
  • Step 2 Preparation of 5-chloro-2- ⁇ 2, methyl-5 - (pentaf ⁇ uorethyl) -4 - (trifluoromethyl) -2, H- ⁇ L3, - bipyrazoll-4-yll-L3-thiazole-4-carboxylic acid ethyl 5-chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [l, 3'-bipyrazol] -4-yl] -l, 3- thi
  • Step 3 Preparation of 5-chloro-N-cyclopropyl-2- [2 , -methyl-5 , - (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H- [L3'-bipyrazol-4-yl-L3 thiazole-4-carboxamide
  • reaction mixture is treated with diatomaceous earth and freed from the solvent under reduced pressure to be purified by flash chromatography (gradient: c-hexane / ethyl acetate).
  • 5-Chloro-N-cyclopropyl-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] - l, 3-thiazole-4-carboxamide (73 mg) as a colorless solid.
  • Agilent 1100 LC system 50 * 4.6 Zorbax Eclipse Plus C18 1.8 microm; Eluent A: acetonitrile (0.1% formic acid); Eluent B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min; Oven temperature 55 ° C; Flow: 2.0 mL / min. Mass detection takes place via an Agilend MSD system.
  • 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 ⁇ ; ⁇ 2 (intensity);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. 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 tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of IH 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, they can, like classical 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
  • 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 1H NMR interpretation.
  • 1 ⁇ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
  • the vials are populated with 5-10 adult dog tick ⁇ Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
  • a substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.
  • the vials are filled with 5-10 adult cat fleas ⁇ Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move uncoordinated are considered dead or struck.
  • a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Emulsifier alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • 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. ?
  • 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 ⁇ of the active ingredient preparation are transferred into microtiter plates and filled with 150 ⁇ l IPL41 insect medium (33% + 15%> sugar) to a final volume of 200 ⁇ . 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.

Abstract

The invention relates, inter alia, to compounds of general formula (I). The invention also relates to methods for synthesizing the compounds of formula (I). The compounds according to the invention are in particular suitable for controlling insects, arachnids and nematodes in agricultural applications and for controlling ectoparasites in veterinary medicine.

Description

PYRAZOLE ZUR BEKÄMPFUNG VON ARTHROPODEN  PYRAZOLE FOR COMBATING ARTHROPODES
Einleitung introduction
[0001] Die vorliegende Anmeldung betrifft neue Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen, vor allem von Arthropoden und insbesondere von Insekten, Spinnentieren und Nematoden. The present application relates to novel compounds, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes.
[0002] Es ist bekannt, dass bestimmte Halogen-substituierte Verbindungen insektizid wirksam sind (EP 1 911 751, WO 2012/069366, WO 2012/080376, WO 2012/107434 und WO 2012/175474). It is known that certain halogen-substituted compounds are insecticidally effective (EP 1 911 751, WO 2012/069366, WO 2012/080376, WO 2012/107434 and WO 2012/175474).
[0003] WO 2011/113756 offenbart Triazol Derivate, die insektizidale Wirkung aufweisen. [0003] WO 2011/113756 discloses triazole derivatives which have insecticidal activity.
[0004] Ferner ist bekannt, dass bestimmte Halogen-substituierte Verbindungen Cytokin-inhibitorische Aktivitäten aufweisen (WO 2000/07980). Furthermore, it is known that certain halogen-substituted compounds have cytokine-inhibitory activities (WO 2000/07980).
[0005] Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nie als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern plant protection products must meet many requirements, for example, in terms of height, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can never be considered complete and there is a constant need for new compounds with improved properties over the known compounds, at least with respect to individual aspects.
[0006] Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. The object of the present invention was to provide compounds by which the spectrum of pesticides widened under various aspects and / or their activity is improved.
[0007] Es wurde nun überraschenderweise gefunden, dass bestimmte Halogen-substituierte Verbindungen sowie deren Salze biologische Eigenschaften aufweisen und sich insbesondere zur Bekämpfung von tierischen Schädlingen eignen, und deshalb besonders gut im agrochemischen Bereich und im Bereich der Tiergesundheit einsetzbar sind. [0008] Ähnliche Verbindungen sind bereits aus WO 2010/051926, WO 2015/193218, WO 2015/101622 und WO 2017/055414 bekannt geworden. It has now surprisingly been found that certain halogen-substituted compounds and their salts have biological properties and are particularly suitable for controlling animal pests, and therefore are particularly useful in the agrochemical field and in the field of animal health. Similar compounds have already become known from WO 2010/051926, WO 2015/193218, WO 2015/101622 and WO 2017/055414.
Ausführungsformen der erfindungsgemäßen Verbindungen Embodiments of the compounds of the invention
[0009] Ein Aspekt der vorliegenden Erfindung bezieht sich auf neue insektizid, akarizid und/oder parasitizid wirksame Halogen-substituierte Verbindungen der allgemeine Formel (I) - - One aspect of the present invention relates to novel insecticidal, acaricidal and / or parasiticidal halogen-substituted compounds of the general formula (I) - -
Figure imgf000003_0001
worin
Figure imgf000003_0001
wherein
R1 für H, jeweils gegebenenfalls mit einem oder mehreren Substitutenten unabhängig voneinander ausgewählt aus Amino, Hydroxy, Halogen, Nitro, Cyano, Isocyano, Mercapto, Isothiocyanato, Ci-C i-Carboxy, Carbonamid, SF5, Aminosulfonyl, Ci-C i-Alkyl, C3-C i-Cycloalkyl, C2-C4- Alkenyl, C3-C4-Cycloalkenyl, C2-C4-Alkinyl, N-Mono-Ci-C4-alkyl-amino, NN-Di-Ci-C4- alkylamino, N-Ci-C4-Alkanoylamino, Ci-C4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, C3-C4-Cycloalkoxy, C3-C4-Cycloalkenyloxy, Ci-C4-Alkoxycarbonyl, C2-C4- C2-C4- Alkenyloxycarbonyl, C2-C4-Alkinyloxycarbonyl, C6-,Cio-,Ci4-Aryloxycarbonyl, C1-C4- Alkanoyl, C2-C4-Alkenylcarbonyl, C2-C4-Alkinylcarbonyl, C6-,Cio-,Ci4-Arylcarbonyl, C1-C4- Alkylsulfanyl, C3-C4-Cycloalkylsulfanyl, Ci-C4-Alkylthio, C2-C4-Alkenylthio, C3-C4- Cycloalkenylthio, C2-C4-Alkinylthio, Ci-C4-Alkylsulfenyl und Ci-C4-Alkylsulfinyl, wobei beide Enantiomere der Ci-C4-Alkylsulfinylgruppe umfasst sind, Ci-C4-Alkylsulfonyl, N-Mono-Ci-C4- alkyl-aminosulfonyl, NN-Di-Ci-C4-alkyl-aminosulfonyl, Ci-C4-Alkylphosphinyl, C1-C4- Alkylphosphonyl, wobei für Ci-C4-Alkylphosphinyl bzw. Ci-C4-Alkylphosphonyl beide Enantiomere umfasst sind, N-Ci-C4-Alkyl-aminocarbonyl, NN-Di-Ci-C4-alkyl-amino-carbonyl, N-Ci-C4-Alkanoyl-amino-carbonyl, N-Ci-C4-Alkanoyl-N-Ci-C4-alkyl-aminocarbonyl, CÖ-,CIO- ,Ci4-Aryl, C6-,Cio-,Ci4-Aryloxy, Benzyl, Benzyloxy, Benzylthio, C6-,Cio-,Ci4-Arylthio, CÖ-,CIO- ,Ci4-Arylamino, Benzylamino, Heterocyclyl und Trialkylsilyl, mit einer Doppelbindung verbundenen Substituenten wie Ci-C4-Alkyliden (z. B. Methyliden oder Ethyliden), einer Oxogruppe, einer Iminogruppe substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl C2-C6-Alkinyl, C3- C7-Cvcloalkyl, C6-.Cio-.Ci4-Aryl(Ci-C3)-alkyl 3. 4, 5. 6. 7. 8. 9 oder 10-gliedrigen-Heterocvclyl (z. B. Thietanyl wie Thiethanyl-3-yL Oxidothiethan wie l -Oxido-thietan-3-yi oder Dioxidothiethan wie l,l-Dioxido-thietan-3-yl oder 3, 4, 5, 6, 7, 8, 9 oder 10-gliedrigen- Heterocyclyl (Ci-CsValkyl steht, bevorzugt für gegebenenfalls mit Halogen oder Cyano substituiertem C3-C7-Cycloalkyl steht; R 1 is H, in each case optionally with one or more substituents selected independently from amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C 4 -alkyl, Alkyl, C 3 -C 10 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkyl-amino, N, N-di-C 1 -C 4 -alkylamino, N -C 1 -C 4 alkanoylamino, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 4 cycloalkoxy, C 3 -C 4 cycloalkenyloxy, C 1 -C 4 alkoxycarbonyl, C 2 -C 4 -C 2 -C 4 - alkenyloxycarbonyl, C2-C4-alkynyloxycarbonyl, C6, CIO, Ci 4 aryloxycarbonyl, C 1 -C4- alkanoyl, C 2 -C 4 alkenylcarbonyl, C 2 -C 4 alkynylcarbonyl, C6, CIO, Ci 4 aryl-carbonyl, C 1 -C4- alkylsulfanyl, C 3 -C 4 -Cycloalkylsulfanyl, Ci-C 4 alkylthio, C 2 -C 4 alkenylthio, C3-C4 Cycloalkenylthio, C2-C4-alkynylthio, Ci-C4 alkylsulfenyl and C 1 -C 4 -alkylsulfinyl, wherein both enantiomers of the C 1 -C 4 -alkylsulfinyl group are included, C 1 -C 4 -alkylsulfonyl, N-mono-C 1 -C 4 -alkyl-amino sulfonyl, N, N-di-C 1 -C 4 -alkylaminosulfonyl, C 1 -C 4 -alkylphosphinyl, C 1 -C 4 -alkylphosphonyl, where for C 1 -C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl both enantiomers are included, N-ci C 4 -alkylaminocarbonyl, N, N-di-C 1 -C 4 -alkylamino-carbonyl, N-C 1 -C 4 -alkanoylamino-carbonyl, N-C 1 -C 4 -alkanoyl-N-C 1 -C 4 -alkyl-aminocarbonyl, C Ö -, CI O - Ci4 aryl, C6, CIO, Ci4 aryloxy, benzyl, benzyloxy, benzylthio, C6, CIO, Ci4-arylthio, COE, CIO, Ci4-arylamino, benzylamino, Heterocyclyl and trialkylsilyl, substituents linked to a double bond, such as C 1 -C 4 -alkylidene (e.g. As methylidene or ethylidene), an oxo group, an imino group substituted Ci-C6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C 7 -Cvcloalkyl, C6-.Cio-.Ci4-aryl (Ci-C3 ) -alkyl 3. 4, 5. 6. 7. 8. 9 or 10-membered heterocyclyl (eg thietanyl, such as thiethanyl-3-yl oxidothiethane, such as 1-oxo-thietan-3-yl or dioxothiethane, such as 1, l-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci-CsValkyl, preferably represents optionally substituted by halogen or cyano-substituted C3-C7-cycloalkyl;
R2 für H oder Ci-C6-Alkyl steht; die Gruppierungen R 2 is H or C 1 -C 6 alkyl; the groupings
Ai, A2 und A3 unabhängig voneinander für N, O, CR3, S oder N-R4 stehen, wobei Ai, A2, A3, Z und das C-Atom des Ringes ein aromatisches System bilden; Ai, A2 and A3 are each independently N, O, CR 3, S, or NR 4, wherein Ai, A2, A3, Z and the C-atom of the ring form an aromatic system;
R3 jeweils unabhängig voneinander für H, Cl, F, I, Br oder gegebenenfalls halogeniertes C1-C4- Alkyl steht; Each R 3 is independently H, Cl, F, I, Br or optionally halogenated C 1 -C 4 alkyl;
R4 jeweils unabhängig für H oder gegebenenfalls halogeniertes Ci-C4-Alkyl steht; Q für O oder S steht; Each R 4 is independently H or optionally halogenated C 1 -C 4 alkyl; Q is O or S;
Z für C oder N steht, besonders bevorzugt für C steht; Z is C or N, particularly preferably C;
T für einen der nachfolgend aufgeführten 5-gliedrigen Heteroaromaten T1-T8 steht, wobei die T is one of the 5-membered heteroaromatics T1-T8 listed below, wherein the
Figure imgf000004_0001
Figure imgf000004_0001
Bindung zu mit einer Raute # gekennzeichnet ist,  Binding to is marked with a rhombus #,
Tl T2 T3 T4 T5 T6 T7 T8 T1 T2 T3 T4 T5 T6 T7 T8
Figure imgf000004_0002
wobei
Figure imgf000004_0002
in which
R5 für optional halogeniertes (Ci-C6)-Alkyl, optional halogeniertes (Ci-C6)-Alkoxy, -S(0)o-2-(Ci- C2)-alkyl oder NO2 steht, bevorzugt für perhalogeniertes (Ci-C4)-Alkyl, perhalogeniertes (C1-C4)- Alkoxy oder -S(0)o-2-(Ci-C2)-alkyl steht, mehr bevorzugt für perfluoriertes (Ci-C4)-Alkyl, perfluoriertes (Ci-C4)-Alkoxy oder -S(0)o-2-(Ci-C2)-alkyl steht, noch mehr bevorzugt für CF3 steht; R 5 is optionally halogenated (C 1 -C 6) -alkyl, optionally halogenated (C 1 -C 6) -alkoxy, -S (O) o-2 (C 1 -C 2) -alkyl or NO 2, preferably perhalogenated (C 1 -C 4 ) -Alkyl, perhalogenated (C 1 -C 4 ) -alkoxy or -S (O) o- ( 2 -C (Ci-C 2 ) -alkyl, more preferably perfluorinated (Ci-C 4 ) -alkyl, perfluorinated (Ci-C 4) alkoxy or -S (0) o-2 - (Ci-C 2) alkyl, more preferably is CF3;
R6 für optional halogeniertes (C3-C6)-Cycloalkyl, optional halogeniertes (Ci-Ce)-Alkoxy oder optional halogeniertes (Ci-C6)-Alkyl steht, bevorzugt für perhalogeniertes (Ci-C4)-Alkyl oder perhalogeniertes (Ci-C4)-Alkoxy steht, mehr bevorzugt für perfluoriertes (Ci-C4)-Alkyl oder perfluoriertes (Ci-C4)-Alkoxy steht, noch mehr bevorzugt für C2F5 steht; - - sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I). R 6 represents optionally halogenated (C 3 -C 6 ) -cycloalkyl, optionally halogenated (C 1 -C 6) -alkoxy or optionally halogenated (C 1 -C 6) -alkyl, preferably perhalogenated (C 1 -C 4 ) -alkyl or perhalogenated (C 1 -C 4 ) -alkyl; C 4) alkoxy, more preferably perfluorinated (C 1 -C 4) -alkyl or perfluorinated (C 1 -C 4) -alkoxy, even more preferably C 2 F 5; - - As well as salts, N-oxides and tautomeric forms of the compounds of formula (I).
[0010] Eine bevorzugte Ausführungsform der vorliegenden Erfindung richtet sich dabei auf Verbindungen gemäß Absatz [0009], wobei R2 für H oder Methyl steht. A preferred embodiment of the present invention is directed to compounds according to paragraph [0009], wherein R 2 is H or methyl.
[0011] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] oder [0010], wobei T für für Tl, T4 oder T5 steht. A further preferred embodiment is directed to compounds according to one of the paragraphs [0009] or [0010], where T is for Tl, T4 or T5.
[0012] In einer weiterhin bevorzugten Ausgestaltung der Verbindungen gemäß der Absätze [0009] oder [0010] steht T für T2, T3, T4, T5, T6, T7 oder T8, besonders bevorzugt für T4 oder T5. In a further preferred embodiment of the compounds according to the paragraphs [0009] or [0010] T stands for T2, T3, T4, T5, T6, T7 or T8, particularly preferably for T4 or T5.
[0013] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] bis [0011], wobei R1 für Cyclopropyl oder 1 -CN-Cyclopropyl steht. [0014] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] bis [0013], wobei Q für O steht. A further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0011], wherein R 1 is cyclopropyl or 1 -CN-cyclopropyl. A further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0013], wherein Q is O.
[0015] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] bis [0014], wobei A3 für S steht. A further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0014], wherein A 3 is S.
[0016] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] bis [0015], wobei Z für C und A2 für C-Hal, wobei Hai bevorzugt für I, Br oder Cl, mehr bevorzugt für Br oder I und insbesondere bevorzugt für Br steht, stehen. A further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0015], wherein Z is C and A 2 is C-Hal, wherein Hal preferably represents I, Br or Cl, more preferably Br or I and especially preferably represents Br stand.
[0017] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß einem der Absätze [0009] bis [0016], wobei A3 für S steht, Z für C und A2 für C-Hal, wobei Hai bevorzugt für Br, I oder Cl, mehr bevorzugt für Cl steht, stehen und Ai für C-H oder N steht. [0018] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen der Formel (Ia), A further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0016], wherein A3 is S, Z is C and A2 is C-Hal, wherein Hal is preferably Br, I or Cl, more preferably represents Cl, and Ai is CH or N. A further preferred embodiment is directed to compounds of the formula (Ia),
Figure imgf000005_0001
Figure imgf000005_0001
(Ia) wonn Q, R1, R2, R5 und R6 und Ai wie für Verbindungen der Formel (I) oder einer bevorzugten Ausführung von Verbindungen der Formel (I) hierin definiert sind und Hai bevorzugt für I, Br oder Cl steht. (Ia) wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined for compounds of formula (I) or a preferred embodiment of compounds of formula (I) herein and Hai is preferably I, Br or Cl.
[0019] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen der Formel (Ib) wonn Q, R1, R2, R5 und R6 und Ai wie für Verbindungen der Formel (I) oder einer bevorzugten Ausführung von Verbindungen der Formel (I) oder einer bevorzugten Ausführung von Verbindungen der Formel (I) hierin definiert sind und Hai bevorzugt für I, Br oder Cl steht. A further preferred embodiment is directed to compounds of the formula (Ib) wonn Q, R 1 , R 2 , R 5 and R 6 and Ai as for compounds of formula (I) or a preferred embodiment of compounds of formula ( I) or a preferred embodiment of compounds of formula (I) are defined herein and Hai is preferably I, Br or Cl.
Figure imgf000006_0001
Figure imgf000006_0001
(Ib) (Ib)
[0020] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen der Formel (Ic) Worin Q, R1, R2, R5 und R6 und Ai wie für Verbindungen der Formel (I) hierin definiert sind und Hai bevorzugt für I, Br oder Cl steht. A further preferred embodiment is directed to compounds of the formula (Ic) Wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined for compounds of the formula (I) herein and Hai is preferably I, Br or Cl stands.
Figure imgf000006_0002
Figure imgf000006_0002
[0021] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß der Formel (Ia) worin Q für O steht, Ai für N oder C-H steht, Hai für Br, I oder Cl steht, R2 für H steht, R1 für gegebenenfalls mit CN substituiertes Cyclopropyl (wie Cyclopropyl oder 1 -CN-Cyclopropyl) steht, R5 für CF3 und R6 für C2F5 steht. A further preferred embodiment is directed to compounds of the formula (Ia) wherein Q is O, Ai is N or CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally substituted by CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
[0022] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß der Formel (Ib) worin Q für O steht, Ai für C-H steht, Hai für Br, I oder Cl steht, R2 für H steht, R1 für gegebenenfalls mit CN substituiertes Cyclopropyl (wie Cyclopropyl oder 1 -CN-Cyclopropyl) steht, R5 für CF3 und R6 für C2F5 steht. A further preferred embodiment is directed to compounds according to formula (Ib) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
[0023] Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß der Formel (Ic) worin Q für O steht, Ai für C-H steht, Hai für Br, I oder Cl steht, R2 für H steht, R1 für gegebenenfalls mit CN substituiertes Cyclopropyl (wie Cyclopropyl oder 1 -CN-Cyclopropyl) steht, R5 für CF3 und R6 für C2F5 steht. A further preferred embodiment is directed to compounds according to formula (Ic) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
[0024] Ein weiterer Aspekt bezieht sich auf ein Insektizides Mittel umfassend mindestens eine Verbindung der Formel (I) gemäß einem der Absätze [0009] bis [0023] und einem Streckmittel und/oder einer oberflächenaktiven Substanz. Another aspect relates to an insecticidal composition comprising at least one compound of the formula (I) according to any one of paragraphs [0009] to [0023] and an extender and / or a surface-active substance.
[0025] Ein weiterer Aspekt bezieht sich auf ein Verfahren zum Schutz von transgenem oder konventionellem Saatgut und der daraus entstehenden Pflanze vor dem Befall von Schädlingen, dadurch gekennzeichnet, dass das Saatgut mit mindestens einer Verbindung gemäß einem der Absätze [0009] bis [0023] behandelt wird. Another aspect relates to a process for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound according to any of paragraphs [0009] to [0023] is treated.
[0026] Ein weiterer Aspekt bezieht sich auf die Verwendung von Verbindungen gemäß einem der Absätze [0009] bis [0023], oder von einem msektiziden Mittel gemäß Absatz [0024] zum Bekämpfen von Schädlingen. Another aspect relates to the use of compounds according to any one of paragraphs [0009] to [0023], or of a insecticidal agent according to paragraph [0024] for controlling pests.
[0027] Ein weiterer Aspekt bezieht sich auf Saatgut, enthaltend eine Verbindung gemäß einem der Absätze [0009] bis [0023] als Bestandteil einer Umhüllung, welche auf das Saatgut aufgebracht ist, oder als weitere Schicht, die zusätzlich zu einer Umhüllung auf das Saatgut aufgebracht ist. Another aspect relates to seeds containing a compound according to any one of paragraphs [0009] to [0023] as part of a casing applied to the seed, or as a further layer in addition to a coating on the seed is applied.
[0028] Ein weiterer Aspekt betrifft ein Verfahren zum Schutz von transgenem oder konventionellem Saatgut und der daraus entstehenden Pflanze vor dem Befall von Schädlingen, dadurch gekennzeichnet, dass das Saatgut mit mindestens einer Verbindung der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben behandelt wird. Another aspect relates to a method for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound of formula (I) or derived from formula (I) Formula is treated as described herein.
[0029] Noch ein weitere Aspekt betrifft die Verwendung von Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben oder von einem msektiziden Mittel wie hierin beschrieben zum Bekämpfen von Schädlingen. Yet another aspect relates to the use of compounds of formula (I) or a formula derived from formula (I) as described herein or of a insecticidal agent as described herein for controlling pests.
[0030] Ein weiterer Aspekt betrifft die Verwendung von Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben in der Vektorkontrolle. η Another aspect relates to the use of compounds of formula (I) or of a formula derived from formula (I) as described herein in the vector control. η
[0031] Noch ein weiterer Aspekt betrifft Saatgut, bei dem eine Verbindung der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung auf das Saatgut aufgebracht ist. Yet another aspect relates to seed in which a compound of formula (I) or a formula derived from formula (I) as described herein is applied to the seed in addition to a casing as part of a casing or as a further layer or layers is.
[0032] Entsprechend betrifft ein weiterer Aspekt ein Verfahren zum Aufbringen einer Umhüllung umfassend mindestens eine Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben oder zum Aufbringen einer Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben, die als Schicht oder weitere Schichten zusätzlich zu einer Umhüllung auf Saatgut aufgebracht wird, umfassend die Schritte, a) mischen von Samen mit einem Überzugsmaterial bestehend aus oder umfassend eine Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel wie hierin beschrieben, b) anreichern der erhaltenen übergezogenen Samenmasse, c) trocknen der erhaltenen angereicherten Samenmasse, d) entballen (dis- oder entagglomerieren) der erhaltenen getrockneten Samenmasse. Accordingly, a further aspect relates to a process for applying a coating comprising at least one compound of formula (I) or a formula derived from formula (I) as described herein or for applying a compound of formula (I) or one of formula ( I) derived formula as herein described, applied as a layer or further layers in addition to a casing on seed, comprising the steps of a) mixing seeds with a coating material consisting of or comprising a compound of formula (I) or one of formula (I) derived formula as described herein, b) enriching the obtained coated seed mass, c) drying the resulting enriched seed mass, d) degumming (disagglomerating or deagglomerating) the obtained dried seed mass.
[0033] Die hier beschriebenen Verbindungen der Formel (I) oder einer von Formel (I) abgeleiteten Formel können gegebenenfalls in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Die Erfindung betrifft sowohl die reinen Isomere als auch die Isomerengemische. The compounds of the formula (I) described herein or of a formula derived from formula (I) may optionally be present in different composition depending on the nature of the substituents as geometric and / or as optically active isomers or corresponding isomer mixtures. The invention relates to both the pure isomers and the isomer mixtures.
[0034] Die erfindungsgemäßen Verbindungen können auch als Metalikomplexe vorliegen. Definitionen [0035] Der Fachmann ist sich bewusst, dass, wenn nicht ausdrücklich angegeben, die Ausdrücke "ein", „eine" oder „eines" wie in dieser Anmeldung genutzt je nach Situation "ein/eine/eines (1)", "ein/eine/eines (1) oder mehr" oder "mindestens ein/eine/eines (1)" bedeuten kann. The compounds of the invention may also be present as metal complexes. Definitions It will be understood by those skilled in the art, unless expressly stated, that the terms "a," "an," or "an" as used in this application, "depending on the situation," "a (1)", " may mean one (1) or more or at least one (1).
[0036] Strukturen mit einer variablen Anzahl an möglichen Kohlenstoffatomen (C- Atomen) können in der vorliegenden Anmeldung als Cuntere Grenze C-Atome~Cobere Grenze C-Atome~ Strukturen (CUG-C0G-Strukturen) bezeichnet werden, umso näher bestimmt zu werden. Beispiel: eine Alkylgruppe kann aus 3 bis 10 C- Atomen bestehen und entspricht dann C3-Cio-Alkyl. Ringstrukturen aus C-Atomen und Heteroatomen können als „uG bis oG-gliedrige" Strukturen bezeichnet werden. Ein Beispiel einer 6-gliedrigen Ringstruktur ist Toluol (eine 6-gliedriges Ringstruktur, die mit einer Methylgruppe substituiert ist). Structures with a variable number of possible carbon atoms (C atoms) can be referred to in the present application as Cuntere limit C atoms ~ Cobere boundary C atoms ~ structures (C U GC 0 G structures), the more determined to become. Example: An alkyl group may consist of 3 to 10 C atoms and then corresponds to C3-Cio-alkyl. Ring structures of C atoms and heteroatoms may be referred to as "uG to oG-membered" structures An example of a 6-membered ring structure is toluene (a 6-membered ring structure substituted with a methyl group).
[0037] Dem Fachmann ist klar, dass in dieser Anmeldung genannte Beispiele nicht als beschränkend anzusehen sind sondern lediglich einige Ausführungsformen näher beschreiben. [0038] Bei Zusammengesetzen Substituenten (z. B. Hydroxyalkyl oder Alkoxy oder Alkylcarbonyl) ist der zweitgenannte Substituente jeweils mit der Grundstruktur Verbunden (z. B. Hydroxymethyl: -CH2- OH oder Methoxy: -O-CH3 oder Methylcarbonyl: -C(=0)-CH3). It is clear to the person skilled in the art that examples mentioned in this application are not to be regarded as limiting but merely describe some embodiments in more detail. When the substituents (eg hydroxyalkyl or alkoxy or alkylcarbonyl) are combined, the second-mentioned substituent is in each case bonded to the basic structure (for example hydroxymethyl: -CH 2 -OH or methoxy: -O-CH 3 or methylcarbonyl: -C ( = 0) -CH 3 ).
[0039] Bei den in den vorstehenden Formeln angegebenen Definitionen der Symbole wurden Sammel- begriffe verwendet, die allgemein repräsentativ für die folgenden Substituenten stehen: In the definitions of the symbols given in the above formulas, collective terms were used which are generally representative of the following substituents:
[0040] Halogen bezieht sich auf die Elemente der 7. Hauptgruppe, bevorzugt Fluor, Chlor, Brom und Iod, mehr bevorzugt Fluor, Chlor und Brom. Halogen refers to the elements of the 7th main group, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine.
[0041] Erfindungsgemäß steht "Alkyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettige oder verzweigte Kohlenwasserstoffe, vorzugsweise mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Isobutyl, s-Butyl, t-Butyl, Pentyl, 1- Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1 ,2-Dimethylpropyl, 1 , 1 -Dimethylpropyl, 2,2- Dimethylpropyl, 1 -Ethylpropyl, Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4- Methylpentyl, 1 ,2-Dimethylpropyl, 1,3-Dimethylbutyl, 1 ,4-Dimethylbutyl, 2,3-Dimethylbutyl, 1,1- Dimethylbutyl, 2,2-Dimethylbutyl, 3,3-Dimethylbutyl, 1,1,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1- Ethylbutyl und 2-Ethylbutyl. Ferner bevorzugt sind Alkyle mit 1 bis 4 Kohlenstoffatomen, wie unter anderem Methyl, Ethyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Isobutyl, s-Butyl oder t-Butyl. Die erfindungsgemäßen Alkyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkyl" - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s Butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 2-dimethylpropyl, 1,3-dimethylbutyl, 1, 4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3 Dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and 2-ethylbutyl. Also preferred are alkyls having 1 to 4 carbon atoms, such as methyl, ethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl, among others. The alkyls according to the invention may be substituted by one or more, identical or different radicals.
[0042] Erfindungsgemäß steht "Alkenyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettige oder verzweigte Kohlenwasserstoffe, vorzugsweise mit 2 bis 6 Kohlenstoffatomen und mindestens einer Doppelbindung, wie beispielsweise Vinyl, 2-Propenyl, 2- Butenyl, 3-Butenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1- Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3- Methyl-3-butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl-2-propenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4- Methyl-2-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2-Methyl-4- pentenyl, 3 -Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl, 1 , 1 -dimethyl-3 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3 -butenyl, 1, 3 -Dimethy 1-2 -butenyl, 2,2-Dimethyl-3 -butenyl, 2,3- Dimethy 1-2 -butenyl, 2,3-Dimethyl-3-butenyl, 1 -Ethyl-2-butenyl, l-Ethyl-3 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3 -butenyl, 1 , 1 ,2-Trimethyl-2-propenyl, 1 -Ethyl- 1 -methyl-2-propenyl und 1 -Ethyl-2-methyl-2- propenyl. Ferner bevorzugt sind Alkenyle mit 2 bis 4 Kohlenstoffatomen, wie unter anderem 2- Propenyl, 2-Butenyl oder 1 -Methyl-2-propenyl. Die erfindungsgemäßen Alkenyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. - -According to the invention "alkenyl" - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl , 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2 -butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl 2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2 pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl , 1, 1-Dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3 -Dimethyl 1-2 - butenyl, 2,2-dimethyl-3-butenyl, 2,3- Dimethy 1-2 -butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 , 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl. Further preferred are alkenyls having 2 to 4 carbon atoms, such as 2-propenyl, 2-butenyl or 1-methyl-2-propenyl, among others. The alkenyls according to the invention may be substituted by one or more identical or different radicals. - -
[0043] Erfindungsgemäß steht "Alkinyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettige oder verzweigte Kohlenwasserstoffe, vorzugsweise mit 2 bis 6 Kohlenstoffatomen und mindestens einer Dreifachbindung wie beispielsweise 2-Propinyl, 2-Butinyl, 3- Butinyl, 1 -Methyl-2-propinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-3-butinyl, 2-Methyl-3- butinyl, 1 -Methyl-2-butinyl, 1 , 1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 2-Hexinyl, 3-Hexinyl, 4- Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, l-Methyl-3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3- pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-2-pentinyl, 1 , 1 -Dimethyl-3 -butinyl, 1,2- Dimethyl-3 -butinyl, 2,2-Dimethyl-3 -butinyl, 1-Ethyl- 3 -butinyl, 2-Ethyl-3 -butinyl, l-Ethyl-l-methyl-2- propinyl und 2,5-Hexadiynyl. Ferner bevorzugt sind Alkinyle mit 2 bis 4 Kohlenstoffatomen wie unter anderem Ethinyl, 2-Propinyl oder 2-Butinyl-2-propenyl. Die erfindungsgemäßen Alkinyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkynyl" - alone or as part of a chemical group - is straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one triple bond such as 2-propynyl, 2-butynyl, 3-butynyl, 1 - Methyl 2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1, 1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-3-butynyl, 1,2-dimethyl-3 - butinyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and 2,5-hexadiynyl. Also preferred are alkynyls having 2 to 4 carbon atoms, such as, inter alia, ethynyl, 2-propynyl or 2-butynyl-2-propenyl. The alkynyls according to the invention may be substituted by one or more, identical or different radicals.
[0044] Erfindungsgemäß steht "Cycloalkyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für mono-, bi- oder tricyclische Kohlenwasserstoffe, vorzugsweise mit 3 bis 10 Kohlenstoffen wie beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Bicyclo[2.2.1]heptyl, Bicyclo[2.2.2]octyl oder Adamantyl. Ferner bevorzugt sind Cycloalkyle mit 3, 4, 5, 6 oder 7 Kohlenstoffatomen, wie unter anderem Cyclopropyl oder Cyclobutyl. Die erfindungsgemäßen Cycloalkyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "cycloalkyl" - alone or as part of a chemical group - for mono-, bi- or tricyclic hydrocarbons, preferably having 3 to 10 carbons such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo 2.2.1] heptyl, bicyclo [2.2.2] octyl or adamantyl. Also preferred are cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms, such as, inter alia, cyclopropyl or cyclobutyl. The cycloalkyls of the invention may be substituted by one or more, identical or different radicals.
[0045] Erfindungsgemäß steht "Alkylcycloalkyl" für mono-, bi- oder tricyclisches Alkylcycloalkyl, vorzugsweise mit 4 bis 10 oder 4 bis 7 Kohlenstoffatomen, wie beispielsweise Methylcyclopropyl, Ethylcyclopropyl, Isopropylcyclobutyl, 3-Methylcyclopentyl und 4-Methyl-cyclohexyl. Ferner bevorzugt sind Alkylcycloalkyle mit 4, 5 oder 7 Kohlenstoffatomen wie unter anderen Ethylcyclopropyl oder 4-Methyl-cyclohexyl. Die erfindungsgemäßen Alkylcycloalkyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. [0046] Erfindungsgemäß steht "Cycloalkylalkyl" für mono, bi- oder tricyclisches Cycloalkylalkyl, vorzugsweise mit 4 bis 10 oder 4 bis 7 Kohlenstoffatomen, wie beispielsweise Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl und Cyclopentylethyl. Ferner bevorzugt sind Cycloalkylalkyle mit 4, 5 oder 7 Kohlenstoffatomen wie unter anderen Cyclopropylmethyl oder Cyclobutylmethyl. Die erfindungsgemäßen Cycloalkylalkyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkylcycloalkyl" is mono-, bi- or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Further preferred are alkylcycloalkyls having 4, 5 or 7 carbon atoms, such as, for example, ethylcyclopropyl or 4-methylcyclohexyl. The alkylcycloalkyls of the invention may be substituted by one or more, identical or different radicals. According to the invention "cycloalkylalkyl" is mono-, bi- or tricyclic cycloalkylalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Also preferred are cycloalkylalkyl having 4, 5 or 7 carbon atoms, such as cyclopropylmethyl or cyclobutylmethyl. The cycloalkylalkyls of the invention may be substituted by one or more, identical or different radicals.
[0047] Erfindungsgemäß steht "Hydroxyalkyl" für geradkettigen oder verzweigten Alkohol, vorzugsweise mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methanol, Ethanol, n-Propanol, Isopropanol, n-Butanol, Isobutanol, s-Butanol und t-Butanol. Ferner bevorzugt sind Hydroxyalkylgruppen mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Hydroxyalkylgruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein - -According to the invention "hydroxyalkyl" is straight-chain or branched alcohol, preferably having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. Further preferred are hydroxyalkyl groups having 1 to 4 carbon atoms. The hydroxyalkyl groups according to the invention may be substituted by one or more identical or different radicals - -
[0048] Erfindungsgemäß steht "Alkoxy" für geradkettiges oder verzweigtes O-Alkyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methoxy, Ethoxy, n-Propoxy, Isopropoxy, n-Butoxy, Isobutoxy, s-Butoxy und t-Butoxy. Ferner bevorzugt sind Alkoxygruppen mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Alkoxygruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkoxy" represents straight-chain or branched O-alkyl, preferably having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Further preferred are alkoxy groups having 1 to 4 carbon atoms. The alkoxy groups according to the invention may be substituted by one or more identical or different radicals.
[0049] Erfindungsgemäß steht "Alkylsulfanyl" für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen, wie beispielsweise Methylthio, Ethylthio, n-Propylthio, Isopropylthio, n-Butylthio, Isobutylthio, s-Butylthio und t-Butylthio. Ferner bevorzugt sind Alkylsulfanylgrappen mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Alkylsulfanylgrappen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkylsulfanyl" is straight-chain or branched S-alkyl, preferably having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio and t-butylthio. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms. The Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
[0050] Erfindungsgemäß steht "Alkylsulfinyl" für geradkettiges oder verzweigtes Alkylsulfinyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen wie beispielsweise Methylsulfinyl, Ethylsulfinyl, n- Propylsulfinyl, Isopropylsulfinyl, n-Butylsulfinyl, Isobutylsulfinyl, s-Butylsulfinyl und t-Butylsulfinyl. Ferner bevorzugt sind Alkylsulfinylgrappen mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Alkylsulfinylgrappen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkylsulfinyl" represents straight-chain or branched alkylsulfinyl, preferably having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl and t-butylsulfinyl. Further preferred are alkylsulfinyl groups having 1 to 4 carbon atoms. The alkylsulfinylgrappen invention can be substituted with one or more, identical or different radicals.
[0051] Erfindungsgemäß steht "Alkylsulfonyl" für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen wie beispielsweise Methylsulfonyl, Ethylsulfonyl, n- Propylsulfonyl, Isopropylsulfonyl, n-Butylsulfonyl, Isobutylsulfonyl, s-Butylsulfonyl und t- Butylsulfonyl. Ferner bevorzugt sind Alkylsulfanylgrappen mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Alkylsulfanylgrappen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkylsulfonyl" represents straight-chain or branched alkylsulfonyl, preferably having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl and t-butylsulfonyl. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms. The Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
[0052] Erfindungsgemäß steht "Alkylcarbonyl" für geradkettiges oder verzweigtes Alkyl-C(=0), vorzugsweise mit 2 bis 7 Kohlenstoffatomen, wie Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, Isopropylcarbonyl, s-Butylcarbonyl und t-Butylcarbonyl. Ferner bevorzugt sind Alkylcarbonyle mit 1 bis 4 Kohlenstoffatomen. Die erfindungsgemäßen Alkylcarbonyle können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkylcarbonyl" is straight-chain or branched alkyl-C (= 0), preferably having 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl and t-butylcarbonyl. Further preferred are alkyl carbonyls having 1 to 4 carbon atoms. The alkylcarbonyls according to the invention may be substituted by one or more identical or different radicals.
[0053] Erfindungsgemäß steht "Cycloalkylcarbonyl" für geradkettiges oder verzweigtes Cycloalkylcarbonyl, vorzugsweise mit 3 bis 10 Kohlenstoffatomen im Cycloalkylteil, wie beispielsweise Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexyl-carbonyl, Cycloheptyl- carbonyl, Cyclooctylcarbonyl, Bicyclo[2.2.1]heptyl, Bycyclo[2.2.2]octylcarbonyl und Adamantylcarbonyl. Ferner bevorzugt sind Cycloalkylcarbonyl mit 3, 5 oder 7 Kohlenstoffatomen im Cycloalkylteil. Die erfindungsgemäßen Cycloalkylcarbonylgrappen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. - -According to the invention, "cycloalkylcarbonyl" represents straight-chain or branched cycloalkylcarbonyl, preferably having 3 to 10 carbon atoms in the cycloalkyl moiety, such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptyl, bycyclo [2.2.2] octylcarbonyl and adamantylcarbonyl. Also preferred are cycloalkylcarbonyl having 3, 5 or 7 carbon atoms in the cycloalkyl moiety. The Cycloalkylcarbonylgrappen invention can be substituted with one or more, identical or different radicals. - -
[0054] Erfindungsgemäß steht "Alkoxycarbonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkoxycarbonyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen oder 1 bis 4 Kohlenstoffatomen im Alkoxyteil, wie beispielsweise Methoxycarbonyl, Ethoxycarbonyl, n-Propoxycarbonyl, Isopropoxycarbonyl, s-Butoxycarbonyl und t- Butoxycarbonyl. Die erfindungsgemäßen Alkoxycarbonylgruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "alkoxycarbonyl" - alone or as part of a chemical group - is straight-chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl. The alkoxycarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
[0055] Erfindungsgemäß steht "Alkylaminocarbonyl" für geradkettiges oder verzweigtes Alkylaminocarbonyl mit vorzugsweise 1 bis 6 Kohlenstoffatomen oder 1 bis 4 Kohlenstoffatomen im Alkylteil, wie beispielsweise Methylaminocarbonyl, Ethylaminocarbonyl, n-Proylaminocarbonyl, Isopropylaminocarbonyl, s-Butylaminocarbonyl und t-Butylaminocarbonyl. Die erfindungsgemäßen Alkylammocarbonylgruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. [0055] In the present invention, "alkylaminocarbonyl" means straight-chain or branched alkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl. The alkylammocarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
[0056] Erfindungsgemäß steht "NN-Dialkylamino-carbonyl" für geradkettiges oder verzweigtes NN- Dialkylaminocarbonyl mit vorzugsweise 1 bis 6 Kohlenstoffatomen oder 1 bis 4 Kohlenstoffatomen im Alkylteil, wie beispielsweise NN-Dimethylamino-carbonyl, Ν.Ν-Diethylamino-carbonyl, NN-Di(n- propylamino)-carbonyl, NN-Di-(isopropylamino)-carbonyl und NN-Di-(s-butylamino)-carbonyl. Die erfindungsgemäßen NN-Dialkylamino-carbonylgruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. According to the invention "NN-dialkylamino-carbonyl" is straight-chain or branched NN-dialkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as NN-dimethylamino-carbonyl, Ν.Ν-diethylamino-carbonyl, NN Di (n-propylamino) carbonyl, N, N'-di (isopropylamino) carbonyl and N, N'-di (s-butylamino) carbonyl. The N, N-dialkylaminocarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
[0057] Erfindungsgemäß steht "Aryl" für ein mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-Kohlenstoffatomen, wie beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, vorzugsweise Phenyl. Ferner steht Aryl auch für mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenyl, wobei die Bindungsstelle am aromatischen System ist. Die erfindungsgemäßen Arylgruppen können mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. [0058] Beispiele substitutierter Aryle stellen die Arylalkyle dar, die gleichfalls mit einem oder mehreren, gleichen oder verschiedenen Resten im Ci-C i-Alkyl- und/oder C6-Ci4-Arylteil substituiert sein können. Beispiele solcher Arylalkyle sind unter anderem Benzyl und 1 -Phenylethyl. According to the invention "aryl" is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl. In addition, aryl also represents polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, where the binding site is on the aromatic system. The aryl groups according to the invention may be substituted by one or more, identical or different radicals. Examples of substituted aryls are the arylalkyls, which may likewise be substituted by one or more identical or different radicals in the C 1 -C -alkyl- and / or C 6 -C 4 -aryl moiety. Examples of such arylalkyls include benzyl and 1-phenylethyl.
[0059] Erfindungsgemäß steht "Heterocyclus", "heterocyclischer Ring" oder "heterocyclisches Ringsystem" für ein carbocyclisches Ringsystem mit mindestens einem Ring, in dem mindestens ein Kohlenstoffatom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P, B, Si, Se und der gesättigt, ungesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1, 2 oder 3 Heteroatome im - - heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei Sauerstoffatome direkt benachbart sein sollen. Die heterocyclischen Ringe enthalten gewöhnlicherweise nicht mehr als 4 Stickstoffatome, und/oder nicht mehr als 2 Sauerstoffatome und/oder nicht mehr als 2 Schwefelatome. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden erfindungsgemäß auch mehrcyclische Systeme umfaßt, wie beispielsweise 8-Aza-bicyclo[3.2.1]octanyl oder l-Aza-bicyclo[2.2.1]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden erfindungsgemäß auch spirocyclische Systeme umfasst, wie beispielsweise l-Oxa-5-aza-spiro[2.3]hexyl. [0060] Erfindungsgemäße Heterocyclylgruppen sind beispielsweise Piperidinyl, Piperazinyl, Morpholinyl, Thiomorpholinyl, Dihydropyranyl, Tetrahydropyranyl, Dioxanyl, Pyrrolinyl, Pyrrolidinyl, Imidazolinyl, Imidazolidinyl, Thiazolidinyl, Oxazolidinyl, Dioxolanyl, Dioxolyl, Pyrazolidinyl, Tetrahydrofuranyl, Dihydrofuranyl, Oxetanyl, Oxiranyl, Azetidinyl, Aziridinyl, Oxazetidinyl, Oxaziridinyl, Oxazepanyl, Oxazinanyl, Azepanyl, Oxopyrrolidinyl, Dioxopyrrolidinyl, Oxomorpholinyl, Oxopiperazinyl und Oxepanyl. According to the invention "heterocycle", "heterocyclic ring" or "heterocyclic ring system" means a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S. , P, B, Si, Se and which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in - - Heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent. The heterocyclic rings usually contain not more than 4 nitrogen atoms, and / or not more than 2 oxygen atoms and / or not more than 2 sulfur atoms. When the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, the invention also includes polycyclic systems, for example 8-azabicyclo [3.2.1] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl, the invention also includes spirocyclic systems, for example 1-oxa-5-aza-spiro [2.3] hexyl. Heterocyclyl groups according to the invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl , Oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxopiperazinyl and oxepanyl.
[0061] Eine besondere Bedeutung kommt Heteroarylen, also heteroaromatischen Systemen zu. Erfindungsgemäß steht der Ausdruck Heteroaryl für heteroaromatische Verbindungen, das heißt vollständig ungesättigte aromatische heterocyclische Verbindungen, die unter die vorstehende Defmiton von Heterocyclen fallen. Vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 3, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen aus der oben genannten Gruppe. Erfindungsgemäße Heteroaryle sind beispielsweise Furyl, Thienyl, Pyrazolyl, Imidazolyl, 1,2,3- und 1 ,2,4-Triazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, 1,2,3-, 1,3,4-, 1,2,4- und 1,2,5-Oxadiazolyl, Azepinyl, Pyrrolyl, Pyridyl, Pyridazinyl, Pyrimidinyl, Pyrazinyl, 1,3,5-, 1,2,4- und 1,2,3-Triazinyl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Oxepinyl, Thiepinyl, 1 ,2,4-Triazolonyl und 1 ,2,4-Diazepinyl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Of particular importance is heteroarylene, ie heteroaromatic systems. In the present invention, the term heteroaryl means heteroaromatic compounds, that is, fully unsaturated aromatic heterocyclic compounds which fall under the above deficient heterocycles. Preferably for 5- to 7-membered rings having 1 to 3, preferably 1 or 2 identical or different heteroatoms from the above-mentioned group. Examples of heteroaryls according to the invention are furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2 , 4- and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3-triazinyl, 1,2, 4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, oxepinyl, thiepinyl, 1, 2,4-triazolonyl and 1,2,4-diazepinyl. The heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals.
Der Begriff „(gegebenenfalls) substituierte" Gruppen/Substituenten, wie ein substituierter Alkyl-, Alkenyl-, Alkinyl-, Alkoxy-, Alkylsulfanyl-, Alkylsulfinyl-, Alkylsulfonyl-, Cycloalkyl-, Aryl-, Phenyl-, Benzyl-, Heterocyclyl- und Heteroarylrest, bedeuten beispielsweise einen vom unsubstituierten Grundkörper abgeleiteten substituierten Rest, wobei die Substituenten beispielsweise ein (1) Substituent oder mehrere Substituenten, vorzugsweise 1, 2, 3, 4, 5, 6, oder 7, ausgewählt sind aus einer Gruppe bestehend aus Amino, Hydroxy, Halogen, Nitro, Cyano, Isocyano, Mercapto, Isothiocyanato, C1-C4- Carboxy, Carbonamid, SF5, Aminosulfonyl, Ci-C i-Alkyl, C3-C i-Cycloalkyl, C2-C i-Alkenyl, C3-C4- Cycloalkenyl, C2-C4-Alkinyl, N-Mono-Ci-C4-alkyl-amino, NN-Di-Ci-C4-alkylamino, N-C1-C4- Alkanoylamino, Ci-C4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, C3-C4-Cycloalkoxy, C3-C4- Cycloalkenyloxy, Ci-C4-Alkoxycarbonyl, C2-C4- C2-C4-Alkenyloxycarbonyl, C2-C4- - -The term "(optionally) substituted" groups / substituents such as a substituted alkyl, alkenyl, alkynyl, alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl, represent, for example, a substituted radical derived from the unsubstituted body, wherein the substituents are, for example, one (1) substituent or more substituents, preferably 1, 2, 3, 4, 5, 6, or 7, selected from a group consisting of amino , Hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C 4 -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C -alkyl, C 3 -C -cycloalkyl, C 2 -C -alkenyl, C 3 -C 4 -cycloalkyl, C 4 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkyl-amino, N-N-di-C 1 -C 4 -alkylamino, N-C 1 -C 4 -alkanoylamino, C 1 -C 4 -alkoxy, C 2 -C 4 -alkoxy Alkenyloxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkoxy, C 3 -C 4 -cycloalkenyloxy, C 1 -C 4 -alkoxycarbonyl, C 2 -C 4 -cyclo C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 -alkoxy - -
Alkinyloxycarbonyl, C6-,Cio-,Ci4-Aryloxycarbonyl, Ci-C i-Alkanoyl, C2-C4-Alkenylcarbonyl, C2-C4- Alkinylcarbonyl, C6-,Cio-,Ci4-Arylcarbonyl, Ci-C4-Alkylsulfanyl, C3-C4-Cycloalkylsulfanyl, C1-C4- Alkylthio, C2-C4-Alkenylthio, C3-C4-Cycloalkenylthio, C2-C4-Alkinylthio, Ci-C4-Alkylsulfenyl und Ci-C4-Alkylsulfinyl, wobei beide Enantiomere der Ci-C4-Alkylsulfinylgruppe umfasst ind, C1-C4- Alkylsulfonyl, N-Mono-Ci-C4-alkyl-aminosulfonyl, NN-Di-Ci-C4-alkyl-aminosulfonyl, C1-C4- Alkylphosphinyl, Ci-C4-Alkylphosphonyl, wobei für Ci-C4-Alkylphosphinyl bzw. C1-C4- Alkylphosphonyl beide Enantiomere umfasst sind, N-Ci-C4-Alkyl-aminocarbonyl, N,N-Di-Ci-C4-alkyl- amino-carbonyl, N-Ci-C4-Alkanoyl-amino-carbonyl, N-Ci-C4-Alkanoyl-N-Ci-C4-alkyl-aminocarbonyl, C6-,Cio-,Ci4-Aryl, C6-,Cio-,Ci4-Aryloxy, Benzyl, Benzyloxy, Benzylthio, C6-,Cio-,Ci4-Arylthio, CÖ-,CIO- ,Ci4-Arylamino, Benzylamino, Heterocyclyl und Trialkylsilyl, mit einer Doppelbindung verbundene Substituenten wie Ci-C4-Alkyliden (z. B. Methyliden oder Ethyliden), eine Oxogruppe, eine Iminogruppe sowie einer substituierten Iminogruppe. Besonders bevorzugte substituierte Gruppen sind halogenierte Gruppen. Diese können eine oder mehrere Halogensubstituenten besitzen, jedoch besitzen diese Gruppen noch mindestens eine C-H Bindung, oder perhalogieniert sein. [0062] Die beispielhaft genannten Substituenten ("erste Substituentenebene") können, sofern sie kohlenwasserstoffhaltige Anteile enthalten, dort gegebenenfalls weiter substituiert sein ("zweite Substitutentenebene"), beispielsweise durch einen oder mehreren der Substituenten jeweils unabhängig voneinander ausgewählt aus Halogen, Hydroxy, Amino, Nitro, Cyano, Isocyano, Azido, Acylamino, einer Oxogruppe und einer Iminogruppe. Vorzugsweise werden vom Begriff "(gegebenenfalls) substituierter" Gruppe nur ein oder zwei Substitutentenebenen umfasst. Alkynyloxycarbonyl, C6, CIO, Ci 4 aryloxycarbonyl, C i-alkanoyl, C 2 -C 4 alkenylcarbonyl, C 2 -C4- alkynylcarbonyl, C6, CIO, C 4 aryl-carbonyl, Ci-C4-alkylsulfanyl , C 1 -C 4 -cycloalkylsulfanyl, C 1 -C 4 -alkylthio, C 2 -C 4 -alkenylthio, C 3 -C 4 -cycloalkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 4 -alkylsulfenyl and C 1 -C 4 -alkylsulfinyl, where both enantiomers of the C4-alkylsulfinyl comprises ind, C1-C4 alkylsulfonyl, N-mono-Ci-C4-alkyl-aminosulfonyl, N, N-di-Ci-C4-alkyl-aminosulfonyl, C 1 -C4- alkylphosphinyl, Ci-C4-alkylphosphonyl, wherein for C 1 -C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl both enantiomers are included, N-C 1 -C 4 -alkylaminocarbonyl, N, N-di-C 1 -C 4 -alkylamino-carbonyl, N-C 1 -C 4 Alkanoylamino-carbonyl, N-Ci-C4-alkanoyl-N-Ci-C4-alkyl-aminocarbonyl, C6, Cio, Ci4-aryl, C6, Cio, Ci4-aryloxy, benzyl, benzyloxy, benzylthio , C6, Cio, Ci4-arylthio, CÖ-, CIO-, Ci4-arylamino, benzylamino, heterocyclyl and trialkylsilyl, with a double bond associated substituents such as Ci-C4-alkylidene n (z. As methylidene or ethylidene), an oxo group, an imino group and a substituted imino group. Particularly preferred substituted groups are halogenated groups. These may have one or more halogen substituents, but these groups still have at least one CH bond, or be perhalogenated. The exemplified substituents ("first substituent level"), if they contain hydrocarbon-containing moieties, optionally further substituted there ("second substituent plane"), for example by one or more of the substituents each independently selected from halogen, hydroxy, amino , Nitro, cyano, isocyano, azido, acylamino, an oxo group and an imino group. Preferably, the term "(optionally) substituted" group includes only one or two substituent levels.
[0063] Die erfindungsgemäßen mit Halogen substituierten chemischen Gruppen bzw. halogenierte Gruppen (wie z. B. Alkyl oder Alkoxy) sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl mit Halogen substituiert. Solche Gruppen werden auch als Halogruppen bezeichnet (wie, Z. B. Haloalkyl). Bei mehrfacher Substitution mit Halogen, können die Halogenatome gleich oder verschieden sein und können alle an eines oder an mehrere Kohlenstoffatome gebunden sein. Dabei steht Halogen insbesondere für Fluor, Chlor, Brom oder Iod, vorzugsweise für Fluor, Chlor oder Brom und besonders bevorzugt für Fluor oder Cl. Insbesondere sind mit Halogen substituierte Gruppen Monohalocycloalkyl wie 1 -Fluor-cyclopropyl, 2-Fluor-cyclopropyl oder 1 -Fluor-cyclobutyl, Monohaloalkyl wie 2-Chlor-ethyl, 2-Fluor-ethyl, 1-Chlor-ethyl, 1 -Fluor- ethyl, Chlormethyl, oder Fluormethyl; Perhaloalkyl wie Trichlormethyl oder Trifluormethyl oder CF2CF3, Polyhaloalkyl wie Difluormethyl, 2-Fluor-2-Chlor-ethyl, Dichlormethyl, 1 , 1 ,2,2-Tetraflourethyl, oder 2,2,2-Trifluorethyl. Weitere Beispiele für Halogenalkyle sind Trichlormethyl, Chlordifluormethyl, Dichlorfluormethyl, Chlormethyl, Brommethyl, 1 -Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2,2,2- Trichlorethyl, 2-Chlor-2,2-difluorethyl, Pentafluorethyl, 3,3,3-Trifluorpropyl und Pentafluor-t-butyl. Bevorzugt sind Halogenalkyle mit 1 bis 4 Kohlenstoffatomen und 1 bis 9, vorzugsweise 1 bis 5 gleichen oder verschiedenen Halogenatomen, die ausgewählt sind unter Fluor, Chlor oder Brom. Besonders - - bevorzugt sind Halogenalkyle mit 1 oder 2 Kohlenstoffatomen und mit 1 bis 5 gleichen oder verschiedenen Halogenatomen, die ausgewählt sind unter Fluor oder Chlor, wie unter anderen Difluormethyl, Trifluormethyl oder 2,2-Difluorethyl. Weitere Beispiele für mit Halogen substituierten Verbindungen sind Haloalkoxy wie OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, OCH2CHF2 und 0CH2CH2C1, Halogenalkylsulfanyle wie Difluormethylthio, Trifluormethylthio, Trichlormethylthio, Chlordifluormethylthio, 1 -Fluorethylthio, 2-Fluorethylthio, 2,2-Difluorethylthio, 1 , 1 ,2,2- Tetrafluorethylthio, 2,2,2-Trifluorethylthio oder 2-Chlor-l,l,2-trifluorethylthio, Halogenalkylsulfinyle wie Difluormethylsulfinyl, Trifluormethylsulfinyl, Trichlormethylsulfinyl, Chlordifluormethylsulfinyl, 1 -Fluorethylsulfinyl, 2-Fluorethylsulfinyl, 2,2-Difluorethylsulfinyl, 1 , 1 ,2,2-Tetrafluorethylsulfinyl, 2,2,2-Trifluorethylsulfinyl und 2-Chlor-l,l,2-trifluorethylsulfinyl, Halogenalkylsulfinyle wie Difluormethylsulfinyl, Trifluormethylsulfinyl, Trichlormethylsulfinyl, Chlordifluormethylsulfinyl, 1 - Fluorethylsulfinyl, 2-Fluorethylsulfinyl, 2,2-Difluorethylsulfinyl, 1 , 1 ,2,2-Tetrafluorethylsulfinyl, 2,2,2- Trifluorethylsulfinyl und 2-Chlor-l,l,2-trifluorethylsulfinyl, Halogenalkylsulfonylgrupen wie Difluormethylsulfonyl, Trifluormethylsulfonyl, Trichlormethylsulfonyl, Chlordifluormethylsulfonyl, 1 - Fluorethylsulfonyl, 2-Fluorethylsulfonyl, 2,2-Difluorethylsulfonyl, 1 , 1 ,2,2-Tetrafluorethylsulfonyl, 2,2,2-Trifluorethylsulfonyl und 2-Chlor- 1 , 1 ,2-trifluorethylsulfonyl. The halogen-substituted chemical groups or halogenated groups (such as, for example, alkyl or alkoxy) according to the invention are monosubstituted or polysubstituted by halogen up to the maximum possible number of substituents. Such groups are also referred to as halo groups (such as, for example, haloalkyl). When substituted several times with halogen, the halogen atoms may be the same or different and may all be bonded to one or more carbon atoms. In this case, halogen is in particular fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferably fluorine or Cl. In particular, halogen-substituted groups are monohalocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl or 1-fluorocyclobutyl, monohaloalkyl, such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroalkyl ethyl, chloromethyl, or fluoromethyl; Perhaloalkyl such as trichloromethyl or trifluoromethyl or CF 2 CF 3, polyhaloalkyl such as difluoromethyl, 2-fluoro-2-chloro-ethyl, dichloromethyl, 1, 1, 2,2-tetrafluoroethyl, or 2,2,2-trifluoroethyl. Further examples of haloalkyls are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2 , 2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl and pentafluoro-t-butyl. Preferred are haloalkyls having 1 to 4 carbon atoms and 1 to 9, preferably 1 to 5 identical or different halogen atoms, which are selected from fluorine, chlorine or bromine. Especially Preferred are halogenoalkyls having 1 or 2 carbon atoms and having 1 to 5 identical or different halogen atoms, which are selected from fluorine or chlorine, such as, inter alia, difluoromethyl, trifluoromethyl or 2,2-difluoroethyl. Further examples of halogen-substituted compounds are haloalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 , OCH 2 CHF 2 and 0CH 2 CH 2 C1, haloalkylsulfanyls such as difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio , 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkylsulfinyls such as difluoromethylsulfinyl, trifluoromethylsulfinyl , Trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl, haloalkylsulfinyls such as difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-Ch lor-1, l, 2-trifluoroethylsulfinyl, haloalkylsulfonyl groups such as difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, chlorodifluoromethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2,2,2- Trifluoroethylsulfonyl and 2-chloro-1, 1, 2-trifluoroethylsulfonyl.
[0064] Bei Resten mit C-Atomen sind solche mit 1 bis 4 C-Atomen, insbesondere 1 oder 2 C-Atomen bevorzugt. Bevorzugt sind in der Regel Substituenten aus der Gruppe Halogen, z.B. Fluor und Chlor, (Ci-C i)Alkyl, vorzugsweise Methyl oder Ethyl, (Ci-C i)Haloalkyl, vorzugsweise Trifluormethyl, (Ci-C4)Alkoxy, vorzugsweise Methoxy oder Ethoxy, (Ci-C i)Haloalkoxy, Nitro und Cyano. Besonders bevorzugt sind dabei die Substituenten Methyl, Methoxy, Fluor und Chlor. For radicals with C atoms, those having 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred. Preferred are usually substituents selected from the group halogen, e.g. Fluorine and chlorine, (Ci-C i) alkyl, preferably methyl or ethyl, (Ci-C i) haloalkyl, preferably trifluoromethyl, (Ci-C4) alkoxy, preferably methoxy or ethoxy, (Ci-C i) haloalkoxy, nitro and cyano. Particularly preferred are the substituents methyl, methoxy, fluorine and chlorine.
[0065] Substituiertes Amino wie mono- oder disubstituiertes Amino bedeutet einen Rest aus der Gruppe der substituierten Aminoreste, welche beispielsweise durch einen bzw. zwei gleiche oder verschiedene Reste aus der Gruppe Alkyl, Hydroxy, Amino, Alkoxy, Acyl und Aryl N-substituiert sind; vorzugsweise N-Mono- und NN-Dialkylamino, (z.B. Methylamino, Ethylamino, NN-Dimethylamino, NN-Diethylamino, NN-Di-n-propylamino, NN-Diisopropylamino oder NN-Dibutylamino), N-Mono- oder NN-Dialkoxyalkylaminogruppen (z.B. N-Methoxymethylamino, N-Methoxyethylamino, NN-Di- (methoxymethyl)-amino oder NN-Di-(methoxyethyl)-amino), N-Mono- und NN-Diarylamino, wie gegebenenfalls substituierte Aniline, Acylamino, NN-diacylamino, N-Alkyl-N-arylamino, N-Alkyl-N- acylamino sowie gesättigte N-Heterocyclen; dabei sind Alkylreste mit 1 bis 4 C-Atomen bevorzugt; Aryl ist dabei vorzugsweise Phenyl oder substituiertes Phenyl; für Acyl gilt dabei die weiter unten genannte Definition, vorzugsweise (Ci-C4)Alkanoyl. Entsprechenes gilt für substituiertes Hydroxylamino oder Hydrazino. Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals, which are N-substituted for example by one or two identical or different radicals from the group alkyl, hydroxy, amino, alkoxy, acyl and aryl ; preferably N-mono- and N, N-dialkylamino, (eg methylamino, ethylamino, N, N-dimethylamino, N, N-diethylamino, N, N-propylamino, N, N-diisopropylamino or N, N-dibutylamino), N-mono- or N, N-dialkoxyalkylamino groups ( for example, N-methoxymethylamino, N-methoxyethylamino, N, N'-di (methoxymethyl) amino or N, N'-di (methoxyethyl) amino), N-mono- and N, N-diarylamino, such as optionally substituted anilines, acylamino, N, N-diacylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and saturated N-heterocycles; while alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; for acyl, the definition given below applies, preferably (C 1 -C 4) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
[0066] Erfindungsgemäß umfasst der Begriff "cyclische Aminogruppen" heteroaromatische oder aliphatische Ringsysteme mit einem oder mehreren Stickstoffatomen. Die Heterocyclen sind gesättigt oder ungesättigt, bestehen aus einem oder mehreren, gegebenenfalls kondensierten Ringsystemen und - 5 - beinhalten gegebenenfalls weitere Heteroatome, wie beispielsweise ein oder zwei Stickstoff-, Sauerstoff- und/oder Schwefelatome. Ferner umfasst der Begriff auch solche Gruppen, die einen Spiroring oder verbrücktes Ringsystem aufweisen. Die Anzahl der Atome, die die cyclische Aminogruppe bilden, ist beliebig und kann z.B. im Falle eines Einringsystems aus 3 bis 8 Ringatomen und im Falle eines Zweiringsystems aus 7 bis 1 1 Atomen. According to the invention, the term "cyclic amino groups" heteroaromatic or aliphatic ring systems having one or more nitrogen atoms. The heterocycles are saturated or unsaturated, consist of one or more, optionally fused ring systems and Optionally contain further heteroatoms, such as one or two nitrogen, oxygen and / or sulfur atoms. Furthermore, the term also includes such groups having a spiro or bridged ring system. The number of atoms that form the cyclic amino group is arbitrary and may, for example, in the case of a single-ring system of 3 to 8 ring atoms and in the case of a two-ring system of 7 to 1 1 atoms.
[0067] Beispielhaft für cyclische Aminogruppen mit gesättigten und ungesättigten monocyclischen Gruppen mit einem Stickstoffatom als Heteroatom seien 1 -Azetidinyl, Pyrrolidino, 2-Pyrrolidin-l -yl, 1 - Pyrrolyl, Piperidino, 1 ,4-Dihydropyrazin-l -yl, 1 ,2,5,6-Tetrahydropyrazin-l -yl, 1 ,4-Dihydropyridin-l -yl, 1 ,2,5,6-Tetrahydropyridin-l -yl, Homopiperidinyl genannt; beispielhaft für cyclische Aminogruppen mit gesättigten und ungesättigten monocyclischen Gruppen mit zwei oder mehreren Stickstoffatomen als Heteroatome seien 1 -Imidazolidinyl, 1 -Imidazolyl, 1 -Pyrazolyl, 1 -Triazolyl, 1 -Tetrazolyl, 1 -Piperazinyl, 1 -Homopiperazinyl, 1 ,2-Dihydro-piperazin- 1 -yl, 1 ,2-Dihydro-pyrimidin- 1 -yl, Perhydropyrimidin- 1 -yl, 1 ,4-Diazacycloheptan-l -yl, genannt; beispielhaft für cyclische Aminogruppen mit gesättigten und ungesättigten monocyclischen Gruppen mit einem oder zwei Sauerstoffatomen und einem bis drei Stickstoffatomen als Heteroatome, wie beispielsweise Oxazolidin-3-yl, 2,3-Dihydroisoxazol-2-yl, Isoxazol-2-yl, l ,2,3-Oxadiazin-2-yl, Morpholino, beispielhaft für cyclische Aminogruppen mit gesättigten und ungesättigten monocyclischen Gruppen mit einem bis drei Stickstoffatomen und einem bis zwei Schwefelatomen als Heteroatome seien Thiazolidin-3-yl, Isothiazolin-2-yl, Thiomorpholino, oder Dioxothiomorpholino genannt; beispielhaft für cyclische Aminogruppen mit gesättigten und ungesättigten kondensierten cyclischen Gruppen seien Indol-l -yl, 1 ,2-Dihydrobenzimidazol-l -yl, Perhydropyrrolo[l ,2-a]pyrazin-2-yl genannt; beispielhaft für cyclische Aminogruppen mit spirocyclischen Gruppen sei das 2-Azaspiro[4,5]decan-2-yl genannt; beispielhaft für cyclische Aminogruppen mit verbrückten heterocyclischen Gruppen sei das 2-Azabicyclo[2,2, l ]heptan-7-yl genannt. [0068] Substituiertes Amino schließt auch quartäre Ammoniumverbindungen (Salze) mit vier organischen Substituenten am Stickstoffatom ein. Examples of cyclic amino groups with saturated and unsaturated monocyclic groups having a nitrogen atom as a heteroatom are 1-azetinyl, pyrrolidino, 2-pyrrolidin-1-yl, 1 - pyrrolyl, piperidino, 1, 4-dihydropyrazine-1-yl, 1 2,5,6-tetrahydropyrazine-1-yl, 1,4-dihydropyridin-1-yl, 1, 2,5,6-tetrahydropyridin-1-yl, called homopiperidinyl; Exemplary of cyclic amino groups with saturated and unsaturated monocyclic groups having two or more nitrogen atoms as heteroatoms are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 1, 2- Dihydro-piperazine-1-yl, 1,2-dihydro-pyrimidin-1-yl, perhydropyrimidin-1-yl, 1,4-diazacycloheptan-1-yl called; exemplified by cyclic amino groups having saturated and unsaturated monocyclic groups having one or two oxygen atoms and one to three nitrogen atoms as heteroatoms, such as oxazolidin-3-yl, 2,3-dihydroisoxazol-2-yl, isoxazol-2-yl, l, 2 , 3-Oxadiazin-2-yl, morpholino, exemplified by cyclic amino groups with saturated and unsaturated monocyclic groups having one to three nitrogen atoms and one to two sulfur atoms as heteroatoms are thiazolidin-3-yl, isothiazolin-2-yl, thiomorpholino, or Dioxothiomorpholino called; Examples of cyclic amino groups having saturated and unsaturated condensed cyclic groups include indol-1-yl, 1,2-dihydrobenzimidazol-1-yl, perhydropyrrolo [1,2-a] pyrazine-2-yl; Exemplary of cyclic amino groups with spirocyclic groups is the 2-azaspiro [4,5] decan-2-yl called; Exemplary of cyclic amino groups with bridged heterocyclic groups is the 2-azabicyclo [2,2, l] heptan-7-yl called. Substituted amino also includes quaternary ammonium compounds (salts) having four organic substituents on the nitrogen atom.
[0069] Gegebenenfalls substituiertes Phenyl ist vorzugsweise Phenyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkoxy , Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4- Halogenalkyl, Ci-C4.Halogenalkoxy, Ci-C4.Alkylsulfanyl, Ci-C4.Halogenalkylsulfanyl, Cyano, Isocyano und Nitro substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyl, 2-, 3- und 4-Fluorphenyl, 2-, 3- und 4-Trifluormethyl- und -Trichlormethylphenyl, 2,4-, 3,5-, 2,5- und 2,3-Dichlorphenyl, o-, m- und p-Methoxyphenyl, 4-Heptafluorphenyl. Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 haloalkyl, Ci-C4 .Halogenalkoxy, Ci-C 4 .Alkylsulfanyl, Ci-C. 4 Haloalkylsulfanyl, cyano, isocyano and nitro, for example, o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4 Trifluoromethyl- and trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl, 4-heptafluorophenyl.
[0070] Gegebenenfalls substituiertes Cycloalkyl ist vorzugsweise Cycloalkyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe - -Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group - -
Halogen, Cyano, Ci-C i-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkoxy , Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkyl und Ci-C4-Halogenalkoxy substituiert ist, insbesondere durch einen oder zwei Ci-C4-Alkylreste substituiert ist. Halogen, cyano, C 1 -C -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 Haloalkoxy is substituted, in particular by one or two Ci-C4-Alkylreste substituted.
[0071] Gegebenenfalls substituiertes Heterocyclyl ist vorzugsweise Heterocyclyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkoxy , Ci-C4-Alkoxy- Ci-C4-alkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Nitro und Oxo substituiert ist, insbesondere ein- oder mehrfach durch Reste aus der Gruppe Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy, C1-C4- Halogenalkyl und Oxo, ganz besonders durch einen oder zwei Ci-C4-Alkylreste substituiert ist. [0072] Beispiele für Alkyl substituierte Heteroaryle sind Furylmethyl, Thienylmethyl, Pyrazolylmethyl, Imidazolylmethyl, 1,2,3- und 1 ,2,4-Triazolylmethyl, Isoxazolylmethyl, Thiazolylmethyl, Isothiazolylmethyl, 1,2,3-, 1,3,4-, 1,2,4- und 1,2,5-Oxadiazolylmethyl, Azepinylmethyl, Pyrrolylmethyl, Pyridylmethyl,, Pyridazinylmethyl, Pyrimidinylmethyl, Pyrazinylmethyl, 1,3,5-, 1,2,4- und 1,2,3- Triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinylmethyl, Oxepinylmethyl, Thiepinylmethyl und 1 ,2,4-Diazepinylmethyl. Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 haloalkoxy groups, nitro, and oxo, in particular mono- or polysubstituted by radicals from the is especially substituted by one or two Ci-C 4 alkyl group halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4 haloalkyl, and oxo. Examples of alkyl substituted heteroaryls are furylmethyl, thienylmethyl, pyrazolylmethyl, imidazolylmethyl, 1,2,3- and 1,2,4-triazolylmethyl, isoxazolylmethyl, thiazolylmethyl, isothiazolylmethyl, 1,2,3-, 1,3,4 , 1,2,4- and 1,2,5-oxadiazolylmethyl, azepinylmethyl, pyrrolylmethyl, pyridylmethyl, pyridazinylmethyl, pyrimidinylmethyl, pyrazinylmethyl, 1,3,5-, 1,2,4- and 1,2,3- Triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinylmethyl, oxepinylmethyl, thiepinylmethyl and 1,2,4-diazepinylmethyl.
[0073] Erfindungsgemäße Verbindungen können in bevorzugten Ausführungsformen vorkommen. Einzelne hierin beschriebene Ausführungsformen können dabei miteinander kombiniert werden. Nicht umfasst sind solche Kombinationen, die den Naturgesetzen widersprechen und die der Fachmann daher aufgrund seines Fachwissens ausgeschlossen hätte. Beispielsweise sind Ringstrukturen mit drei oder mehreren benachbarten O-Atomen ausgeschlossen. Compounds of the invention may occur in preferred embodiments. Individual embodiments described herein may be combined with each other. Not included are those combinations which contradict the laws of nature and which the expert would have excluded because of his expertise. For example, ring structures with three or more adjacent O atoms are excluded.
Isomere isomers
[0074] Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit reine Stereoisomere 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 comprises pure stereoisomers as well as any mixtures of these isomers.
Verfahren und Verwendungen Methods and uses
[0075] Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. ? The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. ?
[0076] Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
[0077] Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel immer auch den Begriff Pflanzenschutzmittel. [0078] Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. In the context of the present application, the term pest control always includes the term pesticides. The compounds of formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the crop and to control animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector.
[0079] Im Rahmen der vorliegenden Patentanmeldung wird unter dem Begriff „Hygiene" die Gesamtheit aller Maßnahmen, Verfahren und Verhaltensweisen verstanden, die das Ziel haben, Erkrankungen - insbesondere Infektionskrankheiten - zu vermeiden und der Gesunderhaltung des Menschen, Tieres und/oder der Umwelt zu dienen und/oder die Sauberkeit zu erhalten. Hierunter fallen erfindungsgemäß insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, vornehmlich aus Glas, Holz, Beton, Porzellan, Keramik, Kunststoff oder auch aus Metall(en), und deren Reinhaltung von Hygieneschädlingen bzw. deren Fäkalien. Erfindungsgemäß ausgeschlossen sind diesbezüglich wiederum Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. In the context of the present patent application, the term "hygiene" is understood to mean the entirety of all measures, methods and behaviors with the goal of avoiding diseases - in particular infectious diseases - and the health of humans, animals and / or the environment Serve and / or maintain the cleanliness.This includes according to the invention in particular measures for cleaning, disinfection and sterilization, for example, textiles or hard surfaces, mainly glass, wood, concrete, porcelain, ceramic, plastic or metal (s), and their In accordance with the invention, in this case, methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are carried out on the human or animal body are excluded.
[0080] Der Begriff „Hygienesektor" umfasst demnach alle Bereiche, technischen Gebiete und gewerblichen Nutzungen, in denen derartige Maßnahmen, Verfahren und Verhaltensweisen zur Hygiene von Wichtigkeit sind, wie beispielsweise die Hygiene in Küchen, Bäckereien, Flughäfen, Bädern, Schwimmbädern, Einkaufshäusern, Hotels, Krankenhäusern, Stallungen, etc. The term "hygiene sector" therefore encompasses all areas, technical areas and commercial uses in which such measures, processes and hygiene behaviors are of importance, such as hygiene in kitchens, bakeries, airports, spas, swimming pools, shopping centers, Hotels, hospitals, stables, etc.
[0081] Unter dem Begriff „Hygieneschädling" werden folglich ein oder mehrere tierischer(e) Schädling(e) verstanden, deren Vorhandensein im Hygienesektor insbesondere aus gesundheitlichen Gründen problematisch ist. Es ist folglich das vornehmliche Ziel, Hygieneschädlinge bzw. den Kontakt mit ihnen im Hygienesektor zu vermeiden bzw. zu minimieren. Dies kann insbesondere durch die Anwendung eines Schädlingsbekämpfungsmittels erfolgen, wobei das Mittel sowohl prophylaktisch als auch erst bei Befall zur Bekämpfung des Schädlings eingesetzt werden kann. Es ist ebenfalls möglich, Mittel einzusetzen, die bewirken, dass ein Kontakt mit dem Schädling vermieden oder reduziert wird. Als Hygieneschädlinge kommen beispielsweise die nachstehend genannten Organismen in Betracht. [0082] Der Begriff„Hygieneschutz" umfasst demnach alle Handlungen zur Aufrechterhaltung und/oder Verbesserung von derartigen Maßnahmen, Verfahren und Verhaltensweisen zur Hygiene. Consequently, the term "hygiene pest" is understood to mean one or more animal pests (e) whose presence in the hygiene sector is problematical, in particular for health reasons, and it is therefore the primary aim to prevent or treat hygiene pests in the hygiene sector This can be done, in particular, by the use of a pest control agent, which can be used both prophylactically and only when infested to control the pest It is also possible to use agents that cause a contact is avoided or reduced with the pest etc. For example, the following organisms may be considered as hygiene pests. The term "hygiene protection" therefore includes all actions for the maintenance and / or improvement of such measures, procedures and behaviors for hygiene.
[0083] 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:
[0084] Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z.B. Acarus spp., z.B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z.B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z.B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z.B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z.B. Eutetranychus banksi, Eriophyes spp., z.B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z.B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z.B. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z.B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z.B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z.B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda z.B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z.B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z.B. Blaniulus guttulatus; aus der Klasse der Insecta, z.B. aus der Ordnung der Blattodea z.B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., z.B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z.B. - -Pests from the strain of the Arthropoda, in particular from the class of the Arachnida eg Acarus spp., For example Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. eg Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., eg Eutetranychus banksi, Eriophyes spp., eg Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., eg Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp. Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Eg Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., eg Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes Spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., eg Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., eg Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the genus of Chilopoda, for example Geophilus spp., Scutigera spp .; from the order or class of Collembola eg Onychiurus armatus; Sminthurus viridis; from the class Diplopoda eg Blaniulus guttulatus; from the class of the Insecta, eg from the order of the Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., eg Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp. eg - -
Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z.B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z.B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z.B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z.B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z.B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z.B. Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z.B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., 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 undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z.B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp., z.B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z.B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z.B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z.B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z.B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, 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, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z.B. Dasineura brassicae, Delia spp., z.B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z.B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z.B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., z.B. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z.B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya oder Pegomyia spp., z.B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., z.B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z.B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z.B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; aus der Ordnung der Hemiptera z.B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiphon spp., z.B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z.B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z.B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z.B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z.B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z.B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z.B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, - - Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Eg Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata , Ceutorrhynchus spp., Eg Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., Eg Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., Eg Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp. , Curculio spp., Eg Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., Eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgi fera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., eg Epilachna borealis, Epilachna varivestis, Epitrix spp., eg Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., eg Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea , Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Eg Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp , Megascelis spp., Melanotus spp., Eg Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., Eg Melolontha melolontha, Migdolus spp., Monocha mus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., eg Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp. , eg Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., eg Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp , eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., eg Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Starchus spp., eg Starchus paludatus, Symphyletes spp., Tanymecus spp., Eg, Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., Eg, Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., eg Zabrus tenebrioides; from the order of the Dermaptera eg Anisolabis maritime, Forficula auricularia, Labidura riparia; - from the order of Diptera eg Aedes spp., eg Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., eg Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., eg Anopheles quadrimaculatus, Anopheles gambiae , Asphondylia spp., Bactrocera spp., Eg Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp. Contarinia spp., Eg Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., Eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp , Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg, Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophil a spp., eg 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., eg Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., eg Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., eg Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., Eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., Eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp. , eg Tipula pa ludosa, Tipula simplex, Toxotrypana curvicauda; from the order of the Hemiptera eg Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiphon spp., eg Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus , Allocaridara malayensis, Amrasca spp., Eg Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., Eg Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., Eg Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., eg Aspidiotus nerii , Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brass icae, Cacopsylla spp., eg 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., Eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, - -
Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z.B. Dysaphis apiifolia, Dysaphis plantagmea, 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, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z.B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z.B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z.B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., z.B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z.B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae,. Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., z.B. Nephotettix cinetieeps,, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia 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 madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z.B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z.B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z.B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z.B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., 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 fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis,Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z.B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z.B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z.B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z.B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z.B. Lygocoris pabulinus, Lygus spp., z.B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion aü-atum, 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, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z.B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z.B. Achroia grisella, Acronicta major, Adoxophyes spp., z.B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z.B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z.B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z.B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa 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 kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z.B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z.B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z.B. Helicoverpa armigera, Helicoverpa zea, Heliothis 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. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z.B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z.b. Lymantria dispar, Lyonetia spp., z.B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., z.B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z.B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z.B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z.B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z.B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z.B. Schoenobius bipunctifer, Scirpophaga spp., z.B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z.B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z.b. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., 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.B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z.B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z.B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z.B. Locusta migratoria, Melanoplus spp., z.B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z.B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Ctenocephalides spp., z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z.B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, 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; Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantagmea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna , Empoasca solana, Empoasca stevensi, Eriosoma spp., Eg 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, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni) , Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., Eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp , Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae ,. Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg, Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Eg Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotu ssp., eg Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella fureifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp. , Toxoptera spp., Eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eg Eushtistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulinus, Lygus spp., Eg Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria , Miridae, Monaionion aumatum, Nezara spp., Eg Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Eg Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis , Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg 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., eg Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera eg Coptotermes spp., eg Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., eg Reticulitermes flavipes, reticulitermes hesperus; from the order of the Lepidoptera eg Achroia grisella, Acronica major, Adoxophyes spp., eg Adoxophyes orana, Aedia leucomelas, Agrotis spp., eg Agrotis segetum, Agrotis ipsilon, Alabama spp., eg Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia Spp., eg Anticarsia gemmatalis, Argyroploce spp., 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., Eg 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., Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Egg dana saccharina, Ephestia spp., eg, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea , Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Eg Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., Eg Heliothis virescens, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., eg Leucoptera coffeella, Lithocolletis spp., eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp., eg Lymantria dispar, Lyonetia spp., eg Lyonetia clerkella, Malacosoma neustria , Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp. , eg Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., eg Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp. eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., eg Pseudaletia unipuncta , Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Eg Schoenobius bipunctifer, Scirpophaga spp., Eg Scirpophaga innotata, Scotia segetum, Sesamia spp., Eg Sesamia inferens, Sparganothis spp., Spodoptera spp., Eg Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., eg Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria eg Acheta domesticus, Dichroplus spp., Gryllotalpa spp., eg Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., eg Locusta migratoria, Melanoplus spp., eg Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera eg Lepinotus spp., Liposcelis spp .; from the order of Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., eg Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg 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., Eg Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, insbesondere aus der Klasse der Bivalvia, z.B. Dreissena spp.; sowie aus der Klasse der Gastropoda z.B. Arion spp., z.B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z.B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the Mollusca strain, in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
[0085] Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, z.B. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., z. B. Brugia malayi, Brugia timori, Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., z. B. Dictyocaulus filaria, Diphyllobothrium spp., z. B. Diphyllobothrium latum, Dipylidium spp., Dirofilaria spp., Dracunculus spp., z. B. Dracunculus medinensis, Echinococcus spp., z.B. Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., z.B. Enterobius vermicularis, Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., z.B. Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., z.B. Loa Loa, Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodiras spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, z.B. Onchocerca volvulus, Opisthorchis spp., Osleras spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., z.B. Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., z.B. Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., z.B. Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., z.B. Trichuris trichuria, Uncinaria spp., Wuchereria spp., z.B. Wuchereria bancrofti; Animal and human parasites from the strains of Platyhelminthes and Nematoda, e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., E.g. Brugia malayi, Brugia timori, Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., E.g. B. Dictyocaulus filaria, Diphyllobothrium spp., Z. Diphyllobothrium latum, Dipylidium spp., Dirofilaria spp., Dracunculus spp., E.g. B. Dracunculus medinensis, Echinococcus spp., E.g. Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., E.g. Enterobius vermicularis, Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp. , eg Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., E.g. Loa Loa, Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodiras spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp. Onchocerca volvulus, Opisthorchis spp., Osleras spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp. , Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Eg Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., E.g. Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., E.g. Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., E.g. Trichuris trichuria, Uncinaria spp., Wuchereria spp., E.g. Wuchereria bancrofti;
[0086] Pflanzenschädlinge aus dem Stamm der Nematoda, d.h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z.B. Aglenchus agricola, Anguina spp., z.B. Anguina tritici, Aphelenchoides spp., z.B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z.B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z.B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopauras spp., z.B. Cacopauras pestis, Criconemella spp., z.B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rasium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z.B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, - 5 -Plant pests from the strain of Nematoda, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopauras spp., Eg Cacopauras pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rasium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, - 5 -
Ditylenchus spp., z.B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z.B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z.B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z.B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmanieila 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., Pratylenchus spp., z.B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z.B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z.B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z.B. Tylenchorhynchus annulatus, Tylenchulus spp., z.B. Tylenchulus semipenetrans, Xiphinema spp., z.B. Xiphinema index. Ditylenchus spp., E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., E.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmanieila 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., E.g. 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, Tylenchulus spp., E.g. Tylenchulus semipenetrans, Xiphinema spp., E.g. Xiphinema index.
[0087] Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia, z.B. Eimeria spp., bekämpfen. Nematoden Furthermore, from the sub-region of the protozoa, the order of coccidia, e.g. Eimeria spp., Fight. nematodes
[0088] Der Begriff „Nematoden" umfasst im vorliegenden Zusammenhang alle Arten des Stammes Nematoda und hierbei insbesondere Arten, die Pflanzen oder Pilze (zum Beispiel Arten der Ordnung Aphelenchida, Meloidogyne, Tylenchida und andere) oder auch Menschen und Tiere (zum Beispiel Arten der Ordnungen Trichinellida, Tylenchida, Rhabditida und Spirurida) parasitieren oder in bzw. an diesen Lebewesen Schädigungen verursachen, sowie andere parasitäre Helminthen. The term "nematodes" in the present context includes all species of the strain Nematoda and in particular species, the plants or fungi (for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others) or even humans and animals (for example species of Trichinellida, Tylenchida, Rhabditida and Spirurida) parasites or causing damage to these animals, as well as other parasitic helminths.
[0089] Ein Nematizid im Pflanzenschutz, wie hier beschrieben, besitzt die Fähigkeit, Nematoden zu kontrollieren. A nematocide in crop protection as described herein has the ability to control nematodes.
[0090] Der Begriff „Nematoden kontrollieren" bedeutet das Abtöten der Nematoden oder das Verhindern oder Erschweren ihrer Entwicklung bzw. ihres Wachstums oder das Verhindern oder Erschweren ihres Eindringens in oder ihres Saugens am pflanzlichen Gewebe. The term "controlling nematodes" means killing the nematodes or preventing or aggravating their development or growth, or preventing or hindering their penetration into or their sucking on the plant tissue.
[0091] Dabei wird die Wirksamkeit der Verbindungen durch einen Vergleich von Mortalitäten, Gallenbildung, Zystenbildung, Nematodendichte pro Bodenvolumen, Nematodendichte pro Wurzel, Anzahl von Nematodeneier pro Bodenvolumen, Mobilität (Beweglichkeit) der Nematoden zwischen einer mit der Verbindung der Formel (I) behandelten Pflanze, Pflanzenteil oder dem behandelten Boden und einer unbehandelten Pflanze, Pflanzenteil oder unbehandelten Boden (100 %) ermittelt. Vorzugsweise wird eine Verringerung um 25-50 % im Vergleich mit einer unbehandelten Pflanze, Pflanzenteil oder unbehandelten Boden, besonders bevorzugt eine Verringerung um 51 - 79 % und ganz besonders bevorzugt das vollständige Abtöten oder die vollständige Verhinderung von Entwicklung und Wachstum der Nematoden durch eine Verringerung um 80 bis 100 % erreicht. Die Kontrolle von Nematoden, wie hier beschreiben, beinhaltet ebenso die Kontrolle der Nematoden- Vermehrung (Entwicklung von Zysten und/oder Eier). Verbindungen der Formel (I) können ebenso verwendet werden, um die Pflanzen oder Tiere gesund zu erhalten und können kurativ, präventiv oder systemisch zur Nematoden- Kontrolle eingesetzt werden. [0092] Dem Fachmann sind Methoden bekannt, wie Mortalitäten, Gallenbildung, Zystenbildung, Nematodendichte pro Bodenvolumen, Nematodendichte pro Wurzel, Anzahl von Nematodeneier pro Bodenvolumen, Mobilität (Beweglichkeit) der Nematoden bestimmt werden. The efficacy of the compounds is compared by a comparison of mortality, bile formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes between one treated with the compound of formula (I) Plant, plant part or the treated soil and an untreated plant, plant part or untreated soil (100%) determined. Preferably, a reduction of 25-50% compared to an untreated plant, plant part or untreated soil, more preferably a reduction of 51-79%, and most preferably complete suppression or complete prevention of development and growth of the nematodes by reduction achieved by 80 to 100%. The control of Nematodes as described herein also include control of nematode proliferation (development of cysts and / or eggs). Compounds of formula (I) may also be used to maintain healthy plants or animals and may be used for curative, preventive or systemic control of nematode control. Methods are known to those skilled in the art, such as mortality, bile formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes.
[0093] Die Verwendung einer Verbindung der Formel (I) kann die Pflanze gesund erhalten und beinhaltet ebenso eine Reduktion der von Nematoden hervorgerufenen Schäden sowie eine Erhöhung der Erntemenge. The use of a compound of formula (I) can keep the plant healthy and also includes a reduction in the damage caused by nematodes as well as an increase in the amount of harvest.
[0094] Der Begriff„Nematoden" bezieht sich im vorliegenden Zusammenhang auf Pflanzennematoden, unter die man alle Nematoden zusammenfasst, die Pflanzen schädigen. Pflanzennematoden umfassen pflanzenparasitäre Nematoden und im Boden lebende Nematoden. Zu den pflanzenparasitären Nematoden zählen Ektoparasiten wie Xiphinema spp., Longidorus spp. und Trichodorus spp.; Halbparasiten wie Tylenchulus spp.; migratorische Endoparasiten wie Pratylenchus spp., Radopholus spp. und Scutellonema spp.; ortsgebundene Parasiten wie Heterodera spp., Globodera spp. und Meloidogyne spp., sowie Stängel- und Blattendoparasiten wie Ditylenchus spp., Aphelenchoides spp. und Hirschmanieila spp.. Besonders schädliche wurzelparasitäre Bodennematoden sind zum Beispiel zystenbildende Nematoden der Gattungen Heterodera oder Globodera, und/oder Wurzelgallennematoden der Gattung Meloidogyne. Schädliche Arten dieser Gattungen sind zum Beispiel Meloidogyne incognita, Heterodera glycines (Sojabohnenzystennematode), Globodera pallida und Globodera rostochiensis (Kartoffelzystennematode), wobei diese Arten wirksam mit dem im vorliegenden Text beschriebenen Verbindungen bekämpft werden. Die Verwendung der im vorliegenden Text beschriebenen Verbindungen ist jedoch keineswegs auf diese Gattungen oder Arten beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Nematoden. The term "nematodes" as used herein refers to plant nematodes, which include all nematodes that cause damage to plants Plant nematodes include plant parasitic nematodes and soil-borne nematodes Plant parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp semi-parasites such as Tylenchulus spp; migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonema spp .; localized parasites such as Heterodera spp., Globodera spp., and Meloidogyne spp., and stalk and leaf endoparasites such as Ditylenchus spp Particularly harmful root parasitic soil nematodes are, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and / or root-knot nematodes of the genus Meloidogyne Harmful species of these genera are, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematem ode), Globodera pallida and Globodera rostochiensis (potato cyst nematode), which species are effectively controlled by the compounds described herein. However, the use of the compounds described herein is by no means limited to these genera or species, but extends equally to other nematodes.
[0095] Zu den Pflanzennematoden zählen z.B. Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria und die Stängel- und Blattendoparasiten Aphelenchoides spp., Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus und Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax) und Criconemella spp., Plant nematodes include e.g. Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria and the stem and Blattendoparasiten Aphelenchoides spp., Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus and Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax) and Criconemella spp.,
[0096] Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum und Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus sowie die Stängel- und Blattendoparasiten Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (=Heterodera - 7 - pallida), Globodera rostochiensis (Kartoffelzystennematode), Globodera solanacearum, Globodera tabacum, Globodera Virginia und die ortsgebundenen zystenbildenden Parasiten Globodera spp., Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus und Helicotylenchus spp., Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (Sojabohnenzystennematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae und die ortsgebundenen zystenbildenden Parasiten Heterodera spp., Hirschmanieila gracilis, Hirschmanieila oryzae, Hirschmanieila spinicaudata und die Stängel- und Blattendoparasiten Hirschmanieila spp., Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola und die Ektoparasiten Longidorus spp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi und die ortsgebundenen Parasiten Meloidogyne spp., Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres und Paratrichodorus spp., Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus und Paratylenchus spp., Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae und die migratorischen Endoparasiten Pratylenchus spp., Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, die migratorischen Endoparasiten Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis und Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis und Rotylenchus spp., Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum und die migratorischen Endoparasiten Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus und die Ektoparasiten Trichodorus spp., Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris und Tylenchorhynchus spp., Tylenchulus - - semipenetrans und die Semiparasiten Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index und die Ektoparasiten Xiphinema spp. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and the stalk and leaf endoparasites Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (= Heterodera - 7 - pallida), Globodera rostochiensis (potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera Virginia and the localized cystic parasites Globodera spp., Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus and Helicotylenchus spp. , Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae and the localized cyst forming parasites Heterodera spp., Hirschmanieila gracilis, Hirschmanieila oryzae, Hirschmanieila spinicaudata and Stem and leaf endoparasites Hirschmanieila spp., Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longi Dorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola and ectoparasites Longidorus spp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallox, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi and the localized parasites Meloidogyne spp., Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus spp., Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus pro jectus and Paratylenchus spp., Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, coffeae, Pratylenchus, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae and the migratory endoparasites Pratylenchus spp., Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, the migratory endoparasites Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyu rum, Scutellonema bradys, Scutellonema clathricaudatum and the migratory endoparasites Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and the ectoparasites Trichodorus spp., Tylenchorhynchus agri, Tylenchorhynchus brassicae , Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and Tylenchorhynchus spp., Tylenchulus - semipenetrans and the semiparasites Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and the ectoparasites Xiphinema spp.
[0097] Zu den Nematoden, zu deren Bekämpfung eine Verbindung der Formel (I) eingesetzt werden kann, zählen Nematoden der Gattung Meloidogyne wie der Southern Root-Knot Nematode (Meloidogyne incognita), der Javanese Root-Knot Nematode (Meloidogyne javanica, der Northern Root-Knot Nematode (Meloidogyne hapla) und der Peanut Root-Knot Nematode (Meloidogyne arenaria); Nematoden der Gattung Ditylenchus wie das Kartoffelkrätzeälchen (Ditylenchus destructor) und das Stock- und Stängelälchen (Ditylenchus dipsaci); Nematoden der Gattung Pratylenchus wie der Cob Root-Lesion Nematode (Pratylenchus penetrans), der Chrysanthemum Root-Lesion Nematode (Pratylenchus fallax), der Kaffeewurzelnematode (Pratylenchus coffeae), der Teewurzelnematode (Pratylenchus loosi) und der Walnut Root-Lesion Nematode (Pratylenchus vulnus); Nematoden der Gattung Globodera wie das Goldfarbene Kartoffelzystenälchen (Globodera rostochiensis) und das Weiße Kartoffelzystenälchen (Globodera pallida); Nematoden der Gattung Heterodera wie der Sojabohnenzystennematode (Heterodera glycines) und das Rübenzystenälchen (Heterodera schachtii); Nematoden der Gattung Aphelenchoides wie der Rice White-tip Nematode (Aphelenchoides besseyi), das Chrysanthemenälchen (Aphelenchoides ritzemabosi) und das Erdbeerälchen (Aphelenchoides fragariae); Nematoden der Gattung Aphelenchus wie der fungivore Nematode (Aphelenchus avenae); Nematoden der Gattung Radopholus, wie der Burrowing-Nematode (Radopholus similis); Nematoden der Gattung Tylenchulus wie der Orangenwurzelnematode (Tylenchulus semipenetrans); Nematoden der Gattung Rotylenchulus wie der reniforme Nematode (Rotylenchulus reniformis); in Bäumen lebende Nematoden, wie der Kiefemholznematode (Bursaphelenchus xylophilus) und der Red Ring Nematode (Bursaphelenchus cocophilus) und dergleichen. Among the nematodes to combat which a compound of formula (I) can be used include nematodes of the genus Meloidogyne such as the Southern Root-Knot Nematode (Meloidogyne incognita), the Javanese Root-Knot Nematode (Meloidogyne Javavanica, Northern Root-knot nematode (Meloidogyne hapla) and the peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as potato scabies (Ditylenchus destructor) and cane and stemlets (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as Cob root Nematode (Pratylenchus penetrans), the Chrysanthemum Root-Lesion Nematode (Pratylenchus fallax), the Coffee Rooted Embryo (Pratylenchus coffeae), the Teewurzelnematode (Pratylenchus loosi) and the Walnut Root-Lesion Nematode (Pratylenchus vulnus), the nematodes of the genus Globodera like the Golden potato cysts (Globodera rostochiensis) and white potato cysts (Globodera pallida); Nematodes of G heteroderms such as soybean cyst nematode (Heterodera glycines) and beet cysts (Heterodera schachtii); Nematodes of the genus Aphelenchoides such as the Rice White-tip Nematode (Aphelenchoides besseyi), the Chrysanthemum (Aphelenchoides ritzemabosi) and the Strawberry (Aphelenchoides fragariae); Nematodes of the genus Aphelenchus such as the fungivorous nematode (Aphelenchus avenae); Nematodes of the genus Radopholus, such as the burrowing nematode (Radopholus similis); Nematodes of the genus Tylenchulus such as the orange root nematode (Tylenchulus semipenetrans); Nematodes of the genus Rotylenchulus such as the reniform nematode (Rotylenchulus reniformis); Nematodes living in trees, such as the Kiefemholz nematode (Bursaphelenchus xylophilus) and the Red Ring Nematode (Bursaphelenchus cocophilus) and the like.
[0098] Zu den Pflanzen, zu deren Schutz eine Verbindung der Formel (I) verwendet werden kann, zählen Pflanzen wie Getreide (zum Beispiel Reis, Gerste, Weizen, Roggen, Hafer, Mais, und dergleichen), Bohnen (Sojabohne, Azukibohne, Bohne, Dicke Bohne, Erbsen, Erdnüsse und dergleichen), Obstbäume/Früchte (Äpfel, Zitrusarten, Birnen, Trauben, Pfirsiche, japanische Aprikosen, Kirschen, Walnüsse, Mandeln, Bananen, Erdbeeren und dergleichen), Gemüsearten (Kohl, Tomate, Spinat, Brokkoli, Salat, Zwiebel, Röhrenlauch, Pfeffer und dergleichen), Hackfrüchte (Karotte, Kartoffel, Süßkartoffel, Rettich, Lotuswurzel, Steckrübe und dergleichen), Pflanzen für industrielle Rohstoffe (Baumwolle, Hanf, Papiermaulbeere, Mitsumata, Raps, Rübe, Hopfen, Zuckerrohr, Zuckerrübe, Olive, Gummi, Palmen, Kaffee, Tabak, Tee und dergleichen), Kürbisgewächse (Kürbis, Gurke, Wassermelone, Melone und dergleichen), Weidepflanzen (Knaulgras, Sorgum, Wiesenlieschgras, Klee, Luzerne und dergleichen), Rasengräser (Maskarenengras, Straußgras und dergleichen), Gewürzpflanzen usw. (Lavendel, Rosmarin, Thymian, Petersilie, Pfeffer, Ingwer und dergleichen) und Blumenpflanzen (Chrysantheme, Rose, Orchidee und dergleichen) erwähnt werden. [0099] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden des Kaffees, insbesondere von Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. sowie aus Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. und Scutellonema spp.. [0100] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Kartoffel, insbesondere von Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci sowie aus Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae und Meloinema spp. The plants for the protection of which a compound of the formula (I) can be used include plants such as cereals (for example rice, barley, wheat, rye, oats, corn and the like), beans (soybean, azuki bean, Bean, broad beans, peas, peanuts and the like), fruit trees / fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries and the like), vegetables (cabbage, tomato, spinach, Broccoli, lettuce, onion, tubeworm, pepper and the like), root crops (carrot, potato, sweet potato, radish, lotus root, rutabaga and the like), plants for industrial raw materials (cotton, hemp, paper mulberry, mitsumata, rape, turnip, hops, sugar cane , Sugar beet, olive, gum, palm, coffee, tobacco, tea and the like), cucurbits (squash, cucumber, watermelon, melon and the like), pasture plants (cocksfoot, sorghum, meadowweed grass, clover, alfalfa and the like), turfgr (lavender, rosemary, thyme, parsley, pepper, ginger and the like) and flower plants (chrysanthemum, rose, orchid and the like) may be mentioned. The compounds of the formula (I) are particularly suitable for controlling nematodes of coffee, in particular Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. and from Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. and Scutellonema spp. The compounds of formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci and Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius , Paratrichodorus nanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radophol similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinema spp.
[0101] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Tomate, insbesondere von Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans und aus Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus und Rotylenchulus reniformis. The compounds of formula (I) are particularly suitable for controlling tomato nematodes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus , Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.
[0102] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden von Gurkengewächsen, insbesondere von Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis und Pratylenchus thornei. [0103] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Baumwolle, insbesondere von Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus und Rotylenchulus reniformis. The compounds of the formula (I) are particularly suitable for controlling nematodes of cucurbits, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei. The compounds of the formula (I) are particularly suitable for controlling cotton nematodes, in particular Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.
[0104] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden des Maises, insbesondere von Belonolaimus longicaudatus, Paratrichodorus minor und aus Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, - -The compounds of the formula (I) are particularly suitable for combating nematodes of maize, in particular Belonolaimus longicaudatus, Paratrichodorus minor and Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, arenaria, Meloidogyne, Meloidogyne arenaria thamesi, graminis Meloidogyne, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, naasi Meloidogyne, Heterodera avenae, Heterodera oryzae, Heterodera zeae, aegyptii Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus, Hoplolaimus magnistylus, - -
Hoplolaimus galeatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus heterocephalus, Criconemella omata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum und Subanguina radiciola. Hoplolaimus galeatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus Heterocephalus, Criconemella Omata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus Clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus , Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina radiciola.
[0105] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Sojabohne, insbesondere vonPratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus und aus Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus und Rotylenchulus reniformis. [0106] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden des Tabaks, insbesondere von Meloidogyne incognita, Meloidogyne javanica und aus Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum, Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp. und Tetylenchus nicotianae. The compounds of the formula (I) are particularly suitable for controlling nematodes of soybean, in particular of Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus and Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis. The compounds of the formula (I) are particularly suitable for controlling nematodes of the tobacco, in particular Meloidogyne incognita, Meloidogyne javanica and Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatus, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum, Criconemella spp. Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp. and Tetylenchus nicotianae.
[0107] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden von Zitrusgewächsen, insbesondere von Pratylenchus coffeae und aus Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus , Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis bzw. Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata und Tylenchulus semipenetrans . [0108] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Banane, insbesondere von Pratylenchus coffeae, Radopholus similis und aus Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera und Rotylenchulus spp.. - -The compounds of the formula (I) are particularly suitable for controlling nematodes of citrus plants, in particular Pratylenchus coffeae and Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita , Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans. The compounds of the formula (I) are particularly suitable for controlling banana nematodes, in particular Pratylenchus coffeae, Radopholus similis and Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp. - -
[0109] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden der Ananas, insbesondere von Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyuras, Pratylenchus goodeyi., Meloidogyne spp., Rotylenchulus reniformis und aus Longidoras elongatus, Longidoras laevicapitatus, Trichodoras primitivus, Trichodoras minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoense und Criconemoides ornatum . The compounds of the formula (I) are particularly suitable for controlling nematodes of the pineapple, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyuras, Pratylenchus goodeyi., Meloidogyne spp., Rotylenchulus reniformis and Longidoras elongatus, Longidoras laevicapitatus, Trichodoras primitivus, Trichodoras minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoense and Criconemoides ornatum.
[0110] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden von Trauben, insbesondere von Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index und aus Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyuras, Pratylenchus thornei und Tylenchulus semipenetrans. The compounds of the formula (I) are particularly suitable for controlling nematodes of grapes, in particular Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus Pratylenchus brachyuras, Pratylenchus thornei and Tylenchulus semipenetrans.
[Ol l i] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden von Baumkulturen - Kernobst, insbesondere von Pratylenchus penetrans und aus Pratylenchus vulnus, Longidoras elongatus, Meloidogyne incognita und Meloidogyne hapla. The compounds of the formula (I) are particularly suitable for combating nematodes of tree crops - pome fruit, in particular Pratylenchus penetrans and Pratylenchus vulnus, Longidoras elongatus, Meloidogyne incognita and Meloidogyne hapla.
[0112] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden von Baumkulturen - Steinfrüchten, insbesondere von Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax und aus Pratylenchus brachyuras, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyuram und Hoplolaimus galeatus. The compounds of the formula (I) are particularly suitable for controlling nematodes of tree crops - stone fruits, in particular Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyuras, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyuram and Hoplolaimus galeatus.
[0113] Die Verbindungen der Formel (I) eignen sich besonders für die Bekämpfung von Nematoden in Baumkulturen, Zuckerrohr und Reis , insbesondere von Trichodoras spp., Criconemella spp. und aus Pratylenchus spp. , Paratrichodoras spp., Meloidogyne spp. , Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp. Heterodera spp, Xiphinema spp. und Cacopauras pestis. [0114] Ebenso bezieht sich der Begriff„Nematoden" im vorliegenden Zusammenhang auf Nematoden, die Menschen oder Tiere schädigen. The compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops, sugarcane and rice, in particular Trichodoras spp., Criconemella spp. and from Pratylenchus spp. , Paratrichodoras spp., Meloidogyne spp. , Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp. Heterodera spp, Xiphinema spp. and Cacopauras pestis. Similarly, the term "nematodes" in the present context refers to nematodes that harm humans or animals.
[0115] Spezifische Nematodenarten, die für den Menschen oder für Tiere schädlich sind, sind: Trichinellida, zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp. Specific nematode species which are harmful to humans or to animals are: Trichinellida, for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.
Aus der Ordnung der Tylenchida zum Beispiel: Micronema spp., Strongyloides spp. From the order of Tylenchida for example: Micronema spp., Strongyloides spp.
Aus der Ordnung der Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp. Aus der Odnung der Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; For example, from the order of Rhabditida: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp. Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp , Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp. Ollulanus spp. For example, from the spout of Spirurida: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
Viele bekannte Nematizide wirken gleichsam gegen andere parasitäre Helminthen und werden daher für die Bekämpfung von human- und tierparasitären Würmern, die nicht unbedingt zu der Gruppe Nematoda gehören, verwendet. Die vorliegende Erfindung bezieht sich auch auf die Verwendung der Verbindungen der Formel (I) als anthelmintische Arzneimittel. Zu den pathogenen endoparasitären Helminthen zählen Platyhelmintha (z.B. Monogenea, Cestodes und Trematodes), Acanthocephala und Pentastoma. Die folgenden Helminthen sind als bevorzugt zu erwähnen: Many known nematicides, as it were against other parasitic helminths and are therefore used for the control of human and animal parasitic worms, which do not necessarily belong to the group Nematoda. The present invention also relates to the use of the compounds of formula (I) as anthelmintic drugs. Pathogenic endoparasitic helminths include platyhelmintha (e.g., Monogenea, Cestodes, and Trematodes), Acanthocephala, and Pentastoma. The following helminths are to be mentioned as preferred:
Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp. Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.
Cestodes: aus der Ordnung der Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp. Aus der Ordnung der Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp. Cestodes: from the order of Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp. For example, from the order of the cyclophyllida: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.
Trematodes: aus der Klasse der Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metorchis spp., Heterophyes spp., Metagonimus spp. Trematodes: from the class of Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp. Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp. Clonorchis spp., Metorchis spp., Heterophyes spp., Metagonimus spp.
Acanthocephala: aus der Ordnung der Oligacanthorhynchida z.B.: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung der Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung der Moniliformida zum Beispiel: Moniliformis spp., Aus der Ordnung der Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. Acanthocephala: from the order of Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order of Polymorphida for example: Filicollis spp .; from the order of Moniliformida for example: Moniliformis spp., From the order of Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung der Porocephalida zum Beispiel Linguatula spp. Pentastoma: from the order of the Porocephalida for example Linguatula spp.
[0116] Auf dem Gebiet der Tiermedizin und in der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) auf bekannte Weise direkt oder enteral, parenteral, dermal oder nasal in Form von geeigneten Anwendungsformen. Die Verabreichung kann prophylaktisch oder therapeutisch erfolgen. In the veterinary and animal husbandry fields, the compounds of formula (I) are administered in a known manner, directly or enterally, parenterally, dermally or nasally in the form of suitable forms of application. The administration can be prophylactic or therapeutic.
[0117] Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. The compounds of formula (I) may optionally also in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Formulierungen formulations
[0118] 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 Penetrationsförderer, z. B. vegetative Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester vegetativer Fettsäuren wie beispielsweise Rapsöloder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze z.B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention 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). Optionally, the use forms contain other pesticides and / or effect-improving Adjuvants such as penetration enhancers, e.g. As vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rape oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention promoting agents such. As dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
[0119] Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einem oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
[0120] Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Ver dicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. Preference is given to formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
[0121] Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktive Stoffe. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
[0122] 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. 5 As adjuvants, it is possible to use those substances which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or to confer biological properties. 5
[0123] Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N-Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). As extenders, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
[0124] Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasser-stoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. [0125] Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z.B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder aliphatische Kohlenwasserstoffe wie z.B. Chlorbenzol, Chlorethylen, oder 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. In the case of using water as extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
[0126] Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z.B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehl, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und /oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. In principle, all suitable carriers can be used. Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
[0127] 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. [0128] Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulphonsäure, Salze von Phenolsulphonsäure oder Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin- Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Also, liquefied gaseous diluents or solvents can be used. Particularly suitable are those extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Examples of emulsifying and / or foam-producing agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysates, lignin sulfite liquors and methyl cellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
[0129] Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. As further adjuvants, in the formulations and the applications derived therefrom, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0130] Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability, may furthermore be present. It may also contain foam-forming agents or defoamers.
[0131] Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und vegetabile Öle sein. In addition, 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-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.
[0132] Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Humectans, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
[0133] Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar Polymere. ? As retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers. ?
[0134] Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Be-tracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Stoffbeweglichkeit (Mobilität) der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettamine Alkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. In the present context, all substances which are customarily used in order to improve the penetration of agrochemical active substances into plants come into consideration as penetration promoters. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
[0135] Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.- % der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. The formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), more preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly preferably between 0 , 5 and 90 wt .-% of the compound of formula (I), based on the weight of the formulation.
[0136] Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pest control agents) 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.
Mischungen mixtures
[0137] Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbizide, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Desweiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteerträge steigern, die Reife beeinflussen, die Qualität und/oder den Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. [0138] Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) in Mischungen mit Mitteln zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. 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 or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved. Furthermore, the compounds of formula (I) may be present in admixture with other active ingredients or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
[0139] 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 according to the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
[0140] 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. If one of the compounds mentioned below can occur in various tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case.
Insektizide / Akarizide / Nematizide Insecticides / acaricides / nematicides
[0141] Die hier mit ihrem„common name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). The active substances mentioned here with their "common name" are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual", 16th Ed., British Crop Protection Council 2012) or searchable on the Internet (eg http: //www.alanwood. net / pesticides).
(1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl 0-(methoxyaminothio- phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B. Chlordane und Endosulfan oder Phenylpyrazole (Fiprole), z.B. Ethiprole und Fipronil. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Disulfone, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothiophosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, triclorfone and vamidothion. (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
(3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin, - -(3) sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, - -
Bioallethrin S-cyclopentenyl Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta- Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, Cyphenothrin [(lR)-trans-Isomere], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomere), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)- Isomere)], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. Bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) - trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR ) trans-isomer), prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) - isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Nikotinerge Acetylcholin-Rezeptor (nAChR) Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nikotin oder Sulfoxaflor oder Flupyradifurone. (4) nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispielsweise Spinosine, z.B. Spinetoram und Spinosad. (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
(6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) chloride channel activators, such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
(7) Juvenilhormon-Imitatoren, wie beispielsweise Juvenilhormon- Analoge, z.B. Hydroprene, Kinoprene und Methoprene oder Fenoxycarb oder Pyriproxyfen. (7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
(8) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise (8) agents with unknown or non-specific mechanisms of action, such as
Alkylhalide, z.B. Methylbromid und andere Alkylhalide; oderChloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein. Alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
(9) Selektive Fraßhemmer, z.B. Pymetrozine oder Flonicamid. (9) Selective feeding inhibitors, e.g. Pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox und Diflovidazin oder Etoxazole. (10) mite growth inhibitors, e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
(11) Mikrobielle Disruptoren der Insektendarmmembran, z.B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und BT Pflanzenproteine: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl . (11) Insect intestinal membrane microbial disruptors, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
(12) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargite oder Tetradifon. (13) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. - -(12) inhibitors of oxidative phosphorylation, ATP disruptors, such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone. (13) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr, DNOC, and sulfluramide. - -
(14) Nikotinerge Acetylcholin-Rezeptor-Antagonisten, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin.
(17) Häutungshemmer (insbesondere bei Dipteren, d.h. Zweiflüglern), wie beispielsweise Cyromazine. (17) Anti-skinning agents (especially in dipterans, i.e., two-wingers), such as cyromazines.
(18) Ecdyson-Rezeptor Agonisten, wie beispielsweise Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. (19) Oktopaminerge Agonisten, wie beispielsweise Amitraz. (18) ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides. (19) Octopaminergic agonists, such as amitraz.
(20) Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (20) Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
(21) Komplex-I-Elektronentransportinhibitoren, beispielsweise METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenone (Derris). (22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone. (21) complex I electron transport inhibitors, for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris). (22) voltage dependent sodium channel blockers, e.g. Indoxacarb or metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat. (23) inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
(24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanid. (25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen. (24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide. (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
(28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide. (28) ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
Weitere Wirkstoffe mit unbekanntem oder nicht eindeutigem Wirkmechanismus, wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide Dicloromezotiaz, Dicofol, Diflovidazin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Lotilaner, Meperfluthrin, Paichongding, Pyflubumide, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Sarolaner, Tetramethylfluthrin, Tetraniliprole, - -Other agents with unknown or ambiguous mechanism of action, such as afidopyropene, afoxolans, azadirachtin, benclothiaz, benzoximate, bifenazates, broflanilides, bromopropylates, quinomethionate, cryolites, cyclaniliproles, cycloxapride, cyhalodiamides, dicloromethzotiaz, dicofol, diflovidazine, flometoquine, fluazaindolizines, fluensulfones, flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Lotilaner, Meperfluthrin, Paichongding, Pyflubumide, Pyralidyl, Pyrifluquinazone, Pyriminostrobin, Sarolaner, Tetramethylfluthrin, Tetraniliprole, - -
Tetrachlorantraniliprole, Tioxazafen, Thiofluoximate, Triflumezopyrim und lodmethan; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) , sowie folgende bekannte wirksame Verbindungen: l- {2-Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-lH- l,2,4-triazol-5-amin (bekannt aus WO2006/043635), {l'-[(2E)-3-(4-Chlorphenyl)prop-2-en-l-yl]-5- fluorspiro[indol-3,4'-piperidin]-l(2H)-yl}(2-chlorpyridin-4-yl)methanon (bekannt ausTetrachlorantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following known active compounds: 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-l, 2,4-triazol-5-amine (known from WO2006 / 043635), {1 '- [(2E) -3- (4-chlorophenyl) prop-2-ene l-yl] -5-fluorospiro [indole-3,4'-piperidin] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from
WO2003/106457), 2-Chlor-N-[2- { 1 -[(2E)-3-(4-chlorphenyl)prop-2-en- 1 -yl]piperidin-4-yl} -4-WO2003 / 106457), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] -piperidin-4-yl} -4-
(trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494), 3-(2,5-Dimethylphenyl)-4- hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009/049851), 3-(2,5- Dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus WO2009/049851), 4-(But-2-in-l -yloxy)-6-(3,5-dimethylpiperidin-l -yl)-5-fluorpyrimidin (bekannt aus WO2004/099160), 4-(But-2-in-l -yloxy)-6-(3-chlorphenyl)pyrimidin (bekannt aus WO2003/076415), PF1364 (CAS-Reg.No. 1204776-60-2), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5- yljcarbonyl} amino)-5-chlor-3-methylbenzoyl]-2-methylhydrazincarboxylat (bekannt aus(trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one ( known from WO2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from WO2009 / 049851 ), 4- (But-2-yn-1-yloxy) -6- (3,5-dimethyl-piperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160), 4- (but-2-yne) l -yloxy) -6- (3-chlorophenyl) pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), methyl 2- [2 - ({[3-bromo- 1- (3-chloropyridin-2-yl) -1H-pyrazol-5-ylcarbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from
WO2005/085216), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5- cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[2-({[3- brom-l-(3-chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2- methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[3,5-dibrom-2-({[3-brom-l -(3- chlorpyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), N-[2-(5-Amino-l,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-l -(3- chlorpyridin-2-yl)-lH-pyrazol-5-carboxamid (bekannt aus CN102057925), 4-[5-(3,5-Dichlorphenyl)-5- (trifluormethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxidothietan-3-yl)benzamid (bekannt aus WO2009/080250), N-[(2E)-l-[(6-Chlorpyridin-3-yl)methyl]pyridin-2(lH)-yliden]-2,2,2- trifluoracetamid (bekannt aus WO2012/029672), l-[(2-Chlor-l,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl- 4H-pyrido[l,2-a]pyrimidin-l -ium-2-olat (bekannt aus WO2009/099929), l-[(6-Chlorpyridin-3- yl)methyl]-4-oxo-3-phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus WO2009/099929), 4- (3- {2,6-Dichlor-4-[(3,3-dichlorprop-2-en-l-yl)oxy]phenoxy}propoxy)-2-methoxy-6- (trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2-(tert-Butylcarbamoyl)-4-chlor-6- methylphenyl] - 1 -(3 -chlorpyridin-2-yl)-3 -(fluormethoxy)- 1 H-pyrazol-5 -carboxamid (bekannt aus WO2008/134969, Butyl-[2-(2,4-dichlorphenyl)-3-oxo-4-oxaspiro[4.5]dec-l-en-l -yl]-carbonat (bekannt aus CN 102060818), 3E)-3-[l-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-l,l,l-trifluor-propan-2-on (bekannt aus WO2013/144213, N-(Methylsulfonyl)-6-[2-(pyridin-3-yl)-l,3-thiazol-5-yl]pyridin-2- carboxamid (bekannt aus WO2012/000896), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-l-methyl-3- (pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-carboxamid (bekannt aus WO2010/051926), 5-Brom- 4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazole-3-carboxamid (bekannt aus CN103232431). - -WO2005 / 085216), methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3 methylbenzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [3,5-dibromo-2 - ({[3-bromo-1 - (3-chloropyridine) 2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), N- [2- (5-amino-l, 3,4-thiadiazole-2 -yl) -4-chloro-6-methylphenyl] -3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide (known from CN102057925), 4- [5- (3, 5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- (1-oxidothietan-3-yl) -benzamide (known from WO2009 / 080250 ), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridine-2 (1H) -ylidene] -2,2,2-trifluoroacetamide (known from WO2012 / 029672), [(2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-1 -ium-2-olate (known from WO2 009/099929), l - [(6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-1-ium-2-olate (known from WO2009 / 099929), 4- (3- {2,6-dichloro-4 - [(3,3-dichloroprop-2-en-1-yl) oxy] phenoxy} propoxy) -2-methoxy-6- (trifluoromethyl ) pyrimidine (known from CN101337940), N- [2- (tert -butylcarbamoyl) -4-chloro-6-methylphenyl] -1- (3-chloropyridin-2-yl) -3- (fluoromethoxy) -1H-pyrazole 5-carboxamide (known from WO2008 / 134969, butyl [2- (2,4-dichlorophenyl) -3-oxo-4-oxaspiro [4.5] dec-1-en-1-yl] carbonate (known from CN No. 102060818), 3E) -3- [1 - [(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1-trifluoro-propan-2-one (known from WO2013 / 144213, N - (methylsulfonyl) -6- [2- (pyridin-3-yl) -l, 3-thiazol-5-yl] -pyridine-2-carboxamide (known from WO2012 / 000896), N- [3- (benzylcarbamoyl) - 4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide (known from WO2010 / 051926), 5-bromo-4-chloro-N- [4-chloro 2-methyl-6- (methylcarbamoyl) phenyl] -2- (3-chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103 232431). - -
Fungizide fungicides
[0142] Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides). [0143] Alle aufgeführten füngiziden Mischpartner der Klassen (1) bis (15) können optional Salze mit entsprechenden Basen oder Säuren bilden, sofern geeignete funktionelle Gruppen vorliegen. Außerdem sind für die aufgeführten füngiziden Mischpartner der Klassen (1) bis (15) auch tautomere Formen eingeschlossen, sofern Tautomerie möglich ist. The drugs specified herein with their "common name" are known, for example as described in the "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides). All of the listed five-component mixed partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. In addition, tautomeric forms are also included for the listed ficcidial mixed partners of classes (1) to (15), provided that tautomerism is possible.
1) Inhibitoren der Ergosterolbiosynthese, zum Beispiel (1.01) Aldimorph, (1.02) Azaconazol, (1.03) Bitertanol, (1.04) Bromuconazol, (1.05) Cyproconazol, (1.06) Diclobutrazol, (1.07) Difenoconazol, (1.08) Diniconazol, (1.09) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorphacetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalilsulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifin, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefürazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafin, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) l-(4-Chlorphenyl)-2-(lH-l,2,4-triazol-l - yl)cycloheptanol, (1.61) 1 -(2,2-Dimethyl-2,3 -dihydro- 1 H-inden- 1 -yl)- 1 H-imidazol-5-carbonsäure- methylester, (1.62) N'- {5-(Difluormethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl} -N-ethyl-N- methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'- {2-methyl-5-(trifluormethyl)-4-[3- (trimethylsilyl)propoxy]phenyl} imidoformamid, ( 1.64) O- [ 1 -(4-Methoxyphenoxy)-3 ,3 -dimethylbutan-2- yl]-lH-imidazol-l-carbothioat, (1.65) Pyrisoxazol, (1.66) 2- {[3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.67) l- {[3-(2-Chlorphenyl)-1) inhibitors of ergosterol biosynthesis, for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate, (1.28) Imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefuzoate, (1.37) penconazole, (1.38) Piperaline, (1.39) prochloroconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.46) tebuconazole, 1.48) Terbinafine, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizole, (1.54) Triforin, (1.55) Triticonazole, (1.56) Uniconazole, (1.57) Uniconazole-p , (1.58) Viniconazole, (1.59) Voriconazole, (1.60) 1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, (1.61) 1- (2,2 -Dimethyl-2,3-dihydro-1H-inden-1-yl) -1 H -imidazole-5-carboxylic acid methyl ester, (1.62) N '- {5- (difluoromethyl) -2-methyl-4- [ 3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (1.63) N -ethyl-N-methyl-N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl ) propoxy] phenyl} imidoformamide, (1.64) O- [1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] -1H-imidazole-1-carbothioate, (1.65) pyrisoxazole, (1.66) 2- {[3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.67 ) l- {[3- (2-chlorophenyl) -
2- (2,4-difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol-5-ylthiocyanat, (1.68) 5-(Allylsulfanyl)-l- {[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol, (1.69) 2-[l-(2,4- Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.70) 2- {[rel(2R,3S)-3-(2-Chlo^henyl)-2-(2,4-difluo^henyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -LH-l, 2,4-triazol-5-ylthiocyanate, (1.68) 5- (allylsulfanyl) -l- {[3- (2- chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.69) 2- [1- (2,4-dichlorophenyl) -5-hydroxy -2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.70) 2- {[rel (2R, 3S) -3- (2-Chlo ^ henyl) -2- (2,4-difluo ^ henyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4-triazol-
3- thion, (1.71) 2- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro- 3H-l,2,4-triazol-3-thion, (1.72) l- {[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-ylthiocyanat, (1.73) l- {[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl} -lH-l,2,4-triazol-5-ylthiocyanat, (1 -74) 5-(Allylsulfanyl)-l- {[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.75) 5- - -3- thion, (1.71) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro- 3H-l, 2,4-triazole-3-thione, (1.72) 1 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl ] methyl} -1H-l, 2,4-triazol-5-ylthiocyanate, (1.73) 1- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane -2-yl] methyl} -LH-l, 2,4-triazol-5-ylthiocyanate, (1-74) 5- (allylsulfanyl) -l- {[rel (2R, 3S) -3- (2-chlorophenyl ) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.75) 5- - -
(Allylsulfanyl)-l- {[rel(2R,3R)-3-(2-chto (Allylsulfanyl) -l- {[rel (2R, 3R) -3- (2-chto
triazol, (1.76) 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, (1.77) 2-[(2R,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-triazole, (1.76) 2 - [(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H -l, 2,4-triazole-3-thione, (1.77) 2 - [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane
4- yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.78) 2-[(2R,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy- 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.79) 2-[(2S,4R,5R)-l-(2,4-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1.78) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5 -hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.79) 2 - [(2S, 4R, 5R) - l- (2,4-
Dichlo^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.80) 2- [(2S,4S,5R)-l-(2,4-Dichlo^henyl)-5-hydroxy-2,6,6-tr^^ Dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.80) 2- [(2S , 4S, 5R) -l- (2,4-Dichlo ^ henyl) -5-hydroxy-2,6,6-tr ^^
3- thion, (1.81) 2-[(2R,4S,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.82) 2-[(2R,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.83) 2-[(2S,4R,5S)-l-(2,4-Dichlorphenyl)- 3-thione, (1.81) 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, (1.82) 2 - [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane -4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.83) 2 - [(2S, 4R, 5S) -l- (2,4-dichlorophenyl) -
5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.84) 2-[4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, (1.85) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.86) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol, (1.87) 2- [2-Chlor-4-(4- chlorphenoxy)phenyl]-l -(lH-l,2,4-triazol-l -yl)butan-2-ol, (1.88) 2-[2-Chlor-4-(2,4- dichlorphenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.89) (2R)-2-(l-Chlorcyclopropyl)-4- [(lR)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.90) (2R)-2-(l-Chlorcyclopropyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.84) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.85) 2- [4- (4-chlorophenoxy) -2- ( trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.86) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1H-1,2,4-triazol-1-yl) pentan-2-ol, (1.87) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1 - (1H- l, 2,4-triazol-1-yl) butan-2-ol, (1.88) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-l, 2,4 -triazol-1-yl) propan-2-ol, (1.89) (2R) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1, 2 , 4-triazol-1-yl) butan-2-ol, (1.90) (2R) -2- (1-chlorocyclopropyl) -
4- [(l S)-2,2-dichlorcyclopropyl]-l -(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.91) (2S)-2-(l- Chlorcyclopropyl)-4- [( 1 S)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.92) (2S)-2- (l-Chlorcyclopropyl)-4-[(lR)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.93) (1 S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -(1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (1.94) (lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (1 -95) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l -(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol. 2) Inhibitoren der Atmungskette am Komplex I oder II, zum Beispiel (2.01) Bixafen, (2.02) Boscalid, (2.03) Carboxin, (2.04) Diflumetorim, (2.05) Feniuram, (2.06) Fluopyram, (2.07) Flutolanil, (2.08) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (Mischung von syn-epimerem Racemat 1RS,4SR,9RS und anti-epimerem Racemat 1RS,4SR,9SR), (2.12) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti-epimeres Enantiomer 1 S,4R,9R), (2.15) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1 S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxan, (2.23) Thifluzamid, (2.24) l-Methyl-N-[2-(l,l,2,2-tetrafluorethoxy)phenyl]-3-(trifluormethyl)-lH- pyrazol-4-carboxamid, (2.25) 3-(Difluormethyl)-l-methyl-N-[2-(l ,l,2,2-tetrafluorethoxy)phenyl]-lH- pyrazol-4-carboxamid, (2.26) 3-(Difluormethyl)-N-[4-fluor-2-(l , 1,2,3,3, 3-hexafluorpropoxy)phenyl]-l - methyl-lH-pyrazol-4-carboxamid, (2.27) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3- (difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4- {[4- - -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1.91) (2S) -2- (1H) Chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.92) (2S) -2 - (1-Chlorocyclopropyl) -4 - [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.93) (1 p , 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.94) (IR, 2S, 5S) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1-95) 5- ( 4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol. 2) respiratory chain inhibitors on complex I or II, for example (2.01) bixafen, (2.02) boscalid, (2.03) carboxin, (2.04) diflumetorim, (2.05) feniuram, (2.06) fluopyram, (2.07) flutolanil, (2.08 ) Fluxapyroxad, (2.09) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti-epimeric racemate 1RS, 4SR, 9SR), (2.12) isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS , 4SR, 9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxine, ( 2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxane, (2.23) Thifluzamide, (2.24) l-Methyl-N- [2- (l, l, 2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) -lH-pyrazole-4-carboxamide, (2.25) 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1H-pyrazole-4-carboxamide, ( 2 .26) 3- (Difluoromethyl) -N- [4-fluoro-2- (1,2,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole-4-carboxamide, (2.27 ) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.28) 5,8-difluoro- N- [2- (2-fluoro-4- {[4- - -
(trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]chmazolm-4-amm, (2.29) Benzovindiflupyr, (2.30) N- [(l S,4R)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4-m^ (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] chmazolm-4-amm, (2.29) benzovindiflupyr, (2.30) N- [(1S, 4R) -9- (dichloromethylene) -l, 2.3 , 4-tetrahydro-l, 4-m ^
methyl- 1 H-pyrazol-4-carboxamid, (2.31) N-[( 1 R,4S)-9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4- methanonaphthalin-5 -yl] -3 -(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.32) 3 - (Difluormethyl)- 1 -methyl-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.33) l,3,5-Trimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.34) 1 -Methyl-3 -(trifluormethyl)-N-( 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, (2.35) l-Methyl-3-(trifluormethyl)-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4- carboxamid, (2.36) 1 -Methyl-3 -(trifluormethyl)-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.37) 3 -(Difluormethyl)- 1 -methyl-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H- inden-4-yl]-lH-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.39) l,3,5-Trimethyl-N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.40) l,3,5-Trimethyl-N-[(3S)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2-Chlor-N-(l ,l,3-trimethyl- 2,3-dihydro-lH-inden-4-yl)pyridin-3-carboxamid, (2.43) Isofetamid, (2.44) 1 -Methyl-3 -(trifluormethyl)- N-[2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.45) N-(4'-Chlorbiphenyl-2-yl)-3- (difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.46) N-(2',4'-Dichlorbiphenyl-2-yl)-3 - (difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.47) 3 -(Difluormethyl)- 1 -methyl-N- [4'- (trifluormethyl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, (2.48) N-(2',5'-Difluorbiphenyl-2-yl)- 1 - methyl-3-(trifluormethyl)-lH-pyrazol-4-carboxamid, (2.49) 3 -(Difluormethyl)- 1 -methyl-N- [4'-(prop-l - in- 1 -yl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, (2.50) 5-Fluor- 1 ,3 -dimethyl-N- [4'-(prop- 1 -in- 1 - yl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (2.51) 2-Chlor-N- [4'-(prop-l -in- l-yl)biphenyl-2- yl]nicotinamid, (2.52) 3 -(Difluormethyl)-N- [4'-(3 ,3 -dimethylbut- 1 -in- 1 -yl)biphenyl-2-yl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (2.53) N-[4'-(3,3-Dimethylbut-l-in-l-yl)biphenyl-2-yl]-5-fluor-l,3-dimethyl-lH- pyrazol-4-carboxamid, (2.54) 3-(Difluormethyl)-N-(4'-ethinylbiphenyl-2-yl)-l-methyl-lH-pyrazol-4- carboxamid, (2.55) N-(4'-Ethinylbiphenyl-2-yl)-5-fluor-l,3-dimethyl-lH-pyrazol-4-carboxamid, (2.56) 2-Chlor-N-(4'-ethinylbiphenyl-2-yl)nicotinamid, (2.57) 2-Chlor-N-[4'-(3,3-dimethylbut-l-in-l- yl)biphenyl-2-yl]nicotinamid, (2.58) 4-(Difluormethyl)-2-methyl-N- [4'-(trifluormethyl)biphenyl-2-yl] - l,3-thiazol-5-carboxamid, (2.59) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-l-in-l -yl)biphenyl-2-yl]-l,3- dimethyl- 1 H-pyrazol-4-carboxamid, (2.60) 2-Chlor-N- [4'-(3 -hydroxy-3 -methylbut- 1 -in- 1 -yl)biphenyl-2- yl]nicotinamid, (2.61) 3 -(Difluormethyl)-N- [4'-(3 -methoxy-3 -methylbut- 1 -in- 1 -yl)biphenyl-2-yl] - 1 - methyl- lH-pyrazol-4-carboxamid, (2.62) 5-Fluor-N-[4'-(3-methoxy-3-methylbut-l-in-l-yl)biphenyl-2- yl] - 1 ,3 -dimethyl- 1 H-pyrazol-4-carboxamid, (2.63) 2-Chlor-N- [4'-(3 -methoxy-3 -methylbut- 1 -in- 1 - yl)biphenyl-2-yl]nicotinamid, (2.64) l,3-Dimethyl-N-(l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH- pyrazol-4-carboxamid, (2.65) l,3-Dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazol-4-carboxamid, (2.66) l,3-Dimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH- pyrazol-4-carboxamid, (2.67) 3- (Difluormethyl) -N-methoxy-1 -methyl-N- [1 -(2,4,6- trichlorphenyl)propan-2-yl]-lH-pyrazol-4-carboxamid, (2.68) 3-(Difluormethyl)-N-(7-fluor-l,l,3- - 5 - trimethyl-2,3-dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazol-4-carboxamid, (2.69) 3-(Difluormethyl)-N- [(3R)-7-fluor-l,l,3 rimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-4-carboxamid, (2.70) 3- (Difluormethyl)-N- [(3 S)-7-fluor- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-pyrazol-4- carboxamid. 3) Inhibitoren der Atmungskette am Komplex III, zum Beispiel (3.01) Ametoctradin, (3.02) Amisulbrom, (3.03) Azoxystrobin, (3.04) Cyazofamid, (3.05) Coumethoxystrobin, (3.06) Coumoxystrobin, (3.07) Dimoxystrobin, (3.08) Enoxastrobin, (3.09) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2- {[6- (3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamid, (3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2- { [( {( 1 E)- 1 - [3 -(trifluormethyl)phenyl] ethyliden} - amino)oxy] methyl }phenyl)acetamid, (3.25) (2E)-2-(Methoxyimino)-N-methyl-2- {2-[(E)-( { 1 -[3- (trifluormethyl)phenyl] ethoxy } imino)methyl]phenyl} acetamid, (3.26) (2E)-2- {2- [( { [( 1 E)- 1 -(3 - { [(E)- 1 - Fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino} oxy)methyl]phenyl} -2-(methoxyimino)-N- methylacetamid, (3.27) Fenaminostrobin, (3.28) 5-Methoxy-2-methyl-4-(2- {[( {(lE)-l-[3- (trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-on, (3.29) (2E)-2- {2-[( {Cyclopropyl[(4-methoxyphenyl)imino]methyl} sulfanyl)methyl]phenyl} -3- methoxyacrylsäuremethylester, (3.30) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2- hydroxybenzamid, (3.31) 2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl} -2-methoxy-N-methylacetamid, (3.32) 2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.33) (2E,3Z)-5- { [ 1 -(4-Chlorphenyl)- 1 H-pyrazol-3 -yl] oxy } -2-(methoxyimino)-N,3 -dimethylpent-3 -enamid. methyl-1H-pyrazole-4-carboxamide, (2.31) N - [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] 3 - (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3 - (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl) -1 H -pyrazole-4-carboxamide, (2.33) l, 3,5-trimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-indene -4-yl) -1H-pyrazole-4-carboxamide, (2.34) 1-methyl-3 - (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-indene-4 -yl) -1 H -pyrazole-4-carboxamide, (2.35) 1-methyl-3- (trifluoromethyl) -N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-indene 4-yl] -1H-pyrazole-4-carboxamide, (2.36) 1-methyl-3 - (trifluoromethyl) -N- [(3S) -1,3,3-trimethyl-2,3-dihydro-1 H-inden-4-yl] -1 H -pyrazole-4-carboxamide, (2.37) 3- (difluoromethyl) -1-methyl-N- [(3 S) -1,3,3-trimethyl-2,3 -dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.38) 3- (difluoromethyl) -l-methyl-N - [(3R) -l, l, 3-trimethyl-2 , 3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.39) 1, 3 , 5-trimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.40) l, 3, 5-trimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, (2.43) isofetamide, (2.44) 1-methyl-3 - ( trifluoromethyl) - N - [2 '- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (2.45) N- (4'-chlorobiphenyl-2-yl) -3- (difluoromethyl) -1 -methyl-1H-pyrazole-4-carboxamide, (2.46) N- (2 ', 4'-dichlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, ( 2.47) 3 - (Difluoromethyl) -1-methyl-N- [4'- (trifluoromethyl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (2.48) N- (2 ', 5'-difluorobiphenyl -2-yl) - 1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, (2.49) 3 - (difluoromethyl) -1-methyl-N- [4 '- (prop-1-yne) 1 -yl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (2.50) 5-fluoro-1,3-dimethyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -lH-pyrazole-4-carboxamide, (2.51) 2-Chloro-N- [4 '- (prop-1-yn-yl) biphenyl-2-yl] nicotinamide, (2.52) 3- (difluoromethyl) -N- [4' - (3, 3-dimethylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.53) N- [4 '- (3,3-dimethylbutyl) in-1-yl) biphenyl-2-yl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.54) 3- (difluoromethyl) -N- (4'-ethynylbiphenyl-2-) yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.55) N- (4'-ethynyl-biphenyl-2-yl) -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, ( 2.56) 2-chloro-N- (4'-ethynylbiphenyl-2-yl) nicotinamide, (2.57) 2-chloro-N- [4 '- (3,3-dimethylbut-1-yn-1-yl) biphenyl- 2-yl] nicotinamide, (2.58) 4- (difluoromethyl) -2-methyl-N- [4 '- (trifluoromethyl) biphenyl-2-yl] -1,3-thiazole-5-carboxamide, (2.59) 5- Fluoro-N- [4 '- (3-hydroxy-3-methylbut-1-yl-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (2.60) 2-chloro-N- [4 '- (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.61) 3- (difluoromethyl) -N- [4'- (3-Methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole ol-4-carboxamide, (2.62) 5-Fluoro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1,3-dimethyl-1 H-pyrazole-4-carboxamide, (2.63) 2-chloro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (2.64) 1 , 3-Dimethyl-N- (1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.65) 1, 3-dimethyl-N- [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.66) l, 3-dimethyl-N - [(3S ) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -LH-pyrazole-4-carboxamide, (2.67) 3- (difluoromethyl) -N-methoxy-1-methyl- N- [1- (2,4,6-trichlorophenyl) propan-2-yl] -1H-pyrazole-4-carboxamide, (2.68) 3- (difluoromethyl) -N- (7-fluoro-1, 1, 3 - 5-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.69) 3- (difluoromethyl) -N- [(3R) -7- fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.70) 3- (difluoromethyl) -N- [(3 S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide. 3) Complex III respiratory chain inhibitors, for example (3.01) ametoctradine, (3.02) amisulbrom, (3.03) azoxystrobin, (3.04) cyazofamide, (3.05) coumethoxystrobin, (3.06) coumoxystrobin, (3.07) dimoxystrobin, (3.08) enoxastrobin , (3.09) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18 ) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) -2- (2- {[6- (3-Chloro-2-methylphenoxy) -5 -fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, (3.24) (2E) -2- (methoxyimino) -N-methyl-2- (2- {[({(1 E) - 1 - [3 - (trifluoromethyl) phenyl] ethylidene} - amino) oxy] methyl} phenyl) acetamide, (3.25) (2E) -2- (methoxyimino) -N-methyl-2- {2 - [( E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} acetamide, (3.26) (2E) -2- {2- [({[(1 E) -1 - (3 - {[(E) -1-fluoro-2-phenylvinyl] ox y} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.27) fenaminostrobin, (3.28) 5-methoxy-2-methyl-4- (2- {[({ (IE) -l- [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one, (3.29) (2E ) -2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate, (3.30) N- (3-ethyl-3,5,5-trimethylcyclohexyl) 3-formamido-2-hydroxybenzamide, (3.31) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.32) 2- {2 - [(2, 5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.33) (2E, 3Z) -5- {[1- (4-chlorophenyl) -1 H -pyrazol-3-yl] oxy} - 2- (methoxyimino) -N, 3-dimethylpent-3-enamide.
4) Inhibitoren der Mitose und Zellteilung, zum Beispiel (4.01) Benomyl, (4.02) Carbendazim, (4.03) Chlorfenazol, (4.04) Diethofencarb, (4.05) Ethaboxam, (4.06) Fluopicolid, (4.07) Fuberidazol, (4.08) Pencycuron, (4.09) Thiabendazol, (4.10) Thiophanat-methyl, (4.11) Thiophanat, (4.12) Zoxamid, (4.13) 5-Chlor-7-(4-methylpiperidin-l -yl)-6-(2,4,6-trifluorphenyl)[l,2,4]triazolo[l,5-a]pyrimidin, (4.14) 3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin. 4) inhibitors of mitosis and cell division, for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6- trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6 trifluorophenyl) pyridazine.
5) Verbindungen, die dazu fähig sind, an mehreren Stellen anzugreifen („Multisite Action"), zum Beispiel (5.01) Bordeaux-Mischung, (5.02) Captafol, (5.03) Captan, (5.04) Chlorothalonil, (5.05) Kupferhydroxid, (5.06) Kupfernaphthenat, (5.07) Kupferoxid, (5.08) Kupferoxychlorid, (5.09) Kupfer(2+)-sulfat, (5.10) Dichlofluanid, (5.11) Dithianon, (5.12) Dodin, (5.13) Dodin freie Base, (5.14) Ferbam, (5.15) Fluorofolpet, (5.16) Folpet, (5.17) Guazatin, (5.18) Guazatinacetat, (5.19) Iminoctadin, (5.20) Iminoctadinalbesilat, (5.21) Iminoctadintriacetat, (5.22) Mancopper, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Metiram-Zink, (5.27) Oxin-Kupfer, (5.28) Propamidin, (5.29) Propineb, (5.30) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram, (5.35) Anilazin. - -5) compounds capable of attacking at multiple sites ("multisite action"), for example (5.01) Bordeaux mixture, (5.02) captafol, (5.03) captan, (5.04) chlorothalonil, (5.05) copper hydroxide, ( 5.06) copper naphthenate, (5.07) copper oxide, (5.08) copper oxychloride, (5.09) copper (2+) sulfate, (5.10) dichlorofluanide, (5.11) dithianon, (5.12) dodin, (5.13) dodine free base, (5.14) Ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinalbesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) Maneb, (5.25) metiram, (5.26) metiram-zinc, (5.27) oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur and sulfur compounds including calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine. - -
6) Verbindungen, die dazu fähig sind, eine Abwehrreaktion des Wirtes zu induzieren, zum Beispiel (6.01) Acibenzolar-S-methyl, (6.02) Isotianil, (6.03) Probenazol, (6.04) Tiadinil, (6.05) Laminarin. 6) Compounds capable of inducing host defense response, for example (6.01) acibenzolar-S-methyl, (6.02) isotianil, (6.03) probenazole, (6.04) tiadinil, (6.05) laminarin.
7) Inhibitoren der Aminosäure- und/oder Proteinbiosynthese, zum Beispiel (7.01) Andoprim, (7.02) Blasticidin-S, (7.03) Cyprodinil, (7.04) Kasugamycin, (7.05) Kasugamycinhydrochlorid-hydrat, (7.06) Mepanipyrim, (7.07) Pyrimethanil, (7.08) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l- yl)chinolin, (7.09) Oxytetracyclin, (7.10) Streptomycin. 7) inhibitors of amino acid and / or protein biosynthesis, for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) mepanipyrim, (7.07) Pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
8) Inhibitoren der ATP-Produktion, zum Beispiel (8.01) Fentinacetat, (8.02) Fentinchlorid, (8.03) Fentinhydroxid, (8.04) Silthiofam. 8) inhibitors of ATP production, for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
9) Inhibitoren der Zellwandsynthese, zum Beispiel (9.01) Benthiavalicarb, (9.02) Dimethomorph, (9.03) Flumorph, (9.04) Iprovalicarb, (9.05) Mandipropamid, (9.06) Polyoxine, (9.07) Polyoxorim, (9.08)9) Inhibitors of Cell Wall Synthesis, for example (9.01) Benthiavalicarb, (9.02) Dimethomorph, (9.03) Flumorph, (9.04) Iprovalicarb, (9.05) Mandipropamide, (9.06) Polyoxynes, (9.07) Polyoxorim, (9.08)
Validamycin A, (9.09) Valifenalat, (9.10) Polyoxin B, (9.11) (2E)-3-(4-tert.-Butylphenyl)-3-(2- chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (9.12) (2Z)-3-(4-tert.-Butylphenyl)-3-(2- chlorpyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -on. Validamycin A, (9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4 -yl) prop-2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4- yl) prop-2-ene-1-one.
10) Inhibitoren der Lipid- und Membransynthese, zum Beispiel (10.01) Biphenyl, (10.02) Chloroneb, (10.03) Dicloran, (10.04) Edifenphos, (10.05) Etridiazol, (10.06) Iodocarb, (10.07) Iprobenfos, (10.08)10) inhibitors of lipid and membrane synthesis, for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08)
Isoprothiolan, (10.09) Propamocarb, (10.10) Propamocarbhydrochlorid, (10.11) Prothiocarb, (10.12) Pyrazophos, (10.13) Quintozen, (10.14) Tecnazen, (10.15) Tolclofos-methyl. Isoprothiolane, (10.09) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene, (10.15) tolclofos-methyl.
11) Inhibitoren der Melaninbiosynthese, zum Beispiel (11.01) Carpropamid, (11.02) Diclocymet, (1 1.03) Fenoxanil, (11.04) Phthalid, (11.05) Pyroquilon, (11.06) Tricyclazol, (11.07) 2,2,2-Trifluorethyl {3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. 11) inhibitors of melanin biosynthesis, for example (11.01) carpropamide, (11.02) diclocymet, (1 1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl { 3-methyl-l - carbamate [(4-methylbenzoyl) amino] butan-2-yl}.
12) Inhibitoren der Nukleinsäuresynthese, zum Beispiel (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacon, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08) Hymexazol, (12.09) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinsäure, (12.14) Octhilinon. 13) Inhibitoren der Signalvermittlung, zum Beispiel (13.01) Chlozolinat, (13.02) Fenpiclonil, (13.03) Fludioxonil, (13.04) Iprodion, (13.05) Procymidon, (13.06) Quinoxyfen, (13.07) Vinclozolin, (13.08) Proquinazid. 12) Inhibitors of Nucleic Acid Synthesis, for example (12.01) Benalaxyl, (12.02) Benalaxyl-M (Kiralaxyl), (12.03) Bupirimat, (12.04) Clozylacone, (12.05) Dimethirimol, (12.06) Ethirimol, (12.07) Furalaxyl, (12.08 ) Hymexazole, (12.09) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid, (12.14) Octhilinone. 13) inhibitors of signal mediation, for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
14) Verbindungen, die als Entkoppler wirken können, zum Beispiel (14.01) Binapacryl, (14.02) Dinocap, (14.03) Ferimzon, (14.04) Fluazinam, (14.05) Meptyldinocap. 15) Weitere Verbindungen, zum Beispiel (15.001) Benthiazol, (15.002) Bethoxazin, (15.003) Capsimycin, (15.004) Carvon, (15.005) Chinomethionat, (15.006) Pyriofenon (Chlazafenon), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Dazomet, - 7 -14) compounds which may act as decouplers, for example (14.01) binapacryl, (14.02) dinocap, (14.03) ferimzone, (14.04) fluazinam, (14.05) meptyldinocap. 15) Further compounds, for example (15.001) Benthiazole, (15.002) Bethoxazine, (15.003) Capsimycin, (15.004) Carvone, (15.005) Quinomethionate, (15.006) Pyriofenone (Chlazafenone), (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Dazomet, - 7 -
(15.012) Debacarb, (15.013) Dichlorophen, (15.014) Diclomezin, (15.015) Difenzoquat, (15.016) Difenzoquatmetilsulfat, (15.017) Diphenylamin, (15.018) Ecomat, (15.019) Fenpyrazamin, (15.020) Flumetover, (15.021) Fluoroimid, (15.022) Flusulfamid, (15.023) Flutianil, (15.024) Fosetyl- Aluminium, (15.025) Fosetyl-Calcium, (15.026) Fosetyl-Natrium, (15.027) Hexachlorbenzol, (15.028) Irumamycin, (15.029) Methasulfocarb, (15.030) Methylisothiocyanat, (15.031) Metrafenon, (15.032) Mildiomycin, (15.033) Natamycin, (15.034) Nickeldimethyldithiocarbamat, (15.035) Nitrothal- isopropyl, (15.036) Oxamocarb, (15.037) Oxyfenthiin, (15.038) Pentachlorphenol und Salze, (15.039) Phenothrin, (15.040) phosphorige Säure und deren Salze, (15.041) Propamocarb-fosetylat, (15.042) Propanosin-Natrium, (15.043) Pyrimorph, (15.044) Pyrrolnitrin, (15.045) Tebufloquin, (15.046) Tecloftalam, (15.047) Tolnifanid, (15.048) Triazoxid, (15.049) Trichlamid, (15.050) Zarilamid, (15.051) 2-Methylpropansäure-(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-ylester, (15.052) l-(4- {4-[(5R)-5-(2,6- Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluormethyl)-lH-pyrazol-l-yl]ethanon, (15.053) l-(4- {4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro- l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yljethanon, (15.054) Oxathiapiprolin, (15.055) lH-Imidazol-l -carbonsäure-l-(4-methoxyphenoxy)-3,3- dimethylbutan-2-ylester, (15.056) 2,3,5, 6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.057) 2,3-Dibutyl-6- chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.058) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrol- l,3,5,7(2H,6H)-tetron, (15.059) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5R)-5- phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)ethanon, (15.060) 2-[5-Methyl-3- (trifluormethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5S)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2- yl}piperidin-l -yl)ethanon, (15.061) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l- {4-[4-(5-phenyl- 4,5-dihydro-l,2-oxazol-3-yl)-l,3-thiazol-2-yl]piperidin-l-yl}ethanon, (15.062) 2-Butoxy-6-iod-3- propyl-4H-chromen-4-on, (15.063) 2-Chlor-5-[2-chlor-l-(2,6-difluor-4-methoxyphenyl)-4-methyl-lH- imidazol-5-yl]pyridin, (15.064) 2-Phenylphenol und Salze, (15.065) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4- dihydroisochinolin-l -yl)chinolin, (15.066) 3,4,5-Trichlorpyridin-2,6-dicarbonsäurenitril, (15.067) 3- Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.068) 4-(4-Chlorphenyl)-5-(2,6- difluorphenyl)-3,6-dimethylpyridazin, (15.069) 5-Amino-l,3,4-thiadiazol-2-thiol, (15.070) 5-Chlor-N'- phenyl-N'-(prop-2-in-l-yl)thiophen-2-sulfonohydrazid, (15.071) 5-Fluor-2-[(4- fluorbenzyl)oxy]pyrimidin-4-amin, (15.072) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.073) 5-Methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin-7-amin, (15.074) (2Z)-3-Amino-2-cyano-3- phenylacrylsäureethylester, (15.075) N'-(4- {[3-(4-Chlorbenzyl)-l,2,4-thiadiazol-5-yl]oxy} -2,5- dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.076) N-(4-Chlorbenzyl)-3 - [3 -methoxy-4-(prop- 2-in-l-yloxy)phenyl]propanamid, (15.077) N-[(4-Chlorphenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2- in-l-yloxy)phenyl]propanamid, (15.078) N-[(5-Brom-3-chlorpyridin-2-yl)methyl]-2,4- dichlornicotinamid, (15.079) N-[l -(5-Brom-3-chlorpyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.080) N-[l -(5-Brom-3-chlorpyridin-2-yl)ethyl]-2-fluor-4-iodnicotinamid, (15.081) N- {(E)-(15.012) debacarb, (15.013) dichlorophene, (15.014) diclomethine, (15.015) difenzoquat, (15.016) difenzoquatmetylsulfate, (15.017) diphenylamine, (15.018) ecomat, (15.019) fenpyrazamine, (15.020) flumetover, (15.021) fluoroimide, (15,022) Flusulfamide, (15,023) Flutianil, (15,024) Fosetyl aluminum, (15,025) Fosetyl calcium, (15,026) Fosetyl sodium, (15,027) Hexachlorobenzene, (15,028) Irumamycin, (15,029) Methasulfocarb, (15,030) Methyl isothiocyanate , (15,031) metrafenone, (15,032) mildiomycin, (15,033) natamycin, (15,034) nickel dimethyldithiocarbamate, (15,035) nitrothal isopropyl, (15,036) oxamocarb, (15,037) oxyfenthiine, (15,038) pentachlorophenol and salts, (15,039) phenothrin, (15,040) phosphorous acid and its salts, (15,041) propamocarb-fosetylate, (15,042) propanosine sodium, (15,043) pyrimorph, (15,044) pyrrole nitrine, (15,045) tebufloquine, (15,046) tecloftalam, (15,047) tolnifanide, (15,048 ) Triazoxide, (15.049) trichlamide, (15.050) zarilamide, (15.051) 2-methylpropanoic acid (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 ester , (15.052) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole 2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.053) 1- (4- {4 - [(5S) - 5- (2,6-Difluorophenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl -3- (trifluoromethyl) -1H-pyrazol-1-yl-isethanone, (15.054) oxathiapiproline, (15.055) 1H-imidazole-1-carboxylic acid 1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl ester, ( 15,056) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (15,057) 2,3-dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 (3H) -one, (15,058) 2,6-Dimethyl-1H, 5H- [1,4] dithiino [2,3-c: 5,6-c '] dipyrrolo, 3,5,7 (2H, 6H) -tetrone, (15,059) 2- [5-Methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4 - [(5R) -5-phenyl-4,5-dihydro-1,2-oxazole 3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.060) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1 - (4- {4 - [(5S) - 5-phenyl-4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.061) 2- [5-methyl-3 - (trifluoromethyl) -1H-pyrazol-1-yl] -1- {4- [4- (5-phenyl-4,5-dihydro-1,2-oxazol-3-yl) -l, 3-thiazole] 2-yl] piperidin-1-yl} ethanone, (15.062) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.063) 2-chloro-5- [2-chloro-1 - (2,6-difluoro-4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl] pyridine, (15.064) 2-phenylphenol and salts, (15.065) 3- (4,4,5-trifluoro- 3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.066) 3,4,5-trichloropyridine-2,6-dicarboxylic acid nitrile, (15.067) 3-chloro-5- (4-chlorophenyl) - 4- (2,6-difluorophenyl) -6-methylpyridazine, (15.068) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (15,069) 5-amino-1, 3,4-thiadiazole-2-thiol, (15.070) 5-chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.071) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.072) 5-fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.073) 5-methyl-6-octyl [l , 2,4] triazolo [l, 5-a] pyrimidin-7-amine, (15. 074) (2Z) -3-Amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.075) N '- (4- {[3- (4-chlorobenzyl) -1,2,4-thiadiazol-5-yl] oxy } -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.076) N- (4-chlorobenzyl) -3 - [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl] propanamide, (15,077) N - [(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-4- (prop-2-in-1-yloxy) -phenyl] -propanamide, (15.078) N - [( 5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronotinamide, (15.079) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronotinamide , (15,080) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodo-nicotinamide, (15.081) N- {(E) -
[(Cyclopropylmethoxy)imino][6-(difluormethoxy)-2,3-difluorphenyl]methyl}-2-phenylacetamid, - -[6- (difluoromethoxy) -2,3-difluorophenyl] [(cyclopropylmethoxy) imino] methyl} -2-phenylacetamide, - -
(15.082) N- {(Z)-[(Cyclopropylmethoxy)imino] [6-(difluormethoxy)-2,3-difluorphenyl]methyl} -2- phenylacetamid, (15.083) N'- {4-[(3-tert.-Butyl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}- N-ethyl-N-methylimidoformamid, (15.084) N-Methyl-2-(l- {[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yl] acetyl} piperidin-4-yl)-N-( 1 ,2,3 ,4-tetrahydronaphthalin- 1 -yl)- 1 ,3 -thiazol-4-carboxamid, (15.085) N- Methyl-2-(l- {[5-methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]acetyl}piperidm^ (15.082) N - {(Z) - [(Cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (15.083) N '- {4 - [(3-tert -Butyl-4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro-5-methylphenyl} -N-ethyl-N-methylimidoformamide, (15.084) N-methyl-2- (l- {[5-Methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalene-1-yl) -1,3 -thiazole-4-carboxamide, (15.085) N-methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidine
tetrahydronaphthalin-l-yl]-l,3-thiazol-4-carboxamid, (15.086) N-Methyl-2-(l- {[5-methyl-3- (trifluormethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [(1S)-1 ,2,3 ,4-tetrahydronaphthalin- 1 -yl] -1,3- thiazol-4-carboxamid, (15.087) {6-[({[(l-Methyl-lH-tetrazol-5- yl)(phenyl)methylen] amino } oxy)methyl]pyridin-2-yl} carbamidsäurepentylester, (15.088) Phenazin- 1 - carbonsäure, (15.089) Chinolin-8-ol, (15.090) Chinolin-8-olsulfat (2: 1), (15.091) {6-[({[(l-Methyl-lH- tetrazol-5-yl)(phenyl)methylen]arnino} oxy)methyl]pyridin-2-yl}carbamidsäure-tert.-butylester, (15.092) (5-Brom-2-methoxy-4-methylpyridin-3 -yl)(2,3 ,4-trimethoxy-6-methylphenyl)methanon, (15.093) N- [2- (4- { [3 -(4-Chlorphenyl)prop-2-in- 1 -yl] oxy } -3 -methoxyphenyl)ethyl] -N2-(methylsulfonyl)valinamid, (15.094) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.095) {6-[({[(Z)-(l -Methyl-lH-tetrazol-5- yl)(phenyl)methylen] amino} oxy)methyl]pyridin-2-yl} carbamidsäurebut-3 -in- 1 -ylester, (15.096) 4- Amino-5-fluorpyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.097) 3,4,5- Trihydroxybenzoesäurepropylester, (15.098) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.099) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.100) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (15.101) 2-Fluor-6-(trifluormethyl)-N-(l ,l,3-trimethyl-2,3-dihydro- lH-inden-4-yl)benzamid, (15.102) 2-(6-Benzylpyridin-2-yl)chinazolin, (15.103) 2-[6-(3-Fluor-4- methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.104) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisochinolin-l -yl)chinolin, (15.105) Abscisinsäure, (15.106) N'-[5-Brom-6-(2,3-dihydro-lH- inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (15.107) N'- {5-Brom-6-[l - (3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (15.108) N'- {5- Brom-6-[(lR)-l -(3,5-difluo^henyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.109) N'- {5-Brom-6-[(l S)-l -(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamid, (15.110) N'- {5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3- yl} -N-ethyl-N-methylimidoformamid, (15.111) N'- {5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (15.112) N-Cyclopropyl-3-(difluormethyl)-5- fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (15.113) N-Cyclopropyl-N-(2- cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.114) N-(2-tert.- Butylbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.115) N- (5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.116) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol- 4-carboxamid, (15.117) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl- lH-pyrazol-4-carboxamid, (15.118) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2- isopropylbenzyl)-! -methyl- lH-pyrazol-4-carboxamid, (15.119) N-Cyclopropyl-N-(2-cyclopropyl-5- - - fluorbenzyl)-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.120) N-(2-Cyclopentyl- 5-fluorbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.121) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l -methyl-lH-pyrazol-4- carboxamid, (15.122) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (15.123) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5- methylbenzyl)-l -methyl- lH-pyrazol-4-carboxamid, (15.124) N-Cyclopropyl-N-(2-cyclopropyl-5- methylbenzyl)-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.125) N-(2-tert.-Butyl- 5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.126) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4- carboxamid, (15.127) N-Cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-N-[5-methyl-2-tetrahydronaphthalene-1-yl] -l, 3-thiazole-4-carboxamide, (15.086) N-methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) - N - [(1S) -1, 2,3, 4-tetrahydronaphthalene-1-yl] -1,3-thiazole-4-carboxamide, (15.087) {6 - [({ [(1-Methyl-1H-tetrazol-5-yl) (phenyl) -methylene] -phenyl (pentyl) -methyl) -pyridin-2-yl} -carbamate, (15.088) phenazine-1-carboxylic acid, (15.089) quinolin-8-ol , (15,090) quinoline-8-olsulfate (2: 1), (15,091) {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) -methylene] -arynino} oxy) -methyl] -pyridine -2-yl} -carbamic acid tert -butyl ester, (15.092) (5-bromo-2-methoxy-4-methylpyridin-3-yl) (2,3,4-trimethoxy-6-methylphenyl) -methanone, (15.093) N- [2- (4- {[3- (4-chlorophenyl) prop-2-yn-1-yl] oxy} -3-methoxyphenyl) ethyl] -N2- (methylsulfonyl) valinamide, (15.094) 4-oxo 4 - [(2-phenylethyl) amino] butanoic acid, (15.095) {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl ] pyridin-2-yl} -carbamic acid-but-3-yn-1-yl-ester, (15.096) 4-amino-5-flu orpyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2 (1H) -one), (15.097) propyl 3,4,5-trihydroxybenzoate, (15,098) [3- (4-chloro-2-fluorophenyl ) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.099) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (15,100) (R) - [3- (4-chloro-2-fluorophenyl) - 5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (15.101) 2-Fluoro-6- (trifluoromethyl) -N- (1, 1, 3 -trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (15.102) 2- (6-benzylpyridin-2-yl) quinazoline, (15.103) 2- [6- (3-fluoro-4- methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.104) 3- (4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.105) abscisic acid, (15.106 ) N '- [5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (15.107) N' {5-bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.108) N '- {5-bromo-6- [(IR) -l - (3,5-difluoro (3-yl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.109) N '- {5-bromo-6 - [(1S) -1- (3,5-difluorophenyl ) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.110) N '- {5-bromo-6 - [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridine-3 - yl} -N-ethyl-N-methylimidoformamide, (15.111) N '- {5-bromo-6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N -methylimidoformamide, (15.112) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (15.113) N-cyclopropyl-N- ( 2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.114) N- (2-tert-butylbenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.115) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl -lH-pyrazole-4-carboxamide, (15.116) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.117) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.118) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro) 2-isopropylbenzyl) -! -methyl-1H-pyrazole-4-carboxamide, (15.119) N-cyclopropyl-N- (2-cyclopropyl-5- - - fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.120) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3 - (difluoromethyl ) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.121) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -l - methyl-1H-pyrazole-4-carboxamide, (15.122) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide , (15.123) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.124) N-cyclopropyl-N (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.125) N- (2-tert-butyl-5-methylbenzyl) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.126) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.127) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2 -
(trifluormethyl)benzyl] - 1 H-pyrazol-4-carboxamid, (15.128) N- [2-Chlor-6-(trifluormethyl)benzyl] -N- cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4-carboxamid, (15.129) N-[3-Chlor-2- fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l -methyl-lH-pyrazol-4- carboxamid, (15.130) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-l - methyl- lH-pyrazol-4-carboxamid, (15.131) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2- isopropylbenzyl)-l -methyl- lH-pyrazol-4-carbothioamid, (15.132) N'-(2,5-Dimethyl-4-phenoxyphenyl)- N-ethyl-N-methylimidoformamid, (15.133) N'- {4-[(4,5-Dichlor-l ,3-thiazol-2-yl)oxy]-2,5- dimethylphenyl} -N-ethyl-N-methylimidoformamid, (15.134) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor- 4-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.135) 9-Fluor-2,2-dimethyl-5-(chinolin-3-yl)-2,3- dihydro-l ,4-benzoxazepin, (15.136) 2- {2-Fluor-6-[(8-fluor-2-methylchinolin-3-yl)oxy]phenyl}propan- 2-ol, (15.137) 2- {2-[(7,8-Difluor-2-methylchinolin-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.138) 4-(2- Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-l ,3-dimethyl-l H-pyrazol-5-amin, (15.139) 4-(2-Chlor-4- fluorphenyl)-N-(2,6-difluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.140) 4-(2-Chlor-4- fluorphenyl)-N-(2-chlor-6-fluorphenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5-amin, (15.141) 4-(2-Brom-4- fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l ,3-dimethyl-l H-pyrazol-5-amin, (15.142) N-(2-Brom-6- fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.143) 4-(2-Brom-4- fluorphenyl)-N-(2-bromphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.144) 4-(2-Brom-4-fluorphenyl)- N-(2-brom-6-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.145) 4-(2-Brom-4-fluorphenyl)-N-(2- chlorphenyl)-l ,3-dimethyl-lH-pyrazol-5-amin, (15.146) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)- l ,3-dimethyl-lH-pyrazol-5-amin, (15.147) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l ,3-dimethyl- 1 H-pyrazol-5-amin, (15.148) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)- 1 ,3-dimethyl- 1 H- pyrazol-5-amin, (15.149) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-l ,3-dimethyl-lH-pyrazol-5- amin, (15.150) N'-(4- {3-[(Difluormethyl)sulfanyl]phenoxy} -2,5-dimethylphenyl)-N-ethyl-N- methylimidoformamid, (15.151) N'-(2,5-Dimethyl-4- {3-[(l , 1 ,2,2- tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.152) N'-(2,5-Dimethyl- 4- {3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.153) N'-(2,5- Dimethyl-4- {3-[(2,2,3,3-tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (15.154) N'-(2,5-Dimethyl-4- {3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- - 5 - methylimidoformamid, (15.155) N'-(4- {[3-(Difluormethoxy)phenyl]sulfanyl} -2,5-dimethylphenyl)-N- ethyl-N-methylimidoformamid, (15.156) N'-(2,5-Dimethyl-4- {[3-(l , 1,2,2- tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.157) N'-(2,5-Dimethyl- 4- {[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.158) N'-(2,5- Dimethyl-4- {[3-(2,2,3,3-tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (15.159) N'-(2,5-Dimethyl-4- {[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamid, (15.160) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l -[4-(4- {5-[2-(prop-2-in-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.161) 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}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.162) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]-l-[4-(4- {5-[2-chlor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2- yl)piperidin-l-yl]ethanon, (15.163) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)-l ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5-yl}phenylmethansulfonat, (15.164) 2- {3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5- dihydro-l,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.165) 2-[3,5-Bis(difluormethyl)-lH-pyrazol- l-yl]-l -[4-(4- {(5S)-5-[2-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2- yl)piperidin-l-yl]ethanon, (15.166) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5R)-5-[2- (prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2-oxazol-3-yl} - 1 ,3-thiazol-2-yl)piperidin- 1 -yljethanon, (15.167) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2-fluor-6-(prop-2-in-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.168) 2-[3,5- Bis(difluormethyl)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- {(5R)-5 - [2-fluor-6-(prop-2-in- 1 -yloxy)phenyl] -4,5- dihydro-1 ,2-oxazol-3-yl} -1 ,3-thiazol-2-yl)piperidin-l -yljethanon, (15.169) 2-[3,5-Bis(difluormethyl)- lH-pyrazol-l-yl]-l-[4-(4- {(5S)-5-[2-chlor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl} - l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.170) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l -yl]-l-[4-(4- {(5R)-5-[2-chlor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin- l-yl]ethanon, (15.171) 2- {(5S)-3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)- l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}phenylmethansulfonat, (15.172) 2- {(5R)-3-[2-(l- {[3,5- Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5- yljphenylmethansulfonat, (15.173) 2- {(5S)-3-[2-(l - {[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenylmethansulfonat, (15.174) 2- {(5R)-3-[2-(l- {[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol^^ yl]-4,5-dihydro-l,2-oxazol-5-yl} -3-chlorphenylmethansulfonat. (trifluoromethyl) benzyl] -1 H -pyrazole-4-carboxamide, (15.128) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl -lH-pyrazole-4-carboxamide, (15.129) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H pyrazole-4-carboxamide, (15.130) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.131) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carbothioamide, (15.132) N '- (2,5-dimethyl- 4-phenoxyphenyl) - N-ethyl-N-methylimidoformamide, (15.133) N '- {4 - [(4,5-dichloro-l, 3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} - N-ethyl-N-methylimidoformamide, (15.134) N- (4-Chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine , (15.135) 9-Fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,136) 2- {2-fluoro-6 - [( 8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15.137) 2- {2 - [(7,8-difl uor-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} -propan-2-ol, (15.138) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -l, 3 dimethyl-1H-pyrazol-5-amine, (15.139) 4- (2-chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (15.140) 4- (2-Chloro-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.141) 4- (2- Bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15,142) N- (2-bromo-6-fluorophenyl) -4 (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.143) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (15.144) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5 -amine, (15.145) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (15.146) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.147) 4- (2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) - 1,3-dimethyl-1H-pyrazol-5-amine, (15.148) 4- (2-bromo-4-fluorophenyl) -N- ( 2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (15.149) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl -lH-pyrazole-5-amine, (15.150) N '- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.151) N' - (2,5-dimethyl-4- {3 - [(1,1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.152) N '- (2.5 Dimethyl 4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.153) N '- (2,5-dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (15.154) N '- (2,5-dimethyl-4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N- - 5 - methylimidoformamide, (15.155) N '- (4- {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.156) N' - (2, 5-Dimethyl-4- {[3- (l, 1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.157) N '- (2,5-dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.158) N '- (2,5-dimethyl-4- {[3- (2 , 2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.159) N '- (2,5-Dimethyl-4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (15.160) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1 - [4- (4- {5- [2- (4- prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.161 ) 2- [3,5-bis (difluoromethyl) -1 H -pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2-in-1 - yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.162) 2- [3,5- Bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5 - [2-chloro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine -l-yl] ethanone, (15.163) 2- {3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} -piperidin-4-yl) -l , 3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenylmethanesulphonate, (15.164) 2- {3- [2- (l- {[3,5-bis ( difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3- chlorophenylmethanesulfonate, (15.165) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1 - [4- (4-{(5S) -5- [2- (prop-2-yn -l-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.166) 2- [3 , 5-Bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4-{(5R) -5- [2- (prop-2-yn-1-ynyloxy) phenyl] -4 , 5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1-yl-1-ylanethanol, (15.167) 2- [3,5-bis (difluoromethyl) -1H-pyrazole -l-yl] -l- [4- (4- {(5S) -5- [2-fluoro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.168) 2- [3,5-bis (difluoromethyl) -1 H -pyrazol-1-yl] -1- [4- (4- {(5R) -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-ylanone, (15.169) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl ] 1- [4- (4- {(5S) -5- [2-chloro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazole 3-yl} - l, 3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.170) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [ 4- (4- {(5R) -5- [2-chloro-6- (prop-2-yn-1-yloxy) -phenyl] -4,5-dihydro-1,2-oxazol-3-yl} - l, 3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.171) 2- {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazole -l-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} phenylmethanesulfonate, (15.172) 2- {( 5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] - 4,5-dihydro-1,2-oxazol-5-yl-phenylmethanesulfonate, (15.173) 2- {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazole-1 - yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenylmethanesulf onat, (15.174) 2- {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1, 3-thiazole ^^ yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenylmethanesulfonate.
Biologische Schädlingsbekämpfungsmittel als Mischungspartner Biological pesticides as a mix partner
[0144] Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. 5 The compounds of formula (I) may be combined with biological pesticides. 5
[0145] Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte, 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.
[0146] 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 which act as biological insecticides, fungicides or nematicides.
[0147] Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of such bacteria that can be used or used as biological pesticides are:
Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, insbesondere B. thuringiensis subspecies israelensis (serotype H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder 5. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD-1372), oder 5. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).
[0148] Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts which can be used as biological pesticides are:
Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii, (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isaria fumosorosea) , insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm VI 17b, Trichoderma atroviride, insbesondere Stamm SCI (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM 1-952). Beauveria bassiana, especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
[0149] Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: - 5 - Examples of viruses that can be used or used as biological pesticides are: - 5 -
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. [0150] Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV. Also included are bacteria and fungi which are added as 'inoculant' plants or plant parts or plant organs and, by virtue of their particular properties, promote plant growth and plant health. Examples are:
Agrobacterium spp., Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolü, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Agrobacterium spp., Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolu, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
[0151] Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of plant extracts and products formed by microorganisms, including proteins and secondary metabolites, which 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 arvense,Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder.
Safener als Mischpartner Safener as mixing partner
[0152] Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloroacetyl)-l,3-oxazolidine (CAS 52836-31-4). Pflanzen und Pflanzenteile The compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) - 1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant parts
[0153] Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte 5 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 desired and undesired ones 5
Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika und Chili, Gurken, Melonen, Karotten, Wassermelonen, Zwiebel, Salat, Spinat, Lauch, Bohnen, Brassica oleracea (z.B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien der Pflanzen verstanden werden, beispielsweise Samen, Stecklinge sowie junge (unreife) Pflanzen bis hin zu reifen Pflanzen. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut (geerntete Pflanzen oder Pflanzenteile) sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. Wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peppers and chilli, cucumbers, melons, carrots, watermelons, Onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plants are to be understood as meaning all stages of development of the plants, for example seeds, cuttings and young (immature) plants through to mature plants. Plant parts are understood to mean all aboveground and subterranean 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 crops (harvested plants or plant parts) as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
[0154] Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. 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 acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
[0155] Wie bereits oben erwähnt können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile" bzw.„Teile von Pflanzen" oder„Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. 5 As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes. 5
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
[0156] 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 Ab Wehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie-Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z.B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Ab Wehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z.B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. 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 Abwehr ability of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes, for example. by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) in the plants are produced, furthermore an increased from defensive ability of the plants against plant-pathogenic mushrooms, bacteria and / or viruses, causes eg systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as increased tolerance of the plants to certain herbicidal agents, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g., "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, rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
Pflanzenschutz - Behandlungsarten Plant protection - types of treatment
[0157] Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-) Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-) Streuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. 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 by dipping, (spraying) spraying, (spraying), Sprinkling, vaporizing, spraying, misting, sprinkling, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layered Enveloping, etc. It is also possible, the compounds of formula (I) according to the ultra-low-volume method or to inject the use form or compound of formula (I) itself into the soil.
[0158] Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. A preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
[0159] Bei systemisch wirksamen Verbindungen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d.h. der Standort der Pflanze (z.B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d.h. die Verbindungen der Formel (I) werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein. Saatgutbehandlung In the case of systemically active compounds, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field. seed treatment
[0160] Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen Insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. - toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. The control of animal pests by the treatment of the seed of plants has long been known and is the subject of constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
[0161] Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. The present invention therefore more particularly relates to a method of protecting seeds and germinating plants from infestation by pests by treating the seeds with one of the compounds of formula (I). The method according to the invention for protecting seed and germinating plants from infestation by pests further comprises a method in which the seed is cultivated simultaneously or sequentially with a compound of the formula (I) and Mixing partner is treated. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
[0162] Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. The invention also relates to the use of the compounds of formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
[0163] Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut enthalten sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungspartner enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und Mischungspartner als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
[0164] Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating - Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. [0165] Einer der auftretenden Vorteile, wenn eine der Verbindungen der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. 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. One of the advantages that occurs when one of the compounds of formula (I) acts systemically is that the treatment of the seed protects not only the seed itself but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
[0166] Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Another advantage is that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
[0167] Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
[0168] Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. 5? Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation comes. 5?
[0169] Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baum-wolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z.B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps, Gemüse und Reis zu. The compounds of the formula (I) are suitable for the protection of seeds 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.
[0170] Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikro- Organismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von trans-genem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. As already mentioned above, the treatment of transgenic seed with a compound of formula (I) is of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly 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.
[0171] Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z.B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Falle von Reissaatgut ist es auch möglich Saatgut zu verwenden, das zum Beispiel in Wasser bis zu einem bestimmten Stadium vorgequollen wurde (pigeon breast Stadium), was zu einer verbesserten Keimung und zu einem gleichmäßigeren Auflaufen führt. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming. In the case of rice seed, it is also possible to use seeds that have been pre-swollen in water, for example, to a certain stage (pigeon breast stage), resulting in improved germination and more even emergence.
[0172] Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. 5 In general, when treating the seed, care must be taken that the amount of compound of formula (I) and / or further additives applied to the seed is chosen so that germination of the seed is not impaired or the resulting seed Plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates. 5
[0173] 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.
[0174] Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coatings, and ULV formulations.
[0175] Diese Formulierungen werden in bekannter Weise hergestellt, indem man Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungsoder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
[0176] 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. Suitable 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.
[0177] Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutyl-naphthalin-Sulfonate. [0178] 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 Arylsulfonat- Formaldehydkondensate. Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. 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.
[0179] 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. 5 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. 5
[0180] 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. [0180] As preservatives, all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention. Examples include dichlorophen and Benzylalkoholhemiformal.
[0181] Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- Hertingen 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 of 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.
[0182] 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.
[0183] Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, 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).
[0184] 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.
[0185] Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel- Formulierungen oder daraus hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichem oder kontinuierlichem Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom, all mixing devices which can usually be used for the dressing can be considered. Specifically, the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.
[0186] Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates at The compound of the formula (I) is 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
[0187] Auf dem Gebiet der Tiergesundheit, d.h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasiten umfasst insbesondere Helminthen und Protozoa wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten und Akariden. In the field of animal health, i. In the veterinary field, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects and acarids.
[0188] 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. In the veterinary field, the compounds of formula (I) which are of low toxicity to warm-blooded animals are useful in the control of parasites used in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals occur. They are effective against all or individual stages of parasite development.
[0189] Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; Fische und Krustentiere, z.B. in der Aquakultur und auch Insekten wie Bienen. For example, farm animals include mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
[0190] Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel, Reptilien, Amphibien und Aquariumfische. Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians, and aquarium fish.
[0191] Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. In a preferred embodiment, the compounds of formula (I) are administered to mammals.
[0192] Gemäß einer weiteren bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel und insbesondere Geflügel, verabreicht. According to a further preferred embodiment, the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
[0193] 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 performance reductions (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and easier animal husbandry is possible and a better well-being of the animals is achievable.
[0194] In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen", dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert werden kann. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindung der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern kann. - -With respect to the field of animal health, the term "controlling" or "controlling" means that by the compounds of the formula (I), the occurrence of the respective parasite in an animal infected with such parasites to a harmless extent is effective , can be reduced. More specifically, "combating" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication. - -
[0195] Zu den Arthropoden zählen: aus der Ordnung Anoplurida, zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina and Ischnocerina, zum Beispiel Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; aus der Ordnung Siphonapterida, zum Beispiel Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. The arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia Spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. , Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .; as well as pests and hygiene pests from the order Blattarida.
[0196] Weiterhin zählen zu den Arthropoden: Furthermore, the arthropods include:
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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; und aus der Ordnung Acaridida (Astigmata), zum Beispiel Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. , Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
[0197] Zu parasitären Protozoen zählen: Parasitic protozoa include:
Mastigophora (Flagellata), wie zum Beispiel Trypanosomatidae, zum Beispiel Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Beispiel Trichomonadidae, zum Beispiel Giardia lamblia, G. canis; Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.; Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G. canis; Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
Apicomplexa (Sporozoa), wie Eimeridae, zum Beispiel Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec, Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec, I. suis, Cystisospora spec, Cryptosporidium spec, insbesondere C. parvum; wie Toxoplasmadidae, zum Beispiel Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, wie Piroplasmea, zum Beispiel Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, wie Adeleina, zum Beispiel Hepatozoon canis, H. spec. Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis , E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. stiedai E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis , Cystisospora spec., Cryptosporidium spec., Especially C. parvum; such as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
[0198] Zu pathogenen Endoparasiten, bei denen es sich um Helminthen handelt, zählen Plattwürmer (z.B. Monogenea, Cestodes und Trematodes), Rundwürmer, Acanthocephala und Pentastoma. Dazu zählen: Pathogenic endoparasites, which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.; aus der Ordnung Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp. , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
Trematodes: aus der Klasse Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., - oi -Trematodes: from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp. , Gastrothylacus spp., Notocotylus spp., Catatropis spp., - oi -
Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.; Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
Rundwürmer: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.; aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Strongyloides spp.; aus der Ordnung Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.; aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Bayhsascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; Roundworms: Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Bayhsascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. [0199] Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch oder therapeutisch erfolgen. Pentastoma: from the order Porocephalida for example Linguatula spp. In the field of veterinary medicine and animal husbandry, the compounds of formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. The administration can be prophylactic or therapeutic.
[0200] So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verwendung einer Verbindung der Formel (I) als Arzneimittel. [0201] Ein weiterer Aspekt bezieht sich auf die Verwendung einer Verbindung der Formel (I) als Antiendoparasitikum, insbesondere als ein Helminthizid oder ein Mittel gegen Protozoen. Verbindungen der Formel (I) eignen sich für die Verwendung als Antiendoparasitikum, insbesondere als ein Helminthizid oder Mittel gegen Protozoen, beispielsweise in der Tierzucht, in der Tierhaltung, in Ställen und auf dem Hygienesektor. [0202] Ein weiterer Aspekt wiederum betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder ein Akarizid Ein weiterer Aspekt betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder Akarizid, zum Beispiel in der Tierhaltung, in der Tierzucht, in Ställen oder auf dem Hygienesektor. Anthelminthische Mischungspartner Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament. Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent. Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector. Another aspect in turn relates to the use of a compound of formula (I) as an anti-parasitic, in particular an arthropodicide such as an insecticide or an acaricide. Another aspect relates to the use of a compound of formula (I) as an anti-topazarasitic, in particular an arthropodicide such as Insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector. Anthelminthic mixture partners
[0203] Beispielhaft seien folgende anthelmintische Mischungspartner genannt: By way of example, the following anthelmintic mixing partners may be mentioned:
[0204] Anthelminthische Wirkstoffe, einschließlich trematicide und cestocide Wirkstoffe: aus der Klasse der macrocyclischen Lactone, z. B.: Abamectin, Doramectin, Emamectin, Eprinomectin, Ivermectin, Milbemycin, Moxidectin, Nemadectin, Selamectin; aus der Klasse der Benzimidazole und Probenzimidazole, z. B.: Albendazol, Albendazol- Sulfoxid, Cambendazol, Cyclobendazol, Febantel, Fenbendazol, Flubendazol, Mebendazol, Netobimin, Oxfendazol, Oxibendazol, Parbendazol, Thiabendazol, Thiophanat, Triclabendazol; aus der Klasse der Cyclooctadepsipeptide, z. B.: Emodepsid, PF1022; aus der Klasse der Aminoacetonitril-Derivate, z. B.: Monepantel; aus der Klasse der Tetrahydropyrimidine, z. B.: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole, z. B.: Butamisol, Levamisol, Tetramisol; aus der Klasse der Salicylanilide, z. B.: Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid, Tribromsalan; aus der Klasse der Paraherquamide, z. B.: Derquantel, Paraherquamid; - 5 - aus der Klasse der Aminophenylamidine, z. B.: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Organophosphate, z. B.: Coumaphos, Crufomat, Dichlorvos, Haloxon, Naphthalofos, Trichlorfon; aus der Klasse der substituierten Phenole, z. B.: Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan, Nitroxynil; aus der Klasse der Piperazinone, z. B.: Praziquantel, Epsiprantel; aus anderen diversen Klassen, z. B. : Amoscanat, Bephenium, Bunamidin, Clonazepam, Clorsulon, Diamfenetid, Dichlorophen, Diethylcarbamazin, Emetin, Hetolin, Hycanthon, Lucanthon, Miracil, Mirasan, Niclosamid, Niridazol, Nitroxynil, Nitroscanat, Oltipraz, Omphalotin, Oxamniquin, Paromomycin, Piperazin, Resorantel. Anthelminthic agents, including trematicide and cestocide agents: from the class of macrocyclic lactones, e.g. Such as: abamectin, doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin, nemadectin, selamectin; from the class of benzimidazoles and sample zimidazoles, e.g. For example: albendazole, albendazole sulfoxide, cambendazole, cyclobendazole, febantel, fenbendazole, flubendazole, mebendazole, netobimine, oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate, triclabendazole; from the class of cyclooctadepsipeptides, e.g. B: emodepside, PF1022; from the class of aminoacetonitrile derivatives, e.g. For example: Monepantel; from the class of tetrahydropyrimidines, e.g. B .: Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, e.g. B .: butamisole, levamisole, tetramisole; from the class of salicylanilides, e.g. For example: bromoxanide, breadanide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide, tribromomalan; from the class of Paraherquamide, z. B .: Derquantel, paraherquamide; - 5 - from the class of Aminophenylamidine, z. For example: amidantel, deacylated amide shell (dAMD), tribendimidine; from the class of organophosphates, e.g. B .: Coumaphos, Crufomat, Dichlorvos, Haloxon, Naphthalofos, Trichlorfon; from the class of substituted phenols, e.g. Bithionol, disophenol, hexachlorophene, nicolofolan, meniclopholan, nitroxynil; from the class of piperazinones, e.g. B .: praziquantel, epsiprantel; from other diverse classes, eg. As: amoscanate, bephenium, bunamidine, clonazepam, clorsulone, diamfenetide, dichlorophen, diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, miracil, mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz, omphalotin, oxamniquine, paromomycin, piperazine, resorantel ,
Vektorkontrolle vector control
[0205] Die Verbindungen der Formel (I) können auch in der Vektorkontrolle eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z.B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z.B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
[0206] Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: Examples of vectors and their transmitted diseases or pathogens are:
1) Mücken 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von Würmern; - Aedes: Gelbfieber, Dengue-Fieber, Filariasis, weitere virale Erkrankungen; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases;
- Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus; - Simulia: transmission of worms, in particular Onchocerca volvulus;
2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus); 2) lice: skin infections, typhus (epidemic typhus);
3) Flöhe: Pest, endemisches Fleckfieber; 4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 3) Fleas: plague, endemic typhus fever; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, virale Hirnhautentzündung (FSME), Krim-Kongo-Fieber, Borreliose; 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
6) Zecken: Borelliosen wie Borrelia duttoni, Frühsommer-Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis). 6) Ticks: Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
[0207] Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten wie Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Examples of vectors for the purposes of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
[0208] Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z.B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. 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, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
[0209] Eine Vektorkontrolle ist auch möglich, wenn die Verbindungen der Formel (I) Resistenzbrechend sind. [0210] Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten bzw. vor Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorkontrolle, z.B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorratsund Materialschutz. Schutz von technischen Materialen Vector control is also possible when the compounds of formula (I) are resistive. Compounds of formula (I) are suitable for use in the prevention of diseases or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials. Protection of technical materials
[0211] Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z.B. aus der Ordnung Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
[0212] 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.
[0213] In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. [0214] In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d.h., es kann ohne weitere n 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 another embodiment, the compounds of formula (I) are present as a ready-to-use pest control agent, ie, it may be readily available n
- 67 - - 67 -
Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder als Fungizide kommen insbesondere die oben genannten in Frage. Changes are applied to the appropriate material. As further insecticides or as fungicides in particular the above-mentioned in question.
[0215] Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Surprisingly, it has also been found that the compounds of formula (I) can be used to protect against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water , Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
[0216] Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. 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.
[0217] Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera , Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
[0218] Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. The application is carried out, for example, in aerosols, pressureless sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
[0219] Ein weiterer Aspekt der Erfindung ist die Verwendung einer Verbindung der Formel (I) als Herbizid. Another aspect of the invention is the use of a compound of formula (I) as a herbicide.
Darstellungsverfahren display method
[0220] Die erfindungsgemäßen Verbindungen können nach üblichen, dem Fachmann bekannten Methoden hergestellt werden. [0221] Im Reaktionsschema 1 ist ein allgemeines Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Ι') abgebildet. The compounds according to the invention can be prepared by customary methods known to the person skilled in the art. Reaction Scheme 1 shows a general method for the preparation of the compounds (Ι ') according to the invention.
Reaktionsschema 1
Figure imgf000069_0001
Reaction Scheme 1
Figure imgf000069_0001
Figure imgf000069_0002
Figure imgf000069_0002
[0222] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein Cl-C4-Alkyl. Q steht für O. Ei, E2 und E3 stehen für N oder CH, jeweils so ausgewählt, dass der Heterozyklus einen fünfgliedrieger Heterozyklen gemäß Tl, T2, T3 und T6 darstellt. U steht für Brom oder Iod wenn M für eine Boronsäure, einen Boronsäureester oder Trifluorboronat oder ein Zinkhalogenid steht. U steht für eine Boronsäure, einen Boronsäureester oder Trifluorboronat oder ein Zinkhalogenid, wenn M für Brom, Iod oder Triflat steht. X steht für F oder Cl. Eine bevorzugte Ausführung erfindungsgemäßer Verbindungen der allgemeinen Struktur Γ sind erfindungsgemäße Verbindungen der allgemeinen Struktur Ia. The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 -alkyl. Q stands for O. Ei, E2 and E3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to Tl, T2, T3 and T6. U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide. U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate. X stands for F or Cl. A preferred embodiment of compounds of the general structure Γ according to the invention are compounds of the general structure Ia according to the invention.
[0223] Durch Aktivierung von Intermediat 7 und anschließender Umsetzung der aktivierten Zwischenstufe mit Aminen der allgemeinen Struktur 8 können erfindungsgemäße Verbindungen der allgemeinen Struktur I' erhalten werden. Für diesen Amidierungsschritt sind zahlreiche Reaktionsbedingungen beschrieben worden. Eine Zusammenfassung findet sich in Houben-Weyl, Methoden der Organischen Chemie, Band E5 (Georg Thieme Verlag Stuttgart), S. 934. Einige dieser Reaktionen verlaufen über intermediäre Carbonsäurechloride, die isoliert oder in-situ erzeugt eingesetzt werden können. Die Amine der allgemeinen Struktur 8 oder ihre Salze sind kommerziell erhältlich oder nach dem Fachmann bekannten Verfahren darstellbar. By activating intermediate 7 and subsequently reacting the activated intermediate with amines of general structure 8, it is possible to obtain compounds of the general structure I 'according to the invention. Numerous reaction conditions have been described for this amidation step. A summary can be found in Houben-Weyl, Methods of Organic Chemistry, Volume E5 (Georg Thieme Verlag Stuttgart), p 934. Some of these reactions proceed via intermediate carboxylic acid chlorides, which can be isolated or used in situ generated. The amines of the general structure 8 or their salts are commercially available or can be prepared by methods known to the person skilled in the art.
[0224] Carbonsäuren der allgemeinen Struktur 7 können aus Carbonsäureestern der allgemeinen Struktur 6 analog literaturbekannten Methoden mittels geeigneter Basen, wie z. B. wässriger Lithiumhydroxid- oder Natriumhydroxid-Lösung, in geeigneten Lösungs- bzw. Verdünnungsmitteln, wie z. B. Dioxan oder THF erhalten werden. [0225] Intermediate der allgemeinen Struktur 6 können durch Reaktion von Intermediaten der allgemeinen Struktur 5 mit Halogenierungsmitteln erhalten werden. Als Halogenierungsmittel werden z.B. N-Halosuccinimide verwendet [siehe z.B. WO 2009/112845, WO 2012/137181]. Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF can be obtained. [0225] Intermediates of general structure 6 can be obtained by reaction of intermediates of general structure 5 with halogenating agents. As halogenating agents, for example, N-halosuccinimides are used [see, for example, WO 2009/112845, WO 2012/137181].
[0226] Verbindungen der allgemeinen Struktur 5 können mittels Palladium katalysierten Reaktionen aus den Reaktionspartnern 3 und 4 hergestellt werden [siehe z.B. WO 2010/071741; WO 2013/170115; Heterocydes 2010, 81, 1509-1516; WO2010/093885; US2014/0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.]. Die Verbindungen der allgemeinen Struktur 4 sind entweder kommerziell erhältlich oder können nach dem Fachmann bekannten Verfahren hergestellt werden [siehe z.B. WO2016/066697; Eur. J. Med. Chem. 2015, 102, 471-476; US2014/0200227; WO2014/033630 für M = Halogen; WO2011//162267 für M = Boronsäure; US2009/0215750 für M = Boronsäureester]. Compounds of general structure 5 can be prepared by palladium catalyzed reactions from reactants 3 and 4 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocydes 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.]. The compounds of general structure 4 are either commercially available or can be prepared by methods known to those skilled in the art [see, e.g. WO2016 / 066697; Eur. J. Med. Chem. 2015, 102, 471-476; US2014 / 0200227; WO2014 / 033630 for M = halogen; WO2011 // 162267 for M = boronic acid; US2009 / 0215750 for M = boronic acid ester].
[0227] Die Verbindungen der allgemeinen Struktur 3 lassen sich nach literaturbekannten Verfahren aus Reaktionspartnern der allgemeinen Struktur 1 und 2 herstellen [siehe z.B. WO2014/122083; WO 2014/135439; WO2016/020441]. Die Verbindungen der allgemeinen Struktur 2 sind kommerziell erhältlich. Verbindungen der allgemeinen Struktur 1 lassen sich nach dem Fachmann bekannten Verfahren herstellen [siehe z.B. WO 2015/181139; WO2016/020441]. The compounds of general structure 3 can be prepared by literature methods from reaction partners of the general structure 1 and 2 [see, for example. WO2014 / 122083; WO 2014/135439; WO2016 / 020441]. The compounds of general structure 2 are commercially available. Compounds of general structure 1 can be prepared by methods known to those skilled in the art [see, e.g. WO 2015/181139; WO2016 / 020441].
[0228] In Reaktionsschema lb ist ein weiteres Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Ι') abgebildet. Reaction scheme 1b shows a further process for the preparation of the compounds (Ι ') according to the invention.
Reaktionsschema lb Reaction scheme lb
Figure imgf000070_0001
Figure imgf000070_0001
Figure imgf000070_0002
Figure imgf000070_0002
[0229] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein Cl-C4-Alkyl. Q steht für O. Ei, E2 und E3 stehen für N oder CH, jeweils so ausgewählt, dass der Heterozyklus einen fünfgliedrieger Heterozyklen gemäß Tl, T2, T3 und T6 darstellt. U steht für Brom oder Iod wenn M für eine Boronsäure, einen Boronsäureester oder Trifluorboronat oder ein Zinkhalogenid steht. U steht für eine Boronsäure, einen Boronsäureester oder Trifluorboronat oder ein Zinkhalogenid, wenn M für Brom, Iod oder Triflat steht. X steht für F oder Cl. Hai steht für Cl, I oder 7 The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 -alkyl. Q stands for O. Ei, E 2 and E 3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to T 1, T 2 , T 3 and T 6. U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide. U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate. X stands for F or Cl. Shark stands for Cl, I or 7
Br. Eine bevorzugte Ausführung erfindungsgemäßer Verbindungen der allgemeinen Struktur Γ sind erfindungsgemäße Verbindungen der allgemeinen Struktur Ia. Br. A preferred embodiment of compounds of the general structure Γ according to the invention are compounds of the general structure Ia according to the invention.
[0230] Durch Aktivierung von Intermediat 7 und anschließender Umsetzung der aktivierten Zwischenstufe mit Aminen der allgemeinen Struktur 8 können erfindungsgemäße Verbindungen der allgemeinen Struktur I' erhalten werden. Für diesen Amidierungsschritt sind zahlreiche Reaktionsbedingungen beschrieben worden. Eine Zusammenfassung findet sich in Houben-Weyl, Methoden der Organischen Chemie, Band E5 (Georg Thieme Verlag Stuttgart), S. 934. Einige dieser Reaktionen verlaufen über intermediäre Carbonsäurechloride, die isoliert oder in-situ erzeugt eingesetzt werden können. Die Amine der allgemeinen Struktur 8 oder ihre Salze sind kommerziell erhältlich oder nach dem Fachmann bekannten Verfahren darstellbar. By activating intermediate 7 and then reacting the activated intermediate with amines of general structure 8, it is possible to obtain compounds of the general structure I 'according to the invention. Numerous reaction conditions have been described for this amidation step. A summary can be found in Houben-Weyl, Methods of Organic Chemistry, Volume E5 (Georg Thieme Verlag Stuttgart), p 934. Some of these reactions proceed via intermediate carboxylic acid chlorides, which can be isolated or used in situ generated. The amines of the general structure 8 or their salts are commercially available or can be prepared by methods known to the person skilled in the art.
[0231] Carbonsäuren der allgemeinen Struktur 7 können aus Carbonsäureestern der allgemeinen Struktur 6 analog literaturbekannten Methoden mittels geeigneter Basen, wie z. B. wässriger Lithiumhydroxid- oder Natriumhydroxid-Lösung, in geeigneten Lösungs- bzw. Verdünnungsmitteln, wie z. B. Dioxan oder THF erhalten werden. [0232] Verbindungen der allgemeinen Struktur 6 können mittels Palladium katalysierten Reaktionen aus den Reaktionspartnern 3 und 16 hergestellt werden [siehe z.B. WO 2010/071741 ; WO 2013/170115; Heterocycles 2010, 81, 1509-1516; WO2010/093885; US2014/0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.]. Die Verbindungen der allgemeinen Struktur 16 sind entweder kommerziell erhältlich oder können nach dem Fachmann bekannten Verfahren hergestellt werden. Verbindungen der allgemeinen Struktur 3 können analog der oben beschriebenen Verfahren hergestellt werden. Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such as. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF can be obtained. Compounds of general structure 6 can be prepared by palladium catalyzed reactions from reactants 3 and 16 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocycles 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.]. The compounds of general structure 16 are either commercially available or can be prepared by methods known to those skilled in the art. Compounds of general structure 3 can be prepared analogously to the methods described above.
[0233] In Reaktionschema 2 ist ein allgemeines Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Ib) dargestellt. Reaction Scheme 2 shows a general method for the preparation of the compounds (Ib) according to the invention.
Reaktionsschema 2 Reaction scheme 2
- 7 - - 7 -
Figure imgf000072_0001
Figure imgf000072_0001
[0234] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein C 1 -C4-Alkyl. Q steht für O. X steht für F oder Cl. [0234] The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 alkyl. Q stands for O. X stands for F or Cl.
[0235] Erfindungsgemäße Verbindungen Ib können aus Intermediaten der Struktur 13 erhalten werden, analog zur mehrstufigen Umsetzung von Intermediaten der allgemeinen Struktur 5 zu den erfindungsgemäßen Verbindungen I'. Compounds Ib of the invention can be obtained from intermediates of structure 13, analogously to the multistage reaction of intermediates of general structure 5 to the compounds I 'according to the invention.
[0236] Intermediate der allgememeinen Struktur 13 können durch Cu-katalysierte (z.B. Chem. Asian ./. 2013, 8, 800 - 808; Tetrahedron Lett. 2012, 53, 1606 - 1609) oder thermische (z.B. Tetrahedron Lett., 2009, 50, 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884) Umsetzung von Aziden der allgemeinen Struktur 12 und Acetylenen der allgemeinen Struktur 10 gewonnen werden. Intermediates of the general structure 13 may be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Lett., 2009, 50, 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 12 and acetylenes of general structure 10 can be obtained.
[0237] Verbindungen der allgemeinen Struktur 10 können durch Reaktion von Intermediaten der allgemeinen Struktur 1 und Trimethylsilylacetylen unter literaturbekannten Bedingungen erhalten werden (siehe z.B. WO2015/193218) Compounds of general structure 10 can be obtained by reaction of intermediates of general structure 1 and trimethylsilylacetylene under conditions known from the literature (see, for example, WO2015 / 193218).
[0238] Intermediate der allgemeinen Struktur 12 können in Analogie zu aus der Literatur bekannten Verfahren ausgehend von Aminen der allgemeinen Struktur 11 erhalten werden (z.B. Tetrahedron Lett. 2013, 54, 1294-1297; Eur. J. Med. Chem. 2014, 84, 545-554; Tetrahedron 2009, 65, 2678-2683). Amine der allgemeinen Struktur 11 sind komerziell erhältlich oder nach dem Fachmann bekannten Verfahren herstellbar. ? Intermediates of the general structure 12 can be obtained analogously to processes known from the literature starting from amines of the general structure 11 (eg Tetrahedron Lett. 2013, 54, 1294-1297; Eur. J. Med. Chem. 2014, 84 , 545-554; Tetrahedron 2009, 65, 2678-2683). Amines of the general structure 11 are commercially available or can be prepared by methods known to the person skilled in the art. ?
[0239] In Reaktionsschema 3 ist ein allgemeines Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Ic) abgebildet. Scheme 3 depicts a general method for the preparation of the compounds (Ic) according to the invention.
Reaktionsschema 3
Figure imgf000073_0001
Reaction scheme 3
Figure imgf000073_0001
17 18 19  17 18 19
Figure imgf000073_0002
Figure imgf000073_0002
22 Ic  22 Ic
[0240] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein Cl-C4-Alkyl. Q steht für O. X1 steht für F oder Cl, X2 steht für Br oder I. The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 -alkyl. Q is O. X 1 is F or Cl, X 2 is Br or I.
[0241] Erfindungsgemäße Verbindungen Ic können aus Intermediaten der Struktur 20 erhalten werden, analog zur mehrstufigen Umsetzung von Intermediaten der allgemeinen Struktur 5 zu den erfindungsgemäßen Verbindungen I' . Compounds Ic according to the invention can be obtained from intermediates of structure 20, analogously to the multistage reaction of intermediates of general structure 5 to give compounds I 'according to the invention.
[0242] Intermediate der allgememeinen Struktur 20 können durch Cu-katalysierte (z.B. Chem. Asian ./. 2013, 8, 800 - 808; Tetrahedron Lett. 2012, 53, 1606 - 1609) oder thermische (z.B. Tetrahedron Letl, 2009, 50, 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884) Umsetzung von Aziden der allgemeinen Struktur 17 und Acetylenen der allgemeinen Struktur 19 gewonnen werden. [0243] Intermediate der allgemeinen Struktur 17 können in Analogie zu aus der Literatur bekannten Verfahren ausgehend von Halogeniden der allgemeinen Struktur 1 durch Umsetzung mit Natriumazid erhalten werden (z.B. US2017/112129 AI, WO2012/80376 AI). Halogenide der allgemeinen Struktur 1 sind komerziell erhältlich oder können nach dem Fachmann bekannten Verfahren herstellbar. Intermediates of the general structure 20 can be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Letl, 2009, 50 , 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 17 and acetylenes of general structure 19 can be obtained. Intermediates of general structure 17 can be obtained in analogy to processes known from the literature starting from halides of general structure 1 by reaction with sodium azide (for example US2017 / 112129 A1, WO2012 / 80376 Al). Halides of general structure 1 are commercially available or can be prepared by methods known to the person skilled in the art.
[0244] Verbindungen der allgemeinen Struktur 19 können durch Reaktion von Intermediaten der allgemeinen Struktur 18 und Trimethylsilylacetylen unter literaturbekannten Bedingungen erhalten ? werden (z.B. EP879814). Intermediate der allgemeinen Struktur 18 sind komerziell erhältlich oder können nach dem Fachmann bekannten Verfahren hergstellt werden. Compounds of general structure 19 can be obtained by reaction of intermediates of general structure 18 and trimethylsilylacetylene under conditions known from the literature ? be (eg EP879814). Intermediates of general structure 18 are commercially available or can be prepared by methods known to those skilled in the art.
[0245] In Reaktionsschema 4 ist ein allgemeines Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Id) abgebildet. Reaktionsschema 3 Reaction Scheme 4 depicts a general method for the preparation of the compounds (Id) according to the invention. Reaction scheme 3
Figure imgf000074_0001
Figure imgf000074_0001
[0246] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein Cl-C4-Alkyl. Q steht für O. [0247] Erfindungsgemäße Verbindungen Id können aus Intermediaten der Struktur 25 erhalten werden, analog zur mehrstufigen Umsetzung von Intermediaten der allgemeinen Struktur 5 zu den erfindungsgemäßen Verbindungen I'. The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 -alkyl. Q stands for O. [0247] Compounds Id according to the invention can be obtained from intermediates of structure 25, analogously to the multistage reaction of intermediates of general structure 5 to give the compounds I 'according to the invention.
[0248] Erfindungsgemäße Intermediate der allgemeinen Struktur 25 können analog zu literaturbekannten Methoden aus Intermediaten der allgemeinen Struktur 24 und 10 erhalten werden. Hierbei werden Oxime 24 zunächst mit geeigneten Halogenierungsmitteln, z.B. N-Halosuccinimiden umsetzt und anschließend mit Acetylenen 10 in Gegenwart einer geeigneten Base, z.B. Triethylamin zur Reaktion bringt (z.B. WO2015/150442). Intermediates of the general structure 25 according to the invention can be obtained analogously to methods known from the literature from intermediates of the general structure 24 and 10. Here, oximes 24 are first treated with suitable halogenating agents, e.g. N-halosuccinimides and then reacted with acetylenes 10 in the presence of a suitable base, e.g. Triethylamine (e.g., WO2015 / 150442).
[0249] Oxime der allgemeinen Struktur 24 sind bekannt oder können analog literaturbekannter Methoden aus Aldehyden der allgemeinen Struktur 23 hergestellt werden (z.B. Bull. Chem. Soc. Jap. 1985, 58, 352-360; J. Chem. Soc. Perk. Trans. 1 1980, 4, 1029-1037). Aldehyde der allgemeinen Struktur 23 sind kommerziell erhältlich oder können nach dem Fachmann bekannten Verfahren hergestellt werden. ? Oximes of the general structure 24 are known or can be prepared from aldehydes of the general structure 23 analogously to literature methods (eg Bull. Chem. Soc., 1985, 58, 352-360; J. Chem. Soc., Perk. Trans 1 1980, 4, 1029-1037). Aldehydes of general structure 23 are commercially available or can be prepared by methods known to those skilled in the art. ?
[0250] In Reaktionsschema 5 ist ein weiteres allgemeines Darstellungsverfahren für die erfindungsgemäßen Verbindungen (Id) sowie (Ie) abgebildet. Reaction Scheme 5 depicts another general method for the preparation of the compounds (Id) and (Ie) according to the invention.
Reaktionsschema 5 Reaction scheme 5
Figure imgf000075_0001
Figure imgf000075_0001
[0251] Die Reste A1, R1, R2, R5, R6 und Hai haben die oben beschriebenen Bedeutungen. Alk steht für ein Cl-C4-Alkyl. Q steht für O. X steht für I, Br oder Cl. The radicals A 1 , R 1 , R 2 , R 5 , R 6 and shark have the meanings described above. Alk is a C 1 -C 4 -alkyl. Q stands for O. X stands for I, Br or Cl.
[0252] Erfindungsgemäße Verbindungen der allgemeinen Struktur Id oder Ie können aus Intermediaten der allgemeinen Struktur 25 oder 25' erhalten werden, analog zur mehrstufigen Umsetzung von Intermediaten der allgemeinen Struktur 5 zu den erfindungsgemäßen Verbindungen I'. Compounds of the general structure Id or Ie according to the invention can be obtained from intermediates of the general structure 25 or 25 ', analogously to the multistage reaction of intermediates of the general structure 5 to the compounds I' according to the invention.
[0253] Intermediate der allgemeinen Struktur 31 oder 31' können analog zu literaturbekannten Verfahren (sihe z.B. Eur. J. Med. Chem. 2016, 117, 85-98; WO2015/075025) nach Metallierung durch geeignete Metallierungsreagenzien, z.B. n-BuLi, mit geeigneten Carboxylierungsreagenzien, z.B. Dialkylcarbonaten oder Chlorameisensäurealkylestem zu Intermediaten der allgemeinen Struktur 25 oder 25" umgesetzt werden. Weiterhin können Intermediaten der allgemeinen Struktur 31 oder 31 ' in Analogie zu literaturbekannten Methoden durch Pd-katalysierte Umsetzung mit CO in Gegenwart von Alkoholen (z.B. MeOH) in geeigneten Lösungsmitteln (z.B. DMSO oder DMF) oder in geeigneten Alkoholen als Lösungsmittel (z.B. MeOH oder EtOH) zu Intermediaten der allgemeinen Struktur 25 oder 25" umgesetzt werden (siehe z.B. WO2011/100433; WO2013/032804; US2008/0269234) Intermediates of the general structure 31 or 31 'can be prepared analogously to processes known from the literature (see, for example, Eur. J. Med. Chem. 2016, 117, 85-98, WO2015 / 075025) after metallation by means of suitable metallating reagents, for example n-BuLi, be reacted with suitable Carboxylierungsreagenzien such as dialkyl carbonates or Chlorameisensäurealkylestem to give intermediates of the general structure 25 or 25 '. Furthermore, intermediates of general structure 31 or 31' to literature methods in analogy by Pd-catalyzed reaction with CO in the presence of alcohols (for example MeOH) in suitable solvents (eg DMSO or DMF) or in suitable alcohols as solvent (eg MeOH or EtOH) to intermediates of general structure 25 or 25 "are reacted (see, eg, WO2011 / 100433; WO2013 / 032804; US2008 / 0269234)
[0254] Die regioisomeren Intermediate der allgemeinen Struktur 31 oder 31' können analog zu literaturbekannten Verfahren durch Kondensation von Intermediaten der allgemeinen Struktur 30 mit Hydroxylamin oder seinem Hydrochlorid erhalten werden (z.B. Eur. J. Med. Chem. 2016, 117, 85-98, WO2009/029632). The regioisomeric intermediates of general structure 31 or 31 'can be prepared analogously to processes known from the literature by condensation of intermediates of general structure 30 Hydroxylamine or its hydrochloride are obtained (eg Eur. J. Med. Chem. 2016, 117, 85-98, WO2009 / 029632).
[0255] Intermediate der allgemeinen Struktur 29 können nach Deprotonierung mit einer geeigneten Base, z.B. NaH oder NaOMe durch Reaktion mit Intermediaten der allgemeinen Struktur 28 zu Intermediaten der allgemeinen Struktur 30 umgesetzt werden (z.B. Eur. J. Med. Chem. 2016, 117, 85- 98; Adv. Synth. Catal. 2016, 358, 2811-2816). Intermediate der allgemeinen Struktur 28 und 29 sind entweder kommerziell erhältlich oder könnnen nach dem Fachmann bekannten oder literaturbekannten Verfahren hergestellt werden. [0255] Intermediates of general structure 29 can be prepared after deprotonation with a suitable base, e.g. NaH or NaOMe can be converted to intermediates of general structure 30 by reaction with intermediates of general structure 28 (eg Eur. J. Med. Chem. 2016, 117, 85-98; Adv. Synth. Catal. 2016, 358, 2811-2816 ). Intermediates of general structure 28 and 29 are either commercially available or can be prepared by methods known to the person skilled in the art or known from the literature.
Experimenteller Teil Darstellung von N-Cyclopropyl-2-iodo-5-r2,-methyl-5,-(pentafluoroethyl -4,-(trifluoromethyl -2,H-l,3'- bipyrazol-4-yllthiophen-3-carboxamid (Ia-1) Experimental Part Preparation of N-cyclopropyl-2-iodo-5-r 2 , -methyl-5 , - (pentafluoroethyl-4 , - (trifluoromethyl-2 , H, 3'-bipyrazol-4-yl-thiophene-3-carboxamide (Ia 1)
Figure imgf000076_0001
Figure imgf000076_0001
Schritt 1 : Herstellung von 2,-Methyl-5,-(pentafluoroethyl -4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl -4,-(trifluoromethyl -2,H-L3,-bipyrazol Step 1: Preparation of 2 , -methyl-5 , - (pentafluoroethyl -4- (4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl-4 , - (trifluoromethyl-2 , H -L3 , -bipyrazole
[0256] 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol (477 mg) und Cs2C03 (1.25 g) werden in DMF (20 ml) vorgelegt und 5 min bei Raumtemperatur gerührt. 5-Fluoro-l-methyl-3- (pentafluoroethyl)-4-(trifluoromethyl)-lH-pyrazol (1.00 g) wird zugegeben und die Reaktionsmischung wird 2 h bei Raumtemperatur gerührt. Das Gemisch wird mit EtOAc verdünnt und auf halbgesättigte wässriger NH iCl-Lösung gegeben. Das Gemisch wird mit EtOAc extrahiert, die organische Phase mit H2O und gesättigter, wässriger NaCl-Lösung gewaschen und über MgS04 getrocknet. Das Lösungsmittel wird unter vermindertem Druck entfernt und der Rückstand mittels Flash- - 7 -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrazole (477 mg) and Cs 2 C0 3 (1.25 g) are dissolved in DMF (20 ml) and stirred for 5 min at room temperature. 5-Fluoro-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (1.00 g) is added and the reaction mixture is stirred for 2 h at room temperature. The mixture is diluted with EtOAc and added to half-saturated aqueous NH 4 Cl solution. The mixture is extracted with EtOAc, the organic phase washed with H 2 O and saturated aqueous NaCl solution and dried over MgSO 4. The solvent is removed under reduced pressure and the residue is flashed. - 7 -
Chromatographie (Gradient: c-Hexan/EtOAc) aufgereinigt. 2'-Methyl-5'-(pentafluoroethyl)-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol wird als farbloser Feststoff erhalten (463 mg). Chromatography (gradient: c-hexane / EtOAc). 2'-methyl-5 '- (pentafluoroethyl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -4' - (trifluoromethyl) -2'H1.3 '-bipyrazole is obtained as a colorless solid (463 mg).
HPLC-MSa): logP = 4.68, Masse (m/z) = 461 [(M+H)]+. 'H-NMR (400 MHz, de-DMSO): 8.50 (s, 1H), 8.07 (s, 1H), 3.74 (s, 3H), 1.30 (s, 12H) HPLC-MS a) : log P = 4.68, mass (m / z) = 461 [(M + H)] +. 'H-NMR (400 MHz, de-DMSO): 8.50 (s, 1H), 8.07 (s, 1H), 3.74 (s, 3H), 1.30 (s, 12H)
Schritt 2: Herstellung von Methyl 5-Γ2,-methyl-5,-(pentafluoroethyl)-4,-(trifluoromethyl)-2,H-L3,- bipyrazol-4-yllthiophen-3-carboxylat Step 2: Preparation of methyl 5- , 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H-L3 , - bipyrazol-4-yl-thiophene-3-carboxylate
2'-Methyl-5'-(pentafluoroethyl)-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-4'-(trifluoromethyl)- 2'H-l,3'-bipyrazol (500 mg), Methyl-5-bromothiophen-3-carboxylat (264 mg), Pd(PPh3)4 (251 mg) und CS2CO3 (1.06 g) werden unter Argonatmosphäre in 1,4-Dioxan (7 ml) gelöst und Η2Ο (3 ml) wird zugegeben. Die Reaktionsmischung wird 2 h unter Mikrowellenbestrahlung gerührt. Das Gemisch wird mit EtOAc verdünnt und mit gesättigter wässriger NaCl-Lösung gewaschen. Die organische Phase wird über MgSÜ4 getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. Der Rückstand wird mittels Flash-Chromatographie (Gradient: c-Hexan/EtOAc) aufgereinigt. Methyl-5-[2'-methyl-5'- (pentafluoroethyl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol-4-yl]thiophen-3-carboxylat wird als gelber Feststoff erhalten (335 mg). 2'-methyl-5 '- (pentafluoroethyl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -4' - (trifluoromethyl) -2'H1.3 '-bipyrazole (500 mg), methyl 5-bromothiophene-3-carboxylate (264 mg), Pd (PPh 3 ) 4 (251 mg) and CS 2 CO 3 (1.06 g) are dissolved under argon atmosphere in 1,4-dioxane (7 ml ) and Η2Ο (3 ml) is added. The reaction mixture is stirred for 2 hours under microwave irradiation. The mixture is diluted with EtOAc and washed with saturated aqueous NaCl solution. The organic phase is dried over MgSO 4 and the solvent removed under reduced pressure. The residue is purified by flash chromatography (gradient: c-hexane / EtOAc). Methyl 5- [2'-methyl-5'- (pentafluoroethyl) -4 '- (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxylate is obtained as a yellow solid (335 mg ).
HPLC-MSa): logP = 4.33, Masse (m/z) = 475 [(M+H)]+. HPLC-MS a) : log P = 4.33, mass (m / z) = 475 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 8.74 (s, 1H), 8.48 (s, 1H), 8.30 (d, 1H), 7.77 (d, 1H), 3.82 (s, 3H), 3,82 (s, 3H) Schritt 3: Herstellung von Methyl-2-iodo-5-r2,-methyl-5,-(pentafluoroethyl)-4,-(trifluoromethyl)-2,H- L3'-bipyrazol-4-yllthiophen-3-carboxylat 'H-NMR (400 MHz, de-DMSO): 8.74 (s, 1H), 8.48 (s, 1H), 8.30 (d, 1H), 7.77 (d, 1H), 3.82 (s, 3H), 3, 82 (s, 3H) Step 3: Preparation of methyl 2-iodo-5-r2 , methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H-L3'-bipyrazol-4-yl-thiophene -3-carboxylate
[0257] Methyl-5-[2'-methyl-5'-(pentafluoroethyl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol-4-yl]thiophen- 3-carboxylat (335 mg) wird in AcOH gelöst und N-Iodsuccinimid (142 mg) wird bei Raumtemperatur zugegeben. Das Reaktionsgemisch wird 2 h bei 50 °C gerührt. N-Iodsucinnimid (16 mg) wird zugegeben und die Mischung wird über Nacht bei 50 °C gerührt. N-Iodsucinnimid (79 mg) wird zugegeben und die Mischung wird 5 h bei 50 °C gerührt. N-Iodsucinnimid (159 mg) wird zugegeben und die Mischung wird über Nacht bei 50 °C gerührt. Die Reaktionsmischung wird auf Raumtemperatur abgekühlt, mit EtOAc verdünnt und nacheinander mit gesättigter wässriger NaHS03-Lösung, Wasser, gesättigter wässsriger NaHC03-Lösung und gesättigter wässriger NaCl-Lösung gewaschen. Das Lösungsmittel wird unter vermindertem Druck entfernt und der Rückstand mittels HPLC (Gradient: H20/Acetonitril) aufgereinigt. Methyl-2-iodo-5-[2'-methyl-5'-(pentafluoroethyl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol-4- yl]thiophen-3-carboxylat wird als farbloser Feststoff erhalten (259 mg). ηη Methyl 5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxylate (335mg) dissolved in AcOH and N-iodosuccinimide (142 mg) is added at room temperature. The reaction mixture is stirred at 50 ° C for 2 h. N-iodosuccinimide (16 mg) is added and the mixture is stirred overnight at 50 ° C. N-iodosuccinimide (79 mg) is added and the mixture is stirred at 50 ° C for 5 h. N-iodosuccinimide (159 mg) is added and the mixture is stirred overnight at 50 ° C. The reaction mixture is cooled to room temperature, diluted with EtOAc and washed successively with saturated aqueous NaHSO 3 solution, water, saturated aqueous NaHCO 3 solution and saturated aqueous NaCl solution. The solvent is removed under reduced pressure and the residue is purified by HPLC (gradient: H 2 O / acetonitrile). Methyl 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxylate becomes a colorless solid received (259 mg). ηη
HPLC-MSa): logP = 4.98, Masse (m/z) = 601 [(M+H)]+. HPLC-MS a) : logP = 4.98, mass (m / z) = 601 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 8.72 (s, 1H), 8.45 (s, 1H), 7.59 (s, 1H), 3.83 (s, 3H), 3.81 (s, 3H). 'H-NMR (400 MHz, de-DMSO): 8.72 (s, 1H), 8.45 (s, 1H), 7.59 (s, 1H), 3.83 (s, 3H), 3.81 (s, 3H).
Schritt 4: Herstellung von 2-Iodo-5-Γ2,-methyl-5,-( entafluoroethyl)-4,-(trifluoromethyl)-2,H-l,3,- bipyrazol-4-yllthiophen-3-carbonsäure [0258] Methyl-2-iodo-5-[2'-methyl-5'-(pentafluoroethyl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol-4- yl]thiophen-3-carboxylat (229 mg) wird in THF gelöst und LiOH (18 mg) gelöst in Wasser wird zugegeben. Das Reaktionsgemisch wird 1.5 h bei 60 °C gerührt. Die Reaktionslösung wird auf Raumtemperatur abgekühlt, mit EtOAc verdünnt und mit wässriger HCl (IM) und gesättigter wässriger NaCl-Lösung gewaschen. Die organische Phase wird über MgSC getrocknet und das Lösungsmittel unter vermindertem Druck entfernt. 2-Iodo-5-[2'-methyl-5'-(pentafluoroethyl)-4'-(trifluoromethyl)-2'H- l,3'-bipyrazol-4-yl]thiophen-3-carbonsäure wird als gelber Feststoff erhalten (217 mg) und ohne weitere Aufreinigung in der Folgereaktion eingesetzt. Step 4: Preparation of 2-iodo-5-Γ 2 , -methyl-5 , - (entafluoroethyl) -4 , - (trifluoromethyl) -2 , H, 3 , -bipyrazol-4-yl-thiophene-3-carboxylic acid. Methyl 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxylate (229mg) dissolved in THF and LiOH (18 mg) dissolved in water is added. The reaction mixture is stirred at 60 ° C for 1.5 h. The reaction solution is cooled to room temperature, diluted with EtOAc and washed with aqueous HCl (IM) and saturated aqueous NaCl solution. The organic phase is dried over MgSC and the solvent removed under reduced pressure. 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H, 1,3'-bipyrazol-4-yl] thiophene-3-carboxylic acid becomes a yellow solid received (217 mg) and used without further purification in the subsequent reaction.
HPLC-MSa): logP = 3.99, Masse (m/z) = 587 [(M+H)]+. HPLC-MS a) : logP = 3.99, mass (m / z) = 587 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 13.1 (s, 1H), 8.07 (s, 1H), 8.44 (s, 1H), 7.56 (s, 1H), 3.81 (s, 3H). Schritt 5: Herstellung von N-Cyclopropyl-2-iodo-5-r2'-methyl-5,-(pentafluoroethyl)-4,-(trifluoromethyl)- 2'H-L3'-bipyrazol-4-yllthiophen-3-carboxamid (Ia-1) 'H-NMR (400 MHz, de-DMSO): 13.1 (s, 1H), 8.07 (s, 1H), 8.44 (s, 1H), 7.56 (s, 1H), 3.81 (s, 3H). Step 5: Preparation of N-Cyclopropyl-2-iodo-5-R2'-methyl-5 - (pentafluoroethyl) -4 - (trifluoromethyl) - 2'H-L3'-bipyrazol-4-yllthiophen-3-carboxamide (Ia-1)
[0259] 2-Iodo-5-[2'-methyl-5'-(pentafluoroethyl)-4'-(trifluoromethyl)-2'H-l,3'-bipyrazol-4-yl]thiophen- 3-carbonsäure (109 mg), 4-Dimethylaminopyridin (68.2 mg), l-(3-Dimethylaminopropyl)-3- ethylcarbodiimidhydrochlorid (107 mg) werde in CH2CI2 (9 ml) und NN-Dimethylformamid (1 ml) vorgelegt und 15 min bei Raumtemperatur gerührt. Cyclopropylamid (26.5 mg) wird zugegeben und die Mischung wird über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mit CH2CI2 verdünnt und mit HCl (IN) gewaschen. Die organische Phase wird über MgSC getrocknet und das Lösungsmittel wird unter vermindertem Druck entfernt. Der Rückstand wird mittels HPLC (Gradient: H20/Acetonitril) aufgereinigt und N-Cyclopropyl-2-iodo-5-[2'-methyl-5'-(pentafluoroethyl)-4'- (trifluoromethyl)-2'H-l,3'-bipyrazol-4-yl]thiophen-3-carboxamid (Ia-1) wird als farbloser Feststoff erhalten (80 mg). 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxylic acid (109 mg ), 4-dimethylaminopyridine (68.2 mg), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (107 mg) are placed in CH 2 Cl 2 (9 ml) and N, N-dimethylformamide (1 ml) and stirred at room temperature for 15 minutes. Cyclopropylamide (26.5 mg) is added and the mixture is stirred overnight at room temperature. The reaction mixture is diluted with CH 2 CI 2 and washed with HCl (IN). The organic phase is dried over MgSC and the solvent is removed under reduced pressure. The residue is purified by HPLC (gradient: H 2 O / acetonitrile) and N-cyclopropyl-2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4'- (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxamide (Ia-1) is obtained as a colorless solid (80 mg).
HPLC-MSa): logP = 4.13, Masse (m/z) = 626 [(M+H)]+. HPLC-MS a) : logP = 4.13, mass (m / z) = 626 [(M + H)] +.
'H-NMR: S. Peak-Liste 'H-NMR: S. peak list
Darstellung von 2-Chlor-N-cyclopropyl-5- { 1 -[1 -methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yl]-lH-L2,3-triazol-4-yl}thiophen-3-carboxamid (Ib-4) Preparation of 2-chloro-N-cyclopropyl-5- {1- [1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-L2,3-triazole-4 -yl} thiophene-3-carboxamide (Ib-4)
Figure imgf000079_0001
Figure imgf000079_0001
Figure imgf000079_0002
Figure imgf000079_0002
Schritt 1 : Herstellung von 5-Azido-l-methyl-3-(pentafluorethyl -4-(trifluormethyl -lH-pyrazol Step 1: Preparation of 5-azido-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
Natriumazid (213 mg) wird in Dimethylsulfoxid (7 mL) vorgelegt und es wird 5-Fluor-l-methyl-3- (pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol (986 mg) bei Raumtemperatur zugegeben. Das Reaktionsgemisch wird über Nacht bei Raumtemperatur gerührt und anschließend ohne weitere Aufarbeitung und Aufreinigung in der Folgestufe eingesetzt. Sodium azide (213 mg) is initially charged in dimethyl sulfoxide (7 mL) and 5-fluoro-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (986 mg) is added at room temperature. The reaction mixture is stirred overnight at room temperature and then used in the subsequent stage without further workup and purification.
Schritt 2 Herstellung von Methyl-5-ethinylthiophen-3-carboxylat Step 2 Preparation of methyl 5-ethynylthiophene-3-carboxylate
Methyl-5-bromthiophen-3-carboxylat (1 g) wird unter Argon in mit Argon gesättigtem N,N- Dimethylformamid (7 mL) und Triethylamin (5.08 g) vorgelegt. Ethynyl(trimethyl)silan (2.04 g), Bis(triphenylphosphin)palladium(II) dichlorid (143 mg) und Kupfer(I)iodid (19 mg) werden zugegeben und das Reaktionsgemisch wird 4 h bei 80 °C gerührt. Die Reaktionslösung wird nach dem Abkühlen mit Ethylacetat versetzt und mit HCl-Lösung (5 %ig) und wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wird in Tetrahydrofuran (13 mL) gelöst, mit Tetra-n-butylammoniumfluorid (6.5 mL, IM in THF) versetzt und 1 h bei Raumtempratur gerührt. Die Reaktionslösung wird mit Ethylacetat verdünnt und mit HCl-Lösung (5%ig), Wasser und wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Methyl-5-ethinylthiophen-3-carboxylat (861 mg), welches ohne weitere Aufreinigung in der Folgestufe eingesetzt wird. Methyl 5-bromothiophene-3-carboxylate (1 g) is placed under argon in argon-saturated N, N-dimethylformamide (7 mL) and triethylamine (5.08 g). Ethynyl (trimethyl) silane (2.04 g), bis (triphenylphosphine) palladium (II) dichloride (143 mg) and copper (I) iodide (19 mg) are added and the reaction mixture is stirred at 80 ° C for 4 h. The reaction solution is added after cooling with ethyl acetate and washed with HCl solution (5%) and aqueous saturated sodium chloride solution. The organic phase is dried and freed from the solvent under reduced pressure. The residue is dissolved in tetrahydrofuran (13 mL), treated with tetra-n-butylammonium fluoride (6.5 mL, III in THF) and stirred for 1 h at room temperature. The reaction solution is diluted with ethyl acetate and washed with HCl solution (5%), water and aqueous saturated sodium chloride solution. The organic phase is dried and freed from the solvent under reduced pressure. Methyl 5-ethynylthiophene-3-carboxylate (861 mg), which is used without further purification in the subsequent stage.
HPLC-MSa): logP = 2,26 HPLC-MS a) : log P = 2.26
'H-NMR (400 MHz, de-DMSO): 8.36 (d, 1H), 7.63 (d, 1H), 4.68 (s, 1H), 3.80 (s, 3H) ? 'H-NMR (400 MHz, de-DMSO): 8.36 (d, 1H), 7.63 (d, 1H), 4.68 (s, 1H), 3.80 (s, 3H) ?
Schritt 3: Herstellung von Methyl-5- {l-ri-methyl-3-(pentafluorethyl -4-(trifluormethyl -lH-pyrazol-5- yll-lH-l,2,3-triazol-4-yl}thiophen-3-carboxylat Step 3: Preparation of methyl 5- {1-ri-methyl-3- (pentafluoroethyl-4-trifluoromethyl-1H-pyrazol-5-yl-1H-1,2,3-triazol-4-yl} thiophene 3-carboxylate
Die Reaktionslösung aus Schritt 1 wird mit Wasser (3.5 mL) verdünnt. Es werden Methyl-5- ethinylthiophen-3-carboxylat (861 mg), Kupfer(II)sulfatpentahydrat (90.5 mg), Natriumascorbat (71.8 mg) und Tris[(l-benzyl-lH-l,2,3-triazol-4-yl)methyl]amin (19.2 mg) zugegeben und es wird bei Raumtemparatur gerührt, bis das Produkt aus Schritt 1 vollständig abreagiert ist. Das Reaktionsgemisch wird mit Ethylacetat verdünnt und mit wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird über Magnesiumsulfat getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wird mittels Flash-Chromatographie (Gradient: c- Hexan/EtOAc) aufgereinigt. Methyl-5- {l-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol- 5-yl]-lH-l,2,3-triazol-4-yl}thiophen-3-carboxylat (906 mg) wird als gelber Feststoff erhalten. The reaction solution from step 1 is diluted with water (3.5 mL). Methyl-5-ethynylthiophene-3-carboxylate (861 mg), copper (II) sulfate pentahydrate (90.5 mg), sodium ascorbate (71.8 mg) and tris [(1-benzyl-1H-1,2,3-triazole-4 -yl) methyl] amine (19.2 mg) is added and it is stirred at room temperature until the product from step 1 is completely reacted. The reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and freed from the solvent under reduced pressure. The residue is purified by flash chromatography (gradient: c-hexane / EtOAc). Methyl 5- {1- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl} thiophene-3 Carboxylate (906 mg) is obtained as a yellow solid.
HPLC-MSa): logP = 4.20, Masse (m/z) = 476 [(M+H)]+. HPLC-MS a) : log P = 4.20, mass (m / z) = 476 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.24 (s, 1H), 8.45 (d, 1H), 7.98 (d, 1H), 3.87 (s, 3H), 3.84 (s, 3H). 'H-NMR (400 MHz, de-DMSO): 9.24 (s, 1H), 8.45 (d, 1H), 7.98 (d, 1H), 3.87 (s, 3H), 3.84 (s, 3H).
Schritt 4: Herstellung von Methyl-2-chlor-5- {l-ri-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yll-lH-l,2,3-triazol-4-yl}thiophen-3-carboxylat Step 4: Preparation of methyl 2-chloro-5- {1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole 4-yl} thiophene-3-carboxylate
Methyl-5- {l-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3-triazol-4- yl}thiophen-3-carboxylat (302 mg) wird in Essigsäure vorgelegt, N-Chlorsuccinimid (127 mg) wird zugegeben und das Gemisch wird 4 h bei Raumtemperatur gerührt. Anschließend wird auf eine Badtemperatur von 50 °C erwärmt und weiter über Nacht gerührt. Das Reaktionsgemisch wird mit Ethylacetat verdünnt und mit wässriger Natriumthiosulfatlösung und wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet, filtriert und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wird mittel pHPLC (Gradient: Acetonitril/Wasser) gereinigt. Man erhält Methyl-2-chlor-5- {l-[l-methyl-3-(pentafluorethyl)-4- (trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3-triazol-4-yl}thiophen-3-carboxylat (128 mg) als farblosen Feststoff. Methyl 5- {1- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl} thiophene-3 carboxylate (302 mg) is charged in acetic acid, N-chlorosuccinimide (127 mg) is added and the mixture is stirred for 4 h at room temperature. It is then heated to a bath temperature of 50 ° C and stirred overnight. The reaction mixture is diluted with ethyl acetate and washed with aqueous sodium thiosulfate solution and aqueous saturated sodium chloride solution. The organic phase is dried, filtered and freed from the solvent under reduced pressure. The residue is purified by means of pHPLC (gradient: acetonitrile / water). There are obtained methyl 2-chloro-5- {1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,3,3-triazole-4 -yl} thiophene-3-carboxylate (128 mg) as a colorless solid.
HPLC-MSa): logP = 4.85, Masse (m/z) = 510 [(M+H)]+. HPLC-MS a) : log P = 4.85, mass (m / z) = 510 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.26 (s, 1H), 7.92 (s, 1H), 3.87 (s, 3H), 3.86 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 9.26 (s, 1H), 7.92 (s, 1H), 3.87 (s, 3H), 3.86 (s, 3H)
Schritt 5: Herstellung von 2-Chlor-5- {l-ri-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5- yll-lH-L2,3-triazol-4-yl}thiophen-3-carbonsäure Methyl-2-chlor-5- {l-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3- triazol-4-yl}thiophen-3-carboxylat (128 mg) wird in Tetrahydrofuran vorgelegt, eine wässrige Lösung aus Lithiumhydroxid (0.72 mL, IM) wird zugetropft und es wird über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mit wässriger HCl-Lösung (IM) angesäuert und mit Ethylacetat extrahiert. Die organische Phase wird getrocknet, filtriert und unter vermindertem Druck vom Lösungsmittel befreit. Man erhält 2-Chlor-5- {l-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yl]-lH-l,2,3-triazol-4-yl}thiophen-3-carbonsäure (122 mg) als gelben Feststoff. HPLC-MSa): logP = 3.85, Masse (m/z) = 496 [(M+H)]+. Step 5: Preparation of 2-chloro-5- {1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-4-yl} thiophene-3-carboxylic acid methyl 2-chloro-5- {1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -LH-l, 2,3- Triazol-4-yl} thiophene-3-carboxylate (128 mg) is initially charged in tetrahydrofuran, an aqueous solution of lithium hydroxide (0.72 mL, 1M) is added dropwise and it is left overnight at room temperature touched. The reaction mixture is acidified with aqueous HCl solution (I.M.) and extracted with ethyl acetate. The organic phase is dried, filtered and freed from the solvent under reduced pressure. This gives 2-chloro-5- {1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl } thiophene-3-carboxylic acid (122 mg) as a yellow solid. HPLC-MS a) : log P = 3.85, mass (m / z) = 496 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 13.43 (s, 1H), 9.24 (s, 1H), 7.87 (s, 1H), 3.87 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 13.43 (s, 1H), 9.24 (s, 1H), 7.87 (s, 1H), 3.87 (s, 3H)
Schritt 6: Herstellung von 2-Chlor-N-cyclopropyl-5- {l -ri-methyl-3-(pentafluorethyl)-4-(trifluormethyl)- lH-pyrazol-5-yll-lH-L2,3-triazol-4-yl}thiophen-3-carboxamid (Ib-4) Step 6: Preparation of 2-chloro-N-cyclopropyl-5- {1 -ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazole 4-yl} thiophene-3-carboxamide (Ib-4)
2-Chlor-5- { 1 -[1 -methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l ,2,3-triazol-4- yl}thiophen-3-carbonsäure (61 mg), Cyclopropylamin (14 μΐ,), Triethylamin (66 μΐ,) und HATU (67 mg) werden in N,N-Dimethylformamid vorgelegt und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mittels pHPLC (Gradient: Acetonitril/Wasser) gereinigt. Man erhält 2-Chlor-N- cyclopropyl-5- { 1 - [1 -methyl-3 -(pentafluorethyl)-4-(trifluormethyl)- lH-pyrazol-5-yl]- 1H- 1 ,2,3-triazol-4- yl}thiophen-3-carboxamid (Ib-4) (55 mg) als farblosen Feststoff. HPLC-MSa): logP = 4.03, Masse (m/z) = 535 [(M+H)]+. 2-Chloro-5- {1 - [1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl} thiophene 3-carboxylic acid (61 mg), cyclopropylamine (14 μΐ,), triethylamine (66 μΐ,) and HATU (67 mg) are charged in N, N-dimethylformamide and stirred overnight at room temperature. The reaction mixture is purified by means of pHPLC (gradient: acetonitrile / water). There are obtained 2-chloro-N-cyclopropyl-5- {1 - [1-methyl-3 - (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazole 4-yl} thiophene-3-carboxamide (Ib-4) (55 mg) as a colorless solid. HPLC-MS a) : log P = 4.03, mass (m / z) = 535 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.13 (s, 1H), 8.46 (d, 1H), 7.73 (s, 1H), 3.86 (s, 3H), 'H-NMR (400 MHz, de-DMSO): 9.13 (s, 1H), 8.46 (d, 1H), 7.73 (s, 1H), 3.86 (s, 3H),
2.85-2.80 (m, 1H), 0.74-0.69 (m, 2H), 0.57-0.53 (m, 2H) 2.85-2.80 (m, 1H), 0.74-0.69 (m, 2H), 0.57-0.53 (m, 2H)
Darstellung von 2-Chlor-N-cyclopropyl-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yll-lH-L2,3-triazol-l-yl}thiophen-3-carboxamid (Ic-4) Preparation of 2-chloro-N-cyclopropyl-5- {4- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazole-1-one yl} thiophene-3-carboxamide (Ic-4)
Figure imgf000081_0001
Figure imgf000081_0001
Figure imgf000081_0002
Schritt 1 : Herstellung von 5-Ethinyl-l-methyl-3-(pentafluorethyl -4-(trifluormethyl -lH-pyrazol
Figure imgf000081_0002
Step 1: Preparation of 5-ethynyl-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
Ethinyl(trimethyl)silan (750 mg) wird unter Argon in Tetrahydrofuran (12 mL) vorgelegt und auf -78 °C gekühlt. n-Butyllithium (3.58 mL, 1.6M) wird zugetropft und es wird 5 Minuten bei -78 °C gerührt. Anschließend wird 5-Fluor-l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol (1.09 g) zugetropft und 30 Minuten bei 0 °C und 60 Minuten bei Raumtemperatur gerührt. Die Reaktion wird wieder auf -78 °C gekühlt und durch Zugabe von Wasser beendet. Nach dem Auftauen wird mit Dichlormethan (3x) extrahiert und die organische Phase wird unter vermindertem Druck vom Lösungsmittel befreit. Man erhält 5-Ethinyl-l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol (1.49 g) als schwarzes Öl, welches ohne weitere Aufreinigung in der Folgestufe eingesetzt wird. HPLC-MSa): logP = 3.72 Ethinyl (trimethyl) silane (750 mg) is placed under argon in tetrahydrofuran (12 mL) and cooled to -78 ° C. n-Butyllithium (3.58 mL, 1.6M) is added dropwise and it is stirred for 5 minutes at -78 ° C. Subsequently, 5-fluoro-l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (1.09 g) is added dropwise and stirred for 30 minutes at 0 ° C and 60 minutes at room temperature. The reaction is cooled again to -78 ° C and terminated by adding water. After thawing, it is extracted with dichloromethane (3x) and the organic phase is freed from the solvent under reduced pressure. 5-ethynyl-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (1.49 g) is obtained as a black oil, which is used without further purification in the subsequent stage. HPLC-MS a) : logP = 3.72
'H-NMR (400 MHz, de-DMSO): 5.47 (s, 1H), 4.03 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 5.47 (s, 1H), 4.03 (s, 3H)
Schritt 2: Herstellung von Methyl-5-azidothiophen-3-carboxylat Step 2: Preparation of methyl 5-azidothiophene-3-carboxylate
Methyl-5-aminothiophen-3-carboxylat (393 mg) wird in Trifluoressigsäure (25 g) vorgelegt. Die Lösung wird auf 0 °C gekühlt, Natriumnitrit (345 mg) zugegeben und 20 Minuten bei 0 °C gerührt. Anschließend wird Natriumazid (488 mg) portionsweise zugegeben und für weitere 30 Minuten gerührt. Das Reaktionsgemisch wird mit Ethylacetat verdünnt und mit Wasser (2x) und wässriger, gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Man erhält Methyl-5-azidothiophen-3-carboxylat (426 mg) als braunes Öl, welches ohne weitere Aufreinigung in der Folgestufe eingesetzt wird. HPLC-MSa): logP = 2.48 Methyl 5-aminothiophene-3-carboxylate (393 mg) is presented in trifluoroacetic acid (25 g). The solution is cooled to 0 ° C, sodium nitrite (345 mg) added and stirred at 0 ° C for 20 minutes. Then, sodium azide (488 mg) is added portionwise and stirred for a further 30 minutes. The reaction mixture is diluted with ethyl acetate and washed with water (2 ×) and aqueous, saturated sodium chloride solution. The organic phase is dried and freed from the solvent under reduced pressure. This gives methyl 5-azidothiophene-3-carboxylate (426 mg) as a brown oil, which is used without further purification in the subsequent stage. HPLC-MS a) : logP = 2.48
'H-NMR (400 MHz, de-DMSO): 8.03 (s, 1H), 8.02 (s, 1H), 3.79 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 8.03 (s, 1H), 8.02 (s, 1H), 3.79 (s, 3H)
Schritt 3: Herstellung von Methyl-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5- yll-lH-L2,3-triazol-l-yl}thiophen-3-carboxylat Step 3: Preparation of methyl 5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-1-yl} thiophene -3-carboxylate
Methyl-5-azidothiophen-3-carboxylat (426 mg) wird in Dimethylsulfoxid (4 mL) und Wasser (2 mL) vorgelegt, 5-Ethinyl-l -methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol (815 mg),Methyl 5-azidothiophene-3-carboxylate (426 mg) is initially charged in dimethyl sulfoxide (4 mL) and water (2 mL), 5-ethynyl-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -H-OH. pyrazole (815 mg),
Kupfer(II)sulfat (51.9 mg), Natriumascorbat (46 mg) und TBTA (12.3 mg) werden zugegeben. Das Gemisch wird 4 h bei Raumtemperatur gerührt, anschließend mit Ethylacetat verdünnt und mit wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird über Magnesiumsulfat getrocknet und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wird mittels Flash-Chromatographie (Gradient: c-Hexan/EtOAc) aufgereinigt, um Methyl-5- {4-[l-methyl-3- (pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3-triazol-l-yl}thiophen-3-carboxylat (540 mg) als braunes Öl zu erhalten. HPLC-MSa): logP = 4.10, Masse (m/z) = 476 [(M+H)]+. Copper (II) sulfate (51.9 mg), sodium ascorbate (46 mg) and TBTA (12.3 mg) are added. The mixture is stirred for 4 h at room temperature, then diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and freed from the solvent under reduced pressure. The residue is purified by flash chromatography (gradient: c-hexane / EtOAc) to give methyl 5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl ] -LH-l, 2,3-triazol-1-yl} thiophene-3-carboxylate (540 mg) as a brown oil. HPLC-MS a) : logP = 4.10, mass (m / z) = 476 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.50 (s, 1H), 8.38 (d, 1H), 8.10 (d, 1H), 4.00 (s, 3H), 3.86 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 9.50 (s, 1H), 8.38 (d, 1H), 8.10 (d, 1H), 4.00 (s, 3H), 3.86 (s, 3H)
Schritt 4: Herstellung von Methyl-2-chlor-5-{4 1-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yl1-lH-l,2,3-triazol-l-yl}thiophen-3-carboxylat Methyl-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl) H-pyrazol-5-yl] H-l,2,3-triazol-l- yl}thiophen-3-carboxylat (260 mg) wird in Essigsäure vorgelegt, N-Chlorsuccinimid (110 mg) wird zugegeben und es wird über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird auf 50 °C Badtemperatur erwärmt und weitere 5 h gerührt. Es wird N-Chlorsuccinimid (37 mg) zugegeben und über Nacht bei 50 °C Badtemperatur gerührt. Es wird nochmals N-Chlorsuccinimid (74 mg) zugegeben und 6 h bei 80 °C gerührt. Anschließend wird N-Chlorsuccinimid (74 mg) zugegeben und über Nacht bei 80°C gerührt. Das Reaktionsgemisch wird wit Ethylacetat verdünnt und mit wässriger gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet, filtriert und unter vermindertem Druck vom Lösungsmittel befeit. Der Rückstand wird mittels pHPLC (Gradient: Acetonitril/Wasser) gereinigt. Man erhält Methyl-2-chlor-5- {4-[l-methyl-3-(pentafluorethyl)-4- (trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3-triazol-l-yl}thiophen-3-carboxylat (159 mg) als farblosen Feststoff. Step 4: Preparation of methyl 2-chloro-5- {4 1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole-1 -yl} thiophene-3-carboxylate Methyl 5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -H-pyrazol-5-yl] H, 2,3-triazol-1-yl } thiophene-3-carboxylate (260 mg) is initially charged in acetic acid, N-chlorosuccinimide (110 mg) is added and the mixture is stirred at room temperature overnight. The reaction mixture is heated to 50 ° C bath temperature and stirred for a further 5 h. Add N-chlorosuccinimide (37 mg) and stir overnight at 50 ° C bath temperature. It is again added N-chlorosuccinimide (74 mg) and stirred at 80 ° C for 6 h. Subsequently, N-chlorosuccinimide (74 mg) is added and stirred at 80 ° C overnight. The reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution. The organic phase is dried, filtered and evaporated from the solvent under reduced pressure. The residue is purified by means of pHPLC (gradient: acetonitrile / water). This gives methyl 2-chloro-5- {4- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -LH-l, 2,3-triazole-l -yl} thiophene-3-carboxylate (159 mg) as a colorless solid.
HPLC-MSa): logP = 4.67, Masse (m/z) = 510 [(M+H)]+. HPLC-MS a) : log P = 4.67, mass (m / z) = 510 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.52 (s, 1H), 8.05 (s, 1H), 3.99 (s, 3H), 3.88 (s, 3H) 'H-NMR (400 MHz, de-DMSO): 9.52 (s, 1H), 8.05 (s, 1H), 3.99 (s, 3H), 3.88 (s, 3H)
Schritt 5: Herstellung von 2-Chlor-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5- yl] - 1H- 1 ,2,3 -triazol- 1 -yl} thiophen-3 -carbonsäure Step 5: Preparation of 2-chloro-5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazole 1 -yl} thiophene-3-carboxylic acid
Methyl-2-chlor-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3- triazol-l-yl}thiophen-3-carboxylat (144 mg) wird in Tetrahydrofuran vorgelegt, Lithiumhydroxid (0.57 mL, IM) wird zugetropft und es wird 1.5 h bei 60 °C gerührt. Das Reaktionsgemisch wird mit Ethylacetat verdünnt und mit HCl-Lösung (IM) und wässriger, gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird, getrocknet filtriert und unter vermindertem Druck vom Lösungsmittel befreit. Man erhält 2-Chlor-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH- pyrazol-5-yl]-lH-l,2,3-triazol-l-yl}thiophen-3-carbonsäure (162 mg) als gelben Feststoff. Methyl 2-chloro-5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-1-yl } thiophene-3-carboxylate (144 mg) is initially charged in tetrahydrofuran, lithium hydroxide (0.57 mL, IM) is added dropwise and it is stirred at 60 ° C for 1.5 h. The reaction mixture is diluted with ethyl acetate and washed with HCl solution (I.M.) and aqueous saturated sodium chloride solution. The organic phase is filtered, dried and freed from the solvent under reduced pressure. There are obtained 2-chloro-5- {4- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-1-yl } thiophene-3-carboxylic acid (162 mg) as a yellow solid.
HPLC-MSa): logP = 3.80, Masse (m/z) = 496 [(M+H)]+. HPLC-MS a) : logP = 3.80, mass (m / z) = 496 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 13.70 (s, 1H), 9.50 (s, 1H), 8.01 (s, 1H), 3.99 (s, 3H) Schritt 6: Herstellung von 2-Chlor-N-cyclopropyl-5- {4-[l-methyl-3-(pentafluorethyl)-4-(trifluormethyl)- lH-pyrazol-5-yll-lH-l,2,3-triazol-l-yl}thiophen-3-carboxamid (Ic-4) - -'H-NMR (400 MHz, de-DMSO): 13.70 (s, 1H), 9.50 (s, 1H), 8.01 (s, 1H), 3.99 (s, 3H) Step 6: Preparation of 2-Chloro-N -cyclopropyl-5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazol-1-yl} thiophene-3 carboxamide (Ic-4) - -
2- Chlor-5- {4-[l -methyl-3-(pentafluorethyl)-4-(tri^ 2-Chloro-5- {4- [l -methyl-3- (pentafluoroethyl) -4- (tri ^
yl}thiophen-3-carbonsäure (81 mg), 4-Dimethylaminopyridin (60 mg) und l -(3-Dimethylaminopropyl)-yl} thiophene-3-carboxylic acid (81 mg), 4-dimethylaminopyridine (60 mg) and 1- (3-dimethylaminopropyl) -
3- ethylcarbodiimidhydrochlorid (94 mg) werden in Dichlormethan (5 mL) und N,N- Dimethylformamid (0.5 mL) vorgelegt und 15 Minuten bei Raumtemperatur gerührt. Anschließend wird Cyclopropylamin (28 μΐ.) zugegeben und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemsich wird mit Dichlormethan verdünnt und mit HCl-Lösung (IM) gewaschen. Die organische Phase wird getrocknet und unter vermindertem Druck vom Lösungsmittel entfernt. Der Rückstand wird mittels pHPLC (Gradient: Acetonitril/Wasser) gereinigt und man erhält 2-Chlor-N-cyclopropyl-5- {4-[l -methyl-3- (pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-yl]-lH-l,2,3-triazol-l-yl}thiophen-3-carboxamid (Ic- 4) (49 mg) als farblosen Feststoff. 3-Ethylcarbodiimide hydrochloride (94 mg) are introduced into dichloromethane (5 mL) and N, N-dimethylformamide (0.5 mL) and stirred for 15 minutes at room temperature. Then cyclopropylamine (28 μΐ.) Was added and stirred overnight at room temperature. The reaction mixture is diluted with dichloromethane and washed with HCl solution (I.M.). The organic phase is dried and removed from the solvent under reduced pressure. The residue is purified by means of pHPLC (gradient: acetonitrile / water) and 2-chloro-N-cyclopropyl-5- {4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole] is obtained. 5-yl] -1H-l, 2,3-triazol-1-yl} thiophene-3-carboxamide (lc-4) (49mg) as a colorless solid.
HPLC-MSa): logP = 4.02, Masse (m/z) = 535 [(M+H)]+. HPLC-MS a) : logP = 4.02, mass (m / z) = 535 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.34 (s, 1H), 8.51 (d, 1H), 7.83 (s, 1H), 3.98 (s, 3H), 'H-NMR (400 MHz, de-DMSO): 9.34 (s, 1H), 8.51 (d, 1H), 7.83 (s, 1H), 3.98 (s, 3H),
2.85-2.81 (m, 1H), 0.75-0.70 (m, 2H), 0.59-0.50 (m, 2H) 2.85-2.81 (m, 1H), 0.75-0.70 (m, 2H), 0.59-0.50 (m, 2H)
Darstellung von 5-Chlor-N-cyclopropyl-2-[2,-methyl-5,-(pentafluorethyl)-4,-(trifluormethyl)-2,H-[L3,- bipyrazoll-4-yll-L3-thiazol-4-carboxamid (Ia-7) Preparation of 5-chloro-N-cyclopropyl-2- [2-methyl-5 - (pentafluoroethyl) -4 - (trifluoromethyl) -2 H- [L3 - bipyrazoll-4-yll-L3-thiazole 4-carboxamide (Ia-7)
Figure imgf000084_0001
Figure imgf000084_0001
Schritt 1 : Herstellung von Ethyl-5-chlor-2-Γ2,-methyl-5,-(pentafluorethyl)-4,-(trifluormethyl)-2,H-ΓL3,- bipyrazoll-4-yll-L3-thiazol-4-carboxylat Step 1: Preparation of ethyl 5-chloro-2-Γ 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H-ΓL3 , - bipyrazol-4-yl-L3-thiazole-4 carboxylate
Ethyl-2-brom-5-chlor-l,3-thiazol-4-carboxylat (100 mg), [2'-Methyl-5'-(pentafluorethyl)-4'- (trifluormethyl)-2'H-[l,3'-bipyrazol]-4-yl]boronsäure (182 mg), Cäsiumcarbonat (301 mg) und 1,1'- Bis(diphenylphosphino)ferrocen-palladium(II)dichlorid- Methylenchlorid-Addukt (30.2 mg) werden unter Argon in ein Reaktionsvail gegeben und mit NN-Dimethylformamid (5 mL) und Wasser (67 μΕ) versetzt. Anschließend wird das Reaktionsvail verschlossen und über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird über Kieselgel filtriert und mit Ethylacetat nachgespült. Das Filtrat - - wird mit Ethylacetat verdünnt und mit Wasser und wässriger, gesättigter Natriumchloridlösung gewaschen. Die organische Phase wird getrocknet, filtriert und unter vermindertem Druck vom Lösungsmittel befreit. Der Rückstand wird mittels Flash-Chromatographie (Gradient: c-Hexan/Ethylacetat) gereinigt. Man erhält Ethyl-5-chlor-2-[2'-methyl-5'-(pentafluorethyl)-4'- (trifluormethyl)-2'H-[l,3'-bipyrazol]-4-yl]-l,3-thiazol-4-carboxylat (80 mg) als farblosen Feststoff. Ethyl 2-bromo-5-chloro-1,3-thiazole-4-carboxylate (100 mg), [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [l , 3'-bipyrazol] -4-yl] boronic acid (182 mg), cesium carbonate (301 mg) and 1,1'-bis (diphenylphosphino) ferrocene palladium (II) dichloride-methylene chloride adduct (30.2 mg) under argon into a reaction vail and added with N, N-dimethylformamide (5 mL) and water (67 μΕ). The reaction vail is then sealed and stirred overnight at room temperature. The reaction mixture is filtered through silica gel and rinsed with ethyl acetate. The filtrate is diluted with ethyl acetate and washed with water and aqueous saturated sodium chloride solution. The organic phase is dried, filtered and freed from the solvent under reduced pressure. The residue is purified by flash chromatography (gradient: c-hexane / ethyl acetate). Ethyl 5-chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] -l, 3-thiazole-4-carboxylate (80 mg) as a colorless solid.
HPLC-MSa): logP = 4.72, Masse (m/z) = 524 [(M+H)]+. HPLC-MS a) : logP = 4.72, mass (m / z) = 524 [(M + H)] +.
'H-NMR (400 MHz, de-DMSO): 9.03 (s, 1H), 8.56 (s, 1H), 4.36 (q, 2H), 3.82 (s, 3H), 1.33 (t, 3H) 'H-NMR (400 MHz, de-DMSO): 9.03 (s, 1H), 8.56 (s, 1H), 4.36 (q, 2H), 3.82 (s, 3H), 1.33 (t, 3H)
Schritt 2: Herstellung von 5-Chlor-2-Γ2,-methyl-5,-(pentafΐuorethyl)-4,-(trifluormethyl)-2,H-ΓL3,- bipyrazoll-4-yll-L3-thiazol-4-carbonsäure Ethyl-5-chlor-2-[2'-methyl-5'-(pentafluorethyl)-4'-(trifluormethyl)-2'H-[l,3'-bipyrazol]-4-yl]-l,3-thiStep 2: Preparation of 5-chloro-2-Γ2, methyl-5 - (pentafΐuorethyl) -4 - (trifluoromethyl) -2, H-ΓL3, - bipyrazoll-4-yll-L3-thiazole-4-carboxylic acid ethyl 5-chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [l, 3'-bipyrazol] -4-yl] -l, 3- thi
4- carboxylat (310 mg) wird in Tetrahydrofuran vorgelegt, Lithiumhydroxid (1.78 mL, IM in Wasser) wird zugetropft und 3 h bei Raumtemperatur gerührt. Anschließend wird weiter über Nacht bei Raumtemperatur gerührt. Das Reaktionsgemisch wird mit Ethylacetat verdünnt und mit HCl-Lösung (IM) gewaschen. Die organische Phase wird mit wässriger, gesättigter Natriumchloridlösung gewaschen, getrocknet, filtriert und unter vermindertem Druck vom Lösungsmittel befreit. Man erhält 5- Chlor-2-[2'-methyl-5'-(pentafluorethyl)-4'-(trifluormethyl)-2'H-[l,3'-bipyrazol]-4-yl]-l,3-thiaz^ carbonsäure (265 mg) als bräunlich gelbes Feststoff. 4-carboxylate (310 mg) is initially charged in tetrahydrofuran, lithium hydroxide (1.78 ml, 1M in water) is added dropwise and the mixture is stirred at room temperature for 3 h. The mixture is then further stirred overnight at room temperature. The reaction mixture is diluted with ethyl acetate and washed with HCl solution (IM). The organic phase is washed with aqueous, saturated sodium chloride solution, dried, filtered and freed from the solvent under reduced pressure. 5-Chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] -l, 3 thiazicarboxylic acid (265 mg) as a brownish yellow solid.
HPLC-MSa): logP = 3.46, Masse (m/z) = 496 [(M+H)]+. HPLC-MS a) : logP = 3.46, mass (m / z) = 496 [(M + H)] +.
Schritt 3: Herstellung von 5-Chlor-N-cyclopropyl-2-[2,-methyl-5,-(pentafluorethyl)-4'-(trifluormethyl)- 2'H-[L3'-bipyrazoll-4-yll-L3-thiazol-4-carboxamid Step 3: Preparation of 5-chloro-N-cyclopropyl-2- [2 , -methyl-5 , - (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H- [L3'-bipyrazol-4-yl-L3 thiazole-4-carboxamide
5- Chlor-2-[2'-methyl-5'-(pentafluorethyl)-4'-(trifluormethyl)-2'H-[l,3'-bipyrazol]-4-yl]-l,3-thiazol-4 carbonsäure (132 mg) wird in Dichlormethan (5 mL) vorgelegt, HBTU (172 mg) und NN- Diisopropylethylamin (139 mL) werden zugegeben und es wird 30 Minuten bei Raumtemperatur gerührt. Anschließend wird Cyclopropylamin (20 μΕ) zugegeben und über Nacht bei Raumtempartur gerührt. Das Reaktionsgemisch wird mit Kieselgur versetzt und unter vermindertem Druck vom Lösungsmittel befreit, um über Flash-Chromatographie (Gradient: c-Hexan/Ethylacetat) gereinigt zu werden. Man erhält 5-Chlor-N-cyclopropyl-2-[2'-methyl-5'-(pentafluorethyl)-4'-(trifluormethyl)-2'H- [l,3'-bipyrazol]-4-yl]-l,3-thiazol-4-carboxamid (73 mg) als farblosen Feststoff. 5-Chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] -1,3-thiazole Carboxylic acid (132 mg) is initially charged in dichloromethane (5 mL), HBTU (172 mg) and N, N-diisopropylethylamine (139 mL) are added and the mixture is stirred at room temperature for 30 minutes. Then cyclopropylamine (20 μΕ) is added and stirred overnight at room temparture. The reaction mixture is treated with diatomaceous earth and freed from the solvent under reduced pressure to be purified by flash chromatography (gradient: c-hexane / ethyl acetate). 5-Chloro-N-cyclopropyl-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] - l, 3-thiazole-4-carboxamide (73 mg) as a colorless solid.
HPLC-MS' l): logP = 4.19, Masse (m/z) = 535 [(M+H)]+. HPLC-MS ' l) : logP = 4.19, mass (m / z) = 535 [(M + H)] +.
H-NMR (400 MHz, de-DMSO): 8.58 (s, 1H), 8.58 (s, 1H), 8.44 (d, 1H), 3.81 (s, 3H), H-NMR (400 MHz, de-DMSO): 8.58 (s, 1H), 8.58 (s, 1H), 8.44 (d, 1H), 3.81 (s, 3H),
2.86-2.81 (m, 1H), 0.75-0.70 (m, 2H), 0.65-0.58 (m, 2H) - 5 - a) Anmerkung zur Bestimmung der logP- Werte und Massendetektion: Die Bestimmung der angegebenen logP- Werte erfolgte gemäß EEC-Direktive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C18).Agilent 1100 LC-System; 50*4,6 Zorbax Eclipse Plus C18 1,8 microm; Eluent A: Acetonitril (0,1 % Ameisensäure); Eluent B: Wasser (0,09 % Ameisensäure); linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril in 4,25 min, dann 95% Acetonitril für weitere 1,25 min; Ofentemperatur 55 °C; Fluß:2,0 mL/min. Die Massendetektion erfolgt über ein Agilend MSD-System. 2.86-2.81 (m, 1H), 0.75-0.70 (m, 2H), 0.65-0.58 (m, 2H) - 5 - a) Note on the determination of the logP values and mass detection: The determination of the indicated logP values was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C18). Agilent 1100 LC system; 50 * 4.6 Zorbax Eclipse Plus C18 1.8 microm; Eluent A: acetonitrile (0.1% formic acid); Eluent B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min; Oven temperature 55 ° C; Flow: 2.0 mL / min. Mass detection takes place via an Agilend MSD system.
Tabelle 1 Table 1
Figure imgf000086_0001
Figure imgf000086_0002
Figure imgf000086_0001
Figure imgf000086_0002
Tabelle 2 - - Table 2 - -
Figure imgf000087_0001
Figure imgf000087_0001
(Ib)  (Ib)
Bsp.-Nr. R1 R2 R5 R6 Ai Hai QExpl R 1 R 2 R 5 R 6 Ai Hai Q
Ib-1 Cyclopropyl H CF3 CF2CF3 CH I 0Ib-1 Cyclopropyl H CF 3 CF 2 CF 3 CH I 0
Ib-2 1 -Cyano-Cyclopropyl H CF3 CF2CF3 CH I 0Ib-2 1 -Cyano-cyclopropyl H CF 3 CF 2 CF 3 CH I 0
Ib-3 1 -Cyano-Cyclopropyl H CF3 CF2CF3 CH Cl 0Ib-3 1 -Cyano-cyclopropyl H CF 3 CF 2 CF 3 CH Cl 0
Ib-4 Cyclopropyl H CF3 CF2CF3 CH Cl 0Ib-4 Cyclopropyl H CF 3 CF 2 CF 3 CH Cl 0
Ib-5 1 -Cyano-Cyclopropyl H CF3 CF2CF3 CH Br 0Ib-5 1 -Cyano-cyclopropyl H CF 3 CF 2 CF 3 CH Br 0
Ib-6 Cyclopropyl H CF3 CF2CF3 CH Br 0 Ib-6 Cyclopropyl H CF 3 CF 2 CF 3 CH Br 0
Figure imgf000087_0002
Figure imgf000087_0003
- 7 -
Figure imgf000087_0002
Figure imgf000087_0003
- 7 -
Figure imgf000088_0001
Figure imgf000088_0001
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. Die Peakliste eines Beispieles hat daher die Form: δι (Intensität^; δ2 (Intensität); ; δ; (Intensität^; ; δη (Intensitätn) 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. The peak list of an example therefore has the form: δι (intensity ^; δ 2 (intensity);; δ; (intensity ^;; δ η (intensity n )
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von IH-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. Die Listen der IH-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. To calibrate the chemical shift of IH-NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of IH 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, they can, like classical 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 1H-NMR-Peaks die gewöhnlichen Lösungsmitte lpeaks, 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, in our lists of 1H NMR peaks, the usual solvent peaks, for example peaks of DMSO in DMSO-D6 and the peak of water, are usually shown in the Average high intensity.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90 %). The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints."
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expectancy 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 1H NMR interpretation.
Weitere Details zu 1H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on 1H NMR peaks can be found in Research Disclosure Database Number 564025.
Bsp.-Nr. Expl
Ia-1 Ia-1 : Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ= 8.6370 (6.1); 8.3382 (6.6); 8.3144 (0.4); 8.3014 (1.9); 8.2913 (1.8); 7.3695 (8.0); 3.8010 (16.0); 3.3193 (86.6); 2.8286 (0.7); 2.8186 (1.0); 2.8100 (1.4); 2.8003 (1.4); 2.7913 (0.9); 2.7818 (0.6); 2.6706 (0.8); 2.6661 (0.7); 2.5061 (112.4); 2.5017 (146.0); 2.4972 (105.8); 2.3329 (0.7); 2.3282 (0.9); 2.3239 (0.7); 0.7292 (0.8); 0.7165 (2.4); 0.7113 (3.4); 0.6993 (3.1); 0.6934 (2.7); 0.6822 (1.1); 0.5700 (1.1); 0.5596 (3.4); 0.5530 (3.2); 0.5436 (2.8); 0.5313 (0.9); 0.1460 (0.4); 0.0079 (3.2); -0.0002 (80.2); -0.0084 (3.6); -0.1495 (0.4) Ia-1 Ia-1: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO): δ = 8.6370 (6.1); 8.3382 (6.6); 8.3144 (0.4); 8.3014 (1.9); 8.2913 (1.8); 7.3695 (8.0); 3.8010 (16.0); 3.3193 (86.6); 2.8286 (0.7); 2.8186 (1.0); 2.8100 (1.4); 2.8003 (1.4); 2.7913 (0.9); 2.7818 (0.6); 2.6706 (0.8); 2.6661 (0.7); 2.5061 (112.4); 2.5017 (146.0); 2.4972 (105.8); 2.3329 (0.7); 2.3282 (0.9); 2.3239 (0.7); 0.7292 (0.8); 0.7165 (2.4); 0.7113 (3.4); 0.6993 (3.1); 0.6934 (2.7); 0.6822 (1.1); 0.5700 (1.1); 0.5596 (3.4); 0.5530 (3.2); 0.5436 (2.8); 0.5313 (0.9); 0.1460 (0.4); 0.0079 (3.2); -0.0002 (80.2); -0.0084 (3.6); -0.1495 (0.4)
Ia-2 Ia-2: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ= 9.2047 (4.0); 8.6515 (6.1); 8.3422 (6.6); 7.4335 (7.5); 3.8041 (16.0); 3.3218 (192.2); 2.6708 (0.9); 2.5062 (118.4); 2.5018 (154.1); 2.4975 (115.0); 2.3289 (0.9); 1.6036 (1.5); 1.5892 (4.0); 1.5825 (4.3); 1.5695 (1.8); 1.2758 (1.8); 1.2622 (4.0); 1.2554 (4.3); 1.2411 (1.6); 0.1462 (0.4); 0.0077 (3.8); -0.0002 - -Ia-2 Ia-2: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO): δ = 9.2047 (4.0); 8.6515 (6.1); 8.3422 (6.6); 7.4335 (7.5); 3.8041 (16.0); 3.3218 (192.2); 2.6708 (0.9); 2.5062 (118.4); 2.5018 (154.1); 2.4975 (115.0); 2.3289 (0.9); 1.6036 (1.5); 1.5892 (4.0); 1.5825 (4.3); 1.5695 (1.8); 1.2758 (1.8); 1.2622 (4.0); 1.2554 (4.3); 1.2411 (1.6); 0.1462 (0.4); 0.0077 (3.8); -0.0002 - -
(80.1); -0.1497 (0.4) (80.1); -0.1497 (0.4)
Ia-3 Ia-3: 'H-NMR^O.O MHz, de-DMSO): δ= 9.2683 (3.5); 8.6821 (6.3); 8.3748 (6.7); 8.3126 (7.8); 7.5587 (8.4); 3.8070 (16.0); 3.3203 (50.9); 3.2955 (2.9); 2.6709 (0.5); 2.6663 (0.4); 2.5105 (30.2); 2.5063 (58.1); 2.5018 (76.3); 2.4973 (57.5); 2.3329 (0.4); 2.3285 (0.5); 2.3241 (0.4); 1.9883 (0.7); 1.6010 (1.6); 1.5868 (3.9); 1.5799 (4.1); 1.5668 (1.8); 1.2815 (1.8); 1.2679 (4.0); 1.2611 (4.2); 1.2467 (1.6); 1.2366 (0.4); 1.1753 (0.5); 1.1678 (0.3); 0.0074 (1.9); -0.0003 (36.9); -0.0084 (1.5) Ia-3 Ia-3: 'H-NMR ^ O.O MHz, de-DMSO): δ = 9.2683 (3.5); 8.6821 (6.3); 8.3748 (6.7); 8.3126 (7.8); 7.5587 (8.4); 3.8070 (16.0); 3,3203 (50.9); 3.2955 (2.9); 2.6709 (0.5); 2.6663 (0.4); 2.5105 (30.2); 2.5063 (58.1); 2.5018 (76.3); 2.4973 (57.5); 2.3329 (0.4); 2.3285 (0.5); 2.3241 (0.4); 1.9883 (0.7); 1.6010 (1.6); 1.5868 (3.9); 1.5799 (4.1); 1.5668 (1.8); 1.2815 (1.8); 1.2679 (4.0); 1.2611 (4.2); 1.2467 (1.6); 1.2366 (0.4); 1.1753 (0.5); 1.1678 (0.3); 0.0074 (1.9); -0.0003 (36.9); -0.0084 (1.5)
Ia-4 Ia-4: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ= 8.6661 (3.7); 8.3703 (4.6); 8.3133 (16.0); 7.4937 (5.0); 3.8038 (9.4); 3.3221 (19.1); 3.2962 (4.1); 2.8241 (0.5); 2.8156 (0.7); 2.8057 (0.8); 2.7967 (0.5); 2.7875 (0.4); 2.5107 (15.1); 2.5065 (30.1); 2.5020 (40.0); 2.4975 (30.2); 2.4934 (15.6); 0.7302 (0.5); 0.7174 (1.4); 0.7123 (2.0); 0.7001 (1.8); 0.6942 (1.5); 0.6828 (0.6); 0.5642 (0.6); 0.5536 (1.9); 0.5471 (1.8); 0.5378 (1.6); 0.5255 (0.5); 0.0079 (0.8); -0.0002 (20.8); -0.0084 (0.9) Ia-4 Ia-4: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO): δ = 8.6661 (3.7); 8.3703 (4.6); 8.3133 (16.0); 7.4937 (5.0); 3.8038 (9.4); 3.3221 (19.1); 3.2962 (4.1); 2.8241 (0.5); 2.8156 (0.7); 2.8057 (0.8); 2.7967 (0.5); 2.7875 (0.4); 2.5107 (15.1); 2.5065 (30.1); 2.5020 (40.0); 2.4975 (30.2); 2.4934 (15.6); 0.7302 (0.5); 0.7174 (1.4); 0.7123 (2.0); 0.7001 (1.8); 0.6942 (1.5); 0.6828 (0.6); 0.5642 (0.6); 0.5536 (1.9); 0.5471 (1.8); 0.5378 (1.6); 0.5255 (0.5); 0.0079 (0.8); -0.0002 (20.8); -0.0084 (0.9)
Ia-5 Ia-5: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.2695 (4.2); 8.6807 (6.2); 8.3728 (6.8); 7.5300 (8.0); 3.8066 (16.0); 3.3184 (188.0); 2.6704 (1.9); 2.5886 (0.3); 2.5757 (0.4); 2.5058 (244.1); 2.5014 (309.9); 2.4970 (224.7); 2.3282 (1.8); 2.3238 (1.4); 2.0736 (1.1); 1.6045 (1.5); 1.5897 (3.8); 1.5831 (4.1); 1.5701 (1.8); 1.2756 (1.8); 1.2623 (4.0); 1.2554 (4.2); 1.2410 (1.5); -0.0002 (9.6) Ia-5 Ia-5: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.2695 (4.2); 8.6807 (6.2); 8.3728 (6.8); 7.5300 (8.0); 3.8066 (16.0); 3.3184 (188.0); 2.6704 (1.9); 2.5886 (0.3); 2.5757 (0.4); 2.5058 (244.1); 2.5014 (309.9); 2.4970 (224.7); 2.3282 (1.8); 2.3238 (1.4); 2.0736 (1.1); 1.6045 (1.5); 1.5897 (3.8); 1.5831 (4.1); 1.5701 (1.8); 1.2756 (1.8); 1.2623 (4.0); 1.2554 (4.2); 1.2410 (1.5); -0.0002 (9.6)
Ia-6 Ia-6: 1H-NMR(400.0 MHz, de-DMSO): δ= 8.6663 (6.2); 8.3697 (8.1); 8.3615 (2.0); 7.4621 (8.6); 3.8040 (16.0); 3.3191 (55.1); 2.8324 (0.6); 2.8228 (0.9); 2.8139 (1.4); 2.8040 (1.4); 2.7956 (0.9); 2.7858 (0.7); 2.6710 (0.6); 2.6664 (0.4); 2.5238 (2.0); 2.5103 (38.7); 2.5061 (75.3); 2.5017 (96.8); 2.4972 (69.2); 2.4931 (33.3); 2.3324 (0.4); 2.3282 (0.6); 2.3240 (0.4); 0.7300 (0.9); 0.7174 (2.4); 0.7121 (3.3); 0.6999 (3.2); 0.6940 (2.6); 0.6827 (1.1); 0.5632 (1.1); 0.5526 (3.4); 0.5463 (3.1); 0.5427 (2.9); 0.5368 (2.8); 0.5247 (0.8); -0.0002 (7.6) Ia-6 Ia-6: 1 H NMR (400.0 MHz, de-DMSO): δ = 8.6663 (6.2); 8.3697 (8.1); 8.3615 (2.0); 7.4621 (8.6); 3.8040 (16.0); 3.3191 (55.1); 2.8324 (0.6); 2.8228 (0.9); 2.8139 (1.4); 2.8040 (1.4); 2.7956 (0.9); 2.7858 (0.7); 2.6710 (0.6); 2.6664 (0.4); 2.5238 (2.0); 2.5103 (38.7); 2.5061 (75.3); 2.5017 (96.8); 2.4972 (69.2); 2.4931 (33.3); 2.3324 (0.4); 2.3282 (0.6); 2.3240 (0.4); 0.7300 (0.9); 0.7174 (2.4); 0.7121 (3.3); 0.6999 (3.2); 0.6940 (2.6); 0.6827 (1.1); 0.5632 (1.1); 0.5526 (3.4); 0.5463 (3.1); 0.5427 (2.9); 0.5368 (2.8); 0.5247 (0.8); -0.0002 (7.6)
Ia-7 Ia-7: 1H-NMR(400.0 MHz, de-DMSO): δ= 8.9794 (7.0); 8.5804 (7.4); 8.4463 (1.7); 8.4357 (1.7); 8.3146 (0.4); 3.8131 (16.0); 3.3176 (31.5); 2.8588 (0.6); 2.8491 (0.8); 2.8404 (1.4); 2.8302 (1.3); 2.8222 (0.8); 2.8121 (0.7); 2.6751 (0.7); 2.6705 (1.0); 2.6661 (0.7); 2.5239 (2.5); 2.5103 (55.9); 2.5060 (118.8); 2.5015 (167.1); 2.4970 (126.0); 2.4928 (61.3); 2.3329 (0.7); 2.3283 (1.0); 2.3240 (0.7); 1.3981 (1.2); 1.2353 (1.3); 0.7497 (0.8); 0.7358 (1.9); 0.7314 (3.0); 0.7195 (2.6); 0.7129 (2.4); 0.7022 (1.1); 0.6649 (0.4); 0.6376 (1.2); 0.6272 (3.4); 0.6190 (2.9); 0.6121 (2.1); 0.5987 (0.8); 0.0079 (1.6); -0.0003 (50.8); -0.0084 (2.0) Ia-7 Ia-7: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.9794 (7.0); 8.5804 (7.4); 8.4463 (1.7); 8.4357 (1.7); 8.3146 (0.4); 3.8131 (16.0); 3.3176 (31.5); 2.8588 (0.6); 2.8491 (0.8); 2.8404 (1.4); 2.8302 (1.3); 2.8222 (0.8); 2.8121 (0.7); 2.6751 (0.7); 2.6705 (1.0); 2.6661 (0.7); 2.5239 (2.5); 2.5103 (55.9); 2.5060 (118.8); 2.5015 (167.1); 2.4970 (126.0); 2.4928 (61.3); 2.3329 (0.7); 2.3283 (1.0); 2.3240 (0.7); 1.3981 (1.2); 1.2353 (1.3); 0.7497 (0.8); 0.7358 (1.9); 0.7314 (3.0); 0.7195 (2.6); 0.7129 (2.4); 0.7022 (1.1); 0.6649 (0.4); 0.6376 (1.2); 0.6272 (3.4); 0.6190 (2.9); 0.6121 (2.1); 0.5987 (0.8); 0.0079 (1.6); -0.0003 (50.8); -0.0084 (2.0)
Ia-8 Ia-8: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.4152 (4.1); 8.9748 (6.9); 8.5701 (7.3); 3.8167 (16.0); 3.3193 (11.1); 2.6713 (0.4); 2.6668 (0.3); 2.5245 (1.1); 2.5067 (51.8); 2.5022 (72.2); 2.4979 (54.7); 2.3289 (0.4); 2.0744 (1.7); 1.6085 (1.4); 1.5940 (3.6); 1.5870 (3.9); 1.5739 (1.7); 1.3437 (1.8); 1.3302 (3.6); 1.3233 (3.9); 1.3087 (1.4); 0.0080 - -Ia-8 Ia-8: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.4152 (4.1); 8.9748 (6.9); 8.5701 (7.3); 3.8167 (16.0); 3.3193 (11.1); 2.6713 (0.4); 2.6668 (0.3); 2.5245 (1.1); 2.5067 (51.8); 2.5022 (72.2); 2.4979 (54.7); 2.3289 (0.4); 2.0744 (1.7); 1.6085 (1.4); 1.5940 (3.6); 1.5870 (3.9); 1.5739 (1.7); 1.3437 (1.8); 1.3302 (3.6); 1.3233 (3.9); 1.3087 (1.4); 0.0080 - -
(0.5); -0.0002 (14.0); -0.0084 (0.5) (0.5); -0.0002 (14.0); -0.0084 (0.5)
Ib-1 Ib-1 : 'H-NMR(400.0 MHz, de-DMSO): δ= 9.2802 (4.1); 8.4392 (1.1); 8.4291 (1.1); 7.6973 (4.7); 3.9745 (10.1); 3.3198 (17.1); 2.8465 (0.4); 2.8370 (0.6); 2.8283 (0.9); 2.8184 (0.8); 2.8099 (0.6); 2.8002 (0.4); 2.6752 (0.3); 2.6712 (0.4); 2.5064 (59.8); 2.5021 (77.6); 2.4980 (56.8); 2.3287 (0.4); 2.0744 (16.0); 0.7504 (0.5); 0.7377 (1.6); 0.7325 (2.1); 0.7203 (2.0); 0.7146 (1.7); 0.7034 (0.7); 0.5806 (0.7); 0.5699 (2.0); 0.5636 (2.0); 0.5543 (1.8); 0.5422 (0.5); 0.0077 (0.4); -0.0002 (9.6) Ib-1 Ib-1: 'H-NMR (400.0 MHz, de-DMSO): δ = 9.2802 (4.1); 8.4392 (1.1); 8.4291 (1.1); 7.6973 (4.7); 3.9745 (10.1); 3.3198 (17.1); 2.8465 (0.4); 2.8370 (0.6); 2.8283 (0.9); 2.8184 (0.8); 2.8099 (0.6); 2.8002 (0.4); 2.6752 (0.3); 2.6712 (0.4); 2.5064 (59.8); 2.5021 (77.6); 2.4980 (56.8); 2.3287 (0.4); 2.0744 (16.0); 0.7504 (0.5); 0.7377 (1.6); 0.7325 (2.1); 0.7203 (2.0); 0.7146 (1.7); 0.7034 (0.7); 0.5806 (0.7); 0.5699 (2.0); 0.5636 (2.0); 0.5543 (1.8); 0.5422 (0.5); 0.0077 (0.4); -0.0002 (9.6)
Ib-2 Ib-2: 'H-NMR^OO.O MHz, de-DMSO): δ= 9.3455 (3.9); 9.2719 (6.5); 7.7598 (7.1); 3.9773 (16.0); 3.3212 (62.0); 2.6712 (0.8); 2.5060 (111.5); 2.5020 (143.8); 2.4980 (110.6); 2.3287 (0.8); 2.0745 (0.8); 1.6267 (1.5); 1.6124 (4.0); 1.6058 (4.2); 1.5926 (1.7); 1.2877 (1.7); 1.2743 (4.0); 1.2677 (4.2); 1.2532 (1.4); -0.0002 (14.9) Ib-2 Ib-2: 'H NMR ^ OO.O MHz, de-DMSO): δ = 9.3455 (3.9); 9.2719 (6.5); 7.7598 (7.1); 3.9773 (16.0); 3.3212 (62.0); 2.6712 (0.8); 2.5060 (111.5); 2.5020 (143.8); 2.4980 (110.6); 2.3287 (0.8); 2.0745 (0.8); 1.6267 (1.5); 1.6124 (4.0); 1.6058 (4.2); 1.5926 (1.7); 1.2877 (1.7); 1.2743 (4.0); 1.2677 (4.2); 1.2532 (1.4); -0.0002 (14.9)
Ib-3 Ib-3: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.4184 (3.8); 9.3317 (6.5); 7.9002 (7.1); 3.9809 (16.0); 3.3207 (45.7); 2.6710 (0.8); 2.5057 (107.4); 2.5018 (136.3); 2.4981 (102.8); 2.3283 (0.8); 2.0743 (0.4); 1.6239 (1.4); 1.6098 (3.9); 1.6028 (4.1); 1.5897 (1.7); 1.2962 (1.7); 1.2828 (3.9); 1.2760 (4.1); 1.2617 (1.4); -0.0004 (16.2) Ib-3 Ib-3: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.4184 (3.8); 9.3317 (6.5); 7.9002 (7.1); 3.9809 (16.0); 3,3207 (45.7); 2.6710 (0.8); 2.5057 (107.4); 2.5018 (136.3); 2.4981 (102.8); 2.3283 (0.8); 2.0743 (0.4); 1.6239 (1.4); 1.6098 (3.9); 1.6028 (4.1); 1.5897 (1.7); 1.2962 (1.7); 1.2828 (3.9); 1.2760 (4.1); 1.2617 (1.4); -0.0004 (16.2)
Ib-4 Ib-4: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.3370 (5.0); 8.5253 (1.3); 8.5157 (1.4); 7.8337 (5.8); 3.9777 (12.2); 3.3203 (69.4); 2.8530 (0.5); 2.8429 (0.7); 2.8344 (1.1); 2.8244 (1.1); 2.8154 (0.7); 2.8065 (0.5); 2.6709 (1.0); 2.5412 (0.7); 2.5059 (137.9); 2.5018 (170.5); 2.4978 (125.6); 2.3287 (1.0); 2.0740 (16.0); 0.7508 (0.6); 0.7380 (2.0); 0.7333 (2.6); 0.7209 (2.5); 0.7153 (2.1); 0.7040 (0.8); 0.5741 (0.9); 0.5634 (2.6); 0.5567 (2.6); 0.5480 (2.3); 0.5353 (0.7); -0.0002 (26.0) Ib-4 Ib-4: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.3370 (5.0); 8.5253 (1.3); 8.5157 (1.4); 7.8337 (5.8); 3.9777 (12.2); 3.3203 (69.4); 2.8530 (0.5); 2.8429 (0.7); 2.8344 (1.1); 2.8244 (1.1); 2.8154 (0.7); 2.8065 (0.5); 2.6709 (1.0); 2.5412 (0.7); 2.5059 (137.9); 2.5018 (170.5); 2.4978 (125.6); 2.3287 (1.0); 2.0740 (16.0); 0.7508 (0.6); 0.7380 (2.0); 0.7333 (2.6); 0.7209 (2.5); 0.7153 (2.1); 0.7040 (0.8); 0.5741 (0.9); 0.5634 (2.6); 0.5567 (2.6); 0.5480 (2.3); 0.5353 (0.7); -0.0002 (26.0)
Ib-5 Ib-5: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.4165 (2.9); 9.3157 (5.2); 7.8700 (5.8); 3.9804 (12.2); 3.3196 (27.6); 2.6708 (0.7); 2.5061 (89.8); 2.5019 (115.3); 2.4976 (83.5); 2.3287 (0.7); 2.0743 (16.0); 1.6274 (1.1); 1.6132 (2.9); 1.6063 (3.1); 1.5931 (1.3); 1.2897 (1.3); 1.2763 (2.9); 1.2694 (3.1); 1.2551 (1.1); 0.0078 (0.8); -0.0001 (20.6) Ib-5 Ib-5: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.4165 (2.9); 9.3157 (5.2); 7.8700 (5.8); 3.9804 (12.2); 3.3196 (27.6); 2.6708 (0.7); 2.5061 (89.8); 2.5019 (115.3); 2.4976 (83.5); 2.3287 (0.7); 2.0743 (16.0); 1.6274 (1.1); 1.6132 (2.9); 1.6063 (3.1); 1.5931 (1.3); 1.2897 (1.3); 1.2763 (2.9); 1.2694 (3.1); 1.2551 (1.1); 0.0078 (0.8); -0.0001 (20.6)
Ib-6 Ib-6: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.3235 (5.2); 8.5162 (1.4); 8.5059 (1.4); 7.8027 (5.6); 3.9774 (12.8); 3.3212 (132.7); 2.8502 (0.5); 2.8415 (0.8); 2.8325 (1.1); 2.8226 (1.1); 2.8138 (0.8); 2.8050 (0.5); 2.6712 (1.5); 2.5059 (214.3); 2.5021 (260.4); 2.3288 (1.5); 2.0739 (16.0); 0.7515 (0.7); 0.7386 (2.1); 0.7337 (2.6); 0.7212 (2.6); 0.7156 (2.1); 0.7045 (0.8); 0.5743 (0.9); 0.5639 (2.7); 0.5574 (2.7); 0.5482 (2.3); 0.5363 (0.7); -0.0001 (40.7) Ib-6 Ib-6: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.3235 (5.2); 8.5162 (1.4); 8.5059 (1.4); 7.8027 (5.6); 3.9774 (12.8); 3.3212 (132.7); 2.8502 (0.5); 2.8415 (0.8); 2.8325 (1.1); 2.8226 (1.1); 2.8138 (0.8); 2.8050 (0.5); 2.6712 (1.5); 2.5059 (214.3); 2.5021 (260.4); 2.3288 (1.5); 2.0739 (16.0); 0.7515 (0.7); 0.7386 (2.1); 0.7337 (2.6); 0.7212 (2.6); 0.7156 (2.1); 0.7045 (0.8); 0.5743 (0.9); 0.5639 (2.7); 0.5574 (2.7); 0.5482 (2.3); 0.5363 (0.7); -0.0001 (40.7)
Ic-1 Ic-1 : 1H-NMR(400.0 MHz, de-DMSO): δ= 9.0881 (8.0); 8.3894 (1.8); 8.3790 (1.8); 7.5955 (8.3); 3.8508 (16.0); 3.3232 (95.5); 3.1755 (0.4); 3.1624 (0.4); 2.8424 (0.6); 2.8329 (0.9); 2.8242 (1.4); 2.8142 (1.4); 2.8057 (0.9); 2.7959 (0.7); 2.6758 (0.3); 2.6711 (0.5); 2.6664 (0.3); 2.5244 (1.1); 2.5109 (28.3); 2.5066 (59.0); 2.5021 (78.8); 2.4976 - -Ic-1 Ic-1: 1 H NMR (400.0 MHz, de-DMSO): δ = 9.0881 (8.0); 8.3894 (1.8); 8.3790 (1.8); 7.5955 (8.3); 3.8508 (16.0); 3.3232 (95.5); 3.1755 (0.4); 3.1624 (0.4); 2.8424 (0.6); 2.8329 (0.9); 2.8242 (1.4); 2.8142 (1.4); 2.8057 (0.9); 2.7959 (0.7); 2.6758 (0.3); 2.6711 (0.5); 2.6664 (0.3); 2.5244 (1.1); 2.5109 (28.3); 2.5066 (59.0); 2.5021 (78.8); 2.4976 - -
(57.2); 2.4932 (28.2); 2.3334 (0.3); 2.3289 (0.5); 2.3241 (0.3); 0.7335 (0.8); 0.7208 (2.3); 0.7156 (3.3); 0.7035 (3.0); 0.6975 (2.6); 0.6863 (1.1); 0.5782 (1.1); 0.5677 (3.3); 0.5613 (3.0); 0.5579 (2.9); 0.5519 (2.7); 0.5397 (0.8); 0.1458 (0.3); 0.0078 (2.4); -0.0002 (72.5); -0.0084 (3.2) (57.2); 2.4932 (28.2); 2.3334 (0.3); 2.3289 (0.5); 2.3241 (0.3); 0.7335 (0.8); 0.7208 (2.3); 0.7156 (3.3); 0.7035 (3.0); 0.6975 (2.6); 0.6863 (1.1); 0.5782 (1.1); 0.5677 (3.3); 0.5613 (3.0); 0.5579 (2.9); 0.5519 (2.7); 0.5397 (0.8); 0.1458 (0.3); 0.0078 (2.4); -0.0002 (72.5); -0.0084 (3.2)
Ic-2 Ic-2: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ= 9.2822 (4.0); 9.0922 (7.8); 7.6685 (7.8); 4.1093 (0.4); 4.0962 (1.1); 4.0830 (1.1); 4.0698 (0.4); 3.8538 (16.0); 3.3191 (46.0); 3.1747 (4.6); 3.1615 (4.5); 2.6749 (0.5); 2.6704 (0.7); 2.6663 (0.6); 2.5237 (1.8); 2.5101 (46.0); 2.5059 (94.0); 2.5016 (124.7); 2.4972 (91.1); 2.3327 (0.5); 2.3280 (0.7); 2.3240 (0.6); 1.6037 (1.4); 1.5894 (3.8); 1.5824 (4.0); 1.5694 (1.7); 1.2897 (1.8); 1.2763 (3.8); 1.2694 (4.1); 1.2551 (1.5); 0.1458 (0.5); 0.0074 (3.4); -0.0003 (95.0); -0.0082 (4.5); -0.1499 (0.5) Ic-2 Ic-2: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO): δ = 9.2822 (4.0); 9.0922 (7.8); 7.6685 (7.8); 4.1093 (0.4); 4.0962 (1.1); 4.0830 (1.1); 4.0698 (0.4); 3.8538 (16.0); 3,3191 (46.0); 3.1747 (4.6); 3.1615 (4.5); 2.6749 (0.5); 2.6704 (0.7); 2.6663 (0.6); 2.5237 (1.8); 2.5101 (46.0); 2.5059 (94.0); 2.5016 (124.7); 2.4972 (91.1); 2.3327 (0.5); 2.3280 (0.7); 2.3240 (0.6); 1.6037 (1.4); 1.5894 (3.8); 1.5824 (4.0); 1.5694 (1.7); 1.2897 (1.8); 1.2763 (3.8); 1.2694 (4.1); 1.2551 (1.5); 0.1458 (0.5); 0.0074 (3.4); -0.0003 (95.0); -0.0082 (4.5); -0.1499 (0.5)
Ic-3 Ic-3: Ή-ΝΜϋ^ΟΟ.Ο MHz, de-DMSO): δ= 9.3438 (3.7); 9.1393 (7.5); 7.8053 (7.6); 3.8585 (16.0); 3.3191 (64.0); 3.1747 (0.7); 3.1616 (0.7); 2.6749 (0.6); 2.6705 (0.9); 2.6660 (0.7); 2.5236 (2.1); 2.5099 (54.5); 2.5058 (112.4); 2.5014 (150.3); 2.4970 (110.5); 2.3325 (0.6); 2.3281 (0.9); 2.3236 (0.7); 1.6030 (1.4); 1.5887 (3.7); 1.5817 (4.0); 1.5686 (1.7); 1.2947 (1.7); 1.2813 (3.7); 1.2744 (4.0); 1.2601 (1.5); 0.1458 (0.6); 0.0076 (4.1); -0.0003 (119.5); - 0.0082 (5.9); -0.1499 (0.6) Ic-3 Ic-3: Ή-ΝΜϋ ^ ΟΟ.Ο MHz, de-DMSO): δ = 9.3438 (3.7); 9.1393 (7.5); 7.8053 (7.6); 3.8585 (16.0); 3.3191 (64.0); 3.1747 (0.7); 3.1616 (0.7); 2.6749 (0.6); 2.6705 (0.9); 2.6660 (0.7); 2.5236 (2.1); 2.5099 (54.5); 2.5058 (112.4); 2.5014 (150.3); 2.4970 (110.5); 2.3325 (0.6); 2.3281 (0.9); 2.3236 (0.7); 1.6030 (1.4); 1.5887 (3.7); 1.5817 (4.0); 1.5686 (1.7); 1.2947 (1.7); 1.2813 (3.7); 1.2744 (4.0); 1.2601 (1.5); 0.1458 (0.6); 0.0076 (4.1); -0.0003 (119.5); - 0.0082 (5.9); -0.1499 (0.6)
Ic-4 Ic-4: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.4313 (0.3); 9.1330 (7.6); 8.4608 (1.6); 8.4500 (1.6); 7.7300 (7.8); 3.8548 (16.0); 3.3232 (224.8); 2.8460 (0.6); 2.8364 (0.8); 2.8277 (1.3); 2.8178 (1.3); 2.8091 (0.8); 2.7996 (0.6); 2.6752 (0.6); 2.6707 (0.9); 2.6663 (0.7); 2.5240 (2.0); 2.5104 (55.5); 2.5062 (115.7); 2.5017 (155.1); 2.4972 (113.3); 2.4930 (56.7); 2.3329 (0.7); 2.3284 (0.9); 2.3241 (0.7); 0.7346 (0.8); 0.7218 (2.3); 0.7166 (3.2); 0.7044 (3.0); 0.6986 (2.5); 0.6873 (1.1); 0.5704 (1.0); 0.5597 (3.1); 0.5532 (2.9); 0.5497 (2.7); 0.5438 (2.7); 0.5317 (0.9); 0.1459 (0.6); 0.0079 (4.0); -0.0002 (127.9); -0.0083 (6.1); -0.1497 (0.6) Ic-4 Ic-4: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.4313 (0.3); 9.1330 (7.6); 8.4608 (1.6); 8.4500 (1.6); 7.7300 (7.8); 3.8548 (16.0); 3.3232 (224.8); 2.8460 (0.6); 2.8364 (0.8); 2.8277 (1.3); 2.8178 (1.3); 2.8091 (0.8); 2.7996 (0.6); 2.6752 (0.6); 2.6707 (0.9); 2.6663 (0.7); 2.5240 (2.0); 2.5104 (55.5); 2.5062 (115.7); 2.5017 (155.1); 2.4972 (113.3); 2.4930 (56.7); 2.3329 (0.7); 2.3284 (0.9); 2.3241 (0.7); 0.7346 (0.8); 0.7218 (2.3); 0.7166 (3.2); 0.7044 (3.0); 0.6986 (2.5); 0.6873 (1.1); 0.5704 (1.0); 0.5597 (3.1); 0.5532 (2.9); 0.5497 (2.7); 0.5438 (2.7); 0.5317 (0.9); 0.1459 (0.6); 0.0079 (4.0); -0.0002 (127.9); -0.0083 (6.1); -0.1497 (0.6)
Ic-5 Ic-5: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.3432 (4.0); 9.1293 (7.8); 7.7705 (8.1); 3.8576 (16.0); 3.3193 (50.6); 2.6750 (0.5); 2.6707 (0.8); 2.6662 (0.6); 2.5238 (1.8); 2.5061 (96.8); 2.5017 (129.0); 2.4972 (94.8); 2.3329 (0.6); 2.3283 (0.8); 2.0742 (0.8); 1.6052 (1.5); 1.5910 (3.8); 1.5840 (4.1); 1.5710 (1.8); 1.3418 (1.4); 1.3145 (1.2); 1.2909 (1.9); 1.2775 (3.9); 1.2706 (4.3); 1.2563 (1.5); 0.1461 (0.5); 0.0077 (4.0); -0.0003 (107.4); -0.0084 (4.9); -0.1498 (0.5) Ic-5 Ic-5: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.3432 (4.0); 9.1293 (7.8); 7.7705 (8.1); 3.8576 (16.0); 3.3193 (50.6); 2.6750 (0.5); 2.6707 (0.8); 2.6662 (0.6); 2.5238 (1.8); 2.5061 (96.8); 2.5017 (129.0); 2.4972 (94.8); 2.3329 (0.6); 2.3283 (0.8); 2.0742 (0.8); 1.6052 (1.5); 1.5910 (3.8); 1.5840 (4.1); 1.5710 (1.8); 1.3418 (1.4); 1.3145 (1.2); 1.2909 (1.9); 1.2775 (3.9); 1.2706 (4.3); 1.2563 (1.5); 0.1461 (0.5); 0.0077 (4.0); -0.0003 (107.4); -0.0084 (4.9); -0.1498 (0.5)
Ic-6 Ic-6: 1H-NMR(400.0 MHz, de-DMSO): δ= 9.1242 (6.8); 8.4526 (2.0); 8.4424 (1.9); 7.6925 (6.7); 3.8532 (16.0); 3.3225 (149.8); 2.8900 (0.4); 2.8437 (0.6); 2.8344 (1.0); 2.8259 (1.4); 2.8159 (1.4); 2.8070 (0.9); 2.7981 (0.6); 2.7310 (0.3); 2.6703 (1.0); 2.5014 (163.4); 2.3279 (1.0); 0.7333 (0.8); 0.7161 (3.3); 0.7032 (3.3); 0.6985 (2.7); 0.6867 (1.0); 0.5701 (1.1); 0.5594 (3.6); 0.5517 (3.6); 0.5444 (2.9); 0.5318 (0.8); 0.1454 (0.5); -0.0005 (94.2); -0.1505 (0.5) - -Ic-6 Ic-6: 1 H-NMR (400.0 MHz, de-DMSO): δ = 9.1242 (6.8); 8.4526 (2.0); 8.4424 (1.9); 7.6925 (6.7); 3.8532 (16.0); 3.3225 (149.8); 2,800 (0.4); 2.8437 (0.6); 2.8344 (1.0); 2.8259 (1.4); 2.8159 (1.4); 2.8070 (0.9); 2.7981 (0.6); 2.7310 (0.3); 2.6703 (1.0); 2.5014 (163.4); 2.3279 (1.0); 0.7333 (0.8); 0.7161 (3.3); 0.7032 (3.3); 0.6985 (2.7); 0.6867 (1.0); 0.5701 (1.1); 0.5594 (3.6); 0.5517 (3.6); 0.5444 (2.9); 0.5318 (0.8); 0.1454 (0.5); -0.0005 (94.2); -0.1505 (0.5) - -
Biologische Beispiele Biological examples
Boophilus microplus -Injektionstest Boophilus microplus injection test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
1 μΐ der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. 1 μΐ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20 μg/Tier: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-6 In this test, e.g. the following compounds of the Preparation Examples have an effect of 100% at an application rate of 20 μg / animal: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ib-1 , Ib-2, Ib-3, Ib-4, Ib-5, Ib-6
Ctenocephalides felis - Oraltest Ctenocephalides felis - Oraltest
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit citriertem Rinderblut erhält man die gewünschte Konzentration. For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
Ca. 20 nüchterne adulte Katzenflöhe {Ctenocephalides felis) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metallzylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält die Blut- Wirkstoffzubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane. After 2 days the kill is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ib-1, Ib-2 - -In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ib-1, Ib-2 - -
Lucilla cuprina - Test Lucilla cuprina - test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Ca. 20 LI -Larven der Australischen Schafgoldfliege {Lucilla cuprina) werden in ein Testgefäß überführt, welches gehacktes Pferdefleisch und die Wirkstoffzubereitung der gewünschten Konzentration enthält. Approximately Twenty LI larvae of the Australian Goldfinch {Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden. After 2 days the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ib-1 In this test, e.g. the following compounds of the Preparation Examples an effect of 100% at an application rate of 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ib-1
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 98 % bei einer Aufwandmenge von 100 ppm: Ib-4 In this test, e.g. the following compounds of the preparation examples an effect of 98% at an application rate of 100 ppm: Ib-4
Musca domestica-Test Musca domestica test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Gefäße, die einen Schwamm enthalten, der mit Zuckerlösung und der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit 10 adulten Stubenfliegen (Musca domestica) besetzt. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. After 2 days the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100 % bei einer Aufwandmenge von 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ib-1 In this test, e.g. the following compounds of the Preparation Examples an effect of 100% at an application rate of 100 ppm: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ib-1
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80 % bei einer Aufwandmenge von 100 ppm: Ib-4 Rhipicephalus sanguineus - in-vitro Kontakttests mit Adulten der braunen Hundezecke In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: Ib-4 Rhipicephalus sanguineus - in vitro contact tests with adults of brown dog tick
Für die Beschichtung der Teströhrchen werden zunächst 9 mg Wirkstoff in 1 ml Aceton p.a. gelöst und anschließend mit Aceton p.a. auf die gewünschte Konzentration verdünnt. 250 μΐ der Lösung werden durch Drehen und Kippen auf einem Rotationsschüttler (2 h Schaukelrotation bei 30 rpm) homogen auf den Innenwänden und dem Boden eines 25ml Glasröhrchens verteilt. Bei 900 ppm Wirkstofflösung und 44,7 cm2 Innenoberfläche wird bei homogener Verteilung eine Flächendosis von 5 μg/cm2 erreicht. For the coating of the test tubes, first 9 mg of active ingredient are dissolved in 1 ml of acetone pa and then diluted with acetone pa to the desired concentration. 250 μΐ of the solution are homogeneously distributed on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h swing rotation at 30 rpm). At 900 ppm active ingredient solution and 44.7 cm 2 inner surface, a surface dose of 5 μg / cm 2 is achieved with homogeneous distribution.
Nach Abdampfen des Lösungsmittels werden die Gläschen mit 5-10 adulten Hundezecken {Rhipicephalus sanguineus) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend im Dunkeln bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Zecken auf den Boden des Gläschens geklopft und auf einer Wärmeplatte bei 45-50°C maximal 5 min. inkubiert. Zecken, die unbeweglich auf dem Boden verbleiben oder sich so unkoordiniert bewegen, dass sie nicht gezielt der Wärme durch nach oben klettern ausweichen können, gelten als tot bzw. angeschlagen. After evaporation of the solvent, the vials are populated with 5-10 adult dog tick {Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
Eine Substanz zeigt gute Wirkung gegen Rhipicephalus sanguineus, wenn in diesem Test bei einer Aufwandmenge von 5 μg/cm2 mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Zecken angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Zecken geschädigt wurden. A substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 μg / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100%) bei einer Aufwandmenge von 5 μg/cm2 (= 500g/ha): Ia-3, Ia-4, Ib-6 Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%o bei einer Aufwandmenge von 5 μg/cm2 (= 500g/ha): Ia-1, Ia-5, Ia-7, Ib-1 In this test, for example, the following compounds of the preparation examples show an effect of 100%) at an application rate of 5 μg / cm 2 (= 500 g / ha): Ia-3, Ia-4, Ib-6 In this test, for example, the following are shown Compounds of the preparation examples an effect of 80% o at a rate of 5 ug / cm 2 (= 500g / ha): Ia-1, Ia-5, Ia-7, Ib-1
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100%) bei einer Aufwandmenge von 1 μg/cm2 (= 100g/ha): Ia-3, Ia-4, Ia-5, Ia-6, Ib-4 In this test, for example, the following compounds of the preparation examples show an effect of 100%) at an application rate of 1 μg / cm 2 (= 100 g / ha): Ia-3, Ia-4, Ia-5, Ia-6, Ib- 4
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%> bei einer Aufwandmenge von 1 μg/cm2 (= 100g/ha): Ia-7, Ib-1 In this test, for example, the following compounds of the preparation examples show an effect of 80%> at an application rate of 1 μg / cm 2 (= 100 g / ha): Ia-7, Ib-1
Ctenocephalides felis - in-vitro Kontakttests mit adulten Katzenflöhen Ctenocephalides felis - in vitro contact tests with adult cat fleas
Für die Beschichtung der Teströhrchen werden zunächst 9 mg Wirkstoff in 1 ml Aceton p.a. gelöst und anschließend mit Aceton p.a. auf die gewünschte Konzentration verdünnt. 250 μΐ der Lösung werden durch Drehen und Kippen auf einem Rotationsschüttler (2 h Schaukelrotation bei 30 rpm) homogen auf den Innenwänden und dem Boden eines 25ml Glasröhrchens verteilt. Bei 900 ppm Wirkstofflösung und 44,7 cm2 Innenoberfläche wird bei homogener Verteilung eine Flächendosis von 5 μg/cm2 erreicht. 5 For the coating of the test tubes, first 9 mg of active ingredient are dissolved in 1 ml of acetone pa and then diluted with acetone pa to the desired concentration. 250 μΐ of the solution are homogeneously distributed on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h swing rotation at 30 rpm). At 900 ppm active ingredient solution and 44.7 cm 2 inner surface, a surface dose of 5 μg / cm 2 is achieved with homogeneous distribution. 5
Nach Abdampfen des Lösungsmittels werden die Gläschen mit 5-10 adulten Katzenflöhen {Ctenocephalides felis) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Gläschen aufrecht gestellt und die Flöhe auf den Boden des Gläschens geklopft. Flöhe die unbeweglich auf dem Boden verbleiben oder sich unkoordiniert bewegen gelten als tot bzw. angeschlagen. After evaporation of the solvent, the vials are filled with 5-10 adult cat fleas {Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move uncoordinated are considered dead or struck.
Eine Substanz zeigt gute Wirkung gegen Ctenocephalides felis, wenn in diesem Test bei einer Aufwandmenge von 5 μg/cm2 mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Flöhe angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Flöhe geschädigt wurden. A substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 μg / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%) bei einer Aufwandmenge von 5 μg/cm2 (= 500g/ha): Ia-4 In this test, for example, the following compounds of the preparation examples show an effect of 80%) at an application rate of 5 μg / cm 2 (= 500 g / ha): Ia-4
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100%o bei einer Aufwandmenge von 5 μg/cm2 (= 500g/ha): Ia-2, Ia-3 Phaedon cochleariae - Sprühtest In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 5 μg / cm 2 (= 500 g / ha): Ia-2, Ia-3 phaedone cochleariae spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in %> bestimmt. Dabei bedeutet 100 %>, dass alle Käferlarven abgetötet wurden; 0 %> bedeutet, dass keine Käferlarven abgetötet wurden. After 7 days the effect is determined in%>. 100% means> that all beetle larvae have been killed; 0%> means that no beetle larvae have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 %> bei einer Aufwandmenge von 100 g/ha: Ia-1, Ia-2, Ia-3, Ia-5, Ia-6, Ia-7, Ib-1, Ib-4, Ib-6, Ic-1, Ic- 2, Ic-3, Ic-4, Ic-5, Ic-6 - - Spodoptera frugiperda - Sprühtest In this test, z. Example, the following compounds of the preparation examples effect of 100%> at an application rate of 100 g / ha: Ia-1, Ia-2, Ia-3, Ia-5, Ia-6, Ia-7, Ib-1, Ib -4, Ib-6, Ic-1, Ic-2, Ic-3, Ic-4, Ic-5, Ic-6 - - Spodoptera frugiperda - spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms {Spodoptera frugiperda) besetzt. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm {Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 100 g/ha: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ia-8, Ib-1, Ib-4, Ic- l, Ic-4, Ic-6 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 100 g / ha: Ia-1, Ia-2, Ia-3, Ia-4, Ia-5, Ia-6, Ia-7, Ia- 8, Ib-1, Ib-4, lc-l, lc-4, lc-6
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 100 g/ha: Ib-6 In this test, z. B. the following compounds of the preparation examples effect of 83% at a rate of 100 g / ha: Ib-6
Tetranychus urticae - Sprühtest, OP-resistent 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 Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
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 100g/ha: Ia-8, Ic-4 Myzus persicae - Oraltest In this test, z. Example, the following compounds of the preparation examples, an effect of 100% at an application rate of 100 g / ha: Ia-8, IC-4 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. 50 μΐ der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150μ1 IPL41 Insektenmedium (33% + 15%> Zucker) auf eine Endvolumen von 200 μΐ aufgefüllt. Anschließend werden die Platten mit 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. 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 of the active ingredient preparation are transferred into microtiter plates and filled with 150 μl IPL41 insect medium (33% + 15%> sugar) to a final volume of 200 μΐ. 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 4ppm: Ia-1, Ia-2 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 4ppm: Ia-1, Ia-2
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90%> bei einer Aufwandmenge von 4ppm: Ic-4 In this test, z. Example, the following compounds of the preparation examples effect of 90%> at a rate of 4ppm: Ic-4

Claims

Patentansprüche claims
1. Verbindungen der allgemeine Formel (I) 1. Compounds of the general formula (I)
Figure imgf000099_0001
Figure imgf000099_0001
worin wherein
R1 für H, jeweils gegebenenfalls mit einem oder mehreren Substitutenten unabhängig voneinander ausgewählt aus Amino, Hydroxy, Halogen, Nitro, Cyano, Isocyano, Mercapto, Isothiocyanato, Ci-C i-Carboxy, Carbonamid, SF5, Aminosulfonyl, C1-C4- Alkyl, C3-C4-Cycloalkyl, C2-C4-Alkenyl, C3-C4-Cycloalkenyl, C2-C4-Alkinyl, N-Mono- Ci-C4-alkyl-amino, NN-Di-Ci-C4-alkylamino, N-Ci-C4-Alkanoylamino, Ci-C4-Alkoxy, C2-C4-Alkenyloxy, C2-C4-Alkinyloxy, C3-C4-Cycloalkoxy, C3-C4-Cycloalkenyloxy, Ci-C4-Alkoxycarbonyl, C2-C4- C2-C4-Alkenyloxycarbonyl, C2-C4-Alkinyloxycarbonyl, C6-,Cio-,Ci4-Aryloxycarbonyl, Ci-C4-Alkanoyl, C2-C4-Alkenylcarbonyl, C2-C4- Alkinylcarbonyl, C6-,Cio-,Ci4-Arylcarbonyl, Ci-C4-Alkylsulfanyl, C3-C1- Cycloalkylsulfanyl, Ci-C4-Alkylthio, C2-C4-Alkenylthio, C3-C4-Cycloalkenylthio, C2-C4-Alkinylthio, Ci-C4-Alkylsulfenyl und Ci-C4-Alkylsulfinyl, wobei beide Enantiomere der Ci-C4-Alkylsulfinylgruppe umfasst sind, Ci-C4-Alkylsulfonyl, N- Mono-Ci-C4-alkyl-aminosulfonyl, NN-Di-Ci-C4-alkyl-aminosulfonyl, C1-C4- Alkylphosphinyl, Ci-C4-Alkylphosphonyl, wobei für Ci-C4-Alkylphosphinyl bzw. Ci-C4-Alkylphosphonyl beide Enantiomere umfasst sind, N-Ci-C4-Alkyl- aminocarbonyl, NN-Di-Ci-C4-alkyl-amino-carbonyl, N-Ci-C4-Alkanoyl-amino- carbonyl, N-Ci-C4-Alkanoyl-N-Ci-C4-alkyl-aminocarbonyl, C6-,Cio-,Ci4-Aryl, CÖ-,CIO- ,Ci4-Aryloxy, Benzyl, Benzyloxy, Benzylthio, C6-,Cio-,Ci4-Arylthio, C6-,Cio-,Ci4- Arylamino, Benzylamino, Heterocyclyl und Trialkylsilyl, mit einer Doppelbindung verbundenen Substituenten wie Ci-C4-Alkyliden (z. B. Methyliden oder Ethyliden), einer Oxogruppe, einer Iminogruppe substituiertes Ci-C6-Alkyl, C2-C6-Alkenyl C2-C6- Alkinyl, OCv-Cvcloalkyl, C6-.Cio-.Ci4-Aryl(Ci -C3)-alkyl 3. 4, 5. 6. 7. 8. 9 oder 10- gliedrigen-Heterocyclyl (z. B. Thietanyl wie Thiethanyl-3-yL Oxidothiethan wie 1 - Oxido-thietan-3-yL oder Dioxidothiethan wie l , l -Dioxido-thietan-3-yl oder 3, 4, 5, 6, 7, 8, 9 oder 10-gliedrigen-Heterocyclyl (Ci-CsValkyl steht, bevorzugt für gegebenenfalls mit Halogen oder Cyano substituiertem C3-C7-Cycloalkyl steht; R 1 is H, in each case optionally with one or more substituents selected independently from amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C 4 -alkyl , C 3 -C 4 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkyl-amino, NN-di- C 1 -C 4 -alkylamino, N-C 1 -C 4 -alkanoylamino, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 3 -C 4 -cycloalkoxy, C 3 -C 4 -cycloalkenyloxy , Ci-C 4 alkoxycarbonyl, C 2 -C4- C 2 -C 4 -alkenyloxycarbonyl, C 2 -C 4 -alkynyloxycarbonyl, C6, CIO, Ci 4 aryloxycarbonyl, Ci-C 4 alkanoyl, C2-C 4 alkenylcarbonyl, C2-C4-alkynylcarbonyl, C6, CIO, C 4 aryl-carbonyl, Ci-C4-alkylsulfanyl, C3-C 1 - cycloalkylsulfanyl, Ci-C4-alkylthio, C2-C4 alkenylthio, C3 -Cycloalkenylthio -C 4, C 2 -C 4 alkynylthio, Ci-C4 alkylsulfenyl, and Ci-C4-alkylsulfinyl, both enantiomers of the Ci-C 4 alkylsulfinyl group are included, Ci -C 4 alkylsulfonyl, N-mono-Ci-C 4 alkyl-aminosulfonyl, N, N-di-Ci-C 4 alkyl-aminosulfonyl, C 1 -C4- alkylphosphinyl, Ci-C 4 -Alkylphosphonyl, wherein for Ci C 4 -alkylphosphinyl or C 1 -C 4 -alkylphosphonyl both enantiomers are included, N-C 1 -C 4 -alkylaminocarbonyl, N, N-C 1 -C 4 -alkylamino-carbonyl, N-C 1 -C 4 - alkanoyl-aminocarbonyl, N-Ci-C 4 alkanoyl-N-Ci-C4-alkyl-aminocarbonyl, C6, CIO, C 4 aryl, C Ö -, CIO, C 4 aryloxy, benzyl , benzyloxy, benzylthio, C6, CIO, Ci 4 arylthio, C6, CIO, C 4 - arylamino, benzylamino, heterocyclyl and trialkylsilyl, having a double bond linked substituents such as Ci-C 4 alkylidene (eg. As methylidene or ethylidene), an oxo group, an imino group substituted Ci-C6-alkyl, C2-C6-alkenyl C2-C6- Alkynyl, C 1 -C 4 -cycloalkyl, C 6 -C 10 -Ci 4 -aryl (C 1 -C 3) -alkyl 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (for example thietanyl, such as thiethanyl) 3-yl oxidothiethane such as 1-oxidothietan-3-yl or dioxide thiethan such as 1,1-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci -CsValkyl, preferably represents optionally substituted by halogen or cyano substituted C3-C7-cycloalkyl;
R2 für H oder Ci-C6-Alkyl steht; die Gruppierungen R 2 is H or C 1 -C 6 alkyl; the groupings
Ai, A2 und A3 unabhängig voneinander für N, O, CR3, S oder N-R4 stehen, wobei Ai, A2, A3, Z und das C-Atom des Ringes ein aromatisches System bilden; Ai, A 2 and A3 are independently N, O, CR 3 , S or NR 4 , with Ai, A 2 , A3, Z and the C atom of the ring forming an aromatic system;
R3 und R4 jeweils unabhängig voneinander für H oder gegebenenfalls halogeniertes Ci-C i-Alkyl stehen; R 3 and R 4 are each independently H or optionally halogenated Ci-C i-alkyl;
Q für O oder S steht; Q is O or S;
Z für C oder N steht; Z is C or N;
T für einen der nachfolgend aufgeführten 5-gliedrigen Heteroaromaten T1 -T8 steht, wobei T is one of the 5-membered heteroaromatics T1-T8 listed below, wherein
Figure imgf000100_0001
Figure imgf000100_0001
die Bindung zu mit einer Raute # gekennzeichnet ist,  the bond to is marked with a rhombus #,
Tl T2 T3 T4 T5 T6 T7 T8 T1 T2 T3 T4 T5 T6 T7 T8
Figure imgf000100_0002
wobei R5 für optional halogeniertes (CI-CÖ)- Alkyl, optional halogeniertes (Ci-C6)-Alkoxy, -S(0)o- 2-(Ci-C2)-alkyl oder NO2 steht, bevorzugt für perhalogeniertes (Ci-C i)-Alkyl, perhalogeniertes (Ci-C4)-Alkoxy oder -S(0)o-2-(Ci-C2)-alkyl steht, mehr bevorzugt für perfluoriertes (Ci-C4)-Alkyl, perfluoriertes (Ci-C4)-Alkoxy oder -S(0)o-2-(Ci-C2)-alkyl steht, noch mehr bevorzugt für CF3 steht;
Figure imgf000100_0002
in which R 5 is optionally halogenated (C 1 -C 6) -alkyl, optionally halogenated (C 1 -C 6) -alkoxy, -S (O) o-2 (C 1 -C 2 ) -alkyl or NO 2 , preferably perhalogenated (C 1 -C 4) -alkyl -C i) -alkyl, perhalogenated (Ci-C4) -alkoxy or -S (0) o- 2 - (Ci-C 2 ) -alkyl, more preferably perfluorinated (Ci-C4) -alkyl, perfluorinated (Ci -C 4) alkoxy or -S (O) o-2- (C 1 -C 2) alkyl, even more preferably CF 3;
R6 für optional halogeniertes (C3-C6)-Cycloalkyl, optional halogeniertes (Ci-Ce)-Alkoxy oder optional halogeniertes (Ci-C6)-Alkyl steht, bevorzugt für perhalogeniertes (C1-C4)- Alkyl oder perhalogeniertes (Ci-C4)-Alkoxy steht, mehr bevorzugt für perfluoriertes (Ci-C4)-Alkyl oder perfluoriertes (Ci-C4)-Alkoxy steht, noch mehr bevorzugt für C2F5 steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I). R 6 is optionally halogenated (C 3 -C 6 ) -cycloalkyl, optionally halogenated (C 1 -C 6) -alkoxy or optionally halogenated (C 1 -C 6) -alkyl, preferably perhalogenated (C 1 -C 4) -alkyl or perhalogenated (C 1 -C 4 ) Alkoxy, more preferably perfluorinated (C 1 -C 4) -alkyl or perfluorinated (C 1 -C 4) -alkoxy, even more preferably C 2 F 5 ; and salts, N-oxides and tautomeric forms of the compounds of the formula (I).
2. Verbindung gemäß Anspruch 1, wobei R2 für H oder Methyl steht. 2. A compound according to claim 1, wherein R 2 is H or methyl.
3. Verbindung gemäß einem der vorherigen Ansprüche, wobei T für Tl, T4 oder T5 steht. 3. A compound according to any one of the preceding claims, wherein T is Tl, T4 or T5.
4. Verbindung gemäß einem der vorherigen Ansprüche, wobei T für T2, T3, T4, T5, T6, T7 oder T8 steht. 4. A compound according to any one of the preceding claims, wherein T is T2, T3, T4, T5, T6, T7 or T8.
5. Verbindung gemäß einem der vorherigen Ansprüche, wobei T für T4 oder T5 steht. 5. A compound according to any one of the preceding claims, wherein T is T4 or T5.
6. Verbindung gemäß einem der vorherigen Ansprüche, wobei R1 für Cyclopropyl oder 1-CN- Cyclopropyl steht. 6. A compound according to any one of the preceding claims, wherein R 1 is cyclopropyl or 1-CN-cyclopropyl.
7. Verbindung gemäß einem der vorherigen Ansprüche, wobei Q für O steht. A compound according to any one of the preceding claims, wherein Q is O.
8. Verbindung gemäß einem der vorherigen Ansprüche, wobei A3 für S steht. 8. A compound according to any one of the preceding claims, wherein A3 stands for S.
Verbindung gemäß einem der vorherigen Ansprüche, wobei wobei Z für C-H und A2 für C-Hal, wobei Hai bevorzugt für I, Br und Clsteht, stehen. A compound according to any one of the preceding claims, wherein Z is CH and A 2 is C-Hal, wherein Hal is preferably I, Br and Cl.
Verbindung gemäß einem der vorherigen Ansprüche, wobei A3 für S steht, Z für C-H und A2 für C-Hal, wobei Hai für I, Br oder Cl steht, stehen und Ai für C-H oder N steht. A compound according to any one of the preceding claims, wherein A3 is S, Z is CH and A 2 is C-Hal, wherein Hal is I, Br or Cl, and Ai is CH or N.
Verbindung gemäß einem der vorherigen Ansprüche, wobei die Verbindung eine Verbindung Foremel (Ia) A compound according to any one of the preceding claims, wherein the compound is a compound Foremel (Ia)
Figure imgf000102_0001
Figure imgf000102_0001
(Ia) ist worin Q, R1, R2, R5 und R6 und Ai wie in einem der vorherigen Ansprüchen definiert sind und Hai bevorzugt für I, Br oder Cl steht. (Ia) wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined in any one of the preceding claims and Hai is preferably I, Br or Cl.
Figure imgf000102_0002
wonn Q, R1, R2, R5 und R6 und Ai wie in einem der vorherigen Ansprüchen definiert sind und Hai bevorzugt für I, Br oder Cl steht.
Figure imgf000102_0002
wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined in any one of the preceding claims, and Hai is preferably I, Br or Cl.
13. Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß Anspruch 1 1 , worin Q für O steht, Ai für N oder C-H steht, Hai für Br, Iod oder Cl steht, R2 für H steht, R1 für gegebenenfalls mit CN substituiertes Cyclopropyl steht, R5 für CF3 und R6 für C2F5 steht. 13. A further preferred embodiment is directed to compounds according to claim 1 1, wherein Q is O, Ai is N or CH, Hai is Br, iodine or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl, R 5 is CF 3 and R 6 is C 2 F 5.
Eine weitere bevorzugte Ausführungsform richtet sich dabei auf Verbindungen gemäß Anspruch 12, worin Q für O steht, Ai für C-H steht, Hai für Br, Iod oder Cl steht, R2 für H steht, R1 für gegebenenfalls mit CN substituiertes Cyclopropyl steht, R5 für CF3 und R6 für C2F5 steht. A further preferred embodiment is directed to compounds according to claim 12, wherein Q is O, Ai is CH, Hai is Br, iodine or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl, R 5 is CF 3 and R 6 is C2F5.
15. Insektizides Mittel umfassend mindestens eine Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 14 und einem Streckmittel und/oder einer oberflächenaktiven Substanz. An insecticidal composition comprising at least one compound of the formula (I) according to one of Claims 1 to 14 and an extender and / or a surface-active substance.
Verfahren zum Schutz von transgenem oder konventionellem Saatgut und der daraus entstehenden Pflanze vor dem Befall von Schädlingen, dadurch gekennzeichnet, dass das Saatgut mit mindestens einer Verbindung gemäß einem der Ansprüche 1 bis 14 behandelt wird. A method of protecting transgenic or conventional seed and the resulting plant from attack by pests, characterized in that the seed is treated with at least one compound according to any one of claims 1 to 14.
17. Verwendung von Verbindungen gemäß einem der Ansprüche 1 bis 14, oder von einem Insektiziden Mittel gemäß Anspruch 15 zum Bekämpfen von Schädlingen. 17. Use of compounds according to any one of claims 1 to 14, or of an insecticidal composition according to claim 15 for controlling pests.
Saatgut, enthaltend eine Verbindung gemäß einem der Ansprüche 1 bis 14 als Bestandteil einer Umhüllung, die auf das Saatgut aufgebracht ist, oder als Bestandteil einer weiteren Schicht, die zusätzlich zu einer Umhüllung auf das Saatgut aufgebracht ist. Seed comprising a compound according to any one of claims 1 to 14 as part of a casing applied to the seed or as part of another layer applied to the seed in addition to a casing.
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