WO2017125340A1 - Condensed bicyclic heterocycle derivatives as pest control agents - Google Patents

Condensed bicyclic heterocycle derivatives as pest control agents Download PDF

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WO2017125340A1
WO2017125340A1 PCT/EP2017/050773 EP2017050773W WO2017125340A1 WO 2017125340 A1 WO2017125340 A1 WO 2017125340A1 EP 2017050773 W EP2017050773 W EP 2017050773W WO 2017125340 A1 WO2017125340 A1 WO 2017125340A1
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alkyl
spp
cycloalkyl
alkoxy
formula
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PCT/EP2017/050773
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German (de)
French (fr)
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Rüdiger Fischer
Laura HOFFMEISTER
David WILCKE
Nina Kausch-Busies
Dominik HAGER
Matthieu WILLOT
Kerstin Ilg
Sascha EILMUS
Ulrich Görgens
Andreas Turberg
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Bayer Cropscience Aktiengesellschaft
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Publication of WO2017125340A1 publication Critical patent/WO2017125340A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to novel condensed bicyclic heterocyclic derivatives of the formula (I) or the formula ( ⁇ ), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular of insects and arachnids, and methods and intermediates their production.
  • condensed bicyclic heterocyclic derivatives which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, better insecticides, acaricidal activity, as well as a good tolerance to crops exemplified.
  • the condensed bicyclic heterocyclic derivatives can be used in combination with other agents for improving the effectiveness in particular against difficult-to-control insects.
  • the present invention therefore relates to novel compounds of the formulas (I) or (II)
  • Aa is nitrogen or ⁇ (a carbon atom with a double bond to Ab or Ad),
  • R 1 alkyl is (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C 6) , (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6)
  • C8 cycloalkylamino, (Ci-C6) alkylcarbonyl-amino, (Ci-C6) alkylthio (Ci-C6) alkyl, (Ci- C 6) haloalkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfinyl- (C 1 -C 6 ) -alkyl,
  • Hetaryl or heterocyclyl substituted (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 3 -C 8 ) cycloalkyl, wherein aryl, hetaryl or heterocyclyl respectively optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, C 6) haloalkyl, (Ci-C 6) haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) alkylsulfinyl,
  • R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another represent hydrogen, cyano, halogen,
  • C8 cycloalkylaminocarbonyl (Ci-C6) alkylsulfonylamino, (Ci-C6) alkylamino, di (Ci- C6) alkylamino, aminosulfonyl, (Ci-C6) alkylaminosulfonyl, di (Ci-Ce) alkyl aminosulfonyl, (C -C6) alkylsulfoximino, aminothiocarbonyl, (
  • C8 cycloalkylamino or NHCO- (Ci-Ce) alkyl ((Ci-C6) alkylcarbonylamino are) hydrogen, acetyl, (Ci-C 4) alkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) haloalkyl, (Ci C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl , (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl, (C 2 -C 4) alky
  • C ⁇ ) alkylcarbonylamino), - or wherein the substituents may be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl , C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN , NO 2 , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, is 0, 1 or 2, stands for 0, 1 or 2,
  • the compounds of the formulas (I) or (II) have very good activity as pesticides, preferably as insecticides and / or acaricides, moreover, as a rule, are very well tolerated by plants, in particular with respect to crop plants.
  • Aa is preferably nitrogen
  • R 1 is preferably (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkylthio (Ci -C 4) alkyl, (Ci-C 4) alkylsulfinyl (CI-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, or represents in each case optionally monosubstituted or disubstitute
  • R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another preferably represent hydrogen
  • R 7 is preferably hydrogen, acetyl, (Ci-C) alkyl, (Ci-C) haloalkyl, (Ci-C) cyanoalkyl, (Ci-C 4 ) alkoxy (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (Ci -C 4) alkylthio (Ci-C 4) alkyl, or represents in each case optionally mono- or disubstituted by identical or different aryl or heterocyclyl substituted (Ci-C 4) alkyl, wherein aryl or heterocyclyl each optionally monosubstituted or disubstitute
  • Q preferably represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to QU, Q14 to Q17 or Q20,
  • R 4 is preferably (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, - -
  • R 5, R 6 independently of one another preferably represent hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxyimino, (C 1 -C 4) -alkylthio,
  • Aa is particularly preferably nitrogen
  • the following structural units are particularly preferably obtained: A5, A6, A7, A8, A9, A10, Al1, A12, A13, A19, A20,
  • R 1 particularly preferably represents (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 3 -C 6 ) -cycloalkyl,
  • R 2 , R 3 , R 8 independently of one another particularly preferably represent hydrogen, cyano, halogen,
  • R 7 particularly preferably represents hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (CI-C 4) cyanoalkyl or (Ci-C 4) alkoxy (Ci-C 4) alkyl,
  • Q particularly preferably represents a 9-membered heteroaromatic bicyclic ring system of the series Q1, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17,
  • R 4 particularly preferably represents (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
  • R 5 is particularly preferably halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy or (C 1 -C 4) haloalkylthio,
  • R 6 is particularly preferably hydrogen, n is particularly preferably 0, 1 or 2, m is particularly preferably 0.
  • Aa is very particularly preferably nitrogen
  • Ad is very particularly preferably -S (0) m -, - -O- or -N (R 7 ) -. where very particular preference is given to the following structural units: A6, A10, Al1, A12, A13,
  • A12 A13 R 1 very particularly preferably represents ethyl
  • R 2 , R 3 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
  • R 7 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, sec-propyl or tert-butyl, very particularly preferably represents a heteroaromatic 9-membered fused bicyclic ring system from the series Q 2 or Q 3,
  • R 4 very particularly preferably represents methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
  • R 5 very particularly preferably represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
  • R 6 is very particularly preferably hydrogen, n is very particularly preferably 0, 1 or 2, m is very particularly preferably 0.
  • Aa stands for nitrogen
  • Ad stands for -S (0) m -, the result being the following structural units: Al 1, R 1 stands for ethyl,
  • R 2 , R 3 are hydrogen
  • R 5 stands for trifluoromethyl
  • R 6 stands for hydrogen, n stands for 0 or 2, m stands for 0. Configuration 5-2
  • Aa stands for nitrogen
  • Ad stands for -S (0) m -, with the following structural units being highlighted: A 11,
  • R 1 stands for ethyl
  • R 2 is hydrogen
  • R 3 is hydrogen or trifluoromethyl
  • R 4 is methyl
  • R 3 stands for trifluoromethyl
  • R 6 is hydrogen, n is 0 or 2, m is highlighted for 0.
  • Aa stands for nitrogen in particular
  • Ad stands in particular for -C (R 13 ) (R 14 ) -,
  • R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 1.
  • Aa stands for nitrogen in particular
  • Ad stands in particular for -C (R 1 ) (R 14 ) -,
  • R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 2.
  • Aa stands for nitrogen in particular
  • Ad stands in particular for -C (R 13 ) (R 14 ) -,
  • R 1 stands for particular (Ci-C 4) alkyl, (Ci-C 4) haloalkyl or (C 3 -C 6) cycloalkyl
  • R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are, independently of one another, particularly hydrogen
  • Q is especially for a heteroaromatic 9-membered annell investigatings bicyclic ring system from the series Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17, R 4 is in particular is (Ci-C 4) alkyl or (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl,
  • R 5 is in particular halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy or (Ci- C4) haloalkylthio,
  • R 6 is in particular hydrogen, n is in particular 0, 1 or 2.
  • Aa stands for nitrogen in particular
  • Ad stands in particular for -C (R 13 ) (R 14 ) -, whereby in particular the following structural units result: AI,
  • R 1 is especially ethyl
  • R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another are especially hydrogen, methyl or ethyl
  • Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q2 or Q3,
  • R 4 is especially methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl, - -
  • R 5 is in particular fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio, R 6 is in particular hydrogen, n is especially 0, 1 or 2.
  • Ab in particular stands for -C (R 9 ) (R 10 ) -
  • Ac stands in particular for -C (R U ) (R 12 ) -
  • ad stands in particular for -C (R 13 ) (R 14 ) -, wherein in particular the following structural units are obtained: Al, R 1 is in particular ethyl,
  • R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are in particular hydrogen
  • Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q3
  • R 4 is especially methyl
  • R 5 is especially trifluoromethyl
  • R 6 is in particular hydrogen, n is insbesosnders for 2.
  • the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1).
  • the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or Embodiment (6-1) or Embodiment (6-2) or Embodiment (6-3) or Embodiment (6-4) - - or embodiment (6-5) have specified meanings.
  • the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1).
  • the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or design (6-1) or design (6-2) or design (6-3) or design (6-4) or design (6-5) have specified meanings.
  • the invention relates to compounds of the formula (I) of the structural unit Al 1
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in embodiment (2) or embodiment (3) or embodiment (4) or embodiment (5-1) or embodiment Have (5-2) indicated meanings.
  • the invention relates to compounds of the formula (I) of the structural unit AI
  • the invention relates to compounds of the formula (I) of the structural unit AI - -
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
  • alkyl either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n
  • alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 -alkenyl radical having at least one double bond, for example vinyl, allyl , 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl , understood.
  • 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1, 4-hexadienyl thereof are C 2 -C 6 alkenyl groups and particularly preferred are C 2 -C 4 -alkenyl.
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 alkynyl having at least one triple bond, for example ethynyl, 1 Propynyl and propargyl, preferably C3-C6 alkynyl radicals and C 3 -C 4 -alkynyl radicals are particularly preferred.
  • the alkynyl radical can also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
  • alkoxy either alone or in combination with other terms, such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • Very particularly preferably used according to the invention are compounds of the formulas (I) or (II) which contain a combination of the meanings given above as being very particularly preferred.
  • the compounds of the formulas (I) or (II) can be used as geometric and / or as optically active isomers or corresponding isomer mixtures in different composition.
  • 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 compounds of the formula (I) in which Q is Q1 to Q9 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
  • R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N (where A 2 and A 3 are not simultaneously N A 4 is O, S or NR 4 and X 1 is halogen. - - Step a)
  • the compounds of the formula (IV) can be prepared in analogy to the process described in US Pat. No. 5,573,335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
  • Compounds of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO2006 / 65703, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715 described method.
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
  • reaction of the compounds of the formula (II) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
  • Nitriles such as acetonitrile or propionitrile
  • aromatic hydrocarbons such as toluene or xylene
  • aprotic polar solvents such as N, N-
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • bases are inorganic bases which are commonly used in such reactions.
  • bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
  • Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
  • the compounds of the formula (V) can be prepared by condensation of the compounds of the formula (IV), for example analogously to those in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, - -
  • the reaction to give compounds of the formula (V) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
  • acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N
  • An example of a suitable chlorinating agent is phosphorus oxychloride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base.
  • Mercaptan derivatives of the formula (IVa) such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods - be prepared, for example analogously to those in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
  • the reaction to give compound of formula (I) wherein n is 0 may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent selected from conventional solvents inert to the prevailing reaction conditions.
  • ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Sodium hydride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • X 1 is preferably a fluorine or chlorine atom.
  • the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
  • the oxidation is generally carried out in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
  • Step e) The compounds of formula (I) wherein n is 2 can be prepared by oxidation of the compounds of formula (I) wherein n is 1.
  • the oxidation is generally in a solvent - - carried out.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
  • the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
  • Process A-2 The compounds of the formula (I) in which Q is Ql to Q9, Q17 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
  • R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N, A 4 is O, S or NR 4 , M is lithium, sodium or potassium and X 1 - - stands for halogen.
  • compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (V).
  • the exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and ⁇ , ⁇ -dimethylformamide.
  • sulfur reagents examples include the lithium, sodium or potassium salts of sulfinic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
  • R 1 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above.
  • a 2 , A 3 , A 4 and A 5 are CH or N (wherein A 2 , A 3 , A 4 and A 5 are not simultaneously N) and X 1 is halo.
  • Carboxylic acids of the formula (III) are converted in analogy to the process described in WO2011 / 75643 or EP2671582 in the presence of ⁇ , ⁇ -dimethylhydroxylamine hydrochloride into Weinreb amides of the formula (VI).
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
  • the compounds of the formula (X) can be prepared by cyclization of the compounds of the formula (VIII) with amines of the formula (IX).
  • the cyclization is carried out, for example, in ethanol, acetonitrile or ⁇ , ⁇ -dimethylformamide by known methods analogously to, for example, WO2005 / 66177, WO2012 / 88411, WO2013 / 3298, US2009 / 203705, US2012 / 258951, WO2012 / 168733, WO2014 / 187762 or J. Med. Chem. 31 (1988) 1590-1595.
  • the compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (X) with the compounds of the formula (Via) in the presence of a base.
  • Mercaptan derivatives of the formula (Via) such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
  • the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
  • the oxidation is carried out by known methods with a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
  • a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
  • the compounds of formula (I) wherein n is 2 may be prepared by oxidation of the compounds of formula (I) wherein n is 1.
  • the oxidation is generally carried out in a solvent.
  • halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
  • the oxidation is generally carried out in a solvent.
  • halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the compounds of the formula (I) in which Q is Q10, QU, Q15 and Q16 can be prepared by known methods, for example analogously to those described in US2009 / 203705, US2012 / 258951, WO2013 / 3298 or J. Med. Chem. 31, (1988) 1590-1595.
  • R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 , A 3 , A 4 and A 5 are CH or N, M is lithium , Sodium or potassium and X 1 is halogen.
  • compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (X).
  • the exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and N, N-dimethylformamide.
  • Suitable sulfur reagents are the lithium, sodium or potassium salts of sulfinic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
  • the compounds of the formula (I) in which Q is Q17 can be prepared by known methods, for example analogously to the processes described in WO2014 / 142292.
  • R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above.
  • X 1 is halogen.
  • the compounds of the formula (XI) can be prepared by reacting, analogously to the process described in US Pat. No. 5,374,446 or Bioorganic and Medicinal Chemistry Letters 2003, 13, 1093-1096
  • Compounds of formula (III) can be prepared with an ammonia source in the presence of a condensing agent.
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
  • the reaction of the compounds of the formula (III) with the source of ammonia is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, dioxane or tetrahydrofuran.
  • a suitable condensing agent is, for example, carbonyldiimidazole.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 70 ° C.
  • the compounds of the formula (XIII) can be prepared in analogy to the process described in WO2014 / 142292 by the reaction of compounds of the formula (XI) with compounds of the formula (XII) in the presence of a palladium catalyst in basic.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 110 ° C.
  • R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above.
  • X 1 is halogen.
  • Step a) The compounds of the formula (XV) can be prepared in analogy to the process described in WO2011 / 073149 or US5576335 by reacting compounds of the formula (XIV) with a carboxylic acid of the formula (III) in the presence of a condensing agent or a base become.
  • Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
  • the reaction of the compounds of the formula (XIV) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine. - -
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
  • bases are inorganic bases which are commonly used in such reactions.
  • bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
  • Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
  • the compounds of formula (XVI) can be prepared by condensation of the compounds of formula (XV) e.g. analogously to the process described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715.
  • the reaction to give compounds of the formula (XVI) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
  • Nitriles such as acetonitrile or propionitrile
  • aromatic hydrocarbons such as toluene or xylene
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
  • suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • An example of a suitable chlorinating agent is phosphorus oxychloride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • Carboxylic acids of the formula (IIIa) with the structural unit AI are either commercially available or can be prepared by known methods, for example from pyrrolidine derivatives analogous to those described in WO2011 / 098904, Chemical Communications, 48 (2012), 3133-3135, Organic Letters , 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013 ), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305 described method. - -
  • R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the meanings described above.
  • X 1 is halogen and R 15 is (Ci-C 6 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a), b), c)
  • the compounds of the formula (XXII) can be prepared by reacting compounds of the formula (XXI) with a propiolate of the formula (XX) under neutral conditions in analogy to the processes described in Chemical Communications, 48 (2012), 3133-3135 and WO2011 / 098904 Conditions in a Michael addition followed by diazotization at the oc-carbon of the Michael adduct using typical diazotization reagents and subsequent cyclization under basic conditions to the desired 6,7-dihydro-5H-pyrrolo [1,2-a] imidazole getting produced.
  • the compounds of formula (XXI) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Letters, 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305.
  • Compounds of formula (XXIII) may be prepared by known methods, for example via direct ortho-lithiation followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or alternatively via a carboxylic acid derivative - -
  • Compounds of the formula (IIIa) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
  • Carboxylic acids of the formula (IIIb) having the structural units A2, A3 or A4 are either commercially available or can be prepared by known methods, for example from oxazolidinone, thiazolidinone or imidazolidinone derivatives analogous to those described in Russian Journal of Organic Chemistry, 46 (US Pat.
  • R 9 , R 10 , R 11 and R 12 have the meanings described above.
  • Ad stands for -S (0) m -, -O- or -N (R 7 ) -.
  • X 1 and X 2 are halogen, R 15 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl and R 16 is -CN or -COOR 17 , wherein R 17 is (Ci-C 4 ) Alkyl.
  • Step a) The compounds of the formula (XXV) can be prepared in analogy to those described in Russian Journal of Organic Chemistry, 46 (2010), 1461-1465, US2005 / 0256164 and US2002 / 0098443 via an alkylation of oxazolidinone, thiazolidinone or Imidazolidinone derivatives of the formula (XXIV) with the corresponding oc-halo or ⁇ -diazo carboxylic acid esters or nitriles are synthesized under acidic or basic conditions.
  • the compounds of formula (XXIV) are either commercially available or can be prepared by known methods, for example analogous to those described in Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787 and Journal of the American Chemical Society, 73 (1951), 4199-4204.
  • Carboxylic acid ester derivatives of the formula (XXIX) are either commercially available or can be prepared by known methods, for example via halogenation. This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
  • Carboxylic acids of the formula (IIIc) having the structural units A5, A6, A7, A8, A9, A10, Al, A12 or Al 3 are either commercially available or can be prepared by known methods, for example analogously to those described in WO2013 / 163244, Farmaco, Ediette Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929, WO2015 / 011082, Journal of Medicinal Chemistry, 58 (2015), 8309- 8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry, 59 (2015), 151-167, Journal of the Chemical Society, (1929), 815-816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946-2948, Helvetica Chimica Acta, 32 (1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092, Journal of the American Chemical Society
  • the compounds of the formula (XXXII) can be prepared, for example, in analogy to those described in WO2013 / 163244, Farmaco, Ediette Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929 and WO2015 / 011082 are synthesized via a condensation of 2-amino heteroaryl derivatives of the formula (XXXI) with a oc-Halopyruvat of formula (XXX).
  • Step b) Compounds of the formula (XXXIII) can be prepared by known methods, for example via halogenation. This may be, for example, via directed ortho-lithiation, followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or, alternatively, via a carboxylic acid derivative-directed halogenation in analogy to that described in Bioorganic - -
  • Compounds of the formula (IIIc) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
  • Carboxylic acids of the formula (IIIa ') having the structural units A15 or A17 are either commercially available or can be prepared by known methods, for example in analogy to the methods described in WO2006 / 130588, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236- 4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
  • the compounds of formula (XLVI) are either commercially available or can be prepared via the methods described in Journal of Organic Chemistry, 65 (2000), 2379-2385; Tetrahedron: Asymmetry, 16 (2005), 2973-2979; Chemische Berichte, 111 (1987), 411-414 and Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 208 (1981), 617-619, via a dibromination of the corresponding olefin compounds.
  • Compounds of formula (XLVIII) are either commercially available or can be prepared via halogenation of the compounds of formula (XL VII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
  • Compounds of the formula (IIIa ') can be prepared by known methods from compounds of the formula (XLVIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
  • Carboxylic acids of the formula (IIIb ") having the structural units A14, A16 or A18 are either commercially available or can be prepared by known methods, for example in analogy to those described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588, WO2010 / 117425, Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587-597, Bulletin of the Chemical Society of Japan, 36 (1963) , 25-29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461, Chemistry Letters, 7 (1985), 939-942, Tetrahedron Letters, 24 (1989). 1983), 1067-1070, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238, Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
  • R 15 is (Ci-Ce) alkyl or aryl (Ci-C 2 ) alkyl.
  • Ab stands for -C (R 9 ) (R 10 ) -, -S (0) m -, -O- or -N (R 7 ) -.
  • Ac is -C (R U) (R 12) -, -S (0) m -, -O- or -N (R 7) -.
  • X 1 is halogen.
  • Nitrosoproline derivatives of the formula (XXXV) are either commercially available or can be prepared by known methods, for example analogously to the methods described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Nitrosation of compounds of the formula (XXXIV).
  • Mesoionic sydnone derivatives of the formula (XXXVI) are either commercially available or can be prepared by known methods, for example analogously to the method described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Compounds of formula (XXXV) by heterocyclization using e.g. B. trifluoroacetic acid anhydride as dehydrating reagent.
  • Compounds of the formula (XXXIX) are either commercially available or can be prepared by known methods via halogenation of the compounds of the formula (XXVIII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
  • Carboxylic acids of the formula (IIIc ') having the structural units A19 or A20 are either commercially available or can be prepared by known methods, for example analogously to those described in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003 / 093280 WO200001 / 016138, WO2008 / 067257, WO2011 / 079230, WO2008 / 015271, WO2004 / 092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of Chemical Society, Perkin Transaction 1: Organic and Organic Biochemistry, 18 (1999), 2639-2644, WO2003 / 035644, WO2013 / 050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry-A European Journal, 18 (2012), 14943-14947 and WO2013 / 036994.
  • X 1 and X 3 are halogen and R 21 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a) - -
  • the compounds of formula (XLI) are either commercially available or can be prepared via the methods described in Journal of the American Chemical Society, 132 (2010), 1264-1266, Organic Preparations and Procedures International, 7 (1975), 149-154 and European Journal of Medicinal Chemistry, 16 (1981), 495-501, via ⁇ -halogenation of the corresponding ketones.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) or of the formula ( ⁇ ) 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) or of the formula (II) as pesticides, in particular pesticides.
  • pest control always always includes the term pesticides.
  • the compounds of the formula (I) or of the formula (II) are suitable for plant protection, favorable toxicity to warm-blooded animals and good environmental compatibility for protecting plants and plant organs against biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, in particular nematodes, and molluscs, which are found in agriculture, horticulture, animal breeding, aquaculture, forestry, gardens and recreational facilities, in the protection of stored products and in the sanitary sector.
  • the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.
  • measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications where these hygiene measures, rules and procedures are important, for example in the - -
  • the term "hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
  • hygiene pests include the organisms mentioned below.
  • the compounds of the formula (I) or the formula (II) can be preferably used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B.
  • Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, - -
  • Phyllophaga spp. Phyllophaga helleri
  • Phyllotreta spp. E.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tanymecus spp. E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B.
  • Delia antiqua Delia coarctata, Delia llorilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus - - floccosus, Allocaridara malayensis, Amrasca spp. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g.
  • Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
  • B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum spp. E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Trioza spp. E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • 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.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp.
  • Heliothis virescens Hofmannophila pseudospretella Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria ilavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
  • Leucoptera coffeella Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
  • Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • Lepinotus spp. Liposcelis from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephalides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips hevens, Frankliniella spp., Z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
  • Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., 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. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
  • the compounds of the formula (I) or of the formula (II) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, Viricides (including anti-viral agents) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) can be used. 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 comprising at least one compound of formula (I) or formula ( ⁇ ).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I) or of the formula (II), further agrochemical active compounds.
  • compositions or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries such as - -
  • 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.
  • These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) or the formula ( ⁇ ) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
  • 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
  • poly ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg.
  • Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. Methanol, ethanol, iso-propanol, - -
  • Suitable carriers can be used.
  • carriers are in particular question: z.
  • ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: z.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
  • alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (I) or formula (II) and / or one of the inert carriers is not soluble in water and when applied in water.
  • auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg.
  • dyes such as inorganic pigments, eg.
  • iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers. - -
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) or formula (II) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • Retentionsiörderer are all those substances that reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the 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, Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • Fettaminalkoxylate 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) or of the formula (II), particularly preferably between 0.01 and 95% by weight of the compound of the formula (I) or of the formula (II ), very particularly preferably between 0.5 and 90% by weight of the compound of the formula (I) or of the formula (II), based on the weight of the formulation.
  • the content of the compound of the formula (I) or the formula (II) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) or the formula (II) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the - -
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) or formula (II) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners , Semiochemicals and / or plant growth regulators are used so z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such.
  • the compounds of the formula (I) or of the formula (II) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of formula (I) or formula ( ⁇ ) can be used to improve plant properties such as growth, yield and quality of the crop.
  • the compounds of the formula (I) or of the formula (II) 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,
  • GABA-controlled chloride channel B loosened such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
  • sodium channel modulators such as pyrethroids, e.g.
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • nAChR nicotinic acetylcholine receptor
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or crushing tartar or methyl isocyanate producers, e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and dillovidazine or etoxazole.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors such as diafenthiuron or organotin compounds, e.g. As azocyclotin, cyhexatin and fenbutatin oxide or
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, novillumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
  • ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidia, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidia, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (22) blocker of the voltage-dependent sodium channel such.
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
  • inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyilumetofen and carboxanilides, such as Pyllubumid.
  • ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxa
  • Fungicides The active ingredients specified here by their "common name” are known and described, for example, in the "Pesticide Manual” (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) ,
  • All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
  • All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetracon
  • N-methylimidoformamide (1.076) ⁇ '- ⁇ 5-bromo-6- [(1 R) -1- (3, 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N- methylimidoformamide, (1.077) N '- ⁇ 5-bromo-6- [(1S) -1- (3,5-difluorohexyl) ethoxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N-methylimidoformamide , (1.078) N '- ⁇ 5-bromo-6- [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N-methylimidoformamide, (1.079) N'- ⁇ 5 - bromo-6- [(trans-4-isopropylcyclo
  • inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isoietamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR , 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1
  • 3) respiratory chain inhibitors on complex III for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(IE)
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3- ⁇ 1 ⁇ -4- (2,6 ⁇ ⁇ 1 ⁇ 6 ⁇ 1) -6- ⁇ 6 ⁇ 1 ⁇ 1-5phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6- difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2 -Brom-4-fluoro-1-yl) -
  • Copper naphthenate (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2 +) sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015 ) Metiram, (5.016) Zinc Metiram, (5.017) Copper Oxine, (5.018) Propineb, (5.019) Sulfur and Sulfur Preparations Including Calcium Polysulfide, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Compounds capable of inducing host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
  • inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil,
  • inhibitors of cell wall synthesis for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
  • Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
  • Inhibitors of melanin biosynthesis for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • 12) inhibitors of nucleic acid synthesis for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • the compounds of the formula (I) or the formula (II) can be combined with biological pesticides.
  • Bio pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 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 B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), - -
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton capsule worm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV Spodoptera frugiperda (armyworm) mNPV
  • Spodoptera littoralis African cotton worm
  • bacteria and fungi which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces 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 the formula (I) or of the formula (II) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4-
  • safeners for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic
  • Plants and Plant Parts can be treated.
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes).
  • Crop plants can be plants 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, such as seeds, cuttings, young (unripe) plants and 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 harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • plants and their parts can be treated.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • the genes which confer the desired properties can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, - -
  • Tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape are particularly emphasized , Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of the formula (I) or the formula ( ⁇ ) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) or the formula (II) by the ultra-low-volume method or the use form or the compound of the formula (I) or the Inject formula ( ⁇ ) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. H. the compounds of the formula (I) or of the formula (II) are applied to the foliage, wherein the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.
  • the compounds of the formula (I) or of the formula (II) 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) or formula ( ⁇ ) on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I) or formula (II), or by the soil application, i. H. the compounds of the formula (I) or the formula (II) according to the invention are introduced into the plant in solid form (for example in the form of granules). In water rice crops, this may also be by metered addition of the compound of formula (I) or formula (II) in a solid form (eg as granules) into a flooded paddy field.
  • Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to 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 have methods of protecting the seed and the germinating plant - - which make unnecessary, 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.
  • seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I) or formula (II).
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) or formula (II) and a mixture component. It also further comprises a method in which the seed is treated at different times with a compound of the formula (I) or the formula (II) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) or of the formula (II) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) or the formula ( ⁇ ) according to the invention.
  • the invention also relates to seed treated at the same time with a compound of formula (I) or formula (II) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of the formula (I) or the formula (II) and a mixture component.
  • the individual substances may be present in different layers on the seed.
  • the layers which comprise a compound of the formula (I) or of the formula (II) and of the mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) or the formula (II) and a mixture component are applied as a constituent of an envelope or as a further layer or further layers in addition to an envelope. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I) or the formula (II), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) or the formula ( ⁇ ) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) or formula (II) 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 occurs an optimized nitrogen fixation comes.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or occurs an optimized nitrogen fixation comes.
  • the compounds of the formula (I) or of the formula (II) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (such as wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
  • transgenic seed with a compound of the formula (I) or the formula (II) is also of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis. - -
  • the compound of the formula (I) or the formula (II) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
  • the compounds of the formula (I) or of the formula (II) 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) or of the formula (II) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the compounds of formula (I) or formula ( ⁇ ) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives , secondary thickeners, glues, gibberellins and even water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives , secondary thickeners, glues, gibberellins and even water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1. - -
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds - - become.
  • 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 seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water
  • all mixing devices which can usually be used for the dressing can be considered.
  • the seed is placed 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) or of the formula (II) in the formulations and according to the seed.
  • the application rates in the compound of the formula (I) or of the formula (II) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) or of formula (II) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of the formula (I) or of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for the control of parasites used in livestock and animal husbandry in livestock, breeding animals, zoo animals, laboratory animals, Experimental animals and pets occur. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees. - -
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
  • the compounds of the formula (I) or the formula (II) are administered to mammals.
  • the compounds of the formula (I) or of the formula (II) are administered to birds, namely caged birds or, in particular, poultry.
  • controlling means that the compounds of the formula (I) or the formula ( ⁇ ) are effective for the occurrence of the respective parasite in an animal that is infected with such parasites is infected to a harmless extent, is reduced. More specifically, “combat” in the present context means that the compounds of the formula (I) or the formula ( ⁇ ) kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomy
  • Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephal
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as: Metamonada: from the order Vaccinonadida, for example Giardia spp., Spironucleus spp.
  • Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
  • Euglenozoa from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
  • Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; out of order - -
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea z.
  • Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Or
  • Nematodes from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • Coperosides spp. Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp , Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp.
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the compounds of the formula (I) or of the formula (II) are administered by methods which are generally known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
  • an embodiment of the present invention relates to the compounds of the formula (I) or the formula ( ⁇ ) for use as a medicament.
  • Another aspect relates to the compounds of formula (I) or formula ( ⁇ ) for use as antiendoparasitic. - -
  • Another specific aspect of the invention relates to the compounds of the formula (I) or of the formula (II) for use as antihelminthic agents, in particular for use as nematicide, platyhelminthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) or formula (II) for use as antiprotozoic.
  • Another aspect relates to the compounds of the formula (I) or the formula ( ⁇ ) for use as anti-topazarasitic, in particular an arthropodicide, very particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of formula (I) or formula (II) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluent), a pharmaceutically acceptable adjuvant (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg solid or liquid diluent
  • a pharmaceutically acceptable adjuvant eg surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) or formula (II) with pharmaceutically acceptable excipients and / or adjuvants, especially conventionally in veterinary medicine
  • Formulations used include pharmaceutically acceptable excipients and / or adjuvants conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by using an effective amount of a compound of the formula (I) or the formula ( ⁇ ) an animal, especially a nonhuman animal, that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of those mentioned here Ectoparasites and endoparasites, by applying a veterinary formulation as defined herein to an animal, especially a non-human animal in need thereof.
  • Another aspect relates to the use of the compounds of the formula (I) or of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular one nonhuman animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of the formula (I) or of the formula (II) with other active substances, in particular with endo- and ectoparasiticides, are provided hereby for the veterinary field.
  • blending not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances should be formulated in a common formulation, or all active substances should be formulated in separate formulations, or mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
  • Active substances with unknown or non-specific mechanisms of action eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
  • Organochlorine compounds e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroids, e.g.
  • Neonicotinoids e.g. B. Nithiazin Dicloromezotiaz, Triflumezopyrim macrocyclic lactones, eg. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
  • Biologicals, hormones or pheromones for example natural products, eg thuringiensin, codlemon or neem components Dinitrophenols, e.g. Dinocap, dinobuton, binapacryl;
  • Benzoylureas eg. Fluazuron, penfluron,
  • Amidine derivatives e.g. B. Chlormebuform, cymiazole, demiditraz
  • Hive varroa acaricides for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides, as a mixture partner include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flu
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
  • all said mixing partners can optionally form salts with suitable bases or acids.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Ticks Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vector control is also possible when the compounds of formula (I) or formula (II) are resistance-disrupting.
  • Compounds of formula (I) or formula (II) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) or formula ( ⁇ ) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials.
  • the compounds of the formula (I) or the formula (II) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the application of the invention for the protection of wood is particularly preferred.
  • the compounds of the formula (I) or of the formula (II) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of the formula (I) or of the formula (II) are present as ready-to-use pesticides, ie they can be applied to the corresponding material without further changes.
  • insecticides or fungicides in particular those mentioned above come into question. - -
  • the compounds of the formula (I) or of the formula (II) protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. can be used.
  • the compounds of the formula (I) or the formula (II) can be used alone or in combinations with other active substances as antifouling agents.
  • the compounds of the formula (I) or of the formula (II) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry.
  • the compounds of the formula (I) or of the formula (II) are used alone or in combination with other active ingredients and / or adjuvants.
  • they are used in household insecticide products.
  • the compounds of formula (I) or formula (II) are effective against sensitive and resistant species as well as 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, non-pressurized sprays, z.
  • the calibration is carried out with un branched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by retention times by linear interpolation between two consecutive alkanones).
  • the NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists.
  • the IH-NMR data of selected examples are recorded in the form of IH-NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; 5i (intensity;; ⁇ ⁇ (intensity);
  • 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.
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints.”
  • the vials are filled with 5-10 adult cat fleas ⁇ Ctenocephalides felis), closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
  • 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.
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. 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.
  • Solvent dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
  • 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 active ingredient preparation 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.
  • IPL41 insect medium 33% + 15% sugar
  • 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) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae j.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
  • 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.
  • Emulsifier alkylaryl polyglycol ether
  • Paprika plants Capsicum annuum which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.

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  • Nitrogen Condensed Heterocyclic Rings (AREA)
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Abstract

The invention relates to new compounds of formula (I) or (I') where R1, Aa, Ab, Ac, Ad, Q and n have the meanings indicated in the description, to the use thereof as acaricides and/or insecticides for controlling animal pests, and to methods and intermediate products for the production thereof.

Description

Kondensierte bicyclische Heterocyclen-Derivate als Schädlingsbekämpfungsmittel  Condensed bicyclic heterocyclic derivatives as pesticides
Die vorliegende Erfindung betrifft neue kondensierte bicyclische Heterocyclen-Derivate der Formel (I) oder der Formel (Γ), deren Anwendung als Akarizide und/oder Insektizide zur Bekämpfung tierischer Schädlinge, vor allem von Arthropoden und insbesondere von Insekten und Spinnentieren und Verfahren und Zwischenprodukte zu ihrer Herstellung. The present invention relates to novel condensed bicyclic heterocyclic derivatives of the formula (I) or the formula (Γ), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular of insects and arachnids, and methods and intermediates their production.
Kondensierte bicyclische Heterocyclen-Derivate mit Insektiziden Eigenschaften sind in der Literatur bereits beschrieben, z.B. in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557, EP 15191440.5, WO 2015/121136, WO 2016/129684, PCT/EP2016/057389, EP 15197267.6, EP 16168252.1, EP 16184163.0, EP16189445.6. Condensed bicyclic heterocyclic derivatives having insecticidal properties have already been described in the literature, e.g. in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557 , EP 15191440.5, WO 2015/121136, WO 2016/129684, PCT / EP2016 / 057389, EP 15197267.6, EP 16168252.1, EP 16184163.0, EP16189445.6.
Die gemäß den oben genannten Schriften bereits bekannten Wirkstoffe weisen aber in ihrer Anwendung teils Nachteile auf, sei es, dass sie nur eine geringe Anwendungsbreite aufweisen, sei es, dass sie keine zufriedenstellende Insektizide oder akarizide Wirkung aufweisen. However, the active ingredients already known according to the abovementioned publications have some drawbacks in their application, be it that they have only a small application range, whether they have no satisfactory insecticides or acaricidal activity.
Es wurden nun neue kondensierte bicyclische Heterocyclen-Derivate gefunden, welche gegenüber den bereits bekannten Verbindungen Vorteile aufweisen, z.B. seien bessere biologische oder ökologische Eigenschaften, breitere Anwendungsmethoden, eine bessere Insektizide, akarizide Wirkung, sowie eine gute Verträglichkeit gegenüber Nutzpflanzen beispielhaft genannt. Die kondensierten bicyclischen Heterocyclen-Derivate können in Kombination mit weiteren Mitteln zur Verbesserung der Wirksamkeit insbesondere gegen schwierig zu bekämpfende Insekten eingesetzt werden. There have now been found new condensed bicyclic heterocyclic derivatives which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, better insecticides, acaricidal activity, as well as a good tolerance to crops exemplified. The condensed bicyclic heterocyclic derivatives can be used in combination with other agents for improving the effectiveness in particular against difficult-to-control insects.
Gegenstand der vorliegenden Erfindung sind daher neue Verbindungen der Formeln (I) oder (Γ) The present invention therefore relates to novel compounds of the formulas (I) or (II)
Figure imgf000002_0001
Figure imgf000002_0001
(I) (Γ) in welchen (Ausgestaltung 1) (I) (Γ) in which (embodiment 1)
Aa für Stickstoff oder ^ (ein Kohlenstoffatom mit einer Doppebindung zu Ab bzw. Ad) steht, Ab für =N-, -S(0)m-, -O-, -N(R7)-, =C(R2)- oder -C(R9)(R10)- steht, - - Aa is nitrogen or ^ (a carbon atom with a double bond to Ab or Ad), Ab for = N-, -S (0) m -, -O-, -N (R 7 ) -, = C (R 2 ) - or -C (R 9 ) (R 10 ) - is, - -
Ac für =N-, -S(0)m-, -O-, -N(R7)-, =C(R3)- oder -C(RU)(R12)- steht, Ac represents = N-, -S (O) m -, -O-, -N (R 7 ) -, = C (R 3 ) - or -C (R U ) (R 12 ) -,
Ad für =N-, -S(0)m-, -O-, -N(R7)-, =C(R8)- oder -C(R13)(R14)- steht, wobei nur einer der Substituenten Ab, Ac oder Ad für Sauerstoff oder -S(0)m- stehen kann, Ad is = N-, -S (O) m -, -O-, -N (R 7 ) -, = C (R 8 ) - or -C (R 13 ) (R 14 ) -, where only one the substituent Ab, Ac or Ad may be oxygen or -S (0) m -,
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, (Ci- C6)Alkoxy-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyl, (C2-R 1 alkyl is (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C 6) , (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -
C6)Alkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(Ci-C6)alkyl, (C2-C6) alkenyloxy (Ci-C6) alkyl, (C2-C6) Halogenalkenyloxy- (Ci-C6) alkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl , (C 2 -C 6) alkynyloxy (Ci-C 6) alkyl, (C 2 -
C6)Halogenalkinyloxy-(Ci-C6)alkyl, (C2-Ce)Halogenalkinyl, (C2-Ce)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, Amino, (Ci-C6)Alkylamino, Di-(Ci-C6)alkyl-amino, (C3-C6) Halogenalkinyloxy- (Ci-C6) alkyl, (C2 -Ce) haloalkynyl, (C2 -Ce) cyanoalkynyl, (C3- C8) cycloalkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl , (Ci-C 6) alkyl (C 3 -C 8) cycloalkyl, halo (C3-C8) cycloalkyl, amino, (Ci-C6) alkylamino, di (Ci-C6) alkyl-amino, (C3-
C8)Cycloalkylamino, (Ci-C6)Alkylcarbonyl-amino, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci- C6)Halogenalkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci- C8) cycloalkylamino, (Ci-C6) alkylcarbonyl-amino, (Ci-C6) alkylthio (Ci-C6) alkyl, (Ci- C 6) haloalkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfinyl- (C 1 -C 6 ) -alkyl,
C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C 6) Halogenalkylsulfinyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-
C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkylthio-(Ci-C6)alkyl, (Ci- C6)Alkoxy-(Ci-C6)alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfonyl-(Ci-C6)alkyl,C 6) haloalkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci-C 6) alkylthio- (Ci-C 6) alkyl, (Ci- C6) alkoxy (Ci-C 6) alkyl alkylsulfinyl (Ci-C 6), (Ci-C6) alkoxy (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl,
(Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl, (Ci- C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxycarbonyl-(Ci-C6)alkyl, (Ci- C6)Alkylsulfonylamino, Aminosulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylaminosulfonyl-(Ci-C6)alkyl, Di-(Ci-C6)alkyl-aminosulfonyl-(Ci-C6)alkyl, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, (Ci-C6) alkylcarbonyl (Ci-C 6) alkyl, (Ci-C6) haloalkylcarbonyl (Ci-C 6) alkyl, (Ci- C6) alkoxycarbonyl (Ci-C6) alkyl, (Ci-C6 ) Haloalkoxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylsulfonylamino, aminosulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminosulfonyl- (C 1 -C 6) -alkyl, di- (C 1 -C 6) -alkylaminosulfonyl - (C 1 -C 6) alkyl, or in each case optionally mono- or polysubstituted, identically or differently, by aryl,
Hetaryl oder Heterocyclyl substituiertes (Ci-Ce)Alkyl, (Ci-C6)Alkoxy, (C2-C6)Alkenyl, (C2- C6)Alkinyl, (C3-C8)Cycloalkyl steht, wobei Aryl, Hetaryl oder Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (Ci- C6)Alkoxy, (Ci-C6)Halogenalkyl, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Alkylsulfinyl,Hetaryl or heterocyclyl substituted (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 3 -C 8 ) cycloalkyl, wherein aryl, hetaryl or heterocyclyl respectively optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, C 6) haloalkyl, (Ci-C 6) haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) alkylsulfinyl,
(Ci-C6)Alkylsulfonyl, (Ci-C6)Alkylsulfimino, (Ci-C6)Alkylsulfimino-(Ci-C6)alkyl, (Ci- C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkylsulfoximino, (Ci-C6)Alkylsulfoximino-(Ci- Ce)alkyl, (Ci-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci- C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Benzyl substituiert sein können, oder R1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (Ci-C6)Alkyl, (C3-C8)Cycloalkyl, (Ci- C6)-Alkoxy, (Ci-C6)Halogenalkyl, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Alkyl- sulfinyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Alkylsulfimino, (Ci-C6)Alkylsulfimino-(Ci-C6)alkyl, (Ci- C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkylsulfoximino, (Ci-C6)Alkylsulfoximino- (Ci-C6)alkyl, (Ci-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci- - - (Ci-C 6) alkylsulfonyl, (Ci-C 6) Alkylsulfimino, (Ci-C 6) Alkylsulfimino- (Ci-C 6) alkyl, (Ci- C6) Alkylsulfimino- (C 2 -C 6) alkylcarbonyl, (Ci- C6) alkylsulfoximino, (C 1 -C 6) -alkylsulfoximino (ci-ce) -alkyl, (C 1 -C 6) -alkylsulfoximino (C 2 -C 6) -alkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -alkylcarbonyl, (C 3 -C 6) -cycloalkyl C6) trialkylsilyl or benzyl, or R 1 is in each case optionally monosubstituted or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) Cycloalkyl, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) haloalkoxy, (Ci-C 6 ) alkylthio, (Ci-C 6 ) alkylsulfinyl, (Ci-C 6 ) alkylsulfonyl, (Ci-C 6) Alkylsulfimino, (Ci-C 6) Alkylsulfimino- (Ci-C 6) alkyl, (Ci- C6) Alkylsulfimino- (C 2 -C 6) alkylcarbonyl, (Ci-C6) Alkylsulfoximino, ( Ci-C6) Alkylsulfoximino- (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfoximino- (C 2 -C 6) alkylcarbonyl, (Ci-C 6) alkoxycarbonyl, (Ci- - -
Ce)Alkylcarbonyl, (C3-C6)Trialkylsilyl, (=0) (nur im Fall von Heterocyclyl) oder (=0)2 (nur im Fall von Heterocyclyl) substituiertes Aryl, Hetaryl oder Heterocyclyl steht, Ce) alkylcarbonyl, (C 3 -C 6) trialkylsilyl, (= 0) (only in the case of heterocyclyl) or (= 0) 2 (only in the case of heterocyclyl) substituted aryl, hetaryl or heterocyclyl,
R2, R3, R8, R9, R10, R11, R12, R13, R14 unabhängig voneinander für Wasserstoff, Cyano, Halogen, R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another represent hydrogen, cyano, halogen,
Nitro, Acetyl, Hydroxy, Amino, SCN, Tri-(Ci-C6)alkylsilyl, (C3-C8)Cycloalkyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)cycloalkyl, Halogen(C3- C8)cycloalkyl, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci- Ce)Hydroxyalkyl, Hydroxycarbonyl-(Ci-Ce)-alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci- C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2- Ce)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci- Ce)Alkoxy, (Ci-Ce)Halogenalkoxy, (Ci-Ce)Cyanoalkoxy, (Ci-C6)Alkoxycarbonyl-(Ci- C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci-C6)Alkylhydroxyimino, (Ci- C6)Alkoxyimino, (Ci-C6)Alkyl-(Ci-C6)alkoxyimino, (Ci-C6)Halogenalkyl-(Ci- C6)alkoxyimino, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-Ce)Alkoxy-(Ci- C6)alkylthio, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl, (Ci- C6)Halogenalkylsulfinyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfinyl, (Ci-C6)Alkylsulfinyl-(Ci- C6)alkyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, (Ci-C6)Alkoxy-(Ci- C6)alkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyloxy, (Ci- Ce)Alkylcarbonyl, (Ci-C6)Alkylthiocarbonyl, (Ci-C6)Halogenalkylcarbonyl, (Ci- Ce)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci-Nitro, acetyl, hydroxy, amino, SCN, tri- (Ci-C 6) alkylsilyl, (C 3 -C 8) cycloalkyl, (C 3 - C 8) cycloalkyl, (C3-C8) cycloalkyl, (Ci-C 6) alkyl- (C 3 -C 8) cycloalkyl, halo (C 3 - C 8) cycloalkyl, (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci- Ce) hydroxyalkyl, hydroxycarbonyl (Ci-Ce) alkoxy, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C 6) alkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 - Ce) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) haloalkynyl, (C 2 -C 6) cyanoalkynyl, (Ci- Ce) Alkoxy, (C 1 -C 6) haloalkoxy, (C 1 -C 6) cyanoalkoxy, (C 1 -C 6) alkoxycarbonyl- (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxy- (C 1 -C 6) alkoxy, (C 1 -C 6) -alkylhydroxyimino , (Ci- C6) alkoxyimino (Ci-C6) alkyl (Ci-C6) alkoxyimino (Ci-C6) haloalkyl (Ci- C 6) alkoxyimino, (Ci-C 6) alkylthio, (Ci-C 6 ) haloalkylthio, (Ci-Ce) alkoxy (Ci- C6) alkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) alkylsulfinyl, (Ci- C 6) haloalkylsulfinyl, (Ci-C 6) alkoxy (Ci-C 6) alkylsulfinyl, (Ci-C 6) Alkylsulfin yl- (Ci- C6) alkyl, (Ci-C 6) alkylsulfonyl, (Ci-C 6) haloalkylsulfonyl, (Ci-C 6) alkoxy (Ci- C6) alkylsulfonyl, (Ci-C 6) alkylsulfonyl (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfonyloxy, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) alkylthiocarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6) alkylcarbonyloxy, (C 1 -C 6) alkoxycarbonyl , (Ci-C6) haloalkoxycarbonyl, aminocarbonyl, (Ci-C6) alkylaminocarbonyl, (Ci-C6) alkylaminothiocarbonyl, di (C
C6)alkyl-aminocarbonyl, Di-(Ci-C6)alkyl-aminothiocarbonyl, (C2-C6) alkylaminocarbonyl, di (Ci-C6) alkylaminothiocarbonyl, (C2-
C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3-C6) alkenylaminocarbonyl, di- (C2-C6) -alkenylaminocarbonyl, (C3-
C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylamino, Di-(Ci- C6)Alkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci-Ce)alkyl- aminosulfonyl, (Ci-C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci- C8) cycloalkylaminocarbonyl (Ci-C6) alkylsulfonylamino, (Ci-C6) alkylamino, di (Ci- C6) alkylamino, aminosulfonyl, (Ci-C6) alkylaminosulfonyl, di (Ci-Ce) alkyl aminosulfonyl, (C -C6) alkylsulfoximino, aminothiocarbonyl, (
C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkyl-aminothiocarbonyl, (C3-C6) alkylaminothiocarbonyl, di (Ci-C6) alkylaminothiocarbonyl, (C3-
C8)Cycloalkylamino oder NHCO-(Ci-Ce)alkyl ((Ci-C6)Alkylcarbonylamino) stehen, für Wasserstoff, Acetyl, (Ci-C4)Alkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C3- C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio- (Ci-C4)alkyl, (Ci-C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci- C4)Halogenalkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl, (Ci- C4)Alkylcarbonyl-(Ci-C4)alkyl, (Ci-C4)Halogenalkylcarbonyl-(Ci-C4)alkyl, - - oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl steht, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, Cyano, (Ci-C4)Alkyl, (C3-C4)Cycloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkyl, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylsulfinyl oder (Ci-C4)Alkylsulfonyl, substituiert sein können, für ein teilweise gesättigtes oder gesättigtes heterozyklisches oder heteroaromatisches 8-, 9-, 10-, 11 - oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem steht, wobei gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und/oder wobei das Ringsystem gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiert ist, und wobei die Substituenten unabhängig voneinander ausgewählt sein können aus Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, Tri-(Ci-C6)alkylsilyl, (C3-C8)Cycloalkyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, Hydroxycarbonyl-(Ci-C6)-alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci- C6)alkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2- C6)Alkinyloxy-(Ci-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-C6)Alkoxy, (Ci- C6)Halogenalkoxy, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyloxy-(Ci-C6)alkyl, (C2- C6)Halogenalkenyloxy-(C i-Ce) alkyl, (C i -Ce)Cy anoalkoxy , (C i -Ce) Alkoxycarbonyl-(C i - Ce)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci-C6)Alkylhydroxyimino, (Ci-C6)Alkoxyimino, (Ci-C6)Alkyl-(Ci-C6)alkoxyimino, (Ci-C6)Halogenalkyl-(Ci-C6)alkoxyimino, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkoxy-(Ci-C6)alkylthio, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci- C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfinyl, (Ci- C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, (Ci- C6)Alkoxy-(Ci-C6)alkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyloxy, (Ci-C6)Alkylcarbonyl, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkylthiocarbonyl, (Ci- Ce)Halogenalkylcarbonyl, (Ci-C6)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci- Ce)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, (Ci- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, Di-(Ci-Ce)alkyl- aminothiocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3- C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylamino, Di-(Ci- C6)Alkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci-C6)alkyl-aminosulfonyl, (Ci-C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci- C6)alkyl-aminothiocarbonyl, (C3-C8)Cycloalkylamino, NHCO-(Ci-C6)alkyl ((Ci- C8) cycloalkylamino or NHCO- (Ci-Ce) alkyl ((Ci-C6) alkylcarbonylamino are) hydrogen, acetyl, (Ci-C 4) alkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) haloalkyl, (Ci C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl , (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4) alkyl, (C 2 - C 4) Halogenalkinyloxy- (Ci-C 4) alkyl, (C2-C 4) haloalkynyl, (C2-C 4) cyanoalkynyl, (C3- C6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci- C 4) alkylthio (Ci-C 4) alkyl, (Ci-C4) haloalkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4) alkyl, (Ci C 4 ) Halogenalkylsulfinyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, (Ci C 4) alkylcarbonyl (Ci-C 4) alkyl, (Ci-C4) haloalkylcarbonyl - (C 1 -C 4 ) alkyl, - or for each optionally mono- or disubstituted by identical or different aryl or heterocyclyl (Ci-C alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, wherein each aryl or heterocyclyl optionally single or double the same or different halogen, cyano, (Ci-C 4) alkyl, (C 3 -C 4) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkyl, (CI-C 4) haloalkoxy, ( Ci-C 4) alkylthio, (Ci-C4) alkylsulphinyl or (Ci-C 4) alkylsulfonyl, may be substituted for a partially saturated or saturated heterocyclic or heteroaromatic 8-, 9-, 10-, 11 -, or 12- wherein the ring system is optionally monosubstituted or polysubstituted, identically or differently, and wherein the substituents can be independently selected from cyano, halogen, nitro, acetyl , Hydroxy, Amino, SCN, tri- (Ci-C 6) alkylsilyl, (C 3 -C 8) cycloalkyl, (C 3 - C 8) cycloalkyl (C 3 -C 8) cycloalkyl, (Ci-C6) alkyl- ( C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, hydroxycarbonyl- (Ci-C6) alkoxy, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C6) alkoxy (Ci- C6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 - C 6) alkynyloxy (Ci-C4) alkyl, (C 2 -C 6) haloalkynyl , (C 2 -C 6) cyanoalkynyl, (Ci-C 6) alkoxy, (Ci- C 6) haloalkoxy, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyloxy (C 1 -C 6 ) alkyl, (C 2 -C 6) haloalkenyloxy (C 1 -C 6) -alkyl, (C 1 -C 6) -cycloalkoxy, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkoxy, (C 1 -C 6) alkoxy- (C 1 -C 6) alkoxy, (C 1 -C 6) alkylhydroxyimino, (C 1 -C 6) alkoxyimino, (C 1 -C 6) alkyl- (C 1 -C 6) alkoxyimino, (C 1 -C 6) -haloalkyl- ( Ci-C6) alkoxyimino (Ci-C6) alkylthio, (Ci-C 6) haloalkylthio, (Ci-C 6) alkoxy (Ci-C 6) alkylthio, (C i-C 6) alkylthio (Ci-C 6) alkyl, (Ci- C6) alkylsulfinyl, (Ci-C 6) haloalkylsulfinyl, (Ci-C 6) alkoxy (Ci-C 6) alkylsulfinyl, (Ci- C 6 ) alkylsulfinyl (Ci-C6) alkyl, (Ci-C 6) alkylsulfonyl, (Ci-C 6) haloalkylsulfonyl, (Ci- C6) alkoxy (Ci-C 6) alkylsulfonyl, (Ci-C 6) alkylsulfonyl - (Ci-C6) alkyl, (Ci-C 6) alkylsulfonyloxy, (Ci-C 6) alkylcarbonyl, (Ci-C6) alkylcarbonyl (Ci-C 6) alkyl, (Ci-C 6) alkylthiocarbonyl, ( Ci- Ce) haloalkylcarbonyl, (C 1 -C 6) alkylcarbonyloxy, (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkylaminocarbonyl, (C 1 -C 6) -alkylaminothiocarbonyl, di- (C 1 -C 6) alkyl-aminocarbonyl, di- (Ci-Ce) alkyl- aminothiocarbonyl, (C 2 -C 6) alkenylaminocarbonyl, di- (C 2 -C 6) -alkenylaminocarbonyl, (C 3 - C 8) cycloalkylaminocarbonyl (Ci-C6) alkylsulfonylamino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamino, aminosulphonyl, (C 1 -C 6) alkylaminosulphonyl, di (C 1 -C 6) alkylaminosulphonyl, (C 1 -C 6) -alkylsulphoximino, aminothiocarbonyl, (C 1 -C 6) Alkylaminothiocarbonyl, di (C C 6 ) alkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylamino, NHCO- (C 1 -C 6 ) -alkyl (C 1 -C 4 )
CÖ) Alkylcarbonylamino) , - - oder wobei die Substituenten unabhängig voneinander ausgewählt sein können aus Phenyl oder einem 5- oder 6-gliedrigen heteroaromatischen Ring, wobei Phenyl oder der Ring gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Ci-C6-Haloalkyl, C2-C6-Haloalkenyl, C2-C6-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy substituiert sein können, für 0, 1 oder 2 steht, für 0, 1 oder 2 steht, CÖ) alkylcarbonylamino), - or wherein the substituents may be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl , C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN , NO 2 , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, is 0, 1 or 2, stands for 0, 1 or 2,
ausgenommen
Figure imgf000006_0001
except
Figure imgf000006_0001
Je nach Definition der Substituenten Aa, Ab, Ac, Ad ergeben sich aromatische, gestättigte oder teilgesättigte Ringe. Depending on the definition of the substituents Aa, Ab, Ac, Ad, aromatic, saturated or partially saturated rings are obtained.
Weiterhin wurde gefunden, dass die Verbindungen der Formeln (I) oder (Γ) eine sehr gute Wirksamkeit als Schädlingsbekämpfungsmittel, vorzugsweise als Insektizide und/oder Akarizide aufweisen, darüber hinaus in der Regel insbesondere gegenüber Kulturpflanzen sehr gut pflanzenverträglich sind. Furthermore, it has been found that the compounds of the formulas (I) or (II) have very good activity as pesticides, preferably as insecticides and / or acaricides, moreover, as a rule, are very well tolerated by plants, in particular with respect to crop plants.
Die erfindungsgemäßen Verbindungen sind durch die Formeln (I) oder (Γ) allgemein definiert. Bevorzugte Substituenten bzw. Bereiche der in der oben und nachstehend erwähnten Formeln aufgeführten Reste werden im Folgenden erläutert: The compounds according to the invention are generally defined by the formulas (I) or (II). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
Ausgestaltung 2 Embodiment 2
Aa steht bevorzugt für Stickstoff, Aa is preferably nitrogen,
Ab steht bevorzugt für =N-, -S(0)m-, -O-, -N(R7)-, =C(R2)- oder -C(R9)(R10)-, Ac steht bevorzugt für =N-, -S(0)m-, =C(R3)- oder -C(RU)(R12)-, Ad steht bevorzugt für =N-, -S(0)m-, -O-, -N(R7)-, =C(R8)- oder -C(R13)(R14)-, wobei nur einer der Substituenten Ab, Ac oder Ad für Sauerstoff oder -S(0)m- stehen kann, wobei sich bevorzugt die folgenden Struktureinheiten AI bis A20 ergeben: - - Ab is preferably = N-, -S (0) m -, -O-, -N (R 7 ) -, = C (R 2 ) - or -C (R 9 ) (R 10 ) -, Ac stands preferably represents = N-, -S (0) m -, C (R 3) = - or -C (R U) (R 12) -, ad preferably represents = N-, -S (0) m -, -O-, -N (R 7 ) -, = C (R 8 ) - or -C (R 13 ) (R 14 ) -, where only one of the substituents Ab, Ac or Ad for oxygen or -S (0) m - may be, preferably giving the following structural units AI to A20: - -
Figure imgf000007_0001
- -
Figure imgf000007_0001
- -
R1 steht bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci- C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-C4)Cycloalkyl, (Ci- C4)Alkoxy oder (Ci-C4)Alkylthio substituiert sein können, oder R 1 is preferably (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkylthio (Ci -C 4) alkyl, (Ci-C 4) alkylsulfinyl (CI-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, or represents in each case optionally monosubstituted or disubstituted by identical or different substituents aryl or heterocyclyl substituted (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (C 3 -C 6) cycloalkyl, wherein aryl or heterocyclyl each optionally monosubstituted or disubstituted by identical or different halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C3-C4) cycloalkyl, (Ci C 4) alkoxy or (Ci-C 4) alkylthio may be substituted, or
R1 steht bevorzugt für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)Halogenalkyl, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (=0) (nur im Fall von Heterocyclyl) oder (=0)2 (nur im Fall von Heterocyclyl) substituiertes Aryl, Hetaryl oder Heterocyclyl, R 1 preferably represents in each case optionally monosubstituted or disubstituted by identical or different halogen, cyano, (Ci-C 4) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4 ) haloalkyl, (CI-C 4) haloalkoxy, (Ci-C 4) alkylthio, (= 0) (only in the case of heterocyclyl) or (= 0) 2 (substituted only in the case of heterocyclyl) aryl, hetaryl or heterocyclyl,
R2, R3, R8, R9, R10, R11, R12, R13, R14 stehen unabhängig voneinander bevorzugt für Wasserstoff, R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another preferably represent hydrogen,
Cyano, Halogen, Nitro, Hydroxy, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3- C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci- C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-Cyano, halo, nitro, hydroxy, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (CI-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) haloalkynyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (CI-C 4) alkylthio, (Ci-C 4) Haloalkylthio, (C 1 -C 4 ) alkylsulfinyl,
C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci- C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Aminosulfonyl, (Ci-C 4) haloalkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C4) haloalkylsulfonyl, (Ci- C4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, aminocarbonyl, (Ci- C4) alkylaminocarbonyl, di- ( Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, aminosulfonyl, (Ci
C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci- C4) Alkylcarbonylamino) , C 4) alkylaminosulfonyl, di (Ci-C 4) alkyl-aminosulfonyl or alkyl (NHCO- (Ci-C 4) (Ci -C 4) alkylcarbonylamino),
R7 steht bevorzugt für Wasserstoff, Acetyl, (Ci-C )Alkyl, (Ci-C )Halogenalkyl, (Ci-C )Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, (Ci-C4)Alkyl, Cyano, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkyl oder (Ci-C4)Halogenalkoxy substituiert sein können, R 7 is preferably hydrogen, acetyl, (Ci-C) alkyl, (Ci-C) haloalkyl, (Ci-C) cyanoalkyl, (Ci-C 4 ) alkoxy (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (Ci -C 4) alkylthio (Ci-C 4) alkyl, or represents in each case optionally mono- or disubstituted by identical or different aryl or heterocyclyl substituted (Ci-C 4) alkyl, wherein aryl or heterocyclyl each optionally monosubstituted or disubstituted by identical or different haloalkoxy may be substituted by halogen, (Ci-C 4) alkyl, cyano, (Ci C 4) alkoxy, (Ci-C 4) -haloalkyl or (Ci-C 4),
Q steht bevorzugt für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql bis QU, Q14 bis Q17 oder Q20, Q preferably represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to QU, Q14 to Q17 or Q20,
Figure imgf000009_0001
Figure imgf000009_0001
R4 steht bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, - - R 4 is preferably (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, - -
C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3- C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl, (C 2 - C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4) alkyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl , (C 1 -C 4 ) alkylsulfinyl
(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl, (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl or (Ci-C 4) alkylcarbonyl (Ci-C 4) alkyl,
R5, R6 stehen unabhängig voneinander bevorzugt für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3- C6)cycloalkyl, (Ci-C )Alkoxy, (Ci-C )Halogenalkoxy, (Ci-C )Alkoxyimino, (Ci-C )Alkylthio,R 5, R 6 independently of one another preferably represent hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxyimino, (C 1 -C 4) -alkylthio,
(Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C )Alkylsulfonyl, (Ci-C )Halogenalkylsulfonyl, (Ci-C )Alkylsulfonyloxy, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl, n steht bevorzugt für 0, 1 oder 2, m steht bevorzugt für 0, 1 oder 2. Ausgestaltung 3 (Ci-C4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (CI-C) alkylsulfonyl, (Ci-C) haloalkylsulfonyl, (Ci-C) alkylsulfonyloxy, (Ci C 4 ) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C 4) alkylamino, di - (Ci- C4) alkylamino, aminosulfonyl, (Ci-C4) alkylaminosulfonyl or di- (Ci-C4) alkylaminosulfonyl, n is preferably 0, 1 or 2, m is preferably 0, 1 or 2. Structuring 3
Aa steht besonders bevorzugt für Stickstoff, Ab steht besonders bevorzugt für =N-, -O-, -N(R7)- oder =C(R2)-, Ac steht besonders bevorzugt für =N- oder =C(R3)-, Aa is particularly preferably nitrogen, Ab is particularly preferably = N-, -O-, -N (R 7 ) - or = C (R 2 ) -, Ac is particularly preferably = N- or = C (R 3 ) -,
Ad steht besonders bevorzugt für =N-, -S(0)m-, -O-, -N(R7)- oder =C(R8)-, wobei nur einer der Substituenten Ab oder Ad für Sauerstoff oder -S(0)m- stehen kann. wobei sich besonders bevorzugt folgende Struktureinheiten ergeben: A5, A6, A7, A8, A9, A10, Al l, A12, A13, A19, A20, Ad is particularly preferably = N-, -S (0) m -, -O-, -N (R 7 ) - or = C (R 8 ) -, wherein only one of the substituents Ab or Ad for oxygen or -S (0) m - can stand. the following structural units are particularly preferably obtained: A5, A6, A7, A8, A9, A10, Al1, A12, A13, A19, A20,
R1 steht besonders bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl oder (C3-C6)Cycloalkyl, R 1 particularly preferably represents (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 3 -C 6 ) -cycloalkyl,
R2, R3, R8 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Cyano, Halogen, R 2 , R 3 , R 8 independently of one another particularly preferably represent hydrogen, cyano, halogen,
Nitro, Hydroxy, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- - - Nitro, hydroxy, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, (Ci-C 4) alkyl, (C -C 4) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4 ) haloalkylthio, - -
C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci- C4)Halogenalkylsulfonyl, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl- aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci-C4)Alkylcarbonylamino), C 4 ) alkylsulfinyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, aminosulfonyl, (C 1 -C 4 ) -alkylaminosulfonyl, di- (C 1 -C 4) -alkylaminosulfonyl or NHCO- (C 1 -C 4) -alkyl ((C 1 -C 4) -alkylcarbonylamino),
R7 steht besonders bevorzugt für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Cyanoalkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl, R 7 particularly preferably represents hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (CI-C 4) cyanoalkyl or (Ci-C 4) alkoxy (Ci-C 4) alkyl,
Q steht besonders bevorzugt für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17, Q particularly preferably represents a 9-membered heteroaromatic bicyclic ring system of the series Q1, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17,
R4 steht besonders bevorzugt für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl , R 4 particularly preferably represents (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
R5 steht besonders bevorzugt für Halogen, (Ci-C4)Halogenalkyl, (Ci-C4)Halogenalkoxy oder (Ci- C4)Halogenalkylthio, R 5 is particularly preferably halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy or (C 1 -C 4) haloalkylthio,
R6 steht besonders bevorzugt für Wasserstoff, n steht besonders bevorzugt für 0, 1 oder 2, m steht besonders bevorzugt für 0. R 6 is particularly preferably hydrogen, n is particularly preferably 0, 1 or 2, m is particularly preferably 0.
Ausj Gestaltung 4 Ausj design 4
Aa steht ganz besonders bevorzugt für Stickstoff, Aa is very particularly preferably nitrogen,
Ab steht ganz besonders bevorzugt für =N- oder = =C(R2)-, Ab is very particularly preferably = N- or = = C (R 2 ) -,
Ac steht ganz besonders bevorzugt für =N- oder = =C(R3)-, Ac is very particularly preferably = N- or = = C (R 3 ) -,
Ad steht ganz besonders bevorzugt für -S(0)m-, - -O- oder -N(R7)-. wobei sich ganz besonders bevorzugt folgende Struktureinheiten ergeben: A6, A10, Al l, A12, A13, Ad is very particularly preferably -S (0) m -, - -O- or -N (R 7 ) -. where very particular preference is given to the following structural units: A6, A10, Al1, A12, A13,
Figure imgf000011_0001
Figure imgf000011_0001
A12 A13 R1 steht ganz besonders bevorzugt für Ethyl, A12 A13 R 1 very particularly preferably represents ethyl,
R2, R3 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, R 2 , R 3 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Iod, Cyano, Methyl, Ethyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Trifluormethylthio,  Bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
R7 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, sec-Propyl oder tert.-Butyl, steht ganz besonders bevorzugt für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q2 oder Q3, R 7 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, sec-propyl or tert-butyl, very particularly preferably represents a heteroaromatic 9-membered fused bicyclic ring system from the series Q 2 or Q 3,
Figure imgf000012_0001
Figure imgf000012_0001
R4 steht ganz besonders bevorzugt für Methyl, Ethyl, i-Propyl, Methoxymethyl oder Methoxyethyl, R 4 very particularly preferably represents methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
R5 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl (CH2CFH2, CHFCH3), Difluorethyl (CF2CH3, CH2CHF2, CHFCFH2), Trifluorethyl, (CH2CF3, CHFCHF2, CF2CFH2), Tetrafluorethyl (CHFCF3, CF2CHF2), Pentafluorethyl, Trifluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy oder Trifluormethylthio, R 5 very particularly preferably represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
R6 steht ganz besonders bevorzugt für Wasserstoff, n steht ganz besonders bevorzugt für 0, 1 oder 2, m steht ganz besonders bevorzugt für 0. R 6 is very particularly preferably hydrogen, n is very particularly preferably 0, 1 or 2, m is very particularly preferably 0.
Ausgestaltung 5-1 Embodiment 5-1
Aa steht hervorgehoben für Stickstoff, Aa stands for nitrogen,
Ab steht hervorgehoben für =C(R2)-, Ab stands for = C (R 2 ) -,
Ac steht hervorgehoben für =C(R3)-, Ac stands for = C (R 3 ) -,
Ad steht hervorgehoben für -S(0)m-, wobei sich hervorgeoben folgende Struktureinheiten ergibt: Al l, R1 steht hervorgehoben für Ethyl, Ad stands for -S (0) m -, the result being the following structural units: Al 1, R 1 stands for ethyl,
R2, R3 stehen hervorgehoben für Wasserstoff, R 2 , R 3 are hydrogen,
Q steht hervorgehoben für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q3, R4 steht hervorgehoben für Methyl, Q stands out for a heteroaromatic 9-membered fused bicyclic ring system from the series Q3, R 4 stands for methyl,
R5 steht hervorgehoben für Trifluormethyl, R 5 stands for trifluoromethyl,
R6 steht hervorgehoben für Wasserstoff, n steht hervorgehoben für 0 oder 2, m steht hervorgehoben für 0. Ausgestaltung 5-2 R 6 stands for hydrogen, n stands for 0 or 2, m stands for 0. Configuration 5-2
Aa steht hervorgehoben für Stickstoff, Aa stands for nitrogen,
Ab steht hervorgehoben für =C(R2)-, Ab stands for = C (R 2 ) -,
Ac steht hervorgehoben für =C(R3)-, Ac stands for = C (R 3 ) -,
Ad steht hervorgehoben für -S(0)m-, wobei sich hervorgehoben folgende Struktureinheiten ergibt : A 11 , Ad stands for -S (0) m -, with the following structural units being highlighted: A 11,
R1 steht hervorgehoben für Ethyl, R 1 stands for ethyl,
R2 steht hervorgehoben für Wasserstoff, R 2 is hydrogen,
R3 steht hervorgehoben für Wasserstoff oder Trifluormethyl, R 3 is hydrogen or trifluoromethyl,
Q steht hervorgehoben für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q3, Q stands out for a heteroaromatic 9-membered fused bicyclic ring system from the series Q3,
R4 steht hervorgehoben für Methyl, R 4 is methyl,
R3 steht hervorgehoben für Trifluormethyl, R 3 stands for trifluoromethyl,
R6 steht hervorgehoben für Wasserstoff, n steht hervorgehoben für 0 oder 2, m steht hervorgehoben für 0. R 6 is hydrogen, n is 0 or 2, m is highlighted for 0.
Ausgestaltung 6-1 Embodiment 6-1
Aa steht insbesonders für Stickstoff,  Aa stands for nitrogen in particular,
Ab steht insbesonders für -C(R9)(R10)-, Ab stands in particular for -C (R 9 ) (R 10 ) -,
Ac steht insbesonders für -C(RU)(R12)-, Ac stands in particular for -C (R U ) (R 12 ) -,
Ad steht insbesonders für -C(R13)(R14)-, Ad stands in particular for -C (R 13 ) (R 14 ) -,
wobei sich insbesonders folgende Struktureinheiten ergibt: AI, in particular the following structural units are obtained: Al,
und Q, R1, R9, R10, R11, R12, R13, R14 und n die in Ausgestaltung 1 angegebenen Bedeutungen haben.and Q, R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 1.
Ausgestaltung 6-2 Embodiment 6-2
Aa steht insbesonders für Stickstoff, Aa stands for nitrogen in particular,
Ab steht insbesonders für -C(R9)(R10)-, Ab stands in particular for -C (R 9 ) (R 10 ) -,
Ac steht insbesonders für -C(Rn)(R12)-, Ac stands in particular for -C (R n ) (R 12 ) -,
Ad steht insbesonders für -C(R1 )(R14)-, Ad stands in particular for -C (R 1 ) (R 14 ) -,
wobei sich insbesonders folgende Struktureinheiten ergibt: AI , in particular the following structural units are obtained: Al,
und Q, R1, R4, R5, R6, R9, R10, R11, R12, R13, R14 und n die in Ausgestaltung 2 angegebenen Bedeutungen haben. and Q, R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 2.
Ausgestaltung 6-3  Embodiment 6-3
Aa steht insbesonders für Stickstoff,  Aa stands for nitrogen in particular,
Ab steht insbesonders für -C(R9)(R10)-, Ab stands in particular for -C (R 9 ) (R 10 ) -,
Ac steht insbesonders für -C(RU)(R12)-, Ac stands in particular for -C (R U ) (R 12 ) -,
Ad steht insbesonders für -C(R13)(R14)-, Ad stands in particular for -C (R 13 ) (R 14 ) -,
wobei sich insbesonders folgende Struktureinheiten ergibt: AI, in particular the following structural units are obtained: Al,
R1 steht insbesonders für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl oder (C3-C6)Cycloalkyl, R9, R10, R11, R12, R13, R14 stehen unabhäbgig voneinander insbesonders für Wasserstoff, (Ci-R 1 stands for particular (Ci-C 4) alkyl, (Ci-C 4) haloalkyl or (C 3 -C 6) cycloalkyl, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are, independently of one another, particularly hydrogen,
C4)Alkyl oder (Ci-C4)Halogenalkyl, C 4 ) alkyl or (C 1 -C 4 ) haloalkyl,
Q steht insbesonders für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17, R4 steht insbesonders für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl, Q is especially for a heteroaromatic 9-membered annelliertes bicyclic ring system from the series Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17, R 4 is in particular is (Ci-C 4) alkyl or (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl,
R5 steht insbesonders für Halogen, (Ci-C4)Halogenalkyl, (Ci-C4)Halogenalkoxy oder (Ci- C4)Halogenalkylthio, R 5 is in particular halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy or (Ci- C4) haloalkylthio,
R6 steht insbesonders für Wasserstoff, n steht insbesonders für 0, 1 oder 2. Ausgestaltung 6-4 R 6 is in particular hydrogen, n is in particular 0, 1 or 2. Embodiment 6-4
Aa steht insbesonders für Stickstoff, Aa stands for nitrogen in particular,
Ab steht insbesonders für -C(R9)(R10)-, Ab stands in particular for -C (R 9 ) (R 10 ) -,
Ac steht insbesonders für -C(RU)(R12)-, Ac stands in particular for -C (R U ) (R 12 ) -,
Ad steht insbesonders für -C(R13)(R14)-, wobei sich insbesonders folgende Struktureinheiten ergibt: AI, Ad stands in particular for -C (R 13 ) (R 14 ) -, whereby in particular the following structural units result: AI,
R1 steht insbesonders für Ethyl, R 1 is especially ethyl,
R9, R10, R11, R12, R13, R14 stehen unabhängig voneinander insbesonders für Wasserstoff, Methyl oder Ethyl, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another are especially hydrogen, methyl or ethyl,
Q steht insbesonders für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q2 oder Q3, Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q2 or Q3,
Figure imgf000015_0001
Figure imgf000015_0001
R4 steht insbesonders für Methyl, Ethyl, i-Propyl, Methoxymethyl oder Methoxyethyl, - - R 4 is especially methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl, - -
R5 steht insbesonders für Fluor, Chlor, Brom, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl (CH2CFH2, CHFCH3), Difluorethyl (CF2CH3, CH2CHF2, CHFCFH2), Trifluorethyl, (CH2CF3, CHFCHF2, CF2CFH2), Tetrafluorethyl (CHFCF3, CF2CHF2), Pentafluorethyl, Trifluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy oder Trifluormethylthio, R6 steht insbesonders für Wasserstoff, n steht insbesonders für 0, 1 oder 2. R 5 is in particular fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio, R 6 is in particular hydrogen, n is especially 0, 1 or 2.
Ausgestaltung 6-5 Embodiment 6-5
Aa steht insbesonders für Stickstoff, Ab steht insbesonders für -C(R9)(R10)-, Ac steht insbesonders für -C(RU)(R12)-, Ad steht insbesonders für -C(R13)(R14)-, wobei sich insbesonders folgende Struktureinheiten ergibt: AI, R1 steht insbesonders für Ethyl, Aa in particular stands for nitrogen, Ab in particular stands for -C (R 9 ) (R 10 ) -, Ac stands in particular for -C (R U ) (R 12 ) -, ad stands in particular for -C (R 13 ) (R 14 ) -, wherein in particular the following structural units are obtained: Al, R 1 is in particular ethyl,
R9, R10, R11, R12, R13, R14 stehen insbesonders für Wasserstoff, Q steht insbesonders für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q3, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are in particular hydrogen, Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q3,
R4 steht insbesonders für Methyl, R 4 is especially methyl,
R5 steht insbesonders für Trifluormethyl, R 5 is especially trifluoromethyl,
R6 steht insbesonders für Wasserstoff, n steht insbeosnders für 2. R 6 is in particular hydrogen, n is insbesosnders for 2.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I), wobei R1, R2, R3, R7, R8, R9, R10, R11, R12, R13, R14, Q, Aa, Ab, Ac, Ad, n und m die in Ausgestaltung (1) angegebenen Bedeutungen haben. In a preferred embodiment, the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1).
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I), wobei R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, Q, Aa, Ab, Ac, Ad, n und m die in Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) oder Ausgestaltung (6-1) oder Ausgestaltung (6-2) oder Ausgestaltung (6-3) oder Ausgestsltung (6-4) - - oder Ausgestaltung (6-5) angegebenen Bedeutungen haben. In a preferred embodiment, the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or Embodiment (6-1) or Embodiment (6-2) or Embodiment (6-3) or Embodiment (6-4) - - or embodiment (6-5) have specified meanings.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (Γ), wobei R1, R2, R3, R7, R8, R9, R10, R11, R12, R13, R14, Q, Aa, Ab, Ac, Ad, n und m die in Ausgestaltung (1) angegebenen Bedeutungen haben. In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (Γ), wobei R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, Q, Aa, Ab, Ac, Ad, n und m die in Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) oder Ausgestaltung (6-1) oder Ausgestaltung (6-2) oder Ausgestaltung (6-3) oder Ausgestaltung (6-4) oder Ausgestaltung (6-5) angegebenen Bedeutungen haben. In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I) der Struktureinheit Al l In a preferred embodiment, the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1). In a preferred embodiment, the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or design (6-1) or design (6-2) or design (6-3) or design (6-4) or design (6-5) have specified meanings. In a preferred embodiment, the invention relates to compounds of the formula (I) of the structural unit Al 1
Figure imgf000017_0001
wobei Q für Q3 steht und R1, R2, R3, R4, R5, R6 und n die in Ausgestaltung (2) oder Ausgestaltung (3) oder Ausgestaltung (4) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) angegebenen Bedeutungen haben.
Figure imgf000017_0001
wherein Q is Q3 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in embodiment (2) or embodiment (3) or embodiment (4) or embodiment (5-1) or embodiment Have (5-2) indicated meanings.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I) der Struktureinheit AI In a preferred embodiment, the invention relates to compounds of the formula (I) of the structural unit AI
Figure imgf000017_0002
wobei Q, R1, R4, R5, R6, R9, R10, R11, R12, R13, R14 und n die in Ausgestaltung (6-1) oder Ausgestaltung (6-2) oder Ausgestaltung (6-3) oder Ausgestaltung (6-4) oder Ausgestaltung (6-5) angegebenen Bedeutungen haben.
Figure imgf000017_0002
wherein Q, R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n in the embodiment (6-1) or embodiment (6-2) or Embodiment (6-3) or embodiment (6-4) or embodiment (6-5) have specified meanings.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I) der Struktureinheit AI - - In a preferred embodiment, the invention relates to compounds of the formula (I) of the structural unit AI - -
Figure imgf000018_0001
wobei Q für Q3 steht und R1, R4, R5, R6, R9, R10, R11, R12, R13, R14 und n die in Ausgestaltung (6-2) oder Ausgestaltung (6-3) oder Ausgestaltung (6-4) oder Ausgestaltung (6-5) angegebenen Bedeutungen haben. In den bevorzugten Definitionen ist, sofern nichts anderes angegeben ist,
Figure imgf000018_0001
wherein Q is Q3 and R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n are in the embodiment (6-2) or embodiment (6 3) or embodiment (6-4) or embodiment (6-5) have given meanings. In the preferred definitions, unless stated otherwise,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
In den besonders bevorzugten Definitionen ist, sofern nichts anderes angegeben ist, In the particularly preferred definitions, unless stated otherwise,
Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkyl, im Rahmen der vorliegenden Erfindung ein Rest einer gesättigten, aliphatischen Kohlenwasserstoffgruppe mit 1 bis 12 Kohlenstoffatomen verstanden, die verzweigt oder unverzweigt sein kann. Beispiele für Ci- Ci2-Alkylreste sind Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sek.-Butyl, tert.-Butyl, n- Pentyl, iso-Pentyl, Neopentyl, tert.-Pentyl, 1-Methylbutyl, 2-Methylbutyl, 1-Ethylpropyl, 1,2- Dimethylpropyl, Hexyl n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl und n-Dodecyl. Von diesen Alkylresten sind Ci-C6-Alkylreste besonders bevorzugt. Insbesondere bevorzugt sind Ci-C4-Alkylreste. Unless otherwise defined elsewhere, the term "alkyl", either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-Dodecyl Of these alkyl radicals, C 1 -C 6 -alkyl radicals are particularly preferred, C 1 -C 4 -alkyl radicals being particularly preferred.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkenyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-Ci2-Alkenylrest, welcher mindestens eine Doppelbindung aufweist, beispielsweise Vinyl, Allyl, 1-Propenyl, Isopropenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1,3-Butadienyl, 1-Pentenyl, 2- Pentenyl, 3-Pentenyl, 4-Pentenyl, 1,3-Pentadienyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl und 1 ,4-Hexadienyl, verstanden. Bevorzugt hiervon sind C2-C6-Alkenylreste und besonders bevorzugt sind C2-C4-Alkenylreste. Unless otherwise defined elsewhere, the term "alkenyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 -alkenyl radical having at least one double bond, for example vinyl, allyl , 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl , understood. preferably, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1, 4-hexadienyl thereof are C 2 -C 6 alkenyl groups and particularly preferred are C 2 -C 4 -alkenyl.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Alkinyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein linearer oder verzweigter C2-Ci2-Alkinylrest, welcher mindestens eine Dreifachbindung aufweist, beispielsweise Ethinyl, 1-Propinyl und Propargyl, verstanden. Bevorzugt hiervon sind C3-C6-Alkinylreste und besonders bevorzugt sind C3-C4-Alkinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Unless otherwise defined elsewhere, the term "alkynyl", either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 alkynyl having at least one triple bond, for example ethynyl, 1 Propynyl and propargyl, preferably C3-C6 alkynyl radicals and C 3 -C 4 -alkynyl radicals are particularly preferred. The alkynyl radical can also have at least one double bond.
Sofern nicht an anderer Stelle anders definiert, wird unter dem Begriff „Cycloalkyl", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, erfindungsgemäß ein C3-C8- Cycloalkylrest verstanden, beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl und Cyclooctyl, verstanden. Bevorzugt hiervon sind C3-C6-Cycloalkylreste. Unless otherwise defined elsewhere, the term "cycloalkyl", either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
Unter dem Begriff „Alkoxy", entweder in Alleinstellung oder aber in Kombination mit weiteren Begriffen, wie beispielsweise Halogenalkoxy, wird vorliegend ein Rest O-Alkyl verstanden, wobei der Begriff„Alkyl" die oben stehende Bedeutung aufweist. The term "alkoxy", either alone or in combination with other terms, such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term "alkyl" having the meaning given above.
Durch Halogen substituierte Reste, z.B. Halogenalkyl (=Haloalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom. Halogen substituted radicals, e.g. Haloalkyl (= haloalkyl) are halogenated once or several times up to the maximum possible number of substituents. For multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gegebenenfalls substituierte Reste können, wenn nichts anderes erwähnt ist, einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Unless otherwise specified, optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.
Erfindungsgemäß bevorzugt verwendet werden Verbindungen der Formeln (I) oder (Γ), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, preference is given to using compounds of the formulas (I) or (II) which contain a combination of the meanings listed above as being preferred.
Erfindungsgemäß besonders bevorzugt verwendet werden Verbindungen der Formeln (I) oder (Γ), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. Particular preference is given in accordance with the invention to compounds of the formulas (I) or (II) in which a combination of the meanings listed above as being particularly preferred is present.
Erfindungsgemäß ganz besonders bevorzugt verwendet werden Verbindungen der Formeln (I) oder (Γ), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt. Very particularly preferably used according to the invention are compounds of the formulas (I) or (II) which contain a combination of the meanings given above as being very particularly preferred.
Erfindungsgemäß hervorgehoben verwendet werden Verbindungen der Formeln (I) oder (Γ), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt. Use is made, in accordance with the invention, of compounds of the formulas (I) or (II) which contain a combination of the meanings listed above as being highlighted.
Die Verbindungen der Formeln (I) oder (Γ) 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 formulas (I) or (II) can be used as geometric and / or as optically active isomers or corresponding isomer mixtures in different composition. 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.
Die erfindungsgemäßen Verbindungen der Formeln (I) oder (Γ) können durch die in den folgenden Schemata dargestellten Verfahren erhalten werden: The compounds of the formula (I) or (II) according to the invention can be obtained by the processes illustrated in the following schemes:
Verfahren A-l Method A-l
Die Verbindungen der Formel (I), bei denen Q für Ql bis Q9 oder Q20 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928, WO2015/000715 sowie WO2015/121136 beschriebenen Verfahren. The compounds of the formula (I) in which Q is Q1 to Q9 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
Figure imgf000020_0001
Figure imgf000020_0001
Figure imgf000020_0002
Figure imgf000020_0002
(I) n=1 (I) n=2  (I) n = 1 (I) n = 2
Die Reste R1, R4, R5, R6, Aa, Ab, Ac, Ad und n haben die oben beschriebenen Bedeutungen, A2 und A3 stehen für CH oder N (wobei A2 und A3 nicht gleichzeitig für N stehen können), A4 steht für O, S oder N-R4 und X1 steht für Halogen. - - Schritt a) The radicals R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N (where A 2 and A 3 are not simultaneously N A 4 is O, S or NR 4 and X 1 is halogen. - - Step a)
Die Verbindungen der Formel (IV) können in Analogie zu dem in US5576335 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (II) mit Carbonsäuren der Formel (III) in Gegenwart eines Kondensationsmittels bzw. einer Base hergestellt werden. Verbindungen der Formel (II) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in US2003/69257, WO2006/65703, WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928 oder WO2015/000715 beschriebenen Verfahren. The compounds of the formula (IV) can be prepared in analogy to the process described in US Pat. No. 5,573,335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base. Compounds of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO2006 / 65703, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715 described method.
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in Verfahren E, F und G beschrieben. Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
Die Umsetzung der Verbindungen der Formel (II) mit Carbonsäuren der Formel (III) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol, oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N- Methylpyrrolidon oder Stickstoffhaltige Verbindungen wie beispielsweise Pyridin. Geeignete Kondensationsmittel sind beispielsweise Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid. The reaction of the compounds of the formula (II) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine. Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
Geeignete Basen sind anorganische Basen, die üblicherweise in solchen Reaktionen verwendet werden. Vorzugsweise werden Basen verwendet, die beispielhaft ausgewählt sind aus der Gruppe bestehend aus Acetaten, Phosphaten, Carbonaten und Hydrogencarbonaten von Alkali- oder Erdalkalimetallen. Besonders bevorzugt sind dabei Natriumacetat, Natriumphosphat, Kaliumphosphat, Caesiumcarbonat, Natriumcarbonat, Kaliumcarbonat, Natriumhydrogencarbonat, Kaliumhydrogencarbonat. Suitable bases are inorganic bases which are commonly used in such reactions. Preferably, bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 180 °C durchgeführt werden, vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 140 °C. Schritt b) The reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C. Step b)
Die Verbindungen der Formel (V) lassen sich herstellen durch Kondensation der Verbindungen der Formel (IV) z.B. analog der in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, - - The compounds of the formula (V) can be prepared by condensation of the compounds of the formula (IV), for example analogously to those in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, - -
WO2012/086848, WO2013/018928, WO2015/000715 sowie WO2015/121136 beschriebenen Verfahren. WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
Die Umsetzung zu Verbindungen der Formel (V) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, tert- Butylmethylether; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N-Methylpyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. The reaction to give compounds of the formula (V) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
Die Reaktion lässt sich durchführen in Gegenwart eines Kondensationsmittels, einer Säure, einer Base oder eines Chlorierungsmittels. The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
Beispiele für geeignete Kondensationsmittel sind Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid; Anhydride wie Essigsäureanhydrid, Trifluoressigsäureanhydrid; eine Mischung aus Triphenylphosphin, einer Base und Tetrachlorkohlenstoff oder eine Mischung aus Triphenylphosphin und einem Azodiester wie z.B. Diethylazodicarbonsäure. Examples of suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonsäure.
Beispiele für geeignete Säuren, die in der beschriebenen Reaktion eingesetzt werden können, sind Sulfonsäuren wie para-Toluolsulfonsäure; Carbonsäuren wie Essigsäure oder Polyphosphorsäuren. Examples of suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
Beispiele für geeignete Basen sind stickstoffhaltige Heterocyclen wie Pyridin, Picolin, 2,6-Lutidin, 1 ,8- Diazabicyclo[5.4.0]-7-undecen (DBU); tertiäre Amine wie Triethylamin und N,N- Diisopropylethylamin; anorganische Basen wie Kaliumphosphat, Kaliumcarbonat und Natriumhydrid. Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Ein Beispiel für ein geeignetes Chlorierungsmittel ist Phosphoroxychlorid. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. An example of a suitable chlorinating agent is phosphorus oxychloride. The reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
Schritt c) Step c)
Die Verbindungen der Formel (I), wobei n für 0 steht, lassen sich herstellen durch Umsetzung der Verbindungen der Formel (V) mit den Verbindungen der Formel (Via) in Gegenwart einer Base. Mercaptanderivate der Formel (Via) wie beispielsweise Methylmercaptan, Ethylmercaptan oder Isopropylmercaptan sind entweder kommerziell erhältlich oder können nach bekannten Methoden - - hergestellt werden, beispielsweise analog der in US2006/25633, US2006/111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 oder Journal of the American Chemical Society, 44 (1922), p. 1329 beschriebenen Verfahren. The compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base. Mercaptan derivatives of the formula (IVa), such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods - be prepared, for example analogously to those in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
Die Umsetzung zu Verbindung der Formel (I), wobei n für 0 steht, kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1,2- Dimethoxyethan, tert.-Butylmethylether; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise Ν,Ν-Dimethylformamid, N-Methylpyrrolidon oder Dimethylsulfoxid. The reaction to give compound of formula (I) wherein n is 0 may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent selected from conventional solvents inert to the prevailing reaction conditions. Preference is given to ethers, for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as Ν, Ν-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
Beispiele für geeignete Basen sind anorganische Basen aus der Gruppe bestehend aus Acetaten, Phosphaten und Carbonaten von Alkali- oder Erdalkalimetallen. Bevorzugt sind dabei Caesiumcarbonat, Natriumcarbonat und Kaliumcarbonat. Weitere geeignete Basen sind Alkalimetallhydride wie z.B. Natriumhydrid. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. Examples of suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Sodium hydride. The reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
In der beschriebenen Reaktion steht X1 bevorzugt für ein Fluor- oder Chloratom. Schritt d) In the reaction described, X 1 is preferably a fluorine or chlorine atom. Step d)
Die Verbindungen der Formel (I), wobei n für 1 steht, lassen sich herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure. Propionsäure oder Wasser. Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid, meta-Chlorperbenzoesäure oder Natriumperiodat. The compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0. The oxidation is generally carried out in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water. Examples of suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
Schritt e) Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 1 steht. Die Oxidation wird generell in einem Lösungsmittel - - durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure. Propionsäure oder Wasser. Step e) The compounds of formula (I) wherein n is 2 can be prepared by oxidation of the compounds of formula (I) wherein n is 1. The oxidation is generally in a solvent - - carried out. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta-Chlorperbenzoesäure. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid. The reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
Schritt f) Step f)
Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich auch in einem einstufigen Prozess herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure. Propionsäure oder Wasser. The compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0. The oxidation is generally carried out in a solvent. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta-Chlorperbenzoesäure. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
Die Verbindungen der Formel (Γ), bei denen Q für Ql bis Q9 oder Q20 steht, lassen sich ebenfalls analog zu Verfahren A herstellen, ausgehend von den entsprechenden Carbonsäuren der Formel (IIP), deren mögliche Herstellungswege in den Verfahren H, I und J beschrieben werden. The compounds of the formula (Γ) in which Q is Ql to Q9 or Q20 can likewise be prepared analogously to Process A, starting from the corresponding carboxylic acids of the formula (IIP), their possible preparation routes in Processes H, I and J. to be discribed.
Verfahren A-2 Die Verbindungen der Formel (I), bei denen Q für Ql bis Q9, Q17 oder Q20 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928, WO2015/000715 sowie WO2015/121136 beschriebenen Verfahren. Process A-2 The compounds of the formula (I) in which Q is Ql to Q9, Q17 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
Figure imgf000024_0001
Die Reste R1, R4, R5, R6, Aa, Ab, Ac, Ad und n haben die oben beschriebenen Bedeutungen, A2 und A3 stehen für CH oder N, A4 steht für O, S oder N-R4, M steht für Lithium, Natrium oder Kalium und X1 - - steht für Halogen. Schritt a)
Figure imgf000024_0001
The radicals R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N, A 4 is O, S or NR 4 , M is lithium, sodium or potassium and X 1 - - stands for halogen. Step a)
Alternativ können Verbindungen der Formel (I), wobei n für 2 steht, auch in einem einstufigen Prozess hergestellt werden, beispielsweise in Analogie zu den in Journal of Organic Chemistry 2005, 70, 2696- 2700 beschriebenen Verfahren durch einen Halogen-Sulfon-Austausch mit einer Verbindung der Formel (VIb) ausgehend von Verbindungen der Formel (V). Der Austausch wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden polar aprotische Lösungsmittel wie beispielsweise Dimethylsulfoxid und Ν,Ν-Dimethylformamid eingesetzt. Alternatively, compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (V). The exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and Ν, Ν-dimethylformamide.
Verbindungen der Formel (VIb) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Synthesis 1977, 57, 88-92; Tetrahedron Letters 1979, 9, 821-824 sowie Bulletin de la Societe Chimique de France 1958, 4, 447-450 beschriebenen Verfahren. Compounds of the formula (VIb) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Synthesis 1977, 57, 88-92; Tetrahedron Letters 1979, 9, 821-824 and Bulletin de la Societe Chimique de France 1958, 4, 447-450.
Beispiele für geeignete Schwefel-Reagenzien sind die Lithium-, Natrium- oder Kalium-Salze der Sulfinsäure. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. Examples of suitable sulfur reagents are the lithium, sodium or potassium salts of sulfinic acid. The reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
Die Verbindungen der Formel (Γ), bei denen Q für Ql bis Q9, Q17 oder Q20 steht, lassen sich ebenfalls analog zu Verfahren A-2 herstellen. The compounds of formula (Γ) wherein Q is Ql to Q9, Q17 or Q20 can also be prepared analogously to Method A-2.
Verfahren B-l Die Verbindungen der Formel (I), bei denen Q für Q10, QU, Q15 und Q16 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in US2009/203705, US2012/258951, WO2013/3298 oder J. Med. Chem. 31, (1988) 1590-1595 beschriebenen Verfahren. Method Bl The compounds of the formula (I) in which Q is Q10, QU, Q15 and Q16 can be prepared by known methods, for example analogously to those described in US2009 / 203705, US2012 / 258951, WO2013 / 3298 or J. Med. Chem. 31, (1988) 1590-1595.
- - - -
Figure imgf000026_0001
Figure imgf000026_0001
(I) n=1 (I) n=2 (I) n = 1 (I) n = 2
Die Reste R1, R5, R6, Aa, Ab, Ac, Ad und n haben die oben beschriebenen Bedeutungen. A2, A3, A4 und A5 stehen für CH oder N (wobei A2, A3, A4 und A5 nicht gleichzeitig für N stehen) und X1 steht für Halogen. Schritt a) The radicals R 1 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above. A 2 , A 3 , A 4 and A 5 are CH or N (wherein A 2 , A 3 , A 4 and A 5 are not simultaneously N) and X 1 is halo. Step a)
Carbonsäuren der Formel (III) werden in Analogie zu dem in WO2011/75643 oder EP2671582 beschriebenen Verfahren in Gegenwart von Ο,Ν-Dimethyl-hydroxylamin Hydrochlorid in Weinreb- Amide der Formel (VI) überführt. Carboxylic acids of the formula (III) are converted in analogy to the process described in WO2011 / 75643 or EP2671582 in the presence of Ο, Ν-dimethylhydroxylamine hydrochloride into Weinreb amides of the formula (VI).
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in Verfahren E, F und G beschrieben. Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
Schritt b, c) Step b, c)
Verbindungen der Formel (VI) lassen sich anschließend nach bekannten Methoden, beispielsweise - - analog dem in WO2011/75643 beschriebenen Verfahren, mit einem Grignard Reagenz wie beispielsweise Methylmagnesiumbromid in Ketone der Formel (VII) überführen. Durch anschließende Halogenierung analog der beispielsweise in US2012/302573 beschriebenen bekannten Methode sind Verbindungen der Formel (VIII) zugänglich. Schritt d) Compounds of the formula (VI) can then be prepared by known methods, for example - - analogously to the method described in WO2011 / 75643, with a Grignard reagent such as methylmagnesium bromide in ketones of the formula (VII). By subsequent halogenation analogous to the known method described for example in US2012 / 302573 known compounds of formula (VIII) are available. Step d)
Die Verbindungen der Formel (X) lassen sich herstellen durch Cyclisierung der Verbindungen der Formel (VIII) mit Aminen der Formel (IX). Die Cyclisierung erfolgt beispielsweise in Ethanol, Acetonitril oder Ν,Ν-Dimethylformamid nach bekannten Methoden analog der beispielsweise in WO2005/66177, WO2012/88411, WO2013/3298, US2009/203705, US2012/258951, WO2012/168733, WO2014/187762 oder J. Med. Chem. 31 (1988) 1590-1595 beschriebenen Verfahren. The compounds of the formula (X) can be prepared by cyclization of the compounds of the formula (VIII) with amines of the formula (IX). The cyclization is carried out, for example, in ethanol, acetonitrile or Ν, Ν-dimethylformamide by known methods analogously to, for example, WO2005 / 66177, WO2012 / 88411, WO2013 / 3298, US2009 / 203705, US2012 / 258951, WO2012 / 168733, WO2014 / 187762 or J. Med. Chem. 31 (1988) 1590-1595.
Die Verbindungen der Formel (IX) sind kommerziell erhältlich. The compounds of the formula (IX) are commercially available.
Schritt e) Steps)
Die Verbindungen der Formel (I), wobei n für 0 steht, lassen sich herstellen durch Umsetzung der Verbindungen der Formel (X) mit den Verbindungen der Formel (Via) in Gegenwart einer Base. Mercaptanderivate der Formel (Via) wie beispielsweise Methylmercaptan, Ethylmercaptan oder Isopropylmercaptan sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in US2006/25633, US2006/111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 oder Journal of the American Chemical Society, 44 (1922), p. 1329 beschriebenen Verfahren. Schritt f, g) The compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (X) with the compounds of the formula (Via) in the presence of a base. Mercaptan derivatives of the formula (Via), such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method. Step f, g)
Die Verbindungen der Formel (I), wobei n für 1 steht, lassen sich herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation erfolgt nach bekannten Methoden mit einem geeigneten Oxidationsmittel wie bespielsweise Wasserstoffperoxid, meta-Chlorperbenzoesäure oder Natriumperiodat. Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 1 steht. The compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0. The oxidation is carried out by known methods with a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate. The compounds of formula (I) wherein n is 2 may be prepared by oxidation of the compounds of formula (I) wherein n is 1.
Die Oxidation wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1,2- Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure. Propionsäure oder Wasser. Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta- Chlorperbenzoesäure. - - The oxidation is generally carried out in a solvent. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid. - -
Schritt h) Step h)
Die Verbindungen der Formel (I), wobei n für 2 steht, lassen sich auch in einem einstufigen Prozess herstellen durch Oxidation der Verbindungen der Formel (I), wobei n für 0 steht. Die Oxidation wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Alkohole wie Methanol oder Ethanol; Ameisensäure, Essigsäure. Propionsäure oder Wasser. Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und meta-Chlorperbenzoesäure. The compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0. The oxidation is generally carried out in a solvent. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water. Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
Die Verbindungen der Formel (Γ), bei denen Q für Q10, QU, Q15 und Q16 steht, lassen sich ebenfalls analog zu Verfahren B herstellen, ausgehend von den entsprechenden Carbonsäuren der Formeln (ΠΓ), deren mögliche Herstellungswege in den Verfahren H, I und J beschrieben werden. The compounds of the formula (Γ) in which Q is Q10, QU, Q15 and Q16 can likewise be prepared analogously to Process B, starting from the corresponding carboxylic acids of the formulas (ΠΓ), their possible preparation routes in Processes H, I and J are described.
Verfahren B-2 Method B-2
Die Verbindungen der Formel (I), bei denen Q für Q10, QU, Q15 und Q16 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in US2009/203705, US2012/258951, WO2013/3298 oder J. Med. Chem. 31, (1988) 1590-1595 beschriebenen Verfahren. The compounds of the formula (I) in which Q is Q10, QU, Q15 and Q16 can be prepared by known methods, for example analogously to those described in US2009 / 203705, US2012 / 258951, WO2013 / 3298 or J. Med. Chem. 31, (1988) 1590-1595.
Figure imgf000028_0001
Figure imgf000028_0001
Die Reste R1, R4, R5, R6, Aa, Ab, Ac, Ad und n haben die oben beschriebenen Bedeutungen, A2, A3, A4 und A5 stehen für CH oder N, M steht für Lithium, Natrium oder Kalium und X1 steht für Halogen. The radicals R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 , A 3 , A 4 and A 5 are CH or N, M is lithium , Sodium or potassium and X 1 is halogen.
Schritt a) Step a)
Alternativ können Verbindungen der Formel (I), wobei n für 2 steht, auch in einem einstufigen Prozess hergestellt werden, beispielsweise in Analogie zu den in Journal of Organic Chemistry 2005, 70, 2696- 2700 beschriebenen Verfahren durch einen Halogen-Sulfon-Austausch mit einer Verbindung der Formel (VIb) ausgehend von Verbindungen der Formel (X). Der Austausch wird generell in einem Lösungsmittel durchgeführt. Bevorzugt werden polar aprotische Lösungsmittel wie beispielsweise Dimethylsulfoxid und N,N-Dimethylformamid eingesetzt. Verbindungen der Formel (VIb) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Synthesis 1977, 57, 88-92; Tetrahedron Letters 1979, 9, 821-824 sowie Bulletin de la Societe Chimique de France 1958, 4, 447-450 - - beschriebenen Verfahren. Alternatively, compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (X). The exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and N, N-dimethylformamide. Compounds of the formula (VIb) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Synthesis 1977, 57, 88-92; Tetrahedron Letters 1979, 9, 821-824 and Bulletin de la Societe Chimique de France 1958, 4, 447-450 - - described procedures.
Beispiele für geeignete Schwefel-Reagenzien sind die Lithium-, Natrium- oder Kalium-Salze der Sulfinsäure. Examples of suitable sulfur reagents are the lithium, sodium or potassium salts of sulfinic acid.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von -20°C °C bis 120 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
Die Verbindungen der Formel (Γ), bei denen Q für Q10, QU, Q15 und Q16 steht, lassen sich ebenfalls analog zu Verfahren B-2 herstellen. The compounds of the formula (Γ) in which Q is Q10, QU, Q15 and Q16 can likewise be prepared analogously to process B-2.
Verfahren C Method C
Die Verbindungen der Formel (I), bei denen Q für Q17 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2014/142292 beschriebenen Verfahren. The compounds of the formula (I) in which Q is Q17 can be prepared by known methods, for example analogously to the processes described in WO2014 / 142292.
Figure imgf000029_0001
Figure imgf000029_0001
Die Reste R4, R5, R6, Aa, Ab, Ac und Ad haben die oben beschriebenen Bedeutungen. X1 steht für Halogen. The radicals R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above. X 1 is halogen.
Schritt a) Step a)
Die Verbindungen der Formel (XI) können in Analogie zu dem in US5374646 oder Bioorganic and Medicinal Chemistry Letters 2003, 13, 1093 - 1096 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (III) mit einer Ammoniakquelle in Gegenwart eines Kondensationsmittels hergestellt werden. The compounds of the formula (XI) can be prepared by reacting, analogously to the process described in US Pat. No. 5,374,446 or Bioorganic and Medicinal Chemistry Letters 2003, 13, 1093-1096 Compounds of formula (III) can be prepared with an ammonia source in the presence of a condensing agent.
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in Verfahren E, F und G beschrieben. Die Umsetzung der Verbindungen der Formel (III) mit der Ammoniakquelle wird vorzugsweise in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Dioxan oder Tetrahydrofuran. Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G. The reaction of the compounds of the formula (III) with the source of ammonia is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, dioxane or tetrahydrofuran.
Ein geeignetes Kondensationsmittel ist beispielsweise Carbonyldiimidazol. Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck durchgeführt werden. Vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 70 °C. A suitable condensing agent is, for example, carbonyldiimidazole. The reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 70 ° C.
Schritt b) Step b)
Die Verbindungen der Formel (XIII) können in Analogie zu dem in WO2014/142292 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (XI) mit Verbindungen der Formel (XII) in Gegenwart eines Palladiumkatalysators im Basischen hergestellt werden. The compounds of the formula (XIII) can be prepared in analogy to the process described in WO2014 / 142292 by the reaction of compounds of the formula (XI) with compounds of the formula (XII) in the presence of a palladium catalyst in basic.
Verbindungen der Formel (XII) können beispielsweise analog der in WO2014/142292 beschriebenen Verfahren hergestellt werden. Als Palladiumkatalysator kann beispielsweise [1,1 '-Bis- (diphenylphosphino)ferrocen]dichlorpalladium(II) verwendet werden. Als Base finden häufig anorganische Basen wie Kaliumtertbutanolat Verwendung. Die Umsetzung erfolgt in einem Lösungsmittel. Häufig wird Toluol verwendet. Compounds of the formula (XII) can be prepared, for example, analogously to the processes described in WO2014 / 142292. As the palladium catalyst, for example, [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) can be used. As base often find inorganic bases such as Kaliumtertbutanolat use. The reaction takes place in a solvent. Often, toluene is used.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck durchgeführt werden. Vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 110 °C. The reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 110 ° C.
Die weitere Umsetzung von Verbindungen der Formel (XIII) zu Verbindungen der Formel (I) erfolgt analog zu Verfahren A. Die Verbindungen der Formel (Γ), bei denen Q für Q17 steht, lassen sich ebenfalls analog zu Verfahren C herstellen, ausgehend von den entsprechenden Carbonsäuren der Formel (IIP), deren mögliche Herstellungswege in den Verfahren H, I und J beschrieben werden. The further reaction of compounds of the formula (XIII) to give compounds of the formula (I) is carried out analogously to process A. The compounds of the formula (II) in which Q is Q17 can likewise be prepared analogously to process C, starting from corresponding carboxylic acids of the formula (IIP), whose possible preparation routes in the methods H, I and J are described.
Verfahren D Method D
Die Verbindungen der Formel (I), bei denen Q für Q14 steht, können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2011/073149 beschriebenen Verfahren. - - The compounds of the formula (I) in which Q is Q14 can be prepared by known methods, for example analogously to the processes described in WO2011 / 073149. - -
Figure imgf000031_0001
Figure imgf000031_0001
Die Reste R4, R5, R6, Aa, Ab, Ac und Ad haben die oben beschriebenen Bedeutungen. X1 steht für Halogen. The radicals R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above. X 1 is halogen.
Schritt a) Die Verbindungen der Formel (XV) können in Analogie zu dem in WO2011/073149 oder US5576335 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (XIV) mit einer Carbonsäure der Formel (III) in Gegenwart eines Kondensationsmittels bzw. einer Base hergestellt werden. Step a) The compounds of the formula (XV) can be prepared in analogy to the process described in WO2011 / 073149 or US5576335 by reacting compounds of the formula (XIV) with a carboxylic acid of the formula (III) in the presence of a condensing agent or a base become.
Verbindungen der Formel (XIV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2008/51493 oder in Bioorganic and Medicinal Chemistry, 22 (2014), 3515 - 3526 beschriebenen Verfahren. Compounds of the formula (XIV) are either commercially available or can be prepared by known methods, for example analogously to the method described in WO2008 / 51493 or in Bioorganic and Medicinal Chemistry, 22 (2014), 3515-3526.
Carbonsäuren der Formel (III) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden. Mögliche Herstellungswege werden in Verfahren E, F und G beschrieben. Die Umsetzung der Verbindungen der Formel (XIV) mit Carbonsäuren der Formel (III) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol, oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N- Methylpyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. - - Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G. The reaction of the compounds of the formula (XIV) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine. - -
Geeignete Kondensationsmittel sind beispielsweise Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid. Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
Geeignete Basen sind anorganische Basen, die üblicherweise in solchen Reaktionen verwendet werden. Vorzugsweise werden Basen verwendet, die beispielhaft ausgewählt sind aus der Gruppe bestehend aus Acetaten, Phosphaten, Carbonaten und Hydrogencarbonaten von Alkali- oder Erdalkalimetallen. Besonders bevorzugt sind dabei Natriumacetat, Natriumphosphat, Kaliumphosphat, Caesiumcarbonat, Natriumcarbonat, Kaliumcarbonat, Natriumhydrogencarbonat, Kaliumhydrogencarbonat. Suitable bases are inorganic bases which are commonly used in such reactions. Preferably, bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 180 °C durchgeführt werden, vorzugsweise erfolgt die Reaktion bei Normaldruck und Temperaturen von 20 bis 140 °C. The reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
Schritt b) Step b)
Die Verbindungen der Formel (XVI) lassen sich herstellen durch Kondensation der Verbindungen der Formel (XV) z.B. analog der in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928 oder WO2015/000715 beschriebenen Verfahren. Die Umsetzung zu Verbindungen der Formel (XVI) kann in Substanz oder in einem Lösungsmittel erfolgen, vorzugsweise wird die Reaktion in einem Lösungsmittel durchgeführt, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Diisopropylether, Dioxan, Tetrahydrofuran, 1 ,2-Dimethoxyethan, tert- Butylmethylether; halogenierte Kohlenwasserstoffe wie beispielsweise Dichlormethan, Chloroform, Tetrachlorkohlenstoff, 1 ,2-Dichlorethan oder Chlorbenzol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise N,N-Dimethylformamid oder N-Methylpyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. The compounds of formula (XVI) can be prepared by condensation of the compounds of formula (XV) e.g. analogously to the process described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715. The reaction to give compounds of the formula (XVI) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preferred are ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
Die Reaktion lässt sich durchführen in Gegenwart eines Kondensationsmittels, einer Säure, einer Base oder eines Chlorierungsmittels. The reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
Beispiele für geeignete Kondensationsmittel sind Carbodiimide wie l-(3-Dimethylaminopropyl)-3- ethylcarbodiimid hydrochlorid (EDCI) oder 1,3-Dicyclohexylcarbodiimid; Anhydride wie Essigsäureanhydrid, Trifluoressigsäureanhydrid; eine Mischung aus Triphenylphosphin, einer Base und Tetrachlorkohlenstoff oder eine Mischung aus Triphenylphosphin und einem Azodiester wie z.B. Diethylazodicarbonsäure. Examples of suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonsäure.
Beispiele für geeignete Säuren, die in der beschriebenen Reaktion eingesetzt werden können, sind Sulfonsäuren wie para-Toluolsulfonsäure; Carbonsäuren wie Essigsäure oder Polyphosphorsäuren. Beispiele für geeignete Basen sind stickstoffhaltige Heterocyclen wie Pyridin, Picolin, 2,6-Lutidin, 1 ,8- Diazabicyclo[5.4.0]-7-undecen (DBU); tertiäre Amine wie Triethylamin und N,N- Diisopropylethylamin; anorganische Basen wie Kaliumphosphat, Kaliumcarbonat und Natriumhydrid. Examples of suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids. Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Ein Beispiel für ein geeignetes Chlorierungsmittel ist Phosphoroxychlorid. An example of a suitable chlorinating agent is phosphorus oxychloride.
Die Reaktion kann im Vakuum, bei Normaldruck oder unter Überdruck und bei Temperaturen von 0 °C bis 200 °C durchgeführt werden. The reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
Die weitere Umsetzung von Verbindungen der Formel (XVI) zu Verbindungen der Formel (I) erfolgt analog zu Verfahren A. The further reaction of compounds of the formula (XVI) to give compounds of the formula (I) is carried out analogously to process A.
Die Verbindungen der Formel (Γ), bei denen Q für Q14 steht, lassen sich ebenfalls analog zu Verfahren D herstellen, ausgehend von den entsprechenden Carbonsäuren der Formel (IIP), deren mögliche Herstellungswege in den Verfahren H, I und J beschrieben werden. The compounds of the formula (Γ) in which Q is Q14 can likewise be prepared analogously to process D, starting from the corresponding carboxylic acids of the formula (IIP), whose possible preparation routes are described in the processes H, I and J.
Verfahren E Method E
Figure imgf000033_0001
Figure imgf000033_0001
(Illa)  (IIIa)
Carbonsäuren der Formel (Illa), mit der Struktureinheit AI, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise aus Pyrrolidin-Derivaten analog der in WO2011/098904, Chemical Communications, 48 (2012), 3133-3135, Organic Letters, 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 und Organic Letters, 8 (2006), 5303-5305 beschriebenen Verfahren. - - Carboxylic acids of the formula (IIIa) with the structural unit AI are either commercially available or can be prepared by known methods, for example from pyrrolidine derivatives analogous to those described in WO2011 / 098904, Chemical Communications, 48 (2012), 3133-3135, Organic Letters , 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013 ), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305 described method. - -
Figure imgf000034_0001
Figure imgf000034_0001
Die Reste R9, R10, R11, R12, R13 und R14 haben die oben beschriebenen Bedeutungen. X1 steht für Halogen und R15 für (Ci-C6)Alkyl oder Aryl(Ci-C2)alkyl. Schritt a), b), c) The radicals R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the meanings described above. X 1 is halogen and R 15 is (Ci-C 6 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a), b), c)
Die Verbindungen der Formel (XXII) können in Analogie zu den in Chemical Communications, 48 (2012), 3133-3135 und WO2011/098904 beschriebenen Verfahren durch die Umsetzung von Verbindungen der Formel (XXI) mit einem Propiolat der Formel (XX) unter neutralen Bedingungen in einer Michael-Addition, gefolgt von einer Diazotierung am oc-Kohlenstoffatom des Michael-Addukts unter Verwendung typischer Diazotierungsreagenzien und einer anschließenden Cyclisierung unter basischen Bedingungen zu dem gewünschten 6,7-Dihydro-5H-pyrrolo[l,2-a]imidazol hergestellt werden. The compounds of the formula (XXII) can be prepared by reacting compounds of the formula (XXI) with a propiolate of the formula (XX) under neutral conditions in analogy to the processes described in Chemical Communications, 48 (2012), 3133-3135 and WO2011 / 098904 Conditions in a Michael addition followed by diazotization at the oc-carbon of the Michael adduct using typical diazotization reagents and subsequent cyclization under basic conditions to the desired 6,7-dihydro-5H-pyrrolo [1,2-a] imidazole getting produced.
Die Verbindungen der Formel (XXI) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Letters, 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 und Organic Letters, 8 (2006), 5303-5305 beschriebenen Verfahren. The compounds of formula (XXI) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Letters, 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305.
Die Verbindungen der Formel (XX) sind kommerziell erhältlich. Schritt d) The compounds of the formula (XX) are commercially available. Step d)
Verbindungen der Formel (XXIII) können nach bekannten Methoden hergestellt werden, beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte - - Compounds of formula (XXIII) may be prepared by known methods, for example via direct ortho-lithiation followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or alternatively via a carboxylic acid derivative - -
Halogenierung in Analogie zu den in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren. Halogenation analogous to that described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
Schritt e) Steps)
Verbindungen der Formel (lila) können nach bekannten Methoden aus Verbindungen der Formel (XXIII) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. Compounds of the formula (IIIa) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
Verfahren F Method F
Figure imgf000035_0001
Figure imgf000035_0001
(Illb)  (IIIb)
Carbonsäuren der Formel (Illb), mit den Struktureinheiten A2, A3 oder A4, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise aus Oxazolidinon-, Thiazolidinon- oder Imidazolidinon-Derivaten analog der in Russian Journal of Organic Chemistry, 46 (2010), 1461-1465, US2005/0256164, US2002/0098443, Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787, Journal of the American Chemical Society, 73 (1951), 4199-4204, Molecules, 19 (2014), 14-18, Chemical Communications, 50 (2014), 9661-9664, Green Chemistry, 15 (2013), 2447-2456, WO2009/ 135927, Khimiko-Farmatsevticheskii Zhurnal, 18 (1984), 290-297, Journal of the American Chemical Society, 135 (2013), 2891-2894; Synlett, 11 (2006), 1663-1666; Helvetica Chimica Acta, 55 (1972), 2295-2300; WO2013/ 149997 sowie European Journal of Organic Chemistry, 29 (2014), 6418-6430 beschriebenen Verfahren. Carboxylic acids of the formula (IIIb) having the structural units A2, A3 or A4 are either commercially available or can be prepared by known methods, for example from oxazolidinone, thiazolidinone or imidazolidinone derivatives analogous to those described in Russian Journal of Organic Chemistry, 46 (US Pat. 2010), 1461-1465, US2005 / 0256164, US2002 / 0098443, Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787, Journal of the American Chemical Society, 73 (1951), 4199-4204 , Molecules, 19 (2014), 14-18, Chemical Communications, 50 (2014), 9661-9664, Green Chemistry, 15 (2013), 2447-2456, WO2009 / 135927, Khimiko-Farmatsevticheskii Zhurnal, 18 (1984), 290-297, Journal of the American Chemical Society, 135 (2013), 2891-2894; Synlett, 11 (2006), 1663-1666; Helvetica Chimica Acta, 55 (1972), 2295-2300; WO2013 / 149997 and European Journal of Organic Chemistry, 29 (2014), 6418-6430.
Figure imgf000035_0002
Figure imgf000035_0002
(XXVI I I) (XXIX) (I l lb) Die Reste R9, R10, R11 und R12 haben die oben beschriebenen Bedeutungen. Ad steht für -S(0)m-, -O- oder -N(R7)-. X1 und X2 stehen für Halogen, R15 steht für (Ci-C4)Alkyl oder Aryl(Ci- C2)alkyl und R16 steht für -CN oder -COOR17, wobei R17 für (Ci-C4)Alkyl steht. (XXVI II) (XXIX) (I l lb) The radicals R 9 , R 10 , R 11 and R 12 have the meanings described above. Ad stands for -S (0) m -, -O- or -N (R 7 ) -. X 1 and X 2 are halogen, R 15 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl and R 16 is -CN or -COOR 17 , wherein R 17 is (Ci-C 4 ) Alkyl.
Schritt a) Die Verbindungen der Formel (XXV) können in Analogie zu den in Russian Journal of Organic Chemistry, 46 (2010), 1461-1465, US2005/0256164 und US2002/0098443 beschriebenen Verfahren über eine Alkylierung von Oxazolidinon-, Thiazolidinon- oder Imidazolidinon-Derivaten der Formel (XXIV) mit den entsprechenden oc-Halo- oder α-Diazo-Carbonsäureestern oder -Nitrilen unter sauren oder basischen Bedingungen synthetisiert werden. Die Verbindungen der Formel (XXIV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787 und Journal of the American Chemical Society, 73 (1951), 4199-4204 beschriebenen Verfahren. Step a) The compounds of the formula (XXV) can be prepared in analogy to those described in Russian Journal of Organic Chemistry, 46 (2010), 1461-1465, US2005 / 0256164 and US2002 / 0098443 via an alkylation of oxazolidinone, thiazolidinone or Imidazolidinone derivatives of the formula (XXIV) with the corresponding oc-halo or α-diazo carboxylic acid esters or nitriles are synthesized under acidic or basic conditions. The compounds of formula (XXIV) are either commercially available or can be prepared by known methods, for example analogous to those described in Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787 and Journal of the American Chemical Society, 73 (1951), 4199-4204.
Schritt b) Step b)
Verbindungen der Formel (XXVI) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise über eine Aminolyse, wobei R16 für -CN steht, bzw. über eine Amidierung, wobei R16 für -COOR17 steht, ausgehend von Verbindungen der Formel (XXV) analog der in Molecules, 19 (2014), 14-18, Chemical Communications, 50 (2014), 9661-9664 und Green Chemistry, 15 (2013), 2447-2456 beschriebenen Verfahren. Compounds of formula (XXVI) are either commercially available or can be prepared by known methods, for example via an aminolysis, wherein R 16 is -CN, or via an amidation, wherein R 16 is -COOR 17 , starting from compounds of Formula (XXV) analogous to that described in Molecules, 19 (2014), 14-18, Chemical Communications, 50 (2014), 9661-9664 and Green Chemistry, 15 (2013), 2447-2456.
Schritt c) Step c)
Verbindungen der Formel (XXVII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden aus Verbindungen der Formel (XXVI) über eine intramolekulare Kondensation hergestellt werden. Dies kann beispielsweise unter Verwendung von Phosphoroxychlorid unter thermischen Bedingungen in Analogie zu den in WO2009/135927 und Khimiko-Farmatsevticheskii Zhurnal, 18 (1984), 290-297 beschriebenen Verfahren durchgeführt werden. Compounds of the formula (XXVII) are either commercially available or can be prepared by known methods from compounds of the formula (XXVI) via an intramolecular condensation. This can be done, for example, using phosphorus oxychloride under thermal conditions in analogy to the methods described in WO2009 / 135927 and Khimiko-Farmatsevticheskii Zhurnal, 18 (1984), 290-297.
Schritt d) Step d)
Verbindungen der Formel (XXVIII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden aus Verbindungen der Formel (XXVII) analog zu den in Journal of the American Chemical Society, 135 (2013), 2891-2894, Synlett, 11 (2006), 1663-1666, Helvetica Chimica Acta, 55 (1972), - - Compounds of formula (XXVIII) are either commercially available or can be prepared by known methods from compounds of formula (XXVII) analogous to those described in Journal of the American Chemical Society, 135 (2013), 2891-2894, Synlett, 11 (2006), 1663 -1666, Helvetica Chimica Acta, 55 (1972), - -
2295-2300, WO2013/149997 sowie European Journal of Organic Chemistry, 29 (2014), 6418-6430 beschriebenen Verfahren über eine Carbonylierung synthetisiert werden. 2295-2300, WO2013 / 149997 and European Journal of Organic Chemistry, 29 (2014), 6418-6430 are synthesized via carbonylation.
Schritt e) Steps)
Carbonsäureester-Derivate der Formel (XXIX) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise über eine Halogenierung. Dies kann beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte Halogenierung in Analogie zu den in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren erfolgen. Carboxylic acid ester derivatives of the formula (XXIX) are either commercially available or can be prepared by known methods, for example via halogenation. This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
Schritt f) Step f)
Verbindungen der Formel (Illb) können nach bekannten Methoden aus Verbindungen der Formel (XXIX) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. Verfahren G Compounds of the formula (IIIb) can be prepared by known methods from compounds of the formula (XXIX) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions. Method G
Figure imgf000037_0001
Figure imgf000037_0001
(I I Ic)  (I I Ic)
Carbonsäuren der Formel (IIIc), mit den Struktureinheiten A5, A6, A7, A8, A9, A10, Al l, A12 oder AI 3, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise in Analogie zu den in WO2013/163244, Farmaco, Edizione Scientifica, 40 (1985), 190- 199,WO2013/087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929, WO2015/011082, Journal of Medicinal Chemistry, 58 (2015), 8309-8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry, 59 (2015), 151-167, Journal of the Chemical Society, (1929), 815- 816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946- 2948, Helvetica Chimica Acta, 32 (1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092, Journal of the American Chemical Society, 73 (1951), 3300-3304, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren. - - Carboxylic acids of the formula (IIIc) having the structural units A5, A6, A7, A8, A9, A10, Al, A12 or Al 3 are either commercially available or can be prepared by known methods, for example analogously to those described in WO2013 / 163244, Farmaco, Edizione Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929, WO2015 / 011082, Journal of Medicinal Chemistry, 58 (2015), 8309- 8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry, 59 (2015), 151-167, Journal of the Chemical Society, (1929), 815-816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946-2948, Helvetica Chimica Acta, 32 (1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092, Journal of the American Chemical Society, 73 (1951), 3300-3304, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146. - -
Figure imgf000038_0001
Figure imgf000038_0001
XXXI) (XXXI I)  XXXI) (XXXI I)
Figure imgf000038_0002
Figure imgf000038_0002
Ab steht für =N- oder =C(R2)-, Ac steht für =N- oder =C(R3)- und Ad steht für =N-, -N(R7)-, -O- oder -S(0)m- X1 und X3 stehen unabhängig voneinander für Halogen. R18 steht für (Ci-C4)Alkyl. Schritt a) Ab is = N- or = C (R 2 ) -, Ac is = N- or = C (R 3 ) - and Ad is = N-, -N (R 7 ) -, -O- or - S (0) m - X 1 and X 3 are each independently halogen. R 18 is (C 1 -C 4 ) alkyl. Step a)
Die Verbindungen der Formel (XXXII) können beispielsweise in Analogie zu den in WO2013/163244, Farmaco, Edizione Scientifica, 40 (1985), 190-199,WO2013/087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929 und WO2015/011082 beschriebenen Verfahren über eine Kondensation von 2- Aminoheteroaryl-Derivaten der Formel (XXXI) mit einem oc-Halopyruvat der Formel (XXX) synthetisiert werden. The compounds of the formula (XXXII) can be prepared, for example, in analogy to those described in WO2013 / 163244, Farmaco, Edizione Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929 and WO2015 / 011082 are synthesized via a condensation of 2-amino heteroaryl derivatives of the formula (XXXI) with a oc-Halopyruvat of formula (XXX).
Die Verbindungen der Formel (XXXI) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Journal of Medicinal Chemistry,The compounds of the formula (XXXI) are either commercially available or can be prepared by known methods, for example analogously to those described in Journal of Medicinal Chemistry,
58 (2015), 8309-8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry,58 (2015), 8309-8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry,
59 (2015), 151-167, Journal of the Chemical Society, (1929), 815-816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946-2948, Helvetica Chimica Acta, 3259 (2015), 151-167, Journal of the Chemical Society, (1929), 815-816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946-2948 , Helvetica Chimica Acta, 32
(1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092 und Journal of the American Chemical Society, 73 (1951), 3300-3304 beschriebenen Verfahren. (1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092 and Journal of the American Chemical Society, 73 (1951), 3300-3304.
Die Verbindungen der Formel (XXX) sind kommerziell erhältlich. The compounds of formula (XXX) are available commercially.
Schritt b) Verbindungen der Formel (XXXIII) können nach bekannten Methoden hergestellt werden, beispielsweise über eine Halogenierung. Dies kann beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte Halogenierung in Analogie zu den in Bioorganic - - Step b) Compounds of the formula (XXXIII) can be prepared by known methods, for example via halogenation. This may be, for example, via directed ortho-lithiation, followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or, alternatively, via a carboxylic acid derivative-directed halogenation in analogy to that described in Bioorganic - -
& Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren erfolgen. & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
Schritt c) Step c)
Verbindungen der Formel (IIIc) können nach bekannten Methoden aus Verbindungen der Formel (XXIII) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. Compounds of the formula (IIIc) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
Verfahren H Method H
Figure imgf000039_0001
Figure imgf000039_0001
(lila') (purple ')
Carbonsäuren der Formel (lila'), mit den Struktureinheiten A15 oder A17, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise in Analogie zu den in WO2006/130588, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren. Carboxylic acids of the formula (IIIa ') having the structural units A15 or A17 are either commercially available or can be prepared by known methods, for example in analogy to the methods described in WO2006 / 130588, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236- 4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
Figure imgf000039_0002
Figure imgf000039_0002
(XLVI I I) (l ila') Die Reste R11, R12, R13 und R14 haben die oben beschriebenen Bedeutungen. Ab steht für -N(R7)-, -O- oder -S-. X1 steht für Halogen, R19 steht für (Ci-C4)Alkyl oder Aryl(Ci-C2)alkyl. (XLVI II) (l ila '), the radicals R 11, R 12, R 13 and R 14 have the meanings described above. Ab is -N (R 7 ) -, -O- or -S-. X 1 is halogen, R 19 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl.
Schritt a) - - Step a) - -
Verbindungen der Formel (XL VII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2006/130588 beschriebenen Verfahren über eine zweifache Alkylierung eines Aminopyrazolo- oder eines Hydroxypyrazolo-Derivates der Formel (XLV) mit einem 1 ,2-Dibromoethan-Derivat der Formel (XLVI) unter Verwendung einer Base sowie thermischen Bedingungen. Compounds of the formula (XL VII) are either commercially available or can be prepared by known methods, for example analogously to the process described in WO2006 / 130588 via a double alkylation of an aminopyrazolo or a hydroxypyrazolo derivative of the formula (XLV) with a 1,2 Dibromoethane derivative of the formula (XLVI) using a base and thermal conditions.
Verbindungen der Formel (XLV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog den in Bioorganic & Medicinal Chemistry, 20 (2012), 714-733, WO2010/127975, Journal of Medicinal Chemistry, 50 (2007), 5161-5167, Journal of Combinatorial Chemistry, 7 (2005), 236-245, WO2010/096115 sowie WO2004/074257 beschriebenen Verfahren. Compounds of formula (XLV) are either commercially available or can be prepared by known methods, for example analogous to those described in Bioorganic & Medicinal Chemistry, 20 (2012), 714-733, WO2010 / 127975, Journal of Medicinal Chemistry, 50 (2007), 5161-5167, Journal of Combinatorial Chemistry, 7 (2005), 236-245, WO2010 / 096115 and WO2004 / 074257.
Die Verbindungen der Formel (XLVI) sind entweder kommerziell erhältlich oder können über die in Journal of Organic Chemistry, 65 (2000), 2379-2385; Tetrahedron: Asymmetry, 16 (2005), 2973-2979; Chemische Berichte, 111 (1987), 411-414 und Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 208 (1981), 617-619 beschriebenen Verfahren über eine Dibromierung der entsprechenden Olefin Verbindungen hergestellt werden. The compounds of formula (XLVI) are either commercially available or can be prepared via the methods described in Journal of Organic Chemistry, 65 (2000), 2379-2385; Tetrahedron: Asymmetry, 16 (2005), 2973-2979; Chemische Berichte, 111 (1987), 411-414 and Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 208 (1981), 617-619, via a dibromination of the corresponding olefin compounds.
Schritt b) Step b)
Verbindungen der Formel (XLVIII) sind entweder kommerziell erhältlich oder können über eine Halogenierung der Verbindungen der Formel (XL VII) hergestellt werden. Dies kann beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte Halogenierung in Analogie zu den in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren erfolgen. Compounds of formula (XLVIII) are either commercially available or can be prepared via halogenation of the compounds of formula (XL VII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
Schritt c) Step c)
Verbindungen der Formel (lila') können nach bekannten Methoden aus Verbindungen der Formel (XLVIII) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. Compounds of the formula (IIIa ') can be prepared by known methods from compounds of the formula (XLVIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
Verfahren I Procedure I
Figure imgf000040_0001
Figure imgf000040_0001
( " H b') - - ("Hb") - -
Carbonsäuren der Formel (Illb"), mit den Struktureinheiten A14, A16 oder A18, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise in Analogie zu den in Organic Process Research & Development, 10 (2006), 712-716, WO2006/130588, WO2010/117425, Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587-597, Bulletin of the Chemical Society of Japan, 36 (1963), 25- 29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461, Chemistry Letters, 7 (1985), 939-942, Tetrahedron Letters, 24 (1983), 1067-1070, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren. Carboxylic acids of the formula (IIIb ") having the structural units A14, A16 or A18 are either commercially available or can be prepared by known methods, for example in analogy to those described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588, WO2010 / 117425, Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587-597, Bulletin of the Chemical Society of Japan, 36 (1963) , 25-29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461, Chemistry Letters, 7 (1985), 939-942, Tetrahedron Letters, 24 (1989). 1983), 1067-1070, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238, Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
Figure imgf000041_0001
Figure imgf000041_0001
(XXXIV) (XXXV) (XXXVI)  (XXXIV) (XXXV) (XXXVI)
Figure imgf000041_0002
Figure imgf000041_0002
(XX)  (XX)
Die Reste R13 und R14 haben die oben beschriebenen Bedeutungen. R15 steht für (Ci-Ce)Alkyl oder Aryl(Ci-C2)alkyl. Ab steht für -C(R9)(R10)-, -S(0)m-, -O- oder -N(R7)-. Ac steht für -C(RU)(R12)-, -S(0)m-, -O- oder -N(R7)-. X1 steht für Halogen. Schritt a) The radicals R 13 and R 14 have the meanings described above. R 15 is (Ci-Ce) alkyl or aryl (Ci-C 2 ) alkyl. Ab stands for -C (R 9 ) (R 10 ) -, -S (0) m -, -O- or -N (R 7 ) -. Ac is -C (R U) (R 12) -, -S (0) m -, -O- or -N (R 7) -. X 1 is halogen. Step a)
Nitrosoprolin-Derivate der Formel (XXXV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Process Research & Development, 10 (2006), 712-716, WO2006/130588 und WO2010/117425 beschriebenen Verfahren über eine Nitrosierung von Verbindungen der Formel (XXXIV). Verbindungen der allgemeinen Formel (XXXIV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587-597, Bulletin of the Chemical Society of Japan, 36 (1963), 25-29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461 sowie Chemistry Letters, 7 (1985), 939-942 beschriebenen Verfahren. - - Nitrosoproline derivatives of the formula (XXXV) are either commercially available or can be prepared by known methods, for example analogously to the methods described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Nitrosation of compounds of the formula (XXXIV). Compounds of general formula (XXXIV) are either commercially available or can be prepared by known methods, for example analogously to those described in Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587 -597, Bulletin of the Chemical Society of Japan, 36 (1963), 25-29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461 and Chemistry Letters 7 (1985), 939-942. - -
Schritt b) Step b)
Mesoionische Sydnon-Derivate der Formel (XXXVI) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Process Research & Development, 10 (2006), 712-716, WO2006/130588 und WO2010/117425 beschriebenen Verfahren aus Verbindungen der Formel (XXXV) durch eine Heterocyclisierung unter Verwendung von z. B. Trifluoressigsäure -Anhydrid als wasserentziehendes Reagenz. Mesoionic sydnone derivatives of the formula (XXXVI) are either commercially available or can be prepared by known methods, for example analogously to the method described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Compounds of formula (XXXV) by heterocyclization using e.g. B. trifluoroacetic acid anhydride as dehydrating reagent.
Schritt c) Step c)
Verbindungen der allgemeinen Formel (XXXVIII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Organic Process Research & Development, 10 (2006), 712-716, WO2006/130588, Tetrahedron Letters, 24 (1983), 1067-1070 und WO2010/117425 beschriebenen Verfahren über eine 1,3-dipolare Cycloaddition aus Verbindungen der Formel (XX) und Ethylpropionate der Formel (XXXVII) und einer anschließenden Cycloreversion unter Freisetzung von CO2. Compounds of the general formula (XXXVIII) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588, Tetrahedron Letters, 24 (1983), 1067-1070 and WO2010 / 117425 described processes for a 1,3-dipolar cycloaddition of compounds of formula (XX) and ethyl propionates of the formula (XXXVII) and a subsequent cycloreversion to release CO2.
Die Verbindungen der Formel (XX) sind kommerziell erhältlich. Schritt d) The compounds of the formula (XX) are commercially available. Step d)
Verbindungen der Formel (XXXIX) sind entweder kommerziell erhältlich oder können nach bekannten Methoden über eine Halogenierung der Verbindungen der Formel (XXVIII) hergestellt werden. Dies kann beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte Halogenierung in Analogie zu den in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren erfolgen. Compounds of the formula (XXXIX) are either commercially available or can be prepared by known methods via halogenation of the compounds of the formula (XXVIII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
Schritt e) Steps)
Verbindungen der Formel (IlhV) können nach bekannten Methoden aus Verbindungen der Formel (XXXIX) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. - - Compounds of the formula (IIhV) can be prepared by known methods from compounds of the formula (XXXIX) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions. - -
Verfahren .T Procedure .T
Figure imgf000043_0001
Figure imgf000043_0001
Carbonsäuren der Formel (IIIc'), mit den Struktureinheiten A19 oder A20, sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise in Analogie zu den in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003/093280, WO2001/016138, WO2008/067257, WO2011/079230, WO2008/015271, WO2004/092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of the Chemical Society, Perkin Transaction 1 : Organic and Bio-Organic Chemistry, 18 (1999), 2639-2644, WO2003/035644, WO2013/050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry - A European Journal, 18 (2012), 14943-14947 und WO2013/036994 beschriebenen Verfahren. Carboxylic acids of the formula (IIIc ') having the structural units A19 or A20 are either commercially available or can be prepared by known methods, for example analogously to those described in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003 / 093280 WO200001 / 016138, WO2008 / 067257, WO2011 / 079230, WO2008 / 015271, WO2004 / 092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of Chemical Society, Perkin Transaction 1: Organic and Organic Biochemistry, 18 (1999), 2639-2644, WO2003 / 035644, WO2013 / 050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry-A European Journal, 18 (2012), 14943-14947 and WO2013 / 036994.
Figure imgf000043_0002
Figure imgf000043_0002
Die Reste R3 und R8 haben die oben beschriebenen Bedeutungen. Ab steht für -S(0)m-, The radicals R 3 and R 8 have the meanings described above. Ab stands for -S (0) m -,
-N(R7)-. X1 und X3 stehen für Halogen und R21 steht für (Ci-C4)Alkyl oder Aryl(Ci-C2)alkyl. Schritt a) - - -N (R 7 ) -. X 1 and X 3 are halogen and R 21 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a) - -
Verbindungen der allgemeinen Formel (XLII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003/093280, WO2001/016138 und WO2008/067257 beschriebenen Verfahren über eine Alkylierung eines 5-Aminopyrazol- (Ab steht für -N(R7)-), eines 5- Mercaptopyrazol- (Ab steht für -S-) oder eines 5-Hydroxypyrazol-Derivats (Ab steht für -0-) mit einem oc-Haloketon der Formel (XLI). Compounds of the general formula (XLII) are either commercially available or can be prepared by known methods, for example analogously to the methods described in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003 / 093280, WO2001 / 016138 and WO2008 / 067257 via an alkylation of a 5-aminopyrazole- (Ab stands for -N (R 7 ) -), a 5-mercaptopyrazole- (Ab stands for -S-) or a 5-hydroxypyrazole derivative (Ab stands for -O-) with an oc-haloketone of the formula (XLI).
Verbindungen der Formel (XL) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2011/079230, WO2008/015271, WO2004/092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of the Chemical Society, Perkin Transaction 1 : Organic and Bio- Organic Chemistry, 18 (1999), 2639-2644 und WO2003/035644 beschriebenen Verfahren. Compounds of the formula (XL) are either commercially available or can be prepared by known methods, for example analogously to WO2011 / 079230, WO2008 / 015271, WO2004 / 092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of the Chemical Society, Perkin Transaction 1: Organic and Bio-Organic Chemistry, 18 (1999), 2639-2644 and WO2003 / 035644.
Die Verbindungen der Formel (XLI) sind entweder kommerziell erhältlich oder können über die in Journal of the American Chemical Society, 132 (2010), 1264-1266, Organic Preparations and Procedures International, 7 (1975), 149-154 und European Journal of Medicinal Chemistry, 16 (1981), 495-501 beschriebenen Verfahren über eine α-Halogenierung der entsprechenden Ketone hergestellt werden. The compounds of formula (XLI) are either commercially available or can be prepared via the methods described in Journal of the American Chemical Society, 132 (2010), 1264-1266, Organic Preparations and Procedures International, 7 (1975), 149-154 and European Journal of Medicinal Chemistry, 16 (1981), 495-501, via α-halogenation of the corresponding ketones.
Schritt b) Step b)
Verbindungen der allgemeinen Formel (XLIII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO2013/050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry - A European Journal, 18 (2012), 14943-14947 und WO2013/036994 beschriebenen Verfahren über eine intramolekulare Kondensation aus Verbindungen der Formel (XLII) hergestellt werden. Compounds of general formula (XLIII) are either commercially available or can be prepared by known methods, for example analogously to those described in WO2013 / 050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry - A European Journal, 18 ( 2012), 14943-14947 and WO2013 / 036994 can be prepared via an intramolecular condensation of compounds of formula (XLII).
Schritt c) Step c)
Verbindungen der Formel (XLIV) sind entweder kommerziell erhältlich oder können nach bekannten Methoden über eine Halogenierung hergestellt werden. Dies kann beispielsweise über eine dirigierte ortho-Lithiierung, gefolgt von einem Abfangen des Carbanions mit einem geeigneten elektrophilen Halogenierungsreagenz oder alternativ über eine Carbonsäurederivat dirigierte Halogenierung in Analogie zu den in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 sowie WO2003/010146 beschriebenen Verfahren erfolgen. Schritt d) Compounds of formula (XLIV) are either commercially available or can be prepared by known methods via halogenation. This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods. Step d)
Verbindungen der Formel (IIIc') können nach bekannten Methoden aus Verbindungen der Formel (XLIV) über eine Esterspaltung unter sauren, basischen, thermischen oder hydrogenolytischen Bedingungen hergestellt werden. - - Compounds of the formula (IIIc ') can be prepared by known methods from compounds of the formula (XLIV) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions. - -
Verfahren und Verwendungen Methods and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) oder der Formel (Γ) 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) or of the formula (Γ) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) oder der Formel (Γ) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. The invention further relates to the use of the compounds of the formula (I) or of the formula (II) as pesticides, in particular pesticides. In the context of the present application, the term pest control always always includes the term pesticides.
Die Verbindungen der Formel (I) oder der Formel (Γ) 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, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. The compounds of the formula (I) or of the formula (II) are suitable for plant protection, favorable toxicity to warm-blooded animals and good environmental compatibility for protecting plants and plant organs against biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, in particular nematodes, and molluscs, which are found in agriculture, horticulture, animal breeding, aquaculture, forestry, gardens and recreational facilities, in the protection of stored products and in the sanitary sector.
Im Rahmen der vorliegenden Patentanmeldung ist der Begriff „Hygiene" so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauberkeit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder therapeutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
Der Begriff„Hygienesektor" deckt alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen wichtig sind, zum Beispiel im - - The term "hygiene sector" covers all areas, technical fields and industrial applications where these hygiene measures, rules and procedures are important, for example in the - -
Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. Hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal husbandry, etc.
Der Begriff„Hygieneschädling" ist daher so zu verstehen, dass damit ein oder mehrere Tierschädlinge gemeint sind, deren Gegenwart im Hygienesektor problematisch ist, insbesondere aus Gesundheitsgründen. Es ist daher ein Hauptziel, das Vorhandensein von Hygieneschädlingen und/oder das Ausgesetztsein ihnen gegenüber im Hygienesektor zu vermeiden oder auf ein Mindestmaß zu begrenzen. Dies lässt sich insbesondere durch die Anwendung eines Pestizids erreichen, das sich sowohl zum Verhindern eines Befalls als auch zum Verhindern eines bereits vorhandenen Befalls einsetzen lässt. Man kann auch Zubereitungen verwenden, die eine Exposition gegenüber Schädlingen verhindern oder reduzieren. Hygieneschädlinge schließen zum Beispiel die unten erwähnten Organismen ein. The term "hygiene pest" should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests For example, hygiene pests include the organisms mentioned below.
Der Begriff „Hygieneschutz" deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen aufrechterhalten und/oder verbessert werden. The term 'hygiene protection' thus covers all activities which maintain and / or improve those hygiene measures, rules and procedures.
Die Verbindungen der Formel (I) oder der Formel (Γ) 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) or the formula (II) can be preferably used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z. B. Acarus spp., z. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z. B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z. B. Eutetranychus banksi, Eriophyes spp., z. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z. B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z. B. Oligonychus 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; Srninthurus 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. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., 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, - - Pests from the strain of Arthropoda, in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Z. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Z. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; - - from the class of Chilopoda z. Geophilus spp., Scutigera spp .; from the order or class of Collembola z. B. Onychiurus armatus; Srninthurus viridis; from the class of Diplopoda z. B. Blaniulus guttulatus; from the class of the Insecta, z. B. from the order of Blattodea z. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agriotes spp., E.g. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., E.g. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., E.g. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferruginus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., E.g. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B. leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megascelis spp., Melanotus spp. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. 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 llorilega, 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, Acyrthosipon 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, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., z. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., z. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, 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., - - Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., E.g. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Stemus spp., E.g. Starchus paludatus, Symphyletes spp., Tanymecus spp., E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of Diptera z. B. Aedes spp., Z. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., E.g. Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., E.g. B. Dasineura brassicae, Delia spp. Delia antiqua, Delia coarctata, Delia llorilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., E.g. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., E.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., E.g. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., E.g. B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., Z. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of Hemiptera z. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus - - floccosus, Allocaridara malayensis, Amrasca spp. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., E.g. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp. , Aspidiella spp., Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. Cacopsylla pyricola, 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. 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. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. Empaasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., E.g. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., E.g. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae, Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., E.g. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., - -
Rhopalosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z. B. Lygocoris pabulinus, Lygus spp., z. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., z. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., z. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z. B. Acromyrmex spp., Athalia spp., z. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., z. B. Diprion similis, Hoplocampa spp., z. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes llavipes, 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 argiUacea, 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 ilavofasciata, 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 llammea, 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 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 Hävens, Frankliniella spp., z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella immaculata; Rhopalosiphum spp., E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. Eustistus heros, Euschistus servus, Eustistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp , Lygocoris pabulinus, Lygus spp., E.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., Z. B. Diprion similis, Hoplocampa spp., Z. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of Isoptera z. B. Coptotermes spp., Z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B. Reticulitermes llavipes, Reticulitermes hesperus; from the order of Lepidoptera z. Achroia grisella, Acronica major, Adoxophyes spp., E.g. Adoxophytes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., Z. Alabama argiUacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. B. anticarsia Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Z. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., E.g. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Efoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., E.g. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria ilavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp. Orthaga spp., Ostrinia spp. Ostrinia nubilalis, Panolis llammea, Parnara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g. Scirpophaga innotata, Scotia segetum, Sesamia spp., E.g. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp ., Trichophaga tapetzella, Trichoplusia spp. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Z. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. Locusta migratoria, melanoplus spp., E.g. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera z. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera z. B. Lepinotus spp., Liposcelis from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephalides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips hevens, Frankliniella spp., Z. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp , B. Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, z. B. aus der Klasse der Bivalvia, z. B. Dreissena spp.; sowie aus der Klasse der Gastropoda z. B. Arion spp., z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., Z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d. h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z. B. Aglenchus agricola, Anguina spp., z. B. Anguina tritici, Aphelenchoides spp., z. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z. B. Cacopaurus pestis, Criconemella spp., z. B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z. B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., z. B. Longidorus africanus, Meloidogyne spp., z. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., z. B. Paratrichodorus minor, Paratylenchus spp., 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. Plant pests from the strain of Nematoda, ie plant parasitic nematodes, in particular Aglenchus spp., Z. Aglenchus agricola, Anguina spp., E.g. Anguina tritici, Aphelenchoides spp., E.g. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., Z. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., 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. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
Die Verbindungen der Formel (I) oder der Formel (Γ) können gegebenenfalls in bestimmten Kon- zentrationen 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 the formula (I) or of the formula (II) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, Viricides (including anti-viral agents) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) can be used. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Formulierungen formulations
Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I) oder der Formel (Γ). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsförderer, z. B. pflanzliche Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester pflanzlicher Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze, z. B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise 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, comprising at least one compound of formula (I) or formula (Γ). Optionally, the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg. As organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such. As dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such. As glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser 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 einer oder mehreren Verbindungen der Formel (I) oder der Formel (Γ) 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) or of the formula (II), further agrochemical active compounds.
Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Verdicker und/oder weitere Hilfsstoffe wie beispielsweise - - They are preferably formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries such as - -
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. Diese Formulierungen werden in bekannter Weise hergestellt, z. B. durch Vermischen der Verbindungen der Formel (I) oder der Formel (Γ) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktiven Stoffen. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder der Formel (Γ) 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. 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). Adjuvants included. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration. These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) or the formula (Γ) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use. As excipients, it is possible to use those substances which are suitable for formulating the compounds of the formula (I) or the formula (II) or the forms of use prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), how to impart certain physical, technical and / or biological properties. Suitable extenders z. As water, polar and nonpolar organic chemical liquids such. B. 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), the ketones (such as acetone, cyclohexanone ), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. In the case of using water as an extender z. As well as organic solvents can be used as an auxiliary solvent. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg. As petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z. B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder chlorierte aliphatische Kohlenwasserstoffe wie z. B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z. B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z. B. Methanol, Ethanol, iso-Propanol, - - In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. 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. Butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z. B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und/oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls 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. As carriers are in particular question: z. For example, ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: z. As broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corncobs and tobacco stems.
Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Also, liquefied gaseous diluents or solvents can be used. In particular, are such extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for. As aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulfonsäure, Salze von Phenolsulfonsäure oder Naphthalinsulfonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulfobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulfate, Sulfonate und Phosphate, z. B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) oder der Formel (Γ) und/oder einer der inerten Träger Stoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g. As alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) or formula (II) and / or one of the inert carriers is not soluble in water and when applied in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. As further auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
Weiterhin enthalten sein können Stabilisatoren wie 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 cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers. - -
Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und pflanzliche 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-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.
Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsiörderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Feuchthaltemittel, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) oder der Formel (Γ) mit jedem festen oder flüssigen Zusatzstoff, welcher für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) or formula (II) may be combined with any solid or liquid additive commonly used for formulation purposes.
Als Retentionsiörderer 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 Retentionsiörderer are all those substances that reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Betracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Beweglichkeit der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettaminalkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the 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, Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.- der Verbindung der Formel (I) oder der Formel (Γ), besonders bevorzugt zwischen 0,01 und 95 Gew.- der Verbindung der Formel (I) oder der Formel (Γ), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.- der Verbindung der Formel (I) oder der Formel (Γ), bezogen auf das Gewicht der Formulierung. The formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I) or of the formula (II), particularly preferably between 0.01 and 95% by weight of the compound of the formula (I) or of the formula (II ), very particularly preferably between 0.5 and 90% by weight of the compound of the formula (I) or of the formula (II), based on the weight of the formulation.
Der Gehalt an der Verbindung der Formel (I) oder der Formel (Γ) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) oder der Formel (Γ) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.- der Verbindung der - - The content of the compound of the formula (I) or the formula (II) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) or the formula (II) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the - -
Formel (I) oder der Formel (Γ), vorzugsweise zwischen 0,00001 und 1 Gew.- , bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. Formula (I) or the formula (Γ), preferably between 0.00001 and 1 wt., Based on the weight of the application form. The application is done in a custom forms adapted to the application.
Mischungen Die Verbindungen der Formel (I) oder der Formel (Γ) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbiziden, 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. Des Weiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteertrag steigern, die Reife beeinflussen, die Qualität und/oder der Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. Mixtures The compounds of formula (I) or formula (II) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners , Semiochemicals and / or plant growth regulators are used so z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting benefits can be facilitated, crop yield and yield, maturity, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
Weiterhin können die Verbindungen der Formel (I) oder der Formel (Γ) 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) oder der Formel (Γ) zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. Furthermore, the compounds of the formula (I) or of the formula (II) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of formula (I) or formula (Γ) can be used to improve plant properties such as growth, yield and quality of the crop.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) oder der Formel (Γ) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. In a particular embodiment of the invention, the compounds of the formula (I) or of the formula (II) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann, sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids.
Insektizide/Akarizide/Nematizide Insecticides / acaricides / nematicides
Die hier mit ihrem „Common Name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben - - oder im Internet recherchierbar (z. B. http://www.alanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen IRAC Mode of Action Classification Scheme. The active substances mentioned here by their "common name" are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual", 16th Ed., British Crop Protection Council 2012) - - or searchable on the Internet (eg http://www.alanwood.net/pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.
(1) Acetylcholinesterase(AChE)-Inhibitoren, wie beispielsweise Carbamate, z. B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan,(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 und Xylylcarb oder Organophosphate, z. B. Acephat, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0-(methoxyaminothio-phosphoryl)salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. Ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC and xylylcarb or organophosphates, e.g. Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulphoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl-0- (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate , Oxydemeton-methyl, Parathion-methyl, Phenthoate, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos , Triclorfone and vamidothion.
(2) GABA-gesteuerte Chlorid- Kanal-B locker, wie beispielsweise Cyclodien-organochlorine, z. B. Chlordan und Endosulfan oder Phenylpyrazole (Fiprole), z. B. Ethiprol und Fipronil. (3) Natrium- Kanal-Modulatoren, wie beispielsweise Pyrethroide, z. B. Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(IR) -Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R) -Isomer], Tralomethrin und Transfluthrin oder DDT oder Methoxy chlor. (2) GABA-controlled chloride channel B loosened, such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil. (3) sodium channel modulators, such as pyrethroids, e.g. A-crinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans isomer], deltamethrin, empenthrin [(EZ) - (IR) isomer], esfenvalerate, etofenprox, Fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR) -trans-isomer], prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [ (1R) -isomer], tralomethrin and transfluthrin or DDT or methoxy-chloro.
(4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Neonicotinoide, z. B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nicotin oder Sulfoxaflor oder Flupyradifurone. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as neonicotinoids, e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), wie beispielsweise Spinosyne, z. B. Spinetoram und Spinosad. - - (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as spinosyn, e.g. B. spinetoram and spinosad. - -
(6) Allosterische Modulatoren des Glutamat-abhängigen Chloridkanals(GluCl), wie beispielsweise Avermectine/Milbemycine, z. B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl), such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
(7) Juvenilhormon-Mimetika, wie beispielsweise Juvenilhormon- Analoge, z. B. Hydropren, Kinopren und Methopren oder Fenoxycarb oder Pyriproxyfen. (8) Verschiedene nicht spezifische (multi-site) Inhibitoren, wie beispielsweise Alkylhalogenide, z. B. Methylbromid und andere Alkylhalogenide; oder Chloropicrin oder Sulfuryliluorid oder Borax oder Brech Weinstein oder Methylisocyanaterzeuger, z. B. Diazomet und Metam. (7) juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Various non-specific (multi-site) inhibitors, such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or crushing tartar or methyl isocyanate producers, e.g. Diazomet and Metam.
(9) Modulatoren chordotonaler Organe, z. B. Pymetrozin oder Flonicamid. (9) modulators of chordotonic organs, e.g. As pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, wie z. B. Clofentezin, Hexythiazox und Dillovidazin oder Etoxazol. (11) Mikrobielle Disruptoren der Insektendarmmembran, wie z. B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und -Pflanzenproteine: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab 1/35 Abi. (10) mite growth inhibitors, such as. Clofentezine, hexythiazox and dillovidazine or etoxazole. (11) Microbial disruptors of insect intestinal membrane such. B. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab 1 / 35 graduation
(12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinn Verbindungen, z. B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder(12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors such as diafenthiuron or organotin compounds, e.g. As azocyclotin, cyhexatin and fenbutatin oxide or
Propargit oder Tetradifon. Propargite or Tetradifone.
(13) Entkoppler der oxidativen Phoshorylierung durch Störung des Protonengradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by disruption of the proton gradient, such as chlorfenapyr, DNOC and sulfluramide.
(14) Blocker des nicotinischen Acetylcholinrezeptorkanals, wie beispielsweise Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Blockers of the nicotinic acetylcholine receptor channel, such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
(15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Dillubenzuron, Flucycloxuron, Flufenoxuron, Hexallumuron, Lufenuron, Novaluron, Novillumuron, Teflubenzuron und Triflumuron. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, novillumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Buprofezin. (17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern), wie beispielsweise Cyromazin. (16) inhibitors of chitin biosynthesis, type 1, such as buprofezin. (17) Skinning disruptor (especially in dipterans, i.e., two-winged), such as cyromazine.
(18) Ecdyson-Rezeptor-Agonisten, wie beispielsweise Chromafenozid, Halofenozid, Methoxyfenozid und Tebufenozid. (18) ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Oktopamin-Rezeptor-Agonisten, wie beispielsweise Amitraz. - - (19) octopamine receptor agonists, such as amitraz. - -
(20) Mitochondriale Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (20) Mitochondrial Complex III Electron Transport Inhibitors such as hydramethylnone or acequinocyl or fluacrypyrim.
(21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, wie beispielsweise METI-Akarizide, z. B. Fenazaquin, Fenpyroximat, Pyrimidiien, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenon (Derris). (21) Mitochondrial Complex I Electron Transport Inhibitors, such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidia, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
(22) Blocker des spannungsabhängigen Natriumkanals, wie z. B. Indoxacarb oder Metallumizone. (22) blocker of the voltage-dependent sodium channel, such. B. Indoxacarb or Metallumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z. B. Spirodiclofen, Spiromesifen und Spirotetramat. (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
(24) Inhibitoren des mitochondrialen Komplex-IV-Elektronentransports, wie beispielsweise Phosphine, z. B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanide, Calciumcyanid, Kaliumcyanid und Natriumcyanid. (24) inhibitors of mitochondrial complex IV electron transport, such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
(25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, wie beispielsweise beta- Ketonitrilderivate, z. B. Cyenopyrafen und Cyilumetofen und Carboxanilide, wie beispielsweise Pyllubumid. (25) inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyilumetofen and carboxanilides, such as Pyllubumid.
(28) Ryanodinrezeptor-Modulatoren, wie beispielsweise Diamide, z. B. Chlorantraniliprol, Cyantraniliprol und Flubendiamid, weitere Wirkstoffe wie beispielsweise Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximat, Bifenazat, Broflanilid, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclaniliprol, Cycloxaprid, Cyhalodiamid, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizin, Fluensulfon, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxametamid, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tioxazafen, Thiofluoximat, Triflumezopyrim und lodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo), sowie folgende Verbindungen: 1- { 2-Fluor-4-methyl-5- [(2,2,2-trifluorethyl)sulfinyl]phenyl } -3-(trifluormethyl)- 1 H- 1 ,2,4-triazol-5 -amin (bekannt aus WO2006/043635) (CAS 885026-50-6), { l'-[(2E)-3-(4-Chlorphenyl)prop-2-en-l-yl]-5- fluorspiro[indol-3 ,4'-piperidin] - 1 (2H)-yl } (2-chlorpyridin-4-yl)methanon (bekannt aus WO2003/106457) (CAS 637360-23-7), 2-Chlor-N-[2-{ l-[(2E)-3-(4-ch^henyl)prop-2-en-l-yl]piperidin-4-yl}-4- (trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494) (CAS 872999-66-1), 3-(4-Chlor- 2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO 2010052161) (CAS 1225292-17-0), 3-(4-Chlor-2, 6-dimethylphenyl)-8-methoxy-2-oxo-l,8- diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus EP 2647626) (CAS-1440516-42-6), 4-(But-2- - - in-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160) (CAS 792914-58-0), PF1364 (bekannt aus JP2010/018586) (CAS-Reg.No. 1204776-60-2), N-[(2E)-l-[(6- Chlorpyridin-3-yl)methyl]pyridin-2(lH)-yliden]-2,2,2-trilluoracetamid (bekannt aus WO2012/029672) (CAS 1363400-41 -2), (3E)-3-[l -[(6-Chlor-3-pyridyl)methyl] -2-pyridyliden]- 1 ,1,1 -trifluorpropan-2-οη (bekannt aus WO2013/144213) (CAS 1461743-15-6), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-l- methyl-3-(pentafluorethyl)-4-(trifluormethyl)-lH-pyrazol-5-carboxamid (bekannt aus WO2010/051926) (CAS 1226889- 14-0), 5 -Brom-4-chlor-N- [4-chlor-2-methyl-6-(methylcarbamoyl)phenyl] -2-(3 -chlor-2- pyridyl)pyrazol-3-carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5- Dichlo henyl)-4,5-dihydro-5-(triί uormethyl)-3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3- thietanyl)benzamid, 4-[5-(3,5-Dichlo henyl)-4,5-dihydro-5-(triί uormethyl)-3-isoxazolyl]-2-methyl-N- (trans-l-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)- 3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid (bekannt aus WO 2013/050317 AI) (CAS 1332628-83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- triί uo ropyl)sulfinyl]propananlid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3- triί uo ropyl)sulfinyl]propananlid und (-)-N-[3-Chlor- 1 -(3 -pyridinyl)- 1 H-pyrazol-4-yl] -N-ethyl-3 - [(3,3,3-trifluoφropyl)sulflnyl]propanamid (bekannt aus WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 AI) (CAS 1477923-37-7), 5-[[(2E)-3-Chlor-2-propen-l-yl]amino]-l-[2,6-dichlor-4- (trifluormethyl)phenyl]-4-[(trifluormethyl)sulfinyl]-lH-pyrazol-3-carbonitrile (bekannt aus CN 101337937 A) (CAS 1105672-77-2), 3-Brom-N-[4-chlor-2-methyl-6- [(methylamino)thioxomethyl]phenyl]-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid, (28) ryanodine receptor modulators, such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozid, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazone, Pyriminostrobin, spirobudiclofen, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following compounds: 1- {2-fluoro-4-methyl-5- [(2,2,2-trifluoroethyl) sulfinyl] phenyl} - 3- (trifluoromethyl) -1 H -1, 2,4-triazole-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {l '- [(2E) -3- (4- Chlorophenyl) prop-2-en-1-yl] -5-fluorospiro [indole-3, 4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone (known from WO2003 / 106457 ) (CAS 637360-23-7), 2-chloro-N- [2- {1 - [(2E) -3- (4-chloro-1-yl) prop-2-en-1-yl] -piperidine-4 yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-1 , 8-diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2, 6-dimethylphenyl) -8-methoxy-2 -oxo-l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), 4- (but-2-yl) - - in-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS Reg. No. 1204776-60-2), N - [(2E) -1 - [(6-chloropyridin-3-yl) methyl] pyridine-2 (1H) -ylidene] -2,2,2 trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41 -2), (3E) -3- [1- (6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1,1 trifluoropropane-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N- [3- (benzylcarbamoyl) -4-chlorophenyl] -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl ) -LH-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N- [4-chloro-2-methyl-6- (methylcarbamoyl) -phenyl ] -2- (3-chloro-2-pyridyl) pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4- [5- (3,5-dichloro) -4,5- dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) benzamide, 4- [5- (3,5-dichloro-4-yl) -4.5 dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (trans-1-oxido-3-thietanyl) benzamide and 4- [ (5S) -5- (3,5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-1-oxido-3-thietanyl) -benzamide ( WO 2013/050317 A1) (CAS 1332628-83-7), N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3 , 3,3-trifluoropropyl) sulfinyl] propane anilide, (+) - N- [3-chloro-1- (3-pyridinyl) -1H-pyrazol-4-yl] -N-ethyl-3 - [(3 , 3,3-trifluoropropyl) sulfinyl] propane and (-) - N- [3-chloro-1 - (3-pyridinyl) -1 H -pyrazol-4-yl] -N-ethyl-3 - [( 3,3,3-trifluoropropyl) sulflyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5 - [[(2E) -3 Chloro-2-propen-1-yl] amino] -1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethyl) sulfinyl] -1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N- [4-chloro-2-methyl-6- [(methylamino) thioxomethyl] phenyl] -1- (3-chloro-2-pyridinyl) -lH-pyrazole-5-carboxamide,
(Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(l,l- dimethylethyl)amino] carbonyl] -6-methylphenyl] - 1 -(3 -chlor-2-pyridinyl)-3-(fluormethoxy)- 1 H-pyrazol- 5-carboxamid (bekannt aus WO 2012/034403 AI) (CAS 1268277-22-0), N-[2-(5-Amino-l,3,4- thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-l-(3-chlor-2-pyridinyl)-lH-pyrazol-5-carboxamid (bekannt aus WO 2011/085575 AI) (CAS 1233882-22-8), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-l- yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN 101337940 A) (CAS 1108184-52-6); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-l-[3-(trifluormethyl)phenyl]ethyliden]-N-[4- (difluormethoxy)phenyl]hydrazincarboxamid (bekannt aus CN 101715774 A) (CAS 1232543-85-9); Cyclopropancarbonsäure-3-(2,2-dichlorethenyl)-2,2-dimethyl-4-(lH-benzimidazol-2-yl)phenylester (bekannt aus CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-Chlor-2,5-dihydro-2- [[(methoxycarbonyl)[4-[(trifluormethyl)thio]phenyl]amino]carbonyl]indeno[l,2-e][l,3,4]oxadiazin- 4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-0- ethyl-2,4-di-0-methyl- 1 - [N-[4- [ 1 -[4-( 1 , 1 ,2,2,2-pentafluorethoxy)phenyl] - 1 H- 1 ,2,4-triazol-3 - yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014/0275503 AI) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- azabicyclo[3.2.1]octan (CAS 1253850-56-4), (8-anti)-8-(2-Cyclopropylmethoxy-4- trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octan (CAS 933798-27- 7), (8-syn)-8-(2-Cyclopropylmethoxy-4-trifluormethylphenoxy)-3-(6-trifluormethylpyridazin-3-yl)-3- - - azabicyclo[3.2.1]octan (bekannt aus WO 2007040280 AI, WO 2007040282 AI) (CAS 934001-66-8) und N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluo ropyl)thio]-propananlid (bekannt aus WO 2015/058021 AI, WO 2015/058028 AI) (CAS 1477919-27-9). (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(1, 1-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1 H -pyrazole - 5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N- [2- (5-amino-l, 3,4-thiadiazol-2-yl) -4-chloro-6 -methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4- [3 [2,6-dichloro-4 - [(3,3-dichloro-2-propen-1-yl) oxy] phenoxy] propoxy] -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN 101337940 A) ( CAS 1108184-52-6); (2E) - and 2 (Z) -2- [2- (4-cyanophenyl) -1- [3- (trifluoromethyl) phenyl] ethylidene] -N- [4- (difluoromethoxy) phenyl] hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); Cyclopropanecarboxylic acid 3- (2,2-dichloroethenyl) -2,2-dimethyl-4- (1H-benzimidazol-2-yl) phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS) -7-chloro-2,5-dihydro-2- [[(methoxycarbonyl) [4 - [(trifluoromethyl) thio] phenyl] amino] carbonyl] indeno [1,2-e] [l, 3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-Deoxy-3-0-ethyl-2,4-di-O-methyl-1 - [N- [4- [1 - [4- (1,1,2,2-pentafluoroethoxy) phenyl] - 1 H-1, 2,4-triazol-3-yl] phenyl] carbamate] -AL-mannopyranose (known from US 2014/0275503 Al) (CAS 1181213-14-8); 8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 1253850-56-4), (8-anti) -8- (2-Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3-azabicyclo [3.2.1] octane (CAS 933798-27-7), (8-syn) -8- (2 -Cyclopropylmethoxy-4-trifluoromethylphenoxy) -3- (6-trifluoromethylpyridazin-3-yl) -3- - - azabicyclo [3.2.1] octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) and N- [3-chloro-1- (3-pyridinyl) -1H-pyrazole-4- yl] -N-ethyl-3 - [(3,3,3-trifluoro-ropyl) thio] -propananlide (known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9).
Fungizide Die hier mit ihrem "Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im "Pesticide Manual" (16. Aufl. British Crop Protection Council) oder im Internet recherchierbar (beispielsweise: http://www.alanwood.net/pesticides) beschrieben. Fungicides The active ingredients specified here by their "common name" are known and described, for example, in the "Pesticide Manual" (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) ,
Alle genannten Mischungspartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. Alle genannten fungiziden Mischungspartner der Klassen (1) bis (15) können gegebenenfalls tautomere Formen einschließen. All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids. All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.011) Imazalil Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazol, (1.026) (lR,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (1.027) (lS,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l-(lH-l,2,4- triazol-l-ylmethyl)cyclopentanol, (1.028) (2R)-2-(l-Chlorcyclopropyl)-4-[(lR)-2,2-dichlorcyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol ( 1.029) (2R)-2-( 1 -Chlorcyclopropyl)-4- [( 1 S)-2,2- dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.030) (2R)-2- [4-(4-Chlorphenoxy)-2- (trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.031) (2S)-2-( 1 -Chlorcyclopropyl)-4- [(1 R)-2,2-dichlorcyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.032) (2S)-2-( 1 -Chlorcyclopropyl)- 4-[(lS)-2,2-dichlorcyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-1) inhibitors of ergosterol biosynthesis, for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (IR, 2S, 5S) -5- (4 -Chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1.027) (IS, 2R, 5R) -5- (4-chlorobenzyl ) -2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4 - [( lR) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol (1.029) (2R) -2- (1-chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] - 1 - (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.031) (2S) -2- (1-chlorocyclopropyl) -4- [(1R) -2, 2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.032) (2S) -2- (1-chlorocyclopropyl) -4 - [(IS) -2,2-dichlorocyclopropyl] -1- (1H-l, 2,4-triazol-1-yl) butan-2-ol, (1033) (2S) -2- [4- (4-
Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.034) (R)- [3 -(4-Chlor- 2-fluo henyl)-5-(2,4-difluo henyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2- fluo henyl)-5-(2,4-difluo henyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-Chlor-2- fluoφhenyl)-5-(2,4-difluoφhenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) l-({(2R,4S)-2-[2- Chlor-4-(4-chlorphenoxy)phenyl] -4-methyl- 1 ,3 -dioxolan-2-yl } methyl)- 1 H- 1 ,2,4-triazol, ( 1.038) 1 - ( { (2S ,4S)-2- [2-Chlor-4-(4-chlorphenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2-yl } methyl)- 1 H- 1 ,2,4-triazol, (1.039) l-{ [3-(2-Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl- thiocyanat, ( 1.040) 1 - { [rel(2R,3R)-3 -(2-Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl } - 1 H- l,2,4-triazol-5-yl-thiocyanat, (1.041) l-{ [rel(2R,3S)-3-(2-Ch^henyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl-thiocyanat, (1.042) 2-[(2R,4R,5R)-l-(2,4-Dich^henyl)-5-hydroxy- - - Chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1034) (R) - [3 - (4-chloro) 2-fluorohexyl) -5- (2,4-difluorohexyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (1.035) (S) - [3- (4-chloro -2-fluorenyl) -5- (2,4-difluorohexyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (1.036) [3- (4-chloro-2- fluoφhenyl) -5- (2,4-difluoro-phenyl) -l, 2-oxazol-4-yl] (pyridin-3-yl) -methanol, (1.037) 1 - ({(2R, 4S) -2- [2- Chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole, (1038) 1 - ({(2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole, (1,039 ) 1- {[3- (2-Chloro-phenyl) -2- (2,4-difluoro-phenyl) -oxiran-2-yl] -methyl} -1H-l, 2,4-triazol-5-yl-thiocyanate, (1040) 1 - {[rel (2R, 3R) -3 - (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole-5 yl-thiocyanate, (1.041) 1- {[rel (2R, 3S) -3- (2-chloro-1-yl) -2- (2,4-difluorophenyl) -oxiran-2-yl] -methyl} -LH-1, 2,4-triazol-5-yl-thiocyanate, (1.042) 2 - [(2R, 4R , 5R) -l- (2,4-Dich ^ henyl) -5-hydroxy- - -
2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-l-(2,4- Dichlo henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.044) 2- [(2R,4S,5R)-l-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazol-3-thion, (1.045) 2-[(2R,4S,5S)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-l-(2,4-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1043) 2 - [(2R, 4R, 5S) -l- ( 2,4-dichloro-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.044) 2- [(2R, 4S, 5R) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4-dihydro-3H-l, 2,4- triazole-3-thione, (1.045) 2 - [(2R, 4S, 5S) -1- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2 , 4-dihydro-3H-1, 2,4-triazole-3-thione, (1.046) 2 - [(2S, 4R, 5R) -1- (2,4-dichloro) -5-hydroxy-2 , 6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (1047) 2 - [(2S, 4R, 5S) -l- (2 , 4-
Dichlo henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.048) 2- [(2S,4S,5R)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol^Dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1048) 2- [(2S, 4S, 5R) -l- (2,4-Dich ^ henyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4-dihydro-3H-l, 2,4-triazol ^
3- thion, (1.049) 2-[(2S,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.050) 2-[l-(2,4-Dichlo henyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.051) 2-[2-Chlor-4-(2,4-dichlorophenoxy)phenyl]-l-(lH- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.052) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 - yl)butan-2-ol, ( 1.053) 2- [4-(4-Chlo henoxy)-2-(triίluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan- 2-ol, ( 1.054) 2-[4-(4-Ch^henoxy)-2-(trinuormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol, (1.055) 2-[4-(4-Ch^henoxy)-2-(trifluormethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.056) 2- { [3 -(2-Chloφhenyl)-2-(2,4-diίluorphenyl)oxiran-2-yl] methyl } -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, (1.057) 2-{ [rel(2R,3R)-3-(2-Ch^henyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H- l,2,4-triazol-3-thion, (1.058) 2-{ [rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- l-(lH-l,2,4-triazol-l-ylmethyl)cyclopentanol, (1.060) 5-(Allylsulfanyl)-l-{ [3-(2-chlorphenyl)-2-(2,4- difluoφhenyl)oxiran-2-yl] methyl } - 1 H- 1 ,2,4-triazol, ( 1.061 ) 5-( Allylsulfanyl)- 1 - { [rel(2R,3R)-3 -(2- chloφhenyl)-2-(2,4-diίluoφhenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol, ( 1.062) 5-(Allylsulfanyl)- 1 - { [rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.063) N'- (2,5-Dimethyl-4- { [3-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] sulfanyl }phenyl)-N-ethyl-N- methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4-{ [3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)- N-ethyl-N-methylimidoformamid, (1.065) N'-(2,5-Dimethyl-4-{ [3-(2,2,3,3- tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.066) N'-(2,5-Dimethyl-3-thione, (1.049) 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, (1050) 2- [1- (2,4-dichloro-5-yl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2 , 4-dihydro-3H-1, 2,4-triazole-3-thione, (1.051) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1, 2, 4-triazol-1-yl) propan-2-ol, (1.052) 2- [2-Chloro-4- (4-chlorophenoxy) phenyl] -1 - (1H-1, 2,4-triazole-1 - yl) butan-2-ol, (1.053) 2- [4- (4-chloro-oxy) -2- (trifluoromethyl) -phenyl] -1- (1H-1,2,4-triazol-1-yl) butane - 2-ol, (1.054) 2- [4- (4-Chhenoxy) -2- (tri-methyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) pentane-2 -ol, (1.055) 2- [4- (4-Chhenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazol-1-yl) propan-2-ol, (1.056) 2- {[3- (2-Chloro-phenyl) -2- (2,4-di-fluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3 -thione, (1.057) 2- {[rel (2R, 3R) -3- (2-chloro-1-yl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro -3H-l, 2,4-triazole-3-thione, (1.058) 2- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.059) 5- (4-chlorobenzyl) - 2- (chloromethyl) -2-methyl-1- (1H-l, 2,4-triazol-1-ylmethyl) cyclopentanol, (1.060) 5- (allylsulfanyl) -l- {[3- (2-chlorophenyl) - 2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1, 2,4-triazole, (1.061) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3 - (2-chloro-phenyl) -2- (2,4-di-fluoro-phenyl) oxiran-2-yl] -methyl} -1H-1,2,4-triazole, (1.062) 5- (allylsulfanyl) -1 - {[rel. 2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-l, 2,4-triazole, (1.063) N '- (2, 5-Dimethyl-4- {[3- (1,1,2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.064) N '- (2,5-dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.065) N '- (2,5-dimethyl-4- {[3- (2 , 2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.066) N '- (2,5-dimethyl)
4- { [3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.067) N'-(2,5- Dimethyl-4-{3-[(l,l,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.068) N'-(2,5-Dimethyl-4-{3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamid, (1.069) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3- tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.070) N'-(2,5-Dimethyl- 4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.071) N'-(2,5- Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (1.072) N'-(4-{ [3- (Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'- (4- { 3 - [(Difluormethyl) sulfanyl] phenoxy } -2, 5 -dimethylphenyl) -N-ethyl-N-methylimidof ormamid, (1.074) N'-[5-Brom-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N- methylimidoformamid, ( 1.075) N'- { 4- [(4,5-Dichlor- 1 ,3-thiazol-2-yl)oxy] -2,5 -dimethylphenyl } -N-ethyl- - - 4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1.067) N '- (2,5-dimethyl-4- {3 - [(l, l, 2, 2-tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1068) N '- (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy } phenyl) -N-ethyl-N-methylimidoformamide, (1.069) N '- (2,5-dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N ethyl N-methylimidoformamide, (1.070) N '- (2,5-dimethyl-4- {3 - [(pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1.071) N'- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1.072) N '- (4- {[3- (difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N- ethyl N -methylimidoformamide, (1.073) N '- (4- {3 - [(Difluoromethyl) sulfanyl] phenoxy} -2, 5-dimethylphenyl) -N-ethyl-N-methylimidoforamido, (1.074) N' - [ 5-Bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (1.075) N '- {4- [( 4,5-dichloro-1,3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl - -
N-methylimidoformamid, ( 1.076) Ν'- { 5-Brom-6- [( 1 R)- 1 -(3 ,5 -difluorophenyl)ethoxy] -2-methylpyridin- 3-yl } -N-ethyl-N-methylimidoformamid, ( 1.077) N'- { 5-Brom-6- [( 1 S)- 1 -(3 ,5 -difluo henyl)ethoxy] -2- methylpyridin-3 -yl } -N-ethyl-N-methylimidoformamid, ( 1.078) N'- { 5-Brom-6- [(cis-4- isopropylcyclohexyl)oxy] -2-methylpyridin-3 -yl } -N-ethyl-N-methylimidoformamid, ( 1.079) N'- { 5 - Brom-6- [(trans-4-isopropylcyclohexyl)oxy] -2-methylpyridin-3 -yl } -N-ethyl-N-methylimidoformamid, (1.080) N'-{ 5-Bromo-6- [ 1 -(3 ,5 -difluorphenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N- methylimidoformamid. N-methylimidoformamide, (1.076) Ν '- {5-bromo-6- [(1 R) -1- (3, 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamide, (1.077) N '- {5-bromo-6- [(1S) -1- (3,5-difluorohexyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide , (1.078) N '- {5-bromo-6- [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.079) N'- {5 - bromo-6- [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1080) N '- {5-bromo-6- [1 - ( 3, 5 -difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide.
2) Inhibitoren der Atmungskette am Komplex I oder II beispielsweise (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isoietamid, (2.010) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.011) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.012) Isopyrazam (anti- epimeres Racemat 1RS,4SR,9SR), (2.013) Isopyrazam (Mischung des syn-epimeren Razemates 1RS,4SR,9RS und des anti-epimeren Razemates 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) l,3-Dimethyl-N-(l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.023) l,3-Dimethyl-N-[(3R)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.024) l,3-Dimethyl-N-[(3S)-l,l,3-trimethyl-2,3- dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.025) 1 -Methyl-3 -(triiluormethyl)-N- [2'- (trilluormethyl)biphenyl-2-yl] - 1 H-pyr azol-4-carboxamid, (2.026) 2-Fluor-6 -(trilluoromethyl) -N-( 1 , 1 , 3 - trimethyl-2,3 -dihydro- 1 H-inden-4-yl)benzamid, (2.027) 3-(Difluormethyl)- 1 -methyl-N-( 1 , 1 ,3 -trimethyl- 2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4-carboxamid, (2.028) 3-(Difluormethyl)-l-methyl-N-[(3R)- 1 , 1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl] - lH-pyrazol-4-carboxamid, (2.029) 3-(Dilluormethyl)- 1 - methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.030) 3- (Dilluormethyl)-N-(7-iluor- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 -methyl- 1 H-pyrazol-4- carboxamid, (2.031) 3-(Dilluormethyl)-N-[(3R)-7-fluor-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l- methyl-lH-pyrazol-4-carboxamid, (2.032) 3-(Diiluoromethyl)-N-[(3S)-7-fluor-l,l,3-trimethyl-2,3- dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.033) 5 ,8-Dilluor-N- [2-(2-lluor-4- { [4- (triiluormethyl)pyridin-2-yl]oxy }phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5- fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.035) N- (2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(dilluormethyl)-5-iluor-l-methyl-lH-pyrazol-4- carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(diiluormethyl)-5-fluor-l-methyl-lH- pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-lluor-l- methyl-lH-pyrazol-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3- (difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.039) N-[(lR,4S)-9-(Dichlormethylen)- l,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.040) N-[( 1 S ,4R)-9-(Dichlormethylen)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3 - - - 2) inhibitors of the respiratory chain on complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isoietamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR , 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), ( 2.015) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.016) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyrazolium , (2.021) Sedaxanes, (2.022) 1,3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, ( 2.023) 1,3-dimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.024) 1,3-Dimethyl-N - [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (2.025) 1 -Methyl-3 - (tri-methyl) -N- [2'- (trifluoromethyl) biphenyl-2-yl] -1 H -pyr-azole-4-carboxamide, (2.026) 2-fluoro-6 - (trifluoromethyl) -N- (1,1,1-trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (2.027) 3- (difluoromethyl) -1-methyl-N- (1, 1, 3-trimethyl) 2,3-dihydro-1H-inden-4-yl) -1H-pyrazole-4-carboxamide, (2.028) 3- (difluoromethyl) -1-methyl-N - [(3R) -1,3,3-trimethyl -2,3-dihydro-1H-inden-4-yl] - lH-pyrazole-4-carboxamide, (2.029) 3- (dillormethyl) -1-methyl-N - [(3S) -l, l, 3 trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide; (2,030) 3- (dilluoromethyl) -N- (7-butyl-1, 1, 3-trimethyl-2 , 3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3- (dilluoromethyl) -N - [(3R) -7-fluoro-1, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3- (diisoromethyl) -N - [(3S) -7 -fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1-methyl- 1 H -pyrazole-4-carboxamide, (2.033) 5,8-dinucuron-N- [2- (2-fluoro-4- {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazoline -4-amine, (2.034) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N - (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (dilloromethyl) -5-iluor-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N- (2-tert-butylbenzyl ) -N-cyclopropyl-3- (diisoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- ( difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-one methyl-1H-pyrazole-4-carboxamide, (2.039) N - [(IR, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3 - (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.040) N - [(1S, 4R) -9- (dichloromethylene) -1,3,3,4-tetrahydro-1, 4- methanonaphthalene-5-yl] -3 - - -
(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.041 ) N- [ 1 -(2,4-Dichlorphenyl)- 1 - methoxypropan-2-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.042) N-[2-Chlor-6- (trifluormethyl)benzyl] -N-cyclopropyl-3 -(difluormethyl) -5 -fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.043) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-l- methyl- lH-pyrazol-4-carboxamid, (2.044) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3- (difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3-(difluormethyl)- 5-fluor- 1 -methyl-N- [5 -methyl -2-(trifluormethyl)benzyl] - 1 H-pyrazol-4-carboxamid, (2.046) N- Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l-methyl-lH-pyrazol-4- carboxamid, (2.047) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-l - methyl- lH-pyrazol-4-carboxamid, (2.048) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2- isopropylbenzyl)-l-methyl-lH-pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3-(difluoromethyl)-5- fluor-N-(2-isopropylbenzyl)-l -methyl-lH-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3-(difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.041) N- [1- (2,4-dichlorophenyl) -1-methoxy-propan-2-yl] -3- (difluoromethyl) -l- methyl-1H-pyrazole-4-carboxamide, (2.042) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole -4-carboxamide, (2.043) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4 carboxamide, (2.044) N- [5-chloro-2- (trifluoromethyl) benzyl] -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1 H -pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3 (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,048) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -l methyl-lH-pyrazol-4-car bothioamide, (2.049) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (2,050) N-cyclopropyl-3-yl
(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.051) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (2.052) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl-lH- pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l- methyl-lH-pyrazole-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor-l-methyl-lH-pyrazole-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl- 5-methylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazole-4-carboxamid, (2.056) N- Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazole-4-carboxamid. (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3- (difluoromethyl) -N- (2) ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-fluorobenzyl) - 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5-fluoro-1-methyl-1H -pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055 ) N-Cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N- (2 -cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-l-methyl-lH-pyrazole-4-carboxamide.
3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[({ [(lE)-l-(3-{ [(E)-l-Fluor-2- phenylvinyl] oxy } phenyl)ethyliden] amino } oxy)methyl] phenyl } -2-(methoxyimino) -N-methylacetamid, (3.022) (2E,3Z)-5-{ [l-(4-Chlorphenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3- enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6- methyl-4,9-dioxo-l,5-dioxonan-7-yl-2-methylpropanoat, (3.026) 2-{2-[(2,5-3) respiratory chain inhibitors on complex III, for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- {2 - [({[(IE) -l- (3- {[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5- {[1- (4-chlorophenyl) -1H-pyrazole] 3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2- methoxy-N-methylacetamide, (3.024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.025) (3S, 6S, 7R, 8R ) -8-benzyl-3 - [({3 - [(isobutyryloxy ) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-l, 5-dioxonan-7-yl-2-methylpropanoate, (3.026) 2- {2- [ (2,5-
Dimethylphenoxy)methyl] phenyl }-2-methoxy-N-methylacetamid, (3.027) N-(3-Ethyl-3,5,5- trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{ [l-(4-Chlor-2-fluo henyl)- 1 H-pyrazol-3 -yl] oxy } -2-(methoxyimino)-N,3 -dimethylpent-3-enamid. - - Dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.027) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3.028) (2E, 3Z) -5- {[1- (4-chloro-2-fluoro-1-yl) -1-H-pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethyl-pent-3-enamide. - -
4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, , (4.009) 3-αη1θΓ-4-(2,6^ίΠυο 1ΐ6ηγ1)-6-ιη6ΐ1ιγ1-5- phenylpyridazin, (4.010) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (4.011) 3- Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.012) 4-(2-Brom-4- fluo henyl)-N-(2,6-difluo henyl)-l,3-dimethyl-lH-pyrazol-5-arnin, (4.013) 4-(2-Brom-4- fluo henyl)-N-(2-brom-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-arnin, (4.014) 4-(2-Brom-4- fluoφhenyl)-N-(2-bromphenyl)-l,3-dimethyl-lH-pyrazol-5-arnin, (4.015) 4-(2-Brom-4-fluoφhenyl)-N- (2-chlor-6-fluoφhenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluoφhenyl)-N-(2- chloφhenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluoφhenyl)- l,3-dimethyl-lH-pyrazol-5-amin, (4.018) 4-(2-Chlor-4-fluoφhenyl)-N-(2,6-difluoφhenyl)-l,3- dimethyl- 1 H-pyrazol-5 -amin, (4.019) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluoφhenyl)- 1,3- dimethyl-lH-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH- pyrazol-5-amin, (4.021 ) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluoφhenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5 -amin, (4.022) 4-(4-Ch^henyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.023) N-(2-Brom-6- fluoφhenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.024) N-(2-Bromphenyl)-4- (2-chlor-4-fluoφhenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.025) N-(4-Chlor-2,6-difluorphenyl)-4-(2- chlor-4-fluorphenyl) -1,3 -dimethyl- 1 H-pyrazol-5 -amin. 4) inhibitors of mitosis and cell division, for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-αη1ΓΓ-4- (2,6 ^ ουο 1ΐ6ηγ1) -6-ιη6ΐ1ιγ1-5phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6- difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2 -Brom-4-fluoro-1-yl) -N- (2,6-difluorohexyl) -1,3-dimethyl-1H-pyrazole-5-arnine, (4.013) 4- (2-bromo-4-fluoro-1-ylene) - N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-arnine, (4.014) 4- (2-bromo-4-fluoro-phenyl) -N- (2-bromophenyl) -l , 3-dimethyl-1H-pyrazole-5-arnine, (4.015) 4- (2-bromo-4-fluoro-phenyl) -N- (2-chloro-6-fluoro-phenyl) -l, 3-dimethyl-1H-pyrazole 5-amine, (4.016) 4- (2-bromo-4-fluoro-phenyl) -N- (2-chloro-phenyl) -l, 3-dimethyl-1H-pyrazol-5-amine, (4.017) 4- (2-bromo 4-fluorophenyl) -N- (2-fluoro-phenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.01 8) 4- (2-chloro-4-fluoro-phenyl) -N- (2,6-difluoro-phenyl) -l, 3-dimethyl-1H-pyrazole-5-amine, (4.019) 4- (2-chloro-4 -fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,020) 4- (2-chloro-4-fluorophenyl) -N- (2 chlorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazole -5-amine, (4.022) 4- (4-chhenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4.023) N- (2-bromo-6-fluoro-phenyl) -4 (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine, (4,024) N- (2-bromophenyl) -4- (2-chloro-4-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.025) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H- pyrazole-5-amine.
5) Verbindungen mit Befähigung zu Multisite-Aktivität, beispielsweise (5.001) Bordeauxmischung, (5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006)5) Compounds capable of multisite activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006)
Kupfernaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinkmetiram, (5.017) Kupfer-Oxin, (5.018) Propineb, (5.019) Schwefel und Schwefelzubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Verbindungen, die zum Auslösen einer Wirtsabwehr befähigt sind, beispielsweise (6.001) Acibenzolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. Copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2 +) sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015 ) Metiram, (5.016) Zinc Metiram, (5.017) Copper Oxine, (5.018) Propineb, (5.019) Sulfur and Sulfur Preparations Including Calcium Polysulfide, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Compounds capable of inducing host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
7) Inhibitoren der Aminosäure- und/oder Protein-Biosynthese, beispielsweise (7.001) Cyprodinil,7) inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil,
(7.002) Kasugamycin, (7.003) Kasugamycinhydrochlorid-hydrat, (7.004) Oxytetracyclin (7.005) Pyrimethanil, (7.006) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l -yl)chinolin. (8) Inhibitoren der ATP-Produktion, beispielsweise (8.001) Silthiofam. (7.002) Kasugamycin, (7.003) Kasugamycin Hydrochloride Hydrate, (7.004) Oxytetracycline (7.005) Pyrimethanil, (7.006) 3- (5-Fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl ) quinoline. (8) Inhibitors of ATP production, for example, (8,001) silthiofam.
9) Inhibitoren der Zellwandsynthese, beispielsweise (9.001) Benthiavalicarb, (9.002) Dimethomorph,9) inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
(9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph, (9.007) Valifenalat, (9.008) (2E)-3-(4-tert.-Butylphenyl)-3-(2-chloφyridin-4-yl)-l-(moφholin-4-yl)prop-2-en- 1-on, (9.009) (2Z)-3-(4-tert.-Butylphenyl)-3-(2-chloφyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on. - - (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamide, (9.006) Pyrimorph, (9.007) Valifenalate, (9.008) (2E) -3- (4-tert-Butylphenyl) -3- (2-chloropyridine) 4-yl) -1- (4-yl) prop-2-en-1-one, (9.009) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridine-4 -yl) -l- (morpholin-4-yl) prop-2-en-l-one. - -
10) Inhibitoren der Lipid- und Membran-Synthese, beispielsweise (10.001) Propamocarb, (10.002) Propamocarbhydrochlorid, (10.003) Tolclofos-Methyl. 10) Inhibitors of lipid and membrane synthesis, for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
11) Inhibitoren der Melanin-Biosynthese, beispielsweise (11.001) Tricyclazol, (11.002) 2,2,2- Triiluorethyl-{3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl}carbamat. 12) Inhibitoren der Nukleinsäuresynthese, beispielsweise (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam). 11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate. 12) inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
13) Inhibitoren der Signaltransduktion, beispielsweise (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 13) inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
14) Verbindungen, die als Entkoppler wirken können, beispielsweise (14.001) Fluazinam, (14.002) Meptyldinocap. 14) compounds which may act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Weitere Verbindungen, beispielsweise (15.001) Abscisinsäure, (15.002) Benthiazol, (15.003) Bethoxazin, (15.004) Capsimycin, (15.005) Carvon, (15.006) Chinomethionat, (15.007) Cufraneb, (15.008) Cyflufenamid, (15.009) Cymoxanil, (15.010) Cyprosulfamid, (15.011) Flutianil, (15.012) Fosetyl-Aluminium, (15.013) Fosetyl-Calcium, (15.014) Fosetyl-Natrium, (15.015) Methylisothiocyanat, (15.016) Metrafenon, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel-Dimethyldithiocarbamat, (15.020) Nitrothal-Isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiprolin, (15.023) Oxyfenthiin, (15.024) Pentachlorphenol und Salze, (15.025) Phosphonsäure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pyriofenone (Chlazafenone) (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanide, (15.031) l-(4-{4-[(5R)-5-(2,6-Difluorphenyl)- 4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluormethyl)-lH- pyrazol-l-yl]ethanon, (15.032) l-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3- thiazol-2-yl Jpiperidin- 1 -yl)-2- [5 -methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] ethanon, ( 15.033) 2-(6- Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrol- l,3,5,7(2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2-in-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.036) 2-[3,5- Bis(difluormethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-chlor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2- oxazol-3-yl } - 1 ,3-thiazol-2-yl)piperidin- 1 -yl]ethanon, ( 15.037) 2-[3,5-Bis(difluormethyl)- lH-pyrazol- 1 - yl]-l-[4-(4-{5-[2-fluor-6-(prop-2-in-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2- yl)piperidin-l-yl] ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.039) 2-{(5R)-3-[2-(l-{ [3,5-Bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4- yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorphenyl methanesulfonat, (15.040) 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-chlo henyl methanesulfonat, (15.041) 2-{2-[(7,8-Difluor-2-methylquinolin-3-yl)oxy]-6- fluorphenyl}propan-2-ol, (15.042) 2-{2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2- ol, (15.043) 2-{3-[2-(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-chlorphenyl-methansulfonat, (15.044) 2-{3-[2-(l-{ [3,5-15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) Cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil , (15,010) Cyprosulfamide, (15,011) Flutianil, (15,012) Fosetyl-aluminum, (15,013) Fosetyl-calcium, (15,014) Fosetyl-sodium, (15,015) Methylisothiocyanate, (15,016) Metrafenone, (15,017) Mildiomycin, (15,018) Natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphonic acid and its salts, (15.026) propamocarb -fosetylate, (15.027) pyriofenone (Chlazafenone) (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1- (4- {4 - [(5R) -5- (2,6-difluorophenyl) - 4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -lH- pyrazol-1-yl] ethanone, (15.032) 1- (4- {4 - [(5S) -5- (2,6-diflu orphenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thiazol-2-yl, Jpiperidin-1-yl) -2- [5-methyl-3 - (trifluoromethyl) -1 H -pyrazol-1-yl] ethanone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline, (15.034) 2,6-dimethyl-1H, 5H- [l, 4] dithiino [2,3- c: 5,6-c '] dipyrrolo, 3,5,7 (2H, 6H) -tetrone, (15,035) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] - 1- [4- (4- {5- [2- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole -2-yl) piperidin-1-yl] ethanone, (15.036) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2 -chloro-6- (prop-2-yn-1-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidine-1 - yl] ethanone, (15.037) 2- [3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -1- [4- (4- {5- [2-fluoro-6- (prop-2 -in-1-yloxy) phenyl] -4,5-dihydro-l, 2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.038) 2- [6- (3-Fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15.039) 2 - {(5R) -3- [2- (1 - {[3,5-bis (difluoromethyl ) -LH-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazole -5-yl} -3-chlorophenyl methanesulfonate, (15.040) 2 - {(5S) -3- [2- (1 - {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] -acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chloro-1-yl-methanesulfonate, (15.041) 2- {2- [ (7,8-Difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} -propan-2-ol, (15.042) 2- {2-Fluoro-6 - [(8-fluoro-2-methylquinoline) 3-yl) oxy] phenyl} propan-2-ol, (15.043) 2- {3- [2- (1- {[3,5-bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidine -4-yl) -l, 3-thiazol-4- - - yl] -4,5-dihydro-l, 2-oxazol-5-yl} -3-chlorophenyl-methanesulfonate, (15.044) 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 yljphenyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-(4,4,5-Trifluor-3,3- dimethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinolin, ( 15.047) 3-(4,4-Difluor-3 ,3 -dimethyl-3 ,4- dihydroisoquinolin-l-yl)quinolin, (15.048) 4-Amino-5-lluorpyrimidin-2-ol (Tautomere Form: 4-Amino- 5-ίluo yrimidin-2(lH)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino- l,3,4-thiadiazol-2-thiol, (15.051) 5-Chlor-N'-phenyl-N'-(prop-2-yn-l-yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-lluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4- methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fluor-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-l,4- benzoxazepin, (15.055) But-3-yn-l-yl {6-[({ [(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.056) Ethyl (2Z)-3-amino-2-cyano- 3-phenylacrylat, (15.057) Phenazin-1 -carbonsäure, (15.058) Propyl 3,4,5-trihydroxybenzoat, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfat (2:1), (15.061) tert-Butyl {6-[({ [(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamat. Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl-phenylmethanesulfonate, 15.045) 2-phenylphenol and its salts, (15.046) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.047) 3- (4.4 Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoro-pyrimidine-2 ( 1H) -one), (15.049) 4-oxo-4 - [(2-phenylethyl) amino] butyric acid, (15.050) 5-amino-1, 3,4-thiadiazole-2-thiol, (15.051) 5-chloro -N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.052) 5-Fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, ( 15,053) 5-Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.054) 9-Fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro -l, 4-benzoxazepine, (15.055) but-3-yn-1-yl {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.056) ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, ( 15,058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinoline-8-ol sulfate (2: 1), (15.061) tert-butyl {6 - [({[(1 -methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate. Biological pesticides as mixture components
Die Verbindungen der Formel (I) oder der Formel (Γ) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. The compounds of the formula (I) or the formula (II) can be combined with biological pesticides.
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.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of such bacteria which can be used as biological pesticides are:
Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, insbesondere B. thuringiensis Subspezies israelensis (Serotyp H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder B. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD- 1372), oder B. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), - - 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 B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. 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 Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts which can be used as biological pesticides are:
Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (neu: Isaria 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, in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874 ), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of viruses that can be used or used as biological pesticides are:
Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapsel wurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton capsule worm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis ( African cotton worm) NPV.
Es sind auch Bakterien und Pilze umfasst, die als Jnokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: It also includes bacteria and fungi, which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
Agrobacterium spp. , Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Agrobacterium spp. , Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoff Wechselprodukte, 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/Pyrethrine, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum - Arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrin, Quassia amara, Quercus, Quillaja, Regalia, "Requiem ™ Insecticide", Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol , Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrine, Viscum album, Brassicacaeen extract, especially rapeseed or mustard powder.
Safener als Mischungskomponenten Safener as a mixture component
Die Verbindungen der Formel (I) oder der Formel (Γ) 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-The compounds of the formula (I) or of the formula (II) can be combined with safeners, for example 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)benzamid (CAS 129531-12-0), 4-(Dichloracetyl)-l-oxa-4- azaspiro[4.5]decan (CAS 71526-07-3), 2,2,5-Trimethyl-3-(dichloracetyl)-l,3-oxazolidin (CAS 52836- 31-4). [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2, 5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (CAS 52836- 31-4).
Pflanzen und Pflanzenteile Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Paprika, Gurke, Melone, Möhre, Wassermelone, Zwiebel, Salat, Spinat, Porree, Bohnen, Brassica oleracea (z. B. Kohl) und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzen sollen alle Entwicklungsstadien wie Saatgut, Stecklinge, junge (unausgereifte) Pflanzen bis hin zu ausgereiften Pflanzen verstanden werden. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und 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 gehören auch geerntete Pflanzen oder geerntete Pflanzenteile sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. Plants and Plant Parts According to the invention, all plants and plant parts can be treated. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes). Crop plants can be plants 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, such as seeds, cuttings, young (unripe) plants and 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 harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) oder der Formel (Γ) erfolgt direkt oder durch Einwirkung der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, - - The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) or of the formula (II) takes place directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, - -
Spritzen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. Spraying, vaporizing, atomising, spreading, brushing, injecting and propagating material, in particular in the case of seeds, further by single-layer or multi-layer coating.
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 Protoplasteniusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw.„Teile von Pflanzen" oder„Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes. Transgenic plant, seed treatment and integration events
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z. B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z. B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z. B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinone, Sulfonylharnstoffe, Glyphosat oder Phosphinotricin (z. B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, - - The preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z. By toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z. For example, systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, - -
Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchte und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. Tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape are particularly emphasized , Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
Pflanzenschutz - Behandlungsarten Plant protection - types of treatment
Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) oder der Formel (Γ) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) oder der Formel (Γ) nach dem Ultra-Low- Volume -Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) oder der Formel (Γ) selbst in den Boden zu injizieren. The treatment of the plants and plant parts with the compounds of the formula (I) or the formula (Γ) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) or the formula (II) by the ultra-low-volume method or the use form or the compound of the formula (I) or the Inject formula (Γ) itself into the soil.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d. h. die Verbindungen der Formel (I) oder der Formel (Γ) 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. H. the compounds of the formula (I) or of the formula (II) are applied to the foliage, wherein the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.
Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) oder der Formel (Γ) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) oder der Formel (Γ) 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) oder der Formel (Γ) getränkt, oder durch die Bodenapplikation, d. h. die erfindungsgemäßen Verbindungen der Formel (I) oder der Formel (Γ) 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) oder der Formel (Γ) in einer festen Anwendungsform (z. B. als Granulat) in ein überflutetes Reisfeld sein. In the case of systemically active substances, the compounds of the formula (I) or of the formula (II) 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) or formula (Γ) on the habitat of the plant. This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I) or formula (II), or by the soil application, i. H. the compounds of the formula (I) or the formula (II) according to the invention are introduced into the plant in solid form (for example in the form of granules). In water rice crops, this may also be by metered addition of the compound of formula (I) or formula (II) in a solid form (eg as granules) into a flooded paddy field.
Saatgutbehandlung 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 auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) oder der Formel (Γ) 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) oder der Formel (Γ) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) oder der Formel (Γ) und einer Mischungskomponente behandelt wird. Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to 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 have methods of protecting the seed and the germinating plant - - which make unnecessary, or at least significantly reduce, the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort. The present invention therefore more particularly relates to a method of protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I) or formula (II). The method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) or formula (II) and a mixture component. It also further comprises a method in which the seed is treated at different times with a compound of the formula (I) or the formula (II) and a mixture component.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) oder der Formel (Γ) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. The invention also relates to the use of the compounds of the formula (I) or of the formula (II) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer erfindungsgemäßen Verbindung der Formel (I) oder der Formel (Γ) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) oder der Formel (Γ) und einer Mischungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) oder der Formel (Γ) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) oder der Formel (Γ) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (I) oder der Formel (Γ) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) oder der Formel (Γ) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) oder der Formel (Γ) einem Filmcoating- Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) or the formula (Γ) according to the invention. The invention also relates to seed treated at the same time with a compound of formula (I) or formula (II) and a mixture component. The invention further relates to seed which has been treated at different times with a compound of the formula (I) or the formula (II) and a mixture component. For seeds which have been treated at different times with a compound of the formula (I) or the formula (II) and a mixture component, the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) or of the formula (II) and of the mixture components may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) or the formula (II) and a mixture component are applied as a constituent of an envelope or as a further layer or further layers in addition to an envelope. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I) or the formula (II), is subjected to a film coating process in order to avoid dust abrasion on the seed.
Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (I) oder der Formel (Γ) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. One of the advantages that occurs when a compound of formula (I) or formula (II) acts systemically is that the treatment of the seed not only protects the seed itself but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) oder der Formel (Γ) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Another advantage is the fact that by treating the seed with a compound of formula (I) or the formula (Γ) germination and emergence of the treated seed can be promoted.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) oder der Formel (Γ) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Likewise, it is considered to be advantageous that compounds of the formula (I) or of the formula (II) can also be used in particular in the case of transgenic seed.
Verbindungen der Formel (I) oder der Formel (Γ) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of formula (I) or formula (II) 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 occurs an optimized nitrogen fixation comes.
Die Verbindungen der Formel (I) oder der Formel (Γ) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baumwolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z. B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps, Gemüse und Reis zu. Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) oder der Formel (Γ) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. - - The compounds of the formula (I) or of the formula (II) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) or the formula (II) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis. - -
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) oder der Formel (Γ) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage"), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. In the context of the present invention, the compound of the formula (I) or the formula (II) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming. In the case of rice seeds, it is also possible to use seeds that have been soaked, for example, in water to a certain stage of the rice embryo ("Pigeon Breast Stage"), which stimulates germination and a more uniform emergence.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) oder der Formel (Γ) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. In general, care must be taken when treating the seed that the amount of compound of formula (I) or formula (Γ) and / or other additives applied to the seed is chosen so as not to affect the germination of the seed or the resulting plant is not damaged. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
Die Verbindungen der Formel (I) oder der Formel (Γ) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. Die Verbindungen der Formel (I) oder der Formel (Γ) 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) or of the formula (II) 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) or of the formula (II) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Verbindungen der Formel (I) oder der Formel (Γ) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing the compounds of formula (I) or formula (Γ) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives , secondary thickeners, glues, gibberellins and even water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. - - Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1. - -
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalinsulfonate, wie Diisopropyl- oder Diisobutylnaphthalinsulfonate. Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise 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 alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401- 412). Gibberellins which may be present in the seed dressing formulations which can be used in accordance with the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).
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 - - become. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature. The seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder dem daraus durch Zugabe von Wasser hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im Einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichen oder kontinuierlichen Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water, all mixing devices which can usually be used for the dressing can be considered. Specifically, in the pickling process, the seed is placed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) oder der Formel (Γ) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) oder der Formel (Γ) 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) or of the formula (II) in the formulations and according to the seed. The application rates in the compound of the formula (I) or of the formula (II) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
Tiergesundheit Auf dem Gebiet der Tiergesundheit, d. h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) oder der Formel (Γ) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. Animal health In the field of animal health, d. H. In the veterinary field, the compounds of formula (I) or of formula (II) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects or acarids.
Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I) oder der Formel (Γ), 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 field of veterinary medicine, the compounds of the formula (I) or of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for the control of parasites used in livestock and animal husbandry in livestock, breeding animals, zoo animals, laboratory animals, Experimental animals and pets occur. They are effective against all or individual stages of parasite development.
Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; oder Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; oder Fische oder Krustentiere, z. B. in der Aquakultur, oder gegebenenfalls Insekten wie Bienen. - - Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees. - -
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel; Reptilien, Amphibien oder Aquariumfische . The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
Gemäß einer bestimmten Ausführungsform werden die Verbindungen der Formel (I) oder der Formel (Γ) an Säugetiere verabreicht. According to a particular embodiment, the compounds of the formula (I) or the formula (II) are administered to mammals.
Gemäß einer weiteren bestimmten Ausführungsform werden die Verbindungen der Formel (I) oder der Formel (Γ) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. According to another specific embodiment, the compounds of the formula (I) or of the formula (II) are administered to birds, namely caged birds or, in particular, poultry.
Durch Verwendung der Verbindungen der Formel (I) oder der Formel (Γ) 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 the formula (I) or the formula (Γ) for the control of animal parasites disease, death and performance reductions (in meat, milk, wool, hides, eggs, honey and the like) are to be reduced or prevented, so that a more economical and easier animal husbandry is possible and a better welfare of the animals is achievable.
In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) oder der Formel (Γ) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) oder der Formel (Γ) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern. With regard to the field of animal health, the term "controlling" or "controlling" in the present context means that the compounds of the formula (I) or the formula (Γ) are effective for the occurrence of the respective parasite in an animal that is infected with such parasites is infected to a harmless extent, is reduced. More specifically, "combat" in the present context means that the compounds of the formula (I) or the formula (Γ) kill the respective parasite, prevent its growth or prevent its replication.
Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilla spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.; aus der Ordnung Siphonapterida, zum Beispiel Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: For example, the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium Spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilla spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests and hygiene pests from the order Blattarida. Further, in arthropods, by way of example and not limitation, the following Akari may be mentioned:
Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Ornithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.; und aus der Ordung der Acaridida (Astigmata), zum Beispiel Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp. From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilaelaps spp., Varroa spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp , Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
Zu Beispielen für parasitäre Protozoen zählen, ohne hierauf beschränkt zu sein: Examples of parasitic protozoa include, but are not limited to:
Mastigophora (Flagellata), wie: Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. Mastigophora (Flagellata), such as: Metamonada: from the order Diplomonadida, for example Giardia spp., Spironucleus spp.
Parabasala: aus der Ordnung Trichomonadida zum Beispiel Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Parabasala: from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
Euglenozoa: aus der Ordnung Trypanosomatida zum Beispiel Leishmania spp., Trypanosoma spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba spp., Centramoebidae, zum Beispiel Acanthamoeba sp., Euamoebidae, z. B. Hartmanella sp. Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung - - Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; out of order - -
Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtonella spp. Piroplasmida z. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtonella spp.
Microspora wie Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., und außerdem z. B. Myxozoa spp. Zu den für Menschen oder Tiere pathogenen Helminthen zählen zum Beispiel Acanthocephala, Nematoden, Pentastoma und Platyhelminthen (z.B. Monogenea, Cestodes und Trematodes). Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp. Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Exemplary helminths include, but are not limited to:
Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Monogenea: z. For example: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .; Cestodes: from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. For example, from the order Cyclophyllida: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp. , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
Trematodes: aus der Klasse Digenea zum Beispiel: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp. Trematodes: from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp. Collyricum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
Nematoden: aus der Ordnung Trichinellida zum Beispiel: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. Nematodes: from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp. For example, from the order Tylenchida: Micronema spp., Parastrangyloides spp., Strongyloides spp.
Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., - - From the order Rhabditina for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., - -
Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp. Coperosides spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp , Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp. Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp , Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
Aus der Ordnung Spirurida zum Beispiel: Acanthocheilonema spp., Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp., For example, from the order Spirurida: Acanthocheilonema spp., Anisakis spp., Ascaridia spp .; Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp .; Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp .; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp., Skjrabinema spp , Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp. Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
Aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. From the order Polymorphida for example: Filicollis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) oder der Formel (Γ) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphylaktisch oder therapeutisch erfolgen. Pentastoma: from the order Porocephalida for example Linguatula spp. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) or of the formula (II) are administered by methods which are generally known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) oder der Formel (Γ) zur Verwendung als Arzneimittel. Thus, an embodiment of the present invention relates to the compounds of the formula (I) or the formula (Γ) for use as a medicament.
Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) oder der Formel (Γ) zur Verwendung als Antiendoparasitikum. - - Another aspect relates to the compounds of formula (I) or formula (Γ) for use as antiendoparasitic. - -
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) oder der Formel (Γ) zur Verwendung als Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platyhelminthizid, Acanthocephalizid oder Pentastomizid. Another specific aspect of the invention relates to the compounds of the formula (I) or of the formula (II) for use as antihelminthic agents, in particular for use as nematicide, platyhelminthicide, acanthocephalicide or pentastomicide.
Ein weiterer spezieller Aspekt der Erfindung betrifft die Verbindungen der Formel (I) oder der Formel (Γ) zur Verwendung als Antiprotozoikum. Another specific aspect of the invention relates to the compounds of formula (I) or formula (II) for use as antiprotozoic.
Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) oder der Formel (Γ) zur Verwendung als Antiektoparasitikum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Another aspect relates to the compounds of the formula (I) or the formula (Γ) for use as anti-topazarasitic, in particular an arthropodicide, very particularly an insecticide or an acaricide.
Weitere Aspekte der Erfindung sind veterinärmedizinische Formulierungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) oder der Formel (Γ) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizinischen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) oder der Formel (Γ) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten Hilfsmitteln umfasst. Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of formula (I) or formula (II) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluent), a pharmaceutically acceptable adjuvant ( eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations. A related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) or formula (II) with pharmaceutically acceptable excipients and / or adjuvants, especially conventionally in veterinary medicine Formulations used include pharmaceutically acceptable excipients and / or adjuvants conventionally used in veterinary formulations.
Ein anderer spezieller Aspekt der Erfindung sind veterinärmedizinische Formulierungen ausgewählt aus der Gruppe ektoparasitizider und endoparasitizider Formulierungen, insbesondere ausgewählt aus der Gruppe anthelmintischer, antiprotozolischer und arthropodizider Formulierungen, ganz besonders ausgewählt aus der Gruppe nematizider, platyhelminthizider, acanthocephalizider, pentastomizider, insektizider und akkarizider Formulierungen, gemäß den erwähnten Aspekten, sowie Verfahren zu ihrer Herstellung. Another specific aspect of the invention are veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) oder der Formel (Γ) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by using an effective amount of a compound of the formula (I) or the formula (Γ) an animal, especially a nonhuman animal, that needs it.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wie hier definierten veterinärmedizinischen Formulierung bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of those mentioned here Ectoparasites and endoparasites, by applying a veterinary formulation as defined herein to an animal, especially a non-human animal in need thereof.
Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) oder der Formel (Γ) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Another aspect relates to the use of the compounds of the formula (I) or of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular one nonhuman animal.
Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung" die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. In the present veterinary or veterinary context, the term "treatment" includes prophylactic, metaphylactic and therapeutic treatment.
Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) oder der Formel (Γ) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das veterinärmedizinische Gebiet bereitgestellt. In a particular embodiment, mixtures of at least one compound of the formula (I) or of the formula (II) with other active substances, in particular with endo- and ectoparasiticides, are provided hereby for the veterinary field.
Auf dem Gebiet der Tiergesundheit bedeutet„Mischung" nicht nur, dass zwei (oder mehr) verschiedene Wirkstoffe in einer gemeinsamen Formulierung formuliert werden und entsprechend zusammen angewendet werden, sondern bezieht sich auch auf Produkte, die für jeden Wirkstoff getrennte Formulierungen umfassen. Dementsprechend können, wenn mehr als zwei Wirkstoffe angewendet werden sollen, alle Wirkstoffe in einer gemeinsamen Formulierung formuliert werden oder alle Wirkstoffe in getrennten Formulierungen formuliert werden; ebenfalls denkbar sind gemischte Formen, bei denen einige der Wirkstoffe gemeinsam formuliert und einige der Wirkstoffe getrennt formuliert sind. Getrennte Formulierungen erlauben die getrennte oder aufeinanderfolgende Anwendung der in Rede stehenden Wirkstoffe. In the animal health field, "blending" not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances should be formulated in a common formulation, or all active substances should be formulated in separate formulations, or mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
Die hier mit ihrem„Common Name" spezifizierten Wirkstoffe sind bekannt und beispielsweise im „Pesticide Manual" (siehe oben) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). The active ingredients specified herein by their "common name" are known and described, for example, in the "Pesticide Manual" (see above) or searchable on the Internet (e.g., http://www.alanwood.net/pesticides).
Beispielhafte Wirkstoffe aus der Gruppe der Ektoparasitizide als Mischungspartner schließen, ohne dass dies eine Einschränkung darstellen soll, die oben ausführlich aufgelisteten Insektizide und Akkarizide ein. Weitere verwendbare Wirkstoffe sind unten gemäß der oben erwähnten Klassifikation, die auf dem aktuellen IRAC Mode of Action Classification Scheme beruht, aufgeführt: (1) Acetylcholinesterase (AChE)-Inhibitoren; (2) GABA-gesteuerte Chlorid-Kanal-Blocker; (3) Natrium-Kanal-Modulatoren; (4) kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (5) allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR); (6) allosterische Modulatoren des Glutamat-abhängigen Chloridkanals (GluCl); (7) Juvenilhormon-Mimetika; (8) verschiedene nichtspezifische (Multi-Site) Inhibitoren; (9) Modulatoren Chordotonaler Organe; (10) Milbenwachstumsinhibitoren; (12) Inhibitoren der mitochondrialen ATP-Synthase, wie ATP- Disruptoren; (13) Entkoppler der oxidativen Phosphorylierung durch Störung des Protonengradienten; (14) Blocker des nicotinischen Acetylcholinrezeptorkanals; (15) Inhibitoren der Chitinbiosynthese, Typ - - Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above. Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of oxidative phosphorylation by disrupting the proton gradient; (14) blocker of the nicotinic acetylcholine receptor channel; (15) inhibitors of chitin biosynthesis, type - -
0; (16) Inhibitoren der Chitinbiosynthese, Typ 1 ; (17) Häutungsdisruptor (insbesondere bei Dipteren, d.h. Zweiflüglern); (18) Ecdyson-Rezeptor-Agonisten; (19) Octopamin-Rezeptor-Agonisten; (21) mitochondriale Komplex-I-Elektronentransportinhibitoren; (25) mitochondriale Komplex-II- Elektronentransportinhibitoren; (20) mitochondriale Komplex-III-Elektronentransportinhibitoren; (22) Blocker des spannungsabhängigen Natriumkanals; (23) Inhibitoren der Acetyl-CoA-Carboxylase; (28) Ryanodinrezeptor-Modulatoren; 0; (16) inhibitors of chitin biosynthesis, type 1; (17) molting disruptor (especially in dipterans, i.e., two-winged); (18) ecdysone receptor agonists; (19) octopamine receptor agonists; (21) mitochondrial complex I electron transport inhibitors; (25) mitochondrial complex II electron transport inhibitors; (20) mitochondrial complex III electron transport inhibitors; (22) blocker of the voltage-dependent sodium channel; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators;
Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, z. B. Fentrifanil, Fenoxacrim, Cyclopren, Chlorobenzilat, Chlordimeform, Flubenzimin, Dicyclanil, Amidoflumet, Quinomethionat, Triarathen, Clothiazoben, Tetrasul, Kaliumoleat, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Brompropylat, Cryolit; Active substances with unknown or non-specific mechanisms of action, eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(- ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton-S-methylsulfon, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos(-methyl), Azinphos(-ethyl), Chlorpyrifos(- ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos; Compounds from other classes, e.g. Butacarb, dimetilane, cloethocarb, phosphocarb, pirimiphos (- ethyl), parathion (-ethyl), methacrifos, isopropyl-o-salicylate, trichlorofon, sulprofos, propaphos, sebufos, pyridathione, prothoate, dichlorofenthione, demeton-S-methylsulfone, isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autothiofos, Aromfenvinfos (-methyl), Azinphos (-ethyl), Chlorpyrifos (- ethyl), Fosmethilane, Iodofenphos, Dioxabenzofos, Formothion, Fonofos, Flupyrazofos, Fensulfothion, Etrimfos;
Organochlorverbindungen, z. B. Camphechlor, Lindan, Heptachlor; oder Phenylpyrazole, z. B. Acetoprol, Pyrafluprol, Pyriprol, Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroide, z. B. (eis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Heptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (HCHs), Organochlorine compounds, e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroids, e.g. Eg, (cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin , Cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs),
Neonicotinoide, z. B. Nithiazin Dicloromezotiaz, Triflumezopyrim makroeyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Neonicotinoids, e.g. B. Nithiazin Dicloromezotiaz, Triflumezopyrim macrocyclic lactones, eg. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
Tripren, Epofenonan, Diofenolan; Triphene, Epofenonan, Diofenolan;
Biologicals, Hormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Codlemon oder Neem-Komponenten Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Biologicals, hormones or pheromones, for example natural products, eg thuringiensin, codlemon or neem components Dinitrophenols, e.g. Dinocap, dinobuton, binapacryl;
Benzoylharnstoffe, z. B. Fluazuron, Penfluron, Benzoylureas, eg. Fluazuron, penfluron,
Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Amidine derivatives, e.g. B. Chlormebuform, cymiazole, demiditraz
Bienenstockvarroa-Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid. Exemplary agents from the group of endoparasiticides, as a mixture partner, include, but are not limited to, anthelmintic agents and antiprotozoal agents.
Zu den anthelmintischen Wirkstoffen zählen, ohne hierauf beschränkt zu sein, die folgenden nematiziden, trematiziden und/oder cestoziden Wirkstoffe: aus der Klasse der makrocyclischen Lactone zum Beispiel: Eprinomectin, Abamectin, Nemadectin, Moxidectin, Doramectin, Selamectin, Lepimectin, Latidectin, Milbemectin, Ivermectin, Emamectin, Milbemycin; aus der Klasse der Benzimidazole und Probenzimidazole zum Beispiel: Oxibendazol, Mebendazol, Triclabendazol, Thiophanat, Parbendazol, Oxfendazol, Netobimin, Fenbendazol, Febantel, Thiabendazol, Cyclobendazol, Cambendazol, Albendazol-sulfoxid, Albendazol, Flubendazol; aus der Klasse der Depsipeptide, vorzugsweise cyclischen Depsipeptide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Levamisol, Tetramisol; aus der Klasse der Aminophenylamidine zum Beispiel: Amidantel, deacyliertes Amidantel (dAMD), Tribendimidin; aus der Klasse der Aminoacetonitrile zum Beispiel: Monepantel; aus der Klasse der Paraherquamide zum Beispiel: Paraherquamid, Derquantel; aus der Klasse der Salicylanilide zum Beispiel: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; aus der Klasse der substituierten Phenole zum Beispiel: Nitroxynil, Bithionol, Disophenol, Hexachlorophen, Niclofolan, Meniclopholan; aus der Klasse der Organophosphate zum Beispiel: Trichlorfon, Naphthalofos, Dichlorvos/DDVP, Crufomat, Coumaphos, Haloxon; aus der Klasse der Piperazinone/Chinoline zum Beispiel: Praziquantel, Epsiprantel; aus der Klasse der Piperazine zum Beispiel: Piperazin, Hydroxyzin; aus der Klasse der Tetracycline zum Beispiel: Tetracyclin, Chlorotetracyclin, Doxycyclin, Oxytetracyclin, Rolitetracyclin; aus diversen anderen Klassen zum Beispiel: Bunamidin, Niridazol, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miracil, Lucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Dianifenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon. Antiprotozoische Wirkstoffe, darunter, ohne hierauf beschränkt zu sein, die folgenden Wirkstoffe: aus der Klasse der Triazine zum Beispiel: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; aus der Klasse Polyletherionophor zum Beispiel: Monensin, Salinomycin, Maduramicin, Narasin; aus der Klasse der makrocyclischen Lactone zum Beispiel: Milbemycin, Erythromycin; aus der Klasse der Chinolone zum Beispiel: Enrofloxacin, Pradofloxacin; aus der Klasse der Chinine zum Beispiel: Chloroquin; aus der Klasse der Pyrimidine zum Beispiel: Pyrimethamin; aus der Klasse der Sulfonamide zum Beispiel: Sulfachinoxalin, Trimethoprim, Sulfaclozin; aus der Klasse der Thiamine zum Beispiel: Amprolium; aus der Klasse der Lincosamide zum Beispiel: Clindamycin; aus der Klasse der Carbanilide zum Beispiel: Imidocarb; aus der Klasse der Nitrofurane zum Beispiel: Nifurtimox; aus der Klasse der Chinazolinonalkaloide zum Beispiel: Halofuginon; aus diversen anderen Klassen zum Beispiel: Oxamniquin, Paromomycin; aus der Klasse der Vakzine oder Antigene aus Mikroorganismen zum Beispiel: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus. The anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole; from the class of depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of tetrahydropyrimidines for example: Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amide shell, deacylated amide shell (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: Monepantel; from the class of Paraherquamide, for example: Paraherquamid, Derquantel; from the class of salicylanilides for example: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; from the class of substituted phenols, for example: nitroxynil, bithionol, disophenol, hexachlorophene, nicolofolane, meniclopholan; from the class of organophosphates, for example: trichlorophone, naphthalofos, dichlorvos / DDVP, crufomat, coumaphos, haloxone; from the class of piperazinones / quinolines for example: praziquantel, epsiprantel; from the class of piperazines for example: piperazine, hydroxyzine; from the class of tetracyclines for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquine, mirasan, miracil, lucanthone, hycanthone, hetoline, emetine, diethylcarbamazine, dichlorophen, dianifenetide, clonazepam, bephenium, amoscanate, clorsulon. Antiprotozoal agents, including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides, for example: imidocarb; from the class of nitrofurans, for example: nifurtimox; from the class of quinazolinone alkaloids, for example: halofuginone; from various other classes for example: oxamniquine, paromomycin; from the class of vaccines or antigens from microorganisms for example: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus ,
Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. In addition, if they are capable of doing so on the basis of their functional groups, all said mixing partners can optionally form salts with suitable bases or acids.
Vektorbekämpfung vector control
Die Verbindungen der Formel (I) oder der Formel (Γ) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z. B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z. B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. The compounds of the formula (I) or the formula (II) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: Examples of vectors and their transmitted diseases or pathogens are:
1) Mücken 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von anderen Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of other worms;
- Aedes: Gelbfieber, Dengue -Fieber, weitere virale Erkrankungen, Filariasis; - Aedes: yellow fever, dengue fever, other viral diseases, filariasis;
- Simulien: Übertragung von Würmern, insbesondere Onchocerca volvulus; - Simulia: transmission of worms, in particular Onchocerca volvulus;
- Psychodidae: Übertragung von Leishmaniose - Psychodidae: transmission of leishmaniasis
2) Läuse: Hautinfektionen, epidemisches Fleckfieber; 2) lice: skin infections, epidemic typhus;
3) Flöhe: Pest, endemisches Fleckfieber, Bandwürmer; 3) fleas: plague, endemic typhus, tapeworms;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
5) Milben: Acariose, epidemisches Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, Frühsommer-Meningoenzephalitis (FSME), Krim- Kongo-Fieber, Borreliose; - - 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis; - -
6) Zecken: Borelliosen wie Borrelia bungdorferi sensu lato., Borrelia duttoni, Frühsommer- Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis), Ehrlichiose. 6) Ticks: Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten, zum Beispiel Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. Examples of vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Psychodide wie Phlebotomus, Lutzomyia, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) oder der Formel (Γ) Resistenz-brechend sind. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans. Vector control is also possible when the compounds of formula (I) or formula (II) are resistance-disrupting.
Verbindungen der Formel (I) oder der Formel (Γ) sind zur Verwendung in der Prävention von Krankheiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) oder der Formel (Γ) zur Vektorbekämpfung, z. B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorrats- und Materialschutz. Compounds of formula (I) or formula (II) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) or formula (Γ) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials.
Schutz von technischen Materialen Protection of technical materials
Die Verbindungen der Formel (I) oder der Formel (Γ) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z. B. aus den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of the formula (I) or the formula (II) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) oder der Formel (Γ) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred. In a further embodiment, the compounds of the formula (I) or of the formula (II) are used together with at least one further insecticide and / or at least one fungicide.
In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) oder der Formel (Γ) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d. h., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. - - In a further embodiment, the compounds of the formula (I) or of the formula (II) are present as ready-to-use pesticides, ie they can be applied to the corresponding material without further changes. As further insecticides or fungicides, in particular those mentioned above come into question. - -
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) oder der Formel (Γ) 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) oder der Formel (Γ) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Surprisingly, it has also been found that the compounds of the formula (I) or of the formula (II) protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. can be used. Likewise, the compounds of the formula (I) or the formula (II) can be used alone or in combinations with other active substances as antifouling agents.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) oder der Formel (Γ) 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, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen, Tierzuchtanlagen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) oder der Formel (Γ) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) oder der Formel (Γ) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. The compounds of the formula (I) or of the formula (II) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry. To combat animal pests, the compounds of the formula (I) or of the formula (II) are used alone or in combination with other active ingredients and / or adjuvants. Preferably, they are used in household insecticide products. The compounds of formula (I) or formula (II) are effective against sensitive and resistant species as well as against all stages of development.
Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z. B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. Herstellungsbeispiele The application is carried out for example in aerosols, non-pressurized sprays, z. 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 straw baits or bait stations. Preparation Examples
5-Ethylsulfonyl-6-[3-methyl-6-(trifluor^  5-ethylsulfonyl-6- [3-methyl-6- (trifluoro ^
(Bsp. 1-1) (Example 1-1)
Figure imgf000090_0001
40 mg 5-Ethylsulfanyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]imidazo
Figure imgf000090_0001
40 mg of 5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] imidazo
(0.10 mmol) wurden in 5.0 mL Dichlormethan gelöst. Es wurden 0.020 mL Ameisensäure (0.52 mmol) und 0.064 mL Wasserstoffperoxid (0.73 mmol) zugegeben und das entstandene Gemisch wurde für 16 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit gesättigter Natriumthiosulfat-Lösung gewaschen. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet und eingeengt. Der Rückstand wurde säulenchromatographisch über eine präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. logP (HCOOH): 2.30; MH+: 416; Ή-NMR (400MHz, CDC13) δ ppm: 8.96 (s, 1H), 8.27 (d, 1H), 8.12 (s, 1H), 7.19 (d, 1H), 4.25 (s, 3H), 4.10 (q, 2H), 1.43 (t, 3H). (0.10 mmol) were dissolved in 5.0 mL dichloromethane. There were added 0.020 ml of formic acid (0.52 mmol) and 0.064 mL hydrogen peroxide (0.73 mmol) and the resulting mixture was stirred for 16 h at room temperature. The reaction mixture was washed with saturated sodium thiosulfate solution. The organic phase was separated, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on a preparative HPLC with a gradient of water / acetonitrile as eluent. logP (HCOOH): 2.30; MH + : 416; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.96 (s, 1H), 8.27 (d, 1H), 8.12 (s, 1H), 7.19 (d, 1H), 4.25 (s, 3H), 4.10 (q , 2H), 1.43 (t, 3H).
5-Ethylsulfanyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]im^ 5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] ^ in
(Bsp. 1-2) (Ex. 1-2)
Figure imgf000090_0002
Figure imgf000090_0002
38 mg 5-Chlor-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[2,l-b]thiazol (0.10 mmol) wurden in 3.0 mL Ν,Ν-Dimethylformamid gelöst. Der Lösung wurden 18 mg Natriumthioethanolat (0.21 mmol) zugegeben. Das Gemisch wurde anschließend 16 h bei Raumtemperatur gerührt, erneut mit 36 mg Natriumthioethanolat (0.42 mmol) versetzt und weitere 16 h gerührt. Das Reaktionsgemisch wurde mit einer Mischung aus Cyclohexan / Ethylacetat verdünnt, über Celite filtriert und eingeengt. Das Rohprodukt wurde ohne weitere Aufreinigung weiter umgesetzt. logP (HCOOH): 2.73; MH+: 384; Ή-NMR (400MHz, CDC13) δ ppm: 8.90 (s, 1H), 8.14 (d, 1H), 7.76 - - 38 mg of 5-chloro-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] imidazo [2, 1b] thiazole (0.10 mmol) were dissolved in 3.0 mL Ν, Ν -Dimethylformamide solved. To the solution was added 18 mg of sodium thioethoxide (0.21 mmol). The mixture was then stirred for 16 h at room temperature, treated again with 36 mg of sodium thioethanolate (0.42 mmol) and stirred for a further 16 h. The reaction mixture was diluted with a mixture of cyclohexane / ethyl acetate, filtered through Celite and concentrated. The crude product was reacted further without further purification. logP (HCOOH): 2.73; MH + : 384; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.90 (s, 1H), 8.14 (d, 1H), 7.76 - -
(s, 1H), 7.05 (d, 1H), 4.30 (s, 3H), 4.47 (q, 2H), 1.22 (t, 3H). (s, 1H), 7.05 (d, 1H), 4.30 (s, 3H), 4.47 (q, 2H), 1.22 (t, 3H).
5-Chlor-6-[3-methyl-6-(trifluormethyl)imidazo[^ 5-chloro-6- [3-methyl-6- (trifluoromethyl) imidazo [^
Figure imgf000091_0001
Figure imgf000091_0001
280 mg 5-Chlorimidazo[2,l-b]thiazol-6-carbonsäure (1.10 mmol), 163 mg N3-methyl-6- (trifluormethyl)pyridin-3,4-diamin (0.85 mmol) und 163 mg N-Ethyl-N'-(3-dimethylaminopropyl)- carbodiimid Hydrochlorid (0.85 mmol) wurden in 10.0 mL Pyridin gelöst. Das Gemisch wurde 16 h relluxiert und anschließend eingeengt. Der Rückstand wurde säulenchromatographisch über eine präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. logP (neutral): 2.35; MH+: 358; Ή-NMR (400MHz, CDC13) δ ppm: 8.90 (s, 1H), 8.16 (s, 1H), 7.54 (d, 1H), 7.11 (d, lH), 4.36 (s, 3). 280 mg of 5-chloroimidazo [2, lb] thiazole-6-carboxylic acid (1.10 mmol), 163 mg of N3-methyl-6- (trifluoromethyl) pyridine-3,4-diamine (0.85 mmol) and 163 mg of N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.85 mmol) was dissolved in 10.0 mL of pyridine. The mixture was relleuxed for 16 h and then concentrated. The residue was purified by column chromatography on a preparative HPLC with a gradient of water / acetonitrile as eluent. logP (neutral): 2.35; MH + : 358; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.90 (s, 1H), 8.16 (s, 1H), 7.54 (d, 1H), 7.11 (d, 1H), 4.36 (s, 3).
5-Chlorimidazo[2,l-b]thiazol-6-carbonsäure 5-chloroimidazo [2, l-b] thiazole-6-carboxylic acid
Figure imgf000091_0002
Figure imgf000091_0002
240 mg Ethyl 5-chlorimidazo[2,l-b]thiazol-6-carboxylat (1.04 mmol) wurden in einem Gemisch aus 30.0 mL Tetrahydrofuran und 10.0 mL Wasser gelöst. Die Suspension wurde anschließend mit 44 mg Lithiumhydroxid Monohydrat (1.04 mmol) versetzt. Das Gemisch wurde 16 h bei Raumtemperatur gerührt, mit 1.0 M Salzsäure (wässrig) angesäuert und anschließend eingeengt. Der Rückstand wurde mit Toluol azeotrop getrocknet. Das Rohprodukt wurde ohne weitere Aufreinigung weiter umgesetzt. logP (HCOOH): 0.44; MH+: 203; Ή-NMR (400MHz, D6-DMSO) δ ppm: 12.95 (br, 1H), 7.96 (d, 1H), 7.55 (d, 1H). Ethyl 5-chlorimidazo[2,l-b]thiazol-6-carboxylat 240 mg of ethyl 5-chloroimidazo [2, 1b] thiazole-6-carboxylate (1.04 mmol) were dissolved in a mixture of 30.0 mL of tetrahydrofuran and 10.0 mL of water. The suspension was then treated with 44 mg of lithium hydroxide monohydrate (1.04 mmol). The mixture was stirred at room temperature for 16 h, acidified with 1.0 M hydrochloric acid (aqueous) and then concentrated. The residue was azeotropically dried with toluene. The crude product was reacted further without further purification. logP (HCOOH): 0.44; MH + : 203; Ή NMR (400MHz, D6-DMSO) δ ppm: 12.95 (br, 1H), 7.96 (d, 1H), 7.55 (d, 1H). Ethyl 5-chloroimidazo [2, 1b] thiazole-6-carboxylate
Figure imgf000091_0003
- -
Figure imgf000091_0003
- -
500 mg Ethyl imidazo[2,l-b]thiazol-6-carboxylat (2.54 mmol) wurden in 50.0 mL Acetonitril gelöst und die Lösung wurde anschließend mit 340 mg N-Chlorsuccinimid (2.54 mmol) versetzt. Das Gemisch wurde 8 h bei 60 °C gerührt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch eingeengt, der Rückstand mit Wasser versetzt und mit Dichlormethan extrahiert. Die organische Phase wurde über Natriumsulfat getrocknet und eingeengt. Das Rohprodukt wurde säulenchromatographisch an Kieselgel in einem Gemisch von Cyclohexan / Ethylacetat gereinigt. logP (HCOOH): 1.52; MH+: 231 ; Ή-NMR (400MHz, CDC13) δ ppm: 7.44 (d, 1H), 7.06 (d, 1H), 4.43 (q, 2H), 1.44 (t, 3H). 500 mg of ethyl imidazo [2, 1b] thiazole-6-carboxylate (2.54 mmol) were dissolved in 50.0 ml of acetonitrile, and then 340 mg of N-chlorosuccinimide (2.54 mmol) were added to the solution. The mixture was stirred at 60 ° C for 8 hours. After cooling to room temperature, the reaction mixture was concentrated, the residue was treated with water and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel in a mixture of cyclohexane / ethyl acetate. logP (HCOOH): 1.52; MH + : 231; Ή NMR (400MHz, CDC1 3 ) δ ppm: 7.44 (d, 1H), 7.06 (d, 1H), 4.43 (q, 2H), 1.44 (t, 3H).
Ethyl imidazo[2,l-b]thiazol-6-carboxylat Ethyl imidazo [2, 1-b] thiazole-6-carboxylate
Figure imgf000092_0001
Figure imgf000092_0001
5.00 g 2-Aminothiazol (49.9 mmol) wurden in 100 mL Ethanol gelöst. Das Gemisch wurde mit 9.74 g Ethyl-3-brompyruvat (49.9 mmol) versetzt und anschließend für 3 h refluxiert. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch eingeengt und der Rückstand säulenchromatographisch an Kieselgel in einem Gemisch von Cyclohexan / Ethylacetat gereinigt. logP (neutral): 0.99; MH+: 197; Ή-NMR (400MHz, D6-DMSO) δ ppm: 8.38 (s, 1H), 7.92 (d, 1H), 7.42 (d, 1H); 4.26 (q, 2H), 1.29 (t, 3H). 5.00 g of 2-aminothiazole (49.9 mmol) were dissolved in 100 mL of ethanol. The mixture was treated with 9.74 g of ethyl 3-bromopyruvate (49.9 mmol) and then refluxed for 3 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by column chromatography on silica gel in a mixture of cyclohexane / ethyl acetate. logP (neutral): 0.99; MH + : 197; Ή-NMR (400MHz, D6-DMSO) δ ppm: 8.38 (s, 1H), 7.92 (d, 1H), 7.42 (d, 1H); 4.26 (q, 2H), 1.29 (t, 3H).
5-Ethylsulfonyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l-b]thiazol (Beispiel 1-3) 5-Ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1-b] thiazole (Example 1-3)
Figure imgf000092_0002
180 mg 5-Ethylsulfanyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l-b]thiazol (0.39 mmol) wurden in 5.0 mL Dichlormethan gelöst. Es wurden 0.075 mL Ameisensäure (1.99 mmol) und 0.24 mL Wasserstoffperoxid (2.79 mmol) zugegeben und das entstandene Gemisch wurde für 16 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit gesättigter Natriumthiosulfat-Lösung gewaschen. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet und eingeengt. Der Rückstand wurde säulenchromatographisch an Kieselgel mit einem Dichlormethan / Methanol Gradienten als Laufmittel gereinigt. logP (HCOOH): 3.38; [M+H]+: 484; Ή-NMR (400MHz, CDCb) δ ppm: 8.98 (s, 1H), 8.90 (s, 1H), 8.13 (s, 1H), 4.27 (s, 3H), 4.19 (q, 2H), 1.46 (t, 3H).
Figure imgf000092_0002
180 mg of 5-ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) -imidazo [2, 1b] thiazole (0.39 mmol) were dissolved in 5.0 mL of dichloromethane. 0.075 mL formic acid (1.99 mmol) and 0.24 mL hydrogen peroxide (2.79 mmol) were added and the resulting mixture was stirred for 16 h at room temperature. The reaction mixture was washed with saturated sodium thiosulfate solution. The organic phase was separated, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel with a dichloromethane / methanol gradient as eluent. logP (HCOOH): 3.38; [M + H] + : 484; Ή NMR (400MHz, CDCb) δ ppm: 8.98 (s, 1H), 8.90 (s, 1H), 8.13 (s, 1H), 4.27 (s, 3H), 4.19 (q, 2H), 1.46 (t, 3H).
5-Ethylsulfanyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2- (trifluormethyl)imidazo[2,l-b]thiazol (Beispiel 1-6) 5-Ethylsulfanyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1-b] thiazole (Example 1-6)
Figure imgf000093_0001
Figure imgf000093_0001
313 mg 5-Brom-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l-b]thiazol (0.66 mmol) wurden in 20.0 mL Tetrahydrofuran gelöst. Der Lösung wurden 448 mg Natriumthioethanolat (5.32 mmol) zugegeben. Das Gemisch wurde anschließend 16 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit einer Mischung aus Ethylacetat / H2O versetzt, über Celite filtriert und eingeengt. Das Rohprodukt wurde säulenchromatographisch an Kieselgel mit einem Dichlormethan / Methanol Gradienten als Laufmittel gereinigt. logP (HCOOH): 3.90; [M+H]+: 452; Ή-NMR (400MHz, CDCI3) δ ppm: 8.92 (s, 1H), 8.43 (s, 1H), 8.16 (s, 1H), 4.30 (s, 3H), 3.14 (q, 2H), 1.24 (t, 3H). 313 mg of 5-bromo-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1b] thiazole (0.66 mmol) were dissolved in 20.0 mL of tetrahydrofuran. To the solution was added 448 mg of sodium thioethanolate (5.32 mmol). The mixture was then stirred for 16 h at room temperature. The reaction mixture was treated with a mixture of ethyl acetate / H 2 O, filtered through Celite and concentrated. The crude product was purified by column chromatography on silica gel with a dichloromethane / methanol gradient as eluent. logP (HCOOH): 3.90; [M + H] + : 452; Ή NMR (400MHz, CDCl3) δ ppm: 8.92 (s, 1H), 8.43 (s, 1H), 8.16 (s, 1H), 4.30 (s, 3H), 3.14 (q, 2H), 1.24 (t, 3H).
5-Brom-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)-imi b]thiazol 5-Bromo-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) -imi- b] thiazole
Figure imgf000093_0002
Figure imgf000093_0002
1.00 g 5-Brom-2-(trifluormethyl)imidazo[2,l-b]thiazol-6-carbonsäure (3.17 mmol), 467 mg N3-methyl- 6-(trifluormethyl)pyridin-3,4-diamin (2.44 mmol) und 468 mg N-Ethyl-N'-(3-dimethylaminopropyl)- carbodiimid Hydrochlorid (2.44 mmol) wurden in 20.0 mL Pyridin gelöst. Das Gemisch wurde mit 464 mg 4-Toluolsulfonsäuremonohydrat (2.44 mmol) versetzt und anschließend für 16 h refluxiert. Das Reaktionsgemisch wurde mit Acetonitril verdünnt, filtriert und das Filtrat eingeengt. Der Rückstand wurde säulenchromatographisch an Kieselgel mit einem Dichlormethan / Methanol Gradienten als Laufmittel gereinigt. logP (neutral): 3.43; [M+H]+: 470; Ή-NMR (400MHz, CDC13) δ ppm: 8.92 (s, 1H), 8.17 (s, 1H), 7.97 (d, 1H), 4.34 (s, 3H). - - 1.00 g of 5-bromo-2- (trifluoromethyl) imidazo [2, 1b] thiazole-6-carboxylic acid (3.17 mmol), 467 mg of N3-methyl-6- (trifluoromethyl) pyridine-3,4-diamine (2.44 mmol) and 468 mg of N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide hydrochloride (2.44 mmol) were dissolved in 20.0 mL of pyridine. To the mixture was added 464 mg of 4-toluenesulfonic acid monohydrate (2.44 mmol) and then refluxed for 16 h. The reaction mixture was diluted with acetonitrile, filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel with a dichloromethane / methanol gradient as eluent. logP (neutral): 3.43; [M + H] + : 470; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.92 (s, 1H), 8.17 (s, 1H), 7.97 (d, 1H), 4.34 (s, 3H). - -
2-(3-Ethylsulfonyl-6,7-dihydro-5H^yrrol[l,2-a]imtö^ 2- (3-ethylsulfonyl-6,7-dihydro-5H ^ yrrol [l, 2-a] ^ imtö
imidazo[4,5-c]pyridin (Beispiel 1-4) imidazo [4,5-c] pyridine (Example 1-4)
Figure imgf000094_0001
Figure imgf000094_0001
160 mg 2-(3-Brom-6,7-dihydro-5H-pyrrol[l,2-a]imidazol-2-yl)-3-m 160 mg of 2- (3-bromo-6,7-dihydro-5H-pyrrolo [1,2-a] imidazol-2-yl) -3-m
c]pyridin (0.20 mmol) wurden in 5.0 mL Dimethylsulfoxid gelöst. Der Lösung wurden 3.9 mg Kupfer (I) iodid (0.02 mmol), 5.7 mg L-Prolin (0.05 mmol) und 241 mg Natriumethansulfinat (2.07 mmol) zugegeben. Das Gemisch wurde anschließend 8 h bei 70 °C gerührt. Das Reaktionsgemisch wurde mit Ethylacetat verdünnt und mit Wasser gewaschen. Die organische Phase wurde abgetrennt, über Na2SC>4 getrocknet, filtriert und eingeengt. Das Rohprodukt wurde säulenchromatographisch über eine präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. logP (HCOOH): 1.97; [M+H]+: 400; Ή-NMR (400MHz, CDCI3) δ ppm: 8.91 (s, 1H), 8.08 (s, 1H), 4.41 (t, 2H), 4.19 (s, 3H), 4.04 (q, 2H), 3.06 (t, 2H), 2.74 (quint, 2H), 1.42 (t, 3H). c] pyridine (0.20 mmol) was dissolved in 5.0 mL dimethyl sulfoxide. To the solution was added 3.9 mg of copper (I) iodide (0.02 mmol), 5.7 mg of L-proline (0.05 mmol) and 241 mg of sodium ethanesulfinate (2.07 mmol). The mixture was then stirred at 70 ° C for 8 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was separated, dried over Na 2 SC> 4, filtered and concentrated. The crude product was purified by column chromatography on a preparative HPLC with a gradient of water / acetonitrile as the eluent. logP (HCOOH): 1.97; [M + H] + : 400; Ή-NMR (400MHz, CDCl3) δ ppm: 8.91 (s, 1H), 8.08 (s, 1H), 4.41 (t, 2H), 4.19 (s, 3H), 4.04 (q, 2H), 3.06 (t, 2H), 2.74 (quint, 2H), 1.42 (t, 3H).
2-(3-Brom-6,7-dihydro-5H^yrrol[l,2-a]imidazol-2-yl)-3-methyl-6-(trifluormethyl)imidazo[4,5- c] yridin 2- (3-Bromo-6,7-dihydro-5H-pyrrolo [1,2-a] imidazol-2-yl) -3-methyl-6- (trifluoromethyl) imidazo [4,5-c] yridine
Figure imgf000094_0002
Figure imgf000094_0002
2.90 g 3-Brom-6,7-dihydro-5H-pyrrol[l,2-a]imidazol-2-carbonsäure Hydrochlorid (10.8 mmol), 1.59 g N3-methyl-6-(trifluormethyl)pyridin-3,4-diamin (8.33 mmol) und 1.60 g N-Ethyl-N'-(3- dimethylaminopropyl)-carbodiimid Hydrochlorid (8.33 mmol) wurden in 50.0 mL Pyridin gelöst. Das Gemisch wurde mit 3.17 g 4-Toluolsulfonsäuremonohydrat (16.6 mmol) versetzt und anschließend für 16 h refluxiert. Das Reaktionsgemisch wurde mit Acetonitril verdünnt, filtriert und das Filtrat eingeengt. Der Rückstand wurde säulenchromatographisch an Kieselgel mit einem Dichlormethan / Methanol Gradienten als Laufmittel gereinigt. logP (neutral): 2.07; [M+H]+: 388; Ή-NMR (400MHz, CDC13) δ ppm: 8.85 (s, 1H), 8.13 (s, 1H), 4.28 (s, 3H), 4.08 (t, 2H), 3.07 (t, 2H), 2.73 (quint, 2H). 5-Ethylsulfonyl-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l-b][l,3,4]thiadiazol (Beispiel 1-5) - - 2.90 g of 3-bromo-6,7-dihydro-5H-pyrrolo [1,2-a] imidazole-2-carboxylic acid hydrochloride (10.8 mmol), 1.59 g of N3-methyl-6- (trifluoromethyl) pyridine-3,4- diamine (8.33 mmol) and 1.60 g of N-ethyl-N '- (3-dimethylaminopropyl) -carbodiimide hydrochloride (8.33 mmol) were dissolved in 50.0 mL of pyridine. To the mixture was added 3.17 g of 4-toluenesulfonic acid monohydrate (16.6 mmol) and then refluxed for 16 h. The reaction mixture was diluted with acetonitrile, filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel with a dichloromethane / methanol gradient as eluent. logP (neutral): 2.07; [M + H] + : 388; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.85 (s, 1H), 8.13 (s, 1H), 4.28 (s, 3H), 4.08 (t, 2H), 3.07 (t, 2H), 2.73 (quint , 2H). 5-Ethylsulfonyl-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1b] [l, 3,4] thiadiazole (Example 1-5) - -
Figure imgf000095_0001
Figure imgf000095_0001
50.0 mg 5-Brom-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l-b][l,3,4]thiadiazol (0.10 mmol) wurden in 2.0 mL Dimethylsulfoxid gelöst. Der Lösung wurden 2.0 mg Kupfer (I) iodid (0.01 mmol), 2.9 mg L-Prolin (0.03 mmol) und 24.6 mg Natriumethansuliinat (0.21 mmol) zugegeben. Das Gemisch wurde anschließend 8 h bei 70 °C gerührt. Es wurden weitere 50.0 mg Natriumethansulfinat (0.42 mmol) zugegeben und für 8 h bei 80 °C gerührt. Anschließend wurden nochmals 50.0 mg Natriumethansulfinat (0.42 mmol) zugegeben und wiederum für 8 h bei 80 °C gerührt. Das Reaktionsgemisch wurde mit Ethylacetat verdünnt und mit Wasser gewaschen. Die organische Phase wurde abgetrennt, über Na2SC>4 getrocknet, filtriert und eingeengt. Das Rohprodukt wurde säulenchromatographisch über eine präparative HPLC mit einem Wasser / Acetonitril Gradienten als Laufmittel gereinigt. logP (HCOOH): 2.68; [M+H]+: 485; Ή-NMR (400MHz, CDC13) δ ρριη: 8.99 (s, 1H), 8.15 (s, 1H), 4.13 (s, 3H), 3.88 (q, 2H), 1.51 (t, 3H). 50.0 mg of 5-bromo-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1b] [l, 3, 4] thiadiazole (0.10 mmol) were dissolved in 2.0 mL dimethyl sulfoxide. 2.0 mg of copper (I) iodide (0.01 mmol), 2.9 mg of L-proline (0.03 mmol) and 24.6 mg of sodium ethanesulphinate (0.21 mmol) were added to the solution. The mixture was then stirred at 70 ° C for 8 h. An additional 50.0 mg of sodium ethanesulfinate (0.42 mmol) was added and the mixture was stirred at 80 ° C. for 8 h. Subsequently, another 50.0 mg of sodium ethanesulfinate (0.42 mmol) were added and again stirred at 80 ° C for 8 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was separated, dried over Na 2 SC> 4, filtered and concentrated. The crude product was purified by column chromatography on a preparative HPLC with a gradient of water / acetonitrile as the eluent. logP (HCOOH): 2.68; [M + H] + : 485; Ή-NMR (400MHz, CDC1 3 ) δρριη: 8.99 (s, 1H), 8.15 (s, 1H), 4.13 (s, 3H), 3.88 (q, 2H), 1.51 (t, 3H).
5-Brom-6-[3-methyl-6-(trifluormethyl)imidazo[4,5-c]pyridin-2-yl]-2-(trifluormethyl)- imidazo[2,l- b][l,3,4]thiadiazol 5-Bromo-6- [3-methyl-6- (trifluoromethyl) imidazo [4,5-c] pyridin-2-yl] -2- (trifluoromethyl) imidazo [2, 1-b] [1,3] 4] thiadiazol
Figure imgf000095_0002
Figure imgf000095_0002
1.10 g 5-Brom-2-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-6-carbonsäure (3.48 mmol) 512 mg N3-methyl-6-(trifluormethyl)pyridin-3,4-diamin (2.67 mmol) und 513 mg N-Ethyl-N'-(3- dimethylaminopropyl)-carbodiimid Hydrochlorid (2.67 mmol) wurden in 30.0 mL Pyridin gelöst. Das Gemisch wurde mit 1.02 g 4-Toluolsulfonsäuremonohydrat (5.35 mmol) versetzt und anschließend für 16 h refluxiert. Anschließend wurde das Reaktionsgemisch erneut mit mit 1.02 g 4- Toluolsulfonsäuremonohydrat (5.35 mmol) versetzt und für weitere 16 h refluxiert. Das Reaktionsgemisch wurde mit Acetonitril verdünnt, filtriert und das Filtrat eingeengt. Der Rückstand wurde über Kieselgel filtriert und eingeengt. Das Rohprodukt wurde ohne weitere Aufreinigung weiter umgesetzt. logP (neutral): 3.33; [M+H]+: 471; Ή-NMR (400MHz, CDC13) δ ppm: 8.94 (s, 1H), 8.19 (s, 1H), 4.33 (s, 3H). - - 1.10 g of 5-bromo-2- (trifluoromethyl) imidazo [2, lb] [l, 3,4] thiadiazole-6-carboxylic acid (3.48 mmol) 512 mg of N3-methyl-6- (trifluoromethyl) pyridine-3,4- Diamine (2.67 mmol) and 513 mg of N-ethyl-N '- (3-dimethylaminopropyl) -carbodiimide hydrochloride (2.67 mmol) were dissolved in 30.0 mL of pyridine. To the mixture was added 1.02 g of 4-toluenesulfonic acid monohydrate (5.35 mmol) and then refluxed for 16 h. Subsequently, the reaction mixture was added again with 1.02 g of 4-toluenesulfonic acid monohydrate (5.35 mmol) and refluxed for a further 16 h. The reaction mixture was diluted with acetonitrile, filtered and the filtrate was concentrated. The residue was filtered through silica gel and concentrated. The crude product was reacted further without further purification. logP (neutral): 3.33; [M + H] + : 471; Ή NMR (400MHz, CDC1 3 ) δ ppm: 8.94 (s, 1H), 8.19 (s, 1H), 4.33 (s, 3H). - -
5-Brom-2-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-6-carbonsäure 5-bromo-2- (trifluoromethyl) imidazo [2, l-b] [l, 3,4] thiadiazol-6-carboxylic acid
Figure imgf000096_0001
Figure imgf000096_0001
1.00 g 2-(Trifluormethyl)imidazo[2,l-b] [l,3,4]thiadiazol-6-carbonsäure (4.21 mmol) wurden in 10.0 mL N.N-Dimethylformamid gelöst und die erhaltene Lösung wurde mit 872 mg N-Bromsuccinimid (4.84 mmol) versetzt. Das Reaktionsgemisch wurde 16 h bei Raumtemperatur gerührt. Das Gemisch wurde anschließend mit Ethylacetat verdünnt. Die organische Phase wurde mit Wasser und Natriumthiosufat- Lösung gewaschen, abgetrennt, über Na2SC>4 getrocknet und eingeengt. logP (HCOOH): 1.64; [M+H]+: 317; Ή-NMR (400MHz, d6-DMSO) δ ppm: 13.3 (br, 1H). 1.00 g of 2- (trifluoromethyl) imidazo [2, 1b] [l, 3,4] thiadiazole-6-carboxylic acid (4.21 mmol) were dissolved in 10.0 ml of N, N-dimethylformamide and the resulting solution was treated with 872 mg of N-bromosuccinimide (4.84 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was then diluted with ethyl acetate. The organic phase was washed with water and sodium thiosulfate solution, separated, dried over Na 2 SC> 4 and concentrated. logP (HCOOH): 1.64; [M + H] + : 317; Ή NMR (400MHz, d 6 -DMSO) δ ppm: 13.3 (br, 1H).
Die Messung der logP Werte erfolgt gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 55°C. The measurement of the logP values is carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 55 ° C.
Die Bestimmung mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 mit 0,1 % wässriger Ameisensäure und Acetonitril (enthält 0,1% Ameisensäure) als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril. In der Tabelle logP (HCOOH) genannt. The determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. In the table called logP (HCOOH).
Die Bestimmung mit der LC-MS im neutralen Bereich erfolgt bei pH 7.8 mit 0,001 molarer wässriger Ammoniumhydrogencarbonat-Lösung und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 95 % Acetonitril. In der Tabelle logP (neutral) genannt. The determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile. In the table called logP (neutral).
Die Eichung erfolgt mit un verzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP- Werte bekannt sind (Bestimmung der logP- Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinander folgenden Alkanonen). Die NMR-Daten ausgewählter Beispiele werden entweder in klassischer Form (δ-Werte, Multiplettaufspaltung, Anzahl der H-Atome) oder als NMR-Peak-Listen aufgeführt. The calibration is carried out with un branched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by retention times by linear interpolation between two consecutive alkanones). The NMR data of selected examples are listed either in classical form (δ values, multiplet splitting, number of H atoms) or as NMR peak lists.
Das Lösungsmittel, in welchem das NMR-Spektrum aufgenommen wurde ist jeweils angegeben. The solvent in which the NMR spectrum was recorded is given in each case.
NMR-Peak-Listenverfahren NMR peak list procedures
Die IH-NMR-Daten ausgewählter Beispiele werden in Form von IH-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^; 82 (Intensität2); ; 5i (Intensität ; ; δη (Intensität) The IH-NMR data of selected examples are recorded in the form of IH-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 ^; 82 (intensity 2);; 5i (intensity;; δ η (intensity);
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 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. To calibrate the chemical shift of 1H NMR spectra, we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
Die Listen der 1H-NMR-Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. The lists of 1H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
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. 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 Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-DÖ und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. 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%). When indicating compound signals in the delta range of solvents and / or water, our lists of 1 H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D δ and the peak of water, which are usually in the Average high intensity. 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-Fingerabdrücken" zu erkennen. Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify 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. Weitere Details zu IH-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden.An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation. Further details on IH NMR peaks can be found in Research Disclosure Database Number 564025.
Figure imgf000098_0001
Figure imgf000098_0001
Beispiel 1-1: 'H-NMR(400.0 MHz, CDC13): Example 1-1: 'H-NMR (400.0 MHz, CDC13):
δ= 8.957(3.49);8.277(2.97);8.266(3.07);8.121(3.65);7.263(34.48);7.195(2.83);7.184(2.8);5.3(7.33);4.362(0.37);4.246(16);4.133(1 .05);4.114(3.37);4.096(3.44);4.077(1.08);1.602(13.94);1.535(0.35);1.516(0.38);1.498(0.37);1.482(0.36);1.478(0.36);1.466(0.36); 8,287 (3.49), 8,277 (2.97), 8,266 (3.07), 8,121 (3.65), 7,263 (34.48), 7,195 (2.83), 7,184 (2.8), 5.3 (7.33), 4,362 (0.37), 4,246 (16 4,113 (1 .05), 4,114 (3.37), 4,096 (3.44), 4,077 (1.08), 1,602 (13.94), 1,535 (0.35), 1,516 (0.38), 1,498 (0.37), 1,482 (0.36), 1,478 (0:36); 1,466 (00:36);
1,449(3.7);1.431(7.6);1.412(3.55);1.285(0.33);1.254(1.9);0.07(0.45);0(3.97) 1,449 (3.7); 1,431 (7.6); 1,412 (3.55); 1,285 (12:33); 1,254 (1.9); 12:07 (0.45) 0 (3.97)
Beispiel 1-2: 1H-NMR(400.0 MHz, CDC13): Example 1-2: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.996(0.34);8.933(1.81);8.9(3.89);8.886(1.57);8.197(1.86);8.19(0.8);8.162(0.46);8.153(3.84);8.13(3.24);8.114(2.78);8.015(2.1 - -δ = 8.996 (0.34), 8.933 (1.81), 8.9 (3.89), 8.886 (1.57), 8.197 (1.86), 8.19 (0.8), 8.162 (0.46), 8.153 (3.84), 8.13 (3.24), 8.114 (2.78 ); 8,015 (2.1 - -
8);7.995(0.39);7.957(0.36);7.756(3.26);7.726(2.82);7.715(2.88);7.691(0.75);7.522(0.87);7.508(0.33);7.502(0.96);7.491(1.01);7.2(7,491; 8); 7.995 (12:39); 7,957 (00:36); 7.756 (3.26); 7,726 (2.82); 7.715 (2.88); 7.691 (0.75); 7.522 (0.87); 7,508 (00:33); 7.502 (0.96) 1.01); 7.2
65(27.22);7.112(0.98);7.109(0.36);7.101(0.93);7.06(2.78);7.049(2.67);5.165(0.53);4.444(0.87);4.437(0.71);4.417(0.46);4.333(0.465 (27.22) 7.112 (0.98); 7,109 (00:36); 7.101 (0.93); 7:06 (2.78); 7.049 (2.67); 5,165 (12:53); 4.444 (0.87); 4.437 (0.71); 4,417 (00:46); 4333 (0.4
6);4.315(1.08);4.309(4.2);4.299(16);4.285(9.58);4.273(0.65);4.259(0.47);4.038(0.39);4.031(8.76);3.846(0.61);3.134(0.47);3.115((3,134; 6); 4.315 (1:08); 4,309 (4.2); 4,299 (16); 4,285 (9:58); 4.273 (0.65); 4,259 (12:47); 4,038 (12:39); 4.031 (8.76); 3.846 (0.61) 12:47); 3.115 (
1.93);3.1(2.83);3.097(4.47);3.082(2.84);3.079(4.47);3.06(1.71);3.043(0.91);3.029(3.53);3.016(3.62);3.001(0.64);2.991(0.44);2.98(2.991; 1.93); 3.1 (2.83); 3,097 (4:47); 3.082 (2.84); 3,079 (4:47); 3:06 (1.71); 3.043 (0.91); 3,029 (3:53); 3.016 (3.62); 3.001 (0.64) 12:44); 2.98
5(0.46);2.956(14.77);2.948(1.51);2.934(1.23);2.929(3.12);2.916(1.36);2.911(3.17);2.893(1.37);2.882(13.31);2.862(0.58);2.851(0.5 (12:46); 2,956 (14.77); 2,948 (1:51); 2.934 (1.23); 2.929 (3.12); 2,916 (1:36); 2.911 (3.17); 2,893 (1:37); 2,882 (13:31); 2,862 (12:58); 2,851 (0th
6);2.843(0.52);2.825(0.55);2.81(0.73);2.792(0.92);2.775(0.9);2.767(0.59);2.756(0.85);2.747(0.56);2.738(0.81);2.731(0.59);2.719(6); 2.843 (00:52); 2,825 (00:55); 2.81 (0.73); 2.792 (0.92); 2,775 (0.9); 2,767 (12:59); 2.756 (0.85); 2,747 (12:56); 2.738 (0.81); 2,731 ( 12:59); 2.719 (
0.71);2.705(0.67);2.687(0.53);2.669(0.39);2.659(0.38);2.641(0.4);2.633(0.35);2.625(0.36);2.554(0.38);2.544(0.46);2.535(0.35);2.(2.535; 0.71); 2.705 (0.67); 2,687 (12:53); 2,669 (12:39); 2,659 (00:38); 2,641 (0.4); 2,633 (12:35); 2,625 (12:36); 2,554 (12:38); 2,544 (12:46) 12:35), 2.
525(0.59);2.505(0.51);2.477(0.44);2.458(0.58);2.452(0.47);2.439(0.5);2.434(0.45);2.429(0.38);2.424(0.32);2.131(1.93);1.439(0.4525 (0:59); 2,505 (12:51); 2,477 (00:44); 2,458 (12:58); 2,452 (00:47); 2,439 (0.5); 2,434 (0.45); 2,429 (12:38); 2,424 (00:32); 2.131 (1.93); 1439 (0.4
1);1.427(0.62);1.421(0.87);1.408(0.49);1.4(2.59);1.394(1.2);1.388(1.32);1.381(5.28);1.376(2.15);1.372(2.27);1.37(2.31);1.363(3.(1:37, 1); 1.427 (0.62); 1.421 (0.87); 1,408 (12:49); 1.4 (2:59); 1,394 (1.2); 1,388 (1.32); 1,381 (28.5); 1.376 (2.15); 1.372 (2.27) 2.31); 1,363 (. 3
52);1.354(1.43);1.351(1.4);1.344(0.97);1.337(0.76);1.324(1.02);1.32(1.01);1.306(1.67);1.287(1.34);1.256(3.74);1.247(3.59);1.23(1.247; 52); 1,354 (1:43); 1,351 (1.4); 1,344 (0.97); 1.337 (0.76); 1.324 (1.02) 1.32 (1.01); 1.306 (1.67); 1,287 (1:34); 1.256 (3.74) 3:59); 1.23
8(7.91);1.229(5.75);1.22(10.47);1.21(3.23);1.201(5.27);1.188(1.43);1.181(1.61);1.177(2.17);1.166(1.97);1.158(3.08);1.156(3.01);8 (7.91) 1,229 (5.75); 1:22 (10:47) 1.21 (3.23); 1.201 (5.27); 1,188 (1:43); 1.181 (1.61); 1.177 (2.17); 1.166 (1.97); 1,158 (3:08); 1.156 (3.01);
1.148(2.8);1.14(1.95);1.13(1.63);1.116(1.14);1.111(1);1.093(1.27);1.075(1);1.058(0.6);0.992(0.44);0.974(0.65);0.964(0.62);0.9551.148 (2.8) 1.14 (1.95); 1.13 (1.63); 1.116 (1.14); 1.111 (1); 1.093 (1.27); 1.075 (1); 1,058 (0.6); 0.992 (12:44); 0.974 (0.65); 0.964 (0.62); 0.955
(0.49);0.946(0.89);0.928(0.53);0.913(0.39);0.895(0.34);0.88(0.34);0(4.13) (0:49); 0.946 (0.89); 0.928 (12:53); 0.913 (12:39); 0.895 (12:34); 0.88 (0:34) 0 (4.13)
Beispiel 1-3: 1H-NMR(400.0 MHz, CDC13): Example 1-3: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.98(3.35);8.901(0.37);8.695(2.52);8.692(2.49);8.428(0.62);8.133(3.56);8.034(0.4);7.262(13.8);5.3(0.45);4.461(1.18);4.44(1.8 8);4.266(16);4.205(0.99);4.187(3.31);4.168(3.37);4.15(1.07);3.143(1.24);3.135(1.35);1.582(7.85);1.479(3.43);1.46(7.32);1.442(3.δ = 8.98 (3.35), 8.901 (0.37), 8.695 (2.52), 8.692 (2.49), 8.428 (0.62), 8.133 (3.56), 8.034 (0.4), 7.262 (13.8), 5.3 (0.45), 4.461 (1.18 4.44 (1.8 8), 4.266 (16), 4.205 (0.99), 4.187 (3.31), 4.168 (3.37), 4.15 (1.07), 3.143 (1.24), 3.135 (1.35), 1.582 (7.85), 1.479 ( 3:43) 1.46 (7:32); 1,442 (. 3
33);1.369(0.38);1.35(0.74);1.332(0.35);0.008(0.5);0(15.53) 33); 1,369 (12:38); 1:35 (0.74); 1,332 (12:35); 0.008 (0.5) 0 (15:53)
Beispiel 1-4: 1H-NMR(400.0 MHz, CDC13): Example 1-4: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.905(3.49);8.081(3.75);7.262(8.81);5.3(8.56);4.423(1.79);4.405(2.55);4.386(1.86);4.289(0.36);4.187(16);4.055(1.04);4.037(3 .39);4.018(3.42);4(1.09);3.074(1.53);3.055(2.72);3.035(2.02);2.781(0.56);2.762(1.44);2.744(1.92);2.724(1.28);2.706(0.42);1.578(δ = 8,905 (3.49), 8,081 (3.75), 7,262 (8.81), 5.3 (8.56), 4,423 (1.79), 4,405 (2.55), 4,386 (1.86), 4,289 (0.36), 4,187 (16), 4,055 (1.04 4,037 (3 .39); 4,018 (3.42); 4 (1.09); 3,074 (1.53); 3,055 (2.72); 3,035 (2,02); 2,781 (0.56); 2,762 (1.44); 2,744 (1.92); 2,724 (1.28); 2,706 (12:42); 1,578 (
3.55);1.435(3.61);1.416(7.63);1.398(3.5);0(5.94) 3.55); 1.435 (3.61); 1,416 (7.63); 1,398 (3.5) 0 (5.94)
Beispiel 1-5: Ή-ΝΜΙ^όΟΙ.ό MHz, CDC13):  Example 1-5: Ή-ΝΜΙ ^ όΟΙ.ό MHz, CDC13):
δ= 9.208(1.11);8.991(3.51);8.321(1.2);8.15(3.76);7.261(31.87);5.298(3.49);4.477(5.33);4.13(16);4.029(1.29);3.892(1.1);3.879(3.δ = 9,208 (1.11), 8,991 (3.51), 8,321 (1.2), 8.15 (3.76), 7,261 (31.87), 5,298 (3.49), 4,477 (5.33), 4.13 (16), 4,029 (1.29), 3,892 (1.1 ); 3,879 (. 3
57);3.867(3.63);3.855(1.15);1.572(5.73);1.512(4.03);1.499(7.96);1.487(3.8);1.256(1.32);0.005(0.8);0(20.58) 57); 3,867 (3.63); 3.855 (1.15); 1.572 (5.73); 1,512 (4:03); 1.499 (7.96); 1,487 (3.8); 1,256 (1.32); 0.005 (0.8) 0 (20:58)
Beispiel 1-6: 1H-NMR(400.0 MHz, CDC13): Example 1-6: 1 H-NMR (400.0 MHz, CDC13):
δ= 8.927(3.45);8.902(1.95);8.552(0.61);8.428(2.76);8.161(3.73);8.122(2.44);8.119(2.48);8.036(2.01);8.021(1.38);8.018(1.37);7.2 62(27.56);5.3(0.69);4.449(2.19);4.441(8.48);4.415(0.38);4.3(16);4.19(0.38);3.378(0.47);3.185(1.21);3.166(3.82);3.148(4.01);3.14 2(1.18);3.138(1.06);3.13(1.46);3.118(0.35);3.057(0.54);3.038(0.5);3.029(0.32);3.01(0.35);1.576(9.91);1.436(0.39);1.426(0.57);1. 407(0.37);1.356(0.79);1.344(0.91);1.337(1.4);1.326(1.03);1.32(1.08);1.308(0.8);1.303(0.72);1.291(0.48);1.285(0.47);1^ δ = 8,927 (3.45), 8,902 (1.95), 8,552 (0.61), 8,428 (2.76), 8,161 (3.73), 8,122 (2.44), 8,119 (2.48), 8,036 (2.01), 8,021 (1.38), 8,018 (1.37 7.2 62 (27.56), 5.3 (0.69), 4.449 (2.19), 4.441 (8.48), 4.415 (0.38), 4.3 (16), 4.19 (0.38), 3.378 (0.47), 3.185 (1.21), 3.166 ( 3.82); 3.148 (4.01); 3.14 2 (1.18); 3.138 (1.06); 3.13 (1.46); 3.118 (0.35); 3.057 (0.54); 3.038 (0.5); 3.029 (0.32); 3.01 (0.35); 1.576 (9.91); 1,436 (12:39); 1,426 (12:57) -1. 407 (0:37); 1.356 (0.79); 1,344 (0.91); 1,337 (1.4); 1,326 (1:03) 1.32 (1:08); 1,308 (0.8); 1,303 (0.72); 1,291 (12:48); 1,285 (12:47); 1 ^
1.251(8.48);1.243(0.86);1.232(4.25);1.215(0.36);0.008(1.06);0(31.75);-0.008(1.33) 1.251 (8:48); 1.243 (0.86); 1.232 (4.25); 1,215 (12:36); 0.008 (1.06) 0 (31.75), - 0.008 (1.33)
Anwendungsbeispiele applications
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. For the coating of the test tubes, first 9 mg of active ingredient are dissolved in 1 ml of acetone pa and then diluted with acetone pa to the desired concentration. 250 μΐ of the solution are homogeneously distributed on the inner walls and the bottom of a 25 ml glass tube by turning and tilting on a rotary shaker (2 h swing rotation at 30 rpm). At 900 ppm active ingredient solution and 44.7 cm 2 inner surface, a surface dose of 5 μg / cm 2 is achieved with homogeneous distribution.
Nach Abdampfen des Lösungsmittels werden die Gläschen mit 5-10 adulten Katzenflöhen {Ctenocephalides felis) besetzt, mit einem gelochten Kunststoffdeckel verschlossen und liegend bei Raumtemperatur und Umgebungsfeuchte inkubiert. Nach 48 h wird die Wirksamkeit bestimmt. Hierzu werden die Gläschen aufrecht gestellt und die Flöhe auf den Boden des Gläschens geklopft. Flöhe, die unbeweglich auf dem Boden verbleiben oder sich unkoordiniert bewegen, gelten als tot bzw. angeschlagen. After evaporation of the solvent, the vials are filled with 5-10 adult cat fleas {Ctenocephalides felis), closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
Eine Substanz zeigt gute Wirkung gegen Ctenocephalides felis, wenn in diesem Test bei einer Aufwandmenge von 5 μg/cm2 mindestens 80% Wirkung erzielt wurde. Dabei bedeutet 100% Wirkung, dass alle Flöhe angeschlagen oder tot waren. 0% Wirkung bedeutet, dass keine Flöhe geschädigt wurden. A substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 μg / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 5 μg/cm2 (= 500 g/ha): 1-3 Ctenocephalides felis - Oraltest 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): 1-3 Ctenocephalides felis oral test
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. 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. For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. 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.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 95% bei einer Aufwandmenge von 100 ppm: 1-3 After 2 days the kill is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 95% at an application rate of 100 ppm: 1-3
Lucilia cuprina - Test Lucilia cuprina - test
Lösungsmittel: Dimethylsulfoxid Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Solvent: dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Ca. 20 LI -Larven der Australischen Schafgoldfliege (Lucilla cuprina) werden in ein Testgefäß überführt, welches gehacktes Pferdefleisch und die Wirkstoffzubereitung der gewünschten Konzentration enthält. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden. Approximately Twenty LI larvae of the Australian Goldfish fly (Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration. 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: 1-3, 1-4 In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 100 ppm: 1-3, 1-4
Musca domestica-Test Lösungsmittel: Dimethylsulfoxid Musca domestica test Solvent: Dimethylsulfoxide
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 Wirkung von 80 % bei einer Aufwandmenge von 100 ppm: 1-3 - - In this test, for example, the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: 1-3 - -
Myzus persicae - Oraltest Myzus persicae - Oraltest
Lösungsmittel: 100 Gewichtsteile Aceton Solvent: 100 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser bis zum Erreichen der gewünschten Konzentration auf. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water until the desired concentration is reached.
50 μΐ der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150μ1 IPL41 Insektenmedium (33% + 15% Zucker) auf eine Endvolumen von 200 μΐ aufgefüllt. Anschließend werden die Platten mit Parafilm verschlossen, durch den eine gemischte Population der Grünen Pfirsichblattlaus (Myzus persicae), die sich in einer zweiten Mikrotiterplatte befindet, hindurchstechen und die Lösung aufnehmen kann. 50 μΐ of the active ingredient preparation are transferred 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.
Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 20 ppm: 1-3, 1-4, 1-5 Myzus persicae - Sprühtest In this test, z. For example, the following compounds of the Preparation Examples Effect of 100% at an application rate of 20 ppm: 1-3, 1-4, 1-5 Myzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine 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), die von allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
Nach 5 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. After 5 days, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 500 g/ha: 1-4 Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 70% bei einer Aufwandmenge von 500 g/ha: 1-1, 1-5 In this test, z. Example, the following compounds of the preparation examples effect of 90% at a rate of 500 g / ha: 1-4 In this test, z. Example, the following compounds of the preparation examples effect of 70% at a rate of 500 g / ha: 1-1, 1-5
Phaedon cochleariae - Sprühtest Phaedon 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 j besetzt. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae j.
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 500 g/ha: 1-3, 1-4, 1-5 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 500 g / ha: 1-3, 1-4, 1-5
Spodoptera frugiperda - Sprühtest 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 Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. - - After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed. - -
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 500 g/ha: 1-3 In this test, z. Example, the following compounds of the preparation examples effect of 100% at a rate of 500 g / ha: 1-3
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 500 g/ha: 1-5 Tetranvchus urticae - Sprühtest, OP-resistent In this test, z. For example, the following compounds of the preparation examples effect of 83% at a rate of 500 g / ha: 1-5 Tetranvchus urticae - spray test, OP-resistant
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.
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 Wirkung von 70% bei einer Aufwandmenge von 500 g/ha: 1-5 Myzus persicae - Sprühtest In this test, z. Example, the following compounds of the preparation examples effect of 70% at a rate of 500 g / ha: 1-5 Myzus persicae - spray test
Lösungsmittel: 14 Gewichtsteile Dimethylformamid Solvent: 14 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. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt. - - To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution. - -
Paprikapflanzen {Capsicum annuum), die stark von der Grünen Pfirsichblattlaus (Myzus persicae) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt. Paprika plants (Capsicum annuum) which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.
Nach 6 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 , dass alle Läuse abgetötet wurden; 0 % bedeutet, dass keine Läuse abgetötet wurden. After 6 days the kill is determined in%. 100 means that all lice have been killed; 0% means that no lice have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 98% bei einer Aufwandmenge von 20ppm: 1-3 In this test, z. For example, the following compounds of the Preparation Examples Effect of 98% at a rate of 20ppm: 1-3

Claims

Patentansprüche l. Verbindungen der Formeln (I) oder (Γ) Claims l. Compounds of the formulas (I) or (II)
Figure imgf000106_0001
Figure imgf000106_0001
(I) (Γ) in welchen (I) (Γ) in which
Aa für Stickstoff oder ^ (ein Kohlenstoffatom mit einer Doppebindung zu Ab bzw. Aa is nitrogen or ^ (a carbon atom with a double bond to Ab or
Ad) steht,  Ad),
Ab für =N-, -S(0)m-, -O-, -N(R7)-, =C(R2)- oder -C(R9)(R10)- steht, From = N-, -S (0) m -, -O-, -N (R 7) -, = C (R 2) - or -C (R 9) (R 10) - group,
Ac für =N-, -S(0)m-, -O-, -N(R7)-, =C(R3)- oder -C(RU)(R12)- steht, Ac represents = N-, -S (O) m -, -O-, -N (R 7 ) -, = C (R 3 ) - or -C (R U ) (R 12 ) -,
Ad für =N-, -S(0)m-, -O-, -N(R7)-, =C(R8)- oder -C(R13)(R14)- steht, wobei nur einer der Substituenten Ab, Ac oder Ad für Sauerstoff oder -S(0)m- stehen kann, Ad is = N-, -S (O) m -, -O-, -N (R 7 ) -, = C (R 8 ) - or -C (R 13 ) (R 14 ) -, where only one the substituent Ab, Ac or Ad may be oxygen or -S (0) m -,
R1 für (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, (Ci- C6)Alkoxy-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyl, (C2- C6)Alkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Alkinyloxy-(Ci-C6)alkyl, (C2-R 1 alkyl is (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) haloalkoxy (Ci-C 6), (C 2 -C 6) alkenyl, (C2 - C6) alkenyloxy (Ci-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C C6) alkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) alkynyloxy (Ci-C 6) alkyl, (C 2 -
C6)Halogenalkinyloxy-(Ci-C6)alkyl, (C2-Ce)Halogenalkinyl, (C2-Ce)Cyanoalkinyl, (C3- C8)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)Cycloalkyl, Halogen(C3-C8)cycloalkyl, Amino, (Ci-C6)Alkylamino, Di-(Ci-C6)alkyl-amino, (C3- C8)Cycloalkylamino, (Ci-C6)Alkylcarbonyl-amino, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci- C6)Halogenalkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6) Halogenalkinyloxy- (Ci-C6) alkyl, (C2 -Ce) haloalkynyl, (C2 -Ce) cyanoalkynyl, (C3- C8) cycloalkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl , (Ci-C 6) alkyl (C 3 -C 8) cycloalkyl, halo (C3-C8) cycloalkyl, amino, (Ci-C6) alkylamino, di (Ci-C6) alkyl-amino, (C3- C8) cycloalkylamino, (Ci-C6) alkylcarbonyl-amino, (Ci-C6) alkylthio (Ci-C6) alkyl, (Ci- C 6) haloalkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfinyl- (C 1 -C 6 ) -alkyl,
C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C 6) Halogenalkylsulfinyl- (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-
C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkylthio-(Ci-C6)alkyl, (Ci- C6)Alkoxy-(Ci-C6)alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl, (Ci- C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxycarbonyl-(Ci-C6)alkyl, (Ci- C6)Alkylsulfonylamino, Aminosulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylaminosulfonyl-(Ci-C6)alkyl, Di-(Ci-C6)alkyl-aminosulfonyl-(Ci-C6)alkyl, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Aryl, Hetaryl oder Heterocyclyl substituiertes (Ci-Ce)Alkyl, (Ci-C6)Alkoxy, (C2-C6)Alkenyl, (C2- C6)Alkinyl, (C3-C8)Cycloalkyl steht, wobei Aryl, Hetaryl oder Heterocyclyl jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, Aminosulfonyl, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (Ci- C6)Alkoxy, (Ci-C6)Halogenalkyl, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Alkylsulfimino, (Ci-C6)Alkylsulfimino-(Ci-C6)alkyl, (Ci- C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkylsulfoximino, (Ci-C6)Alkylsulfoximino-(Ci- Ce)alkyl, (Ci-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci- C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl oder Benzyl substituiert sein können, oder C 6) haloalkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) alkoxy (Ci-C 6) alkylthio- (Ci-C 6) alkyl, (Ci- C6) alkoxy (Ci-C 6) alkylsulfinyl (Ci-C6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C6) alkylcarbonyl (Ci-C 6) alkyl, ( C 1 -C 6 ) haloalkylcarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -halogenalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonylamino, Aminosulfonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminosulfonyl- (C 1 -C 6) -alkyl, Di (Ci-C6) alkyl-aminosulfonyl- (Ci-C6) alkyl, or for each optionally mono- or polysubstituted by identical or different aryl, hetaryl or heterocyclyl (Ci-Ce) alkyl, (Ci-C6) alkoxy, (C 2 -C 6) alkenyl, (C2 - C6) alkynyl, (C3-C8) cycloalkyl, wherein aryl, hetaryl or heterocyclyl each optionally monosubstituted or polysubstituted by identical or different halogen, cyano, nitro, hydroxy, amino, Carboxy, carbamoyl, aminosulfonyl, (Ci-C6) alkyl, (C 3 -C 6 ) cycloalkyl, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) haloalkoxy, (Ci-C 6 ) alkylthio, (Ci-C 6) alkylsulfinyl, (Ci-C 6) alkylsulfonyl, (Ci-C 6) Alkylsulfimino, (Ci-C 6) Alkylsulfimino- (Ci-C 6) alkyl, (Ci- C6) Alkylsulfimino- (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkylsulfoximino, (C 1 -C 6) alkylsulfoximino (ci-C) alkyl, (C 1 -C 6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl , (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl or benzyl, or
R1 für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen, Cyano, Nitro, Hydroxy, Amino, Carboxy, Carbamoyl, (Ci-Ce)Alkyl, (C3- C8)Cycloalkyl, (Ci-C6)-Alkoxy, (Ci-C6)Halogenalkyl, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Alkylsulfimino, (Ci-C6)Alkylsulfimino-(Ci- C6)alkyl, (Ci-C6)Alkylsulfimino-(C2-C6)alkylcarbonyl, (Ci-C6)Alkylsulfoximino, (Ci- C6)Alkylsulfoximino-(Ci-C6)alkyl, (Ci-C6)Alkylsulfoximino-(C2-C6)alkylcarbonyl, (Ci- Ce)Alkoxycarbonyl, (Ci-C6)Alkylcarbonyl, (C3-C6)Trialkylsilyl, (=0) (nur im Fall von Heterocyclyl) oder (=0)2 (nur im Fall von Heterocyclyl) substituiertes Aryl, Hetaryl oder Heterocyclyl steht, R 1 is in each case optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 6 ) - alkoxy, (Ci-C 6) haloalkyl, (Ci-C 6) haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) alkylsulfinyl, (Ci-C 6) alkylsulfonyl, (Ci-C 6) Alkylsulfimino, (C 1 -C 6 ) alkylsulfimino (C 1 -C 6 ) alkyl, (C 1 -C 6) alkylsulfimino (C 2 -C 6) alkylcarbonyl, (C 1 -C 6) alkylsulfoximino, (C 1 -C 6) alkylsulfoximino (C 1 -C 6) -alkyl , (C 1 -C 6) alkylsulfoximino (C 2 -C 6) alkylcarbonyl, (ci -Ce) alkoxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 6) trialkylsilyl, (= O) (only in the case of heterocyclyl) or (= 0) 2 (only in the case of heterocyclyl) substituted aryl, hetaryl or heterocyclyl,
R2, R3, R8, R9, R10, R11, R12, R13, R14 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, Tri-(Ci-C6)alkylsilyl, (C3-C8)Cycloalkyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, Hydroxycarbonyl-(Ci-C6)-alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci- C6)alkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-Ce)Alkoxy, (Ci-Ce)Halogenalkoxy, (Ci- Ce)Cyanoalkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci- C6)Alkylhydroxyimino, (Ci-C6)Alkoxyimino, (Ci-C6)Alkyl-(Ci-C6)alkoxyimino, (Ci- C6)Halogenalkyl-(Ci-C6)alkoxyimino, (Ci-Ce)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci- C6)Alkoxy-(Ci-C6)alkylthio, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl, (Ci- C6)Halogenalkylsulfinyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfinyl, (Ci-C6)Alkylsulfinyl-(Ci- C6)alkyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, (Ci-C6)Alkoxy-(Ci- C6)alkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyloxy, (Ci- Ce)Alkylcarbonyl, (Ci-C6)Alkylthiocarbonyl, (Ci-C6)Halogenalkylcarbonyl, (Ci- Ce)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, Di-(Ci-C6)alkyl-aminothiocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-Ce)- alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci- C6)Alkylamino, Di-(Ci-C6)Alkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci- C6)alkyl-aminosulfonyl, (Ci-C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci-R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another represent hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN, tri- (C 1-6) C 6) alkylsilyl, (C 3 -C 8) cycloalkyl, (C 3 - C 8) cycloalkyl (C 3 -C 8) cycloalkyl, (Ci-C (6) alkyl C 3 -C 8) cycloalkyl, halogen (C 3 -C 8) cycloalkyl, (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, hydroxycarbonyl (Ci-C6) alkoxy , (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C6) alkoxy (Ci- C6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 - C6) haloalkynyl, (C 2 -C 6) cyanoalkynyl, (Ci-Ce) alkoxy, (Ci-Ce) haloalkoxy, (Ci- Ce ) Cyanoalkoxy, (C 1 -C 6) alkoxycarbonyl- (C 1 -C 6) alkoxy, (C 1 -C 6) alkoxy- (C 1 -C 6) alkoxy, (C 1 -C 6) alkylhydroxyimino, (C 1 -C 6) alkoxyimino, (C 1 -C 6) alkyl (Ci-C6) alkoxyimino, (Ci- C6) haloalkyl (Ci-C6) alkoxyimino (Ci-Ce) alkylthio, (Ci-C6) haloalkylthio, (Ci- C6) alkoxy (Ci-C 6 ) alkylthio, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, C 6) alkylsulfinyl, (Ci- C 6) haloalkylsulfinyl, (Ci-C 6) alkoxy (Ci-C 6) alkylsulfinyl, (Ci-C 6) alkylsulfinyl (Ci-C6) alkyl, (Ci-C 6 ) alkylsulfonyl, (Ci-C 6) haloalkylsulfonyl, (Ci-C 6) alkoxy (Ci- C6) alkylsulfonyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C6) alkylsulphonyloxy , (Ce-Ce) alkylcarbonyl, (Ci-C6) alkylthiocarbonyl, (Ci-C6) haloalkylcarbonyl, (Ce-Ce) alkylcarbonyloxy, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6) alkylaminocarbonyl, (C 1 -C 6) alkylaminothiocarbonyl, di (C 1 -C 6) alkylaminocarbonyl, di (C 1 -C 6) alkylaminothiocarbonyl, (C 2 -C 6) alkenylaminocarbonyl, di (C 2 -Ce ) - alkenylaminocarbonyl, (C 3 -C 8) cycloalkylaminocarbonyl, (C 1 -C 6) alkylsulfonylamino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamino, aminosulfonyl, (C 1 -C 6) alkylaminosulfonyl, di (C 1 -C 6) alkyl-aminosulfonyl, (Ci-C6) alkylsulfoximino, aminothiocarbonyl,
C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkyl-aminothiocarbonyl, (C3-C8)Cycloalkylamino oder NHCO-(Ci-C6)alkyl ((Ci-C6)Alkylcarbonylamino) stehen, C 6 ) alkylaminothiocarbonyl, di- (C 1 -C 6 ) -alkyl-aminothiocarbonyl, (C 3 -C 8) -cycloalkylamino or -NHCO- (C 1 -C 6 ) -alkyl ((C 1 -C 6 ) -alkylcarbonylamino),
R7 für Wasserstoff, Acetyl, (Ci-C4)Alkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2- C4)Alkenyl, (C2-C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2- C4)Halogenalkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (C3- C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio- (Ci-C4)alkyl, (Ci-C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci- C4)Halogenalkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl, (Ci- C4)Alkylcarbonyl-(Ci-C4)alkyl, (Ci-C4)Halogenalkylcarbonyl-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl steht, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, Cyano, (Ci-C4)Alkyl, (C3-C4)Cycloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkyl, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylsulfinyl oder (Ci-C4)Alkylsulfonyl, substituiert sein können, R 7 (hydrogen, acetyl, (Ci-C 4) alkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) haloalkyl, (CI-C 4) cyanoalkyl, (Ci-C 4) alkoxy- Ci- C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4) alkyl, (C 2 - C 4) Halogenalkinyloxy- (Ci-C 4) alkyl, (C 2 -C 4) haloalkynyl, (C 2 -C 4) cyanoalkynyl, (C 3 - C 6) Cycloalkyl, (Ci-C 4 ) alkyl (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4) alkyl, (Ci C 4) Halogenalkylsulfinyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl - (Ci-C 4) alkyl, (Ci C 4) alkylcarbonyl (Ci-C 4) alkyl, (Ci-C4) haloalkylcarbonyl (Ci-C 4) alkyl, or represents in each case optionally monosubstituted or disubstituted by identical or substituted differently by aryl or heterocyclyl it (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, where aryl or heterocyclyl each optionally monosubstituted or disubstituted by identical or different halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 4) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkyl, (CI-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) Alkylsulfinyl or (C 1 -C 4 ) -alkylsulfonyl,
Q für ein teilweise gesättigtes oder gesättigtes heterozyklisches oder heteroaromatisches 8-, 9-, 10-, 11- oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem steht, wobei gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und/oder wobei das Ringsystem gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiert ist, und wobei die Substituenten unabhängig voneinander ausgewählt sein können aus Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, Tri-(Ci-C6)alkylsilyl, (C3-C8)Cycloalkyl, (C3- C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-C8)cycloalkyl, Halogen(C3-C8)cycloalkyl, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, Hydroxycarbonyl-(Ci-C6)-alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci- C6)alkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2- C6)Alkinyloxy-(Ci-C4)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-C6)Alkoxy, (Ci- C6)Halogenalkoxy, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyloxy-(Ci-C6)alkyl, (C2- C6)Halogenalkenyloxy-(C 1 -Ce) alkyl, (C 1 -Ce)Cy anoalkoxy , (C 1 -Ce) Alkoxycarbonyl-(C 1 - Ce)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci-C6)Alkylhydroxyimino, (Ci-C6)Alkoxyimino, (Ci-C6)Alkyl-(Ci-C6)alkoxyimino, (Ci-C6)Halogenalkyl-(Ci-C6)alkoxyimino, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkoxy-(Ci-C6)alkylthio, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci- C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (Ci-C6)Alkoxy-(Ci-C6)alkylsulfinyl, (Ci- C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, (Ci- C6)Alkoxy-(Ci-C6)alkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyloxy, (Ci-C6)Alkylcarbonyl, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkylthiocarbonyl, (Ci- Ce)Halogenalkylcarbonyl, (Ci-C6)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci- Ce)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, (Ci- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, Di-(Ci-Ce)alkyl- aminothiocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)-alkenylaminocarbonyl, (C3- C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylamino, Di-(Ci- C6)Alkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci-C6)alkyl-aminosulfonyl, (Ci-C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci- C6)alkyl-aminothiocarbonyl, (C3-C8)Cycloalkylamino, NHCO-(Ci-C6)alkyl ((Ci-Q is a partially saturated or saturated heterocyclic or heteroaromatic 8-, 9-, 10-, 11- or 12-membered fused bicyclic or tricyclic ring system, which may optionally contain at least one carbonyl group and / or wherein the ring system optionally mono- or polysubstituted is substituted identically or differently, and where the substituents can be selected independently of one another from cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri (C 1 -C 6 ) alkylsilyl, (C 3 -C 8 ) cycloalkyl, (C 3 - C 8) cycloalkyl (C 3 -C 8) cycloalkyl, (Ci-C 6) alkyl (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6 ) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, hydroxycarbonyl (Ci-C6) alkoxy, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl , (Ci-C6) alkoxy (Ci- C6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 - C 6) alkynyloxy (Ci-C4) alkyl, (C 2 -C 6) halogen alkynyl, (C 2 -C 6) cyanoalkynyl, (Ci-C 6) alkoxy, (Ci- C 6) haloalkoxy, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) Alkenyloxy- (C 1 -C 6 ) alkyl, (C 2 -C 6 ) haloalkenyloxy- (C 1 -Ce) alkyl, (C 1 -Ce) cyanoalkoxy, (C 1 -Ce) alkoxycarbonyl- (C 1 -C 6) alkoxy , (C 1 -C 6) alkoxy- (C 1 -C 6) alkoxy, (C 1 -C 6) alkylhydroxyimino, (C 1 -C 6) alkoxyimino, (C 1 -C 6 ) alkyl- (C 1 -C 6 ) alkoxyimino, (C 1 -C 6 ) haloalkyl- (C 1 -C 6 ) alkoxyimino, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) haloalkylsulfinyl, (C 1 -C 6 ) alkoxy ( Ci-C 6) alkylsulfinyl, (Ci- C6) alkylsulfinyl (Ci-C6) alkyl, (Ci-C 6) alkylsulfonyl, (Ci-C 6) haloalkylsulfonyl, (Ci- C 6) alkoxy (Ci- C 6) alkylsulfonyl, (Ci-C 6) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) alkylsulfonyloxy, (Ci-C 6) alkylcarbonyl, (Ci-C6) alkylcarbonyl (Ci-C 6 ) alkyl, (C 1 -C 6 ) alkylthiocarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6 ) alkylcarbonyloxy, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 ) haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (Ci - C6) alkylaminothiocarbonyl, di (Ci-C6) alkylaminocarbonyl, di- (Ci-Ce) alkylaminothiocarbonyl, (C2-C6) alkenylaminocarbonyl, di- (C2-C6) -alkenylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl , (C 1 -C 6) alkylsulfonylamino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamino, aminosul (C 1 -C 6 ) alkylaminosulfonyl, di- (C 1 -C 6 ) alkylaminosulfonyl, (C 1 -C 6 ) alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 ) -alkylaminothiocarbonyl, di- (C 1 -C 6 ) -alkylaminothiocarbonyl, ( C 3 -C 8 ) cycloalkylamino, NHCO- (C 1 -C 6 ) -alkyl (C 1 -C 8 )
CÖ) Alkylcarbonylamino) , oder wobei die Substituenten unabhängig voneinander ausgewählt sein können aus Phenyl oder einem 5- oder 6-gliedrigen heteroaromatischen Ring, wobei Phenyl oder der Ring gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Ci-Cö-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, Ci-Ce-Haloalkyl, C2-C6-Haloalkenyl, C2-C6-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, Ci-C4-Alkoxy, Ci-C4-Haloalkoxy substituiert sein können, n für 0, 1 oder 2 steht, m für 0, 1 oder 2 steht, ausgenommen CÖ) alkylcarbonylamino), or wherein the substituents can be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted by Ci-Cö-alkyl, C2-C6 Alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN , NO 2, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, n is 0, 1 or 2, m is 0, 1 or 2, except
Figure imgf000109_0001
Figure imgf000109_0001
Verbindungen der Formeln (I) oder (Γ) gemäß Anspruch 1 , in welcher Compounds of formulas (I) or (II) according to claim 1, in which
Aa für Stickstoff steht, Aa is nitrogen,
Ab für =N-, -S(O) O-, -N(R7)-, =C(R2)- oder -C(R9)(R10)- steht, Ab represents = N-, -S (O) O-, -N (R 7 ) -, = C (R 2 ) - or -C (R 9 ) (R 10 ) -,
Ac für =N-, -S(0)m-, =C(R3)- oder -C(RU)(R12)- steht, Ac represents = N-, -S (0) m -, = C (R 3 ) - or -C (R U ) (R 12 ) -,
Ad für =N-, -S(O) O-, -N(R7)-, =C(R8)- oder -C(R13)(R14)- steht, wobei nur einer der Substituenten Ab, Ac oder Ad für Sauerstoff oder -S(0)m- stehen kann, wobei sich die folgenden Struktureinheiten AI bis A20 ergeben:
Figure imgf000110_0001
Ad is = N-, -S (O) O-, -N (R 7 ) -, = C (R 8 ) - or -C (R 13 ) (R 14 ) -, where only one of the substituents Ab, Ac or Ad can be oxygen or -S (0) m - where the following structural units AI to A20 result:
Figure imgf000110_0001
Figure imgf000110_0002
Figure imgf000110_0002
Figure imgf000110_0003
Figure imgf000110_0004
Figure imgf000110_0005
Figure imgf000110_0003
Figure imgf000110_0004
Figure imgf000110_0005
A18 A1 9 A20 R1 für (Ci-C4)Alkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci- C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl steht, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-C4)Cycloalkyl, (Ci- C4)Alkoxy oder (Ci-C4)Alkylthio substituiert sein können, oder A18 A1 9 A20 R 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkylthio (Ci-C alkyl 4), (Ci-C 4) alkylsulfinyl (CI-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, or represents in each case optionally mono- or disubstituted by identical or different aryl or Heterocyclyl substituted (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, wherein aryl or heterocyclyl each optionally once or twice the same or different by halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 4 ) cycloalkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio may be substituted, or
R1 für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)Halogenalkyl, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (=0) (nur im Fall von Heterocyclyl) oder (=0)2 (nur im Fall von Heterocyclyl) substituiertes Aryl, Hetaryl oder Heterocyclyl steht, R 1 represents in each case optionally monosubstituted or disubstituted by identical or different halogen, cyano, (Ci-C 4) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) halogenoalkyl (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) -alkylthio, (= 0) (only in the case of heterocyclyl) or (= O) 2 (only in the case of heterocyclyl) substituted aryl, hetaryl or heterocyclyl,
R2, R3, R8, R9, R10, R11, R12, R13, R14 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Hydroxy, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3- C6)cycloalkyl, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci- C4)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci- C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are each independently hydrogen, cyano, halogen, nitro, hydroxy, (C 3 -C 6 ) cycloalkyl, (Ci -C 4) alkyl- (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, ( C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl , (Ci C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, ( C 1 -C 4 ) alkylsulfonyl,
C4)Halogenalkylsulfonyl, (Ci-C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci- C4)Alkylamino, Di-(Ci-C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl, Di-(Ci- C4)alkyl-aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci-C4)Alkylcarbonylamino) stehen, C 4) haloalkylsulfonyl, (Ci-C 4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino , (Ci- C4) alkylamino, di- (Ci-C 4) alkylamino, aminosulfonyl, (Ci-C4) alkylaminosulfonyl, di (Ci- C4) alkyl-aminosulfonyl, or NHCO- (Ci-C 4) alkyl ((C 1 -C 4 ) alkylcarbonylamino),
R7 für Wasserstoff, Acetyl, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci- C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl- (C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl steht, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, (Ci-C4)Alkyl, Cyano, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkyl oder (Ci-C4)Halogenalkoxy substituiert sein können, R 7 is hydrogen alkyl, acetyl, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci- C4) alkoxy (Ci-C 4), (Ci- C 4) haloalkoxy (Ci-C 4) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, ( C 1 -C 4 ) alkylthio (C 1 -C 4 ) -alkyl, or in each case optionally monosubstituted or disubstituted by identical or different substituents by aryl or heterocyclyl (C 1 -C 4 ) -alkyl, where aryl or heterocyclyl is in each case optionally monosubstituted or disubstituted by identical haloalkoxy or different may be substituted by halogen, (Ci-C 4) alkyl, cyano, (Ci-C 4) alkoxy, (Ci-C 4) -haloalkyl or (Ci-C 4),
Q für ein heteroaromatisches 9-gliedriges oder 12-gliedriges annelliertes bicyclisches oder tricyclisches Ringsystem aus der Reihe Ql bis QU, Q14 bis Q17 oder Q20 steht, -111-
Figure imgf000112_0001
Q is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to QU, Q14 to Q17 or Q20, -111-
Figure imgf000112_0001
Figure imgf000112_0002
Figure imgf000112_0002
Figure imgf000112_0003
C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht,
Figure imgf000112_0003
C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 - C 4) alkenyloxy (Ci C 4) alkyl, (C2-C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C2-C4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4) alkyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (C -C 4) alkyl- (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl ( Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl or (Ci-C 4) alkylcarbonyl (Ci-C 4) alkyl,
R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3- C6)cycloalkyl, (Ci-C )Alkoxy, (Ci-C )Halogenalkoxy, (Ci-C )Alkoxyimino, (Ci-C )Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C )Alkylsulfonyl, (Ci-C )Halogenalkylsulfonyl, (Ci-C )Alkylsulfonyloxy, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl stehen, n für 0, 1 oder 2 steht, m für 0, 1 oder 2 steht. R 5, R 6 are each independently hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl ( C 3 - C6) cycloalkyl, (Ci-C) alkoxy, (Ci-C) haloalkoxy, (Ci-C) alkoxyimino, (C-C) alkylthio, (Ci-C4) haloalkylthio, (Ci-C4) alkylsulphinyl , (Ci-C 4 ) haloalkylsulfinyl, (Ci-C) alkylsulfonyl, (Ci-C) haloalkylsulfonyl, (Ci-C) alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci -C 4) alkylaminocarbonyl, di (Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C 4) alkylamino, di (Ci- C4) alkylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (C 1 -C 4 ) -alkylaminosulfonyl, n is 0, 1 or 2, m is 0, 1 or 2.
Verbindungen der Formeln (I) oder (Γ) gemäß Anspruch 1 , in welcher Aa für Stickstoff steht, Compounds of the formulas (I) or (II) according to Claim 1, in which Aa is nitrogen,
Ab für =N-, -O-, -N(R7)- oder =C(R2)- steht, Ac für =N- oder =C(R3)- steht, Ab represents = N-, -O-, -N (R 7 ) - or = C (R 2 ) -, Ac represents = N- or = C (R 3 ) -,
Ad für =N-, -S(0)m-, -O-, -N(R7)- oder =C(R8)- steht, wobei nur einer der Substituenten Ab oder Ad für Sauerstoff oder -S(0)m- stehen kann. wobei sich folgende Struktureinheiten ergeben: A5, A6, A7, A8, A9, A10, Al l, A12, A13, A19, A20, Ad is = N-, -S (O) m -, -O-, -N (R 7 ) - or = C (R 8 ) -, wherein only one of the substituents Ab or Ad is oxygen or -S (0 ) m - can stand. wherein the following structural units give: A5, A6, A7, A8, A9, A10, Al, A12, A13, A19, A20,
R1 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl oder (C3-C6)Cycloalkyl steht, R 1 is (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 3 -C 6 ) cycloalkyl,
R2, R3, R8 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Hydroxy, (C3- C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci- C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci-C4)Alkylcarbonylamino) stehen, R 2, R 3, R 8 are each independently hydrogen, cyano, halo, nitro, hydroxy, (C 3 - C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci- C 4 ) haloalkoxy, C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (Ci C 4) alkylsulfonyl, (Ci-C4) haloalkylsulfonyl, aminosulfonyl, (Ci C 4) alkylaminosulfonyl, di (Ci-C 4) alkyl-aminosulfonyl or alkyl (NHCO- (Ci-C 4) (Ci-C4) alkylcarbonylamino) are provided,
R7 für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl oder (Ci- C4)Alkoxy-(Ci-C4)alkyl steht, R 7 is hydrogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl or (Ci- C4) alkoxy (Ci-C 4) alkyl,
Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17 steht, Q represents a heteroaromatic 9-membered fused bicyclic ring system of the series Q1, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17,
R4 für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R 4 is (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
R5 für Halogen, (Ci-C4)Halogenalkyl, (Ci-C4)Halogenalkoxy oder (Ci-C4)Halogenalkylthio steht, R 5 is halogen, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or (C 1 -C 4 ) haloalkylthio,
R6 für Wasserstoff steht, n für 0, 1 oder 2 steht, m für 0 steht. 4. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher Aa für Stickstoff steht, Ab für =N- oder =C(R2)- steht, Ac für =N- oder =C(R3)- steht, Ad für -S(0)m-, -O- oder -N(R7)- steht, wobei sich folgende Struktureinheiten ergeben: A6, A10, Al l, A12, A13, R 6 is hydrogen, n is 0, 1 or 2, m is 0. 4. Compounds of formula (I) according to claim 1, in which Aa is nitrogen, Ab is = N- or = C (R 2 ) -, Ac is = N- or = C (R 3 ) -, Ad is -S (0) m -, -O- or -N (R 7 ) -, where the following structural units give: A6, A10, Al I, A12, A13,
Figure imgf000114_0001
Figure imgf000114_0001
A6 A10 A1 1  A6 A10 A1 1
Figure imgf000114_0002
Figure imgf000114_0002
A12 A13 R1 für Ethyl steht, A12 A13 R 1 is ethyl,
R2, R3 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Trifluormethylthio stehen, R 2 , R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
R7 für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, sec-Propyl oder tert.-Butyl steht, Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus derR 7 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, sec-propyl or tert-butyl, Q is a heteroaromatic 9-membered fused bicyclic ring system of the
Reihe Q2 oder Q3 steht, Series Q2 or Q3 stands,
Figure imgf000115_0001
Figure imgf000115_0001
R4 für Methyl, Ethyl, i-Propyl, Methoxymethyl oder Methoxyethyl steht, R 4 is methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
R5 für Fluor, Chlor, Brom, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl (CH2CFH2, CHFCH3), Difluorethyl (CF2CH3, CH2CHF2, CHFCFFF), Trifluorethyl, (CH2CF3,R 5 is fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CF 2 , CHFCH 3), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFFF), trifluoroethyl, (CH 2 CF 3 ,
CHFCHF2, CF2CFH2), Tetrafluorethyl (CHFCF3, CF2CHF2), Pentafluorethyl, Trifluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy oder Trifluormethylthio steht, CHFCHF 2 , CF 2 CF 2 ), tetrafluoroethyl (CHF CF 3, CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
R6 für Wasserstoff steht, n für 0, 1 oder 2 steht, m für 0 steht. R 6 is hydrogen, n is 0, 1 or 2, m is 0.
5. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher 5. Compounds of formula (I) according to claim 1, in which
Aa für Stickstoff steht, Aa is nitrogen,
Ab für =C(R2)- steht, Ab for = C (R 2 ) - stands,
Ac für =C(R3)- steht, Ad für -S(0)m- steht, wobei sich folgende Struktureinheit ergibt: Al l, Ac is = C (R 3 ) -, Ad is -S (0) m -, giving the following structural unit: Al 1,
R1 für Ethyl steht, R 1 is ethyl,
R2, R3 für Wasserstoff stehen, Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q3 steht, R 2 , R 3 are hydrogen, Q is a 9-membered heteroaromatic fused bicyclic ring system from the Q3 series,
R4 für Methyl steht, R 4 is methyl,
R5 für Trifluormethyl steht, R 5 is trifluoromethyl,
R6 für Wasserstoff steht, n für 0 oder 2 steht, m für 0 steht. R 6 is hydrogen, n is 0 or 2, m is 0.
Verbindungen der Formel (I) gemäß Anspruch 1 mit der Struktureinheit Al l Compounds of the formula (I) according to Claim 1 having the structural unit Al 1
Figure imgf000116_0001
in welcher
Figure imgf000116_0001
in which
Q für Q3 steht und Q stands for Q3 and
R1 für (Ci-C4)Alkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (Ci- C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci- C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl, oder für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Aryl oder Heterocyclyl substituiertes (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl steht, wobei Aryl oder Heterocyclyl jeweils gegebenenfalls einfach oder zweifach gleich oder verschieden durch Halogen, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-C4)Cycloalkyl, (Ci- C4)Alkoxy oder (Ci-C4)Alkylthio substituiert sein können, oder R 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkylthio (Ci-C alkyl 4), (Ci-C 4) alkylsulfinyl (CI-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, or represents in each case optionally mono- or disubstituted by identical or different aryl or Heterocyclyl substituted (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, wherein aryl or heterocyclyl each optionally once or twice the same or different by halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 4 ) cycloalkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio may be substituted, or
R1 für jeweils gegebenenfalls einfach oder zweifach, gleich oder verschieden durch Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)Halogenalkyl, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (=0) (nur im Fall von Heterocyclyl) oder (=0)2 (nur im Fall von Heterocyclyl) substituiertes Aryl, Hetaryl oder Heterocyclyl steht, R 1 represents in each case optionally monosubstituted or disubstituted by identical or different halogen, cyano, (Ci-C 4) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) halogenoalkyl , (Ci C 4) haloalkoxy, (Ci-C 4) alkylthio, (= 0) (only in the case of heterocyclyl) or (= 0) 2-substituted (only in the case of heterocyclyl) aryl, hetaryl or heterocyclyl,
R2, R3 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Hydroxy, (C3- C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci- C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci-C4)Alkylcarbonylamino) stehen, R 2, R 3 are each independently hydrogen, cyano, halogen, nitro, hydroxy, (C 3 - C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkyl, C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) haloalkynyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci- C 4) alkylsulfinyl, (Ci- C4) haloalkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C4) haloalkylsulfonyl, (Ci- C4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl, aminocarbonyl, (Ci C 4) alkylaminocarbonyl, di (Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C 4) alkylamino, di (Ci- C4) alkylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl, di (Ci-C 4) alkyl-aminosulfonyl, or NHCO- (Ci-C 4) alkyl ((Ci-C4) alkylcarbonylamino) are provided,
R4 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci- C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C2-C4)Alkenyl, (C2- C4)Alkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C2-C4)Alkinyl, (C2-C4)Alkinyloxy-(Ci-C4)alkyl, (C2-C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci-C4)Alkylcarbonyl-(Ci-C4)alkyl steht, R 4 alkyl of (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci C 4) alkoxy (Ci-C 4) , (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 - C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (C 4) alkyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4) alkyl, (Ci- C 4) alkylsulfonyl (Ci-C 4) alkyl or (Ci-C 4) alkylcarbonyl (Ci-C 4) alkyl,
R5, R6 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)cycloalkyl, (Ci-C4)Alkyl-(C3- C6)cycloalkyl, (Ci-C )Alkoxy, (Ci-C )Halogenalkoxy, (Ci-C )Alkoxyimino, (Ci-C )Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C )Alkylsulfonyl, (Ci-C )Halogenalkylsulfonyl, (Ci-C )Alkylsulfonyloxy, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl oder Di-(Ci-C4)alkylaminosulfonyl stehen, n für 0, 1 oder 2 steht. R 5, R 6 are each independently hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl ( C 3 - C6) cycloalkyl, (Ci-C) alkoxy, (Ci-C) haloalkoxy, (Ci-C) alkoxyimino, (C-C) alkylthio, (Ci-C4) haloalkylthio, (Ci-C4) alkylsulphinyl , (Ci-C 4 ) haloalkylsulfinyl, (Ci-C) alkylsulfonyl, (Ci-C) haloalkylsulfonyl, (Ci-C) alkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci -C 4) alkylaminocarbonyl, di (Ci-C 4) alkyl-aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C4) alkylamino, di (Ci- C4) alkylamino, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl or di- (C 1 -C 4 ) -alkylaminosulfonyl, n is 0, 1 or 2.
7. Verbindungen der Formel (I) gemäß Anspruch 1 mit der Struktureinheit Al l 7. Compounds of formula (I) according to claim 1 with the structural unit Al l
Figure imgf000117_0001
in welcher
Figure imgf000117_0001
in which
Q für Q3 steht und für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl oder (C3-C6)Cycloalkyl steht, Q stands for Q3 and is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl or (C 3 -C 6) cycloalkyl,
R2, R3 unabhängig voneinander für Wasserstoff, Cyano, Halogen, Nitro, Hydroxy, (C3- C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci- C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-R 2, R 3 are each independently hydrogen, cyano, halogen, nitro, hydroxy, (C3- C6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy , (CI-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (Ci-
C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, Aminosulfonyl, (Ci-C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl oder NHCO-(Ci-C4)alkyl ((Ci-C4)Alkylcarbonylamino) stehen, C 4 ) alkylsulfonyl, (Ci-C 4 ) haloalkylsulfonyl, aminosulfonyl, (Ci-C 4 ) alkylaminosulfonyl, di- (Ci-C 4 ) alkyl-aminosulfonyl or NHCO- (Ci-C 4 ) alkyl ((Ci-C 4 ) Alkylcarbonylamino),
R4 für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R 4 is (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
R5 für Halogen, (Ci-C4)Halogenalkyl, (Ci-C4)Halogenalkoxy oder (Ci-C4)Halogenalkylthio steht, R 5 is halogen, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or (C 1 -C 4 ) haloalkylthio,
R6 für Wasserstoff steht, n für 0, 1 oder 2 steht. R 6 is hydrogen, n is 0, 1 or 2.
8. Verbindungen der Formel (I) gemäß Anspruch 1 mit der Struktureinheit Al l 8. Compounds of formula (I) according to claim 1 with the structural unit Al l
Figure imgf000118_0001
in welcher
Figure imgf000118_0001
in which
Q für Q3 steht und R1 für Ethyl steht, Q is Q3 and R 1 is ethyl,
R2, R3 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Trifluormethylthio stehen, R4 für Methyl, Ethyl, i-Propyl, Methoxymethyl oder Methoxyethyl steht, R 2 , R 3 independently of one another are hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, R 4 is methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl,
R5 für Fluor, Chlor, Brom, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl (CH2CFH2, CHFCH3), Difluorethyl (CF2CH3, CH2CHF2, CHFCFH2), Trifluorethyl, (CH2CF3, CHFCHF2, CF2CFH2), Tetrafluorethyl (CHFCF3, CF2CHF2), Pentafluorethyl, Trifluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy oder Trifluormethylthio steht, R 5 is fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CF 2 , CHFCH 3), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CF 2 ), Tetrafluoroethyl (CHFCF 3, CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
R6 für Wasserstoff steht, WO 2017/125340 _n 8_ PCT/EP2017/050773 n für 0, 1 oder 2 steht. R 6 is hydrogen, WO _ n _ PCT / EP2017 / 050773 n is 0, 1 or 2 2017/125340. 8
Verbindungen der Formel (I) gemäß Anspruch 1 mit der Struktureinheit Al l  Compounds of the formula (I) according to Claim 1 having the structural unit Al 1
Figure imgf000119_0001
Figure imgf000119_0001
in welcher  in which
Q für Q3 steht und  Q stands for Q3 and
R1 für Ethyl steht, R 1 is ethyl,
R2 für Wasserstoff steht, R 2 is hydrogen,
R3 für Wasserstoff oder Trifluormethyl steht, R 3 is hydrogen or trifluoromethyl,
R4 für Methyl steht, R 4 is methyl,
R5 für Trifluormethyl steht, R 5 is trifluoromethyl,
R6 für Wasserstoff steht, R 6 is hydrogen,
n für 0 oder 2 steht.  n stands for 0 or 2.
0. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher  0. Compounds of formula (I) according to claim 1, in which
Aa für Stickstoff steht,  Aa is nitrogen,
Ab für -C(R9)(R10)- steht, Ab for -C (R 9 ) (R 10 ) - stands,
Ac für -C(RU)(R12)- steht, Ac represents -C (R U ) (R 12 ) -,
Ad für -C(R13)(R14)- steht, Ad is -C (R 13 ) (R 14 ) -,
wobei sich folgende Struktureinheit ergibt: AI ,  where the following structural unit results: AI,
und Q, R1, R9, R10, R11, R12, R13, R14 und n die in Anspruch 1 angegebenen Bedeutungen haben.and Q, R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in claim 1.
1. Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher 1. Compounds of formula (I) according to claim 1, in which
Aa für Stickstoff steht, Ab für -C(R9)(R10)- steht, Aa is nitrogen, Ab for -C (R 9 ) (R 10 ) - stands,
Ac für -C(RU)(R12)- steht, Ac represents -C (R U ) (R 12 ) -,
Ad für -C(R13)(R14)- steht, wobei sich folgende Struktureinheit ergibt: AI, und Q, R1, R4, R5, R6, R9, R10, R11, R12, R13, R14 und n die in Anspruch 2 angegebenenAd for -C (R 13 ) (R 14 ) -, the following structural unit being obtained: Al, and Q, R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n specified in claim 2
Bedeutungen haben. Have meanings.
12. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher Aa für Stickstoff steht, 12. Compounds of formula (I) according to claim 1, in which Aa is nitrogen,
Ab für -C(R9)(R10)- steht, Ac für -C(RU)(R12)- steht, Ab stands for -C (R 9 ) (R 10 ) -, Ac stands for -C (R U ) (R 12 ) -,
Ad für -C(R13)(R14)- steht, wobei sich folgende Struktureinheit ergibt: AI, Ad for -C (R 13 ) (R 14 ) -, where the following structural unit results:
R1 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl oder (C3-C6)Cycloalkyl steht, R 1 is (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 3 -C 6 ) cycloalkyl,
R9, R10, R11, R12, R13, R14 unabhängig voneinander für Wasserstoff, (Ci-C4)Alkyl oder (Ci-C4)Halogenalkyl stehen, R 9, R 10, R 11, R 12, R 13, R 14 are independently hydrogen, (Ci-C 4) alkyl or (Ci-C4) haloalkyl,
Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17 steht, Q represents a heteroaromatic 9-membered fused bicyclic ring system of the series Q1, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17,
R4 für (Ci-C4)Alkyl oder (Ci-C4)Alkoxy-(Ci-C4)alkyl steht, R 4 is (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
R5 für Halogen, (Ci-C4)Halogenalkyl, (Ci-C4)Halogenalkoxy oder (Ci-C4)Halogenalkylthio steht, R 5 is halogen, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or (C 1 -C 4 ) haloalkylthio,
R6 für Wasserstoff steht, n für 0, 1 oder 2 steht. R 6 is hydrogen, n is 0, 1 or 2.
13. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher Aa für Stickstoff, Ab für -C(R9)(R10)-, Ac für -C(Ru)(R12)- 13. Compounds of formula (I) according to claim 1, in which Aa is nitrogen, Ab is -C (R 9 ) (R 10 ) -, Ac for -C (R u ) (R 12 ) -
Ad für -C(R13)(R14)- wobei sich folgende Struktureinheit ergibt: AI, Ad for -C (R 13 ) (R 14 ) - giving the following structural unit: Al,
R1 für Ethyl steht, R 1 is ethyl,
R9, R10, R11, R12, R13, R14 unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another represent hydrogen, methyl or ethyl,
Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q2 oder Q3 steht, Q represents a heteroaromatic 9-membered fused bicyclic ring system from the series Q2 or Q3,
R4 für Methyl, Ethyl, i-Propyl, Methoxymethyl oder Methoxyethyl steht, R 4 is methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
R5 für Fluor, Chlor, Brom, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl (CH2CFH2, CHFCH3), Difluorethyl (CF2CH3, CH2CHF2, CHFCFH2), Trifluorethyl, (CH2CF3, CHFCHF2, CF2CFH2), Tetrafluorethyl (CHFCF3, CF2CHF2), Pentafluorethyl, Trifluormethoxy, Difluorchlormethoxy, Dichlorfluormethoxy oder Trifluormethylthio steht, R 5 is fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CF 2 , CHFCH 3), difluoroethyl (CF 2 CH 3, CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3, CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3, CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
R6 für Wasserstoff steht, n für 0, 1 oder 2 steht. R 6 is hydrogen, n is 0, 1 or 2.
Verbindungen der Formel (I) gemäß Anspruch 1 , in welcher Compounds of formula (I) according to claim 1, in which
Aa für Stickstoff steht, Aa is nitrogen,
Ab für -C(R9)(R10)- steht, Ab for -C (R 9 ) (R 10 ) - stands,
Ac für -C(RU)(R12)- steht, Ac represents -C (R U ) (R 12 ) -,
Ad für -C(R13)(R14)- steht, wobei sich folgende Struktureinheit ergibt: AI, Ad for -C (R 13 ) (R 14 ) -, where the following structural unit results:
R1 für Ethyl steht, R 1 is ethyl,
R9, R10, R11, R12, R13, R14 für Wasserstoff stehen, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are hydrogen,
Q für ein heteroaromatisches 9-gliedriges annelliertes bicyclisches Ringsystem aus der Reihe Q3 steht, Q is a 9-membered heteroaromatic fused bicyclic ring system from the Q3 series,
R4 für Methyl steht, R5 für Trifluormethyl steht, R6 für Wasserstoff steht, n für 2 steht. R 4 is methyl, R 5 is trifluoromethyl, R 6 is hydrogen, n is 2.
15. Verbindungen der Formel (I) gemäß Anspruch 1 mit der Struktureinheit AI 15. Compounds of formula (I) according to claim 1 with the structural unit AI
Figure imgf000122_0001
in welcher Q für Q3 steht und R1, R4, R5, R6, R9, R10, R11, R12, R13, R14 und n die oben angegebenen Bedeutungen haben.
Figure imgf000122_0001
in which Q is Q 3 and R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given above.
16. Verbindungen der Formel (I) gemäß Anspruch 1 mit den folgenden Strukturen 16. Compounds of formula (I) according to claim 1 having the following structures
Figure imgf000122_0002
Figure imgf000122_0002
17. Agrochemische Formulierung enthaltend Verbindungen der Formel (I) oder der Formel (Γ) gemäß Anspruch 1 , sowie Streckmittel und/oder oberflächenaktive Substanzen. 17. An agrochemical formulation containing compounds of the formula (I) or of the formula (II) according to claim 1, and extenders and / or surface-active substances.
18. Agrochemische Formulierung gemäß Anspruch 17 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. Verfahren zur Bekämpfung von tierischen Schädlingen dadurch gekennzeichnet, dass man eine Verbindung der Formel (I) oder der Formel (Γ) gemäß Anspruch 1 oder eine agrochemische Formulierung gemäß einem der Ansprüche 17 oder 18 auf die tierischen Schädlinge und/oder ihren Lebensraum einwirken lässt. 18. Agrochemical formulation according to claim 17 additionally containing a further agrochemical active ingredient. Method for controlling animal pests, characterized in that a compound of the formula (I) or of the formula (II) according to claim 1 or an agrochemical formulation according to one of claims 17 or 18 is allowed to act on the animal pests and / or their habitat.
Verwendung von Verbindungen der Formel (I) oder der Formel (Γ) gemäß Anspruch 1 oder von agrochemischen Formulierungen gemäß einem der Ansprüche 17 oder 18 zur Bekämpfung von tierischen Schädlingen. Use of compounds of the formula (I) or of the formula (II) according to claim 1 or of agrochemical formulations according to one of claims 17 or 18 for controlling animal pests.
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