EP4175961A1 - Heterocyclene derivatives as pest control agents - Google Patents

Heterocyclene derivatives as pest control agents

Info

Publication number
EP4175961A1
EP4175961A1 EP21737052.7A EP21737052A EP4175961A1 EP 4175961 A1 EP4175961 A1 EP 4175961A1 EP 21737052 A EP21737052 A EP 21737052A EP 4175961 A1 EP4175961 A1 EP 4175961A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
spp
cycloalkyl
amino
cyano
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21737052.7A
Other languages
German (de)
French (fr)
Inventor
Rüdiger Fischer
Steffen Müller
Yeshua SEMPERE MOLINA
Yolanda Cancho Grande
Matthieu WILLOT
Elke Hellwege
Marc LINKA
Peter Lösel
Olga Malsam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP4175961A1 publication Critical patent/EP4175961A1/en
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P17/00—Pest repellants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Definitions

  • the present invention relates to heterocycle derivatives of the formula (I), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular insects and arachnids, and processes and intermediates for their preparation.
  • heterocycle derivatives have now been found which have advantages over the already known compounds, e.g. better biological or ecological properties, broader application methods, better insecticidal, acaricidal action, and good compatibility with useful plants.
  • the heterocycle derivatives can be used in combination with other agents to improve the effectiveness, in particular against insects which are difficult to control.
  • the present invention therefore relates to new compounds of the formula (I) in which
  • R 2 for hydrogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) hydroxyalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (Ci- C6) haloalkoxy (Ci-C6) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -
  • C6 haloalkinyloxy (Ci-C6) alkyl, (C 2 -C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 3 -
  • C6 haloalkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl, (Ci-
  • C6 haloalkylcarbonyl- (Ci-C6) alkyl, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl or (Ci- C6) haloalkoxycarbonyl- (Ci-C6) alkyl,
  • R 3 is hydrogen, halogen, cyano, nitro, (Ci-C6) alkyl, (C 3 -Cs) cycloalkyl, cyano (C 3 - C 8) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, ( Ci-C6) haloalkoxy, (Ci-C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (Ci- C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, (Ci- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl, (C
  • Aminocarbonyl (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-
  • Cycloalkylthiocarbonylamino (C 3 -C 8) Cycloalkylthiocarbonylamino, (C 3 -C 8) Cycloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C 2 - C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl , (C 3 -Cs) cycloalkyl (C 2) alkenyl, (C 2 - C 6) alkynyl or (C 2 -C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl (C 2) alkynyl, (C 3 -Cs) cycloalkyl- (Ci- C 6 ) alkyl, (Ci-C 6 ) alkylaminocarbonylamino, di- (Ci-C 6 ) alkylaminocarbonylamin
  • C 6 haloalkylaminocarbonyl, (C 2 -C 6 ) alkenylaminocarbonyl, di- (C 2 -Ce) - alkenylaminocarbonyl, (C CslCycloal kyl aminocarbonyl, (C 1 -CA,) A 1 ky 1 sulfony 1 am i no, (Ci - C 6 ) alkylamino, di- (Ci-C 6 ) alkylamino, (C 1 -C,) haloalkylamino, (C 3 -Cs) cycloalkylamino, aminosulfonyl, (C 1 -C 5) A 1 ky 1 aminesu 1 fny 1, di- (Ci-C 6 ) alkylaminosulfonyl, (Ci-
  • R 4 , R 5 , R 6 , R 7 independently of one another represent hydrogen, cyano, halogen, (Ci-C3) alkyl or (Ci- C3) haloalkyl,
  • Z is -NR 8 , oxygen or sulfur
  • R 8 for hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) hydroxyalkyl, (Ci-C 6 ) alkoxy (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkoxy- (Ci-C 6 ) alkyl, (C2-C6) alkenyl, (C2- C 6 ) alkenyloxy- (Ci-C 6 ) alkyl, (C2-C6) haloalkenyloxy- ( Ci-C6) alkyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) haloalkynyl or (C3-Cs) cycloalkyl, m is 0 or 1, n stands for 0 or 1.
  • the compounds of the formula (I) are very effective as pesticides, preferably as insecticides and / or acaricides, and are generally very well tolerated by plants, in particular with respect to crop plants.
  • R 1 preferably represents (Ci-C- alkyl, (Ci-C4) cyanoalkyl, (Ci-C4) alkoxy- (Ci-C4) alkyl, (Ci- C4) haloalkyl, (C2-C4) alkenyl, (C2- C4) haloalkenyl, (C2-C4) alkynyl, (C2- C4) haloalkynyl or (C3-C6) cycloalkyl,
  • R 2 preferably represents hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) cyanoalkyl, (Ci- C4) hydroxyalkyl, (Ci-C4) alkoxy- (Ci-C4) alkyl, ( Ci-C4) haloalkoxy- (Ci-C4) alkyl, (C 3 - C 6 ) cycloalkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (Ci-C4) alkyl- (C3-C6) cycloalkyl, Halogen (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkylthio (Ci-C 4 ) alkyl, (Ci- C 4 ) haloalkylthio (Ci-C 4 ) alkyl, (C
  • R 3 preferably represents hydrogen, halogen, cyano, nitro, (Ci-C6) alkyl, (C 3 -Cs) cycloalkyl, cyano (C 3 -Cs) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy , (Ci-C6) haloalkoxy, (Ci-C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (Ci-C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, (Ci- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbony
  • Aminocarbonyl (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-
  • C ö jCyanohalogenalkyl (C 1 -O,) Hydroxyal kyl, Hydroxycarbonyl- (Ci-C6) -alkoxy, (Ci- C6) alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C6) Alkoxy- (Ci-C6 ) alkyl, (C 2 -Ce) alkenyl, (C 2 - C ö jhaloalkenyl, (C 2 -Ce) cyanoalkenyl, (C 3 -Cs) cycloalkyl- (C 2 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 - C6) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (Ci-C6) alkoxy, (Ci-C6) haloalkoxy, (Ci-O-
  • C6 cyanoalkoxy, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkoxy, (Ci-C6) alkoxy- (Ci-C6) alkoxy, (Ci- C6) alkoxyimino, (Ci-C6) haloalkoxyimino, (Ci-C6 ) alkylthio, (Ci-C6) haloalkylthio, (Ci- C6) alkoxy (Ci-C 6) alkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfmyl, (Ci-C6)
  • C 6 haloalkylsulfinyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkylsulfinyl, (Ci-C 6 ) alkylsulfinyl- (Ci- C6) alkyl, (Ci-C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, (Ci-C6) alkoxy- (Ci-C6) alkylsulfonyl, (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) alkylsulfonyloxy, (Ci-C6) haloalkylsulfonyloxy, (Ci-C6) alkylcarbonyl, ( Ci-C6) haloalkylcarbonyl, (Ci-C6) alkoxy- (Ci-C 6 ) alkylsulfinyl, (
  • C6 haloalkylaminocarbonyl, (C 2 -C 6 ) alkenylaminocarbonyl, di- (C 2 -Ce) - alkenylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, (Ci-C6) alkylsulfonylamino, (Ci- C6) alkylamino, di- ( Ci-C6) alkylamino, (Ci-C6) haloalkylamino, (C 3 -Cs) cycloalkylamino, aminosulfonyl, (Ci-C6) alkylaminosulfonyl, di- (Ci-C6) alkylaminosulfonyl, (Ci-C6) alkylsulfoximino, aminothiocarbonyl, (Ci -C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl
  • R 4 , R 5 , R 6 , R 7 are preferably, independently of one another, hydrogen, cyano, halogen, (Ci- C 3 ) alkyl or (Ci-C 3 ) haloalkyl,
  • Z preferably represents -NR 8 , oxygen or sulfur, where
  • R 8 is preferably hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci- C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy (Ci-C alkyl 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) -haloalkynyl or ( C 3 -C 6) cycloalkyl, m is preferably
  • R 1 particularly preferably represents (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -
  • R 2 particularly preferably represents hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -
  • R 3 particularly preferably represents hydrogen, halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4) alkoxy, (Ci-C 4) haloalkoxy, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci C 4) Halogenalkylaminocarbonyl, (C 3 -C 6) Cycloalkylaminocarbonyl, amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, di- (Ci-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci- C 4 )
  • C 2 haloalkylcarbonyl (Ci-C 2) alkyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, (C 3 - C 6) cycloalkylcarbonyl (Ci-C 2) alkyl amino, (Ci-C4) alkylthiocarbonylamino , (Ci-C2)
  • R 4 , R 5 , R 6 , R 7 are particularly preferably identical and are either hydrogen or fluorine,
  • Z particularly preferably represents —NR 8 or oxygen, where
  • R 8 particularly preferably represents hydrogen or (Ci-C 4 ) alkyl, m particularly preferably represents 0 or 1, n particularly preferably represents 0 or 1.
  • R 1 particularly preferably represents (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -
  • R 2 particularly preferably represents hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -
  • R 3 particularly preferably represents hydrogen, halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4) alkoxy, (Ci-C 4) haloalkoxy, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci C 4) Halogenalkylaminocarbonyl, (C 3 -C 6) Cycloalkylaminocarbonyl, amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, di- (Ci-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci- C 4 )
  • Cyanohalogenalkyl (Ci-C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C alkyl 2), (C 2 -C 4) alkenyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 3 -C 6) cycloalkyl- (C alkenyl 2), (C 2 -C 4) alkynyl, (C 2 - C 4) haloalkynyl, (C 2 -C 4) cyanoalkynyl, (C -C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci-
  • C 4 haloalkoxyimino, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylthio- (Ci- C 2 ) alkyl, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) Haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-
  • Cycloalkylaminothiocarbonyl (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl, (Ci- C 4 ) alkylaminosulfonyl, di- (Ci-C 4 ) alkyl-aminosulfonyl, (Ci-C 4 ) alkylcarbonylamino, (Ci-
  • C 2 haloalkylcarbonyl (Ci-C 2) alkyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, (C 3 - C 6) cycloalkylcarbonyl (Ci-C 2) alkyl amino, (Ci-C4) alkylthiocarbonylamino , (Ci-C2)
  • Z particularly preferably represents —NR 8 or oxygen, where
  • R 8 particularly preferably represents hydrogen or (Ci-C 4 ) alkyl, m particularly preferably represents 0 or 1, n particularly preferably represents 0 or 1.
  • R 1 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or Pentafluoroethyl,
  • R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, Difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
  • R 3 very particularly preferably represents hydrogen, halogen, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or very particularly preferably for each optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the Molecule bridged - phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or imidazolyl, whereby the following are possible as substituents: cyano, fluorine, chlorine, bromine,
  • R 4 , R 5 , R 6 , R 7 are very particularly preferably identical and are either hydrogen or fluorine,
  • Z very particularly preferably represents —NR 8 or oxygen, where
  • R 8 very particularly preferably represents hydrogen or methyl, m very particularly preferably represents 0 or 1, n very particularly preferably represents 0 or 1.
  • R 1 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
  • R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, Difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
  • R 3 very particularly preferably represents hydrogen, halogen, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or very particularly preferably for each optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the Molecular bridges - phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or imidazolyl, whereby the following are possible as substituents: cyano, fluorine, chlorine, bromine, nitro,
  • Z very particularly preferably represents —NR 8 or oxygen, where
  • R 8 very particularly preferably represents hydrogen or methyl, m very particularly preferably represents 0 or 1, and n very particularly preferably represents 0 or 1.
  • R 1 is highlighted for ethyl
  • R 2 is highlighted for methyl
  • R 3 is emphasized for bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl or for phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or each optionally substituted one or more times, identically or differently - bridged via a carbon atom to the remainder of the molecule Imidazolyl, where the possible substituents are: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SFs, 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1- Fluorine-1-cyclopropyl or 1-trifluoromethyl-1-cyclopropyl, or for optionally
  • R 4 , R 5 , R 6 , R 7 are highlighted for fluorine
  • R 8 is highlighted hydrogen or methyl, m is highlighted 0 or 1, n is highlighted 0 or 1.
  • R 1 is highlighted for ethyl
  • R 2 is highlighted for methyl
  • R 3 is emphasized for hydrogen, bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl or for phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl which is optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the molecule, Oxazolyl or imidazolyl, with possible substituents in each case: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SFs, 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1- fluoro-1 -cyclopropyl, 1-trifluoromethyl- 1 -cyclo
  • R 4 , R 5 , R 6 , R 7 are highlighted for fluorine
  • R 8 is highlighted hydrogen or methyl, m is highlighted 0 or 1, n is highlighted 0 or 1.
  • R 1 stands in particular for ethyl
  • R 2 especially stands for methyl
  • R 3 stands in particular for bromine, cyclopropyl, or for phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl, or for optionally monosubstituted - via a carbon atom to the rest of the molecule bridged - pyridyl, with possible substituents in each case: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl, or for each optionally monosubstituted - thiophenyl or thiazolyl which is bridged via a carbon atom to the remainder of the molecule, where Possible substituents in each case are: chlorine or 1-cyano-1-cyclopropyl, or for optionally monosubstituted -triazolyl bridged via a nitrogen atom to the remainder of the molecule
  • R 4 , R 5 , R 6 , R 7 in particular represent fluorine
  • Y especially stands for oxygen
  • Z in particular stands for NR 8 , where
  • R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1.
  • R 1 stands in particular for ethyl
  • R 2 especially stands for methyl
  • R 3 stands in particular for bromine, cyclopropyl, or for phenyl which is optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl,
  • R 4 , R 5 , R 6 , R 7 in particular represent fluorine
  • Y especially stands for oxygen
  • Z in particular stands for NR 8 , where
  • R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1.
  • R 1 stands in particular for ethyl
  • R 2 especially stands for methyl
  • R 3 stands in particular for hydrogen, bromine, cyclopropyl, or for optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl Phenyl, or for phenyl which is optionally twice, identically or differently substituted by fluorine, chlorine, bromine, cyano, or for optionally monosubstituted - pyridyl which is bridged via a carbon atom to the remainder of the molecule, where possible substituents are in each case: cyano, chlorine, bromine , Cyclopropyl, 1-cyano-1-cyclopropyl or pyridyl which is monosubstituted by chlorine or bromine (where pyridyl is bridged via a carbon atom to the remainder of the molecule), or for each optionally monosubstituted - bridged via a carbon
  • R 4 , R 5 , R 6 , R 7 in particular represent fluorine
  • Z stands for NR 8 , where
  • R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1.
  • the invention relates to compounds of the formula (I), where R 4 , R 5 , R 6 , R 7 are fluorine and R 1 , R 2 , R 3 , R 8 , Y, Z, n and m are the in design (1-1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4- 2) or design (5-1) or Design (5-2) or design (6-la) or design (6- lb) or design (6-2) have given meanings.
  • the invention relates to compounds of the formula (I), where R 1 is ethyl, R 2 is methyl, R 4 , R 5 , R 6 , R 7 are fluorine, Z is N-methyl and R is 3 , Y, n and m those in configuration (1-1) or configuration (2-1) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or embodiment (5-1) or embodiment (5-2) or embodiment (6-la) or embodiment (6-lb) or embodiment (6-2) have given meanings.
  • halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
  • aryl also as part of a larger unit, such as arylalkyl is selected from the series phenyl, naphthyl, anthryl, phenanthrenyl and, in turn, is preferably phenyl.
  • alkyl either alone or in combination with other terms, such as haloalkyl, in the context of the present invention is understood to mean a residue of a saturated, aliphatic hydrocarbon group with 1 to 12 carbon atoms, which can be branched or unbranched.
  • C1-C12-alkyl radicals are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, 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.
  • alkyl radicals C 1 -CY alkyl radicals are particularly preferred.
  • Ci-C4-alkyl radicals are particularly preferred.
  • alkenyl is a linear or branched C2-Ci2-alkenyl radical which has at least one double bond, for example vinyl, allyl, 1 -Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2 -Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, understood.
  • C2-C6-alkenyl radicals are preferred and C2-C4-alkenyl radicals are particularly preferred.
  • alkynyl is a linear or branched C2-Ci2-alkynyl radical which has at least one triple bond, for example Ethynyl, 1-propynyl and propargyl.
  • CVCV-alkynyl radicals are preferred and C3-C4-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, is understood according to the invention to be a C3-C8 cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl . Of these, C3-C6-cycloalkyl radicals are preferred.
  • alkoxy either on its own or in combination with other terms such as haloalkoxy, is understood in the present case to be an O-alkyl radical, the term “alkyl” having the meaning given above.
  • Halogen here represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • optionally substituted radicals can be mono- or polysubstituted, and in the case of polysubstitutions the substituents can be identical or different.
  • radical definitions or explanations given above apply to the end products and to the starting products and intermediates accordingly. These radical definitions can be combined with one another as required, i.e. also between the respective preferred areas.
  • compounds of the formula (I) in which there is a combination of the meanings specifically listed above.
  • the compounds of the formula (I) can, depending on the nature of the substituents, be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus includes both pure stereoisomers and any mixtures of these isomers.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above.
  • X 1 and X 2 represent halogen.
  • R 9 stands for linear or branched (Ci-C4) alkyl or benzyl.
  • Compounds of the formula (III) can be prepared from imidazole derivatives of the formula (II), for example by reaction with a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran or by reacting compounds of the formula (II) with NBS in Combination with azobis (isobutyronitrile) (AIBN) in carbon tetrachloride or chloroform, for example analogous to the method described in WO 2013/149997, WO 2014/115077 or WO 2011/123609.
  • a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran
  • AIBN azobis (isobutyronitrile)
  • Imidazole derivatives of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to the processes described in WO 2014/191894, US 2003/229079 or WO 2013/156608. Step b)
  • compounds of the formula (III) in which X 1 preferably represents chlorine or bromine can be mixed with suitable boronic acids [R 3 -B (OH) 2] or boronic esters by known methods (cf. WO 2012/143599, US 2014/094474 , US 2014/243316, US 2015/284358 or Journal of Organic Chemistry 2004, 69, 8829-8835) in the presence of suitable catalysts from the series of transition metal salts to give compounds of the formula (IV).
  • Suitable coupling catalysts are, for example, preferably palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II), bis (triphenylphosphine) palladium (II) dichloride or tetrakis (triphenylphosphine) palladium.
  • Suitable basic reaction auxiliaries for carrying out the process are preferably carbonates of sodium, potassium or cesium.
  • Some of the boronic acid derivatives [R 3 -B (OH) 2] or boronic acid ester derivatives required are known and / or commercially available or can be prepared by generally known methods (cf.
  • the reaction is preferably carried out in a mixture of water and an organic solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Frequently, ethers such as tetrahydrofuran, dioxane or 1,2-dimethoxyethane are used.
  • R'-Sn (n-Bu);] can be used as the coupling partner (cf. US 2013/281433, WO 2004/099177 or WO 2016/071214).
  • R'-Sn (n-Bu);] are partly known and / or commercially available or can be prepared by generally known methods (cf. WO 2016/071214 or WO 2007/148093).
  • a coupling of the halogenated imidazole derivatives of the formula (III) with NH-containing heteroaromatics, such as. B. imidazoles or pyrazoles, optionally substituted as described above, to compounds of the formula (IV) can be carried out by reaction in the basic (for example with sodium hydride in dimethylformamide, cf., for example, WO 2005/058898).
  • the reaction can be salted under an inert gas atmosphere by catalysis with copper (I), for example copper (I) iodide, in the presence of a suitable ligand, e.g. B.
  • Imidazole derivatives of the formula (V), in which X 2 preferably represents halogen from the series for bromine or iodine can be prepared using standard methods from compounds of the formula (IV) by reaction with, for example, bromine or V-bromosuccinimide (NBS), (cf. WO 2009/115572 or WO 2010/091411) or / V-iodosuccinimide (NIS), optionally in the presence of acetic acid or trifluoroacetic acid (cf. WO 2008/063287, WO 2007/087548 or WO 2009/152025).
  • NBS bromine or V-bromosuccinimide
  • NIS V-iodosuccinimide
  • compounds of the formula (V) in which X 2 is preferably halogen from the series bromine or iodine can be reacted with mercaptan derivatives (R'-SH) in the presence of palladium catalysts such as, for example, tris (dibenzylideneacetone) dipalladium [Pd (dba )] to be carried out.
  • palladium catalysts such as, for example, tris (dibenzylideneacetone) dipalladium [Pd (dba )] to be carried out.
  • Amine bases such as triethylamine or /V./V- diisopropylethylamine (DIPEA) and phosphine ligands such as Xantphos are often used (cf.
  • the reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Ethers such as, for example, dioxane or 1,2-dimethoxyethane are preferred.
  • Mercaptan derivatives such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be produced by known methods, for example analogously to those in US 2006/025633, US 2006/111591, US2820062, Chemical Communications 2000, 13, 1163-1164 or Journal of the American Chemical Society 1922, 44, 1323-1333.
  • Esters of the formula (VI) can be converted into carboxylic acids of the formula (VII) using standard methods (cf., for example, WO 2014/191894, US 2006/194779, WO 2014/086663 or European Journal of Organic Chemistry 2009, 213-222) , for example with an alkali hydroxide as the base such as sodium hydroxide or lithium hydroxide in an alcohol such as methanol or ethanol or an ether such as THF as the solvent, preferably in the presence of water.
  • an alkali hydroxide as the base
  • an alcohol such as methanol or ethanol or an ether such as THF as the solvent
  • ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol, ethanol or iso-propanol; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as / V, / V- D i m c t h y 1 f
  • 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 azodiester such as diethylazodicarboxylic acid.
  • 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
  • the reaction can be carried out in the presence of a suitable catalyst such as 1-flyroxybenzotriazole.
  • the reaction can be carried out in the presence of an acid or a base.
  • Examples of an acid which can be used in the reaction described are sulfonic acids such as methanesulfonic acid or para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing fleterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and /V./V-diisopiopylcthylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • nitrogen-containing fleterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and /V./V-diisopiopylcthylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • the oxidation is generally carried out in a solvent.
  • Halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and mefa-chloroperbenzoic acid.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above.
  • X 1 stands for halogen.
  • R 9 stands for linear or branched (Ci-C4) alkyl or benzyl.
  • Compounds of the formula (III) can be prepared from imidazole derivatives of the formula (II), for example by reaction with a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran or by reacting compounds of the formula (II) with NBS in Combination with azobis (isobutyronitrile) (AIBN) in carbon tetrachloride or chloroform, for example analogous to the method described in WO 2013/149997, WO 2014/115077 or WO 2011/123609.
  • a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran
  • AIBN azobis (isobutyronitrile)
  • Imidazole derivatives of the formula (II) are either commercially available or can be prepared according to known ones Methods are produced, for example analogous to the methods described in WO 2014/191894, US 2003/229079 or WO 2013/156608.
  • Imidazole derivatives of the formula (IX) can be prepared using standard methods from compounds of the formula (III) by reaction with a disulfide (R'-SSR 1 ) and, for example, a strong base, preferably lithium diisopropylamide (LDA) in tetrahydrofuran (cf. Bioorganic and Medicinal Chemistry Leiters 2010, 20, 1084-1089) or e.g. hydrogen peroxide and iodine in ethanol (see Synthesis 2015, 47, 659-671).
  • a disulfide R'-SSR 1
  • LDA lithium diisopropylamide
  • Solvents such as methanol, acetonitrile or Touol are suitable.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Y have the meanings described above.
  • suitable alkylating agents are alkyl halides, preferably alkyl bromides or alkyl iodides, and also alkyl sulfonates such as, for example, alkyl methanesulfonates, alkyl tosylates or alkyl trifluoromethanesulfonates.
  • Suitable filler bases are carbonates of sodium, potassium or cesium, sterically hindered and non-nucleophilic amine phases such as /V./V- diisopiopylethylamine or flydride bases such as sodium hydride.
  • Suitable solvents are inert under the reaction conditions chosen in each case.
  • ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether are suitable; 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 or aprotic polar solvents such as acetone, / V, / V-D imcthy 1 frmamid or / V-methyl pyrrolidone.
  • the reaction is carried out using a carbonate base in acetone or / V, / V-D imcthy 1 formamide.
  • Compounds of the formula (XII) can be prepared from dianilines of the formula (XI), for example by reaction with formic acid, formic acid esters or orthoformates. In the presence or absence of a solvent which is inert under the prevailing reaction conditions. If necessary, the reaction can be catalyzed by the addition of Brpnsted or Lewis acids.
  • the compounds of the formula (XI) are either commercially available or can be prepared by known methods, for example analogously to the processes described in Chemistry - A European Journal 2017, 23, 13607-13611 or EP0234449 A2.
  • compounds of formula (XIII) are first treated with a strong base such as tetramethylpiperidinylzinc chloride lithium chloride complex and then reacted with compounds of formula (XIV) in the presence of palladium catalysts such as tetrakis (triphenylphosphine) palladium (0).
  • the reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Ethers such as, for example, dioxane or TF1F are preferred.
  • the compounds of the formula (XIV) can be prepared by known methods, for example analogously to the processes described in WO2020074558 A1.
  • the invention also relates to methods of combating animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to combating animal pests in agriculture and forestry and in material protection. Methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body are also preferably excluded.
  • the invention also relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
  • pesticides always also includes the term pesticides.
  • the compounds of the formula (I) are suitable for protecting plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the harvested crop and for combating animal pests, especially insects, if they are well tolerated by plants, have favorable warm-blooded toxicity and are environmentally friendly.
  • Arachnids, helminths, in particular nematodes, and mollusks that occur in agriculture, horticulture, animal breeding, aquaculture, forests, gardens and leisure facilities, in the protection of stored products and materials, and in the hygiene sector.
  • the term “hygiene” is to be understood to mean any and all measures, regulations and procedures whose aim is to prevent diseases, in particular infectious diseases, and which serve to improve the health of people and to protect animals and / or to protect the environment and / or to maintain cleanliness. According to the invention, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that they are free from hygiene pests and / or their excretions are.
  • surgical or therapeutic treatment regulations to be applied to the human body or the bodies of animals and diagnostic regulations which are carried out on the human body or the bodies of animals are preferably excluded from the scope of protection of the invention.
  • honeygiene sector thus covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels , Hospitals, stables, animal husbandry etc.
  • Hygiene pest should therefore be understood to mean one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons. It is therefore a primary objective to avoid or minimize the presence of hygiene pests and / or exposure to them in the hygiene sector. This can be achieved in particular by using a pesticide that can be used both to prevent an infestation and to cope with an already existing infestation. Preparations that prevent or reduce exposure to pests can also be used.
  • Hygiene pests include, for example, the organisms mentioned below.
  • the term "hygiene protection” thus covers all actions with which these hygiene measures, regulations and procedures are maintained and / or improved.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • the pests mentioned above include:
  • Pests from the strain of the Arthropoda in particular from the class of the Arachnida z. Acarus spp., E.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. B. Aculus fockeui, Aculus sinnendali, 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, z. B.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp.
  • Rhipicephalus spp. Rhipicephalus spp.
  • Stpotarsphalus spp. Scorpene spp. Steneotarsonemus spinki, Tarsonemus spp.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera, for. B.
  • Anoplophora glabripennis Anthonomus spp., E.g. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., E.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. E.g. B.
  • Curculio caryae Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocpopus.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicachnaispa.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia, argenteaes posta, Hajylota elegans, Hylamorpha elegans squamosus, Hypothenemus spp., e.g. B.
  • 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, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus ( Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., Z.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. B. Zabrus tenebrioides; from the order of the Dermaptera z.
  • Aedes spp. E.g. B.
  • Delia antiqua Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. 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., Hippobosca spp., Liriomyza spp., E.g. B.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., E.g. B.
  • Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. B.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa 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., E.g. B.
  • Nephotettix cincticeps Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B.
  • Pemphigus bursarius Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp.
  • E.g. B Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. B.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., E.g. B.
  • Trioza spp. E.g. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of the Heteroptera z.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. B.
  • Nezara spp. E.g. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. B.
  • Piezodorus guildinii Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera, for. E.g., Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., E.g. B.
  • Diprion similis, Hoplocampa spp. E.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. B.
  • Vespa crabro Wasmannia auropunctata, Xeris spp .; from the order of the Isopoda z.
  • B. Coptotermes spp. E.g. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B.
  • Reticulitermes flavipes Reticulitermes hesperus; from the order of the Lepidoptera, for.
  • Dioryctria skemani Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp. ,Eschoviella musculana, Etiella spp., Eudocima spp., Euba spp., Eupoecilia ambiguella, Euproctis spp., E.g. B.
  • Euproctis chrysorrhoea Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., E.g. B. Heliothis virescens, Hepialus spp., E.g. B.
  • Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., E.g. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., E.g. B.
  • Scirpophaga spp. E.g. B. Scirpophaga innotata, Ontario segetum, Sesamia spp., E.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. B.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of the Orthoptera or Saltatoria z.
  • B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., E.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. B. Locusta migratoria, Melanoplus spp., E.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera, for.
  • Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., E.g. B.
  • B. Scutigerella spp. E.g. B. Scutigerella immaculata;
  • Pests from the trunk of the Mollusca e.g. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., E.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. B.
  • Belonolaimus gracilis Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., E.g. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. B. Cacopaurus pestis, Criconemella spp., E.g. B.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. B. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., E.g. B. Xiphinema index.
  • the compounds of the formula (I) can 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 agents against viroids) or be used as a remedy against MLO (Mycoplasma-like organism) and RLO (Rickettsia-like organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations, in particular formulations for controlling undesired animal pests.
  • the formulation can be applied to the animal pest and / or in its habitat.
  • the formulation according to the invention can be provided to the end user as a ready-to-use “application form”, ie the formulations can be applied directly to the plants or seeds by means of a suitable device such as a spray or dust device.
  • the formulations can be provided to the end user in the form of concentrates to be diluted, preferably with water, before use.
  • formulation denotes such a concentrate
  • application form denotes a means ready-to-use solution for the end user, ie usually such a dilute formulation.
  • the formulation of the invention can be prepared in a conventional manner, for example by mixing the compound of the invention with one or more suitable excipients such as those disclosed herein.
  • the formulation comprises at least one compound according to the invention and at least one agriculturally useful adjuvant, e.g. carrier and / or surfactant (s).
  • at least one agriculturally useful adjuvant e.g. carrier and / or surfactant (s).
  • a carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert.
  • the carrier generally improves the application of the compounds, for example to plants, parts of plants or seeds.
  • suitable solid supports include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates and ammonium nitrates, ground natural rock such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel, and ground synthetic rock, such as finely divided silica, alumina and silicates.
  • suitable solid carriers for the production of granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice stone, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic materials such as paper, sawdust, coconut shells , Corn on the cob and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof.
  • suitable solvents include polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride ), Alcohols and polyols (which can also be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), esters (including fats and oils) and (poly) ethers, unsubstituted and substituted
  • the carrier can also be a liquefied gaseous extender, ie a liquid that can be used at normal temperature and under normal pressure is gaseous, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • a liquefied gaseous extender ie a liquid that can be used at normal temperature and under normal pressure is gaseous, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • Preferred solid supports are selected from clays, talc and silica.
  • Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly) ethers.
  • the amount of carrier is typically in the range of 1 to 99.99% by weight, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight and most preferably 20 to 99% by weight. -% of the formulation.
  • Liquid carriers are typically present in a range of 20 to 90% by weight, for example 30 to 80% by weight of the formulation.
  • Solid carriers are typically present in a range of 0 to 50%, preferably 5 to 45%, for example 10 to 30% by weight of the formulation.
  • the areas outlined relate to the total amount of carrier.
  • the surfactant can be an ionic (cationic or anionic), amphoteric or nonionic surfactant such as ionic or nonionic emulsifiers, foaming agents, dispersants, wetting agents, penetration promoters and any mixtures thereof.
  • surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated poly (alpha-substituted) acrylate derivatives, salts of fignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols , Fatty acids or fatty amines (for example polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates such as fatty acid esters, or phenolic acid esters of polyethoxylic acid esters), phosphoric acid esters of polyethoxylic esters
  • Preferred surfactants are from ethoxylated poly (alpha-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, Alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde,
  • Polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.
  • the amount of surfactant is typically in the range of 5 to 40% by weight, for example 10 to 20% by weight, of the formulation.
  • auxiliaries include water-repellent substances, drying agents, binders (adhesives, fixing agents, fixing agents such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic ones Phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan, modified clays, e.g. the products available under the name Bentone, and finely divided silicon dioxide), stabilizers (e.g.
  • cold stabilizers preservatives (e.g. dichlorophone, benzyl alcohol hemiformal, 1, 2- Benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV protection agents, and other agents that improve chemical and / or physical stability), dyes or pigments (such as on organic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), anti-foam agents (e.g.
  • silicone antifoam and magnesium tearate silicone antifoam and magnesium tearate
  • antifreeze glue
  • gibberellins and processing aids mineral and vegetable oils
  • fragrances waxes
  • nutrients including trace nutrients such as salts of iron, manganese , Boron, copper, cobalt, molybdenum and zinc
  • protective colloids including trace nutrients such as salts of iron, manganese , Boron, copper, cobalt, molybdenum and zinc
  • protective colloids including trace nutrients such as salts of iron, manganese , Boron, copper, cobalt, molybdenum and zinc
  • protective colloids thixotropic substances
  • penetrants sequestering agents and complexing agents.
  • excipients depends on the intended use of the compound according to the invention and / or on the physical properties of the compound (s). Furthermore, excipients can be selected so that they impart certain properties (technical, physical and / or biological properties) to the formulations or the application forms produced therefrom. The choice of excipients may make it possible to adapt the formulations to specific requirements.
  • the formulation comprises an insecticidally / acaricidally / nematicidically effective amount of the compound (s) according to the invention.
  • effective amount denotes an amount which is sufficient to control harmful insects / mites / nematodes on cultivated plants or for material protection and which does not significantly damage the treated plants. Such an amount can vary within a wide range and depends on various factors such as the insect / mite / nematode species to be controlled, the cultivated plant or material treated, the climatic conditions and the particular compound according to the invention used.
  • the formulation according to the invention usually contains 0.01 to 99% by weight, preferably 0.05 to 98% by weight, particularly preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, most preferably 1 to 80% by weight of the compound according to the invention. It is possible for a formulation to comprise two or more compounds according to the invention. In such a case, the areas outlined relate to the total amount of the compounds of the present invention.
  • the formulation according to the invention can be in any conventional formulation type, such as solutions (e.g. aqueous solutions), emulsions, water- and oil-based suspensions, powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, scattering granules), Suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers and also microencapsulations in polymeric substances.
  • the compound according to the invention can be in suspended, emulsified or dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g.
  • SF, FS dispersion concentrates
  • DC suspensions and suspension concentrates
  • emulsion concentrates e.g. EC
  • emulsions e.g. EW, EO, ES , ME, SE
  • capsules e.g. CS, ZC
  • pastes lozenges, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressed parts (e.g. BR, TB, DT), granulates (e.g. WG, SG , GR, FG, GG, MG), insecticidal articles (e.g.
  • the formulation according to the invention is preferably in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.
  • emulsions (EW, EO, ES)
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols
  • surfactant e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a suitable grinding device e.g. B. a ball mill
  • 20-60 wt .-% of at least one compound according to the invention with the addition of 2-10 wt .-% surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 wt .-% thickener (e.g. xanthan) and Crushed water into a fine suspension of active ingredients.
  • the water is added in such an amount that a total amount of 100% by weight is obtained.
  • a stable suspension of the active ingredient is obtained by diluting with water.
  • binding agent e.g. polyvinyl alcohol
  • a suitable grinding device e.g. a ball mill
  • 20-60% by weight of at least one compound according to the invention with the addition of 2-10% by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight thickener (e.g. modified clay, especially bentone, or silicon dioxide) and an organic carrier to form a fine active ingredient-oil suspension crushed.
  • surfactant e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether
  • thickener e.g. modified clay, especially bentone, or silicon dioxide
  • an organic carrier e.g. modified clay, especially bentone, or silicon dioxide
  • Water-dispersible granules and water-soluble granules 1-90% by weight, preferably 20-80% by weight, most preferably 50-80% by weight of at least one compound according to the invention are added with the addition of a surfactant (e.g. Sodium lignosulfonate and sodium alkylnaphthylsulfonate) and optionally carrier material finely ground and converted into water-dispersible or water-soluble granules by means of typical technical applications such as extrusion, spray drying, fluidized bed granulation.
  • the amount of surfactant and carrier material used is such that a total amount of 100% by weight is obtained.
  • a stable dispersion or solution of the active ingredient is obtained by diluting with water.
  • Water-dispersible powders and water-soluble powders WP, SP, WS
  • 50-80 wt .-% of at least one compound according to the invention are in a rotor-stator mill with the addition of 1-20 wt .-% surfactant (e.g. sodium lignosulfonate, sodium alkylnaphthylsulfonate) and such an amount of solid support, e.g. silica gel, that one on a total of 100 wt .-% comes, ground.
  • surfactant e.g. sodium lignosulfonate, sodium alkylnaphthylsulfonate
  • solid support e.g. silica gel
  • a ball mill 5-25% by weight of at least one compound according to the invention with the addition of 3-10% by weight of surfactant (e.g. sodium lignosulfonate), 1-5% by weight of binder (e.g. carboxymethyl cellulose) and an amount of water such as that one comes to a total amount of 100 wt .-%, comminuted.
  • surfactant e.g. sodium lignosulfonate
  • binder e.g. carboxymethyl cellulose
  • water e.g. carboxymethyl cellulose
  • 5-20% by weight of at least one compound according to the invention is converted to 5-30% by weight of an organic solvent mixture (e.g. dimethyl amide and cyclohexanone), 10-25% by weight of surfactant mixture (e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and an amount of water such as that one comes to a total amount of 100 wt .-%, given.
  • an organic solvent mixture e.g. dimethyl amide and cyclohexanone
  • surfactant mixture e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate
  • water such as that one comes to a total amount of 100 wt .-%, given.
  • This mixture is stirred for 1 hour, as a result of which a thermodynamically stable microemulsion forms spontaneously.
  • CS microcapsules
  • a protective colloid e.g. polyvinyl alcohol
  • a radical polymerization initiated with a radical initiator leads to the formation of poly (methy) acrylate microcapsules.
  • an oil phase comprising 5-50% by weight of at least one compound according to the invention, 0-40% by weight water-insoluble organic solvent e.g.
  • At least one compound according to the invention is finely ground and intimately mixed with such an amount of solid carrier, e.g. finely divided kaolin, that a total amount of 100% by weight is obtained.
  • solid carrier e.g. finely divided kaolin
  • At least one compound according to the invention is finely ground and associated with such an amount of solid support (e.g. silicate) that a total amount of 100% by weight is obtained.
  • solid support e.g. silicate
  • Ultra-Low-Volume Liquids (UL) 1-50% by weight of at least one compound according to the invention are dissolved in such an amount of organic solvent, for example aromatic hydrocarbon, that a total amount of 100% by weight is achieved .
  • Formulation types i) to xiii) can contain further auxiliaries such as 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoam agents, 0.1-1% by weight of dyes and / or pigments and 5- Comprise 10% by weight antifreeze.
  • the compounds of the formula (I) can also be used as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators to be so z.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators to be so z.
  • active ingredients can affect plant growth and / or tolerance to abiotic factors such. B.
  • the flowering and fruiting behavior can also be improved, germination and rooting can be optimized, harvesting easier and harvest yield increased, ripening can be influenced, the quality and / or the nutritional value of the harvested products can be increased, the shelf life can be extended and / or the workability of the harvested products can be improved.
  • the compounds of the formula (I) can be present as a mixture with further active ingredients or semiochemicals, such as attractants and / or bird repellants and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can also be used to improve the plant properties such as, for example, growth, yield and quality of the harvested material.
  • the compounds of the formula (I) are present in formulations or in the use forms prepared from these formulations as a mixture with further compounds, preferably those as described below.
  • AcetyIchoIinesterase (AChE) inhibitors preferably carbamates selected from Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarbol, Metocamarbol, Methocroarbom, Methocamyl, Furoprobom, Furoathiarbom Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamat, Trimethacarb, XMC and Xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chloro-phos-phos, chlorpyrorphos-methyl S-methyl, Diazinon, Dichlorvos / DDVP,
  • GABA-controlled chloride channel blockers preferably cyclodiene organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiprole) selected from ethiprole and fipronil.
  • Sodium channel modulators preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, beta -Cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans-isomer], [(EZ) - deltamethrin (lR) isomer], esfenvalerate, etofen
  • Nicotinic Acetylcholine Receptor preferably neonicotinoids selected from acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxa class, or beneolide selected from flupyradifuron, or mesoionics selected from triflumezopyrim.
  • Allosteric modulators of the nicotinic acetylcholine receptor preferably spinosyne selected from Spinetoram and Spinosad.
  • Allosteric modulators of the glutamate-dependent chloride channel preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimetics preferably juvenile hormone analogs selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin or sulfuryl fluoride or borax or tartrate or methyl isocyanate producers selected from diazomet and metam.
  • TRPV channel modulators of chordotonal organs preferably pyridinazomethanes, selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene.
  • CHS1 related mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole.
  • Microbial disruptors of the insect intestinal membrane selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, Cryc3 , mCry3A, Cry3Ab, Cry3Bb and Cry34Ab 1/35 Abi.
  • Inhibitors of mitochondrial ATP synthase preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotine, cyhexatin and fenbutatin oxide, or propargite or tetradifon.
  • Blocker of the nicotinic acetylcholine receptor channel selected from bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium.
  • CHS1-related inhibitors of chitin biosynthesis preferably benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and.
  • Inhibitors of chitin biosynthesis type 1 selected from buprofezin.
  • molting disruptor particularly in diptera, i.e. two-winged birds selected from cyromazine.
  • Ecdysone receptor agonists preferably diacylhydrazines, selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists selected from amitraz.
  • Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim, and bifenazate.
  • Mitochondrial complex I electron transport inhibitors preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad and tolfenpyrad, or Rotenone (Derris).
  • Blockers of the voltage-dependent sodium channel preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumizone.
  • Inhibitors of acetyl-CoA carboxylase preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidion and spirotetramat.
  • Inhibitors of mitochondrial complex IV electron transport preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.
  • Inhibitors of mitochondrial complex II electron transport preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.
  • Ryanodine receptor modulators preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.
  • Allosteric modulators of the GABA-dependent chloride channel preferably meta-diamide selected from broflanilide or isoxazole selected from fluxametamide.
  • Baculoviruses preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedro viruses (NPVs) selected from Anticar sia gemmatalis MNPV and Helicoverpa armigera NPV.
  • GVs granuloviruses
  • NPVs nucleopolyhedro viruses
  • Inhibitors of ergosterol biosynthesis for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamide, (1.005) fenpropidine, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009 ) Flutriafol, (F010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019 ) Pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023)
  • Inhibitors of the respiratory chain at complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008 ) Furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS , 4SR, 9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R
  • Inhibitors of the respiratory chain at complex III for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008 , (3.009) famoxadone, (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 - ⁇ [
  • 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) Zoxamid, (4,009) 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4,010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl ) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2- Bromo-4-fluorophenyl) -N- (2,6-difluoroph
  • Inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3- (5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
  • Inhibitors of ATP production for example (8.001) Silthiofam.
  • 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-ButylphenyI) -3- (2-chloropyridin-4-yI) -1- (morphoIin-4-yI) prop-2-en-1-one, (9.009) (2Z) -3 - (4-tert-ButylphenyI) -3- (2-chloropyridin-4-yI) -1- (morphoIin-4-yI) prop-2-en-1-one.
  • 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) ⁇ 3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamic acid 2,2,2-trifluoroethyl ester.
  • 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 transmission for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) procinazid, (13.005) quinoxyfen, (13.006) vinclozoline.
  • fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin , (15.018) natamycin, (15.019) nickel-dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfen
  • the compounds of formula (I) can be combined with biological pesticides.
  • Biological pest control agents include, in particular, bacteria, fungi, yeasts, plant extracts and such products that were formed by microorganisms, including proteins and secondary metabolic products.
  • Biological pest control agents 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, especially B. cereus Strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. 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, especially B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially 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.
  • B. thuringiensis subspecies israelensis serotype H-14
  • strain AM65-52 accesion No. ATCC 1276
  • B. thuringiensis subsp. aizawai especially strain ABTS-1857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-1 or B. thuringiensis subsp.
  • fungi and yeasts that are or 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), Metschnikowiafructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus especially P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, especially strain VI 17b, Trichoderma atroviride, especially strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that are or can be used as biological pesticides are:
  • bacteria and fungi that are added as "inoculants” to plants or parts of plants or plant organs and which, through their special properties, promote 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 cepacici), Gigaspora spp., Glaspora spp., Or Gigaspora monospora spp., Or Gigaspora monospora spp.
  • Lactobacillus buchneri Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp ..
  • plant extracts and such products that were formed by microorganisms including proteins and secondary metabolic products that are or can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, such as, for example, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamid, Dichlormid, Fenchlorazol (-ethyl), Fenclorim, Flurazol, Fluxofenim, Furilazol, Isoxadifen (-ethyl), Mefenpyr (diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa- 4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) - 1,3-oxazolidine (CAS 52836-31-4).
  • plants and parts of plants can be treated according to the invention.
  • Plants are understood here as meaning all plants and parts of plants, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potatoes, sugar beets, sugar cane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage) and other vegetables, cotton, tobacco, rape, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soy, potatoes, sugar beets, sugar cane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica olerace
  • 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 cultivars that can or cannot be protected by plant breeders' rights.
  • Plants are to be understood as meaning all stages of development such as seeds, cuttings, young (immature) plants up to mature plants.
  • Plant parts are to be understood as meaning all above-ground and underground parts and organs of plants such as shoot, leaf, flower and root, with, for example, leaves, needles, stems, stems, flowers, fruiting bodies, 5s
  • the plant parts also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage room by the customary treatment methods, eg. B. by immersion, spraying, evaporation, misting Ver, scattering, brushing on, injecting and in the case of propagation material, especially in the case of seeds, by one or more layers of wrapping.
  • customary treatment methods eg. B. by immersion, spraying, evaporation, misting Ver, scattering, brushing on, injecting and in the case of propagation material, especially in the case of seeds, by one or more layers of wrapping.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars occurring in the wild or obtained by conventional biological breeding methods such as crossing or protoplast fusion, as well as their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above. According to the invention, it is particularly preferred to treat plants of the plant varieties which are commercially available or in use. Plant cultivars are understood to be plants with new properties (“traits”) that have been obtained through conventional breeding, mutagenesis or recombinant DNA techniques. These can be varieties, races, bio and genotypes.
  • the compounds of the formula (I) can advantageously be used for treating transgenic plants, plant cultivars or plant parts which have received genetic material which gives these plants, plant cultivars or plant parts advantageous and / or useful properties (traits). It is therefore contemplated to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof.
  • the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome leads to a transgenic event.
  • the insertion creates a new DNA sequence, which is referred to as an "event" and which is marked by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to the inserted DNA / the inserted DNA flanking it at both ends.
  • traits or transgenic events include, but are not limiting, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, flybridge seed production and herbicide tolerance, the trait being in relation to a plant that has such a trait or a such a transgenic event is absent, is measured.
  • beneficial and / or useful properties are better plant growth, vitality, stress tolerance, stamina, Resistance to storage, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased flowering performance, easier harvest, acceleration of maturity, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products and increased resistance or tolerance to animal and microbial pests such as insects, arachnids, nematodes, mites and snails.
  • beneficial and / or useful properties are better plant growth, vitality, stress tolerance, stamina, Resistance to storage, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased flowering performance, easier harvest, acceleration of maturity, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products
  • Bt-Cry or VIP proteins which include CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof, and also hybrids or combinations thereof, in particular the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA-CrylF proteins or toxic fragments thereof), the proteins of the CrylA type or toxic fragments thereof, preferably the CrylAc- Protein or hybrids derived from the CrylAc protein (e.g.
  • hybrid CrylAb-CrylAc proteins or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the CrylA.105 Protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as in Estruch et al. (1996), Proc Natl Acad Sci US A.
  • cry proteins as described in WO2001 / 47952, the insecticidal proteins from Xenorhabdus (as described in WO98 / 50427), Serratia (in particular from S. entomophila) or strands of the Photorhabdus species, such as Tc proteins from Photorhabdus, as described in WO98 / 08932.
  • Serratia in particular from S. entomophila
  • Tc proteins from Photorhabdus
  • This also includes all variants or mutants of one of these proteins which differ in some amino acids (1-10, preferably 1-5) from any of the above-mentioned sequences, in particular the sequence of their toxic fragment, or which are linked to a transit peptide such as a plastid transit peptide or other protein or peptide are fused.
  • herbicides for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin.
  • DNA sequences coding for proteins which give the transformed plant toes and plants tolerance properties to certain herbicides in particular the bar or PAT gene or the Streptomyces coelicolor gene, which is described in WO2009 / 152359 and which is tolerance to Glufonsine herbicides, a gene that is necessary for a suitable EPSPS (5-enolpyruvylshikimate-3- phosphate synthase), which confers tolerance to herbicides with EPSPS as a target, in particular herbicides such as glyphosate and its salts, a gene coding for glyphosate N-acetyltransferase or a gene coding for glyphosate oxoreductase can be mentioned.
  • EPSPS 5-enolpyruvylshikimate-3- phosphate syntha
  • herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. WO2007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g. US Pat. No. 6,855,533), genes coding for 2,4-D-monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and genes coding for dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).
  • ALS acetolactate synthase
  • a mutated Arabidopsis ALS / AHAS gene e.g. US Pat. No. 6,855,533
  • genes coding for dicamba monooxygenases that confer tolerance to dicamba (3,6-d
  • Particularly useful transgenic events in transgenic plants or plant cultivars include Event 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002 / 034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010 / 117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005 / 103266 or US-A 2005-216969); Event 300
  • Event BLR1 rape, restoration of male sterility, deposited as NCIMB 41193, described in WO2005 / 074671
  • Event CE43-67B cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006 / 128573
  • Event CE44-69D cotton, insect control, not deposited, described in US-A 2010-0024077
  • Event CE44-69D cotton, insect control, not deposited, described in WO2006 / 128571
  • Event CE46-02A cotton, insect control, not deposited, described in WO2006 / 128572
  • Event COT102 cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986
  • Event COT202 cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479
  • Event COT203 cotton, insect control
  • PTA-11041) optionally stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55 (WO2011 / 063413A2), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-10442, WO2011 / 066360A1), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-10442 , WO2011 / 066384A1), Event DP-040416-8 (maize, insect control, ATCC accession no. PTA-11508, WO2011 / 075593A1), event DP-043A47-3 (maize, insect control, ATCC accession no.
  • transgenic events are provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov. The status of this list as it was on the filing date of the present application is relevant for the present application.
  • the genes / events which confer the desired characteristics in question can also be present in combinations with one another in the transgenic plants.
  • transgenic plants examples include important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetables, cotton, Tobacco, rapeseed and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed being particularly emphasized.
  • Traits that are particularly emphasized are the increased resistance of plants to insects, arachnids, nematodes and snails as well as the increased resistance of plants to one or more herbicides.
  • plants, plant parts or plant seeds which can preferably be treated according to the invention, include commercially available products such as plant seeds, which are under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2 YIELD®-, YIELDGARD®-, ROUNDUP READY® 2 XTEN D TM -, INTACTA RR2 PRO®-, VISTIVE GOLD®- and / or XTENDFLEX TM trade names are sold or distributed.
  • plant seeds which are under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2
  • the treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their surroundings, habitat or storage room by the customary treatment methods, e.g. B. by dipping, spraying, atomizing, sprinkling, scattering, foaming, brushing, spreading, injecting, pouring (drenching), drip irrigation and in the case of propagation material, especially in the case of seeds, furthermore by dry dressing, wet dressing, slurry dressing, encrusting , single-layer or multilayer coating, etc. It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the application form or the compound of the formula (I) into the soil itself.
  • the customary treatment methods e.g. B. by dipping, spraying, atomizing, sprinkling, scattering, foaming, brushing, spreading, injecting, pouring (drenching), drip irrigation and in the case of propagation material, especially in the case of seeds, furthermore by dry dressing, wet dressing
  • a preferred direct treatment of the plants is foliar application; H. the compounds of the formula (I) are applied to the foliage, the frequency of treatment and the application rate should be matched to the infestation pressure of the pest in question.
  • the compounds of the formula (I) also get into the plants via the root system.
  • the plants are then treated by the action of the compounds of the formula (I) on the plant's habitat. This can be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (e.g.
  • the compounds of the formula (I) according to the invention are introduced into the location of the plants in solid form (for example in the form of granules) or through Drip application (often also referred to as "chemigation"), ie the compounds of the formula (I) according to the invention are introduced by means of surface or underground drip pipes over certain periods of time together with varying amounts of water at defined locations near the plants. In the case of water rice cultures, this can also be done by metering the compound of the formula (I) in a solid application form (for example as granules) into a flooded rice field.
  • the compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite farming, precision farming or precision agriculture.
  • models support the site-specific management of agricultural facilities with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, Yield, etc., with the aim of optimizing profitability, sustainability and environmental protection.
  • such models can help optimize agronomic decisions, control the precision of pesticide applications and record the work carried out.
  • the compounds according to the invention can be applied to a crop plant according to a corresponding application protocol if the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound according to the invention to the crop plant.
  • the compounds according to the invention can also be used in combination with a smart sprayer such as a device for spot spraying or precision spraying, which is attached to a farm vehicle such as a tractor, a robot, a helicopter, an aircraft, an unmanned aerial vehicle (UAV) such as a drone - or is housed, can be used.
  • a smart sprayer such as a device for spot spraying or precision spraying, which is attached to a farm vehicle such as a tractor, a robot, a helicopter, an aircraft, an unmanned aerial vehicle (UAV) such as a drone - or is housed
  • a device usually comprises input sensors (such as a camera) and a processing unit which is responsible for the analysis of the input data and the provision of a decision, which is based on the analysis of the input data, regarding the application of the compound according to the invention to the crops ( or the weeds) is configured in a specific and precise manner.
  • the use of such smart sprayers usually requires position systems (e.g.
  • GPS receivers with which the recorded data can be localized and farm vehicles controlled or monitored, geographic information systems (GIS) with which the information is displayed on understandable maps, and corresponding farm vehicles for implementation the required agricultural measure such as spraying.
  • GIS geographic information systems
  • pests can be detected from images captured by a camera.
  • the pests can be identified and / or classified based on these images.
  • image processing algorithms can use machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. In this way it is possible to use the connections described here only where they are needed.
  • the present invention therefore also relates in particular to a method for protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of the formula (I).
  • the method according to the invention for protecting seeds and germinating plants from attack by pests further comprises a method in which the seed is treated simultaneously in one process or sequentially with a compound of the formula (I) and a mixture component. It also includes a method in which the seed is treated at different times with a compound of the formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seeds in order to protect the seeds and the plants resulting therefrom from animal pests.
  • the invention further relates to seeds which have been treated with a compound of the formula (I) according to the invention for protection against animal pests.
  • the invention also relates to seeds, which at the same time with a compound of formula (I) and a Mix component has been treated.
  • the invention further relates to seeds which have been treated at different times with a compound of the formula (I) and a mixture component.
  • the individual substances can be present in different layers on the seed.
  • the layers which contain a compound of the formula (I) and mixture components can optionally be separated by an intermediate layer.
  • the invention also relates to seeds in which a compound of the formula (I) and a mixture component are applied as a constituent of a coating or as a further layer or layers in addition to a coating.
  • the invention further relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • Compounds of the formula (I) can also be used in combination with compositions or compounds of signal technology, as a result of which better colonization with symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation .
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi
  • the compounds of the formula (I) are suitable for protecting seeds of any type of plant which is used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are grain seeds (e.g. wheat, barley, rye, millet and oats), maize, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g. Sugar beet and fodder beet), peanuts, vegetables (e.g. tomatoes, cucumbers, beans, cabbage plants, onions and lettuce), fruit plants, lawns and ornamentals.
  • the treatment of the seeds of cereals (such as wheat, barley, rye and oats), maize, soy, cotton, canola, rapeseed, vegetables and rice is of particular importance.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seeds can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seeds which contain at least one heterologous gene which is derived from Bacillus sp. originates. It is particularly preferably a heterologous gene which originates from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
  • the seed can be treated at any point between harvest and sowing.
  • seeds are used that have been separated from the plant and freed from cobs, peels, stems, coats, wool or pulp.
  • seeds can be used that have been harvested, cleaned and dried to a storable moisture content.
  • seeds can also be used which, after drying, for. B. treated with water and then dried again, for example priming.
  • care when treating the seed, care must be taken to ensure that the amount of the compound of the formula (I) and / or further additives applied to the seed is selected so that the germination of the seed is not impaired or the plant resulting therefrom is not damaged will. This is particularly important for active ingredients that can show phytotoxic effects when applied in certain amounts.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to the person skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seeds, and also UFV formulations.
  • formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
  • customary additives such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
  • Suitable dyes which can be contained in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments which are sparingly soluble in water and dyes which are soluble in water can be used here. May be mentioned as examples the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.
  • Suitable wetting agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which are customary for the formulation of agrochemical active ingredients and which promote wetting.
  • Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
  • Suitable dispersants and / or emulsifiers which can be contained 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 ingredients. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • the seed dressing formulations which can be used according to the invention can contain all foam-inhibiting substances customary for the formulation of agrochemical active ingredients as defoamers. Silicone defoamers and magnesium stearate can preferably be used.
  • All substances which can be used in agrochemical agents for such purposes can be present as preservatives in the seed dressing formulations which can be used according to the invention.
  • Examples include dichlorophene and benzyl alcohol hemiformal.
  • Secondary thickening agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which can be used in agrochemical agents for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silicic acid are preferred.
  • adhesives which can be contained in the seed dressing formulations which can be used according to the invention all conventional binders which can be used in seed dressings are suitable.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose may be mentioned as preferred.
  • the gibberellins are known (see R. Wegler “Chemistry of Plant Protection and Pest Control Agents”, 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 treating seeds of the most varied of types.
  • the concentrates or the preparations obtainable from them by diluting them with water can be used for dressing the seeds of grain such as wheat, barley, rye, oats and triticale, as well as the seeds of maize, rice, rape, peas, beans, cotton, Sunflowers, soy and beet or vegetable seeds of the most varied nature.
  • the seed dressing formulations which can be used according to the invention or their diluted application forms can also be used for dressing seeds of transgenic plants.
  • the procedure for dressing is to put the seed in a mixer in batch or continuous mode, add the desired amount of dressing formulations either as such or after prior dilution with water and until the formulation is evenly distributed the seed mixes. If necessary, this is followed by a drying process.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seeds.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of the formula (I), which have a favorable toxicity towards warm-blooded animals, are suitable for combating parasites which occur in animal breeding and keeping in farm animals, breeding animals, zoo animals, laboratory animals, test animals and domestic animals. They are effective against all or individual stages of development of the parasites.
  • the farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and in particular cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aquaculture, or possibly insects such as bees.
  • Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and, in particular, dogs, cats, housebirds; Reptiles, amphibians or aquarium fish.
  • the compounds of the formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely house birds or, in particular, poultry.
  • the use of the compounds of the formula (I) for combating animal parasites is intended to reduce or prevent disease, deaths and reduced performance (in the case of meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal husbandry is possible and better animal welfare can be achieved.
  • control or “control” in the present context means that the compounds of the formula (I) effectively prevent the occurrence of the respective parasite in an animal which is infected with such parasites to a harmless extent , is reduced. More precisely, “combating” in the present context means that the compounds of the formula (I) kill the respective parasite, prevent its growth or prevent its reproduction.
  • the arthropods include, for example, but are not limited to, from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example 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., Chry
  • 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., Rhip
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as:
  • Metamonada from the order Vaccinia 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. B. Hartmanella sp.
  • Alveolata such as Apicomplexa (Sporozoa): e.g. B. 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 e.g. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida e.g. B.
  • Leucocytozoon spp. Plasmodium spp .; from the order Piroplasmida e.g. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida e.g. B. Balantidium spp., Buxtonella spp.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • the helminths pathogenic for humans or animals include, for example, acanthocephala, nematodes, pentastomas and platyhelminths (for example Monogenea, Cestodes and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea e.g. E.g .: 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.
  • Cyclophyllida for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysanie spp., Thysanosoma spp., Thysanosoma spp., Thysanosoma spp.
  • Trematodes from the class Digenea for example: 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., Fasciolides spp ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium s
  • Paragonimus spp. Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.
  • Nematodes from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • Rhabditina 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., Crenosoma spp.
  • Cyclococercus spp. Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Hapalous sp spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagum spp., Oesophagum spp., Oesophagum spp., Oesophagum spp., Oesophag
  • Spirurida for example: 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
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida, for example Linguatula spp.
  • the compounds of the formula (I) are administered by methods generally known in the art, such as enteral, parenteral, dermal or nasal, in the form of suitable preparations. Administration can be prophylactic; metaphylactically or therapeutically.
  • one embodiment of the present invention relates to the compounds of the formula (I) for use as medicaments.
  • Another aspect relates to the compounds of formula (I) for use as
  • Another special aspect relates to the compounds of formula (I) for use as
  • Antihelminthic in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.
  • Another special aspect relates to the compounds of formula (I) for use as
  • Another aspect relates to the compounds of the formula (I) for use as an anti-parasitic agent, in particular an arthropodicide, very particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. solid or liquid diluent), a pharmaceutically acceptable auxiliary (e.g. surfactants), in particular one a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient e.g. solid or liquid diluent
  • auxiliary e.g. surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or auxiliaries, in particular with pharmaceutically acceptable excipients and / or excipients conventionally used in veterinary formulations / or aids.
  • Another special aspect of the invention is veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozolic and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocidal, acanthicidal, insecticidal, insecticidal formulations the aspects mentioned, as well as processes for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, especially a non-human Animal in need of it.
  • Another aspect relates to a method for the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined here in an animal, in particular a non-human animal, the same requirement.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasite infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endo- and ectoparasiticides, are provided for the veterinary field.
  • mixture not only means that two (or more) different active ingredients are formulated in a common formulation and are used accordingly together, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated in separate formulations; Mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow separate or sequential use of the active ingredients in question.
  • active ingredients from the group of ectoparasiticides as mixing partners include, without this being intended to represent a restriction, the insecticides and acaricides listed in detail above. Further active ingredients that can be used are listed below according to the above-mentioned classification, which is based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (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 chordotonal organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase
  • Active ingredients with unknown or non-specific mechanisms of action e.g. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionate, Triarathen, Clothiazoben, Tetrasul, Potassium Oleate, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Bromopropylate, Cryolite;
  • Organochlorine compounds e.g. B. camphechlor, lindane, fleptachlor; or phenylpyrazoles, e.g. B. acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner;
  • Pyrethroids e.g. B. (Eis-, trans-) Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Fieptafluthrin, Fieptafluthrin, Cypthrin-cythrin, clo-methanomethrin, cloethanopermethrin, clo-pyrocythrin, fenopermethrin , Cyhalothrin (lambda-), chlovaporthrin, or halogenated hydrocarbon compounds (FICFls),
  • Neonicotinoids e.g. B. nithiazine
  • Dicloromezotiaz, triflumezopyrim macrocyclic lactones e.g. B. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime
  • Bios, fiormones or pheromones for example natural products, e.g. thuringiensine, codlemon or neem components
  • Dinitrophenols e.g. B. Dinocap, Dinobuton, Binapacryl;
  • Benzoylureas e.g. B. Fluazuron, Penfluron,
  • Amidine derivatives e.g. B. Chlormebuform, Cymiazol, Demiditraz
  • Beehive varroa acaricides for example organic acids, e.g. formic acid, oxalic acid.
  • Exemplary active ingredients from the group of endoparasiticides, as mixing partners, include, without being limited thereto, anthelmintic active ingredients and antiprotozoal active ingredients.
  • the anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematicidal and / or cestocidal active ingredients: from the class of the macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide,
  • Antiprotozoal agents including but not limited to the following agents: from the class of the triazines, for example: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; from the class polyletherionophore, for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of the macrocyclic lactones, for example: milbemycin, erythromycin; from the class of the quinolones, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the class of the pyrimidines, for example: pyrimethamine; from the class of the sulfonamides, for example: sulfachinoxaline, trimethoprim, sulfaclozine; from the class of the thiamines, for example: Amprolium; from the class of the lincosamides, for example: clindamycin
  • the mixing partners mentioned above can also, if appropriate, if they are capable of doing so on the basis of their functional groups, form salts with suitable bases or acids.
  • a vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, which is able to remove pathogens such as. B. viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host.
  • the pathogens can be transmitted to a host either mechanically (e.g. trachoma by non-stinging flies) or after injection (e.g. malaria parasites by mosquitoes) into a host.
  • vectors and the diseases or pathogens they transmit are: 1) mosquitoes
  • Anopheles malaria, filariasis
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • mites acariosis, epidemic typhus, rickettsipox, tularemia, Saint Louis encephalitis, early summer meningoencephalitis (TBE), Crimean Congo hemorrhagic fever, borreliosis;
  • Ticks Borelliosis such as Borrelia bungdorferi sensu lato., Borrelia duttoni, early summer meningoencephalitis, 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.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens that are transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, in horticulture, in gardens and leisure facilities as well as in storage and material protection. Protection of technical materials
  • the compounds of the formula (I) are suitable for protecting industrial materials against attack or destruction by insects, e.g. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • Industrial materials in the present context are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints.
  • non-living materials such as, preferably, plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints.
  • the use of the invention to protect wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of the formula (I) are in the form of a ready-to-use pesticide, i. E. That is, they can be applied to the corresponding material without further changes.
  • a ready-to-use pesticide i. E. That is, they can be applied to the corresponding material without further changes.
  • insecticides or fungicides those mentioned above are particularly suitable.
  • the compounds of the formula (I) can be used to protect against fouling on objects, in particular ship hulls, sieves, nets, structures, quays and signal systems which come into contact with sea or brackish water.
  • the compounds of the formula (I) can also be used as antifouling agents on their own or in combinations with other active ingredients.
  • the compounds of the formula (I) are suitable for combating animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and stored product protection, especially for combating insects, arachnids, ticks and mites that occur in closed rooms, such as apartments, factory halls, offices, vehicle cabins, animal breeding facilities.
  • the compounds of the formula (I) are used alone or in combination with other active ingredients and / or auxiliaries. They are preferably used in household insecticide products.
  • the compounds of the formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests from 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. They are used, for example, in aerosols, pressureless sprays, e.g. B.
  • LC-MS3 Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml / min.
  • LC-MS6 and LC-MS7 Agilent 1290 LC, Agilent MSD, F1TS PAL sample changer. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml / min.
  • LC-MS4 Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column Waters Acquity 1.7 pm 50 mm * 2.1 mm, oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 ml / min.
  • LC-MS5 Agilent 1100 LC system with MSD mass spectrometer and F1TS PAL sample changer (column: Zorbax XDB CI 8 1.8 pm50mm * 4.6 mm, oven temperature 55 ° C). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 ml / min.
  • the retention time indices were determined in all cases according to a homologous series of straight-chain alkanones with 3 to 16 carbons, with the index of the first alkanone set to 300, that of the last to 1600 and linear interpolation between the values of successive alkanones .
  • the measurements of the 1 H-NMR spectra were carried out with a Bruker Avance III 400 MHz spectrometer, equipped with a 1.7 mm TCI probe head, with tetramethylsilane as standard (0.00 ppm) and the measurements were usually recorded from solutions in the solvents CD3CN, CDCL or d6-DMSO.
  • a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements.
  • the measurements were carried out at a probe head temperature of 298 K. If other measuring temperatures were used, this will be noted separately.
  • the 'H-NMR data of selected examples are presented in the form of' H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity is listed in round brackets. The d-value - signal intensity number pairs are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form: di (intensityi); 62 (intensity 2); . ; d, (intensity,); . ; d h (intensity)
  • the intensity of sharp signals correlates with the height of the signals in a printed representation of a 1 H-NMR spectrum in cm and shows the real relationships between the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • Tetramethylsilane is used to calibrate the chemical shift of 'H-NMR spectra or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore the 'H-NMR-Pcclists may contain the tetramethylsilane peak.
  • 1 H-NMR solvent signals, the tetramethylsilane signal and the water signal in the respective solvent are excluded from the relative intensity calibration because the intensity values given for them can be very high.
  • peaks of stereoisomers of the compounds according to the invention and / or peaks of impurities usually have a lower intensity than the peaks of the compounds according to the invention (for example at a purity of> 90%).
  • Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of a manufacturing process based on “by-product fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods can identify the peaks of the target compounds as required, with additional intensity filters being used if necessary. This identification is equivalent to the relevant list of peaks in the classical 'H-NMR interpretation.
  • the solvent used can be read from the JCAMP file with the parameter "solvent”, the measuring frequency of the spectrometer with “observe frequency” and the spectrometer model with "spectrometer / data system”.
  • 13 C-NMR data are given analogously to the 1 H-NMR data as peak lists from broadband decoupled 13 C-NMR spectra.
  • 13 C-NMR solvent signals and tetramethylsilane are removed from the relative intensity calibration because these signals can have very high intensity values.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (CI 8) using the following methods:
  • the logP value is determined by LC-UV measurement in the acidic range, with 0.9 ml / l formic acid in water and 1.0 ml / l formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile ).
  • the logP value is determined by LC-UV measurement in the neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • the calibration was carried out with straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values between successive alkanones are determined by linear regression.
  • aqueous phase was neutralized with 1.0 M aqueous sodium hydroxide solution and extracted exhaustively with ethyl acetate. All organic phases were combined, washed with saturated aqueous sodium chlorine solution, dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (345 mg, 51% of theory).
  • the reaction mixture was stirred at RT overnight. Then, while cooling with ice with water and saturated aqueous solution, the mixture became Sodium bisulfite solution is added and the mixture is stirred at RT for a further night.
  • the mixture was diluted with water (50 mL) and dichloromethane (100 mL). The phases were separated and the organic phase was washed first with water and then with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated. Acetonitrile (4.0 mL) was added to the residue and the mixture was stirred at RT. Filtering off and drying the solids yielded a first amount of the target compound (485 mg, 92% purity, 41% of theory). The mother liquor was concentrated and the residue was concentrated by column chromatography on silica gel, whereby further title compound (114 mg, 93% purity, 12% of theory) could be isolated.
  • Tetrakis (triphenylphosphine) palladium (0) (11.2 mg, 10 pmol) was added and the mixture was heated to 92 ° C overnight. After cooling to RT, the reaction mixture was concentrated to dryness and the residue was taken up in water and dichloromethane. The phases were separated and the organic phase was washed twice with water and then dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (49.3 mg, 88% purity, 52% of theory).
  • the mixture was degassed for 5 minutes in a stream of argon before the vessel was closed and heated to 120 ° C. for 12 minutes in the microwave reactor. After cooling, tetrakis (triphenylphosphine) palladium (0) (9.0 mg, 8.0 pmol) was added and again heated to 120 ° C for 24 min. After cooling, tetrakis (triphenylphosphine) palladium (0) (9.0 mg, 8.0 pmol) was added again and the mixture was again heated to 120 ° C. for 1 h. The cooled reaction mixture was admixed with water and dichloromethane, the phases were separated and the organic phase was washed twice with water and then dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (9.1 mg, 20% of theory).
  • Example 1-12 2- [2- (3-bromophenyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
  • reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (9.3 mg, 18% of theory).
  • Triazole (8.5 mg, 78 pmol) and potassium carbonate (10.7 mg, 78 pmol) in DMF was heated to 96 ° C overnight.
  • 3-Cyclopropyl-1H-l, 2,4-triazole (8.5 mg, 78 pmol) and potassium carbonate (10.7 mg, 78 pmol) were then added again and the mixture was stirred at 96 ° C. for a further 5 hours .
  • the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (23.0 mg, 98% purity, 53% of theory).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
  • Pre-swollen wheat kernels (Triticum aestivum) are incubated for one day in a multiwell plate filled with agar and a little water (5 seeds per well). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Each cavity is then infected with 10-20 Diabrotica balteata beetle larvae. The effect is determined in% after 7 days. 100% means that all wheat plants have grown as in the untreated, non-infected control; 0% means that no wheat plant has grown.
  • Vessels are filled with sand, active ingredient solution, an egg-larva suspension of the southern root knot (Meloidogyne incognita) and lettuce seeds.
  • the lettuce seeds germinate and the plants develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined based on the gall formation in%. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.
  • the active compound preparation 50 ⁇ l of the active compound preparation are transferred to microtiter plates and made up to a final volume of 200 ml with 150 ml of IPL41 insect medium (33% + 15% sugar).
  • the plates are then sealed with parafilm, through which a mixed population of the green peach aphid (Myzus persicae) located in a second microtiter plate can pierce and absorb the solution.
  • Myzus persicae Myzus persicae
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
  • Chinese cabbage leaf disks (Brassica pekinensis) which are 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 in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
  • Barley plants (Hordeum vulgare) are sprayed with an active compound preparation of the desired concentration and infected with larvae of the green rice bug (Nezara viridula).
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
  • Rice plants (Oryza sativa) are sprayed with the preparation of active compound of the desired concentration and then infected with the brown-backed rice leafhopper (Nilaparvata lugens).
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
  • Corn leaf disks (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the army worm (Spodoptera frugiperda).
  • the effect is determined in% after 7 days. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars has been killed.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water. If the addition of ammonium salts and / or penetration enhancers is necessary, these are each added to the preparation solution in a concentration of 1000 ppm. Bell pepper plants (Capsicum annuum) which are heavily infested by the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.

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Abstract

The invention relates to new compounds of the formula (I), wherein R1, R2, R3, R4, R5, R6, R7, Y, Z, n and m 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

Heterocvclen-Derivate als Schädlingsbekämpfungsmittel Heterocvclen derivatives as pesticides
Die vorliegende Erfindung betrifft Heterocyclen-Derivate der Formel (I), deren Verwendung 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 heterocycle derivatives of the formula (I), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular insects and arachnids, and processes and intermediates for their preparation.
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 2013/180193, WOHeterocycle derivatives with 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 2013/180193, WO
2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557, WO 2015/121136, WO 2015/133603, WO 2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO 2016/005263, WO 2016/039441, WO 2015/198817, WO 2016/041819, WO 2016/039441, WO 2016/039444, WO 2016/026848, WO 2016/023954, WO 2016/020286, WO 2016/046071, WO 2016/058928, WO 2016/059145, WO 2016/071214, WO 2016/091731, WO 2016/096584, WO 2016/107742, WO 2016/107831, WO 2016/113155, WO 2016/116338, WO 2016/121997, WO 2016/125621, WO 2016/125622, WO 2016/129684, WO 2016/142326, WO 2016/142327, WO 2016/169882, WO 2016/169886, WO 2018/130437, WO 2018/130443 und WO 2020/002082. 2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO 2016/124563, WO 2016/124557, WO 2015/121136, WO 2015/133603, WO 2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO 2016/005263, WO 2016/039441, WO 2015/198817, WO 2016/041819, WO 2016/039441, WO 2016/039444, WO 2016/026848, WO 2016/023954, WO 2016/020286, WO 2016/046071, WO 2016/058928, WO 2016/059145, WO 2016/071214, WO 2016/091731, WO 2016/096584, WO 2016/107742, WO 2016/107831, WO 2016/113155, WO 2016/116338, WO 2016/121997, WO 2016/125621, WO 2016/125622, WO 2016/129684, WO 2016/142326, WO 2016/142327, WO 2016/169882, WO 2016/169886, WO 2018/130437, WO 2018/130443 and WO 2020/002082.
Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Nützling- und Bestäuberschonung, der Umwelteigenschaften, der Aufwandmengen, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rohe sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss, ferner können Resistenzen auftreten, um nur einige Paramenter zu nennen. Schon aus ah diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nicht als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Questions of toxicity, the protection of beneficial organisms and pollinators, the environmental properties, the application rates, the combinability with other active ingredients or formulation auxiliaries play a role as well as the question of the effort that must be made for the synthesis of an active ingredient; furthermore, resistances can arise for only to name a few parameters. For these reasons alone, the search for new crop protection agents cannot be regarded as complete and there is a constant need for new compounds with properties that are better than the known compounds, at least with regard to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustehen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. It was an object of the present invention to provide compounds by means of which the spectrum of pesticides is broadened under various aspects and / or their activity is improved.
Es wurden nun neue 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 Heterocyclen-Derivate können in Kombination mit weiteren Mitteln zur Verbesserung der Wirksamkeit insbesondere gegen schwierig zu bekämpfende Insekten eingesetzt werden. New heterocycle derivatives have now been found which have advantages over the already known compounds, e.g. better biological or ecological properties, broader application methods, better insecticidal, acaricidal action, and good compatibility with useful plants. The heterocycle derivatives can be used in combination with other agents to improve the effectiveness, in particular against insects which are difficult to control.
Gegenstand der vorliegenden Erfindung sind daher neue Verbindungen der Formel (I) in welcher The present invention therefore relates to new compounds of the formula (I) in which
(Ausgestaltung 1-1) (Arrangement 1-1)
R1 für (Ci-C6)Alkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (Ci- C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl oder (C3-Cs)Cycloalkyl steht, R 1 for (Ci-C 6 ) alkyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) hydroxyalkyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl , (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl or (C 3 -Cs) cycloalkyl,
R2 für Wasserstoff, (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 2 for hydrogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) hydroxyalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (Ci- C6) haloalkoxy (Ci-C6) 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, (C 2 -C 6) Halogenalkenyloxy- (Ci-C 6) 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-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3-C6) haloalkinyloxy (Ci-C6) alkyl, (C 2 -C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 3 -
Cs)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, Cyano(C3-Cs)cycloalkyl, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-Cs) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) alkyl (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, cyano (C 3 -Cs) cycloalkyl, (Ci-C6) alkylthio- (Ci-C6) alkyl, (Ci-
C6)Halogenalkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C 6 ) haloalkylthio (Ci-C 6 ) alkyl, (Ci-C 6 ) alkylsulfinyl (Ci-C 6 ) alkyl, (Ci-
C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C 6 ) haloalkylsulfinyl (Ci-C 6 ) alkyl, (Ci-C 6 ) alkylsulfonyl (Ci-C 6 ) alkyl, (Ci-
C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6) haloalkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl oder (Ci- C6)Halogenalkoxycarbonyl-(Ci-C6)alkyl steht, C6) haloalkylcarbonyl- (Ci-C6) alkyl, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl or (Ci- C6) haloalkoxycarbonyl- (Ci-C6) alkyl,
R3 für Wasserstoff, Halogen, Cyano, Nitro, (Ci-C6)Alkyl, (C3-Cs)Cycloalkyl, Cyano(C3- C8)cycloalkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, SCN, (Ci-C6)Alkylcarbonyl, (Ci- C6)Halogenalkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl,R 3 is hydrogen, halogen, cyano, nitro, (Ci-C6) alkyl, (C 3 -Cs) cycloalkyl, cyano (C 3 - C 8) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, ( Ci-C6) haloalkoxy, (Ci-C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (Ci- C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, (Ci- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl,
Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci- C6)Halogenalkylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (Ci- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkylaminothiocarbonyl, (Ci-Aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-
C6)Halogenalkylaminothiocarbonyl, (C3-C8)Cycloalkylaminothiocarbonyl, Amino, (Ci- C6)Alkylamino, (Ci-C6)Halogenalkylamino, Di-(Ci-C6)Alkylamino, (C3-C8)Cycloalkylamino, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylcarbonylamino, (Ci-C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3-C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci- C6)Alkylthiocarbonylamino, (Ci-C6)Halogenalkylthiocarbonylamino, (Ci-C6)Alkylthiocarbonyl- (Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C6) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, amino, (Ci- C6) alkylamino, (Ci-C6) haloalkylamino, di- (Ci-C6) alkylamino, (C 3 -C 8 ) cycloalkylamino, (Ci- C6) alkylsulfonylamino, (Ci-C6) alkylcarbonylamino, (Ci-C6) haloalkylcarbonylamino, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-C6) haloalkylcarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8 ) Cycloalkylcarbonylamino, (C 3 -C 8 ) Cycloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci- C6) Alkylthiocarbonylamino, (Ci-C6) Haloalkylthiocarbonylamino, (Ci-C6) Alkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-C 6 ) haloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (C 3 -
C8)Cycloalkylthiocarbonylamino, (C3-C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C2- C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2- C6)Alkinyl oder (C2-C6)Halogenalkinyl, (C3-C8)Cycloalkyl-(C2)alkinyl, (C3-Cs)Cycloalkyl-(Ci- C6)alkyl, (Ci-C6)Alkylaminocarbonylamino, Di-(Ci-C6)Alkylaminocarbonylamino, (C3- C8)Cycloalkylaminocarbonylamino, (Ci-C6)Halogenalkylaminocarbonylamino, (Ci- C6)Alkylaminocarbonyl-(Ci-C6)alkyl-amino, Di-(Ci-C6)Alkylaminocarbonyl-(Ci-C6)alkyl- amino, (C3-C8)Cycloalkylaminocarbonyl-(Ci-C6)alkyl-amino oder (Ci-C 8) Cycloalkylthiocarbonylamino, (C 3 -C 8) Cycloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C 2 - C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl , (C 3 -Cs) cycloalkyl (C 2) alkenyl, (C 2 - C 6) alkynyl or (C 2 -C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl (C 2) alkynyl, (C 3 -Cs) cycloalkyl- (Ci- C 6 ) alkyl, (Ci-C 6 ) alkylaminocarbonylamino, di- (Ci-C 6 ) alkylaminocarbonylamino, (C 3 - C 8 ) cycloalkylaminocarbonylamino, (Ci-C 6 ) haloalkylaminocarbonylamino, ( Ci-C 6 ) alkylaminocarbonyl- (Ci-C 6 ) alkyl-amino, di- (Ci-C 6 ) alkylaminocarbonyl- (Ci-C 6 ) alkyl-amino, (C 3 -C 8 ) cycloalkylaminocarbonyl- (Ci-C 6 ) alkyl-amino or (Ci-
C6)Halogenalkylaminocarbonyl-(Ci-C6)alkyl-amino, oder für für einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituierten gesättigten, teilgesättigten oder heteroaromatischen Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist oder für einen einfach oder mehrfach, gleich oder verschieden substituierten gesättigten oder teilgesättigten carbocyclischen Ring oder für einen aromatischen Ring steht, wobei jeweils gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und/oder wobei als Substituenten jeweils in Frage kommen: Cyano, Carboxyl, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, SF5, Tri-(Ci-C6)alkylsilyl, (C3-Cs)Cycloalkyl, (C3-Cs)Cycloalkyl- (C3-Cs)cycloalkyl, (Ci-C6)Alkyl-(C3-Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, Halogen-(C3-Cs)cycloalkyl, Cyano-(C3-Cs)cycloalkyl, (CVO,) Alkyl, ( C 1 - C 5) H a 1 g c n a 1 k y 1 , (Ci- CöjCyanoalkyl, (Ci-CejCyanohalogenalkyl, ( C 1 -CA,) H ydroxyal kyl , Hydroxycarbonyl-(Ci-C6)- alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyl, (C2- CöjHalogenalkenyl, (C2-C6)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2-C6)Alkinyl, (C2- CöjHalogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-CejAlkoxy, (C 1 -O,) Halogcnal koxy, (Ci- CöjCyanoalkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci- CöjAlkoxyimino, ( C 1 -CA,) H alogenal koxy i m i no, (Ci-CejAlkylthio, (C 1 -G, ) Halogcnal kyl th io, (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-G)Alkylsulfinyl-(Ci- Cöjalkyl, ( C 1 - C 5) A 1 k y 1 s u 1 f n y 1 , ( C 1 - C 5) H a 1 gc n a 1 k y 1 s u 1 f n y 1 , (Ci-C6)Alkoxy-(Ci-C 6 ) haloalkylaminocarbonyl (Ci-C 6 ) alkyl-amino, or for a saturated, partially saturated or heteroaromatic ring which is optionally mono- or polysubstituted, identically or differently substituted and in which at least one carbon atom has been replaced by a heteroatom or for one single or multiple, identically or differently substituted, saturated or partially saturated carbocyclic ring or an aromatic ring, where in each case at least one carbonyl group can optionally be included and / or where the following are possible as substituents: cyano, carboxyl, halogen, nitro, acetyl, Hydroxy, amino, SCN, SF 5 , tri- (Ci-C 6 ) alkylsilyl, (C 3 -Cs) cycloalkyl, (C 3 -Cs) cycloalkyl- (C 3 -Cs) cycloalkyl, (Ci-C 6 ) alkyl - (C 3 -Cs) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, halo- (C 3 -Cs) cycloalkyl, cyano- (C 3 -Cs) cycloalkyl, (CVO,) alkyl , (C 1 -C 5) H a 1 gcna 1 ky 1, (Ci- C ö jCyanoalkyl, (Ci-CejCyanohalogenalkyl, (C 1 -CA,) Hydroxyalkyl, Hydro xycarbonyl- (Ci-C 6 ) - alkoxy, (Ci-C 6 ) alkoxycarbonyl- (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 - C ö jHalogenalkenyl, (C 2 -C 6) cyanoalkenyl, (C 3 -Cs) cycloalkyl (C 2) alkenyl, (C 2 -C 6) alkynyl, (C 2 - C ö jHalogenalkinyl, (C 2 -C 6 ) Cyanoalkynyl, (Ci-CejAlkoxy, (C 1 -O,) Halogcnal koxy, (Ci- C ö jCyanoalkoxy, (Ci-C 6 ) Alkoxycarbonyl- (Ci-C 6 ) alkoxy, (Ci- C 6 ) alkoxy (Ci-C 6 ) alkoxy, (Ci- C ö jalkoxyimino, (C 1 -CA,) H alogenal koxy imi no, (Ci-CejAlkylthio, (C 1 -G,) Halogcnal kyl thio, (Ci- C6) alkoxy (Ci-C 6) alkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) alkylsulfinyl, (Ci- C 6) haloalkylsulfinyl, (C -C 6 ) alkoxy- (Ci-C 6 ) alkylsulfinyl, (Ci-G) alkylsulfinyl- (Ci- C ö jalkyl, (C 1 -C 5) A 1 ky 1 su 1 fny 1, (C 1 -C 5 ) H a 1 gc na 1 ky 1 su 1 fny 1, (Ci-C 6 ) alkoxy- (Ci-
Cöjalkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, ( C 1 -C(t) A 1 ky 1 su Ifony loxy , (Ci-C ö jalkylsulfonyl, (Ci-C 6 ) alkylsulfonyl- (Ci-C 6 ) alkyl, (C 1 -C (t) A 1 ky 1 su Ifony loxy, (Ci-
C ,) Halogcnal ky 1 su Ifonyloxy, ( C 1 -C ,) A 1 ky learbony 1 , (C 1 -C ,) Halogcnal kylcarbonyl , (Ci- CölAlkylcarbonyloxy, ( C 1 -O,) A 1 koxycarbony 1 , (Ci-C ,) Halogcnal koxycarbonyl, Aminocarbonyl, (Ci-CejAlkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci-C,) Halogcnal ky 1 su Ifonyloxy, (C 1 -C,) A 1 ky learbony 1, (C 1 -C,) Halogcnal kylcarbonyl, (Ci- C ö lAlkylcarbonyloxy, (C 1 -O,) A 1 koxycarbony 1 , (Ci-C,) Halogcnal koxycarbonyl, aminocarbonyl, (Ci-CejAlkylaminocarbonyl, Di- (Ci-C 6 ) alkyl-aminocarbonyl, (Ci-
C6)Halogenalkylaminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-Ce)- alkenylaminocarbonyl, (C CslCycloal kyl aminocarbonyl, ( C 1 -CA,) A 1 ky 1 sulfony 1 am i no, (Ci- C6)Alkylamino, Di-(Ci-C6)Alkylamino, (C 1 -C ,) Halogcnal kylamino, (C3-Cs)Cycloalkylamino, Aminosulfonyl, ( C 1 - C 5) A 1 k y 1 a m i n s u 1 f n y 1 , Di-(Ci-C6)alkylaminosulfonyl, (Ci-C 6 ) haloalkylaminocarbonyl, (C 2 -C 6 ) alkenylaminocarbonyl, di- (C 2 -Ce) - alkenylaminocarbonyl, (C CslCycloal kyl aminocarbonyl, (C 1 -CA,) A 1 ky 1 sulfony 1 am i no, (Ci - C 6 ) alkylamino, di- (Ci-C 6 ) alkylamino, (C 1 -C,) haloalkylamino, (C 3 -Cs) cycloalkylamino, aminosulfonyl, (C 1 -C 5) A 1 ky 1 aminesu 1 fny 1, di- (Ci-C 6 ) alkylaminosulfonyl, (Ci-
C6)Alkylsulfoximino, Aminothiocarbonyl, (C 1 -CA ) A 1 kyl am i noth iocarbony 1 , Di-(Ci-C 6 ) alkylsulfoximino, aminothiocarbonyl, (C 1 -CA) A 1 kyl am i noth iocarbony 1, di- (Ci-
C6)alkylaminothiocarbonyl, (Ci-C ,) Halogcnal kyl aminothiocarbonyl, (C3-C 6 ) alkylaminothiocarbonyl, (Ci-C,) Halogcnal kyl aminothiocarbonyl, (C 3 -
CslCycloal kyl aminothiocarbonyl, (Ci-CejAlkylcarbonylamino, (Ci- C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-CslCycloal kyl aminothiocarbonyl, (Ci-CejAlkylcarbonylamino, (Ci- C 6 ) haloalkylcarbonylamino, (Ci-C 6 ) alkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3- C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Alkylthiocarbonylamino, (Ci-C 6 ) haloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (C3-C8) cycloalkylcarbonylamino, (C3- C 8 ) cycloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-C 6 ) alkylthiocarbonylamino, (Ci -
C6)Halogenalkylthiocarbonylamino, (Ci-C6)Alkylthiocarbonyl-(Ci-C6)alkyl-amino, (Ci-C 6 ) haloalkylthiocarbonylamino, (Ci-C 6 ) alkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylthiocarbonylamino, (C3- C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, Hetaryl, Oxo-Hetaryl, Halogen-Hetaryl, Halogen-Oxo-Hetaryl, Cyano-Hetaryl, Cyano-Oxo-Hetaryl, (Ci-C6)Halogenalkyl-Hetaryl oder (Ci-C6)Halogenalkyl-Oxo-Hetaryl, C 6 ) haloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (C3-C8) cycloalkylthiocarbonylamino, (C3- C 8 ) cycloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, hetaryl, oxo-hetaryl, halo-hetaryl, Halogen-oxo-hetaryl, cyano-hetaryl, cyano-oxo-hetaryl, (Ci-C 6 ) haloalkyl-hetaryl or (Ci-C 6 ) haloalkyl-oxo-hetaryl,
R4, R5, R6, R7 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (Ci-C3)Alkyl oder (Ci- C3)Halogenalkyl stehen, R 4 , R 5 , R 6 , R 7 independently of one another represent hydrogen, cyano, halogen, (Ci-C3) alkyl or (Ci- C3) haloalkyl,
Y für Sauerstoff, =N-H oder =N-CN steht, Y stands for oxygen, = N-H or = N-CN,
Z für -NR8, Sauerstoff oder Schwefel steht, wobei Z is -NR 8 , oxygen or sulfur, where
R8 für Wasserstoff, (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)Halogenalkinyl oder (C3-Cs)Cycloalkyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. R 8 for hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) hydroxyalkyl, (Ci-C 6 ) alkoxy (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkoxy- (Ci-C 6 ) alkyl, (C2-C6) alkenyl, (C2- C 6 ) alkenyloxy- (Ci-C 6 ) alkyl, (C2-C6) haloalkenyloxy- ( Ci-C6) alkyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C2-C6) alkynyl, (C2-C6) haloalkynyl or (C3-Cs) cycloalkyl, m is 0 or 1, n stands for 0 or 1.
Weiterhin wurde gefunden, dass die Verbindungen der Formel (I) 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. It has also been found that the compounds of the formula (I) are very effective as pesticides, preferably as insecticides and / or acaricides, and are generally very well tolerated by plants, in particular with respect to crop plants.
Die erfindungsgemäßen Verbindungen sind durch die Formel (I) 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 formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
Ausgestaltung 2-1 Design 2-1
R1 steht bevorzugt für (Ci-C- Alkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl oder (C3-C6)Cycloalkyl, R 1 preferably represents (Ci-C- alkyl, (Ci-C4) cyanoalkyl, (Ci-C4) alkoxy- (Ci-C4) alkyl, (Ci- C4) haloalkyl, (C2-C4) alkenyl, (C2- C4) haloalkenyl, (C2-C4) alkynyl, (C2- C4) haloalkynyl or (C3-C6) cycloalkyl,
R2 steht bevorzugt für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci- C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)Cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci- C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-R 2 preferably represents hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) cyanoalkyl, (Ci- C4) hydroxyalkyl, (Ci-C4) alkoxy- (Ci-C4) alkyl, ( Ci-C4) haloalkoxy- (Ci-C4) alkyl, (C 3 - C 6 ) cycloalkyl, (C3-C6) cycloalkyl- (C3-C6) cycloalkyl, (Ci-C4) alkyl- (C3-C6) cycloalkyl, Halogen (C 3 -C 6 ) cycloalkyl, cyano (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-
C4)Halogenalkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci- C4)Halogenalkylsulfonyl-(Ci-C4)alkyl, C 4 ) haloalkylsulfinyl (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfonyl (Ci-C 4 ) alkyl or (Ci- C 4 ) haloalkylsulfonyl (Ci-C 4 ) alkyl,
R3 steht bevorzugt für Wasserstoff, Halogen, Cyano, Nitro, (Ci-C6)Alkyl, (C3-Cs)Cycloalkyl, Cyano(C3-Cs)cycloalkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci- C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, SCN, (Ci-C6)Alkylcarbonyl, (Ci- C6)Halogenalkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl,R 3 preferably represents hydrogen, halogen, cyano, nitro, (Ci-C6) alkyl, (C 3 -Cs) cycloalkyl, cyano (C 3 -Cs) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy , (Ci-C6) haloalkoxy, (Ci-C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (Ci-C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, (Ci- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl,
Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci- C6)Halogenalkylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (Ci- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkylaminothiocarbonyl, (Ci-Aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-
C6)Halogenalkylaminothiocarbonyl, (C3-C8)Cycloalkylaminothiocarbonyl, Amino, (Ci- C6)Alkylamino, (Ci-C6)Halogenalkylamino, Di-(Ci-C6)Alkylamino, (C3-C8)Cycloalkylamino, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylcarbonylamino, (Ci-C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3-C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci- C6)Alkylthiocarbonylamino, (Ci-C6)Halogenalkylthiocarbonylamino, (Ci-CejAlkylthiocarbonyl- (Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C6) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, amino, (Ci- C6) alkylamino, (Ci-C6) haloalkylamino, di- (Ci-C6) alkylamino, (C 3 -C 8 ) cycloalkylamino, (Ci- C6) alkylsulfonylamino, (Ci-C6) alkylcarbonylamino, (Ci-C6) haloalkylcarbonylamino, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-C6) haloalkylcarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8 ) Cycloalkylcarbonylamino, (C 3 -C 8 ) Cycloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci- C6) Alkylthiocarbonylamino, (Ci-C6) Haloalkylthiocarbonylamino, (Ci-CejAlkylthiocarbonyl- (Ci- C6) alkyl-amino, (Ci-C6) haloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C 3 -
C8)Cycloalkylthiocarbonylamino, (C3-C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C2- Ce)Alkenyl, (C2-C6)Halogenalkenyl, (C2-Ce)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2- C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-C8)Cycloalkyl-(C2)alkinyl, (C3-Cs)Cycloalkyl-(Ci- C6)alkyl, (Ci-C6)Alkylaminocarbonylamino, Di-(Ci-C6)Alkylaminocarbonylamino, (C3- C8)Cycloalkylaminocarbonylamino, (Ci-C6)Halogenalkylaminocarbonylamino, (Ci-C8) Cycloalkylthiocarbonylamino, (C 3 -C 8 ) cycloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (C 2 -Ce) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -Ce) cyanoalkenyl, (C 3 -Cs) Cycloalkyl- (C 2 ) alkenyl, (C 2 - C6) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 8 ) cycloalkyl- (C 2 ) alkynyl, (C 3 -Cs) Cycloalkyl- (Ci- C6) alkyl, (Ci-C6) alkylaminocarbonylamino, di- (Ci-C6) alkylaminocarbonylamino, (C 3 - C8) cycloalkylaminocarbonylamino, (Ci-C6) haloalkylaminocarbonylamino, (Ci-
C6)Alkylaminocarbonyl-(Ci-C6)alkyl-amino, Di-(Ci-C6)Alkylaminocarbonyl-(Ci-C6)alkyl- amino, (C3-C8)Cycloalkylaminocarbonyl-(Ci-C6)alkyl-amino oder (Ci-C6) alkylaminocarbonyl- (Ci-C6) alkyl-amino, di- (Ci-C6) alkylaminocarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8 ) cycloalkylaminocarbonyl- (Ci-C 6 ) alkyl-amino or (Ci-
C6)Halogenalkylaminocarbonyl-(Ci-C6)alkyl-amino, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Cyclopentenyl oder Cyclohexenyl, wobei (im Fall von Hetaryl) gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und wobei als Substituenten jeweils in Frage kommen: Cyano, Carboxyl, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, SF5, Tri-(Ci- Cöjalkylsilyl, (C3-Cs)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-Cs)cycloalkyl, (Ci-C6)Alkyl-(C3- Csjcycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, Halogen-(C3-Cs)cycloalkyl, Cyano-(C3- Csjcycloalkyl, fC 1 -CA ) Al kyK ( C 1 -G,) H alogcnal ky 1, (Ci-CöjCyanoalkyl, (Ci-C6) Haloalkylaminocarbonyl- (Ci-C6) alkyl-amino, or for each optionally singly or multiply, identically or differently substituted aryl, hetaryl, cyclopentenyl or cyclohexenyl, where (in the case of hetaryl) at least one carbonyl group may optionally be included and where as substituents in each case are: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF 5, tri (Ci- C ö jalkylsilyl, (C 3 -Cs) cycloalkyl, (C 3 -C 8) cycloalkyl - (C 3 -Cs) cycloalkyl, (Ci-C 6 ) alkyl- (C 3 -Csjcycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, halo- (C 3 -Cs) cycloalkyl, cyano - (C3- Csjcycloalkyl, fC 1 -CA) Al kyK (C 1 -G,) H alogcnal ky 1, (Ci-C ö jCyanoalkyl, (Ci-
CöjCyanohalogenalkyl, ( C 1 -O,) H ydroxyal kyl , Hydroxycarbonyl-(Ci-C6)-alkoxy, (Ci- C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (C2-Ce)Alkenyl, (C2- CöjHalogenalkenyl, (C2-Ce)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2-C6)Alkinyl, (C2- C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C ö jCyanohalogenalkyl, (C 1 -O,) Hydroxyal kyl, Hydroxycarbonyl- (Ci-C6) -alkoxy, (Ci- C6) alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C6) Alkoxy- (Ci-C6 ) alkyl, (C 2 -Ce) alkenyl, (C 2 - C ö jhaloalkenyl, (C 2 -Ce) cyanoalkenyl, (C 3 -Cs) cycloalkyl- (C 2 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 - C6) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (Ci-C6) alkoxy, (Ci-C6) haloalkoxy, (Ci-
C6)Cyanoalkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci- C6)Alkoxyimino, (Ci-C6)Halogenalkoxyimino, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci- C6)Alkoxy-(Ci-C6)alkylthio, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfmyl, (Ci-C6) cyanoalkoxy, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkoxy, (Ci-C6) alkoxy- (Ci-C6) alkoxy, (Ci- C6) alkoxyimino, (Ci-C6) haloalkoxyimino, (Ci-C6 ) alkylthio, (Ci-C6) haloalkylthio, (Ci- C6) alkoxy (Ci-C 6) alkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfmyl, (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)Halogenalkylsulfonyloxy, (Ci-C6)Alkylcarbonyl, (Ci-C6)Halogenalkylcarbonyl, (Ci-C 6 ) haloalkylsulfinyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkylsulfinyl, (Ci-C 6 ) alkylsulfinyl- (Ci- C6) alkyl, (Ci-C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, (Ci-C6) alkoxy- (Ci-C6) alkylsulfonyl, (Ci-C6) alkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) alkylsulfonyloxy, (Ci-C6) haloalkylsulfonyloxy, (Ci-C6) alkylcarbonyl, ( Ci-C6) haloalkylcarbonyl, (Ci-
C6)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci-C6) alkylcarbonyloxy, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl, aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci-
C6)Halogenalkylaminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-Ce)- alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci- C6)Alkylamino, Di-(Ci-C6)Alkylamino, (Ci-C6)Halogenalkylamino, (C3-Cs)Cycloalkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci-C6)alkylaminosulfonyl, (Ci- C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci- C6)alkylaminothiocarbonyl, (Ci-C6)Halogenalkylaminothiocarbonyl, (C3-C6) haloalkylaminocarbonyl, (C 2 -C 6 ) alkenylaminocarbonyl, di- (C 2 -Ce) - alkenylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, (Ci-C6) alkylsulfonylamino, (Ci- C6) alkylamino, di- ( Ci-C6) alkylamino, (Ci-C6) haloalkylamino, (C 3 -Cs) cycloalkylamino, aminosulfonyl, (Ci-C6) alkylaminosulfonyl, di- (Ci-C6) alkylaminosulfonyl, (Ci-C6) alkylsulfoximino, aminothiocarbonyl, (Ci -C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-C6) haloalkylaminothiocarbonyl, (C 3 -
C8)Cycloalkylaminothiocarbonyl, (Ci-C6)Alkylcarbonylamino, (Ci-C8) Cycloalkylaminothiocarbonyl, (Ci-C6) Alkylcarbonylamino, (Ci-
C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6) haloalkylcarbonylamino, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-Cs)Cycloalkylcarbonylamino, (C3- C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Alkylthiocarbonylamino, (Ci-C6) Haloalkylcarbonyl- (Ci-C6) alkyl-amino, (C 3 -Cs) Cycloalkylcarbonylamino, (C 3 - C8) Cycloalkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-C6) Alkylthiocarbonylamino, (Ci-
C6)Halogenalkylthiocarbonylamino, (Ci-C6)Alkylthiocarbonyl-(Ci-C6)alkyl-amino, (Ci-C6) haloalkylthiocarbonylamino, (Ci-C6) alkylthiocarbonyl- (Ci-C6) alkyl-amino, (Ci-
C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylthiocarbonylamino, (C3- C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, Hetaryl, Oxo-Hetaryl, Halogen-Hetaryl, Halogen-Oxo-Hetaryl, Cyano-Hetaryl, Cyano-Oxo-Hetaryl, (Ci-C6)Halogenalkyl-Hetaryl oder (Ci-C6)Halogenalkyl-Oxo-Hetaryl, C6) haloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8 ) cycloalkylthiocarbonylamino, (C 3 -C8) cycloalkylthiocarbonyl- (Ci-C6) alkyl-amino, hetaryl, oxo-hetaryl, halo-hetaryl, halogen -Oxo-hetaryl, cyano-hetaryl, cyano-oxo-hetaryl, (Ci-C6) haloalkyl-hetaryl or (Ci-C6) haloalkyl-oxo-hetaryl,
R4, R5, R6, R7 stehen bevorzugt unabhängig voneinander für Wasserstoff, Cyano, Halogen, (Ci- C3)Alkyl oder (Ci-C3)Halogenalkyl, R 4 , R 5 , R 6 , R 7 are preferably, independently of one another, hydrogen, cyano, halogen, (Ci- C 3 ) alkyl or (Ci-C 3 ) haloalkyl,
Y steht bevorzugt für Sauerstoff, =N-H oder =N-CN, Y preferably represents oxygen, = N-H or = N-CN,
Z steht bevorzugt für -NR8, Sauerstoff oder Schwefel, wobei Z preferably represents -NR 8 , oxygen or sulfur, where
R8 bevorzugt für Wasserstoff, (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)Halogenalkinyl oder (C3- C6)Cycloalkyl steht, m steht bevorzugt für 0 oder 1, n steht bevorzugt für 0 oder 1. R 8 is preferably hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci- C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy (Ci-C alkyl 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) -haloalkynyl or ( C 3 -C 6) cycloalkyl, m is preferably 0 or 1, n preferably represents 0 or 1.
Ausgestaltung 3-1 Design 3-1
R1 steht besonders bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-R 1 particularly preferably represents (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -
C4)Halogenalkenyl oder (C3-C6)Cycloalkyl, C 4 ) haloalkenyl or (C 3 -C 6 ) cycloalkyl,
R2 steht besonders bevorzugt für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-R 2 particularly preferably represents hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -
C6)Cycloalkyl oder Halogen(C3-C6)cycloalkyl, C6) cycloalkyl or halogen (C 3 -C 6 ) cycloalkyl,
R3 steht besonders bevorzugt für Wasserstoff, Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, Cyano(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci- C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, Amino, (Ci-C4)Alkylamino, (Ci-C4)Halogenalkylamino, Di-(Ci-C4)Alkylamino, (C3-C6)Cycloalkylamino, (Ci- C4)Alkylsulfonylamino, (Ci-C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci- C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3- C6)Cycloalkylcarbonylamino, (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3-C6)Cycloalkyl-(C2)alkenyl, oder besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Furanyl, Pyrazolyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei (im Fall von Hetaryl) gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und wobei als Substituenten jeweils in Frage kommen: Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SF5, (C3-C6)Cycloalkyl, (Ci- C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci- C4)Cyanohalogenalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C3-C6)Cycloalkyl-(C2)alkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci- C4)Cyanoalkoxy, (Ci-C4)Alkoxy-(Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci-R 3 particularly preferably represents hydrogen, halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4) alkoxy, (Ci-C 4) haloalkoxy, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci C 4) Halogenalkylaminocarbonyl, (C 3 -C 6) Cycloalkylaminocarbonyl, amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, di- (Ci-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci- C 4 ) alkylsulfonylamino, (Ci- C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci- C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, ( C 3 -C 6 ) cycloalkylcarbonylamino, (C 3 -C 6 ) cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) Cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or particularly preferably for phenyl, pyridyl, pyrimidyl, pyridazinyl, each optionally substituted one or more times, identically or differently , Thiophenyl, furanyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, where (in the case of hetaryl) at least one carbonyl group can optionally be included and where the following are possible as substituents: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl- (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl, cyano- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci- C 4 ) cyanohaloalkyl, (Ci- C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C alkyl 2), (C 2 -C 4) alkenyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 3 -C 6) cycloalkyl- (C alkenyl 2), (C 2 -C 4) alkynyl, (C 2 - C 4) haloalkynyl, (C 2 -C 4) cyanoalkynyl, (Ci-C 4) alkoxy, (C -C 4 ) haloalkoxy, (Ci- C 4 ) cyanoalkoxy, (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkoxy, (Ci-C 4 ) alkoxyimino, (Ci-
C4)Halogenalkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylthio-(Ci- C2)alkyl, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci- C4)Halogenalkylsulfonyl, (Ci-C4)Alkylsulfonyloxy, (Ci-C4)Halogenalkylsulfonyloxy, (Ci- C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, (Ci-C4)Halogenalkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (C3-C 4 ) haloalkoxyimino, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylthio- (Ci- C 2 ) alkyl, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci- C4) haloalkylsulfonyl, (Ci-C4) alkylsulfonyloxy, (Ci-C 4) haloalkylsulfonyloxy, (Ci- C4) alkylcarbonyl, (Ci-C4) haloalkylcarbonyl , Aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (Ci-C 4 ) haloalkylaminocarbonyl, di- (Ci-C 4 ) alkyl-aminocarbonyl, (C 3 -
GjCycloalkyl aminocarbonyl, Aminothiocarbonyl, (Ci-C4)Alkylaminothiocarbonyl, Di-(Ci- C4)alkylaminothiocarbonyl, (Ci-C4)Halogenalkylaminothiocarbonyl, (C3-GjCycloalkyl aminocarbonyl, aminothiocarbonyl, (Ci-C 4 ) alkylaminothiocarbonyl, di- (Ci- C 4 ) alkylaminothiocarbonyl, (Ci-C 4 ) haloalkylaminothiocarbonyl, (C 3 -
Cf.lCycloalkyl aminothiocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, Aminosulfonyl, (Ci- C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl, (Ci-C4)Alkylcarbonylamino, (Ci- C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C f .lCycloalkyl aminothiocarbonyl, (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl , (Ci- C 4 ) alkylaminosulfonyl, di- (Ci-C 4 ) alkyl-aminosulfonyl, (Ci-C 4 ) alkylcarbonylamino, (Ci- C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino , (Ci-
C2)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylcarbonylamino, (C3- C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Alkylthiocarbonylamino, (Ci-C 2) haloalkylcarbonyl (Ci-C 2) alkyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, (C 3 - C 6) cycloalkylcarbonyl (Ci-C 2) alkyl amino, (Ci-C4) alkylthiocarbonylamino , (Ci-
C4)Halogenalkylthiocarbonylamino, (Ci-C4)Alkylthiocarbonyl-(Ci-C2)alkyl-amino, (Ci-C 4 ) haloalkylthiocarbonylamino, (Ci-C 4 ) alkylthiocarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-
C4)Halogenalkylthiocarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylthiocarbonylamino oder (C3-C6)Cycloalkylthiocarbonyl-(Ci-C2)alkyl-amino, C 4 ) haloalkylthiocarbonyl- (Ci-C 2 ) alkyl-amino, (C 3 -C 6 ) cycloalkylthiocarbonylamino or (C 3 -C 6 ) cycloalkylthiocarbonyl- (Ci-C 2 ) alkyl-amino,
R4, R5, R6, R7 sind besonders bevorzugt identisch und stehen entweder für Wasserstoff oder für Fluor,R 4 , R 5 , R 6 , R 7 are particularly preferably identical and are either hydrogen or fluorine,
Y steht besonders bevorzugt für Sauerstoff oder =N-H, Y particularly preferably represents oxygen or = N-H,
Z steht besonders bevorzugt für -NR8 oder Sauerstoff, wobei Z particularly preferably represents —NR 8 or oxygen, where
R8 besonders bevorzugt für Wasserstoff oder (Ci-C4)Alkyl steht, m steht besonders bevorzugt für 0 oder 1 , n steht besonders bevorzugt für 0 oder 1. R 8 particularly preferably represents hydrogen or (Ci-C 4 ) alkyl, m particularly preferably represents 0 or 1, n particularly preferably represents 0 or 1.
Ausgestaltung 3-2 Design 3-2
R1 steht besonders bevorzugt für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-R 1 particularly preferably represents (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -
C4)Halogenalkenyl oder (C3-C6)Cycloalkyl, C 4 ) haloalkenyl or (C 3 -C 6 ) cycloalkyl,
R2 steht besonders bevorzugt für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-R 2 particularly preferably represents hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -
C6)Cycloalkyl oder Halogen(C3-C6)cycloalkyl, C6) cycloalkyl or halogen (C 3 -C 6 ) cycloalkyl,
R3 steht besonders bevorzugt für Wasserstoff, Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, Cyano(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci- C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, Amino, (Ci-C4)Alkylamino, (Ci-C4)Halogenalkylamino, Di-(Ci-C4)Alkylamino, (C3-C6)Cycloalkylamino, (Ci- C4)Alkylsulfonylamino, (Ci-C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci- C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3- C6)Cycloalkylcarbonylamino, (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3-C6)Cycloalkyl-(C2)alkenyl, oder besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Furanyl, Pyrazolyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei (im Fall von Hetaryl) gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und wobei als Substituenten jeweils in Frage kommen: Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SF5, (C3-C6)Cycloalkyl, (Ci- C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-R 3 particularly preferably represents hydrogen, halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4) alkoxy, (Ci-C 4) haloalkoxy, aminocarbonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci C 4) Halogenalkylaminocarbonyl, (C 3 -C 6) Cycloalkylaminocarbonyl, amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, di- (Ci-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci- C 4 ) alkylsulfonylamino, (Ci- C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci- C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, ( C 3 -C 6 ) cycloalkylcarbonylamino, (C 3 -C 6 ) cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) Cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or particularly preferably for phenyl, pyridyl, pyrimidyl, pyridazinyl, each optionally substituted one or more times, identically or differently , Thiophenyl, furanyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, where (in the case of hetaryl) at least one carbonyl group may optionally be included and where as substituents in each case come: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl - (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl, cyano- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4 ) cyanoalkyl, (Ci-
C4)Cyanohalogenalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (C2-C4)Alkenyl, (C2- C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl, (C3-C6)Cycloalkyl-(C2)alkenyl, (C2-C4)Alkinyl, (C2- C4)Halogenalkinyl, (C2-C4)Cyanoalkinyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C 4) Cyanohalogenalkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C alkyl 2), (C 2 -C 4) alkenyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 3 -C 6) cycloalkyl- (C alkenyl 2), (C 2 -C 4) alkynyl, (C 2 - C 4) haloalkynyl, (C 2 -C 4) cyanoalkynyl, (C -C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci-
C4)Cyanoalkoxy, (Ci-C4)Alkoxy-(Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci-C 4 ) cyanoalkoxy, (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkoxy, (Ci-C 4 ) alkoxyimino, (Ci-
C4)Halogenalkoxyimino, (Ci-C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylthio-(Ci- C2)alkyl, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C 4 ) haloalkoxyimino, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylthio- (Ci- C 2 ) alkyl, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) Haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-
C4)Halogenalkylsulfonyl, (Ci-C4)Alkylsulfonyloxy, (Ci-C4)Halogenalkylsulfonyloxy, (Ci-C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylsulfonyloxy, (Ci-C 4 ) haloalkylsulfonyloxy, (Ci-
C4)Alkylcarbonyl, (Ci-C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, (Ci-C4)Halogenalkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (C3-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (Ci-C 4 ) haloalkylaminocarbonyl, di- (Ci-C 4 ) alkyl-aminocarbonyl, (C 3 -
C6)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (Ci-C4)Alkylaminothiocarbonyl, Di-(Ci- C4)alkylaminothiocarbonyl, (Ci-C4)Halogenalkylaminothiocarbonyl, (C3-C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci-C 4 ) alkylaminothiocarbonyl, di- (Ci- C 4 ) alkylaminothiocarbonyl, (Ci-C 4 ) haloalkylaminothiocarbonyl, (C 3 -
C6)Cycloalkylaminothiocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, Aminosulfonyl, (Ci- C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl, (Ci-C4)Alkylcarbonylamino, (Ci-C 6 ) Cycloalkylaminothiocarbonyl, (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl, (Ci- C 4 ) alkylaminosulfonyl, di- (Ci-C 4 ) alkyl-aminosulfonyl, (Ci-C 4 ) alkylcarbonylamino, (Ci-
C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-
C2)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylcarbonylamino, (C3- C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Alkylthiocarbonylamino, (Ci-C 2) haloalkylcarbonyl (Ci-C 2) alkyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, (C 3 - C 6) cycloalkylcarbonyl (Ci-C 2) alkyl amino, (Ci-C4) alkylthiocarbonylamino , (Ci-
C4)Halogenalkylthiocarbonylamino, (Ci-C4)Alkylthiocarbonyl-(Ci-C2)alkyl-amino, (Ci-C 4 ) haloalkylthiocarbonylamino, (Ci-C 4 ) alkylthiocarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-
C4)Halogenalkylthiocarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylthiocarbonylamino, (C3- C6)Cycloalkylthiocarbonyl-(Ci-C2)alkyl-amino oder gegebenenfalls durch Halogen substituiertes Pyridyl, C 4) Halogenalkylthiocarbonyl- (Ci-C 2) alkyl-amino, (C 3 -C 6) Cycloalkylthiocarbonylamino, (C 3 - C 6) Cycloalkylthiocarbonyl- (Ci-C 2) alkyl-amino or optionally halogen-substituted pyridyl,
R4, R5, R6, R7 sind besonders bevorzugt identisch und stehen entweder für Wasserstoff oder für Fluor, Y steht besonders bevorzugt für Sauerstoff oder =N-H, R 4 , R 5 , R 6 , R 7 are particularly preferably identical and either represent hydrogen or fluorine, Y particularly preferably represents oxygen or = NH,
Z steht besonders bevorzugt für -NR8 oder Sauerstoff, wobei Z particularly preferably represents —NR 8 or oxygen, where
R8 besonders bevorzugt für Wasserstoff oder (Ci-C4)Alkyl steht, m steht besonders bevorzugt für 0 oder 1 , n steht besonders bevorzugt für 0 oder 1. R 8 particularly preferably represents hydrogen or (Ci-C 4 ) alkyl, m particularly preferably represents 0 or 1, n particularly preferably represents 0 or 1.
Ausgestaltung 4-1 Design 4-1
R1 steht ganz besonders bevorzugt für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl, R 1 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or Pentafluoroethyl,
R2 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl, R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, Difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R3 steht ganz besonders bevorzugt für Wasserstoff, Halogen, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3- C6)Cycloalkyl-(C2)alkenyl, oder ganz besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Acetyl, Hydroxy, Amino, SF5, ( N-CejCycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl-(C3- Cöjcycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-Cs)cycloalkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkoxy-(Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci- C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci-C4)Alkylcarbonyl, Aminocarbonyl, (Ci- C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, (Ci-R 3 very particularly preferably represents hydrogen, halogen, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or very particularly preferably for each optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the Molecule bridged - phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or imidazolyl, whereby the following are possible as substituents: cyano, fluorine, chlorine, bromine, nitro, acetyl, hydroxy, amino, SF 5 , (N-CejCycloalkyl , (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) haloalkyl (C 3 - C ö jcycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) Alkyl, cyano- (C 3 -Cs) cycloalkyl, (Ci- C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkyl, (Ci C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkoxy- (Ci-C2) alkoxy, (Ci-C4) alkoxyimino, (C - C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci- C 4 ) alkylsulfonyl, (Ci-C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylcarbonyl, aminocarbonyl, (Ci- C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkyl aminocarbonyl, (Ci-C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, (Ci-C 4 ) alkylsulfonylamino , (Ci-C 4 ) alkylamino, di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci-
C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-
C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 3 -
C6)Cycloalkylcarbonylamino oder (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, oder ganz besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes - Pyrazolyl, Triazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Hydroxy, Amino, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy oder Aminocarbonyl, C6) Cycloalkylcarbonylamino or (C 3 -C 6 ) cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, or very particularly preferably for each optionally mono- or polysubstituted, identically or differently substituted - pyrazolyl bridged via a nitrogen atom to the remainder of the molecule, Triazolyl or imidazolyl, with possible substituents in each case: cyano, fluorine, chlorine, bromine, nitro, hydroxy, amino, (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl, (Ci- C 4 ) haloalkyl , (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy or aminocarbonyl,
R4, R5, R6, R7 sind ganz besonders bevorzugt identisch und stehen entweder für Wasserstoff oder für Fluor, R 4 , R 5 , R 6 , R 7 are very particularly preferably identical and are either hydrogen or fluorine,
Y steht ganz besonders bevorzugt für Sauerstoff oder =N-H, Y very particularly preferably represents oxygen or = N-H,
Z steht ganz besonders bevorzugt für -NR8 oder Sauerstoff, wobei Z very particularly preferably represents —NR 8 or oxygen, where
R8 ganz besonders bevorzugt für Wasserstoff oder Methyl steht, m steht ganz besonders bevorzugt für 0 oder 1 , n steht ganz besonders bevorzugt für 0 oder 1. R 8 very particularly preferably represents hydrogen or methyl, m very particularly preferably represents 0 or 1, n very particularly preferably represents 0 or 1.
Ausgestaltung 4-2 Design 4-2
R1 steht ganz besonders bevorzugt für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl, R 1 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R2 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.-Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl, R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, Difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R3 steht ganz besonders bevorzugt für Wasserstoff, Halogen, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci- C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3- C6)Cycloalkyl-(C2)aIkenyl, oder ganz besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Acetyl, Hydroxy, Amino, SF5, (TN-CejCycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl-(C3- Gjcycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-Cs)cycloalkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (Ci- C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Alkoxy-(Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci- C4)Alkylthio, (Ci-C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci- C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci-C4)Alkylcarbonyl, Aminocarbonyl, (Ci- C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, (Ci-R 3 very particularly preferably represents hydrogen, halogen, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or very particularly preferably for each optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the Molecular bridges - phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or imidazolyl, whereby the following are possible as substituents: cyano, fluorine, chlorine, bromine, nitro, acetyl, hydroxy, amino, SF 5 , (TN-CejCycloalkyl , (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) haloalkyl (C 3 - Gjcycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, Cyano- (C 3 -Cs) cycloalkyl, (Ci- C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkyl, alkoxy (Ci -C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkoxy (Ci-C 2), (Ci-C4) alkoxyimino, (Ci- C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci- C 4 ) alkylsulfonyl, (Ci-C 4 ) haloalkylsulfonyl, (Ci-C 4 ) Alkylcarbonyl, aminocarbonyl, (Ci- C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkyl aminocarbonyl, (Ci-C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, (Ci-C 4 ) alkylsulfonylamino, ( Ci-C 4 ) alkylamino, di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci-
C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-
C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 3 -
C6)Cycloalkylcarbonylamino, (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino oder gegebenenfalls einfach durch Chlor oder Brom substituiertes Pyridyl, oder ganz besonders bevorzugt für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes - Pyrazolyl, Triazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Hydroxy, Amino, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl, (Ci- C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy oder Aminocarbonyl, R4, R5, R6, R7 sind ganz besonders bevorzugt identisch und stehen entweder für Wasserstoff oder für Fluor, C 6 ) Cycloalkylcarbonylamino, (C 3 -C 6 ) cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino or pyridyl which is optionally monosubstituted by chlorine or bromine, or very particularly preferably in each case monosubstituted or polysubstituted, identically or differently substituted - via a nitrogen atom bridged to the remainder of the molecule - pyrazolyl, triazolyl or imidazolyl, with possible substituents in each case: cyano, fluorine, chlorine, bromine, nitro, hydroxy, amino, (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) Alkyl, (Ci- C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy or aminocarbonyl, R 4 , R 5 , R 6 , R 7 are very particularly preferably identical and are either hydrogen or fluorine,
Y steht ganz besonders bevorzugt für Sauerstoff oder =N-H, Y very particularly preferably represents oxygen or = N-H,
Z steht ganz besonders bevorzugt für -NR8 oder Sauerstoff, wobei Z very particularly preferably represents —NR 8 or oxygen, where
R8 ganz besonders bevorzugt für Wasserstoff oder Methyl steht, m steht ganz besonders bevorzugt für 0 oder 1 , n steht ganz besonders bevorzugt für 0 oder 1. R 8 very particularly preferably represents hydrogen or methyl, m very particularly preferably represents 0 or 1, and n very particularly preferably represents 0 or 1.
Ausgestaltung 5-1 Design 5-1
R1 steht hervorgehoben für Ethyl, R 1 is highlighted for ethyl,
R2 steht hervorgehoben für Methyl, R 2 is highlighted for methyl,
R3 steht hervorgehoben für Brom, Cyclopropyl, Trifluormethyl, Tetrafluorethyl, Pentafluorethyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, SFs, 2-Cyano-2-propyl, Cyclopropyl, 1 -Cyano- 1 -cyclopropyl, 1- Fluor-1 -cyclopropyl oder 1 -Trifluormethyl- 1 -cyclopropyl, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Trifluormethyl oder Cyclopropyl, R 3 is emphasized for bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl or for phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or each optionally substituted one or more times, identically or differently - bridged via a carbon atom to the remainder of the molecule Imidazolyl, where the possible substituents are: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SFs, 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1- Fluorine-1-cyclopropyl or 1-trifluoromethyl-1-cyclopropyl, or for optionally monosubstituted -triazolyl bridged via a nitrogen atom to the remainder of the molecule, where possible substituents are: cyano, fluorine, chlorine, bromine, trifluoromethyl or cyclopropyl ,
R4, R5, R6, R7 stehen hervorgehoben für Fluor, R 4 , R 5 , R 6 , R 7 are highlighted for fluorine,
Y steht hervorgehoben für Sauerstoff oder =N-H, Y is highlighted for oxygen or = N-H,
Z steht hervorgehoben für -NR8, wobei Z is highlighted for -NR 8 , where
R8 hervorgehoben für Wasserstoff oder Methyl steht, m steht hervorgehoben für 0 oder 1 , n steht hervorgehoben für 0 oder 1. Ausgestaltung 5-2 R 8 is highlighted hydrogen or methyl, m is highlighted 0 or 1, n is highlighted 0 or 1. Design 5-2
R1 steht hervorgehoben für Ethyl, R 1 is highlighted for ethyl,
R2 steht hervorgehoben für Methyl, R 2 is highlighted for methyl,
R3 steht hervorgehoben für Wasserstoff, Brom, Cyclopropyl, Trifluormethyl, Tetrafluorethyl, Pentafluorethyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, SFs, 2-Cyano-2-propyl, Cyclopropyl, 1 -Cyano- 1 -cyclopropyl, 1- Fluor-1 -cyclopropyl, 1 -Trifluormethyl- 1 -cyclopropyl oder gegebenenfalls einfach durch Chlor oder Brom substituiertes Pyridyl, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Trifluormethyl oder Cyclopropyl, R 3 is emphasized for hydrogen, bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl or for phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl which is optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the molecule, Oxazolyl or imidazolyl, with possible substituents in each case: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SFs, 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1- fluoro-1 -cyclopropyl, 1-trifluoromethyl- 1 -cyclopropyl or optionally monosubstituted pyridyl, or optionally monosubstituted triazolyl bridged to the remainder of the molecule via a nitrogen atom, the possible substituents being: Cyano, fluorine, chlorine, bromine, trifluoromethyl or cyclopropyl,
R4, R5, R6, R7 stehen hervorgehoben für Fluor, R 4 , R 5 , R 6 , R 7 are highlighted for fluorine,
Y steht hervorgehoben für Sauerstoff oder =N-H, Y is highlighted for oxygen or = N-H,
Z steht hervorgehoben für -NR8, wobei Z is highlighted for -NR 8 , where
R8 hervorgehoben für Wasserstoff oder Methyl steht, m steht hervorgehoben für 0 oder 1 , n steht hervorgehoben für 0 oder 1. R 8 is highlighted hydrogen or methyl, m is highlighted 0 or 1, n is highlighted 0 or 1.
Ausgestaltung 6-la Design 6-la
R1 steht insbesonders für Ethyl, R 1 stands in particular for ethyl,
R2 steht insbesonders für Methyl, R 2 especially stands for methyl,
R3 steht insbesonders für Brom, Cyclopropyl, oder für gegebenenfalls einfach durch Fluor, Chlor, Brom, Trifluormethyl, 1 -Cyano- 1- cy clopropyl, 1 -Trifluormethyl- 1 -cyclopropyl oder 1 -Fluor- 1 -cyclopropyl substituiertes Phenyl, oder für gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Pyridyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Chlor, Brom, Cy clopropyl oder 1 -Cyano- 1-cyclopropyl, oder für jeweils gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Thiophenyl oder Thiazolyl, wobei als Substituenten jeweils in Frage kommen: Chlor oder 1 -Cyano- 1-cyclopropyl, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl, wobei als Substituenten jeweils in Frage kommen: Cyclopropyl. R 3 stands in particular for bromine, cyclopropyl, or for phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl, or for optionally monosubstituted - via a carbon atom to the rest of the molecule bridged - pyridyl, with possible substituents in each case: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl, or for each optionally monosubstituted - thiophenyl or thiazolyl which is bridged via a carbon atom to the remainder of the molecule, where Possible substituents in each case are: chlorine or 1-cyano-1-cyclopropyl, or for optionally monosubstituted -triazolyl bridged via a nitrogen atom to the remainder of the molecule, the possible substituents being: cyclopropyl.
R4, R5, R6, R7 stehen insbesonders für Fluor, R 4 , R 5 , R 6 , R 7 in particular represent fluorine,
Y steht insbesonders für Sauerstoff, Y especially stands for oxygen,
Z steht insbesonders für NR8, wobei Z in particular stands for NR 8 , where
R8 insbesonders für Wasserstoff oder Methyl steht, m und n stehen insbesonders für 0 oder m und n stehen insbesonders für 1. R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1.
Ausgestaltung 6-lb 6-lb design
R1 steht insbesonders für Ethyl, R 1 stands in particular for ethyl,
R2 steht insbesonders für Methyl, R 2 especially stands for methyl,
R3 steht insbesonders für Brom, Cyclopropyl, oder für gegebenenfalls einfach durch Fluor, Chlor, Brom, Trifluormethyl, 1 -Cyano- 1- cy clopropyl, 1 -Trifluormethyl- 1-cyclopropyl oder 1 -Fluor- 1-cyclopropyl substituiertes Phenyl,R 3 stands in particular for bromine, cyclopropyl, or for phenyl which is optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl,
R4, R5, R6, R7 stehen insbesonders für Fluor, R 4 , R 5 , R 6 , R 7 in particular represent fluorine,
Y steht insbesonders für Sauerstoff, Y especially stands for oxygen,
Z steht insbesonders für NR8, wobei Z in particular stands for NR 8 , where
R8 insbesonders für Wasserstoff oder Methyl steht, m und n stehen insbesonders für 0 oder m und n stehen insbesonders für 1. Ausgestaltung 6-2 R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1. Design 6-2
R1 steht insbesonders für Ethyl, R 1 stands in particular for ethyl,
R2 steht insbesonders für Methyl, R 2 especially stands for methyl,
R3 steht insbesonders für Wasserstoff, Brom, Cy clopropyl, oder für gegebenenfalls einfach durch Fluor, Chlor, Brom, Trifluormethyl, 1 -Cyano- 1- cy clopropyl, 1 -Trifluormethyl- 1-cyclopropyl oder 1 -Fluor- 1-cyclopropyl substituiertes Phenyl, oder für gegebenenfalls zweifach gleich oder verschieden durch Fluor, Chlor, Brom, Cyano substituiertes Phenyl, oder für gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Pyridyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Chlor, Brom, Cy clopropyl, 1 -Cyano- 1-cyclopropyl oder einfach durch Chlor oder Brom substituiertes Pyridyl (wobei Pyridyl über ein Kohlenstoffatom zum Rest des Moleküls verbrückt ist), oder für jeweils gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Thiophenyl oder Thiazolyl, wobei als Substituenten jeweils in Frage kommen: Chlor, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl, wobei als Substituenten jeweils in Frage kommen: Cyclopropyl. R 3 stands in particular for hydrogen, bromine, cyclopropyl, or for optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl Phenyl, or for phenyl which is optionally twice, identically or differently substituted by fluorine, chlorine, bromine, cyano, or for optionally monosubstituted - pyridyl which is bridged via a carbon atom to the remainder of the molecule, where possible substituents are in each case: cyano, chlorine, bromine , Cyclopropyl, 1-cyano-1-cyclopropyl or pyridyl which is monosubstituted by chlorine or bromine (where pyridyl is bridged via a carbon atom to the remainder of the molecule), or for each optionally monosubstituted - bridged via a carbon atom to the remainder of the molecule - thiophenyl or thiazolyl, where possible substituents in each case are: chlorine, or for optionally monosubstituted - via a nitrogen atom to Re st of the molecule bridged -triazolyl, with possible substituents in each case: cyclopropyl.
R4, R5, R6, R7 stehen insbesonders für Fluor, R 4 , R 5 , R 6 , R 7 in particular represent fluorine,
Y steht insbesonders für Sauerstoff oder =N-H, Y especially stands for oxygen or = N-H,
Z steht insbesonders für NR8, wobei In particular, Z stands for NR 8 , where
R8 insbesonders für Wasserstoff oder Methyl steht, m und n stehen insbesonders für 0 oder m und n stehen insbesonders für 1. R 8 in particular stands for hydrogen or methyl, m and n in particular for 0 or m and n in particular for 1.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I), wobei Y für Sauerstoff, m = 1, n = 1 steht und R1, R2, R3, R4, R5, R6, R7, R8 und Z die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) oder Ausgestaltung (6-la) oder Ausgestaltung (6-lb) oder Ausgestaltung (6-2) angegebenen Bedeutungen haben. In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I), wobei R4, R5, R6, R7 für Fluor stehen und R1, R2, R3, R8, Y, Z, n und m die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4- 2) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) oder Ausgestaltung (6-la) oder Ausgestaltung (6- lb) oder Ausgestaltung (6-2) angegebenen Bedeutungen haben. In a preferred embodiment, the invention relates to compounds of the formula (I), where Y is oxygen, m = 1, n = 1 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 4 8 and Z denote in configuration (1-1) or configuration (2-1) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or configuration (5 -1) or design (5-2) or design (6-la) or design (6-lb) or design (6-2) have given meanings. In a preferred embodiment, the invention relates to compounds of the formula (I), where R 4 , R 5 , R 6 , R 7 are fluorine and R 1 , R 2 , R 3 , R 8 , Y, Z, n and m are the in design (1-1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4- 2) or design (5-1) or Design (5-2) or design (6-la) or design (6- lb) or design (6-2) have given meanings.
In einer bevorzugten Ausführungsform betrifft die Erfindung Verbindungen der Formel (I), wobei R1 für Etyhl steht, R2 für Methyl steht, R4, R5, R6, R7 für Fluor stehen, Z für N-Methyl steht und R3, Y, n und m die in Ausgestaltung (1-1) oder Ausgestaltung (2-1) oder Ausgestaltung (3-1) oder Ausgestaltung (3-2) oder Ausgestaltung (4-1) oder Ausgestaltung (4-2) oder Ausgestaltung (5-1) oder Ausgestaltung (5-2) oder Ausgestaltung (6-la) oder Ausgestaltung (6-lb) oder Ausgestaltung (6-2) angegebenen Bedeutungen haben. In a preferred embodiment, the invention relates to compounds of the formula (I), where R 1 is ethyl, R 2 is methyl, R 4 , R 5 , R 6 , R 7 are fluorine, Z is N-methyl and R is 3 , Y, n and m those in configuration (1-1) or configuration (2-1) or configuration (3-1) or configuration (3-2) or configuration (4-1) or configuration (4-2) or embodiment (5-1) or embodiment (5-2) or embodiment (6-la) or embodiment (6-lb) or embodiment (6-2) have given meanings.
In den allgemeinen oder in Vorzugsbereichen aufgeführten Definitionen ist, sofern nichts anderes angegeben ist, Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom. In the definitions given in general or in areas of preference, unless stated otherwise, halogen is selected from the series fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
Aryl (auch als Teil einer größeren Einheit, wie beispielsweise Arylalkyl) ist, sofern nicht an anderer Stelle anders definiert, ausgewählt aus der Reihe Phenyl, Naphthyl, Anthryl, Phenanthrenyl und steht wiederum bevorzugt für Phenyl. Unless otherwise defined, aryl (also as part of a larger unit, such as arylalkyl) is selected from the series phenyl, naphthyl, anthryl, phenanthrenyl and, in turn, is preferably phenyl.
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 C1-C12- 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 C 1 -CY 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 haloalkyl, in the context of the present invention is understood to mean a residue of a saturated, aliphatic hydrocarbon group with 1 to 12 carbon atoms, which can be branched or unbranched. Examples of C1-C12-alkyl radicals are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, 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 -CY alkyl radicals are particularly preferred. Ci-C4-alkyl radicals are 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 is a linear or branched C2-Ci2-alkenyl radical which has at least one double bond, for example vinyl, allyl, 1 -Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2 -Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, understood. Of these, C2-C6-alkenyl radicals are preferred and C2-C4-alkenyl radicals are particularly preferred.
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 CVCVAlkinylrcstc und besonders bevorzugt sind C3-C4-Alkinylreste. Der Alkinylrest kann dabei auch mindestens eine Doppelbindung aufweisen. Unless otherwise defined, the term “alkynyl”, either alone or in combination with other terms, according to the invention is a linear or branched C2-Ci2-alkynyl radical which has at least one triple bond, for example Ethynyl, 1-propynyl and propargyl. Of these, CVCV-alkynyl radicals are preferred and C3-C4-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, the term “cycloalkyl”, either alone or in combination with other terms, is understood according to the invention to be a C3-C8 cycloalkyl radical, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl . Of these, C3-C6-cycloalkyl radicals are preferred.
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 on its own or in combination with other terms such as haloalkoxy, is understood in the present case to be an O-alkyl radical, 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 Halo genatome 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. In the case of multiple halogenation, the halogen atoms can be identical or different. Halogen here represents 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 stated, optionally substituted radicals can be mono- or polysubstituted, and in the case of polysubstitutions the substituents can be identical 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 to the end products and to the starting products and intermediates accordingly. These radical definitions can be combined with one another as required, i.e. also between the respective preferred areas.
Erfindungsgemäß bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt auf geführten Bedeutungen vorliegt. Preference is given in accordance with the invention to using compounds of the formula (I) which contain a combination of the meanings given above as being preferred.
Erfindungsgemäß besonders bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. According to the invention, particular preference is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß ganz besonders bevorzugt verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt.Very particular preference is given in accordance with the invention to using compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Erfindungsgemäß hervorgehoben verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als hervorgehoben aufgeführten Bedeutungen vorliegt. According to the invention, compounds of the formula (I) which contain a combination of the meanings listed above as emphasized are used.
Erfindungsgemäß insbesonders verwendet werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als insbesonders aufgeführten Bedeutungen vorliegt. Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit sowohl reine Stereoisomere als auch beliebige Gemische dieser Isomere. According to the invention, particular use is made of compounds of the formula (I) in which there is a combination of the meanings specifically listed above. The compounds of the formula (I) can, depending on the nature of the substituents, be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus includes both pure stereoisomers and any mixtures of these isomers.
Die erfindungsgemäßen Verbindungen der Formel (I) können durch die in den folgenden Schemata dargestellten Verfahren erhalten werden: erfahren A The compounds of the formula (I) according to the invention can be obtained by the processes shown in the following schemes: experience A
Die Reste R1, R2, R3, R4, R5, R6, R7 und Z haben die oben beschriebenen Bedeutungen. X1 und X2 stehen für Halogen. R9 steht für lineares oder verzweigtes (Ci-C4)Alkyl oder Benzyl. The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above. X 1 and X 2 represent halogen. R 9 stands for linear or branched (Ci-C4) alkyl or benzyl.
Schritt a) Step a)
Verbindungen der Formel (III) können aus Imidazolderivaten der Formel (II) hergestellt werden, beispielsweise durch Umsetzung mit einem Halogenierungsreagenz wie z.B. V-Bromsuccinimid (NBS) in einem Fösungsmittel wie z.B. Tetrahydrofuran oder durch Umsetzung von Verbindungen der Formel (II) mit NBS in Kombination mit Azobis(isobutyronitril) (AIBN) in Tetrachlormethan oder Chloroform, beispielsweise analog der in WO 2013/149997, WO 2014/115077 oder WO 2011/123609 beschriebenen Verfahren. Compounds of the formula (III) can be prepared from imidazole derivatives of the formula (II), for example by reaction with a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran or by reacting compounds of the formula (II) with NBS in Combination with azobis (isobutyronitrile) (AIBN) in carbon tetrachloride or chloroform, for example analogous to the method described in WO 2013/149997, WO 2014/115077 or WO 2011/123609.
Imidazolderivate der Formel (II) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO 2014/191894, US 2003/229079 oder WO 2013/156608 beschriebenen Verfahren. Schritt b) Imidazole derivatives of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to the processes described in WO 2014/191894, US 2003/229079 or WO 2013/156608. Step b)
Verbindungen der Formel (III), in denen X1 bevorzugt für Halogen aus der Reihe Chlor oder Brom steht, können zu Verbindungen der Formel (IV) überführt werden, beispielsweise durch Übergangsmetall vermittelte Kreuzkupplungen [vgl. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed.,Wiley-VCH, Weinheim, 2004] oder durch nukleophile aromatische Substitution (vgl. die in Bioorganic and Medicinal Chemistry Leiters 2007, 17, 5825-5830 oder US 4125726 beschriebenen Verfahren). Compounds of the formula (III) in which X 1 preferably represents halogen from the group consisting of chlorine or bromine can be converted to compounds of the formula (IV), for example cross-couplings mediated by transition metal [cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds .: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004] or by nucleophilic aromatic substitution (see those in Bioorganic and Medicinal Chemistry Leiters 2007, 17, 5825-5830 or US 4125726).
Beispielsweise können Verbindungen der Formel (III), in denen X1 bevorzugt für Chlor oder Brom steht, mit geeigneten Boronsäuren [R3-B(OH)2] oder Boronestern nach bekannten Methoden (vgl. WO 2012/143599, US 2014/094474, US 2014/243316, US 2015/284358 oder Journal of Organic Chemistry 2004, 69, 8829-8835) in Gegenwart geeigneter Katalysatoren aus der Reihe der Übergangsmetallsalze zu Verbindungen der Formel (IV) umgesetzt werden. Als Kupplungskatalysatoren kommen beispielsweise bevorzugt Palladiumkatalysatoren wie [1,1 ’-Bis (diphenylphosphino)ferrocen]dichlorpalladium (II), Bis(triphenylphosphin)palladium(II)dichlorid oder Tetrakis(triphenylphosphin)palladium in Betracht. Als geeignete basische Reaktionshilfsmittel zur Durchführung der Verfahren finden bevorzugt Carbonate des Natriums, Kaliums oder Cäsiums Verwendung. Die benötigten Boronsäurederivate [R3-B(OH)2] bzw. Boronsäureesterderivate sind teilweise bekannt und/oder kommerziell erhältlich bzw. können nach allgemein bekannten Methoden hergestellt werden (vgl. Boronic Acids (Eds.: D. G. Hall), 2nd ed., Wiley- VCH, Weinheim, 2011). Dabei erfolgt die Umsetzung vorzugsweise in einem Gemisch aus Wasser und einem organischen Lösungsmittel, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Häufig werden Ether wie beispielsweise Tetrahydrofuran, Dioxan oder 1 ,2-Dimethoxyethan eingesetzt. For example, compounds of the formula (III) in which X 1 preferably represents chlorine or bromine can be mixed with suitable boronic acids [R 3 -B (OH) 2] or boronic esters by known methods (cf. WO 2012/143599, US 2014/094474 , US 2014/243316, US 2015/284358 or Journal of Organic Chemistry 2004, 69, 8829-8835) in the presence of suitable catalysts from the series of transition metal salts to give compounds of the formula (IV). Suitable coupling catalysts are, for example, preferably palladium catalysts such as [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II), bis (triphenylphosphine) palladium (II) dichloride or tetrakis (triphenylphosphine) palladium. Suitable basic reaction auxiliaries for carrying out the process are preferably carbonates of sodium, potassium or cesium. Some of the boronic acid derivatives [R 3 -B (OH) 2] or boronic acid ester derivatives required are known and / or commercially available or can be prepared by generally known methods (cf. Boronic Acids (Eds .: DG Hall), 2nd ed., Wiley-VCH, Weinheim, 2011). The reaction is preferably carried out in a mixture of water and an organic solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Frequently, ethers such as tetrahydrofuran, dioxane or 1,2-dimethoxyethane are used.
Alternativ können auch Stannanderivate | R'-Sn(n-Bu);] als Kupplungspartner eingesetzt werden (vgl. US 2013/281433, WO 2004/099177 oder WO 2016/071214). Die benötigten Stannanderivate | R'-Sn(n-Bu);] sind teilweise bekannt und/oder kommerziell erhältlich bzw. können nach allgemein bekannten Methoden hergestellt werden (vgl. WO 2016/071214 oder WO 2007/148093). Alternatively, stannane derivatives | R'-Sn (n-Bu);] can be used as the coupling partner (cf. US 2013/281433, WO 2004/099177 or WO 2016/071214). The required stannane derivatives | R'-Sn (n-Bu);] are partly known and / or commercially available or can be prepared by generally known methods (cf. WO 2016/071214 or WO 2007/148093).
Eine Kupplung der halogenierten Imidazolderivate der Formel (III) mit NH-haltigen Heteroaromaten, wie z. B. Imidazole oder Pyrazole, ggf. wie oben beschrieben substituiert, zu Verbindungen der Formel (IV) kann durch Umsetzung im Basischen (z.B. mit Natriumhydrid in Dimethylformamid, vgl. z.B. WO 2005/058898) erfolgen. Alternativ lässt sich die Umsetzung unter Inertgasatmosphäre durch Katalyse mit Kupfer(I)salzen, beispielsweise Kupfer(I)iodid, in Anwesenheit eines geeigneten Liganden, z. B. trans- /V,/V’-Dimethylcyclohexan- 1 ,2-diamin oder R-(+)-Prolin, und einer geeigneten Base, z. B. Kaliumcarbonat oder Kaliumphosphat, in einem geeigneten Lösungsmittel, wie z. B. 1,4-Dioxan oder Toluol, durchführen (vgl. z.B. WO 2016/109559). Schritt c) A coupling of the halogenated imidazole derivatives of the formula (III) with NH-containing heteroaromatics, such as. B. imidazoles or pyrazoles, optionally substituted as described above, to compounds of the formula (IV) can be carried out by reaction in the basic (for example with sodium hydride in dimethylformamide, cf., for example, WO 2005/058898). Alternatively, the reaction can be salted under an inert gas atmosphere by catalysis with copper (I), for example copper (I) iodide, in the presence of a suitable ligand, e.g. B. trans- / V, / V'-dimethylcyclohexane-1, 2-diamine or R - (+) - proline, and a suitable base, e.g. B. potassium carbonate or potassium phosphate, in a suitable solvent, such as. B. 1,4-dioxane or toluene, carry out (see, e.g. WO 2016/109559). Step c)
Imidazolderivate der Formel (V), in denen X2 bevorzugt für Halogen aus der Reihe für Brom oder Iod steht, können unter Verwendung von Standardmethoden aus Verbindungen der Formel (IV) durch Umsetzung mit beispielsweise Brom oder V-Bromsuccinimid (NBS), (vgl. WO 2009/115572 oder WO 2010/091411) oder /V-Iodsuccinimid (NIS), ggf. in Gegenwart von Essigsäure oder Trifluoressigsäure (vgl. WO 2008/063287, WO 2007/087548 oder WO 2009/152025) hergestellt werden. Imidazole derivatives of the formula (V), in which X 2 preferably represents halogen from the series for bromine or iodine, can be prepared using standard methods from compounds of the formula (IV) by reaction with, for example, bromine or V-bromosuccinimide (NBS), (cf. WO 2009/115572 or WO 2010/091411) or / V-iodosuccinimide (NIS), optionally in the presence of acetic acid or trifluoroacetic acid (cf. WO 2008/063287, WO 2007/087548 or WO 2009/152025).
Schritt d) Step d)
Verbindungen der Formel (V), in denen X2 bevorzugt für Halogen aus der Reihe für Brom oder Iod steht, können zu Verbindungen der Formel (VI) überführt werden, beispielsweise im Basischen durch Umsetzung mit Mercaptanderivaten (R'-SH) und Kupfer-(I)-Salzen (vgl. EP257918 oder WO 2009/152025) oder durch nukleophile aromatische Substitution (vgl. Australian Journal of Chemistry 1987, 40, 1415-1425). Compounds of the formula (V) in which X 2 preferably represents halogen from the series for bromine or iodine can be converted to compounds of the formula (VI), for example in the basic by reaction with mercaptan derivatives (R'-SH) and copper (I) salts (cf. EP257918 or WO 2009/152025) or by nucleophilic aromatic substitution (cf. Australian Journal of Chemistry 1987, 40, 1415-1425).
Alternativ kann die Umsetzung von Verbindungen der Formel (V), in denen X2 bevorzugt für Halogen aus der Reihe Brom oder Iod steht, mit Mercaptanderivaten (R'-SH) unter Anwesenheit von Palladiumkatalysatoren wie z.B. Tris(dibenzylidenaceton)dipalladium [Pd (dba) ] durchgefürt werden. Dabei kommen häufig Aminbasen, wie z.B. Triethylamin oder /V./V-Diisopropylcthylamin (DIPEA) sowie Phosphinliganden, wie z.B. Xantphos zur Anwendung (vgl. WO 2013/025958, WO 2013/066869, US 2009/027039, WO 2011/058149, WO 2011/143466 oder Bioorganic and Medicinal Chemistry Leiters 2016, 26, 2984-2987). Dabei erfolgt die Umsetzung vorzugsweise in einem Lösungsmittel, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Dioxan oder 1 ,2-Dimethoxyethan. Alternatively, compounds of the formula (V) in which X 2 is preferably halogen from the series bromine or iodine can be reacted with mercaptan derivatives (R'-SH) in the presence of palladium catalysts such as, for example, tris (dibenzylideneacetone) dipalladium [Pd (dba )] to be carried out. Amine bases such as triethylamine or /V./V- diisopropylethylamine (DIPEA) and phosphine ligands such as Xantphos are often used (cf. WO 2013/025958, WO 2013/066869, US 2009/027039, WO 2011/058149, WO 2011/143466 or Bioorganic and Medicinal Chemistry Leiters 2016, 26, 2984-2987). The reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Ethers such as, for example, dioxane or 1,2-dimethoxyethane are preferred.
Mercaptanderivate wie beispielsweise Methylmercaptan, Ethylmercaptan oder Isopropylmercaptan sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergesteht werden, beispielsweise analog der in US 2006/025633, US 2006/111591, US2820062, Chemical Communications 2000, 13, 1163-1164 oder Journal of the American Chemical Society 1922, 44, 1323- 1333 beschriebenen Verfahren. Mercaptan derivatives such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are either commercially available or can be produced by known methods, for example analogously to those in US 2006/025633, US 2006/111591, US2820062, Chemical Communications 2000, 13, 1163-1164 or Journal of the American Chemical Society 1922, 44, 1323-1333.
Schritt e) Steps)
Ester der Formel (VI) können unter Verwendung von Standardmethoden (vgl. z.B. WO 2014/191894, US 2006/194779, WO 2014/086663 oder European Journal of Organic Chemistry 2009, 213-222) in Carbonsäuren der Formel (VII) überführt werden, beispielsweise mit einem Alkalihydroxid als Base wie Natriumhydroxid oder Lithiumhydroxid in einem Alkohol, wie z.B. Methanol oder Ethanol oder einem Ether wie z.B. THF als Lösungsmittel, bevorzugt in Gegenwart von Wasser. Schritt f) Esters of the formula (VI) can be converted into carboxylic acids of the formula (VII) using standard methods (cf., for example, WO 2014/191894, US 2006/194779, WO 2014/086663 or European Journal of Organic Chemistry 2009, 213-222) , for example with an alkali hydroxide as the base such as sodium hydroxide or lithium hydroxide in an alcohol such as methanol or ethanol or an ether such as THF as the solvent, preferably in the presence of water. Step f)
Verbindungen der Formel (I, m = 0, n = 0) lassen sich aus Verbindungen der Formeln (VII) mit Verbindungen der Formel (VIII) in Gegenwart eines Kondensationsmittels herstellen. Compounds of the formula (I, m = 0, n = 0) can be prepared from compounds of the formula (VII) with compounds of the formula (VIII) in the presence of a condensing agent.
Verbindungen der Formel (VIII) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergesteht werden, beispielsweise analog der in Chemistry - A European Journal 2017, 23, 13607-13611 oder EP0234449 A2 beschriebenen Verfahren. Compounds of the formula (VIII) are either commercially available or can be prepared by known methods, for example analogously to the processes described in Chemistry - A European Journal 2017, 23, 13607-13611 or EP0234449 A2.
Die Umsetzung zu Verbindungen der Formel (I, m = 0, n = 0) 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; Alkohole wie Methanol, Ethanol oder iso-Propanol; Nitrile, wie beispielsweise Acetonitril oder Propionitril; aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol; aprotische polare Lösungsmittel wie beispielsweise /V, /V- D i m c t h y 1 f r m a m i d oder /V- Methyl pyrrolidon oder stickstoffhaltige Verbindungen wie beispielsweise Pyridin. The conversion to compounds of the formula (I, m = 0, n = 0) can be carried out in bulk or in a solvent; the reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol, ethanol or iso-propanol; Nitriles such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as / V, / V- D i m c t h y 1 f r m a m i d or / V-methyl pyrrolidone or nitrogen-containing compounds such as pyridine.
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 azodiester such as diethylazodicarboxylic acid.
Die Reaktion kann durchgeführt werden in Gegenwart eines geeigneten Katalysators wie z.B. 1- Flydroxybenzotriazol. The reaction can be carried out in the presence of a suitable catalyst such as 1-flyroxybenzotriazole.
Die Reaktion lässt sich durchführen in Gegenwart einer Säure oder einer Base. The reaction can be carried out in the presence of an acid or a base.
Beispiele für eine Säure, die in der beschriebenen Reaktion eingesetzt werden kann, sind Sulfonsäuren wie Methansulfonsäure oder para-Toluolsulfonsäure; Carbonsäuren wie Essigsäure oder Polyphosphorsäuren. Examples of an acid which can be used in the reaction described are sulfonic acids such as methanesulfonic acid or para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
Beispiele für geeignete Basen sind stickstoffhaltige Fleterocyclen wie Pyridin, Picolin, 2,6-Lutidin, 1,8- Diazabicyclo[5.4.0]-7-undecen (DBU); tertiäre Amine wie Triethylamin und /V./V-Diisopiopylcthylamin; anorganische Basen wie Kaliumphosphat, Kaliumcarbonat und Natriumhydrid. Examples of suitable bases are nitrogen-containing fleterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and /V./V-diisopiopylcthylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
Schritt g) Step g)
Die Verbindungen der Formel (I, m = 1, n = 0 oder 1) lassen sich herstellen durch Oxidation von Verbindungen der Formel (I, m = 0, n = 0), z.B. analog der in WO 2016/169882 oder WO 2016/124557 beschriebenen Verfahren. 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, m = 1, n = 0 or 1) can be prepared by oxidation of Compounds of the formula (I, m = 0, n = 0), for example analogous to the processes described in WO 2016/169882 or WO 2016/124557. The oxidation is generally carried out in a solvent. Halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene are preferred; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
Beispiele für geeignete Oxidationsmittel sind Wasserstoffperoxid und mefa-Chlorperbenzoesäure. Examples of suitable oxidizing agents are hydrogen peroxide and mefa-chloroperbenzoic acid.
Verfahren B Procedure B
Die Reste R1, R2, R3, R4, R5, R6, R7 und Z haben die oben beschriebenen Bedeutungen. X1 steht für Halogen. R9 steht für lineares oder verzweigtes (Ci-C4)Alkyl oder Benzyl. The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above. X 1 stands for halogen. R 9 stands for linear or branched (Ci-C4) alkyl or benzyl.
Schritt a) Step a)
Verbindungen der Formel (III) können aus Imidazolderivaten der Formel (II) hergestellt werden, beispielsweise durch Umsetzung mit einem Halogenierungsreagenz wie z.B. V-Bromsuccinimid (NBS) in einem Lösungsmittel wie z.B. Tetrahydrofuran oder durch Umsetzung von Verbindungen der Formel (II) mit NBS in Kombination mit Azobis(isobutyronitril) (AIBN) in Tetrachlormethan oder Chloroform, beispielsweise analog der in WO 2013/149997, WO 2014/115077 oder WO 2011/123609 beschriebenen Verfahren. Compounds of the formula (III) can be prepared from imidazole derivatives of the formula (II), for example by reaction with a halogenating reagent such as V-bromosuccinimide (NBS) in a solvent such as tetrahydrofuran or by reacting compounds of the formula (II) with NBS in Combination with azobis (isobutyronitrile) (AIBN) in carbon tetrachloride or chloroform, for example analogous to the method described in WO 2013/149997, WO 2014/115077 or WO 2011/123609.
Imidazolderivate der Formel (II) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in WO 2014/191894, US 2003/229079 oder WO 2013/156608 beschriebenen Verfahren. Imidazole derivatives of the formula (II) are either commercially available or can be prepared according to known ones Methods are produced, for example analogous to the methods described in WO 2014/191894, US 2003/229079 or WO 2013/156608.
Schritt b) Step b)
Imidazolderivate der Formel (IX) können unter Verwendung von Standardmethoden aus Verbindungen der Formel (III) durch Umsetzung mit einem Disulfid (R'-S-S-R1) und beispielsweise einer starken Base, vorzugsweise Lithiumdiisopropylamid (LDA) in Tetrahydrofuran (vgl. Bioorganic and Medicinal Chemistry Leiters 2010, 20, 1084-1089) oder z.B. Wasserstoffperoxid und Iod in Ethanol (vgl. Synthesis 2015, 47, 659-671) hergestellt werden. Imidazole derivatives of the formula (IX) can be prepared using standard methods from compounds of the formula (III) by reaction with a disulfide (R'-SSR 1 ) and, for example, a strong base, preferably lithium diisopropylamide (LDA) in tetrahydrofuran (cf. Bioorganic and Medicinal Chemistry Leiters 2010, 20, 1084-1089) or e.g. hydrogen peroxide and iodine in ethanol (see Synthesis 2015, 47, 659-671).
Schritt c) Step c)
Die Umsetzung von Verbindungen der Formel (IX) zu Verbindungen der Formel (X) erfolgt analog zu Verfahren A, Schritt e). The conversion of compounds of the formula (IX) to compounds of the formula (X) takes place analogously to process A, step e).
Schritt d) Step d)
Die Umsetzung von Verbindungen der Formel (X) mit Verbindungen der Formel (VIII) zu Verbindungen der Formel (I, m = 0, n = 0, R3 = X1) erfolgt analog zu Verfahren A, Schritt f). The reaction of compounds of the formula (X) with compounds of the formula (VIII) to give compounds of the formula (I, m = 0, n = 0, R 3 = X 1 ) takes place analogously to process A, step f).
Schritt e,h) Step e, h)
Die Umsetzung von Verbindungen der Formel (I, m = 0, n = 0, R3 = X1) zu Verbindungen der Formel (I, m = 1, n = 0 oder 1, R3 = X1) sowie die Umsetzung von Verbindungen der Formel (I, m = 0, n = 0) zu Verbindungen der Formel (I, m = 1, n = 0 oder 1) erfolgt analog zu Verfahren A, Schritt g). The conversion of compounds of the formula (I, m = 0, n = 0, R 3 = X 1 ) to compounds of the formula (I, m = 1, n = 0 or 1, R 3 = X 1 ) and the conversion of Compounds of the formula (I, m = 0, n = 0) to compounds of the formula (I, m = 1, n = 0 or 1) are carried out analogously to process A, step g).
Schritt f,g) Step f, g)
Die Umsetzung von Verbindungen der Formel (I, m = 0, n = 0, R3 = X1) zu Verbindungen der Formel (I, m = 0, n = 0) sowie die Umsetzung von Verbindungen der Formel (I, m = 1, n = 0 oder 1, R3 = X1) zu Verbindungen der Formel (I, m = 1, n = 0 oder 1) erfolgt analog zu Verfahren A, Schritt b). erfahren C The conversion of compounds of the formula (I, m = 0, n = 0, R 3 = X 1 ) to compounds of the formula (I, m = 0, n = 0) and the conversion of compounds of the formula (I, m = 1, n = 0 or 1, R 3 = X 1 ) to compounds of the formula (I, m = 1, n = 0 or 1) takes place analogously to process A, step b). experienced C
Die Reste R1, R2, R3, R4, R5, R6, R7, und Z haben die oben beschriebenen Bedeutungen. Y steht für NH. m und n stehen für 0 oder m und n stehen für 1. Schritt a) The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above. Y stands for NH. m and n stand for 0 or m and n stand for 1. Step a)
Die Herstellung von Verbindungen der Formel (I, m = l, n = l, Y = NH) kann beispielsweise aus Verbindungen der Formel (I, m = 0, n = 0) durch Umsetzung mit einem geeigneten Oxidationsmittel und unter Verwendung einer geeigneten Stickstoffquelle in einem geeigneten Lösungs- oder Verdünnungsmittel erfolgen. Entsprechende Umsetzungen sind in der Literatur beschrieben, beispielsweise in Chem. Commun. 2017, 53, 348-351. Als Oxidationsmittel eignet sich beispielsweise (Diacetoxyiod)-benzol. Als Stickstoffquelle eigent sich beispielsweise Ammoniumcarbamat, Ammoniumacetat oder Ammoniak in Methanol. Geeignete Lösungsmittel sind unter den gewählten Reaktionsbedingungen inert. Es eignen sich Lösungsmittel wie beispielsweise Methanol, Acetonitril oder Touol. Beispielhaft kann eine Verbindung der Lormel (I, m = 0, n = 0) durch Behandlung mit (Diacetoxyiod)-benzol und Ammoiniumcarbamat in Methanol bei Raumtemperatur in eine Verbindung der Lormel (I, m = l, n = l, Y = NH) überführt werden. Compounds of the formula (I, m = 1, n = 1, Y = NH) can be prepared, for example, from compounds of the formula (I, m = 0, n = 0) by reaction with a suitable oxidizing agent and using a suitable nitrogen source take place in a suitable solvent or diluent. Corresponding reactions are described in the literature, for example in Chem. Commun. 2017, 53, 348-351. An example of a suitable oxidizing agent is (diacetoxyiod) benzene. Examples of suitable nitrogen sources are ammonium carbamate, ammonium acetate or ammonia in methanol. Suitable solvents are inert under the chosen reaction conditions. Solvents such as methanol, acetonitrile or Touol are suitable. For example, a compound of the Lormel (I, m = 0, n = 0) can be converted into a compound of the Lormel (I, m = 1, n = 1, Y = NH ) are transferred.
Verfahren D Die Reste R1, R2, R3, R4, R5, R6, R7 und Z haben die oben beschriebenen Bedeutungen. X1 steht für Halogen. Y steht für NH. Method D The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings described above. X 1 stands for halogen. Y stands for NH.
Schritt a,d) Step a, d)
Die Umsetzung von Verbindungen der Lormel (I, m = 0, n = 0, R3 = X1) zu Verbindungen der Lormel (I, m = 1, n = 1, R3 = X1) sowie die Umsetzung von Verbindungen der Lormel (I, m = 0, n = 0) zu Verbindungen der Lormel (I, m = 1, n = 1) erfolgt analog zu Verfahren C, Schritt a). Schritt b,c) The implementation of compounds of the Lormel (I, m = 0, n = 0, R 3 = X 1 ) to compounds of the Lormel (I, m = 1, n = 1, R 3 = X 1 ) and the implementation of compounds of the Lormel (I, m = 0, n = 0) to compounds of Lormel (I, m = 1, n = 1) takes place analogously to method C, step a). Step b, c)
Die Umsetzung von Verbindungen der Formel (I, m = 0, n = 0, R3 = X1) zu Verbindungen der Formel (I, m = 0, n = 0) sowie die Umsetzung von Verbindungen der Formel (I, m = 1, n = 1, R3 = X1) zu Verbindungen der Formel (I, m = 1, n = 1) erfolgt analog zu Verfahren A, Schritt b). erfahren E The conversion of compounds of the formula (I, m = 0, n = 0, R 3 = X 1 ) to compounds of the formula (I, m = 0, n = 0) and the conversion of compounds of the formula (I, m = 1, n = 1, R 3 = X 1 ) to compounds of the formula (I, m = 1, n = 1) takes place analogously to process A, step b). experienced E
Die Reste R1, R2, R3, R4, R5, R6, R7, R8 und Y haben die oben beschriebenen Bedeutungen m steht für 0 oder 1, n steht für 0 oder 1. The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Y have the meanings described above.
Schritt a) Step a)
Die Flerstellung von Verbindungen der Formel (I, R8 F Fl) kann beispielsweise aus Verbindungen der Formel (I, R8 = Fl) in Gegenwart eines geeigneten Alkylierungsmittels und einer geeigneten Base in einem geeigneten Lösungs- oder Verdünnungsmittel erfolgen. Als Alkylierungsmittel eignen sich Alkylhalogenide, vorzugsweise Alkylbromide oder Alkyliodide, sowie Alkylsulfonate wie beispielsweise Alkylmethansulfonate, Alkyltosylate oder Alkyltrifluormethansulfonate. Als Flilsbasen eignen sich Carbonate des Natriums, Kaliums oder Cäsiums, sterisch gehinderte und nicht nukleophile Aminhasen wie beispielsweise /V./V-Diisopiopylcthylamin oder Flydridbasen wie beispielsweise Natriumhydrid. Geeignete Lösungsmittel sind unter den jeweils gewählten Reaktionsbedingungen inert. Je nach verwendeter Base eignen sich 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 oder aprotische polare Lösungsmittel wie beispielsweise Aceton, /V , /V- D i m c t h y 1 f r m a m i d oder /V- Methyl pyrrolidon. Vorzugsweise wird die Reaktion unter Verwendung einer Carbonatbase in Aceton oder /V, /V- D i m c t h y 1 f r m a m i d durchgeführt. Compounds of the formula (I, R 8 F Fl) can be prepared, for example, from compounds of the formula (I, R 8 = Fl) in the presence of a suitable alkylating agent and a suitable base in a suitable solvent or diluent. Suitable alkylating agents are alkyl halides, preferably alkyl bromides or alkyl iodides, and also alkyl sulfonates such as, for example, alkyl methanesulfonates, alkyl tosylates or alkyl trifluoromethanesulfonates. Suitable filler bases are carbonates of sodium, potassium or cesium, sterically hindered and non-nucleophilic amine phases such as /V./V- diisopiopylethylamine or flydride bases such as sodium hydride. Suitable solvents are inert under the reaction conditions chosen in each case. Depending on the base used, ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether are suitable; 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 or aprotic polar solvents such as acetone, / V, / V-D imcthy 1 frmamid or / V-methyl pyrrolidone. Preferably the reaction is carried out using a carbonate base in acetone or / V, / V-D imcthy 1 formamide.
Beispielhaft kann eine Verbindung der Formel (I, R8 = H) durch Behandlung mit Iodmethan in Gegenwart von Kaliumcarbonat als Base in Aceton als Lösungsmittel unter Rückflussbedingungen in eine Verbindung der Formel (I, R8 = Me) überführt werden. For example, a compound of the formula (I, R 8 = H) can be converted into a compound of the formula (I, R 8 = Me) by treatment with iodomethane in the presence of potassium carbonate as the base in acetone as the solvent under reflux conditions.
Die Reste R1, R2, R3, R4, R5, R6, R7, R8 haben die oben beschriebenen Bedeutungen. X1 und X2 stehen für Halogen. Schritt a) The radicals R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 have the meanings described above. X 1 and X 2 represent halogen. Step a)
Verbindungen der Formel (XII) können aus Dianilinen der Formel (XI) hergestellt werden, beispielsweise durch Umsetzung mit Ameisensäure, Ameisensäureestern oder Orthoformiaten. In Gegenwart oder Abweseneheit eines bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmittels. Bei Bedarf kann die Reaktion durch Zugabe von Brpnsted- oder Lewis-Säuren katalysiert werden. Die Verbindungen der Formel (XI) sind entweder kommerziell erhältlich oder können nach bekannten Methoden hergestellt werden, beispielsweise analog der in Chemistry - A European Journal 2017, 23, 13607-13611 oder EP0234449 A2 beschriebenen Verfahren. Compounds of the formula (XII) can be prepared from dianilines of the formula (XI), for example by reaction with formic acid, formic acid esters or orthoformates. In the presence or absence of a solvent which is inert under the prevailing reaction conditions. If necessary, the reaction can be catalyzed by the addition of Brpnsted or Lewis acids. The compounds of the formula (XI) are either commercially available or can be prepared by known methods, for example analogously to the processes described in Chemistry - A European Journal 2017, 23, 13607-13611 or EP0234449 A2.
Schritt b) Step b)
Die Umsetzung von Verbindungen der Formel (XII) zu Verbindungen der Formel (XIII) erfolgt analog zu Verfahren E, Schritt a). Schritt c) The conversion of compounds of the formula (XII) to compounds of the formula (XIII) takes place analogously to process E, step a). Step c)
Verbindungen der Formel (I, m = 0, n = 0, R3 = H) können durch Umsetzung von Verbindungen der Formel (XIII) mit Verbindungen der Formel (XIV) hergestellt werden. Dazu werden Verbindungen der Formel (XIII) zunächst mit einer starken Base wie beispielsweise Tetramethylpiperidinylzinkchlorid Lithiumchlorid Komplex behandelt und dann in Gegenwart von Palladiumkatalysatoren wie z.B. Tetrakis(triphenylphosphin)palladium(0) mit Verbindungen der Formel (XIV) umgesetzt. Dabei erfolgt die Umsetzung vorzugsweise in einem Lösungsmittel, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Dioxan oder TF1F. Compounds of the formula (I, m = 0, n = 0, R 3 = H) can be prepared by reacting compounds of the formula (XIII) with compounds of the formula (XIV). For this purpose, compounds of formula (XIII) are first treated with a strong base such as tetramethylpiperidinylzinc chloride lithium chloride complex and then reacted with compounds of formula (XIV) in the presence of palladium catalysts such as tetrakis (triphenylphosphine) palladium (0). The reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Ethers such as, for example, dioxane or TF1F are preferred.
Die Verbindungen der Formel (XIV) können nach bekannten Methoden hergestellt werden, beispielsweise analog der in W02020074558 Al beschriebenen Verfahren. The compounds of the formula (XIV) can be prepared by known methods, for example analogously to the processes described in WO2020074558 A1.
Schritt d) Step d)
Die Flerstellung von Verbindungen der Formel (I, m = 0, n = 0) kann ausgehend von Verbindungen der Formel (I, m = 0, n = 0, R3 = Fl) erfolgen. Dazu werden die Verbindungen der Formel (I, m = 0, n = 0, R3 = Fl) zunächst mit einer starken Base wie beispielsweise Tetramethylpiperidinylzinkchlorid Lithiumchlorid Komplex behandelt und dann in Gegenwart von Palladiumkatalysatoren wie z.B. Tetrakis(triphenylphosphin)palladium(0) mit Arylhalogeniden der Fleteroarylhalogeniden, vorzugsweise Bromide oder Iodide, umgesetzt. Dabei erfolgt die Umsetzung vorzugsweise in einem Lösungsmittel, welches ausgewählt ist aus üblichen, bei den vorherrschenden Reaktionsbedingungen inerten Lösungsmitteln. Bevorzugt werden Ether wie beispielsweise Dioxan oder TF1F. Compounds of the formula (I, m = 0, n = 0) can be prepared starting from compounds of the formula (I, m = 0, n = 0, R 3 = Fl). For this purpose, the compounds of the formula (I, m = 0, n = 0, R 3 = Fl) are first treated with a strong base such as tetramethylpiperidinylzinc chloride lithium chloride complex and then with palladium (0) in the presence of palladium catalysts such as tetrakis (triphenylphosphine) Aryl halides of the fleteroaryl halides, preferably bromides or iodides, reacted. The reaction is preferably carried out in a solvent which is selected from customary solvents which are inert under the prevailing reaction conditions. Ethers such as, for example, dioxane or TF1F are preferred.
Schritt e) Steps)
Die Umsetzung von Verbindungen der Formel (I, m = 0, n = 0) zu Verbindungen der Formel (I, m = 1, n = 0 oder 1) erfolgt analog zu Verfahren A, Schritt g). erfahren und Verwendungen The conversion of compounds of the formula (I, m = 0, n = 0) to compounds of the formula (I, m = 1, n = 0 or 1) takes place analogously to process A, step g). experience and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei denen man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum ein wirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Flierunter 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 of combating animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to combating animal pests in agriculture and forestry and in material protection. Methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body are also preferably excluded.
Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel jeweils immer auch den Begriff Pflanzenschutzmittel. The invention also relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents. In the context of the present application, the term pesticides always also includes the term pesticides.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, insbesondere Nematoden, und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor Vorkommen. The compounds of the formula (I) are suitable for protecting plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the harvested crop and for combating animal pests, especially insects, if they are well tolerated by plants, have favorable warm-blooded toxicity and are environmentally friendly. Arachnids, helminths, in particular nematodes, and mollusks that occur in agriculture, horticulture, animal breeding, aquaculture, forests, gardens and leisure facilities, in the protection of stored products and materials, and in the hygiene sector.
Im Rahmen der vorliegenden Patentanmeldung ist der Begriff „Hygiene“ so zu verstehen, dass damit jegliche und alle Maßnahmen, Vorschriften und Verfahrensweisen gemeint sind, deren Ziel es ist, Krankheiten, insbesondere Infektionskrankheiten, zu verhindern, und die dazu dienen, die Gesundheit von Menschen und Tieren zu schützen und/oder die Umwelt zu schützen, und/oder die Sauberkeit aufrechterhalten. Erfindungsgemäß schließt dies insbesondere Maßnahmen zur Reinigung, Desinfektion und Sterilisation beispielsweise von Textilien oder harten Oberflächen, insbesondere Oberflächen aus Glas, Holz, Zement, Porzellan, Keramik, Kunststoff oder auch Metall(en) ein, um sicherzustellen, dass diese frei von Hygieneschädlingen und/oder ihren Ausscheidungen sind. Vorzugsweise ausgeschlossen vom Schutzbereich der Erfindung sind in dieser Hinsicht chirurgische oder therapeutische, auf den menschlichen Körper oder die Körper von Tieren anzuwendende Behandlungsvorschriften und diagnostische Vorschriften, die am menschlichen Körper oder den Körpern von Tieren durchgeführt werden. In the context of the present patent application, the term “hygiene” is to be understood to mean any and all measures, regulations and procedures whose aim is to prevent diseases, in particular infectious diseases, and which serve to improve the health of people and to protect animals and / or to protect the environment and / or to maintain cleanliness. According to the invention, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal (s), in order to ensure that they are free from hygiene pests and / or their excretions are. In this regard, surgical or therapeutic treatment regulations to be applied to the human body or the bodies of animals and diagnostic regulations which are carried out on the human body or the bodies of animals are preferably excluded from the scope of protection of the invention.
Der Begriff „Hygienesektor“ deckt somit alle Gebiete, technischen Felder und industriellen Anwendungen ab, bei denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen wichtig sind, zum Beispiel im Hinblick auf Hygiene in Küchen, Bäckereien, Flughäfen, Badezimmern, Schwimmbecken, Kaufhäusern, Hotels, Krankenhäusern, Ställen, Tierhaltungen usw. The term "hygiene sector" thus covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels , Hospitals, stables, animal husbandry etc.
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 Bewältigen 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 to mean one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons. It is therefore a primary objective to avoid or minimize the presence of hygiene pests and / or exposure to them in the hygiene sector. This can be achieved in particular by using a pesticide that can be used both to prevent an infestation and to cope with an already existing infestation. Preparations that prevent or reduce exposure to pests can also be used. Hygiene pests include, for example, the organisms mentioned below.
Der Begriff „Hygieneschutz“ deckt somit alle Handlungen ab, mit denen diese Hygienemaßnahmen, -Vorschriften und -Verfahrensweisen aufrechterhalten und/oder verbessert werden. Die Verbindungen der Formel (I) können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The term "hygiene protection" thus covers all actions with which these hygiene measures, regulations and procedures are maintained and / or improved. The compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development. The pests mentioned above 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; Sminthurus viridis; aus der Klasse der Diplopoda z. B. Blaniulus guttulatus; aus der Klasse der Insecta, z. B. aus der Ordnung der Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., z. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; aus der Ordnung der Coleoptera z. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., z. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., z. B. Agriotes linneatus, Agriotes mancus, Agriotes obscurus Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., z. B. Anoplophora glabripennis, Anthonomus spp., z. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, 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, Dendroctonus spp., z. B. Dendroctonus ponderosae, 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., Hoplia argentea, 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, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., z. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., z. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z. B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z. B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus, Rhynchophorus palmarum, Scolytus spp., z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., z. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z. B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z. B. Zabrus tenebrioides; aus der Ordnung der Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; aus der Ordnung der Diptera z. B. Aedes spp., z. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z. B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z. B. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z. B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z. B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z. B. Dasineura brassicae, Delia spp., z. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z. B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., z. B. Lucilia 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 halb, 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., Metcalfa 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 cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., z. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., z. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella 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, Monalonion 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., z. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., z. B. Vespa crabro, Wasmannia auropunctata, Xeris spp.; aus der Ordnung der Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z. B. Coptotermes spp., z. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., z. B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z. B. Achroia grisella, Acronicta major, Adoxophyes spp., z. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., z. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., z. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Euba 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, Hepialus spp., z. B. Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., z. B. Leucoptera coffeella, Lithocolletis spp., z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z. B. Lymantria dispar, Lyonetia spp., z. B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., z. B. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., z. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp., z. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z. B. Schoenobius bipunctifer, Scirpophaga spp., z. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z. B. Locusta migratoria, Melanoplus spp., z. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z. B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z. B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Fepisma saccharina, Fepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z. B. Scutigerella spp., z. B. Scutigerella immaculata; Pests from the strain of the Arthropoda, in particular from the class of the Arachnida z. Acarus spp., E.g. B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. B. Aculus fockeui, Aculus sinnendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., E.g. B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., E.g. B. Eutetranychus banksi, Eriophyes spp., E.g. B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., E.g. B. Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus 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, z. B. Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Stpotarsphalus spp., Scorpene spp. Steneotarsonemus spinki, Tarsonemus spp., E.g. B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the class of the Chilopoda z. B. Geophilus spp., Scutigera spp .; from the order or class of the Collembola z. B. Onychiurus armatus; Sminthurus viridis; from the class of the Diplopoda z. B. Blaniulus guttulatus; from the class of Insecta, e.g. B. from the order of the Blattodea z. B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. B. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of the Coleoptera, for. B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelastica alni, Agrilus spp., E.g. B. Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius, Agriotes spp., E.g. B. Agriotes linneatus, Agriotes mancus, Agriotes obscurus Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp., E.g. B. Anoplophora glabripennis, Anthonomus spp., E.g. B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp., E.g. B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp. E.g. B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., E.g. B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., E.g. B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., E.g. B. Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocpopus. B. Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., E.g. B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicachnaispa. B. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g. B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hoplia, argenteaes posta, Hajylota elegans, Hylamorpha elegans squamosus, Hypothenemus spp., e.g. B. 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, Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (= Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., Z. B. Megacyllene robiniae, Megascelis spp., Melanotus spp., E.g. B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., E.g. B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae., Otp. B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. B. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g. 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, Scolytus spp., Z. B. Scolytus multistriatus, Sinoxylon perforans, Sitophilus spp., E.g. B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., E.g. B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., E.g. B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. B. Zabrus tenebrioides; from the order of the Dermaptera z. B. Anisolabis maritime, Forficula auricularia, Labidura riparia; from the order of the Diptera z. B. Aedes spp., E.g. B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g. B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., E.g. B. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona spp., Chrysozona pluvialis, Cochliomya. 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., E.g. B. Dasineura brassicae, Delia spp. E.g. B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. 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., Hippobosca spp., Liriomyza spp., E.g. B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., E.g. B. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., E.g. B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp., E.g. B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., E.g. B. 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., E.g. B. Tipula paludosa, Tipula simplex, Toxotrypana curvicauda; from the order of the Hemiptera, for. B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., E.g. B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., E.g. B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., E.g. 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 viburniphililla, Arboridytainical, Arboridia. , Aspidiella spp., Aspidiotus spp., E.g. B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. B. Cacopsylla pyricola, Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris Roshalus falicola, Compicidus, Chromicidum, Comphalus fhalidum, Chromicidum, Chromaphis , Coccus spp., E.g. 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., Diuraphis spp., Diuraphis spp. Drosicha spp., Dysaphis spp. E.g. B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., E.g. B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., E.g. B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococus coffeae , Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., E.g. B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g. B. Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., E.g. B. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., E.g. B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa 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., E.g. B. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., E.g. B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g. B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., E.g. B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., E.g. B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., E.g. B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Siphatellauscealis, Siphatella furcifera, Siphatella furcifera, Sogatodes spetrara spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp. e.g. B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., E.g. B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of the Heteroptera z. B. Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g. B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis., Leptocorisa varicornis, Leptoglopus spp . B. Lygocoris pabulinus, Lygus spp., E.g. B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., E.g. B. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g. B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera, for. E.g., Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., E.g. B. Diprion similis, Hoplocampa spp., E.g. B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. B. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of the Isopoda z. B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera, for. B. Coptotermes spp., E.g. B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermes spp., Odontotermes spp., Porotermes spp., Reticulitermes spp., E.g. B. Reticulitermes flavipes, Reticulitermes hesperus; from the order of the Lepidoptera, for. B. Achroia grisella, Acronicta major, Adoxophyes spp., E.g. B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., E.g. B. Agrotis segetum, Agrotis ipsilon, Alabama spp., E.g. B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., E.g. B. Anticarsia gemmatalis, Argyroploce spp., Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulina , Chilo spp., E.g. B. Chilo plejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha sp. B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria zimmermani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g. B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp. ,Eschoviella musculana, Etiella spp., Eudocima spp., Euba spp., Eupoecilia ambiguella, Euproctis spp., E.g. B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., E.g. B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., E.g. B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., E.g. B. Heliothis virescens, Hepialus spp., E.g. B. Hepialus humuli, Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., E.g. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., E.g. B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., E.g. 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., Orthaga spp., Ostrinia spp. E.g. B. Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp., E.g. B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., E.g. B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Podesia spp., E.g. B. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., E.g. B. Schoenobius bipunctifer, Scirpophaga spp., E.g. B. Scirpophaga innotata, Scotia segetum, Sesamia spp., E.g. B. Sesamia inferens, Sparganothis spp., Spodoptera spp., E.g. B. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis spp., Tinealo pellacella, Tinineealo pellacella, Tinealo pellacella ., Trichophaga tapetzella, Trichoplusia spp., E.g. B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of the Orthoptera or Saltatoria z. B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., E.g. B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., E.g. B. Locusta migratoria, Melanoplus spp., E.g. B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of the Phthiraptera z. B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of the Psocoptera, for. B. Lepinotus spp., Liposcelis spp .; from the order of the Siphonaptera z. B. Ceratophyllus spp., Ctenocephalides spp., E.g. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera, for. B. Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., E.g. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips, spp . B. Thrips palmi, Thrips tabaci; from the order of the Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Fepisma saccharina, Fepismodes inquilinus, Thermobia domestica; from the class of the Symphyla z. B. Scutigerella spp., E.g. 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., Fymnaea 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. Pests from the trunk of the Mollusca, e.g. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., E.g. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. B. Deroceras laeve, Galba spp., Fymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .; Plant pests from the strain of the Nematoda, ie plant-parasitic nematodes, in particular Aglenchus spp., E.g. B. Aglenchus agricola, Anguina spp. E.g. B. Anguina tritici, Aphelenchoides spp., E.g. B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., E.g. B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., E.g. B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. B. Cacopaurus pestis, Criconemella spp., E.g. B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., E.g. B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g. B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., E.g. B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmaniella spp., Hoplolaimus spp., Longidorus spp., E.g. B. Longidorus africanus, Meloidogyne spp., E.g. B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. B. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g. B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. B. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., E.g. B. Xiphinema index.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstumsregulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma-like- organism) und RLO (Rickettsia-like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. The compounds of the formula (I) can 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 agents against viroids) or be used as a remedy against MLO (Mycoplasma-like organism) and RLO (Rickettsia-like organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
F ormulierungen/Anwendungsformen Formulations / application forms
Die vorliegende Erfindung betrifft weiterhin Formulierungen, insbesondere Formulierungen zur Bekämpfung unerwünschter tierischer Schädlinge. Die Formulierung kann auf den tierischen Schädling und/oder in dessen Lebensraum angewendet werden. The present invention further relates to formulations, in particular formulations for controlling undesired animal pests. The formulation can be applied to the animal pest and / or in its habitat.
Die erfindungsgemäße Formulierung kann dem Endanwender als anwendungsfertige „Anwendungsform“ bereitgestellt werden, d.h. die Formulierungen können direkt mittels eines geeigneten Geräts wie einem Sprüh- oder Stäubegerät auf die Pflanzen oder Samen aufgebracht werden. Alternativ dazu können die Formulierungen dem Endanwender in Form von vor der Anwendung vorzugsweise mit Wasser zu verdünnenden Konzentraten bereitgestellt werden. Wenn nicht anders angegeben wird mit dem Ausdruck „Formulierung“ somit ein solches Konzentrat bezeichnet, während der Ausdruck „Anwendungsform“ eine für den Endanwender anwendungsfertige Lösung bezeichnet, d.h. gewöhnlich eine solche verdünnte Formulierung. The formulation according to the invention can be provided to the end user as a ready-to-use “application form”, ie the formulations can be applied directly to the plants or seeds by means of a suitable device such as a spray or dust device. Alternatively, the formulations can be provided to the end user in the form of concentrates to be diluted, preferably with water, before use. Unless otherwise stated, the term “formulation” denotes such a concentrate, while the term “application form” denotes a means ready-to-use solution for the end user, ie usually such a dilute formulation.
Die erfindungsgemäße Formulierung kann auf herkömmliche Weise hergestellt werden, zum Beispiel durch Mischen der erfindungsgemäßen Verbindung mit einem oder mehreren geeigneten Hilfsstoffen wie z.B. den hier offenbarten. The formulation of the invention can be prepared in a conventional manner, for example by mixing the compound of the invention with one or more suitable excipients such as those disclosed herein.
Die Formulierung umfasst mindestens eine erfindungsgemäße Verbindung und mindestens einen landwirtschaftlich brauchbaren Hilfsstoff, z.B. Träger und/oder Tensid(e). The formulation comprises at least one compound according to the invention and at least one agriculturally useful adjuvant, e.g. carrier and / or surfactant (s).
Ein Träger ist eine feste oder flüssige, natürliche oder synthetische, organische oder anorganische Substanz, die im Allgemeinen inert ist. Der Träger verbessert im Allgemeinen das Ausbringen der Verbindungen, zum Beispiel auf Pflanzen, Pflanzenteile oder Samen. Beispiele für geeignete feste Träger schließen, wobei dies nicht einschränkend ist, Ammoniumsalze, insbesondere Ammoniumsulfate, Ammoniumphosphate und Ammoniumnitrate, gemahlenes natürliches Gestein, wie Kaoline, Tone, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit und Diatomeenerde, Kieselgel, und gemahlenes synthetisches Gestein, wie feinteiliges Siliciumdioxid, Aluminiumoxid und Silicate, ein. Beispiele für typische geeignete feste Träger zur Herstellung von Granulaten schließen, wobei dies nicht einschränkend ist, gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bimsstein, Sepiolith und Dolomit, synthetische Granulate anorganischer und organischer Mehle und Granulate organischer Materialien wie Papier, Sägespäne, Kokosnussschalen, Maiskolben und Tabakstängel ein. Beispiele für geeignete flüssige Träger schließen, wobei dies nicht einschränkend ist, Wasser, organische Lösungsmittel und Kombinationen davon ein. Beispiele für geeignete Lösungsmittel schließen polare und unpolare organische chemische Flüssigkeiten, zum Beispiel aus den Klassen der aromatischen und nichtaromatischen Kohlenwasserstoffe (wie Cyclohexan, Paraffine, Alkylbenzole, Xylol, Toluol, Tetrahydronaphthalin, Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid), Alkohole und Polyole (die auch substituiert, verethert und/oder verestert sein können, wie Ethanol, Propanol, Butanol, Benzylalkohol, Cyclohexanol oder Glykol), Ketone (wie Aceton, Methylethylketon, Methylisobutylketon, Acetophenon oder Cyclohexanon), Ester (einschließlich Fette und Öle) und (Poly)ether, unsubstituierte und substituierte Amine, Amide (wie Dimethylformamid oder Fettsäureamide) und Ester davon, Lactame (wie N-Alkylpyrrolidone, insbesondere N-Methylpyrrolidon) und Lactone, Sulfone und Sulfoxide (wie Dimethylsulfoxid), Öle pflanzlichen oder tierischen Ursprungs, Nitrile (Alkylnitrile wie Acetonitril, Propionnitril, Butyronitril, oder aromatische Nitrile wie Benzonitril), Kohlensäureester (cyclische Kohlensäureester wie Ethylencarbonat, Propylencarbonat, Butylencarbonat, oder Dialkylcarbonsäureester wie Dimethylcarbonat, Diethylcarbonat, Dipropylcarbonat, Dibutylcarbonat, Dioctylcarbonat) ein. Bei dem Träger kann es sich auch um ein verflüssigtes gasförmiges Streckmittel handeln, d.h. eine Flüssigkeit, die bei normaler Temperatur und unter Normaldruck gasförmig ist, zum Beispiel Aerosoltreibmittel wie Halogenkohlenwasserstoffe, Butan, Propan, Stickstoff und Kohlendioxid. A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the application of the compounds, for example to plants, parts of plants or seeds. Examples of suitable solid supports include, but are not limited to, ammonium salts, especially ammonium sulfates, ammonium phosphates and ammonium nitrates, ground natural rock such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, silica gel, and ground synthetic rock, such as finely divided silica, alumina and silicates. Examples of typical suitable solid carriers for the production of granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice stone, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic materials such as paper, sawdust, coconut shells , Corn on the cob and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride ), Alcohols and polyols (which can also be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), esters (including fats and oils) and (poly) ethers, unsubstituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and esters thereof, lactams (such as N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), vegetable oils or of animal origin, nitriles (Alkyl nitriles such as acetonitrile, propiononitrile, butyronitrile, or aromatic nitriles such as benzonitrile), carbonic acid esters (cyclic carbonic acid esters such as ethylene carbonate, propylene carbonate, butylene carbonate, or dialkyl carbonate such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate). The carrier can also be a liquefied gaseous extender, ie a liquid that can be used at normal temperature and under normal pressure is gaseous, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
Bevorzugte feste Träger sind aus Tonen, Talkum und Siliciumdioxid ausgewählt. Preferred solid supports are selected from clays, talc and silica.
Bevorzugte flüssige Träger sind aus Wasser, Fettsäureamiden und Estern davon, aromatischen und nichtaromatischen Kohlenwasserstoffen, Lactamen, Lactonen, Kohlensäureestern, Ketonen, (Poly)ethern ausgewählt. Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonic acid esters, ketones, (poly) ethers.
Die Menge an Träger liegt typischerweise im Bereich von 1 bis 99,99 Gew.-%, vorzugsweise 5- 99,9 Gew.-%, besonders bevorzugt 10 bis 99,5 Gew.-% und am meisten bevorzugt 20 bis 99 Gew.-% der Formulierung. The amount of carrier is typically in the range of 1 to 99.99% by weight, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight and most preferably 20 to 99% by weight. -% of the formulation.
Flüssige Träger sind typischerweise in einem Bereich von 20 bis 90 Gew.-%, zum Beispiel 30 bis 80 Gew.-% der Formulierung vorhanden. Liquid carriers are typically present in a range of 20 to 90% by weight, for example 30 to 80% by weight of the formulation.
Feste Träger sind typischerweise in einem Bereich von 0 bis 50 Gew.-%, vorzugsweise 5 bis 45 Gew.-%, zum Beispiel 10 bis 30 Gew.-% der Formulierung vorhanden. Solid carriers are typically present in a range of 0 to 50%, preferably 5 to 45%, for example 10 to 30% by weight of the formulation.
Umfasst die Formulierung zwei oder mehr Träger, so beziehen sich die umrissenen Bereiche auf die Gesamtmenge an Träger. If the formulation comprises two or more carriers, the areas outlined relate to the total amount of carrier.
Bei dem Tensid kann es sich um ein ionisches (kationisches oder anionisches), amphoteres oder nichtionisches Tensid wie ionische oder nichtionische Emulgatoren, Schaumbilder, Dispersionsmittel, Netzmittel, Penetrationsförderer und beliebige Mischungen davon handeln. Beispiele für geeignete Tenside schließen, wobei dies nicht einschränkend ist, Salze von Polyacrylsäure, ethoxylierte Poly(alpha- substituierte)acrylatderivate, Salze von Fignosulfonsäure (wie Natriumlignosulfonat), Salze von Phenolsulfonsäure oder Naphthalinsulfonsäure, Polykondensate von Ethylenoxid und/oder Propylenoxid mit oder ohne Alkoholen, Fettsäuren oder Fettaminen (zum Beispiel Polyoxyethylenfettsäureester wie Rizinusölethoxylat, Polyoxyethylenfettalkoholether, zum Beispiel Alkylarylpolyglykolether), substituierte Phenole (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulfobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenolen, Fettsäureester von Polyolen (wie Fettsäureester von Glycerin, Sorbit oder Saccharose), Sulfate (wie Alkylsulfate und Alkylethersulfate), Sulfonate, (zum Beispiel Alkylsulfonate, Arylsulfonate und Alkylbenzolsulfonate), sulfonierte Polymere von Naphthalin/Formaldehyd, Phosphatester, Proteinhydrolysate, Fignosulfitablaugen und Methylcellulose ein. Wird im vorliegenden Absatz auf Salze verwiesen, so bezieht sich dies vorzugsweise auf die betreffenden Alkali-, Erdalkali- und Ammoniumsalze. The surfactant can be an ionic (cationic or anionic), amphoteric or nonionic surfactant such as ionic or nonionic emulsifiers, foaming agents, dispersants, wetting agents, penetration promoters and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, ethoxylated poly (alpha-substituted) acrylate derivatives, salts of fignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols , Fatty acids or fatty amines (for example polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates such as fatty acid esters, or phenolic acid esters of polyethoxylic acid esters), phosphoric acid esters of polyethoxylic esters of glycerine, sorbitol or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates, (for example alkyl sulfonates, aryl sulfonates and alkylbenzenesulfonates), sulfonated polymers of naphthalene / formaldehyde, P phosphate esters, protein hydrolyzates, fignosulfite waste liquors and methyl cellulose. If reference is made to salts in the present paragraph, this preferably refers to the alkali, alkaline earth and ammonium salts concerned.
Bevorzugte Tenside sind aus ethoxylierten Poly(alpha-substituierten)acrylatderivaten, Polykondensaten von Ethylenoxid und/oder Propylenoxid mit Alkoholen, Polyoxyethylenfettsäureestern, Alkylbenzolsulfonaten, sulfonierten Polymeren von Naphthalin/Formaldehyd,Preferred surfactants are from ethoxylated poly (alpha-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, Alkylbenzenesulfonates, sulfonated polymers of naphthalene / formaldehyde,
Polyoxyethylenfettsäureestern wie Rizinusölethoxylat, Natriumlignosulfonat und Arylphenolethoxylat ausgewählt. Polyoxyethylene fatty acid esters such as castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylate.
Die Menge an Tensid liegt typischerweise im Bereich von 5 bis 40 Gew.-%, zum Beispiel 10 bis 20 Gew.-%, der Formulierung. The amount of surfactant is typically in the range of 5 to 40% by weight, for example 10 to 20% by weight, of the formulation.
Weitere Beispiele für geeignete Fiilfsstoffe schließen wasserabweisende Substanzen, Trockenmittel, Bindemittel (Klebstoffe, Fiaftmittel, Fixiermittel wie Carboxymethylcellulose, natürliche und synthetische Polymere in Form von Pulvern, Granulaten oder Latizes, wie Gummi arabicum, Polyvinylalkohol und Polyvinylacetat, natürliche Phospholipide wie Cephaline und Lecithine und synthetische Phospholipide, Polyvinylpyrrolidon und Tylose), Verdickungsmittel und sekundäre Verdickungsmittel (wie Celluloseether, Acrylsäurederivate, Xanthan, modifizierte Tone, z.B. die unter dem Namen Bentone erhältlichen Produkte, und feinteiliges Siliciumdioxid), Stabilisatoren (z.B. Kältestabilisatoren, Konservierungsstoffe (z.B. Dichlorophon, Benzylalkoholhemiformal, 1,2- Benzisothiazolin-3-on, 2-Methyl-4-isothiazolin-3-on), Antioxidationsmittel, Lichtschutzmittel, insbesondere UV-Schutzmittel, und andere Mittel, die die chemische und/oder physikalische Stabilität verbessern), Farbstoffe oder Pigmente (wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid und Berliner Blau; organische Farbstoffe, z.B. Alizarin-, Azo- und Metallphthalocyaninfarbstoffe), Anti schaummittel (z.B. Siliconantischaummittel und Magnesiums tearat), Frostschutzmittel, Kleber, Gibberelline und Verarbeitungshilfsstoffe, Mineral- und Pflanzenöle, Duftstoffe, Wachse, Nährstoffe (einschließlich Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink), Schutzkolloide, thixotropische Substanzen, Penetriermittel, Sequestriermittel und Komplexbildner ein. Further examples of suitable auxiliaries include water-repellent substances, drying agents, binders (adhesives, fixing agents, fixing agents such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic ones Phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan, modified clays, e.g. the products available under the name Bentone, and finely divided silicon dioxide), stabilizers (e.g. cold stabilizers, preservatives (e.g. dichlorophone, benzyl alcohol hemiformal, 1, 2- Benzisothiazolin-3-one, 2-methyl-4-isothiazolin-3-one), antioxidants, light stabilizers, especially UV protection agents, and other agents that improve chemical and / or physical stability), dyes or pigments (such as on organic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), anti-foam agents (e.g. silicone antifoam and magnesium tearate), antifreeze, glue, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including trace nutrients such as salts of iron, manganese , Boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complexing agents.
Die Auswahl an Fiilfsstoffen hängt von der vorgesehenen Anwendungsweise der erfindungsgemäßen Verbindung und/oder von den physikalischen Eigenschaften der Verbindung(en) ab. Weiterhin können Fiilfsstoffe so gewählt werden, dass sie den Formulierungen bzw. den daraus hergestellten Anwendungsformen bestimmte Eigenschaften (technische, physikalische und/oder biologische Eigenschaften) verleihen. Durch die Auswahl an Fiilfsstoffen kann es möglich sein, die Formulierungen an bestimmte Bedürfnisse anzupassen. The choice of excipients depends on the intended use of the compound according to the invention and / or on the physical properties of the compound (s). Furthermore, excipients can be selected so that they impart certain properties (technical, physical and / or biological properties) to the formulations or the application forms produced therefrom. The choice of excipients may make it possible to adapt the formulations to specific requirements.
Die Formulierung umfasst eine insektizid/akarizid/nematizid wirksame Menge der erfindungsgemäßen Verbindung(en). Der Begriff „wirksame Menge“ bezeichnet eine Menge, die zur Bekämpfung von Schadinsekten/-milben/-nematoden auf kultivierten Pflanzen oder beim Materialschutz ausreicht und die die behandelten Pflanzen nicht wesentlich schädigt. Eine solche Menge kann in einem weiten Bereich variieren und hängt von verschiedenen Faktoren wie der zu bekämpfenden Insekten/-milben/- nematodenart, der behandelten kultivierten Pflanze bzw. dem behandelten Material, den Klimabedingungen und der jeweils eingesetzten erfindungsgemäßen Verbindung ab. Gewöhnlich enthält die erfindungsgemäße Formulierung 0,01 bis 99 Gew.-%, vorzugsweise 0,05 bis 98 Gew.-%, besonders bevorzugt 0,1 bis 95 Gew.-%, noch mehr bevorzugt 0,5 bis 90 Gew.-%, am meisten bevorzugt 1 bis 80 Gew.-% der erfindungsgemäßen Verbindung. Es ist möglich, dass eine Formulierung zwei oder mehr erfindungsgemäße Verbindungen umfasst. In einem solchen Fall beziehen sich die umrissenen Bereiche auf die Gesamtmenge der Verbindungen der vorliegenden Erfindung. The formulation comprises an insecticidally / acaricidally / nematicidically effective amount of the compound (s) according to the invention. The term “effective amount” denotes an amount which is sufficient to control harmful insects / mites / nematodes on cultivated plants or for material protection and which does not significantly damage the treated plants. Such an amount can vary within a wide range and depends on various factors such as the insect / mite / nematode species to be controlled, the cultivated plant or material treated, the climatic conditions and the particular compound according to the invention used. The formulation according to the invention usually contains 0.01 to 99% by weight, preferably 0.05 to 98% by weight, particularly preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, most preferably 1 to 80% by weight of the compound according to the invention. It is possible for a formulation to comprise two or more compounds according to the invention. In such a case, the areas outlined relate to the total amount of the compounds of the present invention.
Die erfindungsgemäße Formulierung kann in einem beliebigen herkömmlichen Formulierungstyp vorliegen, wie Fösungen (z.B. wässrige Fösungen), Emulsionen, Suspensionen auf Wasser- und Ölbasis, Pulvern (z.B. Spritzpulvern, löslichen Pulvern), Stäuben, Pasten, Granulaten (z.B. löslichen Granulaten, Streugranulaten), Suspoemulsionskonzentraten, mit der erfindungsgemäßen Verbindung imprägnierten natürlichen oder synthetischen Produkten, Düngemitteln und außerdem Mikroverkapselungen in polymeren Substanzen. Die erfindungsgemäße Verbindung kann in suspendierter, emulgierter oder gelöster Form vorliegen. Beispiele für bestimmte geeignete Formulierungstypen sind Fösungen, wasserlösliche Konzentrate (z.B. SF, FS), Dispersionskonzentrate (DC), Suspensionen und Suspensionskonzentrate (z.B. SC, OD, OF, FS), Emulsionskonzentrate (z.B. EC), Emulsionen (z.B. EW, EO, ES, ME, SE), Kapseln (z.B. CS, ZC), Pasten, Pastillen, Spritzpulver oder Stäube (z.B. WP, SP, WS, DP, DS), Pressteile (z.B. BR, TB, DT), Granulate (z.B. WG, SG, GR, FG, GG, MG), insektizide Artikel (z.B. LN) sowie Gelformulierungen zur Behandlung von Pflanzenfortpflanzungsmaterial wie Samen (z.B. GW, GF). Diese und andere Formulierungstypen sind von der Food and Agriculture Organization of the United Nations (FAO) definiert. Ein Überblick findet sich im „Catalogue of pesticide formulation types and international coding System“, Technical Monograph Nr. 2, 6. Aufl. Mai 2008, Croplife International.The formulation according to the invention can be in any conventional formulation type, such as solutions (e.g. aqueous solutions), emulsions, water- and oil-based suspensions, powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, scattering granules), Suspoemulsion concentrates, natural or synthetic products impregnated with the compound according to the invention, fertilizers and also microencapsulations in polymeric substances. The compound according to the invention can be in suspended, emulsified or dissolved form. Examples of certain suitable formulation types are solutions, water-soluble concentrates (e.g. SF, FS), dispersion concentrates (DC), suspensions and suspension concentrates (e.g. SC, OD, OF, FS), emulsion concentrates (e.g. EC), emulsions (e.g. EW, EO, ES , ME, SE), capsules (e.g. CS, ZC), pastes, lozenges, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressed parts (e.g. BR, TB, DT), granulates (e.g. WG, SG , GR, FG, GG, MG), insecticidal articles (e.g. LN) and gel formulations for the treatment of plant reproductive material such as seeds (e.g. GW, GF). These and other formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview can be found in the “Catalog of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th edition May 2008, Croplife International.
Vorzugsweise hegt die erfindungsgemäße Formulierung in Form einer der folgenden Typen vor: EC, SC, FS, SE, OD, WG, WP, CS, besonders bevorzugt EC, SC, OD, WG, CS. The formulation according to the invention is preferably in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferably EC, SC, OD, WG, CS.
Weitere Details zu Beispielen für Formulierungstypen und ihre Herstellung finden sich unten. Sind zwei oder mehr erfindungsgemäße Verbindungen vorhanden, so bezieht sich die umrissene Menge an erfindungsgemäßer Verbindung auf die Gesamtmenge der Verbindungen der vorliegenden Erfindung. Dies gilt umgekehrt auch für alle weiteren Komponenten der Formulierung, wenn zwei oder mehr Vertreter einer solchen Komponente, z.B. eines Netz- oder Bindemittels, vorliegen. i) Wasserlösliche Konzentrate (SL, LS) Further details on examples of formulation types and their preparation are provided below. If two or more compounds according to the invention are present, the outlined amount of compound according to the invention relates to the total amount of the compounds of the present invention. Conversely, this also applies to all other components of the formulation if two or more representatives of such a component, e.g. a wetting or binding agent, are present. i) Water-soluble concentrates (SL, LS)
10-60 Gew.-% mindestens einer erfindungsgemäßen Verbindung und 5-15 Gew.-% Tensid (z.B. Polykondensate von Ethylenoxid und/oder Propylenoxid mit Alkoholen) werden in einer solchen Menge Wasser und/oder wasserlöslichem Lösungsmittel (z.B. Alkohole wie Propylenglykol und Carbonaten wie Propylencarbonat) gelöst, so dass sich eine Gesamtmenge von 100 Gew.-% ergibt. Vor der Anwendung wird das Konzentrat mit Wasser verdünnt. ii) Dispersionskonzentrate (DC) 5-25 Gew.-% mindestens einer erfindungsgemäßen Verbindung und 1-10 Gew.-% Tensid und/oder Bindemittel (z.B. Polvinylpyrrolidon) werden in einer solchen Menge organischen Lösungsmittels (z.B. Cyclohexan) gelöst, das sich eine Gesamtmenge von 100 Gew.-% ergibt. Das Verdünnen mit Wasser liefert eine Dispersion. iii) Emulsionskonzentrate (EC) 10-60% by weight of at least one compound according to the invention and 5-15% by weight of surfactant (e.g. polycondensates of ethylene oxide and / or propylene oxide with alcohols) are water and / or water-soluble solvents (e.g. alcohols such as propylene glycol and carbonates) in such an amount such as propylene carbonate), so that the total amount is 100% by weight. Before use, the concentrate is diluted with water. ii) dispersion concentrates (DC) 5-25% by weight of at least one compound according to the invention and 1-10% by weight of surfactant and / or binder (e.g. polyvinylpyrrolidone) are dissolved in such an amount of organic solvent (e.g. cyclohexane) that a total amount of 100% by weight % results. Dilution with water provides a dispersion. iii) Emulsion concentrates (EC)
15-70 Gew.-% mindestens einer erfindungsgemäßen Verbindung und 5-10 Gew.-% Tensid (z.B. eine Mischung von Calciumdodecylbenzolsulfonat und Riziniusölethoxylat) werden in einer solchen Menge wasserunlöslichem organischem Lösungsmittel (z.B. aromatischem Kohlenwasserstoff oder Fettsäureamid) und, falls erforderlich, zusätzlichem wasserlöslichem Lösungsmittel gelöst, so dass man auf eine Gesamtmenge von 100 Gew.-% kommt. Durch Verdünnen mit Wasser erhält man eine Emulsion. iv) Emulsionen (EW, EO, ES) 15-70% by weight of at least one compound according to the invention and 5-10% by weight of surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are used in such an amount of water-insoluble organic solvent (e.g. aromatic hydrocarbon or fatty acid amide) and, if necessary, additional Dissolved water-soluble solvent, so that one comes to a total amount of 100 wt .-%. An emulsion is obtained by diluting with water. iv) emulsions (EW, EO, ES)
5-40 Gew.-% mindestens einer erfindungsgemäßen Verbindung und l-10 Gew.-% Tensid (z.B. eine Mischung von Calciumdodecylbenzolsulfonat und Rizinusölethoxylat, oder Polykondensate von Ethylenoxid und/oder Propylenoxid mit oder ohne Alkoholen) werden in 20-40 Gew.-% wasserunlöslichem organischem Lösungsmittel (z.B. aromatischer Kohlenwasserstoff) gelöst. Die Mischung wird mittels einer Emulgiermaschine zu einer solchen Menge an Wasser gegeben, dass man eine Gesamtmenge von 100 Gew.-% erhält. Bei der erhaltenen Formulierung handelt es sich um eine homogene Emulsion. Vor der Anwendung kann die Emulsion weiter mit Wasser verdünnt werden. v) Suspensionen und Suspensionskonzentrate v-1) Auf Wasserbasis (SC, FS) 5-40% by weight of at least one compound according to the invention and 1-10% by weight of surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, or polycondensates of ethylene oxide and / or propylene oxide with or without alcohols) are used in 20-40% by weight % water-insoluble organic solvent (e.g. aromatic hydrocarbon) dissolved. The mixture is added to such an amount of water by means of an emulsifying machine that a total amount of 100% by weight is obtained. The formulation obtained is a homogeneous emulsion. The emulsion can be further diluted with water before use. v) Suspensions and suspension concentrates v-1) Water-based (SC, FS)
In einem geeigneten Mahlgerät, z. B. einer Kugelmühle, werden 20-60 Gew.-% mindestens einer erfindungsgemäßen Verbindung unter Zugabe von 2-10 Gew.-% Tensid (z.B. Natriumlignosulfonat und Polyoxyethylenfettalkoholether), 0,1-2 Gew.-% Verdickungsmittel (z.B. Xanthan) und Wasser zu einer feinen Wirkstoffsuspension zerkleinert. Das Wasser wird in einer solchen Menge zugegeben, dass man eine Gesamtmenge von 100 Gew.-% erhält. Durch Verdünnen mit Wasser erhält man eine stabile Suspension des Wirkstoffs. Für Formulierungen vom FS-Typ werden bis zu 40 Gew.-% Bindemittel (z.B. Polyvinylalkohol) zugesetzt. v-2) Auf Ölbasis (OD, OF) In a suitable grinding device, e.g. B. a ball mill, 20-60 wt .-% of at least one compound according to the invention with the addition of 2-10 wt .-% surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2 wt .-% thickener (e.g. xanthan) and Crushed water into a fine suspension of active ingredients. The water is added in such an amount that a total amount of 100% by weight is obtained. A stable suspension of the active ingredient is obtained by diluting with water. For formulations of the FS type, up to 40% by weight of binding agent (e.g. polyvinyl alcohol) is added. v-2) Oil-based (OD, OF)
In einem geeigneten Mahlgerät, z.B. einer Kugelmühle, werden 20-60 Gew.-% mindestens einer erfindungsgemäßen Verbindung unter Zugabe von 2-10 Gew.-% Tensid (z.B. Natriumlignosulfonat und Polyoxyethylenfettalkoholether), 0,1-2 Gew.-% Verdickungsmittel (z.B. modifizierter Ton, insbesondere Bentone, oder Siliciumdioxid) und einem organischen Träger zu einer feinen Wirkstoff-Öl-Suspension zerkleinert. Der organische Träger wird in einer solchen Menge zugefügt, dass man eine Gesamtmenge von 100 Gew.-% erhält. Durch Verdünnen mit Wasser erhält man eine stabile Dispersion des Wirkstoffs. vi) Wasserdispergierbare Granulate und wasserlösliche Granulate (WG, SG) l-90 Gew.-%, vorzugsweise 20-80 Gew.-%, am meisten bevorzugt 50-80 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden unter Zugabe eines Tensids (z.B. Natriumlignosulfonat und Natriumalkylnaphthylsulfonate) und gegebenenfalls Trägermaterial fein gemahlen und mittels typischer technischer Anwendungen wie z.B. Extrusion, Sprühtrocknung, Wirbelschichtgranulation in wasserdispergierbare oder wasserlösliche Granulate überführt. Tensid und Trägermaterial werden in einer solchen Menge eingesetzt, dass man eine Gesamtmenge von 100 Gew.-% erhält. Durch Verdünnen mit Wasser erhält man eine stabile Dispersion bzw. Lösung des Wirkstoffs. vii) Wasserdispergierbare Pulver und wasserlösliche Pulver (WP, SP, WS) In a suitable grinding device, e.g. a ball mill, 20-60% by weight of at least one compound according to the invention with the addition of 2-10% by weight surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight thickener ( e.g. modified clay, especially bentone, or silicon dioxide) and an organic carrier to form a fine active ingredient-oil suspension crushed. The organic vehicle is added in such an amount that the total amount is 100% by weight. A stable dispersion of the active ingredient is obtained by diluting with water. vi) Water-dispersible granules and water-soluble granules (WG, SG) 1-90% by weight, preferably 20-80% by weight, most preferably 50-80% by weight of at least one compound according to the invention are added with the addition of a surfactant (e.g. Sodium lignosulfonate and sodium alkylnaphthylsulfonate) and optionally carrier material finely ground and converted into water-dispersible or water-soluble granules by means of typical technical applications such as extrusion, spray drying, fluidized bed granulation. The amount of surfactant and carrier material used is such that a total amount of 100% by weight is obtained. A stable dispersion or solution of the active ingredient is obtained by diluting with water. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden in einer Rotor-Stator-Mühle unter Zugabe von 1-20 Gew.-% Tensid (z.B. Natriumlignosulfonat, Natriumalkylnaphthylsulfonate) und einer solchen Menge an festem Träger, z.B. Kieselgel, dass man auf eine Gesamtmenge von 100 Gew.-% kommt, gemahlen. Durch Verdünnen mit Wasser erhält man eine stabile Dispersion bzw. Lösung des Wirkstoffs. viii) Gel (GW, GL) 50-80 wt .-% of at least one compound according to the invention are in a rotor-stator mill with the addition of 1-20 wt .-% surfactant (e.g. sodium lignosulfonate, sodium alkylnaphthylsulfonate) and such an amount of solid support, e.g. silica gel, that one on a total of 100 wt .-% comes, ground. A stable dispersion or solution of the active ingredient is obtained by diluting with water. viii) Gel (GW, GL)
In einer Kugelmühle werden 5-25 Gew.-% mindestens einer erfindungsgemäßen Verbindung unter Zugabe von 3-10 Gew.-% Tensid (z.B. Natriumlignosulfonat), 1-5 Gew.-% Bindemittel (z.B. Carboxymethylcellulose) und einer solchen Menge an Wasser, dass man auf eine Gesamtmenge von 100 Gew.-% kommt, zerkleinert. Hierdurch erhält man eine feine Suspension des Wirkstoffs. Durch Verdünnen mit Wasser erhält man eine stabile Suspension des Wirkstoffs. ix) Mikroemulsion (ME) In a ball mill, 5-25% by weight of at least one compound according to the invention with the addition of 3-10% by weight of surfactant (e.g. sodium lignosulfonate), 1-5% by weight of binder (e.g. carboxymethyl cellulose) and an amount of water such as that one comes to a total amount of 100 wt .-%, comminuted. This gives a fine suspension of the active ingredient. A stable suspension of the active ingredient is obtained by diluting with water. ix) microemulsion (ME)
5-20 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden zu 5-30 Gew.-% organischer Lösungsmittelmischung (z.B. Lettsäuredimethylamid und Cyclohexanon), 10-25 Gew.-% Tensidmischung (z.B. Polyoxyethylenfettalkoholether und Arylphenolethoxylat) und einer solchen Menge an Wasser, dass man auf eine Gesamtmenge von 100 Gew.-% kommt, gegeben. Diese Mischung wird 1 h gerührt, wodurch sich spontan eine thermodynamisch stabile Mikroemulsion bildet. x) Mikrokapseln (CS) 5-20% by weight of at least one compound according to the invention is converted to 5-30% by weight of an organic solvent mixture (e.g. dimethyl amide and cyclohexanone), 10-25% by weight of surfactant mixture (e.g. polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and an amount of water such as that one comes to a total amount of 100 wt .-%, given. This mixture is stirred for 1 hour, as a result of which a thermodynamically stable microemulsion forms spontaneously. x) microcapsules (CS)
Eine Ölphase mit 5-50 Gew.-% mindestens einer erfindungsgemäßen Verbindung, 0-40 Gew.-% wasserunlöslichen organischen Lösungsmittels (z.B. aromatischem Kohlenwasserstoff), 2-15 Gew.-% acrylischen Monomeren (z.B. Methylmethacrylat, Methacrylsäure und einem Di- oder Triacrylat) werden in einer wässrigen Lösung eines Schutzkolloids (z.B. Polyvinylalkohol) dispergiert. Eine mit einem Radikalstarter eingeleitete radikalische Polymerisation führt zur Bildung von Poly(methy)acrylatmikrokapseln. Alternativ dazu wird eine 5-50 Gew.-% mindestens einer erfindungsgemäßen Verbindung, 0-40 Gew.-% wasserunlösliches organisches Lösungsmittel (z.B. aromatischen Kohlenwasserstoff) und ein Isocyanatmonomer (z.B. Diphenylmethen-4,4‘-diisocyanat) umfassende Ölphase in einer wässrigen Lösung eines Schutzkolloids (z.B. Polyvinylakohol) dispergiert, dies führt zur Bildung von Polyharnstoffmikrokapseln. Gegebenenfalls kann man auch die Zugabe eines Polyamins (z.B. Hexamethylendiamin) anwenden, um die Bildung von Polyharnstoffmikrokapseln herbeizuführen. Die Monomere machen 1-10 Gew.-% der gesamten CS -Formulierung aus. xi) Stäubepulver (DP, DS) An oil phase with 5-50 wt .-% of at least one compound according to the invention, 0-40 wt .-% water-insoluble organic solvent (for example aromatic hydrocarbon), 2-15 wt .-% acrylic monomers (for example methyl methacrylate, methacrylic acid and a di- or Triacrylate) dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). A radical polymerization initiated with a radical initiator leads to the formation of poly (methy) acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of at least one compound according to the invention, 0-40% by weight water-insoluble organic solvent (e.g. aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanate) A solution of a protective colloid (e.g. polyvinyl alcohol) dispersed, this leads to the formation of polyurea microcapsules. Optionally, the addition of a polyamine (eg hexamethylenediamine) can also be used to induce the formation of polyurea microcapsules. The monomers make up 1-10% by weight of the total CS formulation. xi) dust powder (DP, DS)
1-10 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden fein gemahlen und innig mit einer solchen Menge an festem Träger, z.B. feinteiligem Kaolin, gemischt, dass man auf eine Gesamtmenge von 100 Gew.-% kommt. xii) Granulate (GR, FG) 1-10% by weight of at least one compound according to the invention is finely ground and intimately mixed with such an amount of solid carrier, e.g. finely divided kaolin, that a total amount of 100% by weight is obtained. xii) granules (GR, FG)
0,5-30 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden fein gemahlen und mit einer solchen Menge an festem Träger (z.B. Silicat) assoziiert, dass man auf eine Gesamtmenge von 100 Gew.-% kommt. xiii) Ultra-Low-Volumen-Flüssigkeiten (UL) l-50 Gew.-% mindestens einer erfindungsgemäßen Verbindung werden in einer solchen Menge an organischem Lösungsmittel, z.B. aromatischem Kohlenwasserstoff, gelöst, dass man auf eine Gesamtmenge von 100 Gew.-% kommt. 0.5-30% by weight of at least one compound according to the invention is finely ground and associated with such an amount of solid support (e.g. silicate) that a total amount of 100% by weight is obtained. xiii) Ultra-Low-Volume Liquids (UL) 1-50% by weight of at least one compound according to the invention are dissolved in such an amount of organic solvent, for example aromatic hydrocarbon, that a total amount of 100% by weight is achieved .
Die Formulierungstypen i) bis xiii) können weitere Hilfsstoffe wie 0,1-1 Gew.-% Konservierungsstoffe, 0,1-1 Gew.-% Antischaummittel, 0,1-1 Gew.-% Farbstoffe und/oder Pigmente und 5-10 Gew.-% Frostschutzmittel umfassen. Formulation types i) to xiii) can contain further auxiliaries such as 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoam agents, 0.1-1% by weight of dyes and / or pigments and 5- Comprise 10% by weight antifreeze.
Mischungen Mixtures
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbiziden, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, 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. The compounds of the formula (I) can also be used as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, bird repellants, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators to be so z. B. to broaden the spectrum of action, to lengthen the duration of action, to increase the speed of action, to prevent repellancy or to prevent the development of resistance. Furthermore, such combinations of active ingredients can affect plant growth and / or tolerance to abiotic factors such. B. high or low temperatures, against drought or against increased water or Improve soil salinity. The flowering and fruiting behavior can also be improved, germination and rooting can be optimized, harvesting easier and harvest yield increased, ripening can be influenced, the quality and / or the nutritional value of the harvested products can be increased, the shelf life can be extended and / or the workability of the harvested products can be improved.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. Furthermore, the compounds of the formula (I) can be present as a mixture with further active ingredients or semiochemicals, such as attractants and / or bird repellants and / or plant activators and / or growth regulators and / or fertilizers. The compounds of the formula (I) can also be used to improve the plant properties such as, for example, growth, yield and quality of the harvested material.
In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. In a particular embodiment according to the invention, the compounds of the formula (I) are present in formulations or in the use forms prepared from these formulations as a mixture with further 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 nicht in jedem Fall explizit genannt wurden. Alle genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktioneilen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. If one of the compounds mentioned below can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in every case. All of the mixing partners mentioned can, if appropriate, if they are capable of doing so on the basis of their functional groups, 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 Pesti idhandhuch („The Pesticide Manual“ 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z. B. http://www.aIanwood.net/pesticides). Die Klassifizierung basiert auf dem zum Zeitpunkt der Einreichung dieser Patentanmeldung gültigen IRAC Mode of Action Classification Scheme. The active ingredients named here with their “Common Name” are known and described, for example, in the Pesti idhandhuch (“The Pesticide Manual” 16th Ed., British Crop Protection Council 2012) or can be researched on the Internet (e.g. http: //www.aIanwood .net / pesticides). The classification is based on the IRAC Mode of Action Classification Scheme valid at the time of filing this patent application.
(1) AcetyIchoIinesterase(AChE)-Inhibitoren, vorzugsweise Carbamate ausgewählt aus Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanat, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamat, Trimethacarb, XMC und Xylylcarb, oder Organophosphate ausgewählt aus 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, IsopropyI-0-(methoxyaminothio-phosphoryI)saIicyIat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoat, 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. (1) AcetyIchoIinesterase (AChE) inhibitors, preferably carbamates selected from Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarbol, Metocamarbol, Methocroarbom, Methocamyl, Furoprobom, Furoathiarbom Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamat, Trimethacarb, XMC and Xylylcarb, or organophosphates selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chloro-phos-phos, chlorpyrorphos-methyl S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoat, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazat, Heptenophos, Imicyafos, Isofenphos, IsopropyIaminothI , Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoat, Oxydemeton-methyl, Parathion-methyl, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthione, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon and Vamidothion.
(2) GABA-gesteuerte Chlorid-Kanal-Blocker, vorzugsweise Cyclodien-organochlorine ausgewählt aus Chlordan und Endosulfan, oder Phenylpyrazole (Fiprole) ausgewählt aus Ethiprol und Fipronil. (2) GABA-controlled chloride channel blockers, preferably cyclodiene organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiprole) selected from ethiprole and fipronil.
(3) Natrium-Kanal-Modulatoren, vorzugsweise Pyrethroide ausgewählt aus Acrinathrin, Allethrin, d-cis- trans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl-Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma- Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta- Cypermethrin, Cyphenothrin [(lR)-trans-Isomer], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomer], Esfenvalerat, Etofenprox, Fenpropathrin, Fenvalerat, Flucythrinat, Flumethrin, tau-Fluvalinat, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(lR)-trans-Isomer], Prallethrin, Pyrethrine (Pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(lR)-Isomer], Tralomethrin und Transfluthrin, oder DDT oder Methoxychlor. (3) Sodium channel modulators, preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, beta -Cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans-isomer], [(EZ) - deltamethrin (lR) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(lR) -trans-isomer], prallethrin (pyrethral) isomer], , Resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(lR) isomer], tralomethrin and transfluthrin, or DDT or methoxychlor.
(4) Kompetitive Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), vorzugsweise Neonicotinoide ausgewählt aus Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam, oder Nicotin, oder Sulfoximine ausgewählt aus Sulfoxaflor, oder Butenolide ausgewählt aus Flupyradifuron, oder Mesoionics ausgewählt aus Triflumezopyrim. (4) Competitive Modulators of the Nicotinic Acetylcholine Receptor (Nachr), preferably neonicotinoids selected from acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxa class, or beneolide selected from flupyradifuron, or mesoionics selected from triflumezopyrim.
(5) Allosterische Modulatoren des nicotinischen Acetylcholin-Rezeptors (nAChR), vorzugsweise Spinosyne ausgewählt aus Spinetoram und Spinosad. (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), preferably spinosyne selected from Spinetoram and Spinosad.
(6) Allosterische Modulatoren des Glutamat-abhängigen Chloridkanals (GluCl), vorzugsweise Avermectine/Milbemycine ausgewählt aus Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (6) Allosteric modulators of the glutamate-dependent chloride channel (GluCl), preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.
(7) Juvenilhormon-Mimetika, vorzugsweise Juvenilhormon-Analoge ausgewählt aus Hydropren, Kinopren und Methopren, oder Fenoxycarb oder Pyriproxyfen. (7) Juvenile hormone mimetics, preferably juvenile hormone analogs selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.
(8) Verschiedene nicht spezifische (multi-site) Inhibitoren, vorzugsweise Alkylhalogenide ausgewählt aus Methylbromid und andere Alkylhalogenide, oder Chloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein oder Methylisocyanaterzeuger ausgewählt aus Diazomet und Metam. (8) Various non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides, or chloropicrin or sulfuryl fluoride or borax or tartrate or methyl isocyanate producers selected from diazomet and metam.
(9) TRPV-Kanal-Modulatoren chordotonaler Organe, vorzugsweise Pyridinazomethane, ausgewählt aus Pymetrozin und Pyrifluquinazon oder Pyropene ausgewählt aus Afidopyropen. (9) TRPV channel modulators of chordotonal organs, preferably pyridinazomethanes, selected from pymetrozine and pyrifluquinazone or pyropenes selected from afidopyropene.
(10) CHS1 betreffende Milbenwachstumsinhibitoren ausgewählt aus Clofentezin, Hexythiazox, Diflovidazin und Etoxazol. (11) Mikrobielle Disruptoren der Insektendarmmembran ausgewählt aus Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und B.t.- Pflanzenproteine ausgewählt aus CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb und Cry34Ab 1/35 Abi. (10) CHS1 related mite growth inhibitors selected from clofentezine, hexythiazox, diflovidazine and etoxazole. (11) Microbial disruptors of the insect intestinal membrane selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, Cryc3 , mCry3A, Cry3Ab, Cry3Bb and Cry34Ab 1/35 Abi.
(12) Inhibitoren der mitochondrialen ATP-Synthase, vorzugsweise ATP-Disruptoren ausgewählt aus Diafenthiuron, oder Organozinnverbindungen ausgewählt aus Azocyclotin, Cyhexatin und Fenbutatin- oxid, oder Propargit oder Tetradifon. (12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotine, cyhexatin and fenbutatin oxide, or propargite or tetradifon.
(13) Entkoppler der oxidativen Phoshorylierung durch Störung des Protonengradienten ausgewählt aus Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupler of oxidative phosphorylation by disrupting the proton gradient selected from chlorfenapyr, DNOC and sulfluramide.
(14) Blocker des nicotinischen Acetylcholinrezeptorkanals ausgewählt aus Bensultap, Cartap- hydrochlorid, Thiocyclam und Thiosultap-Natrium. (14) Blocker of the nicotinic acetylcholine receptor channel selected from bensultap, cartap hydrochloride, thiocyclam and thiosultap sodium.
(15) CHS1 betreffende Inhibitoren der Chitinbiosynthese, vorzugsweise Benzoylharnstoffe, ausgewählt aus Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (15) CHS1-related inhibitors of chitin biosynthesis, preferably benzoylureas, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and.
(16) Inhibitoren der Chitinbiosynthese, Typ 1 ausgewählt aus Buprofezin. (16) Inhibitors of chitin biosynthesis, type 1 selected from buprofezin.
(17) Häutungsdisruptor (insbesondere bei Dipteren, d. h. Zweiflüglern) ausgewählt aus Cyromazin.(17) molting disruptor (particularly in diptera, i.e. two-winged birds) selected from cyromazine.
(18) Ecdyson-Rezeptor- Agonisten, vorzugsweise Diacylhydrazine, ausgewählt aus Chromafenozid, Halofenozid, Methoxyfenozid und Tebufenozid. (18) Ecdysone receptor agonists, preferably diacylhydrazines, selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Oktopamin-Rezeptor- Agonisten ausgewählt aus Amitraz. (19) Octopamine receptor agonists selected from amitraz.
(20) Mitochondriale Komplex-III-Elektronentransportinhibitoren ausgewählt aus Hydramethylnon, Acequinocyl, Fluacrypyrim und Bifenazat. (20) Mitochondrial complex III electron transport inhibitors selected from hydramethylnone, acequinocyl, fluacrypyrim, and bifenazate.
(21) Mitochondriale Komplex-I-Elektronentransportinhibitoren, vorzugsweise METI- Akarizide und Insektizide ausgewählt aus Fenazaquin, Fenpyroximat, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad, oder Rotenon (Derris). (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad and tolfenpyrad, or Rotenone (Derris).
(22) Blocker des spannungsabhängigen Natriumkanals, vorzugsweise Oxadiazine ausgewählt aus Indoxacarb oder Semicarbazone ausgewählt aus Metaflumizon. (22) Blockers of the voltage-dependent sodium channel, preferably oxadiazines selected from indoxacarb or semicarbazones selected from metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, vorzugsweise Tetron- und T etram säurederi vate ausgewählt aus Spirodiclofen, Spiromesifen, Spiropidion und Spirotetramat. (24) Inhibitoren des mitochondrialen KompIex-IV-EIektronentransports, vorzugsweise Phosphide ausgewählt aus Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid, oder Cyanide ausgewählt aus Calciumcyanid, Kaliumcyanid und Natriumcyanid. (23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidion and spirotetramat. (24) Inhibitors of mitochondrial complex IV electron transport, preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.
(25) Inhibitoren des mitochondrialen Komplex-II-Elektronentransports, vorzugsweise beta- Ketonitrilderivate ausgewählt aus Cyenopyrafen und Cyflumetofen, oder Carboxanilide ausgewählt aus Pyflubumid. (25) Inhibitors of mitochondrial complex II electron transport, preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.
(28) Ryanodinrezeptor-Modulatoren, vorzugsweise Diamide ausgewählt aus Chlorantraniliprol, Cyantraniliprol, Cyclaniliprol, Flubendiamid und Tetraniliprol. (28) Ryanodine receptor modulators, preferably diamides selected from chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole.
(29) Modulatoren chordotonaler Organe (mit Undefinierter Zielstruktur) ausgewählt aus Flonicamid.(29) Modulators of chordotonal organs (with undefined target structure) selected from flonicamid.
(30) Allosterische Modulatoren des GABA-abhängigen Chloridkanals, vorzugsweise meta- Diamide ausgewählt aus Broflanilid oder Isoxazole ausgewählt aus Fluxametamid. (30) Allosteric modulators of the GABA-dependent chloride channel, preferably meta-diamide selected from broflanilide or isoxazole selected from fluxametamide.
(31) Baculoviren, vorzugsweise Granuloviren (GVs) ausgewählt aus Cydia pomonella GV und Thaumatotibia leucotreta (GV) oder Nukleopolyhedro viren (NPVs) ausgewählt aus Anticar sia gemmatalis MNPV und Helicoverpa armigera NPV. (31) Baculoviruses, preferably granuloviruses (GVs) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV) or nucleopolyhedro viruses (NPVs) selected from Anticar sia gemmatalis MNPV and Helicoverpa armigera NPV.
(32) Allosterische Modulatoren (Stelle II) des nikotinischen Acetylcholinrezeptors ausgewählt aus GS- omega/kappa-HXTX-Hv 1 a-Peptid. (32) Allosteric modulators (position II) of the nicotinic acetylcholine receptor selected from GS- omega / kappa-HXTX-Hv 1 a peptide.
(33) Weitere Wirkstoffe ausgewählt aus Acynonapyr, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximat, Benzpyrimoxan, Bromopropylat, Chinomethionat, Chloroprallethrin, Cryolit, Cyclobutrifluram, Cycloxaprid, Cyetpyrafen, Cyhalodiamid, Cyproflanilide (CAS 2375110-88-4), Dicloromezotiaz, Dicofol, Dimpropyridaz, epsilon-Metofluthrin, epsilon-Momfluthrin, Flometoquin, Fluazaindolizin, Flucypyriprol (CAS 1771741-86-6), Fluensulfon, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Flupyrimin, Fluralaner, Fufenozid, Flupentiofenox, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodion, Isocycloseram, kappa-Bifenthrin, kappa-Tefluthrin, Fotilaner, Meperfluthrin, Nicofluprol (CAS 1771741-86-6), Oxazosulfyl, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Sarolaner, Spidoxamat, Spirobudiclofen, Tetramethylfluthrin, Tetrachlorantraniliprol, Tigolaner, Tioxazafen, Thiofluoximate, Tyclopyrazoflor, Iodmethan; des Weiteren Präparate auf Basis von Bacillus firmus (1-1582, Votivo) und Azadirachtin (BioNeem), sowie folgende Verbindungen: l-{2- Fluor-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-lH-l,2,4-triazol-5-amin (bekannt aus W02006/043635) (CAS 885026-50-6), 2-Chlor-N-[2-{ l-[(2E)-3-(4-chlorphenyl)prop-2-en- l-yl]piperidin-4-yl}-4-(trifluormethyl)phenyl]isonicotinamid (bekannt aus W02006/003494) (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) (CAS1440516-42-6), PF1364 (bekannt aus JP2010/018586) (CAS 1204776-60-2), (3E)-3-[l-[(6-Chlor-3-pyridyl)methyl]-2- pyridyliden]-l,l,l-trifluorpropan-2-on (bekannt aus WO2013/144213) (CAS 1461743-15-6), N-[3- (Benzylcarbamoyl)-4-chlorphenyl] - 1 -methyl-3-(pentafluorethyl)-4-(trifluormethyl)- lH-pyrazol-5- carboxamid (bekannt aus WO2010/051926) (CAS 1226889-14-0), 5-Brom-4-chlor-N-[4-chlor-2-methyl- 6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazol-3-carboxamid (bekannt aus CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl- N-(cis-l-oxido-3-thietanyl)benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3- isoxazolyl]-2-methyl-N-(trans-l-oxido-3-thietanyl)benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5- dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-l-oxido-3-thietanyl)benzamid (bekannt aus WO 2013/050317 Al) (CAS 1332628-83-7), N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid, (+)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3- [(3,3,3-trifluorpropyl)sulfinyl]propanamid und (-)-N-[3-Chlor-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl- 3-[(3,3,3-trifluorpropyl)sulfinyl]propanamid (bekannt aus WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 Al) (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-(33) Other active ingredients selected from acynonapyr, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclobutrifluram, cycloxaprid, cyetpyrafenol, dehydrozol), cyetofazol, D, D, D , epsilon-metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolizine, flucypyriprole (CAS 1771741-86-6), fluensulfon, flufenerim, flufenoxystrobin, flufiprol, fluhexafon, fluopyramofen, flupyrfleption, fluralaner gu, fufenerimidion , Isocycloseram, kappa-bifenthrin, kappa-tefluthrin, Fotilaner, meperfluthrin, nicofluprole (CAS 1771741-86-6), oxazosulfyl, paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, tiguoline-aminofluoro-tetrachloro, tigluoramate, spirobudoxrole , Tyclopyrazoflor, iodomethane; also preparations based on Bacillus firmus (1-1582, Votivo) and azadirachtin (BioNeem), as well as the following compounds: l- {2- fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -lH-l, 2,4-triazol-5-amine (known from W02006 / 043635) (CAS 885026-50-6), 2-chloro-N- [2- {l- [(2E) -3- (4-chlorophenyl) prop-2-en- l-yl] piperidin-4-yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494) (CAS 872999-66- 1), 3- (4-chloro-2,6-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3- (4-chloro-2,6-dimethylphenyl) -8-methoxy-2-oxo l, 8-diazaspiro [4.5] dec-3-en-4-yl-ethyl carbonate (known from EP 2647626) (CAS1440516-42-6), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), (3E) -3- [l - [(6-chloro-3-pyridyl) methyl] -2- pyridylidene] -l, l, l-trifluoropropan-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- Dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis -1-oxido-3-thietanyl) benzamide, 4- [5- (3,5-dichlorophenyl ) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (trans-1-oxido-3-thietanyl) benzamide and 4 - [(5S) -5- (3, 5-dichlorophenyl) -4,5-dihydro-5- (trifluoromethyl) -3-isoxazolyl] -2-methyl-N- (cis-l-oxido-3-thietanyl) benzamide (known from WO 2013/050317 A1) ( CAS 1332628-83-7), N- [3-chloro-l- (3-pyridinyl) -lH-pyrazol-4-yl] -N-ethyl-3- [(3,3,3-trifluoropropyl) sulfinyl] propanamide, (+) - N- [3-chloro-1- (3-pyridinyl) -1H -pyrazol-4-yl] - N -ethyl-3- [(3,3,3-trifluoropropyl) sulfi nyl] propanamide and (-) - N- [3-chloro-1- (3-pyridinyl) -lH-pyrazol-4-yl] -N-ethyl- 3 - [(3,3,3-trifluoropropyl) sulfinyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 Al) (CAS 1477923-37-7), 5 - [[(2E) -3-chloro-2-propen-l-yl ] amino] -l- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethyl) sulfinyl] -lH-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-chlor-2-pyridinyl)- lH-pyrazol-5-carboxamid, (Liudaibenjiaxuanan, bekannt aus CN 103109816 A) (CAS 1232543-85-9); N-[4-Chlor-2-[[(l,l- dimethylethyl)amino]carbonyl]-6-methylphenyl]-l-(3-chlor-2-pyridinyl)-3-(fluormethoxy)-lH-pyrazol- 5-carboxamid (bekannt aus WO 2012/034403 Al) (CAS 1268277-22-0), N-[2-(5-Amino-l,3,4- thiadiazol-2-yl)-4-chlor-6-methylphenyl] -3-brom- 1 -(3-chlor-2-pyridinyl)- lH-pyrazol-5-carboxamid (bekannt aus WO 2011/085575 Al) (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-[(methylamino) thioxomethyl] phenyl] -1 - (3-chloro-2-pyridinyl) -1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N- [4-chloro-2 - [[(l, l-dimethylethyl) amino] carbonyl] -6-methylphenyl] -1- (3-chloro-2-pyridinyl) -3- (fluoromethoxy) -1H-pyrazole- 5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N- [2- (5-amino-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-l-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) -l- [3- (trifluoromethyl) phenyl] ethylidene] -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[ 1 ,2-e] [ 1 ,3 ,4]oxadiazin- 4a(3H)-carbonsäuremethylester (bekannt aus CN 102391261 A) (CAS 1370358-69-2); 6-Desoxy-3-0- ethyl-2,4-di-0-methyl-l-[N-[4-[l-[4-(l,l,2,2,2-pentafluorethoxy)phenyl]-lH-l,2,4-triazol-3- yl]phenyl]carbamat]-a-L-mannopyranose (bekannt aus US 2014/0275503 Al) (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 Al, WO 2007040282 Al) (CAS 934001-66-8), N- [4-(Aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-brom-l-(3-chlor-2-pyridinyl)- l//-pyrazol-5-carboxamid (bekannt aus CN 103265527 A) (CAS 1452877-50-7), 3-(4-Chlor-2,6- dimethylphenyl)-8-methoxy-l-methyl-l,8-diazaspiro[4.5]decan-2,4-dion (bekannt aus WO 2014/187846 Al) (CAS 1638765-58-8), 3-(4-Chlor-2,6-dimethylphenyl)-8-methoxy-l-methyl-2-oxo-l,8- diazaspiro[4.5]dec-3-en-4-yl-carbonsäureethylester (bekannt aus WO 2010/066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), N-\ 1 -(2,6-Difluorphcnyl)- 1 //-pyrazol-3-yl ]-2-(trifluormcthyl)bcnzamid(difluoromethoxy) phenyl] hydrazine carboxamide (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] [1,3,4 ] oxadiazine-4a (3H) -carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-0-ethyl-2,4-di-0-methyl-1- [N- [4- [1- [4- (l, l, 2,2,2-pentafluoroethoxy) phenyl] - lH-l, 2,4-triazol-3-yl] phenyl] carbamate] -aL-mannopyranose (known from US 2014/0275503 A1) (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), N - [4- (Aminothioxomethyl) -2-methyl-6 - [(methylamino) carbonyl] phenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1 // - pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 3- (4-chloro-2,6- dimethylphenyl) -8-methoxy-l-methyl-l, 8-diazaspiro [4.5] decane-2,4- dion (known from WO 2014/187846 Al) (CAS 1638765-58-8), 3- (4-chloro-2,6-dimethylphenyl) -8-methoxy-1-methyl-2-oxo-l, 8-diazaspiro [4.5] dec-3-en -4-yl-carboxylic acid ethyl ester (known from WO 2010/066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), N- \ 1 - (2,6-Difluororphcnyl) - 1 // - pyrazol-3-yl ] -2- (trifluoromethyl) benzamide
(bekannt aus WO 2014/053450 Al) (CAS 1594624-87-9), /V-[2-(2,6-Difluorphenyl)-2//-l,2,3-triazol-4- yl] -2-(trifluormethyl)benzamid (bekannt aus WO 2014/053450 Al) (CAS 1594637-65-6), N-[l-(3,5- Difluor-2-pyridinyl)-lH-pyrazol-3-yl]-2-(trifluormethyl)benzamid (bekannt aus WO 2014/053450 Al) (CAS 1594626-19-3), (3R)-3-(2-Chlor-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5//- thiazolo[3,2-a]pyrimidinium inneres Salz (bekannt aus WO 2018/177970 Al) (CAS 2246757-58-2); 3- (2-Chlor-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inneres Salz (bekannt aus WO 2018/177970 Al) (CAS 2246757-56-0); /V-|3-Chlor- 1 -(3-pyridinyl)- 1 //-pyrazol- 4-yl]-2-(methylsulfonyl)-propanamid (bekannt aus WO 2019/236274 Al) (CAS 2396747-83-2), N-\ 2- bromo-4-[l,2,2,2-tetrafluoro-l-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4- fluorobenzoyl)amino]-benzamid (known from WO 2019059412 Al) (CAS 1207977-87-4). (known from WO 2014/053450 A1) (CAS 1594624-87-9), / V- [2- (2,6-difluorophenyl) -2 // - l, 2,3-triazol-4-yl] -2 - (Trifluoromethyl) benzamide (known from WO 2014/053450 A1) (CAS 1594637-65-6), N- [1- (3,5-difluoro-2-pyridinyl) -lH-pyrazol-3-yl] -2 - (trifluoromethyl) benzamide (known from WO 2014/053450 Al) (CAS 1594626-19-3), (3R) -3- (2-chloro-5-thiazolyl) -2,3-dihydro-8-methyl-5 , 7-dioxo-6-phenyl-5 // - thiazolo [3,2-a] pyrimidinium inner salt (known from WO 2018/177970 A1) (CAS 2246757-58-2); 3- (2-chloro-5-thiazolyl) -2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo [3,2-a] pyrimidinium inner salt (known from WO 2018 / 177970 A1) (CAS 2246757-56-0); / V- | 3-chloro- 1 - (3-pyridinyl) - 1 // - pyrazol- 4-yl] -2- (methylsulfonyl) -propanamide (known from WO 2019/236274 A1) (CAS 2396747-83-2 ), N- \ 2- bromo-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] -6- (trifluoromethyl) phenyl] -2-fluoro-3 - [(4-fluorobenzoyl) amino] benzamide (known from WO 2019059412 A1) (CAS 1207977-87-4).
Fungizide Fungicides
Die hier mit ihrem “Common Name” spezifizierten Wirkstoffe sind bekannt und beispielsweise im “Pesticide Manual” (16. Aufl. British Crop Protection Council) beschrieben oder im Internet recherchierbar (beispielsweise: www.alanwood.net/pesticides) beschrieben. The active ingredients specified here with their “Common Name” are known and described, for example, in the “Pesticide Manual” (16th edition. British Crop Protection Council) or described on the Internet (for example: 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 mixing partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, can, if appropriate, form salts with suitable bases or acids. All of the named fungicidal mixture partners of classes (1) to (15) can optionally include tautomeric forms.
1) Inhibitoren der Ergosterolbiosynthese, zum Beispiel (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, (F010) Imazalil, (1.011) Imazalilsulfat, (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)cyclo- pentanol, ( 1.027) (IS ,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl- 1 -( 1 H- 1 ,2,4-triazol- 1 - ylmethyl)cyclopentanol, (1.028) (2R)-2-(l-Chlorcyclopropyl)-4-[(lR)-2,2-dichlorcyclopropyl]-l-(lH- 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-dichlorcy clopropyl] - 1 - ( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.032) (2S)-2-( 1 -Chlorcyclopropyl)-4- [( 1 S)-2,2-dichlorcyclopropyl] - 1 -( 1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (1.033) (2S)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 - (lH-l,2,4-triazol-l-yl)propan-2-ol, (1.034) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (1.037) l-({(2R,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4- methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.038) l-({(2S,4S)-2-[2-Chlor-4-(4-chlorphenoxy)- phenyl]-4-methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazol, (1.039) l-{[3-(2-Chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-ylthiocyanat, (1.040) l-{[rel(2R,3R)-3-(2-Chlor- phenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-ylthiocyanat, (1.041) 1-1) Inhibitors of ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamide, (1.005) fenpropidine, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009 ) Flutriafol, (F010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019 ) Pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (IR, 2S, 5S) -5- (4-chlorobenzyl ) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.027) (IS, 2R, 5R) -5- (4-chlorobenzyl ) -2- (chloromethyl) -2-methyl- 1 - (1 H- 1, 2,4-triazol- 1 - ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4- [ (IR) -2,2-dichlorocyclopropyl] -1- (1H-1, 2,4-triazol-1 -yl) butan-2-ol, (1.029) (2R) -2- (1 -chlorocyclopropyl) -4 - [(1 S) -2,2-dichlorocyclopropyl] - 1 - (1 H- 1, 2,4-triazol- 1 -yl) butan-2-ol, (1.030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1 H-1, 2,4-triazol-1 -yl) propan-2-ol, (1.031) (2S) -2- (1 -chlorocyclopropyl) -4- [(1 R) -2.2 -dichlorocyclopropyl] -1 - (1 H-1, 2,4-triazol-1 -yl) butan-2-ol, (1.032) (2S) -2- (1 -chlorocyclopropyl) -4- [(1 S ) -2,2-dichlorocyclopropyl] - 1 - (1H- 1, 2,4-triazol-1 -yl) butan-2-ol, (1.033) (2S) -2- [4- (4-chlorophenoxy) - 2- (trifluoromethyl) phenyl] - 1 - (lH-l, 2,4-triazol-l-yl) propan-2-ol, (1.034) (R) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1, 2- oxazol-4-yl] (pyridin-3-yl) methanol, (1.035) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1, 2-oxazole -4-yl] (pyridin-3-yl) methanol, (1.036) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (1.037) l - ({(2R, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolane-2 -yl} methyl) -1 H -1, 2,4-triazole, (1.038) l - ({(2S, 4S) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl -l, 3-dioxolan-2-yl} methyl) -lH-l, 2,4-triazole, (1.039) l - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane 2-yl] methyl} -lH-1,2,4-triazol-5-ylthiocyanate, (1,040) l - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2, 4-difluorophenyl) oxiran-2-yl] methyl} -lH-l, 2,4-triazol-5-ylthiocyanate, (1.041) 1-
{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-ylthio- cyanat, (1.042) 2-[(2R,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.044) 2-[(2R,4S,5R)-l-(2,4-Dichlor- phenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.045) 2-{[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1,2,4-triazol-5-ylthiocyanate , (1.042) 2 - [(2R, 4R, 5R) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- l, 2,4-triazol-3-thione, (1.043) 2 - [(2R, 4R, 5S) -l- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4- yl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.044) 2- [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5 -hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1.045) 2-
[(2R,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol- 3-thion, (1.046) 2-[(2S,4R,5R)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4- dihydro-3H-l,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.048) 2-[(2S,4S,5R)-l-(2,4-Dichlor- phenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.049) 2-[(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4- triazol-3-thione, (1.046) 2 - [(2S, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2.4 - dihydro-3H-1,2,4-triazol-3-thione, (1.047) 2 - [(2S, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6 trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.048) 2- [(2S, 4S, 5R) -l- (2,4-dichloro - phenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazol-3-thione, (1.049) 2-
[(2S,4S,5S)-l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol- 3-thion, (1.050) 2-[l-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazol-3-thion, ( 1.051 ) 2- [2-Chlor-4-(2,4-dichlorphenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( 1.052) 2- [2-Chlor-4-(4-chlorphenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.053) 2- [4-(4- Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, ( 1.054) 2- [4-(4-Chlor- phenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)pentan-2-ol, ( 1.055) Mefentrifluconazol, (1.056) 2-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3- thion, (1.057) 2-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro- 3H-l,2,4-triazol-3-thion, (1.058) 2-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-l- ( 1H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, ( 1.060) 5-(Allylsulfanyl)- 1 - { [3-(2-chlorphenyl)-2-(2,4- difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.061) 5-(Allylsulfanyl)-l-{[rel(2R,3R)-3-(2- chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol, ( 1.062) 5-(Allylsulfanyl)- 1 - {[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol, (1.063) N'- (2,5-Dimethyl-4-{[3-(l,l,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoform- amid, (1.064) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyl- imidoformamid, (1.065) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3-tetafluorpropoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidoformamid, ( 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 , 1 ,2,2-tetrafluorethyl)- sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.068) N'-(2,5-Dimethyl-4-{3-[(2,2,2- trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.069) N'-(2,5-Dimethyl-4- {3-[(2,2,3,3-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-[(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4- triazol-3-thione, (1,050) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2 , 4-triazol-3-thione, (1.051) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1 - (1 H-1, 2,4-triazol-1 -yl) propane -2-ol, (1.052) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] - 1 - (1H-1, 2,4-triazol-1 -yl) butan-2-ol, ( 1.053) 2- [4- (4- chlorophenoxy) -2- (trifluoromethyl) phenyl] - 1 - (1 H- 1, 2,4-triazol-1 -yl) butan-2-ol, (1.054) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1 - (1 H-1, 2,4-triazol-1 -yl) pentan-2-ol, (1.055) mefentrifluconazole, (1.056 ) 2 - {[3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione , (1.057) 2 - {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1 , 2,4-triazol-3-thione, (1.058) 2 - {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazol-3-t hion, (1.059) 5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H- 1, 2,4-triazol- 1 -ylmethyl) cyclopentanol, (1.060) 5- (allylsulfanyl) - 1 - {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -lH-l, 2,4-triazole, (1.061) 5- (allylsulfanyl) - l - {[rel (2R, 3R) -3- (2- chlorophenyl) -2- (2,4-difluorophenyl) 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} -1 H -1, 2,4 -triazole, (1.063) N'- (2,5-dimethyl-4 - {[3- (l, l, 2,2-tetrafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoform amide, (1.064) N '- (2,5-Dimethyl-4 - {[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methyl-imidoformamide, (1.065) N' - (2,5-Dimethyl-4 - {[3- (2,2,3,3-tetafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimidoformamide, (1,066) N '- (2.5 -Dimethyl-4- {[3- (pentafluoroethoxy) phenyl] sulfanyl} - phenyl) -N-ethyl-N-methylimidoformamide, (1.067) N '- (2,5-dimethyl-4- {3 - [(l, 1,2,2-tetrafluoroethyl) sulfanyl] phenoxy} phe nyl) -N-ethyl-N-methylimidoformamide, (1.068) N '- (2,5-dimethyl-4- {3 - [(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl- N-methylimidoformamide, (1.069) N '- (2,5-dimethyl-4- {3 - [(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimidoformamide, (1,070) N'- (2,5-dimethyl-4- {3 - [( pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N -ethyl-N -methylimidoformamide, (1.071) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (1.072) N' - ( 4 - {[3-
(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'- (4- { 3 - [(Difluormethyl) sulfanyl] phenoxy } -2 ,5 -dimethylphenyl) -N -ethyl-N -methylimidoformamid, (1.074) N'-[5-Brom-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimido- formamid, (1.075) N'-{4-[(4,5-Dichlor-l,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyl- imidoformamid, (1.076) N'-{5-Brom-6-[(lR)-l-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N- ethyl-N-methylimidoformamid, (1.077) N'-{5-Brom-6-[(lS)-l-(3,5-difluorphenyl)ethoxy]-2-methyl- pyridin-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-(Difluoromethoxy) phenyl] sulfanyl} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (1.073) N'- (4- {3 - [(difluoromethyl) sulfanyl] phenoxy} -2, 5 -dimethylphenyl) -N -ethyl- N -methylimidoformamide, (1.074) N '- [5-Bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-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- methyl imidoformamide, (1.076) N '- {5-bromo-6 - [(IR) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N -methylimidoformamide , (1.077) N '- {5-Bromo-6 - [(IS) -l- (3,5-difluorophenyl) ethoxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.078) N '- {5-Bromo-6 - [(cis -4-isopropylcyclohexyl) - oxy] -2-methylpyridin-3-yl} - N -ethyl-N-methylimidoformamide, (1.079) N' - {5 -Bromo-6 - [(trans -4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.080) N'- {5-
Brom-6- [ 1 -(3 ,5-difluorphenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamid, (1.081) Ipfentrifluconazol, (1.082) 2- [4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 - yl)propan-2-ol, (1.083) 2-[6-(4-Bromphenoxy)-2-(trifluormethyl)-3-pyridyl]-l-(l,2,4-triazol-l- yl)propan-2-ol, (1.084) 2-[6-(4-Chlorphenoxy)-2-(trifluormethyl)-3-pyridyl]-l-(l,2,4-triazol-l- yl)propan-2-ol, (1.085) 3-[2-(l-Chlorcyclopropyl)-3-(3-chlor-2-fluorphenyl)-2-hydroxy- propyl]imidazol-4-carbonitril und (1.086) 4-[[6-[rac-(2R)-2-(2,4-Difluorphenyl)-l,l-difluor-2-hydroxy- 3-(5-thioxo-4H- 1 ,2,4-triazol- 1 -yl)propyl] -3-pyridyl]oxy]benzonitril. Bromo-6- [1 - (3, 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (1.081) Ipfentrifluconazole, (1.082) 2- [4- (4- Chlorophenoxy) -2- (trifluoromethyl) phenyl] -1 - (1H-1, 2,4-triazol-1-yl) propan-2-ol, (1.083) 2- [6- (4-bromophenoxy) -2 - (trifluoromethyl) -3-pyridyl] -1- (1,2,4-triazol-l-yl) propan-2-ol, (1.084) 2- [6- (4-chlorophenoxy) -2- (trifluoromethyl) -3-pyridyl] -l- (1,2,4-triazol-l-yl) propan-2-ol, (1.085) 3- [2- (l-chlorocyclopropyl) -3- (3-chloro-2- fluorophenyl) -2-hydroxypropyl] imidazole-4-carbonitrile and (1.086) 4 - [[6- [rac- (2R) -2- (2,4-difluorophenyl) -1, l-difluoro-2-hydroxy - 3- (5-thioxo-4H-1, 2,4-triazol-1-yl) propyl] -3-pyridyl] oxy] benzonitrile.
2) Inhibitoren der Atmungskette an Komplex I oder II, zum Beispiel (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.011) Isopyrazam (anti-epimeres Enantiomer 1S,4R,9R), (2.012) Isopyrazam (anti-epimeres Racemat 1RS,4SR,9SR), (2.013) Isopyrazam (Mischung von syn-epimerem Racemat 1RS,4SR,9RS und anti-epimerem Racemat 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) Sedaxan, (2.022) l,3-Dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazol-4- carboxamid, (2.023) 1 ,3 -Dimethyl-N - [(3R) - 1 , 1 , 3 -trimethyl-2 , 3 -dihydro- 1 H-inden-4-yl] - 1 H-pyr azol-4- carboxamid, (2.024) 1,3 -Dimethyl-N - [(3 S) - 1 , 1 , 3 -trimethyl-2 , 3 -dihydro- 1 H-inden-4-yl] - 1 H-pyr azol-4- carboxamid, (2.025) l-Methyl-3-(trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4- carboxamid, (2.026) 2-Fluor-6-(trifluormethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)benzamid, (2.027) 3 -(Difluormethyl)- 1 -methyl-N-( 1,1,3 -trimethyl-2 , 3 -dihydro- 1 H-inden-4-yl)- 1 H-pyr azol-4- carboxamid, (2.028) Inpyrfluxam, (2.029) 3-(Difluormethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.030) Fluindapyr, (2.031) 3-(Difluormethyl)-N- [(3R) -7-fluor- 1 , 1 ,3 -trimethyl-2 , 3 -dihydro- 1 H-inden-4-yl] - 1 -methyl- 1 H-pyr azol-4-carboxamid, (2.032) 3-(Difluormethyl)-N-[(3S)-7-fluor-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazol-4- carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4-{ [4-(trifluormethyl)pyridin-2- yl]oxy}phenyl)ethyl]chinazolin-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-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.036) N-(2-tert.-2) Inhibitors of the respiratory chain at complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008 ) Furametpyr, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS , 4SR, 9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS, 4SR, 9RS and 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) Pyraziflumid, (2.021) Sedaxan, (2.022) l, 3-dimethyl-N- (l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl) -lH-pyrazol-4-carboxamide, (2.023) 1, 3 -Dimethyl-N - [(3R) - 1, 1, 3 -trimethyl-2, 3-dihydro- 1 H-inden-4-yl] - 1 H-pyrazole-4-carboxamide, (2.024) 1,3-Dimethyl- N - [(3 S) -1, 1, 3 -trimethyl-2,3-dihydro-1 H-inden-4-yl] -1 H -pyrazole-4-carboxamide , (2.025) l-methyl-3- (trifluoromethyl) -N- [2 '- (trifluoromethyl) biphenyl-2-yl] -lH-pyrazole-4-carboxamide, (2.026) 2-fluoro-6- (trifluoromethyl) -N- (l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl) benzamide, (2.027) 3 - (difluoromethyl) -1 -methyl-N- (1,1,3 - trimethyl-2,3-dihydro- 1 H-inden-4-yl) -1 H-pyrazole-4-carboxamide, (2.028) pyrfluxam, (2.029) 3- (difluoromethyl) -l-methyl-N - [( 3S) -l, l, 3-trimethyl-2,3-dihydro-lH-inden-4-yl] -lH-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3- (difluoromethyl) -N- [(3R) -7-fluoro-1, 1, 3-trimethyl-2, 3-dihydro- 1 H-inden-4-yl] -1-methyl-1 H-pyrazole-4-carboxamide, (2.032) 3- (Difluoromethyl) -N - [(3S) -7-fluoro-l, l, 3-trimethyl-2,3-dihydro-1H-inden-4-yl] -l-methyl-1H-pyrazole-4- carboxamide, (2.033) 5,8-difluoro-N- [2- (2-fluoro-4- {[4- (trifluoromethyl) pyridine-2- yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.034) N- (2-cyclopentyl-5-fluorobenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole -4-carboxamide, (2.035) N- (2-tert-butyl-5-methylbenzyl) - N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, ( 2.036) N- (2-tert.-
Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.037) N- (5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-Butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N- (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3- (Difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N- (5-chloro-2-isopropylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1 -methyl-1H-pyrazole-
4-carboxamid, (2.039) N-[(lR,4S)-9-(Dichlormethylen)-l,2,3,4-tetrahydro-l,4-methanonaphthalin-5-yl]- 3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.040) N-[(lS,4R)-9-(Dichlormethylen)-l,2,3,4- tetrahydro- 1 ,4-methanonaphthalin-5-yl] -3-(difluormethyl)- 1 -methyl- lH-pyrazol-4-carboxamid, (2.041) N-[l -(2,4-Dichlorphenyl)- 1 -methoxypropan-2-yl] -3-(difluormethyl)- 1 -methyl- lH-pyrazol-4- carboxamid, (2.042) N-[2-Chlor-6-(trifluormethyl)benzyl] -N-cyclopropyl-3-(difluormethyl)-5-fluor- 1 - methyl- lH-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-Cyclo- propyl-3-(difluormethyl)-5-fluor-l-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-lH-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-(difluormethyl)-5- fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3- (difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid, (2.051) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4- carboxamid, (2.052) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl-lH- pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l- methyl-lH-pyrazol-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor- 1 -methyl- lH-pyrazol-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl-4-carboxamide, (2.039) N - [(IR, 4S) -9- (dichloromethylene) -1, 2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl] -3- (difluoromethyl) -1 -methyl-lH-pyrazole-4-carboxamide, (2.040) N - [(lS, 4R) -9- (dichloromethylene) -l, 2,3,4-tetrahydro- 1,4-methanonaphthalen-5-yl] - 3- (Difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.041) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1 -methyl- 1 H -pyrazole-4-carboxamide, (2.042) N- [2-chloro-6- (trifluoromethyl) benzyl] -N -cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1 H -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-Cyclo-propyl-3- (difluoromethyl) -5-fluoro-1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1H -pyrazole-4-carboxamide, (2.046) N-Cyclopropyl -3- (difluoromethyl) -5-fluoro-N- (2-fluoro-6-isopropylbenzyl) -l-methyl- lH- pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -l -methyl- lH-pyrazole-4-carboxamide, (2.048) N-Cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1 -methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3- (difluoromethyl) -5-fluoro -N- (2-isopropylbenzyl) -l-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) - 1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5-fluoro-1-methyl-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- lH-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N- (2-cyclopropyl-
5-methylbenzyl)-3-(difluormethyl)-5-fluor-l -methyl- lH-pyrazol-4-carboxamid, (2.056) N-Cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl- 1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-
N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (2.057)N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057)
Pyrapropoyn. Pyrapropoyn.
3) Inhibitoren der Atmungskette an Komplex III, zum Beispiel (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- pheny 1 vinyl] 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) Fenpicoxamid, (3.026) Mandestrobin, (3.027) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2- hydroxybenzamid, (3.028) (2E,3Z)-5-{ [l-(4-Chlor-2-fluorphenyl)-lH-pyrazol-3-yl]oxy }-2-3) Inhibitors of the respiratory chain at complex III, for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008 , (3.009) famoxadone, (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-fluoro-2- pheny 1 vinyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylacetamide, (3.022) (2E, 3Z) -5 - {[l- (4-chlorophenyl) - 1 H -pyrazol-3-yl] oxy} -2- (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.023) (2R) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl } -2-methoxy-N-methylacetamide, (3.024) (2S) -2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (3.025) fenpicoxamide, (3.026) mandestrobin, (3.027) N- (3 -Ethyl-3,5,5-trimethylcyclohexyl) -3-formamido-2-hydroxybenzamide, (3.028) (2E, 3Z) -5- {[1- (4-chloro-2-fluorophenyl) -1 H -pyrazole-3 -yl] oxy} -2-
(methoxyimino)-N,3-dimethylpent-3-enamid, (3.029) {5-[3-(2,4-Dimethylphenyl)-lH-pyrazol-l-yl]-2- methylbenzyljcarbamidsäuremethylester, (3.030) Metyltetraprol, (3.031) Florylpicoxamid. (methoxyimino) -N, 3-dimethylpent-3-enamide, (3.029) {5- [3- (2,4-dimethylphenyl) -lH-pyrazol-1-yl] -2-methylbenzylcarbamic acid methyl ester, (3.030) methyltetraprole, ( 3,031) floryl picoxamide.
4) Inhibitoren von Mitose und Zellteilung, zum Beispiel (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat- methyl, (4.008) Zoxamid, (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5-phenylpyridazin, (4.010) 3- Chlor-5-(4-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-fluorphenyl)-N-(2,6-difluorphenyl)- l,3-dimethyl-lH-pyrazol-5-amin, (4.013) 4-(2-Brom-4-fluorphenyl)-N-(2-brom-6-fluorphenyl)-l,3- dimethyl-lH-pyrazol-5-amin, (4.014) 4-(2-Brom-4-fluorphenyl)-N-(2-bromphenyl)-l,3-dimethyl-lH- pyrazol-5-amin, (4.015) 4-(2-Brom-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol- 5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2-chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.018) 4-(2-Chlor-4- fluorphenyl)-N-(2,6-difluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.019) 4-(2-Chlor-4-fluorphenyl)- N-(2-chlor-6-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2- chlorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)- l,3-dimethyl-lH-pyrazol-5-amin, (4.022) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethyl- pyridazin, (4.023) N-(2-Brom-6-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5- amin, (4.024) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-pyrazol-5-amin, (4.025) N- (4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-l,3-dimethyl-lH-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) Zoxamid, (4,009) 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine, (4,010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl ) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2- Bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.013) 4- (2-bromo-4-fluorophenyl) -N- (2 -bromo-6-fluorophenyl) -1, 3- dimethyl-1H-pyrazol-5-amine, (4.014) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1, 3-dimethyl -lH- pyrazol-5-amine, (4.015) 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -l, 3-dimethyl-lH-pyrazol-5-amine, (4.016) 4- (2-Bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1, 3-dimethyl-1 H -pyrazol-5-amine, (4.017) 4- (2-Bromo-4-fluorophenyl ) -N- (2-fluorophenyl) -1, 3-dimethyl-1H-pyrazol-5-amine, (4.018) 4- (2-chloro-4-fluo phenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazol-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-pyrazole -5-amine, (4.021) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) - 1,3-dimethyl-lH-pyrazol-5-amine, (4.022) 4- (4- Chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (4.023) N- (2-bromo-6-fluorophenyl) -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-1 H -pyrazol-5-amine.
5) Verbindungen, die an mehreren Stellen wirken können („Multisite Action“), zum Beispiel (5.001) Bordeaux-Mischung, (5.002) Captafol, (5.003) Captan, (5.004) Chlorthalonil, (5.005) Kupferhydroxid, (5.006) Kupfernaphthenat, (5.007) Kupferoxid, (5.008) Kupferoxychlorid, (5.009) Kupfer(2+)-sulfat, (5.010) Dithianon, (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Metiram-Zink, (5.017) Oxin-Kupfer, (5.018) Propineb, (5.019) Schwefel und Schwefel zubereitungen einschließlich Calciumpolysulfid, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram, (5.023) 6- Ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazol-3-carbonsäurenitril.5) Compounds that can act in several places ("Multisite Action"), for example (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate , (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) Metiram, (5.016) Metiram-Zinc, (5.017) Oxine-Copper, (5.018) Propineb, (5.019) Sulfur and sulfur preparations including calcium polysulphide, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram, (5.023) 6 - Ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo [3 ', 4': 5.6] [1,4] dithiino [2,3-c] [1,2] thiazole-3 -carboxonitrile.
6) Verbindungen, die dazu in der Lage sind, Abwehrreaktionen des Wirtes zu induzieren, zum Beispiel (6.001) Acibenzolar-S-methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil. 6) Compounds capable of inducing defense reactions in the host, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
7) Inhibitoren von Aminosäure- und/oder Proteinbiosynthese, zum Beispiel (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. 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3- (5-fluoro- 3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline.
8) Inhibitoren der ATP-Produktion, zum Beispiel (8.001) Silthiofam. 9) Inhibitoren der Zellwandsynthese, zum Beispiel (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.-ButyIphenyI)-3-(2-chIorpyridin-4-yI)-l-(morphoIin-4-yI)prop-2-en-l-on, (9.009) (2Z)-3-(4-tert.-ButyIphenyI)-3-(2-chIorpyridin-4-yI)-l-(morphoIin-4-yI)prop-2-en-l-on. 8) Inhibitors of ATP production, for example (8.001) Silthiofam. 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-ButylphenyI) -3- (2-chloropyridin-4-yI) -1- (morphoIin-4-yI) prop-2-en-1-one, (9.009) (2Z) -3 - (4-tert-ButylphenyI) -3- (2-chloropyridin-4-yI) -1- (morphoIin-4-yI) prop-2-en-1-one.
10) Inhibitoren der Lipid- und Membransynthese, zum Beispiel (10.001) Propamocarb, (10.002) Propamocarb-hydrochlorid, (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 Melaninbiosynthese, zum Beispiel (11.001) Tricyclazol, (11.002) {3-Methyl-l-[(4- methylbenzoyl)amino]butan-2-yl}carbamidsäure-2,2,2-trifluorethylester. 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) {3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl} carbamic acid 2,2,2-trifluoroethyl ester.
12) Inhibitoren der Nukleinsäuresynthese, zum Beispiel (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam). 12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
13) Inhibitoren der Signalübertragung, zum Beispiel (13.001) Fludioxonil, (13.002) Iprodion, (13.003) Procymidon, (13.004) Proquinazid, (13.005) Quinoxyfen, (13.006) Vinclozolin. 13) Inhibitors of signal transmission, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) procinazid, (13.005) quinoxyfen, (13.006) vinclozoline.
14) Verbindungen, die als Entkoppler wirken können, zum Beispiel (14.001) Fluazinam, (14.002) Meptyldinocap. 14) Compounds that can act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Weitere Fungizide ausgewählt aus der Gruppe bestehend aus (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) phosphorige Säure und deren Salze, (15.026) Propamocarb-fosetylat, (15.027) Pyriofenon (Chlazafenon), (15.028) Tebufloquin, (15.029) Tecloftalam, (15.030) Tolnifanid, (15.031) l-(4-{4-[(5R)-5-(2,6-Difluorphenyl)-4,5-dihydro-l,2-oxazol-15) Other fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin , (15.018) natamycin, (15.019) nickel-dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiine, (15.024) pentachlorophenol and salts, (15.025) phosphorous acid and salts thereof , (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) l- (4- {4 - [(5R) -5- ( 2,6-difluorophenyl) -4,5-dihydro-1,2-oxazole-
3-yl ]- 1 ,3-thiazol-2-yl } piperidin- 1 -yl)-2-|5-mcthyl-3-(trifluormcthyl)- 1 H-pyrazol- 1 -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}piperidin-l-yl)-2-[5- methyl-3-(trifluormethyl)- lH-pyrazol- 1 -yljethanon, ( 15.033) 2-(6-Benzylpyridin-2-yl)chinazolin,3-yl] -1, 3-thiazol-2-yl} piperidin-1-yl) -2- | 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.032) l - (4- {4 - [(5S) -5- (2,6-Difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidine -l-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole-1 -yljethanone, (15.033) 2- (6-benzylpyridin-2-yl) quinazoline,
(15.034) Dipymetitron, (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)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- { 5- [2-chlor-6-(prop-2-in- 1 -yloxy)phenyl] -4,5-dihydro- 1,2- oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanon, (15.037) 2-[3,5-Bis(difluormethyl)-lH-pyrazol-l- yl]-l-[4-(4- { 5-[2-fluor-6-(prop-2-in- 1 -yloxy)phenyl]-4,5-dihydro- 1 ,2-oxazol-3-yl } - 1 ,3-thiazol-2-yl)- piperidin-l-yl]ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]chinazolin, (15.039) Methansulfonsäure-2-{(5R)-3-[2-(l-{[3,5-bis(difluormethyl)-lH-pyrazol-l-yl]acetyl}piperidin-(15.034) Dipymetitron, (15.035) 2- [3,5-bis (difluoromethyl) -lH-pyrazol-l-yl] -l- [4- (4- {5- [2- (prop-2-in l-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15.036) 2- [3, 5- bis (difluoromethyl) -1 H -pyrazol-1 -yl] -1 - [4- (4- {5- [2-chloro-6- (prop-2-yn-1 -yloxy) phenyl] -4 , 5-dihydro-1,2-oxazol-3-yl} -1,3-thiazol-2-yl) piperidin-1-yl] ethanone, (15,037) 2- [3,5-bis (difluoromethyl) -lH -pyrazol-l-yl] -l- [4- (4- {5- [2-fluoro-6- (prop-2-yn-1 -yloxy) phenyl] -4,5-dihydro-1, 2- oxazol-3-yl} - 1,3-thiazol-2-yl) - piperidin-l-yl] ethanone, (15.038) 2- [6- (3-fluoro-4-methoxyphenyl) -5-methylpyridin-2- yl] quinazoline, (15.039) methanesulfonic acid-2 - {(5R) -3- [2- (l - {[3,5-bis (difluoromethyl) -lH-pyrazol-l-yl] acetyl} piperidine-
4-yl)- 1 ,3-thiazol-4-yl]-4,5-dihydro- 1 ,2-oxazol-5-yl } -3-chlorphenylester, ( 15.040) Methansulfonsäure-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-chlorphenylester, (15.041) Ipflufenoquin, (15.042) 2-{2-Fluor-6-[(8-fluor-2- methylchinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) Fluoxapiprolin, (15.044) Methansulfonsäure-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-chlorphenylester, (15.044) Fluoxapiprolin, (15.045) 2-Phenylphenol und Salze, (15.046) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4-dihydroisochinolin-l-yl)chinolin, (15.047) Quinofumelin, (15.048) 4-Amino-5-fluorpyrimidin-2-ol (tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.049) 4-Oxo-4- [(2 -phenylethyl)amino] butansäure, (15.050) 5-Amino-l,3,4-thiadiazol-2-thiol,4-yl) -1, 3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl ester, (15,040) methanesulfonic acid 2- {(5S) -3 - [2- (l - {[3,5-bis (difluoromethyl) -lH-pyrazol-l-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5- dihydro-1,2-oxazol-5-yl} -3-chlorophenyl ester, (15.041) iplufenoquine, (15.042) 2- {2-fluoro-6 - [(8-fluoro-2-methylquinolin-3-yl) oxy] phenyl} propan-2-ol, (15.043) fluoxapiproline, (15.044) methanesulfonic acid 2- {3- [2- (l - {[3,5-bis (difluoromethyl) -lH-pyrazol-l-yl] acetyl} piperidin-4-yl) -1, 3-thiazol-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenyl ester, (15,044) fluoxapiproline, (15,045) 2-phenylphenol and salts, (15,046) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15,047) quinofumeline, (15,048) 4-amino-5-fluoropyrimidine -2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2 (lH) -one), (15.049) 4-oxo-4- [(2-phenylethyl) amino] butanoic acid, (15.050) 5-amino l, 3,4-thiadiazol-2-thiol,
(15.051) 5-Chlor-N'-phenyl-N'-(prop-2-in-l-yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4- fluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fluor-2,2-dimethyl-5-(chinolin-3-yl)-2,3-dihydro-l,4-benzoxazepin, (15.055) { 6-[({ [(Z)-(l - Methyl-lH-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamidsäurebut-3-in-l- ylester, (15.056) (2Z)-3-Amino-2-cyano-3-phenylacrylsäureethylester, (15.057) Phenazin- 1 -carbonsäure, (15.058) 3,4,5-Trihydroxybenzoesäurepropylester, (15.059) Chinolin-8-ol, (15.060) Chinolin- 8 -olsulfat (2:1), (15.061) {6-[({[(l -Methyl- 1 H-tetrazol-5-yl)(phenyl)methylen] amino } oxy)methyl]pyridin-2- yl } carbamidsäure-tert. -butylester, ( 15.062) 5-Fluor-4-imino-3-methyl- 1 - [(4-methylphenyl)sulfonyl] -3,4- dihydropyrimidin-2(lH)-on, (15.063) Aminopyrifen, (15.064) (N'-[2-Chlor-4-(2-fluorphenoxy)-5- methylphenyl]-N-ethyl-N-methylimidoformamid), (15.065) (N'-(2-Chlor-5-methyl-4-phenoxyphenyl)- N-ethyl-N-methylimidoformamid), (15.066) (2-{2-[(7,8-Difluor-2-methylchinolin-3-yl)oxy]-6- fluorphenyl}propan-2-ol), (15.067) (5-Brom-l-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4- dihydroisochinolin), (15.068) (3-(4,4-Difluor-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7- yl)chinolin) , ( 15.069) ( 1 -(4,5-Dimethyl- 1 H-benzimidazol- 1 -yl)-4,4-difluor-3 ,3-dimethyl-3 ,4- dihydroisochinolin), (15.070) 8-Fluor-3-(5-fluor-3,3-dimethyl-3,4-dihydroisochinolin-l-yl)chinolon, (15.071) 8-Fluor-3-(5-fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolon, (15.072) 3-(4,4- Difluor-3,3-dimethyl-3,4-dihydroisochinolin-l-yl)-8-fluorchinolin, (15.073) (N-Methyl-N-phenyl-4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid), (15.074) (Methyl{4-[5-(trifluormethyl)-l,2,4- oxadiazol-3-yl]phenyl}carbamat), (15.075) (N-{4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3- yl]benzyl}cyclopropancarboxamid), (15.076) N-Methyl-4-(5-(trifluormethyl)-l,2,4-oxadiazol-3- yljbenzamid, (15.077) N-[(E)-Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3- yljbenzamid, (15.078) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3- yljbenzamid, (15.079) N-[4-[5-(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-cyclopropancarboxamid, (15.080) N-(2-Fluorphenyl)-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.081) 2,2-Difluor- N-methyl-2-[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-acetamid, (15.082) N-Allyl-N-[[4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl)phenyl]methyl]acetamid, (15.083) N-[(E)-N-Methoxy-C-methyl- carbonimidoyl]-4-(5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]-benzamid, (15.084) N-[(Z)-N-Methoxy-C- methyl-carbonimidoyl]-4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzamid, (15.085) N-Allyl-N-[[4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]-methyl]propanamid, (15.086) 4,4-Dimethyl-l-[[4-[5-(15.051) 5-Chloro-N'-phenyl-N '- (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidine -4-amine, (15.053) 5-fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5- (quinolin-3-yl) -2,3-dihydro-1,4-benzoxazepine, (15,055) {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl ] pyridin-2-yl} carbamic acid but-3-yn-l-yl ester, (15.056) (2Z) -3-amino-2-cyano-3-phenylacrylic acid ethyl ester, (15.057) phenazine-1-carboxylic acid, (15.058) 3, Propyl 4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinoline-8-olsulfate (2: 1), (15.061) {6 - [({[(1 -methyl-1 H-tetrazole-5 -yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamic acid tert. -butyl ester, (15.062) 5-fluoro-4-imino-3-methyl-1 - [(4-methylphenyl) sulfonyl] -3,4-dihydropyrimidin-2 (1H) -one, (15.063) aminopyrifen, (15.064) (N '- [2-Chloro-4- (2-fluorophenoxy) -5-methylphenyl] -N-ethyl-N-methylimidoformamide), (15.065) (N' - (2-chloro-5-methyl-4-phenoxyphenyl ) - N-ethyl-N-methylimidoformamide), (15.066) (2- {2 - [(7,8-Difluoro-2-methylquinolin-3-yl) oxy] -6-fluorophenyl} propan-2-ol), (15.067) (5-bromo-1- (5,6-dimethylpyridin-3-yl) -3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3- (4,4-difluoro-5, 5-dimethyl-4,5-dihydrothieno [2,3-c] pyridin-7-yl) quinoline), (15.069) (1 - (4,5-dimethyl-1 H -benzimidazol-1 -yl) -4, 4-difluoro-3, 3-dimethyl-3, 4- dihydroisoquinoline), (15.070) 8-fluoro-3- (5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinolone, ( 15,071) 8-fluoro-3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinolone, (15,072) 3- (4,4-difluoro-3,3 -dimethyl-3,4-dihydroisoquinolin-1-yl) -8-fluoroquinoline, (15,073) (N-methyl-N-phenyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl ] benzame id), (15.074) (methyl {4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl} carbamate), (15.075) (N- {4- [5- (trifluoromethyl) -l, 2,4-oxadiazol-3-yl] benzyl} cyclopropanecarboxamide), (15,076) N-methyl-4- (5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yljbenzamide, (15,077) N - [(E) -Methoxyiminomethyl] -4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yljbenzamide, (15,078) N - [(Z) -Methoxyiminomethyl] -4- [5- (trifluoromethyl ) -1, 2,4-oxadiazol-3-yljbenzamide, (15,079) N- [4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] cyclopropanecarboxamide, (15,080) N - (2-Fluorophenyl) -4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] benzamide, (15,081) 2,2-difluoro-N-methyl-2- [4- [5 - (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] acetamide, (15.082) N-allyl-N - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazole- 3-yl) phenyl] methyl] acetamide, (15.083) N - [(E) -N-methoxy-C-methyl-carbonimidoyl] -4- (5- (trifluoromethyl) -1, 2,4-oxadiazole-3- yl] benzamide, (15.084) N - [(Z) -N-methoxy-C-methyl-carbonimidoyl] -4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] benzamide, ( 15,085) N-allyl- N - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] propanamide, (15,086) 4,4-dimethyl-1- [[4- [5-
(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-on, (15.087) N-Methyl-4-[5- (trifluormethyl) - 1 ,2 ,4-oxadiazol-3 -yl] -benzencarbothioamid, (15.088) 5 -Methyl- 1 - [ [4- [5 - (trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-on, (15.089) N-((2,3-Difluor-4-[5-(trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] pyrrolidin-2-one, (15,087) N-methyl-4- [5- (trifluoromethyl) -1, 2, 4-oxadiazole- 3 -yl] -benzenecarbothioamide, (15.088) 5-methyl-1 - [[4- [5 - (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] pyrrolidin-2-one, (15,089) N - ((2,3-difluoro-4- [5-
(trifluormethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl] -3,3,3-trifluor-propanamid, (15.090) 1 -Methoxy- 1 - methyl-3-[[4-[5-(trifluormethyl}-l,2,4-oxadiazol-3-yl]phenyl]methyl]harnstoff, (15.091) l,l-Diethyl-3- [ [4- [5 -(trifluormethyl } - 1 ,2 ,4-oxadiazol-3 -yljphenyl] methyljharnstoff , (15.092) N- [ [4- [5 -(trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] -3,3,3-trifluoro-propanamide, (15,090) 1-methoxy-1-methyl-3 - [[4- [5 - (Trifluoromethyl} -1, 2,4-oxadiazol-3-yl] phenyl] methyl] urea, (15.091) l, l-Diethyl-3- [[4- [5 - (trifluoromethyl} -1, 2, 4 -oxadiazol-3-ylphenyl] methyljurea, (15.092) N- [[4- [5 -
(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamid, (15.093) N-Methoxy-N-[[4-[5-(Trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] propanamide, (15.093) N-methoxy-N - [[4- [5-
(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropancarboxamid, (15.094) l-Methoxy-3- methyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]harnstoff, (15.095) N-Methoxy-N- [[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropancarboxamid, (15.096) N,2-(trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] cyclopropanecarboxamide, (15.094) l-methoxy-3-methyl-l - [[4- [5- (trifluoromethyl) -l, 2, 4-oxadiazol-3-yl] phenyl] methyl] urea, (15,095) N-methoxy-N- [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl) cyclopropanecarboxamide, (15.096) N, 2-
Dimethoxy-N-[[4-[5-(trifluormethyl}-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamid, (15.097) N- Ethyl-2-methyl-N-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl)phenyl]methyl]propanamid, (15.098) 1- Methoxy-3-methyl-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]harnstoff, (15.099) 1,3- Dimethoxy-l-[[4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]harnstoff, (15.100) 3-Ethyl-l- methoxy- 1 - [ [4- [5 -(trifluormethyl) - 1 ,2 ,4-oxadiazol-3 -yl] phenyl] methyljharnstoff, (15.101) 1 - [ [4- [5 -Dimethoxy-N - [[4- [5- (trifluoromethyl} -1, 2,4-oxadiazol-3-yl] phenyl] methyl] propanamide, (15.097) N-ethyl-2-methyl-N - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl) phenyl] methyl] propanamide, (15,098) 1-methoxy-3-methyl-1- [[4- [5- (trifluoromethyl) -1 , 2,4-oxadiazol-3-yl] phenyl] methyl] urea, (15,099) 1,3-dimethoxy-1- [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl ] phenyl] methyl] urea, (15.100) 3-ethyl-1-methoxy- 1 - [[4- [5 - (trifluoromethyl) - 1, 2, 4-oxadiazol-3-yl] phenyl] methyljurea, (15.101) 1 - [[4- [5 -
(Trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-on, (15.102) 4,4-Dimethyl-2-[[4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isooxazolidin-3-on, (15.103) 5,5-Dimethyl-2-[[4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.104) 3,3-Dimethyl-l-[[4- [5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-on, (15.105) l-[[3-Fluor-4-(5-(Trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] piperidin-2-one, (15.102) 4,4-dimethyl-2 - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] isooxazolidin-3-one, (15.103) 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazole- 3-yl] phenyl] methyl] isoxazolidin-3-one, (15.104) 3,3-dimethyl-1- [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] piperidin-2-one, (15.105) l - [[3-fluoro-4- (5-
(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-on, (15.106) 4,4-Dimethyl-2-[[4-(5-(trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] azepan-2-one, (15.106) 4,4-dimethyl-2 - [[4- (5-
(trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.107) 5,5-Dimethyl-2-[[4-[5- (trifluormethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-on, (15.108) (l-{4-[5-(trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-one, (15.107) 5,5-dimethyl-2 - [[4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl] methyl] isoxazolidin-3-one, (15.108) (l- {4- [5-
(Trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-pyrazol-4-yl)essigsäureethylester, (15.109) N,N- Dimethyl-l-{4-[5-(trifluormethyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-l,2,4-triazol-3-amin und (15.110) N- { 2 ,3 -Difluor-4- [5 -(trifluormethyl) -1,2 ,4-oxadiazol-3 -yl] benzyl } butanamid. (Trifluoromethyl) -l, 2,4-oxadiazol-3-yl] benzyl} -lH-pyrazol-4-yl) ethyl acetate, (15.109) N, N-dimethyl-1- {4- [5- (trifluoromethyl) - l, 2,4-oxadiazol-3-yl] benzyl} -lH-l, 2,4-triazol-3-amine and (15.110) N- {2,3-difluoro-4- [5 - (trifluoromethyl) - 1,2,4-oxadiazol-3-yl] benzyl} butanamide.
Biologische Schädlingsbekämpfungsmittel als Mischungskomponenten Biological pesticides as mixture components
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. The compounds of formula (I) 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 pest control agents include, in particular, bacteria, fungi, yeasts, plant extracts and such products that were formed by microorganisms, including proteins and secondary metabolic products.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pest control agents 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 that are or 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), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD- 5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, especially B. cereus Strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. 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, especially B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially 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 strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Acession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts that are or 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), Metschnikowiafructicola, 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), Metschnikowiafructicola, 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, especially P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, especially strain VI 17b, Trichoderma atroviride, especially strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of viruses that are or can be used as biological pesticides are:
Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Adoxophyes orana (codling moth) granulosevirus (GV), Cydia pomonella (codling moth) granulosevirus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (sugar beet owl) mNPerwug) (African beet owl) mNPerwug, SpodiperNoptera fredoptera Cotton worm) NPV.
Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant‘ Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fördern. Als Beispiele sind genannt: It also includes bacteria and fungi that are added as "inoculants" to plants or parts of plants or plant organs and which, through their special properties, promote 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 cepacici), 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 cepacici), Gigaspora spp., Glaspora spp., Or Gigaspora monospora spp., Or Gigaspora monospora spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., In particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp ..
Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of plant extracts and such products that were formed by microorganisms including proteins and secondary metabolic products that are or can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrine, Quassia amara, Quercus, Quillaja, 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, sowie bioinsektizide/akarizide Wirkstoffe erhalten aus Olivenöl, insbesondere ungesättigte Fett-/Carbonsäuren mit Carbonkettenlängen C16-C20 als Wirkstoffe wie beispielsweise enthalten im Produkt mit dem Handelsnamen FEiPPER®. 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-traum) Pyrethrins, 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, Brassicaca extract , especially rapeseed or mustard powder, and bioinsecticidal / acaricidal active ingredients obtained from olive oil, especially unsaturated fatty / carboxylic acids with carbon chain lengths C16-C20 as active ingredients such as those contained in the product with the trade name FEiPPER®.
Safener als Mischungskomponenten Safeners as mixture components
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamid, Dichlormid, Fenchlorazol (-ethyl), Fenclorim, Flurazol, Fluxofenim, Furilazol, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalsäureanhydrid, 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)- 1,3-oxazolidin (CAS 52836-31-4). The compounds of the formula (I) can be combined with safeners, such as, for example, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamid, Dichlormid, Fenchlorazol (-ethyl), Fenclorim, Flurazol, Fluxofenim, Furilazol, Isoxadifen (-ethyl), Mefenpyr (diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa- 4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) - 1,3-oxazolidine (CAS 52836-31-4).
Pflanzen und Pflanzenteile Plants and parts of plants
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenteile 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, 5s All plants and parts of plants can be treated according to the invention. Plants are understood here as meaning all plants and parts of plants, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potatoes, sugar beets, sugar cane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (e.g. cabbage) and other vegetables, cotton, tobacco, rape, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars that can or cannot be protected by plant breeders' rights. Plants are to be understood as meaning all stages of development such as seeds, cuttings, young (immature) plants up to mature plants. Plant parts are to be understood as meaning all above-ground and underground parts and organs of plants such as shoot, leaf, flower and root, with, for example, leaves, needles, stems, stems, flowers, fruiting bodies, 5s
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. Fruits and seeds as well as roots, tubers and rhizomes are listed. The plant parts also include harvested plants or harvested plant parts and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung der Verbindungen auf die Umgebung, den Lebensraum oder den Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Eintauchen, Spritzen, Verdampfen, Ver nebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage room by the customary treatment methods, eg. B. by immersion, spraying, evaporation, misting Ver, scattering, brushing on, injecting and in the case of propagation material, especially in the case of seeds, by one or more layers of wrapping.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile“ bzw. „Teile von Pflanzen“ oder „Pflanzenteile“ wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits“), die durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA- Techniken erhalten worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars occurring in the wild or obtained by conventional biological breeding methods such as crossing or protoplast fusion, as well as their parts, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated. The term “parts” or “parts of plants” or “plant parts” has been explained above. According to the invention, it is particularly preferred to treat plants of the plant varieties which are commercially available or in use. Plant cultivars are understood to be plants with new properties (“traits”) that have been obtained through conventional breeding, mutagenesis or recombinant DNA techniques. These can be varieties, races, bio and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Transgenic plant, seed treatment and integration events
Erfindungsgemäß können die Verbindungen der Formel (I) vorteilhaft zum Behandeln von transgenen Pflanzen, Pflanzenkultivaren oder Pflanzenteilen eingesetzt werden, die genetisches Material erhalten haben, das diesen Pflanzen, Pflanzenkultivaren bzw. Pflanzenteilen vorteilhafte und/oder brauchbare Eigenschaften (Traits) verleiht. Es wird daher in Betracht gezogen, die vorliegende Erfindung mit einem oder mehreren rekombinanten Traits oder transgenen Events oder einer Kombination davon zu kombinieren. Für die Zwecke der vorliegenden Anmeldung kommt es durch Insertion eines spezifischen rekombinanten DNA-Moleküls in eine spezifische Position (locus) im Chromosom des Pflanzengenoms zu einem transgenen Event. Durch die Insertion wird eine neue DNA-Sequenz geschaffen, die als „Event“ bezeichnet wird, und die durch das insertierte rekombinante DNA-Molekül und eine gewisse Menge genomischer DNA unmittelbar benachbart zur insertierten DNA/die insertierte DNA an beiden Enden flankierend gekennzeichnet ist. Solche Traits bzw. transgenen Events schließen, wobei dies nicht einschränkend ist, Resistenz gegenüber Schädlingen, Wasserausnutzungseffizienz, Ertragsleistung, Dürretoleranz, Samenqualität, verbesserte Nährstoffqualität, Flybridsamenproduktion und Herbizidtoleranz ein, wobei der Trait in Bezug auf eine Pflanze, der ein solcher Trait bzw. ein solches transgenes Event fehlt, gemessen wird. Konkrete Beispiele für solche vorteilhaften und/oder brauchbaren Eigenschaften (Traits) sind besseres Pflanzenwachstum, Lebenskraft, Stresstoleranz, Standfähigkeit, Resistenz gegenüber Lagern, Nährstoffaufnahme, Pflanzenernährung und/oder Ertrag, insbesondere verbessertes Wachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegenüber Dürre oder Wasser- oder Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Erträge, höhere Qualität und/oder höherer Nährwert der Ernteprodukte, bessere Haltbarkeit und/oder Bearbeitbarkeit der Ernteprodukte und erhöhte Resistenz bzw. Toleranz gegenüber tierischen und mikrobiellen Schädlingen wie gegen Insekten, Spinnentiere, Nematoden, Milben und Schnecken. According to the invention, the compounds of the formula (I) can advantageously be used for treating transgenic plants, plant cultivars or plant parts which have received genetic material which gives these plants, plant cultivars or plant parts advantageous and / or useful properties (traits). It is therefore contemplated to combine the present invention with one or more recombinant traits or transgenic events, or a combination thereof. For the purposes of the present application, the insertion of a specific recombinant DNA molecule into a specific position (locus) in the chromosome of the plant genome leads to a transgenic event. The insertion creates a new DNA sequence, which is referred to as an "event" and which is marked by the inserted recombinant DNA molecule and a certain amount of genomic DNA immediately adjacent to the inserted DNA / the inserted DNA flanking it at both ends. Such traits or transgenic events include, but are not limiting, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutrient quality, flybridge seed production and herbicide tolerance, the trait being in relation to a plant that has such a trait or a such a transgenic event is absent, is measured. Concrete examples of such beneficial and / or useful properties (traits) are better plant growth, vitality, stress tolerance, stamina, Resistance to storage, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased flowering performance, easier harvest, acceleration of maturity, higher yields, higher quality and / or higher nutritional value of the harvested products, better shelf life and / or workability of the harvested products and increased resistance or tolerance to animal and microbial pests such as insects, arachnids, nematodes, mites and snails.
Von den für Proteine, die Resistenz- oder Toleranzeigenschaften gegenüber solchen tierischen und mikrobiellen Schädlingen, insbesondere Insekten, verleihen, codierenden DNA-Sequenzen soll insbesondere das genetische Material von Bacillus thuringiensis erwähnt werden, das für die Bt-Proteine codiert, die in der Literatur ausführlich beschrieben und dem Fachmann gut bekannt sind. Erwähnt werden sollen auch von Bakterien wie Photorhabdus (W097/17432 und WO98/08932) extrahierte Proteine. Insbesondere sollen Bt-Cry- oder VIP-Proteine Erwähnung finden, die CrylA-, CrylAb-, CrylAc-, CryllA-, CrylllA-, CryIIIB2-, Cry9c-, Cry2Ab-, Cry3Bb- und CrylF-Proteine oder toxische Fragmente davon einschließen, und außerdem Hybride oder Kombinationen davon, insbesondere das CrylF-Protein oder von einem CrylF-Protein abgeleitete Hybride (z.B. Hybrid-CrylA-CrylF-Proteine oder toxische Fragmente davon), die Proteine vom CrylA-Typ oder toxische Fragmente davon, vorzugsweise das CrylAc-Protein oder vom CrylAc-Protein abgeleitete Hybride (z.B. Hybrid-CrylAb-CrylAc-Proteine) oder das CrylAb- oder Bt2-Protein oder toxische Fragmente davon, die Cry2Ae-, Cry2Af- oder Cry2Ag- Proteine oder toxische Fragmente davon, das CrylA.105-Protein oder ein toxisches Fragment davon, das VIP3Aal9-Protein, das VIP3Aa20-Protein, die VIP3A-Proteine, die bei den COT202- oder COT203- Baumwoll-Events produziert werden, das VIP3Aa-Protein oder ein toxisches Fragment davon, wie in Estruch et al. (1996), Proc Natl Acad Sei US A. 28;93(ll):5389-94 beschrieben, die wie in WO2001/47952 beschriebenen Cry-Proteine, die insektiziden Proteine aus Xenorhabdus (wie in WO98/50427 beschrieben), Serratia (insbesondere aus S. entomophila ) oder Strängen der Photorhabdus- Art, wie Tc-Proteine aus Photorhabdus, wie in WO98/08932 beschrieben. Dies schließt auch alle Varianten bzw. Mutanten eines dieser Proteine ein, die sich in einigen Aminosäuren (1-10, vorzugsweise 1-5) von beliebigen der oben angeführten Sequenzen, insbesondere der Sequenz ihres toxischen Fragments, unterscheiden, oder die an ein Transitpeptid wie ein Plastidtransitpeptid oder ein anderes Protein oder Peptid fusioniert sind, ein. Of the DNA sequences coding for proteins that impart resistance or tolerance properties to such animal and microbial pests, in particular insects, the genetic material of Bacillus thuringiensis should be mentioned in particular, which codes for the Bt proteins, which are extensively described in the literature and are well known to those skilled in the art. Proteins extracted from bacteria such as Photorhabdus (WO97 / 17432 and WO98 / 08932) should also be mentioned. In particular, mention should be made of Bt-Cry or VIP proteins, which include CrylA, CrylAb, CrylAc, CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF proteins or toxic fragments thereof, and also hybrids or combinations thereof, in particular the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA-CrylF proteins or toxic fragments thereof), the proteins of the CrylA type or toxic fragments thereof, preferably the CrylAc- Protein or hybrids derived from the CrylAc protein (e.g. hybrid CrylAb-CrylAc proteins) or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the CrylA.105 Protein or a toxic fragment thereof, the VIP3Aal9 protein, the VIP3Aa20 protein, the VIP3A proteins produced at the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof, as in Estruch et al. (1996), Proc Natl Acad Sci US A. 28; 93 (II): 5389-94 described the cry proteins as described in WO2001 / 47952, the insecticidal proteins from Xenorhabdus (as described in WO98 / 50427), Serratia ( in particular from S. entomophila) or strands of the Photorhabdus species, such as Tc proteins from Photorhabdus, as described in WO98 / 08932. This also includes all variants or mutants of one of these proteins which differ in some amino acids (1-10, preferably 1-5) from any of the above-mentioned sequences, in particular the sequence of their toxic fragment, or which are linked to a transit peptide such as a plastid transit peptide or other protein or peptide are fused.
Ein anderes und besonders hervorgehobenes Beispiel für solche Eigenschaften ist eine verliehene Toleranz gegenüber einem oder mehreren Herbiziden, zum Beispiel Imidazolinonen, Sulphonylharnstoffen, Glyphosat oder Phospinothricin. Von den für Proteine, die den transformierten Pflanzenzehen und Pflanzen Toleranzeigenschaften gegenüber bestimmten Herbiziden verleihen, codierenden DNA-Sequenzen sollte insbesondere das bar- bzw. PAT-Gen oder das Streptomyces- coelicolor-Gen, das in WO2009/152359 beschrieben ist und das Toleranz gegenüber Glufonsinatherbiziden verleiht, ein Gen, das für eine geeignete EPSPS (5-Enolpyruvylshikimat-3- phosphat-Synthase) codiert, die Toleranz gegenüber Herbiziden mit EPSPS als Target, insbesondere Herbiziden wie Glyphosat und dessen Salzen, verleiht, ein für Glyphosat-N-Acetyltransferase codierendes Gen oder ein für Glyphosatoxoreduktase codierendes Gen erwähnt werden. Weitere geeignete Herbizidtoleranz-Traits schließen mindestens einen ALS(Acetolactatsynthase)-Inhibitor (z.B. W02007/024782), ein mutiertes Arabidopsis ALS/AHAS-Gen (z.B. US-Patentschrift 6,855,533), für 2,4- D-Monooxygenasen codierende Gene, die Toleranz gegenüber 2,4-D (2,4-Dichlorphenoxyessigsäure) verleihen, und für Dicamba-Monooxygenasen codierende Gene, die Toleranz gegenüber Dicamba (3,6- Dichlor-2-methoxybenzoesäure) verleihen, ein. Another and particularly emphasized example of such properties is an imparted tolerance to one or more herbicides, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin. Of the DNA sequences coding for proteins which give the transformed plant toes and plants tolerance properties to certain herbicides, in particular the bar or PAT gene or the Streptomyces coelicolor gene, which is described in WO2009 / 152359 and which is tolerance to Glufonsine herbicides, a gene that is necessary for a suitable EPSPS (5-enolpyruvylshikimate-3- phosphate synthase), which confers tolerance to herbicides with EPSPS as a target, in particular herbicides such as glyphosate and its salts, a gene coding for glyphosate N-acetyltransferase or a gene coding for glyphosate oxoreductase can be mentioned. Further suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g. WO2007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g. US Pat. No. 6,855,533), genes coding for 2,4-D-monooxygenases, tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), and genes coding for dicamba monooxygenases that confer tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).
Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Resistenz gegenüber phytopathogenen Pilzen, Bakterien und/oder Viren, die zum Beispiel auf systemische erworbene Resistenz (Systemic Acquired Resistance, SAR) zurückgeht, Systemin, Phytoalexine, Elizitoren und außerdem Resistenzgene und die entsprechend exprimierten Proteine und Toxine. Further and particularly highlighted examples of such properties are an increased resistance to phytopathogenic fungi, bacteria and / or viruses, which can be traced back, for example, to systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and those expressed accordingly Proteins and toxins.
Besonders brauchbare transgene Events in transgenen Pflanzen oder Pflanzenkultivaren, die vorzugsweise erfindungsgemäß behandelt werden können, schließen Event 531/ PV-GHBK04 (Baumwolle, Insektenbekämpfung, beschrieben in W02002/040677), Event 1143-14A (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in W02006/128569); Event 1143-51B (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in W02006/128570); Event 1445 (Baumwolle, Herbizidtoleranz, nicht hinterlegt, beschrieben in US-A 2002-120964 oder W02002/034946); Event 17053 (Reis, Herbizidtoleranz, hinterlegt als PTA-9843, beschrieben in WO2010/117737); Event 17314 (Reis, Herbizidtoleranz, hinterlegt als PTA-9844, beschrieben in WO2010/117735); Event 281-24-236 (Baumwolle, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als PTA-6233, beschrieben in W02005/103266 oder US-A 2005-216969); Event 3006-210-23 (Baumwolle, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als PTA-6233, beschrieben in US-A 2007-143876 oder W02005/103266); Event 3272 (Mais, Qualitätsmerkmal, hinterlegt als PTA-9972, beschrieben in W02006/098952 oder US- A 2006-230473); Event 33391 (Weizen, Herbizidtoleranz, hinterlegt als PTA-2347, beschrieben in W02002/027004), Event 40416 (Mais, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-11508, beschrieben in WO 11/075593); Event 43A47 (Mais, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-11509, beschrieben in WO2011/075595); Event 5307 (Mais, Insektenbekämpfung, hinterlegt als ATCC PTA-9561, beschrieben in W02010/077816); Event ASR-368 (Bentgras, Herbizidtoleranz, hinterlegt als ATCC PTA-4816, beschrieben in US-A 2006-162007 oder W02004/053062); Event B16 (Mais, Herbizidtoleranz, nicht hinterlegt, beschrieben in US-A 2003- 126634); Event BPS-CV127- 9 (Sojabohne, Herbizidtoleranz, hinterlegt als NCIMB Nr. 41603, beschrieben in W02010/080829); Event BLR1 (Raps, Restauration von Pollensterilität, hinterlegt als NCIMB 41193, beschrieben in W02005/074671), Event CE43-67B (Baumwolle, Insektenbekämpfung, hinterlegt als DSM ACC2724, beschrieben in US-A 2009-217423 oder WO2006/128573); Event CE44- 69D (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in US-A 2010- 0024077); Event CE44-69D (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in WO2006/128571); Event CE46-02A (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in WO2006/128572); Event COT102 (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in US-A 2006-130175 oder W02004/039986); Event COT202 (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in US-A 2007-067868 oder W02005/054479); Event COT203 (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in W02005/054480); ); Event DAS21606-3 / 1606 (Sojabohne, Herbizidtoleranz, hinterlegt als PTA-11028, beschrieben in WO2012/033794), Event DAS40278 (Mais, Herbizidtoleranz, hinterlegt als ATCC PTA-10244, beschrieben in WO2011/022469); Event DAS-44406-6 / pDAB8264.44.06.1 (Sojabohne, Herbizidtoleranz, hinterlegt als PTA-11336, beschrieben in WO2012/075426), Event DAS-14536-7 /pDAB8291.45.36.2 (Sojabohne, Herbizidtoleranz, hinterlegt als PTA-11335, beschrieben in WO2012/075429), Event DAS-59122-7 (Mais, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA 11384, beschrieben in US-A 2006-070139); Event DAS- 59132 (Mais, Insektenbekämpfung - Herbizidtoleranz, nicht hinterlegt, beschrieben in W02009/100188); Event DAS68416 (Sojabohne, Herbizidtoleranz, hinterlegt als ATCC PTA-10442, beschrieben in WO2011/066384 oder WO2011/066360); Event DP-098140-6 (Mais, Herbizidtoleranz, hinterlegt als ATCC PTA-8296, beschrieben in US-A 2009- 137395 oder WO 08/112019); Event DP-305423-1 (Sojabohne, Qualitätsmerkmal, nicht hinterlegt, beschrieben in US-A 2008-312082 oder W02008/054747); Event DP-32138-1 (Mais, Hybridisierungssystem, hinterlegt als ATCC PTA-9158, beschrieben in US-A 2009-0210970 oder W02009/103049); Event DP-356043-5 (Sojabohne, Herbizidtoleranz, hinterlegt als ATCC PTA-8287, beschrieben in US-A 2010-0184079 oder W02008/002872); Event EE-I (Aubergine, Insektenbekämpfung, nicht hinterlegt, beschrieben in WO 07/091277); Event Fil 17 (Mais, Herbizidtoleranz, hinterlegt als ATCC 209031, beschrieben in US-A 2006-059581 oder WO 98/044140); Event FG72 (Sojabohne, Herbizidtoleranz, hinterlegt als PTA-11041, beschrieben in WO2011/063413), Event GA21 (Mais, Herbizidtoleranz, hinterlegt als ATCC 209033, beschrieben in US-A 2005-086719 oder WO 98/044140); Event GG25 (Mais, Herbizidtoleranz, hinterlegt als ATCC 209032, beschrieben in US-A 2005-188434 oder W098/044140); Event GHB119 (Baumwolle, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-8398, beschrieben in W02008/151780); Event GHB614 (Baumwolle, Herbizidtoleranz, hinterlegt als ATCC PTA-6878, beschrieben in US-A 2010-050282 oder W02007/017186); Event GJ11 (Mais, Herbizidtoleranz, hinterlegt als ATCC 209030, beschrieben in US-A 2005-188434 oder W098/044140); Event GM RZ13 (Zuckerrübe, Virusresistenz, hinterlegt als NCIMB-41601, beschrieben in WO2010/076212); Event H7-1 (Zuckerrübe, Herbizidtoleranz, hinterlegt als NCIMB 41158 oder NCIMB 41159, beschrieben in US-A 2004-172669 oder WO 2004/074492); Event JOPLIN1 (Weizen, Krankheitstoleranz, nicht hinterlegt, beschrieben in US-A 2008-064032); Event LL27 (Sojabohne, Herbizidtoleranz, hinterlegt als NCIMB41658, beschrieben in W02006/108674 oder US-A 2008-320616); Event LL55 (Sojabohne, Herbizidtoleranz, hinterlegt als NCIMB 41660, beschrieben in WO 2006/108675 oder US-A 2008- 196127); Event LLcotton25 (Baumwolle, Herbizidtoleranz, hinterlegt als ATCC PTA-3343, beschrieben in W02003/013224 oder US- A 2003-097687); Event LLRICE06 (Reis, Herbizidtoleranz, hinterlegt als ATCC 203353, beschrieben in US 6,468,747 oder W02000/026345); Event LLRice62 ( Reis, Herbizidtoleranz, hinterlegt als ATCC 203352, beschrieben in W02000/026345), Event LLRICE601 (Reis, Herbizidtoleranz, hinterlegt als ATCC PTA-2600, beschrieben in US-A 2008-2289060 oder W02000/026356); Event LY038 (Mais, Qualitätsmerkmal, hinterlegt als ATCC PTA-5623, beschrieben in US-A 2007-028322 oder W02005/061720); Event MIR162 (Mais, Insektenbekämpfung, hinterlegt als PTA-8166, beschrieben in US-A 2009-300784 oder W02007/142840); Event MIR604 (Mais, Insektenbekämpfung, nicht hinterlegt, beschrieben in US-A 2008-167456 oder W02005/103301); Event MON15985 (Baumwolle, Insektenbekämpfung, hinterlegt als ATCC PTA-2516, beschrieben in US-A 2004-250317 oder W02002/100163); Event MON810 (Mais, Insektenbekämpfung, nicht hinterlegt, beschrieben in US-A 2002-102582); Event MON863 (Mais, Insektenbekämpfung, hinterlegt als ATCC PTA-2605, beschrieben in W02004/011601 oder US-A 2006-095986); Event MON87427 (Mais, Bestäubungskontrolle, hinterlegt als ATCC PTA-7899, beschrieben in WO2011/062904); Event MON87460 (Mais, Stresstoleranz, hinterlegt als ATCC PTA-8910, beschrieben in W02009/111263 oder US-A 2011-0138504); Event MON87701 (Sojabohne, Insektenbekämpfung, hinterlegt als ATCC PTA- 8194, beschrieben in US-A 2009-130071 oder W02009/064652); Event MON87705 (Sojabohne, Qualitätsmerkmal - Herbizidtoleranz, hinterlegt als ATCC PTA-9241, beschrieben in US-A 2010- 0080887 oder W02010/037016); Event MON87708 (Sojabohne, Herbizidtoleranz, hinterlegt als ATCC PTA-9670, beschrieben in WO2011/034704); Event MON87712 (Sojabohne, Ertrag, hinterlegt als PTA- 10296, beschrieben in WO2012/051199), Event MON87754 (Sojabohne, Qualitätsmerkmal, hinterlegt als ATCC PTA-9385, beschrieben in WO2010/024976); Event MON87769 (Sojabohne, Qualitätsmerkmal, hinterlegt als ATCC PTA- 8911, beschrieben in US-A 2011-0067141 oder W02009/102873); Event MON88017 (Mais, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-5582, beschrieben in US-A 2008-028482 oder W02005/059103); Event MON88913 (Baumwolle, Herbizidtoleranz, hinterlegt als ATCC PTA-4854, beschrieben in W02004/072235 oder US-A 2006-059590); Event MON88302 (Raps, Herbizidtoleranz, hinterlegt als PTA-10955, beschrieben in WO2011/153186), Event MON88701 (Baumwolle, Herbizidtoleranz, hinterlegt als PTA-11754, beschrieben in WO2012/134808), Event MON89034 (Mais, Insektenbekämpfung, hinterlegt als ATCC PTA-7455, beschrieben in WO 07/140256 oder US-A 2008-260932); Event MON89788 (Sojabohne, Herbizidtoleranz, hinterlegt als ATCC PTA-6708, beschrieben in US-A 2006-282915 oder W02006/130436); Event MSI 1 (Raps, Bestäubungskontrolle - Herbizidtoleranz, hinterlegt als ATCC PTA-850 oder PTA-2485, beschrieben in WO2001/031042); Event MS8 (Raps, Bestäubungskontrolle - Herbizidtoleranz, hinterlegt als ATCC PTA-730, beschrieben in W02001/041558 oder US-A 2003-188347); Event NK603 (Mais, Herbizidtoleranz, hinterlegt als ATCC PTA-2478, beschrieben in US-A 2007-292854); Event PE-7 (Reis, Insektenbekämpfung, nicht hinterlegt, beschrieben in W02008/114282); Event RF3 (Raps, Bestäubungskontrolle - Herbizidtoleranz, hinterlegt als ATCC PTA-730, beschrieben in W02001/041558 oder US-A 2003-188347); Event RT73 (Raps, Herbizidtoleranz, nicht hinterlegt, beschrieben in W02002/036831 oder US-A 2008-070260); Event SYHT0H2 / SYN-000H2-5 (Sojabohne, Herbizidtoleranz, hinterlegt als PTA-11226, beschrieben in WO2012/082548), Event T227-1 (Zuckerrübe, Herbizidtoleranz, nicht hinterlegt, beschrieben in W02002/44407 oder US-A 2009-265817); Event T25 (Mais, Herbizidtoleranz, nicht hinterlegt, beschrieben in US-A 2001-029014 oder W02001/051654); Event T304-40 (Baumwolle, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-8171, beschrieben in US-A 2010-077501 oder W02008/122406); Event T342-142 (Baumwolle, Insektenbekämpfung, nicht hinterlegt, beschrieben in WO2006/128568); Event TC1507 (Mais, Insektenbekämpfung - Herbizidtoleranz, nicht hinterlegt, beschrieben in US-A 2005-039226 oder W02004/099447); Event VIP1034 (Mais, Insektenbekämpfung - Herbizidtoleranz, hinterlegt als ATCC PTA-3925, beschrieben in W02003/052073), Event 32316 (Mais, Insektenbekämpfung-Herbizidtoleranz, hinterlegt als PTA-11507, beschrieben in WO2011/084632), Event 4114 (Mais, Insektenbekämpfung- Herbizidtoleranz, hinterlegt als PTA-11506, beschrieben in W02011/084621), Event EE-GM3 / FG72 (Sojabohne, Herbizidtoleranz, ATCC-Zugangsnr. PTA-11041) gegebenenfalls gestapelt mit Event EE- GM1/LL27 oder Event EE-GM2/LL55 (WO2011/063413A2), Event DAS-68416-4 (Sojabohne, Herbizidtoleranz, ATCC-Zugangsnr. PTA-10442, WO2011/066360A1), Event DAS-68416-4 (Sojabohne, Herbizidtoleranz, ATCC-Zugangsnr. PTA-10442, WO2011/066384A1), Event DP-040416-8 (Mais, Insektenbekämpfung, ATCC-Zugangsnr. PTA-11508, WO2011/075593A1), Event DP-043A47-3 (Mais, Insektenbekämpfung, ATCC-Zugangsnr. PTA-11509, WO2011/075595A1), Event DP- 004114-3 (Mais, Insektenbekämpfung, ATCC-Zugangsnr. PTA-11506, WO2011/084621 Al), Event DP-032316-8 (Mais, Insektenbekämpfung, ATCC-Zugangsnr. PTA-11507, WO2011/084632A1), Event MON-88302-9 (Raps, Herbizidtoleranz, ATCC-Zugangsnr. PTA-10955, WO2011/153186A1), Event DAS-21606-3 (Sojabohne, Herbizidtoleranz, ATCC-Zugangsnr. PTA-11028, WO2012/033794A2), Event MON-87712-4Particularly useful transgenic events in transgenic plants or plant cultivars, which can preferably be treated according to the invention, include Event 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002 / 034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010 / 117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010 / 117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005 / 103266 or US-A 2005-216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US-A 2007-143876 or WO2005 / 103266); Event 3272 (corn, quality feature, deposited as PTA-9972, described in WO2006 / 098952 or US-A 2006-230473); Event 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002 / 027004), Event 40416 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-11508, described in WO 11/075593); Event 43A47 (Corn, Insect Control - Herbicide Tolerance, deposited as ATCC PTA-11509, described in WO2011 / 075595); Event 5307 (corn, insect control, deposited as ATCC PTA-9561, described in WO2010 / 077816); Event ASR-368 (bentgrass, herbicide tolerance, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); Event B16 (corn, herbicide tolerance, not deposited, described in US-A 2003-126634); Event BPS-CV127- 9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO2010 / 080829); Event BLR1 (rape, restoration of male sterility, deposited as NCIMB 41193, described in WO2005 / 074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006 / 128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); Event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986); Event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479); Event COT203 (cotton, insect control, not deposited, described in WO2005 / 054480); ); Event DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012 / 033794); Event DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244, described in WO2011 / 022469); Event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, deposited as PTA-11336, described in WO2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA -11335, described in WO2012 / 075429), Event DAS-59122-7 (corn, insect control - herbicide tolerance, deposited as ATCC PTA 11384, described in US-A 2006-070139); Event DAS-59132 (maize, insect control - herbicide tolerance, not deposited, described in WO2009 / 100188); Event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); Event DP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A 2009-137395 or WO 08/112019); Event DP-305423-1 (soybean, quality mark, not deposited, described in US-A 2008-312082 or WO2008 / 054747); Event DP-32138-1 (maize, hybridization system, deposited as ATCC PTA-9158, described in US-A 2009-0210970 or WO2009 / 103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO2008 / 002872); Event EE-I (eggplant, insect control, not deposited, described in WO 07/091277); Event Fil 17 (corn, herbicide tolerance, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98/044140); Event FG72 (soybean, herbicide tolerance, deposited as PTA-11041, described in WO2011 / 063413), Event GA21 (corn, herbicide tolerance, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98/044140); Event GG25 (corn, herbicide tolerance, deposited as ATCC 209032, described in US-A 2005-188434 or WO98 / 044140); Event GHB119 (Cotton, Insect Control - Herbicide Tolerance, deposited as ATCC PTA-8398, described in WO2008 / 151780); Event GHB614 (cotton, herbicide tolerance, deposited as ATCC PTA-6878, described in US-A 2010-050282 or WO2007 / 017186); Event GJ11 (corn, herbicide tolerance, deposited as ATCC 209030, described in US-A 2005-188434 or WO98 / 044140); Event GM RZ13 (sugar beet, virus resistance, deposited as NCIMB-41601, described in WO2010 / 076212); Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004/074492); Event JOPLIN1 (wheat, disease tolerance, not deposited, described in US-A 2008-064032); Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658, described in WO2006 / 108674 or US-A 2008-320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in WO 2006/108675 or US-A 2008-196127); Event LLcotton25 (cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in WO2003 / 013224 or US-A 2003-097687); Event LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000 / 026345); Event LLRice62 (rice, Herbicide tolerance, deposited as ATCC 203352, described in WO2000 / 026345), Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A 2008-2289060 or WO2000 / 026356); Event LY038 (maize, quality indicator, deposited as ATCC PTA-5623, described in US-A 2007-028322 or WO2005 / 061720); Event MIR162 (corn, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007 / 142840); Event MIR604 (corn, insect control, not deposited, described in US-A 2008-167456 or WO2005 / 103301); Event MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO2002 / 100163); Event MON810 (Corn, Insect Control, not deposited, described in US-A 2002-102582); Event MON863 (corn, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A 2006-095986); Event MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); Event MON87460 (corn, stress tolerance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A 2011-0138504); Event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009 / 064652); Event MON87705 (soybean, quality attribute - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A 2010-00080887 or WO2010 / 037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199), Event MON87754 (soybean, quality feature, deposited as ATCC PTA-9385, described in WO2010 / 024976); Event MON87769 (soybean, quality attribute, deposited as ATCC PTA-8911, described in US-A 2011-0067141 or WO2009 / 102873); Event MON88017 (Corn, Insect Control - Herbicide Tolerance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005 / 059103); Event MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); Event MON88302 (oilseed rape, herbicide tolerance, deposited as PTA-10955, described in WO2011 / 153186), Event MON88701 (cotton, herbicide tolerance, deposited as PTA-11754, described in WO2012 / 134808), Event MON89034 (maize, insect control, deposited as ATCC PTA-7455, described in WO 07/140256 or US-A 2008-260932); Event MON89788 (soybean, herbicide tolerance, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); Event MSI 1 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO2001 / 031042); Event MS8 (Oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); Event NK603 (corn, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); Event PE-7 (rice, insect control, not deposited, described in WO2008 / 114282); Event RF3 (Oilseed Rape, Pollination Control - Herbicide Tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); Event RT73 (rapeseed, herbicide tolerance, not deposited, described in WO2002 / 036831 or US-A 2008-070260); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, deposited as PTA-11226, described in WO2012 / 082548), Event T227-1 (sugar beet, herbicide tolerance, not deposited, described in W02002 / 44407 or US-A 2009-265817 ); Event T25 (corn, herbicide tolerance, not deposited, described in US-A 2001-029014 or WO2001 / 051654); Event T304-40 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO2008 / 122406); Event T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); Event TC1507 (Corn, Insect Control - Herbicide Tolerance, not deposited, described in US-A 2005-039226 or WO2004 / 099447); Event VIP1034 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-3925, described in W02003 / 052073), Event 32316 (corn, insect control herbicide tolerance, deposited as PTA-11507, described in WO2011 / 084632), event 4114 (corn, Insect control herbicide tolerance, deposited as PTA-11506, described in W02011 / 084621), Event EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC accession no. PTA-11041) optionally stacked with Event EE-GM1 / LL27 or Event EE-GM2 / LL55 (WO2011 / 063413A2), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-10442, WO2011 / 066360A1), Event DAS-68416-4 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-10442 , WO2011 / 066384A1), Event DP-040416-8 (maize, insect control, ATCC accession no. PTA-11508, WO2011 / 075593A1), event DP-043A47-3 (maize, insect control, ATCC accession no. PTA-11509, WO2011 / 075595A1), Event DP-004114-3 (maize, insect control, ATCC accession no. PTA-11506, WO2011 / 084621 A1), event DP-032316-8 (maize, Ins ect control, ATCC accession no. PTA-11507, WO2011 / 084632A1), Event MON-88302-9 (canola, herbicide tolerance, ATCC accession no. PTA-10955, WO2011 / 153186A1), event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession no. PTA- 11028, WO2012 / 033794A2), Event MON-87712-4
(Sojabohne, Qualitätsmerkmal, ATCC-Zugangsnr. PTA-10296, WO2012/051199A2), Event DAS- 44406-6 (Sojabohne, gestapelte Herbizidtoleranz, ATCC-Zugangsnr. PTA-11336, WO2012/075426A1), Event DAS-14536-7 (Sojabohne, gestapelte Herbizidtoleranz, ATCC-Zugangsnr. PTA-11335, WO2012/075429A1), Event SYN-000H2-5 (Sojabohne, Herbizidtoleranz, ATCC-Zugangsnr. PTA- 11226, WO2012/082548A2), Event DP-061061-7 (Raps, Herbizidtoleranz, keine Hinterlegungsnr. verfügbar, W02012071039A1), Event DP-073496-4 (Raps, Herbizidtoleranz, keine Hinterlegungsnr. verfügbar, US2012131692), Event 8264.44.06.1 (Sojabohne, gestapelte Herbizidtoleranz, Zugangsnr. PTA-11336, WO2012075426A2), Event 8291.45.36.2 (Sojabohne, gestapelte Herbizidtoleranz, Zugangsnr. PTA-11335, WO2012075429A2), Event SYHT0H2 (Sojabohne, ATCC-Zugangsnr. PTA- 11226, WO2012/082548A2), Event MON88701 (Baumwolle, ATCC-Zugangsnr. PTA-11754, WO2012/134808A1), Event KK179-2 (Luzerne, ATCC-Zugangsnr. PTA-11833, W02013/003558A1), Event pDAB8264.42.32.1 (Sojabohne, gestapelte Herbizidtoleranz, ATCC-Zugangsnr. PTA-11993, WO2013/010094 Al), Event MZDT09Y (Mais, ATCC-Zugangsnr. PTA-13025, WO2013/012775 Al) ein.(Soybean, Quality Mark, ATCC Accession No. PTA-10296, WO2012 / 051199A2), Event DAS-44406-6 (Soybean, Stacked Herbicide Tolerance, ATCC Accession No. PTA-11336, WO2012 / 075426A1), Event DAS-14536-7 ( Soybean, Stacked Herbicide Tolerance, ATCC Accession No. PTA-11335, WO2012 / 075429A1), Event SYN-000H2-5 (Soybean, Herbicide Tolerance, ATCC Accession No. PTA-11226, WO2012 / 082548A2), Event DP-061061-7 (Raps , Herbicide Tolerance, No Accession No. available, W02012071039A1), Event DP-073496-4 (Oilseed Rape, Herbicide Tolerance, No Accession No. available, US2012131692), Event 8264.44.06.1 (Soybean, Stacked Herbicide Tolerance, Accession No. PTA-11336, WO22012075426 8291.45.36.2 (soybean, stacked herbicide tolerance, accession no. PTA-11335, WO2012075429A2), event SYHT0H2 (soybean, ATCC accession no. PTA-11226, WO2012 / 082548A2), event MON88701 (cotton, ATCC accession no. PTA-11 / 134808A1), event KK179-2 (alfalfa, ATCC accession no. PTA-11833, W02013 / 003558A1), event pDAB8264.42.32.1 (p oybean, stacked herbicide tolerance, ATCC accession no. PTA-11993, WO2013 / 010094 A1), Event MZDT09Y (maize, ATCC accession no. PTA-13025, WO2013 / 012775 A1).
Weiterhin wird eine solche Liste transgener Events vom United States Department of Agriculture’s (USDA) Animal and Plant Health Inspection Service (APHIS) bereitgestellt und findet sich auf deren Webseite auf dem World Wide Web bei aphis.usda.gov. Für die vorliegende Anmeldung ist der Status dieser Liste, wie er am Anmeldetag der vorliegenden Anmeldung war, von Relevanz. Die Gene/Events, die die betreffenden gewünschten Merkmale verleihen, können in den transgenen Pflanzen auch in Kombinationen miteinander vorliegen. Beispiele für transgene Pflanzen, die erwähnt werden können, sind wichtige Kulturpflanzen wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Sojabohnen, Kartoffeln, Zuckerrübe, Zuckerrohr, Tomaten, Erbsen und andere Arten von Gemüse, Baumwolle, Tabak, Raps und außerdem Obstpflanzen (mit den Früchten Äpfeln, Birnen, Zitrusfrüchte und Weintrauben), wobei Mais, Sojabohnen, Weizen, Reis, Kartoffeln, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben sind. Traits, die besonders hervorgehoben werden, sind die erhöhte Resistenz der Pflanzen gegenüber Insekten, Spinnentieren, Nematoden und Schnecken sowie die erhöhte Resistenz der Pflanzen gegenüber einem oder mehreren Herbiziden. Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov. The status of this list as it was on the filing date of the present application is relevant for the present application. The genes / events which confer the desired characteristics in question can also be present in combinations with one another in the transgenic plants. Examples of transgenic plants that can be mentioned are important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetables, cotton, Tobacco, rapeseed and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed being particularly emphasized. Traits that are particularly emphasized are the increased resistance of plants to insects, arachnids, nematodes and snails as well as the increased resistance of plants to one or more herbicides.
Im Handel erhältliche Beispiele für solche Pflanzen, Pflanzenteile oder Pflanzensamen, die vorzugsweise erfindungsgemäß behandelt werden können, schließen im Handel erhältliche Produkte wie Pflanzensamen ein, die unter den GENUITY®-, DROUGHTGARD®-, SMARTSTAX®-, RIB COMPLETE®-, ROUNDUP READY®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2 YIELD®-, YIELDGARD®-, ROUNDUP READY® 2 XTEND™-, INTACTA RR2 PRO®-, VISTIVE GOLD®- und/oder XTENDFLEX™-Handelsnamen verkauft bzw. vertrieben werden. Commercially available examples of such plants, plant parts or plant seeds, which can preferably be treated according to the invention, include commercially available products such as plant seeds, which are under the GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY ®-, VT DOUBLE PRO®-, VT TRIPLE PRO®-, BOLLGARD II®-, ROUNDUP READY 2 YIELD®-, YIELDGARD®-, ROUNDUP READY® 2 XTEN D ™ -, INTACTA RR2 PRO®-, VISTIVE GOLD®- and / or XTENDFLEX ™ trade names are sold or distributed.
Pflanzenschutz - Behandlungsarten Plant protection - types of treatment
Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z. B. durch Tauchen, Spritzen, Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, Verstreuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their surroundings, habitat or storage room by the customary treatment methods, e.g. B. by dipping, spraying, atomizing, sprinkling, scattering, foaming, brushing, spreading, injecting, pouring (drenching), drip irrigation and in the case of propagation material, especially in the case of seeds, furthermore by dry dressing, wet dressing, slurry dressing, encrusting , single-layer or multilayer coating, etc. It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the application form or the compound of the formula (I) into the soil itself.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d. h. die Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. A preferred direct treatment of the plants is foliar application; H. the compounds of the formula (I) are applied to the foliage, the frequency of treatment and the application rate should be matched to the infestation pressure of the pest in question.
Bei systemisch wirksamen Wirkstoffen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d. h. der Standort der Pflanze (z. B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d. h. die erfindungsgemäßen Verbindungen der Formel (I) werden in fester Form (z. B. in Form eines Granulats) in den Standort der Pflanzen eingebracht, oder durch Tropfapplikation (oftmals auch als "Chemigation" bezeichnet), d.h. die erfindungsgemäßen Verbindungen der Formel (I) werden mittels Oberflächen- oder Untergrund-Tropfrohren über bestimmte Zeiträume zusammen mit variierenden Mengen an Wasser an definierten Stellen in der Nähe der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z. B. als Granulat) in ein überflutetes Reisfeld sein. In the case of systemically active ingredients, the compounds of the formula (I) also get into the plants via the root system. The plants are then treated by the action of the compounds of the formula (I) on the plant's habitat. This can be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (e.g. soil or hydroponic systems) is soaked with a liquid form of the compounds of formula (I), or by soil application, ie the compounds of the formula (I) according to the invention are introduced into the location of the plants in solid form (for example in the form of granules) or through Drip application (often also referred to as "chemigation"), ie the compounds of the formula (I) according to the invention are introduced by means of surface or underground drip pipes over certain periods of time together with varying amounts of water at defined locations near the plants. In the case of water rice cultures, this can also be done by metering the compound of the formula (I) in a solid application form (for example as granules) into a flooded rice field.
Digitale Technologien Digital technologies
Die erfindungsgemäßen Verbindungen können in Kombination mit z.B. in Computerprogrammen für ortsspezifisches Kulturpflanzenmanagement eingebetteten Modellen, Satelliten-Ackerbau, Präzisionsackerbau bzw. Präzisionslandwirtschaft eingesetzt werden. Solche Modelle unterstützen das ortsspezifische Management landwirtschaftlicher Anlagen mit Daten aus verschiedenen Quellen wie Böden, Wetter, Kulturpflanzen (z.B. Typ, Wachstumsstadium, Pflanzengesundheit), Unkräuter (z.B. Typ, Wachstumsstadium), Krankheiten, Schädlingen, Nährstoffen, Wasser, Feuchtigkeit, Biomasse, Satellitendaten, Ertrag usw., mit dem Ziel, Rentabilität, Nachhaltigkeit und Umweltschutz zu optimieren. Insbesondere können solche Modelle helfen, agronomische Entscheidungen zu optimieren, die Präzision von Pestizidanwendungen zu steuern und die durchgeführten Arbeiten aufzuzeichnen. The compounds according to the invention can be used in combination with, for example, models embedded in computer programs for site-specific crop management, satellite farming, precision farming or precision agriculture. Such models support the site-specific management of agricultural facilities with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, Yield, etc., with the aim of optimizing profitability, sustainability and environmental protection. In particular, such models can help optimize agronomic decisions, control the precision of pesticide applications and record the work carried out.
Beispielsweise kann man die erfindungsgemäßen Verbindungen gemäß einem entsprechenden Anwendungsprotokoll auf eine Kulturpflanze aufbringen, wenn das Modell das Auftreten eines Schädlings moduliert und berechnet, dass eine Schwelle erreicht wurde, bei der es empfohlen wird, die erfindungsgemäße Verbindung auf die Kulturpflanze aufzubringen. For example, the compounds according to the invention can be applied to a crop plant according to a corresponding application protocol if the model modulates the occurrence of a pest and calculates that a threshold has been reached at which it is recommended to apply the compound according to the invention to the crop plant.
Im Handel erhältliche Systeme, die agronomische Modelle einschließen, sind z.B. FieldScriptsTM von The Climate Corporation, XarvioTM von BASF, AGLogicTM von John Deere usw. Commercially available systems that include agronomic models include FieldScripts ™ from The Climate Corporation, Xarvio ™ from BASF, AGLogic ™ from John Deere, etc.
Die erfindungsgemäßen Verbindungen können außerdem in Kombination mit smartem Sprühgerät wie z.B. Gerät zum punktuellen Sprühen oder Präzisionssprühen, das an einem Farmvehikel wie einem Traktor, einem Roboter, einem Helikopter, einem Flugzeug, einem unbemannten Fuftfahrzeug (Unmanned Aerial Vehicle, UAV) wie einer Drohne an - bzw. untergebracht ist, eingesetzt werden. Solches Gerät umfasst gewöhnlich Input-Sensoren (wie z.B. eine Kamera) und eine Bearbeitungseinheit, die für die Analyse der Input-Daten und die Bereitstellung einer Entscheidung, die auf der Analyse der Input-Daten basiert, zur Anwendung der erfindungsgemäßen Verbindung auf den Kulturpflanzen (beziehungsweise den Unkräutern) in spezifischer und präziser Weise konfiguriert ist. Der Einsatz solcher smarten Sprühgeräte erfordert gewöhnlich Positionssysteme (z.B. GPS-Empfänger), mit denen die aufgenommenen Daten lokalisiert und Farmvehikel gesteuert bzw. kontrolliert werden, geografische Informationssysteme (GIS), mit denen die Informationen auf verständlichen Karten dargestellt werden, und entsprechende Farmvehikel zum Durchführen der erforderlichen landwirtschaftlichen Maßnahme wie dem Sprühen. Bei einem Beispiel können Schädlinge aus von einer Kamera aufgenommenen Bildern nachgewiesen werden. Bei einem Beispiel können die Schädlinge auf Basis dieser Bilder identifiziert und/oder klassifiziert werden. Bei einer solchen Identifikation und/oder Klassifikation kann man sich Algorithmen zur Bildverarbeitung bedienen. Solche Algorithmen zur Bildverarbeitung können Algorithmen zum maschinellen Lernen wie künstliche neuronale Netze, Entscheidungsbäume, und Künstliche-Intelligenz- Algorithmen nutzen. Auf diese Weise ist es möglich, die hier beschriebenen Verbindungen nur dort anzuwenden, wo sie benötigt werden. The compounds according to the invention can also be used in combination with a smart sprayer such as a device for spot spraying or precision spraying, which is attached to a farm vehicle such as a tractor, a robot, a helicopter, an aircraft, an unmanned aerial vehicle (UAV) such as a drone - or is housed, can be used. Such a device usually comprises input sensors (such as a camera) and a processing unit which is responsible for the analysis of the input data and the provision of a decision, which is based on the analysis of the input data, regarding the application of the compound according to the invention to the crops ( or the weeds) is configured in a specific and precise manner. The use of such smart sprayers usually requires position systems (e.g. GPS receivers) with which the recorded data can be localized and farm vehicles controlled or monitored, geographic information systems (GIS) with which the information is displayed on understandable maps, and corresponding farm vehicles for implementation the required agricultural measure such as spraying. In one example, pests can be detected from images captured by a camera. In one example, the pests can be identified and / or classified based on these images. With such an identification and / or classification one can use algorithms for image processing. Such image processing algorithms can use machine learning algorithms such as artificial neural networks, decision trees, and artificial intelligence algorithms. In this way it is possible to use the connections described here only where they are needed.
Saatgutbehandlung Seed treatment
Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Be-handlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. -toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und auch der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. The control of animal pests by treating the seeds of plants has long been known and is the subject of constant improvements. Nevertheless, a number of problems arise in the treatment of seeds which cannot always be solved satisfactorily. It is therefore desirable to develop methods for protecting the seeds and the germinating plants which make the additional application of pesticides during storage, after sowing or after emergence of the plants superfluous or at least significantly reduce it. It is also desirable to optimize the amount of active ingredient used in such a way that the seed and the germinating plant are protected as best as possible from attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, methods for treating seeds should also include the intrinsic insecticidal or nematicidal properties of pest-resistant or -tolerant transgenic plants in order to achieve optimal protection of the seed and also of the germinating plant with a minimal expenditure of pesticides.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wird. The present invention therefore also relates in particular to a method for protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of the formula (I). The method according to the invention for protecting seeds and germinating plants from attack by pests further comprises a method in which the seed is treated simultaneously in one process or sequentially with a compound of the formula (I) and a mixture component. It also includes a method in which the seed is treated at different times with a compound of the formula (I) and a mixture component.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. The invention also relates to the use of the compounds of the formula (I) for the treatment of seeds in order to protect the seeds and the plants resulting therefrom from animal pests.
Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer erfindungsgemäßen Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und einer Mischungskomponente behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut vorhanden sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungskomponenten enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und eine Mischungskomponente als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. The invention further relates to seeds which have been treated with a compound of the formula (I) according to the invention for protection against animal pests. The invention also relates to seeds, which at the same time with a compound of formula (I) and a Mix component has been treated. The invention further relates to seeds which have been treated at different times with a compound of the formula (I) and a mixture component. In the case of seed which has been treated at different times with a compound of the formula (I) and a mixture component, the individual substances can be present in different layers on the seed. The layers which contain a compound of the formula (I) and mixture components can optionally be separated by an intermediate layer. The invention also relates to seeds in which a compound of the formula (I) and a mixture component are applied as a constituent of a coating or as a further layer or layers in addition to a coating.
Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating- Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden.The invention further relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
Einer der auftretenden Vorteile, wenn eine Verbindung der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. One of the advantages arising when a compound of the formula (I) acts systemically is that the treatment of the seed not only protects the seed itself, but also the plants resulting therefrom from animal pests after emergence. In this way, there is no need to treat the culture immediately at the time of sowing or shortly afterwards.
Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Another advantage can be seen in the fact that the treatment of the seed with a compound of the formula (I) can promote germination and emergence of the treated seed.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. It is also to be regarded as advantageous that compounds of the formula (I) can also be used, in particular, in the case of transgenic seeds.
Verbindungen der Formel (I) können ferner in Kombination mit Zusammensetzungen oder Verbindungen 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 the formula (I) can also be used in combination with compositions or compounds of signal technology, as a result of which better colonization with symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation .
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Fandwirtschaft, 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. The compounds of the formula (I) are suitable for protecting seeds of any type of plant which is used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are grain seeds (e.g. wheat, barley, rye, millet and oats), maize, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, beet (e.g. Sugar beet and fodder beet), peanuts, vegetables (e.g. tomatoes, cucumbers, beans, cabbage plants, onions and lettuce), fruit plants, lawns and ornamentals. The treatment of the seeds of cereals (such as wheat, barley, rye and oats), maize, soy, cotton, canola, rapeseed, vegetables and rice is of particular importance.
Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants that usually contain at least one heterologous gene that enables the expression of a polypeptide controls with particularly insecticidal or nematicidal properties. The heterologous genes in transgenic seeds can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seeds which contain at least one heterologous gene which is derived from Bacillus sp. originates. It is particularly preferably a heterologous gene which originates from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflan e getrennt und von Kolben, Schalen, Stängeln, Hüllen, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z. B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. Im Fall von Reis-Saatgut ist es auch möglich, Saatgut zu verwenden, das getränkt wurde, zum Beispiel in Wasser bis zu einem bestimmten Stadium des Reisembryos („Pigeon Breast Stage“), wodurch die Keimung und ein einheitlicheres Auflaufen stimuliert wird. In the context of the present invention, the compound of the formula (I) is applied to the seed. The seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment. In general, the seed can be treated at any point between harvest and sowing. Usually seeds are used that have been separated from the plant and freed from cobs, peels, stems, coats, wool or pulp. For example, seeds can be used that have been harvested, cleaned and dried to a storable moisture content. Alternatively, seeds can also be used which, after drying, for. B. 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 up to a certain stage of the rice embryo ("pigeon breast stage"), which stimulates germination and more uniform emergence.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. In general, when treating the seed, care must be taken to ensure that the amount of the compound of the formula (I) and / or further additives applied to the seed is selected so that the germination of the seed is not impaired or the plant resulting therefrom is not damaged will. This is particularly important for active ingredients that can show phytotoxic effects when applied in certain amounts.
Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to the person skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formuherungen überführt werden, wie Fösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie UFV-Formulierungen. The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seeds, and also UFV formulations.
Diese Formulierungen werden in bekannter Weise hergesteht, indem man die Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Fösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing the compounds of the formula (I) with customary additives, such as, for example, customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberelline and also water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formuherungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Suitable dyes which can be contained in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments which are sparingly soluble in water and dyes which are soluble in water can be used here. May be mentioned as examples 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. Suitable wetting agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which are customary for the formulation of agrochemical active ingredients and which promote wetting. Alkyl naphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
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 dispersants and / or emulsifiers which can be contained 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 ingredients. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol 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. The seed dressing formulations which can be used according to the invention can contain all foam-inhibiting substances customary for the formulation of agrochemical active ingredients as defoamers. Silicone defoamers and magnesium stearate can preferably be used.
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. All substances which can be used in agrochemical agents for such purposes can be present as preservatives in the seed dressing formulations which can be used according to the invention. Examples include dichlorophene and benzyl alcohol hemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu-lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln ein-setzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Secondary thickening agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which can be used in agrochemical agents for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silicic acid are preferred.
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. As adhesives which can be contained in the seed dressing formulations which can be used according to the invention, all conventional binders which can be used in seed dressings are suitable. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose may be mentioned as preferred.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline Al, A3 (= Gibberellinsäure), A4 und A7 infrage, be sonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel“, Bd. 2, Springer Verlag, 1970, S. 401- 412). 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 Zu bereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. Gibberellins which can be contained in the seed dressing formulations which can be used according to the invention are preferably the gibberellins A1, A3 (= gibberellic acid), A4 and A7; gibberellic acid is particularly preferably used. The gibberellins are known (see R. Wegler “Chemistry of Plant Protection and Pest Control Agents”, 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 treating seeds of the most varied of types. The concentrates or the preparations obtainable from them by diluting them with water can be used for dressing the seeds of grain such as wheat, barley, rye, oats and triticale, as well as the seeds of maize, rice, rape, peas, beans, cotton, Sunflowers, soy and beet or vegetable seeds of the most varied nature. The seed dressing formulations which can be used according to the invention or their diluted application forms can also be used for dressing seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder den 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 seeds with the seed dressing formulations which can be used according to the invention or the use forms produced therefrom by adding water, all mixing devices which can customarily be used for dressing are suitable. In detail, the procedure for dressing is to put the seed in a mixer in batch or continuous mode, add the desired amount of dressing formulations either as such or after prior dilution with water and until the formulation is evenly distributed the seed mixes. If necessary, this is followed by a drying process.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) hegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seeds. The application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
Tiergesundheit Animal health
Auf dem Gebiet der Tiergesundheit, d. h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasit umfasst insbesondere Helminthen und Protozoen wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten oder Akariden. In the field of animal health, i. H. in the field of veterinary medicine, the compounds of the formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects or acarids.
Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Faboratoriumstieren, 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), which have a favorable toxicity towards warm-blooded animals, are suitable for combating parasites which occur in animal breeding and keeping in farm animals, breeding animals, zoo animals, laboratory animals, test animals and domestic animals. They are effective against all or individual stages of development of the parasites.
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. Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel; Reptilien, Amphibien oder Aquariumfische. The farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer and in particular cattle and pigs; or poultry such as turkeys, ducks, geese and especially chickens; or fish or crustaceans, e.g. B. in aquaculture, or possibly insects such as bees. Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets and, in particular, dogs, cats, housebirds; Reptiles, amphibians or aquarium fish.
Gemäß einer bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. According to a particular embodiment, the compounds of the formula (I) are administered to mammals.
Gemäß einer weiteren bestimmten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel oder insbesondere Geflügel, verabreicht. According to a further specific embodiment, the compounds of the formula (I) are administered to birds, namely house birds or, in particular, poultry.
Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. The use of the compounds of the formula (I) for combating animal parasites is intended to reduce or prevent disease, deaths and reduced performance (in the case of meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal husbandry is possible and better animal welfare can be achieved.
In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen" im vorliegenden Zusammenhang, dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert wird. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindungen der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern. In relation to the field of animal health, the term “control” or “control” in the present context means that the compounds of the formula (I) effectively prevent the occurrence of the respective parasite in an animal which is infected with such parasites to a harmless extent , is reduced. More precisely, “combating” in the present context means that the compounds of the formula (I) kill the respective parasite, prevent its growth or prevent its reproduction.
Zu den Arthropoden zählen beispielsweise, ohne hierauf beschränkt zu sein, aus der Ordnung Anoplurida zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina und Ischnocerina, zum Beispiel Bovicola spp., Damalina spp., Felicola spp.; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp., 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. The arthropods include, for example, but are not limited to, from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp. , Melophagus spp., Morellia spp., Musca spp., 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.
Weiterhin sind bei den Arthropoden beispielhaft, ohne hierauf beschränkt zu sein, die folgenden Akari zu nennen: Furthermore, the following Akari are examples of the arthropods, without being restricted to this:
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-host 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 of the Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes 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: Mastigophora (Flagellata), such as:
Metamonada: aus der Ordnung Diplomonadida zum Beispiel Giardia spp., Spironucleus spp. 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. B. Hartmanella sp.
Alveolata wie Apicomplexa (Sporozoa): z. B. Cryptosporidium spp.; aus der Ordnung Eimeriida zum Beispiel Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; aus der Ordnung Adeleida z. B. Hepatozoon spp., Klossiella spp.; aus der Ordnung Haemosporida z. B. Leucocytozoon spp., Plasmodium spp.; aus der Ordnung Piroplasmida z. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; aus der Ordnung Vesibuliferida z. B. Balantidium spp., Buxtonella spp. Alveolata such as Apicomplexa (Sporozoa): e.g. B. 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 e.g. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida e.g. B. Leucocytozoon spp., Plasmodium spp .; from the order Piroplasmida e.g. B. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida e.g. B. 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. The helminths pathogenic for humans or animals include, for example, acanthocephala, nematodes, pentastomas and platyhelminths (for example Monogenea, Cestodes and Trematodes).
Zu beispielhaften Helminthen zählen, ohne hierauf beschränkt zu sein: Exemplary helminths include, but are not limited to:
Monogenea: z. B.: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.; Monogenea: e.g. E.g .: Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp. Cestodes: from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
Aus der Ordnung Cyclophyllida zum Beispiel: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp. From the order Cyclophyllida, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle , Echinolepis spp., Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysanie spp., Thysanosoma 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 class Digenea for example: 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., Fasciolides spp ., Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis 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., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp. Nematodes: from the order Trichinellida, for example: Capillaria spp., Eucoleus spp., Paracapillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
Aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Parastrangyloides spp., Strongyloides spp.From the order Tylenchida, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.
Aus der Ordnung Rhabditina zum Beispiel: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., 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. 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., Crenosoma spp. , Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Hapalous sp spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp., Oesophagum spp., Oesophagum spp., Oesophagum spp. , Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriaulostomum sppyl., Protostrong 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. From the order Spirurida, for example: 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 sppema, Skjrabinpema ., 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., Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida, for example: Moniliformis spp.,
Aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp. From the order Polymorphida, for example: Filicollis spp .; from the order Echinorhynchida, for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp. Pentastoma: from the order Porocephalida, for example Linguatula spp.
Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch; metaphylaktisch oder therapeutisch erfolgen. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods generally known in the art, such as enteral, parenteral, dermal or nasal, in the form of suitable preparations. Administration can be prophylactic; metaphylactically or therapeutically.
So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verbindungen der Formel (I) zur Verwendung als Arzneimittel. Thus, one embodiment of the present invention relates to the compounds of the formula (I) for use as medicaments.
Ein weiterer Aspekt bezieht sich auf die Verbindungen der Formel (I) zur Verwendung alsAnother aspect relates to the compounds of formula (I) for use as
Antiendoparasitikum. Anti-endoparasitic.
Ein weiterer spezieller Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung alsAnother special aspect relates to the compounds of formula (I) for use as
Antihelminthikum, insbesondere zur Verwendung als Nematizid, Platymelminthizid, Acanthocephalizid oder Pentastomizid. Antihelminthic, in particular for use as a nematicide, platymelminthicide, acanthocephalicide or pentastomicide.
Ein weiterer spezieller Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung alsAnother special aspect relates to the compounds of formula (I) for use as
Antiprotozoikum. Antiprotozoic.
Ein weiterer Aspekt betrifft die Verbindungen der Formel (I) zur Verwendung als Antiektoparasitikum, insbesondere ein Arthropodizid, ganz besonders ein Insektizid oder ein Akarizid. Weitere Aspekte der Erfindung sind veterinärmedizinische Formulierungen, die eine wirksame Menge mindestens einer Verbindung der Formel (I) und mindestens einen der folgenden umfassen: einen pharmazeutisch unbedenklichen Exzipienten (z.B. feste oder flüssige Verdünnungsmittel), ein pharmazeutisch unbedenkliches Hilfsmittel (z.B. Tenside), insbesondere einen herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder ein herkömmlicherweise in veterinärmedizinischen Formulierungen verwendetes pharmazeutisch unbedenkliches Hilfsmittel. Another aspect relates to the compounds of the formula (I) for use as an anti-parasitic agent, in particular an arthropodicide, very particularly an insecticide or an acaricide. Further aspects of the invention are veterinary formulations comprising an effective amount of at least one compound of the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (e.g. solid or liquid diluent), a pharmaceutically acceptable auxiliary (e.g. surfactants), in particular one a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
Ein verwandter Aspekt der Erfindung ist ein Verfahren zur Herstellung einer wie hier beschriebenen veterinärmedizinischen Formulierung, welches den Schritt des Mischens mindestens einer Verbindung der Formel (I) mit pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln, insbesondere mit herkömmlicherweise in veterinärmedizinischen Formulierungen verwendeten pharmazeutisch unbedenklichen Exzipienten und/oder Hilfsmitteln umfasst. A related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or auxiliaries, in particular with pharmaceutically acceptable excipients and / or excipients conventionally used in veterinary formulations / or aids.
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 special aspect of the invention is veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozolic and arthropodicidal formulations, very particularly selected from the group of nematicidal, platyhelminthicidal, acanthocidal, acanthicidal, insecticidal, insecticidal formulations the aspects mentioned, as well as processes for their preparation.
Ein anderer Aspekt bezieht sich auf ein Verfahren zur Behandlung einer parasitischen Infektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, durch Anwendung einer wirksamen Menge einer Verbindung der Formel (I) bei einem Tier, insbesondere einem nichthumanen Tier, das dessen bedarf. Another aspect relates to a method for treating a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, especially a non-human Animal in need of 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 the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined here in an animal, in particular a non-human animal, the same requirement.
Ein anderer Aspekt bezieht sich auf die Verwendung der Verbindungen der Formel (I) bei der Behandlung einer Parasiteninfektion, insbesondere einer Infektion durch einen Parasiten ausgewählt aus der Gruppe der hier erwähnten Ektoparasiten und Endoparasiten, bei einem Tier, insbesondere einem nichthumanen Tier. Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasite infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
Im vorliegenden tiergesundheitlichen oder veterinärmedizinischen Zusammenhang schließt der Begriff „Behandlung“ die prophylaktische, die metaphylaktische und die therapeutische Behandlung ein. Bei einer bestimmten Ausführungsform werden hiermit Mischungen mindestens einer Verbindung der Formel (I) mit anderen Wirkstoffen, insbesondere mit Endo- und Ektoparasitiziden, für das veterinärmedizinische Gebiet bereitgestellt. In the present animal health or veterinary context, the term “treatment” includes prophylactic, metaphylactic and therapeutic treatment. In a certain embodiment, mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endo- and ectoparasiticides, are provided 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, “mixture” not only means that two (or more) different active ingredients are formulated in a common formulation and are used accordingly together, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, if more than two active ingredients are to be used, all active ingredients can be formulated in a common formulation or all active ingredients can be formulated in separate formulations; Mixed forms are also conceivable, in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow separate or sequential use of the active ingredients 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 here with their "Common Name" are known and described, for example, in the "Pesticide Manual" (see above) or can be researched 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 Akarizide 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 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; (30) allosterische Modulatoren des GABA-abhängigen Chlorid-Kanals.Exemplary active ingredients from the group of ectoparasiticides as mixing partners include, without this being intended to represent a restriction, the insecticides and acaricides listed in detail above. Further active ingredients that can be used are listed below according to the above-mentioned classification, which is based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) competitive modulators of the nicotinic acetylcholine receptor (nAChR); (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 chordotonal organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) Decoupler of oxidative phosphorylation by disrupting the proton gradient; (14) nicotinic acetylcholine receptor channel blockers; (15) inhibitors of chitin biosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1; (17) molting disruptor (especially in diptera, i.e. two-winged birds); (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) blockers of the voltage-gated sodium channel; (23) inhibitors of acetyl-CoA carboxylase; (28) ryanodine receptor modulators; (30) Allosteric modulators of the GABA-dependent chloride channel.
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 ingredients with unknown or non-specific mechanisms of action, e.g. B. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionate, Triarathen, Clothiazoben, Tetrasul, Potassium Oleate, Petroleum, Metoxadiazon, Gossyplur, Flutenzin, Bromopropylate, Cryolite;
Verbindungen aus anderen Klassen, z.B. Butacarb, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos(- ethyl), Parathion(-ethyl), Methacrifos, Isopropyl-o-salicylat, Trichlorfon, Tigolaner, 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, Dimetilan, Cloethocarb, Phosphocarb, Pirimiphos (- ethyl), Parathion (-ethyl), Methacrifos, Isopropyl-o-salicylate, Trichlorfon, Tigolaner, Sulprofos, Propaphos, Sebufos, Pyridathion, Prothoat, Dichlofenthion, Demeton-S-methylsulfon, Isazofos, Cyanofenphos, Dialifos, Carbophenothion, Autathiofos, Aromfenvinfos (-methyl), Azinphos (-ethyl), Chlorpyrifos (-ethyl), Fosmethilan, Iodofenphos, Dioxabenzofos, Formothos, E, Fupensulfofrazofos,
Organochlorverbindungen, z. B. Camphechlor, Lindan, Fleptachlor; oder Phenylpyrazole, z. B. Acetoprol, Pyrafluprol, Pyriprol, Vaniliprol, Sisapronil; oder Isoxazoline, z. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Organochlorine compounds, e.g. B. camphechlor, lindane, fleptachlor; or phenylpyrazoles, e.g. B. acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. B. Sarolaner, Afoxolaner, Lotilaner, Fluralaner;
Pyrethroide, z. B. (eis-, trans-)Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Fieptafluthrin, Bioethanomethrin, Biopermethrin, Fenpyrithrin, cis-Cypermethrin, cis-Permethrin, Clocythrin, Cyhalothrin (lambda-), Chlovaporthrin, oder halogenierte Kohlenwasserstoffverbindungen (FICFls),Pyrethroids, e.g. B. (Eis-, trans-) Metofluthrin, Profluthrin, Flufenprox, Flubrocythrinat, Fubfenprox, Fenfluthrin, Protrifenbut, Pyresmethrin, RU15525, Terallethrin, cis-Resmethrin, Fieptafluthrin, Fieptafluthrin, Cypthrin-cythrin, clo-methanomethrin, cloethanopermethrin, clo-pyrocythrin, fenopermethrin , Cyhalothrin (lambda-), chlovaporthrin, or halogenated hydrocarbon compounds (FICFls),
Neonicotinoide, z. B. Nithiazin Neonicotinoids, e.g. B. nithiazine
Dicloromezotiaz, Triflumezopyrim makrocyclische Lactone, z. B. Nemadectin, Ivermectin, Latidectin, Moxidectin, Selamectin, Eprinomectin, Doramectin, Emamectinbenzoat; Milbemycinoxim Dicloromezotiaz, triflumezopyrim macrocyclic lactones, e.g. B. nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime
Tripren, Epofenonan, Diofenolan; Triprene, epofenonane, diofenolane;
Biologicals, Fiormone oder Pheromone, zum Beispiel natürliche Produkte, z.B. Thuringiensin, Codlemon oder Neem-Komponenten Biologicals, fiormones or pheromones, for example natural products, e.g. thuringiensine, codlemon or neem components
Dinitrophenole, z. B. Dinocap, Dinobuton, Binapacryl; Dinitrophenols, e.g. B. Dinocap, Dinobuton, Binapacryl;
Benzoylharnstoffe, z. B. Fluazuron, Penfluron, Benzoylureas, e.g. B. Fluazuron, Penfluron,
Amidinderivate, z. B. Chlormebuform, Cymiazol, Demiditraz Amidine derivatives, e.g. B. Chlormebuform, Cymiazol, Demiditraz
Bienenstockvarroa- Akarizide, zum Beispiel organische Säuren, z.B. Ameisensäure, Oxalsäure. Beehive varroa acaricides, for example organic acids, e.g. formic acid, oxalic acid.
Zu beispielhaften Wirkstoffen aus der Gruppe der Endoparasitizide, als Mischungspartner, zählen, ohne hierauf beschränkt zu sein, anthelmintische Wirkstoffe und antiprotozoische Wirkstoffe. Exemplary active ingredients from the group of endoparasiticides, as mixing partners, include, without being limited thereto, anthelmintic active ingredients and antiprotozoal active ingredients.
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 Depsipetide, insbesondere 24-gliedrigen cyclischen Depsipeptide, zum Beispiel: Emodepsid, PF1022A; aus der Klasse der Tetrahydropyrimidine zum Beispiel: Morantel, Pyrantel, Oxantel; aus der Klasse der Imidazothiazole zum Beispiel: Butamisol, Eevamisol, 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, Miraeil, Eucanthon, Hycanthon, Hetolin, Emetin, Diethylcarbamazin, Dichlorophen, Diamfenetid, Clonazepam, Bephenium, Amoscanat, Clorsulon.The anthelmintic active ingredients include, but are not limited to, the following nematicidal, trematicidal and / or cestocidal active ingredients: from the class of the macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, milbemycin; from the class of benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole; from the class of the depsipeptides, preferably cyclic depsipeptides, in particular 24-membered cyclic depsipeptides, for example: emodepside, PF1022A; from the class of the tetrahydropyrimidines, for example: morantel, pyrantel, oxantel; from the class of the imidazothiazoles, for example: butamisole, eevamisole, tetramisole; from the class of the aminophenylamidines, for example: amide coat, deacylated amide coat (dAMD), tribendimidine; from the class of the aminoacetonitriles, for example: Monepantel; from the class of the paraherquamides, for example: paraherquamid, derquantel; from the class of the salicylanilides, for example: tribromosalan, bromoxanide, bromianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide; from the class of substituted phenols, for example: Nitroxynil, Bithionol, Disophenol, Hexachlorophene, Niclofolan, Meniclopholan; from the class of the organophosphates, for example: Trichlorfon, Naphthalofos, Dichlorvos / DDVP, Crufomat, Coumaphos, Haloxon; from the class of the piperazinones / quinolines, for example: praziquantel, epsiprantel; from the class of the piperazines, for example: piperazine, hydroxyzine; from the class of the tetracyclines, for example: tetracycline, chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline; from various other classes, for example: Bunamidine, Niridazole, Resorantel, Omphalotin, Oltipraz, Nitroscanat, Nitroxynil, Oxamniquin, Mirasan, Miraeil, Eucanthone, Hycanthone, Hetolin, Emetine, Diethylcarbamazine, Dichamulonepazhen, Diamfenetid, Clonazhenium.
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. Antiprotozoal agents, including but not limited to the following agents: from the class of the triazines, for example: Diclazuril, Ponazuril, Letrazuril, Toltrazuril; from the class polyletherionophore, for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of the macrocyclic lactones, for example: milbemycin, erythromycin; from the class of the quinolones, for example: enrofloxacin, pradofloxacin; from the quinine class, for example: chloroquine; from the class of the pyrimidines, for example: pyrimethamine; from the class of the sulfonamides, for example: sulfachinoxaline, trimethoprim, sulfaclozine; from the class of the thiamines, for example: Amprolium; from the class of the lincosamides, for example: clindamycin; from the class of the carbanilides, for example: imidocarb; from the class of nitrofurans, for example: Nifurtimox; from the class of the quinazolinone alkaloids, for example: Halofuginone; from various other classes, for example: Oxamniquin, 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, Dictyarus canis .
Ahe genannten Mischungspartner können außerdem, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. The mixing partners mentioned above can also, if appropriate, if they are capable of doing so on the basis of their functional groups, form salts with suitable bases or acids.
V ektorbekämpfung V ector fight
Die Verbindungen der Formel (I) können auch in der Vektorbekämpfung eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnid, 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 einen Wirt, oder nach Injektion (z. B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. The compounds of the formula (I) can also be used in combating vectors. A vector within the meaning of the present invention is an arthropod, in particular an insect or arachnid, which is able to remove pathogens such as. B. viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host. The pathogens can be transmitted to a host either mechanically (e.g. trachoma by non-stinging flies) or after injection (e.g. malaria parasites by mosquitoes) into a host.
Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: 1) Mücken Examples of vectors and the diseases or pathogens they transmit are: 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, weitere virale Erkrankungen, Filariasis, Übertragung von anderen Würmern; - Culex: Japanese encephalitis, other viral diseases, filariasis, transmission from 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), hämorrhagisches Krim- Kongo-Fieber, Borreliose; 5) mites: acariosis, epidemic typhus, rickettsipox, tularemia, Saint Louis encephalitis, early summer meningoencephalitis (TBE), Crimean Congo hemorrhagic 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: Borelliosis such as Borrelia bungdorferi sensu lato., Borrelia duttoni, early summer meningoencephalitis, 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. Further examples of vectors within the meaning of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. B. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodids such as Phlebotomus, Lutzomyia, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.
Eine Vektorbekämpfung ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Combating vectors is also possible if the compounds of the formula (I) are resistance-breaking.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten und/oder Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorbekämpfung, z. B. in der Landwirtschaft, im Gartenbau, in Gärten und Freizeiteinrichtungen sowie im Vorrats- und Materialschutz. Schutz von technischen Materialen Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens that are transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. B. in agriculture, in horticulture, in gardens and leisure facilities as well as in storage and material protection. Protection of technical materials
Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z. B. aus den Ordnungen Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of the formula (I) are suitable for protecting industrial materials against attack or destruction by insects, e.g. 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. Industrial materials in the present context are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, glues, paper and cardboard, leather, wood, wood processing products and paints. The use of the invention to protect wood is particularly preferred.
In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d. h., sie können ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder Fungizide kommen insbesondere die oben genannten in Frage. In a further embodiment, the compounds of the formula (I) are in the form of a ready-to-use pesticide, i. E. That is, they can be applied to the corresponding material without further changes. As further insecticides or fungicides, those mentioned above are particularly suitable.
Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Kontakt kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect against fouling on objects, in particular ship hulls, sieves, nets, structures, quays and signal systems which come into contact with sea or brackish water. The compounds of the formula (I) can also be used as antifouling agents on their own or in combinations with other active ingredients.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren, Zecken und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen, Tierzuchtanlagen Vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. The compounds of the formula (I) are suitable for combating animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and stored product protection, especially for combating insects, arachnids, ticks and mites that occur in closed rooms, such as apartments, factory halls, offices, vehicle cabins, animal breeding facilities. To control animal pests, the compounds of the formula (I) are used alone or in combination with other active ingredients and / or auxiliaries. They are preferably used in household insecticide products. The compounds of the formula (I) are active against sensitive and resistant species and against all stages of development.
Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. 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. These pests include, for example, pests from 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. They are used, for example, in aerosols, pressureless sprays, e.g. B. pump and atomizer sprays, fog machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive vaporizer systems, moth papers, moth bags and moth gels, as granules or stems in lures or bait stations.
Analytische Bestimmungen Analytical determinations
Die nachstehend beschriebenen Durchführungen der analytischen Bestimmungen beziehen sich auf alle Angaben im gesamten Dokument, sofern die Durchführung der jeweiligen analytischen Bestimmung an der jeweiligen Textstelle nicht gesondert beschrieben ist. The carrying out of the analytical determinations described below relate to all information in the entire document, unless the carrying out of the respective analytical determination is described separately at the relevant text passage.
Massenspektrometrie Mass spectrometry
Die Bestimmung von [M+Fl]+ oder M mittels LC-MS unter sauren chromatographischen Bedingungen wurde mit 1 ml Ameisensäure pro Liter Acetonitril und 0,9 ml Ameisensäure pro Liter Millipore -Wasser als Eluenten durchgeführt. Es wurde die Säule Zorbax Eclipse Plus CI 8 50 mm * 2,1 mm, verwendet, bei einer Temperatur des Säulenofens von 55°C. The determination of [M + Fl] + or M by means of LC-MS under acidic chromatographic conditions was carried out with 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore® water as eluents. The column Zorbax Eclipse Plus CI 8 50 mm * 2.1 mm, at a temperature of the column oven of 55 ° C, was used.
Instrumente: Instruments:
LC-MS3: Waters UPLC mit SQD2 Massenspektrometer und SampleManager Probenwechsler. Linearer Gradient 0,0 bis 1,70 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 1,70 bis 2,40 Minuten konstant 95 % Acetonitril, Fluss 0,85 ml/min. LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml / min.
LC-MS6 und LC-MS7: Agilent 1290 LC, Agilent MSD, F1TS PAL Probenwechsler. Linearer Gradient 0,0 bis 1,80 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 1,80 bis 2,50 Minuten konstant 95 % Acetonitril, Fluss 1 ,0 ml/min. LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD, F1TS PAL sample changer. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml / min.
Die Bestimmung von [M+Fl]+ mittels LC-MS unter neutralen chromatographischen Bedingungen wurde mit Acetonitril und Millipore-Wasser mit 79 mg/1 Ammoniumcarbonat als Eluenten durchgeführt. The determination of [M + Fl] + by means of LC-MS under neutral chromatographic conditions was carried out with acetonitrile and Millipore water with 79 mg / l ammonium carbonate as eluents.
Instrumente: Instruments:
LC-MS4: Waters IClass Acquity mit QDA Massenspektrometer und FTN Probenwechsler (Säule Waters Acquity 1,7 pm 50 mm * 2,1 mm, Ofentemperatur 45°C). Linearer Gradient 0,0 bis 2,10 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 2,10 bis 3,00 Minuten konstant 95 % Acetonitril, Fluss 0,7 ml/min.LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column Waters Acquity 1.7 pm 50 mm * 2.1 mm, oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 ml / min.
LC-MS5: Agilent 1100 LC System mit MSD Massenspektrometer und F1TS PAL Probenwechsler (Säule: Zorbax XDB CI 8 1,8 pm50mm * 4,6 mm, Ofentemperatur 55°C). Linearer Gradient 0,0 bis 4,25 Minuten von 10 % Acetonitril zu 95 % Acetonitril, von 4,25 bis 5,80 Minuten konstant 95 % Acetonitril, Fluss 2,0 ml/min. LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and F1TS PAL sample changer (column: Zorbax XDB CI 8 1.8 pm50mm * 4.6 mm, oven temperature 55 ° C). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 ml / min.
Die Retentionzeit-Indizes wurden in allen Fällen gemäß einer homologen Serie von geradkettigen Alkan- 2-onen mit 3 bis 16 Kohlenstoffen bestimmt, wobei der Index des ersten Alkanons auf 300, der des letzten auf 1600 gesetzt und zwischen den Werten aufeinanderfolgender Alkanone linear interpoliert wurde.The retention time indices were determined in all cases according to a homologous series of straight-chain alkanones with 3 to 16 carbons, with the index of the first alkanone set to 300, that of the last to 1600 and linear interpolation between the values of successive alkanones .
Die Messungen der 1 H-NMR Spektren wurden mit einem Bruker Avance III 400 MHz Spektrometer, ausgestattet mit einem 1,7 mm TCI Probenkopf, mit Tetramethylsilan als Standard (0,00 ppm) durchgeführt und die Messungen wurden aufgezeichnet in der Regel von Lösungen in den Lösungsmitteln CD3CN, CDCL oder d6-DMSO. Alternativ wurde ein Bruker Avance III 600 MHz Spektrometer ausgestattet mit einem 5 mm CPNMP Probenkopf oder ein Bruker Avance NEO 600 MHz Spektrometer ausgestattet mit einem 5 mm TCI Probenkopf für die Messungen verwendet. In der Regel wurden die Messungen bei einer Probenkopftemperatur von 298 K durchgeführt. Sofern andere Messtemperaturen verwendet wurden, wird dies gesondert vermerkt. The measurements of the 1 H-NMR spectra were carried out with a Bruker Avance III 400 MHz spectrometer, equipped with a 1.7 mm TCI probe head, with tetramethylsilane as standard (0.00 ppm) and the measurements were usually recorded from solutions in the solvents CD3CN, CDCL or d6-DMSO. Alternatively, a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements. As a rule, the measurements were carried out at a probe head temperature of 298 K. If other measuring temperatures were used, this will be noted separately.
NMR-Peaklisten-Verfahren NMR peak list method
Die 'H-NMR- Daten ausgewählter Beispiele werden in Form von 'H-NMR -Peaklisten dargestellt. Zu jedem Signalpeak wird erst der d-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die d-Wert - Signalintensitäts- Zahlenpaare werden durch Semikolons voneinander getrennt aufgelistet. The 'H-NMR data of selected examples are presented in the form of' H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity is listed in round brackets. The d-value - signal intensity number pairs are listed separated from each other by semicolons.
Die Peakliste eines Beispiels hat daher die Form: di (Intensitäti); 62 (Intensität 2); . ; d, (Intensität,); . ; dh (Intensität) The peak list of an example therefore has the form: di (intensityi); 62 (intensity 2); . ; d, (intensity,); . ; d h (intensity)
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einer gedruckten Darstellung eines 1 H-NMR-Spcktrums 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 representation of a 1 H-NMR spectrum in cm and shows the real relationships between the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
Zur Kalibrierung der chemischen Verschiebung von 'H-NMR-Spektren wird Tetramethylsilan genutzt oder die chemische Verschiebung des Lösungsmittels, falls die Probe kein Tetramethylsilan enthält. Daher können die 'H-NMR-Pcaklistcn unter Umständen den Tetramethylsilan-Peak enthalten. Tetramethylsilane is used to calibrate the chemical shift of 'H-NMR spectra or the chemical shift of the solvent if the sample does not contain tetramethylsilane. Therefore the 'H-NMR-Pcclists may contain the tetramethylsilane peak.
Die Listen der 'H-NMR-Pcaks sind äquivalent zu den klassischen 1 H-NMR-Darstcllungcn und enthalten somit gewöhnlich alle Peaks, die bei klassischen 1 H-N R- Interpretationen ebenso aufgeführt werden.The lists of 'H-NMR-Pcaks are equivalent to the classic 1 H-NMR representations and thus usually contain all peaks that are also listed in classic 1 HNR interpretations.
Darüber hinaus können sie wie klassische 1 H-NMR-Darstcllungcn Lösungsmittelsignale, Signale von Stereoisomeren der Verbindungen, die gegebenenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. 1 H-NMR-Lösungsmittel signale, das Tetramethylsilan-Signal und das Wassersignal im jeweiligen Lösungsmittel sind von der relativen Intensitätskalibrierung ausgenommen, weil die dafür angegebenen Intensitätswerte sehr hoch sein können. In addition, like classical 1 H-NMR representations, they can show solvent signals, signals of stereoisomers of the compounds which are optionally the subject of the invention, and / or peaks of impurities. 1 H-NMR solvent signals, the tetramethylsilane signal and the water signal in the respective solvent are excluded from the relative intensity calibration because the intensity values given for them can be very high.
Die Peaks von Stereoisomeren der erfindungsgemäßen Verbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich eine geringere Intensität als die Peaks der erfindungsgemäßen Verbindungen (zum Beispiel bei einer Reinheit von >90%). The peaks of stereoisomers of the compounds according to the invention and / or peaks of impurities usually have a lower intensity than the peaks of the compounds according to the invention (for example at a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion eines Herstellungsverfahrens anhand von “Nebenprodukt-Fingerabdrücken” zu erkennen. Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of a manufacturing process based on “by-product fingerprints”.
Ein Experte, 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 identifizieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Identifizierung ist äquivalent zur betreffenden Peak-Auflistung bei der klassischen 'H-NMR- Interpretation. An expert who calculates the peaks of the target compounds with known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can identify the peaks of the target compounds as required, with additional intensity filters being used if necessary. This identification is equivalent to the relevant list of peaks in the classical 'H-NMR interpretation.
Das benutzte Lösungsmittel kann aus der JCAMP-Datei mit dem Parameter „solvent“ ausgelesen werden, die Messfrequenz des Spektrometers mit „observe frequency“ und das Spektrometermodell mit „spectrometer/data System“. The solvent used can be read from the JCAMP file with the parameter "solvent", the measuring frequency of the spectrometer with "observe frequency" and the spectrometer model with "spectrometer / data system".
13C-NMR-Daten werden analog zu den 1 H-NMR Daten als Peaklisten aus breitbandentkoppelten 13C- NMR-Spektren angegeben. 13C-NMR-Lösungsmittelsignale und Tetramethylsilan sind aus der relativen Intensitätskalibrierung herausgenommen, weil diese Signale sehr hohe Intensitätswerte haben können. 13 C-NMR data are given analogously to the 1 H-NMR data as peak lists from broadband decoupled 13 C-NMR spectra. 13 C-NMR solvent signals and tetramethylsilane are removed from the relative intensity calibration because these signals can have very high intensity values.
Weitere Details zu NMR-Daten-Beschreibung mit Peaklisten können entnommen werden aus: “Citation of NMR Peaklist Data within Patent Applications” in der Research Disclosure Database Number 564025. logP- Werte Further details on the description of NMR data with peak lists can be found in: “Citation of NMR Peak List Data within Patent Applications” in the Research Disclosure Database Number 564025. logP values
Die Bestimmung der logP-Werte erfolgte gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (CI 8) mit Hilfe folgender Methoden: The logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (CI 8) using the following methods:
[a] Der logP Wert wird durch LC-UV Messung im sauren Bereich bestimmt, mit 0,9 ml/1 Ameisensäure in Wasser und 1,0 ml/1 Ameisensäure in Acetonitril als Eluenten (linearer Gradient von 10% Acetonitrile bis 95% Acetonitril). [a] The logP value is determined by LC-UV measurement in the acidic range, with 0.9 ml / l formic acid in water and 1.0 ml / l formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile ).
[b] Der logP Wert wird durch LC-UV Messung im neutralen Bereich bestimmt, mit 0,001 molarer Ammoniumacetatlösung in Wasser und Acetonitril als Eluenten (linearer Gradient von 10% Acetonitril bis 95% Acetonitril). Die Kalibrierung wurde mit geradkettigen Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen) mit bekannten logP Werten durchgeführt. Die Werte zwischen aufeinanderfolgender Alkanonen werden durch lineare Regression bestimmt. [b] The logP value is determined by LC-UV measurement in the neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile). The calibration was carried out with straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known logP values. The values between successive alkanones are determined by linear regression.
Abkürzungsverzeichnis DIPEA Diisopropylethylamin DMF N,N-Dimethylformamid DMSO Dimethylsulfoxid dppf 1 , 1 '-Bis(diphenylphosphino)ferrocen EDCI 1 -(3-Dimethylaminopropyl)-3-ethylcarbodiimid hydrochlorid h Stunde(n) List of abbreviations DIPEA diisopropylethylamine DMF N, N-dimethylformamide DMSO dimethyl sulfoxide dppf 1, 1 '-Bis (diphenylphosphino) ferrocene EDCI 1 - (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride h hour (s)
HATU 0-(7-Azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium-hexafluorphosphatHATU 0- (7-Azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate
HPLC Hochleistungsflüssigkeitschromatographie (englisch high performance liquid chromatography) mm Minute(n) MTBE 2-Methoxy-2-methylpropan (Methyl-tert-butylether) RT Raumtemperatur HPLC high performance liquid chromatography mm minute (s) MTBE 2-methoxy-2-methylpropane (methyl tert-butyl ether) RT room temperature
THF Tetrahydrofuran THF tetrahydrofuran
Herstellungsbeispiele Manufacturing examples
Intermediate Intermediate
Intermediat 1A Intermediate 1A
Ethyl-2-brom- 1 -methyl- 1 H-imidazol-4-carboxylat Ethyl 2-bromo-1-methyl-1 H -imidazole-4-carboxylate
30,0 g (195 mmol) Ethyl-1 -methyl- lH-imidazol-4-carboxylat wurden in 1,0 L Tetrahydrofuran gelöst und auf 0 °C gekühlt. Zu dieser Lösung wurden 34,5 g (195 mmol) /V-Bromsuccinimid portionsweise zugegeben und die Reaktionsmischung wurde über Nacht bei Raumtemperatur gerührt. Die Reaktion wurde durch die Zugabe von gesättigter Natriumthiosulfatlösung (Na^S^Ch) beendet und es wurden 800 mL Essigester zugegeben. Die Phasen wurden getrennt und es wurde dreimal mit je 800 mL Essigester extrahiert. Die organischen Phasen wurden vereinigt, über Natriumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Petrolether / Essigester Gradienten (3:1) als Laufmittel gereinigt. 30.0 g (195 mmol) of ethyl 1-methyl-1H-imidazole-4-carboxylate were dissolved in 1.0 L of tetrahydrofuran and cooled to 0.degree. 34.5 g (195 mmol) / V-bromosuccinimide were added in portions to this solution and the reaction mixture was stirred at room temperature overnight. The reaction was ended by the addition of saturated sodium thiosulfate solution (Na ^ S ^ Ch) and 800 ml of ethyl acetate were added. The phases were separated and extracted three times with 800 ml of ethyl acetate each time. The organic phases were combined, dried over sodium sulfate and filtered. The solvent was distilled off in vacuo and the residue was purified by column chromatography using a petroleum ether / ethyl acetate gradient (3: 1) as the mobile phase.
'H-NMR(300 MHz, d6-DMSO) d ppm: 1,26 (t, 3H), 3,64 (s, 3H), 4,22 (q, 2H), 8,07 (s, 1H). Intermediat 2A 'H-NMR (300 MHz, d 6 -DMSO) d ppm: 1.26 (t, 3H), 3.64 (s, 3H), 4.22 (q, 2H), 8.07 (s, 1H ). Intermediate 2A
2-Brom-5-(ethylsulfanyl)- 1 -methyl- 1 H-imidazol-4-carbonsäure 2-Bromo-5- (ethylsulfanyl) -1-methyl-1 H-imidazole-4-carboxylic acid
31,0 g (134 mmol) Ethyl-2-brom-l-methyl-lH-imidazol-4-carboxylat und 24,4 g (200 mmol) Diethyldisulfid wurden in 620 mL Tetrahydrofuran gelöst und auf -78 °C gekühlt. Zu dieser Lösung wurden 100 mL (2M in THL, 200 mmol) Lithiumdiisopropylamid (LDA) zugetropft und die Reaktionsmischung wurde 30 min bei -78 °C gerührt. Die Reaktion wurde durch die Zugabe von gesättigter Ammoniumchloridlösung beendet. Die Phasen wurden getrennt und die wässrige Phase wurde dreimal mit je 300 mL Essigester extrahiert. Die organischen Phasen wurden vereinigt, über Magnesiumsulfat getrocknet und filtriert. Das Lösungsmittel wurde im Vakuum abdestilliert und der Rückstand wurde durch säulenchromatographische Reinigung mit einem Petrolether / Essigester Gradienten als Laufmittel gereinigt. Es wurden 28,5 g (97,3 mmol) Ethyl-2-brom-5-(ethylsulfanyl)-l- methyl-lH-imidazol-4-carboxylat erhalten. Dieses wurde in 300 mL Methanol gelöst und die Lösung wurde auf 0 °C gekühlt. Dann wurden 300 mL Natriumhydroxid (2N in Wasser, 600 mmol) zugegeben und die Mischung wurde 1 h bei Raumtemperatur gerührt. Die Mischung wurde am Rotationsverdampfer konzentriert und durch Zugabe von IN HCl neutralisiert. Dann wurde mit Essigester extrahiert. Das Lösungsmittel wurde im Vakuum abdestilliert und die Zielverbindung erhalten. 31.0 g (134 mmol) of ethyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate and 24.4 g (200 mmol) of diethyl disulfide were dissolved in 620 ml of tetrahydrofuran and cooled to -78 ° C. 100 mL (2M in THL, 200 mmol) lithium diisopropylamide (LDA) were added dropwise to this solution and the reaction mixture was stirred at -78 ° C. for 30 min. The reaction was terminated by the addition of saturated ammonium chloride solution. The phases were separated and the aqueous phase was extracted three times with 300 mL ethyl acetate each time. The organic phases were combined, dried over magnesium sulfate and filtered. The solvent was distilled off in vacuo and the The residue was purified by column chromatography using a petroleum ether / ethyl acetate gradient as the mobile phase. 28.5 g (97.3 mmol) of ethyl 2-bromo-5- (ethylsulfanyl) -l-methyl-1H-imidazole-4-carboxylate were obtained. This was dissolved in 300 mL of methanol and the solution was cooled to 0 ° C. Then 300 mL sodium hydroxide (2N in water, 600 mmol) were added and the mixture was stirred at room temperature for 1 h. The mixture was concentrated on a rotary evaporator and neutralized by adding 1N HCl. Then it was extracted with ethyl acetate. The solvent was distilled off in vacuo and the target compound was obtained.
'H-NMR(300 MHz, d6-DMSO) d ppm: 1,09 (t, 3H), 2,86 (q, 2H), 3,64 (s, 3H), 12,60 (s, 1H). 'H-NMR (300 MHz, d 6 -DMSO) d ppm: 1.09 (t, 3H), 2.86 (q, 2H), 3.64 (s, 3H), 12.60 (s, 1H ).
Intermediat 3A N-(7-Amino-2,2,3,3-tetrafluor-2,3-dihydro-l,4-benzodioxin-6-yl)-2-brom-5-(ethylsulfanyl)-l-methyl- 1 H-i m i da zol -4-carhox am i d Intermediate 3A N- (7-Amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl) -2-bromo-5- (ethylsulfanyl) -l-methyl- 1 Hi mi da zol -4-carhox am id
2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-carbonsäure (557 mg, 2,10 mmol) wurde in DML (40,0 mL) vorgelegt und mit HATU (957 mg, 2,52 mmol) bei RT versetzt und 30 min lang gerührt. Anschließend wurde die Mischung auf -10 °C gekühlt und eine Lösung von 2,2,3,3-Tetrafluor-2,3- dihydro-l,4-benzodioxin-6,7-diamin (500 mg, 2,10 mmol) in DML (10,0 mL) wurde langsam hinzugetropft. Nach beendeter Zugabe wurde 1 h lang bei -10 °C gerührt. Anschließend wurde die Mischung auf Wasser geschüttet und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden zweimal mit 1,0 M Salzsäure und einmal mit gesättigter wässriger Natriumchloridlösung gewaschen und über Natriumsulfat getrocknet. Einengen der Lösung bis zur Trockne lieferte die Titel Verbindung (1,34 g, 73% Reinheit, 96% d. Th.). Die erhaltene Titelverbindung wurde ohne weitere Aufreinigung weiter umgesetzt. 2-Bromo-5- (ethylsulfanyl) -l-methyl-lH-imidazole-4-carboxylic acid (557 mg, 2.10 mmol) was placed in DML (40.0 ml) and mixed with HATU (957 mg, 2.52 mmol) at RT and stirred for 30 min. The mixture was then cooled to -10 ° C. and a solution of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6,7-diamine (500 mg, 2.10 mmol) in DML (10.0 mL) was slowly added dropwise. After the addition had ended, the mixture was stirred at -10 ° C. for 1 h. The mixture was then poured into water and extracted with dichloromethane. The combined organic phases were washed twice with 1.0 M hydrochloric acid and once with saturated aqueous sodium chloride solution and dried over sodium sulfate. Concentration of the solution to dryness gave the title compound (1.34 g, 73% purity, 96% of theory). The title compound obtained was reacted further without further purification.
ESI Masse [m/z]: 484,9 / 486,9 [M+H]+ ESI mass [m / z]: 484.9 / 486.9 [M + H] +
Intermediat 4A 4,4,5 ,5-Tetramethyl-2- { 4- [ 1 -(trifluormethyl)cyclopropyl]phenyl } - 1 ,3 ,2-dioxaborolan Eine Mischung aus l-Brom-4-[l-(trifluormethyl)cyclopropyl]benzol (250 mg, 943 pmol), 4,4,4',4',5,5,5,,5,-Octamethyl-2,2,-bi-l,3,2-dioxaborolan (287 mg, 1132 pmol), Pd(dppf)a2*CH2Cl2, (34,65 mg, 47 pmol) und Kaliumacetat (278 mg, 2,83 mmol) in Acetonitril (4,0 mL) wurde in einem Mikrowellenreaktor 15 min lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kiesegel lieferte die Titel verbidnung (281 mg, 81% Reinheit, 77% d. Th.). Intermediate 4A 4,4,5,5-tetramethyl-2- {4- [1 - (trifluoromethyl) cyclopropyl] phenyl} - 1,3,2-dioxaborolane A mixture of l-bromo-4- [l- (trifluoromethyl) cyclopropyl] benzene (250 mg, 943 pmol), 4,4,4 ', 4', 5,5,5, 5, -Octamethyl-2, 2 , -bi-l, 3,2-dioxaborolane (287 mg, 1132 pmol), Pd (dppf) a 2 * CH 2 Cl 2 , (34.65 mg, 47 pmol) and potassium acetate (278 mg, 2.83 mmol) in acetonitrile (4.0 mL) was heated to 150 ° C for 15 min in a microwave reactor. After cooling to RT, the reaction mixture was concentrated. Purification of the residue by column chromatography on silica gel provided the title compound (281 mg, 81% purity, 77% of theory).
ESI Masse [m/z]: 313,1 [M+H]+ ESI mass [m / z]: 313.1 [M + H] +
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 7.68 (d, 2H), 7.47 (d, 2H), 1.37-1.32 (m, 2H), 1.29 (s, 12H), 1.15-1.09 (m, 2H). Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.68 (d, 2H), 7.47 (d, 2H), 1.37-1.32 (m, 2H), 1.29 (s, 12H), 1.15- 1.09 (m, 2H).
Intermediat 5A tert-Butyl-2-cyclopropyl- 1 -methyl- 1 H-imidazol-4-carboxylat Intermediate 5A tert -Butyl 2-cyclopropyl-1-methyl-1 H -imidazole-4-carboxylate
Zu einer Lösung von tert-Butyl-2-brom-l -methyl- lH-imidazol-4-carboxylat (10,0 g, 38,3 mmol) in THF (300 mL) gab man eine Lösung von Kaliumphosphat (16,0 g, 116 mmol) in Wasser (60 mL). DieA solution of potassium phosphate (16.0 g, 116 mmol) in water (60 mL). the
Mischung wurde 10 min lang unter einer inerten Atmosphäre gerührt bevor X-Phos Pd G2 (CAS: 1310584-14-5, 2.00 g, 2,54 mmol) hinzugegeben wurde. Die Mischung wurde zum Sieden erhitzt, dann wurde eine Lösung von Cyclopropylboronsäure (10,0 g, 116 mmol) in THF (100 mL) über einen Zeitraum von 8 h hinzugetropft. Nach beendeter Zugabe wurde die Mischung über Nacht weiter refluxiert, bevor erneut Kaliumphophat (16,0 g, 116 mmol) gefolgt von einer Lösung aus Cyclopropylboronsäure (10,0 g, 116 mmol) in THF (100 mL) hinzugegeben wurde. Nach beendeter Zugabe wurde die Reaktionsmischung noch 16 h lang refluxiert. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser (1000 mL) verdünnt und mit Essigsäureethylester (2 x 500 mL) extrahiert. Die vereingten organischen Phasen wurden mit gesättigter wässriger Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet, über eine dünne Kiselgelschicht filtriert und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieselgel lieferte die Titel Verbindung (4,00 g, 49% d. Th.). Intermediat 6A tert-Butyl-5-brom-2-cy clopropyl- 1 -methyl- 1 H-imidazol-4-carboxylat The mixture was stirred for 10 min under an inert atmosphere before X-Phos Pd G2 (CAS: 1310584-14-5, 2.00 g, 2.54 mmol) was added. The mixture was heated to boiling, then a solution of cyclopropylboronic acid (10.0 g, 116 mmol) in THF (100 ml) was added dropwise over a period of 8 h. After the addition had ended, the mixture was refluxed further overnight before potassium phosphate (16.0 g, 116 mmol) was added again, followed by a solution of cyclopropylboronic acid (10.0 g, 116 mmol) in THF (100 mL). After the addition had ended, the reaction mixture was refluxed for a further 16 hours. After cooling to RT, the mixture was diluted with water (1000 ml) and extracted with ethyl acetate (2 × 500 ml). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered through a thin layer of silica gel and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (4.00 g, 49% of theory). Intermediate 6A tert -Butyl 5-bromo-2-cyclopropyl-1-methyl-1 H -imidazole-4-carboxylate
Zu einer Lösung von tert-Butyl-2-cy clopropyl- 1 -methyl- lH-imidazol-4-carboxylat (6,00 g, 27,0 mmol) in Dichlormethan (100 mL) wurde eine Lösung von Natriumhydrogencarbonat (2,88 g, 34,3 mmol) in Wasser (12 mL) hinzugegeben. Unter Eisbadkühlung wurde eine Lösung von Brom (1,73 mL, 33,8 mmol) in Dichlormethan (20,0 mL) hinzugetropft. Nach beendeter Zugabe wurde die Reaktionsmischung über Nacht bei RT gerührt. Anschließend wurde die Lösung mit Dichlormethan (200 mL) verdünnt und nacheinander mit gesättigter wässriger Natriumhydrogencarbonatlösung (150 mL), gesättigter wässriger Natriumthiosulfatlösung (150 mL) und gesättigter wässriger Natriumchloridlösung (150 mL) gewaschen. Die organische Phase wurde über Natriumsulfat getrockent und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieslegel lieferte die Titel Verbindung (7,00 g, 23,2 mmol, 86% d. Th.). A solution of sodium hydrogen carbonate (2.88 g, 34.3 mmol) in water (12 mL) was added. A solution of bromine (1.73 mL, 33.8 mmol) in dichloromethane (20.0 mL) was added dropwise while cooling with an ice bath. After the addition had ended, the reaction mixture was stirred at RT overnight. The solution was then diluted with dichloromethane (200 ml) and washed successively with saturated aqueous sodium hydrogen carbonate solution (150 ml), saturated aqueous sodium thiosulfate solution (150 ml) and saturated aqueous sodium chloride solution (150 ml). The organic phase was dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (7.00 g, 23.2 mmol, 86% of theory).
Intermediat 7A tert-Butyl-2-cyclopropyl-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-carboxylat Intermediate 7A tert -Butyl-2-cyclopropyl-5- (ethylsulfanyl) -l-methyl-1H-imidazole-4-carboxylate
Eine Lösung von tert-Butyl-5-brom-2-cyclopropyl-l-methyl-lH-imidazol-4-carboxylat (13,0 g, 43,0 mmol) in THF (200 mL) wurde bei -80 °C tropfenweise mit n-Butyllithium (2,5 M Lösung in Hexanfraktion, 23,0 mL, 57,5 mmol) versetzt. Nach beendeter Zugabe wurde noch 1 h lang bei -80 °C gerührt, bevor Diethyldisulfid (30,0 g, 250 mmol) tropfenweise zugegeben wurde. Nach beendeter Zugabe wurde die Mischung über Nacht bei 50 °C gerührt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit gesättigter wässriger Ammoniumchloridlösung (200 mL) versetzt und mit Essigsäureethylester (3 x 300 mL) extrahiert. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, über Natriumsulfat getrocknet und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieslegel lieferte die Titelverbindung (7,20 g, 25,5 mmol, 78% d. Th.). Intermediat 8A tert-Butyl-2-cyclopropyl-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-carboxylat meta-Chlorperbenzoesäure (13,5 g, 78,0 mmol) wurde bei 0 °C zu einer Lösung von tert-Butyl-2- cyclopropyl-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-carboxylat (7,20 g, 25,5 mmol) in Dichlormethan (100 mL) hinzugegeben und die Mischung wurde anschließend 24 h lang bei RT gerührt. Anschließend wurde die Reaktionsmischung auf 0 °C gekühlt und mit gesättigter wässriger Natriumhydrogencarbonatlösung (150 mL) und gesättigter wässriger Natriumthiosulfatlösung (150 mL) versetzt und anschließend filtriert. Die Phasen wurden getrennt und die organische Phase wurde über Natrium sulfat getrocknet und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieslegel lieferte die Titel Verbindung (7,80 g, 24,8 mmol, 90% d. Th.). A solution of tert-butyl 5-bromo-2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate (13.0 g, 43.0 mmol) in THF (200 mL) was added dropwise at -80 ° C combined with n-butyllithium (2.5 M solution in hexane fraction, 23.0 mL, 57.5 mmol). After the addition had ended, the mixture was stirred for a further 1 hour at -80 ° C. before diethyl disulfide (30.0 g, 250 mmol) was added dropwise. After the addition had ended, the mixture was stirred at 50 ° C. overnight. After cooling to RT, the reaction mixture was combined with saturated aqueous ammonium chloride solution (200 ml) and extracted with ethyl acetate (3 × 300 ml). The combined organic phases were washed with water, dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (7.20 g, 25.5 mmol, 78% of theory). Intermediate 8A tert -Butyl-2-cyclopropyl-5- (ethylsulfonyl) -l-methyl-1H-imidazole-4-carboxylate meta-chloroperbenzoic acid (13.5 g, 78.0 mmol) was added at 0 ° C to a solution of tert-butyl-2-cyclopropyl-5- (ethylsulfanyl) -l-methyl-1H-imidazole-4-carboxylate (7 , 20 g, 25.5 mmol) in dichloromethane (100 mL) were added and the mixture was then stirred for 24 h at RT. The reaction mixture was then cooled to 0 ° C., saturated aqueous sodium hydrogen carbonate solution (150 ml) and saturated aqueous sodium thiosulfate solution (150 ml) were added and then filtered. The phases were separated and the organic phase was dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (7.80 g, 24.8 mmol, 90% of theory).
Intermediat 9A Intermediate 9A
2-Cyclopropyl-5-(ethylsulfonyl)- 1 -methyl- lH-imidazol-4-carbonsäure Trifluoressigsäure (10 mL) wurde bei 0 °C zu einer Lösung von tert-Butyl-2-cyclopropyl-5- (ethylsulfonyl)-l -methyl- lH-imidazol-4-carboxylat (7,80 g, 24,8 mmol) in Dichlormethan (100 mL) hinzugetropft. Nach beendeter Zugabe wurde die Mischung 4 Tage lang bei RT gerührt. Anschließend wurde die Mischung eingeengt und der Rückstand in einer Mischung aus MTBE und Hexan (1:1) verrührt. Der Feststoff wurde abfiltriert. Umkristallisation des so gewonnen Rohprodukts aus Diethylether lieferte die Titelverbindung (6,00 g, 23,2 mmol, 93% d. Th.). 2-Cyclopropyl-5- (ethylsulfonyl) -1-methyl-1H-imidazole-4-carboxylic acid Trifluoroacetic acid (10 mL) was added at 0 ° C to a solution of tert-butyl-2-cyclopropyl-5- (ethylsulfonyl) -1-methyl-1H-imidazole-4-carboxylate (7.80 g, 24.8 mmol) added dropwise in dichloromethane (100 mL). After the addition had ended, the mixture was stirred at RT for 4 days. The mixture was then concentrated and the residue was stirred in a mixture of MTBE and hexane (1: 1). The solid was filtered off. Recrystallization of the crude product obtained in this way from diethyl ether yielded the title compound (6.00 g, 23.2 mmol, 93% of theory).
Intermediat 10A Intermediate 10A
N-(7-Amino-2,2,3,3-tetrafluor-2,3-dihydro-l,4-benzodioxin-6-yl)-2-cyclopropyl-5-(ethylsulfonyl)-l- methyl- 1 H-imidazol-4-carboxamid 2-Cyclopropyl-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-carbonsäure (163 mg, 0,63 mmol) wurde in DMF vorgelegt und mit HATU (287,1 mg, 0,76 mmol) und DIPEA (274 pmol, 1,58 mmol) versetzt. Die Mischung wurde 30 min lang bei RT gerührt und dann auf -10 °C abgekühlt. Bei dieser Temperatur wurde eine Lösung von 2,2,3,3-Tetrafluor-2,3-dihydro-l,4-benzodioxin-6,7-diamin (150 mg, 0,63 mmol) in DMF langsam hinzugetropft. Nach beendeter Zugabe wurde noch 1 h lang bei -10 °C gerührt. Dann wurden erneut HATU (287,1 mg, 0,76 mmol) und DIPEA (274 pmol, 1,58 mmol) hinzugegeben und es wurde 1 h lang bei RT gerührt. Die Reaktionsmischung wurde mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden zweimal mit 1,0 M Salzsäure und einmal mit gesättigter wässriger Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und eingeengt. Aufreinigen des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (163 mg, 54% d. Th.).N- (7-Amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl) -2-cyclopropyl-5- (ethylsulfonyl) -l-methyl-1H -imidazole-4-carboxamide 2-Cyclopropyl-5- (ethylsulfonyl) -l-methyl-lH-imidazole-4-carboxylic acid (163 mg, 0.63 mmol) was placed in DMF and treated with HATU (287.1 mg, 0.76 mmol) and DIPEA (274 pmol, 1.58 mmol) were added. The mixture was stirred for 30 min at RT and then cooled to -10 ° C. At this temperature, a solution of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6,7-diamine (150 mg, 0.63 mmol) in DMF was slowly added dropwise. After the addition had ended, the mixture was stirred at -10 ° C. for a further 1 hour. Then again HATU (287.1 mg, 0.76 mmol) and DIPEA (274 pmol, 1.58 mmol) were added and the mixture was stirred at RT for 1 h. The reaction mixture was mixed with water and extracted with dichloromethane. The combined organic phases were washed twice with 1.0 M hydrochloric acid and once with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (163 mg, 54% of theory).
ESI Masse [m/z]: 479,4 [M+H]+ ESI mass [m / z]: 479.4 [M + H] +
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 9.65 (s, 1H), 7.38 (s, 1H), 6.71 (s, 1H), 5.26 (s, 2H), 3.91 (s, 3H), 3.61 (q, 2H), 2.21-2.10 (m, 1H), 1.21 (t, 3H), 1.08-0.99 (m, 4H). Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 9.65 (s, 1H), 7.38 (s, 1H), 6.71 (s, 1H), 5.26 (s, 2H), 3.91 (s, 3H), 3.61 (q, 2H), 2.21-2.10 (m, 1H), 1.21 (t, 3H), 1.08-0.99 (m, 4H).
Intermediat 11A Intermediate 11A
2- [4-( 1 -Fluorcyclopropyl)phenyl] -4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan 2- [4- (1 -fluorocyclopropyl) phenyl] -4,4,5,5, 5-tetramethyl-1,3,2-dioxaborolane
Eine Mischung aus l-Brom-4-(l-fluorcyclopropyl)benzol (200 mg, 930 pmol), 4, 4, 4', 4', 5, 5, 5', 5'- Octamethyl-2,2'-bi-l,3,2-dioxaborolan (283 mg, 1116 pmol), Pd(dppf)Cl2*CH2Cl2, (34,0 mg, 46 pmol) und Kaliumacetat (274 mg, 2,79 mmol) in Acetonitril (8,0 mL) wurde in einem Mikrowellenreaktor 15 min lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung eingeengt. Wiederholte säulenchromatographische Aufreinigung des Rückstands zunächst an Kiesegel, dann mittels präparativer HPLC lieferte die Titel verbidnung (79,4 mg, 93% Reinheit, 30% d. Th.). A mixture of l-bromo-4- (l-fluorocyclopropyl) benzene (200 mg, 930 pmol), 4, 4, 4 ', 4', 5, 5, 5 ', 5'-octamethyl-2,2'- bi-l, 3,2-dioxaborolane (283 mg, 1116 pmol), Pd (dppf) Cl2 * CH2Cl2, (34.0 mg, 46 pmol) and potassium acetate (274 mg, 2.79 mmol) in acetonitrile (8, 0 mL) was heated to 150 ° C for 15 minutes in a microwave reactor. After cooling to RT, the reaction mixture was concentrated. Repeated purification of the residue by column chromatography, first on silica gel, then by means of preparative HPLC provided the title compound (79.4 mg, 93% purity, 30% of theory).
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 7.68 (d, 2H), 7.26 (d, 2H), 1.57-1.42 (m, 2H), 1.29 (s, 12H), 1.25-1.13 (m, 2H). Intermediat 12A Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.68 (d, 2H), 7.26 (d, 2H), 1.57-1.42 (m, 2H), 1.29 (s, 12H), 1.25- 1.13 (m, 2H). Intermediate 12A
4,4,5,5-Tetramethyl-2-{3-[l-(trifluormethyl)cyclopropyl]phenyl}-l,3,2-dioxaborolan 4,4,5,5-tetramethyl-2- {3- [1- (trifluoromethyl) cyclopropyl] phenyl} -1,3,2-dioxaborolane
Eine Mischung aus l-Brom-3-[l-(trifluormethyl)cyclopropyl]benzol (200 mg, 755 pmol), pmol) und Kaliumacetat (222 mg, 2,26 mmol) in Acetonitril (8,0 mL) wurde in einem Mikrowellenreaktor 15 min lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über Celite filtriert, mit Acetonitril nachgewaschen und das Filtrat wurde eingeengt. Wiederholte säulenchromatographische Aufreinigung des Rückstands zunächst an Kieselgel, dann mittels präparativer HPLC lieferte die Titelverbindung (152 mg, 77% Reinheit, 50% d. Th.). A mixture of l-bromo-3- [l- (trifluoromethyl) cyclopropyl] benzene (200 mg, 755 pmol), pmol) and potassium acetate (222 mg, 2.26 mmol) in acetonitrile (8.0 mL) was heated to 150 ° C for 15 min in a microwave reactor. After cooling to RT, the reaction mixture was filtered through Celite, washed with acetonitrile and the filtrate was concentrated. Repeated purification of the residue by column chromatography, first on silica gel, then by means of preparative HPLC yielded the title compound (152 mg, 77% purity, 50% of theory).
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 7.74 (s, 1H), 7.68-7.64 (m, 1H), 7.61-7.57 (m, 1H), 7.45-7.39 (m, 1H), 1.36-1.32 (m, 2H), 1.30 (s, 12H), 1.15-1.09 (m, 2H). Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.74 (s, 1H), 7.68-7.64 (m, 1H), 7.61-7.57 (m, 1H), 7.45-7.39 (m, 1H ), 1.36-1.32 (m, 2H), 1.30 (s, 12H), 1.15-1.09 (m, 2H).
Intermediat 13A Intermediate 13A
2-[3-(l-Fluorcyclopropyl)phenyl]-4,4,5,5-tetramethyl-l,3,2-dioxaborolan 2- [3- (1-Fluorocyclopropyl) phenyl] -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Eine Mischung aus l-Brom-3-(l-fluorcyclopropyl)benzol (200 mg, 930 pmol), 4, 4, 4', 4', 5, 5,5', 5'- Octamethyl-2,2'-bi-l,3,2-dioxaborolan (283 mg, 1116 pmol), Pd(dppf)Cl2 (31,0 mg, 42 pmol) und Kaliumacetat (274 mg, 2,79 mmol) in Acetonitril (8,0 mL) wurde in einem Mikrowellenreaktor 15 min lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über Celite filtriert, mit Acetonitril nachgewaschen und das Filtrat wurde eingeengt. Wiederholte säulenchromatographische Aufreinigung des Rückstands zunächst an Kieselgel, dann mittels präparativer HPLC lieferte die Titel Verbindung (50,4 mg, 72% Reinheit, 15% d. Th.). A mixture of l-bromo-3- (l-fluorocyclopropyl) benzene (200 mg, 930 pmol), 4, 4, 4 ', 4', 5, 5.5 ', 5'-octamethyl-2,2'- bi-l, 3,2-dioxaborolane (283 mg, 1116 pmol), Pd (dppf) Cl2 (31.0 mg, 42 pmol) and potassium acetate (274 mg, 2.79 mmol) in acetonitrile (8.0 mL) was heated to 150 ° C for 15 minutes in a microwave reactor. After cooling to RT, the reaction mixture was filtered through Celite, washed with acetonitrile and the filtrate was concentrated. Repeated purification of the residue by column chromatography, first on silica gel, then by means of preparative HPLC yielded the title compound (50.4 mg, 72% purity, 15% of theory).
ESI Masse [m/z]: 263,2 [M+H]+ ESI mass [m / z]: 263.2 [M + H] +
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 7.64-7.57 (m, 2H), 7.44-7.35 (m, 2H), 1.53-1.38 (m, 2H), 1.34-1.27 (m, 12H), 1.18-1.11 (m, 2H). Intermediat 14A Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.64-7.57 (m, 2H), 7.44-7.35 (m, 2H), 1.53-1.38 (m, 2H), 1.34-1.27 (m , 12H), 1.18-1.11 (m, 2H). Intermediate 14A
6, 6, 7, 7-Tetrafluor-6,7-dihydro-lH-[l,4]dioxino[2,3-f] benzimidazol 6, 6, 7, 7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus 2,2,3,3-Tetrafluor-2,3-dihydro-l,4-benzodioxin-6,7-diamin (1 00 g, 4,19 mmol) und Ameisensäure (5,0 mL) wurde im Mikrowellenreaktor 30 min lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieselgel lieferte die Titelverbindung (588 mg, 56% d. Th.). A mixture of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6,7-diamine (100 g, 4.19 mmol) and formic acid (5.0 mL) was im Microwave reactor heated to 150 ° C for 30 minutes. After cooling to RT, the reaction mixture was concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (588 mg, 56% of theory).
ESI Masse [m/z]: 249,1 [M+H]+ ESI mass [m / z]: 249.1 [M + H] +
'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 12.77 (br s, 1H), 8.36 (s, 1H), 7.70 (br s, 2H). Intermediat 15A 'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 12.77 (br s, 1H), 8.36 (s, 1H), 7.70 (br s, 2H). Intermediate 15A
6 ,6 ,7 ,7-T etr afluor- 1 -methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 6, 6, 7, 7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
6,6,7,7-Tetrafluor-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (644 mg, 2.59 mmol) wurde auf vier Reaktionsgefäße verteilt (jeweils 161 mg, 0,65 mmol). Jedes der Gefäße wurde mit Iodmethan (101 pL, 1,62 mmol), Kaliumcarbonat (314 mg, 2,27 mmol) und Aceton (1,5 mL) versetzt. Die Gefäße wurden verschlossen und 3 h lang auf 60 °C erhitzt. Nach dem Abkühlen auf RT wurden die vier Reaktionsmischungen vereinigt und zwischen 1.0 M Salzsäure und dichlormethan partitioniert. Die wässrige Phase wurde mit 1.0 M wässriger Natriumhydroxidlösung neutralisiert und erschöpfend mit Essigsäureethyletser extrahiert. Alle organischen Phasen wurden vereinigt, mit gesättigter wässriger Natriumchlorlösung gewaschen, über Natriumsulfat getrocknet und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieselgel lieferte die Titelverbindung (345 mg, 51% d. Th.). 6,6,7,7-Tetrafluoro-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (644 mg, 2.59 mmol) was divided into four reaction vessels (161 mg each, 0 , 65 mmol). Iodomethane (101 pL, 1.62 mmol), potassium carbonate (314 mg, 2.27 mmol) and acetone (1.5 mL) were added to each of the vessels. The jars were sealed and heated to 60 ° C. for 3 hours. After cooling to RT, the four reaction mixtures were combined and partitioned between 1.0 M hydrochloric acid and dichloromethane. The aqueous phase was neutralized with 1.0 M aqueous sodium hydroxide solution and extracted exhaustively with ethyl acetate. All organic phases were combined, washed with saturated aqueous sodium chlorine solution, dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (345 mg, 51% of theory).
ESI Masse [m/z]: 263,3 [M+H] ESI mass [m / z]: 263.3 [M + H]
'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 8.34 (s, 1H), 7.81 (s, 1H), 7.77 (s, 1H), 3.84 (s, 3H). Ausführungsbeispiele 'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 8.34 (s, 1H), 7.81 (s, 1H), 7.77 (s, 1H), 3.84 (s, 3H). Working examples
Beispiel 1-1 Example 1-1
2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [1,4] dioxino [2 , 3 -f] benzimidazol 2- [2-Bromo-5- (ethylsulfanyl) -l-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus N-(7-Amino-2,2,3,3-tetrafluor-2,3-dihydro-l,4-benzodioxin-6-yl)-2-brom-5- (ethylsulfanyl)-l-methyl-lH-imidazol-4-carboxamid (1,02 g, 73% Reinheit, 1,53 mmol) und Toluol-4- sulfonsäure-Monohydrat (878 mg, 4,59 mmol) in Toluol (40 mL) wurde 2 h lang zum Sieden erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die organische Phase wurde bis zur neutralen Reaktion mit Wasser gewaschen, getrocknet und eingeengt. Der Rückstand wurde mittels präparativer HPLC aufgereinigt. Dabei fielen zwei Fraktionen der Titelverbindsung an. Fraktion 1: 207 mg (98% Reinheit, 28% d.Th.); Fraktion 2: 144 mg (88% Reinheit, 18% d. Th.). A mixture of N- (7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl) -2-bromo-5- (ethylsulfanyl) -l-methyl -1H-imidazole-4-carboxamide (1.02 g, 73% purity, 1.53 mmol) and toluene-4-sulfonic acid monohydrate (878 mg, 4.59 mmol) in toluene (40 mL) was added for 2 hours heated to boiling. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water until neutral, dried and concentrated. The residue was purified by means of preparative HPLC. This resulted in two fractions of the title connection. Fraction 1: 207 mg (98% purity, 28% of theory); Fraction 2: 144 mg (88% purity, 18% of theory).
ESI Masse [m/z]: 467,0 / 469,0 [M+H]+ 'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.70-7.48 (m, 2H), 3.72 (s, 3H), 3.03 (q, 2H), 1.11 (t, 3H). ESI mass [m / z]: 467.0 / 469.0 [M + H] + 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.70-7.48 (m, 2H), 3.72 (s, 3H), 3.03 (q, 2H), 1.11 (t, 3H).
Beispiel 1-2 Example 1-2
2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazol Zu einer Lösung von 2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7- dihydro-lH-[l,4]dioxino[2,3-f]benzimidazole (805 mg, 1,72 mmol) in Dichlormethan (5,0 mL) wurden nacheinander Ameisensäure (0,325 mL, 8,61 mmol) und Wasserstoffperoxid (35%ige wässrige Lösung, 1,04 mL, 12,0 mmol) bei RT hinzugegeben. Die Reaktionsmischung wurde über Nacht bei RT gerührt. Anschließend wurde die Mischung unter Eiskühlung mit Wasser und gesättigter wässriger Natriumbisulfitlösung versetzt und eine weitere Nacht bei RT gerührt. Die Mischung wurde mit Wasser (50 mL) und Dichlormethan (100 mL) verdünnt. Die Phasen wurden getrennt und die organische Phase wurde zunächst mit Wasser, dann mit gesättigter wässriger Natriumhydrogencarbonat-Lösung gewaschen, über Natriumsulfat getrocknet und eingeengt. Der Rückstand wurde mit Acetonitril (4,0 mL) versetzt und bei RT verrührt. Abfiltrieren und Trocknen des Festsoffs lieferte eine erste Menge der Zielverbidung (485 mg, 92% Reinheit, 41% d. Th.). Die Mutterlauge wurde eingeengt und der Rückstand säulenchromatographisch an Kieselgel aufgerenigt, wodurch weitere Titelverbindung (114 mg, 93% Reinheit, 12% d. Th.) isoliert werden konnte. 2- [2-Bromo-5- (ethylsulfonyl) -l-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole To a solution of 2- [2-bromo-5- (ethylsulfanyl) -l-methyl-lH-imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-lH- [l , 4] dioxino [2,3-f] benzimidazole (805 mg, 1.72 mmol) in dichloromethane (5.0 mL) were successively formic acid (0.325 mL, 8.61 mmol) and hydrogen peroxide (35% aqueous solution, 1.04 mL, 12.0 mmol) were added at RT. The reaction mixture was stirred at RT overnight. Then, while cooling with ice with water and saturated aqueous solution, the mixture became Sodium bisulfite solution is added and the mixture is stirred at RT for a further night. The mixture was diluted with water (50 mL) and dichloromethane (100 mL). The phases were separated and the organic phase was washed first with water and then with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated. Acetonitrile (4.0 mL) was added to the residue and the mixture was stirred at RT. Filtering off and drying the solids yielded a first amount of the target compound (485 mg, 92% purity, 41% of theory). The mother liquor was concentrated and the residue was concentrated by column chromatography on silica gel, whereby further title compound (114 mg, 93% purity, 12% of theory) could be isolated.
ESI Masse [m/z]: 498,9 / 500,9 [M+H]+ ESI mass [m / z]: 498.9 / 500.9 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 13.37 (s, 1H), 7.81 (br s, 1H), 7.53 (br s, 1H), 4.03 (q, 2H), 3.91 (s, 3H), 1.28 (t, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 13.37 (s, 1H), 7.81 (br s, 1H), 7.53 (br s, 1H), 4.03 (q, 2H), 3.91 (s, 3H), 1.28 (t, 3H).
Beispiel 1-3 Example 1-3
2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazol 2- [2-Bromo-5- (ethylsulfonyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1 H- [1 , 4] dioxino [2,3-f] benzimidazole
2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazol (495 mg, 0,99 mmol) wurde in Aceton vorgelegt und mit Kaliumcarbonat (480 mg, 3,47 mmol) und Iodmethan (154 pL, 2,47 mmol) versetzt. Die Mischung wurde 2 h lang zum Sieden erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung bis zur Trockne eingeengt. Der Rückstand wurde in Dichlormethan aufgenommen und mit 1 ,0 M Salzsäure gewaschen. Die organische Phase wurde mit gesättigter wässriger Natriumchlorid-Lösung gewaschen und über Natriumsulfat getrocknet. Einengen der erhaltenen Lösung bis zur Trockne lieferte die Titel verbidung (469 mg, 90% Reinheit, 83% d. Th.). 2- [2-Bromo-5- (ethylsulfonyl) -l-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (495 mg, 0.99 mmol) was initially charged in acetone, and potassium carbonate (480 mg, 3.47 mmol) and iodomethane (154 pL, 2.47 mmol) were added. The mixture was heated to boiling for 2 hours. After cooling to RT, the reaction mixture was concentrated to dryness. The residue was taken up in dichloromethane and washed with 1.0 M hydrochloric acid. The organic phase was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. Concentration of the resulting solution to dryness gave the title compound (469 mg, 90% purity, 83% of theory).
ESI Masse [m/z]: 513,0 / 515,0 [M+H]+ ESI mass [m / z]: 513.0 / 515.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 3.73 (q, 2H), 1.26 (t, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 3.73 (q , 2H), 1.26 (t, 3H).
Beispiel 1-4 Example 1-4
2-[2-(4-Chlorphenyl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (4-chlorophenyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7- dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (2,9 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (3,1 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (100 mg,A mixture of dioxane (2.9 mL) and 1.0 M aqueous sodium carbonate solution (3.1 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (100 mg,
195 pmol), (4-Chlorphenyl)boronsäure (30,5 mg, 195 pmol) und195 pmol), (4-chlorophenyl) boronic acid (30.5 mg, 195 pmol) and
Tetrakis(triphenylphosphin)palladium(0) (11,2 mg, 10 pmol) hinzugegeben und die Mischung wurde über Nacht auf 92 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung bis zur Trockne eingeengt und der Rückstand in Wasser und Dichlormethan aufgenommen. Die Phasen wurden getrennt und die organische Phase wurde zweimal mit Wasser gewaschen und anschließend über Natriumsulfat getrocknet und eingeengt. Aufreingung des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (49,3 mg, 88% Reinheit, 52% d. Th.). Tetrakis (triphenylphosphine) palladium (0) (11.2 mg, 10 pmol) was added and the mixture was heated to 92 ° C overnight. After cooling to RT, the reaction mixture was concentrated to dryness and the residue was taken up in water and dichloromethane. The phases were separated and the organic phase was washed twice with water and then dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (49.3 mg, 88% purity, 52% of theory).
ESI Masse [m/z]: 545,0 [M+H]+ ESI mass [m / z]: 545.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.87-7.79 (m, 3H), 7.67 (d, 2H), 3.95 (s, 3H), 3.84-3.76 (m, 5H), 1.31 (t, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.89 (s, 1H), 7.87-7.79 (m, 3H), 7.67 (d, 2H), 3.95 (s, 3H), 3.84 -3.76 (m, 5H), 1.31 (t, 3H).
Beispiel 1-5 Example 1-5
2-[5-(Ethylsulfonyl)-2-(4-fluorphenyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazole 2- [5- (Ethylsulfonyl) -2- (4-fluorophenyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazoles
Eine Mischung aus Dioxan (1,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (1,1 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (35,0 mg, 68 pmol), (4-Lluorphenyl)boronsäure (9,5 mg, 68 pmol) und Tetrakis(triphenylphosphin)palladium(0) (3,9 mg, 3 pmol) hinzugegeben und die Mischung wurde 4 h lang auf 92 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan verdünnt und die organische Phase mit gesättigter wässriger Ammoniumchloridlösung gewaschen, getrocknet und eingeengt. Der Rückstand wurde in Dioxan (1,0 mL) aufgenommen und mit 1,0 M wässriger Natriumcarbonat-Lösung (1,1 mL), (4- Fluorphenyl)boronsäure (9,5 mg, 68 pmol) und Tetrakis(triphenylphosphin)palladium(0) (3,9 mg, 3 pmol) versetzt und anschließend erneut 7 h lang auf 92 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung eingeengt. Aufreinugng des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (12,7 mg, 35% d. Th.). A mixture of dioxane (1.0 mL) and 1.0 M aqueous sodium carbonate solution (1.1 mL) was degassed for 30 minutes in a stream of argon. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazole (35.0 mg, 68 pmol), (4-fluorophenyl) boronic acid (9.5 mg, 68 pmol) and tetrakis (triphenylphosphine) palladium (0) (3 , 9 mg, 3 pmol) was added and the mixture was heated to 92 ° C. for 4 h. After cooling to RT, the reaction mixture was diluted with dichloromethane and the organic phase was washed with saturated aqueous ammonium chloride solution, dried and concentrated. The residue was taken up in dioxane (1.0 mL) and treated with 1.0 M aqueous sodium carbonate solution (1.1 mL), (4-fluorophenyl) boronic acid (9.5 mg, 68 pmol) and tetrakis (triphenylphosphine) palladium (0) (3.9 mg, 3 pmol) were added and the mixture was then heated again to 92 ° C. for 7 h. After cooling to RT, the reaction mixture was concentrated. Purification of the residue by means of preparative HPLC gave the title compound (12.7 mg, 35% of theory).
ESI Masse [m/z]: 529,0 [M+H]+ ESI mass [m / z]: 529.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.90-7.84 (m, 3H), 7.83 (s, 1H), 7.50-7.41 (m, 2H), 3.93 (s, 3H), 3.85-3.75 (m, 5H), 2.55-2.52 (m, 2H), 2.08 (s, 1H), 1.31 (t, 3H). 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.90-7.84 (m, 3H), 7.83 (s, 1H), 7.50-7.41 (m, 2H), 3.93 (s, 3H) , 3.85-3.75 (m, 5H), 2.55-2.52 (m, 2H), 2.08 (s, 1H), 1.31 (t, 3H).
Beispiel 1-6 l-{4-[5-(Ethylsulfonyl)-l-methyl-4-(6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3- f]benzimidazol-2-yl)- 1 H-imidazol-2-yl]phenyl } cyclopropancarbonitril Example 1-6 l- {4- [5- (Ethylsulfonyl) -l-methyl-4- (6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazol-2-yl) -1H-imidazol-2-yl] phenyl} cyclopropanecarbonitrile
Eine Mischung aus Dioxan (1,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (1,1 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (35,0 mg, 68 pmol), l-[4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]cyclopropancarbonitril (36,7 mg, 136 pmol) und Tetrakis(triphenylphosphin)palladium(0) (7,8 mg, 7 pmol) hinzugegeben und die Mischung wurde über Nacht auf 92 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die organische Phase wurde mit Wasser, 1.0 M Salzsäure und gesättigter wässriger Natriumchloridlösung gewaschen. Anschließend wurde die organische Phase getrocknet und eingeengt. Aufreinugng des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (48,7 mg, 85% Reinheit, 53% d. Th.). A mixture of dioxane (1.0 mL) and 1.0 M aqueous sodium carbonate solution (1.1 mL) was degassed for 30 minutes in a stream of argon. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (35.0 mg, 68 pmol), l- [4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-2- yl) phenyl] cyclopropanecarbonitrile (36.7 mg, 136 pmol) and tetrakis (triphenylphosphine) palladium (0) (7.8 mg, 7 pmol) were added and the mixture was heated to 92 ° C. overnight. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water, 1.0 M hydrochloric acid and saturated aqueous sodium chloride solution. The organic phase was then dried and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (48.7 mg, 85% purity, 53% of theory).
ESI Masse [m/z]: 576,3 [M+H] ESI mass [m / z]: 576.3 [M + H]
Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.88 (s, 1H), 7.86-7.81 (m, 3H), 7.54 (d, 2H), 3.94 (s, 3H), 3.84-3.77 (m, 5H), 1.89-1.82 (m, 2H), 1.67-1.60 (m, 2H), 1.31 (t, 3H). Beispiel 1-7 Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.88 (s, 1H), 7.86-7.81 (m, 3H), 7.54 (d, 2H), 3.94 (s, 3H), 3.84-3.77 (m, 5H), 1.89-1.82 (m, 2H), 1.67-1.60 (m, 2H), 1.31 (t, 3H). Example 1-7
2-[5-(Ethylsulfonyl)-l-methyl-2-{4-[l-(trifluormethyl)cyclopropyl]phenyl}-lH-imidazol-4-yl]-6,6,7,7- tetrafluor- 1 -methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [5- (Ethylsulfonyl) -l-methyl-2- {4- [1- (trifluoromethyl) cyclopropyl] phenyl} -lH-imidazol-4-yl] -6,6,7,7-tetrafluoro- 1 - methyl-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (2,9 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (3,1 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (82,1 mg, 160 pmol), 4,4,5,5-Tetramethyl-2-{4-[l-(trifluormethyl)cyclopropyl]phenyl}-l,3,2-dioxaborolan (50,0 mg, 160 pmol) und Tetrakis(triphenylphosphin)palladium(0) (9,2 mg, 8 pmol) hinzugegeben und die Mischung wurde über Nacht auf 92 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die organische Phase wurde mit Wasser, 1.0 M Salzsäure und gesättigter wässriger Natriumchloridlösung gewaschen. Anschließend wurde die organische Phase getrocknet und eingeengt. Aufreinugng des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (65,0 mg, 66% d. Th.). A mixture of dioxane (2.9 mL) and 1.0 M aqueous sodium carbonate solution (3.1 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (82.1 mg, 160 pmol), 4,4,5,5-tetramethyl-2- {4- [l- (trifluoromethyl) cyclopropyl] phenyl} - 1,3,2-dioxaborolane (50.0 mg, 160 pmol) and tetrakis (triphenylphosphine) palladium (0) (9.2 mg, 8 pmol) were added and the mixture was heated to 92 ° C. overnight. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water, 1.0 M hydrochloric acid and saturated aqueous sodium chloride solution. The organic phase was then dried and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (65.0 mg, 66% of theory).
ESI Masse [m/z]: 619,1 [M+H]+ ESI mass [m / z]: 619.1 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.86-7.81 (m, 3H), 7.68 (d, 2H), 3.95 (s, 3H), 3.89-3.75 (m, 5H), 1.45-1.37 (m, 2H), 1.31 (t, 3H), 1.26-1.19 (m, 2H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.89 (s, 1H), 7.86-7.81 (m, 3H), 7.68 (d, 2H), 3.95 (s, 3H), 3.89 -3.75 (m, 5H), 1.45-1.37 (m, 2H), 1.31 (t, 3H), 1.26-1.19 (m, 2H).
Beispiel 1-8 Example 1-8
2-[2-Cyclopropyl-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazol 2- [2-Cyclopropyl-5- (ethylsulfonyl) -l-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus N-(7-Amino-2,2,3,3-tetrafluor-2,3-dihydro-l,4-benzodioxin-6-yl)-2-cyclopropyl-5- (ethylsulfonyl)-l-methyl-lH-imidazol-4-carboxamid (163 mg, 341 pmol) und Toluol-4-sulfonsäure- Monohydrat (195 mg, 1022 pmol) in Toluol (3,4 mL) wurde 6 h lang zum Sieden erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die organische Phase wurde bis zur neutralen Reaktion mit Wasser gewaschen, getrocknet und eingeengt um die Titel Verbindung (149 mg, 93% Reinheit, 88% d. Th.) zu erhalten.A mixture of N- (7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl) -2-cyclopropyl-5- (ethylsulfonyl) -l-methyl -lH-imidazole-4-carboxamide (163 mg, 341 pmol) and toluene-4-sulfonic acid monohydrate (195 mg, 1022 pmol) in toluene (3.4 ml) was heated to the boil for 6 h. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water until the reaction was neutral, dried and concentrated in order to obtain the title compound (149 mg, 93% purity, 88% of theory).
ESI Masse [m/z]: 461,3 [M+H]+ ESI mass [m / z]: 461.3 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 12.98 (s, 1H), 7.76 (s, 1H), 7.52 (s, 1H), 3.96 (s, 3H), 3.96- 3.92 (m, 2H), 2.25-2.13 (m, 1H), 1.25 (t, 3H), 1.11-1.01 (m, 4H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 12.98 (s, 1H), 7.76 (s, 1H), 7.52 (s, 1H), 3.96 (s, 3H), 3.96-3.92 (m, 2H), 2.25-2.13 (m, 1H), 1.25 (t, 3H), 1.11-1.01 (m, 4H).
Beispiel 1-9 Example 1-9
2-[2-Cyclopropyl-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2-Cyclopropyl-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1 H- [ 1, 4] dioxino [2,3-f] benzimidazole
2-[2-Cyclopropyl-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (135 mg, 293 pmol) wurde in Aceton (2,0 mL) vorgelegt und mit Kaliumcarbonat (142 mg, 1026 pmol) und Iodmethan (46 pL, 733 pmol) versetzt. Die Mischung wurde 3 h lang zum Sieden erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung eingeengt und der Rückstand zwischen Dichlormethan und 1 ,0 M Salzsäure partitioniert. Die organische Phase wurde mit Wasser gewaschen, getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (74,0 mg, 93% Reinheit, 49% d. Th.). 2- [2-Cyclopropyl-5- (ethylsulfonyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (135 mg, 293 pmol) was placed in acetone (2.0 ml) and potassium carbonate (142 mg, 1026 pmol) and iodomethane (46 pL, 733 pmol) were added. The mixture was heated to boiling for 3 hours. After cooling to RT, the reaction mixture was concentrated and the residue was partitioned between dichloromethane and 1.0 M hydrochloric acid. The organic phase was washed with water, dried and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (74.0 mg, 93% purity, 49% of theory).
ESI Masse [m/z]: 475,4 [M+H]+ ESI mass [m / z]: 475.4 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.84 (s, 1H), 7.78 (s, 1H), 3.96 (s, 3H), 3.73 (s, 3H), 3.67 (q, 2H), 2.25-2.17 (m, 1H), 1.24 (t, 3H), 1.12-0.97 (m, 4H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.84 (s, 1H), 7.78 (s, 1H), 3.96 (s, 3H), 3.73 (s, 3H), 3.67 (q , 2H), 2.25-2.17 (m, 1H), 1.24 (t, 3H), 1.12-0.97 (m, 4H).
Beispiel 1-10 Example 1-10
2-[2-(4-Bromphenyl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol In einem Mikrowellengefäß wurden 2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6, 6,7,7- tetrafluor-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (40,0 mg, 0,078 mmol) und 4- Bromphenylboronsäure (31,3 mg, 0,156 mmol) in Dioxan (3,0 mL) vorgelegt und mit 2,0 M wässriger Natriumcarbonatlösung (195 pL, 0,390 mmol) und Dichlorbis-(tricyclohexylphosphin)-Palladium(II) (5,8 mg, 8,0 pmol) versetzt. Die Mischung wurde 5 min lang im Argonstrom entgast bevor das Gefäß verschlossen und 12 min lang im Mirkowellenreaktor auf 120 °C erhitzt wurde. Nach dem Abkühlen wurde Tetrakis(triphenylphosphin)palladium(0) (9,0 mg, 8,0 pmol) hinzugegeben und erneut 24 min lang auf 120 °C erhitzt. Nach dem Abkühlen wurde erneut Tetrakis(triphenylphosphin)palladium(0) (9,0 mg, 8,0 pmol) hinzugegeben und nochmals 1 h lang auf 120 °C erhitzt. Die erkaltete Reaktionsmischung wurde mit Wasser und Dichlormethan versetzt, die Phasen wurden getrennt und die organische Phase wurde zweimal mit Wasser gewaschen und anschließend über Natriumsulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (9,1 mg, 20% d. Th.). 2- [2- (4-bromophenyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole 2- [2-Bromo-5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1H- [l , 4] dioxino [2,3-f] benzimidazole (40.0 mg, 0.078 mmol) and 4-bromophenylboronic acid (31.3 mg, 0.156 mmol) in dioxane (3.0 mL) and diluted with 2.0 M aqueous Sodium carbonate solution (195 pL, 0.390 mmol) and dichlorobis (tricyclohexylphosphine) palladium (II) (5.8 mg, 8.0 pmol) were added. The mixture was degassed for 5 minutes in a stream of argon before the vessel was closed and heated to 120 ° C. for 12 minutes in the microwave reactor. After cooling, tetrakis (triphenylphosphine) palladium (0) (9.0 mg, 8.0 pmol) was added and again heated to 120 ° C for 24 min. After cooling, tetrakis (triphenylphosphine) palladium (0) (9.0 mg, 8.0 pmol) was added again and the mixture was again heated to 120 ° C. for 1 h. The cooled reaction mixture was admixed with water and dichloromethane, the phases were separated and the organic phase was washed twice with water and then dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (9.1 mg, 20% of theory).
ESI Masse [m/z]: 589,1 / 591,1 [M+H]+ ESI mass [m / z]: 589.1 / 591.1 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.83-7.75 (m, 4H), 3.94 (s, 3H), 3.82 (s, 3H), 3.79 (q, 2H), 1.31 (t, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.83-7.75 (m, 4H), 3.94 (s, 3H), 3.82 (s, 3H), 3.79 (q, 2H), 1.31 (t, 3H).
Beispiel 1-11 Example 1-11
2-{5-(Ethylsulfonyl)-2-[4-(l-fluorcyclopropyl)phenyl]-l-methyl-lH-imidazol-4-yl}-6,6,7,7-tetrafluor-l- methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- {5- (Ethylsulfonyl) -2- [4- (1-fluorocyclopropyl) phenyl] -1-methyl-1 H -imidazol-4-yl} -6,6,7,7-tetrafluoro-1-methyl-6 , 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (45,0 mg, 88,0 m mol), 2-[4-(l-Fluorcyclopropyl)phenyl]-4, 4,5,5- tetramethyl-l,3,2-dioxaborolan (46,0 mg, 175 pmol) und Tetrakis(triphenylphosphin)palladium(0) (20,3 mg, 18,0 pmol) wurden in einem Mirko wellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (30,0 mg, 60% d. Th.). ESI Masse [m/z]: 569,0 [M+H] 2- [2-Bromo-5- (ethylsulfanyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 mol), 2- [4- (l-fluorocyclopropyl) phenyl] -4, 4,5,5-tetramethyl-1,3,2- dioxaborolane (46.0 mg, 175 pmol) and tetrakis (triphenylphosphine) palladium (0) (20.3 mg, 18.0 pmol) were placed in a micro wave vessel and in a degassed mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol) was added. The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (30.0 mg, 60% of theory). ESI mass [m / z]: 569.0 [M + H]
'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.89 (s, 1H), 7.85-7.81 (m, 3H), 7.47 (d, 2H), 3.96 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 1.62-1.49 (m, 2H), 1.36-1.24 (m, 5H). 'H-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.89 (s, 1H), 7.85-7.81 (m, 3H), 7.47 (d, 2H), 3.96 (s, 3H), 3.83 ( s, 3H), 3.80 (q, 2H), 1.62-1.49 (m, 2H), 1.36-1.24 (m, 5H).
Beispiel 1-12 2-[2-(3-Bromphenyl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol Example 1-12 2- [2- (3-bromophenyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (45,0 mg, 88,0 pmol), 4-Bromphenylboronsäure (35,2 mg, 156 pmol) und Tetrakis(triphenylphosphin)palladium(0) (20,3 mg, 18,0 pmol) wurden in einem Mirkowellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natrium sulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (9,3 mg, 18% d. Th.). 2- [2-Bromo-5- (ethylsulfanyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 pmol), 4-bromophenylboronic acid (35.2 mg, 156 pmol) and tetrakis (triphenylphosphine) palladium (0) (20.3 mg, 18.0 pmol) were placed in a microwave vessel and taken up in a degassed mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol). The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (9.3 mg, 18% of theory).
ESI Masse [m/z]: 589,0 / 591,0 [M+H]+ ESI mass [m / z]: 589.0 / 591.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.03-8.01 (m, 1H), 7.89 (s, 1H), 7.84-7.80 (m, 3H), 7.61-7.54 (m, 1H), 3.95 (s, 3H), 3.84-3.76 (m, 5H), 1.31 (t, 3H). Beispiel 1-13 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 8.03-8.01 (m, 1H), 7.89 (s, 1H), 7.84-7.80 (m, 3H), 7.61-7.54 (m, 1H), 3.95 (s, 3H), 3.84-3.76 (m, 5H), 1.31 (t, 3H). Example 1-13
2-[2-(3-Chlorphenyl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (45,0 mg, 88,0 pmol), 3-Chlorphenylboronsäure (27,4 mg, 175 mmol) und Tetrakis(triphenylphosphin)palladium(0) (20,3 mg, 18,0 pmol) wurden in einem Mirkowellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natrium sulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (26,2 mg, 99% Reinheit, 54% d. Th.). ESI Masse [m/z] : 545 ,0 [M+H] + 2- [2- (3-chlorophenyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole 2- [2-Bromo-5- (ethylsulfanyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 pmol), 3-chlorophenylboronic acid (27.4 mg, 175 mmol) and tetrakis (triphenylphosphine) palladium (0) (20.3 mg, 18.0 pmol) were placed in a microwave vessel and taken up in a degassed mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol). The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (26.2 mg, 99% purity, 54% of theory). ESI mass [m / z]: 545.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.90-7.88 (m, 2H), 7.83 (s, 1H), 7.80-7.77 (m, 1H), 7.70-7.60 (m, 2H), 3.95 (s, 3H), 3.83 (s, 3H), 3.79 (q, 2H), 1.31 (t, 3H). 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.90-7.88 (m, 2H), 7.83 (s, 1H), 7.80-7.77 (m, 1H), 7.70-7.60 (m, 2H), 3.95 (s, 3H), 3.83 (s, 3H), 3.79 (q, 2H), 1.31 (t, 3H).
Beispiel 1-14 Example 1-14
2-[5-(Ethylsulfonyl)-2-(3-fluorphenyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [5- (Ethylsulfonyl) -2- (3-fluorophenyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (45,0 mg, 88,0 pmol), 3-Fluorphenylboronsäure (24,5 mg, 175 pmol) und Tetrakis(triphenylphosphin)palladium(0) (20,3 mg, 18,0 pmol) wurden in einem Mirkowellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (22,5 mg, 49% d. Th.). 2- [2-Bromo-5- (ethylsulfanyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 pmol), 3-fluorophenylboronic acid (24.5 mg, 175 pmol) and tetrakis (triphenylphosphine) palladium (0) (20.3 mg, 18.0 pmol) were placed in a microwave vessel and taken up in a degassed mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol). The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (22.5 mg, 49% of theory).
ESI Masse [m/z]: 529,2 [M+H]+ ESI mass [m / z]: 529.2 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.71-7.62 (m, 3H), 7.49-7.43 (m, 1H), 3.96 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 1.31 (t, 3H). Beispiel 1-15 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.71-7.62 (m, 3H), 7.49-7.43 (m, 1H) , 3.96 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 1.31 (t, 3H). Example 1-15
2- { 5-(Ethylsulfonyl)- 1 -methyl-2-[4-(trifluormethyl)phenyl] - lH-imidazol-4-yl } -6,6,7,7-tetrafluor- 1 - methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH-2- {5- (Ethylsulfonyl) -1 -methyl-2- [4- (trifluoromethyl) phenyl] -1H -imidazol-4-yl} -6,6,7,7-tetrafluoro-1-methyl-6,7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole 2- [2-Bromo-5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1H-
[1,4] dioxino [2,3-f] benzimidazol (45,0 mg, 88,0 pmol), [4-(Trifluormethyl)phenyl]boronsäure (33,3 mg, 175 pmol) und Tetrakis(triphenylphosphin)palladium(0) (20,3 mg, 18,0 pmol) wurden in einem Mirkowellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natrium sulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (33,0 mg, 98% Reinheit, 64% d. Th.). [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 pmol), [4- (trifluoromethyl) phenyl] boronic acid (33.3 mg, 175 pmol) and tetrakis (triphenylphosphine) palladium (0) (20.3 mg, 18.0 pmol) were placed in a microwave flask and taken up in a degassed mixture of dioxane (3.0 ml) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol). The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (33.0 mg, 98% purity, 64% of theory).
ESI Masse [m/z]: 579,0 [M+H]+ 'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.06 (d, 2H), 7.97 (d, 2H), 7.89 (s, 1H), 7.84 (s, 1H), 3.98 (s, 3H), 3.84 (s, 3H), 3.81 (q, 2H), 1.36-1.28 (m, 3H). ESI mass [m / z]: 579.0 [M + H] + 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 8.06 (d, 2H), 7.97 (d, 2H), 7.89 (s, 1H), 7.84 (s, 1H), 3.98 (s, 3H), 3.84 (s, 3H), 3.81 (q, 2H), 1.36-1.28 (m, 3H).
Beispiel 1-16 Example 1-16
2-[5-(Ethylsulfonyl)-l-methyl-2-phenyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazol 2- [5- (Ethylsulfonyl) -1-methyl-2-phenyl-1 H -imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1 H- [1 , 4] dioxino [2,3-f] benzimidazole
2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-6,7-dihydro-lH- [l,4]dioxino[2,3-f]benzimidazol (45,0 mg, 88,0 pmol), Phenylboronsäure (21,4 mg, 175 pmol) und Tetrakis(triphenylphosphin)palladium(0) (20,2 mg, 18,0 pmol) wurden in einem Mirkowellengefäß vorgelegt und in einer entgasten Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonatlösung (438 pL, 438 pmol) aufgenommen. Die Reaktionsmischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser versetzt und mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (30,0 mg, 99% Reinheit, 66% d. Th.). 2- [2-Bromo-5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (45.0 mg, 88.0 pmol), phenylboronic acid (21.4 mg, 175 pmol) and tetrakis (triphenylphosphine) palladium (0) (20.2 mg , 18.0 pmol) were placed in a microwave vessel and taken up in a degassed mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (438 pL, 438 pmol). The reaction mixture was heated to 120 ° C. in a microwave reactor for 30 minutes. After cooling to RT, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (30.0 mg, 99% purity, 66% of theory).
ESI Masse [m/z]: 511,3 [M+H]+ 'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.83-7.79 (m, 2H), 7.63-7.58 (m, 3H), 3.95 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 1.35-1.29 (m, 3H). ESI mass [m / z]: 511.3 [M + H] + 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.83-7.79 (m, 2H), 7.63-7.58 (m, 3H), 3.95 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 1.35-1.29 (m, 3H).
Beispiel 1-17 Example 1-17
2-[5-(Ethylsulfonyl)-l-methyl-2-{3-[l-(trifluormethyl)cyclopropyl]phenyl}-lH-imidazol-4-yl]-6,6,7,7- tetrafluor- 1 -methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [5- (Ethylsulfonyl) -l-methyl-2- {3- [1- (trifluoromethyl) cyclopropyl] phenyl} -lH-imidazol-4-yl] -6,6,7,7-tetrafluoro- 1 - methyl-6,7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (0,4 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (41,0 mg, 80 mpioΐ), 4,4,5,5-Tetramethyl-2- { 3-[ 1 -(trifluormethyl)cyclopropyl]phenyl } - 1 ,3,2-dioxaborolan (64,8 mg, 160 pmol) und Tetrakis(triphenylphosphin)palladium(0) (18,5 mg, 16 pmol) hinzugegeben und dieA mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (0.4 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (41.0 mg, 80 mpioΐ), 4,4,5,5-tetramethyl-2- {3- [1 - (trifluoromethyl) cyclopropyl] phenyl} - 1, 3,2-dioxaborolane (64.8 mg, 160 pmol) and tetrakis (triphenylphosphine) palladium (0) (18.5 mg, 16 pmol) were added and the
Mischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (33,5 mg, 68% d. Th.). Mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (33.5 mg, 68% of theory).
ESI Masse [m/z]: 619,2 [M+H]+ ESI mass [m / z]: 619.2 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.90-7.87 (m, 2H), 7.84 (s, 1H), 7.81 (d, 1H), 7.69 (d, 1H), 7.65-7.60 (m, 1H), 3.94 (s, 3H), 3.82 (s, 3H), 3.78 (q, 2H), 1.42-1.38 (m, 2H), 1.31 (t, 3H), 1.25-1.21 (m, 2H). Beispiel 1-18 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 7.90-7.87 (m, 2H), 7.84 (s, 1H), 7.81 (d, 1H), 7.69 (d, 1H), 7.65 -7.60 (m, 1H), 3.94 (s, 3H), 3.82 (s, 3H), 3.78 (q, 2H), 1.42-1.38 (m, 2H), 1.31 (t, 3H), 1.25-1.21 (m , 2H). Example 1-18
2-[2-(6-Cyclopropylpyridin-3-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (6-Cyclopropylpyridin-3-yl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (0,4 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (41,0 mg, 80 pmol), 2-Cyclopropyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin (39,2 mg, 160 pmol) und Tetrakis(triphenylphosphin)palladium(0) (18,5 mg, 16 pmol) hinzugegeben und die Mischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (28,2 mg, 64% d. Th.). A mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (0.4 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazole (41.0 mg, 80 pmol), 2-cyclopropyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2 -yl) pyridine (39.2 mg, 160 pmol) and tetrakis (triphenylphosphine) palladium (0) (18.5 mg, 16 pmol) were added and the mixture was heated to 120 ° C for 30 minutes in a microwave reactor. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (28.2 mg, 64% of theory).
ESI Masse [m/z]: 552,3 [M+H]+ ESI mass [m / z]: 552.3 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.80 (d, 1H), 8.07 (dd, 1H), 7.89 (s, 1H), 7.83 (s, 1H), 7.52 (d, 1H), 3.95 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 2.26-2.20 (m, 1H), 1.31 (t, 3H), 1.08-1.00 (m, 4H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 8.80 (d, 1H), 8.07 (dd, 1H), 7.89 (s, 1H), 7.83 (s, 1H), 7.52 (d , 1H), 3.95 (s, 3H), 3.83 (s, 3H), 3.80 (q, 2H), 2.26-2.20 (m, 1H), 1.31 (t, 3H), 1.08-1.00 (m, 4H).
Beispiel 1-19 Example 1-19
2-[2-(5-Chlor-2-thienyl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (5-chloro-2-thienyl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (0,4 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (41,0 mg, 80 pmol), 2-(5-Chlor-2-thienyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolan (39,1 mg, 160 pmol) und Tetrakis(triphenylphosphin)palladium(0) (18,4 mg, 16 pmol) hinzugegeben und die Mischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (16,9 mg, 38% d. Th.). A mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (0.4 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (41.0 mg, 80 pmol), 2- (5-chloro-2-thienyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (39.1 mg, 160 pmol) and tetrakis (triphenylphosphine) palladium (0) (18.4 mg, 16 pmol) was added and the mixture was heated in a microwave reactor at 120 ° C for 30 minutes. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (16.9 mg, 38% of theory).
ESI Masse [m/z]: 551,1 / 553,0 [M+H]+ ESI mass [m / z]: 551.1 / 553.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.65 (d, 1H), 7.34 (d, 1H), 4.08 (s, 3H), 3.79 (s, 3H), 3.73 (q, 2H), 1.28 (t, 3H). 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.65 (d, 1H), 7.34 (d, 1H), 4.08 (s , 3H), 3.79 (s, 3H), 3.73 (q, 2H), 1.28 (t, 3H).
Beispiel 1-20 Example 1-20
2-{5-(Ethylsulfonyl)-2-[3-(l-fluorcyclopropyl)phenyl]-l-methyl-lH-imidazol-4-yl}-6,6,7,7-tetrafluor-l- methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol Eine Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (0,4 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (41,0 mg, 80 pmol), 2-[3-(l-Fluorcyclopropyl)phenyl]-4,4,5,5-tetramethyl-l,3,2-dioxaborolan (50,4 mg, 192 pmol) und Tetrakis(triphenylphosphin)palladium(0) (18,5 mg, 16 pmol) hinzugegeben und die Mischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natrium sulfat getrocknet und eingeengt. Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (29,3 mg, 97% Reinheit, 60% d. Th.). ESI Masse [m/z]: 569,0 [M+H] 2- {5- (Ethylsulfonyl) -2- [3- (1-fluorocyclopropyl) phenyl] -1-methyl-1 H -imidazol-4-yl} -6,6,7,7-tetrafluoro-1-methyl-6 , 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole A mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (0.4 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [1,4] dioxino [2,3-f] benzimidazole (41.0 mg, 80 pmol), 2- [3- (1-fluorocyclopropyl) phenyl] -4,4,5,5-tetramethyl-1,3 , 2-dioxaborolane (50.4 mg, 192 pmol) and tetrakis (triphenylphosphine) palladium (0) (18.5 mg, 16 pmol) were added and the mixture was heated in a microwave reactor at 120 ° C for 30 minutes. After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (29.3 mg, 97% purity, 60% of theory). ESI mass [m / z]: 569.0 [M + H]
Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.77-7.69 (m, 1H), 7.67-7.59 (m, 2H), 7.50 (d, 1H), 3.94 (s, 3H), 3.82 (s, 3H), 3.78 (q, 2H), 1.59-1.45 (m, 2H), 1.31 (t, 3H), 1.29-1.23 (m, 2H). Beispiel 1-21 Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 7.89 (s, 1H), 7.83 (s, 1H), 7.77-7.69 (m, 1H), 7.67-7.59 (m, 2H), 7.50 (d, 1H), 3.94 (s, 3H), 3.82 (s, 3H), 3.78 (q, 2H), 1.59-1.45 (m, 2H), 1.31 (t, 3H), 1.29-1.23 (m, 2H ). Example 1-21
2-[2-(6-Chlorpyridin-2-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2 ,3 -f] benzimidazol Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (70,0 mg, 136 pmol), 2-Chlor-6- (tributylstannyl)pyridin (71,3 mg, 177 pmol), Lithiumchlorid (15,0 mg, 355 pmol), Kupfer(I)iodid (2,6 mg, 14 pmol) und Tetrakis(triphenylphosphin)palladium(0) (31,5 mg, 27 pmol) in entgastem Dioxan (3,0 mL) wurde in einem Mikrowellenreaktor 1 h lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über eine Kiesegleschicht filtriert und mit einer Mischung aus Dichlormethan und Triethylamin (95:5 vol%) nachgewaschen und das Filtrat wurde eingeengt. Wiederholte chromatographische Aufreinigng des Rückstands zuerst mittels präparativer HPLC und anschließend an Kieselgel lieferte die Titel Verbindung (16,0 mg, 98% Reinheit, 21% d. Th.). 2- [2- (6-chloropyridin-2-yl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [1,4] dioxino [2,3-f] benzimidazole (70.0 mg, 136 pmol), 2-chloro-6- (tributylstannyl) pyridine (71.3 mg, 177 pmol), lithium chloride (15.0 mg, 355 pmol), copper (I) iodide (2.6 mg, 14 pmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 pmol) in degassed dioxane (3.0 mL) was in a Microwave reactor heated to 150 ° C. for 1 hour. After cooling to RT, the reaction mixture was filtered through a layer of silica gel and washed with a mixture of dichloromethane and triethylamine (95: 5% by volume) and the filtrate was concentrated. Repeated chromatographic purification of the residue, first by means of preparative HPLC and then on silica gel, gave the title compound (16.0 mg, 98% purity, 21% of theory).
ESI Masse [m/z]: 546,3 / 538,1 [M+H]+ 'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.17 (m, 1H), 8.07-8.12 (m, 1H), 7.90 (s, 1H), 7.84 (s, 1H), 7.72 (m, 1H), 5.75 (s, 1H), 4.30 (s, 3H), 3.81 (s, 3H), 3.76 (m, 2H), 1.29 (m, 3H). ESI mass [m / z]: 546.3 / 538.1 [M + H] + 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 8.17 (m, 1H), 8.07-8.12 (m, 1H), 7.90 (s, 1H), 7.84 (s, 1H), 7.72 (m, 1H), 5.75 (s, 1H), 4.30 (s, 3H), 3.81 (s, 3H), 3.76 ( m, 2H), 1.29 (m, 3H).
Beispiel 1-22 Example 1-22
2-[2-(6'-Chlor[2,2'-bipyridin]-6-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (6'-chloro [2,2'-bipyridin] -6-yl) -5- (ethylsulfonyl) -1-methyl-1 H -imidazol-4-yl] -6,6,7,7 -tetrafluoro-1-methyl-6, 7 -dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (70,0 mg, 136 m mol), 2-Chlor-6- (tributylstannyl)pyridin (71,3 mg, 177 pmol), Lithiumchlorid (15,0 mg, 355 pmol), Kupfer(I)iodid (2,6 mg, 14 pmol) und Tetrakis(triphenylphosphin)palladium(0) (31,5 mg, 27 pmol) in entgastem Dioxan (3,0 mL) wurde in einem Mikrowellenreaktor 1 h lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über eine Kiesegleschicht filtriert und mit einer Mischung aus Dichlormethan und Triethylamin (95:5 vol%) nachgewaschen und das Filtrat wurde eingeengt. Wiederholte chromatographische Aufreinigng des Rückstands zuerst mittels präparativer HPLC und anschließend an Kieselgel lieferte die Titel Verbindung (4,3 mg, 98% Reinheit, 5% d. Th.). A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [l, 4] dioxino [2,3-f] benzimidazole (70.0 mg, 136 mol), 2-chloro-6- (tributylstannyl) pyridine (71.3 mg, 177 pmol), lithium chloride (15, 0 mg, 355 pmol), copper (I) iodide (2.6 mg, 14 pmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 pmol) in degassed dioxane (3.0 mL) was heated to 150 ° C for 1 h in a microwave reactor. After cooling to RT, the reaction mixture was filtered through a layer of silica gel and washed with a mixture of dichloromethane and triethylamine (95: 5% by volume) and the filtrate was concentrated. Repeated chromatographic purification of the residue, first by means of preparative HPLC and then on silica gel, gave the title compound (4.3 mg, 98% purity, 5% of theory).
ESI Masse [m/z]: 623,3 [M+H]+ ESI mass [m / z]: 623.3 [M + H] +
Tf-NMR (600 MHz, DMF-d7): d [ppm] = 8.59 (d, 1H), 8.52 (d, 1H), 8.37 (d, 1H), 8.28 (m, 1H), 8.14- 8.19 (m, 1H), 7.92 (s, 1H), 7.82 (s, 1H), 7.70 (d, 1H), 4.62 (s, 3H), 4.01 (s, 3H), 3.93 (m, 2H), 1.43 (m, 3H). Beispiel 1-23 Tf-NMR (600 MHz, DMF-d 7 ): d [ppm] = 8.59 (d, 1H), 8.52 (d, 1H), 8.37 (d, 1H), 8.28 (m, 1H), 8.14-8.19 ( m, 1H), 7.92 (s, 1H), 7.82 (s, 1H), 7.70 (d, 1H), 4.62 (s, 3H), 4.01 (s, 3H), 3.93 (m, 2H), 1.43 (m , 3H). Example 1-23
2-[2-(3-Cyclopropyl-lH-l,2,4-triazol-l-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7- tetrafluor- 1 -methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (3-Cyclopropyl-lH-l, 2,4-triazol-l-yl) -5- (ethylsulfonyl) -l-methyl-lH-imidazol-4-yl] -6,6,7, 7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6, 7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (40,0 mg, 78 pmol), 3-Cyclopropyl-lH-l,2,4-A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [l, 4] dioxino [2,3-f] benzimidazole (40.0 mg, 78 pmol), 3-cyclopropyl-lH-l, 2,4-
Triazol (8,5 mg, 78 pmol) und Kaliumcarbonat (10,7 mg, 78 pmol) in DMF wurde über Nacht auf 96 °C erhitzt. Anschlißend wurden erneut 3-Cyclopropyl-lH-l,2,4-Triazol (8,5 mg, 78 pmol) und Kaliumcarbonat (10,7 mg, 78 pmol) hinzugegeben und die Mischung wurde weitere 5 h lang bei 96 °C gerührt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung mit Dichlormethan und Wasser verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (23,0 mg, 98% Reinheit, 53% d. Th.).Triazole (8.5 mg, 78 pmol) and potassium carbonate (10.7 mg, 78 pmol) in DMF was heated to 96 ° C overnight. 3-Cyclopropyl-1H-l, 2,4-triazole (8.5 mg, 78 pmol) and potassium carbonate (10.7 mg, 78 pmol) were then added again and the mixture was stirred at 96 ° C. for a further 5 hours . After cooling to RT, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC gave the title compound (23.0 mg, 98% purity, 53% of theory).
ESI Masse [m/z]: 542,2 [M+H]+ ESI mass [m / z]: 542.2 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 9.04 (s, 1H), 7.90 (s, 1H), 7.85 (s, 1H), 3.94 (s, 3H), 3.80- 3.85 (m, 5H), 2.12-2.19 (m, 1H), 1.31 (m, 3H), 0.99-1.09 (m, 2H), 0.94 (m, 2H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 9.04 (s, 1H), 7.90 (s, 1H), 7.85 (s, 1H), 3.94 (s, 3H), 3.80-3.85 (m, 5H), 2.12-2.19 (m, 1H), 1.31 (m, 3H), 0.99-1.09 (m, 2H), 0.94 (m, 2H).
Beispiel 1-24 Example 1-24
2-[2-(5-Brompyridin-2-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (70,0 mg, 136 m mol), 5-Brom-2- (tributylstannyl)pyridin (79,3 mg, 177 pmol), Lithiumchlorid (15,0 mg, 355 mmol), Kupfer(I)iodid (2,6 mg, 14 pmol) und Tetrakis(triphenylphosphin)palladium(0) (31,5 mg, 27 pmol) in entgastem Dioxan (3,0 mL) wurde in einem Mikrowellenreaktor 1 h lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über eine Kiesegleschicht filtriert und mit einer Mischung aus Dichlormethan und Triethylamin (95:5 vol%) nachgewaschen und das Filtrat wurde eingeengt. Wiederholte chromatographische Aufreinigng des Rückstands zuerst mittels präparativer HPLC und anschließend an Kieselgel lieferte die Titel Verbindung (4,5 mg, 6% d. Th.). 2- [2- (5-bromopyridin-2-yl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [l, 4] dioxino [2,3-f] benzimidazole (70.0 mg, 136 mol), 5-bromo-2- (tributylstannyl) pyridine (79.3 mg, 177 pmol), lithium chloride (15, 0 mg, 355 mmol), copper (I) iodide (2.6 mg, 14 pmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 pmol) in degassed dioxane (3.0 ml) was in heated to 150 ° C for 1 hour in a microwave reactor. After cooling to RT, the reaction mixture was filtered through a layer of silica gel and washed with a mixture of dichloromethane and triethylamine (95: 5% by volume) and the filtrate was concentrated. Repeated chromatographic purification of the residue, first by means of preparative HPLC and then on silica gel, gave the title compound (4.5 mg, 6% of theory).
ESI Masse [m/z]: 589,9 / 591,9 [M+H]+ ESI mass [m / z]: 589.9 / 591.9 [M + H] +
'H-NMR (400 MHz, Acetonitrile-ife): d [ppm] = 8.81-8.83 (m, 1H), 8.08-8.12 (m, 2H), 7.59 (s, 1H), 7.47 (s, 1H), 4.34 (s, 3H), 3.81 (s, 3H), 3.66 (m, 2H), 1.34 (m, 3H). 'H-NMR (400 MHz, acetonitrile-ife): d [ppm] = 8.81-8.83 (m, 1H), 8.08-8.12 (m, 2H), 7.59 (s, 1H), 7.47 (s, 1H), 4.34 (s, 3H), 3.81 (s, 3H), 3.66 (m, 2H), 1.34 (m, 3H).
Beispiel 1-25 2-[2-(5-Brom[2,3'-bipyridin]-6'-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol Example 1-25 2- [2- (5-Bromo [2,3'-bipyridin] -6'-yl) -5- (ethylsulfonyl) -1-methyl-1 H -imidazol-4-yl] -6,6 , 7,7-tetrafluoro-1-methyl-6, 7-dihydro-1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (70,0 mg, 136 pmol), 5-Brom-2- (tributylstannyl)pyridin (79,3 mg, 177 pmol), Lithiumchlorid (15,0 mg, 355 pmol), Kupfer(I)iodid (2,6 mg, 14 pmol) und Tetrakis(triphenylphosphin)palladium(0) (31,5 mg, 27 pmol) in entgastem Dioxan (3,0 mL) wurde in einem Mikrowellenreaktor 1 h lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über eine Kiesegleschicht filtriert und mit einer Mischung aus Dichlormethan und Triethylamin (95:5 vol%) nachgewaschen und das Filtrat wurde eingeengt. Wiederholte chromatographische Aufreinigng des Rückstands zuerst mittels präparativer HPLC und anschließend an Kieselgel lieferte die Titel Verbindung (2,7 mg, 3% d. Th.). A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [1,4] dioxino [2,3-f] benzimidazole (70.0 mg, 136 pmol), 5-bromo-2- (tributylstannyl) pyridine (79.3 mg, 177 pmol), lithium chloride (15.0 mg, 355 pmol), copper (I) iodide (2.6 mg, 14 pmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 pmol) in degassed dioxane (3.0 mL) was in a Microwave reactor heated to 150 ° C. for 1 hour. After cooling to RT, the reaction mixture was filtered through a layer of silica gel and washed with a mixture of dichloromethane and triethylamine (95: 5% by volume) and the filtrate was concentrated. Repeated Chromatographic purification of the residue first by means of preparative HPLC and then on silica gel yielded the title compound (2.7 mg, 3% of theory).
ESI Masse [m/z]: 666,9 / 668,9 [M+H]+ ESI mass [m / z]: 666.9 / 668.9 [M + H] +
'H-NMR (400 MHz, Acetonitrile-Ä): d [ppm] = 9.33-9.36 (m, 1H), 8.81-8.83 (m, 1H), 8.53 (m, 1H), 8.28 (m, 1H), 8.09 (m, 1H), 7.93 (d, 1H), 7.60 (s, 1H), 7.48 (s, 1H), 4.43 (s, 3H), 3.84 (s, 3H), 3.68 (m, 2H), 1.36 (m, 3H). 'H-NMR (400 MHz, acetonitrile-Ä): d [ppm] = 9.33-9.36 (m, 1H), 8.81-8.83 (m, 1H), 8.53 (m, 1H), 8.28 (m, 1H), 8.09 (m, 1H), 7.93 (d, 1H), 7.60 (s, 1H), 7.48 (s, 1H), 4.43 (s, 3H), 3.84 (s, 3H), 3.68 (m, 2H), 1.36 (m, 3H).
Beispiel 1-26 Example 1-26
2-[5-(Ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-2- [5- (Ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-
[l,4]dioxino[2,3-f]benzimidazol [1,4] dioxino [2,3-f] benzimidazole
Zu einer Lösung von 6,6,7,7-Tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (345 mg, 1,32 mmol) in trockenem Dioxan (15,0 mL) wurde hinnen 5 min 2, 2,6,6- Tetramethylpiperidinylzinkchlorid Lithiumchlorid Komplex (1.3 M Lösung in THF, 1,20 mL, 1,58 mmol) hinzugegeben und die Mischung wurde 20 min lang bei RT gerührt. Anschließend wurde eine Lösung von Tetrakis(triphenylphosphin)palladium(0) (152 mg, 132 pmol) in Dioxan (5,0 mL) sowie ein Lösung von 5-(Ethylsulfanyl)-4-iod-l-methyl-lH-imidazol (353 mg, 1,32 mmol) in Dioxan (5,0 mL) hinzugegeben und die Mischung wurde 2 h lang bei 115 °C (Ölbadtemperatur) gerührt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung in halbgesättigte wässrige Ammoniumchloridlösung (40 mL) eingetragen und mit Essigsäureethylester (40 mL) verdünnt. Dabei fiel ein Teil der Zielverbindung aus. Filtration und Trocknen des Feststoffs lieferte eine erste Fraktion der Titel Verbindung (158 mg, 30% d. Th.). To a solution of 6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (345 mg, 1.32 mmol) in dry dioxane (15.0 mL) was added 2, 2,6,6-tetramethylpiperidinylzinc chloride lithium chloride complex (1.3 M solution in THF, 1.20 mL, 1.58 mmol) for 5 min and the mixture was at RT for 20 min touched. Then a solution of tetrakis (triphenylphosphine) palladium (0) (152 mg, 132 pmol) in dioxane (5.0 mL) and a solution of 5- (ethylsulfanyl) -4-iodo-1-methyl-1H-imidazole ( 353 mg, 1.32 mmol) in dioxane (5.0 mL) was added and the mixture was stirred at 115 ° C. (oil bath temperature) for 2 h. After cooling to RT, the reaction mixture was introduced into semi-saturated aqueous ammonium chloride solution (40 mL) and diluted with ethyl acetate (40 mL). Part of the target connection failed. Filtration and drying of the solid yielded a first fraction of the title compound (158 mg, 30% of theory).
Eine zweite Fraktion der Titel Verbindung wurde aus dem Filtrat gewonnen. Dazu wurden die Phasen getrennt und die wässrige Phase wurde mit Essigsäureethylester (2 x 40 mL) extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrockent und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte eine zweite Fraktion der Titelverbindung (166 mg, 31% d. Th.).A second fraction of the title compound was recovered from the filtrate. For this purpose, the phases were separated and the aqueous phase was extracted with ethyl acetate (2 × 40 mL). The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded a second fraction of the title compound (166 mg, 31% of theory).
ESI Masse [m/z]: 403,5 [M+H]+ ESI mass [m / z]: 403.5 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.10 (s, 1H), 7.81 (s, 1H), 7.77 (s, 1H), 3.99 (s, 3H), 3.75 (s, 3H), 2.96 (m, 2H), 1.07 (m, 3H). Beispiel 1-27 l-{6-[5-(Ethylsulfanyl)-l-methyl-4-(6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3- f]benzimidazol-2-yl)-lH-imidazol-2-yl]pyridin-2-yl}cyclopropancarbonitril 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 8.10 (s, 1H), 7.81 (s, 1H), 7.77 (s, 1H), 3.99 (s, 3H), 3.75 (s , 3H), 2.96 (m, 2H), 1.07 (m, 3H). Example 1-27 l- {6- [5- (Ethylsulfanyl) -l-methyl-4- (6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazol-2-yl) -1H-imidazol-2-yl] pyridin-2-yl} cyclopropanecarbonitrile
Zu einer Lösung von 2-[5-(Ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (82,5 mg, 205 pmol) in trockenem Dioxan (15,0 mL) wurde binnen 5 min 2,2,6,6-Tetramethylpiperidinylzinkchlorid Lithiumchlorid Komplex (1.3 M Lösung in THE, 186 pL, 246 pmol) hinzugegeben und die Mischung wurde 20 min lang bei RT gerührt. Anschließend wurde eine Lösung von Tetrakis(triphenylphosphin)palladium(0) (23,7 mg, 21 pmol) in Dioxan (5,0 mL) sowie ein Lösung von l-(6-Brompyridin-2-yl)cyclopropancarbonitril (45,7 mg, 205 pmol) in Dioxan (5,0 mL) hinzugegeben und die Mischung wurde 2 h lang bei 115 °C (Ölbadtemperatur) gerührt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung in halbgesättigte wässrige Ammoniumchloridlösung (40 mL) eingetragen und mit Essigsäureethylester (40 mL) verdünnt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Essigsäureethylester (2 x 40 mL) extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrockent und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (19 mg, 40% Reinheit, 7% d. Th.). To a solution of 2- [5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H- [l , 4] dioxino [2,3-f] benzimidazole (82.5 mg, 205 pmol) in dry dioxane (15.0 mL) was 2,2,6,6-tetramethylpiperidinylzinc chloride lithium chloride complex (1.3 M solution in THE, 186 pL, 246 pmol) was added and the mixture was stirred for 20 min at RT. A solution of tetrakis (triphenylphosphine) palladium (0) (23.7 mg, 21 pmol) in dioxane (5.0 ml) and a solution of 1- (6-bromopyridin-2-yl) cyclopropanecarbonitrile (45.7 mg, 205 pmol) in dioxane (5.0 mL) was added and the mixture was stirred at 115 ° C. (oil bath temperature) for 2 h. After cooling to RT, the reaction mixture was introduced into semi-saturated aqueous ammonium chloride solution (40 mL) and diluted with ethyl acetate (40 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (2 × 40 mL). The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (19 mg, 40% purity, 7% of theory).
ESI Masse [m/z]: 545,2 [M+H]+ ESI mass [m / z]: 545.2 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.14 (d, 1H), 7.99-8.04 (m, 1H), 7.86 (s, 1H), 7.81 (s, 1H), 7.59 (br m, 1H), 4.18 (s, 3H), 4.05 (s, 3H), 2.96-3.03 (m, 2H), 1.82-1.94 (m, 4H), 1.11 (m, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 8.14 (d, 1H), 7.99-8.04 (m, 1H), 7.86 (s, 1H), 7.81 (s, 1H), 7.59 (br m, 1H), 4.18 (s, 3H), 4.05 (s, 3H), 2.96-3.03 (m, 2H), 1.82-1.94 (m, 4H), 1.11 (m, 3H).
Beispiel 1-28 l-{6-[5-(Ethylsulfonyl)-l-methyl-4-(6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3- f]benzimidazol-2-yl)-lH-imidazol-2-yl]pyridin-2-yl}cyclopropancarbonitril l-{6-[5-(Ethylsulfanyl)-l-methyl-4-(6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3- f]benzimidazol-2-yl)-lH-imidazol-2-yl]pyridin-2-yl}cyclopropancarbonitril (17,0 mg, 31,0 pmol) wurde in Dichlormethan (20,0 mL) vorgelegt und mit Ameisensäure (12 pL, 312 pmol) und Wasserstoffperoxid (35%ige wässrige Lösung, 27 pL, 312 pmol) versetzt. Die Mischung wurde über Nacht bei RT gerührt. Anschließend wurde die Reaktionsmischung mit Wasser (50,0 mL) und gesättigter wässriger Natriumbisulfitlösung (15,0 mL) versetzt und 1 h lang gerührt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, über Natriumsulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (7,5 mg, 42% d. Th.). Example 1-28 l- {6- [5- (Ethylsulfonyl) -l-methyl-4- (6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazol-2-yl) -1H-imidazol-2-yl] pyridin-2-yl} cyclopropanecarbonitrile 1- {6- [5- (Ethylsulfanyl) -l-methyl-4- (6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H- [1,4] dioxino [2, 3-f] benzimidazol-2-yl) -1H-imidazol-2-yl] pyridin-2-yl} cyclopropanecarbonitrile (17.0 mg, 31.0 pmol) in dichloromethane (20.0 mL) and mixed with formic acid (12 pL, 312 pmol) and hydrogen peroxide (35% aqueous solution, 27 pL, 312 pmol). The mixture was stirred at RT overnight. The reaction mixture was then combined with water (50.0 mL) and saturated aqueous sodium bisulfite solution (15.0 mL) and stirred for 1 h. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (7.5 mg, 42% of theory).
ESI Masse [m z]: 577,0 [M+H]+ ESI mass [mz]: 577.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.03-8.11 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 7.67 (m, 1H), 4.30 (s, 3H), 3.80 (s, 3H), 3.76 (m, 2H), 1.91-1.95 (m, 2H), 1.82-1.86 (m, 2H), 1.29 (m, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 8.03-8.11 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 7.67 (m, 1H), 4.30 (s, 3H), 3.80 (s, 3H), 3.76 (m, 2H), 1.91-1.95 (m, 2H), 1.82-1.86 (m, 2H), 1.29 (m, 3H).
Beispiel 1-29 Example 1-29
2-[2-(6-Brompyridin-2-yl)-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazole Zu einer Lösung von 2-[5-(Ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (82,5 mg, 205 pmol) in trockenem Dioxan (15,0 mL) wurde binnen 5 min 2,2,6,6-Tetramethylpiperidinylzinkchlorid Lithiumchlorid Komplex (1.3 M Lösung in THF, 186 pL, 246 pmol) hinzugegeben und die Mischung wurde 20 min lang bei RT gerührt. Anschließend wurde eine Lösung von Tetrakis(triphenylphosphin)palladium(0) (23,7 mg, 21 pmol) in Dioxan (5,0 mL) sowie ein Lösung von 2,6-Dibrompyridin (48,6 mg, 205 pmol) in Dioxan (5,0 mL) hinzugegeben und die Mischung wurde 2 h lang bei 115 °C (Ölbadtemperatur) gerührt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung in halbgesättigte wässrige Ammoniumchloridlösung (40 mL) eingetragen und mit Essigsäureethylester (40 mL) verdünnt. Die unlsölichen bestandteile wurden abfiltiert. Die Phasen wurden getrennt und die wässrige Phase wurde mit Essigsäureethylester (2 x 40 mL) extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrockent und eingeengt. Der Rückstand und der zuvor abfiltrierte Festsoff wurden vereinigt. Aufreinigung des so erhaltenen Rohprodukts mittels präparativer HPLC lieferte die Titelverbindung (28,2 mg, 90% Reinheit, 22% d. Th.). 2- [2- (6-bromopyridin-2-yl) -5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazoles To a solution of 2- [5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H- [l , 4] dioxino [2,3-f] benzimidazole (82.5 mg, 205 pmol) in dry dioxane (15.0 mL) was 2.2,6,6-tetramethylpiperidinylzinc chloride lithium chloride complex (1.3 M solution in THF, 186 pL, 246 pmol) was added and the mixture was stirred for 20 min at RT. A solution of tetrakis (triphenylphosphine) palladium (0) (23.7 mg, 21 pmol) in dioxane (5.0 ml) and a solution of 2,6-dibromopyridine (48.6 mg, 205 pmol) in dioxane were then added (5.0 mL) was added and the mixture was stirred at 115 ° C (oil bath temperature) for 2 h. After cooling to RT, the reaction mixture was introduced into semi-saturated aqueous ammonium chloride solution (40 mL) and diluted with ethyl acetate (40 mL). The insoluble components were filtered off. The phases were separated and the aqueous phase was extracted with ethyl acetate (2 × 40 mL). The combined organic phases were dried over sodium sulfate and concentrated. The residue and the solid previously filtered off were combined. Purification of the crude product thus obtained by means of preparative HPLC yielded the title compound (28.2 mg, 90% purity, 22% of theory).
ESI Masse [m/z]: 558,0/560,0 [M+H] ESI mass [m / z]: 558.0 / 560.0 [M + H]
Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 8.23 (m, 1H), 7.91-7.97 (m, 1H), 7.86 (s, 1H), 7.82 (s, 1H), 7.75 (m, 1H), 4.17 (s, 3H), 4.05 (s, 3H), 3.01 (m, 2H), 1.11 (m, 3H). Ή-NMR (400 MHz, DMSO-ifc): d [ppm] = 8.23 (m, 1H), 7.91-7.97 (m, 1H), 7.86 (s, 1H), 7.82 (s, 1H), 7.75 (m, 1H), 4.17 (s, 3H), 4.05 (s, 3H), 3.01 (m, 2H), 1.11 (m, 3H).
Beispiel 1-30 Example 1-30
2-[2-(6-Brompyridin-2-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (6-bromopyridin-2-yl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
2-[2-(6-Brompyridin-2-yl)-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazole (25,0 mg, 45,0 m mol) wurde in Dichlormethan (20,0 mL) vorgelegt und mit Ameisensäure (17 m L, 448 mmol) und Wasserstoffperoxid (35%ige wässrige Lösung, 39 pL, 448 pmol) versetzt. Die Mischung wurde über Nacht bei RT gerührt. Anschließend wurde die Reaktionsmischung mit Wasser (50,0 mL) und gesättigter wässriger Natriumbisulfitlösung (15,0 mL) versetzt und 1 h lang gerührt. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden mit Wasser gewaschen, über Natrium sulfat getrocknet und eingeengt. Aufreinigung des Rückstands mittels präparativer HPLC lieferte die Titel Verbindung (13,7 mg, 52% d. Th.). ESI Masse [m/z]: 590,0/592,0 [M+H]+ 2- [2- (6-bromopyridin-2-yl) -5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (25.0 mg, 45.0 m mol) was placed in dichloromethane (20.0 mL) and mixed with formic acid (17 m L, 448 mmol) and hydrogen peroxide (35% aqueous solution, 39 pL, 448 pmol) are added. The mixture was stirred at RT overnight. The reaction mixture was then combined with water (50.0 mL) and saturated aqueous sodium bisulfite solution (15.0 mL) and stirred for 1 h. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. Purification of the residue by means of preparative HPLC yielded the title compound (13.7 mg, 52% of theory). ESI mass [m / z]: 590.0 / 592.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.85 (d, 1H), 8.15-8.21 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 4.31 (s, 3H), 3.82 (s, 3H), 3.77 (m, 2H), 1.29 (m, 3H). 'H-NMR (400 MHz, DMSO- d 6 ): d [ppm] = 8.85 (d, 1H), 8.15-8.21 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 4.31 (s, 3H), 3.82 (s, 3H), 3.77 (m, 2H), 1.29 (m, 3H).
Beispiel 1-31 Example 1-31
2-[2-(5-Chlorpyridin-2-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl- 6,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol 2- [2- (5-chloropyridin-2-yl) -5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus 2-[2-Brom-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l- methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (90,0 mg, 175 pmol), 5-Chlor-2- (tributylstannyl)pyridin (91,7 mg, 228 pmol), Lithiumchlorid (19,3 mg, 456 pmol), Kupfer(I)iodid (3,3 mg, 18 pmol) und Tetrakis(triphenylphosphin)palladium(0) (40,5 mg, 35 pmol) in entgastem Dioxan (3,0 mL) wurde in einem Mikrowellenreaktor 1 h lang auf 150 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung über eine Kiesegleschicht filtriert und mit einer Mischung aus Dichlormethan und Triethylamin (95:5 vol%) nachgewaschen und das Filtrat wurde eingeengt. Chromatographische Aufreinigng des Rückstands mittels präparativer HPLC lieferte die Titelverbindung (57,8 mg, 98% Reinheit, 59% d. Th.). A mixture of 2- [2-bromo-5- (ethylsulfonyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H - [1,4] dioxino [2,3-f] benzimidazole (90.0 mg, 175 pmol), 5-chloro-2- (tributylstannyl) pyridine (91.7 mg, 228 pmol), lithium chloride (19.3 mg, 456 pmol), copper (I) iodide (3.3 mg, 18 pmol) and tetrakis (triphenylphosphine) palladium (0) (40.5 mg, 35 pmol) in degassed dioxane (3.0 mL) was heated in a microwave reactor at 150 ° C. for 1 hour. After cooling to RT, the reaction mixture was filtered through a layer of silica gel and washed with a mixture of dichloromethane and triethylamine (95: 5% by volume) and the filtrate was concentrated. Chromatographic purification of the residue by means of preparative HPLC yielded the title compound (57.8 mg, 98% purity, 59% of theory).
ESI Masse [m/z]: 546,0/548,0 [M+H]+ ESI mass [m / z]: 546.0 / 548.0 [M + H] +
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 8.85 (d, 1H), 8.15-8.21 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 4.31 (s, 3H), 3.82 (s, 3H), 3.77 (q, 2H), 1.29 (m, 3H). Beispiel 1-32 Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 8.85 (d, 1H), 8.15-8.21 (m, 2H), 7.90 (s, 1H), 7.84 (s, 1H), 4.31 ( s, 3H), 3.82 (s, 3H), 3.77 (q, 2H), 1.29 (m, 3H). Example 1-32
6-[5-(Ethylsulfonyl)-l-methyl-4-(6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3- f]benzimidazol-2-yl)-lH-imidazol-2-yl]nicotinonitril 6- [5- (Ethylsulfonyl) -1-methyl-4- (6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1 H- [1,4] dioxino [2,3-f ] benzimidazol-2-yl) -lH-imidazol-2-yl] nicotinonitrile
Zu einer entgasten Mischung aus Wasser (170 pL) und Cyclopentylmethylether (430 pL) wurden 2-[2- (5-Chlorpyridin-2-yl)-5-(ethylsulfonyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (37,0 mg, 68 pmol), Allylpalladiumchlorid Dimer (7,9 mg, 22 pmol), Kaliumhexacyanoferrat-Trihydrat (57,3 mg, 136 pmol) und 2-Dicyclohexylphosphin-2',4',6'- triisopropylbiphenyl (Xphos, 13,9 mg, 28 pmol) hinzugegeben und die Reaktionsmischung wurde über Nacht auf 100 °C erhitzt. Nach dem Abkühlen auf RT wurde die Mischung mit Wasser verdünnt und mit Essigsäureethylester extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrockent und eingeengt. Aufreinigung des so erhaltenen Rohprodukts mittels präparativer HPLC lieferte die Titel Verbindung (18,7 mg, 51% d. Th.). 2- [2- (5-Chlorpyridin-2-yl) -5- (ethylsulfonyl) -l-methyl-lH-imidazol-4-yl] were added to a degassed mixture of water (170 pL) and cyclopentyl methyl ether (430 pL) -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (37.0 mg, 68 pmol), allyl palladium chloride dimer ( 7.9 mg, 22 pmol), potassium hexacyanoferrate trihydrate (57.3 mg, 136 pmol) and 2-dicyclohexylphosphine-2 ', 4', 6'-triisopropylbiphenyl (Xphos, 13.9 mg, 28 pmol) were added and the The reaction mixture was heated to 100 ° C. overnight. After cooling to RT, the mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the crude product thus obtained by means of preparative HPLC yielded the title compound (18.7 mg, 51% of theory).
ESI Masse [m/z]: 537,4 [M+H]+ ESI mass [m / z]: 537.4 [M + H] +
Ή-NMR (400 MHz, DMSO-d6): d [ppm] = 9.23 (d, 1H), 8.52 (m, 1H), 8.35 (d, 1H), 7.91 (s, 1H), 7.85 (s, 1H), 4.35 (s, 3H), 3.82 (s, 3H), 3.75-3.81 (m, 2H), 1.29 (m, 3H). Ή-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 9.23 (d, 1H), 8.52 (m, 1H), 8.35 (d, 1H), 7.91 (s, 1H), 7.85 (s, 1H), 4.35 (s, 3H), 3.82 (s, 3H), 3.75-3.81 (m, 2H), 1.29 (m, 3H).
Beispiel 1-33 Example 1-33
2-[2-(4-Chlorphenyl)-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7- dihydro- 1 H- [ 1 ,4] dioxino [2 ,3 -f] benzimidazol 2- [2- (4-chlorophenyl) -5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl-6,7- dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole
Eine Mischung aus Dioxan (3,0 mL) und 1,0 M wässriger Natriumcarbonat-Lösung (0,5 mL) wurde 30 min lang im Argonstrom entgast. Anschließend wurden 2-[2-Brom-5-(ethylsulfanyl)-l-methyl-lH- imidazol-4-yl]-6,6,7,7-tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (50,0 mg, 104 mpioΐ), 4-Chlorphenylboronsäure (32,5 mg, 208 mpioΐ) und Tetrakis(triphenylphosphin)palladium(0) (24,0 mg, 21 pmol) hinzugegeben und die Mischung wurde in einem Mikrowellenreaktor 30 min lang auf 120 °C erhitzt. Nach dem Abkühlen auf RT wurde die Reaktionsmischung zur Trockne eingeengt und dann in Dichlormethan und Wasser aufgenommen. Die Phasen wurden getrennt und die wässrige Phase wurde mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet und eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieselgel lieferte die Titelverbindung (30,3 mg, 89% Reinheit, 51% d. Th.). A mixture of dioxane (3.0 mL) and 1.0 M aqueous sodium carbonate solution (0.5 mL) was degassed in a stream of argon for 30 minutes. Then 2- [2-bromo-5- (ethylsulfanyl) -l-methyl-lH- imidazol-4-yl] -6,6,7,7-tetrafluoro-l-methyl-6,7-dihydro-lH- [l, 4] dioxino [2,3-f] benzimidazole (50.0 mg, 104 mpioΐ), 4-chlorophenylboronic acid (32.5 mg, 208 mpioΐ) and tetrakis (triphenylphosphine) palladium (0) (24.0 mg , 21 pmol) was added and the mixture was heated to 120 ° C. for 30 minutes in a microwave reactor. After cooling to RT, the reaction mixture was concentrated to dryness and then taken up in dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. Purification of the residue by column chromatography on silica gel yielded the title compound (30.3 mg, 89% purity, 51% of theory).
ESI Masse [m/z]: 513,0/515,0 [M+H]+ ESI mass [m / z]: 513.0 / 515.0 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.85-7.88 (m, 2H), 7.83 (s, 1H), 7.80 (s, 1H), 7.60-7.66 (m, 2H), 4.03 (s, 3H), 3.86 (s, 3H), 3.00 (m, 2H), 1.13 (m, 3H). 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.85-7.88 (m, 2H), 7.83 (s, 1H), 7.80 (s, 1H), 7.60-7.66 (m, 2H) , 4.03 (s, 3H), 3.86 (s, 3H), 3.00 (m, 2H), 1.13 (m, 3H).
Beispiel 1-34 rac-2-[2-(4-Chlorphenyl)-5-(ethylsulfonimidoyl)- 1 -methyl- lH-imidazol-4-yl] -6,6,7, 7-tetrafluor- 1 - methyl-6 ,7 -dihydro- 1 H- [ 1 ,4] dioxino [2,3-f] benzimidazol Zu einer Lösung von 2-[2-(4-Chlorphenyl)-5-(ethylsulfanyl)-l-methyl-lH-imidazol-4-yl]-6, 6,7,7- tetrafluor-l-methyl-6,7-dihydro-lH-[l,4]dioxino[2,3-f]benzimidazol (30,0 mg, 94% Reinheit, 55 pmol) in Dichlormethan und Methanol wurden Ammoniumcarbamat (8,6 mg, 110 pmol) und (Diacetoxyiodo)benzol (45,2 mg, 137 pmol) hinzugegeben und die Suspension wurde 1 h lang in einem gschlossenen Reaktionsgefäß bei RT gerührt. Anschließend wurde die Reaktionsmischung eingeengt. Säulenchromatographische Aufreinigung des Rückstands an Kieselgel lieferte die Titel Verbindung (16,4 mg, 95% Reinheit, 52% d. Th.). Example 1-34 rac-2- [2- (4-chlorophenyl) -5- (ethylsulfonimidoyl) -1-methyl- 1H-imidazol-4-yl] -6,6,7,7-tetrafluoro-1-methyl- 6, 7 -dihydro- 1 H- [1,4] dioxino [2,3-f] benzimidazole To a solution of 2- [2- (4-chlorophenyl) -5- (ethylsulfanyl) -l-methyl-1H-imidazol-4-yl] -6, 6,7,7-tetrafluoro-1-methyl-6, 7-dihydro-1H- [1,4] dioxino [2,3-f] benzimidazole (30.0 mg, 94% purity, 55 pmol) in dichloromethane and methanol were ammonium carbamate (8.6 mg, 110 pmol) and ( Diacetoxyiodo) benzene (45.2 mg, 137 pmol) was added and the suspension was stirred for 1 h in a closed reaction vessel at RT. The reaction mixture was then concentrated. Purification of the residue by column chromatography on silica gel gave the title compound (16.4 mg, 95% purity, 52% of theory Th.).
ESI Masse [m/z]: 544,4/546,2 [M+H]+ ESI mass [m / z]: 544.4 / 546.2 [M + H] +
'H-NMR (400 MHz, DMSO-d6): d [ppm] = 7.87 (s, 1H), 7.79-7.83 (m, 3H), 7.63-7.68 (m, 2H), 4.76 (s, 1H), 3.98 (s, 3H), 3.76 (s, 3H), 3.42-3.58 (m, 2H), 1.23 (m, 3H). In Analogie zu den Beispielen und gemäß den oben beschriebenen Herstellverfahren lassen sich folgende Verbindungen der Formel (I) erhalten: 'H-NMR (400 MHz, DMSO-d 6 ): d [ppm] = 7.87 (s, 1H), 7.79-7.83 (m, 3H), 7.63-7.68 (m, 2H), 4.76 (s, 1H) , 3.98 (s, 3H), 3.76 (s, 3H), 3.42-3.58 (m, 2H), 1.23 (m, 3H). The following compounds of the formula (I) can be obtained in analogy to the examples and in accordance with the production processes described above:
Anwendungsbeispiele Application examples
Diabrotica balteata - Sprühtest Diabrotica balteata - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight 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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
Vorgequollene Weizenkörner ( Triticum aestivum ) werden in einer mit Agar und etwas Wasser gefüllten Multiwell-Platte für einen Tag inkubiert (5 Saatkörner pro Kavität). Die gekeimten Weizenkörner werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Anschließend wird jede Kavität mit 10-20 Käferlarven von Diabrotica balteata infiziert. Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Weizenpflanzen wie in der unbehandelten, nicht infizierten Kontrolle gewachsen sind; 0 % bedeutet, dass keine Weizenpflanze gewachsen ist. Pre-swollen wheat kernels (Triticum aestivum) are incubated for one day in a multiwell plate filled with agar and a little water (5 seeds per well). The germinated wheat grains are sprayed with an active ingredient preparation of the desired concentration. Each cavity is then infected with 10-20 Diabrotica balteata beetle larvae. The effect is determined in% after 7 days. 100% means that all wheat plants have grown as in the untreated, non-infected control; 0% means that no wheat plant has grown.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 100 g/ha (= 32 pg/Kavität): 1-2, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-18, 1-20, 1-21, 1-24, 1-30, 1-32, 1-34, 1-36, 1-38. In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 100 g / ha (= 32 pg / cavity): 1-2, 1-5, 1-6, 1-7, 1-8, 1-9 , 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-18, 1-20, 1-21, 1-24, 1-30, 1 -32, 1-34, 1-36, 1-38.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 80 % bei einer Aufwandmenge von 100 g/ha (= 32 pg/Kavität): 1-4, 1-23, 1-37. Meloidogyne incognita- Test In this test z. B. the following compounds of the preparation examples effect of 80% at an application rate of 100 g / ha (= 32 pg / cavity): 1-4, 1-23, 1-37. Meloidogyne incognita test
Lösungsmittel: 125,0 Gewichtsteile Aceton Solvent: 125.0 parts by weight acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße werden mit Sand, Wirkstofflösung, einer Ei-Larven-Suspension des südlichen Wurzelgallenälchens (. Meloidogyne incognita ) und Salatsamen gefüllt. Die Salatsamen keimen und die Pflänzchen entwickeln sich. An den Wurzeln entwickeln sich die Gallen. Vessels are filled with sand, active ingredient solution, an egg-larva suspension of the southern root knot (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop at the roots.
Nach 14 Tagen wird die nematizide Wirkung anhand der Gallenbildung in % bestimmt. Dabei bedeutet 100 %, dass keine Gallen gefunden wurden; 0 % bedeutet, dass die Zahl der Gallen an den behandelten Pflanzen der unbehandelten Kontrolle entspricht. After 14 days, the nematicidal effect is determined based on the gall formation in%. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 20 ppm: 1-6, 1-38. In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 20 ppm: 1-6, 1-38.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 20 ppm: 1-4, 1-8, 1-34, 1-37. In this test z. B. the following compounds of the preparation examples effect of 90% at an application rate of 20 ppm: 1-4, 1-8, 1-34, 1-37.
Mvzus persicae - Oraltest Mvzus persicae - oral test
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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the specified parts by weight of solvent and made up with water until the desired concentration is reached.
50 pl der Wirkstoffzubereitung werden in Mikrotiterplatten überführt und mit 150 mΐ IPL41 Insektenmedium (33 % + 15 % Zucker) auf eine Endvolumen von 200 mΐ 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 μl of the active compound preparation are transferred to microtiter plates and made up to a final volume of 200 ml with 150 ml of IPL41 insect medium (33% + 15% sugar). The plates are then sealed with parafilm, through which a mixed population of the green peach aphid (Myzus persicae) located in a second microtiter plate can pierce and absorb 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 none of the aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 20 ppm: 1-8. Mvzus persicae - Sprühtest In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 20 ppm: 1-8. Mvzus persicae - spray test
Lösungsmittel: 78 Gewichtsteile Aceton Solvent: 78 parts by weight 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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted 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 disks (Brassica pekinensis) which are 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 none of the aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 100 g/ha: 1-16, 1-34, 1-38. In this test z. B. the following compounds of the preparation examples effect of 90% at an application rate of 100 g / ha: 1-16, 1-34, 1-38.
Nezara viridula -Sprühtest Nezara viridula spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight 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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
Gerstenpflanzen ( Hordeum vulgare ) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und mit Larven der Grünen Reiswanze ( Nezara viridula ) infiziert. Barley plants (Hordeum vulgare) are sprayed with an active compound preparation of the desired concentration and infected with larvae of the green rice bug (Nezara viridula).
Nach 4 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Reiswanzen abgetötet wurden; 0 % bedeutet, dass keine Reiswanzen abgetötet wurden. After 4 days, the effect is determined in%. 100% means that all rice bugs have been killed; 0% means that none of the rice bugs have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha: 1-6, 1-10, 1- 11 , 1-15, 1-16, 1-18, 1-19, 1-21, 1-23, 1-24, 1-28, 1-30.In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 500 g / ha: 1-6, 1-10, 1- 11, 1-15, 1-16, 1-18, 1-19, 1- 21, 1-23, 1-24, 1-28, 1-30.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 1-14, 1-20, 1-36, 1-38. Nilaparvata lugens -Test In this test z. B. the following compounds of the preparation examples effect of 90% at an application rate of 500 g / ha: 1-14, 1-20, 1-36, 1-38. Nilaparvata lugens test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight acetone
1 ,5 Gewichtsteile Dimethylformamid Emulgator: Alkylarylpolyglykolether 1.5 parts by weight of dimethylformamide 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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water.
Reispflanzen ( Oryza sativa) werden mit der Wirkstoffzubereitung der gewünschten Konzentration gespritzt und anschließend mit der Braunrückigen Reiszikade ( Nilaparvata lugens ) infiziert. Rice plants (Oryza sativa) are sprayed with the preparation of active compound of the desired concentration and then infected with the brown-backed rice leafhopper (Nilaparvata lugens).
Nach 4 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Reiszikaden abgetötet wurden; 0 % bedeutet, dass keine Reiszikaden abgetötet wurden. After 4 days, the effect is determined in%. 100% means that all rice leafhoppers have been killed; 0% means that none of the rice leafhoppers have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha: 1-28, 1-30. In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 500 g / ha: 1-28, 1-30.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90 % bei einer Aufwandmenge von 500 g/ha: 1-21. In this test z. B. the following compounds of the preparation examples Effect of 90% at an application rate of 500 g / ha: 1-21.
Spodoptera frugiperda - Sprühtest Spodoptera frugiperda - spray test
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight acetone
1,5 Gewichtsteile Dimethylformamid Emulgator: Alkylarylpolyglykolether 1.5 parts by weight of dimethylformamide 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 produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted 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. Corn leaf disks (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the army worm (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. The effect is determined in% after 7 days. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 500 g/ha: 1-8. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100 % bei einer Aufwandmenge von 100 g/ha: 1-2, 1-4, 1-5, 1-6, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-18, 1-19, 1-20, 1-21, 1-23, 1-24, 1-25, 1-28, 1-30, 1-31, 1-32, 1-34, 1-36, 1-37, 1-38, 1-39. In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 500 g / ha: 1-8. In this test z. B. the following compounds of the preparation examples Effect of 100% at an application rate of 100 g / ha: 1-2, 1-4, 1-5, 1-6, 1-10, 1-11, 1-12, 1- 13, 1-14, 1-15, 1-16, 1-18, 1-19, 1-20, 1-21, 1-23, 1-24, 1-25, 1-28, 1-30, 1-31, 1-32, 1-34, 1-36, 1-37, 1-38, 1-39.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83 % bei einer Aufwandmenge von 100 g/ha: 1-9. In this test z. B. the following compounds of the preparation examples effect of 83% at an application rate of 100 g / ha: 1-9.
Myzus persicae - Sprühtest 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. Paprikapflanzen ( Capsicum annuum), die stark von der Grünen Pfirsichblattlaus ( Myzus persicae ) befallen sind, werden durch Sprühen mit der Wirkstoffzubereitung in der gewünschten Konzentration behandelt.To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved in the stated parts by weight of solvent and made up with water, which contains an emulsifier concentration of 1000 ppm, until the desired concentration is reached. To produce further test concentrations, it is diluted with emulsifier-containing water. If the addition of ammonium salts and / or penetration enhancers is necessary, these are each added to the preparation solution in a concentration of 1000 ppm. Bell pepper plants (Capsicum annuum) which are heavily infested by 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 destruction is determined in%. 100% means that all the lice have been killed; 0% means that none of the lice have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 99 % bei einer Aufwandmenge von 20 ppm: 1-9. In this test z. B. the following compounds of the preparation examples Effect of 99% at an application rate of 20 ppm: 1-9.

Claims

Patentansprüche Claims
1. Verbindungen der Formel (I) in welcher 1. Compounds of the formula (I) in which
R1 für (Ci-C6)Alkyl, (Ci-C6)Cyanoalkyl, (Ci-C6)Hydroxyalkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (Ci-C6)Halogenalkyl, (C2-C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Alkinyl, (C2-R 1 for (Ci-C6) alkyl, (Ci-C6) cyanoalkyl, (Ci-C6) hydroxyalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -
C6)Halogenalkinyl oder (C3-Cs)Cycloalkyl steht, C6) haloalkynyl or (C 3 -Cs) cycloalkyl,
R2 für Wasserstoff, (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-R 2 for hydrogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) cyanoalkyl, (Ci- C6) hydroxyalkyl, (Ci-C6) alkoxy- (Ci-C6) alkyl, (Ci- C6) haloalkoxy- (Ci-C6) alkyl, (C 2 -
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- C6)Halogenalkinyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkinyl, (C2-C6)Cyanoalkinyl, (C3-C6) alkenyl, (C 2 -C 6 ) alkenyloxy- (Ci-C 6 ) alkyl, (C 2 -C 6 ) haloalkenyloxy- (Ci-C 6 ) alkyl, (C 2 - C6) haloalkenyl, (C 2 - C 6 ) cyanoalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) alkinyloxy (Ci-C 6 ) alkyl, (C 2 - C6) haloalkinyloxy (Ci-C6) alkyl, (C 2 - C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 3 -
Cs)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-C8)Cycloalkyl, (Ci-C6)Alkyl-(C3-Cs)Cycloalkyl, Halogen(C3-Cs)cycloalkyl, Cyano(C3-Cs)cycloalkyl, (Ci-C6)Alkylthio-(Ci-C6)alkyl, (Ci-Cs) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 3 -C 8 ) cycloalkyl, (Ci-C 6 ) alkyl (C 3 -Cs) cycloalkyl, halogen (C 3 -Cs) cycloalkyl, cyano (C 3 -Cs) cycloalkyl, (Ci-C6) alkylthio- (Ci-C6) alkyl, (Ci-
C6)Halogenalkylthio-(Ci-C6)alkyl, (Ci-C6)Alkylsulfinyl-(Ci-C6)alkyl, (Ci-C 6 ) haloalkylthio (Ci-C 6 ) alkyl, (Ci-C 6 ) alkylsulfinyl (Ci-C 6 ) alkyl, (Ci-
C6)Halogenalkylsulfinyl-(Ci-C6)alkyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, (Ci-C 6 ) haloalkylsulfinyl (Ci-C 6 ) alkyl, (Ci-C 6 ) alkylsulfonyl (Ci-C 6 ) alkyl, (Ci-
C6)Halogenalkylsulfonyl-(Ci-C6)alkyl, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl, (Ci-C6) haloalkylsulfonyl- (Ci-C6) alkyl, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl oder (Ci- C6)Halogenalkoxycarbonyl-(Ci-C6)alkyl steht, C6) haloalkylcarbonyl- (Ci-C6) alkyl, (Ci-C6) alkoxycarbonyl- (Ci-C6) alkyl or (Ci- C6) haloalkoxycarbonyl- (Ci-C6) alkyl,
R3 für Wasserstoff, Halogen, Cyano, Nitro, (Ci-C6)Alkyl, (C3-Cs)Cycloalkyl, Cyano(C3- C8)cycloalkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (Ci- C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, SCN, (Ci-C6)Alkylcarbonyl, (Ci- C6)Halogenalkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl,R 3 is hydrogen, halogen, cyano, nitro, (Ci-C6) alkyl, (C 3 -Cs) cycloalkyl, cyano (C 3 - C 8) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, ( Ci-C6) haloalkoxy, (Ci-C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (Ci- C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, (Ci- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl,
Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci- C6)Halogenalkylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (Ci- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkylaminothiocarbonyl, (Ci-Aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (Ci- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (Ci-
C6)Halogenalkylaminothiocarbonyl, (C3-C8)Cycloalkylaminothiocarbonyl, Amino, (Ci- C6)Alkylamino, (Ci-C6)Halogenalkylamino, Di-(Ci-C6)Alkylamino, (C3-Cs)Cycloalkylamino, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylcarbonylamino, (Ci-C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3-C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (G- C6)Alkylthiocarbonylamino, (Ci-C6)Halogenalkylthiocarbonylamino, (G-CejAlkylthiocarbonyl- (Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C6) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, amino, (Ci- C6) alkylamino, (Ci-C6) haloalkylamino, di- (Ci-C6) alkylamino, (C 3 -Cs) cycloalkylamino, (Ci-C6 ) Alkylsulfonylamino, (Ci-C6) alkylcarbonylamino, (Ci-C6) haloalkylcarbonylamino, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-C6) haloalkylcarbonyl- (Ci-C6) alkyl-amino, (C3-C8) Cycloalkylcarbonylamino, (C3-C8) Cycloalkylcarbonyl- (Ci-C6) alkyl-amino, (G- C 6 ) Alkylthiocarbonylamino, (Ci-C 6 ) Haloalkylthiocarbonylamino, (G-CejAlkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-C 6 ) haloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (C3-
C8)Cycloalkylthiocarbonylamino, (C3-C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C2- C6)Alkenyl, (C2-C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2- C6)Alkinyl oder (C2-C6)Halogenalkinyl, (C3-C8)Cycloalkyl-(C2)alkinyl, (C3-Cs)Cycloalkyl-(G- C6)alkyl, (Ci-C6)Alkylaminocarbonylamino, Di-(Ci-C6)Alkylaminocarbonylamino, (C3- C8)Cycloalkylaminocarbonylamino, (Ci-C6)Halogenalkylaminocarbonylamino, (G- C6)Alkylaminocarbonyl-(Ci-C6)alkyl-amino, Di-(G-C6)Alkylaminocarbonyl-(G-C6)alkyl- amino, (C3-C8)Cycloalkylaminocarbonyl-(Ci-C6)alkyl-amino oder (G-C 8 ) Cycloalkylthiocarbonylamino, (C3-C8) Cycloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C2- C 6 ) alkenyl, (C2-C6) haloalkenyl, (C2-C6) cyanoalkenyl, (C3-Cs) cycloalkyl (C2) alkenyl, (C2- C 6 ) alkynyl or (C2-C6) haloalkynyl, (C3-C8) cycloalkyl- (C2) alkynyl, (C3-Cs) cycloalkyl- (G- C 6 ) alkyl, (Ci- C 6 ) alkylaminocarbonylamino, di- (Ci-C 6 ) alkylaminocarbonylamino, (C3- C 8 ) cycloalkylaminocarbonylamino, (Ci-C 6 ) haloalkylaminocarbonylamino, (G- C 6 ) alkylaminocarbonyl- (Ci-C 6 ) alkyl-amino, di - (GC 6 ) alkylaminocarbonyl- (GC 6 ) alkyl-amino, (C3-C8) cycloalkylaminocarbonyl- (Ci-C6) alkyl-amino or (G-
C6)Halogenalkylaminocarbonyl-(Ci-C6)alkyl-amino, oder für für einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituierten gesättigten, teilgesättigten oder heteroaromatischen Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist oder für einen einfach oder mehrfach, gleich oder verschieden substituierten gesättigten oder teilgesättigten carbocyclischen Ring oder für einen aromatischen Ring steht, wobei jeweils gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und/oder wobei als Substituenten jeweils in Frage kommen: Cyano, Carboxyl, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, SF5, Tri-(Ci-C6)alkylsilyl, (G-G)Cycloalkyl, (G-Cs)Cycloalkyl- (C3-C8)cycloalkyl, (Ci-C6)Alkyl-(C3-Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, Halogen-(C3-Cs)cycloalkyl, Cyano-(C3-Cs)cycloalkyl, (CVO,) Alkyl, ( C 1 - C 5) H a 1 g c n a 1 k y 1 , (G- CöjCyanoalkyl, (G-CejCyanohalogenalkyl, ( C 1 -CA,) H ydroxyal kyl , Hydroxycarbonyl-(G-C6)- alkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (C2-C6)Alkenyl, (G- CöjHalogenalkenyl, (C2-C6)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2-C6)Alkinyl, (G- GjHalogenalkinyl, (C2-C6)Cyanoalkinyl, (G-G)Alkoxy, (C 1 -G) Halogcnal koxy, (G- G)Cyanoalkoxy, (Ci-C6)Alkoxycarbonyl-(Ci-C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (G- GjAlkoxyimino, ( C 1 -CA,) H alogcnal koxy i m i no, (G-G)Alkylthio, (G -G ) Halogcnal kyl th io, (G- 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- Cöjalkyl, ( C 1 - C 5) A 1 k y 1 s u 1 f n y 1 , ( C 1 - C 5) H a 1 gc n a 1 k y 1 s u 1 f n y 1 , (Ci-C6)Alkoxy-(Ci-C 6 ) haloalkylaminocarbonyl (Ci-C 6 ) alkyl-amino, or for a saturated, partially saturated or heteroaromatic ring which is optionally mono- or polysubstituted, identically or differently substituted and in which at least one carbon atom has been replaced by a heteroatom or for one single or multiple, identically or differently substituted, saturated or partially saturated carbocyclic ring or an aromatic ring, where in each case at least one carbonyl group can optionally be included and / or where the following are possible as substituents: cyano, carboxyl, halogen, nitro, acetyl, Hydroxy, amino, SCN, SF5, tri- (Ci-C 6 ) alkylsilyl, (GG) cycloalkyl, (G-Cs) cycloalkyl- (C3-C8) cycloalkyl, (Ci-C6) alkyl- (C3-Cs) cycloalkyl , (Ci-C6) haloalkyl- (C3-Cs) cycloalkyl, halo- (C3-Cs) cycloalkyl, cyano- (C3-Cs) cycloalkyl, (CVO,) alkyl, (C 1 -C 5) H a 1 gcna 1 ky 1, (G-C ö j-cyanoalkyl, (G-Cej-cyanohaloalkyl, (C 1 -CA,) hydroxyalkyl, hydroxycarbonyl- (GC 6 ) -alkoxy , (Ci-C 6 ) alkoxycarbonyl- (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkyl, (C2-C6) alkenyl, (G- C ö jhaloalkenyl, (C2- C6) cyanoalkenyl, (C3-Cs) cycloalkyl- (C2) alkenyl, (C2-C6) alkynyl, (G- Gjhaloalkynyl, (C2-C6) cyanoalkynyl, (GG) alkoxy, (C 1 -G) haloalkynyl, ( G- G) cyanoalkoxy, (Ci-C 6) alkoxycarbonyl (Ci-C 6) alkoxy, (Ci-C 6) alkoxy (Ci-C 6) alkoxy, (G- GjAlkoxyimino, (C 1 -CA,) H alogcnal koxy imi no, (GG) alkylthio, (G-G) Halogcnal th io alkyl, (G- C 6) alkoxy (Ci-C 6) 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) alkylsulfinyl (C ö Ci jalkyl, (C 1 - C 5) A 1 ky 1 su 1 fny 1, (C 1 - C 5) H a 1 gc na 1 ky 1 su 1 fny 1, (Ci-C 6 ) alkoxy- (Ci-
Cöjalkylsulfonyl, (Ci-C6)Alkylsulfonyl-(Ci-C6)alkyl, ( C 1 -C(t) A 1 ky 1 su Ifony loxy , (Ci-C ö jalkylsulfonyl, (Ci-C 6 ) alkylsulfonyl- (Ci-C 6 ) alkyl, (C 1 -C (t) A 1 ky 1 su Ifony loxy, (Ci-
C ,) Halogcnal ky 1 su Ifonyloxy, ( C 1 -C ,) A 1 ky learbony 1 , (C 1 -C ,) Halogcnal kylcarbonyl , (Ci- CölAlkylcarbonyloxy, ( C 1 -G.) A 1 koxycarbony 1 , (G-G>) Halogcnal koxycarbonyl, Aminocarbonyl, (Ci-CejAlkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci-C,) Halogcnal ky 1 su Ifonyloxy, (C 1 -C,) A 1 ky learbony 1, (C 1 -C,) Halogcnal kylcarbonyl, (Ci- C ö lAlkylcarbonyloxy, (C 1 -G.) A 1 koxycarbony 1 , (GG >) Halogcnal koxycarbonyl, aminocarbonyl, (Ci-CejAlkylaminocarbonyl, Di- (Ci-C 6 ) alkyl-aminocarbonyl, (Ci-
C ,) Halogcnal kyl aminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-Ce)- alkenylaminocarbonyl, (C CslCycloal kyl aminocarbonyl, ( C 1 -CA,) A 1 ky 1 sulfony 1 am i no, (Ci- C6)Alkylamino, Di-(G-C6)Alkylamino, (C 1 -C ,) Halogcnal kylamino, (C3-Cs)Cycloalkylamino, Aminosulfonyl, ( C 1 - C 5) A 1 k y 1 a m i n o s u 1 f o n y 1 , Di-(G-C6)alkylaminosulfonyl, (Ci-C,) Halogcnal kyl aminocarbonyl, (C2-C6) alkenylaminocarbonyl, di- (C2-Ce) - alkenylaminocarbonyl, (C CslCycloal kyl aminocarbonyl, (C 1 -CA,) A 1 ky 1 sulfony 1 am i no, (Ci- C 6 ) alkylamino, di- (GC 6 ) alkylamino, (C 1 -C,) halogcnal kylamino, (C3-Cs) cycloalkylamino, aminosulfonyl, (C 1 - C 5) A 1 ky 1 aminosu 1 fony 1, di- (GC 6 ) alkylaminosulfonyl, (Ci-
C6)Alkylsulfoximino, Aminothiocarbonyl, (C 1 -G>) A 1 kyl am i noth iocarbony 1 , Di-(G- C6)alkylaminothiocarbonyl, (Ci-C6)Halogenalkylaminothiocarbonyl, (C3-C 6 ) alkylsulfoximino, aminothiocarbonyl, (C 1 -G >) A 1 kyl am i noth iocarbony 1, di- (G- C 6 ) alkylaminothiocarbonyl, (Ci-C 6 ) haloalkylaminothiocarbonyl, (C 3 -
C8)Cycloalkylaminothiocarbonyl, (Ci-C6)Alkylcarbonylamino, (Ci-C 8 ) Cycloalkylaminothiocarbonyl, (Ci-C 6 ) Alkylcarbonylamino, (Ci-
C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C 6 ) haloalkylcarbonylamino, (Ci-C 6 ) alkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3- C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Alkylthiocarbonylamino, (Ci-C 6) haloalkylcarbonyl (Ci-C6) alkyl-amino, (C 3 -C 8) cycloalkylcarbonylamino, (C 3 - C 8) cycloalkylcarbonyl (Ci-C6) alkyl-amino, (Ci-C 6) alkylthiocarbonylamino , (Ci-
C6)Halogenalkylthiocarbonylamino, (Ci-C6)Alkylthiocarbonyl-(Ci-C6)alkyl-amino, (Ci-C 6 ) haloalkylthiocarbonylamino, (Ci-C 6 ) alkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylthiocarbonylamino, (C3- C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, Hetaryl, Oxo-Hetaryl, Halogen-Hetaryl, Halogen-Oxo-Hetaryl, Cyano-Hetaryl, Cyano-Oxo-Hetaryl, (Ci-C6)Halogenalkyl-Hetaryl oder (Ci-C6)Halogenalkyl-Oxo-Hetaryl, C 6) Halogenalkylthiocarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8) Cycloalkylthiocarbonylamino, (C 3 - C 8) Cycloalkylthiocarbonyl- (Ci-C6) alkyl-amino, hetaryl, hetaryl-oxo, halogen -Hetaryl, halo-oxo-hetaryl, cyano-hetaryl, cyano-oxo-hetaryl, (Ci-C 6 ) haloalkyl-hetaryl or (Ci-C 6 ) haloalkyl-oxo-hetaryl,
R4, R5, R6, R7 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (Ci-C3)Alkyl oder (Ci-C3)Halogenalkyl stehen, R 4 , R 5 , R 6 , R 7 independently represent hydrogen, cyano, halogen, (Ci-C 3 ) alkyl or (Ci-C 3 ) haloalkyl,
Y für Sauerstoff, =N-H oder =N-CN steht, Y stands for oxygen, = N-H or = N-CN,
Z für -NR8, Sauerstoff oder Schwefel steht, wobei Z is -NR 8 , oxygen or sulfur, where
R8 für Wasserstoff, (Ci-C6)Alkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Cyanoalkyl, (Ci-R 8 for hydrogen, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (Ci-C6) cyanoalkyl, (Ci-
C6)Hydroxyalkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (Ci-C6)Halogenalkoxy-(Ci-C6)alkyl, (C2- Ce)Alkenyl, (C2-C6)Alkenyloxy-(Ci-C6)alkyl, (C2-C6)Halogenalkenyloxy-(Ci-C6)alkyl, (C2- C6)Halogenalkenyl, (C2-C6)Cyanoalkenyl, (C2-C6)Alkinyl, (C2-C6)Halogenalkinyl oder (C3- Cs)Cycloalkyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. C6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C6) alkyl, (Ci-C6) haloalkoxy (Ci-C6) alkyl, (C 2 - Ce) alkenyl, (C 2 -C 6 ) alkenyloxy ( Ci-C 6) alkyl, (C 2 -C 6) Halogenalkenyloxy- (Ci-C 6) alkyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6 ) haloalkynyl or (C 3 -Cs) cycloalkyl, m is 0 or 1, n is 0 or 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C4)Alkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl oder (C3- C6)Cycloalkyl steht, R 1 for (Ci-C 4 ) alkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) alkoxy- (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 or (C 3 -C6) cycloalkyl,
R2 für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-R 2 for hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-
C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C4)Halogenalkoxy-(Ci-C4)alkyl, (C3- C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3-C6)Cycloalkyl, Halogen(C3-C6)cycloalkyl, Cyano(C3-C6)cycloalkyl, (Ci-C4)Alkylthio-(Ci-C4)alkyl, (Ci- C4)Halogenalkylthio-(Ci-C4)alkyl, (Ci-C4)Alkylsulfinyl-(Ci-C4)alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy (Ci-C 4 ) alkyl, (C 3 - C 6 ) cycloalkyl, (C 3 - C 6 ) cycloalkyl (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, cyano (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-
C4)Halogenalkylsulfinyl-(Ci-C4)alkyl, (Ci-C4)Alkylsulfonyl-(Ci-C4)alkyl oder (Ci- C4)Halogenalkylsulfonyl-(Ci-C4)alkyl steht, R3 für Wasserstoff, Halogen, Cyano, Nitro, (G-CejAlkyl, (G-GjCycloalkyl, Cyano(G- Gjcycloalkyl, (Ci-C6)Halogenalkyl, (Ci-C6)Alkoxy, (Ci-C6)Halogenalkoxy, (Ci-C6)Alkylthio, (Ci-C6)Halogenalkylthio, (Ci-C6)Alkylsulfinyl, (Ci-C6)Halogenalkylsulfinyl, (G- C6)Alkylsulfonyl, (Ci-C6)Halogenalkylsulfonyl, SCN, (Ci-C6)Alkylcarbonyl, (G- C6)Halogenalkylcarbonyl, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl,C 4 ) haloalkylsulfinyl (Ci-C 4 ) alkyl, (Ci-C 4 ) alkylsulfonyl (Ci-C 4 ) alkyl or (Ci- C 4 ) haloalkylsulfonyl (Ci-C 4 ) alkyl, R 3 for hydrogen, halogen, cyano, nitro, (G-CejAlkyl, (G-GjCycloalkyl, Cyano (G-Gjcycloalkyl, (Ci-C6) haloalkyl, (Ci-C6) alkoxy, (Ci-C6) haloalkoxy, (Ci -C6) alkylthio, (Ci-C6) haloalkylthio, (Ci-C6) alkylsulfinyl, (Ci-C6) haloalkylsulfinyl, (G- C6) alkylsulfonyl, (Ci-C6) haloalkylsulfonyl, SCN, (Ci-C6) alkylcarbonyl, ( G- C6) haloalkylcarbonyl, (Ci-C6) alkoxycarbonyl, (Ci-C6) haloalkoxycarbonyl,
Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (G- C6)Halogenalkylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (G- C6)Alkylaminothiocarbonyl, Di-(Ci-C6)alkylaminothiocarbonyl, (G-Aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (Ci-C6) alkyl-aminocarbonyl, (G- C6) haloalkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, aminothiocarbonyl, (G- C6) alkylaminothiocarbonyl, di- (Ci- C6) alkylaminothiocarbonyl, (G-
C6)Halogenalkylaminothiocarbonyl, (C3-C8)Cycloalkylaminothiocarbonyl, Amino, (G- C6)Alkylamino, (Ci-C6)Halogenalkylamino, Di-(Ci-C6)Alkylamino, (C3-C8)Cycloalkylamino, (Ci-C6)Alkylsulfonylamino, (Ci-C6)Alkylcarbonylamino, (Ci-C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3-C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (G- C6)Alkylthiocarbonylamino, (Ci-C6)Halogenalkylthiocarbonylamino, (G-CejAlkylthiocarbonyl- (Ci-C6)alkyl-amino, (Ci-C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (G-C6) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, amino, (G- C6) alkylamino, (Ci-C6) haloalkylamino, di- (Ci-C6) alkylamino, (C 3 -C 8 ) cycloalkylamino, (Ci- C6) alkylsulfonylamino, (Ci-C6) alkylcarbonylamino, (Ci-C6) haloalkylcarbonylamino, (Ci-C6) alkylcarbonyl- (Ci-C6) alkyl-amino, (Ci-C6) haloalkylcarbonyl- (Ci-C6) alkyl-amino, (C 3 -C 8 ) Cycloalkylcarbonylamino, (C 3 -C 8 ) Cycloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (G- C6) Alkylthiocarbonylamino, (Ci-C6) Haloalkylthiocarbonylamino, (G-CejAlkylthiocarbonyl- (Ci- C6) alkyl-amino, (Ci-C6) haloalkylthiocarbonyl- (Ci-C6) alkyl-amino, (G-
C8)Cycloalkylthiocarbonylamino, (C3-C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, (G- Ce)Alkenyl, (C2-C6)Halogenalkenyl, (G-G)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (G- C6)Alkinyl, (C2-C6)Halogenalkinyl, (C3-C8)Cycloalkyl-(C2)alkinyl, (G-G)Cycloalkyl-(G- C6)alkyl, (Ci-C6)Alkylaminocarbonylamino, Di-(Ci-C6)Alkylaminocarbonylamino, (G- C8)Cycloalkylaminocarbonylamino, (Ci-C6)Halogenalkylaminocarbonylamino, (G- C6)Alkylaminocarbonyl-(Ci-C6)alkyl-amino, Di-(G-G)Alkylaminocarbonyl-(G-C6)alkyl- amino, (C3-C8)Cycloalkylaminocarbonyl-(Ci-C6)alkyl-amino oder (G-C8) Cycloalkylthiocarbonylamino, (C 3 -C 8 ) Cycloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (G- Ce) alkenyl, (C 2 -C 6 ) haloalkenyl, (GG) cyanoalkenyl, (C 3 -Cs) Cycloalkyl- (C 2 ) alkenyl, (G- C6) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 8 ) cycloalkyl- (C 2 ) alkynyl, (GG) cycloalkyl- (G- C6) alkyl , (Ci-C6) alkylaminocarbonylamino, di- (Ci-C6) alkylaminocarbonylamino, (G- C8) cycloalkylaminocarbonylamino, (Ci-C6) haloalkylaminocarbonylamino, (G- C6) alkylaminocarbonyl- (Ci-C6) alkylamino, di- ( GG) alkylaminocarbonyl- (G-C6) alkyl-amino, (C 3 -C 8 ) cycloalkylaminocarbonyl- (Ci-C 6 ) alkyl-amino or (G-
C6)Halogenalkylaminocarbonyl-(Ci-C6)alkyl-amino, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Aryl, Hetaryl, Cyclopentenyl oder Cyclohexenyl steht, wobei (im Fall von Hetaryl) gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und wobei als Substituenten jeweils in Frage kommen: Cyano, Carboxyl, Halogen, Nitro, Acetyl, Hydroxy, Amino, SCN, SF5, Tri-(Ci-C6)alkylsilyl, (C3-Cs)Cycloalkyl, (C3-C8)Cycloalkyl-(C3-Cs)cycloalkyl, (G-G)Alkyl- (C3-Cs)cycloalkyl, (Ci-C6)Halogenalkyl-(C3-Cs)cycloalkyl, Halogen-(C3-Cs)cycloalkyl, Cyano- (C3-C8)cycloalkyl, (G-G)Alkyl, ( C -G>) H al ogcn al ky 1 , (Ci-CöjCyanoalkyl, (G-C6) Haloalkylaminocarbonyl- (Ci-C6) alkyl-amino, or for each optionally mono- or polysubstituted, identically or differently substituted aryl, hetaryl, cyclopentenyl or cyclohexenyl, where (in the case of hetaryl) at least one carbonyl group may optionally be included and where Possible substituents are: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF 5 , tri- (Ci-C6) alkylsilyl, (C 3 -Cs) cycloalkyl, (C 3 -C 8 ) Cycloalkyl- (C 3 -Cs) cycloalkyl, (GG) alkyl- (C 3 -Cs) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cs) cycloalkyl, halo- (C 3 -Cs) cycloalkyl, cyano - (C 3 -C 8 ) cycloalkyl, (GG) alkyl, (C -G >) H al ogcn al ky 1, (Ci-C ö j-cyanoalkyl, (G-
CöjCyanohalogenalkyl, ( C -G,) H ydroxyal kyl , Hydroxycarbonyl-(G-C6)-alkoxy, (Ci- C6)Alkoxycarbonyl-(Ci-C6)alkyl, (Ci-C6)Alkoxy-(Ci-C6)alkyl, (C2-Ce)Alkenyl, (C2- CöjHalogenalkenyl, (C2-Ce)Cyanoalkenyl, (C3-Cs)Cycloalkyl-(C2)alkenyl, (C2-C6)Alkinyl, (C2- CöjHalogenalkinyl, (C2-C6)Cyanoalkinyl, (Ci-CejAlkoxy, (C -G,) Halogcnal koxy, (Ci- CöjCyanoalkoxy, (G-C6)Alkoxycarbonyl-(G-C6)alkoxy, (Ci-C6)Alkoxy-(Ci-C6)alkoxy, (Ci- CöjAlkoxyimino, ( C -C ,) H alogcnal koxy i m i no, (Ci-CejAlkylthio, (C -C ,) Halogcnal kyl th io, (G- 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)Halogenalkylsulfonyloxy, (Ci-C6)Alkylcarbonyl, (Ci-C6)Halogenalkylcarbonyl, (Ci- C6)Alkylcarbonyloxy, (Ci-C6)Alkoxycarbonyl, (Ci-C6)Halogenalkoxycarbonyl, Aminocarbonyl, (Ci-C6)Alkylaminocarbonyl, Di-(Ci-C6)alkyl-aminocarbonyl, (Ci-C ö jCyanohalogenalkyl, (C -G,) Hydroxyal kyl, Hydroxycarbonyl- (G-C6) -alkoxy, (Ci- C6) Alkoxycarbonyl- (Ci-C6) alkyl, (Ci-C6) Alkoxy- (Ci-C6) alkyl, (C 2 -Ce) alkenyl, (C 2 -C ö jhaloalkenyl, (C 2 -Ce) cyanoalkenyl, (C 3 -Cs) cycloalkyl- (C 2 ) alkenyl, (C 2 -C 6 ) alkynyl, ( C 2 - C ö jHalogenalkinyl, (C 2 -C 6) cyanoalkynyl, (Ci-CejAlkoxy, (C -G) Halogcnal koxy, (Ci- C ö jCyanoalkoxy, (G-C6) alkoxycarbonyl (G-C6) alkoxy , (Ci-C6) alkoxy- (Ci-C6) alkoxy, (Ci- C ö jalkoxyimino, (C -C,) H alogcnal koxy imi no, (Ci-CejAlkylthio, (C -C,) Halogcnal kyl thio, (G- C 6) alkoxy (Ci-C 6) alkylthio, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6) alkylsulfinyl, (Ci- C 6) haloalkylsulfinyl, (C -C 6) alkoxy (Ci-C 6 alkylsulfinyl), (Ci-C 6) alkylsulfinyl (Ci C 6 ) 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 ) haloalkylsulfonyloxy, (Ci-C 6 ) alkylcarbonyl, (Ci-C 6 ) haloalkylcarbonyl, (Ci-C 6 ) alkylcarbonyloxy, (Ci-C 6 ) alkoxycarbonyl , (Ci-C 6 ) haloalkoxycarbonyl, aminocarbonyl, (Ci-C 6 ) alkylaminocarbonyl, di- (Ci-C 6 ) alkyl-aminocarbonyl, (Ci-
C6)Halogenalkylaminocarbonyl, (C2-C6)Alkenylaminocarbonyl, Di-(C2-C6)- alkenylaminocarbonyl, (C3-C8)Cycloalkylaminocarbonyl, (Ci-C6)Alkylsulfonylamino, (Ci- C6)Alkylamino, Di-(Ci-C6)Alkylamino, (Ci-C6)Halogenalkylamino, (C3-C8)Cycloalkylamino, Aminosulfonyl, (Ci-C6)Alkylaminosulfonyl, Di-(Ci-C6)alkylaminosulfonyl, (Ci- C6)Alkylsulfoximino, Aminothiocarbonyl, (Ci-C6)Alkylaminothiocarbonyl, Di-(Ci- C6)alkylaminothiocarbonyl, (Ci-C6)Halogenalkylaminothiocarbonyl, (C3-C 6 ) haloalkylaminocarbonyl, (C2-C6) alkenylaminocarbonyl, di- (C2-C6) alkenylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, (Ci-C 6 ) alkylsulfonylamino, (Ci- C 6 ) alkylamino, di- (Ci- C 6 ) alkylamino, (Ci-C 6 ) haloalkylamino, (C3-C8) cycloalkylamino, aminosulfonyl, (Ci-C 6 ) alkylaminosulfonyl, di- (Ci-C 6 ) alkylaminosulfonyl, (Ci- C 6 ) alkylsulfoximino, aminothiocarbonyl, (Ci-C 6 ) alkylaminothiocarbonyl, di- (Ci- C 6 ) alkylaminothiocarbonyl, (Ci-C 6 ) haloalkylaminothiocarbonyl, (C3-
C8)Cycloalkylaminothiocarbonyl, (Ci-C6)Alkylcarbonylamino, (Ci-C 8 ) Cycloalkylaminothiocarbonyl, (Ci-C 6 ) Alkylcarbonylamino, (Ci-
C6)Halogenalkylcarbonylamino, (Ci-C6)Alkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C 6 ) haloalkylcarbonylamino, (Ci-C 6 ) alkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylcarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylcarbonylamino, (C3- C8)Cycloalkylcarbonyl-(Ci-C6)alkyl-amino, (Ci-C6)Alkylthiocarbonylamino, (Ci-C 6 ) haloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (C3-C8) cycloalkylcarbonylamino, (C3- C 8 ) cycloalkylcarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-C 6 ) alkylthiocarbonylamino, (Ci -
C6)Halogenalkylthiocarbonylamino, (Ci-C6)Alkylthiocarbonyl-(Ci-C6)alkyl-amino, (Ci-C 6 ) haloalkylthiocarbonylamino, (Ci-C 6 ) alkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (Ci-
C6)Halogenalkylthiocarbonyl-(Ci-C6)alkyl-amino, (C3-C8)Cycloalkylthiocarbonylamino, (C3- C8)Cycloalkylthiocarbonyl-(Ci-C6)alkyl-amino, Hetaryl, Oxo-Hetaryl, Halogen-Hetaryl, Halogen-Oxo-Hetaryl, Cyano-Hetaryl, Cyano-Oxo-Hetaryl, (Ci-C6)Halogenalkyl-Hetaryl oder (Ci-C6)Halogenalkyl-Oxo-Hetaryl, C 6 ) haloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, (C3-C8) cycloalkylthiocarbonylamino, (C3- C 8 ) cycloalkylthiocarbonyl- (Ci-C 6 ) alkyl-amino, hetaryl, oxo-hetaryl, halo-hetaryl, Halogen-oxo-hetaryl, cyano-hetaryl, cyano-oxo-hetaryl, (Ci-C 6 ) haloalkyl-hetaryl or (Ci-C 6 ) haloalkyl-oxo-hetaryl,
R4, R5, R6, R7 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (C1-C3) Alkyl oder (Ci-C3)Halogenalkyl stehen, R 4 , R 5 , R 6 , R 7 independently represent hydrogen, cyano, halogen, (C 1 -C 3 ) alkyl or (Ci-C3) haloalkyl,
Y für Sauerstoff, =N-H oder =N-CN steht, Y stands for oxygen, = N-H or = N-CN,
Z für -NR8, Sauerstoff oder Schwefel steht, wobei Z is -NR 8 , oxygen or sulfur, where
R8 für Wasserstoff, (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)Halogenalkinyl oder (C3- C6)Cycloalkyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. R 8 for hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) cyanoalkyl, (Ci- C4) hydroxyalkyl, (Ci-C4) alkoxy- (Ci-C4) alkyl, (Ci- C4) haloalkoxy- (Ci-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkenyloxy- (Ci-C4) alkyl, (C2-C4) haloalkenyloxy- (Ci-C4) alkyl, (C2-C4 ) Haloalkenyl, (C2-C4) cyanoalkenyl, (C2-C4) alkynyl, (C2-C4) haloalkynyl or (C 3 -C 6 ) cycloalkyl, m is 0 or 1, n is 0 or 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher Compounds of formula (I) according to claim 1, in which
R1 für (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl oder (C3- C6)Cycloalkyl steht, R 1 for (Ci-C4) alkyl, (Ci-C4) haloalkyl, (C2-C4) alkenyl, (C2-C4) haloalkenyl or (C 3 - C 6 ) cycloalkyl,
R2 für Wasserstoff, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (C3-C6)Cycloalkyl oder Halogen(C3-C6)cycloalkyl steht, R 2 represents hydrogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 6 ) cycloalkyl or halogen (C 3 -C 6 ) cycloalkyl,
R3 für Wasserstoff, Halogen, Cyano, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, Cyano(C3- C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-R 3 for hydrogen, halogen, cyano, (Ci-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C6) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy , (Ci-C 4 ) haloalkoxy, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkyl-aminocarbonyl, (Ci-
C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, Amino, (Ci-C4)Alkylamino, (Ci-C4)Halogenalkylamino, Di-(Ci-C4)Alkylamino, (C3-C6)Cycloalkylamino, (Ci- C4)Alkylsulfonylamino, (Ci-C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci- C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3- C6)Cycloalkylcarbonylamino, (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3-C6)Cycloalkyl-(C2)alkenyl, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Furanyl, Pyrazolyl, Thiazolyl, Oxazolyl oder Imidazolyl steht, wobei (im Fall von Hetaryl) gegebenenfalls mindestens eine Carbonylgruppe enthalten sein kann und wobei als Substituenten jeweils in Frage kommen: Cyano, Halogen, Nitro, Acetyl, Hydroxy, Amino, SF5, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl-(C3- Gjcycloalkyl, (Ci-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Cyanoalkyl, (Ci-C4)Cyanohalogenalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (C2-C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2- C4)Cyanoalkenyl, (C3-C6)Cycloalkyl-(C2)alkenyl, (C2-C4)Alkinyl, (C2-C4)Halogenalkinyl, (C2- C4)Cyanoalkinyl, (Ci-C4)Alkoxy, (Ci-C4)Halogenalkoxy, (Ci-C4)Cyanoalkoxy, (Ci-C4)Alkoxy- (Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Halogenalkoxyimino, (Ci-C4)Alkylthio, (Ci-C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, di- (Ci-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkylamino , (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl - (Ci-C 2 ) alkyl-amino, (C 3 -C 6 ) cycloalkylcarbonylamino, (C 3 -C 6) cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or for phenyl, pyridyl, pyrimidyl, pyridazinyl, each optionally substituted one or more times, identically or differently, Thiophenyl, furanyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, where (in the case of hetaryl) at least one carbonyl group may optionally be included and where the following are possible as substituents: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 -C 6 ) cycloalkyl l, (Ci-C4) alkyl- (C3- cycloalkyl, (Ci-C 4 ) haloalkyl- (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl, cyano - (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) cyanohaloalkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy (Ci-C 2) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 - C 4) cyanoalkenyl, (C 3 -C 6) cycloalkyl (C 2) alkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) haloalkynyl, (C 2 - C 4) cyanoalkynyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) cyanoalkoxy , (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkoxy, (Ci-C 4 ) alkoxyimino, (Ci-C 4 ) haloalkoxyimino, (Ci-C 4 ) alkylthio, (Ci-
C4)Halogenalkylthio, (Ci-C4)Alkylthio-(Ci-C2)alkyl, (Ci-C4)Alkylsulfinyl, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylthio (Ci-C 2 ) alkyl, (Ci-C 4 ) alkylsulfinyl, (Ci-
C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci- C4)Alkylsulfonyloxy, (Ci-C4)Halogenalkylsulfonyloxy, (Ci-C4)Alkylcarbonyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-C 4 ) haloalkylsulfonyl, (Ci- C 4 ) alkylsulfonyloxy, (Ci-C 4 ) haloalkylsulfonyloxy, (Ci-C 4 ) alkylcarbonyl, (Ci-
C4)Halogenalkylcarbonyl, Aminocarbonyl, (Ci-C4)Alkylaminocarbonyl, (Ci-C 4 ) haloalkylcarbonyl, aminocarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (Ci-
C4)Halogenalkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (C3-C 4 ) haloalkylaminocarbonyl, di- (Ci-C 4 ) alkyl-aminocarbonyl, (C 3 -
C6)Cycloalkylaminocarbonyl, Aminothiocarbonyl, (Ci-C4)Alkylaminothiocarbonyl, Di-(Ci- C4)alkylaminothiocarbonyl, (Ci-C4)Halogenalkylaminothiocarbonyl, (C3-C 6 ) Cycloalkylaminocarbonyl, aminothiocarbonyl, (Ci-C 4 ) alkylaminothiocarbonyl, di- (Ci- C 4 ) alkylaminothiocarbonyl, (Ci-C 4 ) haloalkylaminothiocarbonyl, (C 3 -
Cf.jCycloalkyl aminothiocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci-C f .jCycloalkyl aminothiocarbonyl, (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, di- (Ci-
C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, Aminosulfonyl, (Ci- C4)Alkylaminosulfonyl, Di-(Ci-C4)alkyl-aminosulfonyl, (Ci-C4)Alkylcarbonylamino, (Ci- C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl, (Ci- C 4 ) alkylaminosulfonyl, di- (Ci-C 4 ) alkyl-aminosulfonyl, (Ci-C 4 ) Alkylcarbonylamino, (Ci- C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-C 2 ) alkyl-amino, (Ci-
C2)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylcarbonylamino, (C3- C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino, (Ci-C4)Alkylthiocarbonylamino, (Ci- C4)Halogenalkylthiocarbonylamino, (Ci-C4)Alkylthiocarbonyl-(Ci-C2)alkyl-amino, (Ci- C4)Halogenalkylthiocarbonyl-(Ci-C2)alkyl-amino, (C3-C6)Cycloalkylthiocarbonylamino, (C3- C6)Cycloalkylthiocarbonyl-(Ci-C2)alkyl-amino oder gegebenenfalls durch Halogen substituiertes Pyridyl, C 2) haloalkylcarbonyl (Ci-C 2) alkyl-amino, (C 3 -C 6) cycloalkylcarbonylamino, (C 3 - C 6) cycloalkylcarbonyl (Ci-C 2) alkyl amino, (Ci-C4) alkylthiocarbonylamino , (Ci- C 4 ) haloalkylthiocarbonylamino, (Ci-C 4 ) alkylthiocarbonyl- (Ci-C 2 ) alkyl-amino, (Ci- C 4 ) haloalkylthiocarbonyl- (Ci-C 2 ) alkyl-amino, (C 3 -C 6 ) cycloalkylthiocarbonylamino, (C 3 -C 6 ) Cycloalkylthiocarbonyl- (Ci-C 2 ) alkyl-amino or optionally halogen-substituted pyridyl,
R4, R5, R6, R7 identisch sind und entweder für Wasserstoff oder für Fluor stehen, R 4 , R 5 , R 6 , R 7 are identical and either represent hydrogen or fluorine,
Y für Sauerstoff oder =N-H steht, Y stands for oxygen or = N-H,
Z für -NR8 oder Sauerstoff steht, wobei R8 für Wasserstoff oder (Ci-C4)Alkyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. Z stands for —NR 8 or oxygen, where R 8 stands for hydrogen or (Ci-C 4 ) alkyl, m stands for 0 or 1, n stands for 0 or 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher Compounds of formula (I) according to claim 1, in which
R1 für Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl steht,R 1 represents methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R2 für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, cyclo-Propyl, n-Butyl, i-Butyl, tert.- Butyl, cyclo-Butyl, Fluormethyl, Difluormethyl, Trifluormethyl, Fluorethyl, Difluorethyl, Trifluorethyl, Tetrafluorethyl oder Pentafluorethyl steht, R 2 for hydrogen, methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, Is tetrafluoroethyl or pentafluoroethyl,
R3 für Wasserstoff, Halogen, (Ci-C4)Alkyl, (C3-C6)Cycloalkyl, (Ci-C4)Halogenalkyl, (C2- C4)Alkenyl, (C2-C4)Halogenalkenyl, (C2-C4)Cyanoalkenyl oder (C3-C6)Cycloalkyl-(C2)alkenyl steht, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Acetyl, Hydroxy, Amino, SF5, (C3- GjCycloalkyl, (Ci-C4)Alkyl-(C3-C6)cycloalkyl, (Ci-C4)Halogenalkyl-(C3-C6)cycloalkyl, Halogen(C3-C6)cycloalkyl, (Ci-C4)Alkyl, Cyano-(C3-Cs)cycloalkyl, (Ci-C4)Halogenalkyl, (Ci- C4)Cyanoalkyl, (Ci-C4)Hydroxyalkyl, (Ci-C4)Alkoxy-(Ci-C2)alkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy, (Ci-C4)Alkoxy-(Ci-C2)alkoxy, (Ci-C4)Alkoxyimino, (Ci-C4)Alkylthio, (Ci- C4)Halogenalkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Halogenalkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci-C4)Halogenalkylsulfonyl, (Ci-C4)Alkylcarbonyl, Aminocarbonyl, (Ci-R 3 is hydrogen, halogen, (Ci-C 4) alkyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) haloalkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl or (C 3 -C 6 ) cycloalkyl- (C 2 ) alkenyl, or phenyl, pyridyl which is optionally mono- or polysubstituted, identically or differently substituted - via a carbon atom to the remainder of the molecule , Pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or imidazolyl, where the following are possible as substituents: cyano, fluorine, chlorine, bromine, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 - GjCycloalkyl, (Ci-C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) haloalkyl- (C 3 -C 6 ) cycloalkyl, halogen (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl, cyano- (C 3 -Cs) cycloalkyl, (Ci-C 4 ) haloalkyl, (Ci- C 4 ) cyanoalkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) alkoxy- (Ci-C 2 ) alkyl, (Ci -C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C 4) alkoxy- (Ci-C2) alkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci- C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylcarbonyl, aminocarbonyl, (Ci-
C4)Alkylaminocarbonyl, Di-(Ci-C4)alkyl-aminocarbonyl, (Ci-C4)Halogenalkylaminocarbonyl, (C3-C6)Cycloalkylaminocarbonyl, (Ci-C4)Alkylsulfonylamino, (Ci-C4)Alkylamino, Di-(Ci- C4)Alkylamino, (Ci-C4)Halogenalkylamino, (C3-C6)Cycloalkylamino, (Ci-C 4 ) alkylaminocarbonyl, di- (Ci-C 4 ) alkyl aminocarbonyl, (Ci-C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, (Ci-C 4 ) alkylsulfonylamino, (Ci-C 4 ) alkylamino, Di- (Ci- C 4 ) alkylamino, (Ci-C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, (Ci-
C4)Alkylcarbonylamino, (Ci-C4)Halogenalkylcarbonylamino, (Ci-C4)Alkylcarbonyl-(Ci-C 4 ) alkylcarbonylamino, (Ci-C 4 ) haloalkylcarbonylamino, (Ci-C 4 ) alkylcarbonyl- (Ci-
C2)alkyl-amino, (Ci-C4)Halogenalkylcarbonyl-(Ci-C2)alkyl-amino, (C3-C 2 ) alkyl-amino, (Ci-C 4 ) haloalkylcarbonyl- (Ci-C 2 ) alkyl-amino, (C 3 -
C6)Cycloalkylcarbonylamino, (C3-C6)Cycloalkylcarbonyl-(Ci-C2)alkyl-amino oder gegebenenfalls einfach durch Chlor oder Brom substituiertes Pyridyl, oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes - Pyrazolyl, Triazolyl oder Imidazolyl steht, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Nitro, Hydroxy, Amino, (C3-C6)Cycloalkyl, (Ci-C4)Alkyl, (Ci-C4)Halogenalkyl, (Ci-C4)Alkoxy, (Ci- C4)Halogenalkoxy oder Aminocarbonyl, C 6 ) Cycloalkylcarbonylamino, (C 3 -C 6 ) Cycloalkylcarbonyl- (Ci-C 2 ) alkyl-amino or optionally pyridyl which is monosubstituted or monosubstituted by chlorine or bromine, or for each optionally monosubstituted or polysubstituted, identically or differently substituted - via a nitrogen atom to The remainder of the molecule is bridged - pyrazolyl, triazolyl or imidazolyl, with possible substituents each being: cyano, fluorine, chlorine, bromine, nitro, hydroxy, amino, (C 3 -C 6 ) cycloalkyl, (Ci-C 4 ) alkyl , (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci- C 4 ) haloalkoxy or aminocarbonyl,
R4, R5, R6, R7 identisch sind und entweder für Wasserstoff oder für Fluor stehen, R 4 , R 5 , R 6 , R 7 are identical and either represent hydrogen or fluorine,
Y für Sauerstoff oder =N-H steht, Y stands for oxygen or = N-H,
Z für -NR8 oder Sauerstoff steht, wobei R8 für Wasserstoff oder Methyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. Z stands for —NR 8 or oxygen, where R 8 stands for hydrogen or methyl, m stands for 0 or 1, n stands for 0 or 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher R1 für Ethyl steht, Compounds of the formula (I) according to Claim 1, in which R 1 represents ethyl,
R2 für Methyl steht, R 2 represents methyl,
R3 für Wasserstoff, Brom, Cyclopropyl, Trifluormethyl, Tetrafluorethyl, Pentafluorethyl oder für jeweils gegebenenfalls einfach oder mehrfach, gleich oder verschieden substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Phenyl, Pyridyl, Pyrimidyl, Pyridazinyl, Thiophenyl, Thiazolyl, Oxazolyl oder Imidazolyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Trifluorethyl, Tetrafluorethyl, Pentafluorethyl, SF5, 2-Cyano-2-propyl, Cyclopropyl, 1 -Cyano- 1 -cyclopropyl, 1- Fluor-1 -cyclopropyl, 1 -Trifluormethyl- 1 -cyclopropyl oder gegebenenfalls einfach durch Chlor oder Brom substituiertes Pyridyl, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl steht, wobei als Substituenten jeweils in Frage kommen: Cyano, Fluor, Chlor, Brom, Trifluormethyl oder Cyclopropyl, R4, R5, R6, R7 für Fluor stehen, R 3 stands for hydrogen, bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl or for phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl or each optionally substituted one or more times, identically or differently - bridged via a carbon atom to the remainder of the molecule Imidazolyl, with possible substituents in each case: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SF 5 , 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1 Fluorine-1-cyclopropyl, 1-trifluoromethyl-1 -cyclopropyl or optionally monosubstituted pyridyl, or optionally monosubstituted triazolyl bridged via a nitrogen atom to the remainder of the molecule, with possible substituents: Cyano, fluorine, chlorine, bromine, trifluoromethyl or cyclopropyl, R 4 , R 5 , R 6 , R 7 represent fluorine,
Y für Sauerstoff oder =N-H steht, Y stands for oxygen or = N-H,
Z für -NR8 steht, wobei Z is -NR 8 , where
R8 für Wasserstoff oder Methyl steht, m für 0 oder 1 steht, n für 0 oder 1 steht. R 8 represents hydrogen or methyl, m represents 0 or 1, n represents 0 or 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher R1 für Ethyl steht, Compounds of the formula (I) according to Claim 1, in which R 1 represents ethyl,
R2 für Methyl steht, R 2 represents methyl,
R3 für Brom, Cyclopropyl, oder für gegebenenfalls einfach durch Fluor, Chlor, Brom, Trifluormethyl, 1 -Cyano- 1- cy clopropyl, 1 -Trifluormethyl- 1 -cyclopropyl oder 1 -Fluor- 1 -cyclopropyl substituiertes Phenyl, oder für gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Pyridyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Chlor, Brom, Cyclopropyl oder 1 -Cyano- 1 -cyclopropyl, oder für jeweils gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Thiophenyl oder Thiazolyl, wobei als Substituenten jeweils in Frage kommen: Chlor oder 1 -Cyano- 1 -cyclopropyl, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl steht, wobei als Substituenten jeweils in Frage kommen: Cyclopropyl.R 3 stands for bromine, cyclopropyl, or for phenyl which is optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl, or optionally monosubstituted pyridyl - bridged to the remainder of the molecule via a carbon atom, with possible substituents in each case: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl, or for each optionally monosubstituted - via a carbon atom to the remainder of the molecule bridged - thiophenyl or thiazolyl, with possible substituents in each case: chlorine or 1-cyano- 1 -cyclopropyl, or optionally monosubstituted - triazolyl bridged via a nitrogen atom to the remainder of the molecule, with possible substituents in each case come: cyclopropyl.
R4, R5, R6, R7 für Fluor stehen, R 4 , R 5 , R 6 , R 7 represent fluorine,
Y für Sauerstoff steht, Y stands for oxygen,
Z für NR8 steht, wobei Z is NR 8 , where
R8 für Wasserstoff oder Methyl steht, m und n für 0 stehen oder m und n für 1 stehen. Verbindungen der Formel (I) gemäß Anspruch 1, in welcher R 8 represents hydrogen or methyl, m and n represent 0 or m and n represent 1. Compounds of formula (I) according to claim 1, in which
R1 für Ethyl steht, R 1 represents ethyl,
R2 für Methyl steht, R 2 represents methyl,
R3 für Wasserstoff, Brom, Cyclopropyl, oder für gegebenenfalls einfach durch Fluor, Chlor, Brom, Trifluormethyl, 1 -Cyano- 1- cyclopropyl, 1 -Trifluormethyl- 1 -cyclopropyl oder 1 -Fluor- 1 -cyclopropyl substituiertes Phenyl, oder für gegebenenfalls zweifach gleich oder verschieden durch Fluor, Chlor, Brom, Cyano substituiertes Phenyl, oder für gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Pyridyl, wobei als Substituenten jeweils in Frage kommen: Cyano, Chlor, Brom, Cyclopropyl, 1 -Cyano- 1 -cyclopropyl oder einfach durch Chlor oder Brom substituiertes Pyridyl (wobei Pyridyl über ein Kohlenstoffatom zum Rest des Moleküls verbrückt ist), oder für jeweils gegebenenfalls einfach substituiertes - über ein Kohlenstoffatom zum Rest des Moleküls verbrücktes - Thiophenyl oder Thiazolyl, wobei als Substituenten jeweils in Frage kommen: Chlor, oder für gegebenenfalls einfach substituiertes - über ein Stickstoffatom zum Rest des Moleküls verbrücktes -Triazolyl steht, wobei als Substituenten jeweils in Frage kommen: Cyclopropyl.R 3 stands for hydrogen, bromine, cyclopropyl, or for phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluorine-1-cyclopropyl, or for phenyl optionally substituted twice, identically or differently by fluorine, chlorine, bromine, cyano, or for optionally monosubstituted - pyridyl bridged via a carbon atom to the remainder of the molecule, where possible substituents are in each case: cyano, chlorine, bromine, cyclopropyl, 1 -Cyano- 1 -cyclopropyl or pyridyl which is substituted by chlorine or bromine (where pyridyl is bridged via a carbon atom to the remainder of the molecule), or for in each case optionally monosubstituted - bridged via a carbon atom to the remainder of the molecule - thiophenyl or thiazolyl, where as Substituents in each case come into question: chlorine, or for optionally monosubstituted - ver via a nitrogen atom to the rest of the molecule bridged triazolyl, with possible substituents in each case: cyclopropyl.
R4, R5, R6, R7 für Fluor stehen, R 4 , R 5 , R 6 , R 7 represent fluorine,
Y für Sauerstoff oder =N-H steht, Y stands for oxygen or = N-H,
Z für NR8 steht, wobei Z is NR 8 , where
R8 für Wasserstoff oder Methyl steht, m und n für 0 stehen oder m und n für 1 steht. R 8 represents hydrogen or methyl, m and n represent 0 or m and n represent 1.
Verbindungen der Formel (I) gemäß Anspruch 1, in welcher die Verbindungen die folgenden Strukturen haben: 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-Compounds of formula (I) according to claim 1, in which the compounds have the following structures: 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8 , 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-
17. 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-17. 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-
35. 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44. 35. 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44.
9. Agrochemische Formulierung enthaltend Verbindungen der Formel (I) gemäß Anspruch 1, sowie Streckmittel und/oder oberflächenaktive Substanzen. 9. Agrochemical formulation containing compounds of the formula (I) according to Claim 1, as well as extenders and / or surface-active substances.
10. Agrochemische Formulierung gemäß Anspruch 9 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. 11. Verfahren zur Bekämpfung von tierischen Schädlingen dadurch gekennzeichnet, dass man eine10. Agrochemical formulation according to claim 9 additionally containing a further agrochemical active ingredient. 11. A method for combating animal pests, characterized in that one
Verbindung der Formel (I) gemäß Anspruch 1 oder eine agrochemische Formulierung gemäß einem der Ansprüche 9 oder 10 auf die tierischen Schädlinge und/oder ihren Lebensraum einwirken lässt. A compound of the formula (I) according to claim 1 or an agrochemical formulation according to one of claims 9 or 10 can act on the animal pests and / or their habitat.
12. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 oder von agrochemischen Formulierungen gemäß einem der Ansprüche 9 oder 10 zur Bekämpfung von tierischen Schädlingen. 12. Use of compounds of the formula (I) according to Claim 1 or of agrochemical formulations according to one of Claims 9 or 10 for combating animal pests.
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