EP3692045A1 - Dérivés hétérocycliques utilisés comme pesticides - Google Patents

Dérivés hétérocycliques utilisés comme pesticides

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Publication number
EP3692045A1
EP3692045A1 EP18774061.8A EP18774061A EP3692045A1 EP 3692045 A1 EP3692045 A1 EP 3692045A1 EP 18774061 A EP18774061 A EP 18774061A EP 3692045 A1 EP3692045 A1 EP 3692045A1
Authority
EP
European Patent Office
Prior art keywords
cycloalkyl
alkyl
haloalkyl
spp
alkynyl
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
EP18774061.8A
Other languages
German (de)
English (en)
Inventor
Dominik HAGER
Rüdiger Fischer
Laura HOFFMEISTER
Nina Kausch-Busies
Marc Mosrin
David WILCKE
Matthieu WILLOT
Kerstin Ilg
Sascha EILMUS
Ulrich Görgens
Andreas Turberg
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 EP3692045A1 publication Critical patent/EP3692045A1/fr
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to heterocyclic derivatives of the formula (I), their use as acaricides and / or insecticides for combating animal pests, in particular arthropods and in particular insects and arachnids, and methods and intermediates for their preparation.
  • Heterocyclic derivatives with insecticidal properties have already been described in the literature, e.g. in WO2010 / 125985, WO2014 / 142292, WO2014 / 148451, WO2016 / 129684, WO2016 / 162318, WO2016 / 023954, WO2016 / 039441, WO2016 / 046071, WO2016 / 059145, WO2016 / 104746, WO2016 / 116338, WO2015 / 121136, WO2017 / 025419, WO2017 / 061497 and JP 2018-70585.
  • 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.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity.
  • heterocyclic derivatives have now been found which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, a better insecticidal, acaricidal effect, as well as a good tolerance to crops exemplified.
  • the heterocyclic derivatives can be used in combination with other agents for improving the effectiveness in particular against difficult-to-control insects.
  • the present invention therefore relates to novel compounds of the formula (I)
  • R 1 is (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C 2 - C 6) alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (C 3 - C 6) cycloalkyl (Ci-C 6) alkyl, (C3-C6) cycloalkyl- (Ci- C 6) haloalkyl, (GC 6) alkyl (C 3 - C 8) cycloalkyl, (Ci-C 6) haloalkyl (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (C 3 - C 8) cycloalkyl, spiro (C
  • C 6 haloalkynyloxy- (C 1 -C 6 ) -alkyl, amino, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (G-C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl ) alkylsulfonyl (Ci-C 6) alkyl, (Ci-C 6) haloalkylthio (Ci- C6) alkyl, (Ci-C 6) Halogenalkylsulfinyl- (Ci-C 6) alkyl, (Ci-C 6) haloalkylsulfonyl - (Ci-C6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkylthio- (Ci-C 6) alkyl, (Ci-C
  • R 2 are independently hydrogen, (C3-C6) cycloalkyl- (Ci-C6) haloalkyl, (Ci- C 6) haloalkyl (C 3 -C 8) cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8) cycloalkyl, (C 4 - C 2) bicycloalkyl, (C 3 -C 8) cycloalkyl, (C2-C6) alkenyl, (C 3 -C 8) cycloalkyl- (C2- C 6) alkynyl, cyano (C 3 -C 6) cycloalkyl, (C 2 -C 6) alkenyloxy (Ci-C6) alkyl, (C 2 -C 6) Halogenalkenyloxy- (Ci- C6) alkyl, (C 2 -C 6 ) alkynyloxy- (C 1 -C 4 )
  • R 4 is (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) hydroxyalkyl, (G-C 6 ) alkoxy- (Ci-C 6 ) alkyl alkyl, (Ci-C 6) haloalkoxy (Ci-C 6), (C 2 -C 6) alkenyl, (C2 - C6) alkenyloxy (Ci-C6) alkyl, (C2-C6) Halogenalkenyloxy- (C C6) alkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) cyanoalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) alkynyloxy (Ci-C 6) alkyl, (C 2 -
  • C6 haloalkoxycarbonyl (Ci-C6) alkyl, aminocarbonyl (Ci-C6) alkyl, (GG) alkylamino (G- C 6) alkyl, di- (Ci-C 6) alkylamino (Ci-C 6) alkyl Tri (C 1 -C 6 ) alkylsilyl or (G-C 8 ) cycloalkylamino (C 1 -C 6 ) alkyl,
  • R 5 is hydrogen, halogen, cyano, hydroxycarbonyl, SCN, SF 5, (Ci-C 6) alkyl, (G- C 6) haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) alkynyl, (G- C6) haloalkynyl, (GG) alkoxy, (GG) haloalkoxy, (C 3 -C 8) cycloalkyl, halo (C 3 - C 8) cycloalkyl, (C 3 -C 6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6) cycloalkyl- (Ci-C 6) -haloalkyl, (Ci- C 6) alkyl, (Ci-C 6) cycloalkyl- (Ci-C 6) -haloalkyl, (Ci
  • R 11 is (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 8 ) cycloalkyl, halogen ( C 3 -C 8) cycloalkyl, (C 3 -C 6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6) cycloalkyl- (Ci-C 6) haloalkyl, (Ci-C 6) alkyl (C 3 -C 8 ) cycloalkyl, (C 1 -C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, spiro (C 3 -
  • C6 haloalkoxycarbonyl, aminocarbonyl, (Ci-C6) alkylaminocarbonyl, di- (GG) alkylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, tri (Ci-C6) alkylsilyl, a phenyl ring or a 3- to 6-membered aromatic, partially saturated or saturated heterocycle, where the phenyl ring or heterocycle may each optionally be monosubstituted or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from halogen, cyano, nitro, hydroxy, hydroxycarbonyl, amino, (G-C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (G-C 6
  • R 13, R 14 are independently hydrogen, (Ci-Ce) alkyl, (Ci-Ce) haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C6) alkyl, (C3-C6) cycloalkyl - (Ci
  • Ci 2 bicycloalkyl, cyano, (C 3 -C 6) cycloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci- C6) alkoxy (Ci-C 6) alkyl, (C 2 - C6) cyanoalkenyl, (C 3 -C 6) cycloalkyl (C 2 -C 6) alkenyl, (C 2 - C 6) cyanoalkynyl, (C3-C6) cycloalkyl- (C 2 -C 6) alkynyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 - C 6) alkenyloxy (Ci-C 6) alkyl, (C 2 -C 6) Halogenalkenyloxy- (Ci-C 6) alkyl, (C 2 - C 6) alkynyloxy (CI-C
  • R 15, R 16 are each independently hydrogen, cyano, hydroxy, (C 2 -C 6) haloalkenyl, (C 2 - C6) haloalkynyl, (Ci-Ce) alkoxy, (Ci-Ce) haloalkoxy, halo (C 3 -C 8) cycloalkyl, (C 3 - C6) cycloalkyl (Ci-C 6) haloalkyl, (Ci-C6) alkyl- (C3-C8) cycloalkyl, (Ci-C6) haloalkyl (C 3 - C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (C 3 -C 8) cycloalkyl, spiro (C 3 -C 8) cycloalkyl- (C 3 -C 8) cycloalkyl, (C4-Ci 2) bicycloalkyl, cyano ( C3-C6)
  • R independently represent hydrogen, (C2 -Ce) alkenyl, (C2 -Ce) haloalkenyl, (C 2 - C 6) alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl , halo (C 3 -C 8) cycloalkyl, (C 3 - C 6) cycloalkyl (Ci-C 6) alkyl, (C3-C6) cycloalkyl- (Ci-C 6) hal
  • C 6 haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (G-C 6 ) haloalkynyl, (GG) alkoxy, (GG) haloalkoxy, ( C 3 -C 8) cycloalkyl, halo (G- C 8) cycloalkyl, (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, (Ci-C 6) alkylsulfinyl, (G- C6) haloalkylsulfinyl, (C -C6) alkylsulfonyl, (C 1 -C 6) haloalkylsulfonyl, (C 1 -C 6) alkoxycarbonyl, aminocarbonyl, (C 1 -C 6) -alkyla
  • R 16 are each independently hydrogen, cyano, hydroxy, (C 2 -C 6) haloalkenyl, (C 2 - C6) haloalkynyl, (Ci-Ce) alkoxy, (Ci-Ce) haloalkoxy, halogen (C 3 -C 8) cycloalkyl, (C 3 - C 6) cycloalkyl (Ci-C 6) haloalkyl, (Ci-C 6) alkyl (C 3 -C 8) cycloalkyl, (Ci-C 6) -haloalkyl - (C 3 -C 8) cycloalkyl, (Ci-C 6) -haloalkyl - (C 3 - C 8) cycloalkyl, (C 3 -C 8)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the meanings given in embodiment 1-2, wherein when R 2 or R 3 is cyano (GG) cycloalkyl, then R 5 is not halogen, (Ci-C6) haloalkyl, (Ci-C6) haloalkylthio, (G - C6) haloalkylsulfinyl or (Ci-C6) haloalkylsulfonyl.
  • the compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides, moreover, as a rule, are very well tolerated by plants, in particular with respect to crop plants.
  • R 1 is preferably (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (C 3 - C 6) cycloalkyl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) haloalkyl, (Ci-C 6) alkyl (C 3 - C 8) cycloalkyl, (Ci-C6) haloalkyl, (Ci-C 6) alkyl (C 3 - C 8) cycloalkyl, (Ci-C6) halo
  • R 2 , R 3 independently of one another preferably represent hydrogen, (C 3 -C 6) -cycloalkyl (C 1 -C 6) -haloalkyl, (C 1 -C 6 ) -haloalkyl- (C 3 -C 8 ) -cycloalkyl, spiro (C 3 -C 8 ) -cycloalkyl - (C3-C8) cycloalkyl, (C4-Ci2) bicycloalkyl, (C3-C8) cycloalkyl (C 2 -C 6) alkenyl, (C 3 -C 8) cycloalkyl (C 2 - C 6 ) alkynyl, cyano (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyloxy- (C 1 -C 6 ) alkyl, (C 2 -
  • R 4 is preferably (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, (C 2 - C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) alkynyl, (C 2 - C 6 ) haloalkynyl, (C 3 -C 8 ) cycloalkyl, (Ci-C6) alkyl- (C3-C8) cycloalkyl, halo (C 3 -C 8) -cycloalkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (G- C 6) alkyl
  • R 13 , R 14 independently of one another preferably represent hydrogen, (GG) alkyl, (G-C 6 ) haloalkyl, (GG) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (G-G) cycloalkyl, halo (C 3 -C 8 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl (GC 6 ) alkyl, (GG) cycloalkyl- (C 1 -C 6 ) -halogenoalkyl , (GG) alkyl (GG) cycloalkyl, (G-C6) haloalkyl- (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl,
  • R 16 independently of one another are preferably hydrogen, cyano, hydroxyl, (G-C 6 ) haloalkenyl, (GG) halo-aikinyl, (GG) aikoxy, (C 1 -C 6 ) -haloalkoxy, halo (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) C 6) cycloalkyl- (Ci-C 6) haloalkyl, (GC 6) alkyl- (G G) cycloalkyl, (Ci-C 6) haloalkyl (C3-C8) cycloalkyl, (GC 8) cycloalkyl (GC 8) cycloalkyl, spiro (C3-C8) cycloalkyl- (C 3 -C 8) cycloalkyl, (C 4 -Ci2) bicycloalkyl, cyano, (C3-C6) cycloalky
  • R 19 independently of one another preferably represent hydrogen, (C2 -Ce) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6) -haloalkynyl, (C 3 -C 8 ) cycloalkyl, halo (C 3 - C 8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C6) alkyl, (C3-C6) cycloalkyl- (Ci-C 6) haloalkyl, (C 6 G ) Alkyl (C 3 -C 8 ) cycloalkyl, (C 1 -C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (GG) cycloalkyl- (G-C 8 ) cycloalkyl, spiro (C 3 -C 8 ) cycloal
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 17 , R 18 , R 19 , n, m and p have the in embodiment 2 -1 given meanings and
  • R 15 , R 16 independently of one another preferably represent hydrogen, cyano, hydroxy, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -haloalkynyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkoxy, halogen (C 3 -C 8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C 6) haloalkyl, (Ci-C 6) alkyl (C 3 - C 8) cycloalkyl, (Ci-C 6) haloalkyl (C 3 - C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the meanings given in embodiment 2-2, where when R 2 or R 3 are cyano (C 3 -C 6) -cycloalkyl, then R 5 is not halogen, (C 1 -C 6) -haloalkyl, (C 1 -C 6) -haloalkylthio, (C 1 -C 6) haloalkylsulfinyl or (C 1 -C 6) haloalkylsulfonyl.
  • R 1 particularly preferably represents (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl or (C 3 -C 5) cycloalkyl
  • R 2 particularly preferably represents hydrogen
  • R 4 particularly preferably represents (Ci-Ce) alkyl, (Ci-C6) haloalkyl, (Ci-Ce) cyanoalkyl, (Ci- C 6) hydroxyalkyl, or (Ci-C 6) alkoxy (Ci-C 6) alkyl .
  • R 5 particularly preferably represents halogen, (C 1 -C 6) haloalkyl, (C 1 -C 6) haloalkoxy, (C 3 -C 5) cycloalkyl, halogeno (C 3 -C 8) cycloalkyl, (C 1 -C 6) cyanoalkyl, cyano (C 3 -C 6) cycloalkyl, C 6) haloalkylthio, (C 1 -C 6) haloalkylsulfinyl or (C 1 -C 6) haloalkylsulfonyl, particularly preferably represents (C 2 -C 6) alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 - C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C
  • R 14 independently of one another particularly preferably represent hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 - C 6) -haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (C 3 -C 6) cycloalkyl- (Ci- C6) alkyl, (C 3 -C 6) Cycloalkyl- (Ci-C 6 ) haloalkyl, (Ci-C 6 ) alkyl- (C 3 -C 8 ) cycloalkyl, (G-C 6 ) haloalkyl- (C 3 -C 8 ) cycloalkyl, (C 3
  • R 16 independently of one another particularly preferably represent hydrogen, cyano, hydroxyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -haloalkynyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -halogenoalkoxy, Halo (C 3 -C 8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C 6) haloalkyl, (Ci-C 6) alkyl (C 3 - C 8) cycloalkyl, (Ci-C 6) -haloalkyl - (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl, spiro (C 3 -C 8 ) cycloalkyl- (C 3 -C 8 ) cycloalkyl
  • R independently of one another particularly preferably represent hydrogen, cyano, hydroxyl, (G-C6) haloalkenyl, (GG) halo-alkynyl, (GG) aikoxy, (C 1 -C 6 ) -haloalkoxy, halo (C 3 -C 8 ) -cycloalkyl, ( C3-C6) cycloalkyl- (Ci-C 6)
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the meanings given in embodiment 3-2, wherein when R 3 is cyano (G-C6) cycloalkyl, then R 5 is not halogen, (GG) haloalkyl, (GC 6 ) haloalkylthio, (GC 6 ) haloalkylsulfinyl or (C-G) haloalkylsulfonyl.
  • R 3 is cyano (G-C6) cycloalkyl
  • R 5 is not halogen, (GG) haloalkyl, (GC 6 ) haloalkylthio, (GC 6 ) haloalkylsulfinyl or (C-G) haloalkylsulfonyl.
  • R very particularly preferably represents (C3-Cs) cycloalkyl, halo (C3-C8) cycloalkyl, (C C6) cycloalkyl- (Ci-C6) alkyl, (C 3 -C 6) cycloalkyl- (Ci-C6) haloalkyl , (C 1 -C 6 ) alkyl- (C 3 -
  • Aa very particularly preferably represents N (nitrogen) or C (H) -
  • Ab very particularly preferably represents N (nitrogen) or C (H) -
  • R 1 very particularly preferably represents (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl or (C 3 -C 5) -cycloalkyl
  • R 2 very particularly preferably represents hydrogen
  • R 3 very particularly preferably represents (C 3 -C 6 ) -cycloalkyl- (C 1 -C 4 ) -halogenoalkyl, (C 1 -C 4 ) -halogenoalkyl- (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 2 -C 4 ) alkenyl, (C 3 -C 6 ) cycloalkyl- (C 2 -C 4) -alkynyl, cyano (C 3 -C 6 ) -cycloalkyl,
  • R 4 is very particularly preferably (C 1 -C 6 ) alkyl, R 5 very particularly preferably halogen, (C 1 -C 6) haloalkyl, (C 1 -C 6) haloalkoxy, (C 3 -C 5 ) cycloalkyl, halogen (C 3 -C 5 ) cycloalkyl, cyano (C3-C6) cycloalkyl, (Ci-Ce) haloalkylthio, (Ci-C6) haloalkylsulfinyl or (Ci-C6) haloalkylsulfonyl,
  • R 11 very particularly preferably represents (C 3 -C 8) cycloalkyl
  • R 12 is very particularly preferably (C 3 -C 8 ) cycloalkyl
  • R 13 is very particularly preferably (C 1 -C 6) alkyl
  • R 14 very particularly preferably represents (C 1 -C 6 ) alkyl, (C 1 -C 6 ) halogenoalkyl, (C 3 -C 5 ) cycloalkyl, halogeno (C 3 -C 8 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl (C 1 -C 4 ) 6 ) alkyl, (C 3 -C 6 ) cycloalkyl- (ci)
  • R 15 is very particularly preferably hydrogen
  • R 16 is very particularly preferably amino, (C 1 -C 6) alkylamino, di (C 1 -C 6) alkylamino, (C 3 -C 8) cycloalkylamino or 4-furanyl-2 (5H) -one, very particularly preferably (C3-Cs) cycloalkyl, halo (C3-C8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C6) alkyl, (C3-C6) cycloalkyl- (Ci- C 6 ) haloalkyl, (C 1 -C 6 ) alkyl- (C 3 - Cs) cycloalkyl or (C 1 -C 6) haloalkyl- (C 3 -C 8) cycloalkyl, R 18 very particularly represents hydrogen,
  • R 19 very particularly preferably represents allyl, (C3-Cs) cycloalkyl, halo (C3-C8) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C6) alkyl, (C3-C6) cycloalkyl- (Ci -C 6 ) haloalkyl, (Ci-C 6 ) alkyl (C 3 -Cs) cycloalkyl, (Ci-C6) haloalkyl- (C3-C8) cycloalkyl, optionally substituted by methyl pyrazolyl or oxazolyl, n is most particularly preferred 0, 1 or 2, m is very particularly preferably 0, 1 or 2, p is very particularly preferably 0, 1 or 2.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the meanings given in embodiment 4-2, wherein when R 3 is cyano (C 3 -C 6) -cycloalkyl, then R 5 is not halogen, (Ci-Ce) haloalkyl, (Ci-C6) haloalkylthio, (Ci -C6) haloalkylsulfinyl or (Ci-C6) haloalkylsulfonyl.
  • Embodiment 5-1 Embodiment 5-1
  • Aa stands for N (nitrogen)
  • R 1 is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, Tetrafluoroethyl or pentafluoroethyl,
  • R 2 is hydrogen
  • R 3 stands for cyanocyclopropyl, cyanocyclobutyl, cyclopropylvinyl,
  • R 19 is methylcyclopropyl, cyclobutyl or cyclopropylmethyl
  • R 4 is methyl or ethyl
  • R 5 is fluoro, chloro, bromo, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, n is 0, 1 or 2.
  • R 1 is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, Tetrafluoroethyl or pentafluoroethyl,
  • R 2 is hydrogen
  • R 3 stands for cyanocyclopropyl, cyanocyclobutyl, cyclopropylvinyl, cyclopropyldifluoromethyl, cyclopropylfluoromethyl,
  • R 19 is allyl, methylcyclopropyl, cyclobutyl or cyclopropylmethyl,
  • R 5 is fluoro, chloro, bromo, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, n is 0, 1 or 2.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the meanings given in embodiment 5-2, where when R 3 is cyanocyclopropyl then R 5 is not fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl ( CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethylthio, trifluor
  • Embodiment 6-1 Aa stands in particular for N (nitrogen),
  • R 19 is 1-methylcyclopropyl, cyclobutyl or cyclopropylmethyl
  • R 4 is especially methyl
  • R 5 stands especially for trifluoromethyl, trifluoromethylthio or trifluoromethylsulfonyl
  • n stands in particular for 2.
  • R 1 is in particular ethyl
  • R 2 is especially hydrogen
  • R 3 is in particular 1-cyanocyclopropyl, 2-cyclopropylvinyl, cyclopropyldifluoromethyl, cyclopropylfluoromethyl,
  • R 19 is allyl, 1-methylcyclopropyl, cyclobutyl or
  • R 5 is in particular trifluoromethyl, pentafluoroethyl, trifluoromethylthio, trifluoromethylsulfonyl or trifluoromethoxy, n is in particular 2.
  • Aa, Ab, R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , n, m and p have the in
  • Embodiment 6-2 given meanings, wherein when R 3 is 1-cyanocyclopropyl, then R 5 is not trifluoromethyl, pentafluoroethyl, trifluoromethylthio, trifluoromethylsulfonyl.
  • R 1 , R 2 , R 3 , R 4 , R 5 and n are those in the embodiment (1-1) or the embodiment (1-2) or the embodiment (1-3) or the configuration (2-1) or the configuration ( 2-2) or design (2-3) or design (3-1) or (design 3-2) or design (3-3) or design (4-1) or design (4-2) or design (4 -3) or design (5-1) or design (5-2) or design (5-3) or design (6-1) or (design 6-2) or design (6-3) have described meanings.
  • R 1 , R 2 , R 3 , R 4 , R 5 and n are those in the embodiment (1-1) or the embodiment (1-2) or the embodiment (1-3) or the configuration (2-1) or the configuration ( 2-2) or design (2-3) or design (3-1) or (design 3-2) or design (3-3) or design (4-1) or design (4-2) or design (4 -3) or design (5-1) or design (5-2) or design (5-3) or design (6-1) or (design 6-2) or design (6-3) have described meanings.
  • R 1 , R 2 , R 3 , R 4 , R 5 and n are those in the embodiment (1-1) or the embodiment (1-2) or the embodiment (1-3) or the configuration (2-1) or the configuration ( 2-2) or design (2-3) or design (3-1) or (design 3-2) or design (3-3) or design (4-1) or design (4-2) or design (4 -3) or design (5-1) or design (5-2) or design (5-3) or design (6-1) or (design 6-2) or design (6-3) have described meanings.
  • R 1 , R 2 , R 3 , R 4 , R 5 and n are those in the embodiment (1-1) or the embodiment (1-2) or the embodiment (1-3) or the configuration (2-1) or the configuration ( 2-2) or design (2-3) or design (3-1) or (design 3-2) or design (3-3) or design (4-1) or design (4-2) or design (4 -3) or design (5-1) or design (5-2) or design (5-3) or design (6-1) or (design 6-2) or design (6-3) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is 1-cyanocyclopropyl and Aa, Ab, R 1 , R 4 , R 5 and n 1-1) or design (1-2) or design (1-3) or design (2-1) or design (2-2) or design (2-3) or design (3-1) or (design 3 -2) or design (3-3) or design (4-1) or design (4-2) or design (4-3) or design (5-1) or design (5-2) or design (5) 3) or embodiment (6-1) or (embodiment 6-2) or embodiment (6-3) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is 2-cyclopropylvinyl and Aa, Ab, R 1 , R 4 , R 5 and n 1-1) or design (1-2) or design (2-1) or design (2-2) 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 (6-1) or (design 6-2) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is cyclopropyldifluoromethyl and Aa, Ab, R 1 , R 4 , R 5 and n are in the form (1) 1) or design (1-2) or design (2-1) or design (2-2) 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 (6-1) or (design 6-2) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is cyclopropylfluoromethyl and Aa, Ab, R 1 , R 4 , R 5 and n are in the form (1) 1) or design (1-2) or design (2-1) or design (2-2) 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 (6-1) or (design 6-2) have described meanings.
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is -NR 15 R 16 and Aa, Ab, R 1 , R 4 , R 5 , R 15 , R 16 and n in the embodiment (1-1) or the embodiment (1-2) or the embodiment (2-1) or the embodiment (2-2) or the configuration (3-1) or (the embodiment 3-2) or the configuration ( 4-1) or design (4-2) or design (5-1) or design (5-2) or design (6-1) or (design 6-2) have described meanings.
  • the invention relates to the compounds of the formula (I) in which Aa is N (nitrogen), Ab is N (nitrogen), R 2 is hydrogen and R 3 is 1-cyanocyclopropyl and R 1 , R 4 , R 5 and n in the embodiment (1-1) or configuration (1-2) or configuration (1-3) or embodiment (2-1) or embodiment (2-2) or embodiment (2-3 ) or Embodiment (3-1) or (Embodiment 3-2) or Embodiment (3-3) or Embodiment (4-1) or Embodiment (4-2) or Embodiment (4-3) or Embodiment (5-1) or design (5-2) or design (5-3) or design (6-1) or (design 6-2) or design (6-3) have meanings described.
  • the invention relates to the compounds of the formula (I) in which Aa is N (nitrogen), Ab is N (nitrogen), R 2 is hydrogen and R 3 is 2-cyclopropylvinyl and R 1 , R 4 , R 5 and n in the embodiment (1-1) or configuration (1-2) or configuration (2-1) or embodiment (2-2) or configuration (3-1) or (embodiment 3-2 ) or design (4-1) or design (4-2) or design (5-1) or design (5-2) or design (6-1) or (design 6-2) have described meanings.
  • the invention relates to the compounds of formula (I) in which Aa is N (nitrogen), Ab is N (nitrogen), R 2 is hydrogen and R 3 is cyclopropyldifluoromethyl and R 1 , R 4 , R 5 and n in the embodiment (1-1) or the embodiment (1- 2) or the embodiment (2-1) or the embodiment (2-2) or the configuration (3-1) or (embodiment 3-2) or Embodiment (4-1) or embodiment (4-2) or embodiment (5-1) or embodiment (5-2) or embodiment (6-1) or (embodiment 6-2) have described meanings.
  • the invention relates to the compounds of formula (I) in which Aa is N (nitrogen), Ab is N (nitrogen), R 2 is hydrogen and R 3 is cyclopropylfluoromethyl and R 1 , R 4 , R 5 and n are in the embodiment (1-1) or the embodiment (1-2) or Embodiment (2-1) or Embodiment (2-2) or Embodiment (3-1) or (Embodiment 3-2) or Embodiment (4-1) or Embodiment (4-2) or Embodiment (5-1) or Embodiment (5-2) or embodiment (6-1) or (embodiment 6-2) have described meanings.
  • the invention relates to the compounds of formula (I) in which Aa is N (nitrogen), Ab is N (nitrogen), R 2 is hydrogen and R 3 is -NR 15 R 16 and R 1 , R 4 , R 5 , R 15 , R 16 and n are in the embodiment (1-1) or embodiment (1-2) or embodiment (2-1) or embodiment (2-2) or embodiment (3- 1) or (Embodiment 3-2) or Embodiment (4-1) or Embodiment (4-2) or Embodiment (5-1) or Embodiment (5-2) or Embodiment (6-1) or (Embodiment 6-2 ) have meanings described.
  • R 17 and R 1 , R 4 , R 5 , R 17 and n are those in the embodiment (1-1) or the embodiment (1-2) or the embodiment (2-1) or the configuration (2-2) or the configuration ( 3-1) or (embodiment 3-2) or design (4-1) or design (4-2) or design (5-1) or design (5-2) or design (6-1) or (design 6-2) have described meanings.
  • P -R 12 and R 1 , R 4 , R 5 , R 12 , p and n are in the embodiment (1-1) or the embodiment (1-2) or the embodiment (2-1) or Embodiment (2-2) or Embodiment (3-1) or (Embodiment 3-2) or Embodiment (4-1) or Embodiment (4-2) or Embodiment (5-1) or Embodiment (5-2) or Embodiment (6-1) or (embodiment 6-2) have been described.
  • Halogen selected from the series fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine.
  • Aryl also as part of a larger moiety, such as arylalkyl selected from the group phenyl, benzyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl.
  • Hetaryl (equivalent to heteroaryl, also as part of a larger unit such as, for example, hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1 , 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2 , 5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,
  • Heterocyclyl for a saturated 4-, 5- or 6-ring containing 1 or 2 nitrogen atoms and / or an oxygen atom and / or a sulfur atom for example, azetidinyl, pyrrolidinyl, piperidinyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thietanyl, tetrahydrothiophenyl , Tetrahydrothiopyranyl, piperazinyl, morpholinyl and thiomorpholinyl.
  • halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine.
  • Aryl also as part of a larger unit, such as arylalkyl selected from the group phenyl, benzyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl,
  • Hetaryl (also as part of a larger unit such as, for example, hetarylalkyl) selected from the series oxazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and tetrazolyl,
  • Heterocyclyl selected from the series oxetanyl, tetrahydrofuryl and piperazinyl.
  • alkyl either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and Of these
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 alkynyl having at least one triple bond, for example ethynyl, 1 Preferred are C 3 -C 6 -alkynyl radicals and particularly preferred are C 5 -C 5 -alkynyl radicals The alkynyl radical may also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
  • alkoxy either alone or in combination with other terms, such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • Very particularly preferably used according to the invention are compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
  • Useful according to the invention are compounds of the formula (I) which contain a combination of the meanings listed above as being highlighted.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any desired mixtures of these isomers.
  • the compounds of the formula (I) according to the invention can be obtained by the processes illustrated in the following schemes:
  • radicals Aa, Ab, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings described above, X 1 is halogen.
  • R 6 is (Ci-C 4 ) alkyl.
  • the compounds of the formula (B) can be prepared by reacting the compounds of the formula (A) with the compounds of the formula (Aa) in the presence of a base.
  • Carboxylic acid esters of the formula (A) are either commercially available or can be prepared by known methods, for example from 2-aminopyridine derivatives analogous to the processes described in WO2011 / 41713.
  • Mercaptan derivatives of the formula (Aa), for example methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
  • the reaction to give compound of the formula (B) may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Sodium hydride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • X 1 is preferably a fluorine, bromine or chlorine atom.
  • the compounds of the formula (C) can be prepared by oxidation of the compounds of the formula (B).
  • the oxidation is generally carried out in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • the compounds of the formula (D) can be prepared by oxidation of the compounds of the formula (C).
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • the compounds of the formula (D) can also be prepared in a one-step process by oxidation of the compounds of the formula (B).
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • the compounds of the formula (E) can be prepared by saponification of the compounds of the formula (D) in the presence of a base.
  • the saponification is generally carried out in a solvent.
  • Preference is given to alcohols such as methanol or ethanol; Water; Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide; or, if appropriate, mixtures of said solvents.
  • Suitable bases are inorganic bases from the group consisting of hydroxides, acetates, phosphates and carbonates of alkali or alkaline earth metals. Preference is given here Sodium hydroxide, lithium hydroxide, cesium carbonate, sodium carbonate and potassium carbonate.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of -20 ° C to 200 ° C.
  • the compounds of the formula (F) can be prepared by reacting compounds of the formula (G) with carboxylic acids of the formula (E) in the presence of a condensing agent or a base.
  • the reaction of the compounds of the formula (G) with carboxylic acids of the formula (E) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene
  • Nitriles such as acetonitrile or propionitrile
  • aromatic hydrocarbons such as toluene or xylene
  • aprotic polar solvents such as ⁇
  • the compounds of the formula (G) are either available commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715 described method.
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • Suitable bases are inorganic bases which are commonly used in such reactions.
  • bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • Other suitable bases are alkali metal hydrides such as sodium hydride.
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
  • Step g) The compounds of formula (H) can be prepared by condensing the compounds of formula (F) e.g. analogously to the process described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 or WO 2015/121136.
  • the reaction to give compounds of the formula (H) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers 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; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
  • acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N
  • An example of a suitable chlorinating agent is phosphorus oxychloride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • R 8 is R 19 when Q and Y are oxygen (O) or when Q is oxygen (O) and Y is NH.
  • R 8 is R 14 when Q is heavy (S) and Y is NH or when Q is sulfur (S) and Y is oxygen (O).
  • the compounds of the formula (I) can be prepared in a one-step process by reacting the compounds of the formula (I) with compounds of the formula (Ia) in analogy to those described in Organic Letters, 2 (2000), 1101-1104 or /. At the. Chem. Soc. 2007, 129, 13001-13007.
  • the compounds of the formula (I) can be prepared analogously to the methods described in process A.
  • the compounds of the formula (Ia) are commercially available.
  • the reaction to give compounds of formula (J) is generally carried out in a solvent in the presence of a base.
  • Preferred solvents are ethers such as, for example, dioxane or ethylene glycol dimethyl ether, preferred bases are, for example, cesium carbonate, potassium phosphate or sodium tert-butoxide.
  • the reaction to compounds of formula (J) is generally carried out in the presence of a catalyst and a ligand.
  • Palladium complexes such as, for example, tris (dibenzylideneacetone) dipalladium (0) or palladium acetate, can be used as the catalyst and organophosphane compounds, for example bis (diphenylphosphine) -9,9-dimethylxanthene (xanthphos), are generally used as ligands.
  • organophosphane compounds for example bis (diphenylphosphine) -9,9-dimethylxanthene (xanthphos)
  • the compounds of formula (K) can be prepared by amide hydrolysis of the compounds of formula (J) in the presence of a base.
  • the hydrolysis is generally carried out in a solvent.
  • Preference is given to alcohols such as methanol or ethanol; Water; Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide; or, if appropriate, mixtures of said solvents.
  • Suitable bases are inorganic bases from the group consisting of hydroxides, acetates, phosphates and carbonates of alkali or alkaline earth metals.
  • Sodium hydroxide, lithium hydroxide, cesium carbonate, sodium carbonate and potassium carbonate are preferred.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the compounds of the formula (L) are commercially available.
  • the reaction to give compounds of the formula (M) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from customary, in the prevailing reaction conditions inert solvents.
  • ethers 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; aprotic polar solvents such as ethyl acetate; or aromatic hydrocarbons such as toluene or xylene.
  • Suitable Cl synthesis equivalents are phosgene, triphosgene, carbonyldiimidazole (CDI), or thiophosgene.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and ⁇ , ⁇ -diisoprop
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the compounds of formula (O) can be prepared in a one-step process by reacting the compounds of formula (K) with compounds of formula (N) in the presence of a base.
  • ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, esters such as ethyl acetate, basic nitrogen-containing compounds such as pyridine, or nitriles such as acetonitrile.
  • ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as he
  • the reaction can be carried out in the presence of a base.
  • bases are nitrogen-containing heterocycles such as pyridine, dimethylaminopyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine or inorganic bases such as potassium carbonate and sodium hydride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of -20 ° C to 200 ° C.
  • radicals Aa, Ab, R 1 , R 2 , R 4 , R 5 and R 17 have the meanings described above, X 1 is halogen.
  • M is a metal atom (Li, Na, K).
  • reaction of the compound of the formula (I) with the compound of the formula (P) and the copper source is generally carried out in a solvent.
  • a solvent Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and ⁇ , ⁇ -dimethylformamide.
  • the copper source used is usually CuBr, Cul or Cu (OAc) 2.
  • Suitable sulfur reagents are sodium salts of the sulfinic acids.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 20.degree. C. to 200.degree.
  • Subst. Z.Bsp. Alkyl, cycloalkyl, etc.
  • Step a) Compounds of the formula (S) can be prepared by carbonylating the compounds of the formula (I) with the aid of a catalyst and a base and subsequent reaction with compounds of the formula (R), for example in analogy to those described in Applied Catalysis A: General , 2014, 481, 54-63.
  • the compounds of the formula (R) are commercially available.
  • the reaction to give compounds of the formula (S) is generally carried out in a solvent.
  • Preferred are ethers such as tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycol dimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatic hydrocarbons such as toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or esters such as ethyl acetate.
  • Palladium complexes can be used as the catalyst, for example tris (dibenzylideneacetone) dipalladium (0) or [1,1'-bis (diphenylphosphino) ferrocenes] -dichloropalladium (II).
  • suitable bases are nitrogen-containing heterocycles such as pyridine, dimethylaminopyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine or inorganic bases such as potassium carbonate and sodium hydride.
  • Compounds of formula (T) may be prepared by cyanomethylation of the compounds of formula (I) with compound of formula (Ra) in the presence of a catalyst, a ligand and a base, for example according to the methods described in J. Am. Chem. Soc. 2002, 124, 9330, J. Am. Chem. Soc. 2005, 127, 15824 or WO2016 / 041819 described method.
  • the compound of the formula (Ra) is commercially available.
  • reaction to give compounds of the formula (T) is generally carried out in a solvent.
  • aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.
  • Palladium complexes can be used as the catalyst, for example tris (dibenzylideneacetone) dipalladium (0) or [1,1'-bis (diphenylphosphino) ferrocenes] -dichloropalladium (II) and, as ligands, organophosphane compounds are usually used, such as bis (diphenylphosphine) -9,9-dimethylxanthene (xanthphos).
  • a suitable base is, for example, zinc fluoride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the cyanomethylation can also be carried out by means of a Suzuki coupling, for example according to the method described in J. Am. Chem. Soc. 2011, 133, 6948-6951. Step b)
  • Compounds of the formula (U) can be prepared by reacting the compounds of the formula (T) with compounds of the formula (V) in the presence of a base, for example by the processes described in WO2016 / 041819.
  • the compounds of the formula (V) are commercially available,
  • the reaction to give compounds of the formula (U) is generally carried out in a solvent.
  • a solvent Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene
  • aprotic polar solvents such as acetone, ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and ⁇ , ⁇ -diisoprop
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • Acids of the formula (F2) can be prepared by the following process F:
  • R 1 and n have the meanings described above, X 1 is halogen, X is chlorine, bromine or iodine, R 6 is (Ci-C alkyl and q is 1 or 2.
  • Step a) The compounds of formula (Y), in analogy to those described in European Journal of Medicinal Chemistry, 29 (1994) 279-286; WO2006 / 71752; WO2012 / 80232; Journal of Medicinal Chemistry, 57
  • the bromopyruvate derivatives of the formula (X) are commercially available.
  • the compounds of formula (W) are either commercially available or can be prepared by known methods, for example analogously to those described in Chemical Communications, 44 (2010), 925-927; Journal of the American Chemical Society, 68 (1946), 453-457; WO2009 / 29625; Journal of the American Chemical Society, 137
  • the compounds of formula (Z) can be prepared from compounds of formula (Y), e.g. analogously to the process described in WO2008 / 36216, WO2004 / 22561, WO2006 / 23707, WO2006 / 133006, WO2014 / 60375, US2004 / 23981 or EP3018125.
  • the reaction to give compounds of the formula (Z) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers 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; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene
  • Nitriles such as acetonitrile or propionitrile
  • aromatic hydrocarbons such as toluene or xylene
  • the reaction can be carried out in the presence of a chlorinating agent and optionally a base.
  • chlorinating agents examples include thionyl chloride, methanesulfonyl chloride, or phosphoryl chloride.
  • suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydroxide.
  • nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydroxide.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the compounds of formula (A2) can be prepared by substitution from compounds of formula (Z), e.g. analogous to that described in US2014 / 57914, EP2036905, J. Agric. Food Chem. 2017, 65, 1272-1280, WO2009 / 114180, or Tetrahedron 2005, 6115.
  • the reaction to give compounds of the formula (A2) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to polar solvents such as dimethyl sulfoxide or ⁇ , ⁇ -dimethylformamide or acetonitrile.
  • the reaction can be carried out in the presence of a cyanating agent.
  • Suitable cyanating agents are sodium cyanide or potassium cyanide.
  • reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • Compounds of the formula (B2) can be prepared by reacting the compounds of the formula (A2) with compounds of the formula (V) in the presence of a base, for example by the processes described in WO2016 / 041819.
  • the compounds of the formula (V) are commercially available.
  • the reaction to give compounds of the formula (A2) is generally carried out in a solvent.
  • a solvent Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene
  • aprotic polar solvents such as acetone, ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitrile
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and ⁇ , ⁇ -diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and ⁇ , ⁇ -diisoprop
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C. Steps)
  • Compounds of the formula (C2) can be prepared by known methods from compounds of the formula (B2) via a halogenation analogous to those described in WO2009 / 23179, WO2010 / 91411, WO2011 / 41713 and Bioorganic and Medicinal Chemistry Letters, 22 (2012), 3460-3466, for example, with N-chlorosuccinimide as the halogenating agent in dimethylformamide as a solvent.
  • the compounds of the formula (D2) can be prepared by reacting the compounds of the formula (C2) with the compounds of the formula (Aa) in the presence of a base.
  • Mercaptan derivatives of the formula (Aa), for example methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods for example, analogously to those described in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
  • the reaction to give compound of the formula (C2) may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Sodium hydride. Step g)
  • the compounds of the formula (E2) can be prepared by oxidation of the compounds of the formula (D2).
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • esters of the formula (E2) can be prepared using standard methods, cf. DE 2221647 and WO2011 / 41713 into which acid of formula (F2) is converted, for example with an alkali hydroxide as base such as sodium hydroxide or lithium hydroxide in an alcohol as solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • an alkali hydroxide as base such as sodium hydroxide or lithium hydroxide in an alcohol as solvent
  • solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • the invention also relates to methods of combating animal pests by allowing compounds of formula (I) to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, in particular nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.
  • measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications 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 is therefore to be understood as referring to 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 determine the presence of hygiene pests and / or to avoid exposure to them in the hygiene sector or to limit them to a minimum. This can be achieved in particular by the use of a pesticide, which can be used both to prevent infestation and to prevent an already existing infestation. It is also possible to use preparations which prevent or reduce exposure to pests.
  • Hygiene pests include, for example, the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Anoplophora glabripennis Anthonomus spp., Z. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
  • Hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., E.g. Megacyllene robiniae, Megascelis spp., Melanotus spp., E.g.
  • Melanotus longulus oregonensis Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g.
  • Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
  • B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Trioza spp. E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria tremani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. Homo. Spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B.
  • Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata; Pests of the strain of Mollusca, z. B. from the class of Bivalvia, z. B. Dreissena spp .; and from the class of Gastropoda z. B. Arion spp., Z. B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., Z. B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
  • Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g.
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as a remedy for MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS).
  • formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants. The preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties.
  • Suitable extenders z As water, polar and nonpolar organic chemical liquids such. B. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), the ketones (such as acetone, cyclohexanone ), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg.
  • Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such.
  • cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • Suitable carriers can be used.
  • As carriers are in particular question: z.
  • ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Minerals such as fumed silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: z.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
  • alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
  • auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg.
  • dyes such as inorganic pigments, eg.
  • iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other auxiliaries may be mineral and vegetable oils.
  • further auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestering agents, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, Semiochemicals and / or plant growth regulators are used to z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of formula (I) can be used to improve plant properties such as growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, e.g.
  • carbamates e.g. B. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosul
  • sodium channel modulators such as pyrethroids, e.g. A-rinathrin, 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], esf
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • nAChR nicotinic acetylcholine receptor
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Microbial disruptors of insect intestinal membrane such.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors such as diafenthiuron or organotin compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • ATP disruptors such as diafenthiuron or organotin compounds, e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
  • ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • octopamine receptor agonists such as amitraz.
  • Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (22) blocker of the voltage-dependent sodium channel, such. Indoxacarb or metaflumizone.
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiro mesifen and spirotetramat.
  • inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
  • inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
  • ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxa
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetracon
  • inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti- epimeric racemate 1RS, 4SR , 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R, 4
  • 3) respiratory chain inhibitors on complex III for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(IE)
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-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-
  • inhibitors of ATP production for example, (8,001) silthiofam.
  • inhibitors of cell wall synthesis for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
  • Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
  • inhibitors of melanin biosynthesis for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1- [(4-methylbenzoyl) amino] butan-2-yl carbamate.
  • inhibitors of nucleic acid synthesis for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • 13) inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • Cyflufenamid (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (15.013) Fosetyl-calcium, (15.014) Fosetyl-sodium, (15.015) Methylisothiocyanate, (15.016) Metrafenone , (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020) Nitrothal isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiproline, (15.023) Oxyfenthiine, (15.024) Pentachlorophenol and salts, (15.025) Phosphonic acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (Chlazafenone) (15.028) tebufloquine,
  • the compounds of formula (I) may be combined with biological pesticides.
  • Bio pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides. Examples of such bacteria that are used as biological pesticides or can be used are:
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • B. thuringiensis subspecies israelensis serotype H-14
  • strain AM65-52 accesion No. ATCC 1276
  • B. thuringiensis subsp. aizawai in particular strain ABTS-1857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-1 or B. thuringiensis subs
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV
  • Spodoptera frugiperda armyworm
  • mNPV Spodoptera littoralis
  • bacteria and fungi which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health.
  • examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalene 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.
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. All plants should be under plants Development stages such as seeds, cuttings, young (immature) plants to mature plants are understood.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z. B.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
  • PAT phosphinotricin
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the application form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is foliar application, ie the compounds of formula (I) are applied to the foliage, the frequency of treatment and the rate should be adjusted to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • This may be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by soil application, ie the compounds of the formula (I) according to the invention are introduced in solid form (eg in the form of granules) in the location of the plants. In water rice crops this may also be by metered addition of the compound of formula (I) in a solid form (eg as granules) into a flooded paddy field.
  • Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention.
  • the invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component.
  • the individual substances may be present in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • a compound of formula (I) acts systemically is that treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous Genes in transgenic seeds can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. There are both in Water sparingly soluble pigments as well as water-soluble dyes usable. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • polyvinylpyrrolidone polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemistry of Crop Protection and Pest Control", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water
  • all mixing devices which can usually be used for the dressing can be considered.
  • the seed is placed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of formula (I) which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or Poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of formula (I) are administered to birds, namely caged birds or, in particular, poultry.
  • birds namely caged birds or, in particular, poultry.
  • deaths and reductions in performance should be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable.
  • controlling means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced. More specifically, “combating” in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomy
  • Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephal
  • Mastigophora (Flagellata), like:
  • Metamonada from the order Vaccinia spp., Spironucleus spp.
  • Parabasala from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp. Euglenozoa: from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
  • Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B.
  • Leucocytozoon spp. Plasmodium spp .; from the order Piroplasmida z. Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp .; from the order Vesibuliferida z. Balantidium spp., Buxtonella spp.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • Acute helminths pathogenic to humans or animals include, for example, Acanfhocephala, nematodes, pentastoma and platyhelminthes (e.g., Monogenea, Cestodes and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea z.
  • Dactylogyrus spp. Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
  • Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Or
  • Nematodes from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • 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., Oesoot
  • 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 well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
  • Another aspect relates to the compounds of formula (I) for use as antiendoparasitic.
  • Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic agents, in particular for use as nematicide, platelet minthicide, acanthocephalicide or pentastomicide.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
  • Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg, solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg, surfactants
  • a related aspect of the invention is a method of making a veterinary formulation as described herein which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, especially pharmaceutically acceptable excipients conventionally used in veterinary formulations; or conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying a veterinary formulation as defined herein to 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 parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of formula (I) with other active ingredients, especially endo and ectoparasiticides, are provided herein for the veterinary field.
  • blending not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances should be formulated in a common formulation, or all active substances should be formulated in separate formulations, or mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
  • Active substances with unknown or non-specific mechanisms of action eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
  • Organochlorine compounds e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner;
  • Pyrethroids e.g. Eg, (cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin , Cyhalothrin (lambda), chlovaporthrin, or halogenated hydrocarbon compounds (HCHs),
  • Neonicotinoids e.g. B. Nithiazine
  • Dicloromezotiaz, triflumezopyrim, macrocyclic lactones e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; Milbemycin oxime, triphene, epofenone, diofenolane; Biologicals, hormones or pheromones, for example natural products, eg thuringiensin, codlemon or neem components
  • Dinitrophenols e.g. Dinocap, dinobuton, binapacryl
  • Benzoylureas eg. As fluazuron, penflurone, amidine derivatives, z. B. Chlormebuform, cymiazole, demiditraz
  • Hive varroa acaricides for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, trematicidal and / or cestozide agents: from the class of macrocytic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
  • all said mixing partners can optionally form salts with suitable bases or acids.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • Examples of vectors and their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • - Culex Japanese encephalitis, filariasis, other viral diseases, transmission of other worms
  • - Aedes yellow fever, dengue fever, other viral diseases, filariasis
  • Ticks Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the supply and material protection.
  • the compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the application of the invention for the protection of wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of the formula (I) are present as ready-to-use pesticides, ie they can be applied to the corresponding material without further changes.
  • insecticides or fungicides in particular those mentioned above come into question.
  • the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out for example in aerosols, non-pressurized sprays, z.
  • the reaction mixture was degassed using nitrogen and stirred at 100 ° C for 2 h in the microwave.
  • the catalyst was removed by filtration through Celite and washed with ethyl acetate.
  • the organic phase was dried over NaiCC, filtered and freed from the solvent under reduced pressure.
  • the crude product was purified by column chromatographic purification via preparative HPLC. logP (sour): 2.28; MH + : 467; 1 H-NMR (300 MHz, D 6 -DMSO) ⁇ ppm: 8.97 (d, 1H), 8.88 (s,
  • the determination of the logP values was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C18) using the following methods: [ ] The logP value is determined by LC-UV measurement in the acidic range determined with 0.9 ml / 1 formic acid in water and 1.0 ml / 1 formic acid in acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • the logP value is determined by LC-UV measurement in the neutral range, with 79 mg / 1 ammonium carbonate in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). Calibration was carried out with a homologous series of straight-chain alkan-2-ones (having 3 to 16 carbon atoms) with known logP values. The values between consecutive alkanones are determined by linear regression.
  • Mass Spectrometry Determination of [M + H] + or M " by LC-MS under acid chromatographic conditions was performed with 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluent to form the Zorbax Eclipse Plus C18 column 50 mm * 2.1 mm, 1.8 ⁇ used, at a temperature of the column oven of 55 ° C.
  • 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 mass spectrometer, HTS 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 ⁇ 50 mm * 2.1 mm, column 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 HTS PAL sample changer (column: Zorbax XDB C18 1.8 ⁇ 50 mm * 4.6 mm, column 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 in all cases determined from a calibration measurement of a homologous series of 3 to 16 carbon straight chain alkan-2-ones with the index of the first alkanone set at 300, the latter at 1600, and linear between the values of successive alkanones was interpolated.
  • the measurements of the ⁇ -NMR spectra were taken with a Bruker Avance III 400 MHz
  • Spectrometer equipped with a 1.7 mm TCI probe, with tetramethylsilane as standard (0.00 ppm) of solutions in the solvents CD 3 CN, CDCL or dö-DMSO performed.
  • 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 measurement temperatures have been used, this will be noted separately.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇ (intensity;; ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of the IH NMR peaks are similar to the classical IH NMR prints and thus usually contain all the peaks that are listed in a classical NMR interpretation.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
  • the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
  • a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • active compound 10 mg are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately 20 Ll larvae of the Australian Sheep Gold Fly (Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
  • Solvent Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
  • ⁇ of the drug solution is injected into the abdomen of 5 wet, adult, female bovine ticks (Boophilus microplus).
  • the animals are transferred to trays and kept in an air-conditioned room.
  • the effect control takes place after the desired time on storage of fertile eggs.
  • Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching.
  • An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • the vials are populated with 5-10 adult dog ticks (Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
  • a substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.
  • Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to the untreated control.
  • the active ingredient preparation 50 ⁇ of the active ingredient preparation are transferred into microtiter plates and filled with 150 ⁇ l IPL41 insect medium (33% + 15% sugar) to a final volume of 200 ⁇ . Subsequently, the plates are sealed with parafilm, through which a mixed population of greens Peach aphid (Myzus persicae), which is located in a second microtiter plate, pierce and absorb the solution.
  • IPL41 insect medium 33% + 15% sugar
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed. In this test, z.
  • the following compounds of Preparation Examples have an effect of 100% at a rate of 4ppm: 1-01, 1-02, 1-03, 1-05, 1-06, 1-07, 1-08, 1-09, 1 -10, 1-12, 1-13, 1-14
  • Myzus persicae - Spray Test Solvent 78 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, it is diluted with emuigly ator ambiencem water.
  • Emulsifier alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, it is diluted with emuigly ator ambiencem water.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Spodoptera frugiperda - spray test solvent 78.0 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, it is diluted with emuigly ator ambiencem water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
  • the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed. In this test, z.
  • the following compounds of Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-04, 1-05, 1-06, 1-08, 1-09, 1-11, 1-12 , 1-13, 1-14, 1-15, 1-17, 1-20, 1-21, 1-22, 1-29
  • Emulsifier alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, it is diluted with emuigly ator ambiencem water.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Phaedon cochleariae - spray test PHAECO
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached.
  • dilute with emulsifier-containing water When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Cabbage leaves (Brassica oleracea) are sprayed with an active compound preparation of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Plutella xylostella - spray test (PLUTMA)
  • Emulsifier alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Cabbage leaves (Brassica oleracea) are sprayed with a preparation of active compound of the desired concentration and infected with larvae of the cabbage (Plutella xylostella).
  • SPODFR Spodoptera frugiperda - spray test
  • Emulsifier alkylaryl polyglycol ether
  • 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached.
  • dilute with emulsifier-containing water When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Cotton leaves Gossypium hirsutum
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, whereby the volume of the earth into which it is compressed must also be taken into account. It must be ensured that a concentration of 40 ppm emulsifier is not exceeded in the soil. To prepare further test concentrations, it is diluted with water. Corn plants (Zea mays) in soil pots are poured with an active compound preparation of the desired concentration and infected with caterpillars of the armyworm (Spodoptera frugiperda).
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • HELIAR Heliothis armigera - spray test
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Cotton plants Gossypium hirsutum
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water dilute with ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Paprika plants Capsicum annuum which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration. After the desired time the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals were killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, whereby the volume of the earth is forced into the vessel. It must be ensured that a concentration of 40 ppm emulsifier is not exceeded in the soil. To prepare further test concentrations, it is diluted with water. Savoy cabbage plants (Brassica oleracea) in pots of soil that are infested by all stages of the Green Peach aphid (Myz s persicae) are infused with an active substance preparation of the desired concentration.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Diabrotica balteata - Drench test (DIABBA D)
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, whereby the volume of the earth is forced into the vessel. It must be ensured that a concentration of 40 ppm emulsifier is not exceeded in the soil. To prepare further test concentrations, it is diluted with water.
  • Each 5 corn kernels are seeded in pots filled with soil (Zea mays) and the next day with the active ingredient preparation of the desired concentration poured. After one day, about 25 L2 larvae of the corn rootworm (Diabrotica balteata) are added.

Abstract

L'invention concerne de nouveaux composés de formule (I) dans laquelle Aa, Ab, R1, R2, R3, R4, R5et n ont les significations mentionnées dans la description, leur utilisation comme acaricides et/ou insecticides pour lutter contre les animaux nuisibles, ainsi que des procédés et des produits intermédiaires pour les produire.
EP18774061.8A 2017-10-04 2018-09-28 Dérivés hétérocycliques utilisés comme pesticides Pending EP3692045A1 (fr)

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US20200291043A1 (en) 2020-09-17
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