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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
• • 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
  • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
  • C07D498/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
  • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
  • C07D513/04—Ortho-condensed systems

Definitions

• the present invention relates to novel condensed bicyclic heterocyclic derivatives of the formula (I), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular insects and arachnids, and methods and intermediates for their preparation.
• condensed bicyclic heterocyclic derivatives which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, better insecticides, acaricidal activity, as well as a good tolerance to crops exemplified.
• the condensed bicyclic heterocyclic derivatives can be used in combination with other agents for improving the effectiveness in particular against difficult-to-control insects.
• the present invention therefore relates to novel compounds of the formula (I)
• R 2 , R 3 independently of one another represent hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN, tri- (Ci-C 6) alkylsilyl, (C 3 -C 8) cycloalkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl, (Ci- C 6) alkyl (C 3 -C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C6) cyanoalkyl, (Ci-C6) hydroxyalkyl, hydroxycarbonyl (Ci-C6 ) alkoxy, (Ci- C 6) alkoxycarbonyl (Ci-C6) alkyl, (Ci-C 6) alkoxy (Ci-C 6) alkyl, (C 2 -
• C 8) cycloalkyl, halo (C 3 -C 8) cycloalkyl, (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci- Ce) cyanoalkyl, (Ci-Ce) hydroxyalkyl, hydroxycarbonyl (Ci- C6) -alkoxy,
• Aminothiocarbonyl (C 1 -C 6) alkylaminothiocarbonyl, di (C 1 -C 6) alkylaminothiocarbonyl, (C 3 -C 8) cycloalkylamino, (C 1 -C 6) alkylcarbonylamino, for a partially saturated or saturated heterocyclic or heteroaromatic 8, 9, 10 , 11- or 12-membered fused bicyclic or tricyclic ring system, wherein optionally at least one carbonyl group may be contained and / or wherein the ring system optionally monosubstituted or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from cyano , halogen, nitro, acetyl, hydroxy, amino, SCN, tri- (Ci-C 6) alkylsilyl, (C 3 -C 8) cycloalkyl, (C 3 - C 8) cycloalkyl (C 3
• C ⁇ ) alkylcarbonylamino or wherein the substituents can be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted, identically or differently, by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, NO 2 , Ci-C4-alkoxy, Ci-C4-haloalkoxy, is 0, 1 or 2, except
• 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.
• Ad is preferably nitrogen or C (H) -, where Aa, Ab, Ac and Ad can not be simultaneously nitrogen, R 1 is preferably (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, ( Ci-C 4) haloalkyl, (CI-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, ( C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy
• R 2 , R 3 independently of one another preferably represent hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN, tri (C 1 -C 4 ) -alkylsilyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6) cycloalkyl (C 3 - C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, (C - C 4) haloalkyl, (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2
• Aa particularly preferably represents nitrogen or C (H) -
• Ab particularly preferably represents nitrogen or C (H) -
• R 1 particularly preferably represents (Ci-C4) alkyl, (Ci-C4) hydroxyalkyl, (Ci-C4) haloalkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4) alkyl or (Ci-C 4) alkylsulfonyl (C 1 -C 4) alkyl,
• R 4 particularly preferably represents (Ci-C alkyl, (Ci-C4) haloalkyl, (Ci-C4) cyanoalkyl, (Ci C 4) hydroxyalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) haloalkenyloxy - (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) cyanoalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) alkynyloxy (Ci-C 4 ) alkyl, (C 2 - C 4) -haloalkynyl,
• Aa, Ab, Ac and Ad can stand for a maximum of two nitrogens
• R 1 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, Trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R 2, R 3 independently of one another very particularly preferably represents hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (CI-C 4) alkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C4) haloalkylthio,
• R 4 very particularly preferably represents (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
• R 5 very particularly preferably represents hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl, (C3-C 6 ) cycloalkyl, (Ci-C 4 ) alkyl (C 3 -C 6 ) cycloalkyl, (Ci-C) alkoxy, (Ci-C) haloalkoxy, (Ci-C) alkoxyimino, (Ci-C) alkylhio, (Ci -C 4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (Ci- C 4 ) alkylsulfonyl, (C 1 -C 4 ) haloalkylsulfonyl, (
• R 6 very particularly preferably represents hydrogen, n very particularly preferably represents 0, 1 or 2.
• R 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropyl
• R 2 independently of one another represents hydrogen, cyano, halogen, (Ci-C4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci- C 4) alkylsulfinyl, (Ci C 4) alkylsulfonyl, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfinyl, (Ci-
• Q stands for a heteroaromatic 9-membered fused bicyclic ring system from the series Q2, Q3, Q10, Q14 or Q16,
• Q14 Q16 stands for methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl, (especially highlighted for methyl),
• R 5 represents hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C3-C6) cycloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy , (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (Ci C 4) alkylsulfonyl, ( Ci-C 4) halogenoalkylsulphonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C4) alkyl aminocarbonyl, (Ci-C4) alkylsulfonylamino, (Ci-C4) alkylaminosulfonyl
• R 6 stands for hydrogen, n stands for 0, 1 or 2.
• R 1 stands in particular for ethyl
• R 2 is in particular hydrogen, chlorine or methylthio (SCH 3 ), R 3 is especially hydrogen,
• Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q2 or Q3,
• the invention relates to compounds of formula (I) wherein Q is Q19 and
• R 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (Ci C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4 ) alkyl or (C 1 -C 4 ) alkylsulfonyl (C 1 -C 4 ) alkyl
• R 2, R 3 are each independently hydrogen, cyano, halogen, nitro, hydroxy, amino, SCN, tri- (Ci-C 4) alkylsilyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl- ( C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (CI-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -
• R 6 represents hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C 3 - C 6) cycloalkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, (Ci-C 4) alkoxy, (Ci C 4) haloalkoxy, (Ci-C4) alkoxyimino, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci C 4) Alkylsulfinyl, (C 1 -
• the invention relates to compounds of formula (I) wherein Q is Q19 and
• R 1 is methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or Pentafluoroethyl stands, R 2 represents hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci-C) haloalkyl, (Ci-C) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C 4) alkylsulfinyl, (Ci- C 4) alkylsulfonyl, (Ci-C4) haloalkylthio, (Ci- C4) haloalky
• R 4 is (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
• R 6 is hydrogen, n is 0, 1 or 2.
• the invention relates to compounds of formula (I) wherein Q is Q19 and
• R 1 is methyl, ethyl, n-propyl, i-propyl or cyclo-propyl
• R 2 is hydrogen, chlorine, fluorine, methyl, trifluoromethyl, methylthio (SCH 3 ), ethylthio (SCH 2 CH 3 ) or ethylsulfonyl,
• R 3 is hydrogen
• R 4 is methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl
• R 6 is hydrogen, n is 0, 1 or 2.
• Ad C (H) -, wherein the following structural unit
• R 1 is ethyl
• R 2 is trifluoromethyl
• R 3 is hydrogen, R 4 is methyl,
• R 6 is hydrogen, n is 0 or 2.
• the invention relates to compounds of the formula (I) in which Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , Q and n have the meanings given in embodiment (1) or (2) have, wherein one of the chemical groups Aa or Ab or Ac or Ad must be nitrogen and wherein the chemical groups Aa, Ab, Ac and Ad can not simultaneously be nitrogen.
• R 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (Ci C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4 ) alkyl or (C 1 -C 4 ) alkylsulfonyl (C 1 -C 4 ) alkyl
• R 2, R 3 are each independently hydrogen, cyano, halogen, nitro, hydroxy, amino, SCN, tri- (Ci-C 4) alkylsilyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl- ( C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (CI-C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -
• Halo (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) alkylsulfinyl (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl or (Ci-C 4) alkylcarbonyl (Ci-C 4) alkyl,
• R 5 , R 6 are independently hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 -C 4) -haloalkynyl, (C 3 - C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl ( C 3 -C 6 ) cycloalkyl,
• R 1 is methyl, ethyl, n-propyl, i-propyl, cyclo-propyl, n-butyl, i-butyl, tert-butyl, cyclo-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or Pentafluoroethyl stands,
• R 2 , R 3 are independently hydrogen, cyano, halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl,
• R is hydrogen, n is 0, 1 or 2.
• the invention relates to compounds of the formula (I) in which (embodiment C)
• R 1 is methyl, ethyl, n-propyl, i-propyl or cyclo-propyl
• R 2 , R 3 are hydrogen
• Q is a heteroaromatic 9-membered fused bicyclic ring system from the series Q2, Q3, Q10, Q14, Q16 or Q19,
• R 4 is methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
• R 5 is hydrogen, cyano, halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) C) alkoxyimino, (Ci-C 4) alkylthio, (Ci- C4) haloalkylthio, (Ci-C 4) alkylsulfinyl, (Ci-C4) haloalkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci-C 4) haloalkylsulfonyl, (Ci-C4) alkylaminocarbonyl, di- (Ci-C 4) alkyl-aminocarbonyl, (Ci- C4) alkylsulfon
• R 6 is hydrogen, n is 0, 1 or 2.
• the invention relates to compounds of the formula (I) in which (embodiment D)
• R 2 is hydrogen
• R 3 is hydrogen
• Q represents a heteroaromatic 9-membered fused bicyclic ring system from the series Q2, or Q3,
• R 4 is methyl
• R 5 is trifluoromethyl or pentafluoroethyl
• R 6 is hydrogen
• n is 0 or 2.
• the invention relates to compounds of the formula (I) in which
• Ad is nitrogen, giving the following structural unit: AI
• Ad C (H) -, giving the following structural unit: A2
• the invention relates to compounds of the formula (I) in which
• Ad C (H) -, giving the following structural unit: A3
• the invention relates to compounds of the formula (I) in which
• Aa is nitrogen
• Ad C (H) -, giving the following structural unit: A4
• the invention relates to compounds of formula (I), wherein Q is Ql and Aa, Ab, Ac, Ad, R 1, R 2, R 3, R 4, R 5, R 6 and n are as in Embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of formula (I), wherein Q is Q2 and Aa, Ab, Ac, Ad, R 1, R 2, R 3, R 4, R 5, R 6 and n are as in Embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q3 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those described in Embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I) wherein Q is Q4 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D ) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q5 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q 6 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of formula (I), wherein Q is Q7 and Aa, Ab, Ac, Ad, R 1, R 2, R 3, R 5, R 6 and n (in embodiment A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of formula (I) wherein Q is Q8 and Aa, Ab, Ac, Ad, R 1, R 2, R 3, R 5, R 6 and n (in embodiment A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of formula (I), wherein Q is Q9 and Aa, Ab, Ac, Ad, R 1, R 2, R 3, R 5, R 6 and n (in embodiment A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q10 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are in the embodiment (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is QU and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n, which in structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q12 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q13 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q14 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q15 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q16 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those described in Embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q17 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q18 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q19 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 4 , R 6 and n are those of the structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I) in which Q is Q20 and Aa, Ab, Ac, Ad, R 1 , R 2 , R 3 , R 5 , R 6 and n, which in structure (A ) or design (B) or design (C) or design (D) have given meanings.
• the invention relates to compounds of the formula (I), wherein Q is Q 2 and
• Ad stands for nitrogen, whereby the following structural unit results: AI and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n those in design (A) or design (B) or design (C) or design (D) given meanings.
• Ad C (H) -, which gives the following structural unit: A2 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I), wherein Q is Q 2 and
• Aa C (H) -
• Ab is nitrogen
• Ad C (H) -, where the following structural unit results: A3 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I), wherein Q is Q 2 and
• Aa is nitrogen
• Ad C (H) -, which gives the following structural unit: A4 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• Ad stands for nitrogen, whereby the following structural unit results: AI and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n those in design (A) or design (B) or design (C) or design (D) given meanings.
• Ad C (H) -, which gives the following structural unit: A2 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• the invention relates to compounds of the formula (I), wherein Q is Q3 and
• Aa C (H) -
• Ab is nitrogen
• Ad C (H) -, where the following structural unit results: A3 and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n in the embodiment (A) or embodiment (B) or embodiment (C) or embodiment (D) have given meanings.
• m relates to the invention compounds of formula (I), wherein Q is for
• the invention relates to compounds of formula (I), wherein Q is for
• the invention relates to compounds of formula (I), wherein Q is for
• the chemical grouping Aa is identical to the chemical grouping A a ; the chemical grouping Ab is identical to the chemical grouping Ab, the chemical grouping Ac is identical to the chemical grouping A c , the chemical grouping is Ad
• Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
• halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine.
• alkyl either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and 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 3 -C 4 -alkynyl radicals
• the alkynyl radical can also have at least one double bond.
• cycloalkyl is understood to mean , either alone or in combination with other terms, understood according to the invention a C3-C8-cycloalkyl understood, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood. Preferred of these are C3-C6-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.
• 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 mixtures of these isomers.
• the compounds of the formula (I) in which Q is Q.sup.1 to Q.sup.9 and Q.sup.19 can be prepared by known methods, for example analogously to those in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715, WO 2015/121136, EP 15153943.4 or EP 15153948.3.
• radicals or chemical groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 represent CH or N (wherein A 2 and A 3 can not simultaneously be N), A 4 represents O, S or NR 4 and X 1 represents halogen.
• the compounds of the formula (IV) can be prepared in analogy to the process described in US Pat. No. 5,573,335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
• Compounds of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO2006 / 65703, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715 described method.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in method E.
• reaction of the compounds of the formula (II) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
• halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
• Nitriles such as acetonitrile or propionitrile
• aromatic hydrocarbons such as toluene or xylene
• aprotic polar solvents such as N, N-
• Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• bases are inorganic bases which are commonly used in such reactions.
• bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
• Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
• the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
• the compounds of formula (V) can be prepared by condensation of the compounds of formula (IV) 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 (V) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
• the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chloride
• suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
• Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
• acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
• suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
• nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
• DBU 1,8-diazabicyclo [5.4.0] -7-undecene
• tertiary amines such as triethylamine and N, N
• An example of a suitable chlorinating agent is phosphorus oxychloride.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
• the compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base.
• Mercaptan derivatives of the formula (Via), such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
• the reaction to give compound of formula (I) wherein n is 0 may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent selected from conventional solvents inert to the prevailing reaction conditions.
• ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-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. Preference is given to cesium carbonate, Sodium carbonate and potassium carbonate.
• suitable bases are alkali metal hydrides such as sodium hydride.
• X 1 is preferably a fluorine or chlorine atom.
• the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
• the oxidation is generally carried out in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• Suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• the compounds of formula (I) wherein n is 2 may be prepared by oxidation of the compounds of formula (I) wherein n is 1.
• the oxidation is generally carried out in a solvent.
• Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
• the oxidation is generally carried out in a solvent.
• halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• Process B The compounds of the formula (I) in which Q is Q10, QU, Q14 and Q15 can be prepared by known methods, for example analogously to those in US2009 / 203705, US2012 / 258951,
• R 1 , R 2 , R 3 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above.
• a 2 , A 3 , A 4 and A 5 are CH or N (wherein A 2 , A 3 , A 4 and A 5 are not simultaneously N) and X 1 is halo.
• Step a) Carboxylic acids of the formula (III) are converted in analogy to the process described in WO2011 / 75643 or EP2671582 in the presence of ⁇ , ⁇ -dimethylhydroxylamine hydrochloride into Weinreb amides of the formula (VI).
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in method E.
• the compounds of the formula (X) can be prepared by cyclization of the compounds of the formula (VIII) with amines of the formula (IX).
• the cyclization is carried out, for example, in ethanol, acetonitrile or ⁇ , ⁇ -dimethylformamide by known methods analogously to, for example, WO2005 / 66177, WO2012 / 88411, WO2013 / 3298, US2009 / 203705, US2012 / 258951, WO2012 / 168733, WO2014 / 187762 or J. Med. Chem. 31 (1988) 1590-1595.
• Step e) The compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (X) with the compounds of the formula (VI) in the presence of a base.
• Mercaptan derivatives of the formula (Via) such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
• the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
• the oxidation is carried out by known methods with a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• the compounds of formula (I) wherein n is 2 may be prepared by oxidation of the compounds of formula (I) wherein n is 1.
• the oxidation is generally carried out in a solvent.
• halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
• the oxidation is generally carried out in a solvent.
• halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the compounds of the formula (I) in which Q is Q16 can be prepared by known methods, for example analogously to the processes described in WO2014 / 142292.
• the compounds of formula (XI) can be prepared in analogy to that described in US5374646 or Bioorganic and Medicinal Chemistry Letters 2003, 13, 1093-1096 by the reaction of compounds of formula (III) with an ammonia source in the presence of a condensing agent.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in method E.
• Ammonia hydroxide is usually used as the source of ammonia.
• the reaction of the compounds of the formula (III) with the source of ammonia is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, dioxane or tetrahydrofuran.
• a suitable condensing agent is, for example, carbonyldiimidazole.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 70 ° C.
• the compounds of the formula (XIII) can be prepared in analogy to the process described in WO2014 / 142292 by the reaction of compounds of the formula (XI) with compounds of the formula (XII) in the presence of a palladium catalyst in basic.
• Compounds of the formula (XII) can be prepared, for example, analogously to the processes described in WO2014 / 142292.
• the palladium catalyst for example, [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) can be used.
• base often find inorganic bases such as Kaliumtertbutanolat use
• the reaction takes place in a solvent. Often, toluene is used.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 110 ° C.
• Method D The compounds of formula (I) wherein Q is Q12, Q13, Q17, Q18 and Q20 may be prepared according to known methods, for example analogously to the method described in WO2010 / 091310, WO 2012/66061 or WO2013 / 099041.
• R 2 , R 3 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above.
• a 2 , A 3 and A 6 are CH or N.
• X 1 and X 2 are halogen.
• the compounds of formula (XIX) can be prepared by reacting compounds of formula (XVII) with compounds of formula (XVIII) under basic conditions, e.g. analogously to the process described in WO2010 / 091310, WO 2012/66061 or WO2013 / 099041.
• Compounds of the formula (XVII) are either commercially available or can be prepared by known methods, for example analogously to the method described in WO2005 / 100353, WO 2012/66061 or in European Journal of Medicinal Chemistry 45 (2010), 2214-2222.
• the bases used are usually inorganic bases such as sodium hydride, potassium carbonate or cesium carbonate.
• the reaction to give compounds of the formula (XIX) is usually carried out in a solvent, preferably in a nitrile, for example acetonitrile or propionitrile, or in an aprotic polar solvent, for example ⁇ , ⁇ -dimethylformamide or N-methylpyrrolidone.
• reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
• reaction of compounds of the formula (XVII) with compounds of the formula (XVIII) to give compounds of the formula (XIX) can also be carried out by palladium-catalyzed N-arylation, for example analogously to that described in Angewandte Chemie Int. Ed. 2011, 50, 8944-8947.
• the further reaction of compounds of the formula (XIX) to give compounds of the formula (I) is carried out analogously to process A.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods, for example from cyanohetaryl derivatives and 2-sulfanyl acetates analogous to those described in Organic & Biomolecular Chemistry, 13 (2015), 6814-6824; Journal of Medicinal Chemistry, 56 (2013), 2606-2618; Bioorganic & Medicinal Chemistry Letters, 22 (2012), 3643-3647; WO2014 / 186035; WO2014 / 062553; Journal of Heterocyclic Chemistry, 24 (1987), 85-89; US2007 / 0049603; WO2015 / 027124, WO2008 / 090944, European Journal of Medicinal Chemistry, 58 (2012), 171-183; Zhongguo Yiyao Gongye Zazhi, 41 (2010), 249-250; Angewandte Chemie International Edition, 54 (2015), 6442-6446 and JP 1994/06220020.
• R 2 , R 3 , Aa, Ab, Ac and Ad have the meanings described above, wherein Aa, Ab, Ac and Ad can not simultaneously be nitrogen.
• X 1 and X 2 are halogen and R 8 is Ci-Ce-alkyl.
• the compounds of formula (XXI) can be prepared in analogy to those described in Organic & Biomolecular Chemistry, 13 (2015), 6814-6824; Journal of Medicinal Chemistry, 56 (2013), 2606-2618; Bioorganic & Medicinal Chemistry Letters, 22 (2012), 3643-3647; WO2014 / 186035; WO2014 / 062553; Journal of Heterocyclic Chemistry, 24 (1987), 85-89; US2007 / 0049603; WO2015 / 027124 and WO2008 / 090944 by reacting compounds of formula (XX) with a suitable mercaptan, for example a 2-sulfanyl acetate derivative, under cooling, at room temperature or under thermal conditions in a suitable solvent such as dimethyl sulfoxide, toluene, Ethanol, acetonitrile or dimethylformamide or in mixtures of these solvents using suitable bases such as tertiary amine bases such as triethylamine, hydroxide bases such
• the 2-sulfanyl acetate derivatives are commercially available.
• the compounds of formula (XX) are either commercially available or can be prepared by known methods, for example analogously to those described in European Journal of Medicinal Chemistry, 58 (2012), 171-183; Zhongguo Yiyao Gongye Zazhi, 41 (2010), 249-250; Angewandte Chemie International Edition, 54 (2015), 6442-6446; WO2014 / 186035 and JP 1994/06220020. Step b) and c)
• Compounds of the formula (XXII) can be prepared by known methods from compounds of the formula (XXI) via a halogenation in analogy to those described in Organic & Biomolecular Chemistry, 13 (2015), 6814-6824; WO2015 / 009837; Journal of Medicinal Chemistry, 56 (2013), 2606-2618; Bioorganic & Medicinal Chemistry Letters, 22 (2012), 3643-3647; WO2014 / 186035; WO2014 / 062553; WO2015 / 027124; WO2008 / 090944 described, for example via a diazotization followed by substitution with a nucleophilic halogenating reagent such.
• copper (II) bromide a mixture of copper (I) bromide and hydrogen bromide or a mixture of hydrogen peroxide and hydrochloric acid in dimethylformamide, acetonitrile or water as a solvent.
• the ester of formula (XXII) can be prepared using standard methods, cf. DE 2221647 or WO2011 / 41713 be converted into the acid of formula (III), for example with an alkali metal hydroxide as a base such as sodium hydroxide or lithium hydroxide in an alcohol as a solvent such as ethanol or a mixture of tetrahydrofuran and water.
• an alkali metal hydroxide as a base such as sodium hydroxide or lithium hydroxide in an alcohol as a solvent such as ethanol or a mixture of tetrahydrofuran and water.
• the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
• the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
• pest control always always includes the term pesticides.
• the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, to improve the quality of the crop and to control 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.
• the term “hygiene 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.
• the term “hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
• hygiene pests include the organisms mentioned below.
• the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the above mentioned pests include:
• Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
• Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
• Panonychus citri Metatetranychus citri
• Panonychus ulmi Metatetranychus ulmi
• Phyllocoptruta oleivora Platytetranychus multidigituli
• Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
• Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
• Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
• Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
• hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B.
• Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
• Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
• Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
• Tanymecus spp. E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B.
• Delia antiqua Delia coarctata, Delia llorilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g.
• Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus lloccosus, 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. Trioza diospyri Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
• Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
• Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
• Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
• Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
• Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp.
• Heliothis virescens Hofmannophila pseudospretella Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria ilavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
• Leucoptera coffeella Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
• Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g.
• Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
• Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
• Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
• Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
• Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g.
• Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
• 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 an anti-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.
• dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
• glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
• Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
• SL water-soluble liquids
• EC emulsion concentrates
• EW emulsions in water
• SC suspension concentrates
• SC SE, SE, FS, OD
• WG water-dispersible granules
• GR granules
• capsule concentrates CS
• the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
• auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
• An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
• Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
• formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
• excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
• the preparation of the formulations is carried out either in suitable systems or before or during use.
• Excipients which can be used are those which are suitable for imparting special properties to the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, usable pesticides such as spray mixtures or seed dressing), such as certain physical, technical and / or to confer biological properties.
• Suitable extenders z As water, polar and nonpolar organic chemical liquids such. 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.
• carriers are in particular question: z.
• ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
• Suitable carriers for granules are: z.
• liquefied gaseous diluents or solvents can be used.
• extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
• aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
• Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
• alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
• a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
• auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg.
• dyes such as inorganic pigments, eg.
• iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
• Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
• formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
• additional auxiliaries may be mineral and vegetable oils.
• auxiliaries may be present in the formulations and in the use forms derived therefrom.
• additives are, for example, perfumes, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
• the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
• retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
• Penetration promoters in the present context include all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
• Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle.
• the method described in the literature can be used to determine this property.
• the formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), more preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly preferably between 0.5 and 90% by weight .- 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 ,
• 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 be so z.
• suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be so z.
• B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance.
• such drug combinations, plant growth and / or tolerance to abiotic factors such. As
• the flowering and fruit behavior can be improved, the germination and rooting can be optimized, the harvest can be improved and the harvest yield can be improved increase the quality and / or nutritional value of the harvested products, extend the shelf life and / or improve the workability of the harvested products.
• 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
• GABA-controlled chloride channel B loosened such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
• sodium channel modulators such as pyrethroids, e.g.
• nAChR nicotinic acetylcholine receptor
• neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxalor or flupyradifurone.
• AUotic nicotinic acetylcholine receptor (nAChR) modulators such as spinosyn, e.g. B. spinetoram and spinosad.
• AUosteric 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.
• Non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or crushing tartar or methyl isocyanate producers, e.g. Diazomet and Metam.
• modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
• mite growth inhibitors such as. Clofentezine, hexythiazox and dillovidazine or etoxazole.
• 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.
• Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
• Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, novillumuron, teflubenzuron and triflumuron.
• inhibitors of chitin biosynthesis type 1, such as buprofezin.
• Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
• ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
• 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).
• (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
• inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
• inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
• ryanodine receptor modulators for example diamides, e.g. B.
• All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
• All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
• inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetracon
• 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) anisulbromo, (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-dino-phenyl) -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-fluoro-1-yl) -N- (2
• Copper naphthenate (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2 +) sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015 ) Metiram, (5.016) Zinc metiram, (5.017) copper oxine, (5.018) propylene, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram.
• Inhibitors of ATP production for example, (8,001) silthiofam.
• inhibitors of cell wall synthesis for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007)
• 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 signal transduction for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
• the compounds of formula (I) may be combined with biological pesticides.
• Bio pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
• Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
• Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 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
• 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 wrapper
• Granulosis virus GV
• Cydia pomonella codling moth
• Granulosis virus GV
• Helicoverpa armiger a cotton capsule worm
• Nuclear polyhedrosis virus NPV
• Spodoptera exigua mNPV Spodoptera frugiperda (armyworm) mNPV
• Spodoptera littoralis Africann cotton worm
• Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacid), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
• plant extracts and products formed by microorganisms including proteins and secondary metabolites, which can be used as biological pest control agents are:
• Safeners as Mixture Components The compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) - 1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (CAS 52
• 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 produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods can be obtained, including transgenic plants and including plant varieties that are protectable or unprotectable by plant variety rights.
• Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants.
• Plant parts are 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.
• all 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 Ab resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
• toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
• systemically acquired resistance SAR
• systemin phytoalexins
• elicitors elicitors
• resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
• herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
• 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, i. H. the compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
• the compounds of the formula (I) also enter the plants via the root system.
• the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
• This may be, for example, by drenching, mixing into the soil or the nutrient solution, 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.
• 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 in different layers may be present 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.
• Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
• Compounds of 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 may consist of 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. Both water-insoluble pigments and water-soluble dyes are useful in this case. As examples mention may be made of 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.
• Preferably usable are silicone defoamers and magnesium stearate.
• Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
• Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
• Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
• Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
• the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
• the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
• the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
• the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
• the 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.
• 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.
• 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
• the following Akari can be mentioned by way of example: 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.
• the family Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., I
• parasitic protozoa examples include, but are not limited to: Mastigophora (Flagellata), such as:
• Metamonada from the order Vaccinia spp., Spironucleus spp.
• Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
• Euglenozoa from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
• Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. 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.
• the human or animal pathogenic helminths include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (eg, 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
• Ollulanus spp . Ollulanus spp .; Ornithostrongylus Spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp.
• Strongylus spp. Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
• 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 which comprise an effective amount of at least one compound of formula (I) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
• a related aspect of the invention is a 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 active substances specified here with their "common name" are known and described, for example, in the "Pesticide Manual” (see above) or searchable on the Internet (eg http://www.alanwood.net / pestici of).
• 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
• Compounds from other classes eg, butacarb, dimetilane, cloethocarb, phosphocarb, pirimiphos (- ethyl), parathion (-ethyl), methacrifos, isopropyl-o-salicylate, trichlorofon, sulprofos, propaphos, sebufos, pyridathion, prothoate, dichlofenthione, demeton S-methylsulfone, isazofos, cyanofen
• 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
• Bios, hormones or pheromones for example natural products, e.g. Thuringiensin, codlemon or neem components dinitrophenols, e.g. Dinocap, dinobuton, binapacryl;
• Benzoylureas eg. Fluazuron, penfluron,
• Amidine derivatives e.g. B. Chlormebuform, cymiazole, demiditraz
• Beehive Varroa acaricides for example organic acids, eg formic acid, oxalic acid.
• exemplary agents from the group of endoparasiticides, as a mixture partner include, but are not limited to, anthelmintic agents and antiprotozoal agents.
• the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flu
• Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
• all said mixing partners can optionally form salts with suitable bases or acids.
• a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
• pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
• the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
• vectors and their transmitted diseases or pathogens are:
• flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
• mites acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;
• Ticks Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
• vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
• Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
• vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. BA gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
• insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. BA 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. Protection of technical materials
• the compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
• the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
• the compounds of formula (I) are present as a ready-to-use pest control agent, i. h., They can be applied to the appropriate material without further changes. As further 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 formula (I) are useful in the control of animal pests in the hygiene sector.
• the invention can be used in household, hygiene and storage especially for controlling insects, arachnids, ticks and mites found in confined spaces, such as homes, factories, offices, vehicle cabins, animal breeding facilities.
• 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.
• Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
• reaction solution was poured into water, extracted with ethyl acetate, and the combined organic phases were washed with saturated NaCl solution and dried over Na 2 SO 4 .
• the solvent was removed and the residue was purified by column chromatography on a preparative HPLC with a water / acetonitrile gradient as eluent.
• the determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
• logP neutral
• the calibration is carried out with un branched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by retention times by linear interpolation between two consecutive alkanones).
• NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists.
• the solvent in which the NMR spectrum was recorded is given in each case.
• the IH-NMR data of selected examples are recorded in the form of IH-NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
• the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇ (intensity;; ⁇ ⁇ (intensity);
• the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
• 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
• 1 H NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D ⁇ and the peak of water, which are usually in the Average high intensity.
• the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
• Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints.”
• 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 become. This isolation would be similar to peak picking in classical 1H NMR interpretation.
• Example 1-029: 1 H-NMR (400.0 MHz, de-DMSO): ⁇ 9.29 (4.16), 8.402 (1.27), 8.397 (1.11), 8.389 (0.83), 8.379 (1.47), 8.355 (1.4), 8.352 (1.28), 8.345 (0.85), 8.338 (1.21), 8.332 (1.48 7,742 (0.59), 7,714 (3.07), 7,705 (2.56), 7.7 (1.57), 7,686 (0.47), 3,892 (16), 3,494 (1.09), 7,724 (1.58), 7,724 (0.51); 3.476 (3.57); 3.45 7 (3.61); 3.439 (1.14); 3.328 (136.28); 2.671 (0.61); 2.668 (0.48); 2.507 (83.22); 2.502 (109.29); 2.498 (82.81); 2.334 ( 0.37), 2.329 (0.62), 2.3 25 (0.49),!
• the vials are filled with 5-10 adult cat fleas ⁇ Ctenocephalides felis), closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
• a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
• active compound 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 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, for example, the following compound of the preparation examples show an effect of 80% at an application rate of 20 ⁇ g / animal: 1-023
• Solvent dimethylsulfoxide To prepare 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.
• the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
• the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: 1-001, 1-002, 1-004, 1-008, 1-009, 1-005, 1-010, 1 -011, I-013, 1-014, 1-016, 1-017, 1-018, 1-020, 1-022, 1-023, 1-025
• 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.
• 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 green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution.
• IPL41 insect medium 33% + 15% sugar
• Emulsifier alkylaryl polyglycol ether 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.
• Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
• 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 Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae j.
• the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed. In this test, z.
• the following compounds of Preparation Examples have an effect of 100% at a rate of 500g / ha: 1-001, 1-002, 1-004, 1-009, 1-010, 1-011, 1-012, 1-013 , 1-014, 1-015, 1-017, 1-018, 1-019
• dimethylformamide 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 Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
• Emulsifier alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
• Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

Landscapes

• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=55587015

Family Applications (1)

Country Status (4)

Cited By (7)

Citations (77)

• 2017
  • 2017-02-16 WO PCT/EP2017/053475 patent/WO2017144341A1/de active Application Filing
  • 2017-02-21 TW TW106105673A patent/TW201741310A/zh unknown
  • 2017-02-21 AR ARP170100427A patent/AR107680A1/es unknown
  • 2017-02-23 UY UY0001037136A patent/UY37136A/es not_active Application Discontinuation

Patent Citations (79)

Non-Patent Citations (20)

Also Published As

Similar Documents

Legal Events