EP3820868A1 - Heterocyclen-derivate als schädlingsbekämpfungsmittel - Google Patents

Heterocyclen-derivate als schädlingsbekämpfungsmittel

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Publication number
EP3820868A1
EP3820868A1 EP19719222.2A EP19719222A EP3820868A1 EP 3820868 A1 EP3820868 A1 EP 3820868A1 EP 19719222 A EP19719222 A EP 19719222A EP 3820868 A1 EP3820868 A1 EP 3820868A1
Authority
EP
European Patent Office
Prior art keywords
spp
cycloalkyl
alkyl
haloalkyl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19719222.2A
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German (de)
English (en)
French (fr)
Inventor
Rüdiger Fischer
Dominik HAGER
Laura HOFFMEISTER
Matthieu WILLOT
Kerstin Ilg
Ulrich Görgens
Andreas Turberg
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Bayer AG
Original Assignee
Bayer AG
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Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP3820868A1 publication Critical patent/EP3820868A1/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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

Definitions

  • the present invention relates to heterocyclic derivatives of the formula (I), their use as Akari zide and / or insecticides for controlling animal pests, especially of arthropods and in particular of insects and arachnids and methods and intermediates for their preparation.
  • Heterocyclic derivatives having insecticidal properties have already been described in the literature, e.g. in WO2010 / 125985, WO2014 / 142292, WO2014 / 148451, WO2016 / 129684, WO2016 / 162318,
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects and / or improve their activity.
  • heterocyclic derivatives which have advantages over the already known connec tions, for example, be better biological or ecological properties, broader application methods, a better insecticidal, acaricidal effect, as well as a good tolerance to crops exemplified.
  • the heterocyclic derivatives can be used in combination with other agents for improving the effectiveness especially against difficult-to-control insects.
  • the present invention therefore relates to novel compounds of the formula (I)
  • a 1 is N (nitrogen) or C (H),
  • a 2 is N (nitrogen) or C (H),
  • a 3 is oxygen or sulfur
  • R 1 is (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 - C6) alkynyl, (C 2 -C 6) haloalkynyl, (C 3 -C 8) cycloalkyl, halo (C3 -CG) cycloalkyl, (C 3 - C6) cycloalkyl (Ci-C 6) alkyl, (C3-C6) cycloalkyl- (Ci-C 6) -haloalkyl , (Ci-C 6 ) alkyl (C 3 -C 8) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cg) cycloalkyl, (C 3 -Cg) cycloalkyl- (C 3 -Cg) cycloalky
  • R 2 , R 3 independently of one another are hydrogen, halogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) -alkoxy, (C 1 -C 6) -haloalkoxy, (C 1 -C 6) -haloalkylthio, C 6 ) haloalkylsulfinyl, (C 1 -C 6 ) haloalkylsulfonyl or (C 1 -C 6 ) haloalkyl (C 3 -C 6 ) cycloalkyl, (C 1 -C 6 ) cyanoalkyl (C 3 -C 6) cycloalkyl,
  • C 6 haloalkyl- (C 3 -Cg) -cyclocycloalkyl, (C 1 -C 6) -haloalkyl- (C 3 -Cg) -cycloalkyl, optionally mono- or polysubstituted by (C 1 -C 6) -alkyl or halogen-substituted cyano (C 3 -C 6 ) -cycloalkyl , optionally mono- or polysubstituted with cyano or halogen substituted spiro (C 3 -Cg) cycloalkyl (C 3 -Cg) cycloalkyl or optionally mono- or polysubstituted with cyano or halogen (C 4 -C 2 ) bicycloalkyl, wherein one of R 2 or R 3 must be selected from Ci-C 6) haloalkyl (C 3 - C g) cycloalkyl, (Ci-C6) cyano
  • R 5 is hydrogen, halogen, cyano, SF 5, (Ci-C6) alkyl, (Ci-C6) haloalkyl, (CF GOAlkcnyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 3 -CG) cycloalkyl, halogeno (C 3 -CG) cycloalkyl, (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) cycloalkyl, C6) haloalkyl, (Ci-C 6) haloalkyl (C 3 -C 6) cycloalkyl, (Ci-C6) cyanoalkyl, cyano (C 3 C ö) cycloal
  • the compounds of the formula (1) have a very good activity as Schwarzsbehimmp colngsstoff, preferably as insecticides and / or acaricides, moreover, in general, especially against crop plants are very well tolerated by plants.
  • a 1 is preferably N (nitrogen) or C (H),
  • a 2 is preferably N (nitrogen) or C (H),
  • a 3 is preferably oxygen or sulfur
  • R 1 is preferably (Ci-C6) alkyl, (Ci-C6) haloalkyl, (C 2 -Ce) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6) haloalkynyl, (C3 -CG) cycloalkyl, halo (C3 -CG) cycloalkyl, (C 3 - C6) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl- (Ci-C 6 ) haloalkyl, (Ci-C 6 ) alkyl (C 3 -Cg) cycloalkyl, (Ci-C 6 ) haloalkyl- (C 3 -Cg) cycloalkyl, (Ci-C6) cyanoalkyl, (Ci C 6) hydroxyalky
  • R 2 , R 3 are preferably each independently hydrogen, halogen, (Ci-C 6 ) alkyl, (Ci- C 6 ) haloalkyl, (Ci-Ce) alkoxy, (Ci-C 6 ) haloalkoxy, (Ci-C 6 ) haloalkylthio, (Ci- C 6) haloalkylsulfinyl, (Ci-C 6) haloalkylsulfonyl, or (Ci-C 6) haloalkyl (C 3 -Cs) cycloalkyl, (Ci-C6) cyanoalkyl (C3 -CG) cycloalkyl, (Ci- C 6) haloalkyl (C 3 -Cs) cyanocycloalkyl, (Ci-C 6) haloalkyl (C 3 -CG) halocycloalkyl, optionally mono- or polysubstituted by (
  • C8 cyanocycloalkyl, (C 1 -C 6 ) haloalkyl- (C 3 -C 8 ) -halocycloalkyl, optionally mono- or polysubstituted by (C 1 -C 4 ) -alkyl or halogen-substituted cyano (C 3 -C 6 ) -cycloalkyl, optionally mono- or polyfunctional several times with cyano or halogen-substituted spiro (C 3 - C 8) cycloalkyl- (C 3 -C 8) cycloalkyl or optionally mono- or polysubstituted by cyano or halogen-substituted (C4-Ci2) bicycloalkyl,
  • R 5 preferably represents hydrogen, halogen, cyano, SF 5, (Ci-C ö) alkyl, (Ci-C6) haloalkyl, (C 2 - C ö) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 3 -C 8 ) cycloalkyl, halo (C 3 -C 8 ) cycloalkyl, (Ci -C6) cyanoalkyl, cyano (C 3 -C 6 ) cycloalkyl, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) haloalkylthio, (C 1 -C 6 ) alkylsulfinyl
  • a 1 particularly preferably represents N (nitrogen) or C (H),
  • a 2 particularly preferably represents N (nitrogen) or C (H),
  • a 3 particularly preferably represents oxygen or sulfur
  • R 1 particularly preferably represents (Ci-C 6) alkyl, (Ci-C 6) haloalkyl or (C3 -CG) cycloalkyl
  • R 2 particularly preferably represents hydrogen, halogen, (Ci-C i) alkyl, (Ci-C 4) haloalkyl, (CI-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C 4) Halogenalkylsulfmyl or (C i -C 4) haloalkylsulfonyl,
  • R 3 particularly preferably represents (Ci-C 4) haloalkyl (C3 -CG) cycloalkyl, spiro (C3 -CG) cycloalkyl- (C 3 -CG) cycloalkyl, (C4-Ci2) bicycloalkyl or optionally cyano (C 3 -C 6 ) cycloalkyl which is monosubstituted or disubstituted by alkyl or halogen,
  • R5 is more preferably halogen, (Ci-C 6) haloalkyl, (Ci-C 6) haloalkoxy, halogen, (C3 -CG) cycloalkyl, (Ci-C 6) cyanoalkyl, cyano (C 3 -C 6) cycloalkyl ,
  • C 6 haloalkylthio, (C 1 -C 6 ) haloalkylsulfinyl or (C 1 -C 6 ) haloalkylsulfonyl and n is particularly preferably 0, 1 or 2.
  • a 1 very particularly preferably represents N (nitrogen) or C (H),
  • a 2 very particularly preferably represents N (nitrogen) or C (H),
  • a 3 is very particularly preferably oxygen or sulfur
  • R 1 very particularly preferably represents (Ci-C 6) alkyl, (Ci-C 6) haloalkyl or (C3 -CG) cycloalkyl,
  • R 2 very particularly preferably represents hydrogen, (Ci-C i) alkyl or halogen
  • R 3 is very particularly preferably represents (Ci-C 4) haloalkyl (C3 -CG) cycloalkyl, spiro (C 3 - C g) cycloalkyl (C 3 -CG) cycloalkyl or cyano (C 3 -C 6) cycloalkyl .
  • R5 is very preferably halogen, (Ci-C 6) haloalkyl, (Ci-C 6) haloalkoxy, halogen, (C3 -CG) cycloalkyl, cyano (C 3 -C 6) cycloalkyl, (Ci-C 6) haloalkylthio, (Ci- C 6) haloalkylsulfinyl or (Ci-C 6) haloalkylsulfonyl and n is very particularly preferably represents 0, 1 or. 2 Embodiment 5-1
  • a 1 stands for N (nitrogen) or C (H),
  • a 2 stands for N (nitrogen) or C (H),
  • a 3 stands for oxygen or sulfur
  • R 1 stands for (Ci-C4) alkyl
  • R 2 is hydrogen
  • R 3 is highlighted as cyano (CVC 6 ) cycloalkyl
  • R 5 is (Ci-C4) haloalkyl, (Ci-C4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfinyl or (Ci-C4) haloalkylsulfonyl and, n is highlighted for 2.
  • a 1 stands for C (H)
  • a 2 stands for C (H)
  • a 3 stands for oxygen
  • R 1 is (Ci-C4) alkyl
  • R 2 is hydrogen
  • R 3 is highlighted as cyano (CVC 6 ) cycloalkyl
  • R 5 is (Ci-C4) haloalkyl, (Ci-C4) haloalkoxy, (Ci-C4) haloalkylthio, (Ci-C4) haloalkylsulfmyl or (Ci-C4) haloalkylsulfonyl and, n is highlighted for 2.
  • Embodiment 6-1 A 1 stands in particular for C (H), A 2 stands in particular for C (H),
  • a 3 stands for oxygen in particular
  • R 1 is especially ethyl
  • R 2 is in particular hydrogen
  • R 3 is in particular 1-cyanocyclopropyl
  • R 5 is in particular trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl and n is especially 2.
  • a 1 stands in particular for C (H)
  • a 2 stands in particular for C (H)
  • a 3 stands for oxygen in particular
  • R 1 is in particular ethyl
  • R 2 is especially hydrogen
  • R 3 is especially 1-cyano-cyclopropyl
  • R 5 is in particular pentafluoroethyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl and n is especially 2.
  • embodiment 5 includes both embodiment 5-1, as well as embodiment 5-2 and the term embodiment 6 both embodiment 6-1, as well as embodiment 6-2.
  • the Bergiff formula (I) in the following course also includes the formula (I) falling formulas (I-A) to (I-D).
  • the invention relates to the compounds of the formula (I) in which n is 2 and where A 1 , A 2 , A 3 , R 1 , R 2 , R 3 and R 5 which are in the configuration (1 ) or design (2) or design (3) or design (4) have described meanings.
  • the invention relates to the compounds of the formula (I) in which A 3 is oxygen or sulfur and where A 1 , A 2 , R 1 , R 2 , R 3 , R 5 and n are as described (5) or embodiment (6) have described meanings.
  • the invention relates to the compounds of the formula (I) in which A 3 is oxygen and where A 1 , A 2 , R 1 , R 2 , R 3 , R 5 and n are in the configuration (1 ) or design (2) or design (3) or design (4) or design (5) have described meanings.
  • the invention relates to the compounds of the formula (I) in which
  • R 1 is (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl or (C 3 -C 9) cycloalkyl and A 1 , A 2 , R 2 , R 3 , R 5 , A 3 and n are those described in ( 1) or embodiment (2) or embodiment (5) or embodiment (6) have described meanings.
  • the invention relates to the compounds of the formula (I) in which
  • R 1 is (Ci-C i) alkyl and A 1 , A 2 , R 2 , R 3 , R 5 , A 3 and n have the meanings described in Embodiment (1) or Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (6).
  • the invention relates to the compounds of the formula (I) in which
  • R 1 is ethyl and A 1 , A 2 , R 2 , R 3 , R 5 , A 3 and n in the embodiment (1) or embodiment (2) or embodiment (3) or embodiment (4) or embodiment (5 ) have meanings described.
  • the invention relates to the compounds of the formula (I) in which
  • R 2 is hydrogen, (Ci-C i) alkyl or halogen and A 1 , A 2 , R 1 , R 3 , R 5 , A 3 and n in the embodiment (1) or embodiment (2) or embodiment (3 ) or embodiment (5) or embodiment (6) have described meanings.
  • the invention relates to the compounds of the formula (I) in which
  • R 2 is hydrogen and A 1 , A 2 , R 1 , R 3 , R 5 , A 3 and n have the meanings described in embodiment (1) or embodiment (2) or embodiment (3) or embodiment (4).
  • the invention relates to the compounds of the formula (I) in which
  • R 3 is (Ci-C4) haloalkyl (C3-Cs) cycloalkyl, spiro- (C3-Cg) cycloalkyl (C3-Cg) cycloalkyl, (C 4 - Ci2) bicycloalkyl or optionally mono- or disubstituted by alkyl or halogen Cyano (C3-C6) cycloalkyl and A 1 , A 2 , R 2 , R 1 , R 5 , A 3 and n in the embodiment (1) or embodiment (2) or embodiment (4) or embodiment (5) or Embodiment (6) have described meanings.
  • the invention relates to the compounds of the formula (I) in which
  • R 3 is cyano (CVC 6 ) cycloalkyl and A 1 , A 2 , R 2 , R 1 , R 5 , A 3 and n have the meanings described in Embodiment (1) or Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (6).
  • the invention relates to the compounds of the formula (I) in which
  • R 3 is 1-Cyanocyclopropyl and A 1 , A 2 , R 2 , R 1 , R 5 , A 3 and n in the embodiment (1) or embodiment (2) or embodiment (3) or embodiment (4) or embodiment (5) have been described.
  • the invention relates to the compounds of the formula (I) in which
  • R 5 is halogen, (Ci-C 6) haloalkyl, (Ci-C 6) haloalkoxy, halo (C3-Cs) cycloalkyl, cyano (C 3 - C ö) cycloalkyl, (Ci-C 6) haloalkylthio, (Ci- C 6 ) haloalkylsulfinyl or (Ci-C 6 ) haloalkylsulfonyl and A 1 , A 2 , R 1 , R 2 , R 3 , A 3 and n in the embodiment (1) or embodiment (2) or embodiment (3) or Embodiment (5) or embodiment (6) have described meanings.
  • the invention relates to the compounds of the formula (I) in which
  • R 5 is (Ci-C i) haloalkyl, (Ci-C i) haloalkoxy, (Ci-C i) haloalkylthio, (Ci- C4) haloalkylsulfinyl or (Ci-C4) haloalkylsulfonyl and A 1 , A 2 , R 1 , R 2 , R 3 , A 3 and n have the meanings described in embodiment (1) or design (2) or design (3) or design (4) or design (6).
  • the invention relates to the compounds of the formula (I) in which R 2 is hydrogen and R 3 is 1-cyanocyclopropyl and A 1 , A 2 , R 1 , R 5 , A 3 and n den in terms of embodiment (1) or design (2) or design (3) or design (4) or design (5) or embodiment (6) have meanings.
  • a 1 , A 2 , A 3 and R 5 have the meanings described in embodiment (1) or design (2) or design (3) or design (4) or design (5) or design (6).
  • R 5 and A 3 have the meaning described in embodiment (1) or design (2) or design (3) or design from (4) or design (5) or embodiment (6).
  • halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series Flu or, chlorine and bromine.
  • alkyl either alone or in combination with other terms such as haloalkyl, in the context of the present invention means a radical of a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms that can be branched or unbranched.
  • Examples of C 1 -C 12 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert.
  • C 1 -C 6 -alkyl radicals are particularly preferred. Particular preference is given to C 1 -C -alkyl radicals.
  • alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having at least one double bond, for example vinyl , Allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1, 3-pentadienyl, 1 Hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1, 4-hexadienyl.
  • Preferred of these are C 2 -C 6 -alkenyl radicals and particularly preferred are C 2 -C 4 -alkenyl radicals.
  • alkynyl is according to the invention a linear or branched C 2 -C 12 -alkynyl radical which has at least one triple bond, for example ethynyl, Propynyl and propargyl, understood. Preferred of these 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 either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclobutyl looctyl, understood. Preferred of these are C3-C6-cycloalkyl radicals.
  • bicyclic Verstan the whose both rings have a common single bond.
  • the two cycles may have the same or a different number of carbon atoms.
  • bicyclo [l.l.0] butane or bicyclo [2.l.0] pentane for example, its called bicyclo [l.l.0] butane or bicyclo [2.l.0] pentane.
  • spiro-cycloalkyl-cycloalkyl either alone or in combination with other terms, according to the invention a compound understood in which two cycloalkyl rings are connected via a common carbon atom. The two cycles may have the same or a different number of carbon atoms. For example, its called spiro [2.2] pentane (spiro (cyclopropyl) - (cyclopropyl)) or spiro [2.3] hexane (spiro (cyclopropyl) - (cyclobutyl)).
  • alkoxy either alone or in combination with other terms such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • Very particularly preferably used according to the invention are compounds of the formula (1) in which a combination of the meanings listed above as being very particularly preferred is present.
  • the compounds of the formula (1) can be present as geometric and / or as optically active isomers or corresponding isomeric 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 (1) may also be present as salts, in particular acid addition salts and metal salt complexes.
  • the compounds of the formula (1) and their acid addition salts and metal salt complexes have good activity, in particular for combating animal pests.
  • Suitable salts of the compounds of the general formula (1) may be mentioned customary non-toxic salts, ie salts with corresponding bases and salts with added acids.
  • salts with inorganic bases such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, dicyclo- hexylammonium, N, N'-dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, Acetates, trifluoroacetates, maleates, tartrates, methanesulf
  • the compounds of the formula (B) can be prepared by reacting the compounds of the formula (A) with the compounds of the formula (Aa) in the presence of a base.
  • Carboxylic acid esters of the formula (A) are either commercially available or can be prepared by known methods, for example from 2-aminopyridine derivatives analogous to those described in US Pat WO2011 / 41713 described method.
  • Mercaptan derivatives of the formula (Aa), such as, for example, methylmercaptan, ethylmercaptan or isoproperyl mercaptan 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 (B) may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent selected from ordinary solvents inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • suitable bases are inorganic bases from the group consisting of acetates, phos phates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Nat riumhydrid.
  • X 1 is preferably a fluorine, bromine or chlorine atom.
  • the compounds of the formula (C) can be prepared by oxidation of the compounds of the formula (B).
  • the oxidation is generally carried out in a solvent which is selected from conventional, under the prevailing reaction conditions inert solvents. 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.
  • reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • the compounds of the formula (D) can be prepared by oxidation of the compounds of the formula
  • 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.
  • reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • the compounds of the formula (D) can also be produced in a one-step process by oxidation of the compounds of the formula (B).
  • the oxidation is generally carried out in a solvent Runaway. Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • Step e) The compounds of formula (E) can be prepared by saponification of the compounds of the formula
  • the saponification is generally carried out in a solvent.
  • a solvent Be preferred alcohols such as methanol or ethanol; Water; Ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as, for example, acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide; or, if appropriate, mixtures of said solvents.
  • suitable bases are inorganic bases from the group consisting of hydroxides, acetates, phosphates and carbonates of alkali or alkaline earth metals.
  • Preferred are sodium hydroxide, lithium hydroxide, cesium carbonate, sodium carbonate and potassium carbonate.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of -20 ° C to 200 ° C.
  • the compounds of the formula (F) can be prepared by reacting compounds of the formula (G) with carboxylic acids of the formula (E) in the presence of a condensing agent or a base.
  • reaction of the compounds of the formula (G) with carboxylic acids of the formula (E) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as, for example, 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
  • the compounds of the formula (G) are either available commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO02006 / 65703, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086,848,
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC1), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC1), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • Suitable bases are inorganic bases which are commonly used in such reactions.
  • bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium umcarbonat, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • Other suitable bases are alkali metal hydrides such as sodium hydride.
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
  • the compounds of formula (I) can be prepared by condensation of the compounds of formula (F) e.g. analogously to the process described in WO2009 / 131237, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 or WO 2015/121136.
  • the reaction to give compounds of the formula (I) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from customary, in the prevailing reaction conditions, inert solvents.
  • ethers such as, for example, diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (ED Cf) 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. Diethyl azodicarboxylic acid.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (ED Cf) or 1,3-dicyclohexylcarbodiimide
  • Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon t
  • 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.
  • reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • radicals R 1 , R 2 , R 3 , R 5 , and n have the meanings described above, A 2 and A 3 are CH or N, A 3 is O or S and X 1 and X 2 are halogen.
  • reaction of the compounds of the formula (H) with carboxylic acids of the formula (E) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as, for example, 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
  • the compounds of the formula (H) are either available commercially available or can be prepared by known methods, for example analogously to the processes described in US2003 / 069257, US2012 / 0319050, WO2011 / 107998 or WO2010 / 91310.
  • Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3- ethylcarbodiimide hydrochloride (EDCI), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • carbodiimides such as 1- (3-dimethylaminopropyl) -3- ethylcarbodiimide hydrochloride (EDCI), 1,3-dicyclohexylcarbodiimide, thionyl chloride, or oxalyl chloride.
  • Suitable bases are inorganic bases which are commonly used in such reactions.
  • bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium umcarbonat, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • Other suitable bases are alkali metal hydrides, e.g. Sodium hydride.
  • the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
  • Thioamides of the formula (K) can be prepared from the carbonamides of the formula (F) by reaction with a sulfurization reagent, for example Lawesson's reagent or P4S 10.
  • a sulfurization reagent for example Lawesson's reagent or P4S 10.
  • the compounds of formula (I) wherein n is 0 can be prepared by condensation of the compounds of formula (F) or (K) in the presence of a base, e.g. analogous to that described in Bioorganic and Medicinal Chemistry (2013), 21, 5480-5487, Organic and Biomolecular Chemistry (2014), 12, 9696-9701, Organicnatinine, acetylcholine, acetylcholine, acetylcholine, a base, e.g. analogous to that described in Bioorganic and Medicinal Chemistry (2013), 21, 5480-5487, Organic and Biomolecular Chemistry (2014), 12, 9696-9701, Organic Leiters (2012), 14, 98-101, Medicinal Chemistry (2011) , 7, 127-134, WO2016 / 33445, WO2016 / 71499 or US2017 / 298081.
  • a base e.g. analogous to that described in Bioorganic and Medicinal Chemistry (2013), 21, 5480-5487, Organic and Biomolecular Chemistry (2014),
  • the reaction to give compounds of the formula (1) 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 which are inert under the prevailing reaction conditions.
  • ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile example; 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.
  • 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.
  • 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.
  • special Preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium umcarbonat, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
  • copper salts can be used, for example copper (I) iodide or copper oxides such as copper (II) oxide, ruthenium salts such as tris (2,2-bipyridine) ruthenium (II) hexafluorophosphate or potassium salts such as potassium hexacyanoferrate ( III).
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • radicals A 1 , A 2 , A 3 , R 1 , R 2 , and R 5 have the meanings described above, X 1 is halogen.
  • Step a) Compounds of the formula (N) can be prepared by cyanomethylation of the compounds of the formula (L) with compound of the formula (M) in the presence of a catalyst, a ligand and a base, for example according to the methods described in J. Am. Chem. Soc. (2002), 124, 9330, J. Am. Chem. Soc. (2005), 127, 15824 or WO2016 / 041819.
  • the compound of the formula (M) is commercially available.
  • the reaction to give compounds of the formula (N) is generally carried out in a solvent. Preference is given to aprotic polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, or dimethyl sulfoxide.
  • Palladium complexes can be used as the catalyst, such as, for example, tris (dibenzylideneacetone) dipalladium (0) or [1,1'-bis (diphenylphosphino) ferrocenes] -dichloropalladium (II) and the ligands used are generally organophosphane compounds, such as bis (diphenylphosphine) -9,9-dimethylxanthene (xanthphos).
  • a suitable base is, for example, zinc fluoride.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the cyanomethylation can also be carried out by means of a Suzuki coupling, for example according to the method described in J. Am. Chem. Soc. (2011), 133, 6948-6951.
  • reaction to give compounds of the formula (I) in which n is 2 is generally carried out in a solvent.
  • a solvent Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
  • aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N-diisopropylethylamine
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • R 1 and n have the meaning described above.
  • X and X 1 are CI, Br or I, R 7 is (Ci-C i) alkyl and q is 1 or 2.
  • the compounds of the formula (R) can be prepared analogously to those described in European Journal of Medicinal Chemistry, 29 (1994) 279-286; WO2006 / 71752; WO2012 / 80232; Journal of Medicinal Chemistry, 57 (2014), 4196-4212; WO2012 / 143599; WO2015 / 48245 and WO2006 / 18725 described by reaction of compounds of formula (P) with a suitable carbonyl compound, for example a Brompyruvat derivative of the formula (Q), at room tem erature or under thermal conditions in a suitable solvent such as Ethanol, T etrahydrofuran, aceto nitrile or dimethylformamide.
  • a suitable carbonyl compound for example a Brompyruvat derivative of the formula (Q)
  • the bromopyruvate derivatives of the formula (Q) are commercially available.
  • the compounds of formula (P) are either commercially available or may be prepared by known methods, for example analogously to those described in Chemical Communications, 44 (2010), 925-927; Journal of the American Chemical Society, 68 (1946), 453-457; WO2009 / 29625; Journal of the American Chemical Society, 137 (2015), 8388-8391; Journal of Medicinal Chemistry, 57 (2014), 4196-4212, Helvetica Chimica Acta, 55 (1972), 565-568 and Synthesis, 9 (1985), 884-886.
  • the compounds of formula (S) can be prepared from compounds of formula (R), e.g. analogously to the process described in WO2008 / 36216, WO2004 / 22561, WO02006 / 23707, WO02006 / 133006, WO2014 / 60375, US2004 / 23981 or EP3018125.
  • the reaction to give compounds of the formula (S) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
  • the reaction can be carried out in the presence of a chlorinating agent and optionally a base.
  • chlorinating agents examples include thionyl chloride, methanesulfonyl chloride, or phosphoryl chloride.
  • suitable bases are nitrogen-containing fatty heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydroxide.
  • nitrogen-containing fatty heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydroxide.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • the compounds of formula (T) can be prepared by substitution from compounds of the formula (S), e.g. analogous to that described in US2014 / 57914, EP2036905, J. Agric. Food Chem. 2017, 65, 1272-1280, W02009 / 114180, or Tetrahedron 2005, 6115.
  • the reaction to give compounds of the formula (T) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to polar solvents such as dimethyl sulfoxide or N, N-dimethylformamide or acetonitrile.
  • the reaction can be carried out in the presence of a cyanating agent.
  • Suitable cyanating agents are sodium cyanide or potassium cyanide.
  • reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
  • Compounds of the formula (V) can be prepared by reacting the compounds of the formula (T) with compounds of the formula (U) in the presence of a base, for example by the processes described in WO2016 / 041819.
  • the compounds of the formula (U) are commercially available.
  • the reaction to give compounds of the formula (V) is generally carried out in a solvent.
  • a solvent Preference is given to halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene, aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as acetonitrile, or esters such as ethyl acetate.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
  • aprotic polar solvents such as acetone, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitriles such as
  • suitable bases are nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • nitrogen-containing heterocycles such as pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, cesium carbonate, potassium carbonate and sodium hydride.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • tertiary amines such as triethylamine and N, N-diisopropylethylamine
  • the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C. Steps)
  • Compounds of the formula (W) can be prepared by known methods from compounds of the formula (V) via halogenation in analogy to those described in WO2009 / 23179, WO2010 / 91411, WO2011 / 41713 and Bioorganic and Medicinal Chemistryêts, 22 (2012), 3460-3466, for example, with N-chlorosuccinimide as the halogenating agent in dimethylformamide as a solvent.
  • the compounds of the formula (X) can be prepared by reacting the compounds of the formula (W) with compounds of the formula (Aa) in the presence of a base.
  • Mercaptan derivatives of the formula (Aa) such as, for example, methylmercaptan, ethylmercaptan or isopro pylmercaptan are either commercially available or can be prepared by known methods, for example analogously to those described in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922 ), p. 1329 described method.
  • the reaction to give compound of the formula (X) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
  • ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; 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, phos phates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Nat riumhydrid.
  • the compounds of the formula (Y) can be prepared by oxidation of the compounds of the formula (X).
  • the oxidation is generally carried out in a solvent.
  • Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid, propionic acid or water.
  • Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
  • the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C to 120 ° C.
  • esters of formula (Y) can be prepared using standard methods, cf. DE 2221647 and WO2011 / 41713 into which acid of the formula (Z) are converted, for example with an alkali hydroxide as base such as sodium hydroxide or lithium hydroxide in an alcohol as solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • an alkali hydroxide as base such as sodium hydroxide or lithium hydroxide
  • an alcohol as solvent such as e.g. Ethanol or a mixture of tetrahydrofuran and water.
  • the invention also relates to methods for controlling animal pests, in which Ver compounds of the formula (I) act on animal pests and / or their habitat. Preference is given to combating animal pests in agriculture, forestry and material protection. Among these, preferably excluded are methods for 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 formula (I) as Shudlingsbehimmp fungsmittel, in particular pesticides.
  • pesticide always always includes the term crop protection agent.
  • the compounds of formula (1) are suitable for good plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the emetic and to control animal pests, in particular insects, arachnids, helminths, especially nematodes, and mollusks found in agriculture, horticulture, livestock, aquaculture, forests, gardens and recreational facilities, in storage and material protection 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 protect the environment and / or maintain cleanliness. According to the invention this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramic, plastic or metal (s) to ensure that they are free from hygiene pests and / or their excretions are.
  • surgical or therapeutic treatment regimes to be applied to the human body or bodies of animals and diagnostic regulations performed on the human body or on the bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, Hospitals, stables, animal husbandry etc.
  • the term “hygiene pest” is therefore to be understood as meaning one or more animal pests whose presence in the hygiene sector is problematic, especially for health reasons. It is therefore a major objective to avoid or minimize the presence of hygiene pests and / or their exposure to them 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 already existing infestation. It is also possible to use preparations which prevent or reduce exposure to pests.
  • Hygienic pests include, for example, the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Omithodorus spp., Omithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranchus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp , Steneotarsonemus spinki, Tarsonemus spp., Z. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g. B.
  • Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
  • Anoplophora glabripennis Anthonomus spp., Z. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., E.g. Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., E.g. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnatoccerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., E.g.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnostema consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., E.g. Megacylle robiniae, Megascelis spp., Melanotus spp., E.g.
  • Melanotus longulus oregonensis Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xantho- graphus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus suri Namenis, Oryzaphagus oryzae, Otiorhynchus spp.
  • Otiorhynchus cribricollis Otiorhynchus li- gustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z.
  • Delia antiqua Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Dro Sophila 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 flocusus, Allocaridara malayensis, Amrasca spp., E.g. B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis saccharia, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cincticeps, 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. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., E.g. 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 vibumi, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. B.
  • Trioza spp. Z. Trioza diospyri, Typhlocyba spp., Unaspis spp., Vitus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g. B.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion 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, Monornorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. Sirex noc- tilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., E.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria tremani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. Homozygous spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g., Heliothis virescens, Hofmannophila pseudospretella, Homoeoso ma spp. 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.
  • Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismo-inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Z. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Cricone mellius rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides femiae, Criconemoides onoense, Criconemoides omatum, 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. Parratrichus minor, Paratylenchus spp., Pratylenchus spp., E.g. B.
  • the compounds of the formula (I) may optionally also be applied in certain concentrations or 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 agent against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms further pest control agent and / or the effect of improving adjuvants such as penetration enhancer, z.
  • 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 fertilizer as in example 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 (1), further agrochemical active substances.
  • adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • Adjuvants are mitel, which require retention, spreading behavior, adherence to the leaf surface or penetration.
  • formulations are prepared in a known manner, for. Example by mixing the Verbindun gene of formula (I) with excipients such as extenders, solvents and / or solid Trä and / or other excipients such as surfactants.
  • excipients such as extenders, solvents and / or solid Trä and / or other excipients such as surfactants.
  • the formulations are prepared either in suitable equipment or before or during use.
  • 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, al kylbenzole, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or etherified), the ketones (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, al kylbenzole, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or ether
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg.
  • Suitable Lissemitel are for example aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such.
  • acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone strong polar solvents such as dimethyl sulfoxide and water.
  • suitable carriers can be used.
  • z For example, ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: z.
  • liquefied gaseous diluents or solvents can be used in particular are such extenders or carriers which are gaseous at normal temperature and under normal pressure, z.
  • 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 nonionic 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 esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, z.
  • alkylaryl polyglycol ethers alkylsulfonates, Alkylsulfa te, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
  • a surfactant is advantageous when one of the compounds of formula (1) 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. Example, iron oxide, titanium oxide, ferrocyan blue and organic colorants such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc be present.
  • dyes such as inorganic pigments, eg. Example, iron oxide, titanium oxide, ferrocyan blue and organic colorants such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc be present.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-form polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural rubber.
  • adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-form polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural rubber.
  • phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention promoters, stabilizers, sequestering agents, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • Suitable retention aids are all those substances which reduce the dynamic surface tension, such as, for example, dioctylsulfosuccinate or which increase the viscoelasticity, for example hydroxypropylguar polymers.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, Fettaminalkoxylate such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or Diammoni- hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • Fettaminalkoxylate such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or Diammoni- hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of the formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms prepared from the formulations (in particular pest control agents) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the Application form, cher.
  • 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 used to be such.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators used to be such.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytot
  • the compounds of the formula (I) may be present in a mixture with other active substances or semio chemicals, such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used to improve plant properties such as, for example, growth, yield and quality of the ence.
  • 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 blockers 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. Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans isomer], deltamethrin, empenthrin [(EZ) (lR) isomer], es
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • allosteric modulators of the nicotinic acetylcholine receptor (nAChR) such as spinosyn, e.g. B. spinetoram and spinosad.
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors such as, for example, diafenthiuron or organotin compounds, eg. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, 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 such as diamides, e.g. Chlorantraniliprole, cyantraniliprole and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoxymate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon- Metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, flaxxafon, fluopyram, fluralan, fluxametamide
  • 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 , (1,099) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) lpconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochloraz, (1,017) propiconazole, (1,018) Prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) te
  • 1,2,4-triazol-5-yl thiocyanate (1.042) 2 - [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4- yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1043) 2 - [(2R, 4R, 5S) -l- (2,4-)
  • 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 lR, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer lS, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate lRS, 4SR, 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate lRS, 4SR, 9RS and the anti-epimeric racemate lRS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric l
  • inhibitors of mitosis and cell division for example, (4.001) carbendazim, (4.002) diethofencarb,
  • Inhibitors of amino acid and / or protein biosynthesis for example (7,001) cyprodinil, (7,002) kasugamycin, (7,003) kasugamycin hydrochloride hydrate, (7,004) oxytetracycline (7,005) pyrimethanil, (7,006) 3- (5 fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-l-yl) quinoline.
  • Inhibitors of ATP production for example, (8,001) silthiofam.
  • inhibitors of cell wall synthesis for example, (9.001) benthi- avalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenate, (9.008) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (9.009) (2Z) - 3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -l- (morpholin-4-yl) prop-2-en-l-one.
  • Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) pro-pamocarb 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 2 ?. 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.
  • 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 (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No ATCC 20874), Paecilomyces lilacinus, in particular P.
  • 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 armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African cotton worm) NPV.
  • GV granulosis virus
  • Cydia pomonella codling moth
  • GV Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus
  • NPV nuclear polyhedrosis virus
  • Spodoptera exigua mNPV Spodoptera frugiperda
  • armyworm mNPV
  • Spodoptera littoralis Africann cotton worm
  • bacteria and fungi which are added as 'inoculant' plants or plant parts or Pflan zenorganen and claim by their special properties, the plant growth and plant health.
  • examples include: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus Spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus
  • the compounds of the formula (I) can be combined with safeners, for example benoxazor, cloquintocet (-mexyl), cyometrinil, cyprosulfamides, dichloromide, fenchlorazoles (-ethyl), fencimer, flurazoles, fluxofenim, furilazoles, isoxadifen ( -ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) -l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazol
  • plants and parts of plants can be treated.
  • plants are all plants and plant populations understood as desirable and unwanted wild plants or crops (including naturally occurring crops), such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybean, potato, sugar beet, sugar cane , Tomatoes, peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples , Pears, citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soybean, potato, sugar beet, sugar cane
  • Tomatoes peppers, cucumbers, melons, carrots, watermelons, onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, oilseed rap
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plants are to be understood as meaning all stages of development, such as seeds, sticklets, young (unripe) plants and mature plants. Sharing plants is 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, fruit bodies, fruits and seeds, and roots, tubers and rhizomes become. The plants also include harvested plants or harvested plant parts as well as vegetative and generative propagation material such as cuttings, tubers, rhizomes, cuttings and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, nebulization, scattering, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild species or plant species and plant cultivars obtained by conventional biological breeding methods such as hybridization or protoplast fusion are treated as well as their parts.
  • transgenic plants and plant varieties which have been obtained by genetic engineering, optionally in combination with conventional methods (Genetically Modified Organisms) and treated their parts.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • Plant varieties are understood to be plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • Pflan zen or plant varieties include all plants that geneti cal material obtained by the genetic engineering modification, which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value the Emte organization, higher Lagerfä ability and / or machinability of Emte economic.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2 , Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, be acts z.
  • systemically acquired resistance SAR
  • systemin phytoalexins
  • elicitors elicitors
  • resistance genes and correspondingly expressed proteins and toxins as well as increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg. "PAT" gene).
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg. "PAT" gene).
  • the genes which confer the desired properties can also be present in combinations with one another in the transgenic plants.
  • 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 special emphasis on maize, soya, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased ability of the plants to repel insects, arachnids, nematodes and snails. Plant protection - types of treatment
  • 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 Ver, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, Encrusting, single or multilayer coating, etc. It is also possible to apply the compounds of the formula (I) according to the ultra-low-volume method or the application form or the compound of formula (I) itself in the soil inject.
  • a preferred direct treatment of the plants is foliar application, i. H. the compounds of formula (I) are applied to the foliage, the frequency of treatment and the amount of effort should be adjusted to the infestation pressure of each pest.
  • the compounds of the formula (1) also enter the plants via the plant root.
  • the treatment of the plants is then carried out by the action of the compounds of formula (1) on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (1), or by the soil application, i. H. the compounds of the formula (1) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops, this may also be by metered addition of the compound of formula (1) in a solid form (eg as Granu lat) into a flooded paddy field.
  • a solid form eg as Granu lat
  • the present invention therefore also relates, in particular, to a method of protecting seed and germinating plants from the infestation of pests by treating the seed with one of the compounds of formula (1).
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (1) and a mixture component. It also also comprises a process in which the seed is treated at different times with a compound of formula (1) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (1) for the treatment of seed for the protection of the seed and the resulting plant from animal Schdlin conditions.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (1) according to the invention.
  • the invention also relates to seed which has been treated at the same time with a compound of formula (1) and a component Primampo.
  • the invention further relates to seed which has been treated at different times with a compound of formula (1) and a mixture component.
  • the individual substances may be present in different layers on the seed.
  • the layers which comprise a compound of the formula (1) and mixing components may optionally be separated by an intermediate layer.
  • the inven tion also relates to seed, in which a compound of formula (1) and a Statskom component are applied as part of a coating or as a further layer or further layers in addition to a sheath.
  • the invention relates to seed which, after treatment with a connec tion of the formula (1) is subjected to a film coating process to avoid dust on the seed ver.
  • One of the advantages that occurs when a compound of formula (1) acts systemically is that the treatment of the seed protects not only the seed itself but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of the formula (I) can also be used in combination with signal technology agents, whereby better colonization with symbionts, such as, for example, rhizobia, mycorrhiza and / or endophytic bacteria or fungi, takes place and / or it becomes an optimized stick fabric fixation is coming.
  • symbionts such as, for example, rhizobia, mycorrhiza and / or endophytic bacteria or fungi
  • 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, oilseed rape, turnip (eg. Peanut and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (such as wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
  • transgenic seed with a connec tion of formula (I) is of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable 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 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 (1) can be converted into the customary seed-dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed-coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the compounds of formula (1) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives , Gibberellins and 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 sparingly soluble pigments and water-soluble dyes can be used. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 has known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are 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 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 before 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 placed in agrochemical compositions for such purposes. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • adhesives which can be contained in the seed dressing formulations which can be used according to the invention all customary binders which can be used in pickling agents are suitable.
  • 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, soybeans and turnips or vegetable seeds of various kinds.
  • 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 mixer in batch or continuous operation, the desired amount of seed dressing formulations either as such or after prior dilution with water and mix until evenly distributed the formulation on 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 (1) in the formulations and on the seed.
  • the application rates for the compound of the formula (1) 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 (1) are effective against animal parasites, in particular ectoparasites or endoparasites.
  • endoparasite includes, in particular, helminths and protozoa, such as coccidia.
  • Ectoparasites are typi cally and preferred arthropods, especially insects or acarids.
  • 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. In aquaculture, or optionally insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aqua fishes.
  • the compounds of the formula (1) are administered to mammals ver.
  • the compounds of formula (1) 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.
  • compound in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its proliferation.
  • 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., Tri- menopon spp., Trinoton spp., Wemeckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chry
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus 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., Omithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp , Hyalomma spp., Ixodes spp., Rhipicephal
  • eyletia spp. Psorergates spp., Trombicula spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocopts spp., Laminosioptes spp., Notoedres spp., Otodectes spp. Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora (Flagellata), like:
  • 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 besides the e.g. B. Myxozoa spp.
  • Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, Ne matoden, Pentastoma and Platyhelminthen (e.g., Monogenea, Cestodes and Trematodes).
  • Exemplary helminths include, but are not limited to:
  • Monogenea z.
  • Dactylogyrus spp. Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp .;
  • Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinocotyle spp. Echinolepis spp.
  • Hydatigera spp. Hymenolepis spp.
  • Joyeuxiella spp. Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp ., Thysanosoma spp.
  • Trematodes 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., Om
  • Nematodes from the order Trichinellida, for example: Capillaria spp., Trichinella spp., Trichomosoid spp., Trichuris spp.
  • Aelurostrongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp.
  • Cyclococercus spp. Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Ha - Emonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp., Obeliscoids spp., Oesophagodontus spp.
  • Oesophagostomum spp. Ollulanus spp .
  • Omithostrongylus spp. Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Paraliphostrongylus 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 eg: 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 antiendoparazitic.
  • a further 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, acanthocephalic acid 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 the formula (I) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary medicinal formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as described herein which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, particularly pharmaceutically acceptable ones conventionally used in veterinary formulations. excipients and / or conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasitic 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 , according to the aspects mentioned, as well as methods for their manufacture.
  • Another aspect relates to a method of 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, especially 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 that needs it.
  • 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 medical field.
  • blending not only means that two (or more) different active ingredients are formulated in a single formulation and used together, but also refers to products that comprise separate formulations for each active ingredient. Accordingly, if more than two drugs are to be used, all drugs can be formulated in a single formulation or all drugs can be formulated in separate formulations; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formu- Alloys permit the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
  • Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
  • Active substances with unknown or non-specific mechanisms of action eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlorodimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, floutenzine, bromopropylate, cryolite;
  • Pyrethroids e.g. (Cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanolmethrin, 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, eprinometine, doramectin, emamectin benzoate; milbemycin
  • Bios, hormones or pheromones for example natural products, e.g. Thuringiensin, Codelmon or Neem components
  • Dinitrophenols e.g. Dinocap, dinobuton, binapacryl
  • Benzoylureas e.g. Fluazuron, penfluron,
  • Amidine derivatives e.g. B. Chlormebuform, cymiazole, demiditraz
  • Hive varroa acaricides for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides 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 cestozide 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, tric-labendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole-sulfoxide, albendazo
  • 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 sense of the present invention is an arthropod, in particular an insect or arachnid, which is capable of producing pathogens such as e.g. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • pathogens may be transmitted either mechanically (eg, trachoma by non-stabbing flies) to a host, or after injection (eg, malaria parasites by mosquitoes) into a host.
  • vectors and their transmitted diseases or pathogens are:
  • - Culex Japanese encephalitis, filariasis, other viral diseases, transmission of other worms
  • - Aedes yellow fever, dengue fever, other viral diseases, filariasis
  • 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 bumetii), Babesia (Babesia canis canis), ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the supply and protection of materials. 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.
  • Technical materials in the present context are non-living materials to ver, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, Holzverar processing products and paints.
  • the application of the invention for the protection of wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of 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 formula (I) can be used to protect against growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage, especially for controlling insects, arachnids, ticks and mites occurring in closed-up areas, such as homes, factories, offices, vehicle cabins, animal husbandry occurrences.
  • 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 genus Arachnida of the genus Scorpiones, Araneae and Opiliones, of the genus Chilopoda and Diplopoda, of the genus Insecta the order Blattodea, of the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hy - Menoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out for example in aerosols, non-pressurized sprays, z.
  • the analyzes of the analytical determinations described below refer to all information in the entire document, unless the performance of the respective analytical determination at the present T extstelle is described separately.
  • LC-MS3 Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml / min.
  • LC-MS6 and LC-MS7 Agilent 1290 LC, Agilent MSD Mass Spectrometer, HTS PAL Sample Changer. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 mPmin).
  • LC-MS4 Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (Column Waters Acquity 1.7 pm 50 mm * 2.1 mm, column oven temperature 45 ° C). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 mPmin.
  • LC-MS5 Agilent 1100 LC system with MSD mass spectrometer and HTS PAL sample changer (column: Zorbax XDB C18 1.8 ⁇ m 50 mm * 4.6 mm, column oven temperature 55 ° C).
  • the logP value is determined by LC-UV measurement in the acidic range, with 0.9 ml / 1 formic acid in water and 1.0 ml / 1 formic acid in acetonitrile as eluent (linear gradient of 10% acetonitrile to 95% acetonitrile).
  • the logP value is determined by LC-UV measurement in the neutral range, with 79 mg / 1 ammonium carbonate in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • the calibration was carried out with a homologous series of straight-chain alkan-2-ones (having 3 to 16 carbon atoms) with known logP values. The values between successive alkanes are determined by linear regression.
  • the measurements of the 'H-NMR spectra were carried out with a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI probe, with tetramethylsilane as standard (0.00 ppm) of solutions in the solvents CD 3 CN, CDCL or ck-DMSO ,
  • a Bruker Avance III 600 MHz spectrometer equipped with a 5 mm CPNMP probe head or a Bruker Avance NEO 600 MHz spectrometer equipped with a 5 mm TCI probe head was used for the measurements.
  • the measurements were carried out at a probe head temperature of 298 K. If other measurement temperatures have been used, this will be noted separately.
  • NMR data of selected examples are listed either in classical form (d values, multiplet splitting, number of H atoms) or as NMR peak lists.
  • the mixture was stirred at room temperature for an additional 40 h and then diluted with water and dichloromethane. Sodium bisulfite solution was added and the mixture stirred at 30 min. The phases were separated and the aqueous phase extracted with dichloromethane. The combined organi cal phase was dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product was purified by column chromatographic purification via preparative HPLC and the two products isolated separately.
  • the organic phase was washed with 1N HCl and saturated sodium chloride solution and then dried over Natriumsul fat, filtered and freed from the solvent under reduced pressure.
  • the residue was initially charged in toluene (4 mL) and 743 mg (3.91 mmol) of p-toluenesulfonic acid and 4 A molecular sieve was added. The mixture was heated at 120 ° C for 3 days. The solvent was removed in vacuo and the residue taken up in ethyl acetate and water. After separation of the phases, the aqueous phase was extracted twice more with ethyl acetate and the combined organic phase was dried over sodium sulfate, filtered and freed from the solvent under reduced pressure.
  • the vials are filled with 5-10 adult cat fleas (Ctenocepha lides felis), closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. To do this, place the jars upright and tap the fleas 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, when at least 80% effect was achieved in this test with an application amount of 5 pg / cm 2 . It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • the vials are populated with 5-10 adult dog ticks (Rhipicephalus sanguineus), closed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the glass and on a hot plate at 45-50 ° C max 5 min. incubated. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
  • One milligram of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not externally visible are stored in the climatic cabinet until larval hatching after about 42 days. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane. After 2 days the kill is determined in%. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
  • 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 Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and some water for one day (5 seeds per well). The germinated wheat grains who sprayed with an active compound preparation of the desired concentration. Each cavity is then infected with 10-20 beetle larvae of Diabrotica balteata.
  • Myzus persicae - Spray Test Solvent 78 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water, which has an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf disks (Brassica pekinensis) infected by all stages of the green peach aphid (Myzus persicae) are sprayed with an active substance 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 until the desired concentration is reached. 50 ml of the active compound preparation are transferred into microtiter plates and made up to a final volume of 200 ml with 150 ml of lPL4llnsekten medium (33% + 15% sugar). Subsequently, the plates are closed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution. After 5 days, the effect is determined in%. 100% means that all leaf lice have been killed; 0% means that no aphids have been killed.
  • Myzus persicae green peach aphid
  • Phaedon cochleariae - Spray Test Solution 78.0 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water, which has an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda). After 7 days, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • Example the following compounds of the preparation examples effect of 100% at a rate of l00g / ha: 1-1, 1-2, 1-3, 1-4.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR120982A1 (es) 2020-01-06 2022-04-06 Syngenta Crop Protection Ag Derivados heterocíclicos activos como plaguicidas con sustituyentes que contienen azufre
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Family Cites Families (86)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820062A (en) 1954-08-11 1958-01-14 Pure Oil Co Preparation of organic thiols
CA962269A (en) 1971-05-05 1975-02-04 Robert E. Grahame (Jr.) Thiazoles, and their use as insecticides
DE3639877A1 (de) 1986-11-21 1988-05-26 Bayer Ag Hetarylalkyl substituierte 5- und 6-ringheterocyclen
PA8535601A1 (es) 2000-12-21 2002-11-28 Pfizer Derivados benzimidazol y piridilimidazol como ligandos para gabaa
GB0213715D0 (en) 2002-06-14 2002-07-24 Syngenta Ltd Chemical compounds
KR101088922B1 (ko) 2002-09-04 2011-12-01 파마코페이아, 엘엘씨. 사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘
FR2844794B1 (fr) 2002-09-25 2004-12-03 Atofina Procede catalytique de fabrication d'alkylmercaptans par addition d'hydrogene
TWI312272B (en) 2003-05-12 2009-07-21 Sumitomo Chemical Co Pyrimidine compound and pests controlling composition containing the same
GB0414438D0 (en) 2004-06-28 2004-07-28 Syngenta Participations Ag Chemical compounds
ES2361845T3 (es) 2004-08-18 2011-06-22 Pfizer, Inc. Inhibidores de arn polimerasa dependiente del arn del virus de la hepatitis c y composiciones y tratamientos que utilizan los mismos.
WO2006023707A2 (en) 2004-08-20 2006-03-02 Bayer Pharmaceuticals Corporation 2-aminothiophenecarboxamides useful as cancer chemotherapeutic agents
RU2394819C2 (ru) 2004-10-20 2010-07-20 Кумиай Кемикал Индастри Ко., Лтд. Инсектицид, акарицид и нематоцид, содержащие в качестве активного компонента производное 3-триазолилфенилсульфида
WO2006065703A1 (en) 2004-12-13 2006-06-22 Sunesis Pharmaceuticals, Inc. Pyrido pyrimidinones, dihydro pyrimido pyrimidinones and pteridinones useful as raf kinase inhibitors
US7635699B2 (en) 2004-12-29 2009-12-22 Bristol-Myers Squibb Company Azolopyrimidine-based inhibitors of dipeptidyl peptidase IV and methods
JP2008545756A (ja) 2005-06-03 2008-12-18 バイエル・ヘルスケア・アクチェンゲゼルシャフト 癌化学療法剤として有用な１−メチル−１ｈ−ピラゾール−４−カルボキサミド類
EA014057B1 (ru) 2005-10-06 2010-08-30 Ниппон Сода Ко., Лтд. Поперечно связанные соединения циклических аминов и средства для борьбы с вредителями
WO2008001930A1 (fr) 2006-06-28 2008-01-03 Aska Pharmaceutical Co., Ltd. Dérivé de pyridylisoxazole
ATE520690T1 (de) 2006-09-18 2011-09-15 Vitae Pharmaceuticals Inc Piperidinderivate als renin-inhibitoren
AU2008287421A1 (en) 2007-08-10 2009-02-19 Glaxosmithkline Llc Nitrogen containing bicyclic chemical entities for treating viral infections
WO2009029625A1 (en) 2007-08-27 2009-03-05 Kalypsys, Inc. 4- [heterocyclyl-methyl] -8-fluoro-quinolin-2-ones useful as nitric oxide synthase inhibitors
EP2265603B1 (en) 2008-03-13 2014-05-07 The General Hospital Corporation Inhibitors of the bmp signaling pathway
JP5369854B2 (ja) 2008-04-21 2013-12-18 住友化学株式会社 有害節足動物防除組成物および縮合複素環化合物
JP5268461B2 (ja) 2008-07-14 2013-08-21 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
CN101337940B (zh) 2008-08-12 2012-05-02 国家农药创制工程技术研究中心 具杀虫活性的含氮杂环二氯烯丙醚类化合物
CN101337937B (zh) 2008-08-12 2010-12-22 国家农药创制工程技术研究中心 具有杀虫活性的n-苯基-5-取代氨基吡唑类化合物
CN101715774A (zh) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 一个具有杀虫活性化合物制备及用途
EP2184273A1 (de) 2008-11-05 2010-05-12 Bayer CropScience AG Halogen-substituierte Verbindungen als Pestizide
GB0820344D0 (en) 2008-11-06 2008-12-17 Syngenta Ltd Herbicidal compositions
CN102245028B (zh) 2008-12-12 2014-12-31 先正达参股股份有限公司 用作农药的螺杂环n-氧基哌啶
AU2010210426B2 (en) 2009-02-06 2015-06-11 Imago Pharmaceuticals, Inc. Inhibitors of Jun N-terminal kinase
WO2010091411A1 (en) 2009-02-09 2010-08-12 Glaxosmithkline Llc Piperidinyl cyclic amido antiviral agents
CN102414195B (zh) 2009-04-28 2014-11-12 住友化学株式会社 稠合的杂环化合物及其用途
US20120245159A1 (en) 2009-09-30 2012-09-27 Sumitomo Chemical Company, Limited Composition and method for controlling arthropod pests
WO2011041713A2 (en) 2009-10-02 2011-04-07 Glaxosmithkline Llc Piperazinyl antiviral agents
JP5540640B2 (ja) 2009-10-07 2014-07-02 住友化学株式会社 複素環化合物及びその有害節足動物防除用途
WO2011085575A1 (zh) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 邻杂环甲酰苯胺类化合物及其合成方法和应用
AR081721A1 (es) 2010-02-25 2012-10-17 Nippon Soda Co Compuesto de amina ciclica y acaricida
AU2010100462A4 (en) 2010-03-03 2010-06-17 Keki Hormusji Gharda A process for the synthesis of Fipronil
KR20130080485A (ko) 2010-05-31 2013-07-12 신젠타 파티서페이션즈 아게 작물 강화 방법
CU24170B1 (es) 2010-08-31 2016-03-31 Meiji Seika Pharma Co Derivados de amina y sus sales para el control de plagas
CN101967139B (zh) 2010-09-14 2013-06-05 中化蓝天集团有限公司 一种含一氟甲氧基吡唑的邻甲酰氨基苯甲酰胺类化合物、其合成方法及应用
WO2012080232A1 (en) 2010-12-17 2012-06-21 Bayer Pharma Aktiengesellschaft 2-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders
CN103261170B (zh) 2010-12-24 2016-08-24 住友化学株式会社 稠杂环化合物及其用于害虫防治的用途
ES2541295T3 (es) 2011-04-21 2015-07-17 Orion Corporation Carboxamidas que modulan el receptor de andrógenos
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
TWI589570B (zh) 2011-08-04 2017-07-01 住友化學股份有限公司 稠合雜環化合物及其在病蟲害防制上之用途
WO2013050317A1 (en) 2011-10-03 2013-04-11 Syngenta Limited Polymorphs of an isoxazoline derivative
CN102391261A (zh) 2011-10-14 2012-03-28 上海交通大学 一种n-取代噁二嗪类化合物及其制备方法和应用
TWI566701B (zh) 2012-02-01 2017-01-21 日本農藥股份有限公司 芳烷氧基嘧啶衍生物及包含該衍生物作為有效成分的農園藝用殺蟲劑及其使用方法
MX2014011829A (es) 2012-03-30 2015-03-19 Basf Se Compuestos de piridinilideno n-sustituidos y derivados para combatir plagas de animales.
EP2647626A1 (en) 2012-04-03 2013-10-09 Syngenta Participations AG. 1-Aza-spiro[4.5]dec-3-ene and 1,8-diaza-spiro[4.5]dec-3-ene derivatives as pesticides
US9282739B2 (en) 2012-04-27 2016-03-15 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US20130291227A1 (en) 2012-04-27 2013-10-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US9670161B2 (en) 2012-10-18 2017-06-06 Bayer Pharma Aktiengesellschaft 5-fluoro-N-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group
CN103232431B (zh) 2013-01-25 2014-11-05 青岛科技大学 一种二卤代吡唑酰胺类化合物及其应用
CN103109816B (zh) 2013-01-25 2014-09-10 青岛科技大学 硫代苯甲酰胺类化合物及其应用
US20140275503A1 (en) 2013-03-13 2014-09-18 Dow Agrosciences Llc Process for the preparation of certain triaryl rhamnose carbamates
UY35421A (es) 2013-03-15 2014-10-31 Nihon Nohyaku Co Ltd Compuesto heterocíclico condensado o su sal, insecticida agrícola u hortícola que comprende el comp uesto y método de uso del insecticida
WO2014148451A1 (ja) 2013-03-19 2014-09-25 日本農薬株式会社 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
CN105228448B (zh) 2013-05-23 2019-03-01 先正达参股股份有限公司 桶混配制品
CN103265527B (zh) 2013-06-07 2014-08-13 江苏省农用激素工程技术研究中心有限公司 邻氨基苯甲酰胺化合物及其制备方法和应用
CA2917262A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
US9745274B2 (en) 2013-07-03 2017-08-29 Shin Nippon Biomedical Laboratories, Ltd. Compound, organic cation transporter 3 detection agent, and organic cation transporter 3 activity inhibitor
CA2924690A1 (en) 2013-09-25 2015-04-02 Vertex Pharmaceuticals Incorporated Imidazopyridazines useful as inhibitors of the par-2 signaling pathway
CN103524422B (zh) 2013-10-11 2015-05-27 中国农业科学院植物保护研究所 苯并咪唑衍生物及其制备方法和用途
EP3057430A4 (en) 2013-10-17 2017-09-13 Dow AgroSciences LLC Processes for the preparation of pesticidal compounds
CN105636440A (zh) 2013-10-17 2016-06-01 美国陶氏益农公司 制备杀虫化合物的方法
US10364243B2 (en) 2014-02-17 2019-07-30 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
TW201613866A (en) 2014-07-07 2016-04-16 Bayer Cropscience Ag Process for preparing fluorinated iminopyridine compounds
EP3178810A4 (en) 2014-08-08 2018-07-04 Kasuma Partners Inc. Condensed heterocyclic compound
EP3180341B1 (en) 2014-08-12 2022-04-27 Syngenta Participations AG Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10479802B2 (en) 2014-08-29 2019-11-19 Chdi Foundation, Inc. Probes for imaging huntingtin protein
WO2016039441A1 (ja) 2014-09-12 2016-03-17 日本農薬株式会社 イミダゾピリダジン化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
JP6695865B2 (ja) 2014-09-16 2020-05-20 シンジェンタ パーティシペーションズ アーゲー 硫黄含有置換基を有する有害生物防除に活性である四環式誘導体
WO2016046071A1 (en) 2014-09-25 2016-03-31 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016059145A1 (en) 2014-10-16 2016-04-21 Syngenta Participations Ag Pesticidally active tetracyclic heterocyclic derivatives with sulphur containing substituents
EP3214936A1 (en) 2014-11-06 2017-09-13 Basf Se 3-pyridyl heterobicyclic compound for controlling invertebrate pests
JP2018052816A (ja) 2014-12-26 2018-04-05 日本農薬株式会社 シクロアルキル基を有する縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
EP3247712B1 (en) 2015-01-19 2022-04-20 Syngenta Participations AG Pesticidally active polycyclic derivatives with sulfur containing substituents
TWI696612B (zh) * 2015-01-29 2020-06-21 日商日本農藥股份有限公司 具有環烷基吡啶基的稠合雜環化合物或其鹽類及含有該化合物的農園藝用殺蟲劑以及其使用方法
HUE057027T2 (hu) * 2015-02-12 2022-04-28 Nissan Chemical Corp Kondenzált heterociklusos vegyületek és peszticidek
EP3259992B1 (en) 2015-02-17 2019-01-02 Nippon Soda Co., Ltd. Agrochemical composition
EP3280716B1 (de) 2015-04-08 2020-02-12 Bayer CropScience AG Imidazo[1,2-a]pyridin-2-yl-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte
US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
WO2017061497A1 (ja) * 2015-10-06 2017-04-13 日本農薬株式会社 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2017072039A1 (de) * 2015-10-26 2017-05-04 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel

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US20210169080A1 (en) 2021-06-10
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