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WO2016174049A1 - Combinaisons anti-parasitaires comprenant des composés à substitution halogène - Google Patents

Combinaisons anti-parasitaires comprenant des composés à substitution halogène Download PDF

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Publication number
WO2016174049A1
WO2016174049A1 PCT/EP2016/059332 EP2016059332W WO2016174049A1 WO 2016174049 A1 WO2016174049 A1 WO 2016174049A1 EP 2016059332 W EP2016059332 W EP 2016059332W WO 2016174049 A1 WO2016174049 A1 WO 2016174049A1
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Prior art keywords
alkyl
methyl
spp
ethyl
nitrogen
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Christina Mertens
Werner Hallenbach
Hans-Georg Schwarz
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Bayer Animal Health GmbH
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Bayer Animal Health GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • Anti-parasitic combinations including halogen-substituted compounds
  • the present application relates to novel anti-parasitic combinations of halogen-substituted compounds, which are useful for controlling animal pests in the field of animal health.
  • the present invention provides: Combinations of compounds of the general formula (I) below with ectoparasiciticides, anthelmintics or anti-protozoal agents.
  • halogen-substituted compounds of the invention are defined by the general formula (I)
  • R ' represents hydrogen, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 - cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )- alkyl, or alternatively
  • R ! represents hydrogen, optionally substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 - cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )- alkyl, the chemical groupings Ai represents CR 2 or nitrogen, A2 represents CR 3 or nitrogen, A3 represents CR 4 or nitrogen and A4 represents CR 3 or nitrogen, but where not more than three of the chemical groupings Ai to A4 simultaneously represent nitrogen;
  • R 2 , R ⁇ R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 - C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N- C 1 -C 6 -alkylamino or 7V,N-di-C 1 - C 6 -alkylamino; if none of the groupings A2 and A3 represents nitrogen, R 3 and R 4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and
  • Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted groupings alkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl or represents a grouping N-alkylamino, N-alkylcarbonylamino, N,N- dialkylamino; or
  • Q represents an unsaturated 6-membered carbocycle which is optionally mono- or polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally mono- or polysubstituted by V, or alternatively
  • (,) represents an unsaturated 6-membered carbocycle which is optionally polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally polysubstituted by V, where in both last cases of Q
  • V represents halogen, cyano, nitro, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, N,N-dialkylamino,
  • T represents one of the 5-membered heteroaromatics T1 -T7 listed below, where the bond to the pyrazole head group is marked with an asterisk,
  • R ' independently of one another represent halogen, cyano, nitro, amino or optionally substituted C 1 - C 6 -alkyl, C 1 -C 6 - alkyloxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 - C 6 -alkylsulphonyl, and n represents the values 0-2;
  • Z 1 represents optionally substituted alkyl and cycloalkyl
  • Z 2 represents hydrogen, halogen, cyano, nitro, amino or optionally substituted alkyl, alkylcarbonyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, and
  • Z 3 represents hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl or hetaryl .
  • R 1 represents hydrogen, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C7- cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )- alkyl, or alternatively
  • R ! represents hydrogen, optionally substituted C 1 -C 6 -alkyl, C2-C 6 -alkenyl, C2-C 6 -alkynyl, C 3 -C7- cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )- alkyl, the chemical groupings Ai represents CR 2 or nitrogen, A2 represents CR 3 or nitrogen, A3 represents CR 4 or nitrogen and A4 represents CR 5 or nitrogen, but where not more than three of the chemical groupings Ai to A4 simultaneously represent nitrogen;
  • R 2 , R ' . R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-alkoxyiminoalkyl, C 1 -C 6 - alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N-C 1 -C 6 -alkylamino, N,N-di- C 1 - C 6 alkylamino; if none of the groupings A2 and A3 represents nitrogen, R 3 and R 4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or if none of
  • W represents oxygen or sulphur
  • Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted groupings C 1 -C 6 - alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 2 -C 5 -heterocy c loa Iky 1, C 1 -C 4 -alkoxy, C 1 - C 6 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )- alkyl or represents a grouping N-C 1 -C 4 -alkylamino, N-C 1 -C 4 -alkylcarbonylamino, N,N-di-C 1 -C 4 - alkyla
  • Q represents an unsaturated 6-membered carbocycle which is optionally mono- or polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally mono- or polysubstituted by V,
  • V independently of one another represent halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-C 1 -C 6 -alkoxy-imino-C 1 -C 3 - alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N,N-di-(C 1 -C 6 - alkyl)amino;
  • T represents one of the 5-membered heteroaromatics T1 -T7 listed below, where the bond to the pyrazole head group is marked with an asterisk,
  • R 1 represents hydrogen or represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 ) -alkyl which are optionally mono- or polysubstituted independently of one another by halogen, cyano, alkoxy and alkoxycarbonyl, the chemical groupings
  • Ai represents CR 2 or nitrogen
  • A2 represents CR ' or nitrogen
  • A3 represents CR 4 or nitrogen and A4 represents CR 3 or nitrogen, but where not more than three of the chemical groupings Ai to A4 simultaneously represent nitrogen;
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 - C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N-C 1 -C 6 -alkylamino or N,N-di-C 1 - C 6 -alkylamino;
  • W represents oxygen or sulphur;
  • Q represents hydrogen, hydroxy, formyl or one of the groupings C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 - alkynyl, C 3 -C 6 -cycloalkyl, C 2 -C 5 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )-alkyl, N-C 1 -C 4 -alkylamino, N-C 1 -C4-alkylcarbonylamino or N,N-di-C 1 -C 4 -alkylamino
  • Q represents aryl substituted by 0 - 4 substituents V or a 5- or 6-membered heteroaromatic substituted by 0 - 4 substituents V, where V independently of one another represent halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-C 1 -C 6 -alkoxy-imino-C 1 -C 3 - alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N,N-di-(C 1 -C 6 - alkyl) amino;
  • T represents one of the 5-membered heteroaromatics T1 -T7 listed below, where the bond to the pyrazole head group is marked with an asterisk,
  • R' independently of one another represent halogen, cyano, nitro, amino or optionally mono- or polyhalogen-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, and n represents the values 0-1 ;
  • Z 1 represents optionally substituted C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, and represents hydrogen, halogen, cyano, nitro, amino or optionally mono- or polysubstituted C 1 -C 6 - alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, and represents hydrogen or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkenyl, C 1 -C 4 - alkynyl, aryl or hetaryl.
  • R 1 represents hydrogen or represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 ) -alkyl which are optionally mono- to pentasubstituted independently of one another by halogen, cyano, alkoxy and alkoxycarbonyl, the chemical groupings A 1 represents CR 2 or nitrogen,
  • a 2 represents CR 3 or nitrogen
  • a 3 represents CR 4 or nitrogen
  • a 4 represents CR 5 or nitrogen, but where not more than three of the chemical groupings Ai to A4 simultaneously represent nitrogen;
  • R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, or represent C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 -C 6 - alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N-C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 - alkylamino which are optionally mono- to pentasubstituted independently of one another by hydroxy, nitro, amino, halogen, alk
  • W represents oxygen or sulphur
  • Q represents hydrogen, hydroxy, formyl or one of the groupings C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 - alkynyl, C 3 -C 6 -cycloalkyl, C 2 -Cs-heterocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )-alkyl, 7V-C 1 -C 4 -alkylamino, N-C 1 -C 4 -alkylcarbonylamino or N,N-di-C 1 -C 4 -alkylamino
  • R 6 independently of one another represent halogen, cyano, nitro, amino or optionally mono- to pentahalogen-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy, C 1 -C 6 -aikylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, and n represents the values 0-1 ;
  • Z 1 represents C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl optionally mono- to pentasubstituted by hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl, and
  • Z 2 represents hydrogen, halogen, cyano, nitro, amino or represents C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl optionally independently of one another mono- to pentasubstituted by hydroxy, nitro, amino, halogen alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl, and
  • Z 3 represents hydrogen or represents C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl C 1 -C 4 -alkenyl, C 1 -C 4 -alkynyl, aryl or hetaryl optionally independently of one another mono- to pentasubstituted by hydroxy, nitro, amino, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl.
  • a 2 represents CR 3 or nitrogen
  • a 3 represents CR 4 or nitrogen
  • a 4 represents CR 5 or nitrogen, but where not more than three of the chemical groupings Ai to A4 simultaneously represent nitrogen;
  • R and R 5 independently of one another represent hydrogen, methyl, fluorine or chlorine and
  • R ' and R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, 2,2,2- trifluoroethyl, methoxy, ethoxy, n-propoxy, 1 -methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichloro fluoromethoxy, trifluoromethoxy, 2,2,2 -trifluoroethoxy, 2-chloro-2,2- difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1 -(N-methoxyimino)ethyl, methylsulfanyl, trifluoromethylsulphanyl, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl
  • W represents oxygen or sulphur
  • Q represents hydrogen, methyl, ethyl, n-propyl, 1 -methylethyl, 1 , 1 -dimethyl ethyl, 1 -methylpropyl, n-butyl, 2 -methylpropyl, 2-methylbutyl, hydroxyethyl, 2 -hydroxypropy 1, cyanomethyl, 2- cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 -trifluoromethylethyl, 2,2- difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1 - cyanocyclopropyl, 1 -methoxycarbonylcyclopropyl, l -(N-methylcarbamoyl)cyclopropyl, 1- carbamoylcyclopropyl, 1 -car
  • R 6 independently of one another represent halogen, cyano, nitro, amino, methyl, ethyl, propyl, 1 - methylethyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, 2,2- difluoroethoxy, 2,2,2 -trifluoroethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methylsulphanyl, methylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl, trifluoromethylsulphanyl, trifluoromethylsulphinyl, and n represents the values 0-1 ;
  • Z 1 represents methyl, ethyl, 1 , 1 -dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1 -fluoroethyl, 1 -fluoro- 1 -methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2- tetrafluoroethyl, 1 -chloro- 1 ,2,2,2 -tetrafluoroethyl, 2,2,2 -trichloroethyl, 2-chloro-2,2-difluoroethyl, 1 , 1 -difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl
  • Z 3 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethenyl, 1 -propenyl, 1 -propynyl, 1 -butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1 -fluoroethyl, 1 -fluoro- 1 -methylethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,5- dichlorophenyl, 3 ,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-dichloro-4-
  • Z 1 represents trifluoromethyl, 1 -chlorocyclopropyl, 1 -fluorocyclopropyl or pentafluoroethyl,
  • Z 2 represents trifluoromethyl, nitro, methylsulphanyl, methylsulphinyl, methylsulphonyl, fluorine, chlorine, bromine, cyano or iodine,
  • Z 3 represents methyl, ethyl, n-propyl or hydrogen
  • ⁇ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, methoxy c arbony 1, ethoxyc arbony 1, n- propoxy c arbony 1, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2- cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl, pyrid-3 -ylmethyl, pyrid-4 -ylmethy 1, 4- chloropyrid-3 -ylmethyl,
  • a 1 , A 2 and A 4 each represent CH, where
  • a 2 may alternatively also represent CH or N,
  • A3 represents CR 4
  • R 4 represents fluorine, chlorine, bromine or iodine
  • R 4 may alternatively also represent methyl, ethyl, fluorine, chlorine, bromine or iodine,
  • T represents one of the 5-membered heteroaromatics T1-T7 listed below, where the bond to the pyrazole head group is marked with an asterisk,
  • R 6 represents hydrogen, methyl, ethyl, 2-methylethyl, 2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, cyano, nitro, trifluoromethyl, amino, or alternatively
  • R 6 represents hydrogen, methyl, ethyl, 2-methylethyl, 2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, amino,
  • W represents oxygen
  • Q represents hydrogen, methyl, ethyl, n-propyl, 1 -methylethyl, 1 , 1 -dimethylethyl, n-butyl, 1- methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxyniethyl, hydroxyethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2 -trifluoroethyl, 1 - trifluoromethylethyl, 2,2-difluoropropyl, 3,3,3 -trifluoropropy 1, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1 -cyanocyclopropyl, 1 -methoxycarbonylcyclopropyl, 1 -(N- methylcarbamoyl)cyclopropyl, 1 -carbamoylcyclo
  • Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene, pyrrole, oxadiazole, thiadiazole substituted by 0, 1, 2 or 3 substituents V, where
  • V independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2- tetrafluoroethyl, 1 -chloro- 1 ,2,2,2 -tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1 , 1 -difluoroethyl, pentafluoroethyl, heptafluoro -n-propy 1, heptafluoroisopropyl, nonafluoro-n- butyl, cyclo
  • Z 1 represents CF 2 CF 3
  • Z 2 represents CF3
  • Z 3 represents methyl, ethyl, phenyl, 4-N02-phenyl, 3 -chloropyridin-2-yl
  • the radicals R 1 , R 6a represent hydrogen or methyl
  • R 6b represents hydrogen, methyl or CF 3
  • a 1 , A 4 represent C-H
  • a 2 represents C-H or C-F
  • a 3 represents C-H or C-Cl
  • W represents oxygen and Q represents one of the radicals 1 -cyanocyclopropyl, benzyl, cyclopropyl, 2 -thienylmethyl, carbamoylthiocyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulphonyl, thietan-3-yl, 1 - c arbamoy Icy c lopropyl .
  • Z 1 represents CF 2 CF 3
  • Z 2 represents CF3
  • Z 3 represents methyl, ethyl, phenyl, 4-N02-phenyl, 3- chloropyridin-2 -y 1
  • the radicals R 1 , R 6a represent hydrogen or methyl
  • R 6b represents hydrogen, methyl or CF 3
  • a 1 , A 4 represent C-H
  • a 2 represents N
  • a 3 represents C-H or C-Cl
  • W represents oxygen and Q represents one of the radicals 1 -cyanocyclopropyl, benzyl, cyclopropyl, 2- thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulphonyl, thietan-3-yl, 1 -carbamoylcyclopropyl.
  • alkyl on its own or as part of a chemical group - represents straight- chain or branched hydrocarbons preferably having 1 to 6 carbon atoms such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 , 1 -dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1 - methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,2-dimethylpropyl, 1 ,3 -dimethylbutyl, 1 ,4-dimethylbutyl, 2,3 -dimethylbutyl, 1
  • alkyl groups having 1 to 4 carbon atoms such as, inter alia, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl.
  • the alkyl groups according to the invention may be substituted by one or more identical or different radicals.
  • alkenyl on its own or as part of a chemical group - represents straight- chain or branched hydrocarbons preferably having 2 to 6 carbon atoms and at least one double bond such as, for example, vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1 -methyl-2 -propenyl, 2 -methyl-2 - propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-2 -butenyl, 2 -methyl -2 -buteny 1, 3 -methyl-2 - butenyl, 1 -methyl-3 -butenyl, 2-methyl-3-butenyl, 3 -methyl-3 -butenyl, 1 , 1 -dimethyl-2 -propenyl, 1,2- dimethyl-2 -propenyl, 1 -ethyl-2 -propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,
  • alkenyl groups having 2 to 4 carbon atoms such as, inter alia, 2-propenyl, 2-butenyl or 1- methyl -2 -propenyl .
  • the alkenyl groups according to the invention may be substituted by one or more identical or different radicals.
  • alkynyl on its own or as part of a chemical group - represents straight- chain or branched hydrocarbons preferably having 2 to 6 carbon atoms and at least one triple bond such as, for example, 2-propynyl, 2-butynyl, 3 -butynyl, 1 -methyl-2 -propynyl, 2-pentynyl, 3-pentynyl, 4- pentynyl, 1 -methyl-3 -butynyl, 2 -methyl-3 -butynyl, 1 -methyl -2 -butynyl, 1 , 1 -dimethyl -2 -propynyl, 1 - ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2 -pentynyl, 1 -methyl-3 - pentynyl,
  • alkynyl groups having 2 to 4 carbon atoms such as, inter alia, ethynyl, 2-propynyl or 2 -butynyl - 2-propenyl.
  • the alkynyl groups according to the invention may be substituted by one or more identical or different radicals.
  • cycloalkyl on its own or as part of a chemical group - represents mono-, bi- or tricyclic hydrocarbons preferably having 3 to 10 carbons such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl.
  • Preference is furthermore given to cycloalkyl groups having 3, 4, 5, 6 or 7 carbon atoms such as, inter alia, cyclopropyl or cyclobutyl.
  • alkylcycloalkyl represents mono-, bi- or tricyclic alkylcycloalkyl preferably having 4 to 10 or 4 to 7 carbon atoms such as, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Preference is furthermore given to alkylcycloalkyl groups having 4, 5 or 7 carbon atoms such as, inter alia, ethylcyclopropyl or 4- methylcyclohexyl.
  • the alkylcycloalkyl groups according to the invention may be substituted by one or more identical or different radicals.
  • cycloalkylalkyl represents mono-, bi- or tricyclic cycloalkylalkyl preferably having 4 to 10 or 4 to 7 carbon atoms such as, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Preference is furthermore given to cycloalkylalkyl groups having 4, 5 or 7 carbon atoms such as, inter alia, eye lopropylmethy 1 or cyclobutylmethyl.
  • the cycloalkylalkyl groups according to the invention may be substituted by one or more identical or different radicals.
  • halogen represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • halogen-substituted chemical groups according to the invention such as, for example, haloalkyl, halocycloalkyl, haloalkyloxy, haloalkylsulphanyl, haloalkylsulphinyl or haloalkylsulphonyl are mono- or polysubstituted by halogen up to the maximum possible number of substituents.
  • the halogen atoms can be identical or different, and can all be attached to one or to a plurality of carbon atoms.
  • halogen represents in particular fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferably fluorine.
  • halocycloalkyl represents mono-, bi- or tricyclic halocycloalkyl having preferably 3 to 10 carbon atoms such as, inter alia, 1 -fluorocyclopropyl, 2-fluorocyclopropyl or 1 - fluorocy c lobuty 1. Preference is furthermore given to halocycloalkyl having 3, 5 or 7 carbon atoms.
  • the halocycloalkyl groups according to the invention may be substituted by one or more identical or different radicals.
  • haloalkyl "hatoalkenyl” or “haloalkynyl” represents halogen-substituted alkyl, alkenyl or alkynyl groups having preferably 1 to 9 identical or different halogen atoms such as, for example, monohaloalkyl such as CH 2 CH 2 C1, CH 2 CH 2 F, CHC1CH 3 , CHFCH3, CH 2 C1, CH 2 F; perhaloalkyl such as CC1 3 or CF 3 or CF 2 CF 3 ; polyhaloalkyl such as CHF 2 , C H. F. CH 2 CHFC1, CHC1 2 , CF2CF2H, CH2CF3.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , ( KTI. F. OCF 2 CF 3 , OCF 2 CF 3 and OCH 2 CH 2 Cl.
  • haloalkyl groups are trichloromethyl, chlorodifluoromethyl, di chlorofluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2- difluoroethyl, pentafluoroethyl and p entafluoro -t-buty 1.
  • haloalkyl groups having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms selected from the group consisting of fluorine and chlorine such as, inter alia, difluoromethyl, trifluoromethyl or 2,2- difluoroethyl.
  • hydroxyalkyl represents a straight-chain or branched alcohol preferably having 1 to 6 carbon atoms such as, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. Preference is furthermore given to hydroxyalkyl groups having 1 to 4 carbon atoms.
  • the hydroxyalkyl groups according to the invention may be substituted by one or more identical or different radicals.
  • alkoxy represents a straight-chain or branched O-alkyl preferably having 1 to 6 carbon atoms such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Preference is furthermore given to alkoxy groups having 1 to 4 carbon atoms.
  • the alkoxy groups according to the invention may be substituted by one or more identical or different radicals.
  • haloalkoxy represents halogen-substituted straight- chain or branched O- alkyl preferably having 1 to 6 carbon atoms such as, inter alia, difluoromethoxy, trifluoromethoxy, 2,2- difluoroethoxy, 1 , 1 ,2,2-tetrafluoroethoxy, 2,2,2 -trifluoroethoxy and 2-chloro- 1 , 1 ,2 -trifluoroethoxy.
  • the haloalkoxy groups according to the invention may be substituted by one or more identical or different radicals.
  • alkylsulphanyl represents straight-chain or branched S-alkyl preferably having 1 to 6 carbon atoms such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- butylthio, isobutylthio, s-butylthio and t-buty lthio. Preference is furthermore given to alkylsulphanyl groups having 1 to 4 carbon atoms.
  • the alkylsulphanyl groups according to the invention may be substituted by one or more identical or different radicals.
  • haloalkylsulphanylalkyl groups i.e. halogen-substituted alkylsulphanyl groups
  • di fluoromethy lthio trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio, 1 - fluoroethylthio, 2 -fluoroethy lthio, 2,2-difluoroethylthio, 1 , 1 ,2,2-tetrafluoroethylthio, 2,2,2- trifluoroethylthio or 2-chloro- 1 , 1 ,2-trifluoroethylthio.
  • alkylsulphinyl represents straight-chain or branched alkylsulphinyl preferably having 1 to 6 carbon atoms such as, for example, methylsulphinyl, ethylsulphinyl, n- propylsulphinyl, isopropylsulphinyl, n-butylsulphinyl, isobutylsulphinyl, s-butylsulphinyl and t- butylsulphinyl. Preference is furthermore given to alkylsulphinyl groups having 1 to 4 carbon atoms.
  • the alkylsulphinyl groups according to the invention may be substituted by one or more identical or different radicals.
  • haloalkylsulphinyl groups i.e. halogen-substituted alkylsulphinyl groups
  • difluoromethylsulphinyl trifluoromethylsulphinyl
  • trichloromethylsulphinyl chlorodifluoromethylsulphinyl, 1 -fluoroethylsulphinyl, 2-fluoroethylsulphinyl, 2,2- difluoroethylsulphinyl, 1 , 1 ,2,2-tetrafluoroethylsulphinyl, 2,2,2 -tri fluoroethylsulphinyl and 2-chloro- 1 , 1 ,2 -trifluoro ethylsulphinyl .
  • alkylsulphonyl represents straight-chain or branched alkylsulphonyl preferably having 1 to 6 carbon atoms such as, for example, methylsulphonyl, ethylsulphonyl, n- propylsulphonyl, isopropylsulphonyl, n-butylsulphonyl, isobutylsulphonyl, s-butylsulphonyl and t- butylsulphonyl. Preference is furthermore given to alkylsulphonyl groups having 1 to 4 carbon atoms.
  • the alkylsulphonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • haloalkylsulphonyl groups i.e. halogen-substituted alkylsulphonyl groups
  • difluoromethylsulphonyl trifluoromethylsulphonyl
  • trichloromethylsulphonyl chlorodifluoromethylsulphonyl, 1 -fluoroethylsulphonyl, 2 - fluoro ethylsulphonyl, 2,2- difluoroethylsulphonyl, 1 , 1 ,2,2-tetrafluoroethylsulphonyl, 2,2,2 -trifluoroethylsulphonyl and 2-chloro- 1 , 1 ,2 -tri fluoroethylsulphonyl.
  • the alkylcarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • cycloalkylcarbonyl represents straight-chain or branched cycloalkylcarbonyl preferably having 3 to 10 carbon atoms in the cycloalkyl moiety such as, for example, eye lopropyle arbonyl, cyclobutylcarbonyl, eye lopenty lc arbonyl, eye lohexyle arbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, bicyclo[2.2. i]heptyl, bicyclo[2.2.2 ] octy lc arbonyl and adamantylcarbonyl.
  • alkoxycarbonyl alone or as a constituent of a chemical group - represents straight- chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms or having 1 to 4 carbon atoms in the alkoxy moiety such as, for example, methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl.
  • the alkoxycarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • alkylaminocarbonyl represents straight-chain or branched alkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl.
  • the alkylaminocarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • N,N-dialkylaminocarbonyl represents straight-chain or branched N,N- dialkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as, for example, iV ⁇ V-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(n- propylamino)carbonyl, N,N-di(isopropylamino)carbonyl and N,N-di-(s-butylamino)carbonyl.
  • the N,N- dialkylaminocarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • aryl represents a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms such as, for example, phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl. Furthermore, aryl also represents polycyclic systems such as tetrahydronaphtyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system.
  • the aryl groups according to the invention may be substituted by one or more identical or different radicals.
  • substituted aryls are the arylalkyl groups which may likewise be substituted by one or more identical or different radicals in the alkyl and/or aryl moiety.
  • arylalkyl groups are inter alia benzyl and 1 -phenylethyl.
  • heterocycle represents a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a heteroatom, preferably by a heteroatom from the group consisting of N, O, S, P, B, Si, Se, and which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted by a substituent Z, where the point of attachment is located at a ring atom.
  • the heterocyclic ring contains preferably 3 to 9 ring atoms, especially 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group consisting of N, O, and S, although no two oxygen atoms should be directly adjacent.
  • the heterocyclic rings usually contain not more than 4 nitrogen atoms and/or not more than 2 oxygen atoms and/or not more than 2 sulphur atoms.
  • heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused to other carbocyclic or heterocyclic rings, in the case of optionally substituted heterocyclyl, the invention also embraces polycyclic systems such as, for example, 8-azabicyclo[3.2.1 Joctanyl or 1 - azabicyclo[2.2. ljheptyl. In the case of optionally substituted heterocyclyl, the invention also embraces spirocyclic systems such as, for example, l-oxa-5-azaspiro[2.3]hexyl.
  • Heterocyclyl groups according to the invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl, oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorph
  • heteroarylene i.e. heteroaromatic systems
  • heteroaryl represents heteroaromatic compounds, i.e. completely unsaturated aromatic heterocyclic compounds which fall under the above definition of heterocycles.
  • Heteroaryl groups according to the invention are, for example, furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,3,4-, 1,2,4- and 1,2,5- oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2,3- triazinyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1 ,2.4- diazepinyl.
  • the heteroaryl groups according to the invention may also be substituted by one or more identical or different radicals.
  • Substituted groups such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical are, for example, a substituted radical derived from the unsubstituted base structure, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group of halogen, alkoxy, alkylsulphanyl, hydroxyl, amino, nitro, carboxyl or a group equivalent to the carboxyl group, cyano, isocyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and N,N-dialkylaminocarbonyl, substituted amino such as acylamino, mono- and N,N-dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted hetero
  • substituted groups such as substituted alkyl etc.
  • substituents in addition to the saturated hydrocarbonaceous radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl, alkenylcarbonyl, alkynylcarbonyl, mono- and N,N-dialkenylaminocarbonyl, mono- and dialkynylaminocarbonyl, mono- and N,N-dialkenylamino, mono- and ⁇ , ⁇ -dialkynylamino, trialkenylsilyl, trialkynylsilyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, phenyl, phenoxy etc.
  • cyclic systems with those substituents bonded to the ring by a double bond are also included, for example those having an alkylidene group such as methylidene or ethylidene, or an oxo group, imino group and a substituted imino group.
  • radicals When two or more radicals form one or more rings, these may be carbocyclic, heterocyclic, saturated, partly saturated, unsaturated, for example also aromatic and further substituted.
  • first substituent level may, if they contain hydrocarbon-containing moieties, optionally be further substituted therein (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • second substituent level may be further substituted therein, for example by one of the substituents as defined for the first substituent level.
  • substituent levels are possible.
  • substituted radical preferably embraces just one or two substituent levels.
  • Preferred substituents for the substituent levels are, for example, amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxyl, carboxamide, SF 5 , aminosulphonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, N-monoalkylamino, N,N- dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkeny loxyc arbony 1, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylsulphanyl, cycloalkylsulphanyl, alkenylthio,
  • Substituents composed of a plurality of substituent levels are preferably alkoxyalkyl, alkylsulphanylalkyl, alkylsulphanylalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, halocycloalkyl, haloalkoxy, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphonyl, haloalkanoyl, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylsulphanyl, haloalkoxyalkanoyl, haloalkoxyalkyl.
  • radicals having carbon atoms preference is given to those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, especially 1 or 2 carbon atoms.
  • substituents from the group of halogen, e.g. fluorine and chlorine, (C 1 -C4)-alkyl, preferably methyl or ethyl, (C 1 -C4) -haloalkyl, preferably trifluoromethyl, (C 1 -C4)-alkoxy, preferably methoxy or ethoxy, (C 1 - C4)-haloalkoxy, nitro and cyano.
  • substituents methyl, methoxy, fluorine and chlorine.
  • Substituted amino such as mono- or disubstituted amino means a radical from the group of the substituted amino radicals which are N- substituted, for example, by one or two identical or different radicals from the group consisting of alkyl, hydroxy, amino, alkoxy, acyl and aryl; preferably N-mono- and TV,N-dialkylamino, (for example methylamino, ethylamino, ⁇ , ⁇ '-dimethylamino, N,N-diethylamino, A T ,7V-di-n-propylamino, N,N-diisopropylamino or N,N-dibutylamino), N-mono- or TV,N- dialkoxyalkylamino groups (for example N-methoxymethylamino, N-methoxyethylamino, N,N- di(methoxymethyl)amino or A r , A- di(methoxy e
  • cyclic amino groups embraces heteroaromatic or aliphatic ring systems having one or more nitrogen atoms.
  • the heterocycles are saturated or unsaturated, consist of one or more optionally fused ring systems and optionally contain further heteroatoms such as, for example, one or two nitrogen, oxygen and/or sulphur atoms.
  • the term also includes groups having a spiro ring or a bridged ring system.
  • the number of atoms which form the cyclic amino group is not limited, and in the case of a one-ring system, for example, can consist of 3 to 8 ring atoms, and in the case of a two-ring system of 7 to 11 atoms.
  • Examples of cyclic amino groups having saturated and unsaturated monocyclic groups having a nitrogen atom as heteroatom which may be mentioned are 1-azetidinyl, pyrrolidino, 2-pyrrolidin- 1 -yl, 1 -pyrrolyl, piperidino, 1 ,4-dihydropyrazin- 1 -yl, 1 ,2,5,6-tetrahydropyrazin- 1 -yl, 1 ,4-dihydropyridin- 1 -yl, 1,2,5,6- tetrahydropyridin- 1 -yl, homopiperidinyl; examples of cyclic amino groups having saturated and unsaturated monocyclic groups having two or more nitrogen atoms as heteroatoms which may be mentioned are 1 -imidazolidinyl, 1 -imidazolyl, 1 -pyrazolyl, 1 -triazolyl, 1 -tetrazolyl, 1 -piperazinyl, 1- homopiperazin
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group of halogen, (C 1 -Gi)-alkyl, (C 1 -GO-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 - C 4 )-haloalkoxy, (C 1 -C 4 )-alkylsulphanyl, (C 1 -C 4 )-haloalkylsulphanyl, cyano, isocyano and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophen
  • Optionally substituted cycloalkyl is preferably cycloalkyl, which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group of halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )- alkyl, (C 1 -C 4 )-haloalkyl and (C 1 -C 4 )-haloalkoxy, especially by one or two (C 1 -C 4 )-alkyl radicals.
  • Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group of halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )- alkyl, (C i -C 4 )-haloalkyl, (C i -C 4 ) -haloalkoxy , nitro and oxo, especially mono- or polysubstituted by radicals from the group of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalky
  • alky 1 - sub stituted heteroaryl groups are furylmethyl, thienylmethyl, pyrazolylmethyl, imidazolylmethyl, 1 ,2,3- and 1 ,2,4-triazolylmethyl, isoxazolylmethyl, thiazolylmethyl, isothiazolylmethyl, 1,2,3-, 1,3,4-, 1 ,2,4- and 1 ,2,5-oxadiazolylmethyl, azepinylmethyl, pyrrolylmethyl, pyridylmethyl, pyridazinylmethyl, pyrimidinylmethyl, pyrazinylmethyl, 1,3,5-, 1,2,4- and 1,2,3- triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- and 1 ,2,6-oxazinylmethyl, oxepinylmethyl, thiepinylmethyl and 1 ,2,4-diazepinylmethyl.
  • the compounds of formula (I) described in detail above are combined with other active compounds, namely (1) ectoparasiciticides in particular having acaricidal and/or insecticidal activity; (2) anthelmintics in particular having nematicidal, trematicidal and/or cestodicial activity; (3) anti-protozoal agents, in order to widen the activity spectrum.
  • active compounds namely (1) ectoparasiciticides in particular having acaricidal and/or insecticidal activity; (2) anthelmintics in particular having nematicidal, trematicidal and/or cestodicial activity; (3) anti-protozoal agents, in order to widen the activity spectrum.
  • Potential mixing components for compounds of the formula (I) according to the invention for applications in animal health may be one or more compounds of the groups of active compounds listed below. The following active compounds can be used in the present combinations:
  • Exemplary active ingredients from the group of ectoparsiticides, as mixing partners, include, without limitation, the following insecticidal and/or acaricidal compounds
  • acetylcholinesterase (AChE) inhibitors for example carbamates, e.g. alanycarb, aldicarb,
  • aldoxycarb aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate, formparanate or organophosphates, e.g.
  • GABA-gated chloride channel antagonists for example organochlorines, e.g. camphechlor,
  • chlordane endosulfan, heptachlor, lindane or m-diamides, e.g. broflanilide or phenylpyrazoles, e.g. flufiprole, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole or arylisoxazo lines, not excluding related classes with pyrroline or pyrrolidine moiety replacing the isoxazoline ring , e.g.
  • sodium channel modulators / voltage-dependent sodium channel blockers for example pyrethroids, e.g. heptafluthrin, tetramethylfluthrin, acrinathrin, allethrin (d-cis-trans, d-trans-), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-s-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin (lambda-), cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin
  • methoxychlor or oxadiazines e.g. indoxacarb or semicarbazones, e.g. metaflumizone;
  • acetylcholine receptor agonists/ antagonists for example neonicotinoids, e.g. imidacloprid, thiacloprid, imidaclothiz, nitenpyram, thiamethoxam, clothianidin, dinotefuran, acetamiprid, nithiazine, paichongding, cycloxaprid, guadipyr, N-[(2E)-l-[(6-chloropyridin-3-yl)methyl]pyridin- 2(lH)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012/029672), (3E)-3-[l-[(6-chloro-3- pyridyl)methyl] -2-pyridylidene]- 1 ,1,1 -trifluoro-propan-2-one (known from WO2013/144213) or sulfoximine insecticides, e.g.
  • sulfoxaflor or butenolides e.g. flupyradifurone or nereistoxin analogues, e.g. cartap, bensultap, thiocyclam, thiosultap sodium, thiocyclam hydrogen oxalate; acetylcholine receptor modulators, for example spinosynes, e.g. spinosad, spinetoram or zwitterionic insecticides, e.g.
  • ligand-gated chloride channel activators for example macrocyclic lactones, e.g. emamectin benzoate, abamectin, ivermectin, milbemectin, milbemycin oxime, latidectin, lepimectin, selamectin, doramectin, eprinomectin, moxidectin, nemadectin or indole diterpenes, e.g.
  • macrocyclic lactones e.g. emamectin benzoate, abamectin, ivermectin, milbemectin, milbemycin oxime, latidectin, lepimectin, selamectin, doramectin, eprinomectin, moxidectin, nemadectin or indole diterpenes, e.g.
  • juvenile hormone mimetics for example juvenile hormon analogues, e.g. diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene;
  • juvenile hormon analogues e.g. diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene;
  • selective homopteran feeding blockers for example triazinones, e.g. pymetrozine or pyridine carboxamides, e.g. flonicamid;
  • Bios, hormones or pheromones for example natural products, e.g. codlemone, thuringiensin or neem components, e.g. azadirachtin A or other classes, e.g. preparations based on bacillus firmus (i-1582; bioneem; votivo);
  • inhibitors of oxidative phosphorylation for example organotin compounds, e.g. azocyclotin, cyhexatin, fenbutatin-oxide or other classes, e.g.
  • decouplers of oxidative phosphorylation by interruption of H-proton gradients for example dinitrophenols, e.g. binapacryl, dinobuton, dinocap, DNOC or pyrroles, e.g. chlorfenapyr or other decouplers, e.g. sulfluramid; inhibitors of chitin biosynthesis or cuticle development, for example benzoylureas, e.g.
  • ecdysone agonists/ disrupters for example diacylhydrazines, e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide, fufenozide;
  • diacylhydrazines e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide, fufenozide;
  • octopaminergic agonists for example amidine derivatives, e.g. amitraz, cymiazole, demiditraz, chlormebuform;
  • mitochondrial complex I electron transport inhibitors for example METIs, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, dicofol or rotenones, e.g.
  • METIs e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, dicofol or rotenones, e.g.
  • mitochondrial complex 11 electron transport inhibitors for example beta-ketonitrile derivatives, e.g. cyenopyrafen, cyflumetofen or hydrazones, e.g. hydramethylnon or other classes, e.g. fluopyram, 4- (7-bromo- 1 ,3 -benzodioxol-5 -yl) - 1 -(3 -methoxypyrazin-2-yl) -3 -(trifluoromethyl) - 1 H-pyrazol-5 - amine (known from WO 2010136145, example 74, CAS No 1257061-92-9);
  • beta-ketonitrile derivatives e.g. cyenopyrafen, cyflumetofen or hydrazones, e.g. hydramethylnon or other classes, e.g. fluopyram, 4- (7-bromo- 1 ,3 -benzodioxol-5
  • mitochondrial complex I I I electron transport inhibitors for example quinones, e.g. acequinocyl or strobilurines, e.g. flufenoxystrobin, pyriminostrobin or other classes, e.g. fluacrypyrim;
  • quinones e.g. acequinocyl or strobilurines, e.g. flufenoxystrobin, pyriminostrobin or other classes, e.g. fluacrypyrim;
  • inhibitors of acetylCoA carboxylase for example tetronic and tetramic acids, e.g. spirodiclofen, spiromesifen, spirotetramat, 3 -(2 , 5 -dimethy lpheny 1) -4 -hydroxy- 8 -methoxy- 1 ,8- diazaspiro[4.5]dec-3-en-2-one (known from WO2009/049851), butyl [2-(2,4-dichlorophenyl)-3- oxo-4-oxaspiro[4.5]dec-l -en-l-yl] carbonate (known from CN 102060818) or other classes, e.g.
  • tetronic and tetramic acids e.g. spirodiclofen, spiromesifen, spirotetramat, 3 -(2 , 5 -dimethy lpheny 1) -4 -hydroxy- 8 -methoxy
  • ryanodine receptor modulators for example phthalic acid diamides, e.g. flubendiamide, cyhalodiamide or anthranilamides, e.g. chlorantraniliprole, cyantraniliprole, tetraniliprole, tetrachloroantraniliprole (SYP9080), cyclaniliprole, methyl 2-[2-( ⁇ [3-bromo- 1 -(3-chloropyridin-2- yl)-lh-pyrazol-5-yl]carbonyl ⁇ amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[3,5-dibromo-2-( ⁇ [3-bromo-l-(3-chloropyridin-2-yl)-lh- pyrazol-5 -yl] carbonyl ⁇ amino)benzoyl]
  • mite growth inhibitors e.g. clofentezine, etoxazole, hexythiazox, amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, chlordimeform, chlorobenzilate, clothiazoben, cycloprene, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, f!ufenerim, flutenzin, gossyplure, japonilure, metoxadiazone, petroleum, potassium oleate, pyridalyl, tetrasul, triarathene or other classes, e.g.
  • diflovidazin, chinomethionat, pyrifluquinazon or feeding inhibitors e.g. cryolite; ⁇ compounds, from other classes, e.g. 4-(but-2-yn-l-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003/076415), fluazaindolizine, afidopyropen, flometoquin, fluensulfone, fluhexafon, iprodione, meperfluthrin, N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-l,3-thiazol-5-yl]pyridine-2- carboxamide (known from WO2012/000896), N-[2-(5-amino-l ,3,4-thiadiazol-2-yl)-4-chloro-6- methylphenyl]-3-bromo-l -(3-chloropyridin-2-y
  • MGK264 N- octylbicycloheptenecarboxamide
  • PBO piperonyl butoxide
  • acetylcholine receptor agonists/ antagonists acetylcholine receptor modulators
  • GABA-gated chloride channel antagonists ligand-gated chloride channel activators
  • octopaminergic agonists sodium channel modulators / voltage- dependent sodium channel blockers.
  • active ingredients from the group of anthelmintics, as mixing partners include, without limitation, the following nematicidally, trematicidally and/or cestocidally active compounds:
  • milbemectin latidectin, lepimectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, nemadectin;
  • amidantel deacylated amidantel (dAMD), tribendimidine ;
  • paraherquamides • from the class of paraherquamides, for example: derquantel, paraherquamide;
  • salicylanilides for example: bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide, tribromsalan;
  • organophosphates for example: coumaphos, haloxon, crufomate,
  • piperazines for example: piperazine, hydroxyzine;
  • tetracyclines for example: chlorotetracycline, doxycyclin, oxytetracyclin,
  • amoscanate bephenium
  • bunamidine clonazepam
  • active ingredients from the group of antiprotozoal active compounds include, without limitation, the following active compounds:
  • monensin • from the class of macrocyclic lactones, for example: erythromycin, milbemycin;
  • sulfonamides for example: sulfaquinoxaline, trimethoprim, sulfaclozin;
  • Babesia canis canis • from the class of vaccines or antigenes from microorganisms, for example: Babesia canis canis, Babesia canis rossi, Babesia canis vogeli, Dictyocaulus viviparus, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria mitis, Eimeria necatrix, Eimeria praecox, Eimeria tenella, Leishmania infantum;
  • the active compounds identified here by their common names are known and are described, for example, in the pesticide handbook ("The Pesticide Manual” 14th Ed., British Crop Protection Council 2006) or can be found on the Internet (e.g. http://www.alanwood.net/pesticides).
  • the active compounds described herein may form salts and in this case may be used in salt form as well.
  • Salts which are suitable according to the invention for example salts with bases or acid addition salts, are all customary non-toxic salts, preferably agriculturally and/or physiologically acceptable salts.
  • salts with bases or acid addition salts Preference is given to salts with inorganic bases such as, for example, alkali metal salts (e.g.
  • alkaline earth metal salts e.g. calcium or magnesium salts
  • ammonium salts or salts with organic bases in particular with organic amines, such as, for example, triethylammonium, dicyclohexylammonium, N,A P - dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts
  • salts with inorganic acids e.g. hydrochlorides, hydrobromides, dihydrosulphates, trihydrosulphates or phosphates
  • salts with organic carboxylic acids or organic sulphoacids e.g.
  • t-amines such as some of the compounds contemplated herein are capable of forming N-oxides, which also represent salts according to the invention.
  • the compounds described herein may, depending on the nature of the substituents, be in the form of geometric and/or optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. If appropriate, the compounds may be present in various polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used in accordance with the invention.
  • the present invention is directed to combinations of compounds of formula (I) with ectoparasiciticides, anthelmintics or anti-protozoal agents.
  • the compounds of the general formula (I) can be mixed or applied jointly with other ectoparasiticidal, anthelmintic or anti-protozoal agents.
  • the spectrum of activity of the agents is widened and/or improved as compared to the the individual active compounds in these applications.
  • the active compounds according to the present invention act against animal parasites, in particular ectoparasites and/or endoparasites.
  • animal parasites in particular ectoparasites and/or endoparasites.
  • endoparasites includes especially helminths such as cestodes, nematodes or trematodes, and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects such as flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids such as ticks, for example hard ticks or soft ticks, or mites such as scab mites, harvest mites, bird mites and the like, and also aquatic ectoparasites such as copepods.
  • insects such as flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like
  • acarids such as ticks, for example hard ticks or soft ticks, or mites such as scab mites, harvest mites, bird mites and the like, and also aquatic ectoparasites such as copepods.
  • parasites include the following ectoparasites (in particular insects, acarids):
  • Anoplurida for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phthirus spp. and Solenopotes spp.; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus;
  • Nematocerina and Brachycerina for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora s
  • Pulex spp. Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.
  • specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp.
  • helminths include platyhelmintha (e.g. monogenea, cestodes and trematodes), nematodes, acanthocephala, and pentastoma. Additional exemplary helminths include , without any limitation:
  • Monogenea e.g.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp..
  • Cestodes From the order of the Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp..
  • Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp..
  • Trematodes From the class of the Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoeluin spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocoty
  • Trichinellida for example: Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp..
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.
  • Acantocephala From the order of the Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; from the order of the Polymorphida for example: Filicollis spp.; from the order of the Moniliformida for example: Moniliformis spp.,
  • Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
  • Pentastoma From the order of the Porocephalida for example Linguatula spp.
  • Exemplary parasitic protozoa include , without any limitation:
  • Mastigophora such as, for example, Trypanosomatidae, for example, Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as, for example, Trichomonadidae, for example, Giardia lamblia, G. canis.
  • Trichomonadidae for example, Giardia lamblia, G. canis.
  • S arcomastigophora such as Entamoebidae, for example, Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp., Harmanella sp. Apicomplexa (Sporozoa), such as Eimeridae, for example, Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bo vis, E. brunetti, E. canis,
  • Besnoitia besnoitii such as Sarcocystidae, for example, Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, such as Leucozoidae, for example,
  • Leucozytozoon simondi such as Plasmodiidae, for example, Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, such as Piroplasmea, for example, Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, such as Adeleina, for example, Hepatozoon canis, H. spec.
  • the combinations according to the invention are also suitable for controlling arthropods, helminths and protozoa which attack animals.
  • the animals include agricultural livestock, for example cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, cultured fish, honey bees.
  • the animals also include domestic animals - also referred to as companion animals - for example dogs, cats, caged birds, aquarium fish, and what are known as test animals, for example hamsters, guinea pigs, rats and mice.
  • control of these ectoparasites - or, in other embodiments, helminths and/or protozoa - should reduce cases of death and improve the performance (for meat, milk, wool, hides, eggs, honey etc.) and the health of the host animal, and so the use of the active compounds according to the invention enables more economically viable and easier animal husbandry.
  • control of the parasites can also contribute to preventing the transmission of infectious substances.
  • control as used herein with regard to the field of animal health means that the active compounds act by reducing the occurrence of the parasite in question in an animal infested with such parasites to a harmless level. More specifically, "control” as used herein means that the active compound kills the parasite in question, retards its growth or inhibits its proliferation.
  • the combinations according to the invention can be employed directly when they are used for the treatment of animals. They are preferably employed in the form of pharmaceutical compositions which may comprise the pharmaceutically acceptable excipients and/or auxiliaries known in the prior art. In general, such compositions comprise from 0.01 to 98% by weight of active compound, preferably from 0.5 to 90% by weight.
  • the combinations are employed (administered) in a known manner, by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal inter alia), implants, by nasal administration, by dermal administration in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, earmarks, tailmarks, limb bands, halters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories
  • parenteral administration for example by injection (intramuscular, subcutaneous
  • the active compounds can be formulated as a shampoo or as suitable formulations applicable in aerosols or unpressurized sprays, for example pump sprays and atomizer sprays, In the case of employment for livestock, poultry, domestic pets, etc., the active compounds can be employed as formulations (for example powders, wettable powders ["WP"], emulsions, emulsifiable concentrates ["EC”], free-flowing compositions, homogeneous solutions and suspension concentrates ["SC”]), which contain the active compounds in an amount of 1 to 80% by weight, directly or after dilution (e.g. 100- to 10 000-fold dilution ), or they can be used as a chemical bath.
  • the compounds according to general formula (I) can be prepared as described in WO2014/122083 .
  • the reaction mixture is concentrated to dryness and the residue is taken up in ethyl acetate.
  • the organic phase is washed twice with water, dried over sodium sulphate, filtered and concentrated to dryness.
  • the crude product is purified by column chromatography on silica gel.
  • the reaction mixture is concentrated to dryness and the residue is taken up in ethyl acetate.
  • the organic phase is washed twice with water, dried over sodium sulphate, filtered and concentrated to dryness.
  • the crude product is purified by column chromatography on silica gel.
  • reaction mixture is acidified with 1M hydrochloric acid and the product is extracted with ethyl acetate.
  • the organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. This gives 127 mg of 2-chloro-5- ⁇ 1 -[ 1 -methyl-3 -(pentafluoroethyl)-4-(trifluoromethyl)- 1 H-pyrazol-5 - yl] - 1 H-imidazol-4-yl ⁇ benzoic acid as a colourless solid.
  • the stated mass is the peak of the isotope pattern of the [M+H] + ion of the highest intensity; if the [M- H ]- ion was detected, the stated mass is marked with 2 .
  • the stated mass is the peak of the isotope pattern of the [M-H]- ion of the highest intensity. If the mass was determined by a GCMS (see below for methods) measurement, the stated mass is marked with 3 . *) Note regarding the determination of the logP values and mass detection: The determination of the given logP values was carried out in accordance with EEC Directive 79/831 Annex V.A8 by 1 1 PLC (High Performance Liquid Chromatography) on a reversed-phase column (CI 8).
  • Agilent 1100 LC system 50*4.6 Zorbax Eclipse Plus C18 1.8 micron; mobile phase A: acetonitrile (0.1% formic acid); mobile phase B: water (0.09% formic acid); linear gradient from 10%i acetonitrile to 95%i acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min; oven temperature 55°C; flow rate: 2.0 ml/min.
  • Mass detection is carried out via an Agilend MSD system.
  • MS instrument Waters SQD; UPLC instrument: Waters U PLC: column: Zorbax SB-Aq (Agilent), 50 mm x 2.1 mm, 1.8 ⁇ m; mobile phase A: water + 0.025%o formic acid, mobile phase B: acetonitrile (ULC) + 0.025% formic acid; gradient: 0.0 min 98%A - 0.9 min 25%A - 1.0 min 5%A - 1.4 min 5%A 1.41 min 98%A - 1 .5 min 98%A; oven: 40°C; flow rate: 0.600 ml/min; UV detection: DAD; 210 nm.
  • Solvent dimethyl sulphoxide To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.
  • Tick nymphs (Amblyomma hehraeum) are placed into perforated plastic beakers and immersed in the desired concentration for one minute. The ticks are transferred on filter paper into a Petri dish and stored in a climate-controlled cabinet. After 42 days, the kill in % is determined. 100% means that all of the ticks have been killed; 0% means that none of the ticks have been killed.
  • Test animals cattle ticks (Boophilus microplus) Parkhurst strain, SP-resistant
  • the active compound solution is diluted with water to the concentration desired in each case.
  • This active compound preparation is pipetted into tubes. 8-10 adult engorged female cattle ticks (Boophilus microplus) are transferred into a further tube with holes. The tube is immersed into the active compound formulation, and all ticks are completely wetted. After the liquid has run out, the ticks are transferred on filter discs into plastic dishes and stored in a climate-controlled room. The activity is assessed after 7 days by laying of fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all eggs are fertile.
  • Boophilus microplus - injection test (BOOPMI Inj)
  • Solvent dimethyl sulphoxide To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent, and the concentrate is diluted with solvent to the desired concentration.
  • the activity is assessed after 7 days by laying of fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all eggs are fertile.
  • the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 ⁇ g/animal: Ia-1, I a -2. Ib-2, Ib-3, Ic-1, Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic-10, Ic-11, Ic-12, Ic-13, Ic- 14, Ic-16, Ic-17, Ic-18, Ic-19, Ic-20, lc-2 1.
  • active compound 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide. Dilution with titrated cattle blood gives the desired concentration. About 20 unfed adult cat fleas ( Ctenocephalides felis) are placed into a chamber which is closed at the top and bottom with gauze. A metal cylinder whose bottom end is closed with a parafilm is placed onto the chamber. The cylinder contains the blood/active ingredient preparation, which can be imbibed by the fleas through the parafilm membrane.
  • the kill in % is determined. 100% means that all of the fleas have been killed; 0% means that none of the fleas have been killed.
  • the following compounds of the Preparation Examples show an efficacy of 100 at an application rate of 100 ppm: Ia-1 , Ia-2, Ib-2, Ib-3, Ic-1, Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic- 11, Ic-12, Ic-13, Ic-16, Ic-18, Ic-19, Ic-20, Ic-21, Ic-22, Ic-23, Ic-24, Ic-27, Ic-28, Ic-29, lc-3 1.
  • Solvent dimethyl sulphoxide To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate is diluted with water to the desired concentration.
  • the following compounds of the Preparation Examples show an efficacy of 100%o at an application rate of 100 ppm: Ia-1 , Ia-2, Ib-2, Ib-3, Ic-1, Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic- 10, Ic-11, Ic-12, Ic-13, Ic-14, Ic-16, Ic-17, Ic-18, Ic- 19, Ic-20, Ic-2 ! .
  • Ic-22, Ic-23, lc-24 show an efficacy of 100%o at an application rate of 100 ppm: Ia-1 , Ia-2, Ib-2, Ib-3, Ic-1, Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic- 10, Ic-11, Ic-12, Ic-13, Ic-14, Ic-16, Ic-17, Ic-18, Ic- 19, Ic-20, Ic-2 ! .
  • Vessels containing a sponge treated with sugar solution and the active compound preparation of the desired concentration are populated with 10 adult houseflies ⁇ Musca domestica).
  • the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.
  • the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of lOO ppm: Ib-2, Ib-3, Ic-1, Ic-2, Ic-3, Ic-7, Ic-11, Ic- 12, Ic-16, Ic-18, Ic-19, Ic-21, Ic-23, Ic-24.
  • the tubes After evaporation of the solvent, the tubes are populated with 5-10 adult cat fleas ( Ctenocephalides felis), sealed with a perforated plastic lid and incubated in a horizontal position at room temperature and ambient humidity. After 48 h, the efficacy is determined. To this end, the test tubes are stood upright and the fleas are knocked to the floor of the tube. Fleas which remain motionless on the floor or move in an uncoordinated manner are considered to be dead or moribund. A substance shows good activity against Ctenocephalides felis if, in this test, an efficacy of at least 80% was achieved at an application rate of 5 ⁇ g/cm 2 . An efficacy of 100% means that all fleas were dead or moribund. 0% efficacy means that none of the fleas had been damaged.
  • the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 5 ⁇ g/cm 2 : Ia-1, Ia-2, Ib-2, lb-3.
  • the tubes After evaporation of the solvent, the tubes are populated with 5-10 adult dog ticks ⁇ Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated in a horizontal position in the dark at room temperature and ambient humidity. After 48 h, the efficacy is determined. To this end, the ticks are knocked to the floor of the tube and incubated on a hotplate at 45-50°C for at most 5 min. Ticks which remain motionless on the floor or move in an uncoordinated manner such that they are not able to deliberately avoid the heat by climbing upwards are considered to be dead or moribund.
  • a substance shows good activity against Rhipicephalus sanguineus if, in this test, an efficacy of at least 80% was achieved at an application rate of 5 ⁇ g/cm 2 .
  • An efficacy of 100% means that all ticks were dead or moribund. 0% efficacy means that none of the ticks had been damaged.
  • the following compounds of the Preparation Examples show an efficacy of 100%o at an application rate of 1 ⁇ g/cm 2 : Ia-1, Ia-2, Ib-3. Ic-1, Ic-2, Ic-11 , Ic-16, Ic-18, Ic-19, Ic-21, Ic- 23, Ic-24, Ic-25, Ic-27, Ic-36, Ic-37, Ic-43, Ic-46, Ic-47, Ic-48, Ic-49, Ic-54, Ic-59, Ic-66, Ic-68, Ic-70, Ic- 77, Ic-78, Ic-81, Ic-83, Ic-84, Ic-85, Ic-86, Ic-87, Ic-90, Ic-94, Ic-95, Ic-96, Ic- 103, Ic-109, Ic- 111, Ic- 112, Ic-143, Ic-151, Ic-152.
  • the tubes are populated with 5-10 adult castor bean ticks ⁇ Ixodes ricinus), sealed with a perforated plastic lid and incubated in a horizontal position in the dark at 22°C and 90%) humidity in a climate-controlled cabinet. After 48 h, the efficacy is determined. To this end, the ticks are knocked to the floor of the tube and incubated on a hotplate at 45-50°C for at most 5 min. Ticks which remain motionless on the floor or move in an uncoordinated manner such that they are not able to deliberately avoid the heat by climbing upwards are considered to be dead or moribund.
  • a substance shows good activity against Ixodes ricinus if, in this test, an efficacy of at least 80% was achieved at an application rate of 5 ⁇ g/cm 2 .
  • An efficacy of 100%> means that all ticks were dead or moribund. 0%> efficacy means that none of the ticks had been damaged.
  • the following compounds of the Preparation Examples show an efficacy of 100 at an application rate of 5 ⁇ g/cm 2 : Ia-1, la-2. Ic- 1, Ic-2, Ic-11, Ic-16, Ic-21, Ic-23, Ic-37, Ic-47, Ic- 48, Ic-81, Ic-83, Ic-84, Ic-86, Ic-87, Ic-90, Ic-94
  • the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 5 ⁇ g/cm 2 : ib-3.
  • Ic-18 In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 1 ⁇ g/cm 2 : Ia-1, Ia-2. Ic- 1, Ic-2, Ic-16, Ic-23, Ic-37, Ic-81, Ic-84, Ic-90, Ic- 94
  • the tubes are populated with 5-10 bont tick nymphs (Amblyomma hebraeum), sealed with a perforated plastic lid and incubated in a horizontal position in the dark at 27°C and 85%) humidity in a climate-controlled cabinet. After 48 h, the efficacy is determined. To this end, the ticks are knocked to the floor of the tube and incubated on a hotplate at 45-50°C for at most 5 min. Ticks which remain motionless on the floor or move in an uncoordinated manner such that they are not able to deliberately avoid the heat by climbing upwards are considered to be dead or moribund.
  • a substance shows good activity against Amblyomma hebraeum nymphs if, in this test, an efficacy of at least 80% was achieved at an application rate of 5 ⁇ g/cm 2 .
  • An efficacy of 100%> means that all ticks were dead or moribund. 0%> efficacy means that none of the ticks had been damaged.
  • mice 5 rats per group are used, the results are reported as arithmetic means.
  • all rats Prior to the tick infestations, all rats are provided with collars.
  • the rats are sedated with 30-50 ⁇ of medetomidine hydrochloride (e.g. Domitor®) s.c/rat.
  • All rats are infested on day 0 (at least 1 h after the treatemt), day 7, day 14 etc. with 30 un engorged Dermacentor variabilis nymphs.
  • day 2 day 9, day 16 etc. the collar is removed and the entire body of the sedated rats is examined systematically for ticks. Ticks are removed with tweezers and, by being squashed on blotting paper, examined for blood sucked.
  • the efficacy of the treatment is determined by comparison with a placebo-treated control group.
  • a compound is considered to be highly effective if, at a dosage of 10 mg/kg, it shows an efficacy of 90% against nymphs of the American dog tick (Dermacentor variabilis) on day 2 after intraperitoneal treatment. The effect is considered to be longer-lasting if the efficacy on day 9 is still higher than 80%.
  • the rats are sedated with 30-50 ⁇ of medetomidine hydrochloride (e.g. Domitor®) s.c/rat. All rats are infested on day 0 (at least 1 h after the treatemt), day 7, day 14 etc. with 30 unfed Ctenocephalides felis adults. On day 2, day 9, day 16 etc. the collar is removed and the entire body of the sedated rats is examined systematically for fleas using a flea comb. The fleas are counted and removed.
  • medetomidine hydrochloride e.g. Domitor®
  • the efficacy of the treatment is determined by comparison with a placebo-treated control group.
  • a compound is considered to be highly effective if, at a dosage of 10 mg/kg, it shows an efficacy of 95% against adult fleas ( Ctenocephalides felis) on day 2 after intraperitoneal treatment. The effect is considered to be longer-lasting if the efficacy on day 9 is still higher than 90%.
  • the following compounds of the Preparation Examples show an efficacy of >95% against fleas on day 2 at an application rate of 10 mg/kg: Ic-1, Ic-2
  • the kill in % is determined. 100% means that all of the larvae have been killed; 0% means that none of the larvae have been killed. in this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 20 ppm: Ic-1, Ic-16

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Abstract

La présente invention concerne de nouvelles combinaisons anti-parasitaire de composés à substitution halogène, qui sont utiles pour lutter contre les animaux nuisibles dans le domaine de la santé animale.
PCT/EP2016/059332 2015-04-30 2016-04-27 Combinaisons anti-parasitaires comprenant des composés à substitution halogène Ceased WO2016174049A1 (fr)

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US12502390B2 (en) 2019-08-14 2025-12-23 Vetoquinol Sa Compositions comprising tigolaner for controlling parasites

Citations (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
WO2000007980A1 (fr) 1998-08-04 2000-02-17 Astrazeneca Ab Derives d'amides utiles comme inhibiteurs de cytokine
WO2003076415A1 (fr) 2002-03-12 2003-09-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et utilisation de ceux-ci comme pesticides
WO2003106457A1 (fr) 2002-06-14 2003-12-24 Syngenta Limited Derives de spiroindolinepiperidine
WO2004035545A2 (fr) 2002-10-18 2004-04-29 E.I. Du Pont De Nemours And Company Herbicides a base d'azolecarboxamide
WO2004099160A1 (fr) 2003-05-12 2004-11-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et compostion de lutte contre les animaux nuisibles contenant ces composes
WO2004106324A1 (fr) 2003-05-27 2004-12-09 E.I. Dupont De Nemours And Company Herbicides a base d'azolecarboxamide
WO2005085216A1 (fr) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
US20060069132A1 (en) 2004-04-07 2006-03-30 Armel Gregory R Azolecarboxamide herbicides
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
WO2008029084A1 (fr) 2006-09-06 2008-03-13 Syngenta Limited Composés et compositions herbicides
EP1911751A1 (fr) 2005-06-21 2008-04-16 Mitsui Chemicals, Inc. Derive d'amide et pesticide contenant un tel compose
WO2008134969A1 (fr) 2007-04-30 2008-11-13 Sinochem Corporation Composés benzamides et leurs applications
CN101337940A (zh) 2008-08-12 2009-01-07 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
WO2009049851A1 (fr) 2007-10-15 2009-04-23 Syngenta Participations Ag Dérivés pyrrolidine dione spirohétérocycliques utiles comme pesticides
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2009099929A1 (fr) 2008-02-06 2009-08-13 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2010136145A1 (fr) 2009-05-29 2010-12-02 Bayer Cropscience Ag Pyrazinylpyrazoles
CN102060818A (zh) 2011-01-07 2011-05-18 青岛科技大学 一种新型螺螨酯类化合物及其制法与用途
CN102057925A (zh) 2011-01-21 2011-05-18 陕西上格之路生物科学有限公司 一种含噻虫酰胺和生物源类杀虫剂的杀虫组合物
WO2012000896A2 (fr) 2010-06-28 2012-01-05 Bayer Cropscience Ag Composés hétérocycliques utilisés en tant qu'agents de lutte contre les parasites
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles
WO2012069366A1 (fr) 2010-11-23 2012-05-31 Syngenta Participations Ag Composés insecticides
WO2012080376A1 (fr) 2010-12-17 2012-06-21 Syngenta Participations Ag Composés insecticides
WO2012107434A1 (fr) 2011-02-09 2012-08-16 Syngenta Participations Ag Composés insecticides
US20120329832A1 (en) 2011-06-27 2012-12-27 Jean Delaveau Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
WO2014122083A1 (fr) 2013-02-06 2014-08-14 Bayer Cropscience Ag Dérivés de pyrazole halosubstitués en tant qu'agents phytosanitaires
WO2015193216A1 (fr) * 2014-06-18 2015-12-23 Bayer Cropscience Aktiengesellschaft Pyrazolyl-triazolyl-pyridines en tant qu'agents de lutte contre les nuisibles
WO2016020441A1 (fr) * 2014-08-08 2016-02-11 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2016020436A1 (fr) * 2014-08-08 2016-02-11 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par un halogène
WO2016026789A1 (fr) * 2014-08-19 2016-02-25 Bayer Cropscience Aktiengesellschaft Procédé de préparation de 5-fluoro-1h-pyrazoles à partir d'hexafluoropropène

Patent Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
WO2000007980A1 (fr) 1998-08-04 2000-02-17 Astrazeneca Ab Derives d'amides utiles comme inhibiteurs de cytokine
WO2003076415A1 (fr) 2002-03-12 2003-09-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et utilisation de ceux-ci comme pesticides
WO2003106457A1 (fr) 2002-06-14 2003-12-24 Syngenta Limited Derives de spiroindolinepiperidine
WO2004035545A2 (fr) 2002-10-18 2004-04-29 E.I. Du Pont De Nemours And Company Herbicides a base d'azolecarboxamide
WO2004099160A1 (fr) 2003-05-12 2004-11-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et compostion de lutte contre les animaux nuisibles contenant ces composes
WO2004106324A1 (fr) 2003-05-27 2004-12-09 E.I. Dupont De Nemours And Company Herbicides a base d'azolecarboxamide
WO2005085216A1 (fr) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
US20060069132A1 (en) 2004-04-07 2006-03-30 Armel Gregory R Azolecarboxamide herbicides
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
EP1911751A1 (fr) 2005-06-21 2008-04-16 Mitsui Chemicals, Inc. Derive d'amide et pesticide contenant un tel compose
WO2008029084A1 (fr) 2006-09-06 2008-03-13 Syngenta Limited Composés et compositions herbicides
WO2008134969A1 (fr) 2007-04-30 2008-11-13 Sinochem Corporation Composés benzamides et leurs applications
WO2009049851A1 (fr) 2007-10-15 2009-04-23 Syngenta Participations Ag Dérivés pyrrolidine dione spirohétérocycliques utiles comme pesticides
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2009099929A1 (fr) 2008-02-06 2009-08-13 E. I. Du Pont De Nemours And Company Pesticides mésoioniques
CN101337940A (zh) 2008-08-12 2009-01-07 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
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2010136145A1 (fr) 2009-05-29 2010-12-02 Bayer Cropscience Ag Pyrazinylpyrazoles
US20120190687A1 (en) * 2009-05-29 2012-07-26 Bayer Cropscience Ag Pyrazinylpyrazoles
WO2012000896A2 (fr) 2010-06-28 2012-01-05 Bayer Cropscience Ag Composés hétérocycliques utilisés en tant qu'agents de lutte contre les parasites
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles
WO2012069366A1 (fr) 2010-11-23 2012-05-31 Syngenta Participations Ag Composés insecticides
WO2012080376A1 (fr) 2010-12-17 2012-06-21 Syngenta Participations Ag Composés insecticides
CN102060818A (zh) 2011-01-07 2011-05-18 青岛科技大学 一种新型螺螨酯类化合物及其制法与用途
CN102057925A (zh) 2011-01-21 2011-05-18 陕西上格之路生物科学有限公司 一种含噻虫酰胺和生物源类杀虫剂的杀虫组合物
WO2012107434A1 (fr) 2011-02-09 2012-08-16 Syngenta Participations Ag Composés insecticides
US20120329832A1 (en) 2011-06-27 2012-12-27 Jean Delaveau Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
WO2014122083A1 (fr) 2013-02-06 2014-08-14 Bayer Cropscience Ag Dérivés de pyrazole halosubstitués en tant qu'agents phytosanitaires
WO2015193216A1 (fr) * 2014-06-18 2015-12-23 Bayer Cropscience Aktiengesellschaft Pyrazolyl-triazolyl-pyridines en tant qu'agents de lutte contre les nuisibles
WO2016020441A1 (fr) * 2014-08-08 2016-02-11 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2016020436A1 (fr) * 2014-08-08 2016-02-11 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par un halogène
WO2016026789A1 (fr) * 2014-08-19 2016-02-25 Bayer Cropscience Aktiengesellschaft Procédé de préparation de 5-fluoro-1h-pyrazoles à partir d'hexafluoropropène

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"The Pesticide Manual, 14th ed.,", 2006, BRITISH CROP PROTECTION COUNCIL
J. HETEROCYCL. CHEM., vol. 35, no. 6, 1998, pages 1493 - 1499
J. ORG. CHEM., vol. 62, no. 17, 1997, pages 5908 - 5919

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