EP3157905A1 - Composés substitués par un halogène - Google Patents

Composés substitués par un halogène

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Publication number
EP3157905A1
EP3157905A1 EP15728550.3A EP15728550A EP3157905A1 EP 3157905 A1 EP3157905 A1 EP 3157905A1 EP 15728550 A EP15728550 A EP 15728550A EP 3157905 A1 EP3157905 A1 EP 3157905A1
Authority
EP
European Patent Office
Prior art keywords
spp
alkyl
formula
methyl
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP15728550.3A
Other languages
German (de)
English (en)
Inventor
Michael Maue
Anne Decor
Julia Johanna Hahn
Werner Hallenbach
Reiner Fischer
Hans-Georg Schwarz
Ulrich Görgens
Kerstin Ilg
Klaus Raming
Johannes KÖBBERLING
Walter Hübsch
Andreas Turberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Animal Health GmbH
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Bayer Animal Health GmbH
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Filing date
Publication date
Application filed by Bayer Animal Health GmbH filed Critical Bayer Animal Health GmbH
Publication of EP3157905A1 publication Critical patent/EP3157905A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • A01N43/48—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
    • A01N43/64—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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • 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

Definitions

  • the present application relates to novel halogen-substituted compounds, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes. It is known that certain halogen-substituted compounds have B-Raf-inhibitory activities for the treatment of cancer (WO 2009/003999). Furthermore, for certain halogen-substituted compounds, inhibition of cytokines (WO 2005/090333) and protein tyrosine phosphatases (US 2004/0167188) are described.
  • the object of the present invention was to provide compounds by which the spectrum of pesticides widened under various aspects and / or their activity is improved.
  • One aspect of the present invention relates to a compound of the general formula (I)
  • R 1 represents hydrogen, or an optionally substituted with at least one radical M 1 group selected from (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C2-C6) -alkynyl, (C3-C7 ) - cycloalkyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, aryl (C 1 -C 3) -alkyl, and heteroaryl (C 1 -C 3) -alkyl; the chemical groups
  • a 3 is CR 4 or nitrogen
  • A4 represents CR 5 or nitrogen; wherein not more than three of the chemical groups Ai to A 4 are simultaneously nitrogen;
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, amino, nitro or a group optionally substituted by at least one radical M 1 selected from (C 1 -C 6 ) -alkyl, (C 3 - C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, N- (C 1 -C 6 ) -alkoxy-immo- (C 1 -C 3 ) -alkyl, (C 1 -C 6 ) -alkylsulfanyl, (C 1 -C 4 ) -cycloalkyl; 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, N- (C 1 -C 6 ) -alkylamino and N, N- (di- (C 1 -C 6 ) -alkylamino, when none of the groups A
  • W is oxygen or sulfur
  • Q is hydrogen, hydroxy, or an optionally substituted by at least one radical M 1 selected from amino, N- (Ci-C6) alkylamino, N- (Ci-Cö) - alkylcarbonylamino, NN-di- (Ci-C 6 ) alkylamino, (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C 2 - C 6) alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) - Cycloalkyl, heterocycloalkyl of 3 to 9 Ring atoms, (C 1 -C 6 ) cycloalkyl- (C 1 -C 6 ) alkyl, (C 6 ) aryl- (C 1 -C 6 ) alkyl, heteroaryl (C 1 -C 4) alkyl having 5 to 7 ring atoms; or
  • Q represents an optionally monosubstituted to poly-substituted unsaturated 6-membered carbocycle, or is an optionally mono- to polysubstituted by V, unsaturated 5- or 6-membered heterocyclic ring;
  • V independently represents halogen, cyano, amino, nitro or optionally substituted with at least one radical M 1 group selected from (Ci-C6) alkyl, (C2-C4) alkenyl, (C 2 -C 4) alkynyl , (C 3 -C 6) cycloalkyl, (Ci-C 6) -alkoxy, N- (Ci-C 6) alkoxy imino (Ci-C 3) alkyl, (Ci-C 6) alkylsulphanyl (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl, N- (C 1 -C 6 ) -alkylamino, and N, N-di- (C 1 -C 6 ) -alkyl) amino;
  • T is one of the 5-membered heteroaromatics T1-T8 listed below, the bond to the pyrazole head group [C3N2Z1Z2Z3] being indicated by an asterisk *,
  • Z 2 is hydrogen, halogen, cyano, nitro, or a group optionally substituted by at least one radical M 1 selected from (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, (C 1 -C 6 ) -alkylsulfanyl, ( C 1 -C 6 ) -alkylsulfmyl, and (C 1 -C 6 ) -alkylsulfonyl;
  • Z 3 is hydrogen or an optionally substituted with at least one radical M 1
  • M 1 represents halogen, cyano, isocyano, azido, hydroxy, nitro, formyl, carboxy or a carboxy group equivalent group, or a group optionally substituted by at least one radical M 2 selected from amino, (Ci-C4) alkyl, (C1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkoxy C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfanyl, (C 1 -C 4 ) -haloalkylsulfanyl (C 1 -C 4 )
  • M 2 is amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy and carbonamide.
  • a preferred embodiment relates to compounds of the formula (I) in which Z 1 and Z 2 independently of one another are perhalogenated (C 1 -C 4 ) -alkyl and Z 3 is (C 1 -C 4 ) -alkyl and the other parameters as defined above.
  • Another preferred embodiment relates to compounds of formula (I) wherein Z 1 is perfluorinated ethyl (C 2 F 5), Z 2 is perfluorinated methyl (CF 3) and Z 3 is methyl and the other parameters are as defined above ,
  • a further preferred embodiment relates to compounds of the formula (I) in which T is Tl (formula (Ic)), T6 (formula (If), T7 (formula (Ig)) or T8 (formula (Ih)) stands and the other parameters are as defined above.
  • a further preferred embodiment relates to compounds of formula (I) wherein T is T3 (formula (Ic)), T6 (formula (If), T7 (formula (Ig)) or T8 (formula (Ih)) stands and the other parameters are as defined above.
  • a further preferred embodiment relates to compounds of formula (I) wherein Q is hydrogen, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -alkoxy or benzyl stands and the other parameters are as defined above.
  • a further preferred embodiment relates to compounds of formula (I) wherein n in a structure Tl to T8 has the value 0 and the remaining parameters are as defined above.
  • Another preferred embodiment relates to compounds of formula (I) wherein
  • T is T3 (formula (Ic)), T6 (formula (If), T7 (formula (Ig)) or T8 (formula (Ih)) and n is 0 in T;
  • Ai is CP2 wherein R2 is hydrogen
  • A2 is CR3 wherein R3 is hydrogen
  • a 3 is CR 4 where R 4 is hydrogen, halogen, (C 1 -C 4) -alkyl or (C 1 -C 4) -alkoxyl, preferably halogen, selected from chlorine, fluorine, bromine or iodine;
  • A4 is CR5 wherein R5 is hydrogen
  • W is oxygen; n is 0 in T;
  • Z 1 is halogenated (C 1 -C 4) -alkyl
  • Z 2 is halogenated (C 1 -C 4) -alkyl
  • Z 3 is (C 1 -C 4 ) -alkyl
  • Ri is hydrogen or (Ci-C4) -alkyl; preferred for hydrogen;
  • Q is hydrogen or optionally substituted by at least one radical M 1
  • T is T3 (formula (Ic)), T6 (formula (If), T7 (formula (Ig)) or T8 (formula (Ih)) and n is 0 in T;
  • Ai is CR2 wherein R2 is hydrogen;
  • A2 is CR3, wherein R3 is hydrogen;
  • A3 is CR4, wherein R is chloro
  • A4 is CR5, wherein R5 is hydrogen
  • W is oxygen; n is 0 in T; Z 1 is perfluorinated ethyl;
  • Z 2 is perfluorinated methyl
  • Z 3 is methyl
  • Ri is hydrogen or (Ci-C4) -alkyl; preferred for hydrogen;
  • Q is (C3-C6) -cycloalkyl, preferably cyclopropyl.
  • Another aspect of the present invention relates to the use of a compound of formula (I) as defined in this application for controlling insects, arachnids and nematodes.
  • Another aspect of the present invention relates to a pharmaceutical composition containing at least one compound of formula (I) as defined in this application.
  • Another aspect of the present invention relates to a compound of formula (I) as defined in this application for use as a medicament.
  • Another aspect of the present invention relates to a use of a compound of formula (I) as defined in this application for the preparation of pharmaceutical compositions for controlling parasites on animals.
  • Another aspect of the present invention relates to a process for the preparation of pesticides comprising a compound of the formula (I) as defined in this application, as well as conventional extenders and / or surface-active substances.
  • Another aspect of the present invention relates to the use of a compound of the formula (I) as defined in this application for the protection of the propagation material of plants, preferably for the protection of seed.
  • alkyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbon hydrocarbons, preferably having 1 to 6 carbon atoms particularly preferably having 1, 2, 3 or 4 carbon atoms, such as methyl, ethyl, n- Propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl
  • the alkyls according to the invention can be optionally substituted by one or more, identical or different radicals M 1 .
  • alkenyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbon hydrocarbons, preferably having 2 to 6 carbon atoms particularly preferably having 2, 3 or 4 carbon atoms, and at least one double bond, such as vinyl, second Propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, etc.
  • the alkenyls of the invention may be substituted by one or more the same or different radicals M 1 may be optionally substituted.
  • alkynyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbon hydrocarbons, preferably with 2 to 6 Carbon atoms particularly preferably having 2, 3 or 4 carbon atoms, and at least one triple bond such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl , 1-methyl-3-butynyl, etc.
  • the alkynyls according to the invention may optionally be substituted by one or more, identical or different radicals M 1 .
  • cycloalkyl alone or as part of a chemical group - for mono-, bi- or tricyclic hydrocarbons, preferably having 3 to 10 carbons such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl or adamantyl, particularly preferred for cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms, such as. As cyclopropyl or cyclobutyl.
  • the cycloalkyls of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • alkylcycloalkyl is mono-, bi- or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, especially b crizt for alkylcycloalkyls having 4, 5 or 7 carbon atoms such as.
  • alkylcycloalkyl is connected via the cycloalkyl with the basic structure.
  • the Alkylcycloalkyle invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • cycloalkylalkyl is mono-, bi- or tricyclic cycloalkylalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, particularly preferably for Cycloalkylalkyle with 4, 5 or 7 carbon atoms such as cyclopropylmethyl or cyclobutylmethyl, wherein the alkylcycloalkyl on the alkyl with the basic structure is connected.
  • the Cycloalkylalkyle invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • alkoxy represents straight-chain or branched O-alkyl, preferably having 1 to 6 carbon atoms, more preferably alkoxy groups having 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy or t-butoxy.
  • the alkoxy groups of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • alkylsulfanyl is straight-chain or branched S-alkyl, preferably having 1 to 6 carbon atoms, more preferably for alkylsulfanyl groups having 1 to 4 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio , s-butylthio and t-butylthio.
  • the alkylsulfanyl groups according to the invention may optionally be substituted by one or more, identical or different radicals M 1 . - -
  • alkylsulfinyl means straight-chain or branched alkylsulfinyl preferably having 1 to 6 carbon atoms, more preferably alkylsulfinyl groups having 1 to 4 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfmyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s Butylsulfinyl and t-butylsulfinyl.
  • the alkylsulfinyl groups of the present invention may be optionally substituted with one or more, identical or different radicals M 1 .
  • alkylsulfonyl means straight-chain or branched alkylsulfonyl, preferably having 1 to 6 carbon atoms, more preferably alkylsulfonyl groups having 1 to 4 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s Butylsulfonyl and t-butylsulfonyl.
  • the alkylsulfonyl groups according to the invention may optionally be substituted by one or more, identical or different radicals M 1 .
  • X 1 and X 2 each independently represent an optionally the same with one or more.
  • radicals M 1 represents a substituted group selected from alkyl, alkylene (-CnF n-), alkoxy, alkoxylene (-O-CnF n-), amino, mono- or di-alkylamino or hydrogen or a radical X 1 or X 2 a bond to the basic structure of a compound of formula (I).
  • the Alkylcarbonyle invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • cycloalkylcarbonyl represents straight-chain or branched cycloalkylcarbonyl, preferably having 3 to 10 carbon atoms in the cycloalkyl moiety, more preferably cycloalkylcarbonyl having 3, 5 or 7 carbon atoms in the cycloalkyl moiety such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptyl carbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptyl, bycyclo [2.2.2] octylcarbonyl and adamantylcarbonyl.
  • the cycloalkylcarbonyl invention may be substituted by one or more identical or different radicals M 1 if necessary. - -
  • alkoxycarbonyl alone or as part of a chemical group - is straight-chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms, more preferably having 1, 2, 3 or 4 carbon atoms in the alkoxy, such as methoxycarbonyl, ethoxycarbonyl , n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl.
  • the alkoxycarbonyl groups of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • halogen is fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • haloalkyl refers to at least one Halogen-substituted alkyl, alkenyl, alkynyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfinyl or alkylsulfonyl (each preferably having from one to six carbon atoms, more preferably one, two, three or four carbon atoms)
  • the halogen atoms may be the same or different and may all be bonded to one or more carbon atoms, in which case halogen is in particular fluorine,
  • haloalkyl Perfluorinated methyl (trifluoromethyl; CF3) or perfluorinated ethyl (pentafluoroethyl; C2F5).
  • Haloalkylsulfonyl are trichloromethyl (CCI3), trifluoromethyl (CF3), chlorodifluoromethyl (CCIF2), dichlorofluoromethyl (CCHF), 2,2-difluoroethyl (F 2 HCCH 2), 2,2,2-trifluoroethyl (F3CCH2), pentafluoroethyl (C2F5 ), 2,2-difluoroethenyl (CHCF 2 ), 2-chloroethynyl (CHCCl), trifluoromethoxy-OCF 3 , difluoromethoxy-OCHF 2, 1, 1, 2,2-tetrafluoroethylthio, 2-chloro-1, 2-trifluoroethylsulfinyl, Trichloromethylsulfonyl, etc.
  • halo groups of the present invention may be optionally substituted with one or more identical or different radicals M 1 as long as at least one hydrogen atom on a carbon atom of the halogeno group is replaced by a halogen
  • M 1 substituted haloalkyl 2-cyano-2,2-difluoroethyl (C (CN) F 2 CH 2 ).
  • An amino group (-NH 2 ) may optionally be substituted by one or more, identical or different radicals M 1 .
  • Substituted amino such as mono- or disubstituted amino is a radical from the group of substituted amino radicals, which, for example, by one or two identical or various radicals are selected from the group consisting of alkyl, hydroxy, amino, alkoxy, acyl and aryl N-substituted; preferably N-mono- and N, N-dialkylamino, (eg methylamino, ethylamino, N, N-dimethylamino, N, N-diethylamino, N, N-propylamino, N, N-diisopropylamino or N, N-dibutylamino), N-mono- or N, N-dialkoxyalkylamino groups ( for example, N-methoxymethylamino, N-methoxyethylamino, N, N'-di (methoxymethyl) amino or N, N'-di (methoxyethyl) amino), N
  • hydroxyalkyl is straight-chain or branched alcohol, preferably having 1 to 6 carbon atoms, more preferably having 1, 2, 3 or 4 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol , s-butanol and t-butanol.
  • the hydroxyalkyl groups according to the invention may be substituted by one or more, identical or different radicals M 1
  • alkylaminocarbonyl means straight-chain or branched alkylaminocarbonyl having preferably 1 to 6 carbon atoms, more preferably 1, 2, 3 or 4 carbon atoms in the alkyl portion such as methylaminocarbony (-CONHCH3), ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s Butylaminocarbonyl and t-butylaminocarbonyl.
  • the alkylaminocarbonyl groups according to the invention may optionally be substituted by one or more, identical or different radicals M 1 .
  • the NN- dialkylamino carbonyl groups of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • a carbocycle is a Ce to C14 monobi or tricyclic aryl.
  • a carbocycle may be optionally substituted with one or more, identical or different radicals M 1 . - -
  • aryl is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl. Furthermore, aryl also represents polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, where the binding site is on the aromatic system.
  • the aryl groups of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • arylalkyl is an aryl-substituted alkyl radical having preferably 6 to 14, in particular 6 to 10, ring carbon atoms in the aryl part and 1 to 6, in particular 1 to 4, carbon atoms in the alkyl part. be substituted identical or different substituents in the alkyl and / or aryl moiety.
  • arylalkyl include benzyl and 1 phenylethyl.
  • the arylalkyl 'groups of the invention may be substituted by one or more identical or different radicals M 1 if necessary.
  • heterocycle for 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 N, O, S. , P, B, Si, Se and which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted by a substituent Z, wherein the binding site is located on a ring atom.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 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 N, O, and S, but not 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 sulfur atoms.
  • the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • the invention also includes polycyclic systems, for example 8-azabicyclo [3.2.1] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • the invention also includes spirocyclic systems, for example 1-oxa-5-aza-spiro [2.3] hexyl.
  • the groups "heterocycle”, “heterocyclic ring” or “heterocyclic ring system” according to the invention may optionally be substituted by one or more, identical or different radicals M 1 .
  • 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, - -
  • heteroarylene ie heteroaromatic systems.
  • heteroaryl means heteroaromatic compounds, that is, fully unsaturated aromatic heterocyclic compounds falling within the above definition of heterocycles.
  • heteroaryls are 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 of the invention may further be substituted with one or more identical or different radicals M 1 if necessary.
  • Substituted group or "at least one radical M 1 substituted” group in the context of the present invention is generally a group containing at least one hydrocarbon or nitrogen-containing moiety in which the hydrogen is replaced by another atom or atomic group M 1 .
  • such a group is a substituted group derived from the unsubstituted skeleton, wherein the skeleton is substituted with one or more substituent (s) M 1 , preferably 1, 2 or 3 residues M 1 , and the substituent M 1 respectively independently of one another selected from the group consisting of halogen, hydroxyl, nitro, formyl, carboxy, cyano, amino, isocyano, azido, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 5) alkenyl, (C2-C4) -alkynyl, (C 3 -C 6) cycloalkyl (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkoxy- (C -C 4) alkoxy, (Ci-C4) - alkoxy- (Ci-C 6) alkyl,
  • radicals M 1 may be unsubstituted or optionally (such as alkyl or amino), if they contain hydrocarbon or nitrogen-containing fractions, be substituted with one or more, preferably 1, 2 or 3 radicals M 2 , wherein M 2 independently is selected from the group consisting of amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy and carbonamide.
  • radicals form one or more rings, these may be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated, for example also aromatic and further substituted.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably mono-, di- or trisubstituted by identical or different radicals selected from the group halogen, cyano, isocyano, nitro, optionally substituted by at least one radical M 2 ( Ci-C 4) alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, (Ci-C 4) alkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (Ci- C 4) alkoxy (Ci-C 4) alkyl, (C 3 -C 6) -cycloalkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, (Ci-C4) alkylsulfanyl, (Ci C 4 ) haloalkylsulfanyl, for example o-
  • Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group halogen, Haloaklyl, cyano, (Ci-C 4) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, and (Ci-C 4) haloalkoxy is substituted.
  • Optionally substituted heterocyclyl is preferably heterocyclyl is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals from the group halogen, cyano, (Ci-C 4) alkyl, (Ci-C 4) alkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro and Oxo is substituted, in particular one or more times by radicals from the group halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkyl and oxo, very particularly by one or two (Ci -C 4 ) alkyl radicals is substituted.
  • alkyl-substituted heteroaryls 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.
  • halogen-substituted compounds of the invention are represented by the general formula (I)
  • R 1 represents hydrogen, or an optionally substituted with at least one radical M 1 group selected from (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C2-C6) -alkynyl, (C3-C7 ) - cycloalkyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 6) -alkoxycarbonyl, aryl (C 1 -C 3) -alkyl, and heteroaryl (C 1 -C 3) -alkyl; the chemical groups
  • a 3 is CR 4 or nitrogen
  • A4 represents CR 5 or nitrogen; wherein not more than three of the chemical groups Ai to A 4 are simultaneously nitrogen;
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, amino, nitro or a group optionally substituted by at least one radical M 1 selected from (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 ) -alkylsulfanyl, (C 1 -C 6 ) -Alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, N- (C 1 -C 6 ) -alkylamino and N, Ni- (C 1 -C 6 ) -alkylamino, when none of the moieties A 2 and A3 is nitrogen, R 3 and R 4
  • W is oxygen or sulfur
  • Q is hydrogen, hydroxy, or an optionally substituted by at least one radical M 1 selected from amino, N- (Ci-C6) alkylamino, N- (Ci-Cö) - alkylcarbonylamino, NN-di- (Ci-C 6 ) alkylamino, (Ci-C 6) -alkyl, (Ci-C 6) alkoxy, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C3-C6) cycloalkyl, heterocycloalkyl with 3 to 9 ring atoms, (C 1 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 6 ) -aryl (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl with 5 to 7 ring atoms; or
  • Q is an optionally mono- to polysubstituted with V, unsaturated 6-membered carbocycle, or represents an optionally mono- to polysubstituted with V, unsaturated 5- or 6-membered heterocyclic ring, wherein
  • V independently of one another are halogen, cyano, amino, nitro or a group optionally substituted by at least one radical M 1 selected from (C 1 -C 6 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 3 -C 6) -cycloalkyl, (Ci-C 6) -alkoxy, N- (Ci-C 6) alkoxy-real (Ci-C 3) alkyl, (Ci-C6) alkylsulfanyl, (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, N- (C 1 -C 6 ) -alkylamino, and N, N- (di- (C 1 -C 6 ) -alkyl) amino;
  • T is one of the 5-membered heteroaromatics T1-T8 listed below, the bond to the pyrazole head group [C3N2Z1Z2Z3] being indicated by an asterisk *,
  • R 6 is independently of one another halogen, cyano, nitro, or a group optionally substituted by at least one radical M 1 selected from amino, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) - Alkylcarbonyl, (C 1 -C 6 ) -alkylsulfanyl, (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl, N- (C 1 -C 6 ) -alkylamino, and N, N-di- (C 1 -C 6 ) -alkyl ) -alkyl) amino; n is 0, 1 or 2;
  • Z 1 an optionally at least one radical M 1 substituted group selected from (Ci-C6) alkyl, (Ci-C i) alkoxy, cyano, hydroxycarbonyl, (Ci-C i) alkoxycarbonyl, (Ci- C4) - Alkylcarbamoyl, (C 3 -C 6) -cycloalkylcarbamoyl, phenyl-substituted (C 1 -C 4) -haloalkyl, preferably a (C 1 -C 6) -alkyl optionally substituted by at least one radical M 1 ;
  • Z 2 represents hydrogen, halogen, cyano, nitro, or a group optionally substituted by at least one radical M 1 selected from (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylcarbonyl, (C 1 -C 6) -alkylsulfanyl, (Ci -C 6) alkylsulfmyl, and (C 1 -C 6) alkylsulfonyl; u
  • Z 3 is hydrogen or a group optionally substituted by at least one radical M 1 selected from (C 1 -C 6) -alkyl, C 1 -C 6 -cycloalkyl, (C 1 -C 6) -alkenyl, (C 1 -C 6) -alkynyl, (C 6) -Aryl and hetaryl having 5 or 6 ring atoms;
  • M 1 is halogen, cyano, isocyano, azido, hydroxy, nitro, formyl, carboxy or a carboxy group equivalent group, or a group optionally substituted by at least one radical M 2 selected from amino, (Ci-C4) alkyl, (Ci -C 4) haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) haloalkoxy, (Ci-C 4) alkoxy (Ci-C 4) alkoxy, (Ci-C 4) -alkoxy - (Ci-C 4) alkyl, (Ci-C4) alkylsulfanyl, (Ci-C 4) -Halogenalkylsulfanyl (C1-C4) - alkoxycarbonyl, (Ci-C4) alkylcarbonyl, carbamoyl, mono- and NN- Di (C 1 -C 4) -alkylaminocarbonyl, (C 1
  • M 2 is amino, hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy and carbonamide.
  • R 1 is hydrogen, C 1 -C 6 -alkyl optionally substituted by at least one radical M 1 , C 1 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 6 is alkoxycarbonyl, aryl (C 1 -C 3) alkyl, heteroaryl (C 1 -C 3) alkyl;
  • W is oxygen
  • Q is hydrogen, formyl, hydroxy or one of the optionally substituted with at least one radical M 1 groupings amino, Ci-Cö-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C2-C7-heterocycloalkyl , C 1 -C -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, aryl- (C 1 -C 3 ) -alkyl, heteroaryl- (C 1 -C 3 ) -alkyl, N- (C 1 -C 4 ) -Alkylamino, N- (C 1 -C 4 ) -alkylcarbonylamino, N, N- (di- (C 1 -C 4 ) -alkylamino; or
  • Q is an optionally mono- to polysubstituted with V, unsaturated 6-membered carbocycle, or represents an optionally mono- to polysubstituted with V, unsaturated 5- or 6-membered heterocyclic ring, wherein
  • T is one of the 5-membered heteroaromatics T1-T8 as defined in paragraph [0058], wherein
  • R 6 in T 1 -T 8 in formula (I) independently of one another represent halogen, cyano, nitro, an amino optionally substituted by at least one radical M 1 or a group consisting of (C 1 -C 6) -alkyl substituted by at least one halogen in each case Ci-Ce) - alkoxy, (Ci-C 6) alkylcarbonyl, (Ci-C6) alkylsulfanyl, (Ci-C 6) -Alkylsulfmyl, (Ci-C 6) - alkylsulfonyl wherein the j stays awhile with at least one Halogen-substituted group may optionally be substituted by at least one radical M 1 ; n in T1 -T8 stands for the values 0 or 1;
  • Z 1 represents a (Ci-C6) -haloalkyl optionally substituted by at least one radical M 1 ;
  • Z 2 represents hydrogen, halogen, cyano, nitro, or an optionally substituted with at least one radical M 1 amino, (Ci-C6) alkyl, (Ci-C6) alkylcarbonyl, (Ci-C6) alkylsulfanyl, (Ci-C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl,
  • Z 3 is hydrogen or an optionally with at least one radical M 1 is substituted (Ci- C6) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) Alkynyl, aryl or hetaryl; and all other parameters (such as Ai to A4 but not more than three of the chemical moieties Ai to A4 are nitrogen at the same time) are defined as in paragraph [0058].
  • Another preferred embodiment relates to compounds of formula (I) wherein - -
  • R 1 is hydrogen, optionally one to seven times independently of one another with fluorine, chlorine, cyano, (C 1 -C 6) -alkoxy and (C 1 -C 6) -alkoxycarbonyl-substituted (C 1 -C 6) -alkyl, (C 3 -C 6) -alkenyl , (C 3 -C 6) -alkynyl, (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylcarbonyl, (Ci-C 6) alkoxycarbonyl, aryl (Ci-C 3) alkyl, heteroaryl (C 1 -C 3 ) alkyl;
  • R 2 , R 3 , R 4 and R 5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, or optionally monosubstituted to pentavalent independently from each other by hydroxy, amino, nitro, fluoro,
  • Q is hydrogen, amino or one of optionally independently of one another one to five times with hydroxyl, nitro, amino, fluorine, chlorine, (Ci-C6) alkyl, (Ci-C6) alkoxy, cyano, hydroxycarbonyl, (C C i) -alkoxycarbonyl, (C 1 -C 4) -alkylcarbamoyl, (C 3 -C 4) -cycloalkylcarbamoyl, optionally substituted by at least one phenyl which may in turn optionally be substituted by at least one M 2 , 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 ) -heterocycloalkyl, (C 1 -C 4 ) -alkoxy
  • Q represents a 6-membered aryl substituted by 0-4 substituent V, or a 5- or 6-membered heteroaromatic radical substituted by 0-4 substituent V, where
  • V independently represents halogen, cyano, nitro, optionally with mine least one radical M 1 is substituted (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -
  • V independently represents halogen, cyano, nitro, optionally with mine least one radical M 1 is substituted (Ci-C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -alkynyl, (C 3 -C 6) cycloalkyl, (C1-C4) - alkoxy, N- (Ci-C 4) -alkoxy-imino (Ci-C 3) alkyl, (C1-C4) - alkylsulfanyl, (Ci-C 4 ) -Alkylsulfmyl,
  • T is one of the listed 5-membered heteroaromatics T1-T8 as defined in paragraph [0058]; - - in which
  • R 6 in T1-T8 are each independently fluorine, chlorine, bromine, iodine, cyano, nitro, amino, or an optionally substituted independently one to five times by fluorine and / or chlorine-substituted (Ci-C 6) alkyl, (Ci- C 6 ) alkoxy, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) alkylsulfanyl, (C 1 -C 6 ) -alkylsulfmyl, (C 1 -C 6 ) -alkylsulfonyl; n in T1-T8 stands for the values 0 or 1;
  • Z 1 represents a (Ci-C6) -haloalkyl optionally substituted by at least one radical M 1 ;
  • Z 2 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, or an optionally substituted independently one to five times by fluorine and / or chlorine-substituted (Ci-C6) alkyl, (Ci-C 6) alkylcarbonyl , (C 1 -C 6 ) -alkylsulfanyl, (C 1 -C 6 ) -alkylsulfinyl, (C 1 -C 6 ) -alkylsulfonyl;
  • Z 3 is hydrogen or an optionally substituted (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl (C 3 -C 4 ) -alkenyl, (C 3 -C 4 ) -alkynyl, 6-membered aryl and 5 or 6-membered hetaryl ; all other parameters (such as Ai to A4 but not more than three of the chemical moieties Ai to A4 are simultaneously nitrogen) are defined as in paragraph [0058].
  • Another preferred embodiment relates to compounds of formula (I) wherein
  • R 1 represents hydrogen, optionally mono- or pentasubstituted independently by fluorine, chlorine, cyano, Ci-C4-alkoxy and Ci-C4-alkoxycarbonyl-substituted (Ci-C 4) -alkyl, (C 2 - C 4) - alkenyl, (C 2 -C 4) -alkynyl, (C 3 -C 6) cycloalkyl, (Ci-C 4) alkylcarbonyl, (C1-C4) - alkoxycarbonyl, aryl (Ci-C 2) alkyl, heteroaryl (C 1 -C 2 ) -alkyl;
  • R 2 , R 3 , R 4 and R 5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, optionally independently of one another one to five times with hydroxy, nitro, amino, fluorine, chlorine, ( C 4 ) alkoxy, cyano, hydroxycarbonyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl or phenyl-substituted (C 1 -C 4 ) -alkyl, C 3 -C 6 -cycloalkyl, (C 1 -C 4 ) -Alkoxy, N- (C 1 -C 4 ) -alkoxy-imino-C 1 -C 2 -alkyl, (C 1 -C 4 ) -alkylsulfanyl, (C 1 -C 4 ) -
  • Q is hydrogen, amino or one of optionally independently of one another one to five times with hydroxyl, nitro, amino, halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, cyano, hydroxycarbonyl. (C 1 -C 4) -alkoxycarbonyl, (C 1 -C 4) -alkylcarbamoyl, (C 3 -C 6) -
  • Cycloalkylcarbamoyl, phenyl-substituted moieties (C 1 -C 4) -alkyl, (C 2 -Ce) - - - -
  • Q is an aryl substituted by 0, 1, 2, 3 or 4 substituents V, or a 5 or 6-membered heteroaromatic radical substituted by 0, 1, 2, 3 or 4 substituents V, where
  • V independently of one another for fluorine, chlorine, bromine, iodine, cyano, nitro, optionally independently of one another one to five times with hydroxy, nitro, amino, fluorine, chlorine, bromine, iodine, (Ci-C 4 ) alkyl, (Ci -C 4 ) alkoxy, cyano, hydroxycarbonyl.
  • R 6 in T1-T8 independently of one another represent fluorine, chlorine, cyano, nitro, amino or a (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl which is optionally mono- to trisubstituted by fluorine and / or chlorine -C 6) alkylcarbonyl, (Ci-C6) alkylsulfanyl, (Ci-C 6) -Alkylsulfmyl, (Ci- C6) alkylsulfonyl group; n in T1-T8 stands for the values 0 or 1;
  • Z 1 represents an optionally independently of one another once or twice with (Ci-C 4 ) -alkoxy, cyano, hydroxycarbonyl.
  • Z 2 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino or an optionally independently of one another one to three times with hydroxy, nitro, amino, fluorine, chlorine, (C 1 -C 4) -alkoxy, cyano, hydroxycarbonyl , (C 1 -C 4 ) -alkoxycarbonyl, C 1 -C 4 -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl, phenyl-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylsulfanyl , (C 1 -C 4 ) -alkylsulfinyl, (C 1 -C 4 ) -alkylsulfonyl,
  • Z 3 is hydrogen or an optionally independently of one another one to three times with hydroxy, nitro, amino, (Ci-C4) alkoxy, cyano, fluorine, chlorine, hydroxycarbonyl. (C1-C4) -alkoxycarbonyl, (C 1 -C 4 ) -alkylcarbamoyl, C 3 -C 6 -cycloalkylcarbamoyl, phenyl-substituted (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4 ) Alkenyl, (C 2 -C 4 ) alkynyl, phenyl and hetaryl; and all other parameters (such as Ai to A4 but not more than three of the chemical groups Ai to A4 are nitrogen at the same time) are defined as in paragraph [0058].
  • R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n Butylcarbonyl, i-butylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,
  • a 3 is CR 4 or nitrogen
  • A4 is CR 5 or nitrogen, but not more than three of the chemical groups Ai to A4 are simultaneously nitrogen;
  • R 2 and R 5 are independently hydrogen, methyl, fluoro and chloro
  • R 3 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, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1 - (N-methoxyimino) - ethyl, methylsulfanyl, trifluoromethylsulfanyl, methylsulfonyl, methylsulfinyl, trifluoromethylsulf
  • W is oxygen or sulfur
  • Q is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1, 1-dimethylethyl, 1-methylpropyl, n-butyl, 2-methylpropyl, 2-methylbutyl, 2-hydroxyethyl, 2-hydroxypropyl, 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-methyl-cyclopropyl, 1-cyano-cyclopropyl, 1-methoxycarbonyl-cyclopropyl, 1- (N-methylcarbamoyl) -cyclopropyl, 1-carbamoyl-cyclopropyl, 1-carbamothioyl-cyclopropyl, 1- (N-cyclopropylcarbamoyl) -cyclopropyl, Cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, bis (cyclopropyl) methyl, 2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluor
  • R 6 in T1-T8 independently of one another are fluorine, chlorine, 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, methylsulfanyl, methylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, and n in T1-T8 are 0 or 1;
  • Z 1 is 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, Heptafluoro-isopropyl, nonafluoro-n-butyl and
  • Z 2 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, methyl, ethyl, 1,1-t-butyl, 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, heptafluoro
  • Z 3 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, 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.
  • Z 1 is trifluoromethyl or pentafluoroethyl
  • Z 2 is trifluoromethyl, nitro, methylsulfanyl, methylsulfinyl, methylsulfonyl, fluoro, chloro, bromo, cyano or iodo;
  • Z is methyl, ethyl, n-propyl or hydrogen
  • R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n Butylcarbonyl, i-butylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-
  • Ai and A4 are CH;
  • a 2 is CR 3 or N;
  • a 3 is CR 4 ;
  • R 3 and R 4 are fluorine, chlorine, bromine, iodine, methyl, ethyl, methylsulfanyl, methylsulfmyl or methylsulfonyl;
  • T is one of the 5-membered heteroaromatics T1-T8 as defined above; wherein R 6 in T1-T8 is hydrogen, methyl, ethyl, 2-methylethyl, 2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, amino; n in T1 -T8 stands for the values 0 or 1; preferably represents 0;
  • W is oxygen
  • Q is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1, 1-dimethylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxyethyl, 2-hydroxypropyl, cyanomethyl,
  • Q is phenyl, naphthyl, pyridazine, pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene, pyrrole, oxadiazole, substituted by 0, 1, 2 or 3 substituents V, Thiadiazole stands; in which
  • V independently of one another are 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-propyl, heptafluoro-isopropyl, nonafluoro-n-butyl, cyclopropyl, cyclo
  • a preferred embodiment relates to compounds of the formulas (Ic), (If), (Ig) and (Ih), in other words to compounds of the formula (I) in which T is T 3 (formula (Ic)), is T6 (formula (If), T7 (formula (Ig)) or T8 (formula (Ih)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T 1 (formula (Ia)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T2 (formula (Ib)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T3 (formula (Ic)).
  • a further preferred embodiment relates to compound of formula (I) wherein T is T4 (formula (Id)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T5 (formula (Ie)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T6 (formula (If)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T7 (formula (Ig)).
  • Another preferred embodiment relates to the compound of formula (I) wherein T is T8 (formula (Ih)).
  • a further preferred embodiment relates to compounds of formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), wherein Ai is CR 2 , A 2 is CR 3 , A 3 is CR 4 , and A4 is CR 5 , wherein R 2 , R 3 , R 4 and R 5 are independently hydrogen, halogen, cyano, nitro, or optionally substituted (Ci-C6) 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 ) -alkylsulfanyl, (C 1 -C 6 ) - Alkylsulfmyl, (Ci-C 6 ) -alkylsulfonyl, N- (Ci-C 6 ) -al
  • a further preferred embodiment relates to compounds of the formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), wherein Z 1 , Z 2 and Z 3 independently of one another optionally together with fluorine or chlorine-substituted (C 1 -C 6) -alkyl, with particular preference being given to Z 1 and Z 2 being (C 1 -C 6) -alkyl substituted by fluorine or chlorine, and Z 3 being (C 1 -C 6) -alkyl, particularly preferably is here that Z 1 and Z 2 is perfluorinated (C 1 -C 4) -alkyl and Z 3 is (C 1 -C 4) -alkyl, very particular preference is given to the fact that Z 1 is perfluorinated ethyl (C 2 F 5), Z 2 is perfluorinated methyl (CF 3 ) and Z 3 is methyl.
  • a further preferred embodiment relates to compounds of formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), wherein W is oxygen.
  • a further preferred embodiment relates to compounds of the formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), wherein Q is hydrogen or an optionally cyano- or halogen-substituted group selected from (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -alkoxy.
  • a further preferred embodiment relates to compounds of the formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), in which n in T is 0 or 1 and R 6 is fluorine, chloro, bromo, iodo, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci- C i) alkoxy, (Ci-C4) -haloalkoxy, cyano, nitro or amino.
  • a further preferred embodiment relates to compounds of the formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), wherein R 1 is hydrogen, (Ci-C 4 ) alkyl or (Ci-C 4 ) - haloalkyl.
  • a further preferred embodiment relates to compounds of the formula (I), preferably formulas (Ic), (If), (Ig) and (Ih), in which
  • Ai is CR 2
  • a 2 is CR 3
  • a 3 is CR 4
  • A4 is CR 5 and where R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, cyano, nitro, C6) -alkyl, (Ci-Ce) -haloalkyl, (Ci-Ce) -alkoxy or (Ci-C6) -haloalkoxy, particularly preferably for hydrogen, fluorine, chlorine, iodine, bromine, (Ci-C i) -alkyl or (Ci-C i) -alkoxy,
  • Z 1 and Z 2 are each independently perfluorinated (Ci-C i) -alkyl and Z 3 is (Ci-C i) -alkyl, very particularly preferred is that Z 1 is perfluorinated ethyl (C 2 F 5), Z is 2 is perfluorinated methyl (CF 3 ) and Z 3 is methyl.
  • W is oxygen n in T is 0 or 1 and R 6 is fluorine, chlorine, bromine, iodine, halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) - Alkoxy, (Ci-C4) haloalkoxy, cyano, nitro or amino
  • R 1 represents hydrogen, (Ci-C 4) -alkyl or (Ci-C 4) -haloalkyl.
  • Another preferred embodiment relates to compounds of formula (I) selected from formulas (Ic), (If), (Ig) and (Ih), wherein
  • Ai is CR 2
  • a 2 is CR 3
  • a 3 is CR 4
  • A is CR 5 and wherein R 2 , R 3 , R 4 and R ⁇ independently of one another represent hydrogen, fluorine, chlorine, iodine, bromine or (C 1 -C 12) -alkyl,
  • Z 1 and Z 2 are each independently perfluorinated (Ci-C i) -alkyl and Z 3 is (Ci-C i) -alkyl, very particularly preferred is that Z 1 is perfluorinated ethyl (C 2 F 5), Z is 2 is perfluorinated methyl (CF 3 ) and Z 3 is methyl.
  • W is oxygen
  • n in T is 0 or 1 and R 6 is fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy, (Ci-C4) haloalkoxy, cyano, nitro or amino
  • R 1 represents hydrogen, (Ci-C 4) -alkyl or (Ci-C 4) -haloalkyl.
  • Reaction Scheme 1 shows the general method A for the compounds (I-c) according to the invention.
  • the 5-H-pyrazoles 3 can be prepared, for example, by decarboxylation of the pyrazole-5-carboxylic acid 2 (see, for example, Can. J. Chem. 1986, 64, 11, 2211-2219; Eur. J. Org. Chem , 30, 6811-6822).
  • the compounds of general structure 5 and 6 are either commercially available or can be prepared by methods known to those skilled in the art.
  • Scheme 2 depicts general method B for the compounds (I-g) according to the invention.
  • Compounds of general structure 6 may, for. B. by amide formation from the corresponding acids 11 or by halogen exchange from corresponding intermediates of the general formula 6 '(see, for example, J. Am. Chem. Soc., 2002, 124, 14844-14845).
  • Compounds of general structures 11 and 6 ' are either commercially available or can be prepared by methods known to those skilled in the art.
  • the compounds of general structure 9 can be prepared by literature methods z.
  • Scheme 3 shows the general method of preparation B for the compounds (I-f) according to the invention.
  • the radicals A1-A4, R 1 , R 6 , Q, W and Z'-Z 3 have the meanings described above.
  • U is bromine, iodine or triflate while M is boronic, boronic or trifluoroboronate.
  • Compounds according to the invention of the general structure (If) can be prepared by literature methods by reacting 1,2,3-triazoles of the general structure 12 with boron compounds of Lett., 2008, 10, 5389-5392; Bioorg. Med. Chem. Lett., 2003, 13, 1665-1668.]
  • Triazoles of the general structure 12 can be prepared, for example, as described in US Pat from alkynes of the general structure 9 can be prepared by reaction with azides [see, for example, Org. Lett., 2008, 10, 3171-3174].
  • B. from the corresponding halogen compounds 6 are prepared [see, for. WO2006 / 080884; WO2006 / 025783].
  • Reaction Scheme 4 shows the general method of preparation B for the compounds (I-h) according to the invention.
  • M is a boronic acid, boronic acid ester or trifluoroboronate.
  • Ih can be prepared by literature methods by reacting tetrazoles of the general structure 13 with boron compounds of general structure 6 "[see, for example, US Pat. B. Tetrahedron Lett. 1998, 39, 2941-2944; Chem. Commun. 2012, 48, 2719-2721]. Tetrazoles of the general structure 13 may, for. Example, nitriles of the general structure 14 by reaction with azides are prepared [see, for. US2007 / 23876; WO2014 / 2109].
  • Reaction Scheme 5 shows the general method of preparation B for the compounds (Id) according to the invention. - -
  • the radicals A1-A4, R 1 , R 6 , Q, W and Z'-Z 3 have the meanings described above.
  • U is bromine, iodine, triflate, boronic acid, boronic acid ester or trifluoroboronate.
  • Compounds of the general structure (Id) according to the invention can be prepared by literature methods by reacting halogen or boron compounds of general structure 6 with pyrazoles of general structure 15 [see, for example, US Pat. WO2011 / 59619; Tetrahedron 2011, 67, 5282-5288; WO2009 / 140342].
  • Pyrazoles of general structure 15 may, for. B. from enamines of the general structure 16 and hydrazine compounds are prepared [see, for. US2011 / 212949].
  • Enaminones of general structure 16 may e.g. B. from ketones of the general formula 17 z. Example, be prepared by reaction with Dialkylam iddialkylacetalen [see, for. WO2012 / 139930; US2011 / 212949].
  • Ketones of general formula 17 may, for. B. be represented by reaction of the corresponding Weinrebamide 18 with Grignard reagents [see, for. WO2006 / 133885; US2010 / 222332].
  • the Weinrebamide of the general formula 18 are in turn known to those skilled in the process by amide formation from the corresponding carboxylic acids of the general structure 2 representable.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The invention thus comprises pure stereoisomers as well as any mixtures of these isomers. - 5 - Procedures and uses
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular crop protection agents.
  • pest control always includes the term pesticides.
  • the compounds of formula (I) are suitable with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, to improve the quality of the crop and to control animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hi
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Homoeosoma spp. Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., Eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Eg Lobesia botrana, Loxagrotis albicosta , Lymantria spp., Eg Lymantria dispar, Lyonetia spp., Eg Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp.
  • Oria spp., Orthaga spp., Ostrinia spp., Eg Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Eg Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculi
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests of the Mollusca strain in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp.
  • Clonorchis spp. Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp.
  • Hyostrongylus spp. Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria sp Paraglia spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma s
  • Strongyloides spp. Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
  • Plant pests from the Nematoda strain ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata
  • Paratrichodorus spp. Eg Paratrichodorus - - minor, Pratylenchus spp., eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.
  • the order of coccidia can be determined, e.g. Eimeria spp. fight.
  • the compounds of formula (I) may optionally in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving the plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • Formulations The present invention further relates to formulations and application forms prepared therefrom as pesticides, such as pesticides.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • extenders e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solvents are, for example, aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride
  • Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: e.g.
  • Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydro
  • dyes such as inorganic pigments, eg iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc may be present. 5
  • Stabilizers such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability, may furthermore be present. It may also contain foam-forming agents or defoamers.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-form polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be included in the formulations and the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
  • the formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I), more preferably between 0.01 and 95% by weight of the compound of the formula (I), very particularly preferably between 0 , 5 and 90 wt .-% of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application. mixtures
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or or plant growth regulators are used, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
  • the compounds of formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos,
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- Cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], e
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • Chloride channel activators such as avermectins / milbemycins, eg, abamectin, emamectin benzoate, lepimectin, and milbemectin.
  • Juvenile hormone imitators such as juvenile hormone analogs, eg, hydroprene, kinoprenes and methoprenes, or fenoxycarb or pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as
  • Alkyl halides e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • Bacillus thuringiensis subspecies israelensis Bacillus sphaericus
  • Bacillus thuringiensis subspecies aizawai Bacillus thuringiensis subspecies kurstaki
  • Bacillus thuringiensis subspecies tenebrionis and BT plant proteins CrylAb, CrylAc, CrylFa, Cry2Ab, mCry
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and Fenbutatin-oxide or Propargite or Tetradifon.
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and Fenbutatin-oxide or Propargite or Tetradifon.
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and Fenbutatin-oxide or Propargite or Tetradifon.
  • Decoupling of oxidative phosphorylation by interruption of the H proton gradient such as chlorfenapyr, DNOC, and sulfluramide.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, Thiocyclam and Thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Anti-skinning agents especially in dipterans, i.e., two-toed, such as Cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Dicofol, Diflovidazine, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazone, pyriminostrobin, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacill
  • inhibitors of ergosterol biosynthesis such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1
  • inhibitors of respiration such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS)
  • inhibitors of mitosis and cell division such as (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolide, (4.7) fuberidazole, (4.8) pencycuron , (4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6 trifluorophenyl) [l, 2,4] niazolo [l, 5-a] pyrimidine and (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2, 4,6-trifluorophenyl) pyridazine.
  • resistance inducers such as (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil, and (6.5) laminarin.
  • inhibitors of amino acid and protein biosynthesis such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin. - 5 -
  • inhibitors of ATP production such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.
  • inhibitors of cell wall synthesis such as (9.1) benthia-valicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) Valifenalate and (9.10) Polyoxin B.
  • inhibitors of lipid and membrane synthesis such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb , (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazene and (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis such as (11.1) carpropamide, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilone, (11.6) tricyclazole, and (11.7) 2,2,2 Trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • inhibitors of nucleic acid synthesis such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, ( 12.8) Hymexazole, (12.9) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid and (12.14) Octhilinone.
  • Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide.
  • decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap.
  • the compounds of formula (I) may be combined with biological pesticides.
  • biological pest control agents include bacteria, fungi, yeasts, plant extracts, and such products formed by microorganisms including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides. 5
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV
  • Spodoptera frugiperda armyworm
  • mNPV Spodoptera littoralis
  • bacteria and fungi that are added as 'inoculant' plants or parts of plants or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and those products formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pest control agents are:
  • Safeners as Mixture Partners The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- ( Dichloroacetyl) -l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 5283
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants produced by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods can be obtained, including transgenic plants and including those protected by plant breeders' rights or non-protectable plant varieties.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
  • plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties ("traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Such properties are an increased resistance of the plants against animal and Microbial pests, such as insects, arachnids, nematodes, mites, snails, cause, for example, by toxins formed in the plants, in particular those caused by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (C), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, also an increased Ab resistance of the plants against phytopathogenic fungi, bacteria and / or viruses, for example, by systemically Acquired resistance ( SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of the formula (I), or by the soil application, ie the compounds of formula (I) are introduced in solid form, (for example in the form of granules) in the location of the plants.
  • this may also be by metered addition of the compound of formula (I) in a solid form (eg as granules) into a flooded paddy field.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers containing a compound of formula (I) and mixing partners may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation comes.
  • the compounds of the formula (I) are useful for the protection of seeds of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals eg wheat, barley, rye, millet and oats
  • corn eg wheat, barley, rye, millet and oats
  • corn cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet)
  • peanut eg tomato, cucumber, bean, cabbage, onions and lettuce
  • fruit plants turf and ornamental plants.
  • seeds of cereals such as wheat, barley, rye and oats
  • corn soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of formula (I) is of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seed which contains at least one contains heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation.
  • suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coatings, and ULV formulations.
  • These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, Gibberellins and also water.
  • Suitable dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all those which are customary for the formulation of agrochemical active compounds and which require wetting.
  • alkylnaphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds become.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I) which have a favorable toxicity to warm-blooded animals, for the control of parasites used in livestock and animal husbandry in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals occur. They are effective against all or individual stages of parasite development.
  • farm animals include mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and crustaceans, eg in aquaculture and insects such as bees. n
  • Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians, and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • controlling means that by the compounds of the formula (I), the occurrence of the respective parasite in an animal infected with such parasites to a harmless extent is effective , can be reduced. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • arthropods include: - -
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as 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 Trichomonadidae, for example Giardia lamblia, G. canis;
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
  • Toxoplasmadidae for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum,
  • Theileria spec such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (eg, Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order 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 genus 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., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle
  • Roundworms Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp.
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp ., Cooperia spp., Nippostrongylus spp., 7
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from the order Porocephalida, for example Linguatula spp ..
  • the compounds of formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as anti-topazarasitic, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as anti-topazarasitic, in particular an arthropodicide such as Insecticide or acaricide, for example in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • vectors and the diseases or pathogens they carry are: 1) mosquitoes
  • Anopheles malaria, filariasis
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors for the purposes of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, Fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans. ?
  • Compounds of formula (I) are suitable for use in the prevention of diseases or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, i.e., it can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question are present as a ready-to-use pest control agent, i.e., it can be applied to the corresponding material without further changes.
  • the compounds of formula (I) can be used to protect against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water , Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera , Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out, for example, in aerosols, pressureless sprays, eg pump and atomizer sprays, smoke machines, foggers, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems , Moth papers, moth sacs and moth gels, as granules or dusts, in straw baits or bait stations.
  • Reaction Scheme 6 shows the synthesis of the compound Ic-1 according to the invention. Reaction scheme 6
  • Step 1 Synthesis of 1-methyl-3- (1,1,2,2-pentafluoroethyl) -4- (trifluoromethyl) pyrazole
  • Step 2 Synthesis of 1-methyl-3- (1,1,2,2-pentafluoroethyl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -4- (trifluoromethyl) pyrazole 3.03 ml (4.85 mmol) of a butyllithium solution (1.6 M in hexane) are added under argon to a solution of 1.00 g at -78 ° C. within 10 min. 3.73 mmol) of 1-methyl-3- (1,1,2,2-pentafluoroethyl) -4- (trifluoromethyl) pyrazole in 20 ml of tetrahydrofuran.
  • Step 3 Synthesis of 5- (4-bromopyrazol-1-yl) -2-chloro-N-cyclopropylbenzamide
  • reaction mixture is filtered through Tonsil, washed with ethyl acetate and concentrated on a rotary evaporator under reduced pressure. Further purification is carried out by chromatography on silica gel (eluent cyclohexane / ethyl acetate)
  • Step 4 Synthesis of N- ⁇ 2-Fluoro-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] benzyl ⁇ propanamide (Ic-1)
  • reaction mixture is filtered through Tonsil, washed with ethyl acetate and concentrated on a rotary evaporator under reduced pressure. Further purification is carried out by chromatography on silica gel (eluent cyclohexane / ethyl acetate) and then on silica gel RP-18 (acetonitrile, HCOOH, water).
  • Reaction Scheme 7 shows the synthesis of the compound Ig-1 Reaction Scheme 7 of the invention
  • Step 1 Synthesis of 5-ethynyl-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole
  • Step 2a (Alternative A): Synthesis of 2-chloro-A r cyclopropyl-5-iodobenzamide [0209] To a suspension of 19.0 g (67.3 mmol) of 2-chloro-5-iodobenzoic acid in dichloromethane (215 mL ) are added 9.39 g (74.0 mmol) of oxalic acid dichloride and a few drops of N, N-dimethylformamide. The reaction mixture is stirred for 30 min at room temperature and for 30 min at 35 ° C, then concentrated on a rotary evaporator under reduced pressure. The residue is dissolved in dry dichloromethane (220 ml), cooled to 0 ° C.
  • Reaction Scheme 8 shows the synthesis of the compound of the invention If-1 Reaction Scheme 8
  • Step 1 Synthesis of 4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazole
  • a solution of 0 , 71 mL (9.53 mmol) of a 37% aqueous formaldehyde solution and 0.08 mL (1.43 mmol) of acetic acid in dioxane after stirring for 15 minutes, 92.9 mg (1.43 mmol) of sodium azide and 464 mg of the crude product from step 1 of the synthesis of 2-chloro-N-cyclopropyl-5- ⁇ 4- [1-methyl-3 - (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] - 1 H -1,3,3-triazol-1-yl ⁇ benzamide containing ca.
  • Step 2 Synthesis of [4-chloro-3- (cyclopropylcarbamoyl) phenyl] boronic acid
  • Step 3 Synthesis of 2-chloro-A r cyclopropyl-5- ⁇ 4- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -lH-pyrazol-5-yl] -2H-l, 2 , 3-triazol-2-yl ⁇ benzamide (If-1)
  • Reaction Scheme 9 shows the synthesis of the compound Ih-1 according to the invention. Reaction scheme 9
  • Step 1 Synthesis of 5- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -2H-tetrazole
  • Step 2 Synthesis of 1-chloro-2-cyclopropyl-S-JS-1-methyl-S-ipentafluoroethyl) - (trifluoromethyl) -1H-pyrazol-5-yl] -2H-tetrazol-2-yl ⁇ benzamide ( Ih-1)
  • reaction mixture is stirred for 4 d at room temperature, then diluted with dichloromethane, adsorbed on kieselguhr and purified by column chromatography (S1O 2 , cyclohexane / ethyl acetate) and purified by preparative HPLC (Phenomenex Gemini 5 micron C18, water / acetonitrile / formic acid). 4 mg of 2-chloro-N-cyclopropyl-5- ⁇ 5- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -2H-tetrazole are obtained. 2-yl ⁇ benzamide as a colorless solid.
  • Reaction Scheme 10 shows the synthesis of the compound Id-1 according to the invention. Reaction scheme 10
  • Step 1 Synthesis of A r -Methoxy-A r , l -dimethyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxamide
  • l-Methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole-5-carboxylic acid in dichloromethane (250 mL) is added five drops of N, N-dimethylformamide and 42.8 mL (481 mmol) of oxalic acid dichloride.
  • the reaction mixture is heated to reflux for 90 minutes, then cooled and concentrated on a rotary evaporator under reduced pressure.
  • the residue is dissolved in dichloromethane (250 mL) and added to a solution of 18.8 g (192 mmol) N O-dimethylhydroxylamine hydrochloride in dichloromethane (250 mL), then 55.8 mL (400 mmol) of triethylamine are added dropwise.
  • the reaction mixture is stirred overnight at room temperature, then diluted with dichloromethane and stirred into 1N hydrochloric acid.
  • the mixture is extracted with dichloromethane.
  • the combined organic phases are washed with 1N sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator under reduced pressure.
  • Step 2 Synthesis of 1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] ethanone
  • 150 mL (449 mmol) of a Methylmagnesiumbromid Solution (3M in ether) is added dropwise so slowly that the temperature does not rise above 0 ° C.
  • Step 4 Synthesis of 2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -1H, 2'H-3,3'-bipyrazole
  • Step 5 Synthesis of 2-chloro-A r cyclopropyl-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) - lH, 2'H-3,3'-bipyrazol-l -yl] benzamide (Id-1)
  • reaction mixture After cooling to room temperature, the reaction mixture is diluted with ethyl acetate and water and extracted with ethyl acetate. The combined organic phases are washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator under reduced pressure. The residue is purified by column chromatography (S1O 2 , cyclohexane / ethyl acetate) and by preparative HPLC (Phenomenex Gemini 5 micron C18, water / acetonitrile / formic acid).
  • the given mass is the peak of the isotopic pattern of the highest intensity [M + H] + ion; if that was [MH] "Ion detected, the stated mass is characterized by 2.
  • the vials are filled with 5-10 adult cat fleas ⁇ Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move uncoordinated are considered dead or struck.
  • a substance shows good activity against Rhipicephalus sanguineus, if at least 80% effect was achieved in this test at an application rate of 5 ⁇ g / cm 2 . It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.
  • Tick nymphs (Amblyomma hebraeum) are placed in perforated plastic cups and dipped for one minute at the desired concentration. The ticks are transferred to filter paper in a Petri dish and stored in a climate cabinet.
  • the kill is determined in%. 100% means that all ticks have been killed; 0%> means that none of the ticks have been killed.
  • Boophilus microplus - Diptest BOOPMI Dip
  • the active ingredient 10 mg are dissolved in 0.5 ml of dimethyl sulfoxide.
  • the active compound solution is diluted with water to the particular desired concentration.
  • This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female cattle ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ppm: Ic-1, Ig-1
  • Boophilus microplus injection test (BOOPMI Inj)
  • ⁇ ⁇ of the drug solution is injected into the abdomen of 5 wet, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room. The effect control takes place after the desired time on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • CTECFE Ctenocephalides felis - Oral test
  • Solvent dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • Approx. 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. On the chamber, a metal cylinder is placed, whose Bottom is closed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • the kill is determined in%. 100% means> that all fleas have been killed; 0% means that none of the fleas have been killed.
  • Lucilla cuprina - test (LUCICU)
  • the kill is determined in%. 100% means> that all larvae have been killed; 0%> means that no larvae have been killed.
  • Vessels containing sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica). After 2 days, the kill is determined in%. 100% means> that all flies have been killed; 0% means that none of the flies have been killed.
  • active compound preparation 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Chinese cabbage leaf disks (Brassica pekinensis) infested with all stages of the green peach aphid ⁇ Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
  • Phaedon cochleariae - spray test PHAECO
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • Emulsifier Alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Bean leaf disks Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

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Abstract

L'invention concerne entre autres des composés substitués par un halogène des composés de formules générales (I) dans lesquelles les radicaux A1-A4, T, W, Q, R1 et Z1-Z3 ont les significations indiquées dans la description. L'invention concerne en outre des procédés de production des composés de formules (I). Les composés selon l'invention sont en particulier appropriés pour la lutte contre les insectes, les arachnides et les nématodes dans l'agriculture et contre les ectoparasites en médecine vétérinaire.
EP15728550.3A 2014-06-18 2015-06-15 Composés substitués par un halogène Withdrawn EP3157905A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14172922 2014-06-18
PCT/EP2015/063277 WO2015193218A1 (fr) 2014-06-18 2015-06-15 Composés substitués par un halogène

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EP (1) EP3157905A1 (fr)
JP (1) JP2017519761A (fr)
CN (1) CN106795119A (fr)
AR (1) AR100817A1 (fr)
AU (1) AU2015276315A1 (fr)
BR (1) BR112016029361A2 (fr)
CA (1) CA2952525A1 (fr)
CL (1) CL2016003248A1 (fr)
MX (1) MX2016016837A (fr)
RU (1) RU2017101427A (fr)
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WO (1) WO2015193218A1 (fr)
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AR101816A1 (es) * 2014-04-02 2017-01-18 Bayer Cropscience Ag Derivados de 3-[(pirazol-5-il)-heteroaril]-benzamidas como agentes pesticidas
BR112018016794B1 (pt) 2016-02-18 2022-07-19 Syngenta Participations Ag Compostos derivados de pirazol ativos em termos pesticidas, composição pesticida, método para controle de pragas, método para a proteção de material de propagação vegetal do ataque por pragas e material de propagação vegetal
WO2018177993A1 (fr) 2017-03-31 2018-10-04 Bayer Cropscience Aktiengesellschaft Pyrazoles pour lutter contre les arthropodes
AU2018241748B2 (en) * 2017-03-31 2023-02-09 Elanco Animal Health Gmbh Tricyclic carboxamides for controlling arthropods
US11040962B2 (en) 2017-04-05 2021-06-22 Syngenta Participations Ag Pesticidally active pyrazole derivatives
EP3606918A1 (fr) 2017-04-05 2020-02-12 Syngenta Participations AG Dérivés pyrazole actifs sur le plan pesticide
EP3606919A1 (fr) 2017-04-05 2020-02-12 Syngenta Participations AG Dérivés de pyrazole actifs sur le plan pesticide
WO2019030358A1 (fr) 2017-08-11 2019-02-14 Syngenta Participations Ag Dérivés de pyrazole actifs sur le plan pesticide
WO2019030355A1 (fr) 2017-08-11 2019-02-14 Syngenta Participations Ag Dérivés de pyrazole actifs sur le plan pesticide
AR112672A1 (es) 2017-08-11 2019-11-27 Syngenta Participations Ag Derivados de tiofeno activos como plaguicidas
AR112673A1 (es) 2017-08-11 2019-11-27 Syngenta Participations Ag Derivados de pirazol activos como plaguicidas
EP3692031B1 (fr) 2017-10-06 2021-09-01 Syngenta Participations AG Dérivés de pyrrole actifs sur le plan pesticide
EP3692038A1 (fr) 2017-10-06 2020-08-12 Syngenta Participations AG Dérivés de pyrrole actifs sur le plan pesticide
WO2020164994A1 (fr) 2019-02-13 2020-08-20 Syngenta Crop Protection Ag Dérivés de pyrazole à action pesticide
WO2020164993A1 (fr) 2019-02-13 2020-08-20 Syngenta Crop Protection Ag Dérivés de pyrazole à action pesticide

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CN102803217B (zh) * 2009-05-15 2015-06-17 诺华股份有限公司 作为醛固酮合酶抑制剂的芳基吡啶
CN103313971B (zh) * 2010-11-15 2015-12-02 拜耳知识产权有限责任公司 N-芳基吡唑（硫代）甲酰胺
AR085318A1 (es) * 2011-02-09 2013-09-25 Syngenta Participations Ag Derivados de triazol que tienen actividad insecticida

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TW201625547A (zh) 2016-07-16
AR100817A1 (es) 2016-11-02
WO2015193218A1 (fr) 2015-12-23
CL2016003248A1 (es) 2017-08-04
ZA201700302B (en) 2019-06-26
JP2017519761A (ja) 2017-07-20
CN106795119A (zh) 2017-05-31
BR112016029361A2 (pt) 2017-10-31
RU2017101427A (ru) 2018-07-18
AU2015276315A1 (en) 2017-01-12
MX2016016837A (es) 2017-10-12
CA2952525A1 (fr) 2015-12-23

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