WO2018177993A1 - Pyrazoles pour lutter contre les arthropodes - Google Patents

Pyrazoles pour lutter contre les arthropodes Download PDF

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WO2018177993A1
WO2018177993A1 PCT/EP2018/057612 EP2018057612W WO2018177993A1 WO 2018177993 A1 WO2018177993 A1 WO 2018177993A1 EP 2018057612 W EP2018057612 W EP 2018057612W WO 2018177993 A1 WO2018177993 A1 WO 2018177993A1
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spp
methyl
alkyl
compounds
formula
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PCT/EP2018/057612
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German (de)
English (en)
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Tobias HARSCHNECK
Alexander ARLT
Robert Velten
Michael Maue
Kerstin Ilg
Ulrich Görgens
Andreas Turberg
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Bayer Cropscience Aktiengesellschaft
Bayer Aktiengesellschaft
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Publication of WO2018177993A1 publication Critical patent/WO2018177993A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid

Definitions

  • the present application relates to novel compounds, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes.
  • WO 2011/113756 discloses triazole derivatives which have insecticidal activity.
  • 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 novel insecticidal, acaricidal and / or parasiticidal halogen-substituted compounds of the general formula (I) - -
  • R 1 is H, in each case optionally with one or more substituents selected independently from amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C 4 -alkyl, Alkyl, C 3 -C 10 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -cycloalkenyl, C 2 -C 4 -alkynyl, N-mono-C 1 -C 4 -alkyl-amino, N, N-di-C 1 -C 4 -alkylamino, N -C 1 -C 4 alkanoylamino, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 4 cycl
  • an oxo group As methylidene or ethylidene), an oxo group, an imino group substituted Ci-C6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C 7 -Cvcloalkyl, C6-.Cio-.Ci4-aryl (Ci-C3 ) -alkyl 3. 4, 5. 6. 7. 8.
  • thietanyl such as thiethanyl-3-yl oxidothiethane, such as 1-oxo-thietan-3-yl or dioxothiethane, such as 1, l-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci-CsValkyl, preferably represents optionally substituted by halogen or cyano-substituted C3-C7-cycloalkyl;
  • thietanyl such as thiethanyl-3-yl oxidothiethane, such as 1-oxo-thietan-3-yl or dioxothiethane, such as 1, l-dioxo-thietan-3-yl or 3, 4, 5, 6, 7, 8, 9 or 10-membered heterocyclyl (Ci-CsValkyl, preferably represents optionally substituted by halogen or cyano-substituted C3
  • R 2 is H or C 1 -C 6 alkyl
  • Ai, A2 and A3 are each independently N, O, CR 3, S, or NR 4, wherein Ai, A2, A3, Z and the C-atom of the ring form an aromatic system;
  • Each R 3 is independently H, Cl, F, I, Br or optionally halogenated C 1 -C 4 alkyl;
  • Each R 4 is independently H or optionally halogenated C 1 -C 4 alkyl; Q is O or S;
  • Z is C or N, particularly preferably C
  • T is one of the 5-membered heteroaromatics T1-T8 listed below, wherein the
  • Binding to is marked with a rhombus #
  • R 5 is optionally halogenated (C 1 -C 6) -alkyl, optionally halogenated (C 1 -C 6) -alkoxy, -S (O) o-2 (C 1 -C 2) -alkyl or NO 2, preferably perhalogenated (C 1 -C 4 ) -Alkyl, perhalogenated (C 1 -C 4 ) -alkoxy or -S (O) o- ( 2 -C (Ci-C 2 ) -alkyl, more preferably perfluorinated (Ci-C 4 ) -alkyl, perfluorinated (Ci-C 4) alkoxy or -S (0) o-2 - (Ci-C 2) alkyl, more preferably is CF3;
  • R 6 represents optionally halogenated (C 3 -C 6 ) -cycloalkyl, optionally halogenated (C 1 -C 6) -alkoxy or optionally halogenated (C 1 -C 6) -alkyl, preferably perhalogenated (C 1 -C 4 ) -alkyl or perhalogenated (C 1 -C 4 ) -alkyl; C 4) alkoxy, more preferably perfluorinated (C 1 -C 4) -alkyl or perfluorinated (C 1 -C 4) -alkoxy, even more preferably C 2 F 5; - - As well as salts, N-oxides and tautomeric forms of the compounds of formula (I).
  • a preferred embodiment of the present invention is directed to compounds according to paragraph [0009], wherein R 2 is H or methyl.
  • a further preferred embodiment is directed to compounds according to one of the paragraphs [0009] or [0010], where T is for Tl, T4 or T5.
  • T stands for T2, T3, T4, T5, T6, T7 or T8, particularly preferably for T4 or T5.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0011], wherein R 1 is cyclopropyl or 1 -CN-cyclopropyl.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0013], wherein Q is O.
  • a further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0014], wherein A 3 is S.
  • a further preferred embodiment is directed to compounds according to any of paragraphs [0009] to [0015], wherein Z is C and A 2 is C-Hal, wherein Hal preferably represents I, Br or Cl, more preferably Br or I and especially preferably represents Br stand.
  • a further preferred embodiment is directed to compounds according to any one of paragraphs [0009] to [0016], wherein A3 is S, Z is C and A2 is C-Hal, wherein Hal is preferably Br, I or Cl, more preferably represents Cl, and Ai is CH or N.
  • a further preferred embodiment is directed to compounds of the formula (Ia),
  • a further preferred embodiment is directed to compounds of the formula (Ib) wonn Q, R 1 , R 2 , R 5 and R 6 and Ai as for compounds of formula (I) or a preferred embodiment of compounds of formula ( I) or a preferred embodiment of compounds of formula (I) are defined herein and Hai is preferably I, Br or Cl.
  • a further preferred embodiment is directed to compounds of the formula (Ic) Wherein Q, R 1 , R 2 , R 5 and R 6 and Ai are as defined for compounds of the formula (I) herein and Hai is preferably I, Br or Cl stands.
  • a further preferred embodiment is directed to compounds of the formula (Ia) wherein Q is O, Ai is N or CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally substituted by CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • a further preferred embodiment is directed to compounds according to formula (Ib) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • a further preferred embodiment is directed to compounds according to formula (Ic) wherein Q is O, Ai is CH, Hai is Br, I or Cl, R 2 is H, R 1 is optionally CN substituted cyclopropyl (such as cyclopropyl or 1 -CN-cyclopropyl), R 5 is CF 3 and R 6 is C 2 F 5 .
  • Another aspect relates to an insecticidal composition
  • an insecticidal composition comprising at least one compound of the formula (I) according to any one of paragraphs [0009] to [0023] and an extender and / or a surface-active substance.
  • Another aspect relates to a process for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound according to any of paragraphs [0009] to [0023] is treated.
  • Another aspect relates to the use of compounds according to any one of paragraphs [0009] to [0023], or of a insecticidal agent according to paragraph [0024] for controlling pests.
  • Another aspect relates to seeds containing a compound according to any one of paragraphs [0009] to [0023] as part of a casing applied to the seed, or as a further layer in addition to a coating on the seed is applied.
  • Another aspect relates to a method for the protection of transgenic or conventional seed and the resulting plant from the infestation of pests, characterized in that the seed with at least one compound of formula (I) or derived from formula (I) Formula is treated as described herein.
  • Yet another aspect relates to the use of compounds of formula (I) or a formula derived from formula (I) as described herein or of a insecticidal agent as described herein for controlling pests.
  • Another aspect relates to the use of compounds of formula (I) or of a formula derived from formula (I) as described herein in the vector control.
  • Yet another aspect relates to seed in which a compound of formula (I) or a formula derived from formula (I) as described herein is applied to the seed in addition to a casing as part of a casing or as a further layer or layers is.
  • a further aspect relates to a process for applying a coating comprising at least one compound of formula (I) or a formula derived from formula (I) as described herein or for applying a compound of formula (I) or one of formula ( I) derived formula as herein described, applied as a layer or further layers in addition to a casing on seed, comprising the steps of a) mixing seeds with a coating material consisting of or comprising a compound of formula (I) or one of formula (I) derived formula as described herein, b) enriching the obtained coated seed mass, c) drying the resulting enriched seed mass, d) degumming (disagglomerating or deagglomerating) the obtained dried seed mass.
  • the compounds of the formula (I) described herein or of a formula derived from formula (I) may optionally be present in different composition depending on the nature of the substituents as geometric and / or as optically active isomers or corresponding isomer mixtures.
  • the invention relates to both the pure isomers and the isomer mixtures.
  • the compounds of the invention may also be present as metal complexes.
  • Definitions It will be understood by those skilled in the art, unless expressly stated, that the terms “a,” “an,” or “an” as used in this application, “depending on the situation,” “a (1)”, “ may mean one (1) or more or at least one (1).
  • C atoms Structures with a variable number of possible carbon atoms (C atoms) can be referred to in the present application as Cuntere limit C atoms ⁇ Cobere boundary C atoms ⁇ structures (C U GC 0 G structures), the more determined to become.
  • An alkyl group may consist of 3 to 10 C atoms and then corresponds to C3-Cio-alkyl.
  • Ring structures of C atoms and heteroatoms may be referred to as "uG to oG-membered" structures
  • An example of a 6-membered ring structure is toluene (a 6-membered ring structure substituted with a methyl group).
  • Halogen refers to the elements of the 7th main group, preferably fluorine, chlorine, bromine and iodine, more preferably fluorine, chlorine and bromine.
  • alkyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s Butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 2-dimethylpropyl, 1,3-dimethylbutyl, 1, 4-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3 Dimethylbutyl
  • alkyls having 1 to 4 carbon atoms such as methyl, ethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl, among others.
  • the alkyls according to the invention may be substituted by one or more, identical or different radicals.
  • alkenyl - alone or as part of a chemical group - for straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one double bond, such as vinyl, 2-propenyl, 2-butenyl, 3-butenyl , 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2 -butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl 2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl
  • alkenyls having 2 to 4 carbon atoms such as 2-propenyl, 2-butenyl or 1-methyl-2-propenyl, among others.
  • the alkenyls according to the invention may be substituted by one or more identical or different radicals. - -
  • alkynyl alone or as part of a chemical group - is straight-chain or branched hydrocarbons, preferably having 2 to 6 carbon atoms and at least one triple bond such as 2-propynyl, 2-butynyl, 3-butynyl, 1 - Methyl 2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1, 1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 2-methyl-4-pent
  • alkynyls having 2 to 4 carbon atoms such as, inter alia, ethynyl, 2-propynyl or 2-butynyl-2-propenyl.
  • the alkynyls according to the invention may be substituted by one or more, identical or different radicals.
  • 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, cycloheptyl, cyclooctyl, bicyclo 2.2.1] heptyl, bicyclo [2.2.2] octyl or adamantyl. Also preferred are cycloalkyls having 3, 4, 5, 6 or 7 carbon atoms, such as, inter alia, cyclopropyl or cyclobutyl.
  • the cycloalkyls of the invention may be substituted by one or more, identical or different radicals.
  • alkylcycloalkyl is mono-, bi- or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as methylcyclopropyl, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Further preferred are alkylcycloalkyls having 4, 5 or 7 carbon atoms, such as, for example, ethylcyclopropyl or 4-methylcyclohexyl.
  • the alkylcycloalkyls of the invention may be substituted by one or more, identical or different radicals.
  • cycloalkylalkyl is mono-, bi- or tricyclic cycloalkylalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and cyclopentylethyl. Also preferred are cycloalkylalkyl having 4, 5 or 7 carbon atoms, such as cyclopropylmethyl or cyclobutylmethyl.
  • the cycloalkylalkyls of the invention may be substituted by one or more, identical or different radicals.
  • hydroxyalkyl is straight-chain or branched alcohol, preferably having 1 to 6 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, s-butanol and t-butanol. Further preferred are hydroxyalkyl groups having 1 to 4 carbon atoms.
  • the hydroxyalkyl groups according to the invention may be substituted by one or more identical or different radicals - -
  • alkoxy represents straight-chain or branched O-alkyl, preferably having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Further preferred are alkoxy groups having 1 to 4 carbon atoms.
  • the alkoxy groups according to the invention may be substituted by one or more identical or different radicals.
  • alkylsulfanyl is straight-chain or branched S-alkyl, preferably having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio and t-butylthio. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms.
  • the Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
  • alkylsulfinyl represents straight-chain or branched alkylsulfinyl, preferably having 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl and t-butylsulfinyl. Further preferred are alkylsulfinyl groups having 1 to 4 carbon atoms.
  • the alkylsulfinylgrappen invention can be substituted with one or more, identical or different radicals.
  • alkylsulfonyl represents straight-chain or branched alkylsulfonyl, preferably having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl and t-butylsulfonyl. Further preferred are alkylsulfanyl groups having 1 to 4 carbon atoms.
  • the Alkylsulfanylgrappen invention can be substituted with one or more, identical or different radicals.
  • the alkylcarbonyls according to the invention may be substituted by one or more identical or different radicals.
  • cycloalkylcarbonyl represents straight-chain or branched cycloalkylcarbonyl, preferably having 3 to 10 carbon atoms in the cycloalkyl moiety, such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptyl, bycyclo [2.2.2] octylcarbonyl and adamantylcarbonyl. Also preferred are cycloalkylcarbonyl having 3, 5 or 7 carbon atoms in the cycloalkyl moiety.
  • the Cycloalkylcarbonylgrappen invention can be substituted with one or more, identical or different radicals. - -
  • alkoxycarbonyl alone or as part of a chemical group - is straight-chain or branched alkoxycarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkoxy moiety, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl.
  • the alkoxycarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
  • alkylaminocarbonyl means straight-chain or branched alkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl.
  • the alkylammocarbonyl groups according to the invention may be substituted by one or more, identical or different radicals.
  • N-dialkylamino-carbonyl is straight-chain or branched NN-dialkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl moiety, such as NN-dimethylamino-carbonyl, ⁇ . ⁇ -diethylamino-carbonyl, NN Di (n-propylamino) carbonyl, N, N'-di (isopropylamino) carbonyl and N, N'-di (s-butylamino) carbonyl.
  • the N, N-dialkylaminocarbonyl groups according to the invention may be substituted by one or more identical or different radicals.
  • aryl 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.
  • aryl also represents polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, where the binding site is on the aromatic system.
  • the aryl groups according to the invention may be substituted by one or more, identical or different radicals.
  • substituted aryls are the arylalkyls, which may likewise be substituted by one or more identical or different radicals in the C 1 -C -alkyl- and / or C 6 -C 4 -aryl moiety.
  • arylalkyls include benzyl and 1-phenylethyl.
  • heterocycle means 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, 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 - - 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.
  • Heterocyclyl groups according to the invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxolanyl, dioxolyl, pyrazolidinyl, tetrahydrofuranyl, dihydrofuranyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl , Oxazetidinyl, oxaziridinyl, oxazepanyl, oxazinanyl, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholin
  • heteroarylene ie heteroaromatic systems.
  • heteroaryl means heteroaromatic compounds, that is, fully unsaturated aromatic heterocyclic compounds which fall under the above deficient 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 according to the invention may furthermore be substituted by one or more identical or different radicals.
  • substituents such as a substituted alkyl, alkenyl, alkynyl, alkoxy, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl, represent, for example, a substituted radical derived from the unsubstituted body, wherein the substituents are, for example, one (1) substituent or more substituents, preferably 1, 2, 3, 4, 5, 6, or 7, selected from a group consisting of amino , Hydroxy, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, C 1 -C 4 -carboxy, carbonamide, SF 5, aminosulfonyl, C 1 -C -alkyl, C 3 -C -cycloalkyl, C 2 -C -alken
  • an oxo group As methylidene or ethylidene), an oxo group, an imino group and a substituted imino group.
  • Particularly preferred substituted groups are halogenated groups. These may have one or more halogen substituents, but these groups still have at least one CH bond, or be perhalogenated.
  • the exemplified substituents (“first substituent level"), if they contain hydrocarbon-containing moieties, optionally further substituted there (“second substituent plane"), for example by one or more of the substituents each independently selected from halogen, hydroxy, amino , Nitro, cyano, isocyano, azido, acylamino, an oxo group and an imino group.
  • the term "(optionally) substituted" group includes only one or two substituent levels.
  • halogen-substituted chemical groups or halogenated groups are monosubstituted or polysubstituted by halogen up to the maximum possible number of substituents.
  • groups are also referred to as halo groups (such as, for example, haloalkyl).
  • the halogen atoms may be the same or different and may all be bonded to one or more carbon atoms.
  • halogen is in particular fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferably fluorine or Cl.
  • halogen-substituted groups are monohalocycloalkyl, such as 1-fluorocyclopropyl, 2-fluorocyclopropyl or 1-fluorocyclobutyl, monohaloalkyl, such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroalkyl ethyl, chloromethyl, or fluoromethyl; Perhaloalkyl such as trichloromethyl or trifluoromethyl or CF 2 CF 3, polyhaloalkyl such as difluoromethyl, 2-fluoro-2-chloro-ethyl, dichloromethyl, 1, 1, 2,2-tetrafluoroethyl, or 2,2,2-trifluoroethyl.
  • monohaloalkyl such as 2-chloroethyl, 2-fluoroethyl, 1-chloroethyl, 1-fluoroalkyl ethyl, chloromethyl,
  • haloalkyls are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2 , 2-difluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl and pentafluoro-t-butyl.
  • haloalkyls having 1 to 4 carbon atoms and 1 to 9, preferably 1 to 5 identical or different halogen atoms, which are selected from fluorine, chlorine or bromine.
  • halogenoalkyls having 1 or 2 carbon atoms and having 1 to 5 identical or different halogen atoms, which are selected from fluorine or chlorine, such as, inter alia, difluoromethyl, trifluoromethyl or 2,2-difluoroethyl.
  • halogen-substituted compounds are haloalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 , OCH 2 CHF 2 and 0CH 2 CH 2 C1, haloalkylsulfanyls such as difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio , 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio or 2-chloro-1,1,2-trifluoroethylthio, haloalkylsulfinyls such as difluoromethylsulfinyl, trifluoromethylsulfinyl , Trichloromethylsulfin
  • radicals with C atoms those having 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred.
  • Preferred are usually substituents selected from the group halogen, e.g. Fluorine and chlorine, (Ci-C i) alkyl, preferably methyl or ethyl, (Ci-C i) haloalkyl, preferably trifluoromethyl, (Ci-C4) alkoxy, preferably methoxy or ethoxy, (Ci-C i) haloalkoxy, nitro and cyano.
  • Particularly preferred are the substituents methyl, methoxy, fluorine and chlorine.
  • Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals, which are N-substituted for example by one or two identical or different radicals from the group alkyl, hydroxy, amino, alkoxy, acyl and aryl ; 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-mono- and
  • cyclic amino groups heteroaromatic or aliphatic ring systems having one or more nitrogen atoms.
  • the heterocycles are saturated or unsaturated, consist of one or more, optionally fused ring systems and Optionally contain further heteroatoms, such as one or two nitrogen, oxygen and / or sulfur atoms.
  • the term also includes such groups having a spiro or bridged ring system.
  • the number of atoms that form the cyclic amino group is arbitrary and may, for example, in the case of a single-ring system of 3 to 8 ring atoms and in the case of a two-ring system of 7 to 1 1 atoms.
  • Examples of cyclic amino groups with saturated and unsaturated monocyclic groups having a nitrogen atom as a heteroatom are 1-azetinyl, pyrrolidino, 2-pyrrolidin-1-yl, 1 - pyrrolyl, piperidino, 1, 4-dihydropyrazine-1-yl, 1 2,5,6-tetrahydropyrazine-1-yl, 1,4-dihydropyridin-1-yl, 1, 2,5,6-tetrahydropyridin-1-yl, called homopiperidinyl;
  • Exemplary of cyclic amino groups with saturated and unsaturated monocyclic groups having two or more nitrogen atoms as heteroatoms are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 1, 2- Dihydro-piperazine-1-yl, 1,2-dihydro-pyrimidin-1-
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 haloalkyl, Ci-C4 .Halogenalkoxy, Ci-C 4 .Alkylsulfanyl, Ci-C.
  • Haloalkylsulfanyl, cyano, isocyano and nitro for example, o-, m- and p-tolyl, dimethylphenols, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4 Trifluoromethyl- and trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl, 4-heptafluorophenyl.
  • Optionally substituted cycloalkyl is preferably cycloalkyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group - -
  • Halogen, cyano, C 1 -C -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 Haloalkoxy is substituted, in particular by one or two Ci-C4-Alkylreste substituted.
  • Optionally substituted heterocyclyl is preferably heterocyclyl which is unsubstituted or mono- or polysubstituted, preferably up to three times by identical or different radicals from the group halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 haloalkoxy groups, nitro, and oxo, in particular mono- or polysubstituted by radicals from the is especially substituted by one or two Ci-C 4 alkyl group halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4 haloalkyl, and oxo.
  • 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.
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. ?
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always 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, 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.
  • the term "hygiene” is understood to mean the entirety of all measures, methods and behaviors with the goal of avoiding diseases - in particular infectious diseases - and the health of humans, animals and / or the environment Serve and / or maintain the cleanliness.
  • This includes according to the invention in particular measures for cleaning, disinfection and sterilization, for example, textiles or hard surfaces, mainly glass, wood, concrete, porcelain, ceramic, plastic or metal (s), and their
  • measures for cleaning, disinfection and sterilization for example, textiles or hard surfaces, mainly glass, wood, concrete, porcelain, ceramic, plastic or metal (s), and their
  • methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are carried out on the human or animal body are excluded.
  • honeygiene sector therefore encompasses all areas, technical areas and commercial uses in which such measures, processes and hygiene behaviors are of importance, such as hygiene in kitchens, bakeries, airports, spas, swimming pools, shopping centers, Hotels, hospitals, stables, etc.
  • the term “hygiene pest” is understood to mean one or more animal pests (e) whose presence in the hygiene sector is problematical, in particular for health reasons, and it is therefore the primary aim to prevent or treat hygiene pests in the hygiene sector This can be done, in particular, by the use of a pest control agent, which can be used both prophylactically and only when infested to control the pest It is also possible to use agents that cause a contact is avoided or reduced with the pest etc. For example, the following organisms may be considered as hygiene pests.
  • the term “hygiene protection” therefore includes all actions for the maintenance and / or improvement of such measures, procedures and behaviors for hygiene.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests from the strain of the Arthropoda in particular from the class of the Arachnida eg Acarus spp., For example 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.
  • Acarus siro Ac
  • Curculio spp. Eg Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., Eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgi fera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.
  • Contarinia spp. Eg Contarinia johnsoni, Contarina nasturtii, Contarina pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., Eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp , Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg, Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophil a spp., eg Drosophila melanogaster, Drosophila suzukii, E
  • Diaphorina citri Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., Eg Dysaphis apiifolia, Dysaphis plantagmea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna , Empoasca solana, Empoasca stevensi, Eriosoma spp., Eg Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geo
  • Nephotettix spp. Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon
  • Toxoptera spp. Eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunetus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops, Tri
  • Cydia spp. Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Egg dana saccharina, Ephestia spp., eg, Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea , Euxoa spp., Felt
  • 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, e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., E.g.
  • Echinococcus spp. E.g. Echinococcus granulosus, Echinococcus multilocularis, Echinostoma spp., Enterobius spp., E.g.
  • Enterobius vermicularis Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp. , eg Hymenolepis nana, Hyostrongylus spp., Litomosoides spp., Loa spp., E.g.
  • Loa Loa Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodiras spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp.
  • Opisthorchis spp. Onchocerca volvulus, Opisthorchis spp., Osleras spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp.
  • Schistosoma spp. Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Eg Strongyloides fuelleborni, Strongyloides stercoralis, Strongylus spp., Syngamus spp., Taenia spp., E.g. Taenia saginata, Taenia solium, Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., E.g.
  • Trichinella spiralis Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., E.g. Trichuris trichuria, Uncinaria spp., Wuchereria spp., E.g. Wuchereria bancrofti;
  • Ditylenchus spp. E.g. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., E.g. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., E.g. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., E.g. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hirschmanieila spp., Hoplolaimus spp., Longidorus spp., E.g.
  • Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. Tylenchulus semipenetrans, Xiphinema spp., E.g. Xiphinema index.
  • nematodes in the present context includes all species of the strain Nematoda and in particular species, the plants or fungi (for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others) or even humans and animals (for example species of Trichinellida, Tylenchida, Rhabditida and Spirurida) parasites or causing damage to these animals, as well as other parasitic helminths.
  • the plants or fungi for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others
  • humans and animals for example species of Trichinellida, Tylenchida, Rhabditida and Spirurida
  • a nematocide in crop protection as described herein has the ability to control nematodes.
  • controlling nematodes means killing the nematodes or preventing or aggravating their development or growth, or preventing or hindering their penetration into or their sucking on the plant tissue.
  • the efficacy of the compounds is compared by a comparison of mortality, bile formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes between one treated with the compound of formula (I) Plant, plant part or the treated soil and an untreated plant, plant part or untreated soil (100%) determined.
  • a reduction of 25-50% compared to an untreated plant, plant part or untreated soil more preferably a reduction of 51-79%, and most preferably complete suppression or complete prevention of development and growth of the nematodes by reduction achieved by 80 to 100%.
  • Nematodes as described herein also include control of nematode proliferation (development of cysts and / or eggs).
  • Compounds of formula (I) may also be used to maintain healthy plants or animals and may be used for curative, preventive or systemic control of nematode control. Methods are known to those skilled in the art, such as mortality, bile formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, mobility (motility) of the nematodes.
  • the use of a compound of formula (I) can keep the plant healthy and also includes a reduction in the damage caused by nematodes as well as an increase in the amount of harvest.
  • nematodes refers to plant nematodes, which include all nematodes that cause damage to plants
  • Plant nematodes include plant parasitic nematodes and soil-borne nematodes
  • Plant parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp semi-parasites such as Tylenchulus spp; migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonema spp .; localized parasites such as Heterodera spp., Globodera spp., and Meloidogyne spp., and stalk and leaf endoparasites such as Ditylenchus spp
  • Particularly harmful root parasitic soil nematodes are, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and / or root-k
  • nematodes to combat which a compound of formula (I) can be used include nematodes of the genus Meloidogyne such as the Southern Root-Knot Nematode (Meloidogyne incognita), the Javanese Root-Knot Nematode (Meloidogyne Javavanica, Northern Root-knot nematode (Meloidogyne hapla) and the peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as potato scabies (Ditylenchus destructor) and cane and stemlets (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as Cob root Nematode (Pratylenchus penetrans), the Chrysanthemum Root-Lesion Nematode (Pratylenchus fallax), the Coffee Rooted
  • the plants for the protection of which a compound of the formula (I) can be used include plants such as cereals (for example rice, barley, wheat, rye, oats, corn and the like), beans (soybean, azuki bean, Bean, broad beans, peas, peanuts and the like), fruit trees / fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries and the like), vegetables (cabbage, tomato, spinach, Broccoli, lettuce, onion, tubeworm, pepper and the like), root crops (carrot, potato, sweet potato, radish, lotus root, rutabaga and the like), plants for industrial raw materials (cotton, hemp, paper mulberry, mitsumata, rape, turnip, hops, sugar cane , Sugar beet, olive, gum, palm, coffee, tobacco, tea and the like), cucurbits (squash, cucumber, watermelon, melon and the like),
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of coffee, in particular Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. and from Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. and Scutellonema spp.
  • the compounds of formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci and Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodor
  • the compounds of formula (I) are particularly suitable for controlling tomato nematodes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus , Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of cucurbits, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei.
  • the compounds of the formula (I) are particularly suitable for controlling cotton nematodes, in particular Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.
  • the compounds of the formula (I) are particularly suitable for combating nematodes of maize, in particular Belonolaimus longicaudatus, Paratrichodorus minor and Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, arenaria, Meloidogyne, Meloidogyne arenaria thamesi, graminis Meloidogyne, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, naasi Meloidogyne, Heterodera avenae, Heterodera oryzae,
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of soybean, in particular of Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus and Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus colum
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of the tobacco, in particular Meloidogyne incognita, Meloidogyne javanica and Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatus, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp.,
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of citrus plants, in particular Pratylenchus coffeae and Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita , Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans.
  • the compounds of the formula (I) are particularly suitable for controlling banana nematodes, in particular Pratylenchus coffeae, Radopholus similis and Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp. - -
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of the pineapple, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyuras, Pratylenchus goodeyi., Meloidogyne spp., Rotylenchulus reniformis and Longidoras elongatus, Longidoras laevicapitatus, Trichodoras primitivus, Trichodoras minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopho
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of grapes, in particular Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus Pratylenchus brachyuras, Pratylenchus thornei and Tylenchulus semipenetrans.
  • Pratylenchus vulnus Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus Praty
  • the compounds of the formula (I) are particularly suitable for combating nematodes of tree crops - pome fruit, in particular Pratylenchus penetrans and Pratylenchus vulnus, Longidoras elongatus, Meloidogyne incognita and Meloidogyne hapla.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes of tree crops - stone fruits, in particular Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyuras, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyuram and Hoplolaimus galeatus.
  • the compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops, sugarcane and rice, in particular Trichodoras spp., Criconemella spp. and from Pratylenchus spp. , Paratrichodoras spp., Meloidogyne spp. , Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp. Heterodera spp, Xiphinema spp. and Cacopauras pestis.
  • the term "nematodes" in the present context refers to nematodes that harm humans or animals.
  • Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.
  • 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., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp.
  • Ollulanus spp. For example, from the spout of Spirurida: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa s
  • the present invention also relates to the use of the compounds of formula (I) as anthelmintic drugs.
  • Pathogenic endoparasitic helminths include platyhelmintha (e.g., Monogenea, Cestodes, and Trematodes), Acanthocephala, and Pentastoma. The following helminths are to be mentioned as preferred:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.
  • Cestodes from the order of Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.
  • Trematodes from the class of Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia 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 spp., Fischoederius spp , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis
  • Acanthocephala from the order of Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order of Polymorphida for example: Filicollis spp .; from the order of Moniliformida for example: Moniliformis spp., From the order of Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.
  • Pentastoma from the order of the Porocephalida for example Linguatula spp.
  • the compounds of formula (I) are administered in a known manner, directly or enterally, parenterally, dermally or nasally in the form of suitable forms of application.
  • the administration can be prophylactic or therapeutic.
  • the compounds of formula (I) may optionally also 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.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain 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 vegetable fatty acids such as rape oil or soybean oil methyl esters or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention promoting agents such.
  • dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); 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.
  • suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g.
  • Cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters
  • ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strong polar solvents such as dimethyl sulfoxide and water.
  • 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 foam-producing 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, for example alkylarylpolyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates
  • dyes such as inorganic pigments, e.g. 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.
  • inorganic pigments e.g. 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.
  • 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-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, 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 the formula (I) in the forms of application prepared from the formulations (in particular pest control agents) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence 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.
  • the compounds of formula (I) may be present in admixture with other active ingredients 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, eg 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], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, momfluoroth
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • nAChR nicotinergic acetylcholine receptor
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene 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
  • inhibitors of oxidative phosphorylation, ATP disruptors such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • ATP disruptors such as, for example, diafenthiuron or organotin compounds, eg azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Decoupling of oxidative phosphorylation by interruption of the H proton gradient such as chlorfenapyr, DNOC, and sul
  • 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, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Anti-skinning agents especially in dipterans, i.e., two-wingers, such as cyromazines.
  • 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).
  • voltage dependent sodium channel blockers e.g. Indoxacarb or metaflumizone.
  • (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.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
  • agents with unknown or ambiguous mechanism of action such as afidopyropene, afoxolans, azadirachtin, benclothiaz, benzoximate, bifenazates, broflanilides, bromopropylates, quinomethionate, cryolites, cyclaniliproles, cycloxapride, cyhalodiamides, dicloromethzotiaz, dicofol, diflovidazine, flometoquine, fluazaindolizines, fluensulfones, flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, Lotilaner, Meperfluthrin, Paichongding, Pyflubumide,
  • the drugs specified herein with their "common name” are known, for example as described in the "Pesticide Manual” or on the Internet (for example: http://www.alanwood.net/pesticides). All of the listed five-component mixed partners of classes (1) to (15) can optionally form salts with corresponding bases or acids, provided that suitable functional groups are present. In addition, tautomeric forms are also included for the listed ficcidial mixed partners of classes (1) to (15), provided that tautomerism is possible.
  • inhibitors of ergosterol biosynthesis for example (1.01) aldimorph, (1.02) azaconazole, (1.03) bitertanol, (1.04) bromuconazole, (1.05) cyproconazole, (1.06) diclobutrazole, (1.07) difenoconazole, (1.08) diniconazole, (1.09 ) Dinemonazole-M, (1.10) dodemorph, (1.11) dodemorphoacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis,
  • inhibitors of mitosis and cell division for example (4.01) benomyl, (4.02) carbendazim, (4.03) chlorfenazole, (4.04) diethofencarb, (4.05) ethaboxam, (4.06) fluopicolide, (4.07) fuberidazole, (4.08) pencycuron, (4.09) 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] triazolo [l, 5-a] pyrimidine, (4.14) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6 trifluorophenyl) pyridazine.
  • inhibitors of amino acid and / or protein biosynthesis for example (7.01) andoprim, (7.02) blasticidin-S, (7.03) cyprodinil, (7.04) kasugamycin, (7.05) kasugamycin hydrochloride hydrate, (7.06) mepanipyrim, (7.07) Pyrimethanil, (7.08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (7.09) oxytetracycline, (7.10) streptomycin.
  • inhibitors of ATP production for example (8.01) fentin acetate, (8.02) fentin chloride, (8.03) fentin hydroxide, (8.04) silthiofam.
  • Validamycin A (9.09) Valifenalate, (9.10) Polyoxin B, (9.11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4 -yl) prop-2-en-1-one, (9.12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4- yl) prop-2-ene-1-one.
  • inhibitors of lipid and membrane synthesis for example (10.01) biphenyl, (10.02) chloroneb, (10.03) diclorane, (10.04) edifenphos, (10.05) etridiazole, (10.06) iodocarb, (10.07) Iprobenfos, (10.08)
  • Isoprothiolane (10.09) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene, (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis for example (11.01) carpropamide, (11.02) diclocymet, (1 1.03) fenoxanil, (11.04) phthalide, (11.05) pyroquilone, (11.06) tricyclazole, (11.07) 2,2,2-trifluoroethyl ⁇ 3-methyl-l - carbamate [(4-methylbenzoyl) amino] butan-2-yl ⁇ .
  • inhibitors of signal mediation for example (13.01) chlozolinate, (13.02) fenpiclonil, (13.03) fludioxonil, (13.04) iprodione, (13.05) procymidone, (13.06) quinoxyfen, (13.07) vinclozoline, (13.08) proquinazide.
  • the compounds of formula (I) may be combined with biological pesticides. 5
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. 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: - 5 -
  • 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
  • NPV Africann Cotton worm
  • bacteria and fungi which are added as 'inoculant' plants or plant parts or plant organs and, by virtue of their particular properties, promote 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 products formed by microorganisms including proteins and secondary metabolites, which can be used as biological pest control agents are:
  • the compounds of formula (I) may be combined with safeners such as Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (- ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531-12-0), 4- (dichloroacetyl) - 1-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant parts
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired ones 5
  • Wild plants or crops for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peppers and chilli, cucumbers, melons, carrots, watermelons, Onions, lettuce, spinach, leeks, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plants are to be understood as meaning all stages of development of the plants, for example seeds, cuttings and young (immature) plants through to mature plants.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops (harvested plants or plant parts) as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by 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. 5
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased Abwehr ability of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes, for example.
  • toxins produced in the plants in particular those produced 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 as well as their combinations) in the plants are produced, furthermore an increased from defensive ability of the plants against plant-pathogenic mushrooms, bacteria and / or viruses, causes eg 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 agents, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g., "PAT" gene).
  • SAR systemically acquired resistance
  • systemin phytoalexins
  • elicitors elicitors
  • 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, 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 formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, (spraying) spraying, (spraying), Sprinkling, vaporizing, spraying, misting, sprinkling, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layered Enveloping, etc. It is also possible, the compounds of formula (I) according to the ultra-low-volume method or to inject the use form or compound of formula (I) itself 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 may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site.
  • this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from infestation by pests by treating the seeds with one of the compounds of formula (I).
  • the method according to the invention for protecting seed and germinating plants from infestation by pests further comprises a method in which the seed is cultivated simultaneously or sequentially with a compound of the formula (I) and Mixing partner is treated. 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 which comprise a compound of the formula (I) and mixture 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.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • a compound of 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. 5?
  • the compounds of the formula (I) are suitable 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, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
  • transgenic seed with a compound of 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 useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, 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.
  • 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.
  • 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 under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are 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.
  • 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. 5
  • all substances which can be used for such purposes in agrochemical compositions can be present in the seed dressing formulations which can be used according to the invention.
  • examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed-dressing formulations of the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the 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 at The compound of the formula (I) is 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.
  • 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 are of low toxicity to warm-blooded animals are useful in the control of parasites used in livestock and livestock 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 shellfish, e.g. in aquaculture and also insects like bees.
  • 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, Tb gambiense, Tb 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.
  • Trypanosomatidae for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L.
  • 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, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
  • Eimeridae for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E.
  • gallopavonis E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. sitesdai E. suis, E. tenella, E.
  • S. suihominis such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (e.g., 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
  • Plagiorchis spp. Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
  • 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., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia s
  • 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 in the form of suitable 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.
  • Another aspect in turn relates to the use of a compound of formula (I) as an anti-parasitic, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of formula (I) as an 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.
  • an arthropodicide such as Insecticide or acaricide
  • Anthelminthic agents including trematicide and cestocide agents: from the class of macrocyclic lactones, e.g. Such as: abamectin, doramectin, emamectin, eprinomectin, ivermectin, milbemycin, moxidectin, nemadectin, selamectin; from the class of benzimidazoles and sample zimidazoles, e.g.
  • albendazole albendazole, albendazole sulfoxide, cambendazole, cyclobendazole, febantel, fenbendazole, flubendazole, mebendazole, netobimine, oxfendazole, oxibendazole, parbendazole, thiabendazole, thiophanate, triclabendazole; from the class of cyclooctadepsipeptides, e.g. B: emodepside, PF1022; from the class of aminoacetonitrile derivatives, e.g. For example: Monepantel; from the class of tetrahydropyrimidines, e.g.
  • B . Morantel, Pyrantel, Oxantel; from the class of imidazothiazoles, e.g. B .: butamisole, levamisole, tetramisole; from the class of salicylanilides, e.g. For example: bromoxanide, breadanide, clioxanide, closantel, niclosamide, oxyclozanide, rafoxanide, tribromomalan; from the class of Paraherquamide, z.
  • B . Derquantel, paraherquamide; - 5 - from the class of Aminophenylamidine, z.
  • amidantel deacylated amide shell (dAMD), tribendimidine
  • organophosphates e.g. B .: Coumaphos, Crufomat, Dichlorvos, Haloxon, Naphthalofos, Trichlorfon
  • substituted phenols e.g. Bithionol, disophenol, hexachlorophene, nicolofolan, meniclopholan, nitroxynil
  • piperazinones e.g. B .: praziquantel, epsiprantel; from other diverse classes, eg.
  • amoscanate bephenium, bunamidine, clonazepam, clorsulone, diamfenetide, dichlorophen, diethylcarbamazine, emetine, hetolin, hycanthone, lucanthone, miracil, mirasan, niclosamide, niridazole, nitroxynil, nitroscanate, oltipraz, omphalotin, oxamniquine, paromomycin, piperazine, resorantel ,
  • 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 their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • - Culex Japanese encephalitis, filariasis, other viral diseases, transmission of worms
  • - Aedes yellow fever, dengue fever, filariasis, other viral 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.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. 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.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. 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.
  • Vector control is also possible when the compounds of formula (I) are resistive.
  • 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. Protection of technical 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, ie, it may be readily available n
  • 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.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera , Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out, for example, in aerosols, pressureless sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • aerosols pressureless sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Another aspect of the invention is the use of a compound of formula (I) as a herbicide.
  • reaction Scheme 1 shows a general method for the preparation of the compounds ( ⁇ ') according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • Ei, E2 and E3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to Tl, T2, T3 and T6.
  • U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide.
  • U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate.
  • X stands for F or Cl.
  • a preferred embodiment of compounds of the general structure ⁇ according to the invention are compounds of the general structure Ia according to the invention.
  • Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such.
  • suitable bases such as aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as.
  • dioxane or THF can be obtained.
  • Intermediates of general structure 6 can be obtained by reaction of intermediates of general structure 5 with halogenating agents.
  • halogenating agents for example, N-halosuccinimides are used [see, for example, WO 2009/112845, WO 2012/137181].
  • Compounds of general structure 5 can be prepared by palladium catalyzed reactions from reactants 3 and 4 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocydes 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.].
  • the compounds of general structure 4 are either commercially available or can be prepared by methods known to those skilled in the art [see, e.g. WO2016 / 066697; Eur. J. Med. Chem.
  • the compounds of general structure 3 can be prepared by literature methods from reaction partners of the general structure 1 and 2 [see, for example. WO2014 / 122083; WO 2014/135439; WO2016 / 020441].
  • the compounds of general structure 2 are commercially available.
  • Compounds of general structure 1 can be prepared by methods known to those skilled in the art [see, e.g. WO 2015/181139; WO2016 / 020441].
  • Reaction scheme 1b shows a further process for the preparation of the compounds ( ⁇ ') according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • Ei, E 2 and E 3 stand for N or CH, in each case selected so that the heterocycle represents a five-membered heterocycles according to T 1, T 2 , T 3 and T 6.
  • U is bromine or iodine when M is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide.
  • U is a boronic acid, a boronic acid ester or trifluoroboronate or a zinc halide when M is bromine, iodine or triflate.
  • X stands for F or Cl. Shark stands for Cl, I or 7
  • a preferred embodiment of compounds of the general structure ⁇ according to the invention are compounds of the general structure Ia according to the invention.
  • Carboxylic acids of general structure 7 can be prepared from carboxylic acid esters of general structure 6 analogously to literature methods by means of suitable bases, such as. As aqueous lithium hydroxide or sodium hydroxide solution, in suitable solvents or diluents, such as. As dioxane or THF can be obtained.
  • Compounds of general structure 6 can be prepared by palladium catalyzed reactions from reactants 3 and 16 [see, e.g. WO 2010/071741; WO 2013/170115; Heterocycles 2010, 81, 1509-1516; WO2010 / 093885; US2014 / 0274689; J. Am. Chem. Soc. 2010, 132, 14073-14075; Eur. J. Org. Chem. 2016, 2013-2023.].
  • the compounds of general structure 16 are either commercially available or can be prepared by methods known to those skilled in the art.
  • Compounds of general structure 3 can be prepared analogously to the methods described above.
  • Reaction Scheme 2 shows a general method for the preparation of the compounds (Ib) according to the invention.
  • Alk is a C 1 -C 4 alkyl.
  • Q stands for O.
  • X stands for F or Cl.
  • Intermediates of the general structure 13 may be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Lett., 2009, 50, 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 12 and acetylenes of general structure 10 can be obtained.
  • Compounds of general structure 10 can be obtained by reaction of intermediates of general structure 1 and trimethylsilylacetylene under conditions known from the literature (see, for example, WO2015 / 193218).
  • Scheme 3 depicts a general method for the preparation of the compounds (Ic) according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q is O.
  • X 1 is F or Cl, X 2 is Br or I.
  • Intermediates of the general structure 20 can be prepared by Cu-catalyzed (eg Chem. Asian ./. 2013, 8, 800-808, Tetrahedron Lett. 2012, 53, 1606-1609) or thermal (eg Tetrahedron Letl, 2009, 50 , 2358-2362; Eur. J. Org. Chem. 2010, 1875-1884). Reaction of azides of general structure 17 and acetylenes of general structure 19 can be obtained. Intermediates of general structure 17 can be obtained in analogy to processes known from the literature starting from halides of general structure 1 by reaction with sodium azide (for example US2017 / 112129 A1, WO2012 / 80376 Al). Halides of general structure 1 are commercially available or can be prepared by methods known to the person skilled in the art.
  • Reaction Scheme 4 depicts a general method for the preparation of the compounds (Id) according to the invention. Reaction scheme 3
  • oximes 24 are first treated with suitable halogenating agents, e.g. N-halosuccinimides and then reacted with acetylenes 10 in the presence of a suitable base, e.g. Triethylamine (e.g., WO2015 / 150442).
  • suitable halogenating agents e.g. N-halosuccinimides
  • acetylenes 10 in the presence of a suitable base, e.g. Triethylamine (e.g., WO2015 / 150442).
  • Oximes of the general structure 24 are known or can be prepared from aldehydes of the general structure 23 analogously to literature methods (eg Bull. Chem. Soc., 1985, 58, 352-360; J. Chem. Soc., Perk. Trans 1 1980, 4, 1029-1037). Aldehydes of general structure 23 are commercially available or can be prepared by methods known to those skilled in the art. ?
  • Reaction Scheme 5 depicts another general method for the preparation of the compounds (Id) and (Ie) according to the invention.
  • Alk is a C 1 -C 4 -alkyl.
  • Q stands for O.
  • X stands for I, Br or Cl.
  • the regioisomeric intermediates of general structure 31 or 31 ' can be prepared analogously to processes known from the literature by condensation of intermediates of general structure 30 Hydroxylamine or its hydrochloride are obtained (eg Eur. J. Med. Chem. 2016, 117, 85-98, WO2009 / 029632).
  • Intermediates of general structure 29 can be prepared after deprotonation with a suitable base, e.g. NaH or NaOMe can be converted to intermediates of general structure 30 by reaction with intermediates of general structure 28 (eg Eur. J. Med. Chem. 2016, 117, 85-98; Adv. Synth. Catal. 2016, 358, 2811-2816 ).
  • Intermediates of general structure 28 and 29 are either commercially available or can be prepared by methods known to the person skilled in the art or known from the literature.
  • Step 1 Preparation of 2 , -methyl-5 , - (pentafluoroethyl -4- (4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl-4 , - (trifluoromethyl-2 , H -L3 , -bipyrazole
  • Step 2 Preparation of methyl 5- , 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H-L3 , - bipyrazol-4-yl-thiophene-3-carboxylate
  • N-iodosuccinimide (159 mg) is added and the mixture is stirred overnight at 50 ° C.
  • the reaction mixture is cooled to room temperature, diluted with EtOAc and washed successively with saturated aqueous NaHSO 3 solution, water, saturated aqueous NaHCO 3 solution and saturated aqueous NaCl solution.
  • the solvent is removed under reduced pressure and the residue is purified by HPLC (gradient: H 2 O / acetonitrile).
  • Step 4 Preparation of 2-iodo-5- ⁇ 2 , -methyl-5 , - (entafluoroethyl) -4 , - (trifluoromethyl) -2 , H, 3 , -bipyrazol-4-yl-thiophene-3-carboxylic acid.
  • reaction mixture is stirred at 60 ° C for 1.5 h.
  • the reaction solution is cooled to room temperature, diluted with EtOAc and washed with aqueous HCl (IM) and saturated aqueous NaCl solution.
  • IM aqueous HCl
  • the organic phase is dried over MgSC and the solvent removed under reduced pressure.
  • 2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H, 1,3'-bipyrazol-4-yl] thiophene-3-carboxylic acid becomes a yellow solid received (217 mg) and used without further purification in the subsequent reaction.
  • the reaction mixture is diluted with CH 2 CI 2 and washed with HCl (IN).
  • the organic phase is dried over MgSC and the solvent is removed under reduced pressure.
  • the residue is purified by HPLC (gradient: H 2 O / acetonitrile) and N-cyclopropyl-2-iodo-5- [2'-methyl-5 '- (pentafluoroethyl) -4'- (trifluoromethyl) -2'Hl, 3'-bipyrazol-4-yl] thiophene-3-carboxamide (Ia-1) is obtained as a colorless solid (80 mg).
  • Step 1 Preparation of 5-azido-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
  • Methyl 5-bromothiophene-3-carboxylate (1 g) is placed under argon in argon-saturated N, N-dimethylformamide (7 mL) and triethylamine (5.08 g).
  • bis (triphenylphosphine) palladium (II) dichloride 143 mg
  • copper (I) iodide (19 mg) are added and the reaction mixture is stirred at 80 ° C for 4 h.
  • the reaction solution is added after cooling with ethyl acetate and washed with HCl solution (5%) and aqueous saturated sodium chloride solution.
  • the organic phase is dried and freed from the solvent under reduced pressure.
  • Step 3 Preparation of methyl 5- ⁇ 1-ri-methyl-3- (pentafluoroethyl-4-trifluoromethyl-1H-pyrazol-5-yl-1H-1,2,3-triazol-4-yl ⁇ thiophene 3-carboxylate
  • the reaction solution from step 1 is diluted with water (3.5 mL). Methyl-5-ethynylthiophene-3-carboxylate (861 mg), copper (II) sulfate pentahydrate (90.5 mg), sodium ascorbate (71.8 mg) and tris [(1-benzyl-1H-1,2,3-triazole-4 -yl) methyl] amine (19.2 mg) is added and it is stirred at room temperature until the product from step 1 is completely reacted. The reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and freed from the solvent under reduced pressure.
  • Step 4 Preparation of methyl 2-chloro-5- ⁇ 1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole 4-yl ⁇ thiophene-3-carboxylate
  • Methyl 5- ⁇ 1- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazol-4-yl ⁇ thiophene-3 carboxylate (302 mg) is charged in acetic acid, N-chlorosuccinimide (127 mg) is added and the mixture is stirred for 4 h at room temperature. It is then heated to a bath temperature of 50 ° C and stirred overnight. The reaction mixture is diluted with ethyl acetate and washed with aqueous sodium thiosulfate solution and aqueous saturated sodium chloride solution.
  • Step 5 Preparation of 2-chloro-5- ⁇ 1-ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-4-yl ⁇ thiophene-3-carboxylic acid methyl 2-chloro-5- ⁇ 1- [l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -LH-l, 2,3- Triazol-4-yl ⁇ thiophene-3-carboxylate (128 mg) is initially charged in tetrahydrofuran, an aqueous solution of lithium hydroxide (0.72 mL, 1M) is added dropwise and it is left overnight at room temperature touched.
  • lithium hydroxide (0.72 mL, 1M
  • Step 6 Preparation of 2-chloro-N-cyclopropyl-5- ⁇ 1 -ri-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazole 4-yl ⁇ thiophene-3-carboxamide (Ib-4)
  • Step 1 Preparation of 5-ethynyl-1-methyl-3- (pentafluoroethyl -4- (trifluoromethyl-1H-pyrazole
  • Ethinyl (trimethyl) silane 750 mg is placed under argon in tetrahydrofuran (12 mL) and cooled to -78 ° C.
  • n-Butyllithium (3.58 mL, 1.6M) is added dropwise and it is stirred for 5 minutes at -78 ° C.
  • 5-fluoro-l-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole (1.09 g) is added dropwise and stirred for 30 minutes at 0 ° C and 60 minutes at room temperature. The reaction is cooled again to -78 ° C and terminated by adding water.
  • Step 3 Preparation of methyl 5- ⁇ 4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-L2,3-triazol-1-yl ⁇ thiophene -3-carboxylate
  • Methyl 5-azidothiophene-3-carboxylate (426 mg) is initially charged in dimethyl sulfoxide (4 mL) and water (2 mL), 5-ethynyl-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -H-OH.
  • pyrazole (815 mg)
  • Step 4 Preparation of methyl 2-chloro-5- ⁇ 4 1 -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl-1H-1,2,3-triazole-1 -yl ⁇ thiophene-3-carboxylate
  • reaction mixture is heated to 50 ° C bath temperature and stirred for a further 5 h.
  • N-chlorosuccinimide 37 mg
  • N-chlorosuccinimide 74 mg
  • 80 ° C for 6 h 80 ° C for 6 h.
  • N-chlorosuccinimide 74 mg
  • the reaction mixture is diluted with ethyl acetate and washed with aqueous saturated sodium chloride solution.
  • the organic phase is dried, filtered and evaporated from the solvent under reduced pressure.
  • the residue is purified by means of pHPLC (gradient: acetonitrile / water).
  • Step 5 Preparation of 2-chloro-5- ⁇ 4- [l -methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-1,2,3-triazole 1 -yl ⁇ thiophene-3-carboxylic acid
  • 3-Ethylcarbodiimide hydrochloride (94 mg) are introduced into dichloromethane (5 mL) and N, N-dimethylformamide (0.5 mL) and stirred for 15 minutes at room temperature. Then cyclopropylamine (28 ⁇ .) was added and stirred overnight at room temperature. The reaction mixture is diluted with dichloromethane and washed with HCl solution (I.M.). The organic phase is dried and removed from the solvent under reduced pressure.
  • Step 1 Preparation of ethyl 5-chloro-2- ⁇ 2 , -methyl-5 , - (pentafluoroethyl) -4 , - (trifluoromethyl) -2 , H- ⁇ L3 , - bipyrazol-4-yl-L3-thiazole-4 carboxylate
  • reaction vail is then sealed and stirred overnight at room temperature.
  • the reaction mixture is filtered through silica gel and rinsed with ethyl acetate.
  • the filtrate is diluted with ethyl acetate and washed with water and aqueous saturated sodium chloride solution.
  • the organic phase is dried, filtered and freed from the solvent under reduced pressure.
  • the residue is purified by flash chromatography (gradient: c-hexane / ethyl acetate).
  • Step 2 Preparation of 5-chloro-2- ⁇ 2, methyl-5 - (pentaf ⁇ uorethyl) -4 - (trifluoromethyl) -2, H- ⁇ L3, - bipyrazoll-4-yll-L3-thiazole-4-carboxylic acid ethyl 5-chloro-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [l, 3'-bipyrazol] -4-yl] -l, 3- thi
  • Step 3 Preparation of 5-chloro-N-cyclopropyl-2- [2 , -methyl-5 , - (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H- [L3'-bipyrazol-4-yl-L3 thiazole-4-carboxamide
  • reaction mixture is treated with diatomaceous earth and freed from the solvent under reduced pressure to be purified by flash chromatography (gradient: c-hexane / ethyl acetate).
  • 5-Chloro-N-cyclopropyl-2- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- [1,3'-bipyrazol] -4-yl] - l, 3-thiazole-4-carboxamide (73 mg) as a colorless solid.
  • Agilent 1100 LC system 50 * 4.6 Zorbax Eclipse Plus C18 1.8 microm; Eluent A: acetonitrile (0.1% formic acid); Eluent B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for a further 1.25 min; Oven temperature 55 ° C; Flow: 2.0 mL / min. Mass detection takes place via an Agilend MSD system.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; ⁇ 2 (intensity);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of IH NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation. In addition, they can, like classical 1H-NMR prints solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
  • 1 ⁇ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not 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.
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
  • the vials are populated with 5-10 adult dog tick ⁇ Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated. Ticks that remain immobile on the ground or move so uncoordinated that they can not deliberately avoid the heat by climbing up, are considered dead or struck.
  • a substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.
  • 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 Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • 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.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • Emulsifier alkylaryl polyglycol ether 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 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
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration. ?
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water until the desired concentration is reached. 50 ⁇ of the active ingredient preparation are transferred into microtiter plates and filled with 150 ⁇ l IPL41 insect medium (33% + 15%> sugar) to a final volume of 200 ⁇ . Subsequently, the plates are sealed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution. After 5 days, the effect is determined in%. 100% means> that all aphids have been killed; 0% means that no aphids have been killed.

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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Diabetes (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
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Abstract

L'invention concerne entre autres des composés de formule générale (I). L'invention concerne également des procédés de préparation des composés de formule (I). Les composés selon l'invention sont particulièrement adaptés à la lutte contre les insectes, les arachnides et les nématodes en agriculture, et contre les ectoparasites en médecine vétérinaire.
PCT/EP2018/057612 2017-03-31 2018-03-26 Pyrazoles pour lutter contre les arthropodes WO2018177993A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021239835A1 (fr) * 2020-05-27 2021-12-02 Vetoquinol Sa Procédé de préparation de 2-chloro-n-(1-cyanocyclopropyle)-5-[2'-méthyl-5'-(pentafluoroéthyl)-4'- (trifluorométhyl)-2'h-1,3'-bipyrazol-4-yl]benzamide

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021239835A1 (fr) * 2020-05-27 2021-12-02 Vetoquinol Sa Procédé de préparation de 2-chloro-n-(1-cyanocyclopropyle)-5-[2'-méthyl-5'-(pentafluoroéthyl)-4'- (trifluorométhyl)-2'h-1,3'-bipyrazol-4-yl]benzamide
CN115605468A (zh) * 2020-05-27 2023-01-13 威隆股份公司（Fr） 用于制备2-氯-n-(1-氰基环丙基)-5-[2’-甲基-5’-(五氟乙基)-4’-(三氟甲基)-2’h-1,3’-联吡唑-4-基]苯甲酰胺的方法

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