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WO2017097870A1 - Amides d'acide malonique substitués utilisés comme insecticides - Google Patents

Amides d'acide malonique substitués utilisés comme insecticides Download PDF

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Publication number
WO2017097870A1
WO2017097870A1 PCT/EP2016/080166 EP2016080166W WO2017097870A1 WO 2017097870 A1 WO2017097870 A1 WO 2017097870A1 EP 2016080166 W EP2016080166 W EP 2016080166W WO 2017097870 A1 WO2017097870 A1 WO 2017097870A1
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alkyl
spp
cyano
alkoxy
nitro
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English (en)
Inventor
Markus Heil
Michael Maue
Laura HOFFMEISTER
Kerstin Ilg
Daniela Portz
Bernd Alig
Silvia Cerezo-Galvez
Sascha EILMUS
Ulrich Görgens
Andreas Turberg
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Bayer CropScience AG
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel substituted malonic acid amides, processes for their preparation and their use for controlling animal pests, especially arthropods and in particular insects, arachnids and nematodes.
  • WO2009099929 described as an intermediate for insecticidal agents.
  • Other substituted malonic acid amides having insecticidal properties are known from JP2013241403.
  • the active ingredients known according to the above-mentioned publication have some drawbacks in their application, whether they have only a small application range, whether they have no satisfactory insecticides or acaricidal activity.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity.
  • A stands for O or S,
  • GG-haloalkoxy-GG-alkyl GG-aikoxy-GG-alkyloxy, cyano-GG-alkyl.
  • GG-cycloalkyl-GG-alkyl C 2 -C 6 -alkenyl, GG-alkynyl, C 1 -C 4 -alkyl-S (0) p -, GG-alkylcarbonyl, GG-cyclioalkylcarbonyl, GG-alkenylcarbonyl, GG-haloalkylcarbonyl , C 1 -C 6 -alkoxycarbonyl, C 1 -G -alkoxyimino-G-alkyl, GG-haloalkylsulfonyl, GG-alkylaminocarbonyl or di- (C 1 -C 6) -alkylaminocarbonyl, for GG-alkyl, GG-alkenyl or GG- Alkynyl, where the
  • Ci-C 4 alkyl-S (0) p -, C 4 -Haiogenalkoxy, Ci-C 4 haloalkyl-S (0) p -, nitro or cyano can be substituted
  • E represents the radicals O, N-OR 2 N-CN, and NN (R 3 ) (R 4 ),
  • C 1 -C 4 -alkyl, G-G; -haloalkyl, G-G; -alkoxy or GG-haloalkoxy may be substituted and wherein the ring N atoms in U-17, U-18, U-19, U-26, U-27 and U-28 are not halogen, nitro, OH.
  • C 1 -C 6 -alkylthio, GG-alkylsulfmyl, (C 1 -C 6 -alkoxy-C; -g-alkyloxy are substituted,
  • R 1 is a radical from the group consisting of hydrogen, halogen, cyano, nitro, SF 5 , SCN, amino, GG-alkylamino, di (GG) -alkylamino, hydroxy, COOK, GG-alkyl, GG-cycloalkyl, GG-haloalkyl , G-G-alkoxy, GG-haloalkoxy, GG-halocycloalkyl, GG-alkoxy-GG-alkyl, G-C-haloalkoxy-GG-alkyl.
  • G-Ce-alkylcarbonyl C 3 -C 6 -cycloalkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylamino carbonyl, di- ( G-C6) -alkylaminocarbonyi, aryl, hetaryl, aryl-G -C-alkyl] or hetaryl-GG-aikyl, where aryl, hetaryl, aryl-G -Ct-alkyl and hetaryl-G-Ci-alkyl optionally simple or multiply, identically or differently, by halogen, cyano, nitro, hydroxy, G-Ce-acyl, GG-alkenyl, C 2 -C 6 -alkynyl,
  • Haloalkoxy or G-G-Aikylthio can be substituted
  • R la is GG-alkyl
  • R 2 is hydrogen or G-G-alkyl, GG-alkenyl, GG-alkynyl, Cs-Ce-cycloalkyl or C ; G-cycloalkyl-G - - alkyl, wherein the aforementioned radicals optionally independently of one another monosubstituted to trisubstituted by halogen or simply by nitro, cyano, GG-alkoxy, GG-Halogenaikoxy or GC 4 -Alkyi-S (0) p can be, or is aryl, hetaryl, aryl -G -G-A Ikyl or hetaryl-GG-alkyl, where the abovementioned radicals are optionally independently of one another mono- to trisubstituted by halogen, G-alkyl, GG-haloalkyl, G -G Alkoxy, GC 4 -Alkyi-S (0) p -, GG-halo
  • R 3 is hydrogen or G-Galkyl, GG-alkenyl, GC-alkynyl, C 3 -C 6 -cycloalkyl or C-G-cycloalkyl-G-G-alkyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen or simply by cyano, nitro, hydroxy, G-alkyl, GG-cycloalkyl, G-alkoxy, GG-haloalkoxy, GC 4 -alkyl-S (O) p -, G-Ce-alkoxycarbonyl or GG Alkylcarbonyl may be substituted, or
  • R 3 for aryl, hetaryl.
  • R 4 represents hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -G-Alkinyi, GG-Cyc oalkyi, Ci-C 4 alkoxy, Ci-C4-alkoxy-Ci-C6 aikyl, GG-alkoxycarbonyl, GG-alkylcarbonyl, GG-alkylsulfonyl, arylcarbonyl, arylsulfonyl or hetarylcarbonyl, wherein arylcarbonyl, arylsulfonyl and hetarylcarbonyl are in each case monosubstituted to trisubstituted by halogen, cyano, nitro, GC; -alkyl, GG-haloalkyl, Ci -C 4 -alkoxy or GC 4 -Haioalkoxy may be substituted, or
  • R 3 and R 4 may be connected to each other via two to six carbon atoms and form a ring which optionally additionally contains another atom from the series OS or N and which optionally monosubstituted to fourfold with G-alkyl, halogen, cyano, amino or GG alkoxy can be substituted,
  • R 3a and R 4a independently of one another represent hydrogen, GG-alkyl, GG-alkenyl, C 2 -C 6 -alkynyl, G-G-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl , GG-alkoxyearbonyl, GG-alkylcarbonyl, GG-alkylsulfonyl, arylcarbonyl, arylsulfonyl or hetarylcarbonyl, where, arylcarbonyl, arylsulfonyl or hetarylcarbonyl in each case monosubstituted to trisubstituted by halogen, cyano, nitro, GC 4 -alkyl, GC 4 -haloalkyl, GC 4 Alkoxy or GC 4 -Ha! Oalkoxy can be substituted,
  • CVCV alkyl is hydrogen or GG-Aikyi, C 2 -C 6 -alkenyl, C, where the aforementioned radicals is optionally mono- to trisubstituted by halogen or may be substituted by nitro, cyano, iC, - alkoxy, G-Ce-haloalkoxy or GC 4 -alkyl-S (0) p -, or aryl, hetaryl, aryl-CVCi-alkyl or hexyl aryl -C: -C -a is 1 ky 1, where the aforementioned radicals is optionally mono- to trisubstituted independently of one another by halogen, Ci-C 4 alkyl, GC 4 - haloalkyl, GC 4 alkoxy, GC 4 alkyl-S (0 ) p
  • R 7a , R 7b , R 7c independently of one another are C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or aryl, where aryl may optionally be monosubstituted to trisubstituted and the substituents independently are selected from among halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl! or C 1 -C 4 -alkoxy,
  • R 9 is hydrogen, fluorine, chlorine, GC 4 -alkyl, C 3 -C 6 -cycloalkyl or GC 4 -Haioaikyi
  • R 9a is hydrogen, fluorine, chlorine.
  • R ! 0 is hydrogen, fluorine, chlorine or GC 4 alkyl
  • R 10a is hydrogen, fluorine, chlorine or GC 4 alkyl m is 0,1,2 or 3
  • n is 0,1, 2 or 3
  • p is 0,1 or 2.
  • the compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
  • the substituted malonic acid amides are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below.
  • Preferred (embodiment 2-1) are the compounds of formula (I) in which
  • A stands for O or S,
  • Q is one of Ql, Q-5 or Q-6, is phenyl, pyridyl, pyrimidinyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, or furanyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen, cyano, nitro, SF 5 , hydroxy, amino, C 1 -C 4 -alkyl, G -C 1 Haloalkyl, G-G-alkoxy, G-G-haloalkoxy.
  • Ci-C4-Aikyl-S (0) p -, C 2 -C 6 -alkoxycarbonyl or C 2 -C 6 -alkylcarbonyl may be substituted for T 1 , when A is O, or T 2 , when A is S is C 1 -C 4 -alkyl, GG-alkenyl or C 2 -C 6 -alkynyl, where the abovementioned radicals are represented by a substituent selected from cyano, nitro, hydroxy, C (O) OR 2 , OC (O) R 5 , S (0) p R 6 , Si (R 7a ) (R 7b ) (R 7c ) are substituted, or is C: -G -Alkenvl or G-CVAlkinyl, where the aforementioned radicals optionally independently of one another from one to three times by halogen or for phenylmethyl, phenylethyl, phenylpropyl, bisphen
  • Ci-C 4 alkoxy, Ci-C 4 -Haioaikoxy, Ci-C 4 -alkyl-S (0) p -, GG Alkoxycarbonyi or C2-C4-alkylcarbonyl can be substituted or for GG-cycloalkyl, C 3 - C 6 -Cycloalkenyl, C 4 -C 3 bicycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 4 alkyl, azetidinyl, oxetanyl, oxolanyl, oxanyl. Dioxanyl.
  • T 2 is phenylmethyl, phenylethyl, phenyipropyl, pyridylmethyl, pyrimidinylmethyl, thiazolylmethyl, oxazolylmethyl, pyra / olylmethyl.
  • Ci-C 4 alkoxy, Ci-C 4 -Haioalkoxy, Ci-C 4 alkyl-S (0) p -, C 2 -C 6 alkoxycarbonyl or C 2 - may be substituted Ci-alkylcarbonyl, or T 2 for C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl or C 4 -C 8 -bicycloalkyl, where the abovementioned radicals, where appropriate, independently of one another, may be monosubstituted to trisubstituted by halogen or simply by cyano, nitro, SF 5 , hydroxy, amino , Ci-C 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy, C CVHaloalkoxy.
  • X a is halogen, nitro, cyano, SF 5, C 4 -Alkyi, Ci-C 4 haloalkyl, GC 4 alkoxy, GC 4 - haloalkoxy, Ci-C4-alkoxy-Ci-C 4 alkyl, cyano-Ci-C 4 alkyl, C 2 C 4 alkenyl, C 3 -C 4 alkynyl, Ci-C 4 alkyl-S (0) p, Ci-C4-alkylcarbonyl, alkoxycarbonyl GC 4 , Ci-C4-alkoxyimino-Ci-C 4 - alkyl or Ci-C4-haloalkylsulfonyl group,
  • R 1 4 -Alkyi, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 is halo, nitro, cyano, GC - haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, cyano -C id-alkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl, Ci-C 4 alkyl-S (0) p -, Ci-C4-alkylcarbonyl, Ci-C 4 -Aikoxycarbonyl or C 1 -C 4 alkoxyimino-C 1 - C 4 -alkyl, R la for Ci-C4-alkyl;
  • R 2 is hydrogen, C 1 -C 4 -alkyl, GC 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-Ci C 4 alkyl, phenyl, pyridyl, phenylmethyl or pyridylmethyl, wherein phenyl, pyridyl, phenylmethyl and pyridylmethyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, GC 4 -alkyl, GC 4 -haloalkyl, C s -C 1 -alkoxy or GC 4 -Hioiogenalkoxy can be substituted, R 5 is hydrogen, G-CVAlkyl, Ci-C 4 haloalkyl, C 3 -C, phenyl, pyr
  • R 6 is C 1 -C 4 -alkyl, GC 4 -Haiogenalkyl, GG-cycloalkyl, phenyl or phenylmethyl, where phenyl and phenylmethyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, C 1 -C 4 -alkyl, GC 4 -haloalkyl, C 1 -C 4 -alkoxy, GC 4 - haloalkoxy, C 1 -C 4 -alkyl-S (0) p - or C 1 -C 4 -alkoxycarbonyl may be substituted, R 7a , R 7b , R 7c independently each other represents GC 4 alkyl,
  • R 9 is hydrogen, fluorine, chlorine or G -C -alkyl
  • R'o f lir hydrogen, fluorine, chlorine or GC 4 alkyl, m is 0,1,2 or 3; n is 0,1, 2 or 3, and p is 0,1 or 2.
  • Q is one of Ql, Q-5 or Q-6;
  • Y is phenyl, pyridyl, pyrimidinyl, thiazyl, oxazolyi, pyrazolyl, thienyl or furanyl, where the abovementioned radicals are optionally monosubstituted to trisubstituted by halogen, cyano, nitro, SF 5, hydroxy, amino, G -CVAlkyl, GC 4 haloalkyl, Ci-C 4 alkoxy, GC 4 -haloalkoxy, C 1 -C 4 alkyl-S (0) p T, C2-C6-alkoxycarbonyl, GG-alkylcarbonyl, T is T 1 , when A is O, or T is T 2 , when A is S, is (s-C 1-6 -alkyl, C: -G, -alkenyl or C.-C, -alkynyl, where the abovement
  • T is etrahydropyranylmethyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen, cyano, nitro, SF% hydroxy, amino, GC 4 -alkyl, GC 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy , C 1 -C 4 -alkyl-S (0) p -, C 2 -C 6 -alkoxycarbonyl or C 2 -C 4 -alkylcarbonyl, for phenylmethyl, phenylethyl, phenylpropyl, pyridylmethyl, pyrimidinylmethyl, thiazolylmethyl, oxazolylmethyl, pyrazolylmethyl, Thienylmethyl, furanylmethyl or furanonylmethyl, where the abovementioned radicals, where appropriate, independently
  • Ci-C 4 -Aikoxy, j -CVHaloalkoxy Ci-C 4 -Aikoxy, j -CVHaloalkoxy.
  • C 1 -C 4 -alkyl-S (0) p, C 2 -C 6 -alkoxycarbonyl or C 2 -C 4 -alkylcarbonyl may be substituted, or
  • T 2 is Cs-Ce-cycloalkyl, C 3 -C 6 -cycloalkenyl or CVCs-bicycloalkyl, where the abovementioned radicals, where appropriate, independently of one another, are monosubstituted to trisubstituted by halogen or simply by cyano, nitro, SF 2, hydroxy, amino, C 2 -C 4 -alkyl, G - VHaloalkyl, GC 4 -alkoxy, Ci-C4-haloalkoxy, Ci-C 4 alkyl-S (0) p -, C 2 -C 6 -Aikoxycarbonyl, C 2 -C 4 -
  • Alkylcarbonyl may be substituted
  • U is a cycle of the series U-2, U-4, U-5, U-6, U-9, U-20, U-23, U-24 or U-25,
  • X a is halogen, nitro, cyano, SF 5, C 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, GC 4 - Halogenaikoxy, Ci-C 4 -alkoxy-Ci-C 4 - Alkyl, cyano-Ci-C 4 -alkyl, C 2 -C 4 -Aikenyi, C -.- ( ' . ⁇ .- Al kinyl.
  • R 1 is halogen, nitro, cyano, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy, GC 4 - haloalkoxy, i -CVAlkoxy-C; -CValky !, cyano-Ci-C 4 alkyl, C.-C alkenyl, C3-C4-alkynyl, Ci-C 4 -alkyl-S (0) p, ⁇ , -C 4 - 1 A kl carbon I, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkoxyimino-C i -
  • R la is 4 -alkyl represents C-C
  • R 2 represents hydrogen, Ci-C 4 -Alkyi, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-Ci-C 4 - alkyl.
  • R 5 is hydrogen, GC 4 -alkyl, Ci-C 4 -Halogenaikyl, C 3 -C 6 cycloalkyl, C 3 -Ce-Cy cloalky 1-C i -C 4 - alkyl, phenyl, pyridyl, phenylmethyl or pyridylmethyl where phenyl, pyridyl, phenylmethyl and pyridylmethyl optionally mono- or polysubstituted by identical or different halogen, cyano, nitro, GC 4 -alkyl, GC 4 -haloalkyl, GC 4 -alkoxy, GC 4 -haloalkoxy, GC 4 -alkyl-S (0) p - or C i -C 4 -alkoxycarbonyl may be substituted,
  • R 6 is Cr (--Alcyl, GC 4 -haloalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenylmethyl, where phenyl and phenylmethyl are optionally mono- or polysubstituted, identical or different, by halogen, cyano, nitro, GC 4 -alkyi , GC 4 -Haiogenaikyl, GC 4 -Aikoxy, GC 4 -
  • Haloalkoxy, C 1 -C 4 -alkyl-S (0) p - or C i -C 4 -alkoxycarbonyl may be substituted, R 7a , R 7b , R 7c independently of one another for CVC i-Alky! stand,
  • R 9 is hydrogen, fluorine, chlorine or G-CValkyl
  • R ! 0 is hydrogen, fluorine, chlorine or C 1 -C 4 -alkyl, m is 0, 1, 2 or 3, n is 0, 1, 2 or 3, and p is 0, 1 or 2.
  • A is O
  • Q is one of the radicals Q-1, Q-5 or Q-6,
  • Y is phenyl, pyrazolyl or thienyl, where the abovementioned radicals can optionally be monosubstituted to trisubstituted, identically or differently, and the substituents are selected independently of one another from halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl.
  • G is -G-alkoxy, C; -Ci-Ha! Oa! Koxy.
  • C 1 -C 4 -alkyl-S (0) p C 1 -C 4 -alkoxycarbonyl or C 2 -C 4 -cycloyl-carbonyl
  • T is T ',
  • T 1 is G-G-alkyl, CC-alkenyl or GG-alkynyl, where the abovementioned radicals are represented by a substituent from the series cyano, nitro, hydroxy, C (O) OR 2 , OC (O) R 5 , S ( 0) p R 6 , Si (R 7a ) (R 7b ) (R 7c ) are substituted, or T 1 is C 2 -C 6 alkenyl or GG-alkynyl, where the abovementioned radicals are optionally mono- to trisubstituted by halogen or may be monosubstituted by GG-alkoxy or G-G-halogeno, or
  • T 1 is phenylmethyl, phenylethyl, phenylpropyl, bis-phenylmethyl, pyridylmethyl, pyrimidinylmethyl, thiazolylmethyl, oxazolylmethyl, pyrazolylmethyl, thienylmethyl,
  • Furanylmethyl or furanonylmethyl where the abovementioned radicals can optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or isopropyl, trifluoromethyl, Difluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl, ethoxycarbonyl, or
  • T 1 represents cyclopropyl, cyclobutyl, cyclohexyl, cyclohexenyl, bicycloheptane, azetidinyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, oxothiethanol, dioxothiethanol, thianyl.
  • Bromine cyano, nitro, methyl, ethyl, n- or iso-propyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl or
  • G is -C (R 9 ) (R ! 0 ) -
  • U is a cycle of the series U-2, U-9 or U-23,
  • X a is halogen, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl,
  • R la is methyl or ethyl
  • R - is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
  • I is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, Cs-Ce-Cycioaikyi, phenyl, pyridyl, phenylmethyl or pyridylmethyl, wherein phenyl , Pyridyl, phenylmethyl and pyridylmethyl may optionally be monosubstituted to trisubstituted and the substituents are independently selected from fluorine, chlorine.
  • Bromine cyano, nitro, methyl, ethyl, n- or iso-propyl, Trifluoromethyl, difluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl or ethoxycarbonyl,
  • R is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, phenyl or phenylmethyl, where phenyl and phenylmethyl may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another from fluorine, chlorine, bromine, cyano,
  • R “, R 7b , R 7c independently of one another represent methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl,
  • R ' is hydrogen, fluorine, methyl or ethyl
  • R 10 is hydrogen, fluorine or methyl, m is 0,1,2 or 3, n is 0,1,2 or 3, and p is 0,1 or 2.
  • A stands for O or S,
  • Q is one of the radicals Q-1, Q-5 or Q-6
  • Y is phenyl, pyrazolyl or thienyl
  • the abovementioned radicals may optionally be monosubstituted to trisubstituted by identical or different substituents and the substituents are selected independently of one another Halogen, cyano, nitro, C 2 -C 4 -alkyl, C 1 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C -haloalkoyl.
  • T is T 1 , when A is O, or
  • T is T 2 when A is S, represents (s-Ci-alkyl, C; -G, alkenyl or C.-CY-alkynyl, where the abovementioned radicals by a substituent from the series cyano, nitro, hydroxy, C (0) OR 2 , OC (0 ) R 5 , S (0) p R 6 , Si (R 7a ) (R 7b ) (R 7c ) are substituted, or represents C 2 -C 6 alkenyl or C; -G alkynyl, where the abovementioned radicals are optionally simple up to three times by halogen or simply by G-Ce-Aikoxy or G-Ce-haloalkoxy, or is phenylmethyl, phenylethyl, phenylpropyl, bis-phenylethyl, pyridylmethyl, pyrimidinylmethyl, thiazolylmethyl, oxazolylmethyl, pyrazoly
  • Trifluoromethyl difluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl or ethoxycarbonyl,
  • G is -C (R 9 ) (R 10 ) -,
  • U is a cycle of the series U-2, U-4, U-5, U-9, U-23, U-24 or U-25,
  • X represents halogen, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl,
  • R 1 is halogen, cyano, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl, trifluoromethyl, methoxy, ethoxy, n-, iso-propoxy, trifluoromethoxy, methylthio, ethylthio, Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or methoxycarbonyl,
  • R la is methyl or ethyl
  • R is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
  • R 5 is hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, C 3 -C 6 -cycloalkyl, phenyl, pyridyl, phenylmethyl or pyridylmethyl, where Phenyl, pyridyl, phenylmethyl and pyridylmethyl may optionally be monosubstituted to trisubstituted and the substituents are independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, n- or iso-propyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methoxy , Ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsul
  • R ' is methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, phenyl or phenylmethyl, where phenyl and phenylmethyl may optionally be monosubstituted to trisubstituted and the substituents are selected independently of one another made of fluorine, chlorine. Bromine.
  • Cyano nitro, methyl, ethyl, n- or iso-propyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl or ethoxycarbonyl,
  • R 7a , R 7b , R 7c independently of one another are methyl, ethyl, n- or isopropyl. n-, iso-, sec- or tert-butyl,
  • R 9 is hydrogen, fluorine, methyl or ethyl
  • R 10 is hydrogen, fluorine or methyl
  • m is 0,1,2 or 3
  • n is 0,1,2 or 3
  • p is 0,1 or 2.
  • Particularly preferred (embodiment 4-1) are the compounds of the formula (I) in which A is O,
  • Q is one of the radicals Q-1 or Q-6,
  • Y is optionally monosubstituted to trisubstituted by identical or different substituents, the substituents being selected independently of one another from fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy and methylthio,
  • T stands for T 1 ,
  • T 1 is phenylmethyl, pyrid-2-ylmethyl, pyrid-3-ylmethyl or pyrid-4-ynamethyi, where the abovementioned radicals can optionally be monosubstituted to trisubstituted and substituents are independently selected from fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfmyl or
  • U is a cycle of the series U-2, U-9 or U-23,
  • X a represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
  • R 1 for fluorine, chlorine. Bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio,
  • R ia is methyl
  • R 9 is hydrogen or methyl
  • R 10 is hydrogen
  • m is 0.1 or 2
  • n is 0, 1 or 2.
  • A is O or S
  • Q is one of the radicals Q-1 or Q-6
  • Y is optionally monosubstituted to trisubstituted by identical or different substituents, the substituents being selected independently of one another from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio,
  • T is T 1 when A is O or T is T 2 when A is S,
  • U is a cycle of the series U-2, U-5, U-9, U-23, U-24 or U-25,
  • X a represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
  • R 1 is fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio,
  • R la is methyl
  • R 9 is hydrogen or methyl
  • R '° is hydrogen, m is 0.1 or 2, and n is 0.1 or 2.
  • A stands for O
  • Q is one of the radicals Q-1 or Q-6, Y is phenyl,
  • T stands for T '
  • T 1 is phenylmethyl
  • G is -C (R 9 ) (R 10 ) -,
  • U is a cycle of the series U-2, U-9 or U-23, X 'is chlorine, R 1 is methyl, R la is methyl, R 9 is hydrogen, R ! 0 is hydrogen, m is 0 or 1, and n is 0 or 1.
  • Q is one of the radicals Q-1 or Q-6,
  • Y is phenyi, where the abovementioned radicals may optionally be substituted and the substituents are independently selected from chlorine, nitro, trifluoromethyl and
  • T stands for T 1 ,
  • T 1 is phenylmethyl, where phenyl may be substituted by chlorine and where methyl may be substituted by methyl, cyano, cyanomethyl, vinyl or ethoxycarbonyl, or is phenylethyl or pyridylmethyl, where pyridyl may be substituted by chlorine, or is cyclohexyl, wherein cyclohexyl may be subtituted by methyl and isopropyl, or is cyclopropyl, where cyclopropyl may be substituted by methyl, or is cyclohexylmethyl or cyclopropylmethyl, where cyclopropyl may be monosubstituted to trisubstituted and the substituents are independently selected from methyl or fluoro, or is ethyl, wherein ethyl is monosubstituted or disubstituted by ethoxycarbonyl, or is ethyl, wherein ethyl is
  • G is -C (R 9 ) (R 10 ) -,
  • X a is hydrogen and chlorine
  • R 1 is methyl
  • R ia is methyl
  • R 9 is hydrogen
  • R 10 is hydrogen
  • n 0 or 1
  • n 0 or 1.
  • T T 2 .
  • T 2 is cyclohexyl or phenylmethyl
  • G stands for TM C (R 9 ) (R 10 ) -
  • U is a cycle of the series U-2, U-9 or U-23,
  • X J is hydrogen and chlorine
  • R ' is hydrogen
  • R '° is hydrogen, m is 0, and n is 0 or 1.
  • the invention relates to the compounds of the formula (I) in which A is O.
  • the invention relates to the compounds of the formula (I) in which A is S.
  • the invention relates to compounds of the formula (1-1).
  • U in formula (1-1) is U-2, U-5, U-9, U-23, U-24 or U-25.
  • the invention relates to compounds of the formula (IA) in which U is U-2, U-5, U-9, U-23, U-24 or U-25.
  • the invention relates to compounds of the formula (IB) in which U represents U-2, U-5, U-9, U-23, U-24 or U-25.
  • the invention relates to compounds of the formula (IC) in which U is U-2, U-5.
  • the invention relates to the compounds of the formula (iE).
  • the invention relates to the compounds of the formula (IF).
  • the invention relates to the compounds of the formula (IG),
  • soft R is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio.
  • the invention relates to the compounds of the formula (II)
  • R 11 is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio.
  • the invention relates to the compounds of the formula (IJ)
  • R is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy or methylthio.
  • the invention relates to compounds of the formula (1-2).
  • the structural elements U, G, Q and Y have the above in the embodiment (1-1) or in the embodiment (2-1) or in the embodiment (2-2) or in the embodiment (3-1 ) or in embodiment (3-2) or in embodiment (4-1) or in embodiment (4-2) or in embodiment (5-1) or in embodiment (5-2) or in embodiment (5-3) described Meaning, unless stated otherwise.
  • T 2 the meaning described in embodiment (2-1) applies independently of the definitions of the further structural elements.
  • U in formula (1-2) is U-2, U-5, U-9, U-23, U-24 or U-25. Of these, the following are particularly preferred embodiments:
  • the invention relates to compounds of the formula (I-2) in which all the structural elements described above in the embodiment (1 -1) or in the embodiment (2-1) or in the embodiment (2-2) or in the embodiment (3-1) or in the embodiment (3-2) or in the embodiment (4-1) or in the embodiment (4-2) or in the embodiment (5-1) or in the embodiment (5-3) have meaning described unless otherwise stated.
  • T 2 the definition of T applies, as long as T 2 is not explicitly defined, which is the case, for example, in relation to embodiment (1-1).
  • U in these compounds of formula (1-2) is U-2, U-5, U-9, U-23, U-24 or U-25.
  • Embodiment 5-2 or in embodiment 5-3.
  • substituted radicals may be monosubstituted or polysubstituted, wherein
  • substituents may be the same or different.
  • the compounds of the formula (I) may optionally also vary depending on the nature of
  • stereoisomers ie as geometric and / or optical isomers or Isomer mixtures are present in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their
  • Mixtures for controlling animal pests including arthropods and in particular insects.
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • Alk i either alone or in combination with other terms such as halogenoyl, in the context of the present invention means a radical of a saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms
  • C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-Pentyi, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and Of these alkyl radicals, G-Ce-alkyl radical
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched GG 2 -Aikinylrest having at least one triple bond, for example, ethynyl, 1-propynyl and Preference is given here to GG-alkynyl radicals and particular preference is given to C 3 -C 4 -alkynyl radicals
  • the alkynyl radical may also have at least one double bond.
  • cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
  • Cycloheptyl and cyclooctyl are C3-C6-Cycloaikyireste.
  • aryl according to the invention is understood to mean an aromatic radical having 6 to 14 carbon atoms, preferably phenyl, naphthyl, antirlyl or phenanthrenyl, particularly preferably phenyl.
  • aralkyl refers to a combination of radicals "aryl” and “alkyi” as defined according to the invention, the radical generally being bound via the alkyl group, examples being benzyl, phenylethyl or Methylbenzyl, with benzyl being particularly preferred.
  • hetary Means a mono-, bi-, or tricyclic heterocyclic group of C atoms and at least one heteroatom, wherein at least one cycle is aromatic,
  • the hetaryl group contains 3, 4, 5 or 6 C atoms selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, oxa / olyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3 -Oxadiazoyl, 1,2,4-oxadiazoyl, 1,3,4-oxadia / olyl, 1,2,5-oxadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,3,4-thiadi azolyl, 1, 2,5-thiadiazolyl, pyridyl, pyrimidin
  • heterocyclyl means a monocyclic, saturated or partially saturated 4-, 5-, 6- or 7-membered ring of C atoms and at least one heteroatom in the ring
  • the heterocyclyl group contains 3, 4, 5 or 6 C atoms and 1 or 2 heteroatoms from the series oxygen, sulfur or nitrogen
  • heterocyclyl are azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyi, thiethanyl, thiolanyl, thianyl, tetrahy dr o furyl.
  • halo-substituted radicals for example “haloalkyl”, are understood to mean halogenated radicals mono- or polysubstituted to the maximum possible number of substituents In the case of multiple halogenation, the halogen atoms may be identical or different.
  • Halogen here stands for fluorine. Chlorine, bromine or iodine, preferably fluorine or chlorine.
  • alkoxy either alone or in combination with other terms, such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
  • the compounds of formula (IV) are either commercially available or can be prepared in analogy to those described in Journal of Organic Chemistry, 51 (1986), 263-265; Organ ic Synthesis, 34 (1954), 26-29; Tetrahedron, 57 (2001), 2781-2786 and Journal of the American Chemical Society, 114 (1992), 3441-3445 by the reaction of compounds of formula (II) with a suitable alcohol under acidic or thermal conditions or to form an intermediate
  • the compounds of formula (VI) can be prepared in analogy to those described in Angewandte Chemie, International Edition, 51 (2012), 1028-1032; Chemistry A European Journal, 10 (2004), 5607-5622;
  • Step c) The compounds of the formula (VII) can be prepared in analogy to those described in WO2008 / 150487; Tetrahedron Letters, 49 (2008), 4434-4436; Journal of Organic Chemistry, 65 (2000), 5834-5836 and US2001 / 6300499 by saponification of compounds of formula (VI) using one equivalent of base.
  • compounds of formula (VII) are commercially available, for example 3-benzyloxy-3-oxo-2-phenyl-propanoic acid, 3- (2-ethoxy-1-methyl-2-oxo-ethoxy) -3-oxo-2 phenyl-propanoic acid, 3- (cyclohexoxy) -3-oxo-2-phenyl-propanoic acid and 3- (2-ethoxy-2-oxo-1-phenyl-ethoxy) -3-oxo-2-phenyl-propanoic acid.
  • the compounds of formula (VIII) may be prepared in analogy to those described in CN2013 / 103159672; Organic & Biomolecular Chemistry, 12 (2014), 8386-8389; Organi & Biomolecuiar Chemistry, 12 (2014), 9822-9830 and Chemical & Pharmaceutical Bulletin, 33 (1985), 61-66 described by reaction of compounds of formula (VII) with chlorinating reagents such. For example, oxalyl chloride, thionyl chloride or phosphorus oxychloride are prepared.
  • Step e) The compounds of formula (I) can be prepared in analogy to those described in Helvetica Chimica Acta, 96 (2013), 2160-2172; Organic Letters, 1 1 (2009), 2820-2823; WO201 1/024872 and US2007 / 0249596 described by reaction of compounds of formula (VIII) with amines of
  • Formula (IX) can be prepared under basic or acidic conditions.
  • Amines of the formula (IX) are either commercially available, for example N - [(6-chloro-3-pyridyl) methyl] pyridin-2-amine, N- (pyrimidin-5-ylmethyl) pyridin-2-amine, N- [ (2-chlorothiazol-5-yl) methyl] pyridin-2-amine and N - [(2-chlorothiazol-5-yl) methyl] -3-methyl-pyridin-2-amine, or may in analogy to processes known from the literature (cf., for example, Medicinal Chemistry Research, 23 (2014), 5043-5057, WO2009 / 099929, WO201 1/017351 or WO2012 / 0921 15).
  • the compounds of the formula (XII) can be prepared analogously to those described in WO2008 / 150487; Tetrahedron Letters, 49 (2008), 4434-4436; Journal of Organic Chemistry, 65 (2000), 5834-5836 and US2001 / 6300499 by hydrolysis of compounds of formula (XI) under acidic or basic conditions.
  • compounds of formula (XII) are commercially available, for example 2- (3-
  • Methoxyphenyl) propanedioic acid 2-phenylpropanedioic acid, 2- (4-methoxyphenyl) propanedioic acid, 2- [3-
  • the compounds of formula (VII) can be prepared in analogy to those described in Organi Letters, 4 (2002), 1415-1418; Journal of Organic Chemistry, 54 (1989), 5395-5397; Bioorganic & Medicinal Chemistry, 13 (2003), 2659-2662 and Synthetic Communiquations, 44 (2014), 275-279, by reacting compounds of formula (XII) with about one equivalent of the corresponding alcohol of formula (T '). ) -OH under acidic or thermal conditions or to form an intermediate active ester.
  • the compounds of the formula (XIV) can be prepared in analogy to those described in WO2010 / 057121; Journal of Medicinal Chemistry, 54 (201 1), 3348-3359; Helvetica Chimica Acta, 96 (2013), 2160-2172 and Organic Letters, 11 (2009), 2820-2823, by reaction of compound (XIII) with amines of formula (IX).
  • the compounds of the formula (XV) can be prepared in analogy to those described in WO2008 / 150487; Tetrahedron Letters, 49 (2008), 4434-4436; Journal of Organic Chemistry, 65 (2000), 5834-5836 and US2001 / 6300499 by hydrolysis of compounds of formula (XFV) under acidic or basic conditions. Step c)
  • the compounds of the formula (XVI) can be prepared in analogy to those described in Organic Letters, 4 (2002), 1415-1418; Journal of Organic Chemistry, 54 (1989), 5395-5397; Bioorganic & Medicinal Chemistry, 13 (2003), 2659-2662 and Synthetic Communications, 44 (2014), 275-279, by reacting compounds of formula (XV) with the corresponding alcohol of formula (T ') - OH under acidic conditions or thermal conditions or to form an intermediate active ester.
  • the compounds of formula (1-1) can be prepared in analogy to those described in Angewandte Chemie, International Edition, 51 (2012), 1028-1032; Chemistry - A European Journal, 10 (2004), 5607-5622; US2010 / 0069440 and Journal of Organic Chemistry, 67 (2002), 541-555 by the reaction of a compound of formula (XVI) with a compound (V) under basic
  • the compounds of formula (XVIII) can be prepared in analogy to those described in Chemical Communications, 48 (2012), 42-144; Organ ic Letters, 11 (2009), 5630-5633 and Journal of the American Chemical Society, 116 (1994), 73-81 by carboxylation of the 2-position of the corresponding substituted arylacetonitriles of formula (XVII) using carbon dioxide.
  • the compounds of formula (XIX) can be prepared in analogy to those described in CN2013 / 103159672; Organic & Biomolecular Chemistry, 12 (2014), 8386-8389; Organic & Biomolecular Chemistry, 1 2 (2014), 9822-9830 and Chemical & Pharmaceutical Bulletin, 33 (1985), 61-66; Helvetica Chimica Acta, 96 (2013), 2160-2172; Organic Letters, 1 1 (2009), 2820-2823; WO201 1/024872 and US2007 / 0249596 described by reaction of carboxylic acids of the formula (XVIII) in the corresponding acid halides and then in the presence of a base such. B. triethylamine or NS r - dimethylaminopyridine are converted into the carboxylic acid eamide.
  • the compounds of the formula (I-2) can be prepared in analogy to the processes described in Synthesis, 1 (1993), 964 and WO2012 / 137982 by reacting nitriles of the formula (XIX) with the corresponding mercaptans of the formula (XX) in the presence of a suitable Bransted or Lewis acid, such as. Hydrochloric acid or AICI3 under anhydrous conditions.
  • a suitable Bransted or Lewis acid such as. Hydrochloric acid or AICI3 under anhydrous conditions.
  • L 2 is G-CValkyl
  • Hai is halogen
  • the compounds of formula (XI) can be prepared in analogy to those described in Angewandte Chemie, International Edition, 51 (2012), 1028-1032; Chemistry - A European Journal, 10 (2004), 5607-5622; US2010 / 0069440 and Journal of Organic Chemistry, 67 (2002), 541-555 by reacting a compound of formula (X) with a compound (V) under basic copper-catalyzed conditions.
  • Step b) The compounds of the formula (XII) can be prepared analogously to those described in WO2008 / 150487; Tetrahedron Letters, 49 (2008), 4434-4436; Journal of Organic Chemistry, 65 (2000), 5834-5836 and US2001 / 6300499 by hydrolysis of compounds of formula (XI) under acidic or basic conditions.
  • Step c) The compounds of formula (XXI) can be prepared in analogy to those described in Organi & Biomolecular Chemistry, 11 (2013), 4449-4458; Biochemistry, 51 (2012), 4568-4579; Nature Chemical Biolog ⁇ ', 10 (2014), 251-258 and Journal of Organi Chemistry, 78 (2013), 6412-6426 by reacting compounds of formula (XII) with about one equivalent of the corresponding thiol of formula (T ) -OH under acidic or thermal conditions or to form an intermediate active ester.
  • Step e) The compounds of formula (1-2) can be prepared in analogy to those described in Helvetica Chimica Acta, 96 (2013), 2160-2172; Organic Letters, 1 1 (2009), 2820-2823; WO201 1/024872 and US2007 / 0249596 method described by reacting compounds of formula (XXII) with amines of formula (IX) under basic or acidic conditions.
  • compounds of formula (I) can be prepared by the methods described above. If individual compounds can not be prepared by the methods described above, the synthesis is possible by derivatization of other compounds of formula (I) or by individual modifications of the methods described. For example, it may be advantageous to prepare certain compounds of formula (I) from other compounds of formula (I) and, for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, oxygenation, halogenation. Acylation, alkylation and the like.
  • the processes according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents.
  • Halogenated hydrocarbons eg chlorohydrocarbons, such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzo, chlorotoluene, trichlorobenzene), alcohols (eg Methanol, ethanol, isopropanol, butanol), ethers (eg ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether, di-n-
  • Bromobenzene, nitrobenzene, xylene, esters eg, methyl, ethyl, butyl, isobutyl acetate, dimethyl, dibutyl, ethylene carbonate
  • Amides eg, hexamethylenephosphoric triamide, formamide, N-methylformamide, N, N-dimethylformamide, N, N-dipropylformamide, N, N-dibutylformamide, N-methyl-pyrrolidine, N-methyl-caprolactam, 1 , 3-dimethyl-3, 4,5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone, Octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, ⁇ , ⁇ '-diformyl-piperazine) and ketones (eg acetone, acetophenone, methyl ethyl ketone
  • reaction temperatures can be varied within a substantial range when carrying out the processes according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 bar and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature.
  • a protective gas atmosphere e.g., under nitrogen, argon or helium
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • amidine bases or guanidine bases eg 7-methyl-1,5, 7-triaza- bicyclo (4.4.0) dec-5-ene (MTBD), diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1, 8-diazabicyclo (5.4.0) undecene (DBU ), Cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), ⁇ , ⁇ , ⁇ , ⁇ -tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine) and amines, especially ter
  • mineral acids for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, Hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphorous acid, nitric acid
  • Lewis acids eg aluminum (III) chloride, boron trifluoride or its etherate, titanium (IV) chloride, tin (IV) chloride
  • organic acids eg formic acid, Acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid).
  • 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 both pure stereoisomers and 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 always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, to increase crop yields, improve the quality of the crop and to control animal pests, in particular insects , Arachnids, helminths, in particular nematodes, and mollusks, which are found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreational facilities, in storage and materials protection and in the hygiene sector.
  • the term "hygiene” is to be understood as meaning any and all measures, regulations and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect one's health Protecting people and animals and / or protecting the environment, and / or maintaining cleanliness. According to the invention, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces of glass, wood. Cement, porcelain, ceramics, plastic or metal (s) to ensure that they are free of hygiene damage and / or their excreta.
  • surgical or therapeutic treatment regimens to be applied to the human body or bodies of animals and diagnostic provisions made on the human body or bodies of animals.
  • honeygiene sector covers all areas, technical fields and industrial applications where these hygiene measures, regulations and procedures are important, for example with regard to hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels , Hospitals, stables, animal husbandry etc.
  • the term "hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
  • hygiene pests include the organisms mentioned below.
  • the compounds of the formula (I) can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or one / a development stages.
  • the above mentioned pests include:
  • Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko. Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Blatta orientalis Blueella asahinai, Blattelia germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Peripianeta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supelia longipalpa; from the order of Coleoptera z.
  • Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Diciadispa armigera, Dilobodems spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
  • hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Leina spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B.
  • Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Ouiema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyilotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tanymecus spp. E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B.
  • Acyrthosiphon pisum Acrogonia spp., Aeneoiamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. B. Ainrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
  • B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp. Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g. B.
  • Paratrioza cockerelli Parlatoria spp .. Pemphigus spp. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp .. Phenacoccus spp .. z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoidus titanus, Schizaphis graminum.
  • Trio / a diospyri Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Biissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dicheiops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Psallus spp. Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp .; from the order of Hymenoptera z. Acromyrmex spp., Athalia spp., E.g. B. Athalia rosae, Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp., Z. B. Diprion similis, Hoplocampa spp., Z. B.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp. Paravespula spp., Plagiolepis spp., Sirex spp. Solenopsis invicta, Tapinoma spp. Technomyrmex albipes, Urocerus spp. , Vespa spp .. z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Choristoneura spp. Chrysodixis chalcites, Clysia ambigueila, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedyiepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp.
  • Heliothis virescens Hofmannophila pseudospretelia Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
  • Leucoptera coffeella Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
  • Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Piuteila xylostella ( Piutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaietia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g.
  • Ctenocephalides canis, Ctenocephalides felis, Pul ex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
  • Heliothrips spp. Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp. z.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B.
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp. Cacopaurus pestis, Criconemella spp. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp. B.
  • Meloidogyne spp. E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne liapla, 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., Radophoius spp., E.g. Radopholus citrophiius, Radopholus simiiis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., E.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g.
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as an agent against MLO (Mycoplasma-like-organism) and RI O (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 S cbirdlingsb ehimmp fungsmittel such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g.
  • penetration enhancers e.g.
  • vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soy aölmethylester or Aikanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • dioctylsulfosuccinate or hydroxy xypropyl guar polymers and / or humectants such.
  • glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
  • Formulations of the invention may be aqueous or non-aqueous.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in
  • EW Water
  • SC suspension concentrates
  • SE FS, OD
  • WG water-dispersible granules
  • GR granules
  • CS capsule concentrates
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are middle, which promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for shaping the formulation of the compounds of the formula (I) or the formulations prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings)
  • Suitable extenders z As water, polar and nonpolar organic chemical liquids such. From the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkyl benzoic, alkylnaphthalenes, chlorobenzenes), alcohols and polyol (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, alkyl benzoic, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyol which may also be substituted, etherified and / or esterified
  • ketones such
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic carbon monoxide such as chlorobenzenes. Chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Suitable solvents are, for example, aromatic hydrocarbons such. B. xylene, Tokyo! or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic Kohlenwas s réelleo ffe such.
  • cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. As methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such. As acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • Suitable carriers can be used.
  • carriers are in particular question: z.
  • ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: z.
  • liquefied gaseous diluents or solvents can be used.
  • extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
  • a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
  • dyes such as inorganic pigments, eg., iron oxide, titanium oxide, Ferrocyanblau and organic Dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and / or physical stability can also be present. It may also contain foam-forming agents or defoamers.
  • auxiliaries and adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be contained in the formulations and the application forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestering agents, complexing agents. Humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) Appiikationsbrühe and / or from the fuel / coating in the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property.
  • alcohol alkoxides such as, for example, coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, such as rapeseed oil or soyailate, fatty amine alkoxylates, such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts, such as, for example, ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxides such as, for example, coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
  • fatty acid esters such as rapeseed oil or soyailate
  • fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts, such as, for example, ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of 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 chelating agents) can vary widely.
  • the concentration of the compound of formula (I) in the application forms can usually be between 0.00000001 and 95 wt .-% of the compound of formula (I), preferably between 0.00001 and 1 wt .-%, based on the weight of Application form, lie.
  • the application is done in a forms adapted to the application customary way.
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be so z.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be so z.
  • B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance.
  • drug combinations may include plant growth and / or tolerance to abioti see factors
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • Formula (I) for improving the plant properties such as growth, yield and quality of the crop are used.
  • 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.
  • carbamates e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methi
  • Triazamates trimethacarb, XMC and xylylcarb or organophosphates, e.g. Acephate, azamethiphos, azinphos-ethyl, azinophos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chloroforms, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-s-methyl, diazinon, di-clororos DD VP, dicrotophos, dimethoate, dimethylvinphos , Disuifoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl 0- (methoxyaminothio-phosphoryl) salicylate, Isoxathion, Mala
  • Phenthoate Phorat, Phosalon, Phosmet, Phosphamidone, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos. Sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone and vamidothion.
  • GABA-controlled chloride channel blockers such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
  • sodium channel modulators such as pyrethroids, e.g. Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin.
  • nAChR nicotinic acetylcholine receptor
  • neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Allosteric modulators of the nicotinic acetylcholine receptor (nAChR) such as spinosyn, e.g. B. spinetoram and spinosad.
  • allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar embryo or methyl isocyanate producers, e.g. Diazomet and Metam.
  • modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
  • mite growth inhibitors such as. As clofentezine, hexythiazox and Di flo vi da / in or Etoxazol.
  • inhibitors of mitochondrial ATP synthase such as ATP disruptors, such as
  • Diafenthiuron or organotin compounds e.g. As azocyclotine, cyhexatin and fenbutatin oxide or propargite or tetradifone.
  • Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • inhibitors of chitin biosynthesis type 0, such as bistrifluron, Chlorflua / uron. Diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
  • ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • octopamine receptor agonists such as amitraz.
  • Mitochondrial complex-I 1 electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
  • Mitochondrial Complex I Elctron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone
  • inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. Aluminum phospho-sphid, calcium ciumpho sphid, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
  • Inhibitors of mitochondrial complex-i -levelase transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyflumetofen and carboxanilides such as Pyflubumid.
  • ryanodine receptor modulators such as diamides, e.g. As chlorantraniliprole, cyanotriliprol and flubendiamide, other agents such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, Ben / oximat. Bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin. Cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol.
  • diamides e.g. As chlorantraniliprole, cyanotriliprol and flubendiamide
  • other agents such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, Ben / oximat. Bifenazate, broflanilide, brom
  • epsilon-metofsuthrin epsilon-momfluthrin, flometoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, flaxxafon, fluopyram, fluralan, fluxametamide, fufenocide, guadipyr, heptafluthrin. Imidaclothiz, iprodione, kappa-bi-enthrin.
  • All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
  • All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
  • inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetrac
  • inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fuxapyroxad, (2.008) furametpyr , (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1 R.4S.9S).
  • inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3-chloro-4- (2,6-dithiaphenyl) -6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl ) -6-methylpyridazine, (4:01 1) 3-chloro-5 - (6-ch ⁇ o ⁇ yridin-3-yl) -6-methyl -4- (2,4,6-trifluoi * phenyl) pyridazine (4.012) of 4- (2-bromo-4-fluorophenyl)
  • inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil,
  • Inhibitors of melanin biosynthesis for example (1,001) tricyclazole, (1,002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate
  • 12) inhibitors of nucleic acid synthesis for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
  • the compounds of formula (I) may be combined with biological chelating agents.
  • biological chelating agents include bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms including proteins and secondary metabolites.
  • Biological damage control agents 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 1-1 62 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, in particular 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 QST71 3 (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 AM -52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, especially strain ABTS! 857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • B. thuringiensis subspecies israelensis serotype H-14
  • strain AM -52 accesion No. ATCC 1276
  • B. thuringiensis subsp. aizawai especially strain ABTS! 857 (SD-1372)
  • B. thuringiensis subsp. kurstaki strain HD-1 or B. thuringiensis subs
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91 -8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain U RO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y -30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFC 200613, or strain Apopka 97 (Accesion No.
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel wrapper
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosus evirus GV
  • Helicoverpa ar igera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua sucgar beetle mNPV
  • Spodoptera frugiperda armyworm
  • Spodoptera littoralis Africann cotton worm
  • bacteria and fungi that are added as 'inoculant' plants or parts of plants or plant organs and promote by their special properties, plant growth and plant health. Examples are:
  • Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp.
  • plant extracts and products formed by microorganisms including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N- ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531 -12-0), 4- (dichloroacetyl) -l-oxa 4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31 -4).
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber. Melon, carrot, watermelon, onion, lettuce, spinach, leek. Beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • cereals wheat, rice, triticale, barley, rye, oats
  • corn soybeans
  • potatoes sugar beets
  • sugarcane tomatoes
  • Paprika cucumber.
  • Beans, Brassica oleracea eg cabbage
  • other vegetables cotton, tobacco, oilseed rape, as well
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants such as shoot, leaf, flower and root, exemplarily leaves, needles, stems. Stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhino never be listed.
  • the plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by the action of the compounds on the environment, the habitat or the storage space according to the usual treatment methods, eg. B. by immersion, spraying, evaporation, Nebulizing, spreading, brushing, injecting and propagating material, especially in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as hybridization or protoplast fusion and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties (“traits”) have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), (ryllA.CrylllA.CryIIIB2), Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, furthermore an increased resistance of the plants to phytopathogenic fungi, bacteria and / or viruses, eg by systemically acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins, as well as an increased tolerance of the plants to certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene) ”) genes can also be present in combinations with one another in the transgenic plants.”
  • the important crop plants such as cereals (whe
  • Tomatoes Tomatoes, peas and other vegetables, cotton, tobacco. Rapeseed, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) mentioned, whereby maize, soy, wheat, rice, potato, cotton, sugarcane, tobacco and oilseed rape are particularly emphasized. Traits that are particularly emphasized are the increased immunity of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) by the ultra-low volume method or to inject the application form or the compound of the formula (I) itself into the soil.
  • a preferred direct treatment of the plants is the blue application, i. H. the compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of
  • Drenchen be mixed in the soil or the nutrient solution, d. Ii. the location of the plant (eg.
  • Soil or hydroponic systems is impregnated with a liquid form of the compounds of formula (I), or by the soil application, i. H. the compounds of the formula (I) according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants.
  • Application form (eg as granules) in a flooded rice field.
  • seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
  • the present invention therefore more particularly relates to a method of protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I).
  • the method according to the invention for the protection of seeds and germinating plants from infestation of pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and a mixture component. It also further comprises a process in which the seed is treated at different times with a compound of formula (I) and a mixture component.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) according to the invention.
  • the invention also relates to seed treated at the same time with a compound of formula (I) and a mixture component.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and a mixture component.
  • the individual substances may be present in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture components may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and a mixture component are applied as part of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
  • Compounds of formula (I) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or optimized nitrogen fixation occurs.
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco.
  • Canola, rape, turnip eg sugar beet and fodder
  • peanut eg tomato, cucumber, bean, cabbage, onions and lettuce
  • fruit plants eg tomato, cucumber, bean, cabbage, onions and lettuce
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly 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 forms! (I) applied to the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
  • seeds may be used that have been harvested, cleaned and dried to a moisture content that is storable.
  • seed can be used that after drying z. B. was treated with water and then dried again, for example, priming.
  • the compounds of the formula (I) can be converted into the customary mordanting formulations, such as solutions, emulsions, suspensions, powders, foams, whiskers or other seed coating compositions, as well as ULV formulations.
  • Water sparingly soluble pigments as well as water-soluble dyes usable are water sparingly soluble pigments as well as water-soluble dyes usable. Examples which may be mentioned under the names Rhodaini n B, CI Pigment Red 1 12 and C ' .l. Solvent Reil 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 alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are Ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or modified 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 customary foam-inhibiting substances for the formulation of agrochemical active compounds.
  • silicone defoamers and magnesium stearate.
  • 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 which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Celiuio derivatives, acrylic acid derivatives, xanthan, modified clays and highly dispersed silicic acid are preferably suitable.
  • 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 dressing is carried out in such a way that the seed is placed in a mixer in batch or continuous operation, which adds any desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed. animal Health
  • Formula (I) against animal parasites in particular ectoparasites or endoparasites, effective.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects or acarids.
  • the compounds of formula (I) which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of development of the parasites.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry like turkeys.
  • mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry like turkeys.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
  • the compounds of the formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely birds or, in particular, poultry.
  • birds namely birds or, in particular, poultry.
  • Illness, deaths and reductions in benefits in meat, milk, wool, hides, eggs, honey and The like
  • benefits in meat, milk, wool, hides, eggs, honey and The like
  • controlling means that the compounds of formula (I) effectively affect the appearance of the respective parasite in an animal infected with such parasites to a harmless extent , is reduced. More specifically, “combating” in the present context means that the compounds of formula (I) kill the respective parasite, prevent its growth or prevent its replication.
  • arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp. Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damali na spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomy
  • Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Phiiipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp.
  • Tabanus spp. Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pul exspp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, / for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests and hygiene pests from the order Blattarida.
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Omithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Omithodorus spp., Otobius spp.
  • Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (
  • Chorioptes spp. Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp , Pterolichus spp., Sarcoptes spp., Trixacarus spp., Tyrophagus spp.
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora (Flagellata), like:
  • Metamonada from the order Vacciniadida for example Giardia spp., Spironucleus spp.
  • Parabasala from the order Trichomonadida for example Histomonas spp., Pentatrichomonas spp. Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
  • Euglenozoa from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp. Alveoiata such as Apicomplexa (Sporozoa): z.
  • Cryptosporidium spp . from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp. Plasmodium spp .; from the order Piroplasmida z.
  • Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
  • Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
  • helminths include, but are not limited to:
  • Monogenea z.
  • Dactylogyrus spp. Gyrodactylus spp., Microbothrium spp., Polystoma spp., Trogiecephaius spp .;
  • Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
  • Echinoiepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
  • Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
  • Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobiiharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotyius spp., Opisthorchis spp.
  • Paragonimus spp. Paramphi stomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Trogiotrema spp., Typhlocoeium spp.
  • Nematodes from the order Trichineilida for example: Capiliaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
  • Aeluro strongylus spp. Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp , Cyciococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.
  • Haemonchus spp. Heligmosomoides spp., Hyostrongylus spp., Arshallagia spp. Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neo strongylus spp., Nippo strongylus spp., Obeliscoides spp., Oesophagodontus spp.
  • Oesophagostomum spp. Ollulanus spp .; Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp , Strongylus spp., Syngamus spp., Teladorsagia spp., Trichonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.
  • Acanthoc ephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp. Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
  • one embodiment of the present invention relates to the compounds of formula (I) for use as pharmaceuticals.
  • Another aspect relates to the compounds of formula (I) for use as antiendoparasitic.
  • Another specific aspect of the invention relates to the compounds of the formula (I) for use as antihelminthic, in particular for use as nematicide, platymelic acidicide, acanthoc ephalicidal or pentastomicidal.
  • Another specific aspect of the invention relates to the compounds of formula (I) for use as antiprotozoic.
  • Another aspect relates to the compounds of formula (I) for use as anti-topazarasitic, in particular an arthropodicide, more particularly an insecticide or an acaricide.
  • veterinary formulations comprising an effective amount of at least one compound of formula (I) and at least one of a pharmaceutically acceptable excipient (eg, solid or liquid diluents), a pharmaceutically acceptable adjuvant (eg, surfactants), especially one Pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary formulations.
  • a pharmaceutically acceptable excipient eg, solid or liquid diluents
  • a pharmaceutically acceptable adjuvant eg, surfactants
  • a related aspect of the invention is a process for the preparation of a veterinary formulation as herein described, which comprises the step of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or adjuvants, particularly pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or adjuvants conventionally used in veterinary formulations.
  • veterinary formulations selected from the group of ectoparasitic and endoparasitic formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group consisting of (nematocidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal Formulations according to the aspects mentioned, as well as processes for their preparation.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by applying an effective amount of a compound of the formula (I) to an animal, in particular a non-human Animal that needs it.
  • Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of ectoparasites and endoparasites mentioned herein, by applying a veterinary formulation as defined herein to an animal, in particular a non-human animal its needs.
  • Another aspect relates to the use of the compounds of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular a non-human animal.
  • treatment includes prophylactic, metaphylactic and therapeutic treatment.
  • mixtures of at least one compound of the formula (I) with other active substances, in particular with endo- and ectoparasiticides are provided hereby for the veterinary field.
  • "blending" not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. when applied more than two active ingredients be formulated, all active substances in a common formulation or all active substances in separate formulations formulated; Also conceivable are mixed forms in which some of the active ingredients are formulated together and some of the active ingredients are formulated separately. Separate formulations allow the separate or sequential use of the active substances in question.
  • Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
  • Other useful agents are listed below according to the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetyl cholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
  • Active substances with unknown or non-specific mechanisms of action eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, aliumoleate. Petroleum, Metoxadiazone, Gossyplur, Flutenzine, Bromopropylate, Cryolite;
  • Qrganochlorharmen z. B. Campfaechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralan he;
  • Pyrethroids e.g. Eg, (cis, trans) metofluthrin, profuthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, teralletfarin, cis-resmethrin, heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin .
  • Cyhalothrin (lambda), chlovaporthrin, or halogenated carbon dioxide hydrogen compounds (HCHs), neonicotinoids, eg. B. Nithiazine
  • Dicloromezotiaz, triflumezopyrim, macrocyclic lactones e.g. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
  • Triphene Epofenonan, Diofenolan; Bioiogicals, hormones or pheromones, for example natural products, e.g. thuringiensin,
  • Dinitrophenols e.g. Dinocap, dinobuton, binapacryl
  • Benzoylureas eg. B. Fiuazuron, Penflnron, amidine derivatives, z. Chormorman, cymiazole, demiditraz hive varroa acaricides, for example organic acids, e.g. Formic acid, oxalic acid.
  • agents from the group of endoparasiticides include, but are not limited to, anthelmintic agents and antiprotozoal agents.
  • the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazoi, albendazole sulfoxide, albendazole, flu
  • oxantel from the class of imidazothiazoles, for example: butamisole, levamisole, tetramisole; from the class of aminophenylamidines, for example: amide shell, deacylated amide shell (dAMD), tribendimidine; from the class of aminoacetonitriles, for example: Monepantel; from the class of Paraherquamide, for example: Paraherquamid, Derquantel; from the class of salicylanilides for example: Tribromsalan, Bromoxanid, Brotianid, Clioxanid, Closantel, Niclosamid, Oxyclozanid, Rafoxanid; from the class of substituted phenols, for example: nitroxynil, bithionois, disophenol, hexachlorophene, nicolofolan, meniclopholan; from the class of organophosphates for example: triclilorfon.
  • imidazothiazoles for
  • Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class Poiyletherionophor for example: Monensin, Salinomycin, Maduramicin, Narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinine for example: chioroquin; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amproiium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
  • Examples of vectors and their transmitted diseases or pathogens are:
  • Anopheia malaria, filariasis;
  • Culex Japanese encephalitis, filariasis, other viral diseases, transmission of other worms;
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • mites acariosis, epidemic typhus, rickettsipox, tularemia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean Congo fever, borreliosis;
  • Ticks Berel Mosen, such as Borrelia bungdorferi sensu lato., Borrel ia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), Ehrlichiosis.
  • vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips. the plants can transfer vi to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Vectors are also possible if the compounds of the formula (I) are resistance-breaking.
  • Compounds of formula (I) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the supply and material protection. Protection of technical materials
  • the compounds of the formula (I) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of formula (I) are present as a ready-to-use pest control agent, i. Ii., They can be applied to the corresponding material without further changes.
  • insecticides or fungicides in particular those mentioned above come into question.
  • the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents. Control of animal pests in the hygiene sector
  • 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 contactor, especially for controlling insects, arachnids, ticks and mites in indoor areas, such as homes, factories, offices. Vehicle cabins, animal breeding plants occur.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out for example in aerosols, non-pressurized sprays, z.
  • foggers As pump and Zerstäubersprays, foggers, Foggem, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propel lcrget ri level evaporators, energy-less or passive evaporation systems, moth papers, mantle sacs and moth gels, as granules or dusts, in straw baits or bait stations.
  • Step 1 Benzyl 3-chloro-3-oxo-2-phenylpropanoate
  • Step 1 3 -Benzyloxy-3-oxo-2- [3 - (trifluoromethyl) phenyl] propanoic acid (Compound No. VII-28)
  • Step 2 Benzyl 3-chloro-3-oxo-2- [3- (trifluoromethyl) phenyl] propanoate
  • Step 3 Benzyl 3) xo-3- [2-pyridyl (pyrimidin-5-ylmethyl) amino] -2- [3- (trifluoromethyl) phenyl] propanoate
  • Step 1 1- (5-chloro-1,3-thiazol-2-yl) -N- (pyridin-2-yl) methanimine
  • Step 2 N - [(5-chloro-1,3-thiazol-2-yl) methyl] pyridin-2-amine
  • the IH-NMR data of selected examples are recorded in the form of IH-NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity) '; ⁇ (intensity 2); ; ⁇ ; (Intensity ⁇ ;; ⁇ (Inten sity n)
  • ⁇ intensity
  • ⁇ intensity 2
  • ⁇ Intensity ⁇
  • ⁇ Inten sity n
  • the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of 1H 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 identify the reproduction of our manufacturing process by "by-product fingerprints.”
  • Example 1-1-05: 1 H NMR (601, 6 MHz, CDCb): ⁇ 8.466 (3.3), 8.441 (3.4), 8.142 (5.8), 8.138 (5.8); 7.726 (0.4), 7.722 (0.4), 7.713 (0.4), 7.709 (0.4), 7.6 43 (1, 8), 7.630 (1, 9), 7.557 (1, 7 7,574 (1,7), 7,564 (3,3), 7,561 (3,2), 7,551 (1, 9), 7,548 (1, 8), 7,403 (0,6), 7,389 (0,5) 7.366 (0.4); 7.361 (0.4); 7.357 (1, 0); 7.354 (0.7); 7.350 (1, 5); 7.347 (1, 6): 7.342 (6.7); 7.339 (5.2); 7.333 (13.6); 7.330 (14.1); 7.325 (3.8): 7.322 (2.0), 7.315 (0.6), 7.311 (0.5), 7.292 (0.4): 7.289 (0.6), 7.279 (7.9): 7.275 (7) 6.8), 7.2
  • Example 1-1-07: 1 H-NMR (400.0 MHz, de-DMSO): 6 8.451 (3.6), 8.448 (3.8), 8.439 (3.8), 8.436 (3.8 ); 8,314 (0.4); 7,862 (2.2); 7,857 (2.4); 7,842 (4.2); 7,837 (4.3); 7,823 (2.7); 7,818 (2.7); 7,663 (1.0); 7,476 (10.2); 7,385 (2.9); 7,372 (3.2); 7,367 (3.1), 7.354 (2.8), 7.338 (0.4), 7.296 (9.7), 7.291 (11, 2), 7.283 (16.0), 7.279 (13.1), 7.268 ( 6.4): 7.265 (10.8), 7.247 (4.9), 7.243 (4.6), 7.236 (1.9), 7.230 (6.4), 7.222 (11, 6), 7.218 (11 7,211 (5.9); 7,202 (10,4); 5,190 (1, 0); 5,122 (0,9); 5,082 (3,2); 5,063 (4,3); 5,024 (1); 1);

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des composés de formule (I) appropriés pour la lutte contre les animaux nuisibles, tels que les arthropodes et notamment les insectes, les acariens, et les nématodes, les éléments structuraux Q, G, U, Y, A et T de ces composés étant définis dans la description. L'invention concerne par ailleurs un procédé pour les préparer et leur utilisation en tant qu'insecticides.
PCT/EP2016/080166 2015-12-11 2016-12-08 Amides d'acide malonique substitués utilisés comme insecticides Ceased WO2017097870A1 (fr)

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US10329286B2 (en) 2016-06-13 2019-06-25 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10421730B2 (en) 2016-06-13 2019-09-24 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11225473B2 (en) 2019-01-15 2022-01-18 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US20220363677A1 (en) * 2019-07-29 2022-11-17 Les Laboratoires Servier 6,7-dihydro-5h-pyrido[2,3-c]pyridazine derivatives and related compounds as bcl-xl protein inhibitors and pro-apoptotic agents for treating cancer
US11524005B2 (en) 2019-02-19 2022-12-13 Gilead Sciences, Inc. Solid forms of FXR agonists
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US10485795B2 (en) 2011-07-13 2019-11-26 Gilead Sciences, Inc. FXR (NR1H4) binding and activity modulating compounds
US10220027B2 (en) 2011-07-13 2019-03-05 Gilead Sciences, Inc. FXR (NR1H4) binding and activity modulating compounds
US11739065B2 (en) 2016-06-13 2023-08-29 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10329286B2 (en) 2016-06-13 2019-06-25 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10421730B2 (en) 2016-06-13 2019-09-24 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10774054B2 (en) 2016-06-13 2020-09-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10981881B2 (en) 2016-06-13 2021-04-20 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11247986B2 (en) 2016-06-13 2022-02-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US12358903B2 (en) 2016-06-13 2025-07-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
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US11225473B2 (en) 2019-01-15 2022-01-18 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11524005B2 (en) 2019-02-19 2022-12-13 Gilead Sciences, Inc. Solid forms of FXR agonists
US12102625B2 (en) 2019-02-19 2024-10-01 Gilead Sciences, Inc. Solid forms of FXR agonists
US20220363677A1 (en) * 2019-07-29 2022-11-17 Les Laboratoires Servier 6,7-dihydro-5h-pyrido[2,3-c]pyridazine derivatives and related compounds as bcl-xl protein inhibitors and pro-apoptotic agents for treating cancer

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