WO2015107133A1 - Dérivés de quinoléine utilisés comme insecticides et acaricides - Google Patents

Dérivés de quinoléine utilisés comme insecticides et acaricides Download PDF

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WO2015107133A1
WO2015107133A1 PCT/EP2015/050732 EP2015050732W WO2015107133A1 WO 2015107133 A1 WO2015107133 A1 WO 2015107133A1 EP 2015050732 W EP2015050732 W EP 2015050732W WO 2015107133 A1 WO2015107133 A1 WO 2015107133A1
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spp
alkyl
stands
cyano
methyl
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PCT/EP2015/050732
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German (de)
English (en)
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Markus Heil
Michael Maue
Eike Kevin Heilmann
Peter Jeschke
Ulrich Görgens
Kerstin Ilg
Arnd Voerste
Andreas Turberg
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Bayer Cropscience Ag
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Publication of WO2015107133A1 publication Critical patent/WO2015107133A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention relates to novel Quinolinderivate, processes for their preparation and their use for controlling animal pests, especially of arthropods and in particular of insects, arachnids and nematodes.
  • Insecticidal indole or benzimidazolecarboxamides are already known, see WO-A-2011/054436 or WO-A-2012/119984.
  • certain novel quinoline derivatives e.g. Quiolin-2-carboxamides, strong insecticides and acaricidal properties with good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility possess.
  • the novel compounds of the invention have not been disclosed.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity. It has now surprisingly been found that certain new quinoline derivatives and their N-oxides and salts have strong insecticidal and acaricidal properties with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility. The novel compounds of the invention have not been disclosed.
  • the present invention is therefore compounds of the general formula (I)
  • R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen-substituted Ci-Ce-alkyl, C 3 -C 6 -cycloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci -C 6 - alkylsulfonyl, Ci-Cö-alkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkoxyimino-Ci-C6-alkyl or Ci-Cö-alkylsulfonyloxy, or
  • R 1 is an optionally 1 or 2 heteroatoms containing Ci-C i carbon chain which is bonded to two adjacent ring positions and forms an aliphatic, aromatic, heteroaromatic or heterocyclic ring, which may be mono- or polysubstituted by Ci-Cö-alkyl or Halogen is then substituted, wherein n is then 1 and wherein the heteroatoms are selected from the group consisting of N, S and O, n is 1,2, 3, 4 or 5,
  • R 2 is hydrogen, halogen, cyano, hydroxyl or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy, where the substituents are independent are selected from fluorine, chlorine, bromine or iodine
  • R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C i-alkylcarbonyl or Ci-C i-alkoxycarbonyl, wherein the substituents independently of one another are selected from cyano, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
  • Q 1 is CR 4 or N
  • Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
  • R 4 is hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
  • R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 6 alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, CI-C east - Alkoxy, (C 1 -C 6 -alkoxy) carbonyl, C 1 -C 6 -alkylamino, formyl, (C 1 -C 6 -alkyl) carbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -dialkylamino, (C 1 -C 6 alkylamino) carbonyl, (CI-COE dialkylamino) carbonyl, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl,
  • X is Ci-C6-haloalkyl, which may optionally additionally be monosubstituted to trisubstituted, where the substituents are independently selected from hydroxy, cyano or Ci-C i-alkoxy,
  • W stands for O or S
  • G stands for a free electron pair or for oxygen
  • R 13 , R 16 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, cyano-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl i-alkylcarbonyl, Ci-C i-alkoxycarbonyl or C2-C 4 alkenyl stand,
  • R 14 , R 15 independently of one another represent hydrogen or C 1 -C 4 -alkyl or R 14 , R 15 together form a 3-6-membered aliphatic ring,
  • Y is hydrogen or optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl or C 1 -C 12 -cycloalkenyl wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C 4 -Alkylaminothiocarbonyl, Ci-C 4 -Halogenalkylaminocarbonyl, di- (Ci-C 4 alkyl) aminocarbonyl, di- (Ci-C 4 alkyl) - aminothiocarbonyl, hydroxycarbonyl, Ci-C 4 alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, Ci- C6
  • the respective number of substituents n in the formula (I) includes only the substituents which are different from hydrogen. For this reason, hydrogen is not included in the definition of R 1 either. Of course, the substituent is always hydrogen, if no substituent R 1 is present at the respective site.
  • 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 quinolinecarboxylic 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
  • R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl or C 1 -C 4 - Alkylsulfonyl or Ci-C 4 alkylsulfonyloxy, n is 1, 2, 3, 4 or 5 stands
  • R 2 is hydrogen or optionally monosubstituted to trisubstituted Ci-Cö-alkyl, wherein the substituents are independently selected from fluorine, chlorine, bromine or iodine
  • R 3 is hydrogen, optionally mono- or polysubstituted, identically or differently substituted Ci-C i-alkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, Ci-C4-alkylcarbonyl or Ci-C4-alkoxycarbonyl, wherein the Substituents are independently selected from cyano, halogen or Ci- C4-alkoxy
  • Q 1 is CR 4 or N
  • Q 4 is CR 4 or N where Q 1 is CR 4 when Q 4 is N and Q 4 is CR 4 when Q 1 is N.
  • R 4 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
  • R 6 is hydrogen, halogen, nitro, cyano, optionally mono- or polysubstituted by identical or different substituents, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl , C 1 -C 4 alkoxy, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 4 alkyl) carbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, or C 1 -C 4 alkylsulfonyl, where the substituents are independent are selected from among halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
  • X is Ci-C4-haloalkyl
  • W is O
  • G is a lone pair of electrons or oxygen
  • R 13 is hydrogen, C 1 -C 4 -alkyl, cyanomethyl, C 1 -C 4 -alkoxymethyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or C 2 -C 4 -alkenyl stands, Y is hydrogen or or optionally mono- or polysubstituted by identical or different substituents Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cs-Ce-cycloalkyl or C 3 -C 6 -cycloalkenyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C i-alkyl, Ci-C i-haloalkyl, C3-Cs-cycloalkyl, CI-C
  • Y is an optionally mono- or polysubstituted by identical or different substituent, phenyl, or an optionally monosubstituted or polysubstituted heterocycle selected from the group consisting of thienyl, furanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, 1,2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl,
  • Particularly preferred (embodiment 3-1) are the compounds of formula (I) in which R 1 is halogen, nitro, cyano, optionally mono- or polysubstituted by fluorine or chlorine-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfmyl, C 1 -C 4 -alkyl, C 4 -alkylsulfonyl or C 1 -C 4 -alkylsulfonyloxy, n is 1, 2, 3, 4 or 5, R 2 is hydrogen,
  • R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
  • Q 2 is CR 4
  • Q 3 is CR 4
  • R 4 is hydrogen, fluorine or chlorine
  • R 6 represents hydrogen, halogen, nitro, cyano, or represents optionally monosubstituted to trisubstituted by halogen C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, X represents trifluoromethyl, difluoromethyl or pentafluoroethyl,
  • G stands for a lone pair of electrons
  • R 13 is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl, optionally substituted once to three times, identically or differently substituted Ci-Cö Alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, or C 1 -C 6 -cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-alkyl Ci-C i-haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C 2 -C 4 - Alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alky
  • Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
  • R 2 is hydrogen
  • R 3 is hydrogen, methyl, cyanomethyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl,
  • Q is CR
  • Q is CR
  • X is trifluoromethyl, difluoromethyl or pentafluoroethyl
  • W is O
  • G stands for a free electron pair or for oxygen
  • R is hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, ethoxymethyl, cyclopropyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl or prop-2-en-l-yl
  • Y is optionally mono- to trisubstituted by identical or different substituents Ci-Cö Alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or Cs-Ce-cycloalkyl, wherein the substituents are selected from halogen, nitro, cyano, hydroxy, aminothiocarbonyl, aminocarbonyl, Ci-C4-AlkyL-Ci-C4 haloalkyl, C3-Cs-cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 -Alkyl
  • Y represents optionally mono- to trisubstituted by identical or different substituents phenyl, phenylmethyl, 3-oxetan-1-yl, 3-thietan-1-yl, 3-oxidothietan-1-yl, 3,3-dioxideothietan-1-yl, Pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridin-2-yl-methyl, pyridin-3-yl-methyl, pyridin-4-yl-methyl, 1,3-
  • Very particularly preferred are the compounds of the formula (I) in which R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethoxy, trifluoromethoxy or trifluoromethylsulfonyloxy, n is 1, 2 , 3, 4 or 5 stands
  • R is hydrogen, is hydrogen, CR 4 , CR 4 , CR 4 , CR 4 , hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl, trifluoromethyl
  • O stands for a lone pair of electrons
  • NR 13 - stands, wherein the former (left) attachment site on the ring and the second-mentioned (right) attachment site to Y, and wherein hydrogen or methyl is methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2-yl, 1-butyne 3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanomethyl, 2-cyanoprop-1-y
  • R 2 is hydrogen
  • R 3 is hydrogen, Q 1 is CR 4 ,
  • R 4 is hydrogen
  • R 6 is fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl
  • X is trifluoromethyl
  • G stands for a free electron pair or for oxygen
  • R 13 is hydrogen or methyl, methyl, ethyl, propan-1-yl, propan-2-yl, butan-1-yl, butan-2-yl, 2-methylpropan-1-yl, 2-methylpropan-2 yl, l-butyn-3-yl, cyclopropyl, cyclobutyl, cyanomethyl, 1-methoxycarbonylmethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3 Cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyano-cyclopropyl, 2-cyanoprop-2-ene
  • R 1 , R 3 , R 4 ie R 4a and R 4b independently of one another have the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-1) describes a preferred embodiment of the erfindungeswashen compounds of formula (I).
  • R 2 is H
  • W is O
  • Q 1 and Q 2 are CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • A is - CO-NR 13 -.
  • G stands for a free Elektonenpar.
  • the invention relates to the compounds of the formula (I-2)
  • R 1 , R 3 , R 4 ie R 4a has the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those in embodiment (1 -1) or embodiment ( 2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-2) describes a preferred embodiment of the inventive compounds of the formula (I).
  • R 2 is H
  • W is O
  • Q 1 and Q 2 is CH
  • Q 3 is CR 4a
  • Q 4 is N
  • A is -CO- NR 13 -.
  • G stands for a free Elektonenpar.
  • the invention relates to the compounds of the formula (I-3)
  • R 1 , R 3 , R 4 ie R 4a and R 4b independently of one another have the meaning described above for R 4
  • R 6 , R 13 , Y and n have the meanings described above, in particular those described in 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • the formula (1-3) describes a preferred embodiment of the inventive compounds of the formula (I).
  • R 2 is H
  • W is O
  • Q 1 is N
  • Q 2 is CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • G stands for a free Elektonenpar.
  • G is a lone electron pair and Q 1 , Q 2 , Q 3 and Q 4 are CR 4 , where all other groups, radicals and substituents are above in embodiment (1 -1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-2) have described meanings.
  • G is a free electron pair and R 2 is hydrogen and X is trifluoromethyl, where all other groups, radicals and substituents are those described above in the embodiment (1). 1) or design (2-1) or design (3-1) or design (3-2) or design (4-1) or design (4-2) have described meanings.
  • W is O
  • G is a lone electron pair
  • Q 1 , Q 2 , Q 3 and Q 4 are CR 4
  • A is -CO-NR 13 -, where all other groups, radicals and substituents are as defined above in embodiment (1-1) or embodiment (2-1) or embodiment (3-1) or embodiment (3-2) or embodiment (4-1) or embodiment (4-5). 2) have described meanings.
  • preferred compounds according to the invention are the compounds of the general formula (I) or (1-1) shown in Table 1.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • the compounds of the formula (I) may also be present as stereoisomers, ie as geometric and / or optical isomers or mixtures of isomers in different compositions. Both the pure Stereoisomers as well as any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the 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, which include 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.
  • the present compounds of the general formula (I) may optionally have a chiral carbon atom.
  • these substituents may have both an (R) and an (S) configuration.
  • the present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
  • alkyl either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms
  • Examples of C 1 -C 12 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n
  • alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkenyl radical having at least one double bond, for example vinyl, allyl, 1 -Propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1, 3-pentadienyl, 1 -hexenyl, 2 Hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl, preferred are C2-C6-alkenyl radicals and particularly preferred are C2-C4-alkenyl radicals.
  • alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 12 alkynyl having at least one triple bond, for example, ethynyl, 1-propynyl C 3 -C 6 -alkynyl radicals are preferred and C 3 -C 4 -alkynyl radicals are particularly preferred.
  • 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, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
  • aryl according to the invention is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl.
  • arylalkyl is understood to mean a combination of radicals "aryl” and “alkyl” 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.
  • hetaryl 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 carbon atoms.
  • hetaryl is pyridinyl or pyrimidinyl.
  • 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, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl.
  • halo-substituted radicals for example “haloalkyl” are radicals which are mono- or polysubstituted to the maximum possible number of substituents halogenated radicals can be the same or different halogen atoms.
  • 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 invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always includes the term pesticides.
  • the compounds of 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, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hi
  • Aulacorthum solani Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Plutella xylostella Plutella maculipennis
  • Prays spp. Prodenia spp.
  • Protoparce spp. Pseudaletia spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Eg Schoenobius bipunctifer, Scirpophaga spp.
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests from the strain of Mollusca in particular from the class of bivalvia, for example Dreissena spp .; and from the class of Gastropoda eg Arion spp., eg Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., eg Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda eg Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp , Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp.
  • Dracunculus spp. Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp , Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp.
  • Plant pests from the Nematoda strain ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., Eg Criconemella curvata, Criconemella onoensis, Criconemella ornata
  • Paratrichodorus spp. Eg Paratrichodorus minor, Pratylenchus spp., Eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., Eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp , Scutellonema spp., Subanguina spp., Trichodorus spp., Eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., Eg Tylenchorhynchus annulatus, Tylenchulus spp., Eg Tylenchulus semipenetrans, Xiphinema spp., Eg Xiphinema
  • the compounds of the formula (I) may 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 RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • Formulations The present invention furthermore relates to formulations and use forms prepared therefrom as pesticides, such as, for example, pesticides.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
  • organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solvents are, for example, aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as methanol, Ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene, or methylene chloride
  • Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers , Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Particularly suitable are those extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons as well as 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 lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydroly
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • auxiliaries also adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate ,
  • the formulations preferably contain between 0.00000001 and 98 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 pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application. mixtures
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators
  • suitable fungicides bactericides, acaricides, molluscicides, ne
  • 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) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Suitable mixing partners are, for example, the following compounds: insecticides / acaricides / nematicides:
  • acetylcholinesterase (AChE) inhibitors such as carbamates, eg alanycarb, aldicarb, bendocarb, benfuracarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, Pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, eg acephates, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrif
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- Cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], e
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfbxaflor.
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as Alkyl halides, eg methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and fenbutatin oxide or propargite or
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as Bupro fezin.
  • Anti-skinning agents especially in dipterans, i.e., two-toed, such as Cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • Voltage-dependent sodium channel blockers eg indoxacarb or metaflumizone.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Dicofol, Diflovidazine, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazone, pyriminostrobin, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacill
  • inhibitors of ergosterol biosynthesis such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole cis, (1.21)
  • inhibitors of respiration such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS),
  • inhibitors of amino acid and protein biosynthesis such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin.
  • inhibitors of ATP production such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.
  • inhibitors of cell wall synthesis such as (9.1) benthia-valicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) Valifenalate and (9.10) Polyoxin B.
  • inhibitors of lipid and membrane synthesis such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8)
  • Isoprothiolane (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb ,, (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazenes and (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis such as (11.1) carpropamide, (11.2) diclocymet,
  • inhibitors of nucleic acid synthesis such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, ( 12.8) Hymexazole, (12.9) Metalaxyl, (12.10) Metalaxyl-M (mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinic acid and (12.14) Octhilinone.
  • Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide.
  • decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap.
  • Other compounds such as (15.1) benthiazole, (15.2) betoxazine, (15.3) capsimycin,
  • the compounds of formula (I) may be combined with biological pesticides.
  • biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus Strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession No. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, in particular strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV
  • Spodoptera frugiperda armyworm
  • mNPV Spodoptera littoralis
  • Examples of plant extracts and products formed by microorganisms including proteins and secondary metabolites used as biological pest control agents can, 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 , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants 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.
  • Plant parts should be understood as meaning all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root.
  • leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) takes place directly or by acting on their environment, habitat or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing on, injecting and in the case of propagation material , in particular in the case of seeds, continue to be coated in one or more layers.
  • all plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “parts of plants” has been explained above.
  • Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
  • PV plants are understood as meaning plants with new properties ("traits") have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, caused for example by toxins formed in the plants, in particular those caused by the genetic material from Bacillus Thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against phytopathogenic fungi, bacteria and / or viruses, eg through systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and accordingly expressed proteins and toxins, as well as an increased tolerance of the plants against certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (SAR), systemin,
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails. Plant protection - types of treatment
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds further by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to dispense the compounds of formula (I) by the ultra-low-volume method or the use form or the compound of formula ( I) inject myself into the soil.
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant.
  • This can be, for example, by drenching, mixing in the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I), or by the soil application, ie the compounds of Formula (I) are introduced in solid form, (eg in the form of granules) in the location of the plants.
  • a solid application form eg as granules
  • 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 by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of 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 formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers which contain a compound of the formula (I) and mixture partners may optionally be replaced by a Interlayer be separated.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating.
  • the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • compounds of the formula (I) can also be used in 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.
  • 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 beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seed which contains at least one contains heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates for the compound of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I), which have 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 parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and crustaceans, eg in aquaculture and insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • control means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • the arthropods include: 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 Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Omithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis;
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis,
  • Toxoplasmadidae for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum,
  • Theileria spec such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (eg, Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
  • Cestodes from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp ., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from 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.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or acaricide
  • an arthropodicide such as an insecticide or acaricide
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • vectors and their transmitted diseases or pathogens are:
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, especially the genera Aedes, Anopheles, eg A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies , Mites and ticks that can transmit pathogens to animals and / or humans.
  • vector control is also possible when the compounds of formula (I) are resistance-disrupting.
  • Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • 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, that is, it can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question are present as a ready-to-use pest control agent, that is, it can be applied to the corresponding material without further changes.
  • 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.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the compounds of formula (I) are used alone or in Combination with other active ingredients and / or excipients used.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • the application is carried out, for example, in aerosols, pressureless sprays, eg pump and atomizer sprays, smoke machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, Moth sacs and moth gels, as granules or dusts, in straw baits or bait stations.
  • the compounds of the formula (I) can be prepared by the method described below.
  • the substituent eg, R 1, n, Q 1, etc.
  • R 1, n, Q 1, etc. have if not explicitly described otherwise the meanings described above.
  • the dicarboxylic acid of the general formula (II) can firstly be converted into an acid halide and then reacted in the presence of a base such as, for example, triethylamine or sodium hydroxide.
  • a base such as, for example, triethylamine or sodium hydroxide.
  • the carboxylic acid can also be carried out using coupling reagents such as dicyclohexylcarbodiimide and additives such as 1-hydroxybenzotriazole [Chem. Ber. 1970, 788].
  • coupling reagents such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, ⁇ , ⁇ -carbonyl-1H-imidazole, N- [(1H-benzotriazol-1-ylxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate , and similar compounds.
  • Suitable coupling reagents for carrying out the dartelling process are all those which are suitable for the preparation of an ester or amide bond (cf., for example, Bodansky et al. Peptide Synthesis, 2nd Ed., Wiley & Sons, New York, 1976; Gross, Meienhofer, The Peptides: Analysis, Synthesis, Biology (Academic Press, New York, 1979), use.
  • condensation reagent such as, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide or ⁇ , ⁇ -carbonyl-1H-imidazole, N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N- methylmethanaminiumhexafluorophosphat converted into compounds of general formula (1-1), wherein G then stands for a free electron pair.
  • a condensation reagent such as, for example, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide or ⁇ , ⁇ -carbonyl-1H-imidazole, N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N- methylmethanaminiumhexafluorophosphat converted into compounds of general formula (1-1), wherein G then stands for a free electron pair.
  • the compounds of the formula (IV) can also be first converted into the corresponding acid chloride, for example by reaction with thionyl chloride or sulfuryl chloride, and then reacted with amines of the formula (VII) in the presence of a base such as triethylamine to give compounds of the formula (Ia) ,
  • R a , R, R 0 and R independently of one another have the meaning described above for R are partially known or can be obtained by hydrolysis of corresponding ester precursors (see, for example, quinoline-2,6-dicarboxylic acid: Journal of Heterocyclic Chemistry (1989 ), 26 (4), 929-31; 4-chloroquinoline-2,6-dicarboxylic acid: CAS registry number 902742-45-4; 2-methoxycarbonyl-4-methyl-quinoline-6-carboxylic acid: WO 9613485; methylquinoline-2,6-dicarboxylate: Bioorganic & Medicinal Chemistry (2006), 14 (13), 4600-4609).
  • Quinoline dicarboxylic acids of the formula (II-1a) are obtained here in analogy to known processes from nitriles of the formula (A-9) by alkaline hydrolysis, for example with LiOH in methanol.
  • Nitriles of the formula (A-9) can be obtained from quinoline N oxides of the formula (A-8) by reaction with a cyanide, for example trimethylsilyl cyanide in the presence of a base, for example triethylamine (cf., for example, WO-A-2011 / 9540).
  • Quinoline N-oxides of the formula (A-8) can be obtained by oxidation of a quinoline of the formula (A-7), for example with m-chloroperbenzoic acid (cf., for example, WO-A-2011/9540).
  • Quinolines of the formula (A-7) can be obtained in analogy to known processes by reacting an aniline of the formula (A-6) with glycerol in the presence of sulfuric acid (cf., for example, Heterocyles 29 (12) 2345-51, 1989).
  • Compounds of the formula (A-6) are commercially available, known from the literature or obtainable in analogy to processes known from the literature Quinazoline carboxylic acids of the formula ⁇ -2),
  • R a , R and R 0 independently of one another have the meaning described above for R are partially known or can be obtained by hydrolysis of corresponding ester precursors (cf., for example l, 8-naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92 (5), 959-966; 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047).
  • ester precursors cf., for example l, 8-naphthyridine-2,6-dicarboxylic acid: Helvetica Chimica Acta (2009), 92 (5), 959-966; 5-hydroxy-1,8-naphthyridine-2,6-dicarboxylic acid: WO-A-2010/017047.
  • Quinazolinecarboxylic acids of the formula (II-2a) are hereby obtained in analogy to known processes from compounds of the formula (A-12) by oxidation of the methyl group, for example with potassium permanganate or selenium dioxide (cf., WO-A-2010/101949, J. Het 1989, 26, 929-31)
  • Compounds of the formula (A-12) can be obtained by halogenation of the corresponding hydroxy compounds of the formula (A-11), for example with phosphorus oxychloride or phosphorus oxybromide (cf., WO-A-2008/133753).
  • the compound of the formula (A-11) can be obtained by reacting 2-amino-6-methylpyridine with dimethyl 2- (methoxymethylene) propanedioate (see US2001 / 46989, J. Med. Chem. 1997, 40, 2674).
  • Quinazolinecarboxylic acids of the formula ⁇ -3) can be obtained by reacting 2-amino-6-methylpyridine with dimethyl 2- (methoxymethylene) propanedioate (see US2001 / 46989, J. Med. Chem. 1997, 40, 2674).
  • Quinazolinecarboxylic acids of the formula (II-3a) are hereby prepared in analogy to generally known processes from compounds of the formula (A-18) by hydrolysis of the cyano group, e.g. obtained with sodium hydroxide solution.
  • Nitriles of formula (A-18) can be obtained from the corresponding bromo compounds of formula (A-17) by reaction with cyanide (see WO-A-2012/177728, WO-A-2003/010146).
  • Quinazoline carboxylic acids of formula (A-17) may be e.g. by reaction of aminomethyl compounds of the formula (A-16) with ethyl 2-oxoacetates are obtained (see Bioorg., Med. Chem. 2009, 17, 8221-8233).
  • Compounds of the formula (A-16) can be obtained by generally known processes in a multistage synthesis from anilines of the formula (A-13) (see Organic Letters 15 (2013), 3766).
  • Amines of the general formula (III) are known from the literature or can be obtained analogously to processes known from the literature (cf., for example, WO-A-2011/054436, WO-A-2012/119984).
  • compounds of formula (I) and (II) can be prepared by the methods described above. If individual connections do not follow the procedure described above can be prepared, the synthesis by derivatization of other compounds of formulas (I) and (II) is possible or by individual modifications of the described methods. For example, it may be advantageous to prepare certain compounds of formulas (I) or (II) from other compounds of formulas (I) and (II), for example, by hydrolysis, esterification, amide formation, reduction, etherification, oxidation, olefination, halogenation, acylation , Alkylation and the like.
  • Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. As examples are :.
  • Halogenated hydrocarbons eg chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (eg.
  • chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane,
  • Octylcaprolactam 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, ⁇ , ⁇ '-diformyl-piperazine) and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
  • ketones e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
  • the process according to the invention is 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 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), N, N, N, N-tetramethyl-l, 8-naphthalenediamine,
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • Pentamethylpiperidine and amines, especially tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, ⁇ , ⁇ -dimethyl-toluidine, N, N-dimethyl-p-aminopyridine , N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline , ⁇ -picoline, ⁇ -picoline, pyrimidine, acridine, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylenediamine, ⁇ ,
  • mineral acids for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids for example aluminum (III) chloride, boron trifluoride or etherate
  • Titanium (IV) chloride, tin (IV) chloride 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
  • hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids for example aluminum (III) chloride,
  • Step 2 Methyl 5-bromoquinolines-6-carbox late / methyl-7-bromoquinolines-6-carboxylates
  • Step 3 Methyl 5-bromo-1-oxido-quinoline-1 -ium-6-carboxylate / methyl-7-bromo-1-oxo-quinoline-l-ium-6-carboxylate
  • Methyl-5-bromo-2-cyano-quinoline-6-carboxylate (0.183 g, 0.629 mmol) was suspended in ethanol (25 mL) and sodium hydroxide solution (45%, 201 mg, 5.029 mmol) was added. The reaction mixture was stirred for 18 hours at 50 ° C and then stirred into 10 ml of ice water. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. There were obtained 0.128 g (68% of theory) of 5-bromoquinolines-2,6-dicarboxylic acid.
  • Step 6 5-Bromo-2 - [[2,2,2-trifluoro-1- (4-fluoro-3- (trifluoromethyl) phenyl] ethyl] cw
  • 5-Bromoquinolines-2,6-dicarboxylic acid 60 mg, 0.203 mmol was dissolved in N, N-dimethylformamide (1.0 mL) and sequentially 2,2,2-trifluoro-l- [4-fluoro-3- ( trifluoromethyl) phenyl] ethanamine (66.15 mg, 0.253 mmol), N - [(1H-benzotriazol-1-yloxy) (dimethylamino) methylene] -N-methylmethanaminium hexafluorophosphate (76.9 mg, 0.203 mmol); Methylmorpholine (81.99 mg, 0.811 mmol) was added.
  • Methyl 5-nitroquinoline-6-carboxylate 5-Nitroquinoline-6-carboxylic acid (6200 mg, 28.4 mmol) (eg known from WO9812180) was suspended in dichloromethane (125.0 mL) and treated at 0 ° C with oxalyl chloride ( 4328 mg, 34.1 mmol). The reaction mixture was first stirred for 1 h at room temperature and then for a further 1 h at reflux temperature. After distilling off the solvent, methanol (23 mL, 18211 mmol) was added and stirred at room temperature for 18 hours. The excess methanol was distilled off for the most part and the residue was mixed with 300 mL of water.
  • Methyl 5-aminoquinoline-6-carboxylate Methyl 5-nitroquinoline-6-carboxylate (600 mg, 25.8 mmol) was dissolved in methanol / THF (250.0 mL / 7.5 mL) and treated with Pd-C hydrogenated as catalyst (274 mg, 2.58 mmol) at 1 bar pressure. The reaction mixture was filtered through kieselguhr, washed with methanol and the solvent was distilled off under reduced pressure.
  • Methyl 5-iodoquinoline-6-carboxylate Methyl 5-aminoquinoline-6-carboxylate (4800 mg, 23.7 mmol) was slowly added at 100 ° C to a mixture of 3-methylbutyl nitrite (4449 mg, 37.9 mmol). and methylene diiodide (38.2 mL, 474 mmol). After stirring for 0.5 h at 100 ° C, the reaction mixture was mixed with water and extracted several times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and then concentrated.
  • 3-methylbutyl nitrite 4449 mg, 37.9 mmol
  • methylene diiodide 38.2 mL, 474 mmol
  • Methyl 5-iodoquinoline-6-carboxylate 1-oxide Methyl 5-aminoquinoline-6-carboxylate (2500 mg, 7.98 mmol) was initially charged in dichloromethane (15.0 mL) and hydrogen peroxide (50%, 1086 mg, 15.9 mmol) and methyltrioxorhenium (VII) (39.8 mg, 0.16 mmol). The reaction mixture was stirred for 18 h, then extracted repeatedly with water and the aqueous phase with ethyl acetate.
  • Methyl 2-cyano-5-iodoquinoline-6-carboxylate (600mg, 1.82mmol) was dissolved at 0 ° C in a solution of potassium cyanide (237mg, 3.64 mmol) in water (7.8 mL). To this was added benzoyl chloride (0.432 mL, 3.64 mmol) and stirred for 1 h under ice cooling. The aqueous phase was decanted off and the residue was stirred with 1M potassium carbonate solution. After addition of dichloromethane, the phases were separated, washed with water, dried over magnesium sulfate and the solvent removed in vacuo.
  • 5-iodoquinoline-2,6-dicarboxylic acid methyl 2-cyano-5-iodoquinoline-6-carboxylate (326 mg, 0.96 mmol) was suspended in ethanol (8.0 mL) and washed with sodium hydroxide solution (45%, 685 mg, 7.71 mmol). The reaction mixture was stirred for 18 hours at 50 ° C and then in 200 ml of ice water stirred. After acidification with 30% hydrochloric acid, the precipitated solid was filtered off with suction and dried. 243 mg (71% of theory) of 5-iodoquinoline-2,6-dicarboxylic acid were obtained.
  • R 2 is H
  • W is O
  • Q 1 and Q 2 are CH
  • Q 3 is CR 4a
  • Q 4 is CR 4b
  • A is -CO-NR 13 -
  • G is a free one Elektonenjo.
  • Example 1-1-01 1 H-NMR (400.0 MHz, de-DMSO): See Synthesis Example 1
  • Example 1-1-04 1 H-NMR (400.0 MHz, de-DMSO):
  • ⁇ 10.135 (2.0); 10.122 (2,1); 9.675 (2.5); 8,899 (10.1); 8.884 (10.9); 8,883 (10.3); 8,332 (10,2); 8,325 (15.4); 8,318 (11,6); 8,317 (11.0); 8,310 (16.0); 8,302 (10.9); 8,154 (5.8); 8,141 (6,2); 7,952 (14.8); 7,937 (14,3); 7,841 (5.5); 7,828 (7.0); 7,744 (5.1); 7,731 (8.7); 7,718 (3.9); 6.378 (2.6); 6,366 (1.9); 4,040 (0.6); 4.028 (0.6); 3,417 (0.4); 3,413 (0.3); 3,367 (653.8); 3,324 (0.4); 2,622 (0.4); 2,531 (0.7); 2,528 (0.9); 2,525 (0.9); 2,516 (23.7); 2,513 (49,7); 2,510 (67.9); 2,507 (49,7); 2,505 (23.8); 2,394 (0.4); 2,092 (10.2);
  • ⁇ 10.113 (1.9); 10,089 (2.0); 8.815 (2.4); 8,793 (2.6); 8,568 (2,1); 8,557 (2,1); 8.528 (1.1); 8,509 (1.9); 8.490 (1.1); 8.317 (0.5); 8,199 (3.8); 8,177 (3.7); 8.132 (2.3); 8.110 (2.5); 7.751 (3.5); 7,730 (3,1); 6,465 (0.8); 6.433 (1.1); 6,420 (0.8); 3,324 (95.7); 3.175 (1.1); 3.162 (1.0); 2,925 (0.6); 2,916 (0.9); 2.907 (1.3); 2,897 (1.3); 2,889 (0.8); 2,879 (0.6); 2,667 (16.0); 2,524 (4,6); 2,511 (51.5); 2,507 (100.9); 2,502 (131.4); 2,498 (94.5); 2,493 (45.9); 2.333 (0.6); 2,329 (0.9); 2.325 (0.6); 0.756 (0.9); 0.743 (2.5); 0.738 (3.3); 0.726 (3.0);
  • Example 1-1-16 1 H NMR (400.0 MHz, d 6 -DMSO):
  • ⁇ 10.147 (0.4); 10.131 (3.5); 10,106 (3,6); 8,884 (5.1); 8,862 (5.5); 8,861 (5.4); 8,650 (1.0); 8,640 (2.7); 8.628 (2.7); 8.617 (0.9); 8.366 (0.7); 8,307 (12,7); 8,299 (7.6); 8,285 (7.9); 8,277 (5.8); 8,155 (3,1); 8,136 (3,1); 7.921 (0.5); 7,908 (7,8); 7,899 (0.6); 7,886 (7.2); 7,840 (2.8); 7,821 (3.8); 7,744 (2.8); 7,724 (4.4); 7,705 (1.8); 6,421 (0.4); 6,399 (1.5); 6,377 (2,2); 6,354 (1.6); 6,333 (0.5); 3,619 (0.5); 3,608 (0.5); 3.602 (1.3); 3.596 (0.5); 3.586 (0.5); 3,331 (78.2); 2,850 (16.0); 2,838 (15,8); 2,698 (0.5); 2,686 (0.5); 2,677 (
  • ⁇ 10.135 (1.7); 10.111 (1.7); 8,879 (2,4); 8.857 (2.6); 8,593 (1.6); 8,574 (1.6); 8,308 (6,1); 8,297 (2.7); 8,286 (3.6); 8.275 (2.7); 8,159 (1.3); 8.140 (1.4); 7,881 (3.6); 7,859 (3.3); 7.841 (1.2); 7,821 (1.7); 7,745 (1.3); 7,726 (2.0); 7.706 (0.8); 6,399 (0.7); 6,377 (1.0); 6,354 (0.7); 5,759 (0.4); 4.147 (0.7); 4.113 (1.0); 4.112 (1.0); 4,095 (0.7); 4,039 (0.7); 4,021 (0.7); 3,334 (72.6); 2,673 (0.3); 2,526 (0.9); 2,512 (21.3); 2,508 (42.4); 2,504 (55.1); 2,499 (39.5); 2,495 (19.0); 2,331 (0.4); 1,990 (3.0); 1,208 (16,0); 1,191 (16.0); 1.176 (1.8);
  • ⁇ 10.122 (3.0); 10.098 (3.1); 9,784 (2.7); 9,222 (6.4); 8,972 (2.7); 8,871 (4,1); 8.849 (4.5); 8,323 (2,9); 8,300 (16.0); 8,278 (6.0); 8,268 (7.3); 8.246 (3.5); 8.157 (2.5); 8.138 (2.6); 7,843 (2.2); 7,823 (3,1); 7.746 (2.3); 7,727 (3.5); 7,707 (1.5); 6,421 (0.4); 6,400 (1.3); 6.379 (1.8); 6.356 (1.3); 6.334 (0.4); 3,337 (128.3); 2,678 (0.4); 2,674 (0.5); 2,670 (0.4);
  • ⁇ 10.163 (1.3); 10.139 (1.3); 8,882 (1.7); 8.860 (1.8); 8,693 (1.2); 8,673 (1.2); 8,407 (0.9); 8,392 (0.9); 8,308 (3.3); 8,289 (2,2); 8,286 (3,2); 8.260 (0.6); 7,893 (2,4); 7.871 (2.3); 7,680 (0.7); 7.655 (1.0); 7.632 (0.7); 6,435 (0.5); 6,413 (0.8); 6,391 (0.6); 4,210 (0.6); 4.191 (0.7); 4.174 (0.6); 4.056 (0.3); 4.038 (1.1); 4.021 (1.1); 4.003 (0.4); 3,326 (43.1); 2,729 (0.6); 2,712 (0.6); 2,696 (1.2); 2,678 (1.3); 2,668 (0.3); 2,642 (1.0); 2,625 (1.0); 2.609 (0.5); 2,592 (0.5); 2,525 (1.0); 2,512 (22.3); 2,507 (44.2); 2,503 (57.6); 2,498 (42.3);
  • ⁇ 10.205 (3.5); 10.181 (3.6); 9,571 (3.9); 9,552 (4.0); 8,925 (4,6); 8,924 (4,6); 8,903 (5.1); 8,902 (5.2); 8,513 (1.9); 8.494 (3,4); 8.475 (1.9); 8,349 (8.2); 8,343 (4,8); 8,341 (4,7); 8,326 (8.0); 8,321 (5,3); 8,320 (5.3); 7,957 (7.9); 7.935 (7.4); 6.491 (0.4); 6,470 (1.3); 6.449 (1.8); 6,426 (1.4); 6,404 (0.5); 5.758 (1.1); 5.104 (0.5); 5,086 (2.3); 5,068 (3.6); 5,050
  • Example 1-1-55 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-56 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-58 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-59 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-61 1 H-NMR (400.0 MHz, d6-DMSO):
  • Example 1-1-63 1 H-NMR (400.0 MHz, d6-DMSO):
  • ⁇ 10.170 (1.2); 10.145 (1.2); 9.496 (0.6); 9,482 (1.4); 9,468 (0.6); 8.861 (1.6); 8.839 (1.8); 8.408 (0.8); 8.391 (0.8); 8.365 (1.6); 8,343 (1.8); 8.322 (2.4); 8,300 (2,4); 8.275 (0.4); 8.269 (0.5); 8.261 (0.5); 8.254 (0.5); 8.248 (0.5); 7.905 (2.4); 7.884 (2.3); 7,682 (0.7); 7.656 (0.9); 7.633 (0.7); 6.442 (0.4); 6,420 (0.7); 6.397 (0.5); 5,759 (1.2); 4,440 (3,1); 4,426 (3,1); 4.057 (1.2); 4,039 (3.7); 4,021 (3.7); 4.004 (1.3); 3,336 (44.3); 2,528 (0.5); 2,514 (11,7); 2,510 (23.8); 2,505 (31.5); 2,501 (23.1); 2,496 (11.4); 1,991 (16.0); 1.338 (1.2);
  • Example 1-1-66 1 H-NMR (400.0 MHz, d6-DMSO):
  • NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists.
  • the 'H NMR data of selected examples are noted in terms of' H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in parentheses 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: ⁇ 1 (intensity I); ⁇ 2 (intensity 2); ; ⁇ i (intensity i); ; ⁇ n (intensity n)
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 'H NMR interpretation.
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-1-01, 1-1-05, 1-1-06, 1-1-07, 1-1-08, 1-1-09, 1-1-10, 1-1-11, 1-1-12, 1-1-13, 1-1-14, 1-1-15, 1-1-16, 1- 1-17, 1-1-18, 1-1-19, 1-1-20, 1-1-21, 1-1-22, 1-1-23, 1-1-24, 1-1- 25, 1-1-26, 1-1-27, 1-1-28, 1-1-29, 1-1-30, 1-1-31, 1-1-32, 1-1-33, 1-1-34, 1-1-35, 1-1-36, 1-1-37, 1-1-38, 1-1-39, 1-1-40, 1-1-41, 1- 1-42, 1-1-43, 1-1-44, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-49, 1-1- 50, 1-1-51, 1-1-52, 1-1- 53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1-1-59, 1-1-60, 1-1-6
  • Emulsifier alkylaryl polyglycol ether
  • 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z.
  • the following compounds of Preparation Examples have an effect of 90% at a rate of 100 g / ha: 1-1-01, 1-1-07, 1-1-11, 1-1-16, 1-1-32 , 1-1-56, 1-1-59
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid ⁇ Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
  • SPODFR Spodoptera frugiperda - spray test
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • active compound 10 mg are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
  • Tick nymphs Ambfyomma hebraeum
  • the ticks are put on filter paper in one
  • Petri dish transferred and stored in a climatic cabinet.
  • Boophilus microplus - Diptest BOOPMI Dip
  • Test animals Bovine tick (Boophilus microplus) strain Parkhurst, SP-resistant Solvent: Dimethylsulfoxide
  • the active ingredient 10 mg are dissolved in 0.5 ml of dimethyl sulfoxide.
  • the active compound solution is diluted with water to the particular desired concentration.
  • This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female bovine ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
  • the following compounds of the preparation examples show an effect of 80% at an application rate of 100 ppm: 1-1-43, 1-1-47, 1-1-55, 1-1-56, 1-1- 62 90% at a rate of 100 ppm: 1-1-57
  • Boophilus microplus injection test (BOOPMI Inj)
  • Solvent Dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
  • CTECFE Ctenocephalides felis - Oral test
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. On the chamber, a metal cylinder is placed, whose Bottom is closed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • Lucilla cuprina - test (LUCICU)
  • active compound 10 mg are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty LI larvae of the Australian Goldfinch ⁇ Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the vials are filled with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move uncoordinated are considered dead or struck.
  • a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100%) effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 5 ⁇ g / cm 2 : 1-1-01, 1-1-03, 1-1-14, 1-1-20, 1 -1-21, 1-1-25, 1-1-27, 1-1-28, 1-1-29, 1-1-31, 1-1-32, 1-1-33, 1-1 -35, 1-1-37, 1-1-42, 1-1-43, 1-1-45, 1-1-46, 1-1-47, 1-1-48, 1-1-50 , 1-1- 51.1-1-52, 1-1-53, 1-1-54, 1-1-55, 1-1-56, 1-1-57, 1-1-58, 1 -1-59, 1-1-60, 1-1-61 Rhipicephalus sanguineus - in vitro contact tests with adults of brown dog tick
  • the vials are populated with 5-10 adult dog tick ⁇ Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated lying in the dark at room temperature and ambient humidity. After 48 h the efficacy is determined. For this, the ticks are tapped on the bottom of the jar and on a hot plate at 45-50 ° C for a maximum of 5 min. incubated.
  • a substance shows good activity against Rhipicephalus sanguineus, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all ticks were struck or dead. 0% effect means that no ticks have been damaged.

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

Abstract

L'invention concerne des composés de formule générale (I), dans laquelle R1 à R6, A, Y, X, G, Q1 à Q4 et n ont les significations données dans la description, ainsi qu'un procédé pour les préparer et leur utilisation en tant qu'insecticides et acaricides.
PCT/EP2015/050732 2014-01-20 2015-01-16 Dérivés de quinoléine utilisés comme insecticides et acaricides WO2015107133A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9802895B2 (en) 2014-02-17 2017-10-31 Bayer Cropscience Aktiengesellschaft Indole and benzimidazolecarboxamides as insecticides and acaricides
EP3597041A4 (fr) * 2017-03-17 2021-03-24 Meiji Seika Pharma Co., Ltd. Agent de lutte contre l'acarien mésostigmates

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9802895B2 (en) 2014-02-17 2017-10-31 Bayer Cropscience Aktiengesellschaft Indole and benzimidazolecarboxamides as insecticides and acaricides
EP3597041A4 (fr) * 2017-03-17 2021-03-24 Meiji Seika Pharma Co., Ltd. Agent de lutte contre l'acarien mésostigmates

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