WO2015158603A1 - Composés d'oxime de malononitrile - Google Patents

Composés d'oxime de malononitrile Download PDF

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WO2015158603A1
WO2015158603A1 PCT/EP2015/057739 EP2015057739W WO2015158603A1 WO 2015158603 A1 WO2015158603 A1 WO 2015158603A1 EP 2015057739 W EP2015057739 W EP 2015057739W WO 2015158603 A1 WO2015158603 A1 WO 2015158603A1
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alkyl
alkoxy
cycloalkyl
unsubstituted
substituted
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Pascal BINDSCHÄDLER
Sebastian SÖRGEL
Matthias Pohlman
Ralph Paulini
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/50—Spiro compounds

Definitions

  • the invention relates to aryl alkyl malononitriles, thioamides and amides, a method for their preparation and their use for combating animal pests, an agricultural composition or seeds comprising said malononitriles, thioamides or amides, a method for combating animal pests, a method for protecting crops from attack or infestation by animal pests, a method for protecting seeds from soil insects and the seedlings' roots and shoots from soil and foliar insects.
  • Pesticidal compounds having a dicyanoalkane moiety have been disclosed in a number of pa- tent applications, e.g. JP 2002 284608, WO 02/089579, WO 02/090320, WO 02/090321 , WO 04/006677, WO 04/020399, JP 2004 99593, JP 2004 99597, WO 05/068432, WO 05/064823, EP 1555259, WO 05/063694, WO 2007/071609, and WO 2007/147888.
  • JP 2002 284608 WO 02/089579, WO 02/090320, WO 02/090321 , WO 04/006677, WO 04/020399, JP 2004 99593, JP 2004 99597, WO 05/068432, WO 05/064823, EP 1555259, WO 05/063694, WO 2007/071609, and WO 2007/147888.
  • Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R 5 ; or naphthyl un- substituted or substituted with 1 , 2, 3, 4, 5, 6 or 7 substituents R 5 ;
  • Q is C3-C8-cycloalkyl or Cs-Cs-cycloalkenyl, wherein Cs-Cs-cycloalkyl and Cs-Cs-cycloalkenyl are substituted with
  • R 1 is hydrogen, halogen, cyano, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl, C3-C6-cycloalkenyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, Ci-C6-alkylthio, (C1-C6- alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1 , 2 or 3 substituents R 7 ;
  • R 2 is hydrogen or halogen
  • R 1 and R 2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R 5 , R 6 is independently halogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R a ;
  • each R b is independently halogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkyny
  • each R c is independently halogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
  • each R d is independently halogen, cyano, azido, nitro, -SCN, SF 5 , Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C3-C6-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
  • each R e is independently halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxyalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C6-haloalkoxyalkyl,
  • each R f is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, C3-C6-cycloalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
  • each R h is independently hydrogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C6- cycloalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
  • each R' is independently hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C6- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
  • R' on one nitrogen atom are together a C2-C7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2, and wherein the alkylene chain is unsubstituted or substituted with halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl; each R m is independently hydrogen, -SCN, SF 5 , Ci-C6-alkyl
  • each R A is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, trime- thylsilyl, triethylsilyl, tert-butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the four last mentioned radi- cals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
  • each R B is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radi- cals selected from C1-C4 alkoxy;
  • each R D is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the four last mentioned radi- cals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy;
  • phenyl benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy and (Ci-C6-alkoxy)carbonyl,
  • each R E is independently cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldi
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from Ci-C4-alkoxy,
  • each R E is independently C1-C4 alkyl, C1-C6 cycloalkyl, C1-C4 alkoxyalkyl, phenyl or benzyl; each R G is independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 haloalkoxyalkyl; each R H is independently hydrogen, cyano, Ci-C6-alkylsulfinyl, Ci-C6-alkylsul
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R K is independently hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkyl-C3-C6-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygen- ated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy,
  • each R N is independently hydrogen, OH, SH , -SCN , SF 5 , Ci-Ce-alkoxy, Ci-C 6 -haloalkoxy, Ci- C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy; each R Q is independently hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert- butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
  • each R s is independently hydrogen, OH, SH, -SCN , SF 5 , Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci- C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C1-C4 alkoxy;
  • an agricultural and/or veterinary composition comprising at least one compound of formula (I) according to the invention or a salt thereof.
  • said composition further comprises at least one inert liquid and/or at least one solid carrier.
  • a method for combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof.
  • a method for protecting crops from attack or infestation by animal pests which comprises contacting the crop with a pesticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof.
  • a method for protecting seeds from soil insects and the seedlings' roots and shoots from soil and foliar insects which comprises contacting the seeds before sowing and/or after pregermination with at least one compound of formula (I) according to the invention or a salt thereof.
  • seeds comprising at least one compound of formula (I) according to the invention or a salt thereof.
  • a method for treating or protecting animals against infestation or infection by parasites which comprises orally, topically or parenteral- ly administering or applying to the animals a parasiticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof.
  • a method for the preparation of a composition for treating or protecting animals against infestation or infection by parasites which com- prises mixing a parasiticidally effective amount of at least one compound of formula (I) according to the invention or a salt thereof and at least one solid carrier.
  • the present invention also relates to plant propagation materials, in particular seeds, comprising at least one compound of formula I or a salt thereof.
  • the present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • the compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) or modifications which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula I, mixtures of different crystalline states or modifications of the respective compound I, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of formula I are preferably agriculturally and/or veterinarily acceptable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally or veterinarily useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammoni- urn in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, di- methylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl- ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammo- nium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • halogen refers to fluoro, chloro, bromo and iodo.
  • partially or fully halogenated means that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • C n -C m -alkyl refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g.
  • 1 to 10 carbon atoms preferably 1 to 6 or 1 to 4 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbut
  • Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.
  • Ci-C4-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichlorome- thyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlo- rodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroeth
  • Ci-Cio-haloalkyl, Ci-C6-haloalkyl or Ci-C4-haloalkyl in particular comprise Ci-C2-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
  • C n -C m -alkoxy and "C n -C m -alkylthio" (or the term “C n -C m -alkylsulfenyl", respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group.
  • Ci-C4-alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy
  • futher Ci-C4-alkylthio such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.
  • C n -C m -haloalkoxy and "C n -C m -haloalkylthio” (or the term “C n -C m - haloalkylsulfenyl", respectively) refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.
  • Ci-C2-haloalkoxy such as chloromethoxy, bromomethoxy, dichloro- methoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluorometh- oxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoro- ethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- chloro-2,2-difluoroethoxy, 2,2-dichlor
  • Ci-C2-fluoroalkoxy and “Ci-C2-fluoro- alkylthio” refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxy- gen atom or a sulfur atom, respectively.
  • C2-C m -alkenyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 or 2 to 4 carbon atoms and a double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl-1 -butenyl, 3- methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 -methyl-2-
  • C2-C m -alkynyl refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 or 2 to 4 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl and the like.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group.
  • C3-C m -cycloalkyl refers to a monocyclic 3- to m-membered saturated cycloaliphatic radical, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooc- tyl and cyclodecyl.
  • aryl refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
  • naphthyl refers to 1 -naphthyl and 2-naphthyl.
  • naphthyl is
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobu- tane, cyclopentane and cyclohexane rings.
  • 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO2 refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl include:
  • oxiranyl aziridinyl, azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3- tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4- isothiazolidinyl, 5-isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4
  • Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclyl include:
  • 4-, 5-, 6- or 7-membered aromatic heterocyclyl is 5- or 6-membered aromatic heterocyclyl (hetaryl).
  • Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4- pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5-thiazolyl, 2- imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4- pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • C2-C7-alkylene refers to a divalent branched or preferably un- branched saturated aliphatic chain having 2 to 7 carbon atoms, for example CH2CH2, -CH(CHs)-, CH2CH2CH2, CH(CH 3 )CH 2 , CH 2 CH(CH 3 ), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2 and CH2CH2CH2CH2CH2CH2CH2.
  • tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl refers to C2-C4-alkynyl substituted with tri-(Ci-C4-alkyl)silyl.
  • (trimethylsilyl)ethynyl refers to ethynyl substituted with trimethylsilyl.
  • Ci-C6-alkyl-C3-C8-cycloalkyl refers to Cs-Cs-cycloalkyl substituted with Ci-C6-alkyl.
  • Ci-C4-alkyl-C3-C6-cycloalkyl refers to C3-C6- cycloalkyl substituted with Ci-C4-alkyl.
  • phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R 5 / R 6 means "phenyl unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of substituents R 5 / R 6 ", and also preferably "phenyl unsubstituted or substituted with 1 , 2, 3 or 4 substituents R 5 / R 6 ", more preferably "phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R 5 / R 6 ", even more preferably "phenyl unsubstituted or sub- stituted with 1 or 2 substituents R 5 / R 6 ", and particularly preferably "phenyl unsub
  • the term "naphthyl unsubstituted or substituted with 1 , 2, 3, 4, 5, 6 or 7 substituents R 5 " means “naphthyl unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of substituents R 5 ", more preferably “naphthyl unsubstituted or substituted with up to 3 substituents R 5 ", even more preferably “naphthyl unsubstituted or substituted with up to 2 substituents R 5 ", and particularly preferably "naphthyl unsubstituted or substituted with up to 1 substituent R 5 ".
  • the term "unsubstituted or substituted with up to 5 R c / R d / R E e.g. in connection with phenyl or a heterocyclic ring, means “unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of R c / R d / R E ", more preferably “unsubstituted or substituted with up to 2 or in the case of halogen up to the maximum possible number of R c / R d / R E ", also more preferably "unsubstituted or substituted with up to 3 R c / R d / R E ", and even more preferably "unsubstituted or substituted with up to 2 R c / R d / R E ".
  • the term "unsubstituted or substituted with one or more”, e.g. in connection with substituents R 6 , R a , R b or R M , means "unsubstituted or substituted with up to 5 or in the case of halogen up to the maximum possible number of", more preferably “unsubstituted or substituted with up to 3 or in the case of halogen up to the maximum possible number of", even more preferably "unsubstituted or substituted with up to 2 or in the case of halogen up to the maximum possible number of", also more preferably "unsubstituted or substituted with up to 5", also even more preferably "unsubstituted or substituted with up to 3", and particularly preferably "unsubstituted or substituted with up to 2".
  • R 1 is H, halogen, cyano, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or (Ci-C6-alkoxy)carbonyl,
  • R 1 is H, Me, Et, iPr, cPr, CH 2 CN, CF 3 , CHF 2 , CH 2 F, CH2CH2F, CH2CHF2, CH2CF3, CN, halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, C0 2 Me, C0 2 Et, CH 2 C0 2 Me or CH 2 C0 2 Et.
  • each R 5 is independently halogen, cyano, SF 5 , tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl or (
  • each R 5 is independently halogen (particularly F, CI, Br), Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, CN, CF 3 , OCF 3 , SF 5 , CHF 2 , OCHF 2 , SMe, S(0)Me, S(0) 2 Me, SCF 3 , S(0)CF 3 , S(0) 2 CF 3 , SCHF 2 , S(0)CHF 2 , S(0) 2 CHF 2 , CH 2 OMe or CH 2 OEt;
  • each R 6 is independently halogen, nitro, cyano, SF 5 , tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (Ci-C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)amino- carbonyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C 3 -C6-cycloalkyl, Ci-C6-alkoxy, C 3 -C6-cycloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkoxy)carbony
  • each R 6 is independently halogen (particularly F, CI, Br), Me, Et, iPr, cPr, tBu, OMe, OEt, OnPr, OiPr, OtBu, ethynyl, (trimethylsilyl)ethynyl, vinyl, N0 2 , CN, CF 3 , OCF 3 , SF 5 , CHF 2 , OCHF2, SMe, S(0)Me, S(0) 2 Me, SCF 3 , S(0)CF 3 , S(0) 2 CF 3 , SCHF 2 , S(0)CHF 2 , S(0) 2 CHF 2 , CH 2 OMe, CH 2 OEt, fluoromethyl, 2,2,2-trifluoroethyl, 1 ,2,2,2-tetrafluoro- 1 -(trifluoromethyl)ethyl, dimethoxymethyl, chloro(difluoro)methoxy, 2,2,2-trifluor
  • R bb is CN.
  • R cc is independently hydrogen, C1-C4- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl.
  • each R ff is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or Ci-C4-alkoxy-Ci-C2-alkyl.
  • each R 99 is independently H, halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkoxy, phenoxy or benzyloxy, wherein phenoxy and benzyloxy are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from cyano, OH, Ci-C4-alkyl, Ci-C4-alkoxy, halogen, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R hh is H, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- cyanoalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, Ci-C4-alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4- alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfonyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkenyl, C2-C6-al
  • each R kk is independently H, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-cyanoalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C 4 -alkyl, Ci-C 4 -haloalkylthio-Ci-C 4 -alkyl, C 1 -C 4 -a I ky I s u If i ny l-C 1 -C 4 -a I ky I , C1-C4- haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfonyl-Ci-C4-alkyl, Ci-C
  • each R99 is independently H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, C 2 -C6-alkenyloxy, C 2 -C6-haloalkenyloxy, C 2 -C6-alkynyloxy, C3-C6-cycloalkoxy, C3- C6-cycloalkyl-Ci-C4-alkoxy, phenoxy or benzyloxy, wherein phenoxy and benzyloxy are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from cyano, OH, Ci-C4-alkyl, Ci-C4-alkoxy, halogen, Ci-C4-haloalkyl and Ci-C4-haloalkoxy;
  • R hh is H, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -cyanoalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, C1-C4- alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, C 2 -C6-alkenyl, C 2 -C6-halo
  • R99 is Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 - haloalkenyloxy, C 2 -C6-alkynyloxy, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkoxy, phenoxy or benzyloxy, wherein phenoxy and benzyloxy are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from cyano, OH, Ci-C4-alkyl, Ci-C4-alkoxy, halogen, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; and
  • R hh is H, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -cyanoalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, C1-C4- alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, C 2 -C6-alkenyl, C 2 -C6-halo
  • R hh is H, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -cyanoalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, C1-C4- alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, C 2 -C6-alkenyl, C 2 -C6-halo
  • R 6 optionally 1 , 2 or 3 substituents R 6 . More preferred are compounds of formula (I) wherein R 1 is H, Me, Et, CN, CH2CN, CH2CF3, halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 C0 2 Me or CH 2 C0 2 Et, and in particular the ones wherein R 1 is H. More preferred are compounds of formula (I) wherein R 2 is H or halogen, and in particular the ones wherein R 2 is H.
  • each R 5 is independently halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy or Ci-C6-alkylthio, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated;
  • each R 5 is independently halogen (particularly CI, F, Br), Me, OMe, CN, CF 3 , OCF 3 or ethynyl. More preferred are compounds of formula (I) wherein each R 6 is independently halogen, nitro, cyano, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, dimethoxymethyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-alkylthio or Ci-C6-alkylsulfonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; and in particular the ones wherein each R 6 is independently halogen (particularly CI, F, Br), Me, OMe,
  • each R cc is independently H, Me, Et, pro- pargyl, allyl, CH 2 OMe or CH 2 OEt.
  • R aa is or CN; and each R cc is independently H, Me, Et, propargyl, allyl, CH 2 OMe or CH 2 OEt.
  • each R 5 is independently F, CI, Br or CF 3 .
  • each R 6 is independently F, ethynyl or CF 3 .
  • Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R 5 ; or naphthyl un- substituted or substituted with 1 or 2 substituents R 5 ;
  • Q is C4-C8-cycloalkyl or Cs-Cz-cycloalkenyl, wherein C4-C8-cycloalkyl and Cs-Cz-cycloalkenyl are substituted with
  • R 1 is H, halogen, cyano, Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 3 -C6-cycloalkyl or (C1-C6- alkoxy)carbonyl,
  • R 2 is H or halogen
  • R 1 and R 2 form together with the carbon atom to which they are attached a methylene group; each R 5 is independently halogen, cyano, SF 5 , tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (C1-C6- alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C
  • each R 6 is independently halogen, nitro, cyano, SF 5 , tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, (Ci- C6-alkyl)aminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine- 4-carbonyl, acetamido, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, (C1-C6- alkoxy)carbonyl, (Ci-C6-alkyl)amino, di-
  • R bb is CN
  • each R cc is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6- cycl oa I ky I , C 1 -C4-a I koxy-C 1 -C2-a I ky I ;
  • each R ff is independently hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6- cycloalkyl, Ci-C4-alkoxy-Ci-C2-alkyl;
  • each R99 is independently H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkoxy, C3- C6-cycloalkyl-Ci-C4-alkoxy, phenoxy or benzyloxy, wherein phenoxy and benzyloxy are unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from cyano, OH, Ci-C4-alkyl, Ci-C4-alkoxy, halogen, Ci-C4-haloalkyl and Ci-C4-haloalkoxy;
  • R hh is H, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -cyanoalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C1-C4- haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, C1-C4- alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkeny
  • Y is phenyl unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R 5 ;
  • Q is C4-C6-cycloalkyl or C6-cycloalkenyl, wherein C4-C6-cycloalkyl and C6-cycloalkenyl are substituted with
  • R is H, Me, Et, CN, CH 2 CN, CH2CF3, halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 C0 2 Me or CH 2 C0 2 Et;
  • R 2 is H or halogen
  • each R 5 is independently halogen, cyano, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl, Ci-C6-alkoxy or Ci-C6-alkylthio,
  • each R 6 is independently halogen, nitro, cyano, tri-(Ci-C4-alkyl)silyl-C2-C4-alkynyl, dimethox- ymethyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6- cycloalkoxy, Ci-C6-alkylthio or Ci-C6-alkylsulfonyl,
  • R bb is CN
  • each R cc is independently H, Me, Et, propargyl, allyl, CH 2 OMe, CH 2 OEt;
  • Y is phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R 5 ;
  • Q is C4-C6-cycloalkyl or C6-cycloalkenyl, wherein C4-C6-cycloalkyl and C6-cycloalkenyl are substituted with
  • R is H, F, Me, Et, CN, CH 2 CN or CH 2 OMe;
  • each R 5 is independently F, CI, Br or CF 3 ;
  • each R 6 is independently F, ethynyl or CF 3 ;
  • Y is 4-fluorophenyl, 3- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 3,5- difluorophenyl, 3,4-difluorophenyl or 3,4,5-trifluorophenyl.
  • Q is C4-C6-cycloalkyl substituted with
  • Q is C4-C6-cycloalkyl substituted with
  • Q is C4-C6-cycloalkyl substituted with
  • Z NOR hh ;
  • R hh is H, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -cyanoalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 - haloalkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkylthio-Ci-C4-alkyl, C1-C4- alkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-alkylsulfonyl-Ci-C4-alkyl, Ci- C4-haloalkylsulfonyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkeny
  • Q is C4-C6-cycloalkyl substituted with
  • Q is C4-C6-cycloalkyl substituted with
  • Q is C4-C6-cycloalkyl substituted with
  • R cc is H when R aa or R bb is CN.
  • R cc is H.
  • R ff is H.
  • R cc is H; and R ff is H.
  • R aa is CN; and R bb is CN.
  • R 1 and R 2 do not form together with the carbon atom to which they are attached a methylene group. In a further embodiment R 1 and R 2 do not form together with the carbon atom to which they are attached a cyclopropyl group. In yet a further embodiment R 1 and R 2 do not form together with the carbon atom to which they are attached a methylene group; and R 1 and R 2 do not form together with the carbon atom to which they are attached a cyclopropyl group.
  • Q is not substituted with a substituent R 6 .
  • Further preferred compounds of formula (I) are compounds of formulae (la-1 ), (la-2), (la-3), (la- 4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la- 17), (la-18), (la-19) or (la-20),
  • R 5 is phenyl substituted with 1 , 2, 3, 4 or 5 substituents R 5 ;
  • R aa is CN;
  • R bb is CN;
  • R 1 is H, Me, Et, CF3 or CN;
  • R 2 is H;
  • Q is C4-C6-cycloalkyl substituted with one group Z;
  • Z is as defined in formula (I);
  • R 5a , R 5b , R 5c , R 5d and R 5e are as defined in table A.
  • the symbol "-" in any of columns R 5a , R 5b , R 5c , R 5d or R 5e in table A means that the phenyl ring does not carry a substituent R 5 in the respective position, i.e. the phenyl ring carries an H in the respective position.
  • R 5a is R 5 or H
  • R 5b is R 5 or H
  • R 5c is R 5 or H
  • R 5d is R 5 or H
  • R 5e is R 5 or H.
  • Table 1 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la- 20), wherein Z is O; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 2b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is S; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 3b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is CF2; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 4b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is CC ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 5b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is CBr2; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 6b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(F)CI; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 7b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(F)Br; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 8b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(CI)Br; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 10b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is H; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 1 1 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is Me; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 12b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is Et; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 13b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is n-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 14b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is i-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 15b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is n-Bu; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 16b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is sec-Bu; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 17b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is i-Bu; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 18b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is t-Bu; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 19b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 C(CH 3 )3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 20b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 21 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CHF 2 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 22b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 F; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 23b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH(CF 3 )CH 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 24b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH(CF 3 ) 2 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 25b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 26b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH2CH2CH2CF3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 27b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CN; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 28b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH2CH2CN; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 29b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH2CH2OCH3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 30b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH2CH2OCF3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 31 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH2CH2SCH3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 32b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-
  • Table 33b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 S(0)2CH3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 34b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la-
  • Table 35b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 S(0)CF3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 36b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 S(0)2CF3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 49b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is C ⁇ CH; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 50b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 C ⁇ CH; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 51 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH(CH 3 )C ⁇ CH; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 52b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 C ⁇ CCH 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 53b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 CH 2 C ⁇ CH; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 54b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is cyclopropyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 55b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 -(cyclopropyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 56b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is cyclobutyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 57b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 -(cyclobutyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 58b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is cyclopentyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 59b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 -(cyclopentyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 60b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is cyclohexyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 61 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is CH 2 -(cyclohexyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 62b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is phenyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 63b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is NOR hh ; R hh is benzyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 64b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is OMe; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 65b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is OEt; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 66b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is O-n-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 67b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is O-i-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 68b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is OCH 2 CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 69b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is OCH 2 CHF 2 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 70b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is OCH 2 CH 2 F; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 71 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is OCH(CF 3 )CH 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 72b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; R99 is OCH(CF 3 )2; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 73b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rgg is OCH2CH2CF3; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 77b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is OCH 2 C ⁇ CH ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 78b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is O-cyclopropyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 79b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is 0-CH 2 -(cyclopropyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 80b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is O-cyclobutyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 81 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is 0-CH 2 -(cyclobutyl); and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 82b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is O-phenyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 83b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; R99 is O-benzyl; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 84b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is Chb; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 85b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)F; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 86b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)CI; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 87b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Br; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 88b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rgg is Me; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 89b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; R99 is CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 90b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H) R99; Rgg is Et; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 91 b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is C 2 F 5 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 92b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)Rgg; Rgg is n-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 93b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is i-Pr; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 94b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is CH 2 CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 95b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is CH 2 CHF 2 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 96b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rss is CH 2 CH 2 F; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 97b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; is CH(CF 3 )CH 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 98b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; R99 is CH(CF 3 ) 2 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Table 99b Compounds of formulae (la-1 ), (la-2), (la-3), (la-4), (la-5), (la-6), (la-7), (la-8), (la- 9), (la-10), (la-1 1 ), (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), (la-18), (la-19) and (la-20), wherein Z is C(H)R99; Rgg is CH 2 CH 2 CF 3 ; and R 5a , R 5b , R 5c , R 5d and R 5e correspond in each case to a row of table A.
  • Particularly preferred compounds of formula (I) are compounds of formula (la-1 ),
  • Y is phenyl substituted with 1 , 2, 3, 4 or 5 substituents R 5 ;
  • R aa is CN;
  • R bb is CN;
  • R 1 is H;
  • R 2 is H;
  • Q is cyclohexyl substituted with one group Z;
  • R 5a , R 5b , R 5c , R 5d and R 5e are as defined in table A;
  • Z is as defined in tables 1 b to 99b.
  • Y is phenyl unsubstituted or substituted with 1 , 2 or 3 substituents R 5 ;
  • Q is C4-C6-cycloalkyl or C6-cycloalkenyl, wherein C4-C6-cycloalkyl and C6-cycloalkenyl are substituted with
  • R is H, F, Me, Et, CN, CH 2 CN or CH 2 OMe;
  • each R 5 is independently F, CI, Br or CF3;
  • each R 6 is independently F, ethynyl or CF3;
  • the compounds of formula (I) according to the present invention can be prepared e.g. according to preparation methods and preparation schemes described below.
  • R bb ' is not R bb
  • R aa ' is R aa and R bb ' is R bb
  • R aa ' is R aa or a precursor of R aa ;
  • R bb ' is R bb or a precursor of R bb ;
  • Q' is Q or a precursor of Q.
  • Compounds of formula (C) wherein R aa ' is R aa , and wherein R bb ' is R bb , and wherein Q' is Q correspond to compounds of formula (I).
  • Compounds of formula (C) wherein R aa ' is not R aa , or wherein R bb ' is not R bb , or wherein Q' is not Q represent synthetic intermediates, which can be further converted to compounds of formula (I).
  • R aa ' in formula (A) generally corresponds to R aa ' in formula (C).
  • R bb ' in formula (A) generally corresponds to R bb ' in formula (C).
  • Q' in formula (B) generally corresponds to Q' in formula (C).
  • R bb is not CN
  • R bb is CN
  • R bb ' is CN by treatment with a suitable amine, NH(R ff )2.
  • R ff is H
  • the amine is NH3.
  • a suitable amine NH(R ff )2.
  • the amine is NH3.
  • R aa is and wherein R bb is CN
  • R cc is H
  • the amine is NH3.
  • R cc is H
  • the amine is NH3.
  • Suitable functional group interconversions are described in e.g. WO 2003/99276; US 4740228; US 4304930; Journal of the American Chemical Society 1937, vol. 59, p. 1901 ; Synthesis 2004, p. 2625-2628; US 201 1/183960; WO 2008/1 10488; Journal of Medicinal Chemistry 1994, vol. 37, p. 371 -380; N. N. Dykhanov, Zhurnal Prikladnoi Khimii (Sankt Russia Federa- tion) 1961 , 34, p. 1588-91 .
  • Compounds of formula (I) wherein R aa and R bb are CN are generally prepared from compounds of formula (A) wherein R aa ' and R bb ' are CN.
  • R aa ' and R ' are CN
  • R aa and R are CN
  • the ketones can, for example, be converted to the corresponding thioketones by treatment with P4S10 or Lawesson's reagent.
  • the ketones can, for example, be converted to the corresponding olefins using an olefination reaction such as a Wittig reaction or a Peterson olefination. Representative procedures are described in e.g. Journal of the American Chemical Society, vol. 88, (1966), p. 5654- 5656; Organic Letters, vol. 3, (2001 ), p. 2945-2948; Tetrahedron, vol. 62, (2006), p. 9232-9236; Synthesis, (2004), p. 1457-1465 or US 2012/193577.
  • the ketones can, for example, be converted to the corresponding allenes using a sequence as described e.g. in Synlett, (2006), p. 2577-2580 or Journal of the American Chemi- cal Society, vol. 105, (1983), p. 1626-1631 .
  • the ketones can, for example, be converted to the corresponding oximes by treat- ment with a suitable hydroxylamine H2N-OR hh , optionally in the presence of an acid or optionally in the presence of a base and/or optionally in the presence of a dehydrating agent.
  • Suitable solvents are e.g. methanol, ethanol, toluene, dichloromethane or the like.
  • Typical acids include para-toluenesulfonic acid ("pTsOH”), AcOH, HCI or the like.
  • Typical bases include K2C0 3 , Na- HC0 3 , Na2C0 3 , NaOAc, Et 3 N or the like.
  • Typical dehydrating agents include molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POCI 3 , Burgess reagent, trifluoroacetic anhydride ("TFAA”), p-toluene sulfonic acid (“pTsOH”), anhy- drous HCI or sulfuric acid. Representative procedures are described in e.g. WO 2009/0051 10, WO 2006/135763 or WO 2010/072781 .
  • the ketones can, for example, be converted to the corresponding imines by treatment with a suitable amine N H2R kk , optionally in the presence of a base and/or a dehydrating agent. Representative procedures are described in e.g. US 2010/48554, WO 2013/33228 or WO 2013/41591 .
  • the ketones can, for example, be converted to the corresponding hydrazones by treatment with a suitable hydrazine H2N-N(R kk )2, optionally in the presence of a base and/or a dehydrating agent. Representative procedures are described in e.g. Journal of Medicinal Chemistry, 51 , (2008), p. 1333-1343.
  • Representative procedures are described in e.g. WO 2010/072781 or European Journal of Medicinal Chemistry, vol. 39, (2004), p. 729-734.
  • a suitable diol e.g. HOCH2CH2OH
  • a suitable dithiol e.g. HSCH2CH2SH
  • R aa ' and R bb ' are CN
  • R aa ' and R bb ' are CN
  • Alcohols B-2 can be oxidized to aldehyds B-3 using e.g. a Swern oxidation or using e.g. Dess- Martin periodane.
  • Compounds of formula (B-2) or (B-4) can be converted into compounds of formula (B-5) or (B-6) respectively by means of activating the hydroxyl group e.g. via mesylation or tosylation as described in WO 2012/085645. Alternatively, they can be treated with phosphortribromide to convert the hydroxyl group into the respective bromide as described in WO 2012/022487, or they can be treated with iodine, triphenylphosphine and imidazole to convert the hydroxyl group into the respective iodide as described in US 2002/103199. lodo compounds of formula (A-1 ) as well as ester compounds of formula (B-1 ) can be chased or synthesized according to known literature methods.
  • the compounds of formula (I) can be prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds (I) or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds (I) can advantageously be prepared from other compounds (I) by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from vola- tile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration with an appropriate solvent.
  • Preferred bases include triethylamine, trimethylamine, N-ethyldiisopropylamine, triisopropylamine, ammonia, pyridine, lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8- diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN).
  • DMAP dimethylamino)pyridine
  • DBU diazabicyclo[5.4.0]undec-7-ene
  • DBN 1,5-diazabicyclo[4.3.0]non-5-ene
  • the reaction is preferably carried out in a solvent.
  • Preferred solvents include dimethylformamide, dimethyla- cetamide, sulfolane, N-methylpyrrolidinone, 1 ,3-dimethylimazolidinone, dimethyl sulfoxide, water, dichloromethane, toluene, benzene, dioxane or mixtures thereof.
  • hbS can be used as a gas.
  • hbS can be used as a solution.
  • L is a leaving group
  • Q * is C3-C8-cycloalkyl or Cs-Cs-cycloalkenyl, wherein C 3 -Cs-cycloalkyl and Cs-Cs- cycloalkenyl are substituted with two geminal substituents that are together a bridge selected from OCH2CH2O, OCH(CH 3 )CH(CH 3 )0, OC(CH 3 )2C(CH 3 )20, OCH 2 CH 2 CH 2 0 and form together with the carbon atom the two geminal substituents are bonded to a ring; optionally in the presence of a base, to obtain a compound of formula (XIII)
  • Q * is defined as in formula (XII); i-2) reacting the compound of formula (XIII) with water and an acid to obtain a compound of formula (XIV),
  • the reaction of the compound of formula (XI) with the compound of formula (XII) is carried out in the absence of a base.
  • reaction of the compound of formula (XI) with the compound of formula (XII) is carried out in the presence of a base.
  • Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XI) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).
  • Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XII) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).
  • L is halogen or OS(0) 2 R * ;
  • R * is Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-nitroalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C6-alkyl, wherein each phenyl is independently unsubstituted or substituted with up to 5 substituents selected from halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl or C1-C6- alkoxy.
  • L is CI, Br, I or OS(0) 2 R * ;
  • R * is Ci-C6-alkyl, Ci-C6-haloalkyl or phenyl, wherein phenyl is unsubstituted or substituted with up to 5 substituents selected from halogen, NO2, Ci-C6-alkyl or Ci-C6-alkoxy.
  • L is CI, Br, I or OS(0) 2 R * ;
  • R * is Me, CF 3 , C4F9, phenyl or tolyl.
  • the molar ratio of the compound of formula (XI) to the compound of formula (XII) is generally in the range of 1 :0.5-2, preferably in the range of 1 :0.5-1 .5, more preferably in the range of 1 :0.8- 1 .2.
  • Suitable bases for the use in step i-1 ) are carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, silver carbonate, magnesium carbonate, calcium carbonate, barium carbonate; hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide, aluminum hydroxide; oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide, barium oxide, iron oxide, silver oxide; hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride; phosphates such as potassium phosphate, calcium phosphate; alkoxides such sodium, potassium or mag- nesium alkoxides; nitrogen-containing bases such as triethylamine, trimethylamine, N-ethyl- diisopropylamine, triisopropylamine, ammonia, pyridine, luti
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the molar ratio of the compound of formula (XI) to the base is generally in the range of 1 :0.8-3, preferably in the range of 1 :1 -2, more preferably in the range of 1 :1 -1.5.
  • reaction of the compound of formula (XI) with the compound of formula (XII) in the presence of a base is carried out in a solvent.
  • Suitable solvents for the use in step i-1 ) are dipolar aprotic solvents such as N,N- dimethylformamide (DMF), ⁇ , ⁇ -dimethylacetamide (DMAc), 1 -methyl-2-pyrrolidinone (NMP),
  • DMF N,N- dimethylformamide
  • DMAc ⁇ , ⁇ -dimethylacetamide
  • NMP 1 -methyl-2-pyrrolidinone
  • alcohols such as methanol, ethanol, isopropanol, 1 -butanol, 2-butanol, isobutanol, tert-butanol, hexafluoro isopropanol; halogenated hydrocarbons such as dichloromethane, di- chloroethane, carbon tetrachloride; aliphatic hydrocarbons such as hexane, cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylenes, mesitylene, chlorobenzene.
  • alcohols such as methanol, ethanol, isopropanol, 1 -butanol, 2-butanol, isobutanol, tert-butanol, hexafluoro isopropanol
  • halogenated hydrocarbons such as dichloromethane, di- chloroethane, carbon tetrachloride
  • Preferred solvents for the use in step i-1 ) include acetone, DMF, DMAc, 1 ,2-dimethoxyethane, DMI, dichloromethane, diethylether and THF.
  • solvent as used herein also includes mixtures of two or more of the above compounds.
  • the reaction of the compound of formula (XI) with the compound of formula (XII) in the presence of a base is generally carried out at a temperature in the range of from -40 to 80 °C, preferably in the range of from -20 to 40 °C, more preferably in the range of from 0 to 30 °C.
  • An acid is used in step i-2).
  • Typical acids for the use in step i-2) include para-toluenesulfonic acid ("pTsOH”), AcOH or HCI.
  • Step i-2) is preferably carried out in the presence of a solvent.
  • Preferred solvents for the use in step i-2) include aqueous acetic acid, aqueous THF or aqueous acetone.
  • a compound of formula (XV) is used in step i-3).
  • Preferred, more preferred, even more preferred and particularly preferred compounds of formula (XV) are the ones leading to the respective preferred, more preferred, even more preferred and particularly preferred compounds of formula (I).
  • Step i-3) is optionally carried out in the presence of an acid.
  • Typical acids for the use in step i-3) include para-toluenesulfonic acid ("pTsOH”), AcOH or HCI.
  • Step i-3) is optionally carried out in the presence of a base.
  • Typical bases for the use in step i-3) include K 2 C0 3 , NaHCOs, Na 2 C0 3 , NaOAc or Et 3 N.
  • Step i-3) is optionally carried out in the presence of a dehydrating agent.
  • Typical dehydrating agents for the use in step i-3) include molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POC , Burgess reagent, trifluoroacetic anhydride ("TFAA”), p-toluene sulfonic acid (“pTsOH”), anhydrous HCI or sulfuric acid.
  • TFAA trifluoroacetic anhydride
  • pTsOH p-toluene sulfonic acid
  • Step i-3) is preferably carried out in the presence of a solvent.
  • Preferred solvents for the use in step i-3) include methanol, ethanol, toluene or dichloromethane. Pests
  • Preferred animal pests are invertebrate pests.
  • invertebrate pest encompasses animal populations, such as arthro- pode pests, including insects and arachnids, as well as nematodes, which may attack plants thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • animal populations such as arthro- pode pests, including insects and arachnids, as well as nematodes, which may attack plants thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • the compounds of the formula I, and their salts are in particular suitable for efficiently control- ling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.
  • insects from the order of the lepidopterans ⁇ Lepidoptera for example Acronicta major, Adox- ophyes orana, Aedia leucomelas, Agrotis spp.
  • Chilo suppressalis such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp.
  • Feltia subterranean such as Feltia subterranean; Galleria mellonella, Grapholitha fune- brana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp.
  • Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkel- la, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mods repanda, Mythim- na separata, Orgyia pseudotsugata, Oria spp., Ostrinia spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absolutea, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera spp.
  • Atomaria linearis such as Atomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp.
  • Leptinotarsa decemlineata such as Leptinotarsa decemlineata; Limonius californicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolon- tha hippocastani, Melolontha melolontha, Migdolus spp., Monochamus spp.
  • Phyllotreta chrysocephala such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp.
  • Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp.
  • Anopheles albimanus such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculi- pennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp.
  • Chrysomya bezziana such as Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia anthropophaga, Culex spp.
  • Lucilia caprina such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetio- la destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscinella spp. such as Oscinella frit; Pe- gomya hysocyami, Phlebotomus argentipes, Phorbia spp.
  • Phorbia antiqua Phorbia brassicae, Phorbia coarctata
  • Prosimulium mixtum Psila rosae, Psorophora columbiae, Psoro- phora discolor, Rhagoletis cerasi, Rhagoletis pomonella
  • Sarcophaga spp. such as Sarcophaga haemorrhoidalis
  • Simulium vittatum Stomoxys spp. such as Stomoxys calcitrans
  • Calotermes flavicollis Coptotermes formosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermes tenuis, Leucotermes flavipes, Odontotermes spp., Reti- culitermes spp. such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalen- sis, cockroaches (Blattaria - Blattodea), e.g.
  • Aphis fabae such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossulariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp.
  • Dysaphis plantaginea such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as Dysdercus cingula- tus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as Empoasca fabae, Em- poasca solana; Eriosoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integri- ceps; Euscelis bilobatus, Euschistus spp.
  • Euschistuos heros such as Euschistuos heros, Euschistus impictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyomorpha halys; He- liopeltis spp., Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lac- tucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepi- dosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp.
  • Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae, Macrosiphum euphorbiae; Mahanarva fim- briolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Met- cafiella spp., Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp.
  • Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.
  • Pentomidae Peregrinus ma id is, Perkinsiella saccharicida, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humu- li, Phylloxera spp., Piesma quadrata, Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta per- sea, Pseudaulacaspis pentagona, Pseudococcus spp.
  • Pseudococcus comstocki such as Pseudococcus comstocki; Psylla spp. such as Psylla mail, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Que- sada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp.
  • Rhopalosiphum pseudobrassicas such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum ma id is, Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mail, Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Stephanitis nashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp.
  • Thyanta perditor such as Thyanta perditor; Tibraca spp., Tinocallis caryaefoliae, To- maspis spp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis ya- nonensis; and Viteus vitifolii, ants, bees, wasps, sawflies (Hymenoptera), e.g.
  • Atta capiguara Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Campo- notus floridanus, Crematogaster spp., Dasymutilla occidentals, Diprion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp.
  • Amblyomma spp. e.g. Amblyomma americanum, Amblyomma variegatum, Amblyom- ma maculatum
  • Argas spp. e.g. Argas persicus
  • Boophilus spp. e.g. Boophilus annulatus, Boophilus decoloratus, Boophilus microplus
  • Dermacentor silvarum, Dermacentor andersoni Dermacentor variabilis
  • Hyalomma spp. e.g. Hyalomma truncatum
  • Ixodes spp. e.g.
  • Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.
  • Eotetranychus spp. such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasates lycopersici; Araneida, e.g.
  • Earwigs e.g. forficula auricularia, lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pe- diculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Haematopinus euryster- nus, Haematopinus suis; Linognathus spp.
  • Linognathus vituli such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., springtails ⁇ Collembola ), e.g. Onychiurus ssp.
  • Onychiurus armatus are also suitable for controlling nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelenchoides besseyi ; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus lignic
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the class of the Bivalva, for example, Dreissena spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example, Ancy- lostoma duodena le, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., As- caris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.
  • pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indi- cus, Chilo polychrysus, Chortiocetes terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum, Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera, Diloboderus spp.
  • Diloboderus abderus such as Diloboderus abderus; Edessa spp., Epinotia spp., Formici- dae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta, Leptocorsia orato- rius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma- rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microthe- ca spp., Mods latipes, Murgantia spp., Mythemin
  • Orseolia oryzae such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triacifer, Psylloides spp., Rachiplu- sia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarc- tata; Sesamia spp.
  • Sesamia inferens such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spis- sistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta deroga- ta, Telehin licus, Trichostrongylus spp..
  • insects preferably sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera, in particular the following species:
  • Thysanoptera Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips pa Imi and Thrips tabaci,
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles free- borni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Cu- lex quinquef
  • Nezara spp. such as Nezara viridula.
  • Compounds of the formula I are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera.
  • Compounds of the formula I are particularly useful for controlling Hemiptera, in particular Nezara spp. such as Nezara viridula.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a pesticidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful pests on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the animal pests species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Mono-graph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphtha- lene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo- hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. toluene, paraffin, tetrahydronaphtha
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N- methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsul- fonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrroli- done, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I according to the invention 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%.
  • the active substance dissolves upon dilution with water.
  • a compound I according to the invention 5-25 wt% of a compound I according to the invention and 1 -10 wt% dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
  • dispersant e.g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water- insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I according to the invention 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosul- fonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • dispersants and wetting agents e.g. sodium lignosul- fonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • water ad 100 wt% 100 wt% to give a fine active substance suspension.
  • Dilution with water gives a stable suspension of the active substance.
  • binder e.g. poly- vinylalcohol
  • a compound I according to the invention 50-80 wt% of a compound I according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt%and prepared as water-dispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water ad 100 %.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization ini- tiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g.
  • an isocy- anate monomer e.g. diphenylmethene-4,4'-diisocyanatae
  • a protective colloid e.g. polyvinyl alcohol
  • the addition of a polyamine results in the formation of a polyurea microcapsules.
  • the monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • a compound I according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
  • solid carrier e.g. finely divided kaolin
  • Granules (GR, FG)
  • a compound I according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • Granulation is achieved by extrusion, spray- drying or the fluidized bed.
  • organic solvent e.g. aromatic hydrocarbon
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • auxiliaries such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions for seed treatment (LS), Suspo-emulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble pow- ders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying compound I and com- positions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • these agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemi- cal composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds I, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds I, can be applied jointly (e.g. after tank mix) or consecutively.
  • individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e.g. components comprising compounds I and/or active substances from the groups M.1 to M.UN.X or F.I to F.XII
  • either individual components of the composition according to the invention or partially premixed components e.g. components comprising compounds I and/or active substances from the groups M.1 to M.UN.X or F.I to F.XII, can be applied jointly (e.g. after tank mix) or consecutively.
  • Acetylcholine esterase (AChE) inhibitors from the class of
  • a carbamates for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodi- carb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of
  • M.1 B organophosphates for example acephate, azamethiphos, azinphos-ethyl, azinphosme- thyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimetho- ate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam,
  • GABA-gated chloride channel antagonists such as:
  • M.2A cyclodiene organochlorine compounds as for example endosulfan or chlordane; or
  • M.2B fiproles phenylpyrazoles
  • fipronil phenylpyrazoles
  • flufiprole pyrafluprole
  • pyriprole phenylpyrazoles
  • M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifen- thrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,
  • M.3B sodium channel modulators such as DDT or methoxychlor
  • M.4A neonicotinoids for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, niten- pyram, thiacloprid and thiamethoxam; or the compounds
  • M.4A.1 1 -[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-Epoxy-1 H- imidazo[1 ,2-a]azepine; or
  • M.4A.2 1 -[(6-chloro-3-pyridyl)methyl]-2-nitro-1 -[(E)-pentylideneamino]guanidine; or
  • M4.A.3 1 -[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H- imidazo[1 ,2-a]pyridine;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
  • M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
  • M.8A alkyl halides as methyl bromide and other alkyl halides, or
  • M.1 1 Microbial disruptors of insect midgut membranes for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cry1 Ac, Cry1 Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase for example
  • M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C pro- pargite, or M.12D tetradifon;
  • M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient for example chlorfenapyr, DNOC or sulfluramid
  • M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • benzoylureas as for example bistriflu- ron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novalu- ron, noviflumuron, teflubenzuron or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 as for example buprofezin; M.17 Moulting disruptors, Dipteran, as for example cyromazine;
  • Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide; M.19 Octopamin receptor agonists, as for example amitraz;
  • M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
  • M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or
  • M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides as for example flubendiamide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), or the phthalamide compounds M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -(trifluormethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid and
  • M.28.2 (S)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -(trifluormethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, or the compound M.28.3: 3-bromo-N- ⁇ 2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl ⁇ -1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide (proposed ISO name: cyclaniliprole), or the compound
  • M.28.4 methyl-2-[3,5-dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl ⁇ amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5I):
  • M.UN.X insecticidal active compounds of unknown or uncertain mode of action as for example afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinome- thionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butox- ide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds
  • M.UN.X.2 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[2- oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1 -carboxamide, or the compound
  • M.UN.X.3 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1 -en-10-one, or the compound M.UN.X.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3-en-2- one, or the compound
  • M.UN.X.5 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H- 1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or
  • M.UN.X.6a (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • M.UN.X.6b (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
  • M.UN.X.6d E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • M.UN.X.6e E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • M.UN.X.6 ⁇ E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide
  • M.UN.X.7 3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1 -(pyrimidin-5-ylmethyl)pyrido[1 ,2- a]pyrimidin-1 -ium-2-olate; or
  • M.UN.X.9 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or
  • M.UN.X.10 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole.
  • the quinoline derivative flometoquin is shown in WO2006/013896.
  • the aminofuranone compounds flupyradifurone is known from WO 2007/1 15644.
  • the sulfoximine compound sulfoxaflor is known from WO2007/149134.
  • the pyrethroid momfluorothrin is known from US6908945.
  • the pyrazole acaricide pyflubumide is known from WO2007/020986.
  • the isoxazoline compounds have been described likewise M.UN.X.1 in WO2005/085216, M.UN.X2. in WO2009/002809 and in WO201 1/149749 and the isoxazoline M.UN.X.9 in WO2013/050317.
  • the pyripyropene derivative afidopyropen has been described in WO 2006/129714.
  • the spiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known from WO2006/089633 and the biphenyl-substituted spi- rocyclic ketoenol derivative M.UN.X.4 from WO2008/06791 1.
  • triazoylphenylsulfide like M.UN.X.5 have been described in WO2006/043635 and biological control agents on basis of bacillus firmus in WO2009/124707.
  • the neonicotionids 4A.1 is known from WO20120/069266 and WO201 1/06946, the M.4.A.2 from WO2013/003977, the M4.A.3.from WO2010/069266.
  • the Metaflumizone analogue M.22C is described in CN 10171577.
  • the phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540.
  • the anthranilamide M.28.3 has been de- scribed in WO2005/077934.
  • the hydrazide compound M.28.4 has been described in WO 2007/043677.
  • the anthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO 2007/006670, WO2013/024009 and WO2013/024010, the anthranilamide ⁇ .28.5 ⁇ ) is described in WO201 1/085575, the M.28.5j) in WO2008/134969, the M.28.5k) in US201 1/046186 and the M.28.5I) in WO2012/034403.
  • the diamide compounds M.28.6 and M.28.7 can be found in CN102613183.
  • the compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in WO2012/029672.
  • the mesoionic antagonist compound M.UN.X.7 was described in WO2012/0921 15, the nematicide M.UN.X.8 in WO2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO2010/060379.
  • Inhibitors of complex III at Qo site e.g. strobilurins
  • strobilurins azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metom- inostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyri- bencarb, trifloxystrobin, methyl (2-chloro-5 [1 -(3-methylbenzyloxyimino)ethyl]benzyl)carbamate and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;
  • oxazolidinediones and imidazolinones famoxadone, fenamidone;
  • Inhibitors of complex II e.g. carboxamides
  • carboxanilides benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole-5-carboxanilide, N- (3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4 carboxamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1 -methyl-1 H pyrazole-4-carboxamide and N- (2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5
  • Inhibitors of complex III at Qi site cyazofamid, amisulbrom;
  • nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, nitrthal-isopropyl,
  • organometal compounds fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; F.ll) Sterol biosynthesis inhibitors (SBI fungicides)
  • triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, dinicona- zole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hex- aconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, pen- conazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triad- imefon, triadimenol, triticonazole, uniconazole;
  • imidazoles imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;
  • pyrimidines, pyridines and piperazines fenarimol, nuarimol, pyrifenox, triforine;
  • F.II-2 Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph;
  • piperidines fenpropidin, piperalin;
  • spiroketalamines spiroxamine
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, met- alaxyl-M (mefenoxam), ofurace, oxadixyl;
  • isoxazoles and iosothiazolones hymexazole, octhilinone;
  • Tubulin inhibitors benzimidazoles and thiophanates: benomyl, carbendazim, fuber- idazole, thiabendazole, thiophanate-methyl;
  • benzamides and phenyl acetamides diethofencarb, ethaboxam, pencycuron, fluopicolide, zox- amide;
  • Actin inhibitors benzophenones: metrafenone; F.V) Inhibitors of amino acid and protein synthesis
  • anilino-pyrimidines cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;
  • F.V-2 Protein synthesis inhibitors (anilino-pyrimidines)
  • antibiotics blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, strep- tomycin, oxytetracyclin, polyoxine, validamycin A;
  • MAP / Histidine kinase inhibitors e.g. anilino-pyrimidines
  • dicarboximides fluoroimid, iprodione, procymidone, vinclozolin;
  • phenylpyrroles fenpiclonil, fludioxonil;
  • F.VI-2 G protein inhibitors: quinolines: quinoxyfen;
  • organophosphorus compounds edifenphos, iprobenfos, pyrazophos;
  • dithiolanes isoprothiolane
  • cinnamic or mandelic acid amides dimethomorph, flumorph, mandiproamid, pyrimorph;
  • valinamide carbamates benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1 -(1 -(4- cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
  • Inorganic active substances Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • F.VIII-2 Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, methasulphocarb, metiram, propineb, thiram, zineb, ziram;
  • Guanidines guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
  • Inhibitors of glucan synthesis validamycin, polyoxin B;
  • F.IX-2 Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;
  • phosphonates fosetyl, fosetyl-aluminum, phosphorous acid and its salts;
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6- dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine, paclobutrazol, prohexadione (prohexadione- calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodo- be
  • Bacillus substilis strain with NRRL No. B-21661 e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.
  • Bacillus pu- milus strain with NRRL No. B-30087 e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA
  • Ulocladium oudemansii e.g. the product BOTRY-ZEN from BotriZen Ltd., New Zealand
  • Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., New Zealand
  • the animal pest i.e. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compounds of formula I or composition(s) containing them by any application method known in the art.
  • "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the com- pounds/compositions to the locus of the animal pest or plant).
  • the compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of com- pounds of formula I.
  • crop refers both to growing and harvested crops.
  • the compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugar- beet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with a insecticidally effective amount of the active compounds.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.
  • the present invention also includes a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of a mixture of at least one active compound I.
  • animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I.
  • the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
  • the compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.
  • the compounds of formula I may be also used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I.
  • "contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
  • “Locus” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. pota- toes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • cultivadas plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural re- combination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenyl- ated, acetylated or farnesylated moieties or PEG moieties (e.g.
  • cultiva plants is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxy- genase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g.
  • HPPD hydroxyphenylpyruvate dioxy- genase
  • ALS acetolactate synthase
  • sulfonyl ureas see e.g.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • GS glutamine synthetase
  • EP-A-0242236, EP-A-242246) or oxynil herbicides see e.g. US 5,559,024.
  • mutagenesis for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox.
  • cultiva plants is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp.
  • delta-endotoxins e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other in- sect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701 ).
  • Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxo- nomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).
  • cultivars are to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato So- lanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato So- lanum bulbocastanum
  • T4-lysozym e.g. potato cultivars capable
  • cultiva plants is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), toler- ance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e.g. bio mass production, grain yield, starch content, oil content or protein content
  • toler- ance to drought e.g. bio mass production, grain yield, starch content, oil content or protein content
  • salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants e.g. bio mass production, grain yield, starch content, oil content or protein content
  • cultiva plants is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nex- era® rape).
  • cultiva plants is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .
  • Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
  • the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.
  • the compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
  • the compounds of the invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches.
  • non-crop insect pests such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches.
  • compounds of formula I are preferably used in a bait composition.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks.
  • Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources.
  • Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
  • the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey.
  • Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.
  • Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
  • the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
  • Formulations of compounds of formula I as aerosols are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
  • kerosenes having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifi- ers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
  • auxiliaries such as emulsifi- ers such as sorbitol monooleate, oleyl e
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the content of active ingredient is from 0.001 to 80 weight %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
  • the compounds of formula I and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • Methods to control infectious diseases transmitted by insects e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • compounds of formula I and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like.
  • Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.

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  • Chemical Kinetics & Catalysis (AREA)
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  • Animal Behavior & Ethology (AREA)
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Abstract

L'invention concerne un composé de formule (I) ou un sel de celui-ci, les symboles et indices étant définis dans la description. Les composés de formule (I) sont utiles pour lutter contre les animaux nuisibles et pour combattre des parasites chez et sur les animaux.
PCT/EP2015/057739 2014-04-16 2015-04-09 Composés d'oxime de malononitrile WO2015158603A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2015247463B2 (en) * 2014-04-17 2018-03-29 Basf, Se Use of malononitrile compounds for protecting animals from parasites
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002284608A (ja) * 2001-01-18 2002-10-03 Sumitomo Chem Co Ltd 殺虫剤および殺虫方法
WO2002089579A1 (fr) * 2001-05-09 2002-11-14 Sumitomo Chemical Company, Limited Composition pesticide comprenant des composes de malononitrile
EP1555259A1 (fr) * 2004-01-16 2005-07-20 Sumitomo Chemical Company, Limited Dérives de malononitrile comme pesticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002284608A (ja) * 2001-01-18 2002-10-03 Sumitomo Chem Co Ltd 殺虫剤および殺虫方法
WO2002089579A1 (fr) * 2001-05-09 2002-11-14 Sumitomo Chemical Company, Limited Composition pesticide comprenant des composes de malononitrile
EP1555259A1 (fr) * 2004-01-16 2005-07-20 Sumitomo Chemical Company, Limited Dérives de malononitrile comme pesticides

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DATABASE WPI Week 200323, Derwent World Patents Index; AN 2003-233496, XP002741638 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2015247463B2 (en) * 2014-04-17 2018-03-29 Basf, Se Use of malononitrile compounds for protecting animals from parasites
US10857121B2 (en) 2014-04-17 2020-12-08 Merial Inc. Use of malononitrile compounds for protecting animals from parasites
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds

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