WO2015028501A1 - Composés d'anthranilamide et leur utilisation comme pesticides - Google Patents

Composés d'anthranilamide et leur utilisation comme pesticides Download PDF

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WO2015028501A1
WO2015028501A1 PCT/EP2014/068157 EP2014068157W WO2015028501A1 WO 2015028501 A1 WO2015028501 A1 WO 2015028501A1 EP 2014068157 W EP2014068157 W EP 2014068157W WO 2015028501 A1 WO2015028501 A1 WO 2015028501A1
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alkyl
radicals
substituted
cycloalkyl
group
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PCT/EP2014/068157
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Jean-Yves WACH
Matthias Pohlman
Karsten KÖRBER
Jochen Dietz
Wolfgang Von Deyn
Nina Gertrud Bandur
Arun Narine
Raffael KOLLER
Joachim Dickhaut
Deborah L. Culbertson
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to anthranilamide compounds and the stereoisomers, salts, tautomers and N-oxides thereof and to compositions comprising the same.
  • the invention also relates to the use of the anthranilamide compounds or of the compositions comprising such compounds for combating invertebrate pests. Furthermore, the invention relates to methods of applying such compounds.
  • Invertebrate pests and in particular insects, arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes.
  • WO 03/016284, WO 2007/020877, WO 2012/004208 and WO 2013/024008 describe inter alia anthranilamide compounds with a 2-[1 -(het)arylpyrazol-5-yl-carbonylamino] group and a potentially substituted hydroxyiminmethyl group in position 5 as well as their uses as pesticides.
  • the compounds should show a broad activity spectrum against a large number of different invertebrate pests, in particular against difficult to control insects, arachnids and nematodes.
  • anthranilamide compounds of the general formula (I), as defined below including their stereoisomers, their salts, in particular their agriculturally or veterinarily acceptable salts, their tautomers and their N-oxides.
  • k is 0, 1 , 2 or 3;
  • Q is N or CH
  • R 1 is selected from the group consisting of hydrogen, halogen, SF 5 , -SCN, nitro, azido, Ci-Cs- alkyl, Ci-Cs-haloalkyl, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, cyano, C2-Cs-alkenyl, C2-C8- haloalkenyl, C2-Cs-alkynyl, C2-C8-haloalkynyl, wherein the radicals Ci-Cs-alkyl, Ci-Cs- haloalkyl, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, C2-Cs-alkenyl, C2-C8-haloalkenyl, C2-C8- alkynyl, C2-C8-haloalkynyl may optionally be substituted by 1 , 2 or 3 radicals R a ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R e , and
  • heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e ;
  • Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R a , Cs-Cs-cycloalkyI which may be partially or fully halogenated and/or may be substituted by one or more radicals R a , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R a , C2-C6- alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R a , -Si(R f )2R 9 , -OR b , -OS(0) n R b , -SR b , -S(0) m R b ,
  • R 5a and R 5b are, independently of each other, selected from the group consisting of
  • Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, or 3 radicals R a , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8- cycloalkyl-Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a ,
  • Ci-C6-alkylthio, Ci-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by 1 , 2 or 3 radicals R a , Cs-Cs-cycloalkoxy which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8-cycloalkyl-Ci-C4-alkoxy where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C6-alkenyloxy which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , C2-C6-alkynyloxy which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , or R 5a and R
  • R 5c and R 5d are, independently of each other, selected from the group consisting of
  • Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by 1 , 2 or 3 radicals R a , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8-cycloalkyl-Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by 1
  • R 5e , R 5f are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, phenyl which may be substituted by 1 , 2, 3, 4, or 5 radicals R e ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatom
  • R 6 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, benzyl which is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e , phenyl which is unsubstituted or may be substituted by 1 , 2, 3, 4 or 5 radicals R
  • Y is N or C-R 7 ,
  • R 7 is selected from the group consisting of hydrogen, halogen, CN, C1-C6 alkyl and C1-C6 haloalkyl;
  • Z is CN or a moiety of the formula Z1 ,
  • X 1 is O, S, N-R 9 , N-O-R 9 or N-S-R 9 ;
  • R 8 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl,
  • R 9 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl,
  • R 10 is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Cs-Cs-cycloalkoxy, Cs-Cs-halocycloalkoxy, where the alkyl or cycloalkyi
  • R 8 and R 9 together may form a linear C2-Cs-alkylene group, where one Chb moiety of the linear C2-Cs-alkylene group, which is not adjacent to X 1 and X 2 , may be replaced by O, S, NR' or a carbonyl group, where R' is hydrogen or C1-C6 alkyl, and where 1 , 2, 3 or 4 hydrogen atoms of the linear C2-Cs-alkylene group may be replaced by halogen or C1-C6 alkyl;
  • R 11 b are, independently of each other, selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by 1 , 2 or 3 radicals R a , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8-cycloalkyl-Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C
  • phenyl which is unsubstituted may be substituted by 1 , 2, 3, 4 or 5 radicals RP, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 , as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals RP; or two geminally bound radicals R a together form a group selected from
  • 6- 7- or 8-membered saturated or partially unsaturated carbocyclic ring or a 3-, 4-, 5-, 6-,
  • each R c , R d independently of their occurrence are, independently from one another, selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs- cycloalkyl, cyano, C 2 -C6-alkenyl and C 2 -C6-alkynyl, where the radicals Ci-C6-alky
  • R e independently of its occurrence, is independently selected from the group consisting of halogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, cyano, C2-C6-alkenyl and C2-C6-alkynyl, where the radicals Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl may be
  • phenyl, benzyl, pyridyl and phenoxy to be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkoxy, and C1-C6 haloalkoxy ; where in the case of more than one R e , R e can be identical or different;
  • R f , R9 independently of their occurrence, are, independently of each other, selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl, phenyl and benzyl;
  • R' independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl
  • R j independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl,
  • Ci-C6-haloalkyl (Ci-C6-alkoxy)carbonyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy;
  • R k and R' together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy;
  • R m independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein one or more
  • phenyl, benzyl, pyridyl and phenoxy wherein the radicals phenyl, benzyl, pyridyl and phenoxy may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, (Ci-C6-alkoxy)carbonyl, C1-C6- alkoxy and Ci-C6-haloalkoxy;
  • R n R° independently of their occurrence, are, independently from one another, selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, Cs-Cs- cycloalkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals Ci-C6-alkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, may be
  • Rp independently of its occurrence, is selected from the group consisting of halogen, C1-C6- alkyl, Cs-Cs-cycloalkyl, cyano, C2-C6-alkenyl and C2-C6-alkynyl where the radicals C1-C6- alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl may be unsubstituted, partially or fully halogenated and/or wherein one or two Chb groups may be replaced by a CO group, and/or may carry 1 -2 radicals selected from Ci-C6-alkoxycarbonyl, Ci-C4-alkoxy, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, C1-C6- haloalkyls
  • R x is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6- haloalkynyl, said substituents R x being identical or different from one another if more than one substituent R x is present,
  • Ry is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl and Cs-Cs-cycloalkyl- Ci-C 4 -alkyl; or a stereoisomer, a salt, a tautomer or N-oxide thereof.
  • a specific embodiment of the present invention relates to compounds of formula (I), wherein k is 0, 1 , 2 or 3;
  • Q is N or CH; is selected from the group consisting of hydrogen, halogen, SF 5 , -SCN, nitro, azido, Ci-Cs- alkyl, Ci-Cs-haloalkyI, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyI, cyano, C2-Cs-alkenyl, C2-C8- haloalkenyl, C2-Cs-alkynyl, C2-Cs-haloalkynyl, wherein the radicals d-Cs-alkyl, C-i-Cs- haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyI, C2-Cs-alkenyl, C2-Cs-haloalkenyl, C2-C8- alkynyl, C2-Cs-haloalkynyl may optionally be substituted by 1 , 2 or 3 radicals R a ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R e , and
  • R 5a and R 5b are, independently of each other, selected from the group consisting of
  • Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, or 3 radicals R a , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8- cycloalkyl-Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a ,
  • N-bound, 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e ;
  • R 5c and R 5d are, independently of each other, selected from the group consisting of
  • Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3 radicals R a , Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by 1 , 2 or 3 radicals R a , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C3-C8-cycloalkyl-Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2, 3 or 4 radicals R a , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by 1
  • R e and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e ; or R 5c and R 5d , together represent a C2-Cg-alkylene, C2-Cg-alkenylene or
  • R 5e , R 5f are, independently of each other and independently of each occurrence, selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, phenyl which may be substituted by 1 , 2, 3, 4, or 5 radicals R e ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatom
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, benzyl which is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e , phenyl which is unsubstituted or may be substituted by 1 , 2, 3, 4 or 5 radicals R e
  • Y is N or C-R 7 ,
  • R 7 is selected from the group consisting of hydrogen, halogen, CN, C1-C6 alkyl and C1-C6 haloalkyl;
  • Z is CN or a moiety of the formula Z1 ,
  • X 1 is O, S, N-R 9 , N-O-R 9 or N-S-R 9 ;
  • X 2 is O, S or NR 10 ;
  • R 8 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl,
  • R 10 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, C3-Cs-halocycloalkyl-Ci-C4-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, benzyl which is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals R e , phenyl which is unsubstituted or may be substituted by 1 , 2, 3, 4 or 5 radicals R
  • phenyl which is unsubstituted may be substituted by 1 , 2, 3, 4 or 5 radicals RP, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 , as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2, 3, 4, or 5 radicals RP; or two geminally bound radicals R a together form a group selected from
  • 6- 7- or 8-membered saturated or partially unsaturated carbocyclic ring or a 3-, 4-, 5-, 6-,
  • each R c , R d independently of their occurrence are, independently from one another, selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs- cycloalkyl, cyano, C 2 -C6-alkenyl and C 2 -C6-alkynyl, where the radicals Ci-C6-alky
  • R e independently of its occurrence, is independently selected from the group consisting of halogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, cyano, C2-C6-alkenyl and C2-C6-alkynyl, where the radicals Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl may be
  • phenyl, benzyl, pyridyl and phenoxy to be unsubstituted, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkoxy, and C1-C6 haloalkoxy ; where in the case of more than one R e , R e can be identical or different;
  • R f , R9 independently of their occurrence, are, independently of each other, selected from the group consisting of Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl,
  • R' independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl
  • R k and R' together with the nitrogen atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, wherein one or more CH2 groups of the
  • phenyl, benzyl, pyridyl and phenoxy wherein the radicals phenyl, benzyl, pyridyl and phenoxy may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, (Ci-C6-alkoxy)carbonyl, C1-C6- alkoxy and Ci-C6-haloalkoxy;
  • R° independently of their occurrence are, independently from one another, selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, C3-C8- cycloalkyl, cyano, C2-C6-alkenyl, C2-C6-alkynyl, where the radicals Ci-C6-alkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, may be
  • Rp independently of its occurrence, is selected from the group consisting of halogen, C1-C6- alkyl, Cs-Cs-cycloalkyl, cyano, C2-C6-alkenyl and C2-C6-alkynyl where the radicals C1-C6- alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl may be unsubstituted, partially or fully halogenated and/or wherein one or two CH2 groups may be replaced by a CO group, and/or may carry 1 -2 radicals selected from Ci-C6-alkoxycarbonyl, Ci-C4-alkoxy, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, C1-C6- haloalkyls
  • R g , R r independently of their occurrence, are, independently from one another, selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, cyano, C2-C6- alkenyl, C2-C6-alkynyl, SF 5 , -SCN, nitro and azido, where the radicals Ci-C6-alkyl, Cs-Cs- cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl may be unsubstituted, partially or fully halogenated and/or oxygenated, and/or may carry 1 or 2 radicals selected from C1-C4- alkyl; Ci-C4-haloalkyl; Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, d-Ce-alkylsulf
  • R x is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl,
  • R y is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl and Cs-Cs-cycloalkyl- Ci-C 4 -alkyl; or a stereoisomer, a salt, a tautomer or N-oxide thereof.
  • the invention relates to the compounds of formula (I), their stereoisomers, N-oxides and their salts which are particularly useful for controlling invertebrate pests, in particular for controlling arthropods and nematodes and especially insects. Furthermore, the invention relates to processes for the synthesis of compounds according to the invention and to intermediate compounds for the synthesis of compounds of formula (I).
  • the present invention also relates to and includes the following aspects:
  • an agricultural or veterinary composition comprising at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, and at least one liquid and/or solid carrier.
  • a method for combating or controlling invertebrate pests comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, or a composition as defined herein.
  • a method for protecting growing plants from attack or infestation by invertebrate pests comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, or a composition as defined herein.
  • - a method for the protection of plant propagation material, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the plant propagation material respectively seeds before sowing and/or after pregermination with at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, or a composition as defined herein.
  • - plant propagation material, in particular seed comprising a compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of the plant propagation material.
  • a method for treating a non-human animal infested or infected by parasites or for preventing a non-human animal from getting infested or infected by parasites or for protecting a non- human animal against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the non-human animal a parasiticidally effective amount of a compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or a veterinarily acceptable salt thereof or a composition as defined in claim herein.
  • the wavy line between the the variable Y and the group O-R 6 in the formula (I) indicates that the group O-R 6 is either in the Z- or in the E-position. Accordingly, the E-isomers and the Z-isomers of the compounds of the formula (I) are illustrated by the following formulae (I.E) and (I.Z), respectively,
  • R 1 , R 3 , R 4 , R 5 , R 6 , k, Q, Y and Z are as defined herein for the compounds of the formula (I).
  • the invention relates both to the pure E- and Z-isomers of formulae I.E and I.Z, their salts, their tautomers and their N-oxidis as well as to mixtures of the E- and Z-isomers of formulae I.E and I.Z, their salts, their tautomers and their N-oxides.
  • the compounds of the formula (I), their tautomers and their stereoisomers may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.
  • Suitable compounds of the formula (I), their tautomers and their stereoisomers also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • N-oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) 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), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • Suitable agriculturally acceptable 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 pesticidal action of the compounds according to the present invention.
  • Suitable cations are in particular the 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 ammonium 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, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltnmethylammonium and benzl-triethylammonium, 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, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Veterinarily acceptable salts of the compounds of the present invention encompass the salts of those cations or the acid addition salts which are known and accepted in the art for the formation of salts for veterinary use.
  • Suitable acid addition salts e.g. formed by compounds of the present invention containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulfates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, e.g. the monoacid salts or diacid salts of maleic acid, dimaleic acid, fumaric acid, e.g.
  • Cn-Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • partially or fully halogenated will be taken to mean 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.
  • a partially or fully halogenated radical is termed below also “halo-radical”.
  • partially or fully halogenated alkyl is also termed haloalkyl.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 12 or 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Examples of Ci-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl,
  • Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl,
  • Ci-Cio-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl,
  • alkylene or alkanediyl as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkyl as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms ("Ci-Cio-haloalkyl”), frequently from 1 to 6 carbon atoms (“C1-C6- haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-Cio-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
  • haloalkyl as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g
  • haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • Examples for C1-C2- fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl,
  • Ci-C2-haloalkyl examples are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl,
  • Ci-C4-haloalkyl examples are, apart those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trif I uoroprop-2-yl ,
  • cycloalkyl as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-Cio-cycloalkyl”), preferably 3 to 8 carbon atoms (“Cs-Cs-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C3-C6- cycloalkyl").
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1 ]hexyl, bicyclo[2.2.1 ]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1 ]heptyl, bicyclo[2.2.2]octyl and
  • cycloalkylene (or cycloalkanediyl) as used herein in each case denotes an cycloalkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • halocycloalkyi as used herein (and in the halocycloalkyi moieties of other groups comprising an halocycloalkyi group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine.
  • Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl and the like.
  • cycloalkyl-alkyl used herein denotes a cycloalkyl group, as defined above, which bound to the remainder of the molecule via an alkylene group.
  • Cs-Cs-cycloalkyl- Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutyl propyl, cyclopentylmethyl, cyclopentylethyl, cyclopentyl propyl, cyclohexyl methyl, cyclohexylethyl, cyclohexylpropyl, and the like.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 10 (“C2-Cio-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C6-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl,
  • alkenylene (or alkenediyl) as used herein in each case denotes an alkenyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkenyl as used herein, which may also be expressed as "alkenyl which may be substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 ("C 2 -Cio-haloalkenyl") or 2 to 6 ("C 2 -C 6 -haloalkenyl”) or 2 to 4 (“C 2 -C 4 -haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
  • alkynyl denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10 (“C 2 -Cio-alkynyl”), frequently 2 to 6 (“C 2 -C 6 -alkynyl”), preferably 2 to 4 carbon atoms (“C2-C4-alkynyl”) and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl- 2-propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl,
  • alkynylene (or alkynediyl) as used herein in each case denotes an alkynyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkynyl as used herein, which is also expressed as “alkynyl which may be substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10 carbon atoms (“C2-Cio-haloalkynyl”), frequently 2 to 6 (“C2-C6- haloalkynyl”), preferabyl 2 to 4 carbon atoms (“C2-C4-haloalkynyl”), and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C2-Cio-haloalkynyl unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10 carbon atoms
  • C2-C6- haloalkynyl frequently 2 to 6
  • C2-C4-haloalkynyl preferabyl 2 to 4 carbon
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 10 carbon atoms ("Ci-Cio-alkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-alkoxy”), preferably 1 to 4 carbon atoms (“Ci-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy,
  • Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 10 carbon atoms ("Ci-Cio-haloalkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4- haloalkoxy”), more preferably 1 to 3 carbon atoms (“Ci-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH2CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,
  • Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy,
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy
  • 6-chlorohexoxy 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 10, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Ci-C6-Alkoxy-Ci-C6-alkyl is a Ci-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2-(1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)- ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl,
  • haloalkoxy-alkyl denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 10, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Examples are fluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 -difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl,
  • pentafluoroethoxymethyl 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 - ethyl, 1 ,2-difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -ethyl, 1 ,2,2-trifluoroethoxy-1 -ethyl, 2,2,2-trifluoroethoxy-1 -ethyl, pentafluoroethoxy-1 -ethyl,
  • alkylthio (also alkylsulfanyl or alkyl-S-)" as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 10 carbon atoms ("Ci-Cio-alkylthio"), frequently comprising 1 to 6 carbon atoms (“Ci-C6-alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio,
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio,
  • Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
  • haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHCI 2 , SCCI 3 ,
  • chlorofluoromethylthio dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio,
  • 2-chloroethylthio 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,
  • Ci-C4-Haloalkylthio is additionally, for example,
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
  • alkylsulfinyl and S(0) m -alkyl (wherein m is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • alkylsulfinyl and “S(0) m -alkyl” (wherein m is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Si-C2-a I kylsu If i nyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butyl sulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl).
  • Ci-C6-alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl,
  • haloalkylsulfinyl and "S(0) m -haloalkyl” (wherein m is 1 ) are equivalent and, as used herein, denote a haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • S(0) m -Ci-C4-haloalkyl (wherein m is 1 ), i.e. "Ci-C4-haloalkylsulfinyl”
  • Ci-C4-haloalkyl group as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-haloalkylsulfinyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C2- Haloalkylsulfinyl is, for example, S(0)CH 2 F, S(0)CHF 2 , S(0)CF 3 , S(0)CH 2 CI, S(0)CHCI 2 , S(0)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl,
  • Ci-C4-haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl,
  • C1-C6- Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5- brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl,
  • alkylsulfonyl and S(0) m -alkyl are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • C1-C2- alkylsulfonyl refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-alkylsulfonyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C6-alkylsulfonyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl.
  • Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl,
  • Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
  • haloalkylsulfonyl and “S(0) m -haloalkyl” are equivalent and, as used herein, denote a haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • S(0) m -Ci-C4-haloalkyl (wherein m is 2), i.e. "Ci-C4-haloalkylsulfonyl”
  • Ci-C4-haloalkyl group as defined above, attached via a sulfonyl [S(0)2] group.
  • C1-C6- haloalkylsulfonyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C 2 -Haloalkylsulfonyl is, for example, S(0) 2 CH 2 F, S(0) 2 CHF 2 , S(0) 2 CF 3 , S(0) 2 CH 2 CI, S(0)2CHCl2, S(0)2CCl3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,
  • chlorodifluoromethylsulfonyl 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2- fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,
  • Ci-C4-Haloalkylsulfonyl is additionally, for example,
  • Ci-C6-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl,
  • 5-chloropentylsulfonyl 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
  • alkylamino denotes in each case a group -NHR, wherein R is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("(C1-C6- alkyl)amino"), preferably 1 to 4 carbon atoms("(Ci-C4-alkyl)amino").
  • (C1-C6- alkyl)amino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino, tert-butylamino, and the like.
  • dialkylamino denotes in each case a group-NRR', wherein R and R', independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms (“di-(Ci-C4- alkyl)-amino").
  • Examples of a di-(Ci-C6-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl- butyl-amino, ethyl-isobutyl-amino, and the like.
  • cycloalkylamino denotes in each case a group -NHR, wherein R is a cycloalkyi radical usually having from 3 to 8 carbon atoms ("Cs-Cs-cycloalkylamino"), preferably 3 to 6 carbon atoms("C3-C6-cycloalkylamino").
  • C3-C6-cycloalkylamino are cyclopropylamino, cyclobutylarnino, cyclopentylamino, cyclohexylamino, and the like.
  • (alkyl)cycloalkylamino denotes in each case a group-NRR', wherein R is a cycloalkyi radical usually having from 3 to 8 carbon atoms and R' is a straight-chain or branched alkyl group having 1 to 4 carbon atoms ("(Ci-C4-alkyl)C3-C8-cycloalkylamino").
  • Examples are (methyl)cyclopropylamino, (ethyl)cyclobutylamino, (iso-propyl)cyclopentylarnino and (methyl)cyclohexylamino, and the like.
  • alkylaminosulfonyl denotes in each case a straight-chain or branched alkylamino group as defined above, which is bound to the remainder of the molecule via a sulfonyl [S(0)2] group.
  • alkylaminosulfonyl group examples include methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl, 2-butylaminosulfonyl, iso-butylaminosulfonyl, tert-butylaminosulfonyl, and the like.
  • dialkylaminosulfonyl denotes in each case a straight-chain or branched alkylamino group as defined above, which is bound to the remainder of the molecule via a sulfonyl [S(0)2] group.
  • S(0)2 sulfonyl
  • dimethylaminosulfonyl diethylaminosulfonyl, dipropylaminosulfonyl, dibutylaminosulfonyl, methyl-ethyl-aminosulfonyl, methyl-propyl-aminosulfonyl, methyl-isopropylaminosulfonyl, methyl-butyl-aminosulfonyl, methyl-isobutyl-aminosulfonyl, ethyl-propyl-aminosulfonyl, ethyl- isopropylaminosulfonyl, ethyl-butyl-aminosulfonyl, ethyl-isobutyl-aminosulfonyl, and the like.
  • haloalkylcarbonyl aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.
  • aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
  • heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.
  • Fully unsaturated 5- or 6- membered heterocyclic rings are aromatic.
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-yl, imidazolidin-yl, imidazolidin-
  • Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3- dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,
  • tetrahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,
  • a 3-, 4-, 5-, 6- or 7-membered fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered fully unsaturated (including aromatic) heterocyclic ring.
  • Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1
  • R 5a and R 5b together with the nitrogen atom to which they are bound form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring which may additionally contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, this is an N-bound heterocyclic ring which in addition to the nitrogen ring atom may contain 1 , 2, 3 or 4 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • Examples are aziridin-1 -yl, azetidin-1 -yl, pyrrolidine-1 -yl, pyrazolidin-1 -yl, imidazolin-1 -yl, oxazolidin-3-yl, isoxazolidin-3-yl, thiazolidin-1 - yl, isothiazolidin-1 -yl, triazolidin-1 -yl, piperdon-1 -yl, piperazine-1 -yl, morpholin-4-yl,
  • thiomorpholin-1 -yl 1 ,1 -dioxothiomorpholin-4-yl, pyrrol in-1 -yl, , imidazolin-1 -yl, dihydropyridin-1 - yl, tetrahydropyridin-1 -yl, pyrrol-1 -yl, pyrazo-1 -yl, imidazol-1 -yl and the like.
  • the term "optionally substituted” indicates that a moiety may be substituted or unsubstituted by one or more, in particular 1 , 2, 3 or 4 radicals.
  • Suitable substituents are, if not indicated otherwise, halogen, such as fluorine, chlorine or bromine, hydroxyl, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, cyano and nitro.
  • halogen such as fluorine, chlorine or bromine
  • hydroxyl Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, cyano and nitro.
  • substituents optionally substituted with from one to three substituents" and the like indicate that the moiety may be unsubstituted or from one to three of the available positions on the moiety may be substituted.
  • R 2 When a moiety contains a substituent which can be hydrogen, for example R 2 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said moiety being unsubstituted.
  • Preferred compounds according to the invention are compounds of formula (I) or a
  • Further preferred compounds according to the invention are compounds of formula (I) or a stereoisomer or salt thereof, especially an agriculturally or veterinarily acceptable salt.
  • Particularly preferred compounds according to the invention are compounds of formula (I) or a salt thereof, especially an agriculturally or veterinarily acceptable salt thereof.
  • R 1 is selected from hydrogen; halogen; cyano; Ci-C6-alkyl; Ci-C6-haloalkyl; Cs-Cs-cycloalkyl; C3-C8- halocycloalkyl; C2-C6-alkenyl; C2-C6-haloalkenyl; C2-C6-alkynyl; C2-C-haloalkynyl; wherein the radicals d-Cs-alkyl, C-i-Cs-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-Cs-alkenyl, C2-Cs-haloalkenyl, C2-Cs-alkynyl and C2-Cs-haloalkynyl may optionally be substituted by 1 , 2 or 3, preferably 1 or 2, in particular 1 , radicals R a ; -OR
  • R 1 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members and where the heterocyclic ring may be substituted by 1 , 2 or 3, preferably 1 or 2, in particular 1 radical R e .
  • R 1 is selected from hydrogen, cyano, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, specifically from cyano, halogen, Ci-C2-alkyl, Ci-C2-fluoroalkyl, Ci-C2-alkoxy and Ci-C2-fluoroalkoxy, more specifically from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and
  • R 2 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl. More preferably R 2 is hydrogen. Alternatively, R 2 is Ci-C2-alkyl, in particular methyl. According to a further alternative embodiment R 2 is C1-C2- haloalkyl and in particular halomethyl.
  • R 3 is selected from hydrogen; halogen; cyano; Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C2-C6-alkyny
  • R 3 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a , Ci-C6-alkoxy, Ci-C6-haloalkoxy, a 5-or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S, as ring members, where the heterocyclic ring may be substituted by 1 or 2, in particular 1 , radicals R e .
  • R 3 is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-alkyl substituted with a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S, as ring members and where the heterocyclic ring may be substituted by 1 or 2, in particular 1 , radicals RP, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, and a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S, as ring members and where the heterocyclic ring may be substituted by 1 or 2, in particular 1 , radicals R e .
  • R 3 is different from hydrogen. More particularly, R 3 is selected from halogen, Ci-C2-alkyl, C1-C2- haloalkyl, Ci-C2-alkyl substituted with a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S, as ring members and where the heterocyclic ring may be substituted by 1 radical RP selected from Ci-C2-alkyl and Ci-C2-haloalkyl, C1-C2- alkoxy, Ci-C2-haloalkoxy, and a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N and O, as ring members and where the heterocyclic ring may be substituted by 1 radical R e selected from Ci-C2-alkyl and Ci-C2-haloalkyl.
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy,
  • 5-trifluoromethyl-1 ,2,3,4-tetrazol-1 -yl-methyl more specifically from bromine, CF3, CHF2, CH2F, 2,2,2-trifluoroethoxy, OCH 3 , OCHF 2 , OCH 2 F and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl, and even more specifically form bromine, CF3, CHF2, 2,2,2-trifluoroethoxy, OCH3 and
  • Particular groups of embodiments relate to compounds of formula (I), wherein the variable Q is O or N, and k is 0, 1 or 2 and in particular is 1. According to particularly preferred embodiments Q is N, k is 1 and R 4 is located in the ortho-position with regard to the attachment point of the heterocycle containing Q.
  • R 4 is selected from halogen and Ci-C4-haloalkyl.
  • R 4 is selected from CI, Br and CF3, specifically from CI and CF3 and more specifically is CI.
  • Q is N
  • k is 1
  • R 4 is CI which is located in the ortho-position (corresponding to the 3-position of the 2-pyridyl moiety).
  • R 5 is a radical of the formula R 5 -a, wherein R 5a and R 5b are as defined herein and preferably, independently of each other, are selected from the group consisting of hydrogen; cyano; Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, radicals R a ; Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkyl- Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C2-C6-alkenyl which may be partially or fully halogenated
  • radicals R 5a or R 5b may also be OH; Ci-C6-alkoxy; Ci-C6-haloalkoxy; C1-C6- alkylthio; Ci-C6-haloalkylthio, where the alkyl moiety in the four last-mentioned radicals may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkoxy which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C3-C8-cycloalkyl-Ci-C4-alkoxy where the cycloalkyl moiety may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ;
  • R 5a and R 5b together with the nitrogen atom to which they are bound, may form an N-bound, 4-, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may additionally containing 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is unsubstituted or may be substituted by 1 , 2 or 3 radicals R e .
  • R 5a and R 5b are selected from hydrogen; Ci-Ce- alkyI, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl; Ci-C6-alkyl which is partially or fully halogenated and/or which is substituted by 1 , 2 or 3, more preferably 1 or 2, radicals R a ; Cs-Cs-cycloalkyl- Ci-C4-alkyl where the cycloalkyl moiety may be partially or fully halogenated and/or may be
  • R 5a and R 5b are selected from hydrogen, Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl, Ci-C6-haloalkyl, such as bromomethyl, chloromethyl, dichloromethyl, trichlor
  • -CH 2 CH NOCH 2 CH 2 CH 2 CH 3
  • Ci-C 4 -alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio or isobutylthio
  • -S(0) m -Ci-C 4 -alkyl such as -S(0)CH 3 , -S(0)CH 2 CH 3 , -S(0)CH 2 CH 2 CH 3 , -S(0)CH 2 CH 2 CH 2 CH 3 , -S(0) 2 CH 3 , -S(0) 2 CH 2 CH 3 , -S(0) 2 CH 2 CH 3 or -S(0) 2 CH 2 CH 2 CH 2 CH 3
  • C 3 -C6-cycloalkyl-Ci-C 4 -alkyl such as cyclopropylmethyl
  • R 5 is a radical of the formula R 5 -b, wherein R 5c and R 5d are as defined herein and preferably, independently of each other, are selected from the group consisting of hydrogen; cyano; C1-C6- alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Ci-C6-alkoxy; Ci-C6-haloalkoxy, where the alkyl moiety in the two last-mentioned radicals may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C 3 -C8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; C 3 -C 3 - cycloalkyl-
  • R 5c and R 5d are selected from Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl; Ci-C6-alkyl which is partially or fully halogenated and/or which is substituted by 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 or 2, in particular 1 , radicals R a ; Cs-Cs-Cs-cycloalkyl which may
  • R 5c and R 5d are independently selected from C1-C6- alkyl, d-Ce-haloalkyl, d-Ce-alkenyl, C3-C 7 -cylcoalkyl and C3-C 7 -cycloalkyl-Ci-C4-alkyl, or R 5c and R 5d together represent a linear C3-C7-alkylene or linear C3-C7-alkenylene forming together with the sulfur atom to which they are attached a 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated ring, wherein 1 or 2, in particular 1 , of the CH2 groups in the C3-C7-alkylene chain or 1 or 2, in particular 1 , of any of the CH2 or CH groups in the C3-C7-alkenylene chain may be replaced by 1 or 2, in particular 1 , groups independently selected from the group consisting of O, S and NRy, and wherein the carbon atoms in the C
  • R 5c and R 5d are independently selected from C1-C6- alkyl, d-Ce-haloalkyl, d-Ce-alkenyl, C3-C 7 -cylcoalkyl and C3-C 7 -cycloalkyl-Ci-C4-alkyl, or R 5c and R 5d together represent a linear d-Gs-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or 7-membered ring, wherein 1 or 2, in particular 1 , of the CH2 groups in the C 4 -C6-alkylene chain may be replaced by 1 or 2, in particular 1 , groups independently selected from the group consisting of O and NH, and wherein the carbon atoms in the C4-C6-alkylene chain may be substituted with 1 to 3, in particular 1 , identical or different substituents selected from halogen and Ci-C4-alkyl. More specifically R 5c and R 5d are
  • Ci-C6-alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl, Ci-C6-haloalkyl, such as bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,
  • cyclopropylpropyl cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl or cyclohexylbutyl; and even more specifically are independently selected from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl.
  • R 6 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl and benzyl which is unsubstituted or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R e .
  • R 6 is selected from Ci-C4-alkyl, Ci-C 4 -haloalkyl, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy-Ci-C 2 -alkyl, C 4 -C 7 -cycloalkyl, C4-C7- halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl.
  • R 6 is selected from Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 6 is selected from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Particular groups of embodiments relate to compounds of formula (I), wherein Y is N or C-R 7 with R 7 being selected from hydrogen, bromine, chlorine, fluorine, CN, Ci-C2-alkyl and C1-C2- haloalkyl, more preferably from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular hydrogen and Ci-C2-alkyl, and specifically R 7 is hydrogen.
  • Y is N or CH.
  • R 8 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, benzyl which is unsubstituted or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R e , and phenyl which is unsubstituted or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R e .
  • R 8 is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C2-alkoxy- Ci-C2-alkyl, Ci-C2-haloalkoxy-Ci-C2-alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C3-C7- cycloalkyl-Ci-C2-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and phenyl which is unsubstituted or may be substituted by 1 or 2, in particular 1 , radicals R e .
  • R 8 is selected from hydrogen, Ci-C4-alkyl, C3-C5-cycloalkyl-Ci-C2-alkyl, C2-C4-alkenyl, C2-C4-alkynyl and phenyl which is unsubstituted or may be substituted by 1 radical R e selected from halogen and Ci-C2-alkyl.
  • R 8 is selected from hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, Cs-Cs-cycloalkyl-methyl, such as cyclopentylmethyl or cyclopropylmethyl, C2-C4-alkenyl, such as ethenyl, prop-2-enyl or but-3-enyl, C2-C4-alkynyl, such as ethynyl, prop- 2-ynyl or but-3-ynyl and phenyl which is unsubstituted or may be substituted by 1 radical R e selected from chlorine, bromine and methyl, and more specifically from hydrogen, methyl, ethyl, isopropyl, cyclopropylmethyl, prop-2-enyl, prop-2-ynyl and phenyl which may or may not be substituted by 1 radical R e selected from chlorine and methyl.
  • Ci-C4-alkyl
  • R 9 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl and benzyl which is unsubstituted or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R e .
  • R 9 is selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy-Ci-C 2 -alkyl, C4-C7- cycloalkyl, C4-C7-halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl.
  • R 9 is selected from hydrogen Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 9 is selected from hydrogen and Ci-C4-alkyl, and more specifically from hydrogen, methyl, ethyl, n-propyl and isopropyl.
  • R 8 and R 9 together form a linear C2-C4-alkylene group, where one CH2 moiety of the linear C2-C4-alkylene group, which is not adjacent to the variables X 1 and X 2 of the formula Z1 , may be replaced by O, S, NR' or a carbonyl group, where R' is hydrogen or Ci-C4-alkyl, and where 1 , 2 or 3, more preferably 1 or 2, in particular 1 , hydrogen atoms of the linear C2-Cs-alkylene group may be replaced by halogen or Ci-C4-alkyl.
  • R 8 and R 9 together form a linear C2-C4-alkylene group, where 1 or 2, in particular 1 , hydrogen atoms of the linear C2-Cs-alkylene group may be replaced by Ci-C2-alkyl.
  • R 8 and R 9 together form a linear C2-C4-alkylene group, and more specifically form a linear C2-C3-alkylene group, such as ethylene or propylene.
  • R 10 is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Cs-Cs-cycloalkoxy and benzyl which is
  • R 10 is selected from hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C2- alkoxy-Ci-C2-alkyl, C4-C7-cycloalkyl, C2-C4-alkenyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Cs-Cs- cycloalkoxy.
  • R 10 is selected from CN, Ci-C4-alkyl, Ci-C4-haloalkyl and C1-C4- alkoxy.
  • R 10 is selected from CN, Ci-C2-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy; and more specifically from CN, methyl, ethyl, CH 2 CI, CH2CH2CI, CH 2 F, CHF 2 , CF 3 , CH 2 CH 2 F, CH2CF3, methoxy and ethoxy.
  • Particular groups of embodiments relate to compounds of formula (I), wherein Z is a moiety of the formula Z1 with X 2 -R 8 being a radical of formulae X-a or X-b, wherein R 11a and R 11b are as defined herein and preferably, independently of each other, are selected from the group consisting of hydrogen; cyano; Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Ci-C6-alkoxy; Ci-C6-haloalkoxy, where the alkyl moiety in the two last-mentioned radicals may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R
  • R 11a and R 11b are selected from Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl; Ci-C6-alkyl which is partially or fully halogenated and/or which is substituted by 1 or 2, in particular 1 , radicals R a ; Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by 1 or 2, in particular 1 , radicals R a ; Cs-Cs-Cs-cycloalkyl which may
  • R 11a and R 11b are independently selected from C1-C6- alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 7 -cylcoalkyl and C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, or R 11a and R 11b together represent a linear C3-C7-alkylene or linear C3-C7-alkenylene forming together with the sulfur atom to which they are attached a 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated ring, wherein 1 or 2, in particular 1 , of the CH2 groups in the C3-C7-alkylene chain or 1 or 2, in particular 1 , of any of the CH2 or CH groups in the C3-C7-alkenylene chain may be replaced by 1 or 2, in particular 1 , groups independently selected from the group consisting of O, S and NR y , and wherein the
  • R 11a and R 11b are independently selected from C1-C6- alkyl, Ci-C 6 -haloalkyl C 2 -C 6 -alkenyl, C 3 -C 7 -cylcoalkyl and C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, or R 11a and R 11b together represent a linear C 4 -C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or 7-membered ring, wherein 1 or 2, in particular 1 , of the CH2 groups in the C 4 -C6-alkylene chain may be replaced by 1 or 2, in particular 1 , groups
  • R 11a and R 11b are independently selected from Ci-C6-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 1 ,2-dimethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl or 1 -ethyl-2-methylpropyl, Ci-C6-haloalkyl, such as bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,
  • cyclopropylpropyl cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl or cyclohexylbutyl; and even more specifically are independently selected from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl.
  • a particular group of embodiments relate to compounds of formula (I), wherein Z is CN.
  • Preferred compounds of formula (I) are those wherein Z is a moiety of the formula Z1 , wherein X 1 is O, S, N-R 9 or N-O-R 9 , preferably O, S or N-R 9 , and X 2 is O, S or NR 10 , wherein R 8 is selected from hydrogen, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, C 4 -C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C2-alkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl and phenyl which is unsubstituted or may be substituted by 1 or 2, in particular 1 , radicals R e , more preferably selected from hydrogen, Ci-C 4 -alkyl, C3-C5-cycloalkyl-Ci-C2-alkyl,
  • Particularly preferred compounds of formula (I) are those wherein Z is a moiety of the formula Z1 , wherein X 1 is O or S, in particular O, and X 2 is O, S or NR 10 , in particular O or NR 10 , and R 8 is hydrogen, Ci-C 4 -alkyl, C 3 -C 5 -cycloalkyl- methyl, C2-C4-alkenyl, C2-C4-alkynyl or phenyl, in particular hydrogen, methyl, ethyl, isopropyl, cyclopropylmethyl, prop-2-enyl, prop-2-ynyl or phenyl, and R 10 is CN, Ci-C2-alkyl, C1-C2- haloalkyl or Ci-C2-alkoxy, in particular, CN, methyl, methoxy or CH2CH2CI.
  • Further particularly preferred compounds of formula (I) according to the aforementioned embodiments are those wherein Z is a moiety of the formula Z1 , wherein X 1 is N-R 9 or N-O-R 9 , and X 2 is O, and R 8 and R 9 together form a linear C2-C 4 -alkylene group.
  • Further particular groups of embodiments relate to compounds of formula (I), wherein Z is a moiety of the formula Z1 , wherein X 1 is O, S or N-R 9 , preferably O or S, and X 2 -R 8 is a radical of formulae X-a or X-b with R 11a and R 11b each having one of the general meanings defined herein, or, in particular, one of the preferred meanings given above.
  • Preferred compounds of formula (I) are those wherein Z is a moiety of the formula Z1 , wherein X 1 is O, S or N-R 9 , preferably O or S, X 2 -R 8 is a radical of formulae X-a or X-b, wherein R 11a and R 11b are independently selected from C1-C6- alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 7 -cylcoalkyl and C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, or R 11a and R 11b together represent a linear C 4 -C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or 7-membered ring, wherein 1 or 2, in particular 1 , of the CH2 groups in the C 4 -C6-alkylene chain may be replaced by 1 or 2, in particular
  • R 11a and R 11b are independently selected Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C7-cylcoalkyl and C3-C7-cycloalkyl-Ci- C 4 -alkyl, or R 11a and R 11b together represent a linear C 4 -C5-alkylene forming together with the sulfur atom to which it is attached a 5- or 6-membered ring, wherein one of the CH2 groups in the C 4 -C5-alkylene chain may be replaced by O or NH, and wherein the carbon atoms in the C 4 -C5-alkylene chain may be substituted with one substituent selected from halogen and C1-C
  • R 1 is selected from cyano, halogen, Ci-C 2 -alkyl, Ci-C 2 -fluoroalkyl Ci-C 2 -alkoxy and Ci-C 2 - fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, specifically from chlorine, bromine and methyl, and more specifically from methyl and chlorine;
  • R 2 is selected from hydrogen, Ci-C 2 -alkyl and Ci-C 2 -haloalkyl, in particular from hydrogen and Ci-C 2 -alkyl, specifically from hydrogen and methyl, and more specifically is hydrogen;
  • R 3 is selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -haloalkyl, Ci-C 2 -alkyl substituted with a 5- or
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl, and specifically from bromine, CF 3 , CHF 2 , 2,2,2-trifluoroethoxy, OCH 3 , and
  • R 4 is selected from halogen and Ci-C4-haloalkyl, in particular from CI, Br and CF3, specifically from CI and CF3 and more specifically is CI;
  • -CH 2 CH NOCH 2 CH 3 , methylthio, ethylthio, -S(0)CH 3 , -S(0)CH 2 CH 3 , -S(0) 2 CH 3 ,
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C7-cylcoalkyl and C3-C7-cycloalkyl-Ci-C4-alkyl, or R 5c and R 5d together represent a linear C4-C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or
  • p is 0 or 1 , in particular is 0;
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C2-alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl, in particular selected from Ci-C4-alkyl and Ci-C4-haloalkyl, specifically from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • Z is selected from CN, a moiety of the formula Z1 , wherein X 1 is O or S, in particular O, and X 2 is O, S or NR 10 , in particular O or NR 10 , and R 8 is hydrogen, Ci-C 4 -alkyl, C3-C5- cycloalkyl-methyl, C2-C4-alkenyl, C2-C4-alkynyl and phenyl, in particular hydrogen, methyl, ethyl, isopropyl, cyclopropylmethyl, prop-2-enyl, prop-2-ynyl and phenyl, and R 10 is CN, Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C2-alkoxy, in particular, CN, methyl, methoxy or
  • R 1 is selected from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl,
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is methyl;
  • R 2 is hydrogen
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy
  • 2,2,2-trifluoroethoxy and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl in particular from bromine, CF 3 , CHF 2 , 2,2,2-trifluoroethoxy, OCH 3 and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2- yl-methyl, specifically from CF 3 and CHF 2 , and more specifically is CHF 2 ;
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl,
  • -CH 2 CH NO-Ci-C 4 -alkyl
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, C 3 -C6-cylcoalkyl and C 3 -C6- cycloalkyl-Ci-C 4 -alkyl, in particular from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl, and specifically from methyl, ethyl and isopropyl;
  • p is 0; is selected from Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • R 7 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, and specifically is hydrogen;
  • R 1 is selected from cyano, halogen, Ci-C2-alkyl, Ci-C2-fluoroalkyl Ci-C2-alkoxy and C1-C2- fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, and specifically from chlorine, bromine and methyl;
  • R 2 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, specifically from hydrogen and methyl, and more specifically is hydrogen;
  • R 3 is selected from halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, and a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N and O, as ring members and where the heterocyclic ring may be substituted by 1 radical R e selected from Ci-C2-alkyl and Ci-C2-haloalkyl; in particular R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and
  • k 0, 1 or 2, and in particular is 1 ;
  • R 4 is selected from halogen and Ci-C4-haloalkyl, in particular from CI, Br and CF 3 , specifically from CI and CF 3 and more specifically is CI;
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C7-cylcoalkyl and C3-C7-cycloalkyl-Ci-C4-alkyl, or R 5c and R 5d together represent a linear C4-C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or
  • p is 0 or 1 , in particular is 0;
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C2-alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl, in particular selected from Ci-C4-alkyl and Ci-C4-haloalkyl, specifically from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is methyl;
  • R 2 is hydrogen
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and
  • 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl in particular from bromine, CF3, CHF2, CH2F, OCH3 OCHF2 and OCH2F, and specifically from CF 3 and CHF 2 ;
  • Q is N; k is 1 ;
  • R 4 is chlorine which is located in the ortho-position with regard to the attachment point of the heterocycle containing Q;
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and
  • C3-C6-cycloalkyl-Ci-C4-alkyl in particular from hydrogen, Ci-C4-alkyl and C3-C6-cycloalkyl-
  • Ci-C3-alkyl specifically from hydrogen, methyl, isopropyl, tert-butyl and 1 -cyclopropyl- ethyl, and more specifically from hydrogen and methyl;
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, C3-C6-cylcoalkyl and C3-C6- cycloalkyl-Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl, and specifically from methyl, ethyl and isopropyl;
  • R 6 is selected from Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, and specifically is hydrogen;
  • variables R a , R b , R c , R d , R e , R f , Rs, R', R j , R k , R', R m , R n , RP, R ⁇ , R r , R x and R y independently of each other, preferably have one of the following meanings:
  • R a is preferably selected from the group consisting of Cs-Cs-cycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-alk
  • each R b is independently selected from the group consisting of Ci-C4-alkyl, C1-C4- haloalkyl, Cs-Cs-cycloalkyl, phenyl and benzyl.
  • R c and R d are, independently of each other and independently of their occurrence, selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl- CH 2 , C3-Cs-cycloalkyl, cyano, benzyl, phenyl and Ci-C4-alkoxy;
  • R c and R d together with the nitrogen atom to which they are bound may form a saturated 5-, 6- or 7-membered N-heterocycle, which may contain 1 or 2 further heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents selected from Ci-C4-alkyl.
  • each R e is independently selected from the group consisting of halogen, in particular fluorine, chlorine or bromine, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxycarbonyl, cyano, C1-C4- alkoxy and Ci-C4-haloalkoxy, especially from the group consisting of halogen, in particular fluorine, chlorine or bromine, methyl, halomethyl, e.g. trifluoromethyl, difluoromethyl or bromodifluoromethyl, cyano, methoxy and halomethoxy, e.g. trifluoromethoxy, difluoromethoxy or fluoromethoxy.
  • halogen in particular fluorine, chlorine or bromine
  • R f and Rs are, independently of each other and independently of their occurrence, selected from the group consisting of Ci-C4-alkyl and are in particular methyl.
  • each R' is independently selected from the group consisting of Ci-C4-alkyl, C1-C4- haloalkyl, Cs-Cs-cycloalkyl, phenyl and benzyl.
  • each Ri is independently selected from the group consisting of Ci-C4-alkyl, C1-C4- haloalkyl, Cs-Cs-cycloalkyl, phenyl and benzyl.
  • R k and R' are, independently of each other and independently of their occurrence, selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-Cs-cycloalkyl- CH2, Cs-Cs-cycloalkyl, cyano, benzyl, phenyl and Ci-C4-alkoxy;
  • R k , R' together with the nitrogen atom, to which they are bound may form a saturated 5-, 6- or 7-membered N-heterocycle, which may contain 1 or 2 further heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents selected from Ci-C4-alkyl.
  • each R m is independently selected from the group consisting of Ci-C4-alkyl, C1-C4- haloalkyl, Cs-Cs-cycloalkyl, phenyl and benzyl.
  • R n and R° are, independently of each other and independently of their occurrence, selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-Cs-cycloalkyl- CH2, C3-Cs-cycloalkyl, cyano, benzyl, phenyl and Ci-C4-alkoxy;
  • R n , R° together with the nitrogen atom, to which they are bound may form a saturated 5-, 6- or 7-membered N-heterocycle, which may contain 1 or 2 further heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents selected from Ci-C 4 -alkyl.
  • each RP is independently selected from the group consisting of halogen, in particular fluorine, chlorine or bromine, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxycarbonyl, cyano, C1-C4- alkoxy and Ci-C4-haloalkoxy especially from the group consisting of halogen, in particular fluorine, chlorine or bromine, methyl, halomethyl, e.g. trifluoromethyl, difluoromethyl or bromodifluoromethyl, cyano, methoxy and halomethoxy, e.g. trifluoromethoxy, difluoromethoxy or fluoromethoxy.
  • R r are, independently of each other and independently of their occurrence, selected from the group consisting of hydrogen, halogen, cyano and Ci-C6-alkyl.
  • R x is independently selected from the group consisting of halogen and Ci-C4-alkyl, in particular from the group consisting of fluorine, chlorine and methyl, especially from Ci-C4-alkyl, and specifically methyl.
  • R is R x is independently selected from the group consisitng of Ci-C4-alkyl, and especially is methyl.
  • the compound of formula (I) is of the general formula (l-a).
  • R 1 , R 3 , R 5a , R 5b , R 6 , Y and Z have one of the general meanings, or, in particular, one of the preferred meanings given above.
  • R 1 is selected from cyano, halogen, Ci-C2-alkyl, Ci-C2-fluoroalkyl Ci-C2-alkoxy and C1-C2- fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, specifically from chlorine, bromine and methyl;
  • R 3 is selected from halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkyl substituted with a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S, as ring members and where the heterocyclic ring may be substituted by 1 radical RP selected from Ci-C2-alkyl and Ci-C2-haloalkyl, Ci-C2-alkoxy, and C1-C2- haloalkoxy; in particular R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl, and specifically from bromine, CF3, CHF2, 2,2,2-trifluoroethoxy, OCH3,
  • R 6 is selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C2-alkyl, C 4 -C7-cycloalkyl, C 4 -C7-halocycloalkyl, C2-C 4 -alkenyl and C2-C 4 -haloalkenyl, in particular selected from Ci-C 4 -alkyl and Ci-C 4 -haloalkyl, specifically from Ci-C 4 -alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • Z is selected from CN, a moiety of the formula Z1 , wherein X 1 is O or S, in particular O, and X 2 is O, S or NR 10 , in particular O or NR 10 , and R 8 is hydrogen, Ci-C 4 -alkyl, C3-C5- cycloalkyl-methyl, C2-C 4 -alkenyl, C2-C 4 -alkynyl and phenyl, in particular hydrogen, methyl, ethyl, isopropyl, cyclopropylmethyl, prop-2-enyl, prop-2-ynyl and phenyl, and R 10 is CN, Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C2-alkoxy, in particular, CN, methyl, methoxy or CH2CH2CI, a moiety Z1 , wherein X 1 is O or S and X 2 -R 8 is a radical of formulae X-a or X-
  • R 1 is selected from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl,
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is chlorine or methyl;
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy
  • 2,2,2-trifluoroethoxy and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl in particular from bromine, CF 3 , CHF 2 , 2,2,2-trifluoroethoxy, OCH 3 and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2- yl-methyl, and specifically from CF 3 and CHF 2 ;
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl,
  • R 6 is selected from Ci-C 4 -alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, Ci-C 2 -alkyl and Ci-C 2 -haloalkyl, in particular from hydrogen and Ci-C 2 -alkyl, and specifically is hydrogen;
  • R 1 is methyl
  • R 3 is selected from CF3 and CHF2;
  • R 5a and R 5b are independently selected from hydrogen and methyl
  • R 6 is methyl
  • Y is N or C-H
  • R 1 is selected from cyano, halogen, Ci-C 2 -alkyl, Ci-C 2 -fluoroalkyl Ci-C 2 -alkoxy and Ci-C 2 - fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, specifically from chlorine, bromine and methyl;
  • R 3 is selected from halogen, Ci-C 2 -alkyl, Ci-C 2 -haloalkyl, Ci-C 2 -alkoxy, Ci-C 2 -haloalkoxy, and a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N and O, as ring members and where the heterocyclic ring may be substituted by 1 radical R e selected from Ci-C 2 -alkyl and Ci-C 2 -haloalkyl; in particular R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy- Ci-C 2 -alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C 2 -C4-alkenyl and C 2 -C4-haloalkenyl, in particular selected from Ci-C4-alkyl and Ci-C4-haloalkyl, specifically from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • R 1 is selected from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl,
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is methyl;
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and
  • 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl in particular from bromine, CF 3 , CHF 2 , CH 2 F, OCH 3 ,
  • OCHF2 and OCH2F and specifically from CF 3 and CHF 2 ;
  • R 5a and R 5b are independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl and
  • C 3 -C6-cycloalkyl-Ci-C 4 -alkyl in particular from hydrogen, Ci-C 4 -alkyl and C 3 -C6-cycloalkyl- Ci-C 3 -alkyl, specifically from hydrogen, methyl, isopropyl, tert-butyl and 1 -cyclopropyl- ethyl, and more specifically from hydrogen and methyl;
  • R 6 is selected from Ci-C 4 -alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, and specifically is hydrogen;
  • compounds of formula (l-a) the N-oxides and the salts thereof, where
  • R 1 is methyl
  • R 3 is selected from CF 3 and CHF2;
  • R 5a and R 5b are independently selected from hydrogen and methyl
  • R 6 is methyl
  • the compound of formula (I) is of the general formula (l-b).
  • R 1 , R 3 , R 5C , R 5D , p, R 6 , Y and Z have one of the general meanings, or, in particular, one of the preferred meanings given above.
  • R 1 is selected from cyano, halogen, Ci-C2-alkyl, Ci-C2-fluoroalkyl Ci-C2-alkoxy and C1-C2- fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, and specifically from chlorine, bromine and methyl;
  • R 3 is selected from halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkyl substituted with a 5- or
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy and 5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl-methyl, and specifically from bromine, CF3, CHF2, 2,2,2-trifluoroethoxy, OCH3, and
  • R 5C and R 5D are independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C7-cylcoalkyl and C3-C7-cycloalkyl-Ci-C4-alkyl, or R 5C and R 5D together represent a linear C4-C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or
  • p is 0 or 1 , in particular is 0;
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C2-alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl, in particular selected from Ci-C4-alkyl and Ci-C4-haloalkyl, specifically from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • Z is selected from CN, a moiety of the formula Z1 , wherein X 1 is O or S, in particular O, and X 2 is O, S or NR 10 , in particular O or NR 10 , and R 8 is hydrogen or Ci-C4-alkyl, in particular hydrogen, methyl, ethyl or isopropyl, and R 10 is CN, Ci-C2-alkyl, Ci-C2-haloalkyl or C1-C2- alkoxy, in particular, CN, methyl, methoxy or CH2CH2CI, a moiety Z1 , wherein X 1 is O or S and X 2 -R 8 is a radical of formulae X-a or X-b, and R 11a and R 11 b are, independently of each other, selected from Ci-C4-alkyl, in particular from methyl ethyl and isopropyl; and a moiety Z1 , wherein X 1 is N-R 9 or N-O-R 9
  • R 1 is selected from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl,
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is methyl;
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, C3-C6-cylcoalkyl and C3-C6- cycloalkyl-Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl, and specifically from methyl, ethyl and isopropyl;
  • R 6 is selected from Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, and specifically is hydrogen;
  • R 1 is methyl
  • R 3 is selected from CF 3 and CHF2;
  • R 5c and R 5d are independently selected from ethyl and isopropyl
  • R 6 is methyl
  • Y is N or C-H
  • R 1 is selected from cyano, halogen, Ci-C2-alkyl, Ci-C2-fluoroalkyl Ci-C2-alkoxy and C1-C2- fluoroalkoxy, in particular from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl, difluoromethyl, difluoromethoxy and trifluoromethoxy, and specifically from chlorine, bromine and methyl;
  • R 3 is selected from halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, and a 5- or 6-membered aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N and O, as ring members and where the heterocyclic ring may be substituted by 1 radical R e selected from Ci-C2-alkyl and Ci-C2-haloalkyl; in particular R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, fluoromethyl, methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and (5-trifluoromethyl-1 ,2,3,4-tetrazol-2-yl), and specifically from bromine, CF3, CHF2, CH2F,
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C7-cylcoalkyl and C3-C7-cycloalkyl-Ci-C4-alkyl, or R 5c and R 5d together represent a linear C4-C6-alkylene forming together with the sulfur atom to which it is attached a 5-, 6- or
  • p is 0 or 1 , in particular is 0;
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-haloalkoxy- Ci-C2-alkyl, C4-C7-cycloalkyl, C4-C7-halocycloalkyl, C2-C4-alkenyl and C2-C4-haloalkenyl, in particular selected from Ci-C4-alkyl and Ci-C4-haloalkyl, specifically from Ci-C4-alkyl, and more specifically from methyl, ethyl, n-propyl and isopropyl.
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, bromine, chlorine, fluorine, CN, C1-C2- alkyl and Ci-C2-haloalkyl, in particular from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, specifically from hydrogen and Ci-C2-alkyl, and more specifically is hydrogen;
  • R 1 is selected from fluorine, chlorine, bromine, CN, methyl, methoxy, trifluoromethyl,
  • difluoromethyl, difluoromethoxy and trifluoromethoxy in particular from chlorine, bromine and methyl, and specifically is methyl;
  • R 3 is selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl,
  • fluoromethyl methoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy and
  • R 5c and R 5d are independently selected from Ci-C6-alkyl, C3-C6-cylcoalkyl and C3-C6- cycloalkyl-Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl, isopropyl, 2-butyl, isobutyl and cyclopentyl, and specifically from methyl, ethyl and isopropyl;
  • R 6 is selected from Ci-C4-alkyl, in particular from methyl, ethyl, n-propyl and isopropyl, and specifically from methyl and ethyl;
  • Y is N or C-R 7 , wherein R 7 is selected from hydrogen, Ci-C2-alkyl and Ci-C2-haloalkyl, in particular from hydrogen and Ci-C2-alkyl, and specifically is hydrogen;
  • R 1 is methyl
  • R 3 is selected from CF 3 and CHF 2 ;
  • R 5c and R 5d are independently selected from ethyl and isopropyl
  • R 6 is methyl
  • Y is N or C-H
  • Examples of preferred compounds of the present invention are the individual anthranilamide derivatives of the formula (l-a) as listed in the following tables 1 to 6 and physiologically tolerated salts thereof.
  • Table 12 Compounds of the formula (l-b) wherein R 1 is bromine, R 6 is ethyl, p is 0 and the combination of R 3 , R 5c , R 5d , R 6 , Y and Z for a compound corresponds in each case to one row of Table B (B-1 to B-120).

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Abstract

La présente invention concerne des composés d'anthranilamide de formule I et ses stéréoisomères, sels, tautomères et N-oxydes de ainsi que des compositions les comprenant. L'invention concerne en outre l'utilisation des composés d'anthranilamide ou des compositions comprenant de tels composés pour lutter contre des organismes nuisibles invertébrés. En outre, l'invention concerne des procédés d'application de tels composés. Dans la formule, k vaut 0, 1, 2 ou 3 ; Q est N ou CH ; R1 est entre autres hydrogène, halogène, SF5, -SCN, nitro, azido, un groupe alkyle en C1-C8, un groupe halogénoalkyle en C1-C8 etc., R2 est entre autres choisi parmi hydrogène, un groupe alkyle en C1-C6 etc.; R3 est choisi dans le groupe constitué par hydrogène, halogène, cyano, azido, nitro, -SCN, SF5, un groupe alkyle en C1-C6 pouvant être partiellement ou totalement halogéné etc.; R4 est hydrogène, halogène ou un groupe halogénoalkyle en C1-C4 ; R5 est un radical R5-a ou R5-b où p vaut 0 ou 1 ; et où R5a et R5b sont tels que définis dans les revendications : R6 est choisi dans le groupe constitué d'un groupe alkyle en C1-C6, haloalkyle en C1-C6, alcoxy en C1-C4-alkyle en C1-C4, halogénoalcoxy en C1-C4-alkyle en C1-C4, etc ; Y est N ou C-R7, où R7 est tel que défini dans les revendications ; Z est CN ou une fraction de la formule Z1, où X1 est O, S, N-R9, N-O-R9 ou N-S-R9 ; X2 est O, S ou NR10, ou X2-R8 est un radical de la formule X-a ou de la formule X-b tel que défini dans les revendications ; où R8, R9 et R10 sont tels que définis dans les revendications.
PCT/EP2014/068157 2013-08-27 2014-08-27 Composés d'anthranilamide et leur utilisation comme pesticides WO2015028501A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105061396A (zh) * 2015-08-13 2015-11-18 南阳师范学院 一种酰胺衍生物及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003016284A1 (fr) * 2001-08-16 2003-02-27 E. I. Du Pont De Nemours And Company Anthranilamides substitues utilises dans le controle des depredateurs invertebres
WO2006000336A2 (fr) * 2004-06-28 2006-01-05 Bayer Cropscience Ag Anthranilamides
WO2012004208A1 (fr) * 2010-07-09 2012-01-12 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique utilisés comme pesticides
WO2013024006A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés d'anthranilamide et leur utilisation en tant que pesticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003016284A1 (fr) * 2001-08-16 2003-02-27 E. I. Du Pont De Nemours And Company Anthranilamides substitues utilises dans le controle des depredateurs invertebres
WO2006000336A2 (fr) * 2004-06-28 2006-01-05 Bayer Cropscience Ag Anthranilamides
WO2012004208A1 (fr) * 2010-07-09 2012-01-12 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique utilisés comme pesticides
WO2013024006A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés d'anthranilamide et leur utilisation en tant que pesticides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105061396A (zh) * 2015-08-13 2015-11-18 南阳师范学院 一种酰胺衍生物及其制备方法

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