WO2013167633A1 - Composés d'acrylamide pour la lutte contre des animaux nuisibles invertébrés - Google Patents

Composés d'acrylamide pour la lutte contre des animaux nuisibles invertébrés Download PDF

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Publication number
WO2013167633A1
WO2013167633A1 PCT/EP2013/059547 EP2013059547W WO2013167633A1 WO 2013167633 A1 WO2013167633 A1 WO 2013167633A1 EP 2013059547 W EP2013059547 W EP 2013059547W WO 2013167633 A1 WO2013167633 A1 WO 2013167633A1
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alkyl
cycloalkyl
group
substituents
heterocyclic ring
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PCT/EP2013/059547
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English (en)
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Pascal BINDSCHÄDLER
Wolfgang Von Deyn
Karsten KÖRBER
Florian Kaiser
Ralph Paulini
Deborah L. Culbertson
Paul Neese
Franz Josef Braun
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Basf Se
Basf Schweiz Ag
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Priority to BR112014027133A priority Critical patent/BR112014027133A2/pt
Publication of WO2013167633A1 publication Critical patent/WO2013167633A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

Definitions

  • Acrylamide compounds for combating invertebrate pests Description
  • the present invention relates to acrylamide compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them.
  • the invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
  • Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, 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, in particular insects, arachnids and nematodes.
  • the invention relates to acrylamide compounds of formula I
  • B 1 , B 2 , B 3 , B 4 and B 5 are each independently selected from the group consisting of N and C-R 2 , with the proviso that at most two of B 1 , B 2 , B 3 , B 4 and B 5 are N;
  • G 1 , G 4 and G 5 are each independently selected from the group consisting of N and C-R 4 ;
  • G 2 and G 3 are each independently selected from the group consisting of N, C-A and C-R 4 ; with the proviso that one of G 2 and G 3 is C-A; with the proviso that at most two of G 1 , G 2 , G 3 , G 4 and G 5 are N;
  • A is a group A 1 , A 2 , A 3 , A 4 or A 5 ,
  • a 2 is a group of following formula: wherein
  • W is selected from O and S;
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic 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 heteromono- or
  • heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 11 ;
  • radicals selected from Ci-C6-alkoxy, and C3-C6- cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of Ci-C6-alkyl and Ci-C6-alkoxy;
  • each R 2 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic 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 heteromono- or heterobicyclic ring may be substituted by one or more, e.g.
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g.
  • each R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N,
  • heteromonocyclic or heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 11 ;
  • q and p are independently selected from 0 and 1 ;
  • R 6 is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g.
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g.
  • substituents R 11 1 , 2 or 3, preferably 1 , substituents R 11 ; or R 5 and R 6 , together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO2 as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R 17 ; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may
  • phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , and
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g.
  • each R 8 is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF 5 , C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ,
  • R 8 together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ; and
  • R 8 as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl,
  • C2-C6-alkynyl and C2-C6-haloalkynyl where the aliphatic moieties in these six radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ; and
  • heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R 16 ;
  • R 9 is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last- mentioned radicals may be substituted by one or more, e.g.
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ; and
  • R 9 in the groups -S(0) n R 9 and -OSO2R 9 is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;
  • heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or
  • R 10b independently of each other and independently of each occurrence, are 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, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-
  • heterocyclic ring 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 10a and R 10c form together with the nitrogen atom they are bonded to a 3-
  • heterocyclic ring 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 11 is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or
  • radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S
  • R 12 is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, 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-, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • R 13 is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF 5 , d-Ce-alkoxy, Ci-C 6 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4 cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3, in
  • R 13 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , substituents selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
  • R 14 is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;
  • cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ; and R 14b , independently of each other, have one of the meanings given for R 14 ; or
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally
  • heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R 15 is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • each R 16 is independently selected from the group consisting of halogen, nitro,
  • Ci-C6-haloalkylsulfonyl trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;
  • Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
  • two R 16 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, and wherein the ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;
  • R 17 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy,
  • each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof.
  • the invention relates to acrylamide compounds of formula I
  • B 1 , B 2 , B 3 , B 4 and B 5 are each independently selected from the group consisting of N and C-R 2 , with the proviso that at most two of B 1 , B 2 , B 3 , B 4 and B 5 are N;
  • G 4 and G 5 are each independently selected from the group consisting of N and C-R 4 ; and G 3 are each independently selected from the group consisting of N, C-A and C-R 4 ; with the proviso that one of G 2 and G 3 is C-A; with the proviso that at most two of G 1 , G 2 , G 3 , G 4 and G 5 are N; A is a group A 1 , A 2 , A 3 , A 4 or A 5 ,
  • a 2 is a group of following formula: wherein
  • W is selected from O and S;
  • a 3 is a group of following formula:
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic 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 heteromono- or
  • heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 11 ;
  • radicals selected from Ci-C6-alkoxy, and C3-C6- cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals selected from the group consisting of Ci-C6-alkyl and Ci-C6-alkoxy;
  • each R 2 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic 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 heteromono- or
  • heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 11 ; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkylsulfonyl, wherein the aliphatic and cycloaliphatic moieties in the five last-mentioned radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 8 ;
  • R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N,
  • heteromonocyclic or heterobicyclic ring may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 11 ;
  • q and p are independently selected from 0 and 1 ; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g.
  • phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , and
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g.
  • substituents R 11 1 , 2 or 3, preferably 1 , substituents R 11 ; or R 5 and R 6 , together with the nitrogen atom to which they are bound, form a 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO2 as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R 17 ; is selected from the group consisting of hydrogen, cyano, Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may
  • phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , and
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, e.g.
  • R 8 is independently selected from the group consisting of cyano, azido, nitro, -SCN, -SF 5 , C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ,
  • R 8 together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ; and
  • R 8 as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 3 ; and
  • R 9 is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last- mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ; and
  • R 9 in the groups -S(0) n R 9 and -OSO2R 9 is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;
  • heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or
  • R 10b independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-
  • heterocyclic ring 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 10a and R 10c form together with the nitrogen atom they are bonded to a 3-
  • heterocyclic ring 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 11 is independently selected from the group consisting of halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , radicals R 8 ,
  • phenyl optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected independently from R 16 ;
  • radicals selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S
  • R 12 is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, 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-, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; each R 13 is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF 5 , d-Ce
  • Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3,
  • R 13 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , substituents selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
  • R 14 is independently selected from the group consisting of hydrogen, cyano, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;
  • cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, preferably 1 , substituents R 16 ;
  • R 14a and R 14b independently of each other, have one of the meanings given for R 14 ;
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally
  • heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • each R 15 is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • Ci-C4-alkylsulfonyl and oxo are examples of compounds having the following properties:
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
  • R 16 is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl,
  • Ci-C6-haloalkylsulfonyl trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;
  • Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
  • two R 16 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, and wherein the ring optionally carries one or more, e.g. 1 , 2 or 3, preferably 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy;
  • R 17 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy,
  • each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof.
  • the present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • the present invention also provides a veterinary composition
  • a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid or solid carrier.
  • the present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein.
  • the present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein.
  • the present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.
  • steroisomers 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).
  • the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • One center of chirality is the carbon atom carrying radicals R 1 and L.
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
  • Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • the term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).
  • the compounds of formula I may also be present in the form of the respective tautomers.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally 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 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 (NH 4+ ) 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, isopropylammoni
  • benzyltriethylammonium furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Suitable acid addition salts e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • inorganic acids for example hydrochlorids, sulphates, phosphates, and nitrates
  • salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • invertebrate pest encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • the plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • plants comprises any types of plants including “non-cultivated plants” and in particular "cultivated plants”.
  • non-cultivated plants refers to any wild type species or related species or related genera of a cultivated plant.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e.g. by glycosylation or polymer additions such as prenylated, acetylated or
  • HPPD hydroxylphenylpyruvate dioxygenase
  • PDS phytoene desaturase
  • ALS acetolactate synthase
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • GS glutamine synthetase
  • protoporphyrinogen-IX oxidase inhibitors lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering.
  • plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e.g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.g. imazamox, or ExpressSun ® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e.g.
  • mutagenesis e.g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.g. imazamox, or ExpressSun ® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e.g.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,
  • ⁇ -endotoxins e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,
  • VIP vegetative insecticidal proteins
  • VIP1 e.g. VIP1 , VIP2, VIP3 or VIP3A
  • insecticidal proteins of bacteria colonizing nematodes e.g. Photorhabdus spp. or Xenorhabdus spp.
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins
  • agglutinins e.g., fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy- steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases.
  • RIP ribosome-inactivating proteins
  • RIP ribosome-inactivating proteins
  • steroid metabolism enzymes such as 3-hydroxy
  • insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e.g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e.g., in
  • WO 03/18810 und WO 03/52073 The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.g. in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e.g. EP-A 392 225), plant disease resistance genes (e.g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e.g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e.g. potato cultivars capable of synth
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e.g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 (“Ci-C 3 -alkyl"),1 to 4 (“Ci-C 4 -alkyl”), 1 to 6 (“Ci-C 6 -alkyl”), 1 to 8 (“Ci-C 8 -alkyl”) or 1 to 10 (“Ci-Cio-alkyl”) carbon atoms.
  • Ci-C 2 -Alkyl is methyl or ethyl.
  • d-Cs-Alkyl is additionally propyl and isopropyl.
  • Ci-C 4 -Alkyl is additionally butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl).
  • Ci-C6-Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof.
  • Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
  • haloalkyl as used herein, which is also expressed as “alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C 2 -haloalkyl”), 1 to 3 (“Ci-C 3 -haloalkyl”), 1 to 4 (“Ci-C 4 -haloalkyl”), 1 to 6 (“Ci-C 6 - haloalkyl”), 1 to 8 (“Ci-C 8 -haloalkyl”) or 1 to 10 (“Ci-Cio-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,
  • Ci-C3-haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl,
  • Ci-C4-haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
  • Ci-C6-haloalkyl are, apart those mentioned for Ci-C4-haloalkyl, 5-chloropentyl, 6-chlorohexyl and the like.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl,
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C2-C3-alkenyl"), 2 to 4 (“C 2 -C4-alkenyl"), 2 to 6 (“C 2 -C 6 -alkenyl”), 2 to 8 (“C 2 -C 8 -alkenyl”) or 2 to 10 (“C 2 -Cio-alkenyl”) carbon atoms and a double bond in any position, for example C 2 -C3-alkenyl, such as ethenyl,
  • haloalkenyl as used herein, which is also expressed as “alkenyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C 2 -C 4 -haloalkenyl"), 2 to 6 (“C 2 -C 6 -haloalkenyl"), 2 to 8 (“C 2 -C 6 -haloalkenyl”) or 2 to 10 (“C 2 -Cio-haloalkenyl”) carbon atoms and a double bond 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, for example chlorovinyl, chloroallyl and the like.
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C 3 -alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl”), 2 to 6 (“C 2 -C 6 -alkynyl”), 2 to 8 (“C2-C8-alkynyl”), or 2 to 10 (“C2-Cio-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C2-C3-alkynyl, such as ethynyl, 1 -propynyl or
  • haloalkynyl refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 ("C 2 -C 4 -haloalkynyl"), 3 to 4 ("C 3 -C 4 -haloalkynyl"), 2 to 6 (“C 2 -C 6 -haloalkynyl”), 2 to 8 ("C 2 -C 8 -
  • cycloalkyi refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl"), in particular 3 to 6 carbon atoms (“C3-C6-cycloalkyl”) or 3 to 5 carbon atoms (“Cs-Cs-cycloalkyl”) or 3 or 4 carbon atoms (“C3-C4-cycloalkyl”).
  • C3-C4-cycloalkyl, Cs-Cs-cycloalkyl and C3-C6- cycloalkyl are monocyclic. Examples for C3-C4-cycloalkyl are cyclopropyl and cyclobutyl.
  • Examples of monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.
  • 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.
  • bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • cycloalkyi denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyi which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 (“Cs-Cs-halocycloalkyl” ) or preferably 3 to 6 (“C3-C6- halocycloalkyl”) or 3 to 5 (“Cs-Cs-halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • cycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group ("Cs-Cs-cycloalkyl- Ci-C4-alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl”), more preferably a C3-C4-cycloalkyl group (“C3-C4-cycloalkyl-Ci-C4-alkyl”) as defined above (preferably a monocyclic cycloalkyi group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples for C3-C4-cycloalkyl-Ci- C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl, Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl,
  • C3-C8-cycloalkyl-Ci-C4-alkyl apart those mentioned for C3-C6-cycloalkyl-Ci-C4-alkyl, are cycloheptylmethyl, cycloheptylethyl, cyclooctylmethyl and the like.
  • C3-C8-cycloalkyl-Ci-C6-alkyl refers to a Cs-Cs-cycloalkyl group as defined above (preferably a monocyclic cycloalkyi group) which is bound to the remainder of the molecule via a Ci-C6-alkyl group, as defined above.
  • Examples for C3-Cs-cycloalkyl-Ci-C6-alkyl, apart those mentioned for C3-Cs-cycloalkyl-Ci-C4-alkyl, are cyclopropylpentyl, cyclopropylhexyl, cyclobutylpentyl, cyclobutylhexyl,
  • C3-C8-halocycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-alkoxy is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C3-Alkoxy is additionally, for example, n-propoxy and
  • Ci-C4-Alkoxy is additionally, for example, butoxy,
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -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.
  • Ci-C2-haloalkoxy is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-haloalkoxy is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-haloalkoxy is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-haloalkoxy is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-haloalkoxy is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Haloalkoxy is, for example, OCH2F, OCH F2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,
  • Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5,
  • Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy-Ci-C6-alkyl refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl,
  • Ci-C6-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are
  • Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms. Examples are
  • CH3OCF2 difluoromethoxy-methyl
  • Ci-C2-alkylthio is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-alkylthio is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-alkylthio is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-alkylthio is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-Cio-alkylthio is a Ci-Cio-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C3-Alkylthio is additionally, for example, n-propylthio or 1 -methylethylthio (isopropylthio).
  • Ci-C4-Alkylthio is additionally, for example, butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio,
  • Ci-Ce-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.
  • Ci-C2-haloalkylthio is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-haloalkylthio is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-haloalkylthio is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-haloalkylthio is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom.
  • C1-C10- haloalkylthio is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHC , SCCI 3 , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio,
  • C1-C3- Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2.2- difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,
  • Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio,
  • Ci-C 2 -alkylsulfinyl is a Ci-C 2 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl is a C1-C6- alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C10- alkylsulfinyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-Alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl
  • Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,
  • d-Cs-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
  • Ci-C 2 -haloalkylsulfinyl is a Ci-C 2 -haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-haloalkylsulfinyl is a C1-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.
  • Ci-Cio-haloalkylsulfinyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -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)CCI 3 , chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2.2- difluoroethylsulfinyl, 2,2,2-trifluoroethyl
  • Ci-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl,
  • Ci-C 2 -alkylsulfonyl is a Ci-C 2 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C3-alkylsulfonyl is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C4-alkylsulfonyl is a C1-C4- alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C1-C6- alkylsulfonyl is a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-Cio-alkylsulfonyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C 2 -Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.
  • Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or
  • Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl),
  • Ci-C6-Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl,
  • d-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfonyl is additionally, for example,
  • Ci-C2-haloalkylsulfonyl is a Ci-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C3-haloalkylsulfonyl is a C1-C3- haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-haloalkylsulfonyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • the term "Ci-C6-haloalkylsulfonyl” is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • C1-C10- haloalkylsulfonyl is a Ci-Cio-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 ,
  • dichlorofluoromethylsulfonyl chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,
  • Ci-C3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl,
  • Ci-C6-Haloalkylsulfonyl is additionally, for example,
  • Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.
  • Ci-C6-haloalkylcarbonyl a Ci-C6-haloalkylcarbonyl
  • Ci-C4-haloalkylcarbonyl Ci-C4-haloalkylcarbonyl
  • alkoxycarbonyl is a Ci-C6-alkoxy (“Ci-C6-alkoxycarbonyl”), preferably a
  • Ci-C6-haloalkoxycarbonyl Ci-C6-haloalkoxycarbonyl
  • Ci-C4-haloalkoxycarbonyl Ci-C4-haloalkoxycarbonyl
  • Examples are trifluoromethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl and the like.
  • Ci-C6-alkylamino is a group -N(H)Ci-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
  • di-(Ci-C6-alkyl)amino is a group -N(Ci-C6-alkyl)2. Examples are
  • Ci-C4-alkylaminocarbonyl is a group -C(0)N(H)Ci-C4-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,
  • di-(Ci-C4-alkyl)aminocarbonyl is a group -N(Ci-C4-alkyl)2. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl,
  • dipropylaminocarbonyl diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisopropylaminocarbonyl, ethylpropylaminocarbonyl,
  • heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 denotes a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. Partially unsaturated rings contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximum unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximum unsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and 8-membered rings cannot be aromatic. They are homoaromatic (7-membered ring, 3 double bonds) or have 4 double bonds (8-membered ring).
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, 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:
  • piperazin-1 -yl piperazin-2-yl, 1 ,3,5-hexahydrotriazin-1 -yl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1 -oxothiomorpholin-2-yl,
  • Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-d ihyd rofur-3-yl , 2,4-dihydrofur-2-yl, 2,4-d ihyd rofur-3-yl , 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,
  • tetrahydropyridinyl 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl,
  • Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl,
  • the "heterobicyclic rings” contain two rings which have at least one ring atom in common. At least one of the two rings contains a heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2 as ring member.
  • the term comprises condensed (fused) ring systems, in which the two rings have two
  • Examples for a 7-, 8-, 9- or 10-membered saturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 8-, 9- or 10-membered partially unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 8-, 9- or 10-membered maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • bridged 7-, 8-, 9- or 10-membered heterobicyclic rings containing 1 , 2 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, ring members are examples of bridged 7-, 8-, 9- or 10-membered heterobicyclic rings containing 1 , 2 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, ring members.
  • # denotes the attachment point to the remainder of the molecule.
  • the attachment point is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms (if the latter are not part of a double bond).
  • heterobicyclic rings formed by R 5 and R 6 together with the nitrogen atom they are bound to are the above heterobicyclic systems, which contain however at least one NH as a ring member and in which the attachment point # is on a nitrogen atom of such an NH group (where it replaces the hydrogen atom)
  • heteromonocyclic rings such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl, pyrrolidine-2,5-dionyl, piperidine-2- only, piperidine-2,6-dionyl and the like.
  • substituents R 16 ; or R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated
  • heterocyclic ring wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl and in particular from hydrogen and Ci-C4-alkyl;
  • each R 16 has one of the above general meanings, or, in particular, one of the below preferred meanings; and is preferably independently selected from the group consisting of halogen, cyano, nitro, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and
  • R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings; or
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 5- or 6- membered saturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, d-Ce-haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl.
  • the heterocyclic ring optionally carries one or
  • R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • each R 16 has one of the above general meanings, or, in particular, one of the below preferred meanings; and is preferably independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl and C2-C4-haloalkynyl; and
  • R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and in particular from hydrogen and Ci-C4-alkyl;
  • R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings; or R 10a and R 10b form together a group -(Chbjp-, where p is 4 or 5.
  • R 14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci
  • k 0, 1 , 2 or 3,
  • each R 16a is independently hydrogen or has one of the meanings given below for R 16 ;
  • each R 16 is independently selected from the group consisting of halogen
  • Ci-C4-alkyl Ci-C4-haloalkyl
  • Ci-C4-alkoxy Ci-C4-haloalkoxy
  • Ci-C4-alkylthio Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl
  • R 14a is selected from hydrogen and methyl and is specifically hydrogen
  • R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R 16 ;
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 14a is selected from hydrogen and Ci-C4-alkyl, preferably from hydrogen and methyl, and is specifically hydrogen;
  • R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl-, where the cycloalkyi moieties in the last-mentioned radical may carry a CN group; Ci-C4-alkyl substituted with a CN group, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl and in particular from hydrogen and Ci-C4-alkyl;
  • R 10b is selected from Ci-C4-alkyl and a 5- or 6-membered heteroaromatic ring
  • heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ; and preferably from Ci-C4-alkyl and a 6- membered heteroaromatic ring comprising 1 or 2, preferably 1 , nitrogen ring atoms.
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 10a and R 10b are preferably selected, independently of each other, from the group consisting of hydrogen, C1-C6- alkyl, d-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2-Ce-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl,
  • heterocyclic ring 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated
  • heterocyclic ring wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the above preferred meanings.
  • R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl, or, together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further hetero
  • R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl; and are specifically hydrogen or Ci-C6-alkyl.
  • a 1 is
  • R 9 , R 10a and R 10c have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 9 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, and preferably from Ci-C6-alkyl, C1-C6- haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and
  • R 10c is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a and R 10c Preferably, in the above radicals R 10a and R 10c ,
  • R 14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 14a is selected from hydrogen and methyl and is specifically hydrogen
  • R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R 16 ;
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • A is A 2 .
  • W 1 is preferably O.
  • M is preferably where R 9 and m have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • each R 9 is independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g.
  • R 13 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • each R 9 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , or
  • each R 16 is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • each R 9 is independently selected from Ci-C6-alkyl, or
  • each R 16 is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • each R 9 is independently selected from Ci-C6-alkyl, or
  • the two R 9 in the group form together a group -(Chb - where r is 4 or 5.
  • m is preferably 0 or 1 and is in particular 0.
  • R 9 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • each R 9 is independently selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g.
  • each R 9 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , or
  • each R 16 is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • each R 9 is independently selected from Ci-C6-alkyl, or
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • each R 9 is independently selected from Ci-C6-alkyl, or
  • R 10a is selected from hydrogen, Ci- C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, C1-C6- haloalkylcarbonyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where
  • M is where R 8 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • each R 8 is independently selected from d-Ce-alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 - haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and
  • cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R 13 ; phenyl, optionally substituted with 1 , 2, 3, 4 or 5, prefeably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 , wherein R 13 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings; or
  • each R 13 is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R 13 as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.
  • each R 16 is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 16 is bound to a nitrogen atom, it is preferably selected from Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and is specifically Ci-C4-alkyl.
  • each R 8 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , wherein each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-
  • each R 16 is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
  • R 8 in the group together with the carbon atom they are bound to , form a 5- or 6-membered saturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R 16 ; wherein R 16 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • the two radicals R 8 together with the carbon atom they are bound to, form a 5- or 6-membered saturated heterocyclic ring, where the heterocyclic ring comprises 1 or 2 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, preferably from N and S, as ring members, and where the heterocyclic ring is optionally substituted with one or more substituents R 16 ; wherein R 16 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • A is A 3 .
  • W 2 is preferably O.
  • R 9 is preferably selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4- alkyl-, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g.
  • each R 13 is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R 13 as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.
  • each R 16 is independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 9 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl and a 5-, 6- or 7-membered saturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g.
  • R 5 in A 3 is -SO2[N(R 10a )R 10b ].
  • phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated
  • heterocyclic ring wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, e.g.
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 14b is selected from hydrogen, d-C 6 -alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 14a is selected from hydrogen and methyl and is specifically hydrogen
  • R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R 16 ;
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 10a and R 10b in -SO2[N(R 10a )R 10b ] as a meaning for R 5 are
  • Ci-C6-alkyl independently of each other hydrogen or Ci-C6-alkyl and are in particular
  • R 9 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, e.g.
  • R 10a is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 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 optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ;
  • n, R 13 , R 14a , R 14b , R 15 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • each R 13 is independently preferably selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R 13 as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.
  • each R 15 is independently preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and is in particular Ci-C6-alkyl.
  • R 14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy
  • R 14a is selected from hydrogen and methyl and is specifically hydrogen
  • R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyi moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from S, SO and SO2 as ring member (ring E-44), where the heterocyclic ring is optionally substituted with one or more, preferably 1 or 2, in particular 1 , substituents R 16 ;
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 9 is d-Ce-alkyl
  • R 10a is -S(0) 2 R 15 , wherein R 15 is Ci-C 6 -alkyl.
  • each R 9 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl, C 2 -C6-alkenyl, C 2 -
  • radicals R 13 phenyl, optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ; and is preferably Ci-C6-alkyl; wherein each R 13 is independently selected from the group consisting of cyano, nitro, Ci-
  • R 13 as a substituent on a cycloalkyl moiety is additionally selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynyl; and each R 16 is independently selected from the group consisting of halogen,
  • R 6 is preferably selected from the group consisting of hydrogen, Ci-C 4 -alkyl, C 2 -C3-alkynyl, -CH 2 -CN and Ci-C6-alkoxy-methyl-, and preferably from hydrogen and Ci-C 4 -alkyl.
  • radicals R 8 , and phenyl which may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 11 ; wherein R 8 and R 11 have one of the above general or, in particular, one of the below preferred meanings.
  • Suitable heterobicyclic rings formed by N, R 5 and R 6 are for example the following:
  • heterobicyclic rings may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R 17 , wherein each R 17 has independently one of the above general, or in particular, one of the below preferred meanings.
  • k is 0, 1 , 2, 3, 4 or 5, preferably 0, 1 , 2 or 3, more preferably 1 or 2, in particular 0 or 1 ;
  • q 0, 1 or 2;
  • the attachment point of the radical(s) R 17 is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom (if the latter is not part of a double bond).
  • A is A 4 .
  • a 4 is selected from rings of formulae D-1 to D-184
  • k 0, 1 , 2 or 3;
  • q 0, 1 or 2;
  • R 11 has one of the above general meanings or, in particular, one of the below
  • R 11a is hydrogen or has one of the above general meanings or, in particular, one of the below preferred meanings given for R 11 , where however R 11a is not halogen;
  • a 4 is selected from D-59, D-63 and D-64 and is in particular D-59.
  • each R 11 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 11a is independently selected from hydrogen and Ci-C4-alkyl.
  • k is preferably 0 or 1 and specifically 0. specifically
  • A is A 5 .
  • R 10a and R 10b independently of each other, are selected from hydrogen and C1-C6- alkyl
  • R 8 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R 13 ;
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more, e.g. 1 , 2 or 3, in particular 1 , substituents R 16 ,
  • R 13 and R 16 have one of the above general meanings, or in particular, one of the below preferred meanings.
  • R 10a and R 10b are selected, independently of each other, from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g.
  • R 13 is selected from CN, Ci-C4-alkoxy, Ci-C4-alkylthio and phenyl. More preferabyl, R 10a and R 10b are selected, independently of each other, from hydrogen, d-Ce-alkyl, Ci-C 6 -haloalkyl, CH 2 CN, CH 2 -S-Ci-C 4 -alkyl, benzyl and phenyl.
  • R 10a and R 10b independently of each other, are selected from hydrogen and C1-C6- alkyl
  • R 8 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more, e.g.
  • R 13 and R 16 have one of the above general meanings, or in particular, one of the below preferred meanings.
  • each R 13 is independently selected from the group consisting of cyano, nitro, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl; where R 13 as a substituent on a cycloalkyl moiety is additionally selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkyn
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • B 1 and B 5 are CH and B 2 , B 3 and B 4 are CR 2 , where R 2 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • B 1 and B 5 are CH
  • B 2 is CR 2 , where R 2 is not hydrogen
  • B 3 and B 4 are CR 2 , where R 2 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 2 is selected from hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, C3-C 0 -cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, e.g.
  • R 2 is selected from hydrogen, halogen and Ci-C2-haloalkyl, preferably from hydrogen, F, CI, Br and CF3, in particular from hydrogen, CF3, F and CI, and specifically from hydrogen, CF3 and CI.
  • B 1 and B 5 are CH
  • B 2 is CR 2 , where R 2 is selected from CF3, F and CI, and specifically from CF3 and CI
  • B 3 and B 4 are CR 2 , where R 2 is selected from hydrogen, CF3, F and CI and specifically from hydrogen, CF3 and CI.
  • G 1 , G 4 and G 5 are C-R 4 ; and G 2 and G 3 are C-A or C-R 4 ; with the proviso that one of G 2 and G 3 is C-A.
  • G 1 , G 4 and G 5 are C-H; and G 2 and G 3 are C-A or C-R 4 ; with the proviso that one of G 2 and G 3 is C-A.
  • G 1 , G 4 and G 5 are C-H; and G 2 and G 3 are C-A or C-R 4 , where R 4 is different from hydrogen; with the proviso that one of G 2 and G 3 is C-A.
  • R 4 is different from hydrogen
  • G 3 is C-A in case that A is A 1 , A 2 , A 3 or A 4
  • G 2 is C-A in case that A is A 5 . This is especially preferred for the case that E and R 4 do not form a ring.
  • G 1 , G 4 and G 5 are CH; and in case that G 3 is C-A, G 2 is C-R 4 ; and in case that G 2 is C-A, G 3 is C-R 4 .
  • G 1 , G 4 and G 5 are CH; and in case that G 3 is C-A, G 2 is C-R 4 , where R 4 is different from hydrogen; and in case that G 2 is C-A, G 3 is C-R 4 , where R 4 is different from hydrogen. This is of course only possible for the case that E and R 4 do not form a ring.
  • R 4 is preferably selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C5-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkyl, Ci-C4-haloalkyl,, Ci-C6-alkoxy-Ci-C6-alkyl-, C1-C4- alkylthio and Ci-C4-haloalkylthio, more preferably from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, even more preferably from hydrogen, CI, methyl, CF3 and methoxy, specifically from hydrogen, CI,
  • R 4 is different from hydrogen, it is preferably selected from halogen, cyano, C1-C4- alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkyl, Ci-C4-haloalkyl,, C1-C6- alkoxy-Ci-C6-alkyl-, Ci-C4-alkylthio and Ci-C4-haloalkylthio, and more preferably from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy. If R 4 is different from hydrogen, it is specifically CI, methyl, CF3 or methoxy
  • R 1 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl C3-C6-halocycloalkyl or C1-C4- alkoxycarbonyl, more preferably, from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C4-alkoxycarbonyl, even more preferably from Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxycarbonyl, and particularly preferably from C1-C4- haloalkyl and Ci-C4-alkoxycarbonyl.
  • R 1 is Ci-C4-haloalkyl, specifically Ci-C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluoromethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.
  • L is selected from hydrogen and Ci-C4-alkyl, and is more preferably hydrogen.
  • E is selected from hydrogen, halogen and Ci-C4-alkyl, and is more preferably hydrogen.
  • X is selected from hydrogen, halogen and Ci-C4-alkyl, and is more preferably hydrogen.
  • R 3 is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, -CH2-CIM and Ci-C6-alkoxy-methyl-, more preferably from hydrogen and Ci-C4-alkyl and is specifically hydrogen.
  • Z is preferably O.
  • R 8 , R 9 , R 10a , R 10b , R 10c , R 11 , R 12 , R 13 , R 14 , R 14a , R 14b , R 15 and R 16 have following preferred meanings:
  • R 16 1 , 2 or 3, in particular 1 , radicals R 16 ; where R 9 , R 10a , R 10b and R 16 have one of the meanings given above or in particular one of the preferred meanings given below. In particular it is selected from the group consisting of cyano, C3-C6-cycloalkyl, C3-C6- halocycloalkyl,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g.
  • R 8 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy.
  • R 8 as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.
  • R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 , -SR 9 , -N(R 10a )R 10 , phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially uns
  • R 8 is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, -N(R 10a )R 10 , phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.
  • each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 ; and a 3-,
  • heterocyclic ring 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , radicals R 16 , where R 16 has one of the meanings given above or in particular one of the preferred meanings given below.
  • each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 16 ; and a 5- or 6-membered
  • heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring may be substituted by one or more, e.g. 1 , 2 or 3, in particular 1 , radicals R 16 ; where R 16 has one of the meanings given above or in particular one of the preferred meanings given below.
  • R 10a and R 10b are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, C3-C6-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or hetero
  • R 10a and R 10b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may 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 carry 1 or 2, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
  • R 10a and R 10b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N , O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, e.g.
  • R 10c is preferably selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, C1-C4- haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C3-C6- halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3
  • R 10a and R 10c together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may 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 carry 1 or 2, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C 4 -haloalkylthio.
  • R 10c is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, e.g.
  • Each R 11 and each R 16 are independently of each occurrence and independently of each other preferably selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4- haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • Each R 12 is preferably selected from Ci-C4-alkyl and is in particular methyl.
  • R 13 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, -SH, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 13 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, -OH, -SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3, in particular 1 , radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-
  • R 13 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy.
  • R 13 as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.
  • R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3, in particular 1 , radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 14 , R 14a and R 14b are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or, R 14a and R 14b , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further
  • R 14 , R 14a and R 14b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may 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 carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • Each R 15 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • Each R 16 is preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • the invention relates to a compound of formula I.A or I.B
  • a a is A 1 , A 2 , A 3 or A 4 ;
  • R 2a , R 2b and R 2c independently of each other, have one of the general, or in particular, one of the preferred meanings given above for R 2 ;
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and A 5 have one of the general, or in particular, one of the
  • a a is A 1 , A 2 , A 3 or A 4 ;
  • R 2a , R 2b and R 2c independently of each other, have one of the general, or in particular, one of the preferred meanings given above for R 2 ;
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and A 5 have one of the general, or in particular, one of the
  • R N is selected from the group of Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkoxy, and is in particular Ci-C6-alkyl.
  • Examples of preferred compounds are compounds of the following formulae 1.1 to 1.42 and their tautomers (especially of compounds 1.30 to 1.32), where R 2a , R 2b and R 2c have one of the general or one of the preferred meanings given above for R 2 , R 9a and R 9b have one of the general or one of the preferred meanings given above for R 9 (except for compound 1.10, where R 9a and R 9b have one of the general or one of the preferred meanings given above for R 8 ) and the other variables have one of the general or preferred meanings given above.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 1616 below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • Tables 51 to 75 Compounds of the formula 1.3 in which R 14b is as defined in any of tables 1 to 25 and the combination of R 2a , R 2b , R 2c and R 4 for a compound corresponds in each case to one row of Table A

Abstract

La présente invention porte sur des composés d'acrylamide (I) qui sont utiles pour combattre ou lutter contre des animaux nuisibles invertébrés, en particulier des animaux nuisibles arthropodes et des nématodes, et sur un procédé pour leur production. L'invention porte également sur un procédé pour la lutte contre des animaux nuisibles invertébrés utilisant ces composés et sur un matériel de propagation de plante, une composition agricole et une composition vétérinaire comprenant lesdits composés.
PCT/EP2013/059547 2012-05-09 2013-05-08 Composés d'acrylamide pour la lutte contre des animaux nuisibles invertébrés WO2013167633A1 (fr)

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