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WO2017016883A1 - Procédé de préparation de composés cyclopentène - Google Patents

Procédé de préparation de composés cyclopentène Download PDF

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Publication number
WO2017016883A1
WO2017016883A1 PCT/EP2016/066734 EP2016066734W WO2017016883A1 WO 2017016883 A1 WO2017016883 A1 WO 2017016883A1 EP 2016066734 W EP2016066734 W EP 2016066734W WO 2017016883 A1 WO2017016883 A1 WO 2017016883A1
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Prior art keywords
partially
alkyl
unsubstituted
ring
same
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Inventor
Karsten Koerber
Gopal Krishna DATTA
Pascal Bindschaedler
Wolfgang Von Deyn
Franz-Josef Braun
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BASF SE
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BASF SE
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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/02—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
    • A01N43/20—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 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
    • A01N43/34—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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/80—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 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/04—Four-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Definitions

  • the present invention relates to a process for preparing cyclopentene compounds of formula I
  • A is a group A 1 , A 2 or A 3 ;
  • a 1 is:
  • W is O, or S
  • Y is H, N(R 5 )R 6 , or OR 9
  • a 3 is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated
  • heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, or
  • B 1 , B 2 and B 3 are each independently selected from N and CR 2 , with the proviso that at most two of B 1 , B 2 , and B 3 are N;
  • G 1 , G 2 , G 3 and G 4 are each independently selected from N and CR 4 , with the proviso that at most two of G 1 , G 2 , G 3 , and G 4 are N;
  • R 1 is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl-, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C 3 -
  • each R 2 is independently H, halogen, CN, N 3 , N0 2 , SCN, SF 5 , CrC 6 -alkyl, C 3 -C 8 -cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R 8 ,
  • phenyl which may be partially or fully substituted by R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R 11 , preferably the unsubstituted or substituted HET;
  • R 3a , R 3b , R 3c are each independently H, halogen, OH, C0 2 R 3d , Ci-C 3 -alkyl, Ci-C 3 -haloalkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkylthio, C1-C3- haloalkylthio, Ci-C3-alkylsulfonyl and Ci-C3-haloalkylsulfonyl;
  • R 3d is H, Ci-Ce-alkyl, or Ci-C 3 -alkyloxy-Ci-C 3 -alkyl;
  • each R 3e is independently H, halogen, CH3, or CF3;
  • each R 4 is independently selected from the meanings mentioned for R 2 ,
  • R 4 bonded to adjacent carbon atoms may form a five- or sixmembered saturated
  • each R 5 is independently H, CN, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl,
  • each R 6 is independently selected from the meanings mentioned for R 2 ;
  • R 7a , R 7b are each independently H, halogen, CN, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R 8 ;
  • R 7a and R 4 in position G 3 may together form a -ChbCI-b-chain
  • each R 8 is independently CN, N 3 , NO2, SCN, SF 5 , Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains may be substituted by one or more radicals R 13 ;
  • phenyl which is unsubstituted or partially or fully substituted by same or different R 16 , or a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by same or different R 16 , or
  • R 8 together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R 16 ; and
  • R 8 as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 13 ; and
  • each R 9 is independently H, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 13 , or
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 16 ;
  • R 9 in the groups S(0) n R 9 and OS0 2 R 9 may additionally be d-C 6 -alkoxy, or C C 6 - haloalkoxy;
  • R 10a , R 10 are independently from one another H, Ci-C 6 -alkyl, Ci-Ce-haloalkyI, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 13 ;
  • phenyl which is unsubstituted, or partially or fully substituted by same or different R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 16 , preferably unsubstituted or substituted HET; 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 or fully unsaturated heterocyclic ring, which ring may additionally contain one or two heteroatoms N, O, and/or S as ring members, which ring is is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, phenyl which may be partially or fully substituted by R 16
  • R 11 is halogen, CN, N 3 , N0 2 , SCN, SF 5 , Ci-Cio-alkyl, C 3 -C 8 -cycloalkyl, C 2 -Cio-alkenyl, C2-C10- alkynyl, which groups are unsubstituted, partially or fully halogenated, and/or may be substituted by same or different R 8 , or
  • phenyl which is unsubstituted, or partially or fully substituted by same or different R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated aromatic
  • heterocyclic ring comprising 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 16 ; or two R 11 present on the same ring carbon atom of an unsaturated or partially unsaturated
  • each R 12 is independently Ci-C4-alkyl and phenyl, which is unsubstituted, or partially or fully substituted by same or different Ci-C4-alkyl;
  • Cs-Cs-cycloalkyl which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 same or different Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and/or oxo; phenyl, benzyl, phenoxy, where the phenyl moiety may be substituted by one or more same or different R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2, or 3 heteroatoms N, O, and/or S, as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 16 ; or
  • each R 14 is independently H , CN , Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, SO n -Ci-C 6 -alkyl, SO n -Ci- Ce-haloalkyl, Si(R 2 ) 3 ;
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 CN , Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO n -Ci-C4- alkyl, C3-C6-cycloalkyl which is unsubstituted or substituted by 1 or 2 substituents halogen and CN ;
  • Cs-Cs-cycloalkyI which is unsubstituted, or partially or fully halogenated or substituted by 1 or 2 CN
  • 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, or fully unsaturated heterocyclic ring, wherein the ring may additionally contain 1 or 2 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy; or
  • heteroatoms N , O, and/or S as ring members which ring is unsubstituted, or partially or fully substituted by same or different halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy, or C1-C4- haloalkoxy;
  • each R 15 is independently H , CN , Si(R 12 ) 3
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals C3-C4-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, SO n -Ci-C6-alkyl, or oxo;
  • Ci-C4-alkyl which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 radicals Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, SO n -Ci-C6-alkyl, or oxo; phenyl, benzyl, pyridyl, and phenoxy, which rings are unsubstituted, partially or fully halogenated, or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl;
  • each R 16 is independently halogen, NO2, CN, OH, SH, d-Ce-alkoxy, Ci-Ce-haloalkoxy, SO n - Ci-C6-alkyl, SO n -Ci-C6-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, C1-C4- alkoxycarbonyl, Ci-C4-haloalkoxycarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, di- (Ci-C4-alkyl)-aminocarbonyl, Si(R 12 )3;
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated, or substituted by 1 or 2 radicals CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, or oxo;
  • Cs-Cs-cycloalkyI which is unsubstituted, partially or fully halogenated or substituted by 1 or 2 radicals CN, Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, or oxo;
  • Ci-C6-alkyl Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, or (Ci-C6-alkoxy)carbonyl; or
  • 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 or fully unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy;
  • each n is independently 0, 1 , or 2;
  • each m is independently 0, or 1 ; by cyclisation under basic conditions of a ketone of formula II
  • Q 1 is independently selected from Ci-C4-alkyl or phenyl
  • Q 2 is independently selected from Ci-C4-alkyl, Ci-C4-alkoxy, phenyl, halophenyl, phenoxy, or halophenoxy;
  • M is a metal selected from Li, Mg, Zn, or Cu or a combination of one or two or three or four of the aforementioned metals, and
  • X is halogen
  • the invention relates to novel compounds of formula I, which correspond to formulae IA, IB, IC, ID, and IE, resp., as defined below, as well as methods for controlling invertebrate pests, in particular arthropod pests and nematodes, by using these compounds and to plant propagation material and to agricultural and a veterinary compositions comprising said compounds.
  • Cyclopentene compounds of formula I are obtained by cyclisation of an intermediate of formula II.
  • Compounds of formula II are novel.
  • Z is is SiQ 1 3 wherein Q 1 is independently selected from Ci-C4-alkyl or phenyl; or
  • Q 2 is independently selected from Ci-C4-alkyl, Ci-C4-alkoxy, phenyl, halophenyl, phenoxy, or halophenoxy,
  • Q 1 is C1-C4 alkyl
  • Q 2 is independently selected from C1-C4 alkyl, more preferably Q 1 is independently selected from methyl, ethyl or propyl and Q 2 is independently selected from methyl, ethyl or propyl.
  • This transformation is usually carried out at temperatures of from -78°C to +150°C, preferably from -78°C to +80°C, in an inert solvent, in the presence of a base or an acid, preferably a base [cf. Ager, D. J., Science of Synthesis, 47a, 85-104; 2010; or Ager, D. J., Science of Synthesis, 4 (2001 ), p.789].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, 0-, m-, and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.-butylmethyl ether, dimethoxy ethylene, 1 ,4-dioxane, anisole, 2-methyl-tetrahydrofuran (2-CH 3 -THF) and tetrahydrofuran (THF), preferably ethers such as diethyl ether, THF or 2-CH3-THF. It is also possible to use mixtures of the solvents mentioned.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether
  • aromatic hydrocarbons such as toluene, 0-, m-, and p-xylene
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as LiOH, NaOH, KOH and Ca(OH)2, alkali metal and alkaline earth metal oxides, such as U2O, Na20, CaO, and MgO, alkali metal and alkaline earth metal hydrides, such as LiH, NaH, KH and CaH 2 , alkali metal and alkaline earth metal carbonates, such as U2CO3, K2CO3 and CaCC>3, and also alkali metal bicarbonates, such as NaHCC>3, alkali metal alcoholates, such as NaOCH3, NaOC2Hs, Na-tert.-butylate, K-tert.-butylate, moreover organic bases, for example tertiary amines, such as N(CH3)3, N(C2H5)3, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine,
  • organometallic bases alkali metal alcoholates and alkali metal hydrides. Particular preference is given to bases selected from K2CO3, Na 2 C0 3 , Cs 2 C0 3 , DBU, DABCO, sodium bis(trimethylsilyl)amide
  • NaHMDS lithium bis(trimethylsilyl)amide
  • LiHMDS lithium bis(trimethylsilyl)amide
  • K-tert-butoxide Na-tert-butoxide
  • Li- diisopropylamide NaH, KH, NaOCH 3 , NaOC2H 5 , NaOH, and KOH.
  • the bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.
  • the lewis acid is used in 0.0001 to 2 preferably 0.001 to 1 , particularly 0.01 to 0.95 mol-% of compound II.
  • Suitable acids and acidic catalysts are in general anorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulphuric acid und perchloric acid, Lewis acids, such as boron tri fluoride, aluminium tri chloride, iron III chloride, tin IV chloride, titanium IV chloride and zinc II chloride, moreover organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluene sulphonic acid, benzene sulphonic acid, camphor sulphonic acid, citric acid, and trifluoro acetic acid.
  • the acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.
  • M is a metal selected from Li, Mg, Zn, or Cu or a combination of one or two or three or four of the aforementioned metals, preferably Mg, Zn or Cu, and X is a nucleophilic leaving group, such as halogen, preferably CI, Br or I;
  • transformation is usually carried out at temperatures of from -78°C to +100°C, preferably from - 50°C to +50°C, in an inert solvent, optionally in the presence of a catalyst [cf. Knochel et al., J. Org. Chem., 1988, 53 (10), pp 2390- 2392].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, ethers such as diethyl ether, diisopropyl ether, tert.-butylmethyl ether, dimethoxy ethylene, 1 ,4-dioxane, anisole, 2-methyl tetrahydrofuran and tetrahydrofuran, preferably ethers such as diethyl ether, THF or 2-CH3-THF, nitrils such as acetonitrile, and propionitrile. It is also possible to use mixtures of the solvents mentioned.
  • Suitable acids and acidic catalysts are in general anorganic acids such as HF, HCI, HBr, H2SO4 and HCIO4, Lewis acids, such as BF 3 , AICI 3 , FeCI 3 , ZnCI 4 , TiCI 4 and ZnC , SiCI(CH 3 ) 3 , CI3S1H, SiCI 4 , BF3OC2H5, SiF 4 , (C2H 5 )3SiNTf 2 , (CH 3 ) 3 SiCI04, TiCI 4 , or SnCI 4 , moreover organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluene sulphonic acid, benzene sulphonic acid, camphor sulphonic acid, citric acid, and trifluoro acetic acid.
  • Lewis acids such as BF 3 , AICI 3 , FeCI 3 , ZnCI 4 , TiCI 4 and ZnC , SiCI(CH 3
  • Lewis acid organocatalysts Topics in current chemistry, Sereda Oksana; Tabassum Sobia; Wilhelm Rene Vol. 291 , p. 349-93 (2010); Schinzer D Selectivities in Lewis acid promoted reactions, Kluwer Academic, 1989, Dordrecht); preferably the lewis acid is selected from SiCI(CH3)3, C SiH, SiCI 4 , and BF 3 *OC 2 H 5 .
  • the catalyst is preferably used in an amount of 0.01 mol-% to 50 mol-% of compound III.
  • the acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of IV, based on III.
  • the compounds of formula III are preferably obtained by condensation of a ketone of formula V with an acetyl compound of formula VI
  • This transformation is usually carried out at temperatures of from 0°C to +150°C, preferably from 20°C to +120°C, in an inert solvent, in the presence of a base [cf. WO 2013092943]
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as CH2CI2, CHCI3, dichloroethane (DCE), and chlorobenzene, ethers such as diethyl ether, diisopropylether, tert.-butylmethyl ether, 1 ,4-dioxane, anisole, and THF, nitrils such as acetonitrile, and propionitrile, alcohols such as methanol (MeOH), ethanol, n-propanol, isopropanol, n-butanol, and tert.-butanol, preferably aliphatic hydrocarbons or halogenated hydrocarbons such as DCE. It is also possible to use mixtures of the solvents mentioned
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as LiOH, NaOH , KOH and Ca(OH)2, alkali metal and alkaline earth metal oxides, such as U2O, Na20, CaO, and MgO, alkali metal and alkaline earth metal hydrides, such as LiH, NaH, KH and Cahb, alkali metal and alkaline earth metal carbonates, such as L12CO3, K2CO3 and CaCC>3, and also alkali metal bicarbonates, such as NaHCC>3, moreover organic bases, for example tertiary amines, such as N(CH3)3, N(C2H5)3,
  • alkali metal and alkaline earth metal hydroxides such as LiOH, NaOH , KOH and Ca(OH)2
  • alkali metal and alkaline earth metal oxides such as U2O, Na20, CaO, and MgO
  • triisopropylethylamine and N-methylpiperidine pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.
  • alkali metal and alkaline earth metal carbonates and organic bases especially sodium or potassium carbonate and triethylamine.
  • the bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent. It is also possible to use mixtures of the bases mentioned.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products.
  • Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.
  • a further embodiment of the invention relates to a process for preparation of compounds of formula I , which correspond to the following formula:
  • R 1 is Ci-C4-haloalkyl or COOR 15 , preferably halomethyl, particularly CF 3 ;
  • R2a R2b are independently H, CI, or F, preferably R 2a is H, and R 2b is F; R 3 is H;
  • R 4A is halogen, CN, or Ci-C 4 -alkyl, preferably F, CI, or CH 3 ;
  • R 5a is H or Ci-C 2 -alkyl, preferably H or CH 3 ;
  • R 6 is H, halogen, CN, N 3 , N0 2 , SCN, SF 5 , Ci-C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R 8 ,
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 11 , preferably the unsubstituted or substituted heterocyclic ring;
  • each R 8 is independently CN, N 3 , N0 2 , SCN, SF 5 , C 3 -C8-cycloalkyl, C 3 -C8-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R 13 ;
  • phenyl which is unsubstituted, or partially or fully substituted by same or different R 16 ; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R 16 , preferably the unsubstituted heterocyclic ring, or
  • R 8 together with the carbon atoms of the 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, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or substituted by one or more same or different R 16 ; and
  • R 8 as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6- alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, and C 2 -C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R 13 ; and
  • R 15 is H or Ci-C 4 -alkyl.
  • A' is A or a precursor of A.
  • Typical precursors of A are a halogen atom, CN, carboxy, CC>2-R z1 , such as tert-butoxycarbonyl (carboxy and C(0)OR z1 are of course only "precursors" if in the desired compound I W is S and/or R z1 is not the desired radical R 9 and/or if Y is to be -NR 5 R 6 ), an acetale group, a protected aldehyde group or -OS02-R z1 , where R z1 is Ci- C4-alkyl, Ci-C4-haloalkyl or phenyl which may be substituted by 1 , 2 or 3 groups Ci-C4-alkyl, Ci- C4-haloalkyl Ci-C4-alkoxy, or Ci-C4-haloalkoxy.
  • Compounds V is Ci- C4-alkyl, Ci- C4-haloalkyl
  • Dehydration either occurs spontaneously or with the help of dehydrating agents, such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POCI3, Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI, or sulfuric acid.
  • dehydrating agents such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POCI3, Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI, or sulfuric acid.
  • the water formed may alternatively be removed, e.g. by azeotropic distillation, e.g. with benzene/toluene as entrainer, e
  • the cyclopentanone 2 can be prepared by decarboxylation of the carboxylic acid 8, e.g. under heat, as shown below.
  • This acid can in turn be prepared by hydrolysis of the ester 7, where R' is a Ci-C4-alkyl group.
  • Hydrolysis can be carried out under acidic or, preferably, basic conditions.
  • Suitable bases are for example inorganic bases such as alkali metal hydroxides, e.g. LiOH, NaOH or KOH, or carbonates, such as Na2CC>3 or K2CO3.
  • hydrolysis and decarboxylation can be carried out in a single step reaction using sulfuric acid, and water.
  • the ester 7 can be prepared as shown below by a Claisen (Dieckmann) condensation of the diester 9.
  • R and R' are Ci-C4-alkyl groups.
  • the condensation reaction is carried out in the presence of a strong base, such as NaOCH 3 , NaOC 2 H 5 , KO'butyl, NaNH 2 , NaH, or LDA.
  • the diester 9 can in turn be prepared in an addition of 11 to the acrylate 10, as shown below.
  • X is MgZ, ZnZ or Li, where Z is CI, Br, or I.
  • the addition reaction is generally carried out under condition suitable for Grignard reactions, especially under anhydrous conditions.
  • Compounds I, wherein A is a group A 1 , in which W is O can be prepared by reacting a compound 1 ' wherein A' is CI, Br, I, or triflate with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C4-alkyl or R 9 , to a compound of formula 18.
  • Suitable palladium catalysts are for example those described in WO 201 1/161 130.
  • This ester is then hydrolyzed to the respective carboxylic acid, which is the reacted under standard amidation conditions with an amine NHR 5 R 6 .
  • Hydrolyzation can be carried out under standard conditions, e.g. under acidic conditions using for example hydrochloric acid, sulfuric acid or trifluoroacetic acid, or under basic conditions using for example an alkali metal hydroxide, such as LiOH, NaOH, or KOH.
  • Amidation is preferably carried out by activation of the carboxylic acids with oxalylchloride [(COCI)2] or thionylchloride (SOCI2) to the respective acid chlorides, followed by reaction with an amine NHR 5 R 6 .
  • amidation is carried out in the presence of a coupling reagent.
  • Suitable coupling reagent are well known and are for instance selected from carbodiimides, such as DCC (dicyclohexylcarbodiimide) and DIC (diisopropylcarbodiimide), benzotriazol derivatives, such as HATU (0-(7-azabenzotriazol-1 -yl)- ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethyluronium hexafluorophosphate), HBTU ((0-benzotriazol-1-yl)-N,N,N',N'- tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 -[bis(dimethyl- amino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1 -yloxy)
  • BOP
  • Compounds 1.1 wherein A is a group A 1 , wherein W is S, can be prepared by reacting the corresponding oxo-compound (W is O) with Lawesson's reagent (CAS 19172-47-5), see for example Jesberger et al., Synthesis, 2003, 1929-1958 and references therein. Solvents such as HMPA or THF at an elevated temperature such as 60°C to 100°C can be used. Preferred reaction conditions are THF at 65°C.
  • Compounds I wherein A is a group A 2 , wherein R 7a and R 7b are hydrogen, can be prepared by reducing a compound 18 or 19 for example with LAH (lithium aluminium hydride) or DIBAL-H (diisobutyl aluminium hydride) to a compound 20.
  • LAH lithium aluminium hydride
  • DIBAL-H diisobutyl aluminium hydride
  • the OH group can first be converted into a better leaving group, e.g. into a sulfonate (for example mesylate, tosylate or a triflate group).
  • R 6 is a group -C(0)R 8
  • Compounds 1.1 wherein A is a group A 2 , wherein R 7a is optionally substituted alkyl or optionally substituted cycloalkyl and R 7b is hydrogen, can be prepared by subjecting a ketone 22 (see below scheme 10), where R 7a is optionally substituted Ci-C6-alkyl or optionally substituted C3- Ce-cycloalkyl, to a reductive amination to furnish compounds 21 .
  • Typical conditions for the reductive amination are: Reacting ketone 16 with an amine H2NR 5 to yield the corresponding imine which is reduced to amine 21 with a reducing agent reagent such as NaBH 3 CN.
  • the reaction from ketone 22 to amine 21 may also be carried out as a one pot procedure.
  • the ketone 22 is prepared from the carbonyl compound 19 which is reacted with a Grignard reagent R 7a -MgHal, where Hal is CI, Br or I, or an organolithium compound R 7a -Li to obtain an alcohol of formula 23, which is then oxidized to a carbonyl compound of formula 22, as shown below.
  • R 7a and R 7b are optionally substituted alkyl, optionally substituted cycloalkyi, optionally substituted alkenyl or optionally substituted alkynyl, carbonyl compounds such as 22, where R 7a is optionally substituted Ci-C6-alkyl, optionally substituted C3-C8-cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, is reacted with a Grignard reagent R 7b -MgHal, where Hal is CI, Br or I, or an organolithium compound R 7b -Li, where R 7b is optionally substituted Ci-C6-alkyl, optionally substituted C3-C8- cycloalkyl, optionally substituted C2-C6-alkenyl or optionally substituted C2-C6-alkynyl, to obtain an alcohol of formula 24.
  • Alcohol 24 can then be converted into amine 25 via the corresponding azide, as described, for example, in Organic Letters, 2001 , 3(20), 3145-3148.
  • This imine is then reacted with a compound H-R 7a in an addition reaction under conditions as described for example in J. Am. Chem. Soc. 2009, 3850-3851 and the references cited therein, or, for introducing CN as a group R 7a , Chemistry - A European Journal 2009, 15, 1 1642-1 1659.
  • Compounds 1.1 wherein A is a group A 2 , wherein both R 7a and R 7b are optionally substituted alkyl, alkenyl, alkynyl, cycloalkyi or CN, can be prepared analogously by converting a ketone 22, wherein R 7a is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyi or CN, into an imine by reaction with an amine derivative NH2R 6 , wherein R 6 is tert-butyl sulfinyl, for preparing an imine compound 27.
  • This imine is then reacted with a compound H-R 7b in an addition reaction under conditions as described for example in J. Org. Chem 2002, 67, 7819-7832 and the references cited therein, or, for introducing CN as a group R 7a , Chemistry - A European Journal 2009, 15, 1 1642-1 1659. If desired, R 6 can then be removed to yield an amino group Nh .
  • Compounds 19 can be prepared by reaction of a compound 1.1 ', in which A' is CI, Br, I or - OS02-R z1 , where R z1 is as defined above, with carbon monoxide and a hydride source, such as triethylsilane, in the presence of a transition metal complex catalyst, preferably a palladium catalyst, to the aldehyde 19.
  • a transition metal complex catalyst preferably a palladium catalyst
  • Compounds 1.1 wherein A is A 3 can be prepared by standard ring coupling reactions.
  • compounds, wherein A 3 is an N-bound heterocyclic ring can be prepared by reacting a compound 1.1 ' wherein A' is CI, Br or I with the respective ring A 3 -H (H being on the nitrogen ring atom to be coupled) under Ullmann coupling conditions, such as described, for example, in WO 2007/075459.
  • copper(l) iodide or copper(l) oxide and a ligand such as 1 ,2-cyclohexyl- diamine is used, see for example Kanemasa et al., European Journal of Organic Chemistry, 2004, 695-709.
  • reaction is typically run in a polar aprotic solvent such as N,N-di- methylformamide, ⁇ , ⁇ -dimethylacetamide or N-methylpyrrolidone, and in the presence of an inorganic base such as sodium, potassium or cesium carbonate.
  • a polar aprotic solvent such as N,N-di- methylformamide, ⁇ , ⁇ -dimethylacetamide or N-methylpyrrolidone
  • a 3 is a C-bound heterocyclic ring
  • a typical catalyst is tetra- kis(triphenylphosphine)palladium(0).
  • Solvents such as tetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable.
  • the boronic acids A 3 -B(OH)2 are either commercially available or can be prepared by known methods. Other methods for introduction of the heterocyclic groups A 3 are the Heck, Stille, Kumada and Buchwald-Hartwig coupling procedures; see for example Tetrahedron, 2004, 60, 8991-9016.
  • the compounds of formula I including their stereoisomers, salts, and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula (I) can advantageously be prepared from other compounds of formula (I) by derivati- zation, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • derivati- zation e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by
  • a further embodiment of the invention relates to a process for preparation of compounds of formula I, which correspond to the following formula:
  • R 1 is CrC 4 -haloalkyl or COOR 15 , preferably halomethyl, particularly CF 3 ;
  • R 3 is H
  • R 6 is H, halogen, CN, N 3 , N0 2 , SCN, SF 5 , Ci-C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R 8 ,
  • phenyl which is unsubstituted, or substituted by one or more same or different R 11 ; or 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R 11 , preferably the unsubstituted or substituted heterocyclic ring;
  • each R 8 is independently CN, N 3 , NO2, SCN, SF 5 , C 3 -C8-cycloalkyl, C 3 -C8-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R 13 ;
  • phenyl which is unsubstituted, or substituted by one or more same or different R 16 ; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and S as ring members, which ring is
  • R 16 unsubstituted, or substituted by one or more same or different R 16 , preferably the unsubstituted or substituted heterocyclic ring, or
  • R 8 together with the carbon atoms of the 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, which heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms N, O, and/or S as ring members, and which ring is unsubstituted, or substituted by one or more same or different R 16 ; and R 8 as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R 13 ; and
  • R 8 in the groups C( 0)R 8 and may additionally be H, halogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different R 13 ,
  • R 8 is independently CN, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or substituted by one or more same or different R 13 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2, or 3 heteroatoms N, O, and S as ring members, which ring is
  • a further embodiment of the invention relates to a process for preparation of compounds of formula I, which correspond to the following formula:
  • R 1 is Ci-C4-haloalkyl, preferably halomethyl, particularly CF3;
  • R 2a , R 2b are independently H, CI, or F, preferably R 2a is H, and R 2b is F;
  • R 3 is H
  • R 4A is halogen, CN, or Ci-C 4 -alkyl, preferably CN;
  • a 3 is is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated
  • heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring may be substituted by one or more same or different R 11 , preferably A 3 is 1 -pyrazole, 2-oxazole, 2-thiazole or 1 ,2,4-triazole which rings are unsubstituted, or substituted by 0,1 or 2 R 11 ,
  • R 11 has one of the meanings given for R 11 above and is preferably halogen, CN, NO2, SCN, SF5, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated.
  • Such compounds correspond to formula IC.
  • Compounds of formula IC are obtainable by the process outlined in the outset using the accordingly designed precursors of formulae II, IV, V, and VI, resp., being I IC, IVC, VC, and VIC, resp., wherein the variables have the meanings as outlined for formula IC, and Z and MX are as defined in the outset.
  • R 1 is Ci-C4-haloalkyl, preferably halomethyl, particularly CF 3 ;
  • R 2a , R 2b are independently H, CI, or F, preferably R 2a is CI, and R 2b is F;
  • R 3 is H
  • R 9 is H, CN, d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl-, C 3 - Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or substituted by one or more same or different SO n -Ci-
  • phenyl which is unsubstituted, or substituted by one or more same or different R 16 ; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R 16 , preferably
  • R 1 is Ci-C 4 -haloalkyl or COOR 15 ;
  • R 2a , R 2b are independently H , CI , or F, preferably R 2a is H , and R 2b is F;
  • R 3 is H ;
  • R 4A is halogen, CN , or Ci-C 4 -alkyl, preferably CI, or CH 3 ;
  • R 6 is H , halogen, CN , N 3 , N0 2 , SCN , SF 5 , Ci-C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R 8 ,
  • R 6 is phenyl which may be partially or fully substituted by R 1 1 ; or
  • heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms N , O, and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 1 1 ;
  • R 7a is H , halogen, CN , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R 8 ;
  • each R 8 is independently CN , N 3 , NO2, SCN , SF 5 , Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, wherein the carbon chains are unsubstituted, or partially or fully substituted by same or different R 13 ;
  • R 8 as a substituent on a cycloalkyl ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 13 ; and
  • R 15 is H or Ci-C 4 -alkyl.
  • halogen denotes in each case fluorine, bromine, chlorine, or iodine, in particular fluorine, chlorine, or bromine.
  • 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-C 2 -alkyl"), 1 to 3 (“C C 3 -alkyl”),1 to 4 (“C C 4 - alkyl”), or 1 to 6 (“Ci-C 6 -alkyl").
  • Ci-C 4 -Alkyl is methyl, ethyl, propyl, isopropyl, butyl, 1 - methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl).
  • haloalkyl refers to straight-chain or branched alkyl groups having 1 to 4 (“Ci-C 4 -haloalkyl”), carbon atoms (as mentioned above), wherein 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, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl,
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C2-C3-alkenyl”), 2 to 4 (“C2-C4-alkenyl”), carbon atoms and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl or 1 -methylethenyl; C2-C4-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1 - methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1-propenyl, 1- methyl-2-propenyl or 2-methyl-2-propenyl.
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C2-C3-alkynyl”), 2 to 4 (“C2-C4-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C2-C4-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like.
  • cycloalkyl refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl”), in particular 3 to 6 (“C3-C6-cycloalkyl”) or 3 to 5 (“Cs-Cs-cycloalkyl”) carbon atoms.
  • monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl (C-C3H5), cyclobutyl (c- C4H7), cyclopentyl (C-C5H9) and cydohexyl (c-CeHu).
  • 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.
  • cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • cycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group ("C3-Cs-cycloalkyl-Ci-C4- alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl”), more preferably a C 3 -C 4 -cycloalkyl group (“C 3 -C 4 -cycloalkyl-CrC 4 -alkyl”) as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • C3-C6-cycloalkyl-Ci-C4-alkyl apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
  • C3-C6-cycloalkylmethyl is for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl.
  • Ci-C2-alkoxy is a Ci-C2-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.
  • CrC6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
  • CrCio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-Alkoxy is, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 - dimethylethoxy (tert-butoxy).
  • Ci-C4-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • 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 methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.
  • SO n -Ci-C6-alkyl is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom, in case n is 0 (also referred to as alkylthio group). If n is 1 , the term refers to a Ci-C6-alkyl group attached via a sulfinyl group (also referred to as alkylsulfinyl group). If n is 2, the term refers to a Ci-C6-alkyl group attached via a sulfonyl group (also referred to as alkylsulfonyl group).
  • Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n- butylcarbonyl and the like.
  • Ci-C 4 -alkylamino is a group -N(H)Ci-C 4 -alkyl.
  • Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
  • the term "di-(Ci-C 4 -alkyl)amino" is a group -N(Ci-C 4 -alkyl) 2 . Examples are dimethylamino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.
  • Ci-C 4 -alkylaminocarbonyl is a group -C(0)N(H)Ci-C 4 -alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and the like.
  • the term "3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms N, O, and/or S, as ring members" denotes a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or fully unsaturated heteromonocyclic ring or a 8-, 9- or 10-membered saturated, partially or fully unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms which are selected from N, O, and S as ring members.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Fully unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Fully unsaturated include aromatic heterocyclic rings.
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. 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.
  • N and S ring atoms may be oxidized, if not mentioned otherwise. The oxidized ring atoms constitue an N- oxide, Sulfoxide (SO), and a sulfone (SO2), resp., wherein the only the N- or S atom is a ring member.
  • Examples of a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heteromonocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydro- furan-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrroli- din-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imida- zolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-
  • Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3- dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,
  • Examples for a 3-, 4-, 5-, 6- or 7-membered fully unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1- pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1 -pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1-yl, 1 ,3,4-triazol-2-yl, 1 ,2,4-triazol-1-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxo- pyridin-2-yl,
  • a group of preferred heterocycles is the following: 2-pyridyl (E-1 ), 3-pyridyl (E-2), 4-pyridyl (E- 3), 3-pyridazinyl (E-4), 4-pyrimidinyl (E-5), 2-pyrazinyl (E-6), 2-pyrimidinyl (E-7), thiophen-2-yl (E-8), thiophen-3-yl (E-9), furan-2-yl (E-10), and furan-3-yl (E-1 1 ); heterocycles E-1 , E-2, and E- 7 are particularly prefered, which rings E-1 to E-1 1 are unsubstituted or substituted by up to 3 same or different substituents.
  • Another particulary preferred heterocycle is 1 ,2,4-triazol-1 -yl.
  • Preferred 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic rings comprising 1 , 2 or 3 heteroatoms N, O, and/or S as ring members (HET) are in any positions of formula I, the following: azetidin-3-yl (H-1 ), dioxin-6-yl (H-2), 1 ,3-dioxolan-2-yl (H-3), 1 ,1- dioxotetrahydrothiophen-3-yl (H-4), 1 ,1-dioxothietan-2-yl (H-5), 1 ,1 -dioxothietan-3-yl (H-6), imidazol-2-yl (H-7), imidazol-4-yl (H-8), imidazol-5-yl (H-9), isothiazol-3-yl (H-10), isothiazol-4-yl (H-1 1 ), isothiazol-5-yl (
  • H-42 5- pyrimidinyl
  • H-43 pyrrolidin-3-yl
  • More preferred rings HET are the following: E-1 , E-7 and H-6, H-21 , H-33 and H-35. Rings E-2 and E-7 are particularly preferred.
  • A is A 1 .
  • W is O.
  • Y is N(R 5 )R 6 ; wherein R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings:
  • R 5 is H, d-Cs-alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, CH 2 CN or Ci-C 2 -alkoxy-CrC 2 -alkyl;
  • R 6 is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which is unsubstituted or substituted by one R 8 ; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which is
  • R 9 is H, Ci-Ce-alkyl or Ci-Ce-haloalkyI
  • R 10a in -N(R 10a )R 10b as a meaning for R 6 is H;
  • R 14a is H or Ci-Ce-alkyl
  • R 14 is H, Ci-Ce-alkyl, Ci-Ce-haloalkyI, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, CH2-CN, Ci-C 4 -alkoxy or Ci-C 4 -haloalkoxy; and R 11 and R 16 ; independently of each occurrence and independently of each other, are
  • Ci-C 4 -alkyl Ci-C 4 -haloalkyl
  • Ci-C 4 -alkoxy Ci-C 4 -haloalkoxy
  • N(R 5 )R 6 as a radical Y,
  • R 5 is H
  • R 9 is selected from Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 10a is H
  • R 10b is a heteroaromatic ring of formulae E-1 to E-11 , or H-6, H-21 , H-33 and H-35 as defined above, wherein
  • R 14a is H or Ci-Ce-alkyl
  • R 14b is H, Ci-Ce-alkyI, Ci-Ce-haloalkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, CH2-CN, Ci-C 4 -alkoxy or Ci-C 4 -haloalkoxy; and R 11 and R 16 ; independently of each occurrence and independently of each other, are
  • a 1 Y is H.
  • R 9 has one of the above general meanings, or, in particular, is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R 13 , where R 13 has one of the above general meanings, or, in particular, one of the following preferred meanings: CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl and a heterocyclic ring selected from E-1 to E-1 1 as defined above, which rings are unsubstituted or substituted by up to 3 R 16 ;
  • each R 16 is independently selected from halogen, CN, NO2, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci- C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkylsulfinyl, Ci-
  • R 9 is selected from H, Ci-C6-alkyl and Ci-C6-haloalkyl, and specifically from H and Ci-Ce-alkyI.
  • W is O and Y is -N(R 5 )R 6 .
  • W is O and Y is H.
  • W is O and Y is OR 9 , wherein R 9 has one of the above general meanings, or, is preferably H, Ci-C6-alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R 13 , where R 13 has one of the above general meanings, or, is preferably CN, Ci-C6-alk- oxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkyl- sulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above.
  • W is O and R 9 is H, Ci-C6-alkyl or Ci-C6-
  • Compounds I wherein Y is OR 9 have biological activity, but are also useful as intermediate compounds in the preparation of compounds I wherein Y is N(R 5 )R 6 .
  • the invention also relates to intermediate compounds I wherein A is A 1 wherein Y is -OR 9 , wherein R 9 has one of the above-defined general meanings or, preferably, one of the above-defined preferred meanings; and to the use of such compounds in the preparation of compounds I wherein Y is N(R 5 )R 6 .
  • Compounds I wherein Y is H have biological activity, too, but are especially useful as intermediate compounds in the preparation of compounds I wherein Y is N(R 5 )R 6 .
  • the invention also relates to intermediate compounds I wherein A is A 1 wherein Y is H; and to the use of such compounds in the preparation of compounds I wherein Y is N(R 5 )R 6 .
  • N(R 5 )R 6 as a radical Y, preferably
  • R 5 is selected from H, Ci-C6-alkyl, C2-C3-alkynyl and Ch -CN, particularly H or Ci-C3-alkyl;
  • R 6 is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R 8 , wherein R 8 is as defined below; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;
  • each R 11 is independently selected from the group consisting of halogen, CN, NO2, Ci-
  • R 10a is H or Ci-C 6 -alkyl
  • R 10b is H, d-Ce-alkyl, Ci-C 6 -haloalkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, CH 2 -CN, Ci-C6-alkoxy or Ci-C6-haloalkoxy; and each R 16 as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci- C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfon
  • R 5 is H
  • R 6 is selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl substituted by one R 8 , C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F and CN;
  • R 8 is CN, Cs-Ce-cycloalkyI which is unsubstituted or substituted by a CN;
  • Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, CrC 6 -haloalkylsulfinyl, CrC 6 -alkylsulfonyl, C1-C6- haloalkylsulfonyl, -C( O)N(R 10a )R 10b , phenyl which is unsubstituted or substituted by one or more same or different R 16 , and a heterocyclic ring selected from rings E-1 to E-1 1 as defined above; wherein
  • R 9 is selected from H, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 10a in -N(R 10a )R 10 as a meaning for R 6 is H;
  • R 14b is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, Cs-Ce- halocycloalkyl, CH2-CN, Ci-C4-alkoxy and Ci-C4-haloalkoxy; and
  • R 11 and R 16 independently of each occurrence and independently of each other (also in rings E-1 to E-1 1 ), are selected from halogen, CN, NO2, CrC4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C3- C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, Ci-C
  • A is A 2 .
  • R 7a and R 7b in group A 2 are independently of each other selected from H, CN, Ci- C 4 -alkyl and CrC 4 -haloalkyl, and more preferably from H, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl. Even more preferably, one of R 7a and R 7b is H and the other is H or CH3. Specifically, both are H.
  • groups R 5 and R 6 are preferably defined as outlined above for preferred embodiments.
  • R 5 is selected from H, Ci-C 4 -alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy-methyl- and
  • R 9 , R 10a , R 10b , 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 10 in C( O)N(R 10a )R 10 and N(R 10a )R 10 as a meaning of R 8 in the group
  • Cs-Ce-cycloalkyI which is unsubstituted or substituted by 1 CN; and Cs-Cs-halocycloalkyl; and more preferably from H, Ci-C6-alkyl, Ci-C6-haloalkyl, CH 2 -CN, C2-C4-alkenyl, C2-C4-alky- nyl, C 3 -C6-cycloalkyl, C 3 -C6-halocycloalkyl, C 3 -C6-cycloalkylmethyl-, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • each R 16 as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently selected from H, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-halo- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2- C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkylcarbonyl, Ci-
  • R 9 is H, d-Ce-alkyl or Ci-C 6 -haloalkyl
  • R 10a is H, Ci-C 4 -alkyl, CrC 4 -haloalkyl and C 3 -C 6 -cycloalkyl, and preferably H and CrC 4 -alkyl;
  • R 13 is selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio,
  • Ci-C6-alkylsulfinyl Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, -
  • R 14a is selected from H and Ci-Ce-alkyl
  • R 14 is selected from H, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, CH 2 -CN, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -
  • each R 16 as a substituent on phenyl or heterocyclic rings E-1 to E-1 1 is independently
  • A is A 3 .
  • a 3 is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heteromonocyclic ring containing 1 , 2, 3, or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or substituted by up to 3 R 11 .
  • a 3 is preferably selected from pyrazoles, oxazoles, thiazoles, and triazoles, which rings are unsubstituted or substituted by R 11 , more preferably the rings are selected from 1 -pyrazolyl and 1 ,2,4-triazolyl, which are substituted by (R 11 ) k .
  • a 3 is selected from 1-pyrazole, 2-oxazole, 2-thiazole and 1 ,2,4-triazole which rings are unsubstituted or substituted by (R 11 )k.
  • a 3 is 1-Pyrazolyl, or 1 ,2,4-Triazolyl which rings are unsubstituted or substituted by (R 11 )k.
  • heterocycle in A 3 is unsubstituted.
  • k is 1 or 2.
  • each R 11 is independently selected from halogen, CN, NO2, Ci-C4-alkyl, Ci-C 4 -ha- loalkyl, Ci-C 4 -alkoxy, CrC 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C3-C6-halo- cycloalkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl, C2-C 4 -haloalkynyl, Ci-C 4 -alkylcarbo- nyl, Ci-C 4 -
  • Particularyl preferred R 11 is selected from halogen, CN, NO2, SCN, SF 5 , Ci-Cio-alkyl, C3-C8- cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, which groups are unsubstituted, or partially or fully halogenated.
  • B 1 , B 2 and B 3 are CR 2 , wherein R 4 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • B 1 and B 2 are CR 2 , with R 2 being H, CI or F, and B 3 is CCI.
  • B 1 is H or CI
  • B 2 is H or F
  • B 3 is CI
  • G 1 , G 2 , G 3 and G 4 are CR 4 , where R 4 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • G 1 , G 3 and G 4 are CH and G 2 is CR 4 , wherein R 4 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • G 3 and G 4 are CH and G 1 and G 2 together form a five- or
  • G 1 , G 2 and G 4 are CH, and G 3 is CR 4 , wherein R 4 together with R 7a forms a -CH 2 CH 2 - chain.
  • R 4 is selected from H, halogen, CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Cs-Cs-cycloalkyl, C3-C5-halocycloalkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl, C2-C 4 -haloalkynyl, C1-C4- alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and Ci-C 4 -haloalkylthio, and in particular from H, F, CI, Br, CN, CH 3 and CF 3 .
  • R 1 is halomethyl, specifically fluoromethyl, such as CH2F, CHF2, and CF3, and is particularly CF3.
  • R 8 , R 9 , R 10a , R 10b , R 11 , R 12 , R 13 , R 15 and R 16 have following preferred meanings:
  • R 8 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, OR 9 , SR 9 ,
  • R 8 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of cyano, 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 cyano, 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, C3-C8- halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 , -SR 9 , - N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 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 N, O, S, 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.
  • R 8 is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 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 N, O, S, wherein N and/or S may be oxidized, as ring members, which ring is unsubstituted or partially or fully substituted by same or different R 16 ; wherein R 10a , R 10b and R 16 have has one of the meanings given above or
  • each R 9 is independently selected from the group consisting of H, Ci-C6-alkyl, Ci- C6-haloalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 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 hetero- atom groups selected from N, O, S, NO, SO and S0 2 , as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 or 2, more preferably 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 is unsubstituted or partially or fully substituted by same or different 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 is unsubstituted or partially or fully substituted by 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, C 2 -C4-alkenyl, C 2 -C4-haloalkenyl, C 2 -C4-alkynyl, C 2 -C4-haloalkynyl, C 3 -C6-cyclo- alkyl, C 3 -C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocar- bonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl, C3-C6-halocycloalkyl- aminocarbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1
  • 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, wherein the heterocyclic is unsubstituted or substituted by 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C 2 -C4-haloalkenyl, C 2 -C4-alkynyl, C 2 -C4-haloalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halocycloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, and Ci-C4-hal
  • R 10a and R 10b are, independently of each other, selected from H, 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, preferably 1 , 2 or 3, in particular 1 , substituents halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy or Ci-C4-haloalkoxy; and are specifically, independently of each other, H, Ci-C4-alkyl or Ci-C4-haloalkyl.
  • 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, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-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 CN, Cs-Cs-cycloalkyl, C 3 -C 8 -halocycloalkyl, OH, SH, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci- C4-haloalkylsulfonyl and phenyl which is unsunstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-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 CN, Ci-C6-al- kyl, Ci-Ce-haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, OH, SH, Ci-C 4 -alkoxy, Ci-C 4 -halo- alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-al- kylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which is unsubstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alky
  • R 13 is a substituent on a cycloalkyl group, it is even more preferably selected from 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 H, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, OH, SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3 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 H, 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, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • 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 may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, wherein the heterocyclic ring is unsubstituted or substituted by 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy.
  • R 14 , R 14a and R 14b are, independently of each other, selected from H, C1-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 Ci-C4-haloalkoxy;
  • 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 may contain 1 or 2 further heteroatoms or heteroatom groups N, O, S, NO, SO or SO2, as ring members, wherein the heterocyclic ring is unsubstituted or substituted by 1 or 2, in particular 1 , substituents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • Each R 15 is preferably selected from H, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, which rings are unsubstituted or substituted by 1 , 2 or 3 substituents Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy.
  • R 2a and R 3 are both H, and R 2b is F
  • R 2a and R 3 are both H, and R 2b is F
  • Such compounds correspond to formula IA.1 , wherein the variables are as defined and preferred for formula IA, and R 5a is preferably H.
  • R 4A is preferably halogen, such as CI, or Ci-C4-alkyl, such as CH3.
  • R 6 is Ci-C4-alkyl, preferably ethyl, which is substituted by halogen, cycloalkyl, halocycloalkyl, S(0) n -CrC2-alkyl, oxo, alkylamino, or haloalkylamino.
  • R 6 is a 5- or 6-membered heteroaryl group, preferably selected from thietan, oxothietan, dioxothietan, pyrimidin, pyrrolidin, isoxazolidin, bonded ether directly or via a CH2 bridge.
  • the rings are prefereably unsubstituted, or may be substituted by halogen, Ci-C4-alkyl, or oxo. Further preferred embodiments are listed in Table A.
  • the compounds of general formula I particularly of formulae IA.1 , IB.1 , Id , ID.1 , and IE.1 , which are indicated in Tables 1 to 167 below, and their stereoisomers, salts, tautomers and N- oxides, represent per se preferred embodiments of the present invention.
  • the meanings for the variables indicated in Tables 1 to 167, and particularly in Tables A, B, and C, resp., below represent embodiments of the invention which are likewise preferred independently of one another and especially in combination.
  • Table 1 Compounds of formula IA.1 in which R 1 is CF 3 , R 4A is Br, R 5a is CH 3 , and R 6 for a compound corresponds in each case to one row of Table A
  • Table 17 Compounds of formula IA.1 in which R 1 is CF 3 , R 4A is CH 3 , R 5a is H, and R 6 for a compound corresponds in each case to one row of Table A
  • Table 18 Compounds of formula IA.1 in which R 1 is COOCH 3 , R 4A is CH 3 , R 5a is H, and R 6 for a compound corresponds in each case to one row of Table A
  • A-140 CH 2 -CONHCH 2 CH CH 2 A-182 CH 2 -(2-CI-thiazol-5-yl)
  • A-230 CH NOCH 2 CF 3 4-yl
  • R 6 is Ci-C 4 -alkyl, preferably ethyl, which is substituted by halogen, cycloalkyl, halocycloalkyl, S(0) n -Ci-C 2 -alkyl, oxo, alkylamino, or haloalkylamino constitute a preferred embodiment.
  • R 6 is a 5- or 6-membered heteroaryl group, preferably selected from thietan, oxothietan, dioxothietan, pyrimidin, pyrrolidin, isoxazolidin, bonded ether directly or via a CH 2 bridge.
  • the rings are prefereably unsubstituted, or may be substituted by halogen, Ci-C 4 -alkyl, or oxo. Further preferred embodiments are listed in Table A.
  • Table 22 Compounds of formula Id in which R 4A is F, and A 3 for a compound corresponds in each case to one row of Table B
  • Table 23 Compounds of formula IC.1 in which R 4A is CI, and A 3 for a compound corresponds in each case to one row of Table B
  • R 9 is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C8-cycloalkyl, C 3 - C8-cycloalkyl-Ci-C4-alkyl-, C 3 -C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, SO n -Ci-C6- alkyl, SO n -Ci-C6-haloalkyl, with n being 0, 1 , or 2, are particularly preferred embodiments. Further preferred embodiments are listed in Table 27.
  • R 1 is CF 3 , COOCH 3 , R 4A is CN, F, CI, Br, CH 3 , R 6 and R 7a are both H, and R 9 is Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C8-cycloalkyl, C 3 -C8-cycloalkyl-Ci-C 4 -alkyl, C 3 -C 8 -halocycloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, SO n -Ci-C6-alkyl, SO n -Ci-C6-haloalkyl, phenyl, which is unsubstituted, or partially or fully substituted by same or different R 16 ; or 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1 , 2 or 3 hetero
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • Table 98 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is F, R 6 is n-C 3 H 7 , R 7a is CH 3 , and R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 12 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is Br, R 6 is CH 2 CN, R 7a is H, and R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 14 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is CN, R 6 is CH 2 CN, R 7a is H, and R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 15 Compounds of formula IE.1 in which R 1 is COOCH 3 , R 4A is CN, R 6 is CH 2 CN, R 7a is
  • Table 1 16 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is CH 3 , R 6 is CH 2 CN, R 7a is H, and R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 17 Compounds of formula IE.1 in which R 1 is COOCH 3 , R 4A is CH 3 , R 6 is CH 2 CN, R 7a is H, and R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 18 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is F, R 6 is CH 2 CN, R 7a is CH 3 , and R 9 for a compound corresponds in each case to one row of Table C
  • Table 1 19 Compounds of formula IE.1 in which R 1 is COOCH 3 , R 4A is F, R 6 is CH 2 CN, R 7a is
  • Table 141 Compounds of formula IE.1 in which R 1 is COOCH 3 , R 4A is CI, R 6 is CH 2 C ⁇ CH, R 7a is CH 3 , and R 9 for a compound corresponds in each case to one row of Table C
  • Table 142 Compounds of formula IE.1 in which R 1 is CF 3 , R 4A is Br, R 6 is CH 2 C ⁇ CH, R 7a is
  • R 9 for a compound corresponds in each case to one row of Table C
  • the compounds of the present invention may be used for controlling invertebrate pests.
  • the present invention also relates to a mixture of at least one compound of the present invention, being particulary of formulae IA, IB, IC, ID, and IE, with at least one mixing partner as defined herein after.
  • Preferred are binary mixtures of one compound of the present invention as component I with one mixing partner as defined herein after as component II.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofu- ran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfen
  • GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopente- nyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fen
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
  • M.9 Selective homopteran feeding blockers for example M.9B pymetrozine, or M.9C flonicamid;
  • M.10 Mite growth inhibitors for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
  • M.1 1 Microbial disruptors of insect midgut membranes for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus
  • CrylAb CrylAc
  • Cryl Fa Cry2Ab
  • mCry3A Cry3Ab
  • Cry3Bb Cry34/35Ab1
  • M.12 Inhibitors of mitochondrial ATP synthase for example M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 as for example buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
  • Octopamin receptor agonists as for example amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors, for example M.20A
  • M.21 Mitochondrial complex I electron transport inhibitors for example M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers for example M.22A indoxacarb, or M.22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
  • M.24 Mitochondrial complex IV electron transport inhibitors for example M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendi- amide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or the phthalamides
  • M.28.1 (R)-3-Chlor-N1- ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluormethyl)ethyl]phe- nyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid
  • M.28.2 (S)-3-Chloro-N1 - ⁇ 2-methyl-4- [1 ,2,2,2 - tetrafluor-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthal- amid, or the compound M.28.3: 3-bromo-N-
  • M.29. insecticidal active compounds of unknown or uncertain mode of action as for example afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bro- mopropylate, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluen- sulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or M.29.3: 1 1 -(4- chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azad
  • M.29.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxo- thietan-3-yl)benzamide; or M.29.9.b): fluxametamide; or
  • M.29.10 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; or a compound selected from the group of M.29.1 1 , wherein the compound is selected from M.29.1 1 b) to M.29.1 1 p): M.29.1 1 .b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexa- fluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.29.1 1.c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M.29
  • M.29.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; or
  • M.29.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5- dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M.29.16d) 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M.29.16e N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carbox- amide
  • M.29.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide
  • M.29.16h N-methyl-1 -(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide
  • M.29.16i 1 -(4,4-difluorocyclohexyl)-N-ethyl-5-
  • M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j): M.29.17a) N-(1 - methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.29.17b) N-cyclopropyl-2-(3-pyridi- nyl)-2H-indazole-4-carboxamide; M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; M.29.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide; M.29.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide; M.29.17
  • M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d): M.29.18a) N-[3- chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide; M.29.18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;
  • M.29.18c N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N- ethyl-propanamide; M.29.18d) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopro- pyl)methylsulfinyl]-N-ethyl-propanamide; or
  • M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456, M.4A.2, also to be named as guadipyr, is known from WO2013/003977, and the M.4A.3 (approved as
  • M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994.
  • the phthalamides M.28.1 and M.28.2 are both known from WO2007/101540.
  • the anthranilamide M.28.3 is described in WO2005/077934.
  • the hydrazide M.28.4 is described in WO2007/043677.
  • M.28.5h are described in WO 2007/006670, WO2013/024009 and WO2013/024010
  • the anthranilamide ⁇ .28.5 ⁇ is described in WO201 1/085575
  • M.28.5j in WO2008/134969
  • M.28.5k in US201 1/046186 and M.28.5I) in WO2012/034403.
  • the diamide M.28.6 can be found in WO 2012/034472.
  • the spiroketal-substituted cyclic ketoenol M.29.3 is known from WO2006/089633 and the biphenyl-substituted spirocyclic ketoenol M.29.4 from WO2008/06791 1.
  • the triazoyl- phenylsulfide M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707.
  • the compounds M.29.6a) to M.29.6i) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO 2013/129688.
  • the nematicide M.29.8 is known from WO2013/055584.
  • the pyridalyl-type analogue M.29.10 is known from WO2010/060379.
  • the carboxamides broflanilide and M.29.1 1.b) to M.29.1 1.h) are described in WO2010/018714, and the carboxamides M.29.1 1 i) to M.29.1 1 .p) in WO2010/127926.
  • the pyridylthiazoles M.29.12.a) to M.29.12.C) are known from WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.f) to M.29.12.m) from WO2010/129497.
  • the compounds M.29.14a) and M.29.14b) are known from WO2007/101369.
  • the pyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and the pyrazoles M.29.16i) and M.29.16j) are described in US 61/891437.
  • the pyridinyl- indazoles M.29.17a) to M.29.17.j) are described in WO2015/038503.
  • the pyridylpyrazoles M.29.18a) to M.29.18d) are described in US2014/0213448.
  • the isoxazoline M.29.19 is described in WO2014/036056.
  • the isoxazoline M.29.20 is known from WO2014/090918.
  • Inhibitors of complex III at Q 0 site e. g. strobilurins: azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), mandestrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxy.
  • azoxystrobin A.1 .1
  • coumethoxy- strobin A.1 .2
  • coumoxystrobin A.1.3
  • dimoxystrobin A.1.4
  • strobin (A.1 .13), pyraclostrobin (A.1 .14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1.16), trifloxystro- bin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2- methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl-pyra- zol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[
  • inhibitors of complex III at Qi site cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(3S,6S,7R,8R)- 8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan- 7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy- pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbony
  • - inhibitors of complex II e. g. carboxamides: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1-methyl-1 H-pyrazo
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim (A.4.1 ), (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides)
  • SBI fungicides Sterol biosynthesis inhibitors
  • DMI fungicides triazoles: azaconazole (B.1 .1 ), bitertanol (B.1 .2), bromuconazole (B.1 .3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1 .6), diniconazole-M (B.1.7), epoxiconazole (B.1 .8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1.12), hexaconazole (B.1 .13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazo
  • Delta 14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • phenylamides or acyl amino acid fungicides benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1.3), metalaxyl (C.1 .4), metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim
  • triazolopyrimidines 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidine (D1 .6);
  • diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);

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Abstract

La présente invention concerne un procédé permettant de préparer des composés cyclopentène de formule (I) dans laquelle les variables ont la signification telle que définie dans la description, par cyclisation dans des conditions basiques d'une cétone de formule (II) qui est obtenue en faisant réagir un composé de formule (III) avec un composé de formule (IV), de nouveaux composés de formule (I), des méthodes et des utilisations de ces composés et des combinaisons pour lutter contre les nuisibles invertébrés tels que les insectes, les arachnides ou les nématodes sur et dans les végétaux et pour protéger le matériel de propagation des végétaux tel que les semences.
PCT/EP2016/066734 2015-07-24 2016-07-14 Procédé de préparation de composés cyclopentène Ceased WO2017016883A1 (fr)

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Cited By (4)

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WO2018197466A1 (fr) * 2017-04-26 2018-11-01 Basf Se Dérivés de succinimide substitués utilisés en tant que pesticides
US10526264B2 (en) 2016-07-07 2020-01-07 Basf Se Oxy-cope rearrangement for the manufacture of insecticidal cyclopentene compounds
US10961213B2 (en) 2017-01-25 2021-03-30 Basf Se Process for preparation of benzylic amides
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds

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US10526264B2 (en) 2016-07-07 2020-01-07 Basf Se Oxy-cope rearrangement for the manufacture of insecticidal cyclopentene compounds
US10961213B2 (en) 2017-01-25 2021-03-30 Basf Se Process for preparation of benzylic amides
WO2018197466A1 (fr) * 2017-04-26 2018-11-01 Basf Se Dérivés de succinimide substitués utilisés en tant que pesticides
CN110582492A (zh) * 2017-04-26 2019-12-17 巴斯夫欧洲公司 作为农药的取代的琥珀酰亚胺衍生物

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