WO2015169723A1 - Composés insecticides à base de dérivés de thiophène - Google Patents

Composés insecticides à base de dérivés de thiophène Download PDF

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WO2015169723A1
WO2015169723A1 PCT/EP2015/059661 EP2015059661W WO2015169723A1 WO 2015169723 A1 WO2015169723 A1 WO 2015169723A1 EP 2015059661 W EP2015059661 W EP 2015059661W WO 2015169723 A1 WO2015169723 A1 WO 2015169723A1
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substituted
methyl
aryl
trifluoromethyl
formula
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PCT/EP2015/059661
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English (en)
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Girish RAWAL
Rupesh PATRE
Jérôme Yves CASSAYRE
Guillaume Berthon
Myriem El Qacemi
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

Definitions

  • the present invention relates to certain arylthioacetamides and derivatives thereof, to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.
  • a 1 , A 2 , A 3 ,and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • G is oxygen or sulfur
  • G 2 is oxygen or sulfur
  • G 3 is oxygen or sulfur
  • R is hydrogen, d-C 8 alkyl, d-C 8 alkoxy, Ci-C 8 alkylcarbonyl, or d-C 8 alkoxycarbonyl;
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 3 , C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene or C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 3 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 4 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , heterocyclyl or heterocyclyl substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , hetero
  • R 3 is d-Cshaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 5 , or heteroaryl or heteroaryl substituted by one to five R 5 ;
  • R 6a and R 6b are each independently hydrogen, halogen, cyano, Ci-C 8 alkyl, Ci-C 8 haloalkyl, or C 3 - Cscycloalkyl, or R 6a and R 6b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;
  • R 7 is hydrogen, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 alkylcarbonyl, or Ci-C 8 alkoxycarbonyl;
  • R 8 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 3 , C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene or C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 3 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 4 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , or heterocyclyl or heterocyclyl substituted by one to five R 4 , R 9 is hydrogen, Ci-C 8 alkyl, Ci-C 8
  • R 0 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 3 , C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene or C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 3 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 4 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , heterocyclyl or heterocyclyl substituted by one to five R 4 ;
  • each R is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 - Cshaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, d- C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, d- C 8 haloalkylsulfonyl, Ci-C 8 alkylcarbonyl, or Ci-C 8 alkoxycarbonyl;
  • each R 2 is independently halogen, cyano, nitro, hydroxy, amino, Ci-C 8 alkylamino, (d- C 8 alkyl) 2 amino, Ci-C 8 alkylcarbonylamino, Ci-C 8 haloalkylcarbonylamino, d-C 8 alkoxy, Ci-C 8 haloalkoxy, aryloxy or aryloxy substituted by one to five R 6 , aryloxy-d-dalkylene or aryloxy-d-dalkylene wherein the aryl moiety is substituted by one to five R 6 , d-C 8 alkylcarbonyl, d-C 8 alkoxycarbonyl, mercapto, d- C 8 alkylthio, Ci-C 8 haloalkylthio, d-dalkylsulfinyl, Ci-C 8 haloalkylsulfinyl, d-dalkylsulfonyl, d-
  • each R 3 is independently halogen, cyano, d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, or d-dalkoxy,
  • each R 4 is independently halogen, cyano, nitro, d-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 cyanoalkyl, C 2 -
  • each R 6 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or d-
  • each R 9 is hydrogen, Ci-C 8 alkyl or Ci-C 8 haloalkyl
  • each Z is independently halogen, cyano, Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , nitro, hydroxyl, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, d- C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, or Ci-C 8 haloalkylsulfonyl;
  • n 1 or 2;
  • p 0, 1 , 2, 3, 4, or 5;
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are independently of one another C-H, C-R 5a or nitrogen;
  • G is oxygen or sulfur
  • G 2 is oxygen or sulfur
  • G 3 is oxygen or sulfur
  • R is hydrogen, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 alkylcarbonyl, or Ci-C 8 alkoxycarbonyl;
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 3 , C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene or C 3 -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 3 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 4 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- substituted by one to five R 4 , aryl or aryl substituted
  • C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Ci-C 8 haloalkylaminocarbonyl-Ci-C 4 alkylene, C 3 -C 8 cycloalkyl- aminocarbonyl-Ci-C 4 alkylene, aryl-CH 2 -aminocarbonyl-Ci-C 4 alkylene or aryl-CH 2 -aminocarbonyl-d- C 4 alkylene wherein the aryl is substituted by one to five R 4 , Ci-C 8 alkylaminocarbonyl, d- C 8 haloalkylaminocarbonyl, C 3 -C 6 cycloalkylaminocarbonyl, or d-C 6 haloalkyl-0- N CH-;
  • R 3 is d-Cshaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 5 , or heteroaryl or heteroaryl substituted by one to five R 5 ;
  • R 6a and R 6b are each independently hydrogen, halogen, cyano, d-C 8 alkyl, d-dhaloalkyl, or C 3 - dcycloalkyl, or R 6a and R 6b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;
  • R 7 is hydrogen, d-C 8 alkyl, d-C 8 alkoxy, d-dalkylcarbonyl, or d-C 8 alkoxycarbonyl;
  • R 8 is d-dalkyl or d-C 8 alkyl substituted by one to five R 2 , d-Ci 0 cycloalkyl or C 3 -d 0 cycloalkyl substituted by one to five R 3 , d-Ci 0 cycloalkyl-d-dalkylene or d-Ci 0 cycloalkyl-d-dalkylene substituted by one to five R 3 , aryl-d-dalkylene- or aryl-d-dalkylene- substituted by one to five R 4 , heterocyclyl-d-C 4 alkylene- or heterocyclyl-Ci-dalkylene- substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , or heterocyclyl or heterocyclyl substituted by one to five R 4 , each R ! is independently hydrogen, d-C 8 alkyl, d-C 8 alkoxy, d-C
  • R 0 is d-C 8 alkyl or d-dalkyl substituted by one to five R 2 , C 3 -d 0 cycloalkyl or d-Ci 0 cycloalkyl substituted by one to five R 3 , C 3 -d 0 cycloalkyl-d-C 4 alkylene or d-Ci 0 cycloalkyl-d-dalkylene substituted by one to five R 3 , aryl-d-dalkylene- or aryl-d-dalkylene- substituted by one to five R 4 , heterocyclyl-Ci-dalkylene- or heterocyclyl-d-C 4 alkylene- substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 , heterocyclyl or heterocyclyl substituted by one to five R 4 ;
  • each R is independently halogen, cyano, nitro, d-C 8 alkyl, d-C 8 haloalkyl, d-dalkenyl, C 2 - dhaloalkenyl, d-dalkynyl, d-dhaloalkynyl, hydroxy, d-C 8 alkoxy, d-dhaloalkoxy, mercapto, Ci- C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, d- C 8 haloalkylsulfonyl, Ci-C 8 alkylcarbonyl, or Ci-C 8 alkoxycarbonyl;
  • each R 2 is independently halogen, cyano, nitro, hydroxy, amino, Ci-C 8 alkylamino, (d- C 8 alkyl) 2 amino, Ci-C 8 alkylcarbonylamino, Ci-C 8 haloalkylcarbonylamino, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, aryloxy or aryloxy substituted by one to five R 6 , aryloxy-Ci-C 4 alkylene or aryloxy-Ci-C 4 alkylene wherein the aryl moiety is substituted by one to five R 6 , Ci-C 8 alkylcarbonyl, Ci-C 8 alkoxycarbonyl, mercapto, d- C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, d
  • each R 3 is independently halogen, cyano, Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, or Ci-C 8 alkoxy,
  • each R 4 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 cyanoalkyl, C 2 - C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -Ci 0 cycloalkyl, C 3 -Ci 0 cycloalkyl-Ci- C 4 alkylene, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, d- C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, Ci-C 8 haloalkylsulfonyl, Ci-C 8
  • each R 6 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or d- C 4 haloalkoxy;
  • each R 9 is hydrogen, Ci-C 8 alkyl or Ci-C 8 haloalkyl
  • each Z is independently halogen, cyano, Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , nitro, hydroxyl, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, d- C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, or Ci-C 8 haloalkylsulfonyl;
  • n 1 or 2;
  • p 0, 1 , 2, 3, 4, or 5;
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.
  • the compounds of the invention may contain one or more asymmetric carbon atoms, for example, in the -CR 3 R 4 - group and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. Further, where any group is SO, the compounds of the invention are sulfoxides, which can also exist in two enantiomeric forms.
  • the number of substituents does not exceed the number of available C-H and N-H bonds, for example in the group Ci-C 8 alkyl substituted by one to five R 2 has only one to three substituents if dalkyl thus methyl is meant.
  • Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2-methyl-prop-1-yl or 2-methyl-prop-2-yl.
  • the alkyl groups are preferably Ci-C 6 , more preferably C1-C4, most preferably C1-C3 alkyl groups. Where an alkyl moiety is said to be substituted , the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 - , -CH2-CH2-, -CH(CH 3 )-, -CH2-CH2-CH2-, -CH(CH 3 )-CH 2 - or -CH(CH 2 CH 3 )-.
  • the alkylene groups are preferably Ci-C 3 , more preferably C1-C2, most preferably Ci alkylene groups.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configu ration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C 2 - C 6 , more preferably C 2 -C 4 , most preferably C 2 -C 3 alkenyl groups.
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C 6 , more preferably C 2 -C 4 , most preferably C 2 -C 3 alkynyl groups.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl, chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.
  • Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.
  • Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 1-chloro-prop-2-ynyl.
  • Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl.
  • the cycloalkyl groups are preferably C 3 - C 8 , more preferably C 3 -C 6 cycloalkyl groups.
  • the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1 ,3]dioxolanyl, piperidinyl, piperazinyl, [1 ,4]dioxanyl, and morpholinyl or their oxidised versions such as 1-oxo-thietanyl and 1 ,1-dioxo-thietanyl.
  • bicyclic groups examples include 2,3-dihydro- benzofuranyl, benzo[1 ,4]dioxolanyl, benzo[1 ,3]dioxolanyl, chromenyl, and 2,3-dihydro-benzo[1 ,4]dioxinyl.
  • a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Preferred values of P1 , P2, P3, A 1 , A 2 , A 3 , A 4 , G , G 2 , G 3 , R , R 2 , R 3 , R 4 , R 5 , , R 6a , R 6b , R 7 , R 8 , R 9 , R 0 , R 11 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 20 , k, n, p, and q are, in any combination (including combinations of preferred values with the original values) as set out below.
  • a 2 , A 3 and A 4 are nitrogen.
  • a 2 is C-H, C-R 5a or N, more preferably A 2 is C-H or C-R 5a , most preferably A 2 is C-H.
  • a 3 is C-H or N, most preferably A 3 is C-H.
  • a 4 is C-H or N, most preferably A 4 is C-H.
  • a 2 , A 3 and A 4 are C-H or N, wherein no more than two of A 2 , A 3 and A 4 are N and wherein A 3 and A 4 are not both N.
  • a 2 is C-H and A 3 and A 4 are C-H or one of A 3 and A 4 is N. More preferably A 2 , A 3 and A 4 are C-H.
  • G is oxygen
  • G 2 is oxygen
  • G 3 is oxygen
  • G , G 2 and G 3 are oxygen.
  • G , G 2 and G 3 are oxygen.
  • R is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 2 is d-C 8 alkyl or d-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 - docycloalkyl substituted by one to five R 3 , C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- or heterocyclyl-C(R 7 )(R 18 )- wherein the heterocyclyl is substituted by one to five R 4 , aryl or aryl substituted by one to five R 4
  • heterocyclyl is a 4 to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0 2 , N, and N(R 20 ) as ring atoms.
  • aryl is phenyl
  • R 7 and R 8 are independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d- C 4 alkoxy, Ci-C 4 haloalkoxy or C 3 -C 6 cycloalkyl;
  • R 7 and R 8 together form a three to six membered carbocycle
  • R 20 is hydrogen or R 4 .
  • R 2 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 8 cycloalkyl or
  • heterocyclyl is a 4- to 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, S0 2 , N and N(R 20 ) as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo, and wherein the ring is optionally substituted by one or two R 4 ,
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, characterized by the ring is optionally substituted by one to three R 4 ; wherein aryl is phenyl;
  • R 7 is hydrogen or Ci-C 4 alkyl
  • R 8 is independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy or C 3 -C 6 cycloalkyl;
  • R 7 and R 8 together form a 3- to 6-membered carbocycle
  • R 20 is hydrogen or R 4 .
  • R 2 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 8 cycloalkyl or
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, wherein the ring is optionally substituted by one or two methyl; or heterocyclyl is a 5 or 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms selected from N(R 20 ), N, S and O as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo;
  • heterocycyl is a 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyl;
  • each R 2 is independently halogen, d-C 8 alkoxy, Ci-C 8 haloalkoxy-mercapto, d- C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, or d- Cshaloalkylsulfonyl;
  • R 7 is hydrogen or d-dalkyl
  • R 8 is independently hydrogen, cyano, halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy or C 3 -C 6 cycloalkyl;
  • R 7 and R 8 together form a three to six membered carbocycle
  • R 9 is H or d-dalkyl
  • R 20 is hydrogen, d-dalkyl, d-dalkenyl, d-dalkynyl, d-dcycloalkyl, C 3 - dcycloalkyl-CH 2 , d-dhaloalkyl, d-dalkoxyalkyl, d-dhaloalkoxyalkyl, d-dalkoxy-d-dalkyl, d- dalkoxy, d-dalkylcarbonyl, d-dhaloalkylcarbonyl, phenyl-CH 2 -alkyl- or phenyl-CH 2 - wherein the phenyl moiety is substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, furanyl or furanyl substituted by one to three groups
  • halogen independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, thietanyl, oxetanyl, 1-oxo-thietanyl, or 1 ,1-dioxo-thietanyl.
  • R 2 is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 3 , C 3 - C 8 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 8 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 5- or 6-membered saturated heterocyclic ring containing N(R 20 ) and optionally an O atom as ring atoms, wherein one carbon ring atom is substituted by oxo;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy; _din
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 9 is hydrogen or Ci-C 4 alkyl
  • R 20 is hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 - C 6 cycloalkyl-CH 2 -, Ci-C 4 haloalkyl or Ci-C 4 alkoxy.
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, d-
  • heterocyclyl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, thiolanyl, thiolanyl 1 -oxide, thiolanyl 1 ,1 -dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1-dioxo-thietanyl,
  • aryl is phenyl
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 9 is hydrogen or d-dalkyl
  • R 20 is hydrogen, d-dalkyl, d-dalkenyl, C 2 -C 4 alkynyl, d-dcycloalkyl, d- dcycloalkyl-CH 2 -, d-dhaloalkyl or d-dalkoxy.
  • R 2 is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, d-dcycloalkyl or d-dcycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or d-dcycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , hetero
  • heterocyclyl is selected from tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 ,1- dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1 ,-dioxothietanyl each optionally substituted by methyl; or heterocyclyl is 3-oxo-isoxazolidinyl, 2,5-dioxo-1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, wherein each is substituted on the nitrogen atom by Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C3-C 6 cycloalkyl-CH 2 or Ci-C 4 haloalkyl; or heterocycyl is 4-oxo-1 ,3-oxazinanyl, piperidinyl, tetrahydropyranyl, thiazolin
  • aryl is phenyl
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , aryl or aryl substituted by
  • each R 4 is independently halogen, cyano, methyl, halomethyl, methoxy or halomethoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 20 is Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-CH 2 -, or Ci-C 4 haloalkyl;
  • R 2 is C 4 -C 5 cycloalkyl, pyridyl-CH 2 -, Ci-C 4 alkylaminocarbonyl-CH 2 -, d- C 4 haloalkylaminocarbonyl-CH 2 -,;
  • R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl, most preferably trifluoro- methyl.
  • R 4 is aryl or aryl substituted by one to five R 5 , more preferably aryl substituted by one to three R 5 , more preferably phenyl substituted by one to three R 5 .
  • X 2 is C-X 6 or nitrogen (preferably C-X 6 );
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X 1 , X 3 and X 6 are not hydrogen.
  • R 4 is 3,5-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-fluoro-4-chlorophenyl, 3,4- dichlorophenyl, 3-chloro-4-bromophenyl, 3,5-dichloro-4-fluorophenyl, 3,4,5-trichlorophenyl, 3,5-dichloro-4- iodophenyl, 3,4,5-trifluorophenyl, 3-chloro-5-bromophenyl, 3-chloro-5-fluorophenyl, 3-chloro-5- (trifluoromethyl)phenyl, 3,4-dichloro-5-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 4-chloro-3,5- bis(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 2,6-dichloro-4-pyridyl, 2,6-bis(trifluoromethyl)-4
  • R 4 is 3,5-dichloro-4-fluorophenyl-. In one group of compounds R 4 is 3,4,5-trichlorophenyl-. In one group of compounds R 4 is 3,5- bis(trifluoromethyl)phenyl.
  • each R 5 is independently hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 8 alkyl, C-i-C 8 halo- alkyl, C 3 -C 5 cycloalkyl, C 3 -C 5 halocycloalkyl, Ci-C 8 alkenyl, Ci-C 8 haloalkenyl, d-C 8 alkoxy, or C-i-C 8 halo- alkoxy, preferably halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C 3 -C 5 cycloalkyl, C 3 - C 5 halocycloalkyl, Ci-C 2 alkoxy, Ci-C 2 haloalkoxy, more preferably hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, more preferably
  • R 6a and R 6b is hydrogen or Ci-C 8 alkyl, and the other is selected from hydrogen, halogen, cyano, Ci-C 8 alkyl, Ci-C 8 haloalkyl and C 3 -C 8 cycloalkyl, or R 6a and R 6b together from a 3- to 6-membered carbocyclic ring, more preferably at least one of R 6a and R 6b is hydrogen or methyl and the other is hydrogen, methyl, ethyl or cyclopropyl or R 6a and R 6b together form a 3- to 4-membered carbocyclic ring, most preferably one of R 6a and R 6b is hydrogen and the other is hydrogen or methyl.
  • R 7 is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 8 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 - docycloalkyl substituted by one to five R 3 , C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- or heterocyclyl-C(R 7 )(R 18 )- wherein the heterocyclyl is substituted by one to five R 4 , aryl or aryl substituted by one to five R 4 ,
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0 2 , N, and N(R 14 ) as ring atoms;
  • aryl is phenyl; and wherein R 7 and R 8 are independently selected from hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyl.
  • R 8 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 3 , C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or d-docycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , or heterocyclyl;
  • heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, S0 2 and N(R 20 ) as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo, and wherein the ring is optionally substituted by one or two R 4 ;
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, characterized by the ring is optionally substituted by one to three R 4 ; wherein aryl is phenyl;
  • R 7 is hydrogen
  • R 8 is independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d- C 4 alkoxy, Ci-C 4 haloalkoxy or C 3 -C 6 cycloalkyl;
  • R 20 is hydrogen or R 4 .
  • R 8 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 3 , C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , or heterocyclyl;
  • heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, S0 2 and N(R 20 ) as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy;
  • each R 2 is independently halogen, d-C 8 alkoxy, Ci-C 8 haloalkoxy-mercapto, d- dalkylthio, d-dhaloalkylthio, d-dalkylsulfinyl, d-dhaloalkylsulfinyl, d-dalkylsulfonyl, or d- dhaloalkylsulfonyl;
  • each R 3 is independently halogen, cyano, or d-dalkyl
  • each R 4 is independently halogen, cyano, nitro, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, or d-dhaloalkoxy;
  • R 7 is hydrogen
  • R 8 is independently hydrogen, cyano, halogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, d-dhaloalkoxy or C 3 -C 6 cycloalkyl;
  • R 9 is hydrogen or d-dalkyl
  • R 20 is hydrogen or R 4 . More preferably R is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, and wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;
  • each R 4 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or Ci-C 4 haloalkoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, d- C 4 alkylthio, Ci-C 4 alkylsulfinyl and Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 - C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl
  • heterocyclyl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, thiolanyl, thiolanyl 1 -oxide, thiolanyl 1 ,1 -dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1-dioxo-thietanyl,
  • each R 4 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or Ci-C 4 haloalkoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently _ _.
  • heterocyclyl is tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 , 1-dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 , 1 ,-dioxothietanyl each optionally substituted by methyl;
  • heterocycyl is piperidinyl, tetrahydropyranyl, pyridyl, or thiazolyl, each optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;
  • aryl is phenyl
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by
  • each R 4 is independently halogen, cyano methyl, halomethyl, methoxy or halomethoxy; wherein R 7 is hydrogen;
  • R 8 is hydrogen or methyl
  • R 9 is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 0 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 2 , C 3 -Ci 0 cycloalkyl or C 3 - docycloalkyl substituted by one to five R 3 , C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 10 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- or heterocyclyl-C(R 7 )(R 18 )- wherein the heterocyclyl is substituted by one to five R 4 , aryl or aryl substituted by one to five R 4
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0 2 , N, and N(R 14 ) as ring atoms;
  • aryl is phenyl
  • R 7 and R 8 are independently selected from hydrogen, cyano, halogen, Ci-C 4 alkyl,
  • Ci-C 4 haloalkyl Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyl.
  • R 0 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, characterized by the ring is optionally substituted by one to three R 4 ; wherein aryl is phenyl;
  • R 7 is hydrogen
  • R 8 is independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d- C 4 alkoxy, Ci-C 4 haloalkoxy or C 3 -C 6 cycloalkyl.
  • R 0 is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 3 , C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , or heterocyclyl;
  • heterocyclyl is a 4 or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy;
  • each R 2 is independently halogen, d-C 8 alkoxy, Ci-C 8 haloalkoxy-mercapto, d- C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, or d- C 8 haloalkylsulfonyl;
  • each R 3 is independently halogen, cyano, or d-dalkyl
  • each R 4 is independently halogen, cyano, nitro, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, or d-dhaloalkoxy;
  • R 7 is hydrogen
  • R 8 is independently hydrogen, cyano, halogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, d-dhaloalkoxy or C 3 -C 6 cycloalkyl;
  • R 9 is hydrogen or d-dalkyl.
  • R 0 is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, and wherein the ring is optionally substituted by one or two methyl; or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;
  • each R 4 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, or Ci-C 4 haloalkoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 0 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, d- C 4 alkylthio, Ci-C 4 alkylsulfinyl and Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 - C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the ary
  • heterocyclyl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, thiolanyl, thiolanyl 1 -oxide, thiolanyl 1 ,1 -dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1-dioxo-thietanyl,
  • each R 4 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or Ci-C 4 haloalkoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 0 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl- C(R 7 )
  • heterocyclyl is tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 ,1-dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1 ,-dioxothietanyl each optionally substituted by methyl;
  • heterocycyl is piperidinyl, tetrahydropyranyl, pyridyl, or thiazolyl, each optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;
  • aryl is phenyl
  • R 8 is hydrogen or methyl
  • R 0 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl- C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is
  • each R 4 is independently halogen, cyano methyl, halomethyl, methoxy or halomethoxy; wherein R 7 is hydrogen;
  • R 8 is hydrogen or methyl
  • each R is independently hydrogen, halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-
  • Ci-C 4 haloalkoxy more preferably hydrogen, bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably hydrogen, bromo, chloro, fluoro, cyano or methyl, most preferably hydrogen.
  • each R 2 is independently halogen, cyano, nitro, hydroxy, d-C 8 alkoxy, d- dhaloalkoxy, Ci-C 8 alkylcarbonyl, Ci-C 8 alkoxycarbonyl, mercapto, Ci-Csalkylthio, Ci-Cshaloalkylthio, Ci- C 8 alkylsulfinyl, d-C 8 haloalkylsulfinyl, d-C 8 alkylsulfonyl, or d-C 8 haloalkylsulfonyl, more preferably halogen, cyano, nitro, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Ci-C 8 alkylthio, or Ci- Cshaloalkylthio, more preferably halogen, cyano, d-C 8 alkoxy, d-C 8 haloalkoxy, mercapto
  • each R 4 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 - C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, Ci-C 8 haloalkylsulfonyl, Ci-C 8 alkylcarbonyl, Ci-C 8 alkoxycarbonyl, aryl or aryl substituted by one to five R 6 , or heterocyclyl or heterocyclyl substituted by one
  • each R 5 is independently halogen, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkoxy, Ci- C 8 haloalkoxy, d-C 8 alkylthio, or Ci-C 8 haloalkylthio, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably trifluoromethyl, fluoro or chloro.
  • each R 6 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
  • n 1 ;
  • p is 0, 1 , or 2, preferably 0 or 1 , most preferably 0;
  • (E2) P is P1 .
  • Embodiment (E3) P is P2.
  • a 1 is C-R 5 , A 2 is CH, A 3 is CH and A 4 is CH
  • a 1 is CH
  • a 2 is CH
  • a 3 is CH
  • a 4 is CH
  • a 1 is CH
  • a 2 is CH
  • a 3 is CH
  • a 4 is CH and P is P1.
  • a 1 is CH
  • a 2 is CH
  • a 3 is CH and A 4 is CH and P is P2.
  • a 2 is CH
  • a 1 is C-R 5
  • a 2 is C-R 5
  • a 1 is C-R 5
  • a 2 is C-R 5
  • a 3 is C-R 5
  • a 4 is C-R 5
  • a 3 is C-R 5
  • a 4 is C-R 5
  • a 2 is CH
  • G , G 2 , G 3 and G 4 are oxygen
  • a 1 , A 2 , and A 3 are C-H;
  • R , R 7 and R 9 are hydrogen
  • R 2 is Ci-C 6 alkyl or d-C 6 alkyl substituted by one to five R 2 , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to five R 3 , C 3 -C 8 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 8 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , heterocyclyl, Ci-C 6 alkylaminocarbonyl-CH 2 -, Ci-C 6 haloalkyla
  • heterocyclyl is a 4 or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocyclyl is a 5 or 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms selected from, N(R 20 ), N, S and O as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo; doctrine declaration
  • -20- or heterocycyl is a 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyl;
  • R 3 is trifluoromethyl or chlorodifluoromethyl
  • R 4 is group (C)
  • X 2 is C-X 6 or nitrogen (preferably C-X 6 );
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least one of X 1 , X 3 and X 6 is not hydrogen;
  • R 5 is hydrogen, chloro, bromo, fluoro, methyl, ethyl or trifluoromethyl
  • R 6a and R 6b are hydrogen or methyl and the other is hydrogen, methyl, ethyl or cyclopropyl or R 6a and R 6b together form a 3- to 4-membered carbocyclic ring,
  • R 8 is Ci-C 6 alkyl or d-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 3 , C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , or heterocyclyl;
  • heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, S0 2 and N(R 20 ) as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy;
  • R 0 is Ci-C 6 alkyl or d-C 6 alkyl substituted by one to five R 2 , C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 3 , C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to five R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl-C(R 7 )(R 18 )- , aryl or aryl substituted by one to five R 4 , or heterocyclyl;
  • heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, S0 2 and N(R 20 ) as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy;
  • each R 2 is independently halogen, d-C 8 alkoxy, d-C 8 haloalkoxy-mercapto, d-
  • R 7 is hydrogen or Ci-C 4 alkyl
  • R 8 is independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy,
  • R 7 and R 8 together form a three to six membered carbocycle
  • R 9 is H or Ci-C 4 alkyl
  • R 20 is hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 - C 6 cycloalkyl-CH 2 , Ci-C 4 haloalkyl, Ci-C 4 alkoxyalkyl, Ci-C 4 haloalkoxyalkyl, Ci-C 4 alkoxy-Ci-C 4 alkyl, d- C 4 alkoxy, Ci-C 4 alkylcarbonyl, Ci-C 4 haloalkylcarbonyl, phenyl-CH 2 -alkyl- or phenyl-CH 2 - wherein the phenyl moiety is substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, furanyl or furanyl substituted by one to three groups
  • halogen independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, thietanyl, oxetanyl, 1-oxo-thietanyl, or 1 ,1-dioxo-thietanyl.
  • each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 or 2, p is 0.
  • G , G 2 and G 3 are oxygen
  • a , A 2 , A 3 and A 4 are C-H;
  • R , R 7 and R 9 are hydrogen
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and d- C 4 alkylsulfonyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 3 , C 3 -C 8 cycloalkyl- C(R 7 )(R 18 )- or C 3 -C 8 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyl is substituted by one to three groups R 3 , aryl-C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl is substituted by one to five R 4 , heterocyclyl- C
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 5- or 6-membered saturated heterocyclic ring containing N(R 20 ) and optionally an O atom as ring atoms, wherein one carbon ring atom is substituted by oxo;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;
  • R 3 is trifluoromethyl or chlorodifluoromethyl
  • R 4 is group (C)
  • X 2 is C-X 6 or nitrogen (preferably C-X 6 );
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least one of X 1 , X 3 and X 6 is not hydrogen;
  • R 5 is hydrogen, chloro, bromo, fluoro, or methyl
  • R 6a and R 6b are independently hydrogen or methyl
  • R 8 is R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and d- C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, and wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy.
  • R 0 is R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and d- C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R 7 )(R 18 )- or aryl-C(R 7 )(R 18 )- wherein the aryl
  • heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0 2 as ring atoms, and wherein the ring is optionally substituted by one or two methyl;
  • heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, characterized by the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy.
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 9 is hydrogen or Ci-C 4 alkyl; and wherein R is hydrogen, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 3 - C 6 cycloalkyl-CH 2 -, Ci-C 4 haloalkyl or Ci-C 4 alkoxy.
  • each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 , p is 0; k is 0 or 1.
  • P is selected from P1 and P2, or P and R 5 together are P3, or H2 or H6;
  • G , G 2 and G 3 are oxygen
  • a 1 , A 2 , A 3 and A 4 are C-H;
  • R , R 7 and R 9 are hydrogen
  • R 2 is -
  • R 2 is selected from groups A1-A12 and B1-B6 (preferably A2, A8 and B1 )
  • R 3 is trifluoromethyl or chlorodifluoromethyl
  • R 4 is group (C)
  • X 2 is C-X 6 or nitrogen (preferably C-X 6 );
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least one of X 1 , X 3 and X 6 is not hydrogen;
  • R 5 is hydrogen, chloro, bromo, fluoro, or methyl
  • R 6a and R 6b are independently hydrogen or methyl
  • R 8 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and d-
  • R 0 is Ci-C 4 alkyl or Ci-C 4 alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C 4 alkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulfinyl and d- C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- or C 3 -C 6 cycloalkyl-C(R 7 )(R 18 )- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl-terrorism
  • each R 4 is independently halogen, cyano, methyl, halomethyl, methoxy or halomethoxy;
  • R 7 is hydrogen
  • R 8 is hydrogen or methyl
  • R 20 is d-C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-CH 2 -, or C 1 -C 4 haloalkyl;
  • each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 , p is 0; q is 0, 1 or 2; k is 0 or 1.
  • P is P and R , R 2 , G , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 and A 4 are as defined in embodiment E17.
  • P is P2 and R 5 , R 6a , R 6b , R 7 , R 8 , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 and A 4 are as defined in embodiment E17.
  • P is P and R 1 , R 2 , G , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 and A 4 are as defined in embodiment E18.
  • Embodiment (E28) P is P2 and R 5 , R 6a , R 6b , R 7 , R 8 , R 3 , R 4 , R 5 , A 1 , A 2 , A 3 and A 4 are as defined in embodiment E18.
  • a 2 , A 3 and A 4 are independently of one another C-H, C-R 5a or nitrogen;
  • each R 5a is independently hydrogen, halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, d- C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -Ci 0 cycloalkyl, Ci-C 8 alkoxy, d-
  • each R 5b is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkenyl, C 2 - Cshaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -Ci 0 cycloalkyl, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, d-
  • a 1 , A 2 , A 3 ,and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • a 1 is C-R 5 and A 2 , A 3 ,and A 4 each C-H;
  • G , G 2 and G 3 are oxygen
  • R is hydrogen
  • R 2 is Ci-C 4 alkyl or d-C 4 haloalkyl
  • R 3 is C 1 -C 4 haloalkyl
  • R 4 is phenyl or phenyl substituted by one to five halogene atoms
  • R 5 is hydrogen, halogen, cyano, d-C 4 alkyl, Ci-C 4 haloalkyl;
  • R 6a and R 6b are each independently hydrogen, halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl;
  • R 7 is hydrogen, Ci-C 4 alkyl, preferably hydrogen
  • R 8 is Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkylthioCi-C 4 alkyl or C 3 -Ci 0 cycloalkyl;
  • R 9 is hydrogen, d-C 8 alkyl
  • R 0 is Ci-C 4 alkyl, Ci-C 4 haloalkyl, or C 3 -Ci 0 cycloalkyl;
  • R is hydrogen
  • n 0;
  • a 1 , A 2 , A 3 ,and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • a 1 is C-R 5 and A 2 , A 3 ,and A 4 each C-H;
  • G , G 2 and G 3 are oxygen
  • R is hydrogen
  • R 2 is ethyl, 2,2,2-trifluoroethyl- or cyclopropyl
  • R 3 is trifluoromethyl
  • R 4 is phenyl or phenyl substituted by one to three halogene atoms preferably by two halogen atoms;
  • R 5 is hydrogen, halogen, methyl, ethyl, preferably halogen or methyl;
  • R 6a and R 6b are each independently hydrogen, methyl, ethyl, preferably hydrogen or methyl;
  • R 7 is hydrogen
  • R 8 is cyclopropyl, isopropyl, ethyl, chloromethyl, methylthiomethyl or 2,2,2-trifluoroethyl-;
  • R 9 is hydrogen
  • R 0 is methyl, cyclopropyl or isopropyl
  • R is hydrogen
  • a 1 , A 2 , A 3 ,and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • a 1 is C-R 5 and A 2 , A 3 ,and A 4 each C-H;
  • G , G 2 and G 3 are oxygen
  • R is hydrogen
  • R 2 is ethyl, 2,2,2-trifluoroethyl- or cyclopropyl
  • R 3 is trifluoromethyl
  • R 4 is phenyl or phenyl substituted by one to three halogene atoms preferably by two halogen atoms;
  • R 5 is preferably halogen or methyl;
  • R 6a and R 6b are each hydrogen or methyl
  • R 7 is hydrogen
  • R 8 is cyclopropyl, isopropyl, ethyl, chloromethyl, methylthiomethyl or 2,2,2-trifluoroethyl-;
  • R 9 is hydrogen
  • R 10 is methyl, cyclopropyl or isopropyl
  • R is hydrogen
  • n 0.
  • the invention provides compounds of formula lnt-1
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compound of formula I or a salt or N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for compounds of formula I.
  • a 1 , A 2 , A 3 , A 4 , R 3 , R 4 , G and n are as defined for the compound of formula I, and R is OH, d- C 6 alkoxy, CI, F or Br or a salt or N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , R 3 , R 4 , G and n are as defined for compounds of formula I.
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compound of formula I, R is d-C 6 alkyl or d- C 6 alkyl optionally substituted by aryl or a salt or N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for compounds of formula I.
  • Aryl is e.g. phenyl or phenyl optionally substituted by one to three groups selected from cyano, halogen, d-C 4 alkyl, d-C 4 haloalkyl, d-C 4 methoxy or d- dhalomethoxy.
  • a 1 , A 2 , A 3 , A 4 , R 3 , R 4 , R 6a and R 6b are as defined for compounds of formula I.
  • R a and R b are independently hydrogen, tert-butoxycarbonyl or R a and R b together form group D.
  • at least one of R a and R b is not hydrogen.
  • a further group of novel intermediates are compounds of formula Int-V
  • a 2 , A 3 , A 4 , R 3 , R 4 , R and n are as defined for compounds of formula I and R a and R b , are as defined for the compounds of formula Int-IV. or a salt or A/-oxide thereof.
  • the preferred definitions of A 2 , A 3 , A 4 , R 3 , R 4 , R and n are as defined for compounds of formula I.
  • the preferred definitions of R a and R are as defined for the compounds of formula Int-IV.
  • a leaving group as referred to herein may be for example a halogen, d-C 8 alkoxy, d- C 8 alkylsulfonyloxy, Ci-C 8 haloalkylsulfonyloxy, Ci-C 8 arylsulfonyloxy, optionally substituted d- C 8 arylsulfonyloxy ( ar y

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Abstract

La présente invention concerne des composés de formule (I), où P est choisi parmi P1 et P2, ou P et A1 = C-R5 sont ensemble P3 et où les substituants A1, A2, A3, A4, G1, G2, G3, R1, R2, R3, R4, R5, R6a, R6b, R7, R8, R9, R10, R11 et p sont tels que définis dans les revendications. L'invention se rapporte également à des procédés et à des intermédiaires permettant de préparer lesdits composés, à des compositions insecticides, acaricides, nématicides et molluscicides comprenant lesdits composés, ainsi qu'à des procédés d'utilisation desdits composés pour lutter contre les nuisibles de type insectes, acariens, nématodes et mollusques.
PCT/EP2015/059661 2014-05-09 2015-05-04 Composés insecticides à base de dérivés de thiophène WO2015169723A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017153217A1 (fr) 2016-03-09 2017-09-14 Basf Se Dérivés spirocycliques
WO2018082962A1 (fr) 2016-11-02 2018-05-11 Basf Se Procédé de préparation de dérivés de tétrahydrothiophène
RU2657508C1 (ru) * 2017-07-04 2018-06-14 Александр Анатольевич Хахалин Комбинированное противопаразитарное средство для лечения и профилактики гельминтозов и арахноэнтомозов плотоядных животных

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JP2007106756A (ja) 2005-09-14 2007-04-26 Nissan Chem Ind Ltd 置換イソキサゾリン化合物及び有害生物防除剤
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2013135674A1 (fr) * 2012-03-12 2013-09-19 Syngenta Participations Ag Composés de 2-aryl-acétamide insecticides
WO2014079941A1 (fr) * 2012-11-21 2014-05-30 Syngenta Participations Ag Composés insecticides à base de dérivés de carboxamide n-(arylsulfanylmethyl)

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JP2007106756A (ja) 2005-09-14 2007-04-26 Nissan Chem Ind Ltd 置換イソキサゾリン化合物及び有害生物防除剤
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2013135674A1 (fr) * 2012-03-12 2013-09-19 Syngenta Participations Ag Composés de 2-aryl-acétamide insecticides
WO2014079941A1 (fr) * 2012-11-21 2014-05-30 Syngenta Participations Ag Composés insecticides à base de dérivés de carboxamide n-(arylsulfanylmethyl)

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"Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations", 2010
"McCutcheon's Detergents and Emulsifiers Annual", 1981, MC PUBLISHING CORP.
"Pesticide Manual", BRITISH CROP PRODUCTION COUNCI
COMPENDIUM OF PESTICIDE COMMON NAMES, Retrieved from the Internet <URL:http://www.alanwood.net/pesticides/index.html>
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017153217A1 (fr) 2016-03-09 2017-09-14 Basf Se Dérivés spirocycliques
CN108699075A (zh) * 2016-03-09 2018-10-23 巴斯夫欧洲公司 螺环衍生物
WO2018082962A1 (fr) 2016-11-02 2018-05-11 Basf Se Procédé de préparation de dérivés de tétrahydrothiophène
RU2657508C1 (ru) * 2017-07-04 2018-06-14 Александр Анатольевич Хахалин Комбинированное противопаразитарное средство для лечения и профилактики гельминтозов и арахноэнтомозов плотоядных животных

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