WO2014172871A1 - Dérivés de dihydrobenzofurane en tant que composés insecticides - Google Patents

Dérivés de dihydrobenzofurane en tant que composés insecticides Download PDF

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WO2014172871A1
WO2014172871A1 PCT/CN2013/074708 CN2013074708W WO2014172871A1 WO 2014172871 A1 WO2014172871 A1 WO 2014172871A1 CN 2013074708 W CN2013074708 W CN 2013074708W WO 2014172871 A1 WO2014172871 A1 WO 2014172871A1
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substituted
formula
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alkyl
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PCT/CN2013/074708
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Long Lu
Jérome Yves CASSAYRE
Torsten LUKSCH
Myriem El Qacemi
Yaming Wu
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

Definitions

  • the present invention relates to certain dihydrobenzofuran derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
  • isoxazoline derivatives with insecticidal properties are disclosed, for example, in EP 1,731,512.
  • new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.
  • the present invention provides compounds of formula (I)
  • Q is Ql or Q2
  • G 1 is oxygen or sulfur
  • Y 1 is oxygen, sulfur or CH 2 ;
  • Y 3 J and Y 4 are each independently C-H, C-R 5 or nitrogen, wherein no more than one Y 3 J and Y 4 is C-R 5 ;
  • Y 5 is hydrogen, halogen, CpCgalkyl, Ci-Cghaloalkyl or Ca-Cgcycloalkyl;
  • Y 6 is hydrogen, halogen, cyano, Ci-Cgalkyl, Ci-Cghaloalkyl or CrCgcycloalkyl;
  • R la is hydrogen, C r C 8 alkyl, Q-Cgalkoxy, CpCgalkylcarbonyl or CpCgalkoxycarbonyl;
  • R lb is hydrogen, Ci-Qalkyl, CpCgalkylcarbonyl or CpCgalkoxycarbonyl;
  • R 2a is CpCgalkyl or CpCgalkyl substituted by one to five R 7 , C 2 -Cgalkenyl or C 2 -Cgalkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -Cgalkynyl substituted by one to five R 7 , Cr
  • Ciocycloalkyl or CrCiocycloalkyl substituted by one to five R 8 C 3 -Ciocycloalkyl-Ci-C 4 alkylene or C 3 - Ciocycloalkyl-Ci-C 4 alkylene substituted by one to five R 8 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 9 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- substituted by one to five R 9 , aryl or aryl substituted by one to five R 9 , heterocyclyl or heterocyclyl substituted by one to five R 9 , Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Ci-C 8 haloalkylaminocarbonyl-Ci-C alkylene, C 3 -
  • R 2b is C r C 8 alkyl or CpQalkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 , Ci-C 8 alkoxy- Ci-C 8 alkyl or Ci-C 8 alkoxy-Ci-C 8 alkyl substituted by one to five R 7 , C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 8 , C3-Ciocycloalkyl-Ci-C 4 alkylene or C3-Ciocycloalkyl-Ci-C 4 alkylene substituted by one to five R 8 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 9
  • R 3 is Ci-Cghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 10 , or heteroaryl or heteroaryl substituted by one to five R 10 ;
  • each R 5 is independently halogen, cyano, CrQalkyl, Ci-C haloalkyl, CpQalkoxy or C r
  • R a is hydrogen, cyano, Ci-C 8 alkyl, Ci-C 8 haloalkyl or C3-C 8 cycloalkyl;
  • R b is hydrogen, cyano, CpC 8 alkyl, Ci-C 8 haloalkyl or C3-C 8 cycloalkyl;
  • R a and R b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;
  • each R 7 is independently halogen, cyano, nitro, hydroxy, amino, C r C 8 alkyl, C 2 -C 8 alkenyl, C 2 - C 8 alkynyl, Ci-C 8 alkylamino, (Ci-C 8 alkyl) 2 amino, Ci-C 8 alkylcarbonylamino, Cp
  • R 8 is independently halogen, cyano, 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, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, C3-C 6 cycloalkyl or Cp C 8 akoxycarbonyl;
  • each R 9 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, C3-Ciocycloalkyl, C3-Ciocycloalkyl-Cr C 4 alkylene, hydroxy, CpCgalkoxy, CpCghaloalkoxy, mercapto, C r C 8 alkylthio, CpCghaloalkylthio, C r
  • each R 10 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 - Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Ci-C 8 alkoxy, CpCghaloalkoxy, mercapto, Cp Cgalkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfmyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, Cp Cghaloalkylsulfonyl, d-C 8 alkylcarbonyl or CpC 8 alkoxycarbonyl;
  • each R 11 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Cp Qhaloalkoxy;
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms.
  • the compounds of the invention may contain one or more asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. 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 include N-oxides and salts.
  • 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-l -yl or 2-methyl-prop-2- yl.
  • the alkyl groups are preferably C r C 6 , more preferably Ci-C , most preferably C 1 -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 - , -CH 2 -CH 2 -, -CH(CH 3 )-, -CH 2 -CH 2 -CH 2 -, -CH(CH 3 )-CH 2 -, or -CH(CH 2 CH 3 )-.
  • the alkylene groups are preferably C 1 -C3, more preferably C 1 -C 2 , most preferably C ⁇ alkylene groups. Where an alkylene moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C 2 -C ⁇ 5, more preferably C 2 -C , most preferably C 2 -C 3 alkenyl groups. Where an alkenyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkynyl groups. Where an alkynyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • 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,
  • 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, l-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 C3-C8, more preferably C3-C6 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.
  • Preferred heterocyclyl groups are a 4 to 7-membered heterocyclic rings containing one to three heteroatoms independently selected from O, S, SO, S0 2 , N, and N(R 14 ) as ring atoms, wherein R 14 is hydrogen, oxygen or R 9 .
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, dihydrofuranyl, tetrahydrofuranyl, dihydropyranyl, tetrahydropyranyl, dihydrothiophenyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, morpholinyl, thiophenyl, [l,3]dioxolanyl, piperidinyl,
  • bicyclic groups examples include 2,3-dihydro-benzofuranyl, benzo[l,4]dioxolanyl,
  • 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.
  • Prefered heterocyclyl groups are thiophene, thiophene 1 -oxide, thiophene 1 , 1 -dioxide, dihydrothiophene, dihydrothiophene 1 -oxide, dihydrothiophene 1 , 1 -dioxide, pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, and tetrazoyl.
  • Somespecific examples of heterocycles are groups A1-A12 wherein q is 0,1 or 2, and Bl to B6 wherein R 14 is hydrogen or R 9 .
  • Heterocyclyl groups (and heteroaryl groups) according to the present invention do not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms.
  • Preferred values of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , G 1 , R la , R lb , R 2a , R 2b , R 3 , R 4 , R 5 , R a , R b , R 7 , R 8 , R 9 ' R 10 , R 11 are, in any combination (including combinations of preferred values with the original values) as set out below.
  • G 1 is oxygen
  • Y 1 is oxygen
  • Y 2 , Y 3 and Y 4 are nitrogen.
  • Y 2 is C-H or N, more preferably C-H.
  • Y 3 isC-H or C-R 5 , more preferably C-H.
  • Y 4 is C-H or C-R 5 , more preferably C-H.
  • Y 5 is hydrogen, halogen, C r C 8 alkyl or CpQhaloalkyl, more preferably hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl, even more preferably hydrogen, halogen, Ci-C 2 alkyl or C r C 2 haloalkyl, most preferably hydrogen, methyl, chloro, bromo or trifluoromethyl.
  • Y is hydrogen, halogen, cyano, CpC 8 alkyl or Ci-C 8 haloalkyl, more preferably hydrogen, halogen, cyano, Ci-C 4 alkyl or Ci-Czihaloalkyl, even more preferably hydrogen, halogen, cyano, Ci-C 2 alkyl or Ci-C 2 haloalkyl, most preferably hydrogen or methyl.
  • At least one of Y 5 and Y 6 is hydrogen.
  • R la is hydrogen, methyl, halomethyl, ethyl, haloethyl, methylcarbonyl or
  • methoxycarbonyl more preferably hydrogen, methyl, halomethyl, ethyl or haloethyl most preferably hydrogen.
  • R la is hydrogen, methyl, halomethyl, ethyl, haloethyl, methylcarbonyl or
  • methoxycarbonyl more preferably hydrogen, methyl, halomethyl, ethyl or haloethyl most preferably hydrogen.
  • R 2a is Ci-C 8 alkyl or C r C 8 alkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 - Qalkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 , C 3 - Ciocycloalkyl or CrCiocycloalkyl substituted by one to five R 8 , C3-Ciocycloalkyl-C(R 12 )(R 13 )- or Cr C 10 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to five R 9 , heterocyclyl-C(R 12 )
  • 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 12 and R 13 are independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Cp C 4 alkoxy, Ci-C 4 haloalkoxy or C 3 -C 6 cycloalkyl;
  • R 12 and R 13 together form a three to six membered carbocycle
  • R 14 is hydrogen, oxygen or R 9 ;
  • R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to five R 9 .
  • R 2a is Ci-Cealkyl or Ci-Cealkyl substituted by one to five R 7 , C 2 -Cealkenyl or C 2 - Cealkenyl substituted by one to five R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to five R 7 , C 3 - C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to five R 8 , CrC 8 cycloalkyl-C(R 12 )(R 13 )- or Cr C 8 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to five R 9 , heterocyclyl-C(R 12 )
  • heterocyclyl is a 4- to 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, SO 2 , N and N(R 14 ) as ring atoms;
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms independently selected from O, N and S as ring atoms;
  • aryl is phenyl
  • R 12 is hydrogen or CrQalkyl
  • R 13 is hydrogen or Ci-C 4 alkyl
  • R 14 is hydrogen, oxygen or R 9 ;
  • R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to five R 9 .
  • R 2a is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to three R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to three R 7 , C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by one to three R 7 , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 8 , C 3 -C 8 cycloalkyl-C(R 12 )(R 13 )- or C 3 -C 8 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to three R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to threeR 9 , heterocycl
  • 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 14 ) as ring atoms;
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms independently selected from O, N and S as ring atoms;
  • aryl is phenyl
  • each R 7 is independently halogen, cyano,hydroxy, Ci-C alkyl, C 2 -C alkenyl, C 2 - Qalkynyl, Q-Qalkoxy, C -C cycloalkyl, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, C r
  • each R 8 is independently halogen, cyano, CrQalkyl or C 3 -C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, CrQalkyl, Ci-C 4 haloalkyl, d-Qalkoxy or Ci-C 4 haloalkoxy;
  • R 12 is hydrogen or CrQalkyl
  • R 13 is hydrogen or Ci-C 4 alkyl; and wherein R 14 is hydrogen, oxygen or R 9 ;
  • R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to three R 9 .
  • R 2a is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to three R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to three R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to three R 7 , C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to three R 8 , C 3 -C 8 cycloalkyl-C(R 12 )(R 13 )- or C 3 -C 8 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to three R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to threeR 9 , heterocycly
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C 4 cycloalkyl,mercapto, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Cp
  • each R 8 is independently halogen, cyano, Ci-C 4 alkyl or C -C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • R 12 is hydrogen or methyl
  • R 13 is hydrogen or methyl
  • R 14 is hydrogen, oxygen or R 9 ;
  • R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to three R 9 .
  • R 2a is CpCealkyl or CpCealkyl substituted by one to three R 7 or C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five R 8 , wherein each R 7 is independently halogen, cyano, Ci-C 4 alkoxy, C -C 4 cycloalkyl, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, C r C 4 alkylsulfinyl, Ci-C 4 haloalkylsulfinyl, Ci-C 4 alkylsulfonyl or Ci-C 4 haloalkylsulfonyl and each R 8 is independently halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl.
  • R 2b is C r C 8 alkyl or C r C 8 alkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 - C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 , Cp C 6 alkoxy-Ci-C 6 alkyl or Ci-Cealkoxy-Ci-Cealkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl or C 3 - Ciocycloalkyl substituted by one to five R 8 , C 3 -Ciocycloalkyl-C(R 12 )(R 13 )-or C 3 -Ciocycloalkyl- C(R 12 )(R 13 )-substituted by one to five R 8 , aryl-C(R 12 )(R 13 )-substi
  • aryl is phenyl
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S, SO, SO 2 , N and N(R 14 ) as ring atoms;
  • R 12 and R 13 are independently hydrogen, cyano, halogen, Ci-C 4 alkyl, Ci-Czihaloalkyl, Cp C 4 alkoxy, Ci-Czihaloalkoxy or C3-C 6 cycloalkyl, preferably hydrogen or Ci-C 4 alkyl;
  • R 14 is hydrogen, oxygen or R 9 .
  • R 2b is C r C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 7 , C 2 -C 6 alkenyl or C 2 - Cealkenyl substituted by one to five R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to five R 7 , Cp C 6 alkoxy-Ci-C 6 alkyl or Ci-Cealkoxy-Ci-Cealkyl substituted by one to five R 7 , C3-Ciocycloalkyl or C3- Ciocycloalkyl substituted by one to five R 8 , C3-Ciocycloalkyl-C(R 12 )(R 13 )-or C3-Ciocycloalkyl- C(R 12 )(R 13 )-substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-Cl substitute
  • aryl is phenyl
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S, SO, SO 2 , N and N(R 14 ) as ring atoms;
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C cycloalkyl, mercapto, Ci-C alkylthio, Ci-C haloalkylthio, Cp
  • each R 8 is independently halogen, cyano, CrQalkyl or C3-C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, CrQalkyl, Ci-C 4 haloalkyl, d-Qalkoxy or Ci-C 4 haloalkoxy;
  • R 12 is hydrogen or d-Qalkyl
  • R 13 is hydrogen or Ci-C alkyl
  • R 14 is hydrogen, oxygen or R 9 .
  • R 2b is CpCealkyl or CpCealkyl substituted by one to five R 7 , C 2 -Cealkenyl or C 2 - Cealkenyl substituted by one to five R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to five R 7 , Cp C 6 alkoxy-Ci-C 6 alkyl or Ci-C 6 alkoxy-Ci-C 6 alkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl or C 3 - Ciocycloalkyl substituted by one to five R 8 , C 3 -Ciocycloalkyl-C(R 12 )(R 13 )-or C 3 -Ci 0 cycloalkyl- C(R 12 )(R 13 )-substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl; wherein each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 - C 4 alkynyl, Ci-C 4 alkoxy, C 3 -C cycloalkyl, mercapto, Ci-C alkylthio, Ci-C haloalkylthio, Cp
  • each R 8 is independently halogen, cyano, CrQalkyl or C 3 -C cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, CrQalkyl, Ci-C 4 haloalkyl, d-Qalkoxy or Ci-C 4 haloalkoxy;
  • R 12 is hydrogen or methyl
  • R 13 is hydrogen or methyl
  • R 14 is hydrogen, oxygen or R 9 ;
  • R 2b is CpCealkyl or CpCealkyl substituted by one to three R 7 or C3-C 6 cycloalkyl or C3-C 6 cycloalkyl substituted by one to five R 8 , wherein each R 7 is independently halogen, cyano, Cp Qalkoxy, C3-C 4 cycloalkyl, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Ci-C 4 alkylsulfinyl, Ci-C 4 haloalkyl- sulfinyl, Ci-C 4 alkylsulfonyl or Ci-C 4 haloalkylsulfonyl and each R 8 is independently halogen, Ci-C 4 alkyl or Ci-C haloalkyl.
  • R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl, most preferably trifluoromethyl.
  • R 4 is aryl or aryl substituted by one to five R 10 , more preferably aryl substituted by one to three R 10 , more preferably phenyl substituted by one to three R 10 .
  • R 4 is group (A)
  • X 2 is C-X 4 or nitrogen (preferably C-X 4 );
  • X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X 1 , X 3 and X 4 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 halogen, cyano, methyl, halomethyl, methoxy or
  • halomethoxy more preferably chloro, fluoro, cyano or methyl.
  • R a is hydrogen, cyano, Ci-C 4 alkyl more preferably hydrogen, cyano, Ci-C 2 alkyl orCi-C 2 haloalkyl,even more preferably hydrogen or methyl.
  • R b is hydrogen, cyano, Ci-C 4 alkyl or Ci-C 4 haloalkyl, more preferably hydrogen, cyano, Ci-C 2 alkyl or Ci-C 2 haloalkyl, even more preferably hydrogen or methyl, most preferably hydrogen.
  • Ci-C 4 haloalkylthio Ci-C 4 haloalkylthio,Ci-C 4 alkylsulfinyl or Ci-C 4 alkylsulfonyl, even more preferably halogen, cyano, Ci-C 4 alkoxy, Ci-C 4 haloalkylthio, Ci-C 4 alkylsulfinyl, Ci-C 4 haloalkylsulfinyl, Ci-C 4 alkylsulfonyl or most preferably halogen, cyano, methoxy, methylthio, methylsulfinyl or methysulfonyl.
  • each R 8 is independently halogen, cyano, Ci-C 4 alkyl Ci-C 4 alkoxy or C 3 -C 6 cycloalkyl, more preferably halogen, cyano, methyl, propyl or butyl, more preferably chloro, fluoro, cyano, methyl or propyl, most preferably fluoro, cyano, methyl or propyl.
  • each R 9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, hydroxy, CpCgalkoxy, CpCghaloalkoxy, mercapto, CpCgalkylthio, CpCghaloalkylthio, Ci-Cgalkylsulfinyl, Cp Cghaloalkylsulfinyl, Ci-Cgalkylsulfonyl or Ci-Cghaloalkylsulfonyl, more preferably halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy, most preferably halogen, cyano, methyl, halomethyl, methoxy or halomethoxy.
  • each R 10 is independently halogen, CpCgalkyl, Ci-Cghaloalkyl, CpCgalkoxy, Cp Cghaloalkoxy, CpCgalkylthio or Ci-Cghaloalkylthio, more preferably bromo, chloro, fluoro,
  • trifluoromethyl methoxy or methylthio, most preferably trifluoromethyl, fluoro or chloro.
  • each R 11 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.
  • the compound of formula I is in the trans configuration.
  • E1Q is Ql.
  • E2 Q is Q2.
  • Embodiment E5 is embodiment El wherein the compound of formula I is in the trans configuration.
  • Embodiment E6 is embodiment E2 wherein the compound of formula I is in the trans configuration.
  • Embodiment E7 is embodiment E2 wherein Y 5 and Y 6 are hydrogen.
  • Embodiment E8 is embodiment El wherein G 1 is oxygen.
  • Embodiment E9 is embodiment E2 wherein G 1 is oxygen.
  • E10Y 2 is C-H and Y 3 and Y 4 are C-H or C-R 5 wherein no more than one of Y 3 and Y 4 is C-R 5 .
  • Embodiment El 1 is embodiment E10 wherein Y 1 is oxygen.
  • Embodiment El 2 is embodiment E10 wherein R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
  • Embodiment El 3 is embodiment E10 wherein R 4 is group A.
  • Embodiment El 4 is embodiment El l wherein R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
  • Embodiment El 5 is embodiment El l wherein R 4 is group A.
  • Embodiment El 6 is embodiment E14 wherein R 4 is group A.
  • Embodiment El 7 is embodiment E10 wherein G 1 is oxy ⁇ *en.
  • Embodiment El 8 is embodiment El l wherein G 1 is oxy ⁇ *en.
  • Embodiment El 9 is embodiment E12 wherein G 1 is oxy ⁇ *en.
  • Embodiment E20 is embodiment E13 wherein G 1 is oxy ⁇ *en.
  • Embodiment E21 is embodiment E14 wherein G 1 is oxy ⁇ *en.
  • Embodiment E22 is embodiment E15 wherein G 1 is oxy ⁇ *en.
  • Embodiment E22 is embodiment E16 wherein G 1 is oxy ⁇ *en.
  • G 1 is oxygen; Y 1 is oxygen;
  • Y 2 is C-H
  • Y 3 and Y 4 are C-H or C-R 5 ,wherein no more than one of Y 3 and Y 4 is C-R 5 ;
  • Y 5 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl
  • Y 6 is hydrogen, halogen, cyano, Ci-C 4 alkyl or Ci-C 4 haloalkyl;
  • R la is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R lb is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R 2a is CpCgalkyl or CpCgalkyl substituted by one to five R 7 , C 2 -Cgalkenyl or C 2 -Cgalkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -Cgalkynyl substituted by one to five R 7 , C3- Ciocycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 8 , C 3 -Ci 0 cycloalkyl-C(R 12 )(R 13 )- or C 3 - Ciocycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to five R 9 , heterocyclyl-C(R 12
  • 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 la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to five R 9 ;
  • R 2b is C r C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -Cgalkynyl substituted by one to five R 7 , CpCealkoxy- CpCealkyl or Ci-Cealkoxy-Ci-Cealkyl substituted by one to five R 7 , C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 8 , C 3 -Ci 0 cycloalkyl-C(R 12 )(R 13 )-or C 3 -Ci 0 cycloalkyl-C(R 12 )(R 13 )-substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or
  • aryl is phenyl
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S, SO, S0 2 , N and N(R 14 ) as ring atoms;
  • R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl
  • R 4 is group A, wherein X 2 is C-X 4 or nitrogen and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, providing that at least one of X 1 , X 3 and X 4 is not hydrogen;
  • R 5 is halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • R a is hydrogen, cyano, Ci-C 4 alkyl or Ci-C 4 haloalkyl
  • R b is hydrogen, cyano, d-Qalkyl or Ci-C 4 haloalkyl.
  • R 12 and R 13 are independently hydrogen, cyano, halogen, CpQalkyl, Ci-C haloalkyl, Q- Qalkoxy, Ci-C 4 haloalkoxy or C3-C 6 cycloalkyl; or R 12 and R 13 together form a three to six membered carbocycle; and
  • R 14 is hydrogen, oxygen or R 9 .
  • G 1 is oxygen
  • Y 1 is oxygen
  • Y 2 is C-H
  • Y 3 and Y 4 are C-H or C-R 5 , wherein no more than one of Y 3 and Y 4 is C-R 5 ;
  • Y 5 is hydrogen, halogen, Ci-C 2 alkyl or Ci-C 2 haloalkyl
  • Y 6 is hydrogen, halogen, cyano, Ci-C 2 alkyl or Ci-C 2 haloalkyl;
  • R la is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R lb is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R 2a is CpCealkyl or CpCealkyl substituted by one to five R 7 , C 2 -Cealkenyl or C 2 -Cealkenyl substituted by one to five R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to five R 7 , Ca-Cgcycloalkyl or C3-C 8 cycloalkyl substituted by one to five R 8 , C3-C 8 cycloalkyl-C(R 12 )(R 13 )- or Ca-Cgcycloalkyl- C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R 12 )(R 13 )- wherein the aryl is substituted by one to five R 9 , heterocyclyl-C(R 12 )(R
  • 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 14 ) as ring atoms;
  • heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms independently selected from O, N and S as ring atoms;
  • aryl is phenyl
  • R la and R 2a together form a 4- or 5 -membered ring fragment containing carbon atoms as ring members, optionally substituted by one to five R 9 ;
  • R 2b is C r C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to five R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to five R 7 , CpCealkoxy- CpCealkyl or Ci-Cealkoxy-Ci-Cealkyl substituted by one to five R 7 , C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 8 , C 3 -C 10 cycloalkyl-C(R 12 )(R 13 )-or C 3 -C 10 cycloalkyl-C(R 12 )(R 13 )-substituted by one to five R 8 , aryl-C(R 12 )(R 13 )- or aryl-
  • aryl is phenyl
  • heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S, SO, SO 2 , N and N(R 14 ) as ring atoms;
  • R 3 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl
  • R 4 is group A, wherein X 2 is C-X 4 or nitrogen and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, proving that at least one of X 1 , X 3 and X 4 is not hydrogen;
  • R 5 is halogen, cyano, methyl, halomethyl, methoxy or halomethoxy
  • R a is hydrogen, cyano, Ci-C 2 alkyl or Ci-C 2 haloalkyl
  • R b is hydrogen, cyano, Ci-C 2 alkyl or Ci-C 2 haloalkyl
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Cp Cgalkoxy, C3-C 4 cycloalkyl, mercapto, Ci-Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfmyl, Cp Cghaloalkylsulfinyl, Ci-Cgalkylsulfonyl or Ci-Cghaloalkylsulfonyl;
  • each R 8 is independently halogen, cyano, C r C 4 alkyl or C 3 -C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Q- C 4 haloalkoxy;
  • R 12 is hydrogen or Ci-C 4 alkyl
  • R 13 is 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 12 and R 13 together form a 3 - to 6-membered carbocycle
  • R 14 is hydrogen, oxygen or R 9 .
  • G 1 is oxygen
  • Y 1 is oxygen
  • Y 2 , Y 3 and Y 4 are C-H;
  • Y 5 is hydrogen, methyl, chloro, bromo or trifluoromethyl
  • Y 6 is hydrogen or methyl
  • R la is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R lb is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R 2a is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to three R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to three R 7 , C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by one to three R 7 , C 3 - Cgcycloalkyl or Ca-Cgcycloalkyl substituted by one to three R 8 , C3-C 8 cycloalkyl-C(R 12 )(R 13 )- or C3- C 8 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to three R 8 , aryl-C(R 12 )(R 13 )- or aryl-C(R )(R )- wherein the aryl is substituted by one to three R , heterocyclyl-C(R )(R )
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl; or R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to three R 9 .
  • R 2b is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to three R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to three R 7 , C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by one to three R 7 ,
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl
  • R 3 is trifluoromethyl
  • R 4 is group A, wherein X 2 is C-X 4 and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, proving that at least one of X 1 , X 3 and X 4 is not hydrogen;
  • R a is hydrogen or methyl
  • R b is hydrogen or methyl
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C r C 4 alkoxy, C 3 -C 4 cycloalkyl, mercapto, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Ci-C 4 alkylsulfinyl, Cp C 4 haloalkylsulfinyl, Ci-C 4 alkylsulfonyl or Ci-C 4 haloalkylsulfonyl;
  • each R 8 is independently halogen, cyano, C r C 4 alkyl or C -C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Cp C 4 haloalkoxy;
  • R 12 is hydrogen or methyl
  • R 13 is hydrogen or methyl.
  • G 1 is oxygen
  • Y 1 is oxygen
  • Y 2 , Y 3 and Y 4 are C-H;
  • Y 5 is hydrogen, methyl, chloro, bromo or trifluoromethyl
  • Y 6 is hydrogen or methyl
  • R la is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R 2a is CpCealkyl or CpCealkyl substituted by one to three R 7 , C 2 -Cealkenyl or C 2 -Cealkenyl substituted by one to three R 7 , C 2 -Cealkynyl or C 2 -Cealkynyl substituted by one to three R 7 , C 3 - Cgcycloalkyl or CrCgcycloalkyl substituted by one to three R 8 , C 3 -C 8 cycloalkyl-C(R 12 )(R 13 )- or C 3 - C 8 cycloalkyl-C(R 12 )(R 13 )- wherein the cycloalkyl is substituted by one to three R 8 , aryl-C(R 12 )(R 13 )- or
  • aryl-C(R )(R )- wherein the aryl is substituted by one to three R , heterocyclyl-C(R )(R )-, aryl or aryl substituted by one to three R 9 , heterocyclyl or heterocyclyl substituted by one to three R 9 , C r C 4 alkyl-0-
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, tnazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl
  • R la and R 2a together form a 4- or 5-membered ring fragment containing carbon atoms as ring members, optionally substituted by one to three R 9 .
  • R 3 is trifluoromethyl
  • R 4 is group A, wherein X 2 is C-X 4 and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, proving that at least one of X 1 , X 3 and X 4 is not hydrogen;
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C2-C 4 alkenyl, C2-C 4 alkynyl, Cp Qalkoxy, C 3 -C cycloalkyl, mercapto, Ci-C alkylthio, Ci-C haloalkylthio, Ci-C alkylsulfinyl, C r Qhaloalkylsulfinyl, Ci-C alkylsulfonyl or Ci-C haloalkylsulfonyl;
  • each R 8 is independently halogen, cyano, C r C alkyl, or C 3 -C cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, CrQalkyl, Ci-C haloalkyl, CpQalkoxy or Q- Qhaloalkoxy;
  • R 12 is hydrogen or methyl
  • R 13 is hydrogen or methyl.
  • G 1 is oxygen
  • Y 1 is oxygen
  • Y 2 , Y 3 and Y 4 are C-H;
  • Y 5 is hydrogen or methyl
  • Y 6 is hydrogen or methyl
  • R lb is hydrogen, methyl, halomethyl, ethyl or haloethyl
  • R 2b is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to three R 7 , C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted by one to three R 7 , C 2 -C 6 alkynyl or C 2 -C 6 alkynyl substituted by one to three R 7 ,
  • heterocyclyl is pyridyl, pyridyl-N-oxide, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl or group Al to A12 (preferably pyridyl or A2);
  • aryl is phenyl;
  • R 3 is trifluoromethyl;
  • R 4 is group A, wherein X 2 is C-X 4 and X 1 , X 3 and X 4 are independently hydrogen, halogen or trihalomethyl, proving that at least one of X 1 , X 3 and X 4 is not hydrogen;
  • R a is hydrogen or methyl
  • R b is hydrogen or methyl
  • each R 7 is independently halogen, cyano, hydroxy, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, Cp C 4 alkoxy, C3-C 4 cycloalkyl, mercapto, Ci-C 4 alkylthio, Ci-C 4 haloalkylthio, Ci-C 4 alkylsulfinyl, Cp C 4 haloalkylsulfinyl, Ci-C 4 alkylsulfonyl or Ci-C 4 haloalkylsulfonyl;
  • each R 8 is independently halogen, cyano, C r C 4 alkyl, or C 3 -C 4 cycloalkyl;
  • each R 9 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or Q- C 4 haloalkoxy;
  • R 12 is hydrogen or methyl
  • R 13 is hydrogen or methyl.
  • Y 1 is oxygen
  • Y 1 is sulfur
  • Y 1 is CH 2 .
  • Q is Ql and R 2a is CpCgalkyl or CpCgalkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 .
  • Q is Ql and R 2a is C 3 -Ci 0 cycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 8 , C 3 -Ciocycloalkyl-Ci-C 4 alkylene or C -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 8 .
  • Q is Ql and R 2a is aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 9 , aryl or aryl substituted by one to five R 9 .
  • Q is Ql and R 2a is heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Cr C 4 alkylene- substituted by one to five R 9 , heterocyclyl or heterocyclyl substituted by one to five R 9 .
  • Q is Q2 and R 2b is CpCgalkyl or CpCgalkyl substituted by one to five R 7 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 7 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 7 , Ci-Cgalkoxy-CpCgalkyl or CpCgalkoxy-Ci-Cgalkyl substituted by one to five R 7 .
  • Q is Q2 and R 2b is C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 8 , C -Ci 0 cycloalkyl-Ci-C 4 alkylene or C -Ci 0 cycloalkyl-Ci-C 4 alkylene substituted by one to five R 8 .
  • Q is Q2 and R 2b is aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- substituted by one to five R 9 , aryl or aryl substituted by one to five R 9 .
  • Q is Q2 and R 2b is heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Cr C 4 alkylene- substituted by one to five R 9 , heterocyclyl or heterocyclyl substituted by one to five R 9 .
  • the present invention also provides intermediates useful for the preparation of compounds of formula I.
  • Y , Y , Y% Y , Y Y , R , R j , R , R 6a and R 6b are as defined for compounds of formula I, or a salt or N-oxide thereof
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , R 1 , R 3 , R 4 , R a and R b are as defined for compounds of formula I.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , R 3 , R 4 , R a and R b are as defined for compounds of formula I and or a salt or N-oxide thereof
  • the preferred definitions of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , R 1 , R 4 , R a and R b are as defined for compounds of formula I.
  • R is a leaving group (preferably hydroxy, C r C 15 alkoxy, CI, F or Br),and Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , G 1 , R 3 and R 4 are as defined for compounds of formula I and or a salt or N-oxide thereof.
  • a leaving group is for example 1 -pyrrolyl, 1 -benzotriazolyl, 1 -pyrazolyl, 1 -tetrazolyl, N-succinimidyloxy, N- phthalimidyloxy, 1 -benzotriazolyloxy, N-piperidyloxy, N-l,2,3-benzotriazin-4-onyloxy, SCl -ClOalkyl, SAryl, pentafluorophenoxy, 4-nitrophenoxy, 3-pyridyloxy, 2,4,5 -trichlorophenoxy, or
  • R a is hydroxy, PPh 3 , Br or CI
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , R 3 and R 4 are as defined for compounds of formula I or a salt or N-oxide thereof.
  • the preferred definitions of Y , Y , Y , Y , Y , R and R are as defined for compounds of formula I.
  • R a is OH.
  • In another group of compounds of formula Int-IV R a is PPh 3 .
  • Int-IV is Br or CI.
  • Y 1 is hydroxy
  • R b is nitro or halogen
  • R 31 is nitro, cyano, fluoro, chloro, bromo, iodo or C(0)R' wherein R' is hydroxy, Ci-Ci 5 alkoxyor Ci 2 3 4 3 4
  • Y 6 is hydrogen, hydroxy, halogen, CpCgalkyl, CpCghaloalkyl or C 3 -C 8 cycloalkyl and Y 1 , Y 2 , Y 3 , Y 4 , R 3 and R 4 are as defined for compounds of formula I, or a salt or N-oxide thereof.
  • R c is NH 2 or R , wherein R is nitro, cyano, halogen (e.g. fluoro, chloro, bromo,
  • each R JJ is independently C r C 6 alkyland Y , Y ⁇ Y ⁇ Y Y°, R J and R" are as defined for compounds of formula I, or a salt or N-oxide thereof.
  • the preferred definitions of and Y 1 , Y 2 , Y 3 , Y 4 , Y 6 , R 3 and R 4 are as defined for compounds of formula I.
  • compounds of formula I** are more biologically active than compounds of formula I*.
  • the invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1, e.g. 10:1 to 1 : 10, e.g. a substantially 50:50 molar ratio.
  • the molar proportion of compound I** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.Each compound disclosed in Tables 1 to 179represents a disclosure of a compound according to the compound of formula I*, and a disclosure according to the compound of formula I**.
  • Table 1 provides 192 compounds of formula IA wherein R2a is l-oxo-tetrahydrofuran-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 2 provides 192 compounds of formula LA wherein R2a is l -oxo-thietan-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 3 provides 192 compounds of formula LA wherein R2a is l,l-dioxo-tetrahydrofuran-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 4 provides 192 compounds of formula LA wherein R2a is l,l -dioxo-thietan-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 5 provides 192 compounds of formula IA wherein R2a is (l,l -dioxo-thietan-2-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 6 provides 192 compounds of formula IA wherein R2a is 4-oxo-2-(trifluoromethyl)-l,3- oxazinan-5-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 7 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-(cyclopropylmethyl)- isoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 8 provides 192 compounds of formula IA wherein R2a is 2,5 -dioxo-1 -(2,2,2- trifluoroethyl)pyrrolidin-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 9 provides 192 compounds of formula LA wherein R2a is N-(3,3,3-trifluoropropyl)acetamid-2- yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 10 provides 192 compounds of formula LA wherein R2a is N-(2,2,2-trifluoroethyl)acetamid-2- yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 11 provides 192 compounds of formula IA wherein R2a is 2-methoxy-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 12 provides 192 compounds of formula IA wherein R2a is 3-chloroprop-l -yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 13 provides 192 compounds of formula LA wherein R2a is 3,3,3-trifluoro-propyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 14 provides 192 compounds of formula LA wherein R2a is (thietan-2-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 15 provides 192 compounds of formula IA wherein R2a is l-oxo-thietan-3-yl-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 16 provides 192 compounds of formula IA wherein R2a is (oxetan-2-yl)-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 17 provides 192 compounds of formula LA wherein R2a is (thiazol-4-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 18 provides 192 compounds of formula IA wherein R2a is (2-pyrimid-2-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 19 provides 192 compounds of formula LA wherein R2a is (thietan-3-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 20 provides 192 compounds of formula LA wherein R2a is (l,l-dioxo-thietan-3-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 21 provides 192 compounds of formula LA wherein R2a is (N-methoxypiperid-4-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 22 provides 192 compounds of formula LA wherein R2a is (tetrahydrofuran-2-yl)-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 23 provides 192 compounds of formula IA wherein R2a is (2-pyridyl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 24 provides 192 compounds of formula LA wherein R2a is phenylmethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 25 provides 192 compounds of formula IA wherein R2a is (cyclobutyl)methyl, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 26 provides 192 compounds of formula IA wherein R2a is (2-fluorophenyl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 27 provides 192 compounds of formula LA wherein R2a is N-ethylacetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 28 provides 192 compounds of formula IA wherein R2a is N-(but-2-yl)acetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 29 provides 192 compounds of formula IA wherein R2a is 2,2,2-trifluoro-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 30 provides 192 compounds of formula IA wherein R2a is tetrahydrofuran-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 31 provides 192 compounds of formula LA wherein R2a is thietan-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 32 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-(3,3,3-trifluoro-propyl)- isoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 33 provides 192 compounds of formula IA wherein R2a is 3-oxetanyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 34 provides 192 compounds of formula LA wherein R2a is tetrahydrofuran-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 35 provides 192 compounds of formula LA wherein R2a is 2-oxo-l -(2,2,2- trifluoroethyl)pyrrolidin-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 36 provides 192 compounds of formula IA wherein R2a is cyclobutyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 37 provides 192 compounds of formula LA wherein R2a is 2-norbornyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 38 provides 192 compounds of formula LA wherein R2a is cyclopropyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 39 provides 192 compounds of formula LA wherein R2a is 3-(hydroxyimino)-cyclobutyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 40 provides 192 compounds of formula LA wherein R2a is 3-(ethoxyimino)-cyclobutyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 41 provides 192 compounds of formula LA wherein R2a is 2-oxopyrrolidin-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 42 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-(2,2,2-trifluoro-ethyl)- isoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 43 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-(2,2-difluoro-ethyl)- isoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 44 provides 192 compounds of formula LA wherein R2a is 3-methyloxetan-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 45 provides 192 compounds of formula LA wherein R2a is l -phenyleth-l-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 46 provides 192 compounds of formula IA wherein R2a is 1 -cyanocyclopropyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 47 provides 192 compounds of formula IA wherein R2a is 2-fluoro-cycloprop-l -yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 48 provides 192 compounds of formula IA wherein R2a is l,l,l-trifluoroprop-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 49 provides 192 compounds of formula LA wherein R2a is 2-methylsulfanyl-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 50 provides 192 compounds of formula IA wherein R2a is N-methoxyethaniminyl, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 51 provides 192 compounds of formula LA wherein R2a is 3-(methoxyimino)-cyclobutyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 52 provides 192 compounds of formula LA wherein R2a is N-ethoxyethaniminyl, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 53 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-ethylisoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 54 provides 192 compounds of formula LA wherein R2a is 2-oxo-l-(ethyl)pyrrolidin-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 55 provides 192 compounds of formula LA wherein R2a is but-l-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 56 provides 192 compounds of formula LA wherein R2a is but-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 57 provides 192 compounds of formula IA wherein R2a is 1 -methoxy-prop-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 58 provides 192 compounds of formula LA wherein R2a is 2-oxo-l-methylpyrrolidin-3-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 59 provides 192 compounds of formula LA wherein R2a is 3-oxo-2-methylisoxazolidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 60 provides 192 compounds of formula LA wherein R2a is prop-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 61 provides 192 compounds of formula LA wherein R2a is methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 62 provides 192 compounds of formula IA wherein R2a is ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 63 provides 192 compounds of formula LA wherein R2a is prop-l -yl, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 64 provides 192 compounds of formula IA wherein R2a is 2,2-difluoro-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 65 provides 192 compounds of formula IA wherein R2a is l -oxo-thietan-3-yl-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 66 provides 192 compounds of formula IA wherein R2a is tetrahydropyran-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 67 provides 192 compounds of formula LA wherein R2a is 2-fluoro-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 68 provides 192 compounds of formula LA wherein R2a is thietan-3-yl-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 69 provides 192 compounds of formula LA wherein R2a is cyclopentyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 70 provides 192 compounds of formula LA wherein R2a is (2-cyclopropyl-l-oxa-3,4-diazol-5- yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 71 provides 192 compounds of formula LA wherein R2a is 2-thiazolinyl, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 72 provides 192 compounds of formula LA wherein R2a is 4-cyanopyrimid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 73 provides 192 compounds of formula IA wherein R2a is (pyrimidin-5-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 74 provides 192 compounds of formula LA wherein R2a is 2-chloropyrid-5-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 75 provides 192 compounds of formula LA wherein R2a is (pyrazin-2-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 76 provides 192 compounds of formula LA wherein R2a is (2-chlorothiazol-5-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 77 provides 192 compounds of formula IA wherein R2a is 2-methylsulfmyl-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 78 provides 192 compounds of formula LA wherein R2a is 2-(methylsulfonyl)-ethyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 79 provides 192 compounds of formula LA wherein R2a is N-methylpiperidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 80 provides 192 compounds of formula IA wherein R2a is N-(3,3,3- trifluoropropanoyl)piperidin-4-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 81 provides 192 compounds of formula LA wherein R2a is l-(2-chloro-pyrid-5-yl)eth-l-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 82 provides 192 compounds of formula LA wherein R2a is N-cyclopropylacetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 83 provides 192 compounds of formula IA wherein R2a is (2-chloro-pyrid-3-yl)-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 84 provides 192 compounds of formula IA wherein R2a is 3-oxo-2-propargylisoxazolidin-4- yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 85 provides 192 compounds of formula IA wherein R2a is (3-fluorophenyl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 86 provides 192 compounds of formula IA wherein R2a is (2-fluorophenyl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 87 provides 192 compounds of formula IA wherein R2a is (l -oxo-thietan-3-yl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 88 provides 192 compounds of formula IA wherein R2a is N-(cyclopropyl)acetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 89 provides 192 compounds of formula IA wherein R2a is (4-chlorophenyl)methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 90 provides 192 compounds of formula IA wherein R2a is l-methyl-l -(pyrid-2-yl)eth-l -yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 91 provides 192 compounds of formula IA wherein R2a is 1 -(2-pyridyl)cyclopropyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 92 provides 192 compounds of formula IA wherein R2a is (2-chloro-pyrid-5-yl)-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 93 provides 192 compounds of formula IA wherein R2a is (2-chloro-pyrid-4-yl)-methyl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 94 provides 192 compounds of formula IA wherein R2a is N-(benzyl)acetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 95 provides 192 compounds of formula IA wherein R2a is N-(2-fluorobenzyl)acetamid-2-yl-, and R3, R4, Y5, Y6 and cis/trans are as defined in Table P.
  • Table 96 provides 144 compounds of formula IB wherein R2b is ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 97 provides 144 compounds of formula IB wherein R2b is 2,2,2-trifluoro-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 98 provides 144 compounds of formula IB wherein R2b is prop-2-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 99 provides 144 compounds of formula IB wherein R2b is methyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 100 provides 144 compounds of formula IB wherein R2b is 2-fluoro-cycloprop-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 101 provides 144 compounds of formula IB wherein R2b is prop-l -yl, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 102 provides 144 compounds of formula IB wherein R2b is 2-fluoro-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 103 provides 144 compounds of formula IB wherein R2b is 2-cyano-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 104 provides 144 compounds of formula IB wherein R2b is 1 -fluoroethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 105 provides 144 compounds of formula IB wherein R2b is 2-methylprop-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 106 provides 144 compounds of formula IB wherein R2b is propen-2-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 107 provides 144 compounds of formula IB wherein R2b is cyclopropylmethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 108 provides 144 compounds of formula IB wherein R2b is 2-methoxy-ethyl-, R3 is
  • R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 109 provides 144 compounds of formula IB wherein R2b is 3-methyloxetan-3-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 110 provides 144 compounds of formula IB wherein R2b is 1 -methylcyclopropyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 111 provides 144 compounds of formula IB wherein R2b is dihydrofuran-4-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 112 provides 144 compounds of formula IB wherein R2b is cyclopropyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 113 provides 144 compounds of formula IB wherein R2b is cyclobutyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 114
  • Table 114 provides 144 compounds of formula IB wherein R2b is methylsulfonylmethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 115 provides 144 compounds of formula IB wherein R2b is propen-l -yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 116 provides 144 compounds of formula IB wherein R2b is methylsulfanylmethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 117 provides 144 compounds of formula IB wherein R2b is 1 -methoxyeth-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 118 provides 144 compounds of formula IB wherein R2b is 5-pyrimidyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 119 provides 144 compounds of formula IB wherein R2b is but-2-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 120 provides 144 compounds of formula IB wherein R2b is l -fluoroprop-2-yl-, R3 is
  • R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 121 provides 144 compounds of formula IB wherein R2b is 2-methylpropen-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 122 provides 144 compounds of formula IB wherein R2b is 1 -cyanocyclopropyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 123 provides 144 compounds of formula IB wherein R2b is N-formylaminomethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 124 provides 144 compounds of formula IB wherein R2b is 2-methylsulfinyl-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 125 provides 144 compounds of formula IB wherein R2b is 2-(methylsulfonyl)-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 126 provides 144 compounds of formula IB wherein R2b is l -oxo-tetrahydrofuran-3-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 127 provides 144 compounds of formula IB wherein R2b is l-oxo-thietan-3-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 128 provides 144 compounds of formula IB wherein R2b is l,l-dioxo-tetrahydrofuran-3-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 129 provides 144 compounds of formula IB wherein R2b is l,l -dioxo-thietan-3-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 130 provides 144 compounds of formula IB wherein R2b is 3-chloroprop-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 131 provides 144 compounds of formula IB wherein R2b is 3,3,3-trifluoro-propyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 132 provides 144 compounds of formula IB wherein R2b is 3,3,3-trifluoro-propyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 132 provides 144 compounds of formula IB wherein R2b is 3,3,3-trifluoro-propyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 132 provides 144 compounds of formula IB wherein R2b is 3,3,3-trifluoro-propyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and
  • Table 132 provides 144 compounds of formula IB wherein R2b is thietan-3-yl-, R3 is tnfluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 133 provides 144 compounds of formula IB wherein R2b is 3-oxetanyl-, R3 is tnfluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 134 provides 144 compounds of formula IB wherein R2b is tetrahydrofuran-2-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 135 provides 144 compounds of formula IB wherein R2b is l,l,l-trifluoroprop-2-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 136 provides 144 compounds of formula IB wherein R2b is but-l-yl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 137 provides 144 compounds of formula IB wherein R2b is 2,2-difluoro-ethyl-, R3 is trifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 138 provides 144 compounds of formula IB wherein R2b is ethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 139 provides 144 compounds of formula IB wherein R2b is 2,2,2-trifluoro-ethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 140 provides 144 compounds of formula IB wherein R2b is prop-2-yl-, R3 is
  • Table 141 provides 144 compounds of formula IB wherein R2b is methyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 142 provides 144 compounds of formula IB wherein R2b is 2-fluoro-cycloprop-l-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 143 provides 144 compounds of formula IB wherein R2b is prop-l-yl, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 144 provides 144 compounds of formula IB wherein R2b is 2-fluoro-ethyl-, R3 is
  • Table 145 provides 144 compounds of formula IB wherein R2b is 2-cyano-ethyl-, R3 is
  • Table 146 provides 144 compounds of formula IB wherein R2b is 1 -fluoroethyl-, R3 is
  • Table 147 provides 144 compounds of formula IB wherein R2b is 2-methylprop-l-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 148 provides 144 compounds of formula IB wherein R2b is propen-2-yl-, R3 is
  • Table 149 provides 144 compounds of formula IB wherein R2b is cyclopropylmethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 150
  • Table 150 provides 144 compounds of formula IB wherein R2b is 2-methoxy-ethyl-, R3 is
  • Table 151 provides 144 compounds of formula IB wherein R2b is 3-methyloxetan-3-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 152 provides 144 compounds of formula IB wherein R2b is 1 -methylcyclopropyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 153 provides 144 compounds of formula IB wherein R2b is dihydrofuran-4-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 154 provides 144 compounds of formula IB wherein R2b is cyclopropyl-, R3 is
  • Table 155 provides 144 compounds of formula IB wherein R2b is cyclobutyl-, R3 is
  • Table 156 provides 144 compounds of formula IB wherein R2b is methylsulfonylmethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 157 provides 144 compounds of formula IB wherein R2b is propen-l -yl-, R3 is
  • Table 158 provides 144 compounds of formula IB wherein R2b is methylsulfanylmethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 159 provides 144 compounds of formula IB wherein R2b is 1 -methoxyeth-l-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 160 provides 144 compounds of formula IB wherein R2b is 5-pyrimidyl-, R3 is
  • Table 161 provides 144 compounds of formula IB wherein R2b is but-2-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 162 provides 144 compounds of formula IB wherein R2b is l -fluoroprop-2-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 163 provides 144 compounds of formula IB wherein R2b is 2-methylpropen-l-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 164 provides 144 compounds of formula IB wherein R2b is 1 -cyanocyclopropyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 165 provides 144 compounds of formula IB wherein R2b is N-formylaminomethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 166 provides 144 compounds of formula IB wherein R2b is 2-methylsulfinyl-ethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 167 provides 144 compounds of formula IB wherein R2b is 2-(methylsulfonyl)-ethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 168
  • Table 168 provides 144 compounds of formula IB wherein R2b is l -oxo-tetrahydrofuran-3-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 169 provides 144 compounds of formula IB wherein R2b is l -oxo-thietan-3-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 170 provides 144 compounds of formula IB wherein R2b is l,l -dioxo-tetrahydrofuran-3-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 171 provides 144 compounds of formula IB wherein R2b is l,l -dioxo-thietan-3-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 172 provides 144 compounds of formula IB wherein R2b is 3-chloroprop-l-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 173 provides 144 compounds of formula IB wherein R2b is 3,3,3-trifluoro-propyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 174 provides 144 compounds of formula IB wherein R2b is thietan-3-yl-, R3 is
  • Table 175 provides 144 compounds of formula IB wherein R2b is 3-oxetanyl-, R3 is
  • Table 176 provides 144 compounds of formula IB wherein R2b is tetrahydrofuran-2-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 177 provides 144 compounds of formula IB wherein R2b is l,l,l-trifluoroprop-2-yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 178 provides 144 compounds of formula IB wherein R2b is but-l -yl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • Table 179 provides 144 compounds of formula IB wherein R2b is 2,2-difluoro-ethyl-, R3 is chlorodifluoromethyl and R4, Y5, R6a, R6b and cis/trans are as defined in Table Q.
  • the compounds of the invention may be made by a variety of methods as shown in the following Schemes.
  • Compounds of formula (la) wherein G 1 is oxygen can be prepared by reacting an amine of formula (II) with a compound of formula (III) wherein G 1 is oxygen and X A is OH, Ci-C 6 alkoxy or CI, F or Br.
  • X A is OH
  • a coupling reagent such as ⁇ , ⁇ '-dicyclohexyl-carbo-diimide (“DCC”), l-ethyl-3-(3-dimethyl-amino-propyl)-carbodiimide hydrochloride (“EDC”) or bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-C1”)
  • DCC ⁇ , ⁇ '-dicyclohexyl-carbo-diimide
  • EDC l-ethyl-3-(3-dimethyl-amino-propyl)-carbodiimide hydrochloride
  • BOP-C1 bis(2-oxo-3-oxazolidinyl)phosphonic chloride
  • HOBT hydroxybenzo-triazole
  • X A is CI
  • such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst for example dimethylaminopyridine.
  • a nucleophilic catalyst for example dimethylaminopyridine.
  • X A is CpCealkoxy it is sometimes possible to convert the ester directly to the amide by heating the ester and amine together in a thermal process.
  • Suitable bases include pyridine, triethylamine, 4-(dimethylamino)-pyridine (“DMAP”) or diisopropylethylamine (Hunig's base).
  • Preferred solvents are NN-dimethylacetamide, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane, ethyl acetate and toluene.
  • the reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature.
  • Compounds of formula (III) are either known in the literature or can be prepared using methods known to a person skilled in the art. Some of these methods are described in the preparation Examples.
  • Compounds of formula (la), wherein G 1 is sulfur may be made by treatment of a compound of formula (III), wherein G 1 is oxygen and X A is OH, Ci-C 6 alkoxy or CI, F or Br, with a thio-transfer reagent such as Lawesson's reagent or phosphorus pentasulfide prior to progressing to compounds of formula (la), as described under 1).
  • a thio-transfer reagent such as Lawesson's reagent or phosphorus pentasulfide prior to progressing to compounds of formula (la), as described under 1).
  • R When R is OH such reactions are usually carried out in the presence of a coupling reagent, such as ⁇ , ⁇ '-dicyclohexylcarbodiimide (“DCC”), l-ethyl-3-(3- dimethylamino-propyl)carbodiimide hydrochloride (“EDC”) or bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-Cl”), in the presence of a base, and optionally in the presence of a nucleophilic catalyst, such as hydroxybenzotriazole (“HOBT").
  • DCC ⁇ , ⁇ '-dicyclohexylcarbodiimide
  • EDC l-ethyl-3-(3- dimethylamino-propyl)carbodiimide hydrochloride
  • BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphonic chloride
  • R When R is CI, such reactions are usually carried out in the presence of
  • a biphasic system comprising an organic solvent, preferably ethyl acetate, and an aqueous solvent, preferably a solution of sodium hydrogen carbonate.
  • R is Ci-C 6 alkoxy it is sometimes possible to convert the ester directly to the amide by heating the ester and amine together in a thermal process.
  • Suitable bases include pyridine, triethylamine, 4-(dimethylamino)-pyridine (“DMAP”) or diisopropylethylamme (Hunig's base).
  • Preferred solvents are NN-dimethylacetamide, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane, ethyl acetate and toluene.
  • the reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature.
  • Amines of formula (XI) are either known in the literature or can be prepared using methods known to a person skilled in the art. Some of these methods are described in the preparation Examples.
  • Acid halides of formula (IX), wherein G 1 is oxygen and R is CI, F or Br, may be made from carboxylic acids of formula (IX), wherein G 1 is oxygen and R is OH, under standard conditions, as described for example in WO 2009/080250.
  • Carboxylic acids of formula (IX), wherein G 1 is oxygen and R is OH may be formed from esters of formula (IX), wherein G 1 is oxygen and R is Q-Cealkoxy as described for example in WO 2009/080250.
  • Phosphonium (XIV) is deprotonated with a strong base for example K 2 C0 3 , BuLi, tBuOK, LiHMDS or LDA in an aprotic solvent for example toluene or THF and then adding a carbonyl or formula (XIII).
  • a strong base for example K 2 C0 3 , BuLi, tBuOK, LiHMDS or LDA
  • an aprotic solvent for example toluene or THF
  • R is aryl and X is CI or Br can be prepared by treating compounds of formula (XIX) wherein X is CI or Br with a phosphine of formula (XVI) wherein R is aryl using conditions described in 17).
  • Alcohols of formula of formula (XX) wherein Y 5 is hydrogen, CpCgalkyl, CpCghaloalkyl or C 3 -C 8 cycloalkyl can be prepared by reduction of carbonyls of formula (XXI) using a hydride source for example NaBH 4 , LiAlH 4 , diisobutylaluminum hydride, H 2 in presence of a transition catalyst such as Ni and Pd using well-established methods known to a person skilled in the art specific examples are described in the experimental section.
  • a hydride source for example NaBH 4 , LiAlH 4 , diisobutylaluminum hydride, H 2
  • a transition catalyst such as Ni and Pd
  • Alcohols of formula of formula (XX) wherein Y 5 is hydrogen, CpCgalkyl, Cp Cghaloalkyl or C 3 -Cgcycloalkyl can be prepared by reduction of compounds of formula (XXII) wherein R 31 is C0 2 R using a hydride source for example LiAlH 4 or diisobutylaluminum hydride when R is Cp C 6 alkyl and BH 3 when R is hydrogen using well-established methods known to a person skilled in the art and specific examples are described in the experimental section.
  • a hydride source for example LiAlH 4 or diisobutylaluminum hydride when R is Cp C 6 alkyl
  • BH 3 when R is hydrogen
  • Ketone of formula of formula (XXI) wherein Y 5 CpCgalkyl or C 3 -Cgcycloalkyl can be prepared by treating compounds of formula (XXII) wherein R 31 is cyano or C(0)NMeOMe with an organomagnesium reagent of formula Y 5 MgX wherein X is CI, Br or I or with an organolithium reagent of formula Y 5 Li in an aprotic solvent for example tetrahydrofiiran using well-established methods known to a person skilled in the art and described in the experimental section.
  • ketones of formula of formula (XXI) wherein Y 5 CpCgalkyl, CpCghaloalkyl or C 3 -C 8 cycloalkyl can be prepared by treating compounds of formula (XXII) wherein R 31 is bromo or iodo with an organolithium, for example butyllithium, or an organomagnesium, for example
  • Alcohols of formula of formula (XX) wherein Y 5 CpCghaloalkyl can be prepared by reaction aldehydes of formula (XXI) wherein Y 5 is hydrogen with nucleophilic haloalkyl source for example trimethylsilyltrifluoromethane in presence of a nucleophilic activator for example CsF.
  • nucleophilic haloalkyl source for example trimethylsilyltrifluoromethane
  • CsF nucleophilic activator for example CsF
  • Ketone of formula (XXI) wherein Y 5 is hydrogen, CpCgalkyl or CpCghaloalkyl can be prepared by oxidation of alcohols of formula of formula (XX) wherein Y 5 is hydrogen, CpCgalkyl or Cp Cghaloalkyl with oxidants for example pyridinium chlorochromate, Dess-Martin periodinane or Swern- type oxidations using well-established methods known to a person skilled in the art and specific examples are described in the experimental section.
  • Cgcycloalkyl and Y 6 is hydrogen, a halogen, Ci-Qalkyl, Ci-C 8 haloalkyl, C -C 8 cycloalkyl or cyano can be prepared through a Horner-Wadsworth-Emmons reaction between carbonyl (XXI) wherein Y 5 is hydrogen, CpCgalkyl, CpCghaloalkyl, or C -C 8 cycloalkyland phosphonate (XXIII) wherein A 1 is C r C 4 alkyl or or aryl, Y 6 is hydrogen, a halogen, CpCgalkyl, Ci-Cghaloalkyl, or C 3 - Cgcycloalkyl, G 1 is oxygen or sulfur and R is Ci-C 4 alkoxy or NR la R 2a wherein R la and R 2a are as defined in claim 1.
  • Phosphonates (XXIII) are treated with a strong base for example NaH, KHMDS, tBuOK, or a weaker base DBU with an additional activator such as LiCl or MgC ⁇ in an aprotic solvent for example tetrahydrofuran or dimethoxyethane and then carbonyl (XXI) is added.
  • a strong base for example NaH, KHMDS, tBuOK, or a weaker base DBU
  • an additional activator such as LiCl or MgC ⁇
  • an aprotic solvent for example tetrahydrofuran or dimethoxyethane
  • Y 5 is hydrogen, CpCgalkyl, CpCghaloalkyl, or C 3 - Cgcycloalkyl
  • Y 6 is hydrogen, CpCgalkyl, CpCghaloalkyl, Q-Cgcycloalkyl or cyano
  • Y 5 is hydrogen, CpCgalkyl, CpCghaloalkyl, Q-Cgcycloalkyl or cyano
  • Y 5 is hydrogen, CpCgalkyl, CpCghaloalkyl, Q-Cgcycloalkyl or cyano
  • Y 6 is hydrogen, CpCgalkyl, CpCghaloalkyl, Q-Cgcycloalkyl or cyano
  • a palladium catalyst for example Pd(OAc) 2 (DTPF) (DTPF: l,l '-bis(ditertbutylphosphino)ferrocene), and a base for example dicyclohexylmethylamine, an
  • Aledhydes of formula (XXV) wherein X is bromo or chloro and Y 6 is hydrogen, CpCgalkyl, CpCghaloalkyl, C 3 -C 8 cycloalkyl or cyano can be obtained by reacting ketones of formula (XXVI)with Vilsmeyer reagent, obtained from reaction of POX 3 or COX 2 wherein X is chloro or bromo with dimethylformamide using well-established methods known to a person skilled in the art and specific examples are described in the experimental section.
  • Ketones of formula (XXVI) wherein Y 6 is hydrogen, CpCgalkyl, CpCghaloalkyl, C3- Cgcycloalkyl or cyano can be obtained by treating ketones of formula (XXI) wherein Y 6 is Ci-C 9 alkyl, Ci- 7 haloalkylmethyl, Ca-Cgcycloalkylmethyl or cyanomethyl with ⁇ , ⁇ -dimethylformamide dimethyl acetal in a polar solvent for example dimethylformamide using well-established methods known to a person skilled in the art and specific examples are described in the experimental section.
  • Anilines of formula (XXVIII) can be obtained by reduction of compounds of formula (XXXVII) by using a suitable reducing agent as described extensively in Kabalka, G. W.; Varma, R. S., Reduction of Nitro and Nitroso Compounds. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, L, Eds. Pergamon Press: Oxford, 1991 ; Vol. 8, p 363.
  • Suitable reducing agent can be for example iron, magnesium, zinc, tin(II) chloride in protic solvent for example water, ethanol, methanol, acetic acid, aqueous HC1.

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Abstract

La présente invention concerne des composés de formule (I) dans laquelle Q est (Q1) ou (Q2) G1 représente l'oxygène ou le soufre ; Y1 représente l'oxygène, le soufre ou CH2 ; Y2, Y3 et Y4 représentent chacun indépendamment C-H, C-R5 ou l'azote, dans laquelle pas plus d'un parmi Y2, Y3 et Y4 représente C-R5 ; Y5 représente l'hydrogène, un halogène, un alkyle en C1 à C8, un haloalkyle en C1 à C8 ou un cycloalkyle en C3 à C8 ; Y6 représente l'hydrogène, un halogène, un cyano, un alkyle en C1 à C8, un haloalkyle en C1 à C8 ou un cycloalkyle en C3 à C8 ; R1a représente l'hydrogène, un alkyle en C1 à C8, un alcoxy en C1 à C8, un alcoxylkylcarbonyle en C1 à C8 ou un alcoxycarbonyle en C1 à C8 ; R1b représente l'hydrogène, un alkyle en C1 à C8, un alkylcarbonyle en C1 à C8 ou un alcoxycarbonyle en C1 à C8 ; R3 représente un haloalkyle en C1 à C8 ; R4 représente un aryle ou un aryle substitué par un à cinq R10, ou un hétéroaryle ou un hétéroaryle substitué par un à cinq R10 ; R6a représente l'hydrogène, un cyano, un alkyle en C1 à C8, un haloalkyle en C1 à C8 ou un cycloalkyle en C3 à C8 ; R6b représente l'hydrogène, un cyano, un alkyle en C1 à C8, un haloalkyle en C1 à C8 ou un cycloalkyle en C3 à C8 ; ou R6a et R6b conjointement avec l'atome de carbone auquel ils sont liés peuvent former un noyau carbocyclique comportant 3 à 6 chaînons ; et R2a, R2b, R et R sont tels que définis dans les revendications. L'invention concerne également des procédés de lutte contre les insectes, les acariens, les nématodes ou les mollusques, comprenant l'application à un nuisible, à un locus d'un nuisible, ou à une plante susceptible d'être attaquée par un nuisible d'une quantité efficace sur le plan insecticide, acaricide, nématicide ou molluscicide d'un composé de formule I.
PCT/CN2013/074708 2013-04-25 2013-04-25 Dérivés de dihydrobenzofurane en tant que composés insecticides WO2014172871A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4881967A (en) * 1986-12-10 1989-11-21 E. I. Du Pont De Nemours And Company Heterocyclic 2,3-dihydrobenzofuran herbicides
DE102004023605A1 (de) * 2003-05-19 2004-12-23 Syngenta Participations Ag Neue Herbizide
CN1780825A (zh) * 2003-04-30 2006-05-31 Fmc有限公司 杀虫剂(二卤代丙烯基)苯基烷基取代的二氢苯并呋喃和二氢苯并吡喃衍生物
WO2012061698A2 (fr) * 2010-11-05 2012-05-10 Senomyx, Inc. Composés utiles en tant que modulateurs de trpm8

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4881967A (en) * 1986-12-10 1989-11-21 E. I. Du Pont De Nemours And Company Heterocyclic 2,3-dihydrobenzofuran herbicides
CN1780825A (zh) * 2003-04-30 2006-05-31 Fmc有限公司 杀虫剂(二卤代丙烯基)苯基烷基取代的二氢苯并呋喃和二氢苯并吡喃衍生物
DE102004023605A1 (de) * 2003-05-19 2004-12-23 Syngenta Participations Ag Neue Herbizide
WO2012061698A2 (fr) * 2010-11-05 2012-05-10 Senomyx, Inc. Composés utiles en tant que modulateurs de trpm8

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds
US11452711B2 (en) 2020-09-03 2022-09-27 Pfizer Inc. Nitrile-containing antiviral compounds
US11541034B2 (en) 2020-09-03 2023-01-03 Pfizer Inc. Nitrile-containing antiviral compounds

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