WO2014079935A1 - Composés insecticides à base de dérivés d'arylthioacétamide - Google Patents

Composés insecticides à base de dérivés d'arylthioacétamide Download PDF

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WO2014079935A1
WO2014079935A1 PCT/EP2013/074394 EP2013074394W WO2014079935A1 WO 2014079935 A1 WO2014079935 A1 WO 2014079935A1 EP 2013074394 W EP2013074394 W EP 2013074394W WO 2014079935 A1 WO2014079935 A1 WO 2014079935A1
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formula
methyl
trifluoromethyl
compound
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PCT/EP2013/074394
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WO2014079935A9 (fr
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Jérôme Yves CASSAYRE
Myriem El Qacemi
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Syngenta Participations Ag
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
    • C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
    • C07D291/04—Five-membered rings

Definitions

  • the present invention relates to 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 is C-R 5b ;
  • n 0, 1 or 2;
  • R 2 is C r C 8 alkyl or C r C 8 alkyl substituted by one to five R 6 , C 2 -C 8 alkenyl or C 2 -C 8 alkenyl substituted by one to five R 6 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - Ciocycloalkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl-Ci-C 4 alkylene or C 3 -Ci 0 cycloalkyl-Ci- C 4 alkylene substituted by one to five R 7 , aryl-Ci-C 4 alkylene or aryl-Ci-C 4 alkylene wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene or heterocyclyl-Ci-C 4 al
  • R 3 is C C 8 haloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ; each R 5a is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 - Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C3-Ciocycloalkyl, d-Cgalkoxy, CpCghaloalkoxy, Cp Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl- or d- Cghaloalkylsulfonyl-;
  • R 5b is halogen, C r C 8 alkyl, C C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 - C 8 haloalkynyl, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 7 ,
  • each R 6 is independently halogen, cyano, nitro, hydroxy, C3-Ciocycloalkyl, Ci-C 8 alkoxy, Cp
  • Ci-C 8 alkylcarbonyl Ci-C 8 alkoxycarbonyl, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, or Ci-C 8 haloalkylsulfonyl;
  • each R 7 is independently halogen, cyano, C r C 8 alkyl or Ci-C 8 haloalkyl;
  • each R 8 and R 9 is independently halogen, cyano, nitro, CpQalkyl, Q-Qhaloalkyl, 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, C r C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, CpQalkylsulfonyl, C r C 8 haloalkylsulfonyl, Ci-C 8 alkylcarbonyl, Q-Qalkoxycarbonyl, aryl or aryl substituted by one to five R 10 or heterocyclyl or heterocyclyl substituted by one to five R 10
  • each R 10 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or C r
  • 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.
  • 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 are preferably Q-C3, more preferably C r C 2 , most preferably Q 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) -configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C2-C6, more preferably C2-C4, most preferably C2-C3 alkynyl groups.
  • alkynyl groups contain one or more carbon-carbon triple bonds, each of which may be located at any point on the chain.
  • 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.
  • 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 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.
  • 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, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,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[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,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 A 1 , A 2 , A 3 , A 4 , G 1 , n, R 1 , R 2 , R 3 , R 4 , R 5a , R 5b , R 6 , R 7 , R 8 , R 9 , R 10 and R 12 are, in any combination, 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 1 is oxygen
  • R 1 is hydrogen, methyl, ethyl, methylcarbonyl or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, even more preferably hydrogen or methyl, most preferably hydrogen.
  • R 2 is Ci-C 8 alkyl or Ci-Cgalkyl substituted by one to five R 6 , C 2 -C 8 alkenyl or C 2 - Cgalkenyl substituted by one to five R 6 , C 2 -C 8 alkynyl or C2-Cgalkynyl substituted by one to five R 6 , C 3 - Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl-Ci-C 4 alkylene or C 3 - Ciocycloalkyl-Ci-C 4 alkylene substituted by one to five R 7 , aryl-Ci-C 4 alkylene or aryl-Ci-C 4 alkylene wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene or heterocyclyl-Cr C 4 alkylene wherein the heterocyclyl moiety is substitute
  • each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
  • R 2 is C r C 8 alkyl or C r C 8 alkyl substituted by one to five R 6 , C 2 -C 8 alkenyl or C 2 - Cgalkenyl substituted by one to five R 6 , C 2 -C 8 alkynyl or C 2 -C 8 alkynyl substituted by one to five R 6 , C 3 - Ciocycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl-Ci-C 4 alkylene or C 3 - Ciocycloalkyl-Ci-C 4 alkylene substituted by one to five R 7 , phenyl-Ci-C 4 alkylene or phenyl-Ci-C 4 alkylene wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene or pyridyl-C 4 al
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five halogen, C 3 -C 6 cyclo- alkyl or C 3 -C 6 cycloalkyl substituted by one to five groups independently selected from halogen, methyl and halomethyl, C 3 -C 6 cycloalkyl-methylene or C 3 -C 6 cycloalkyl-methylene substituted by one to five - groups independently selected from halogen, methyl and halomethyl, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen.
  • R 3 is chlorodifluoromethyl or trifluoromethyl, most preferably trifluoromethyl.
  • R 4 is aryl or aryl substituted by one to three R 9 , more preferably R 4 is phenyl or phenyl substituted by one to three R 9 , even more preferably R 4 is phenyl substituted by one to three R 9 , more preferably R 4 is
  • X is C-R 12 or nitrogen (preferably C-R 12 ) and each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen.
  • each R 5a is independently halogen, cyano, nitro, CpCgalkyl, C3-Cgcycloalkyl, d- Cghaloalkyl, C 2 -Cgalkenyl, more preferably halogen, cyano, nitro, CpCgalkyl, C 2 -Cgalkenyl, C3- Cgcycloalkyl, Ci-Cghaloalkyl, even more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, vinyl, most preferably bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl or methyl.
  • R 5b is halogen, Ci-Cgalkyl, C3-Cgcycloalkyl, Ci-Cghaloalkyl, C 2 -Cgalkenyl, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, vinyl, even more preferably bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl or methyl, most preferably bromo, chloro, or methyl, most preferably chloro, bromo or methyl.
  • R 5b is bromo.
  • R 5b is chloro.
  • R 5b is methyl.
  • R 5b is chloro or bromo.
  • each R 6 is independently halogen, nitro, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Q- C 4 alkoxy, Ci-C 4 haloalkoxy, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, even more preferably chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy, most preferably bromo, chloro, fluoro, or trifluoromethyl.
  • each R 7 is independently chloro, fluoro, cyano, or methyl or trifluoromethyl, most preferably fluoro, cyano, or methyl.
  • each R 8 is independently halogen, cyano, nitro, Ci-Cgalkyl, Ci-Cghaloalkyl, C 2 - Cgalkenyl, C 2 -Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, hydroxy, Ci-Cgalkoxy, Ci-Cghaloalkoxy, mercapto, Ci-Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl, Ci-Cghaloalkylsulfinyl, d- Cgalkylsulfonyl, Ci-Cghaloalkylsulfonyl, Ci-Cgalkylcarbonyl, Ci-Cgalkoxycarbonyl, aryl or aryl substituted by one to five R 10 or heterocyclyl or heterocyclyl substituted by one to five R 10 , more preferably each R 8 is independently halogen,
  • each R 10 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 is 0. In another group of compounds n is 1. In another group of compounds n is 2. Preferably n is 0.
  • a 2 is C-H and A 3 and A 4 are C-H or one ofA 3 and A 4 is N;
  • G 1 is O, R 3 is chlorodifluoromethyl or trifluoromethyl;
  • 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-,
  • a 2 is C-H and A 3 and A 4 are C-H or one ofA 3 and A 4 is N;
  • G 1 is O, R 1 is H, R 3 is chlorodifluoromethyl or trifluoromethyl;
  • 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-
  • a 2 , A 3 and A 4 are C-H; G 1 is O, R 1 is H, R 3 is chlorodifluoromethyl or trifluoromethyl; R 4 is 33,5-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-ch
  • a 2 , A 3 and A 4 are C-H; G 1 is O, R 1 is H, R 3 is chlorodifluoromethyl or trifluoromethyl; 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
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are C-H;
  • G 1 is O;
  • R 1 is hydrogen;
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five halogen, C3-C 6 cycloalkyl or C3-C 6 cycloalkyl substituted by one to five groups independently selected from halogen, methyl and halomethyl, C 3 - C 6 cycloalkyl-methylene or C 3 -C 6 cycloalkyl-methylene substituted by one to five groups independently selected from halogen, methyl and halomethyl, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen;
  • R 3 is chlorodifluoromethyl or trifluoromethyl;
  • X is C-R or nitrogen (preferably C-R ) and each R is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen; R 5b is chloro, bromo or methyl.
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are C-H;
  • G 1 is O;
  • R 1 is hydrogen;
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five halogen, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl substituted by one to five groups independently selected from halogen, methyl and halomethyl, C 3 - C 6 cycloalkyl-methylene or C 3 -C 6 cycloalkyl-methylene substituted by one to five groups independently selected from halogen, methyl and halomethyl, C 2 -C 4 alkenyl or C 2 -C 4 alkenyl substituted by one to five halogen, C 2 -C 4 alkynyl or C 2 -C 4 alkynyl substituted by one to five halogen;
  • R 3 is trifluoromethyl;
  • R 4 is group Alwherein
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are C-H;
  • G 1 is oxygen;
  • R 1 is hydrogen;
  • R 2 is ethyl, propyl, butyl, fluoroethyl, fluoropropyl, fluorobutyl, difluoroethyl, difluoropropyl, difluorobutyl, trifluoroethyl, trifluoropropyl, trifluorobutyl, cyclopropyl, cyclobutyl,
  • a 1 , A 2 , A 3 , A 4 , R 3 , R 4 , G 1 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 1 and 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 11 is Ci-Cealkyl or Q- 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, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 inethoxy or d- C 4 halomethoxy.
  • a , A , A , A , G , n, R and R 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 , G 1 , n, R 1 and R 2 are as defined for compounds of formula I.
  • a 1 , A 2 , A 3 , A 4 , R 3 , R 4 , n, G 1 and n are as defined for the compound of formula I, and R is OH, Ci-Cealkoxy, CI, F or Br, Z 1 is hydrogen, halogen, cyano, Ci-Cgalkyl, optionally substituted aryl-Cr C 4 alkylene-, Ci-Cgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio- or a salt or N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , G 1 , n, R 3 and R 4 are as defined for compounds of formula I.
  • Z 1 is preferably hydrogen, benzyl, halogen (preferably chloro) or cyano.
  • Aryl preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C 4 alkyl, C -C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • Aryl is e.g. phenyl or phenyl optionally substituted by one to three groups selected from cyano, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 methoxy or Ci-C 4 halomethoxy.
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compound of formula I, and Z 1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C 4 alkylene-, Ci-Cgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio- 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, Ci-C 4 alkyl, C r C 4 haloalkyl, Ci-C 4 methoxy or Ci-C 4 halomethoxy.
  • a leaving group as referred to herein may be for example a halogen, Q-Cgalkoxy, Q-
  • R is methyl or ethyl
  • R is methyl or ethyl
  • Table 1 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 2 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 2 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 3 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 4 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 5 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 6 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 7 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 8
  • Table 8 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 9
  • Table 9 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 10 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 11 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is
  • Table 12 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 13 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is
  • Table 14 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 15 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 16
  • Table 16 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 17 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 18 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 19 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 20
  • Table 20 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 21
  • Table 21 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 22 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 22 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 23 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 24 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 25 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 26 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 27 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 28 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 29 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 30 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 31 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 32 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 33 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 34 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 35 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 36 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 37 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 38 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 39 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 40 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 42 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 43 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 44
  • Table 44 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 45 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 46 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 47 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 48 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 49 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 50 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 51 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 52 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 53 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 54 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 55 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 56 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 57 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 58 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 59 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 60 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 61 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 62 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 63 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 64 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 65 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is
  • Table 66 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 67 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is
  • Table 68 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 69 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 70
  • Table 70 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 71 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 72 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 73 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 74
  • Table 74 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 75
  • Table 75 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 76
  • Table 76 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 77 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 78 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 78 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 78 provides 672 compounds of formula IA wherein R
  • Table 78 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 79 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 80
  • Table 80 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 81
  • Table 81 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 82 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 83 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 84 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 85 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 86 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 87 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 88 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3 -chloro-5 -(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 89 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 90 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 91 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 92 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 93 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 94 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 95 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 96 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 97 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 98 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 99 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 100 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 101 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 102 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 103 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 104 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 105 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 106 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 107 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.
  • Table 109 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 111 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 113 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 114 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 115 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 116 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 117 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 118 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 119 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is
  • Table 120 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 121 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is
  • Table 122 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 123 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 124 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 125 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 126 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 127 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 128
  • Table 128 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 129
  • Table 129 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 130
  • Table 130 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 131 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 132 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 133 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 134 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 135 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 136
  • Table 136 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 137 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3 -chloro-5 -fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 138 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 139 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 140 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3 -chloro-5 -(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 141 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 142
  • Table 142 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 143 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 144 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 145 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 146 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 147 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 148 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 149 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 150 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 151 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 152 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 152 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 152 provides 672 compounds of formula IA wherein Rl is hydrogen, R3
  • Table 152 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 153 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 154 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 155 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 156 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 157 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is trifluoromethyl-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 158 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is trifluoromethyl-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 159 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is trifluoromethyl-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 160 provides 672 compounds of formula IA wherein Rl is hydrogen, R3 is difluorochloro-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 161 provides 672 compounds of formula IA wherein Rl is methyl-, R3 is difluorochloro-, R4 is 3-bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Table 162 provides 672 compounds of formula IA wherein Rl is ethyl-, R3 is difluorochloro-, R4 is 3- bromo-5-(trifluoromethyl)phenyl , A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.
  • Compounds of formula I include at least one chiral centre and may exist as compounds of formula I* or compounds of formula I**.
  • Each compound listed in Tables 1 to 162 represents a specific disclosure corresponding to the compound of formula I* and a specific disclosure corresponding to the compound 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.
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.
  • Each compound disclosed in Tables 1 to 162 represents a specific disclosure of a compound according to formula I*, as well as a specific disclosure of a compound according to formula I**.
  • the compound of formula Int-I may exist as a compound of formula Int-I* and Int-I**
  • the invention includes mixtures of compounds Int-I* and Int-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 Int-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 Int-I** are preferred.
  • the compound of formula Int-II may exist as a compound of formula Int-II* and Int- II**
  • the invention includes mixtures of compounds Int-II* and Int-II** 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 Int-II** 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 Int-II** are preferred.
  • the compound of formula Int-III may exist as a compound of formula Int-III* and Int- III**
  • the invention includes mixtures of compounds Int-III* and Int-III** 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 Int-III** 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 Int-III** are preferred.
  • the compounds of the invention may be made by a variety of methods as shown in the following Schemes.
  • Compounds of formula (IA) wherein G 1 is oxygen can be prepared by reacting a compound of formula (II) wherein G 1 is oxygen and R is OH, Ci-C 6 alkoxy or CI, F or Br, with an amine of formula
  • R is CI
  • such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.
  • a base preferably ethyl acetate
  • 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 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.
  • Amines 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.
  • Acid halides of formula (II), wherein G 1 is oxygen and R is CI, F or Br may be made from carboxylic acids of formula (II), wherein G 1 is oxygen and R is OH, under standard conditions, as described for example in WO2009/080250.
  • Carboxylic acids of formula (II), wherein G 1 is oxygen and R is OH may be formed from esters of formula (II), wherein G 1 is oxygen and R is Ci-C 6 alkoxy as described for example in
  • Compounds of formula (IA), wherein G 1 is sulfur may be made by treatment of a compound of formula (II), wherein G 1 is oxygen and R 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 elaborating to compounds of formula (I), as described under 1).
  • a thio-transfer reagent such as Lawesson' s reagent or phosphorus pentasulfide prior to elaborating to compounds of formula (I), as described under 1).
  • compounds of formula (IA) wherein G 1 is oxygen can be prepared by various methods from an intermediate of formula (IV) as shown in Scheme 2 wherein G 1 is oxygen and X B is a leaving group, for example a halogen, such as bromo or X B is cyano, formyl, acid, amide or acetyl according to similar methods to those described in WO2009/080250.
  • An intermediate of formula (IV) can be prepared for example from an intermediate of formula (V) as described in Scheme 1.
  • Ar stands for roup Arl, Ar2, Ar3, Ar4 or A5:
  • a 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 11 , G 1 , R and n are as defined for compounds of formula I, Int-I, Int-II and Int-III and X c is a leaving group for example a halogen, Q-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • phosphonate esters e.g. -OP(0)(OR) 2, wherein R is methyl or ethyl
  • R is methyl or ethyl
  • oxidising reagent Two equivalents of oxidising reagent are required to convent a sulfide to a sulfone.
  • Preferred solvents are ethanol, methanol, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, ethyl acetate, toluene, dichloromethane and water, or mixtures thereof.
  • the reaction is optionally carried out in the presence of a base, for example a carbonate, such as sodium hydrogen carbonate.
  • 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.
  • phosphonate esters e.g. -OP(0)(OR) 2, wherein R is methyl or ethyl
  • R is methyl or ethyl
  • X c is a leaving group, for example a halogen, such as fluoro, chloro or bromo, with a mercaptan of formula (X) wherein R is OH or d-Cealkoxy, for example methoxy or tert-butyloxy.
  • a base such as an amine or a carbonate, for example potassium or cesium carbonate in solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, dimethylacetamide at a temperature of from 0°C to 150°C, preferably from 25°C to 100°C.
  • reaction can be carried out in the presence of a catalyst, for a example a palladium catalyst, and a ligand, for example a phosphine ligand in a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene at a temperature of from 0°C to 150°C, preferably from 80°C to 130°C.
  • a catalyst for a example a palladium catalyst
  • a ligand for example a phosphine ligand in a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene
  • a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene
  • This reaction can be carried out under microwave i
  • compounds of formula (XIII) wherein G 1 is oxygen and n is 1 or 2 can be prepared by reacting an intermediate of formula (IX) wherein X c is a leaving group for example a halogen, d- Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • phosphonate esters e.g. -OP(0)(OR)3 ⁇ 4 wherein R is methyl or ethyl
  • R is methyl or ethyl
  • compounds of formula (XI) wherein G 1 is oxygen, R is OH or Ci-C 6 alkoxy can be prepared by alkylation of an intermediate of formula (XIV) with a reagent of formula (XV) wherein
  • Hal is chloro or bromo. Such reactions can be carried out under well established methods, described for example in Journal of Organic Chemistry, 45(24), 4961-5; 1980.
  • compounds of formula (XIII) wherein G 1 is oxygen can be prepared by alkylation of an intermediate of formula (XIV) with a reagent of formula (XVI) wherein Hal is chloro or bromo.
  • Ci-Cgarylsulfonyloxy optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 _) , phosphonate esters (e.g. -OP(0)(OR) 2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride.
  • diazonium salts e.g. -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 _
  • phosphonate esters e.g. -OP(0)(OR) 2; wherein R is methyl
  • reaction can be carried out with a transition metal catalyst, such as copper, nickel and palladaium, a sulfur source such as sulfur, thiourea, and alkali thiosulfate.
  • a transition metal catalyst such as copper, nickel and palladaium
  • sulfur source such as sulfur, thiourea
  • alkali thiosulfate Such reactions can be carried out under well established methods, described for example in U.S. 5338886 (Ni and thiourea), Tetrahedron Letters (2011), 52, 205-208 (palladium and thiourea) and Chinese Journal of Chemistry (2010), 28, 1441 -1443 (copper and thioruea).
  • compounds of formula (XI) can be prepared by reaction of an intermediate of formula (IX) wherein X c is a halogen, such as fluoro and chloro and an excess of alkali alkyl thiolate, such as sodium thiolate at a temperature between 50°C and a 180°C.
  • X c is a halogen, such as fluoro and chloro
  • alkali alkyl thiolate such as sodium thiolate
  • Such reactions can be carried out in the presence of a base such as an amine or a carbonate, for example potassium or cesium carbonate in solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, dimethylacetamide at a temperature of from 0°C to 150°C, preferably from 25°C to 100°C.
  • a base such as an amine or a carbonate, for example potassium or cesium carbonate
  • solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, dimethylacetamide
  • the reaction can be carried out in the presence of a catalyst, for a example a palladium catalyst, and a ligand, for example a phosphine ligand in a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene at a temperature of from 0°C to 150°C, preferably from 80°C to 130°C.
  • a catalyst for a example a palladium catalyst
  • a ligand for example a phosphine ligand in a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene
  • a solvent such as tetrahydrofuran, dioxane, 1,2- dimethoxyethane, ethyl acetate, or toluene
  • This reaction can be carried out under microwave
  • Such reactions can be carried out in the presence of an acid or a Lewis acid such as an sulfonic acid, carboxylic acid for example methylsulfonic acid, paratoluenesulfonic acid, trifluoroacetic acid, aluminum trichloride or mercury(II) acetate in solvents such as acetic acid, trifluoroacetic acid, toluene, dichloromethane, water at a temperature of from -78°C to 150°C, preferably from 0°C to 110°C.
  • an acid or a Lewis acid such as an sulfonic acid, carboxylic acid for example methylsulfonic acid, paratoluenesulfonic acid, trifluoroacetic acid, aluminum trichloride or mercury(II) acetate
  • solvents such as acetic acid, trifluoroacetic acid, toluene, dichloromethane, water at a temperature of from -78°C to 150°C, preferably from
  • Such reactions can be performed optionally in the presence of a base, such as sodium hydroxide, sodium ethoxide, sodium methoxide, sodium tert-butoxide or potassium hydroxide.
  • a base such as sodium hydroxide, sodium ethoxide, sodium methoxide, sodium tert-butoxide or potassium hydroxide.
  • an acid for example p-toluenesulfonic acid, hydrochloric acid, acetic acid
  • a solvent such as methanol, ethanol, NN-dimethylformamide, toluene, dichloromethane, ethyl acetate, acetonitrile or chlorobenzene or water, or mixtures thereof, at a temperature of from 0°C to 100°C, preferably from ambient temperature to 80°C.
  • Such conditions are described, for example, in Journal of the American Chemical Society (1949), 71, 3554-5 or in Tetrahedron: Asymmetry (2003), 14(1), 113-117 and Journal
  • Such reactions are carried out in the presence of a base, for example an organic base, such as triethylamine or sodium acetate, or an inorganic base, such as sodium hydrogen carbonate, optionally in the presence of a solvent, for example an alcohol, such as methanol or ethanol, or water, or mixtures thereof.
  • a base for example an organic base, such as triethylamine or sodium acetate, or an inorganic base, such as sodium hydrogen carbonate
  • a solvent for example an alcohol, such as methanol or ethanol, or water, or mixtures thereof.
  • Such reactions can also be carried out in the presence of an acid or not, for example p-toluenesulfonic acid, hydrochloric acid, acetic acid, optionnally in the presence of a solvent, for example an alcohol, such as methanol or ethanol, or toluene,
  • the reaction can be carried our in the presence or the absence of a dehydrating agent, such as anhydrous magnesium sulfate or molecular sieves. It can also be perfomed using a Dean Stark or Soxhlet apparatus that enables a constant removal of the water formed during the reaction.
  • a dehydrating agent such as anhydrous magnesium sulfate or molecular sieves. It can also be perfomed using a Dean Stark or Soxhlet apparatus that enables a constant removal of the water formed during the reaction.
  • 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 (I) wherein P is as defined for compounds (I) can be obtained by cyclising a compound of formula (XXXII) wherein Z 3 is aryl substituted Ci-Cgalkylsulfinyl-.
  • Such reactions are usually carried out in the presence of an acid or not, for example p-toluenesulfonic acid, trifluoroacetic acid or hydrochloric acid, optionnally in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene.
  • the reaction is carried out at a temperature of from 0°C to 200°C, preferably from 25°C to 100°C.
  • Such reactions usually involve first the deprotection of the thiol to give a compound of formula (XXXII) wherein Z 3 is thiol, followed by the cyclization.
  • Z 1 is hydrogen or Ci-Cgalkyl or aryl-Ci-C 4 alkylene-or Ci-Cgalkylcarbonyl- or arylsulfonyl- or arylthio-
  • Z 2 is hydrogen or hydroxyl or d-Cgalkoxy- or Ci-Cgalkylsulfonyloxy- or Ci-Cgarylsulfonyloxy- or aryl-Ci-C 4 alkylene-or aryl.
  • Such reactions usually involve the deprotection of Z 1 and of Z 2 or of both groups.
  • the reaction can then involve the following intermediates (with substituents defined as for compounds of formula I and Ar as defined in Scheme 3 :
  • Such reactions are usually carried out in the presence of an oxidant, for example iodine, bromine, thionyl chloride, Bis(trifluoroacetoxy)iodobenzene;
  • an oxidant for example iodine, bromine, thionyl chloride, Bis(trifluoroacetoxy)iodobenzene;
  • the reaction can be carried our in the presence of an acid or not, such as trifluoroacetic acid or acetic acid, optionnally in the presence of a
  • compounds of formula (I-I) wherein P is as defined for compounds (I) can be obtained from a compound of formula (XXXb) wherein Z 1 is arylsulfonyl- or arylthio-, by an oxidation step, are described in Journal of Organic Chemistry (1990), 55(13), 4156-62.
  • reaction can be carried out in the presence of a solvent, for example
  • compounds of formula (I) can be obtained directly from a compound of formula (XXIX) wherein Z 1 is hydrogen.
  • Such reactions are usually carried out in the presence chloramines, formed in situ from ammonia and chlorine or sodium hypochlorite or hypochlorous acid, optionally in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene.
  • a solvent for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene.
  • the reaction is carried out at a temperature of from -80°C to 40°C,
  • compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z 1 is halogen, cyano, arylsulfonyl- or arylthio-.
  • Such reactions are usually carried out in the presence ammonia, optionally in the presence of a solvent, for example dichloroethane, tetrahydrofuran, methanol, ethanol, toluene, dichloromethane or chlorobenzene.
  • a solvent for example dichloroethane, tetrahydrofuran, methanol, ethanol, toluene, dichloromethane or chlorobenzene.
  • compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z 1 is aryl-Ci-C 4 alkylene.
  • Such reactions are usually carried out in two steps- The first one involves the treatment of a compound of formula (XXIX) wherein Z 1 is aryl-Ci-C 4 alkylene by a suitable oxidant, such as sulfuryl chloride or chlorine, in the presence of a solvent, for example
  • the second step then involves the treatment a compound of formula (XXIX) wherein Z 1 is chlorine by an ammonia source, such as ammonia or ammonium bromide in the presence of a base, in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, tetrahydrofuran, dichloromethane or chlorobenzene.
  • an ammonia source such as ammonia or ammonium bromide
  • a solvent for example dichloroethane, methanol, ethanol, toluene, tetrahydrofuran, dichloromethane or chlorobenzene.
  • compounds of formula (I) can be obtained directly from a compound of formula (XXIX) wherein Z 1 is hydrogen.
  • a suitable nitrogen electrophile such as Hydroxylamine-O-sulfonic acid.
  • Such reactions are carried out in the presence of a base, for example an organic base, such as triethylamine or sodium acetate, or an inorganic base, such as sodium hydrogen carbonate, sodium hydroxide or potassium hydroxide optionally in the presence of a solvent, for example tetrahydrofuran, toluene, an alcohol, such as methanol or ethanol, or water, or mixtures thereof.
  • the reaction is carried out at a temperature of from -80°C to 80°C.
  • the compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
  • the pests which may be combated and controlled by the use of the compounsd of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
  • the compounds of the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.
  • Compositions comprising the compound of formula I may be used on ornamental garden plants (e.g.
  • compositions comprising the compound of formula I may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars.
  • the compounds of the invention may be effective against harmful insects, without substantially imposing any harmful side effects to cultivated plants.
  • Application of the compounds of the invention may increase the harvest yields, and may improve the quality of the harvested material.
  • the compounds of the invention may have favourable properties with respect to amount appled, residue formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents.
  • pest species which may be controlled by the compounds of formula (I) include: coleopterans, for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum,
  • Epilachna vigintioctomaculata Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis; lepidopterans, for example, Lymantria dispar, Malacosoma neustria), Pieris rapae,
  • nematodes for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp..
  • Examples of further pest species which may be controlled by the compounds of formula (I) include: from the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.; from the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyal
  • Pentomidae Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp.,
  • Pemphigus spp. Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictoce
  • Hymenoptera for example, Diprion spp., Hoplocampa spp., Lasius spp., Mono- morium pharaonis, Vespa spp.; from the order of the Isopoda, for example, Armadillidium vulgar e, Oniscus asellus, Porcellio scaber; from the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.; from the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumifer
  • Orthoptera for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria; from the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla for example, Scutigerella immaculata
  • Thysanoptera for example, Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura for example, Lepisma saccharina.
  • the phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp.,
  • the compounds of the invention may be used to control the following pest spcies: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp.
  • Kalotermitidae for example Neotermes spp.
  • the Rhinotermitidae for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis
  • the Termitidae for example Globitermes sulfureus
  • Solenopsis geminata fire ant
  • Monomorium pharaonis pharaoh's ant
  • Damalinia spp. and Linognathus spp. biting and sucking lice
  • Meloidogyne spp. root knot nematodes
  • Globodera spp. and Heterodera spp. cyst nematodes
  • Pratylenchus spp. lesion nematodes
  • Rhodopholus spp. banana burrowing nematodes
  • Tylenchulus spp. citrus nematodes
  • Haemonchus contortus barber pole worm
  • Caenorhabditis eelworm Trichostrongylus spp.
  • Trichostrongylus spp. gastro intestinal nematodes
  • Deroceras reticulatum slug
  • the compound of formula I may be used for pest control on various plants, including soybean (e.g. in some cases 10-70g/ha), corn (e.g. in some cases 10-70g/ha), sugarcane (e.g. in some cases 20- 200g/ha), alfalfa (e.g. in some cases 10-70g/ha), brassicas (e.g. in some cases 10-50g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70g/ha), potatoes (including sweet potatoes) (e.g. in some cases 10- 70g/ha), cotton (e.g. in some cases 10-70g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g.
  • citrus e.g. in some cases 60-200g/ha
  • almonds e.g. in some cases 40-180g/ha
  • fruiting vegetables cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.) (e.g. in some cases 10-80g/ha)
  • tea e.g. in some cases 20-150g/ha
  • bulb vegetables e.g. onion, leek etc.
  • grapes e.g. in some cases 30-180g/ha
  • pome fruit e.g. apples, pears etc.
  • stone fruit e.g. pears, plums etc.
  • the compounds of the invention may be used for pest control on various plants, including soybean, corn, sugarcane, alfalfa, brassicas, oilseed rape (e.g. canola), potatoes (including sweet potatoes), cotton, rice, coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulb vegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples, pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.
  • the compounds of the invention may be used on soybean to control, for example, Elasmopalpus lignosellus, Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., aphids,
  • Sternechus subsignatus Formicidae, Agrotis ypsilon, Julus spp., Murgantia spp., Halyomorpha spp., Thyanta spp., Megascelis ssp., Procornitermes ssp., Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp., Neomegalotomus spp., Cerotoma trifurcata, PopilUa japonica, Edessa spp., Liogenys fuscus, Euschistus heros, stalk borer, Scaptocoris castanea, phyllophaga spp., Migdolus spp.,
  • Pseudoplusia includens, Anticarsia gemmatalis, Epinotia spp., Rachiplusia spp., Spodoptera spp., Bemisia tabaci, Tetranychus spp., Agriotes spp., Euschistus spp..
  • the compounds of the invention are preferably used on soybean to control Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, Popillia japonica, Euschistus heros, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Agriotes spp., Euschistus spp..
  • the compounds of the invention may be used on corn to control, for example, Euschistus heros, Euschistus spp., Dichelops furcatus, Diloboderus abderus, Thyanta spp., Elasmopalpus lignosellus, Halyomorpha spp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Agrotis ypsilon, Diabrotica speciosa, aphids, Heteroptera, Procornitermes spp., Scaptocoris castanea, Formicidae, Julus ssp., Dalbulus maidis, Diabrotica virgifera, Diabrotica spp., Mods latipes, Bemisia tabaci, heliothis spp., Tetranychus spp., thrips spp., phyllophaga spp.,
  • Euschistus spp. Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Diabrotica speciosa, Diabrotica virgifera, Diabrotica spp., Tetranychus spp., Thrips spp., Phyllophaga spp., Migdolus spp., Scaptocoris spp., Agriotes spp..
  • the compounds of the invention may be used on sugar cane to control, for example,
  • Sphenophorus spp. termites, Migdolus spp., Diloboderus spp., Telchin licus, Diatrea saccharalis, Mahanarva spp., Mealybugs.
  • the compounds of the invention may be used on alfalfa to control, for example, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collops spp., Empoasca solana, Epitrix spp., Geocoris spp., Lygus hesperus, Lygus lineolaris, Spissistilus spp., Spodoptera spp., Aphids, Trichoplusia ni.
  • the compounds of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix spp., Lygus hesperus, Lygus lineolaris, Trichoplusia ni.
  • the compounds of the invention may be used on oil seed rape, e.g. canola, to control, for example, Meligethes spp., Ceutorhynchus napi, Halotydeus destructor, Psylloides spp..
  • the compounds of the invention may be used on potatoes, including sweet potatoes, to control, for example, Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladera matrida, Agriotes spp., Aphids, wireworms.
  • the compounds of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Agriotes spp..
  • the compounds of the invention may be used on cotton to control, for example, Anthonomus grandis, Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisia tabaci, Trialeurodes spp., Aphids, Lygus spp., phyllophaga spp., Scaptocoris spp., Austroasca viridigrisea, Creontiades spp., Nezara spp., Piezodorus spp., Halotydeus destructor, Oxycaraenus hyalinipennis, Dysdercus cingulatus.
  • Anthonomus grandis Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp
  • the compounds of the invention are preferably used on cotton to control Anthonomus grandis, Tetranychus spp., Empoasca spp., thrips spp., Lygus spp., phyllophaga spp., Scaptocoris spp..
  • the compounds of the invention may be used on rice to control, for example, Leptocorisa spp., Cnaphalocrosis spp., Chilo spp., Scirpophaga spp., Lissorhoptrus spp., Oebalus pugnax, Scotinophara spp., Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix spp., Mealybugs, Sogatella furcifera, Nilaparvata lugens, Orseolia spp., Cnaphalocrocis medinalis, Marasmia spp., Stenchaetothrips biformis, Thrips spp., Hydrellia philippina, Grasshoppers, Pomacea canaliculata, Scirpophaga innotata
  • the compounds of the invention may be used on coffee to control, for example, Hypothenemus
  • the compounds of the invention are preferably used on coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.
  • the compounds of the invention may be used on citrus to control, for example, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., Thrips spp., Unaspis spp., Ceratitis capitata, Phyllocnistis spp., Aphids, Hardscales, Softscales, Mealybugs.
  • the compounds of the invention are preferably used on citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., thrips spp., Phyllocnistis spp..
  • the compounds of the invention may be used on almonds to control, for example, Amyelois transitella, Tetranychus spp..
  • the compounds of the invention may be used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control, for example, Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp., Bemisia tabaci, Trialeurodes spp., Aphids, Paratrioza spp., Frankliniella occidentalis, Frankliniella spp., Anthonomus spp., Phyllotreta spp., Amrasca spp., Epilachna spp., Halyomorpha spp., Scirtothrips spp., Leucinodes spp., Neoleucinodes spp.
  • Maruca spp. Fruit flies, Stinkbugs, Lepidopteras, Coleopteras.
  • the compounds of the invention are preferably used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp., Paratrioza spp., Frankliniella
  • the compounds of the invention may be used on tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp., Caloptilia theivora, Tetranychus spp..T e compounds of the invention are preferably used on tea to control Empoasca spp., Scirtothrips spp..
  • the compounds of the invention may be used on bulb vegetables, including onion, leek etc. to control, for example, Thrips spp., Spodoptera spp., heliothis spp..
  • the compounds of the invention are preferably used on bulb vegetables, including onion, leek etc. to control Thrips spp..
  • the compounds of the invention may be used on grapes to control, for example, Empoasca spp., Lobesia spp., Eupoecilia ambiguella, Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Eotetranychus Willamettei, Erythroneura Elegantula, Scaphoides spp., Scelodonta strigicollis, Mealybugs.
  • the compounds of the invention are preferably used on grapes to control Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Scaphoides spp..
  • the compounds of the invention may be used on pome fruit, including apples, pears etc., to control, for example, Cacopsylla spp., Psylla spp., Panonychus ulmi, Cydia pomonella, Lepidopteras, Aphids, Hardscales, Softscales.
  • the compounds of the invention are preferably used on pome fruit, including apples, pears etc., to control Cacopsylla spp., Psylla spp., Panonychus ulmi.
  • the compounds of the invention may be used on stone fruit to control, for example, Grapholita molesta, Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp., Aphids, Hardscales, Softscales, Mealybugs.
  • the compounds of the invention are preferably used on stone fruit to control Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp..
  • the compounds of the invention may be used on cereals to control, for example, Aphids, Stinkbugs, earthmites, Eurygaster integriceps, Zabrus tenebrioides, Anisoplia austriaca, Chaetocnema aridula, Phyllotreta spp., Oulema melanopus, Oscinella spp., Delia spp., Mayetiola spp., Contarinia spp., Cephus spp., Steneotarsonemus spp., Apamea spp..
  • compounds of formula I and mixtures of the invention may be used on rice to control Baliothrips biformis (Thrips), Chilo spp. (e.g. Chilo polychrysus (Dark headed striped borer), Chilo suppressalis (Rice stemborer), Chilo indicus (Paddy stem borer), Chilo polychrysus (Dark- headed rice borer), Chilo suppressalis (Stripe stem borer)), Cnaphalocrocis medinalis (Rice leaf folder), Dicladispa armigera (Hispa), Hydrellia philipina (Rice whorl-maggot), Laodelphax spp. (Smaller brown planthopper) (e.g.
  • Nephottetix spp. Green leafhopper ) (e.g. Nephotettix cincticeps, Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens), Nilaparvata lugens (Brown
  • Planthopper Nymphula depunctalis (Rice caseworm), Orseolia oryzae (Rice Gall midge), Oulema oryzae (Rice leafbeetle), Scirpophaga incertulas (Yellow Stemborer), Scirpophaga innotata (White Stemborer), Scotinophara coarcicide (Rice black bug), Sogaella frucifera (White -backed planthopper), Steneotarsonemus spinki.
  • the compounds of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.
  • the compounds of the invention may be used to control ornamental pests including: Ants (Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets,
  • Cutworms Eastern tent caterpillars, Elm leaf beetles, European sawflies, Fall web worms, Flea beetles, Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beetles (adults), Lace bugs, Leaf- feeding caterpillars, Leafhoppers, Leafminers (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs, Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock moth larvae, Wasps, Broadmites, Brown softscales, California redscales (crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spider mite
  • the compounds of the invention may be used to control turf pests including: Ants (Including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sod webworms, Sow bugs, Ticks (including species which transmit Lyme disease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult), Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult), Mole crickets (nymphs and young adults), Mole Crickets (mature adults), Chinch Bugs.
  • Ants including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquit
  • the compounds of formula (I) and mixture of the invention may be used for soil applications, including as a seed application, to target at least the following: sucking pests such as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs, white flies (e.g. on cotton and vegetables), mites; on soil pests such as corn root worm, wireworms, white grubs, zabrus, termites (e.g. on sugar cane, soy, pasture), maggots, cabbage root fly, red legged earth mite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus , plutella (e.g.
  • brassica stem borers, leaf miners, flea beetle, Sternechus; on nematicides, such as Heterodera glycines (e.g. on soybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn), P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables), Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g. on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus (e.g. on cereals), thornei (e.g. on cereals).
  • Heterodera glycines e.g. on soybean
  • Pratylenchus brachyurus e.g. on corn
  • P. zeae e.g.
  • the compounds of formula (I) and mixture of the invention may be used for seed applications at least on the following: soil grubs for corn, soybeans, sugarcane: Migdolus spp; Phyllophaga spp.; Diloboderus spp; Cyclocephala spp; Lyogenys fuscus; sugarcane weevils: Sphenophorus levis & Metamasius hemipterus; termites for soybeans, sugarcane, pasture, others: Heterotermes tenuis; Heterotermes longiceps; Cornitermes cumulans; Procornitermes triacifer ; Neocapritermes opacus; Neocapritermes parvus; corn root worms for corn and potatoes: Diabrotica spp., seed Maggot: Delia platura; soil stinkbugs: Scaptocoris castanea; wireworms: Agriotes spp; Athous spp Hipnodes bicolor; Ctenicera de
  • Lissorhoptrus oryzophilus Red Legged earth mites: Halotydeus destructor.
  • the invention therefore provides a method of combating and/or controlling an animal pest, e.g. an invertebrate animal pest, which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I).
  • an animal pest e.g. an invertebrate animal pest
  • applying to the pest to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I).
  • the invention provides a method of combating and/or controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest,
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • plants as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names RoundupReady® and
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
  • Compounds of formula I may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
  • the preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Pesticidal proteins may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like.
  • pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of Wales ⁇ see also, Crickmore et al. (1998) Microbiol. Mol. Biol. Rev. 62:807-813).
  • Other pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp.
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome- inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl -transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium
  • pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073.
  • Agrisure®CB corn producing Cryl Ab
  • Agrisure®RW corn producing mCry3A
  • Agrisure® Viptera corn hybrids producing Vip3Aa
  • Agrisure300GT corn hybrids producing Cryl Ab and mCry3A
  • YieldGard® corn hybrids producing the Cryl Ab protein
  • YieldGard® Plus corn hybrids producing CrylAb and Cry3Bbl
  • Genuity® SmartStax® corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb
  • Herculex® I corn hybrids producing CrylFa
  • Herculex®RW corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]
  • NuCOTN®33B cotton cultivar
  • transgenic crops are:
  • Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer ⁇ Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,
  • NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • CP4 EPSPS obtained from Agrobacterium sp. strain CP4
  • Roundup® contains glyphosate
  • CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • transgenic plants and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto), HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g.
  • Optimum GAT® plants stacked with STS® and Roundup Ready® or plants stacked with STS® and Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto).
  • soybean plants carrying trains conferring resistance to 2.4D e.g. Enlist®
  • glyphosate e.g. Roundup Ready®, Roundup Ready 2 Yield®
  • sulfonylurea e.g. STS®
  • glufosinate e.g. Liberty Link®, Ignite®
  • Dicamba (Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta).
  • Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto).
  • glyphosate and sulfonyl-urea tolerance e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®
  • dicamba glyphosate tolerance
  • cotton transgenic events include MON 531 / 757 / 1076 (Bollgard I ® - Monsanto), MON1445 (Roundup ready cotton ®- Monsanto), MON531 x MON1445 (Bollgard I + RR ®- Monsanto), MON15985 (Genuity Bollgard II cotton ®- Monsanto), MON88913 (Genuity RR FLEX cotton ®- Monsanto), MON15985 x MON1445 (Genuity Bollgard II + RR FELX cotton ®- Monsanto), MON15983 x MON88913 (Genuity Bollgard II + RR FLEX cotton ® - Monsanto), MON15985
  • MON88913 x MON15985 (FibreMax LL GlyTol Bollgard II cotton ® - Monsanto), MON88913
  • Soy transgenic events include MON87701 x MON89788 (Genuity Roundup ready 2 Yield soybeans® - Monsanto), MON89788 (Roundup Ready2Yield®, RR2Y® - Monsanto), MON87708 (Monsanto), 40-3-2 (Roundup Ready®, RRl® - Monsanto), MON87701 (Monsanto), DAS-68416 (Enlist Weed Control System® - Dow), DP356043 (Optimum GAT® - Pioneer), A5547-127 (LibertyLink soybean® - Bayercropscience), A2704-12 (Bayercropscience), GU262 (Bayercropscience), W62 W98 (Bayercropscience), CRV127 (Cultivance® - BASF / EMBRAPA) SYHT0H2 (WO2012/082548).
  • Maize transgenic events include T25 (LibertyLink®, LL® - Bayerscropscience), DHT-1 (Dow), TC1507 (Herculex I® - Dow), DAS59122-7 (Herculex RW® - Dow), TC1507 + DAS59122-7 - Herculex Xtra® - Dow), TCI 507 x DAS-59122-7 x NK603 (Herculex Xtra + RR® - Dow), TC1507 x DAS-59122- x MON88017 x MON89034 (Genuity Smartstax corn®, Genuity
  • a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • compositions both solid and liquid formulations
  • the composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from 0.1 g to 10kg per hectare, preferably from 1 g to 6kg per hectare, more preferably from lg to 1kg per hectare.
  • the present invention provides a composition
  • molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor.
  • the composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
  • compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
  • the formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
  • Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulfate
  • water-soluble organic solids such as a polysaccharide
  • compositions may also be granulated to form water soluble granules (SG).
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, mineral carbonates, sulfates or phosphates
  • Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
  • One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
  • DC Dispersible Concentrates
  • a compound of formula (I) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether.
  • organic solvent such as a ketone, alcohol or glycol ether.
  • surface active agent for example to improve water dilution or prevent crystallization in a spray tank.
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVES SO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg-Qo fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVES SO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as cyclo
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs.
  • An ME may be either an oil-in- water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
  • SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane).
  • a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non- pressurized, hand-actuated spray pumps.
  • a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment.
  • a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
  • a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
  • DS powder for dry seed treatment
  • SS water soluble powder
  • WS water dispersible powder for slurry treatment
  • CS capsule suspension
  • the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
  • Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
  • Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-z ' opropyl- and tri-wopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3 -sulfate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);
  • alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof
  • fatty alcohols such as oleyl alcohol or cetyl alcohol
  • alkylphenols such as octylphenol, nonylphenol or octylcresol
  • partial esters derived from long chain fatty acids or hexitol anhydrides condensation products of said partial esters with ethylene oxide
  • alkanolamides alkanolamides
  • simple esters for example fatty acid polyethylene glycol esters
  • amine oxides for example lauryl dimethyl amine oxide
  • lecithins alkanolamides
  • simple esters for example fatty acid polyethylene glycol esters
  • amine oxides for example lauryl dimethyl amine oxide
  • lecithins lecithins
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides,
  • polyvinylpyrrolidone or sodium carboxymethylcellulose and swelling clays (such as bentonite or attapulgite).
  • a compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water- soluble bag) in soil or an aqueous environment.
  • a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • a compound of formula (I) may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of formula (I). The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).
  • fertilizers for example nitrogen-, potassium- or phosphorus-containing fertilizers.
  • Suitable formulation types include granules of fertilizer.
  • the mixtures preferably contain up to 25% by weight of the compound of formula (I).
  • the invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate.
  • An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient will depend upon the intended utility of the composition.
  • Suitable pesticides include the following:
  • a) Pyrethroids such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin and gamma cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox or
  • Organophosphates such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methy 1, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • Pyrazoles such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate;
  • Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin or spinetoram;
  • Organochlorine compounds such as endosulfan (in particular alpha-endosulfan), benzene hexachloride, DDT, chlordane or dieldrin;
  • Amidines such as chlordimeform or amitraz
  • Fumigant agents such as chloropicrin, dichloropropane, methyl bromide or metam
  • Neonicotinoid compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or nithiazine;
  • Diphenyl ethers such as diofenolan or pyriproxifen
  • Ketoenols such as Spirotetramat, spirodiclofen or spiromesifen
  • Diamides such as flubendiamide, chlorantraniliprole (Rynaxypyr®) or cyantraniliprole;
  • Essential oils such as Bugoil® - (Plantlmpact); or
  • a comopund selected from buprofezine, flonicamid, acequinocy 1, bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin, fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin, iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen, flupyradifurone, 4-[(6-Chloro-pyridin-3- ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one (DE 102006015467), CAS: 915972-17-7
  • pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition.
  • selective insecticides for particular crops for example stemborer specific insecticide (combinations such as cartap ) or hopper specific insecticides (combinations such as buprofezin ) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, to give combinations such as clofentezine, flubenzimine, hexythiazox or tetradifon ; acaricidal motilicides, to give combinations such as dicofol or propargite ; acaricides, to give combinations such as bromopropylate or chlorobenzilate ; or growth regulators, such as
  • fungicidal compounds and combinations which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-l -sulfonamide,
  • acibenzolar-S-methyl alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim , chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds to give combintations such as copper oxychloride, copper oxyquinolate, copper sulfate, copper tallate and Bordeaux mixture, cyclufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyri
  • the active ingredients combinations described above comprising a compound selected of the invention, in particulary from Tables 1 to 162 and an active ingredient as described above are preferably combined in a mixing ratio of from 100: 1 to 1 :6000, especially from 50: 1 to 1 :50, more especially in a ratio of from 20: 1 to 1 :20, even more especially from 10: 1 to 1 : 10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2: 1 to 1 :2, and a ratio of from 4: 1 to 2: 1 being likewise preferred, above all in a ratio of 1 :1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 : 150, or
  • biological agents may be included in the composition of the invention e.g. Baciullus species such as Bacillus firmus, Bacillus cereus, Bacillus subtilis, and Pasteuria species such as Pasteuria penetrans and Pasteuria nishizawae.
  • Bacillus firmus strain is strain CNCM 1-1582 which is commercially available as BioNemTM.
  • a suitable Bacillus cereus strain is strain CNCM 1-1562. Of both Bacillus strains more details can be found in US 6,406,690.
  • Other biological organisms that may be included in the compositions of the invention are bacteria such as Streptomyces spp. such as S.
  • avermitilis and fungi such as Pochonia spp. such as P. chlamydosporia.
  • Pochonia spp. such as P. chlamydosporia.
  • Metarhizium spp. such as M. anisopliae
  • Pochonia spp. such as P. chlamydosporia.
  • the compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
  • Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
  • An example of a rice selective herbicide which may be included is propanil.
  • An example of a plant growth regulator for use in cotton is PIXTM.
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • the compounds of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal.
  • pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots.
  • the animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.
  • the invention relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a compound of the invention.
  • the administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body.
  • the invention relates to a compound of the invention for controlling parasitic invertebrate pests in or on an animal.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal
  • the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticidally effective amount of a compound of the invention to the environment in which an animal resides.
  • the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention.
  • the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.
  • the invention provides a method of treating an animal suffering from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention.
  • the invention relates to a compound of the invention for use in treating an animal suffering from a parasitic invertebrate pest.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for treating an animal suffering from a parasitic invertebrate pest.
  • the invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.
  • the compounds of the invention may be used alone or in combination with one or more other biologically active ingredients.
  • the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a compound of the invention and component B is a compound as described below.
  • the compounds of the invention may be used in combination with anthelmintic agents.
  • anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-444964 and EP-594291.
  • Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole,
  • Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel.
  • Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.
  • the compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • ectoparasiticides for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • the compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers W095/19363 or WO04/72086, particularly the compounds disclosed therein.
  • Organophosphates acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, me
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) - (1 R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta - cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)- cyclopentylisomer), bioresmethrin, bifenthrin, NCT85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fen
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • antiparasitics acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydr
  • Fungicides acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamid, captafol, captan, carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine
  • fenpropimorph fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin, fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl- aluminium, furalaxyl, furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, krsoxim- methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole,
  • metominostrobin/fenominostrobin metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifluzamide, thiophanate -methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin.
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • the compounds of the invention are preferably used in combination with the following (where "Tx" means a compound of formula (I), and in particular a compound selected from Tables 1 to 150, which may result in a synergistic combination with the given active ingredient): imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen
  • omeprazole tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel,
  • ratios of the compound of formula I to any mixing partner described herein include
  • 30 of the invention may comprise a pesticidally effective amount of a compound of formula I and
  • salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts
  • salts of compounds of the invention may be useful for control of invertebrate pests and animal parasites.
  • Salts include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the compounds of the invention also include N-oxides. Accordingly, the invention comprises combinations of compounds of the invention including N-oxides and salts thereof and an additional active ingredient including N-oxides and salts thereof.
  • compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone -vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the compounds of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • One method of application involves spraying a water dispersion or refined oil solution of the combination products.
  • Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
  • Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aerosol spray can.
  • Such spray compositions can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propellants, foaming agents, etc. as the case may be. Of note is a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier.
  • a spray composition comprises a pesticidally effective amount of a compound of the invention and a propellant.
  • propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing.
  • a spray composition (and a method utilizing such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horse flies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and the like, including individually or in combinations.
  • the controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internal parasites that are parasitic to the inside of the body of the host animal (e.g., stomach, intestine, lung, veins, under the skin, lymphatic tissue).
  • External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas.
  • Internal parasites include heartworms, hookworms and helminths.
  • the compounds of the invention may be particularly suitable for combating external parasitic pests.
  • the compounds of the invention may be suitable for systemic and/or non- systemic control of infestation or infection by parasites on animals.
  • the compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild, livestock and agricultural working animals.
  • Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers and/or wool), cultured fish, honeybees.
  • fatalities and performance reduction in terms of meat, milk, wool, skins, eggs, etc.
  • controlling parasites may help to prevent the transmittance of infectious agents, the term "controlling" referring to the veterinary field, meaning that the active compounds are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels, e.g. the active compound is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation.
  • the compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.
  • companion animals and pets e.g., dogs, cats, pet birds and aquarium fish
  • research and experimental animals e.g., hamsters, guinea pigs, rats and mice
  • the animal is preferably a vertebrate, and more preferably a mammal, avian or fish.
  • the animal subject is a mammal (including great apes, such as humans).
  • Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters).
  • Avians include Anatidae (swans, ducks and geese),
  • Columbidae e.g., doves and pigeons
  • Phasianidae e.g., partridges, grouse and turkeys
  • Thesienidae e.g., domestic chickens
  • Psittacines e.g., parakeets, macaws, and parrots
  • game birds e.g., ratites (e.g., ostriches).
  • Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, Columbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaws and parrots raised for the pet or collector market, among others.
  • Anatidae such as swans, geese, and ducks
  • Columbidae such as doves and domestic pigeons
  • Phasianidae such as partridge, grouse and turkeys
  • Thesienidae such as domestic chickens
  • Psittacines such as parakeets, macaws and parrots raised for the pet or collector market, among others.
  • fish is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts. Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping. Examples of potential fish recipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.

Abstract

La présente invention concerne des composés représentés par la formule (I), dans laquelle R1, R2, R3, R4, G1, n, A1, A2, A3 et A4 sont tels que définis dans les revendications. L'invention concerne aussi des procédés et des produits intermédiaires utiles dans la préparation de ces composés, ainsi que des compositions insecticides, acaricides, nématocides et molluscicides comprenant ces composés, et des procédés d'utilisation de ces composés pour lutter contre des insectes, des acariens, des nématodes et des mollusques parasites.
PCT/EP2013/074394 2012-11-21 2013-11-21 Composés insecticides à base de dérivés d'arylthioacétamide WO2014079935A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014202751A1 (fr) * 2013-06-21 2014-12-24 Basf Se Procédés permettant de lutter contre les nuisibles dans le soja
US9420793B2 (en) 2015-01-16 2016-08-23 Avista Pharma Solutions Antiparasitic compounds
US10807992B2 (en) 2017-11-16 2020-10-20 Avista Pharma Solutions, Inc. Single enantiomer antiparasitic compounds
US11618751B1 (en) 2022-03-25 2023-04-04 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives

Citations (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0357460A2 (fr) 1988-09-02 1990-03-07 Sankyo Company Limited Dérivés de la milbémycine, leur préparation et leur utilisation
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0444964A1 (fr) 1990-03-01 1991-09-04 Sankyo Company Limited Dérivés d'éthers milbémycine, leur préparation et leur utilisation comme anthelmintiques
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
EP0594291A1 (fr) 1992-09-01 1994-04-27 Sankyo Company Limited Procédés pour la préparation de dérivés des milbémycines ayant un groupe d'éther sur la position 13
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
US5338886A (en) 1992-05-21 1994-08-16 Eastman Chemical Company Process for preparation of aromatic thiols
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003024222A1 (fr) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Traitement arthropodicide a l'anthranilamide
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
WO2006129714A1 (fr) 2005-06-01 2006-12-07 Meiji Seika Kaisha, Ltd. Agent antiparasitaire
EP1731512A1 (fr) * 2004-03-05 2006-12-13 Nissan Chemical Industries, Ltd. Compose benzamide substitue par de l'isoxazoline et agent de contrôle d'organisme nocif
WO2007020986A1 (fr) 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Dérivé anilide d'acide pyrazolecarboxylique substitué ou son sel, son intermédiaire, agent pour utilisation horticole et agricole, et son utilisation
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
WO2007102059A1 (fr) 2006-03-06 2007-09-13 Pfizer Japan Inc. Derives de sulfonyl benzimidazole
DE102006015467A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
EP1878730A1 (fr) * 2006-07-12 2008-01-16 Bayer Schering Pharma Aktiengesellschaft Isoxazolines substituées, compositions pharmaceutiques les comprenant, procédés pour leur préparation et leur usage
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011147952A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2011147953A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012156400A1 (fr) * 2011-05-18 2012-11-22 Syngenta Participations Ag Composés insecticides à base de dérivés d'arylthiacétamide
WO2013037626A1 (fr) * 2011-09-13 2013-03-21 Syngenta Participations Ag Dérivés d'isothiazoline en tant que composés insecticides

Patent Citations (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0357460A2 (fr) 1988-09-02 1990-03-07 Sankyo Company Limited Dérivés de la milbémycine, leur préparation et leur utilisation
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0444964A1 (fr) 1990-03-01 1991-09-04 Sankyo Company Limited Dérivés d'éthers milbémycine, leur préparation et leur utilisation comme anthelmintiques
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
US5338886A (en) 1992-05-21 1994-08-16 Eastman Chemical Company Process for preparation of aromatic thiols
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
EP0594291A1 (fr) 1992-09-01 1994-04-27 Sankyo Company Limited Procédés pour la préparation de dérivés des milbémycines ayant un groupe d'éther sur la position 13
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
US7030295B2 (en) 2001-08-31 2006-04-18 Syngenta Participations Ag Modified Cry3A toxins and nucleic acid sequences coding therefor
WO2003024222A1 (fr) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Traitement arthropodicide a l'anthranilamide
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
EP1731512A1 (fr) * 2004-03-05 2006-12-13 Nissan Chemical Industries, Ltd. Compose benzamide substitue par de l'isoxazoline et agent de contrôle d'organisme nocif
WO2006129714A1 (fr) 2005-06-01 2006-12-07 Meiji Seika Kaisha, Ltd. Agent antiparasitaire
WO2007020986A1 (fr) 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Dérivé anilide d'acide pyrazolecarboxylique substitué ou son sel, son intermédiaire, agent pour utilisation horticole et agricole, et son utilisation
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
WO2007102059A1 (fr) 2006-03-06 2007-09-13 Pfizer Japan Inc. Derives de sulfonyl benzimidazole
DE102006015467A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
EP1878730A1 (fr) * 2006-07-12 2008-01-16 Bayer Schering Pharma Aktiengesellschaft Isoxazolines substituées, compositions pharmaceutiques les comprenant, procédés pour leur préparation et leur usage
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
WO2011066384A1 (fr) 2009-11-24 2011-06-03 Dow Agrosciences Llc Événement 416 de la transformation aad-12, lignées de soja transgéniques associées, et leur identification spécifique à l'événement
WO2011147952A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2011147953A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2012082548A2 (fr) 2010-12-15 2012-06-21 Syngenta Participations Ag Soja comprenant le mécanisme de transformation syht04r, et compositions et procédés de détection de ce mécanisme
WO2012156400A1 (fr) * 2011-05-18 2012-11-22 Syngenta Participations Ag Composés insecticides à base de dérivés d'arylthiacétamide
WO2013037626A1 (fr) * 2011-09-13 2013-03-21 Syngenta Participations Ag Dérivés d'isothiazoline en tant que composés insecticides

Non-Patent Citations (22)

* Cited by examiner, † Cited by third party
Title
"Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999", JOURNAL OF THE CHEMICAL SOCIETY, 1985, pages 153 - 7
CHEMICAL COMMUNICATIONS, 2009, pages 5236 - 5238
CHINESE JOURNAL OF CHEMISTRY, vol. 28, 2010, pages 1441 - 1443
CRICKMORE ET AL., MICROBIOL. MOL. BIOL. REV., vol. 62, 1998, pages 807 - 813
D. S. KETTLE: "Medical and Veterinary Entomology", JOHN WILEY AND SONS
E. J. L. SOULSBY: "Monnig's Veterinary Helminthology and Entomology", WILLIAMS AND WILKINS CO., article "Helminths, Arthropods and Protozoa"
E. J. L. SOULSBY: "Textbook of Veterinary Clinical Parasitology", vol. 1, F. A. DAVIS CO., article "Helminths"
JOURNAL OF ORGANIC CHEMISTRY, vol. 45, no. 24, 1980, pages 4961 - 5
JOURNAL OF ORGANIC CHEMISTRY, vol. 46, no. 4, 1981, pages 771
JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 13, 1990, pages 4156 - 62
JOURNAL OF ORGANIC CHEMISTRY, vol. 61, 1996, pages 1986
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, 2011, pages 6403 - 6410
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 71, 1949, pages 3554 - 5
MCCUTCHEON'S: "Functional Materials, annual International and North American editions", vol. 2, MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
ORGANIC LETTERS, vol. 8, no. 21, 2006, pages 4811 - 4813
ORGANOMETALLICS, vol. 26, 2007, pages 897 - 909
R. O. DRUMMAND; J. E. GEORGE; S. E. KUNZ: "Control of Arthropod Pests of Livestock: A Review of Technology", CRC PRESS
SYNLETT, vol. 8, 2006, pages 1255 - 1259
SYNTHESIS, 1983, pages 751 - 5
T. W. GREEN; P. G. M. WUTS: "Protective Groups in Organic Synthesis", 1999, WILEY-INTERSCIENCE, pages: 564 - 566,740-
TETRAHEDRON LETTERS, vol. 52, 2011, pages 205 - 208
TETRAHEDRON: ASYMMETRY, vol. 14, no. 1, 2003, pages 113 - 117

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014202751A1 (fr) * 2013-06-21 2014-12-24 Basf Se Procédés permettant de lutter contre les nuisibles dans le soja
US9420793B2 (en) 2015-01-16 2016-08-23 Avista Pharma Solutions Antiparasitic compounds
US9686991B2 (en) 2015-01-16 2017-06-27 Avista Pharma Solutions, Inc. Antiparasitic compounds
US9883674B2 (en) 2015-01-16 2018-02-06 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10092001B2 (en) 2015-01-16 2018-10-09 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10342234B2 (en) 2015-01-16 2019-07-09 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10772331B2 (en) 2015-01-16 2020-09-15 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10807992B2 (en) 2017-11-16 2020-10-20 Avista Pharma Solutions, Inc. Single enantiomer antiparasitic compounds
US11618751B1 (en) 2022-03-25 2023-04-04 Ventus Therapeutics U.S., Inc. Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives

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