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WO2013135674A1 - Composés de 2-aryl-acétamide insecticides - Google Patents

Composés de 2-aryl-acétamide insecticides Download PDF

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Publication number
WO2013135674A1
WO2013135674A1 PCT/EP2013/054969 EP2013054969W WO2013135674A1 WO 2013135674 A1 WO2013135674 A1 WO 2013135674A1 EP 2013054969 W EP2013054969 W EP 2013054969W WO 2013135674 A1 WO2013135674 A1 WO 2013135674A1
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spp
substituted
fluoro
alkylene
hydrogen
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Inventor
Jérôme Yves CASSAYRE
Myriem El Qacemi
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Syngenta Participations AG
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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
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to certain amide derivatives, 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 ;
  • a 2 , A 3 and A 4 are independently of one another C-H or C-R 5a , or nitrogen;
  • G 1 is oxygen
  • Xi is halogen
  • X2 is hydrogen, or halogen
  • R 1 is hydrogen, Ci-Cgalkyl, d-Cgalkoxy, Ci-Cgalkylcarbonyl, or Ci-Cgalkoxycarbonyl;
  • R 2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R 6 , Ci-Cgalkenyl or Ci-Cgalkenyl substituted by one to five R 6 , Q-Cgalkynyl or Q-Cgalkynyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - Ciocycloalkyl 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 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbon
  • R J is CrCghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9
  • R 5a is halogen, cyano, nitro, Ci-Cgalkyl, Ci-Cghaloalkyl, Ci-Cgalkenyl, Ci -Cghaloalkenyl, Ci-Cgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, d-Cgalkoxy, Ci-Cghaloalkoxy, Ci-Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-;
  • R 5b is hydrogen, halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, Ci-Cgalkenyl, Ci -Cghaloalkenyl, Cp Cgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, d-Cgalkoxy, Ci-Cghaloalkoxy, Ci-Cgalkylthio, Ci- Cghaloalkylthio, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or C r
  • each R 6 is independently halogen, cyano, nitro, hydroxy, CpCgalkoxy, Ci-Cghaloalkoxy, C r
  • each R 7 is independently halogen or CpCgalkyl
  • each R 8 and R 9 are independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C 2 -C 8 alkenyl, C 2 - Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Q-Cgalkoxy, Ci-Cghaloalkoxy, mercapto, C r Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl, Ci-Cghaloalkylsulfinyl, Ci-Cgalkylsulfonyl, d- 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 ;
  • each R 10 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C ihaloalkyl, Ci-C 4 alkoxy, or d- C 4 haloalkoxy;
  • R 11 is hydrogen, CpCgalkyl or Ci-Cgalkyl substituted by one to five R 6 , Ci-Cgalkenyl or Ci-Cgalkenyl substituted by one to five R 6 , Ci-Cgalkynyl or Ci-Cgalkynyl substituted by one to five R 6 , C3- Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 7 , C3-Ciocycloalkyl-Ci-C 4 alkylene or C3- 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 substituted by one to five R 8
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers salts and N-oxides of the compounds of the invention.
  • the compounds of the invention may contain one or more asymmetric carbon atoms, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2 -methyl-prop -1-yl or 2-methyl-prop-2- yl.
  • the alkyl groups are preferably C 1 -C6, more preferably C 1 -C4, most preferably C 1 -C3 alkyl groups. Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 - , -CH 2 -CH 2 -, -CH(CH 3 )-, -CH 2 -CH 2 -CH 2 -, -CH(CH 3 )-CH 2 -, or -CH(CH 2 CH 3 )-.
  • the alkylene groups are preferably C 1 -C3, more preferably C 1 -C 2 , most preferably Ci alkylene groups.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z) -configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C 2 -C 6 , more preferably C 2 -C 4 , most preferably C 2 -C 3 alkenyl groups.
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C 6 , more preferably C 2 -C 4 , most preferably C 2 -C 3 alkynyl groups.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl,
  • Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.
  • Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, l-chloro-prop-2-ynyl.
  • Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl.
  • the cycloalkyl groups are preferably C 3 -Cg, more preferably C 3 -C6 cycloalkyl groups.
  • the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Carbocycles are cycloalkyl groups.
  • Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [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.
  • Heterocycles are heterocyclyl groups.
  • R 10 , R u , R 12 and R 13 are, in any combination, as set out below.
  • a 2 , A 3 and A 4 are nitrogen.
  • 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 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.
  • Xi is fluorine
  • X 2 is hydrogen or fluorine, most preferably fluorine, more preferably Xi is fluorine, and X 2 is hydrogen or fluorine.
  • X 1 is fluorine and X 2 is hydrogen.
  • X 1 and X 2 are both fluorine.
  • 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 CpCgalkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - Ciocycloalkyl 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 alkylene - wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C i alkylene, C3-Cgcycloalky
  • R 2 is CpCgalkyl or Q-Cgalkyl substituted by one to five R 6 , C3-Ciocycloalkyl or
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 , C4-C 6 cyclo- alkyl or C4-C 6 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Cr C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl or thietanyl substituted by one to five R 8 , oxo-thietanyl or oxo-thietanyl substituted by one to five R 8 , dioxo-thietanyl or dioxo- thietanyl substituted by one to five R 8 ,
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 , C 4 -C 6 cycloalkyl or
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 .
  • R 2 is C 4 -C 6 cycloalkyl or C 4 -C 6 cycloalkyl substituted by one to five
  • R 2 is phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , or pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 ,
  • R 2 is thietanyl or thietanyl substituted by one to five R 8 , oxo-thietanyl or oxo-thietanyl substituted by one to five R 8 , dioxo-thietanyl or dioxo-thietanyl substituted by one to five R 8 .
  • the thietany moiety is linked at the 3 position.
  • R 2 is group Al .
  • 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 .
  • R 4 is group B 1
  • X 3 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.
  • Example of R 4 include 3,5-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-dichlorophenyl, 3-chloro-4-bromophenyl, 3,5-dichloro-4-fluorophenyl, 3,4,5-trichlorophenyl, 3,5- dichloro-4-iodophenyl, 3,4,5-trifluorophenyl, 3-chloro-5-bromophenyl, 3-chloro-5-fluorophenyl, 3- chloro-5-(trifluoromethyl)phenyl, 3,4-dichloro-5-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 4-chloro-3,5-bis(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 2,6-dichloro-4-pyridyl, 2,6- bis(trifluoromethyl)-4-pyr
  • R 4 is 3,5- dichloro-phenyl. In one group of compounds R 4 is 3,5-dichloro-4-fluorophenyl-. In one group of compounds R 4 is 3,4,5-trichlorophenyl-. In one group of compounds R 4 is 3,5-bis(trifluoromethyl)phenyl.
  • each R 5a is independently halogen, cyano, nitro, CpCgalkyl, C3-Cgcycloalkyl, d- Cghaloalkyl, C2-Cgalkenyl, more preferably halogen, cyano, nitro, CpCgalkyl, C2-Cg alkenyl, C3- Cgcycloalkyl, Ci-Cghaloalkyl, even more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, vinyl, yet even more preferably bromo, chloro, fluoro, cyclopropyl, trifluoromethyl, vinyl, or methyl.
  • R 5b is hydrogen, halogen, cyano, nitro, CpCgalkyl, C3-Cgcycloalkyl, Ci-Cghaloalkyl, C 2 -C 8 alkenyl, more preferably hydrogen, halogen, cyano, Q-Cgalkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, C r Cghaloalkyl, even more preferably hydrogen, bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, vinyl, even more preferably hydrogen, bromo, chloro, fluoro, methyl or trifluoromethyl, most preferably hydrogen, bromo, chloro, fluoro or methyl. In one group of compounds R 5b is bromo, chloro, fluoro or methyl.
  • each R 6 is independently halogen, nitro, cyano, Ci-C 4 alkyl, Ci-C ihaloalkyl, Q-
  • Ci-C ihaloalkoxy more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, more preferably chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, or trifluoromethoxy, most preferably bromo, chloro, or trifluoromethyl.
  • each R 7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
  • each R 8 is independently halogen, cyano, nitro, CpCsalkyl, Ci-Cshaloalkyl, Q- C 8 alkoxy, Ci-Cghaloalkoxy, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably bromo, chloro, fluoro, cyano or methyl.
  • each R 9 is independently halogen, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkoxy, d-
  • Ci-Cgalkylthio Ci-Cghaloalkylthio, more preferably bromo, chloro, fluoro,
  • 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.
  • R 11 is Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 cyanoalkyl, C3-C 6 cycloalkyl, C3-C 6 cycloalkyl- Ci-C 2 alkylene, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, oxetanyl, thietanyl, oxo- thietanyl, dioxo-thietanyl, benzyl or benzyl substituted by one to three R 13 , or R 11 is pyridyl -methyl- or pyridyl-methyl- substituted by one to three R 13 ; more preferably Ci-C 4 alkyl, Ci-C 4 haloalkyl, most preferably methyl, ethyl or trifluoroethyl.
  • R 11 examples include methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl- methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 13 , or R 11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R 13 .
  • Each R 13 is independently halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or C r
  • C 4 haloalkoxy more preferably fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
  • R 3 , R 4 , R 5b , X 1 , X 2 , R 1 and R 2 are as defined for compounds of formula I.
  • R 5b is hydrogen, bromo, chloro, fluoro, or methyl.
  • X 1 is fluorine and X 2 is hydrogen or fluorine.
  • CH CH- bridge (wherein R 5a and R 5b are on adjacent carbon atoms).
  • a 2 is C-H and A 3 and A 4 are C-H or one of A 3 and A 4 is N; G 1 is O, R 3 is chlorodifluoromethyl or trifluoromethyl; R 4 is group B l .
  • a 2 is C-H and A 3 and A 4 are C-H or one of A 3 and A 4 is N; G 1 is O, R 1 is H, R 3 is chlorodifluoromethyl or trifluoromethyl; R 4 is group B l .
  • 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 group B l .
  • 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 group Bl ; R 5b is hydrogen, bromo, chloro, fluoro, or methyl.
  • 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 group B l , and R 5b is bromo, chloro, fluoro, or methyl.
  • Xi is halogen
  • X 2 is hydrogen or halogen
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 , C 4 -C 6 cycloalkyl or C 4 -C 6 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl or thietanyl substituted by one to five R 8 , oxo-thietanyl or oxo-thietanyl substituted by one to five R 8 , dioxo-thietanyl
  • X 1 is fluorine and X 2 is hydrogen or fluorine and R 2 is Ci-C 4 alkyl or
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are independently of one another C-H;
  • G 1 is oxygen
  • Xi is halogen
  • X 2 is hydrogen or halogen
  • R 1 is hydrogen
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 , C 4 -C 6 cycloalkyl or C 4 -C 6 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl or thietanyl substituted by one to five R 8 , oxo-thietanyl or oxo-thietanyl substituted by one to five R 8 , dioxo-thietanyl or dioxo-thietanyl substituted by one to five R 8 , Ci-
  • R is chlorodifluoromethyl or trifluoromethyl
  • R 4 is group B 1
  • X is C-R or nitrogen
  • R 5B is hydrogen, bromo, chloro, fluoro, methyl or trifluoromethyl
  • each R 6 is independently halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy;
  • each R 7 is independently halogen or Q-Cgalkyl
  • each R 8 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkoxy, Q- Cghaloalkoxy;
  • R 11 is d-Qalkyl or C r C 4 haloalkyl
  • each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen; or a salt or N-oxide thereof.
  • a S C-R 5 '; A 2 , A 3 and A 4 are independently of one another C-H;
  • G 1 is oxygen
  • Xi is fluorine
  • X2 is hydrogen or fluorine
  • R 1 is hydrogen
  • R 2 is Ci-C 4 alkyl or Ci-C 4 alkyl substituted by one to five R 6 , C 4 -C 6 cycloalkyl or C 4 -C 6 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl or thietanyl substituted by one to five R 8 , oxo-thietanyl or oxo-thietanyl substituted by one to five R 8 , dioxo-thietanyl or dioxo-thietanyl substituted by one to five R 6 , dio
  • R 3 is chlorodifiuoromethyl or trifiuoromethyl
  • R 4 is group B 1
  • X 3 is C-R 12 ;
  • R 5b is hydrogen, bromo, chloro, fluoro, methyl or trifiuoromethyl
  • each R 6 is independently halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, CrQalkoxy, Ci-C 4 haloalkoxy;
  • each R 7 is independently chloro, fluoro or methyl
  • each R 8 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkoxy, Q- Cghaloalkoxy;
  • each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen; or a salt or N-oxide thereof.
  • a 1 , A 2 , A 3 , A 4 , X 1 and X 2 are as defined for the compound of formula I; R is OH or Ci-C 6 alkoxy, and X B is a leaving group, e.g. halogen, such as bromo, or X B is cyano, formyl or acetyl, or a salt of N- oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , X 1 and X 2 are as defined for compounds of formula I.
  • a , A X 1 , X R , and R" are as defined for the compound of formula I; and X is a leaving group, e.g. halogen, such as bromo, or X B is cyano, formyl or acetyl, or a salt of N-oxide thereof.
  • a 1 , A 2 , A 3 , A 4 , X 1 , X 2 , R 3 and R 4 are as defined for the compound of formula I, R is OH or Q- C 6 alkoxy, or a salt of N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , X 1 , X 2 , R 3 and R 4 are as defined for compounds of formula I.
  • a 1 , A2, R1 , R2 R3 J and R 4 * are as defined for the compound of formula I, or a salt of N-oxide thereof.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , X 1 , X 2 , R 1 , R 2 , R 3 and R 4 are as defined for compounds of formula I.
  • Y b Y 2 , Y 3 , A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compound of formula I, R is OH or Ci-Cealkoxy, or a salt of N-oxide thereof, wherein compounds wherein R is OCH 3 or OCH 2 CH 3 are excluded.
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for compounds of formula I.
  • Y b Y 2 , Y 3 , A 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 and R 4 are as defined for the compound of formula I, or a salt of N-oxide thereof, wherein compounds with the following combinations of R 1 and R 2 are excluded: R 1 is H and R 2 is CH 3 , R 1 is H and R 2 is CH 2 CH 3 , R 1 is H and R 2 is CH 2 CH 2 CH 3 , R 1 is H and R 2 is CH 2 CH 2 CH 3 , R 1 is H and R 2 is CH 2 CF 3 .
  • Preferred definitions of A 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 and R 4 are as defined for compounds of formula I
  • a 1 is C-R 5b ;
  • a 2 , A 3 and A 4 are independently of one another C-H or C-R 5a , or nitrogen;
  • G 1 is oxygen or sulfur
  • Xi is halogen, Q-Cgalkyl, Ci-Cghaloalkyl, hydroxyl, cyano, Q-Cgalkoxy, Q-Cgalkenyl, C r
  • X 2 is hydrogen, halogen, cyano, Q-Cgalkyl, CpCghaloalkyl, Q-Cgalkoxy, Q-Cgalkenyl, C r
  • R 1 is hydrogen, Ci-Cgalkyl, d-Cgalkoxy, Ci-Cgalkylcarbonyl, or Ci-Cgalkoxycarbonyl;
  • R 2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R 6 , Ci-Cgalkenyl or Ci-Cgalkenyl substituted by one to five R 6 , Q-Cgalkynyl or CpCgalkynyl substituted by one to five R 6 , C3-Ciocycloalkyl or C3- Ciocycloalkyl 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 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbonyl-C
  • R 3 is d-Cghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ;
  • R 5a is hydrogen, halogen, cyano, nitro, Q-Cgalkyl, CpCghaloalkyl, CpCgalkenyl, CpCghaloalkenyl, C r Cgalkynyl, Ci-Cghaloalkynyl, C 3 -Ci 0 cycloalkyl, Q-Cgalkoxy, CpCghaloalkoxy, Ci-C 8 alkylthio, C r Cghaloalkylthio, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or C r
  • R 5b is halogen, cyano, nitro, Q-Qalkyl, Q-Qhaloalkyl, d-Cgalkenyl, Ci-Cghaloalkenyl, Q-Qalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, Q-Qalkoxy, Q-Qhaloalkoxy, Ci-Cgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Q-Qalkoxy, Q-Qhaloalkoxy, Cp
  • each R 7 is independently halogen or Q-Qalkyl
  • each R 8 and R 9 are independently halogen, cyano, nitro, Q-Qalkyl, Ci-Cghaloalkyl, C 2 -C 8 alkenyl, Q- Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Q-Qalkoxy, Ci-Cghaloalkoxy, mercapto, Q- Cgalkylthio, Q-Qhaloalkylthio, Ci-Cgalkylsulfinyl, Ci-Cghaloalkylsulfinyl, Q-Qalkylsulfonyl, Q-
  • each R 10 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or Q- C 4 haloalkoxy;
  • R 11 is hydrogen, Q-Qalkyl or Q-Qalkyl substituted by one to five R 6 , Q-Qalkenyl or Q-Qalkenyl substituted by one to five R 6 , Ci-Cgalkynyl or Ci-Cgalkynyl substituted by one to five R 6 , Q- Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , C 3 -Ciocycloalkyl-Ci-C 4 alkylene or Q- Ciocycloalkyl-Ci-C 4 alkylene substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Q -Qalkylene - wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Q- Qalkylene- wherein the heterocyclyl moiety is substituted by one to five R 8
  • Xi is halogen
  • X 2 is hydrogen, or halogen
  • R 5b is hydrogen, bromo, chloro, fluoro, or methyl.
  • R 2 is CpC 8 alkyl or CpC 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or Q- Ciocycloalkyl substituted by one to five R 7 , phenyl-CpC 4 alkylene- or phenyl-Ci -Qalkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci -Qalkylene- or pyridyl-Q -Qalkylene- wherein the pyridyl moiety is substituted by one to four R 8 , oxetanyl or oxetanyl substituted by one to five R 8 , thietanyl-CpQ alkylene or thietanyl-Q-Q alkylene wherein the thietanyl moiety is substituted by one to five R 8 , oxo-thietanyl-CpQ alky
  • R 3 is chlorodifluoromethyl or trifluoromethyl.
  • R 4 is group B 1 wherein X 3 is C-R 12 or nitrogen and each R 12 is independently hydrogen, halogen or trihalomethyl, wherein at least two R 12 are not hydrogen.
  • 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 group B 1 , and R 5b is hydrogen, bromo, chloro, fluoro, or methyl.
  • Compounds of formula I include at least one chiral centre and may exist as compounds of formula I* or compounds of formula I**.
  • compounds of formula I** are more biologically active than compounds of formula I*.
  • the invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to 99:1, e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio.
  • the molar proportion of compound I** compared to the total amount of both enantiomers is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%>.
  • the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimerically) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%>.
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.
  • Each of the compounds disclosed in Tables IP to 33P and 1Q to 33Q represets a disclosure of a compound of formula I* and a disclosure of a compound of formula I**.
  • R When R is OH such reactions are usually carried out in the presence of a coupling reagent, such as ⁇ , ⁇ '-dicyclohexylcarbodiimide (“DCC”), l-ethyl-3-(3-dimethylamino-propyl)- carbodiimide hydrochloride (“EDC”) or bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-Cl”), in the presence of a base, and optionally in the presence of a nucleophilic catalyst, such as hydroxybenzotriazole (“HOBT").
  • DCC ⁇ , ⁇ '-dicyclohexylcarbodiimide
  • EDC l-ethyl-3-(3-dimethylamino-propyl)- carbodiimide hydrochloride
  • BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphonic chloride
  • R When R is CI, such reactions are usually carried out in
  • a biphasic system comprising an organic solvent, preferably ethyl acetate, and an aqueous solvent, preferably a solution of sodium hydrogen carbonate.
  • R is Ci-C 6 alkoxy it is sometimes possible to convert the ester directly to the amide by heating the ester and amine together in a thermal process.
  • Suitable bases include pyridine, triethylamine, 4-(dimethylamino)-pyridine (“DMAP”) or 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 WO09080250.
  • compounds of formula (IA) wherein G 1 is oxygen can be prepared by various methods from an intermediate of formula (VII) 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 or acetyl according to similar methods to those described in WO09080250.
  • An intermediate of formula (VII) can be prepared for example from an intermediate of formula (VIII) as described in Scheme 1.
  • Intermediates of formula (VIII) are either known or can be obtained by known methods to the person skilled in the art.
  • Intermediates of formula (X) can be prepared by various methods, for example from a compound of formula (XI) wherein X B is a leaving group, for example a halogen, such as bromo, by treatment with an magnesium or an organometallic reagent such as butyl lithium or isopropyl magnesium bromide followed by addition of diethyl oxalate, as described in the preparation example 1.
  • X B is a leaving group, for example a halogen, such as bromo
  • an magnesium or an organometallic reagent such as butyl lithium or isopropyl magnesium bromide followed by addition of diethyl oxalate, as described in the preparation example 1.
  • leaving groups includes leaving groups such as halogen, Q-Cgalkoxy, Ci-C 8 alkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, C r
  • aryl is preferably phenyl
  • diazonium salts e.g. the leaving group may be selected from -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 _
  • phosphonate esters e.g. -OP(0)(OR)3 ⁇ 4 wherein R is methyl or ethyl
  • 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., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici; from the class of the Bivalva, for example, Dreissena spp.; from the order of the Chilopoda, for example, Geophilus spp., Scut
  • 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,
  • 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.,
  • Tylenchorhynchus spp. Tylenchulus spp.
  • Tylenchulus semipenetrans Tyiphinema 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. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis
  • Kalotermitidae for example Neotermes spp.
  • Rhinotermitidae for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis
  • Termitidae for example
  • Rhodopholus spp. banana burrowing nematodes
  • Tylenchulus spp. citrus nematodes
  • Haemonchus contortus barber pole worm
  • Caenorhabditis eelworm Trichostrongylus spp.
  • 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-
  • 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 Ugnosellus, 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, PopilUa 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 Ugnosellus, Halyomorpha spp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, PopilUa 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., Mi
  • the compounds of the invention are preferably used on corn to control Euschistus heros, Euschistus spp., Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotoma trifurcata, PopilUa 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, Hyper a 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 Uneolaris, Trichoplusia ni.
  • the compounds of the invention may be used on brassicas to control, for example, Plutella xylostella, Pieris spp., Mamestra spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Spodoptera spp., Empoasca spp., thrips spp., Delia spp., Murgantia spp., Trialeurodes spp., Bemisia spp., Microtheca spp., Aphids.
  • the compounds of the invention are preferably used on brassicas to control Plutella xylostella, Pieris spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp..
  • 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 are preferably used on rice to control Leptocorisa spp., Lissorhoptrus spp., Oebalus pugnax, Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix spp., Sogatella furcifera, Stenchaetothrips biformis, Thrips spp., Hydrellia philippina, Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Chilo suppressalis, Chilo polychrysus, Oulema oryzae.
  • the compounds of the invention may be used on coffee to control, for example, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychus spp., Brevipalpus spp., Mealybugs.
  • 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 occidentalis, Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp., Neoleucinodes spp..
  • 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
  • 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.
  • 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 destructor; Limonius canu; Limonius californicus; rice water weevil:
  • 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 LibertyLink®.
  • 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).
  • Compounds of formula I 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.
  • 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
  • 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
  • pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; 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, ec
  • 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 CrylAb
  • Agrisure®RW corn producing mCry3A
  • Agrisure® Viptera corn hybrids producing Vip3Aa
  • Agrisure300GT corn hybrids producing CrylAb and mCry3A
  • YieldGard® corn hybrids producing the CrylAb 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:
  • 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
  • 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 O.lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
  • a compound of formula (I) When used in a seed dressing, a compound of formula (I) is generally used at a rate of 0.000 lg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
  • 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.
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 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-Cio fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as cycl
  • 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); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • 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, nonyl
  • 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.
  • compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
  • These concentrates which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • 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).
  • 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;
  • Carbamates including aryl carbamates
  • pirimicarb triazamate
  • cloethocarb carbofuran
  • furathiocarb furathiocarb
  • ethiofencarb aldicarb
  • thiofurox carbosulfan
  • bendiocarb fenobucarb
  • propoxur methomyl or oxamyl
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • f) Pyrazoles such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate
  • g) 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;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide
  • 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 (WO 2006129714; WO2011/147953; WO2011/147952), CAS: 26914-55-8 (WO 2007020986), chlorfenapyr, pymet
  • 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 hydramethylnon , cyromazine , methoprene , chlorfluazuron or diflubenzuron ).
  • acaricidal ovo-larvicides to give combinations such as clofentezine , flubenzimine , hexythiazox or tetradifon
  • acaricidal motilicides to give combinations such as dicofol or propargite
  • 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 , a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone , 4-chloro-2-cyano-N,N-dimethyl-5-f>- tolylimidazole-1 -sulfonamide (IKF-916, cyamidazosulfamid) , 3-5-dichloro-N-(3-chloro-l-ethyl-l- methyl-2-oxopropyl)-4-methylbenzamide (RH-7281, zo
  • 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, be
  • the active ingredients combinations described above comprising a compound selected of the invention, in particulary from Tables IP to 33P and Tables 1Q to 33Q 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
  • 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 provides a compound of the invention for use in a method of therapeutic treatment.
  • the invention in a further aspect 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 paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazo lines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
  • 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.
  • 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: 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, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, tric
  • triclabendazole epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide; more preferably, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenb
  • enrofloxacin praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon or pyrantel.
  • ratios of the compound of formula I to any mixing partner described herein include 100: 1 to 1 :6000, 50: 1 to 1 :50, 20: 1 to 1 :20, even more especially from 10:1 to 1 : 10, 5: 1 to 1 :5, 2:1 to 1 :2, 4: 1 to 2: 1, 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 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :
  • a combination product of the invention may comprise a pesticidally effective amount of a compound of formula I and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action.
  • salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.
  • 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., game birds, and ratites (e.g., ostriches).
  • ratites e.g., ostriches.
  • Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture.
  • 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.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un composé de formule I (I), dans laquelle A1 représente C-R5b ; A2, A3 et A4 représentent indépendamment les uns des autres C-H ou C-R5a, ou l'azote ; G1 représente l'oxygène ; Y1--Y2-Y3 représente -C=N-O- ; X1 représente un halogène ; X2 représente l'hydrogène ou un halogène ; R3 représente un haloalkyle en C1-C8 ; R4 représente aryle ou aryle substitué par un à cinq R9, ou hétéroaryle ou hétéroaryle substitué par un à cinq R9 ; et R1, R2, R5a, R5b et R9 sont tels que définis dans les revendications. L'invention concerne également des procédés d'élimination d'insectes, d'acariens, de nématodes ou de mollusques, lesdits procédés comprenant l'application sur un animal nuisible, sur un locus d'un animal nuisible ou sur une plante susceptible d'être attaquée par un animal nuisible d'une quantité insecticide, acaricide, nématicide ou molluscicide efficace d'un composé de formule I.
PCT/EP2013/054969 2012-03-12 2013-03-12 Composés de 2-aryl-acétamide insecticides Ceased WO2013135674A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015169723A1 (fr) * 2014-05-09 2015-11-12 Syngenta Participations Ag Composés insecticides à base de dérivés de thiophène
US12304903B2 (en) 2020-07-24 2025-05-20 Elanco Us Inc. Process for making an isoxazoline compound and intermediate thereof

Citations (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR960510A (fr) 1950-04-20
DE2845293A1 (de) * 1978-10-18 1980-05-08 Basf Ag Alpha -azolyl- alpha -phenylessigsaeurederivate
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
US4977270A (en) * 1988-12-01 1990-12-11 Ici Americas Inc. Substituted 2,4-dioxodiazolidines and -thiadiazolidines and their use as herbicides
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
WO1991012265A1 (fr) * 1990-02-19 1991-08-22 Rhone-Poulenc Rorer S.A. N-phenyl n-alcoxycarbonylalkyle glycinamides, leur preparation et les medicaments les contenant
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
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
US6358971B1 (en) * 1998-05-20 2002-03-19 Eli Lilly And Company Anti-viral compounds
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
WO2005085216A1 (fr) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
WO2006088920A1 (fr) * 2005-02-16 2006-08-24 Schering Corporation Pyridyle a liaison amine et piperazine-piperidines substituees a activite agoniste cxcr3
WO2006113471A2 (fr) * 2005-04-19 2006-10-26 Merck & Co., Inc. Antagonistes de nmda/nr2b a base de n-alkyl-azacycloalkyle
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
WO2007053436A1 (fr) * 2005-10-31 2007-05-10 Janssen Pharmaceutica N.V. Piperazines et piperidines substituees en tant que modulateurs du recepteur du neuropeptide y2
DE102006015467A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
WO2008078350A2 (fr) * 2006-12-27 2008-07-03 F.I.S. Fabbrica Italiana Sintetici S.P.A. Procédé de préparation d'acides fluorophénylacétiques et de dérivés de ceux-ci
EP1997813A1 (fr) * 2006-03-10 2008-12-03 Nissan Chemical Industries, Ltd. Compose isoxazoline substitue et agent antiparasite
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
US20100022598A1 (en) * 2006-10-20 2010-01-28 David Chen Substituted inmidazoles as bombesin receptor subtype-3 modulators
WO2010019899A1 (fr) * 2008-08-14 2010-02-18 Takeda Pharmaceutical Company Limited Inhibiteurs de cmet
EP2199287A1 (fr) * 2007-09-10 2010-06-23 Nissan Chemical Industries, Ltd. Composé isoxazoline substitué et agent de lutte contre les organismes nuisibles
EP2246343A1 (fr) * 2008-02-29 2010-11-03 Nissan Chemical Industries, Ltd. Procédé pour la production d'un composé thiophène et intermédiaire pour celui-ci
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
WO2011091187A1 (fr) 2010-01-20 2011-07-28 Subject Company, Inc. Gestion de contacts et communication
WO2011092287A1 (fr) * 2010-02-01 2011-08-04 Basf Se Composés d'isoxazoline cétoniques substitués et leurs dérivés pour lutter contre des animaux nuisibles
WO2011147953A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2011147952A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
US20120053174A1 (en) * 2010-09-01 2012-03-01 Hadd Michael J Quinazoline compounds and methods of use thereof
US20120053176A1 (en) * 2010-09-01 2012-03-01 Ambit Biosciences Corp. Adenosine a3 receptor modulating compounds and methods of use thereof
WO2012030944A2 (fr) * 2010-09-01 2012-03-08 Ambit Biosciences Corporation Composés quinoléine et isoquinoléine et leurs procédés d'utilisation
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
WO2012097744A1 (fr) * 2011-01-20 2012-07-26 Merck Sharp & Dohme Corp. Antagonistes du récepteur des minéralocorticoïdes
EP2502898A1 (fr) * 2009-11-18 2012-09-26 Central Glass Company, Limited Procédé d'élaboration d'ester d'acide difluoroacétique aromatique
WO2012177603A2 (fr) * 2011-06-19 2012-12-27 Viamet Pharmaceuticals, Inc. Composés inhibiteurs de métalloenzymes
US20120329802A1 (en) * 2011-06-23 2012-12-27 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds

Patent Citations (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR960510A (fr) 1950-04-20
DE2845293A1 (de) * 1978-10-18 1980-05-08 Basf Ag Alpha -azolyl- alpha -phenylessigsaeurederivate
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
US4977270A (en) * 1988-12-01 1990-12-11 Ici Americas Inc. Substituted 2,4-dioxodiazolidines and -thiadiazolidines and their use as herbicides
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
WO1991012265A1 (fr) * 1990-02-19 1991-08-22 Rhone-Poulenc Rorer S.A. N-phenyl n-alcoxycarbonylalkyle glycinamides, leur preparation et les medicaments les contenant
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
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
US6358971B1 (en) * 1998-05-20 2002-03-19 Eli Lilly And Company Anti-viral compounds
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
WO2005085216A1 (fr) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
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
WO2006088920A1 (fr) * 2005-02-16 2006-08-24 Schering Corporation Pyridyle a liaison amine et piperazine-piperidines substituees a activite agoniste cxcr3
WO2006113471A2 (fr) * 2005-04-19 2006-10-26 Merck & Co., Inc. Antagonistes de nmda/nr2b a base de n-alkyl-azacycloalkyle
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
WO2007053436A1 (fr) * 2005-10-31 2007-05-10 Janssen Pharmaceutica N.V. Piperazines et piperidines substituees en tant que modulateurs du recepteur du neuropeptide y2
EP1997813A1 (fr) * 2006-03-10 2008-12-03 Nissan Chemical Industries, Ltd. Compose isoxazoline substitue et agent antiparasite
DE102006015467A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
US20100022598A1 (en) * 2006-10-20 2010-01-28 David Chen Substituted inmidazoles as bombesin receptor subtype-3 modulators
WO2008078350A2 (fr) * 2006-12-27 2008-07-03 F.I.S. Fabbrica Italiana Sintetici S.P.A. Procédé de préparation d'acides fluorophénylacétiques et de dérivés de ceux-ci
EP2199287A1 (fr) * 2007-09-10 2010-06-23 Nissan Chemical Industries, Ltd. Composé isoxazoline substitué et agent de lutte contre les organismes nuisibles
WO2009080250A2 (fr) 2007-12-24 2009-07-02 Syngenta Participations Ag Composés insecticides
EP2246343A1 (fr) * 2008-02-29 2010-11-03 Nissan Chemical Industries, Ltd. Procédé pour la production d'un composé thiophène et intermédiaire pour celui-ci
WO2010019899A1 (fr) * 2008-08-14 2010-02-18 Takeda Pharmaceutical Company Limited Inhibiteurs de cmet
EP2502898A1 (fr) * 2009-11-18 2012-09-26 Central Glass Company, Limited Procédé d'élaboration d'ester d'acide difluoroacétique aromatique
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
WO2011091187A1 (fr) 2010-01-20 2011-07-28 Subject Company, Inc. Gestion de contacts et communication
WO2011092287A1 (fr) * 2010-02-01 2011-08-04 Basf Se Composés d'isoxazoline cétoniques substitués et leurs dérivés pour lutter contre des animaux nuisibles
WO2011147953A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
WO2011147952A1 (fr) 2010-05-28 2011-12-01 Basf Se Mélanges pesticides
US20120053176A1 (en) * 2010-09-01 2012-03-01 Ambit Biosciences Corp. Adenosine a3 receptor modulating compounds and methods of use thereof
WO2012030944A2 (fr) * 2010-09-01 2012-03-08 Ambit Biosciences Corporation Composés quinoléine et isoquinoléine et leurs procédés d'utilisation
US20120053174A1 (en) * 2010-09-01 2012-03-01 Hadd Michael J Quinazoline compounds and methods of use thereof
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
WO2012097744A1 (fr) * 2011-01-20 2012-07-26 Merck Sharp & Dohme Corp. Antagonistes du récepteur des minéralocorticoïdes
WO2012177603A2 (fr) * 2011-06-19 2012-12-27 Viamet Pharmaceuticals, Inc. Composés inhibiteurs de métalloenzymes
US20120329802A1 (en) * 2011-06-23 2012-12-27 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds

Non-Patent Citations (29)

* Cited by examiner, † Cited by third party
Title
"McCutcheon's Volume 2: Functional Materials, annual International and North American editions", vol. 2, MCCUTCHEON'S DIVISION
A. J. SPEZIALE ET AL: "Reactions of Phosphorus Compounds. XIII. Kinetics and Mechanism of the Reaction of Triphenylphosphine with [alpha],[alpha]-Dihaloamides", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 31, no. 8, 1 August 1966 (1966-08-01), pages 2450 - 2454, XP055064441, ISSN: 0022-3263, DOI: 10.1021/jo01346a005 *
CATERINA FATTORUSSO ET AL: "Specific Targeting Highly Conserved Residues in the HIV-1 Reverse Transcriptase Primer Grip Region. Design, Synthesis, and Biological Evaluation of Novel, Potent, and Broad Spectrum NNRTIs with Antiviral Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 23, 1 November 2005 (2005-11-01), pages 7153 - 7165, XP055064516, ISSN: 0022-2623, DOI: 10.1021/jm050257d *
CHEN GUO ET AL: "Palladium-Catalyzed Cross-Coupling of Ethyl [alpha]-Bromo-[alpha]-fluoroacetate with Arylboronic Acids: Facile Synthesis of [alpha]-Aryl-[alpha]-fluoroacetates", SYNTHESIS, vol. 2010, no. 11, 1 June 2010 (2010-06-01), pages 1837 - 1844, XP055064482, ISSN: 0039-7881, DOI: 10.1055/s-0029-1218740 *
CHRISTOPHE SABOUREAU ET AL: "Electroreductive coupling of trifluoromethylarenes with electrophiles: synthetic applications", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 16, 1 January 1989 (1989-01-01), pages 1138, XP055064519, ISSN: 0022-4936, DOI: 10.1039/c39890001138 *
CLARK A J ET AL: "1,4-Aryl migration under copper(I) atom transfer conditions", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 50, no. 40, 7 October 2009 (2009-10-07), pages 5609 - 5612, XP026496745, ISSN: 0040-4039, [retrieved on 20090722], DOI: 10.1016/J.TETLET.2009.07.089 *
CRICKMORE ET AL., MICROBIOL. MOL. BIOL. REV., vol. 62, 1998, pages 807 - 813
D. S. KETTLE: "Medical and Veterinary Entomology", JOHN WILEY AND SONS
DATABASE REGISTRY accession no. 15972-17-7
DATABASE REGISTRY accession no. 6914-55-8
FOTSCH CHRISTOPHER ET AL: "Further Studies with the 2-Amino-1,3-thiazol-4(5H)-one Class of 11 beta-Hydroxysteroid Dehydrogenase Type 1 Inhibitors: Reducing Pregnane X Receptor Activity and Exploring Activity in a Monkey Pharmacodynamic Model", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 51, no. 24, 1 December 2008 (2008-12-01), pages 7953 - 7967, XP002582999, ISSN: 0022-2623, [retrieved on 20081119], DOI: 10.1021/JM801073Z *
GIUSEPPE FRACCHIOLLA ET AL: "Synthesis, biological evaluation and molecular investigation of fluorinated peroxisome proliferator-activated receptors / dual agonists", BIOORGANIC & MEDICINAL CHEMISTRY, PERGAMON, GB, vol. 20, no. 6, 16 January 2012 (2012-01-16), pages 2141 - 2151, XP028465326, ISSN: 0968-0896, [retrieved on 20120128], DOI: 10.1016/J.BMC.2012.01.025 *
GRECO G ET AL: "A comparitive Field analysis model for 6-arylpyrrolo[2,1-d][1,5]benzothiazaepines binding selectively to the mitochondrial benzodiazepine receptor", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 37, no. 24, 1 January 1994 (1994-01-01), pages 4100 - 4108, XP002167537, ISSN: 0022-2623, DOI: 10.1021/JM00050A007 *
H. L. HALLER ET AL: "The Chemical Composition of Technical DDT", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 67, no. 9, 19 September 1945 (1945-09-19), pages 1591 - 1602, XP055064526, ISSN: 0002-7863, DOI: 10.1021/ja01225a058 *
HELMINTHS, E.; J. L. SOULSBY; F. A. DAVIS CO.; PHILADELPHIA, PA.: "Textbook of Veterinary Clinical Parasitology", vol. 1
HELMINTHS; ARTHROPODS; PROTOZOA: "Monnig's Veterinary Helminthology and Entomology", WILLIAMS AND WILKINS CO.
JAGUELIN S ET AL: "Opening of gem dicyano epoxides with amino hydrohalides: application to the synthesis of structural analogs of tetramisole and biological evaluation", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, EDITIONS SCIENTIFIQUE ELSEVIER, PARIS, FR, vol. 26, no. 3, 1 April 1991 (1991-04-01), pages 313 - 321, XP023870239, ISSN: 0223-5234, [retrieved on 19910401], DOI: 10.1016/0223-5234(91)90064-T *
KENICHI FUJIKAWA ET AL: "A New Method for Aromatic Difluoromethylation: Copper-Catalyzed Cross-Coupling and Decarboxylation Sequence from Aryl Iodides", ORGANIC LETTERS, vol. 13, no. 20, 21 October 2011 (2011-10-21), pages 5560 - 5563, XP055064465, ISSN: 1523-7060, DOI: 10.1021/ol202289z *
LEE S M ET AL: "Selective electrolytic fluorinations in 70% HF/30% pyridine", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 77, no. 1, 1 March 1996 (1996-03-01), pages 65 - 70, XP004020420, ISSN: 0022-1139, DOI: 10.1016/0022-1139(95)03379-3 *
MARIE-GABRIELLE LE PIRONNEC ET AL: "A General and Simple Synthesis of alpha-Halo Amides vie alpha,alpha-Dicyano Epoxides", SYNTHESIS, no. 2, 1 February 1997 (1997-02-01), pages 229 - 232, XP055064437 *
N. ILAYARAJA ET AL: "The effect of substituents and operating conditions on the electrochemical fluorination of alkyl phenylacetates in Et3N.4HF medium", JOURNAL OF FLUORINE CHEMISTRY, vol. 129, no. 3, 1 March 2008 (2008-03-01), pages 185 - 192, XP055064514, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2007.10.007 *
N.S. KOZLOV: "SYNTHESIS AND SOME PROPERTIES OF 1,3- DIARYL- 2.2- DIBROMOAZIRIDINES", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 10, 1 January 1974 (1974-01-01), pages 73 - 74, XP055064440 *
P. LEGREL ET AL: "Synthese en une etape d'[alpha]-alcoxyhydrazides, de derives d'[alpha]-aminoacides et d'[alpha]-hydroxyacides a partir des [alpha]-halogenohydrazides. Etude du mecanisme de la reaction.", TETRAHEDRON, vol. 44, no. 15, 1 January 1988 (1988-01-01), pages 4805 - 4814, XP055064522, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)86184-6 *
R. O. DRUMMAND; J. E. GEORGE; S. E. KUNZ: "Control of Arthropod Pests of Livestock: A Review of Technology", CRC PRESS
ROBERT V. HOFFMAN ET AL: "Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 57, no. 21, 1 October 1992 (1992-10-01), pages 5700 - 5707, XP055064439, ISSN: 0022-3263, DOI: 10.1021/jo00047a024 *
SHINGO NAKAMURA ET AL: "Enantioselective Protonation of Silyl Enol Ethers and Ketene Disilyl Acetals with Lewis Acid-Assisted Chiral Brønsted Acids: Reaction Scope and Mechanistic Insights", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 34, 1 August 2000 (2000-08-01), pages 8120 - 8130, XP055064476, ISSN: 0002-7863, DOI: 10.1021/ja001164i *
STEVEN BLOOM ET AL: "Tricomponent Catalytic [alpha],[alpha]-Difluorination of Acid Chlorides", ORGANIC LETTERS, vol. 13, no. 19, 7 October 2011 (2011-10-07), pages 5068 - 5071, XP055064426, ISSN: 1523-7060, DOI: 10.1021/ol2019295 *
TAKAHIRO SAWAMURA ET AL: "Use of Task-Specific Ionic Liquid for Selective Electrocatalytic Fluorination", ORGANIC LETTERS, vol. 12, no. 3, 5 February 2010 (2010-02-05), pages 644 - 646, XP055064533, ISSN: 1523-7060, DOI: 10.1021/ol9028836 *
YAO Z-J ET AL: "Synthesis of Fmoc-Protected 4-Carboxydifluoromethyl-L-phenylalanine: A Phosphotyrosyl Mimetic of Potential Use for Signal Transduction Studies", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 55, no. 10, 5 March 1999 (1999-03-05), pages 2865 - 2874, XP004157124, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(99)00076-9 *

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