WO2020141135A1 - Pesticidally active heterocyclic derivatives with sulfur containing substituents - Google Patents

Pesticidally active heterocyclic derivatives with sulfur containing substituents Download PDF

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WO2020141135A1
WO2020141135A1 PCT/EP2019/086976 EP2019086976W WO2020141135A1 WO 2020141135 A1 WO2020141135 A1 WO 2020141135A1 EP 2019086976 W EP2019086976 W EP 2019086976W WO 2020141135 A1 WO2020141135 A1 WO 2020141135A1
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formula
compounds
spp
provides
compound
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PCT/EP2019/086976
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French (fr)
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Indira SEN
Vikas SIKERVAR
Andrew Edmunds
Michel Muehlebach
Sebastian RENDLER
Anke Buchholz
Daniel EMERY
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Syngenta Crop Protection Ag
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to pesticidally active, in particular insecticidally active heterocyclic derivatives containing sulfur substituents, to processes for their preparation, to compositions comprising those compounds, and to their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina.
  • the present invention accordingly relates to compounds of formula I,
  • A is CH or N
  • X is S, SO or S0 2 ;
  • Ri is Ci-C4alkyl, or C3-C6cycloalkyl-Ci-C4alkyl;
  • R2 IS Ci-C6alkyl, Ci-C6haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl substituted with cyano, Ci- C6cyanoalkyl, Ci-C4alkoxyCi-C4alkyl, halogen, cyano, Ci-C4haloalkoxy, Ci-C4alkoxy, aminocarbonyl, Ci-C4alkoxycarbonyl, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, and Ci-C4alkylsulfonyl, Ci- C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, and Ci-C4haloalkylsulfonyl;
  • n 0, 1 or 2;
  • Q is a radical selected from the group consisting of formula Qi to Q4
  • X2 is O or NR5, wherein R5 is Ci-C 4 alkyl
  • R3 is halogen, Ci-C6haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci-C 4 haloalkylsulfinyl, Ci-C 4 haloalkylsulfonyl or Ci-C6haloalkoxy;
  • Gi is N or CH
  • G2 and G3 are, independently from each other, N or CH; or
  • Compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as Ci-C 4 alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as Ci-C 4 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by
  • Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.
  • bases for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts
  • salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethy
  • the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book“Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991 .
  • the compounds of formula I according to the invention also include hydrates which may be formed during the salt formation.
  • substituents are indicated as being itself further substituted, this means that they carry one or more identical or different substituents, e.g. one to four substituents. Normally not more than three such optional substituents are present at the same time. Preferably not more than two such substituents are present at the same time (i.e. the group is substituted by one or two of the substituents indicated). Where the additional substituent group is a larger group, such as cycloalkyl or phenyl, it is most preferred that only one such optional substituent is present. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio.
  • Ci-C x alkyl refers to a saturated straight-chain or branched hydrocarbon radical attached via any of the carbon atoms having 1 to x carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1 - ethylpropyl, n-hexyl, n-pentyl, 1 , 1 -dimethylpropyl, 1 , 2-dimethylpropyl, 1 - methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 , 1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 , 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1 -e
  • Ci-C x haloalkyl refers to a straight-chain or branched saturated alkyl radical attached via any of the carbon atoms having 1 to x carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of chloromethyl, dichloromethyl, trich loro methyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2- fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2, 2-difluoroe
  • Ci-C2-fluoroalkyl would refer to a Ci-C2-alkyl radical which carries 1 ,2, 3,4, or 5 fluorine atoms, for example, any one of difluoromethyl, trifluoromethyl, 1 - fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 1 ,1 , 2, 2-tetrafluoroethyl or pentafluoroethyl.
  • Ci-C x alkoxy refers to a straight-chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via an oxygen atom, i.e., for example, any one of methoxy, ethoxy, n-propoxy, 1 -methylethoxy, n-butoxy, 1 -methylpropoxy, 2- methylpropoxy or 1 , 1 -dimethylethoxy.
  • Ci-C x haloalkoxy refers to a Ci-C x alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoro methoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2- bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluorine, chlorine, bromine and/
  • Ci-C ralkylsulfanyl refers to a straight chain or branched saturated alkyl radical having 1 to n carbon atoms (as mentioned above) which is attached via a sulfur atom, i.e., for example, any one of methylthio, ethylthio, n-propylthio, 1 -methylethylthio, butylthio, 1 -methylpropylthio, 2- methylpropylthio or 1 , 1 -dimethylethylthio.
  • Ci-C x alkylsulfinyl refers to a straight chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via the sulfur atom of the sulfinyl group, i.e., for example, any one of methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1 -methylethyl- sulfinyl, n-butylsulfinyl, 1 -methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 , 1 -dimethyl- ethylsulfinyl, n- pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methyl- butylsulfinyl, 1 , 1 , 1
  • Ci-C x alkylsulfonyl refers to a straight chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via the sulfur atom of the sulfonyl group, i.e., for example, any one of methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1 -methylpropylsulfonyl, 2-methylpropylsulfonyl or t-butylsulphonyl.
  • Ci-C x haloalkylsulfanyl refers to a C1 -C x alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2, 2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro- 2,2-difluoroethylthio, 2, 2-dichloro-2
  • Ci-C x haloalkylsulfinyl and “Ci-C n haloalkylsulfonyl” refers to the groups above but with the sulfur in oxidations state 1 or 2 respectively.
  • Ci-C x alkoxycarbonyl refers to a straight chain or branched alkoxy radical having 1 to x carbon atoms (as mentioned above) which is attached via the carbon atom of the carbonyl group, i.e., for , any one of methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1- methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 , 1- dimethylethoxycarbonyl.
  • Ci-Cxcyanoalkyl refers to a straight chain or branched saturated alkyl radicals having 1 to x carbon atoms (as mentioned above) which is substituted by a cyano group, for example cyanomethylene, cyanoethylene, 1 ,1-dimethylcyanomethyl, cyanomethyl, cyanoethyl, and 1- dimethylcyanomethyl.
  • C3-C6cycloalkyl refers to 3-6 membered cycloylkyl groups such as cyclopropane, cyclobutane, cyclopropane, cyclopentane and cyclohexane.
  • Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl
  • Embodiments according to the invention are provided as set out below.
  • Embodiment 1 provides compounds of formula I, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined above.
  • Embodiment 2 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiment 1 wherein:
  • A is CH or N
  • X is S, SO or S0 2 ;
  • Ri is Ci-C3alkyl or C3-C6cycloalkyl-Ci-C 2 alkyl
  • R2 IS Ci-C 4 alkyl, Ci-C 4 haloalkyl, C3-C 4 cycloalkyl, C3-C 4 cycloalkyl substituted with cyano, Ci- C2cyanoalkyl, Ci-C3alkoxyCi-C 2 alkyl, fluoro, chloro, bromo, cyano, Ci-C3haloalkoxy, Ci-C 4 alkoxy, aminocarbonyl, Ci-C2alkoxycarbonyl, Ci-C2alkylsulfanyl, Ci-C2alkylsulfinyl, Ci-C2alkylsulfonyl, Ci- C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl or Ci-C2haloalkylsulfonyl;
  • n 0 or 1 ;
  • Q is a radical selected from the group consisting of formula Qi , Q2 or C
  • Xi is NR4, wherein R4 is Ci-C 2 alkyl
  • X2 is O or NR5, wherein R5 is Ci-C2alkyl
  • R3 is fluoro, chloro, bromo, Ci-C 2 haloalkyl, Ci-C 2 haloalkylsulfanyl, Ci-C 2 haloalkylsulfinyl, Ci- C 2 haloalkylsulfonyl or Ci-C 2 haloalkoxy;
  • Gi is N or CH
  • G 3 is N or CH.
  • Embodiment 3 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiment 1 wherein:
  • A is CH or N
  • X is S, SO or SO 2 ;
  • Ri is ethyl, propyl, isopropyl or cyclopropylmethyl
  • R 2 IS Ci-C3alkyl, Ci-C 2 haloalkyl, cyclopropyl, cyclopropyl substituted with cyano, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, fluoro, chloro, bromo, cyano, Ci- C 2 haloalkoxy, Ci-C3alkoxy, aminocarbonyl, methoxycarbonyl, Ci-C 2 alkylsulfanyl, Ci-C 2 alkylsulfinyl, Ci- C 2 alkylsulfonyl, Ci-C 2 haloalkylsulfanyl, Ci-C 2 haloalkylsulfinyl or Ci-C 2 haloalkylsulfonyl;
  • n 0 or 1 ;
  • Q is a radical selected from the group consisting of formula Qi or C
  • Xi is NCH 3 ;
  • X 2 is NCH 3 ;
  • R3 is bromo, trifluoromethyl, pentafluoroethyl, 1 , 1 -difluoroethyl, difluoromethyl, difluorochloromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, difluoromethylsulfanyl, difluoromethylsulfinyl, difluoromethylsulfony, difluoromethoxy, difluorobromomethoxy or
  • Gi is N or CH.
  • Embodiment 4 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that when Q is C and X2 is NRs, then Gi is CH.
  • Embodiment 5 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that F3 ⁇ 4 is not Ci- C2haloalkyl when Q is C , Gi is N and X2 is NMe.
  • Embodiment 6 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that R2 is not trifluoromethyl when Q is C , Gi is N and X2 is NMe.
  • Embodiment 7 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that the compound 2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5- b] pyridine is excluded.
  • a preferred group of compounds of formula I is represented by the compounds of formula 1-1
  • A is CH or N;
  • X is S, SO or SO2;
  • Ri is Ci-C 4 alkyl;
  • R2 is Ci-C 4 haloalkyl, halogen, cyano, aminocarbonyl, or Ci-C2alkoxycarbonyl;
  • R3 is Ci-C 4 haloalkyl, Ci- C 4 haloalkylsulfanyl, Ci-C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • n is 0 or 1 ;
  • A is CH or N;
  • X is S or SO2;
  • Ri is Ci-C3alkyl;
  • R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl;
  • R3 is Ci-C 2 fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl;
  • n is 0 or 1 ;
  • A is CH; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C 2 fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; n is 0 or 1 ; Xi is NCH3; and Gi is CH.
  • Gi is CH
  • Xi is NMe and A is CH.
  • Ri is Ci-C3alkyl; preferably ethyl, propyl, or isopropyl
  • R2 is 1 , 1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl
  • R3 is Ci-C 2 fluoroalkyl, Ci-C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci- C2fluoroalkylsulfonyl; preferably trifloromethyl.
  • A, X, Ri , R2, R3, n, Xi and Gi are as defined under formula I above; preferably A is CH or N, more preferably A is CH; preferably Ri is Ci-C2alkyl, more preferably Ri is ethyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; more preferably R2 is pentafluoroethyl, trifluoromethyl, bromo, cyano, aminocarbonyl, or methoxycarbonyl; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; more
  • A, X, Ri , R2, R3, Xi and Gi are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula 1-1 .
  • A is CH or N;
  • X is S, SO or S0 2 ;
  • Ri is Ci-C 4 alkyl;
  • R2 is Ci-C 4 haloalkyl, halogen or cyano;
  • R3 is Ci-C 4 haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci- C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • n is 0 or 1 ;
  • G3 is N or CH.
  • A is CH or N;
  • X is S, SO or SO2;
  • Ri is Ci- C3alkyl;
  • R2 is Ci-C2haloalkyl, halogen or cyano;
  • R3 is Ci-C 2 haloalkyl, Ci-C2haloalkylsulfanyl, Ci- C2haloalkylsulfinyl, or Ci-C2haloalkylsulfonyl;
  • n is 0 or 1 ; and
  • G3 is N or CH.
  • A, X, Ri , R2, R3, n and G3 are as defined under formula I above; preferably A is CH or N; preferably X is S, SO or SO2; preferably Ri is Ci-C2alkyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen or cyano; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; preferably n is 0 or 1 ; more preferably n is 1 ; and preferably G3 is N or CH.
  • A, X, Ri , R2, R3 and G3 are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-2.
  • a further preferred group of compounds of formula I is represented by the compounds of formula i-3
  • A is CH or N;
  • X is S, SO or S0 2 ;
  • Ri is Ci-C 4 alkyl;
  • R2 is Ci-C 4 haloalkyl, halogen or cyano;
  • R3 is Ci-C 4 haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci- C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • n is 0 or 1 ;
  • G2 is N and G3 is CH.
  • A is CH or N;
  • X is S, SO or SO2;
  • Ri is Ci- C3alkyl;
  • R2 is Ci-C 4 haloalkyl, halogen or cyano;
  • R3 is Ci-C 4 haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci- C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • n is 0 or 1 ;
  • G2 is CH and G3 is N.
  • A, X, Ri , R2, R3, n, G2 and G3 are as defined under formula I above; preferably A is CH or N; X is S, SO or SO2; preferably Ri is Ci-C2alkyl; preferably R2 is 1 , 1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen or cyano; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; preferably n is 0 or 1 ; more preferably n is 1 ; in one prefered embodiment G2 is N and G3 is CH; and in another prefered embodiment G2 is CH and G3 is N.
  • A, X, Ri , R2, R3, G2 and G3 are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-3.
  • A is CH or N;
  • X is S, SO or S0 2 ;
  • Ri is Ci-C 4 alkyl;
  • R2 is Ci-C 4 haloalkyl, halogen, cyano;
  • R3 is Ci-C 4 haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci- C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • n is 0 or 1 ;
  • A is CH or N;
  • X is S or SO2;
  • Ri is Ci-C3alkyl;
  • R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl;
  • R3 is Ci-C 2 fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl;
  • n is 0 or 1 ;
  • A is CH; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C 2 fluoroalkyl, Ci-
  • Ri is Ci-C2alkyl; preferably ethyl; R2 is 1 ,1 - difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, or cyano; and R3 is Ci-C 2 fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; preferably trifloromethyl.
  • Gi is CH
  • X2 is NMe
  • A is CH
  • Gi is CH
  • X2 is O
  • A is CH
  • Gi is N
  • X2 is NMe
  • A is CH.
  • R2 IS not Ci-C2haloalkyl when Gi is N, X2 is NMe and A is CH.
  • R2 IS not trifluoromethyl when Gi is N, X2 is NMe and A is CH.
  • the compound 2-[6-ethylsulfonyl-2-(1 ,1 ,2,2,2- pentafluoroethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine is excluded.
  • A, X, Ri , R2, R3, n, X2 and Gi are as defined under formula I above; preferably A is CH or N, more preferably A is CH; preferably Ri is ethyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or
  • R2 is pentafluoroethyl, trifluoromethyl, bromo, cyano,
  • R3 is trifluoromethyl, pentafluoroethyl
  • R3 is trifluoromethyl; preferably n is 0 or 1 ; more preferably n is 1 ; preferably X2 is O or NCH3; more preferably X2 is NCH3; and preferably Gi is N or CH; more preferably Gi is CH.
  • Another preferred embodiment of the compounds of formula I-4 is represented by the formula l-4a wherein A, X, Ri , R2, R3, X2 and Gi are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-4.
  • Another especially preferred group of compounds of formula I are those represented by the compounds of formula 1-1 , I-2, I-3, or i-4 wherein
  • A is CH or N, preferably A is CH;
  • Ri is ethyl, propyl or isopropyl; preferably Ri is ethyl;
  • R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or
  • R3 is trifluoromethyl
  • n is 0 or 1 ; preferably n is 1 .
  • A is CH or N
  • X is S, SO or S0 2 ;
  • Ri is Ci-C 4 alkyl
  • R3 is Ci-C 4 haloalkyl, Ci-C 4 haloalkylsulfanyl, Ci-C 4 haloalkylsulfinyl, or Ci-C 4 haloalkylsulfonyl;
  • R6 and R7 are, independently, hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, halogen, cyano, aminocarbonyl, or Ci-C2alkoxycarbonyl;
  • Xi is O or NMe
  • Gi and G2 are, independently, N orCH.
  • Another preferred group of compounds of formula I is represented by the compounds of formula I-6 (1 -6)
  • A is CH or N
  • X is S, SO or S0 2 ;
  • Ri is Ci-C4alkyl
  • R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl;
  • R6 and R7 are, independently, hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, halogen, or cyano;
  • G 3 is N or CH.
  • A is CH or N
  • X is S, SO or S0 2 ;
  • Ri is Ci-C4alkyl
  • R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl;
  • R6 and R7 are, independently, hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, halogen, or cyano;
  • Gi is N and G2 IS CH, or Gi is CH and G2 IS N.
  • Compounds according to the invention may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability or environmental profile).
  • advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability or environmental profile.
  • certain compounds of formula (I) may show an advantageous safety profile with respect to non-target arthropods, in particular pollinators such as honey bees, solitary bees, and bumble bees.
  • Apis mellifera is particularly, bumble bees.
  • the present invention provides a composition
  • a composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I-5), (I-6) and (I-7), and, optionally, an auxiliary or diluent.
  • a compound of formula (I) or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I-5), (I-6) and (I-7), and, optionally, an auxiliary or diluent.
  • the present invention provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I-5), (I-6) and (I-7) (above) or a composition as defined above.
  • a compound of formula (I) or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I
  • the present invention provides a method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition as defined above.
  • Compounds of formula V may be prepared following scheme 1 .
  • Compounds of formula V, wherein R3, Gi , A, X are as defined above and Rn and Rn ⁇ may be independently R2 as defined above, may be prepared from compound IV, wherein R3, Gi, A, X are as defined above and Rn is R2 as defined above and Xo3 is halogen, by reacting with compounds Rn2-Mo, wherein Mo is a boronic acid, and Rn ⁇ is R2 in the presence of a palladium catalyst.
  • the reaction is usually carried out in the presence of a base, for example potassium carbonate, cesium carbonate, or potassium phosphate, in an inert solvent, such as dioxane, optionally in the presence of water, with a palladium(O) catalyst, for example tetrakis(triphenylphosphine)palladium, at a temperature between 80-120°C.
  • a base for example potassium carbonate, cesium carbonate, or potassium phosphate
  • an inert solvent such as dioxane
  • a palladium(O) catalyst for example tetrakis(triphenylphosphine)palladium
  • a halogenating agent such as N-chlorosuccinamide, N- bromosuccinamide, or N-iodosuccinamide
  • Compounds of formula III, wherein R3, Gi, A, X are as defined above and Rn is R2 as defined above, can be prepared by reacting a compound of formula II wherein R3, Gi, A, X are as defined above with a compound of formula VI wherein X02 is a halogen or a leaving group OSO2R8 (wherein Rs is phenyl, toluol, Ci-C 4 alkyl or Ci- C 4 haloalkyl) and R n is R2 as defined above, optionally in the presence of a suitable base in an inert solvent in the temperature range from 100 °C to 200 °C.
  • an amination reaction which involves for example, reacting compounds of formula XIII, wherein R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, with amino reagents like, for example, ammonia NH3, or ammonia equivalent ammonium hydroxide NH4OH, ammonium chloride NH4CI, ammonium acetate NhUOAc, ammonium carbonate (NH 4 ) 2 C03, and other NH3 surrogates.
  • R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluo
  • This transformations is preferably performed in suitable solvents (or diluents) such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are methanol, ethanol, 2,2,2-trifluoroethanol, propanol, iso-propanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation.
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols,
  • deprotecting reagents for -NHSC> 2 CH 2 CH 2 Si(CH3)3 include cesium fluoride, tetramethylammonium fluoride, tetra-n- butylammonium fluoride amongst others.
  • Amination reaction to convert compounds of formula XIII, wherein R3, Gi, A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, to compounds of formula II, wherein R3, Gi , A, X, Xi are as defined above may be performed optionally in the presence of suitable transition metal catalysts like, for example palladium(ll) acetate Pd(OAc)2, tris(dibenzylideneacetone)dipalladium(0) Pd 2 dba3, [1 ,1 - Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) Pd(dppf)Cl2, Palladium(TT-cinnamyl) chloride dimer [(Cinnamyl)PdCI]2, Cu powder,
  • This transformations is preferably performed in suitable solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are methanol, ethanol, 2,2,2- trifluoroethanol, propanol, iso-propanol, ethylene glycol, N,N-dimethylformamide, N,N- dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation.
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, est
  • Figure 2 Compounds offormula XIII, wherein Ri , R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl- sulfonate such as trifluoromethanesulfonate, can be prepared following scheme 3.
  • reaction can be performed with reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert-butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate.
  • reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert-butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate.
  • compounds of formula XXV can be prepared by treatment of compounds of formula XXIII with dicyclohexyl carbodiimide (DCC) or 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species XXIV, wherein LG3 is LG3a and LG3b respectively, in an inert solvent, e.g. pyridine, or THF optionally in the presence of a base, e.g. triethylamine, at temperatures between 50-180 °C.
  • DCC dicyclohexyl carbodiimide
  • EDC 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • Subgroups of compounds of formula XXIII may be obtained from compound of formula XXII, wherein Ri , X, A, are as defined in formula I above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, by hydrolysis reaction employing suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others.
  • suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others.
  • reaction as described in the synthesis of XIII in scheme 3 can be performed with reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert- butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate.
  • reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert- butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate.
  • compounds of formula XXII may be obtained from compounds of formula XXI via nucleophilic aromatic substitution and regiocontrolled SnAr reaction using R1-X-M reagents, wherein R1 and X are as defined in formula I above and M is monovalent metal such as Na, K, Li, optionally in the presence of transition metal complexes such as palladium complex, copper complex for example Pd(PPh3)4, Pd(OAc)2, Pd2dba3, Cul, CU2O in combination with monodentate or bidendate ligands such as tricyclohexylphosphine PCy3, tri-tert-butylphosphine P(f-Bu)3, N,N'- dimethylethylenediamine, 2-diphenylphosphoryl-2'-diphenylphosphino-1 ,T-biphenyl, 2,2'- bis(diphenylphosphino)-1 ,T-biphenyl amongst others.
  • R1 and X are
  • This transformations is preferably performed in suitable solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation.
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, esters, ethers, nitriles and water
  • suitable solvents such as alcohols, amides, esters, ethers
  • Compounds of formula XXI wherein A is C or N, R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, LGi and LG2 are leaving groups like, for example, chlorine, bromine or iodine, or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, may be prepared via esterification reactions from compounds of formula XX.
  • Such reactions are well known to those skilled in the state of art and may performed under basic conditions in the presence of alkyl halide, haloalkyl halide or benzyl halide in the presence of suitable base such as trimethylamine, pyridine, potassium carbonate, cesium carbonate amongst others.
  • suitable base such as trimethylamine, pyridine, potassium carbonate, cesium carbonate amongst others.
  • these reactions may be performed in the presence of acid or Lewis acids and suitable alcohols, examples of acid include HCI, H2SO4, TFA, tosic acid amongst others and example of Lewis acid include Scandium triflate Sc(OTf)2, FeCL, Yb(OTf)2 amongst others to convert compounds of formula XX to compounds of formula XXI.
  • aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate
  • XXVIII wherein R3, G3 are as described in formula (I) with a compound of formula XXIX wherein X01 is a halogen or a leaving group aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and A, X are as defined in formula (I), optionally in the presence of a suitable base in an inert solvent.
  • a further process to prepare compounds of formula XIV involves reacting a compound of formula
  • halogenation XXVII I with a compound of XXX in the presence of a Lewis acid, such as Zinc(l l)iodide or Indium(ll l) triflate, in an inert solvent such as chlorobenzene or 1 ,2, dichlorobenzene, with a catalytic copper(ll) salt, such as Cu(l l)acetate, under an oxygen or air atmosphere at temperatures between 100-180 °C, preferably 1 10-140 °C.
  • a Lewis acid such as Zinc(l l)iodide or Indium(ll l) triflate
  • an inert solvent such as chlorobenzene or 1 ,2, dichlorobenzene
  • a catalytic copper(ll) salt such as Cu(l l)acetate
  • an acyl halide of formula XXIIIa is converted to a Weinreb amide XXIIIb upon reaction with L/,O-Dimethylhydroxylamine by methods known to those skilled in the art and described for example in Synthesis 2015, 47, 1413-1422.
  • the Weinreb amide of formula XXIIIb is then reacted with a Grignard reagent of formula ChhMgHal according to the method of Weinreb ( Tetrahedron Letters 1981 , 22, 3815- 3818) to give compounds of formula XXX.
  • Compounds of formula XXXI can be halogenated to compounds of formula XXIX, with for example mixtures of bromine and hydrobromic acid in acetic acid (as described in Phosphorus, Sulfur and Silicon and the Related Elements, 2013, 188(12), 1835-1844) or with, for example, copper(ll)bromide in an inert solvent, for example chloroform, ethyl acetate and the like, as described in J. Med. Chem., 2013, 56(1 ), 84-96.
  • compounds of formula XXX can be prepared directly from compounds of formula XXIIIa by treatment with diazomethane or trimethyl silyl diazomethane and subsequent treatment with an halogen acid, for example, hydrobromic acid or hydrochloric acid in an inert solvent such as diethyl ether.
  • an halogen acid for example, hydrobromic acid or hydrochloric acid in an inert solvent such as diethyl ether.
  • this reaction may be conducted in presence of a metal catalyst, for example a Cu(l) catalyst, such as Cul, CuBr, CuCI or CuCN , or more generally with transition metals, in combination with a ligand such as tetramethylethylenediamine, 2,2'-bipyridine or 1 ,10-phenanthroline.
  • a metal catalyst for example a Cu(l) catalyst, such as Cul, CuBr, CuCI or CuCN , or more generally with transition metals, in combination with a ligand such as tetramethylethylenediamine, 2,2'-bipyridine or 1 ,10-phenanthroline.
  • Suitable solvents may include use of e toluene, chlorobenzene, or xylene, at temperatures between room temperature and 200°C, preferably between 100 and 160°C, optionally under microwave heating conditions.
  • reductive cyclisation reaction conditions were described in, for example, Organic Letters, 2011 , Vol. 13, No. 13, 3542-3545, US 2017/0260183,
  • Compounds of formula XXXIII may be prepared by the reaction of compounds of formula XIII and organo-azide or an ammonia derivatives for example NH4OH, NH3, NH2B0C in the presence of a suitable base and in the presence or absence of Lewis acids and solvent at temperatures between 50 °C and 200 °C.
  • organo-azide include TMSN3, sodium azide, diphenyl phosphoryl azide or tosyl azide and suitable solvent may be toluene, xylene, THF or acetonitrile.
  • suitable Lewis acid may include Zn(OTf)2 amongst others.
  • X, Ri , A and F3 ⁇ 4 are as defined above and Q is Cte may be represented by compounds of formula X, wherein R3, G3, X, R1 , A are as define in formula I above, and Rn ⁇ and Rn are independently R2 as described in formula I above, may be prepared using carboxylic acid XXXV to form either halo ketone XXXVIII or ketone XXXIX and reacting with amine XXVIII analogous to procedure described in scheme 4, scheme 5 and scheme 6.
  • X, Ri , A and F3 ⁇ 4 are as defined above and Q is Cb may be represented by compounds of formula XI, wherein R3, G3, X, R1 , A are as define in formula I above, and Rn ⁇ and Rn are independently R2 as described in formula I above, may be prepared using carboxylic acid XXXV and azido aldehyde XXXI analogous to procedure described in scheme 7. People skilled in the state of art will realize amine XXXX serves as a key intermediate for the synthesis of XI in this procedure.
  • Compounds of formula XXXVIII may be obtained from compound of formula XXXVII, wherein Ri, X, A, are as defined in formula I above and Rn is R2 as defined in formula I above and R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, by hydrolysis reaction employing suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others.
  • suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others.
  • Compounds of formula XXXVII may be obtained from compounds of formula XXXVI analogous to procedure described in scheme 4.
  • Compounds of formula XXXVI may be obtained from compounds of formula XXII analogous to procedure described in scheme 2.
  • Salts of compounds of formula I can be prepared in a manner known per se.
  • acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
  • Salts of compounds of formula I can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
  • Salts of compounds of formula I can be converted in a manner known per se into other salts of compounds of formula I, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
  • a salt of inorganic acid such as hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the compounds of formula I which have saltforming properties can be obtained in free form or in the form of salts.
  • the compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.
  • Diastereomer mixtures or racemate mixtures of compounds of formula I, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.
  • Enantiomer mixtures such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid
  • N-oxides can be prepared by reacting a compound of the formula I with a suitable oxidizing agent, for example the H2C>2/urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride.
  • a suitable oxidizing agent for example the H2C>2/urea adduct
  • an acid anhydride e.g. trifluoroacetic anhydride.
  • the compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • Table Z-1 provides 17 compounds Z-1 .001 to Z-1 .017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-2 provides 17 compounds Z-2.001 to Z-2.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-3 provides 17 compounds Z-3.001 to Z-3.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-4 provides 17 compounds Z-4.001 to Z-4.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-5 provides 17 compounds Z-5.001 to Z-5.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-6 provides 17 compounds Z-6.001 to Z-6.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-7 provides 17 compounds Z-7.001 to Z-7.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-8 provides 17 compounds Z-8.001 to Z-8.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-9 provides 17 compounds Z-9.001 to Z-9.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-10 provides 17 compounds Z-10.001 to Z-10.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 1 provides 17 compounds Z-1 1 .001 to Z-1 1 .017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-12 provides 17 compounds Z-12.001 to Z-12.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-13 provides 17 compounds Z-13.001 to Z-13.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-14 provides 17 compounds Z-14.001 to Z-14.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-15 provides 17 compounds Z-15.001 to Z-15.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-16 provides 17 compounds Z-16.001 to Z-16.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-17 provides 17 compounds Z-17.001 to Z-17.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-18 provides 17 compounds Z-18.001 to Z-18.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-19 provides 17 compounds Z-19.001 to Z-19.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-20 provides 17 compounds Z-20.001 to Z-20.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-21 provides 17 compounds Z-21 .001 to Z-21 .017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-22 provides 17 compounds Z-22.001 to Z-22.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-23 provides 17 compounds Z-23.001 to Z-23.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-24 provides 17 compounds Z-24.001 to Z-24.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-25 provides 17 compounds Z-25.001 to Z-25.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-26 provides 17 compounds Z-26.001 to Z-26.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-27 provides 17 compounds Z-27.001 to Z-27.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-28 provides 17 compounds Z-28.001 to Z-28.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-29 provides 17 compounds Z-29.001 to Z-29.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-30 provides 17 compounds Z-30.001 to Z-30.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-31 provides 17 compounds Z-31 .001 to Z-31 .017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-32 provides 17 compounds Z-32.001 to Z-32.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-33 provides 17 compounds Z-33.001 to Z-33.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-34 provides 17 compounds Z-34.001 to Z-34.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-35 provides 17 compounds Z-35.001 to Z-35.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-36 provides 17 compounds Z-36.001 to Z-36.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-37 provides 17 compounds Z-37.001 to Z-37.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-38 provides 17 compounds Z-38.001 to Z-38.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-39 provides 17 compounds Z-39.001 to Z-39.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-40 provides 17 compounds Z-40.001 to Z-40.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-41 provides 17 compounds Z-41 .001 to Z-41 .017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-42 provides 17 compounds Z-42.001 to Z-42.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-43 provides 17 compounds Z-43.001 to Z-43.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-44 provides 17 compounds Z-44.001 to Z-44.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-45 provides 17 compounds Z-45.001 to Z-45.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-46 provides 17 compounds Z-46.001 to Z-46.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-47 provides 17 compounds Z-47.001 to Z-47.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-48 provides 17 compounds Z-48.001 to Z-48.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-49 provides 17 compounds Z-49.001 to Z-49.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-50 provides 17 compounds Z-50.001 to Z-50.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-51 provides 17 compounds Z-51 .001 to Z-51 .017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-52 provides 17 compounds Z-52.001 to Z-52.017 of formula A wherein R3 is CF2CF3, Xi is
  • Table Z-53 provides 17 compounds Z-53.001 to Z-53.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-54 provides 17 compounds Z-54.001 to Z-54.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-55 provides 17 compounds Z-55.001 to Z-55.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-56 provides 17 compounds Z-56.001 to Z-56.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-57 provides 17 compounds Z-57.001 to Z-57.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-58 provides 17 compounds Z-58.001 to Z-58.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-59 provides 17 compounds Z-59.001 to Z-59.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-60 provides 17 compounds Z-60.001 to Z-60.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-61 provides 17 compounds Z-61 .001 to Z-61 .017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-62 provides 17 compounds Z-62.001 to Z-62.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-63 provides 17 compounds Z-63.001 to Z-63.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-64 provides 17 compounds Z-64.001 to Z-64.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-65 provides 17 compounds Z-65.001 to Z-65.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-66 provides 17 compounds Z-66.001 to Z-66.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-67 provides 17 compounds Z-67.001 to Z-67.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-68 provides 17 compounds Z-68.001 to Z-68.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-69 provides 17 compounds Z-69.001 to Z-69.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-70 provides 17 compounds Z-70.001 to Z-70.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-71 provides 17 compounds Z-71 .001 to Z-71 .017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-72 provides 17 compounds Z-72.001 to Z-72.017 of formula A wherein R3 is CF 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-73 provides 17 compounds Z-73.001 to Z-73.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-74 provides 17 compounds Z-74.001 to Z-74.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-75 provides 17 compounds Z-75.001 to Z-75.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-76 provides 17 compounds Z-76.001 to Z-76.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-77 provides 17 compounds Z-77.001 to Z-77.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-78 provides 17 compounds Z-78.001 to Z-78.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-79 provides 17 compounds Z-79.001 to Z-79.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-80 provides 17 compounds Z-80.001 to Z-80.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-81 provides 17 compounds Z-81 .001 to Z-81 .017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-82 provides 17 compounds Z-82.001 to Z-82.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-83 provides 17 compounds Z-83.001 to Z-83.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-84 provides 17 compounds Z-84.001 to Z-84.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-85 provides 17 compounds Z-85.001 to Z-85.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-86 provides 17 compounds Z-86.001 to Z-86.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-87 provides 17 compounds Z-87.001 to Z-87.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-88 provides 17 compounds Z-88.001 to Z-88.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-89 provides 17 compounds Z-89.001 to Z-89.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-90 provides 17 compounds Z-90.001 to Z-90.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-91 provides 17 compounds Z-91 .001 to Z-91 .017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-92 provides 17 compounds Z-92.001 to Z-92.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-93 provides 17 compounds Z-93.001 to Z-93.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-94 provides 17 compounds Z-94.001 to Z-94.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-95 provides 17 compounds Z-95.001 to Z-95.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-96 provides 17 compounds Z-96.001 to Z-96.017 of formula A wherein R3 is CF 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-97 provides 17 compounds Z-97.001 to Z-97.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-98 provides 17 compounds Z-98.001 to Z-98.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-99 provides 17 compounds Z-99.001 to Z-99.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-100 provides 17 compounds Z-100.001 to Z-100.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-101 provides 17 compounds Z-101 .001 to Z-101 .017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-102 provides 17 compounds Z-102.001 to Z-102.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-103 provides 17 compounds Z-103.001 to Z-103.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-104 provides 17 compounds Z-104.001 to Z-104.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-105 provides 17 compounds Z-105.001 to Z-105.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-106 provides 17 compounds Z-106.001 to Z-106.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-107 provides 17 compounds Z-107.001 to Z-107.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-108 provides 17 compounds Z-108.001 to Z-108.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-109 provides 17 compounds Z-109.001 to Z-109.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-1 10 provides 17 compounds Z-1 10.001 to Z-1 10.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 1 1 provides 17 compounds Z-1 1 1 .001 to Z-1 1 1 .017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-1 12 provides 17 compounds Z-1 12.001 to Z-1 12.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 13 provides 17 compounds Z-1 13.001 to Z-1 13.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-1 14 provides 17 compounds Z-1 14.001 to Z-1 14.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 15 provides 17 compounds Z-1 15.001 to Z-1 15.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-1 16 provides 17 compounds Z-1 16.001 to Z-1 16.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 17 provides 17 compounds Z-1 17.001 to Z-1 17.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-1 18 provides 17 compounds Z-1 18.001 to Z-1 18.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-1 19 provides 17 compounds Z-1 19.001 to Z-1 19.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-120 provides 17 compounds Z-120.001 to Z-120.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-121 provides 17 compounds Z-121 .001 to Z-121 .017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-122 provides 17 compounds Z-122.001 to Z-122.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-123 provides 17 compounds Z-123.001 to Z-123.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-124 provides 17 compounds Z-124.001 to Z-124.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-125 provides 17 compounds Z-125.001 to Z-125.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-126 provides 17 compounds Z-126.001 to Z-126.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-127 provides 17 compounds Z-127.001 to Z-127.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-128 provides 17 compounds Z-128.001 to Z-128.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-129 provides 17 compounds Z-129.001 to Z-129.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-130 provides 17 compounds Z-130.001 to Z-130.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-131 provides 17 compounds Z-131 .001 to Z-131 .017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-132 provides 17 compounds Z-132.001 to Z-132.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-133 provides 17 compounds Z-133.001 to Z-133.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-134 provides 17 compounds Z-134.001 to Z-134.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-135 provides 17 compounds Z-135.001 to Z-135.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-136 provides 17 compounds Z-136.001 to Z-136.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-137 provides 17 compounds Z-137.001 to Z-137.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-138 provides 17 compounds Z-138.001 to Z-138.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-139 provides 17 compounds Z-139.001 to Z-139.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-140 provides 17 compounds Z-140.001 to Z-140.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-141 provides 17 compounds Z-141 .001 to Z-141 .017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-142 provides 17 compounds Z-142.001 to Z-142.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-143 provides 17 compounds Z-143.001 to Z-143.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-144 provides 17 compounds Z-144.001 to Z-144.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-145 provides 17 compounds Z-145.001 to Z-145.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-146 provides 17 compounds Z-146.001 to Z-146.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-147 provides 17 compounds Z-147.001 to Z-147.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-148 provides 17 compounds Z-148.001 to Z-148.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-149 provides 17 compounds Z-149.001 to Z-149.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-150 provides 17 compounds Z-150.001 to Z-150.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-151 provides 17 compounds Z-151 .001 to Z-151 .017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-152 provides 17 compounds Z-152.001 to Z-152.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-153 provides 17 compounds Z-153.001 to Z-153.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-154 provides 17 compounds Z-154.001 to Z-154.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-155 provides 17 compounds Z-155.001 to Z-155.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-156 provides 17 compounds Z-156.001 to Z-156.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-157 provides 17 compounds Z-157.001 to Z-157.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-158 provides 17 compounds Z-158.001 to Z-158.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-159 provides 17 compounds Z-159.001 to Z-159.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-160 provides 17 compounds Z-160.001 to Z-160.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-161 provides 17 compounds Z-161 .001 to Z-161 .017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-162 provides 17 compounds Z-162.001 to Z-162.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-163 provides 17 compounds Z-163.001 to Z-163.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-164 provides 17 compounds Z-164.001 to Z-164.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-165 provides 17 compounds Z-165.001 to Z-165.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-166 provides 17 compounds Z-166.001 to Z-166.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-167 provides 17 compounds Z-167.001 to Z-167.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-168 provides 17 compounds Z-168.001 to Z-168.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-169 provides 17 compounds Z-169.001 to Z-169.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-170 provides 17 compounds Z-170.001 to Z-170.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-171 provides 17 compounds Z-171 .001 to Z-171 .017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-172 provides 17 compounds Z-172.001 to Z-172.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-173 provides 17 compounds Z-173.001 to Z-173.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-174 provides 17 compounds Z-174.001 to Z-174.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-175 provides 17 compounds Z-175.001 to Z-175.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-176 provides 17 compounds Z-176.001 to Z-176.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-177 provides 17 compounds Z-177.001 to Z-177.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-178 provides 17 compounds Z-178.001 to Z-178.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-179 provides 17 compounds Z-179.001 to Z-179.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-180 provides 17 compounds Z-180.001 to Z-180.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-181 provides 17 compounds Z-1 17.001 to Z-1 17.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-182 provides 17 compounds Z-182.001 to Z-182.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-183 provides 17 compounds Z-183.001 to Z-183.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-184 provides 17 compounds Z-184.001 to Z-184.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-185 provides 17 compounds Z-185.001 to Z-185.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-186 provides 17 compounds Z-186.001 to Z-186.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-187 provides 17 compounds Z-187.001 to Z-187.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-188 provides 17 compounds Z-188.001 to Z-188.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-189 provides 17 compounds Z-189.001 to Z-189.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-190 provides 17 compounds Z-190.001 to Z-190.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-191 provides 17 compounds Z-191 .001 to Z-191 .017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-192 provides 17 compounds Z-192.001 to Z-192.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-193 provides 17 compounds Z-193.001 to Z-193.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-194 provides 17 compounds Z-194.001 to Z-194.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-195 provides 17 compounds Z-195.001 to Z-195.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-196 provides 17 compounds Z-196.001 to Z-196.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-197 provides 17 compounds Z-197.001 to Z-197.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-198 provides 17 compounds Z-198.001 to Z-198.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-199 provides 17 compounds Z-199.001 to Z-199.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-200 provides 17 compounds Z-200.001 to Z-200.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-201 provides 17 compounds Z-201 .001 to Z-201 .017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-202 provides 17 compounds Z-202.001 to Z-202.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-203 provides 17 compounds Z-203.001 to Z-203.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is CH and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-204 provides 17 compounds Z-204.001 to Z-204.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-205 provides 17 compounds Z-205.001 to Z-205.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-206 provides 17 compounds Z-206.001 to Z-206.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is S, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-207 provides 17 compounds Z-207.001 to Z-207.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-208 provides 17 compounds Z-208.001 to Z-208.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-209 provides 17 compounds Z-209.001 to Z-209.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-210 provides 17 compounds Z-210.001 to Z-210.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-21 1 provides 17 compounds Z-21 1 .001 to Z-21 1 .017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-212 provides 17 compounds Z-212.001 to Z-212.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-213 provides 17 compounds Z-213.001 to Z-213.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-214 provides 17 compounds Z-214.001 to Z-214.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-215 provides 17 compounds Z-215.001 to Z-215.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-216 provides 17 compounds Z-216.001 to Z-216.017 of formula A wherein R3 is SO 2 CF3, Xi is NMe, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-217 provides 17 compounds Z-217.001 to Z-217.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-218 provides 17 compounds Z-218.001 to Z-218.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and F3 ⁇ 4, R7 are as defined in table Y.
  • Table Z-219 provides 17 compounds Z-219.001 to Z-219.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is S, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-220 provides 17 compounds Z-220.001 to Z-220.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-221 provides 17 compounds Z-221 .001 to Z-221 .017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-222 provides 17 compounds Z-222.001 to Z-222.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-223 provides 17 compounds Z-223.001 to Z-223.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-224 provides 17 compounds Z-224.001 to Z-224.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-225 provides 17 compounds Z-225.001 to Z-225.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-226 provides 17 compounds Z-226.001 to Z-226.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-227 provides 17 compounds Z-227.001 to Z-227.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-228 provides 17 compounds Z-228.001 to Z-228.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is N, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-229 provides 17 compounds Z-229.001 to Z-229.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is S, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-230 provides 17 compounds Z-230.001 to Z-230.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
  • Table Z-231 provides 17 compounds Z-231 .001 to Z-231 .017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-232 provides 17 compounds Z-232.001 to Z-232.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is S, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-233 provides 17 compounds Z-233.001 to Z-233.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-234 provides 17 compounds Z-234.001 to Z-234.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO, Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-235 provides 17 compounds Z-235.001 to Z-235.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-236 provides 17 compounds Z-236.001 to Z-236.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO, Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-237 provides 17 compounds Z-237.001 to Z-237.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
  • Table Z-238 provides 17 compounds Z-238.001 to Z-238.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is CH, G 2 is N and R6, R7 are as defined in table Y.
  • Table Z-239 provides 17 compounds Z-239.001 to Z-239.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is CH and R6, R7 are as defined in table Y.
  • Table Z-240 provides 17 compounds Z-240.001 to Z-240.017 of formula A wherein R3 is SO 2 CF3, Xi is O, A is CH, X is SO 2 , Gi is N, G 2 is N and R6, R7 are as defined in table Y.
  • Table Za-1 provides 17 compounds Za-1 .001 to Za-1 .017 of formula B wherein R3 is CF3, A is CH, X is S, G3 is CH and F3 ⁇ 4, R7 are as defined in table X.
  • Table Za-2 provides 17 compounds Za-2.001 to Za-2.017 of formula B wherein R3 is CF3, A is CH, X is S, G3 is N and F3 ⁇ 4, R7 are as defined in table X.
  • Table Za-3 provides 17 compounds Za-3.001 to Za-3.017 of formula B wherein R3 is CF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-4 provides 17 compounds Za-4.001 to Za-4.017 of formula B wherein R3 is CF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-5 provides 17 compounds Za-5.001 to Za-5.017 of formula B wherein R3 is CF3, A is CH, X is SO2, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-6 provides 17 compounds Za-6.001 to Za-6.017 of formula B wherein R3 is CF3, A is CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
  • Table Za-7 provides 17 compounds Za-7.001 to Za-7.017 of formula B wherein R3 is CF3, A is N, X is S, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-8 provides 17 compounds Za-8.001 to Za-8.017 of formula B wherein R3 is CF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
  • Table Za-9 provides 17 compounds Za-9.001 to Za-9.017 of formula B wherein R3 is CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-10 provides 17 compounds Za-10.001 to Za-10.017 of formula B wherein R3 is CF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-1 1 provides 17 compounds Za-1 1 .001 to Za-1 1 .017 of formula B wherein R3 is CF3, A is N, X is SO2, G3 is CH and F3 ⁇ 4, R7 are as defined in table X.
  • Table Za-12 provides 17 compounds Za-12.001 to Za-12.017 of formula B wherein R3 is CF3, A is N, X is SO2, G3 is N and R6, R7 are as defined in table X. , , , ,
  • N is S
  • G3 is CH
  • R6, R7 are as defined in table X.
  • N is S
  • G3 is N
  • R6, R7 are as defined in table X.
  • Table Za-21 provides 17 compounds Za-21 .001 to Za-21 . 017 of formula B wherein R3 is CF2CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • N is SO
  • G3 is N
  • R6, R7 are as defined in table X. , , ,
  • N is SO2
  • G3 is N
  • R6, R7 are as defined in table X.
  • Table Za-25 provides 17 compounds Za-25.001 to Za-25.017 of formula B wherein R3 is SCF3, A is
  • Table Za-26 provides 17 compounds Za-26.001 to Za-26.017 of formula B wherein R3 is SCF3, A is CH, X is S, G3 is N and F3 ⁇ 4, R7 are as defined in table X.
  • Table Za-27 provides 17 compounds Za-27.001 to Za-27.017 of formula B wherein R3 is SCF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-28 provides 17 compounds Za-28.001 to Za-28.017 of formula B wherein R3 is SCF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-29 provides 17 compounds Za-29.001 to Za-29.017 of formula B wherein R3 is SCF3, A is CH, X is SO2, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-30 provides 17 compounds Za-30.001 to Za-30.017 of formula B wherein R3 is SCF3, A is CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
  • Table Za-31 provides 17 compounds Za-31 .001 to Za-31 .017 of formula B wherein R3 is SCF3, A is N, X is S, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-32 provides 17 compounds Za-32.001 to Za-32.017 of formula B wherein R3 is SCF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
  • Table Za-33 provides 17 compounds Za-33.001 to Za-33.017 of formula B wherein R3 is SCF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-34 provides 17 compounds Za-34.001 to Za-34.017 of formula B wherein R3 is SCF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-35 provides 17 compounds Za-35.001 to Za-35.017 of formula B wherein R3 is SCF3, A is N, X is SO2, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-36 provides 17 compounds Za-36.001 to Za-36.017 of formula B wherein R3 is SCF3, A is N, X is SO2, G3 is N and R6, R7 are as defined in table X.
  • Table Za-37 provides 17 compounds Za-37.001 to Za-37.017 of formula B wherein R3 is SOCF3, A is CH, X is S, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-38 provides 17 compounds Za-38.001 to Za-38.017 of formula B wherein R3 is SOCF3, A is CH, X is S, G3 is N and R6, R7 are as defined in table X.
  • Table Za-39 provides 17 compounds Za-39.001 to Za-39.017 of formula B wherein R3 is SOCF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-40 provides 17 compounds Za-40.001 to Za-40.017 of formula B wherein R3 is SOCF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-41 provides 17 compounds Za-41 .001 to Za-41 .017 of formula B wherein R3 is SOCF3, A is CH, X is SO2, G3 is CH and F3 ⁇ 4, R7 are as defined in table X.
  • N is S
  • G3 is N
  • R6, R7 are as defined in table X. , , ,
  • N is SO
  • G3 is N
  • R6, R7 are as defined in table X.
  • N is SO2
  • G3 is CH and R6, R7 are as defined in table X.
  • N is SO2
  • G3 is N
  • R6, R7 are as defined in table X.
  • Table Za-51 provides 17 compounds Za-51 .001 to Za-51 .017 of formula B wherein R3 is SO2CF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-55 provides 17 compounds Za-55.001 to Za-55.017 of formula B wherein R3 is SO2CF3, A is
  • Table Za-56 provides 17 compounds Za-56.001 to Za-56.017 of formula B wherein R3 is SO 2 CF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
  • Table Za-57 provides 17 compounds Za-57.001 to Za-57.017 of formula B wherein R3 is SO 2 CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-58 provides 17 compounds Za-58.001 to Za-58.017 of formula B wherein R3 is SO 2 CF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X.
  • Table Za-59 provides 17 compounds Za-59.001 to Za-59.017 of formula B wherein R3 is SO 2 CF3, A is N, X is SO2, G3 is CH and R6, R7 are as defined in table X.
  • Table Za-60 provides 17 compounds Za-60.001 to Za-60.017 of formula B wherein R3 is SO 2 CF3, A is N, X is SO 2 , G3 is N and R6, R7 are as defined in table X.
  • Table Zb-1 provides 34 compounds Zb-1 .001 to Zb-1 .34 of formula C wherein R3 is CF3, A is CH, X is S and F3 ⁇ 4, R7, Gi , G2 are as defined in table W.
  • Table Zb-2 provides 34 compounds Zb-2.001 to Zb-2.34 of formula C wherein R3 is CF3, A is CH, X is SO and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-3 provides 34 compounds Zb-3.001 to Zb-3.34 of formula C wherein R3 is CF3, A is CH, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
  • Table Zb-4 provides 34 compounds Zb-4.001 to Zb-4.34 of formula C wherein R3 is CF3, A is N, X is S and R6, R7, Gi , G 2 are as defined in table W.
  • Table Zb- 5 provides 34 compounds Zb-5.001 to Zb-5.34 of formula C wherein R3 is CF3, A is N, X is SO and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-6 provides 34 compounds Zb-6.001 to Zb-6.34 of formula C wherein R3 is CF3, A is N, X is SO2 and F3 ⁇ 4, R7, Gi , G2 are as defined in table W.
  • Table Zb- 7 provides 34 compounds Zb-7.001 to Zb-7.34 of formula C wherein R3 is CF 2 CF3, A is CH, X is S and F3 ⁇ 4, R7, Gi , G 2 are as defined in table W.
  • Table Zb-8 provides 34 compounds Zb-8.001 to Zb-8.34 of formula C wherein R3 is CF 2 CF3, A is CH, X is SO and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-9 provides 34 compounds Zb-9.001 to Zb-9.34 of formula C wherein R3 is CF 2 CF3, A is CH, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
  • Table Zb-10 provides 34 compounds Zb-10.001 to Zb-10.34 of formula C wherein R3 is CF 2 CF3, A is N, X is S and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-1 1 provides 34 compounds Zb-1 1 .001 to Zb-1 1 .34 of formula C wherein R3 is CF2CF3, A is N, X is SO and R6, R7, Gi , G2 are as defined in table W.
  • Table Zb-12 provides 34 compounds Zb-12.001 to Zb-12.34 of formula C wherein R3 is CF 2 CF3, A is N, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
  • Table Zb-13 provides 34 compounds Zb-13.001 to Zb-13.34 of formula C wherein R3 is SCF3, A is CH, X is S and R6, R7, Gi , G2 are as defined in table W.
  • Table Zb-14 provides 34 compounds Zb-14.001 to Zb-14.34 of formula C wherein R3 is SCF3, A is CH, X is SO and Re, R7, Gi, G 2 are as defined in table W.
  • Table Zb-15 provides 34 compounds Zb-15.001 to Zb-15.34 of formula C wherein R3 is SCF3, A is CH, X is SO2 and Re, R7, Gi , G2 are as defined in table W.
  • Table Zb-16 provides 34 compounds Zb-16.001 to Zb-16.34 of formula C wherein R3 is SCF3, A is N,
  • X is S and Re, R7, Gi , G2 are as defined in table W.
  • Table Zb-17 provides 34 compounds Zb-17.001 to Zb-17.34 of formula C wherein R3 is SCF3, A is N,
  • X is SO and Re, R7, Gi, G2 are as defined in table W.
  • Table Zb-18 provides 34 compounds Zb-18.001 to Zb-18.34 of formula C wherein R3 is SCF3, A is N,
  • X is SO2 and Re, R7, Gi , G2 are as defined in table W.
  • Table Zb-19 provides 34 compounds Zb-19.001 to Zb-19.34 of formula C wherein R3 is SOCF3, A is CH, X is S and Re, R7, Gi, G 2 are as defined in table W.
  • Table Zb-20 provides 34 compounds Zb-20.001 to Zb-20.34 of formula C wherein R3 is SOCF3, A is CH, X is SO and Re, R7, Gi , G 2 are as defined in table W.
  • Table Zb-21 provides 34 compounds Zb-21 .001 to Zb-21 .34 of formula C wherein R3 is SOCF3, A is CH, X is SO2 and Re, R7, Gi , G2 are as defined in table W.
  • Table Zb-22 provides 34 compounds Zb-22.001 to Zb-22.34 of formula C wherein R3 is SOCF3, A is N, X is S and F3 ⁇ 4, R7, Gi , G 2 are as defined in table W.
  • Table Zb-23 provides 34 compounds Zb-23.001 to Zb-23.34 of formula C wherein R3 is SOCF3, A is N, X is SO and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-24 provides 34 compounds Zb-24.001 to Zb-24.34 of formula C wherein R3 is SOCF3, A is N, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
  • Table Zb-25 provides 34 compounds Zb-25.001 to Zb-25.34 of formula C wherein R3 is SO 2 CF3, A is CH, X is S and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-26 provides 34 compounds Zb-26.001 to Zb-26.34 of formula C wherein R3 is SO 2 CF3, A is CH, X is SO and R6, R7, Gi , G 2 are as defined in table W.
  • Table Zb-27 provides 34 compounds Zb-27.001 to Zb-27.34 of formula C wherein R3 is SO 2 CF3, A is CH, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
  • Table Zb-28 provides 34 compounds Zb-28.001 to Zb-28.34 of formula C wherein R3 is SO 2 CF3, A is N, X is S and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-29 provides 34 compounds Zb-29.001 to Zb-29.34 of formula C wherein R3 is SO 2 CF3, A is N, X is SO and R6, R7, Gi, G 2 are as defined in table W.
  • Table Zb-30 provides 34 compounds Zb-30.001 to Zb-30.34 of formula C wherein R3 is SO 2 CF3, A is N, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
  • the compounds of formula I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.
  • the active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina, nematodes or molluscs.
  • the insecticidal, nematicidal, molluscicidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e.
  • Panonychus spp. Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp.;
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;
  • Agriotes spp. Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megas
  • Acyrthosium pisum Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spec
  • Macrosiphum spp. Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria
  • Coptotermes spp Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate
  • Blatta spp. Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and Schistocerca spp.;
  • Thysanura for example, Lepisma saccharina.
  • the active ingredients according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
  • Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts,
  • compositions and/or methods of the present invention may be also used on any ornamental and/or vegetable crops, including flowers, shrubs, broad-leaved trees and evergreens.
  • the invention may be used on any of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g. B. elatior, B. semperfiorens, B. tubereux), Bougainvillea spp., Brachycome spp., Brassica spp.
  • Coreopsis spp. Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (/.
  • Iresines spp. Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp., Beilis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp.
  • Salvia spp. Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfmia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.
  • the invention may be used on any of the following vegetable species: Allium spp. (A. sativum, A. cepa, A. oschaninii, A. Porrum, A. ascalonicum, A. fistulosum), Anthriscus cerefolium, Apium graveolus, Asparagus officinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B. Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus, Cucumis spp. (C. sativus, C.
  • Preferred ornamental species include African violet, Begonia, Dahlia, Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper, tomato and cucumber.
  • the active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and
  • the active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
  • the active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and
  • the active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
  • the invention may also relate to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolai
  • Needle nematodes Longidorus elongatus and other Longidorus species; Pin nematodes,
  • Pratylenchus species Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans,
  • the compounds of the invention may also have activity against the molluscs.
  • examples of which include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus);
  • Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae Helicigona arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as d-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • d-endotoxins for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated CrylAb, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
  • deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses a
  • transgenic crops are:
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'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 Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- 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-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 c 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 CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain
  • Lepidoptera include the European corn borer. Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fiir Bio und Nachhalttechnik, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.
  • fungal for example Fusarium, Anthracnose, or Phytophthora
  • bacterial for example Pseudomonas
  • viral for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus
  • Crops also include those that have enhanced resistance to nematodes, such as the soybean cyst nematode.
  • Crops that are tolerance to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g.
  • compositions according to the invention are the protection of stored goods and store rooms and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animals and productive livestock against pests of the mentioned type.
  • the present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http://www.who.int/malaria/vector_control/irs/en/).
  • the method for controlling pests comprises applying the compositions of the invention to the target pests, to their locus or to a surface or substrate by brushing, rolling, spraying, spreading or dipping.
  • an IRS (indoor residual spraying) application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention.
  • the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate.
  • a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate.
  • Such application may be made by brushing, rolling, spraying, spreading or dipping the pesticidal composition of the invention.
  • an IRS application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface.
  • it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.
  • Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrylonitrile or the like.
  • the polyesters are particularly suitable.
  • the methods of textile treatment are known, e.g. WO 2008/151984, WO 2003/034823, US 5631072, WO 2005/64072, W02006/128870, EP 1724392, WO 2005113886 or WO 2007/090739.
  • compositions according to the invention are the field of tree injection/trunk treatment for all ornamental trees as well all sort of fruit and nut trees.
  • the compounds according to the present invention are especially suitable against wood-boring insects from the order Lepidoptera as mentioned above and from the order Coleoptera, especially against woodborers listed in the following tables A and B:
  • the present invention may be also used to control any insect pests that may be present in turfgrass, including for example beetles, caterpillars, fire ants, ground pearls, millipedes, sow bugs, mites, mole crickets, scales, mealybugs ticks, spittlebugs, southern chinch bugs and white grubs.
  • the present invention may be used to control insect pests at various stages of their life cycle, including eggs, larvae, nymphs and adults.
  • the present invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g. masked chafer, C. lurida),
  • white grubs such as Cyclocephala spp. (e.g. masked chafer, C. lurida)
  • Rhizotrogus spp. e.g. European chafer, R. majalis
  • Cotinus spp. e.g. Green June beetle, C. nitida
  • Popillia spp. e.g. Japanese beetle, P. japonica
  • Phyllophaga spp. e.g. May/June beetle
  • Ataenius spp. e.g. Black turfgrass ataenius, A. spretulus
  • Maladera spp. e.g. Asiatic garden beetle, M.
  • the present invention may also be used to control insect pests of turfgrass that are thatch dwelling, including armyworms (such as fall armyworm Spodoptera frugiperda, and common armyworm Pseudaletia unipuncta), cutworms, billbugs ( Sphenophorus spp. , such as S. venatus verstitus and S. parvulus), and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).
  • armyworms such as fall armyworm Spodoptera frugiperda, and common armyworm Pseudaletia unipuncta
  • cutworms such as Sphenophorus spp. , such as S. venatus verstitus and S. parvulus
  • sod webworms such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis.
  • the present invention may also be used to control insect pests of turfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southern chinch bugs, Blissus insulahs), Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug ( Propsapia bicincta), leafhoppers, cutworms ( Noctuidae family), and greenbugs.
  • the present invention may also be used to control other pests of turfgrass such as red imported fire ants ( Solenopsis invicta) that create ant mounds in turf.
  • compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
  • ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
  • Anoplurida Haematopinus spp., Linognathus spp., Pediculus spp. and Phtirus spp., Solenopotes spp..
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp., Call
  • Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..
  • Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,
  • Pterolichus spp. Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..
  • compositions according to the invention are also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildings.
  • compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium
  • rufovillosum Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec.,Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes,
  • Reticulitermes santonensis Reticulitermes lucifugus
  • Mastotermes darwiniensis Zootermopsis nevadensis and Coptotermes formosanus
  • bristletails such as Lepisma saccharina.
  • the compounds according to the invention can be used as pesticidal agents in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances.
  • formulation adjuvants such as carriers, solvents and surface-active substances.
  • the formulations can be in various physical forms, e.g.
  • Such formulations can either be used directly or diluted prior to use.
  • the dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
  • the formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns.
  • the active ingredients contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, A/,A/-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, di
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
  • a large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.
  • Surface- active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes.
  • Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosu coin ate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters
  • Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
  • compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • the amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied.
  • the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared.
  • Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively).
  • Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.
  • inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.
  • the rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • Preferred formulations can have the following compositions (weight %):
  • Emulsifiable concentrates are:
  • active ingredient 1 to 95 %, preferably 60 to 90 %
  • surface-active agent 1 to 30 %, preferably 5 to 20 %
  • liquid carrier 1 to 80 %, preferably 1 to 35 %
  • active ingredient 0.1 to 10 %, preferably 0.1 to 5 %
  • solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • active ingredient 5 to 75 %, preferably 10 to 50 %
  • surface-active agent 1 to 40 %, preferably 2 to 30 %
  • active ingredient 0.5 to 90 %, preferably 1 to 80 %
  • surface-active agent 0.5 to 20 %, preferably 1 to 15 %
  • solid carrier 5 to 95 %, preferably 15 to 90 %
  • active ingredient 0.1 to 30 %, preferably 0.1 to 15 %
  • solid carrier 99.5 to 70 %, preferably 97 to 85 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • the combination is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • the finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1).
  • This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51 .6 parts of water until the desired particle size is achieved.
  • To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
  • EC emulsion concentrate
  • SC suspension concentrate
  • SE suspo- emulsion
  • CS capsule suspension
  • WG water dispersible granule
  • Example H1 Preparation of 2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-alpyridin-7-yl1-3-methyl- 6-(trifluoromethyl)imidazo[4,5-clpyridine (Compound P4, Table P)
  • Step 1 Preparation of 2-chloro-5-ethylsulfanyl-pyridine-4-carboxylic acid.
  • Step 2 Preparation of 2-chloro-5-ethylsulfanyl-N-[5-(methylamino)-2-(trifluoromethyl)-4- pyridyllpyridine-4-carboxamide
  • 2-chloro-5-ethylsulfanyl-pyridine-4-carboxylic acid 0.4 g, 1 .837 mmol
  • dichloromethane 10 mL
  • DMF 0.1 ml
  • Step 3 Preparation of 2-(2-chloro-5-ethylsulfanyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- clpyridine
  • Step 4 Preparation of 2-(2-chloro-5-ethylsulfonyl-4-pyridyr)-3-methyl-6-(trifluoromethvDimidazo[4,5- clpyridine
  • Step 5 Preparation of 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4.5-clpyridin-2-yllpyridin-
  • Example H2 Preparation of methyl 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5- clpyridin-2-yl1imidazo[1 .2-alpyridine-2-carboxylate ( Compound P1 1 , Table P)
  • TX means“one compound selected from the group consisting of the compounds described in Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P of the present invention”
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name)
  • an acaricide selected from the group of substances consisting of 1 ,1 -bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1 -naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870
  • TX amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) +
  • TX TX
  • TX buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (lUPAC name) (1 1 1) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbophenothion (947) + TX, CGA 50’439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulfide (971) + TX, chlorfenvinphos (131) + T
  • TX quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) +
  • TX thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triarathene (1443) +
  • TX triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714)
  • an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin
  • TX hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (lUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (61 1) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV
  • Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp.
  • TX TX
  • crotamiton alternative name
  • crotoxyphos 1010) + TX
  • crufomate 1011
  • cryolite alternative name
  • TX TX
  • CS 708 development code
  • cyanofenphos 1019
  • TX TX
  • cyanophos 184
  • TX cyanthoate
  • cyclethrin TX
  • flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1 171) + TX, flumethrin (372) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, fonofos (1 191) + TX, formetanate (405) + TX, formetanate hydrochloride (405)
  • iodomethane (lUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl 0-(methoxy- aminothiophosphoryl)salicylate (lUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (altern
  • TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (lUPAC name) (1057) + TX, 0,0-diethyl 0-4-methyl-2-oxo-2/-/-chromen-7-yl phosphorothioate (lUPAC name) (1074) + TX, 0,0-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (lUPAC name) (1075) + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate (lU
  • development code (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129
  • TX spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TE
  • TX zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121- 52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1 ] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, triflumezopyrim (
  • TX 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541
  • phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (lUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1 ] + TX, fluopyram + TX, a
  • bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) +
  • TX chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1 183) + TX, flupropadine hydrochloride (1 183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (lUPAC name) (542) + TX, lindane (430) + TX, magnesium pho
  • TX hexaconazole [79983-71 -4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08-1 ] + TX, isotianil [224049-04-1 ] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures described in
  • TX triticonazole [131983-72-7] + TX, ancymidol [12771 -68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71 -9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221 -53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91 -4] + TX, spiroxamine [1 18134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61 -2] + TX, mepanipyrim [1 10235-47-7] + TX, pyrimethanil [531 12-28-0] + TX, fenpiclonil
  • TX myclozoline [54864-61 -8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471 -44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691 -80-3] + TX, flutolanil [66332-96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814-41 -0] + TX, oxycarboxin [5259-88-1 ] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [1 12-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystro
  • TX Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX,
  • Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp.
  • Bacillus subtilis strain AQ178 + TX Bacillus subtilis strain QST 713 (CEASE® + TX, Serenade® + TX, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus subtilis var.
  • amyloliquefaciens strain FZB24 (Taegro® + TX, Rhizopro®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1 Ab + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis israelensis (BMP123® + TX, Aquabac® + TX, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bonide® + TX, Scutella WP® + TX, Turilav WP ® +
  • TX Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari® + TX, DiPel®) + TX, bacteria spp.
  • Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp.
  • TX Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reuêtii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp.
  • TX Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX,
  • Cryptococcus laurentii + TX TX
  • Cupriavidus campinensis + TX Cydia pomonella granulovirus (CYD-X®) + TX
  • Drechslera hawaiinensis + TX Enterobacter cloacae + TX
  • Enterobacteriaceae + TX Entomophtora virulenta (Vektor®) + TX
  • Epicoccum nigrum + TX Epicoccum purpurascens + TX, Epicoccum
  • TX Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus
  • TX Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, Isoflavone - formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp.
  • Helicovex® Helicoverpa armigera nucleopolyhedrovirus
  • Myconate® Isoflavone - formononetin
  • Myconate® Isoflavone - formononetin
  • TX Lagenidium giganteum (Laginex®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertiki I®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®)
  • TX Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX,
  • Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp.
  • TX Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX,
  • Trichoderma asperellum T34 Biocontrol®
  • Trichoderma gamsii TX
  • Trichoderma atroviride Plantmate®
  • Trichoderma harzianum rifai Mycostar®
  • Trichoderma harzianum T-22 Trianum- P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp.
  • LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX,
  • Plant extracts including: pine oil (Retenol®) + TX, azadirachtin (Plasma Neem Oil® + TX, AzaGuard® + TX, MeemAzal® + TX, Molt-X® + TX, Botanical IGR (Neemazad® + TX, Neemix®) + TX, canola oil (Lilly Miller Vegol®) + TX, Chenopodium ambrosioides near ambrosioides (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, extract of neem oil (Trilogy®) + TX, essentials oils of Labiatae (Botania®) + TX, extracts of clove rosemary peppermint and thyme oil (Garden insect killer®) + TX, Glycinebetaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil +
  • Macrobials including: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline
  • TX Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica + TX, Dacnusa sibirica
  • Diglyphus isaea (Diminex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp.
  • TX Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C® + TX, Millenium® + TX, BioNem C® + TX, NemAttack®
  • TX Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator, and other biologicals including: abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporio
  • a biologically active compound selected from Quinofumelin + TX, mefentrifluconazol + TX, fenpicoxamid + TX, fluindapyr + TX, inpyrfluxam + TX or indiflumetpyr + TX, isoflucypram + TX, pyrapropoyne + TX, florylpicoxamid + TX, metyltetraprole + TX, ipflufenoquin + TX, pyridachlometyl + TX or chlopyridiflu + TX, tetrachlorantraniliprole + TX, tetrachloraniliprole + TX, Tyclopyrazoflor + TX, flupyrimin + TX or pyrifluramide + TX, benzpyrimoxan + TX, Benzosufyl + TX or oxazosulfyl + TX, etpyrafen + TX
  • the active ingredient mixture of the compounds of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P with active ingredients described above comprises a compound selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and an active ingredient as described above preferably 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
  • the mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
  • the mixtures comprising a compound of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and one or more active ingredients as described above can be applied, for example, in a single“ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a“tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and the active ingredients as described above is not essential for working the present invention.
  • compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides
  • compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • compositions that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention.
  • Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient.
  • the rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.
  • a preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question.
  • the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.
  • the compounds of the invention and compositions thereof are also be suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type.
  • the propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing.
  • the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling.
  • These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention.
  • Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • the present invention also comprises seeds coated or treated with or containing a compound of formula I.
  • coated or treated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application.
  • the present invention makes available a plant propagation material adhered thereto with a compound of formula I including those selected from Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P.
  • a composition comprising a plant propagation material treated with a compound of formula I including those selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P.
  • Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the seed treatment application of the compound formula I can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.
  • Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10'OOO ppm DMSO stock solutions. After drying the leaf discs were infested with adult white flies. The samples were checked for mortality 6 days after incubation.
  • Biological Example B2 Activity against Diabrotica balteata (Corn root worm) Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.
  • Diabrotica balteata Corn root worm
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P1 , P5, P6, P7, P8, P9, and P10.
  • Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P5, P9, and P10.
  • 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10'OOO ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation.
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P1 , P4, P5, P6, and P7.
  • 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P9, and P10.
  • Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P1 , P7, P8, P9, and P10.
  • Roots of pea seedlings infested with an aphid population of mixed ages were placed directly into aqueous test solutions prepared from 10 ⁇ 00 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings into test solutions.
  • 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P9, and P10.
  • Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.
  • Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10 ⁇ 00 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.
  • Biological Example B11 Activity against Heterodera schachtii (Juvenile mobility in vitro profiling in 96 well plate) Test solutions are prepared from 10 ⁇ 00 ppm DMSO stock solutions with a TECAN robot to achieve 20 pL of 500, 100, 50, 25, 12.5 and 6.25 ppm. For each concentration three replicates are produced. Per well, 80 pl_ nematode solution is added containing 100 to 150 freshly harvested second stage juveniles of Heterodera schachtii. The plates are covered and stored at room temperature in the dark and incubated for 48 h. Mobility of the exposed juveniles in a treated well is measured using an imaging tool and compared to an average of 12 untreated replicates.
  • Rice plants were treated with the diluted test solutions in a spray chamber. After drying plants were infested with ⁇ 20 N3 nymphs. 7 days after the treatment samples were assessed for mortality and growth regulation.
  • the following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 50 ppm: P7, P10.
  • Rice plants were treated with the diluted test solutions in a spray chamber. After drying plants were infested with ⁇ 20 N3 nymphs. 7 days after treatment adults were removed and 15 days after the treatment samples were assessed for effect on F1 generation.
  • Rice plants cultivated in a nutritive solution were treated with the diluted test solutions into nourishing cultivation system. 1 day after application plants were infested with ⁇ 20 N3 nymphs. 7 days after infestation samples were assessed for mortality and growth regulation.

Abstract

Compounds of the formula (I), wherein the substituents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling animal pests, including arthropods and in particular insects, molluscs or representatives of the order Acarina.

Description

Pesticidally active heterocyclic derivatives with sulfur containing substituents
The present invention relates to pesticidally active, in particular insecticidally active heterocyclic derivatives containing sulfur substituents, to processes for their preparation, to compositions comprising those compounds, and to their use for controlling animal pests, including arthropods and in particular insects or representatives of the order Acarina.
Heterocyclic compounds with pesticidal action are known and described, for example, in JP
2019/112398, WO 2017/077968, WO 2016/091731 and WO 2016/107742. There have now been found novel pesticidally active derivatives with sulfur containing bicyclic ring systems with a bridgehead nitrogen
The present invention accordingly relates to compounds of formula I,
Figure imgf000002_0001
wherein
A is CH or N;
X is S, SO or S02;
Ri is Ci-C4alkyl, or C3-C6cycloalkyl-Ci-C4alkyl;
R2 IS Ci-C6alkyl, Ci-C6haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl substituted with cyano, Ci- C6cyanoalkyl, Ci-C4alkoxyCi-C4alkyl, halogen, cyano, Ci-C4haloalkoxy, Ci-C4alkoxy, aminocarbonyl, Ci-C4alkoxycarbonyl, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, and Ci-C4alkylsulfonyl, Ci- C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, and Ci-C4haloalkylsulfonyl;
n is 0, 1 or 2;
Q is a radical selected from the group consisting of formula Qi to Q4
Figure imgf000002_0002
wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein Xi is O or NR4, wherein R4 is Ci-C4alkyl;
X2 is O or NR5, wherein R5 is Ci-C4alkyl
R3 is halogen, Ci-C6haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl or Ci-C6haloalkoxy;
Gi is N or CH;
G2 and G3 are, independently from each other, N or CH; or
an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.
Compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as Ci-C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as Ci-C4alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.
In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.
N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book“Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991 .
The compounds of formula I according to the invention also include hydrates which may be formed during the salt formation.
Where substituents are indicated as being itself further substituted, this means that they carry one or more identical or different substituents, e.g. one to four substituents. Normally not more than three such optional substituents are present at the same time. Preferably not more than two such substituents are present at the same time (i.e. the group is substituted by one or two of the substituents indicated). Where the additional substituent group is a larger group, such as cycloalkyl or phenyl, it is most preferred that only one such optional substituent is present. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio.
The term "Ci-Cxalkyl" as used herein refers to a saturated straight-chain or branched hydrocarbon radical attached via any of the carbon atoms having 1 to x carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1 - ethylpropyl, n-hexyl, n-pentyl, 1 , 1 -dimethylpropyl, 1 , 2-dimethylpropyl, 1 - methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 , 1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 , 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 , 2- trimethylpropyl, 1 ,2, 2-trimethylpropyl, 1 -ethyl-1 - methylpropyl, or 1 -ethyl-2-methylpropyl.
The term "Ci-Cxhaloalkyl" as used herein refers to a straight-chain or branched saturated alkyl radical attached via any of the carbon atoms having 1 to x carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of chloromethyl, dichloromethyl, trich loro methyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2- fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2, 2-trichloroethyl,
pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2- difluoropropyl, 2, 3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2, 3-dichloropropyl, 2- bromopropyl, 3-bromopropyl, 3,3, 3-trifluoropropyl, 3,3, 3- trichloropropyl, 2,2, 3,3, 3- pentafluoropropyl, heptafluoropropyl, 1 -(fluoromethyl)-2-fluoroethyl, 1 - (chloromethyl)-2-chloroethyl, 1 -(bromomethyl)-2-bromoethyl, 4-flu orobutyl, 4-ch loro butyl, 4-bromobutyl or nonafluorobutyl. According a term "Ci-C2-fluoroalkyl" would refer to a Ci-C2-alkyl radical which carries 1 ,2, 3,4, or 5 fluorine atoms, for example, any one of difluoromethyl, trifluoromethyl, 1 - fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 1 ,1 , 2, 2-tetrafluoroethyl or pentafluoroethyl.
The term "Ci-Cxalkoxy" as used herein refers to a straight-chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via an oxygen atom, i.e., for example, any one of methoxy, ethoxy, n-propoxy, 1 -methylethoxy, n-butoxy, 1 -methylpropoxy, 2- methylpropoxy or 1 , 1 -dimethylethoxy.
The term "Ci-Cxhaloalkoxy" as used herein refers to a Ci-Cxalkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoro methoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2- bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluoroeth- oxy, 2- fluoropropoxy, 3-fluoropropoxy, 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2- chloropropoxy, 3- chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3, 3-trichloropropoxy, 2,2, 3,3, 3- pentafluoropropoxy, heptafluoropropoxy, 1 - (fluoromethyl)-2- fluoroethoxy, 1 - (chloromethyl)-2-chloroethoxy, 1 -(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4- chlorobutoxy, or 4-bromobutoxy.
The term“Ci-C ralkylsulfanyl” as used herein refers to a straight chain or branched saturated alkyl radical having 1 to n carbon atoms (as mentioned above) which is attached via a sulfur atom, i.e., for example, any one of methylthio, ethylthio, n-propylthio, 1 -methylethylthio, butylthio, 1 -methylpropylthio, 2- methylpropylthio or 1 , 1 -dimethylethylthio.
The term "Ci-Cxalkylsulfinyl" as used herein refers to a straight chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via the sulfur atom of the sulfinyl group, i.e., for example, any one of methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1 -methylethyl- sulfinyl, n-butylsulfinyl, 1 -methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 , 1 -dimethyl- ethylsulfinyl, n- pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methyl- butylsulfinyl, 1 , 1 - dimethylpropylsulfinyl, 1 , 2-dimethylpropylsulfinyl, 2,2- dimethylpropylsulfinyl or 1 -ethylpropylsulfinyl.
The term "Ci-Cxalkylsulfonyl" as used herein refers to a straight chain or branched saturated alkyl radical having 1 to x carbon atoms (as mentioned above) which is attached via the sulfur atom of the sulfonyl group, i.e., for example, any one of methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, 1 -methylpropylsulfonyl, 2-methylpropylsulfonyl or t-butylsulphonyl.
The term "Ci-Cxhaloalkylsulfanyl" as used herein refers to a C1 -Cxalkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, any one of fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2, 2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro- 2,2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3- fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2- difluoropropylthio, 2,3-difluoropropylthio, 2, 3-dichloropropylthio, 3,3, 3- trifluoropropylthio, 3,3, 3- trichloropropylthio, 2,2, 3,3, 3-pentafluoropropylthio, heptafluoropropylthio, 1 - (fluoromethyl)-2- fluoroethylthio, 1 - (chloromethyl)-2-chloroethylthio, 1 - (bromomethyl)-2-bromoethylthio, 4- fluorobutylthio, 4-ch loro butylthio, or 4- bromobutylthio.
The term "Ci-Cxhaloalkylsulfinyl” and "Ci-Cnhaloalkylsulfonyl” refers to the groups above but with the sulfur in oxidations state 1 or 2 respectively. The term "Ci-Cxalkoxycarbonyl" as used herein refers to a straight chain or branched alkoxy radical having 1 to x carbon atoms (as mentioned above) which is attached via the carbon atom of the carbonyl group, i.e., for , any one of methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1- methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 , 1- dimethylethoxycarbonyl.
The term“Ci-Cxcyanoalkyl” as used herein refers to a straight chain or branched saturated alkyl radicals having 1 to x carbon atoms (as mentioned above) which is substituted by a cyano group, for example cyanomethylene, cyanoethylene, 1 ,1-dimethylcyanomethyl, cyanomethyl, cyanoethyl, and 1- dimethylcyanomethyl.
The term“C3-C6cycloalkyl” as used herein (including as a prefix before Ci-C4alkyl) refers to 3-6 membered cycloylkyl groups such as cyclopropane, cyclobutane, cyclopropane, cyclopentane and cyclohexane.
Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl
Embodiments according to the invention are provided as set out below.
Embodiment 1 provides compounds of formula I, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined above.
Embodiment 2 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiment 1 wherein:
A is CH or N;
X is S, SO or S02;
Ri is Ci-C3alkyl or C3-C6cycloalkyl-Ci-C2alkyl;
R2 IS Ci-C4alkyl, Ci-C4haloalkyl, C3-C4cycloalkyl, C3-C4cycloalkyl substituted with cyano, Ci- C2cyanoalkyl, Ci-C3alkoxyCi-C2alkyl, fluoro, chloro, bromo, cyano, Ci-C3haloalkoxy, Ci-C4alkoxy, aminocarbonyl, Ci-C2alkoxycarbonyl, Ci-C2alkylsulfanyl, Ci-C2alkylsulfinyl, Ci-C2alkylsulfonyl, Ci- C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl or Ci-C2haloalkylsulfonyl;
n is 0 or 1 ; and
Q is a radical selected from the group consisting of formula Qi , Q2 or C
Figure imgf000006_0001
Q wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein
Xi is NR4, wherein R4 is Ci-C2alkyl;
X2 is O or NR5, wherein R5 is Ci-C2alkyl
R3 is fluoro, chloro, bromo, Ci-C2haloalkyl, Ci-C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl, Ci- C2haloalkylsulfonyl or Ci-C2haloalkoxy;
Gi is N or CH; and
G3 is N or CH.
Embodiment 3 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiment 1 wherein:
A is CH or N;
X is S, SO or SO2;
Ri is ethyl, propyl, isopropyl or cyclopropylmethyl;
R2 IS Ci-C3alkyl, Ci-C2haloalkyl, cyclopropyl, cyclopropyl substituted with cyano, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, fluoro, chloro, bromo, cyano, Ci- C2haloalkoxy, Ci-C3alkoxy, aminocarbonyl, methoxycarbonyl, Ci-C2alkylsulfanyl, Ci-C2alkylsulfinyl, Ci- C2alkylsulfonyl, Ci-C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl or Ci-C2haloalkylsulfonyl;
n is 0 or 1 ; and
Q is a radical selected from the group consisting of formula Qi or C
Figure imgf000007_0001
wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein
Xi is NCH3;
X2 is NCH3;
R3 is bromo, trifluoromethyl, pentafluoroethyl, 1 , 1 -difluoroethyl, difluoromethyl, difluorochloromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, difluoromethylsulfanyl, difluoromethylsulfinyl, difluoromethylsulfony, difluoromethoxy, difluorobromomethoxy or
trifluoromethoxy; and
Gi is N or CH.
Embodiment 4 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that when Q is C and X2 is NRs, then Gi is CH. Embodiment 5 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that F¾ is not Ci- C2haloalkyl when Q is C , Gi is N and X2 is NMe.
Embodiment 6 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that R2 is not trifluoromethyl when Q is C , Gi is N and X2 is NMe.
Embodiment 7 provides compounds, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to embodiments 1 , 2, or 3 with the proviso that the compound 2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5- b] pyridine is excluded.
A preferred group of compounds of formula I is represented by the compounds of formula 1-1
Figure imgf000008_0001
(1-1)
wherein A, X, Ri , R2, R3, n, Xi and Gi are as defined under formula I above.
In one preferred group of compounds of formula 1-1 , A is CH or N; X is S, SO or SO2; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen, cyano, aminocarbonyl, or Ci-C2alkoxycarbonyl; R3 is Ci-C4haloalkyl, Ci- C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; Xi is O or NCH3; and Gi is N or CH.
In another preferred group of compounds of formula 1-1 , A is CH or N; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; n is 0 or 1 ; Xi is O or NCH3; and Gi is N or CH.
In another preferred group of compounds of formula 1-1 , A is CH; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; n is 0 or 1 ; Xi is NCH3; and Gi is CH.
In another preferred group of compounds of formula 1-1 , Gi is CH, Xi is NMe and A is CH. In a further preferred group of compounds of formula 1-1 , Ri is Ci-C3alkyl; preferably ethyl, propyl, or isopropyl; R2 is 1 , 1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; and R3 is Ci-C2fluoroalkyl, Ci-C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci- C2fluoroalkylsulfonyl; preferably trifloromethyl.
In compounds of formula 1-1 and all of the preferred embodiments of compounds of formula 1-1 mentioned above, unless otherwise specified, A, X, Ri , R2, R3, n, Xi and Gi are as defined under formula I above; preferably A is CH or N, more preferably A is CH; preferably Ri is Ci-C2alkyl, more preferably Ri is ethyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; more preferably R2 is pentafluoroethyl, trifluoromethyl, bromo, cyano, aminocarbonyl, or methoxycarbonyl; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; more preferably R3 is trifluoromethyl; preferably n is 0 or 1 ; more preferably n is 1 ; preferably Xi is O or NChh; more preferably Xi is NChh; and preferably Gi is N or CH; more preferably Gi is CH.
Another preferred embodiment of the compounds of formula 1-1 is represented by the formula 1-1 a
Figure imgf000009_0001
(1-1 a)
wherein A, X, Ri , R2, R3, Xi and Gi are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula 1-1 .
Another preferred group of compounds of formula I is represented by the compounds of formula I-2
Figure imgf000009_0002
(i-2)
wherein A, X, Ri , R2, R3, n and G3 are as defined under formula I above.
In one preferred group of compounds of formula I-2, A is CH or N; X is S, SO or S02; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; and G3 is N or CH. In another preferred group of compounds of formula i-2, A is CH or N; X is S, SO or SO2; Ri is Ci- C3alkyl; R2 is Ci-C2haloalkyl, halogen or cyano; R3 is Ci-C2haloalkyl, Ci-C2haloalkylsulfanyl, Ci- C2haloalkylsulfinyl, or Ci-C2haloalkylsulfonyl; n is 0 or 1 ; and G3 is N or CH.
In compounds of formula i-2 and all of the preferred embodiments of compounds of formula i-2 mentioned above, unless otherwise specified, A, X, Ri , R2, R3, n and G3 are as defined under formula I above; preferably A is CH or N; preferably X is S, SO or SO2; preferably Ri is Ci-C2alkyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen or cyano; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; preferably n is 0 or 1 ; more preferably n is 1 ; and preferably G3 is N or CH.
Another preferred embodiment of the compounds of formula 1-2 is represented by the formula l-2a
Figure imgf000010_0001
wherein A, X, Ri , R2, R3 and G3 are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-2.
A further preferred group of compounds of formula I is represented by the compounds of formula i-3
Figure imgf000010_0002
wherein A, X, Ri , R2, R3, n, G2 and G3 are as defined under formula I above.
In one preferred group of compounds of formula I-3, A is CH or N; X is S, SO or S02; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; G2 is N and G3 is CH.
In another preferred group of compounds of formula i-3, A is CH or N; X is S, SO or SO2; Ri is Ci- C3alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; G2 is CH and G3 is N. In compounds of formula I-3 and all of the preferred embodiments of compounds of formula I-3 mentioned above, unless otherwise specified, A, X, Ri , R2, R3, n, G2 and G3 are as defined under formula I above; preferably A is CH or N; X is S, SO or SO2; preferably Ri is Ci-C2alkyl; preferably R2 is 1 , 1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen or cyano; preferably R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; preferably n is 0 or 1 ; more preferably n is 1 ; in one prefered embodiment G2 is N and G3 is CH; and in another prefered embodiment G2 is CH and G3 is N.
Another preferred embodiment of the compounds of formula I-3 is represented by the formula l-3a
Figure imgf000011_0001
wherein A, X, Ri , R2, R3, G2 and G3 are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-3.
Another preferred group of compounds of formula I is represented by the compounds of formula I-4
Figure imgf000011_0002
wherein A, X, Ri , R2, R3, n, X2 and Gi are as defined under formula I above.
In one preferred group of compounds of formula I-4, A is CH or N; X is S, SO or S02; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen, cyano; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; X2 is O or NCH3; and Gi is N or CH.
In another preferred group of compounds of formula I-4, A is CH or N; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; n is 0 or 1 ; X2 is O or NCH3; and Gi is N or CH.
In another preferred group of compounds of formula I-4, A is CH; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci-
Figure imgf000012_0001
In a further preferred group of compounds of formula I-4, Ri is Ci-C2alkyl; preferably ethyl; R2 is 1 ,1 - difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, or cyano; and R3 is Ci-C2fluoroalkyl, Ci- C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci-C2fluoroalkylsulfonyl; preferably trifloromethyl.
In another preferred group of compounds of formula I-4, Gi is CH, X2 is NMe and A is CH.
In another preferred group of compounds of formula I-4, Gi is CH, X2 is O and A is CH.
In a further preferred group of compounds of formula I-4, Gi is N, X2 is NMe and A is CH.
In a further preferred group of compounds of formula i-4, R2 IS not Ci-C2haloalkyl when Gi is N, X2 is NMe and A is CH.
In a further preferred group of compounds of formula i-4, R2 IS not trifluoromethyl when Gi is N, X2 is NMe and A is CH.
In a further preferred group of compounds of formula i-4, the compound 2-[6-ethylsulfonyl-2- (trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine is excluded.
In a further preferred group of compounds of formula I-4, the compound 2-[6-ethylsulfonyl-2-(1 ,1 ,2,2,2- pentafluoroethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine is excluded.
In compounds of formula I-4 and all of the preferred embodiments of compounds of formula I-4 mentioned above, unless otherwise specified, A, X, Ri , R2, R3, n, X2 and Gi are as defined under formula I above; preferably A is CH or N, more preferably A is CH; preferably Ri is ethyl; preferably R2 is 1 ,1 -difluoroethyl, pentafluoroethyl, trifluoromethyl, halogen, cyano, aminocarbonyl, or
methoxycarbonyl; more preferably R2 is pentafluoroethyl, trifluoromethyl, bromo, cyano,
aminocarbonyl, or methoxycarbonyl; preferably R3 is trifluoromethyl, pentafluoroethyl,
trifluoromethylsulfanyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; more preferably R3 is trifluoromethyl; preferably n is 0 or 1 ; more preferably n is 1 ; preferably X2 is O or NCH3; more preferably X2 is NCH3; and preferably Gi is N or CH; more preferably Gi is CH.
Another preferred embodiment of the compounds of formula I-4 is represented by the formula l-4a wherein A, X, Ri , R2, R3, X2 and Gi are as defined under formula I above or as defined under any of the preferred embodiments of the compounds of formula I-4.
Another especially preferred group of compounds of formula I are those represented by the compounds of formula 1-1 , I-2, I-3, or i-4 wherein
A is CH or N, preferably A is CH;
Ri is ethyl, propyl or isopropyl; preferably Ri is ethyl;
R3 is trifluoromethyl, pentafluoroethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, or
trifluoromethylsulfonyl; preferably R3 is trifluoromethyl; and
n is 0 or 1 ; preferably n is 1 .
Another preferred group of compounds of formula I is represented by the compounds of formula I-5
Figure imgf000013_0001
i-5
wherein
A is CH or N;
X is S, SO or S02;
Ri is Ci-C4alkyl;
R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl;
R6 and R7 are, independently, hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, halogen, cyano, aminocarbonyl, or Ci-C2alkoxycarbonyl;
Xi is O or NMe; and
Gi and G2 are, independently, N orCH.
Another preferred group of compounds of formula I is represented by the compounds of formula I-6 (1 -6)
wherein
A is CH or N;
X is S, SO or S02;
Ri is Ci-C4alkyl;
R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl;
R6 and R7 are, independently, hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, halogen, or cyano; and
G3 is N or CH.
Another preferred group of compounds of formula I is represented by the compounds of formula I-7
Figure imgf000014_0001
wherein
A is CH or N;
X is S, SO or S02;
Ri is Ci-C4alkyl;
R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl;
R6 and R7 are, independently, hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, halogen, or cyano; and
Gi is N and G2 IS CH, or Gi is CH and G2 IS N.
Compounds according to the invention may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability or environmental profile). In particular, it has been surprisingly found that certain compounds of formula (I) may show an advantageous safety profile with respect to non-target arthropods, in particular pollinators such as honey bees, solitary bees, and bumble bees. Most particularly, Apis mellifera. In another aspect the present invention provides a composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I-5), (I-6) and (I-7), and, optionally, an auxiliary or diluent.
In a further aspect the present invention provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, as defined in any of the embodiments under compounds of formula (1-1), (I-2), (I-3), (I-4), (I-5), (I-6) and (I-7) (above) or a composition as defined above.
In a yet further aspect, the present invention provides a method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition as defined above.
The process according to the invention for preparing compounds of formula I is carried out by methods known to those skilled in the art.
Compounds of formula I, where Q is Qi may be represented by formula V or formula III, where Ri , R3, Gi , A, X are as defined above and Rn and Rnå may be independently hydrogen or R2 as defined above.
Scheme 1 :
Figure imgf000015_0001
Compounds of formula V may be prepared following scheme 1 . Compounds of formula V, wherein R3, Gi , A, X are as defined above and Rn and Rnå may be independently R2 as defined above, may be prepared from compound IV, wherein R3, Gi, A, X are as defined above and Rn is R2 as defined above and Xo3 is halogen, by reacting with compounds Rn2-Mo, wherein Mo is a boronic acid, and Rnå is R2 in the presence of a palladium catalyst. When Mo is a boronic acid, the reaction is usually carried out in the presence of a base, for example potassium carbonate, cesium carbonate, or potassium phosphate, in an inert solvent, such as dioxane, optionally in the presence of water, with a palladium(O) catalyst, for example tetrakis(triphenylphosphine)palladium, at a temperature between 80-120°C. Such Suzuki reactions are well precedented in the literature, see for example Masuda, Naoyuki et al, WO 2012/133607. Halogenation of compounds of formula III, wherein R3, Gi, A, X are as defined above and Rn is R2 as defined above, with a halogenating agent such as N-chlorosuccinamide, N- bromosuccinamide, or N-iodosuccinamide, in a polar aprotic solvent such as acetonitrile or dimethylformamide, at ambient temperature, leads to compounds of formula IV wherein R3, Gi , A, X are as defined above and Rn is R2 as defined above and X03 is halogen. Compounds of formula III, wherein R3, Gi, A, X are as defined above and Rn is R2 as defined above, can be prepared by reacting a compound of formula II wherein R3, Gi, A, X are as defined above with a compound of formula VI wherein X02 is a halogen or a leaving group OSO2R8 (wherein Rs is phenyl, toluol, Ci-C4alkyl or Ci- C4haloalkyl) and Rn is R2 as defined above, optionally in the presence of a suitable base in an inert solvent in the temperature range from 100 °C to 200 °C.
Those skilled in the art would realise that below compounds of formula I, wherein Q is Q2, Cb and CU which can be represented by compounds of formula X, XI, XII respectively, wherein Ri , R3, Gi, G2, G3, A, X are as defined above and Rn and Rnå are independently R2 as defined above, could be prepared analogous to above procedure as well from compounds of formula VII, VIII and IX respectively, wherein Ri , R3, Gi , G2, G3, A and X are as defined above.
Figure 1 :
Figure imgf000016_0001
Compounds of formula II, wherein Ri , R3, Gi, A, X, Xi are as defined above can be prepared as shown in scheme 2:
Scheme 2:
Figure imgf000017_0001
or (CH3)3Si(CH2)2S02NH2
followed by deprotection
by an amination reaction, which involves for example, reacting compounds of formula XIII, wherein R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, with amino reagents like, for example, ammonia NH3, or ammonia equivalent ammonium hydroxide NH4OH, ammonium chloride NH4CI, ammonium acetate NhUOAc, ammonium carbonate (NH4)2C03, and other NH3 surrogates. This transformations is preferably performed in suitable solvents (or diluents) such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are methanol, ethanol, 2,2,2-trifluoroethanol, propanol, iso-propanol, N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation. This transformation may also be performed in the presence of protected ammonia source such as for example fe/ -Butyl carbamate NH2B0C, benzophenone imine Ph2C=NH, or 2- (trimethylsilyl)ethanesulfonamide (CH3)3SiCH2CH2SC>2NH2 which may be deprotected in the presence of suitable reagents. Examples of suitable deprotecting reagents include for example trifluoroacetic acid and hydrochloric acid for the deprotection of -NHBoc and -N=CPti2. Examples of suitable deprotecting reagents for -NHSC>2CH2CH2Si(CH3)3 include cesium fluoride, tetramethylammonium fluoride, tetra-n- butylammonium fluoride amongst others. Amination reaction to convert compounds of formula XIII, wherein R3, Gi, A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, to compounds of formula II, wherein R3, Gi , A, X, Xi are as defined above may be performed optionally in the presence of suitable transition metal catalysts like, for example palladium(ll) acetate Pd(OAc)2, tris(dibenzylideneacetone)dipalladium(0) Pd2dba3, [1 ,1 - Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) Pd(dppf)Cl2, Palladium(TT-cinnamyl) chloride dimer [(Cinnamyl)PdCI]2, Cu powder, copper oxide CuO or Cu20, copper sulfate CUSO4 in combination with ligands for example triphenylphosphine PtbP, tricyclohexylphosphine PCy3, tri-tert-butylphosphine P(f-Bu)3, N,N'-Dimethylethylenediamine, or bidentate bisphosphine ligands such as 2- Diphenylphosphoryl-2'-diphenylphosphino-1 ,1 '-biphenyl, 2, 2'-Bis(diphenylphosphino)-1 ,1 '-biphenyl amongst others. This transformations is preferably performed in suitable solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are methanol, ethanol, 2,2,2- trifluoroethanol, propanol, iso-propanol, ethylene glycol, N,N-dimethylformamide, N,N- dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation. Such transformations are known in the literature and reported in Org. Process Res. Dev., 2017, 21 (9), 1447-1451 , Chem. Commun., 2010, 46, 925-927, J. Org. Chem. , 2004, 69 (19), 6504-6506, Chem. Eur. J. 2010, 16, 1983-1991 .
Those skilled in the art would realise that below compounds of formula XVII, XVIII, XIX, wherein Gi , G2, G3, A, Ri , R2, R3, X are as defined above, could be prepared analogous to above procedure as well from compounds of formula XIV, XV and XVI respectively, wherein Gi , G2, G3, A, Ri , R2, R3 and X2 are as defined above (figure 2).
Figure 2: Compounds offormula XIII, wherein Ri , R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl- sulfonate such as trifluoromethanesulfonate, can be prepared following scheme 3. Compounds of formula XIII, wherein R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, can be prepared by oxidation of compounds of formula XIII, wherein Ri , R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or Scheme 3:
Figure imgf000019_0001
iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate. The reaction can be performed with reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert-butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate. These reactions can be performed in various organic or aqueous solvents compatible to these conditions, by temperatures from below 0 °C up to the boiling point of the solvent system. Compounds offormula XIII, wherein Ri , R3, Gi , A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl- sulfonate such as trifluoromethanesulfonate, may be obtained by dehydrative cyclization, e.g. by heating the compounds in a microwave, in the presence of an acid catalyst, for example methane sulfonic acid, or para-toluene sulfonic acid, in an inert solvent such as N-methyl pyrollidine at temperatures between 25-180 °C, preferably 130-170 °C. Such processes have been described previously in WO 2010125985. Alternatively, compounds of formula XXV can be converted to compounds of formula XIII (wherein Xi is O) using triphenyl phosphine, di-isopropyl azo dicarboxylate in an inert solvent such as THF at temperatures between 25-50°C. Such Mitsunobu conditions have been previously described for such transformations (see WO2009131237). Compounds of formula XXV, wherein Ri , R3, Gi, A, X, Xi are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, may be prepared from compound of formula XXIII by carboxylic group activation to form compounds of formula XXIV wherein A, X are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and LG3 is a leaving group like, for example chlorine, bromine or iodine (preferably chlorine), and then treating with compounds of formula XXVI, wherein R3, Gi, Xi are as defined above, optionally in the presence of base e.g. triethylamine or pyridine. Such transformations are known to the person skilled in the art and are described in for example Tetrahedron, 61 (46) , 10827- 10852, 2005. For example compound XIV where LG3 is halogen are formed by treatment with for example, oxallyl chloride orthionyl chloride in the presence of catalytic quantities of DMF in inert solvents such as methylene chloride or THF at temperatures between 20 °C to 100 °C., preferably 25 °C. Alternatively, compounds of formula XXV can be prepared by treatment of compounds of formula XXIII with dicyclohexyl carbodiimide (DCC) or 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species XXIV, wherein LG3 is LG3a and LG3b respectively, in an inert solvent, e.g. pyridine, or THF optionally in the presence of a base, e.g. triethylamine, at temperatures between 50-180 °C.
Figure imgf000020_0001
Subgroups of compounds of formula XXIII may be obtained from compound of formula XXII, wherein Ri , X, A, are as defined in formula I above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, by hydrolysis reaction employing suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others. Compound of formula XXII, wherein Ri , A, are as defined in formula I above and X is SO or SO2, and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and R is C1-C6 alkyl, C1-C6 haloalkyl or benzyl, may be obtained from compounds of formula XXII, wherein Ri , A, are as defined in formula I above and X is S or SO, and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, via oxidation reaction. The reaction as described in the synthesis of XIII in scheme 3 can be performed with reagents such as a peracid, for example peracetic acid or m-chloroperbenzoic acid, or a hydroperoxide, as for example, hydrogen peroxide or tert- butylhydroperoxide, or an inorganic oxidant, such as a monoperoxo-disulfate salt or potassium permanganate. Alternatively compounds of formula XXII may be obtained from compounds of formula XXI via nucleophilic aromatic substitution and regiocontrolled SnAr reaction using R1-X-M reagents, wherein R1 and X are as defined in formula I above and M is monovalent metal such as Na, K, Li, optionally in the presence of transition metal complexes such as palladium complex, copper complex for example Pd(PPh3)4, Pd(OAc)2, Pd2dba3, Cul, CU2O in combination with monodentate or bidendate ligands such as tricyclohexylphosphine PCy3, tri-tert-butylphosphine P(f-Bu)3, N,N'- dimethylethylenediamine, 2-diphenylphosphoryl-2'-diphenylphosphino-1 ,T-biphenyl, 2,2'- bis(diphenylphosphino)-1 ,T-biphenyl amongst others. This transformations is preferably performed in suitable solvents such as alcohols, amides, esters, ethers, nitriles and water, particularly preferred are N,N-dimethylformamide, N,N-dimethylacetamide, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, ethyl acetate, water or mixtures thereof, optionally in presence of a base, at temperatures between 0-150°C, preferably at temperatures ranging from room temperature to the boiling point of the reaction mixture, optionally under microwave irradiation. Such transformations are described for example in Synthesis 2013, 45(11), 1489-1496 and Chemistry - A European Journal, 2014, 20(39), 12584-12594. Compounds of formula XXI, wherein A is C or N, R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, LGi and LG2 are leaving groups like, for example, chlorine, bromine or iodine, or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, may be prepared via esterification reactions from compounds of formula XX. Such reactions are well known to those skilled in the state of art and may performed under basic conditions in the presence of alkyl halide, haloalkyl halide or benzyl halide in the presence of suitable base such as trimethylamine, pyridine, potassium carbonate, cesium carbonate amongst others. Alternatively these reactions may be performed in the presence of acid or Lewis acids and suitable alcohols, examples of acid include HCI, H2SO4, TFA, tosic acid amongst others and example of Lewis acid include Scandium triflate Sc(OTf)2, FeCL, Yb(OTf)2 amongst others to convert compounds of formula XX to compounds of formula XXI. These reactions have been reported in literature for example in Synthesis, 2008, 3407-3410, Chem. Commun., 1997, 351-352, J. Org. Chem., 2006, 71, 3332-3334. Such reactions are known by the name of Fischer-Speier esterification. Alternatively transformation of compound of formula XX to compound of formula XXI may also be performed in the presence of trimethylsilyl (TMS) derivative of diazomethane and suitable alcohol reagent ROH, wherein R is C1-C6 alkyl, C1-C6 haloalkyl or benzyl. Such reactions are preferably performed in the presence of solvent or combination of solvents such as for example toluene, diethyl ether, tetrahydrofuran. Such reactions are described in Angew. Chem. int. Ed. 2007, 46, 7075 -7078.
Those skilled in the art would realize that compounds of formula XXVII, wherein Ri , R3, Gi , X2, A, X are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, may be prepared in analogous method following the above protocol.
Figure imgf000022_0001
The subgroup of compounds of formula XXIV, wherein R3, G3, A, X, Ri, are as defined above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an
Figure imgf000022_0002
aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, can be prepared by reacting a compound of formula XXVIII wherein R3, G3 are as described in formula (I) with a compound of formula XXIX wherein X01 is a halogen or a leaving group aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, and A, X are as defined in formula (I), optionally in the presence of a suitable base in an inert solvent.
Scheme 4:-
Figure imgf000023_0001
A further process to prepare compounds of formula XIV, involves reacting a compound of formula
Scheme 5:-
Figure imgf000023_0002
halogenation XXVII I with a compound of XXX in the presence of a Lewis acid, such as Zinc(l l)iodide or Indium(ll l) triflate, in an inert solvent such as chlorobenzene or 1 ,2, dichlorobenzene, with a catalytic copper(ll) salt, such as Cu(l l)acetate, under an oxygen or air atmosphere at temperatures between 100-180 °C, preferably 1 10-140 °C. Such reactions have previously been described in the literature (see Adv. Synth. Catal. 2013, 355, 1741 - 1747, and J. Org. Chem., 2013 , 78 , 12494-12504). Compounds of formula XXIX and XXX can be prepared from compounds of formula XXI I I by, for example, the methods shown in scheme 6.
Scheme 6:-
In scheme 6, an acyl halide of formula XXIIIa is converted to a Weinreb amide XXIIIb upon reaction with L/,O-Dimethylhydroxylamine by methods known to those skilled in the art and described for example in Synthesis 2015, 47, 1413-1422. The Weinreb amide of formula XXIIIb is then reacted with a Grignard reagent of formula ChhMgHal according to the method of Weinreb ( Tetrahedron Letters 1981 , 22, 3815- 3818) to give compounds of formula XXX. Compounds of formula XXXI can be halogenated to compounds of formula XXIX, with for example mixtures of bromine and hydrobromic acid in acetic acid (as described in Phosphorus, Sulfur and Silicon and the Related Elements, 2013, 188(12), 1835-1844) or with, for example, copper(ll)bromide in an inert solvent, for example chloroform, ethyl acetate and the like, as described in J. Med. Chem., 2013, 56(1 ), 84-96. Alternatively compounds of formula XXX, can be prepared directly from compounds of formula XXIIIa by treatment with diazomethane or trimethyl silyl diazomethane and subsequent treatment with an halogen acid, for example, hydrobromic acid or hydrochloric acid in an inert solvent such as diethyl ether. Such procedures are well known in the literature, for example see Eu. J. Med. Chem., 1387, 22(5), 457-62 and WO 2009010455.
Compounds of the formula XV, wherein R3, G2, G3, Ri , A, X are as defined in formula I above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate,
Scheme 71-
Figure imgf000025_0001
may be prepared (scheme 7) via N-N bond forming reaction of azido imines of compounds of the formula (XXXIV), wherein R3, G2, G3, Ri, A, X are as defined in formula I above, under pyrolytic condition which facilitates extrusion of N2 Alternatively, this reaction may be conducted in presence of a metal catalyst, for example a Cu(l) catalyst, such as Cul, CuBr, CuCI or CuCN , or more generally with transition metals, in combination with a ligand such as tetramethylethylenediamine, 2,2'-bipyridine or 1 ,10-phenanthroline. Suitable solvents may include use of e toluene, chlorobenzene, or xylene, at temperatures between room temperature and 200°C, preferably between 100 and 160°C, optionally under microwave heating conditions. Such reductive cyclisation reaction conditions were described in, for example, Organic Letters, 2011 , Vol. 13, No. 13, 3542-3545, US 2017/0260183,
Compounds of the formula (XXXIV), wherein R3, G2, G3, Ri , A, X are as defined in formula I above, and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, may be prepared by reaction between compounds of formula (XXXI), wherein R3, G2, G3 are as defined in formula I, and compounds of formula (XXXII), wherein R1 , X are as defined in formula I above and LGi is a leaving group like, for example, chlorine, bromine or iodine (preferably chlorine or bromine), or an aryl- or (halo)alkyl-sulfonate such as trifluoromethanesulfonate, usually upon heating at temperatures between room temperature and 200°C, preferably between 40 °C and 160°C, optionally under microwave heating conditions, in suitable solvents that may include, for example, f-BuOH, toluene or xylene or combinations of two or more solvents. The formation of compounds of formula (XXXIV) may require water removal, either by azeotropic distillation, or by means of a drying agent such as for example TiCU or molecular sieves. Such formation of Schiff bases of formula (XXXIV) is known to those skilled in the art, and are described in, for example, WO 2017/134066. Compounds of formula XXXI, wherein G2 is C, G3 is N, R3 is CF3 are reported in literature with CAS 221 1908-96-0 and reported in WO 2018/052136.
Compounds of the formula XXXII, may be prepared by the reaction of compound of formula XXXIII in the presence of acid such as HCI, H2SO4, H3PO4, HNO3, TFA. Such deprotection reaction of N-linked carbamate are well known to those skilled in the art and described for example in RSC Advances, 5(5), 3200-3205; 2015
Compounds of formula XXXIII, may be prepared by the reaction of compounds of formula XIII and organo-azide or an ammonia derivatives for example NH4OH, NH3, NH2B0C in the presence of a suitable base and in the presence or absence of Lewis acids and solvent at temperatures between 50 °C and 200 °C. Examples of organo-azide include TMSN3, sodium azide, diphenyl phosphoryl azide or tosyl azide and suitable solvent may be toluene, xylene, THF or acetonitrile. Example of suitable Lewis acid may include Zn(OTf)2 amongst others. Such reactions of converting carboxylic acids to amines are well known to those skilled in the art by the name of Curtius rerrangement and reported in Org. Lett. , 2005, 7, 4107-41 10; Journal of Medicinal Chemistry, 49(12), 3614-3627; 2006.
Alternatively compounds of formula I,
Figure imgf000026_0001
wherein Q, X, Ri , A and R2 are as defined above may be prepared using carboxylic acid derivative XXXV, wherein X, Ri and R2 are as described in formula I above. For example compound of formula I, wherein Q is Q1 may be represented by formula V, wherein R3, Gi, Xi , X, Ri are as described in formula I and Rnå and Rn are independently R2 as defined in formula I, may be prepared following scheme 8 analogous to procedure described in scheme 3. People skilled in the state of art will realize compounds of formula I wherein Q is CU may also be prepared following procedure analogous to scheme 8. Scheme 8:-
Figure imgf000027_0001
Alternatively compounds of formula I,
Figure imgf000027_0002
wherein X, Ri , A and F¾ are as defined above and Q is Cte may be represented by compounds of formula X, wherein R3, G3, X, R1 , A are as define in formula I above, and Rnå and Rn are independently R2 as described in formula I above, may be prepared using carboxylic acid XXXV to form either halo ketone XXXVIII or ketone XXXIX and reacting with amine XXVIII analogous to procedure described in scheme 4, scheme 5 and scheme 6.
Figure imgf000027_0003
XXVIII Alternatively compounds of formula I,
Figure imgf000028_0001
wherein X, Ri , A and F¾ are as defined above and Q is Cb may be represented by compounds of formula XI, wherein R3, G3, X, R1 , A are as define in formula I above, and Rnå and Rn are independently R2 as described in formula I above, may be prepared using carboxylic acid XXXV and azido aldehyde XXXI analogous to procedure described in scheme 7. People skilled in the state of art will realize amine XXXX serves as a key intermediate for the synthesis of XI in this procedure.
Figure imgf000028_0002
Compounds of formula XXXV, wherein Ri , X, A are as defined above and Rnå is H and Rn is R2 as described in formula I above, may be represented by compounds of formula XXXVIII. Scheme 9:-
Figure imgf000029_0001
Compounds of formula XXXVIII may be obtained from compound of formula XXXVII, wherein Ri, X, A, are as defined in formula I above and Rn is R2 as defined in formula I above and R is C1-C6 alkyl, C1-C6 haloalkyl, or benzyl, by hydrolysis reaction employing suitable hydrolyzing agent such as for example NaOH, LiOH, KOH, amongst others. Compounds of formula XXXVII may be obtained from compounds of formula XXXVI analogous to procedure described in scheme 4. Compounds of formula XXXVI may be obtained from compounds of formula XXII analogous to procedure described in scheme 2. Compounds of formula XXXV wherein Ri , X, A are as defined in formula I above and Rn and Rnå are independently R2 as described in formula I above, may be prepared from compounds of formula XXXVII analogues to procedure described in scheme 1 for the transformation of compounds of formula III to compounds of formula V.
Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
Salts of compounds of formula I can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
Salts of compounds of formula I can be converted in a manner known per se into other salts of compounds of formula I, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
Depending on the procedure or the reaction conditions, the compounds of formula I, which have saltforming properties can be obtained in free form or in the form of salts.
The compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.
Diastereomer mixtures or racemate mixtures of compounds of formula I, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.
Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid
chromatography (HPLC) on acetyl celulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents.
Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or
enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.
N-oxides can be prepared by reacting a compound of the formula I with a suitable oxidizing agent, for example the H2C>2/urea adduct in the presence of an acid anhydride, e.g. trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561 -73,
1989 or WO 2000/15615.
It is advantageous to isolate or synthesize in each case the biologically more effective isomer, for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.
The compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
The compounds according to the following Tables Z-1 to Z-240, Za-1 - Za-60, and Zb-1 - Zb30 below can be prepared according to the methods described above. The examples which follow are intended to illustrate the invention and show certain preferred compounds of formula I.
The tables Z below illustrate specific compounds of the invention.
Figure imgf000031_0001
Table Z-1 provides 17 compounds Z-1 .001 to Z-1 .017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Y: Substituent definitions of R6 and R7for the compounds of formula A in tables Z:
Figure imgf000032_0001
Table Z-2 provides 17 compounds Z-2.001 to Z-2.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-3 provides 17 compounds Z-3.001 to Z-3.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-4 provides 17 compounds Z-4.001 to Z-4.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-5 provides 17 compounds Z-5.001 to Z-5.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-6 provides 17 compounds Z-6.001 to Z-6.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-7 provides 17 compounds Z-7.001 to Z-7.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-8 provides 17 compounds Z-8.001 to Z-8.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-9 provides 17 compounds Z-9.001 to Z-9.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-10 provides 17 compounds Z-10.001 to Z-10.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-1 1 provides 17 compounds Z-1 1 .001 to Z-1 1 .017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-12 provides 17 compounds Z-12.001 to Z-12.017 of formula A wherein R3 is CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-13 provides 17 compounds Z-13.001 to Z-13.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-14 provides 17 compounds Z-14.001 to Z-14.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-15 provides 17 compounds Z-15.001 to Z-15.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-16 provides 17 compounds Z-16.001 to Z-16.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-17 provides 17 compounds Z-17.001 to Z-17.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-18 provides 17 compounds Z-18.001 to Z-18.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-19 provides 17 compounds Z-19.001 to Z-19.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-20 provides 17 compounds Z-20.001 to Z-20.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-21 provides 17 compounds Z-21 .001 to Z-21 .017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-22 provides 17 compounds Z-22.001 to Z-22.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y. Table Z-23 provides 17 compounds Z-23.001 to Z-23.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-24 provides 17 compounds Z-24.001 to Z-24.017 of formula A wherein R3 is CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-25 provides 17 compounds Z-25.001 to Z-25.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-26 provides 17 compounds Z-26.001 to Z-26.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-27 provides 17 compounds Z-27.001 to Z-27.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-28 provides 17 compounds Z-28.001 to Z-28.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-29 provides 17 compounds Z-29.001 to Z-29.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-30 provides 17 compounds Z-30.001 to Z-30.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-31 provides 17 compounds Z-31 .001 to Z-31 .017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-32 provides 17 compounds Z-32.001 to Z-32.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-33 provides 17 compounds Z-33.001 to Z-33.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-34 provides 17 compounds Z-34.001 to Z-34.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-35 provides 17 compounds Z-35.001 to Z-35.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-36 provides 17 compounds Z-36.001 to Z-36.017 of formula A wherein R3 is CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-37 provides 17 compounds Z-37.001 to Z-37.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y. Table Z-38 provides 17 compounds Z-38.001 to Z-38.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and F¾, R7 are as defined in table Y.
Table Z-39 provides 17 compounds Z-39.001 to Z-39.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-40 provides 17 compounds Z-40.001 to Z-40.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-41 provides 17 compounds Z-41 .001 to Z-41 .017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-42 provides 17 compounds Z-42.001 to Z-42.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-43 provides 17 compounds Z-43.001 to Z-43.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-44 provides 17 compounds Z-44.001 to Z-44.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-45 provides 17 compounds Z-45.001 to Z-45.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-46 provides 17 compounds Z-46.001 to Z-46.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-47 provides 17 compounds Z-47.001 to Z-47.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-48 provides 17 compounds Z-48.001 to Z-48.017 of formula A wherein R3 is CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-49 provides 17 compounds Z-49.001 to Z-49.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-50 provides 17 compounds Z-50.001 to Z-50.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-51 provides 17 compounds Z-51 .001 to Z-51 .017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-52 provides 17 compounds Z-52.001 to Z-52.017 of formula A wherein R3 is CF2CF3, Xi is
NMe, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y. Table Z-53 provides 17 compounds Z-53.001 to Z-53.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-54 provides 17 compounds Z-54.001 to Z-54.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-55 provides 17 compounds Z-55.001 to Z-55.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-56 provides 17 compounds Z-56.001 to Z-56.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-57 provides 17 compounds Z-57.001 to Z-57.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-58 provides 17 compounds Z-58.001 to Z-58.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-59 provides 17 compounds Z-59.001 to Z-59.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-60 provides 17 compounds Z-60.001 to Z-60.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-61 provides 17 compounds Z-61 .001 to Z-61 .017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-62 provides 17 compounds Z-62.001 to Z-62.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-63 provides 17 compounds Z-63.001 to Z-63.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-64 provides 17 compounds Z-64.001 to Z-64.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-65 provides 17 compounds Z-65.001 to Z-65.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-66 provides 17 compounds Z-66.001 to Z-66.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-67 provides 17 compounds Z-67.001 to Z-67.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-68 provides 17 compounds Z-68.001 to Z-68.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-69 provides 17 compounds Z-69.001 to Z-69.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-70 provides 17 compounds Z-70.001 to Z-70.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-71 provides 17 compounds Z-71 .001 to Z-71 .017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-72 provides 17 compounds Z-72.001 to Z-72.017 of formula A wherein R3 is CF2CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-73 provides 17 compounds Z-73.001 to Z-73.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-74 provides 17 compounds Z-74.001 to Z-74.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-75 provides 17 compounds Z-75.001 to Z-75.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-76 provides 17 compounds Z-76.001 to Z-76.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-77 provides 17 compounds Z-77.001 to Z-77.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-78 provides 17 compounds Z-78.001 to Z-78.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-79 provides 17 compounds Z-79.001 to Z-79.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-80 provides 17 compounds Z-80.001 to Z-80.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-81 provides 17 compounds Z-81 .001 to Z-81 .017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-82 provides 17 compounds Z-82.001 to Z-82.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y. Table Z-83 provides 17 compounds Z-83.001 to Z-83.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-84 provides 17 compounds Z-84.001 to Z-84.017 of formula A wherein R3 is CF2CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-85 provides 17 compounds Z-85.001 to Z-85.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-86 provides 17 compounds Z-86.001 to Z-86.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-87 provides 17 compounds Z-87.001 to Z-87.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-88 provides 17 compounds Z-88.001 to Z-88.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-89 provides 17 compounds Z-89.001 to Z-89.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-90 provides 17 compounds Z-90.001 to Z-90.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-91 provides 17 compounds Z-91 .001 to Z-91 .017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-92 provides 17 compounds Z-92.001 to Z-92.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-93 provides 17 compounds Z-93.001 to Z-93.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-94 provides 17 compounds Z-94.001 to Z-94.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-95 provides 17 compounds Z-95.001 to Z-95.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-96 provides 17 compounds Z-96.001 to Z-96.017 of formula A wherein R3 is CF2CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-97 provides 17 compounds Z-97.001 to Z-97.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y. Table Z-98 provides 17 compounds Z-98.001 to Z-98.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and F¾, R7 are as defined in table Y.
Table Z-99 provides 17 compounds Z-99.001 to Z-99.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-100 provides 17 compounds Z-100.001 to Z-100.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-101 provides 17 compounds Z-101 .001 to Z-101 .017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-102 provides 17 compounds Z-102.001 to Z-102.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-103 provides 17 compounds Z-103.001 to Z-103.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-104 provides 17 compounds Z-104.001 to Z-104.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-105 provides 17 compounds Z-105.001 to Z-105.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-106 provides 17 compounds Z-106.001 to Z-106.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-107 provides 17 compounds Z-107.001 to Z-107.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-108 provides 17 compounds Z-108.001 to Z-108.017 of formula A wherein R3 is SCF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-109 provides 17 compounds Z-109.001 to Z-109.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-1 10 provides 17 compounds Z-1 10.001 to Z-1 10.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-1 1 1 provides 17 compounds Z-1 1 1 .001 to Z-1 1 1 .017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-1 12 provides 17 compounds Z-1 12.001 to Z-1 12.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y. Table Z-1 13 provides 17 compounds Z-1 13.001 to Z-1 13.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-1 14 provides 17 compounds Z-1 14.001 to Z-1 14.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-1 15 provides 17 compounds Z-1 15.001 to Z-1 15.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-1 16 provides 17 compounds Z-1 16.001 to Z-1 16.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-1 17 provides 17 compounds Z-1 17.001 to Z-1 17.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-1 18 provides 17 compounds Z-1 18.001 to Z-1 18.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-1 19 provides 17 compounds Z-1 19.001 to Z-1 19.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-120 provides 17 compounds Z-120.001 to Z-120.017 of formula A wherein R3 is SCF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-121 provides 17 compounds Z-121 .001 to Z-121 .017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-122 provides 17 compounds Z-122.001 to Z-122.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-123 provides 17 compounds Z-123.001 to Z-123.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-124 provides 17 compounds Z-124.001 to Z-124.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-125 provides 17 compounds Z-125.001 to Z-125.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-126 provides 17 compounds Z-126.001 to Z-126.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-127 provides 17 compounds Z-127.001 to Z-127.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-128 provides 17 compounds Z-128.001 to Z-128.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and F¾, R7 are as defined in table Y.
Table Z-129 provides 17 compounds Z-129.001 to Z-129.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-130 provides 17 compounds Z-130.001 to Z-130.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-131 provides 17 compounds Z-131 .001 to Z-131 .017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-132 provides 17 compounds Z-132.001 to Z-132.017 of formula A wherein R3 is SCF3, Xi is O, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-133 provides 17 compounds Z-133.001 to Z-133.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-134 provides 17 compounds Z-134.001 to Z-134.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-135 provides 17 compounds Z-135.001 to Z-135.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-136 provides 17 compounds Z-136.001 to Z-136.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-137 provides 17 compounds Z-137.001 to Z-137.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-138 provides 17 compounds Z-138.001 to Z-138.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-139 provides 17 compounds Z-139.001 to Z-139.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-140 provides 17 compounds Z-140.001 to Z-140.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-141 provides 17 compounds Z-141 .001 to Z-141 .017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-142 provides 17 compounds Z-142.001 to Z-142.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y. Table Z-143 provides 17 compounds Z-143.001 to Z-143.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-144 provides 17 compounds Z-144.001 to Z-144.017 of formula A wherein R3 is SCF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-145 provides 17 compounds Z-145.001 to Z-145.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-146 provides 17 compounds Z-146.001 to Z-146.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-147 provides 17 compounds Z-147.001 to Z-147.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-148 provides 17 compounds Z-148.001 to Z-148.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-149 provides 17 compounds Z-149.001 to Z-149.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-150 provides 17 compounds Z-150.001 to Z-150.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-151 provides 17 compounds Z-151 .001 to Z-151 .017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-152 provides 17 compounds Z-152.001 to Z-152.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-153 provides 17 compounds Z-153.001 to Z-153.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-154 provides 17 compounds Z-154.001 to Z-154.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-155 provides 17 compounds Z-155.001 to Z-155.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-156 provides 17 compounds Z-156.001 to Z-156.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-157 provides 17 compounds Z-157.001 to Z-157.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y. Table Z-158 provides 17 compounds Z-158.001 to Z-158.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and F¾, R7 are as defined in table Y.
Table Z-159 provides 17 compounds Z-159.001 to Z-159.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-160 provides 17 compounds Z-160.001 to Z-160.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-161 provides 17 compounds Z-161 .001 to Z-161 .017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-162 provides 17 compounds Z-162.001 to Z-162.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-163 provides 17 compounds Z-163.001 to Z-163.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-164 provides 17 compounds Z-164.001 to Z-164.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-165 provides 17 compounds Z-165.001 to Z-165.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-166 provides 17 compounds Z-166.001 to Z-166.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-167 provides 17 compounds Z-167.001 to Z-167.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-168 provides 17 compounds Z-168.001 to Z-168.017 of formula A wherein R3 is SOCF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-169 provides 17 compounds Z-169.001 to Z-169.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-170 provides 17 compounds Z-170.001 to Z-170.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-171 provides 17 compounds Z-171 .001 to Z-171 .017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-172 provides 17 compounds Z-172.001 to Z-172.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y. Table Z-173 provides 17 compounds Z-173.001 to Z-173.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-174 provides 17 compounds Z-174.001 to Z-174.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-175 provides 17 compounds Z-175.001 to Z-175.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-176 provides 17 compounds Z-176.001 to Z-176.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-177 provides 17 compounds Z-177.001 to Z-177.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-178 provides 17 compounds Z-178.001 to Z-178.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-179 provides 17 compounds Z-179.001 to Z-179.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-180 provides 17 compounds Z-180.001 to Z-180.017 of formula A wherein R3 is SOCF3, Xi is O, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-181 provides 17 compounds Z-1 17.001 to Z-1 17.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-182 provides 17 compounds Z-182.001 to Z-182.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-183 provides 17 compounds Z-183.001 to Z-183.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-184 provides 17 compounds Z-184.001 to Z-184.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-185 provides 17 compounds Z-185.001 to Z-185.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-186 provides 17 compounds Z-186.001 to Z-186.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-187 provides 17 compounds Z-187.001 to Z-187.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-188 provides 17 compounds Z-188.001 to Z-188.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and F¾, R7 are as defined in table Y.
Table Z-189 provides 17 compounds Z-189.001 to Z-189.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-190 provides 17 compounds Z-190.001 to Z-190.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-191 provides 17 compounds Z-191 .001 to Z-191 .017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-192 provides 17 compounds Z-192.001 to Z-192.017 of formula A wherein R3 is SOCF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-193 provides 17 compounds Z-193.001 to Z-193.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-194 provides 17 compounds Z-194.001 to Z-194.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-195 provides 17 compounds Z-195.001 to Z-195.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-196 provides 17 compounds Z-196.001 to Z-196.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-197 provides 17 compounds Z-197.001 to Z-197.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-198 provides 17 compounds Z-198.001 to Z-198.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-199 provides 17 compounds Z-199.001 to Z-199.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-200 provides 17 compounds Z-200.001 to Z-200.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-201 provides 17 compounds Z-201 .001 to Z-201 .017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-202 provides 17 compounds Z-202.001 to Z-202.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y. Table Z-203 provides 17 compounds Z-203.001 to Z-203.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is CH and F¾, R7 are as defined in table Y.
Table Z-204 provides 17 compounds Z-204.001 to Z-204.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-205 provides 17 compounds Z-205.001 to Z-205.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-206 provides 17 compounds Z-206.001 to Z-206.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-207 provides 17 compounds Z-207.001 to Z-207.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-208 provides 17 compounds Z-208.001 to Z-208.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-209 provides 17 compounds Z-209.001 to Z-209.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-210 provides 17 compounds Z-210.001 to Z-210.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-21 1 provides 17 compounds Z-21 1 .001 to Z-21 1 .017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-212 provides 17 compounds Z-212.001 to Z-212.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-213 provides 17 compounds Z-213.001 to Z-213.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-214 provides 17 compounds Z-214.001 to Z-214.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-215 provides 17 compounds Z-215.001 to Z-215.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-216 provides 17 compounds Z-216.001 to Z-216.017 of formula A wherein R3 is SO2CF3, Xi is NMe, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-217 provides 17 compounds Z-217.001 to Z-217.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y. Table Z-218 provides 17 compounds Z-218.001 to Z-218.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is S, Gi is CH, G2 is N and F¾, R7 are as defined in table Y.
Table Z-219 provides 17 compounds Z-219.001 to Z-219.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-220 provides 17 compounds Z-220.001 to Z-220.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-221 provides 17 compounds Z-221 .001 to Z-221 .017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-222 provides 17 compounds Z-222.001 to Z-222.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-223 provides 17 compounds Z-223.001 to Z-223.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-224 provides 17 compounds Z-224.001 to Z-224.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-225 provides 17 compounds Z-225.001 to Z-225.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-226 provides 17 compounds Z-226.001 to Z-226.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-227 provides 17 compounds Z-227.001 to Z-227.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-228 provides 17 compounds Z-228.001 to Z-228.017 of formula A wherein R3 is SO2CF3, Xi is O, A is N, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-229 provides 17 compounds Z-229.001 to Z-229.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-230 provides 17 compounds Z-230.001 to Z-230.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is S, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-231 provides 17 compounds Z-231 .001 to Z-231 .017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is S, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-232 provides 17 compounds Z-232.001 to Z-232.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is S, Gi is N, G2 is N and R6, R7 are as defined in table Y. Table Z-233 provides 17 compounds Z-233.001 to Z-233.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-234 provides 17 compounds Z-234.001 to Z-234.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO, Gi is CH, G2 is N and R6, R7 are as defined in table Y. Table Z-235 provides 17 compounds Z-235.001 to Z-235.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is CH and R6, R7 are as defined in table Y.
Table Z-236 provides 17 compounds Z-236.001 to Z-236.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO, Gi is N, G2 is N and R6, R7 are as defined in table Y.
Table Z-237 provides 17 compounds Z-237.001 to Z-237.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is CH and R6, R7 are as defined in table Y.
Table Z-238 provides 17 compounds Z-238.001 to Z-238.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO2, Gi is CH, G2 is N and R6, R7 are as defined in table Y.
Table Z-239 provides 17 compounds Z-239.001 to Z-239.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is CH and R6, R7 are as defined in table Y. Table Z-240 provides 17 compounds Z-240.001 to Z-240.017 of formula A wherein R3 is SO2CF3, Xi is O, A is CH, X is SO2, Gi is N, G2 is N and R6, R7 are as defined in table Y.
The tables Za below illustrate further specific compounds of the invention.
Figure imgf000048_0001
Table Za-1 provides 17 compounds Za-1 .001 to Za-1 .017 of formula B wherein R3 is CF3, A is CH, X is S, G3 is CH and F¾, R7 are as defined in table X.
Table X: Substituent definitions of R6 and R7 for the compounds of formula B in tables Za
Figure imgf000048_0002
Figure imgf000049_0001
Table Za-2 provides 17 compounds Za-2.001 to Za-2.017 of formula B wherein R3 is CF3, A is CH, X is S, G3 is N and F¾, R7 are as defined in table X.
Table Za-3 provides 17 compounds Za-3.001 to Za-3.017 of formula B wherein R3 is CF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
Table Za-4 provides 17 compounds Za-4.001 to Za-4.017 of formula B wherein R3 is CF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X.
Table Za-5 provides 17 compounds Za-5.001 to Za-5.017 of formula B wherein R3 is CF3, A is CH, X is SO2, G3 is CH and R6, R7 are as defined in table X. Table Za-6 provides 17 compounds Za-6.001 to Za-6.017 of formula B wherein R3 is CF3, A is CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
Table Za-7 provides 17 compounds Za-7.001 to Za-7.017 of formula B wherein R3 is CF3, A is N, X is S, G3 is CH and R6, R7 are as defined in table X.
Table Za-8 provides 17 compounds Za-8.001 to Za-8.017 of formula B wherein R3 is CF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
Table Za-9 provides 17 compounds Za-9.001 to Za-9.017 of formula B wherein R3 is CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
Table Za-10 provides 17 compounds Za-10.001 to Za-10.017 of formula B wherein R3 is CF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X. Table Za-1 1 provides 17 compounds Za-1 1 .001 to Za-1 1 .017 of formula B wherein R3 is CF3, A is N, X is SO2, G3 is CH and F¾, R7 are as defined in table X.
Table Za-12 provides 17 compounds Za-12.001 to Za-12.017 of formula B wherein R3 is CF3, A is N, X is SO2, G3 is N and R6, R7 are as defined in table X.
Figure imgf000050_0001
, , ,
Figure imgf000050_0002
CH, X is S, G3 is N and R6, R7 are as defined in table X.
Figure imgf000050_0003
, , ,
Figure imgf000050_0004
CH, X is SO, G3 is N and R6, R7 are as defined in table X.
Figure imgf000050_0005
CH, X is SO2, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000050_0006
, , ,
Figure imgf000050_0007
N, X is S, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000050_0008
N, X is S, G3 is N and R6, R7 are as defined in table X.
Table Za-21 provides 17 compounds Za-21 .001 to Za-21 . 017 of formula B wherein R3 is CF2CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000050_0009
N, X is SO, G3 is N and R6, R7 are as defined in table X.
Figure imgf000050_0010
, , ,
Figure imgf000050_0011
N, X is SO2, G3 is N and R6, R7 are as defined in table X.
Table Za-25 provides 17 compounds Za-25.001 to Za-25.017 of formula B wherein R3 is SCF3, A is
CH, X is S, G3 is CH and R6, R7 are as defined in table X. Table Za-26 provides 17 compounds Za-26.001 to Za-26.017 of formula B wherein R3 is SCF3, A is CH, X is S, G3 is N and F¾, R7 are as defined in table X.
Table Za-27 provides 17 compounds Za-27.001 to Za-27.017 of formula B wherein R3 is SCF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
Table Za-28 provides 17 compounds Za-28.001 to Za-28.017 of formula B wherein R3 is SCF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X.
Table Za-29 provides 17 compounds Za-29.001 to Za-29.017 of formula B wherein R3 is SCF3, A is CH, X is SO2, G3 is CH and R6, R7 are as defined in table X.
Table Za-30 provides 17 compounds Za-30.001 to Za-30.017 of formula B wherein R3 is SCF3, A is CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
Table Za-31 provides 17 compounds Za-31 .001 to Za-31 .017 of formula B wherein R3 is SCF3, A is N, X is S, G3 is CH and R6, R7 are as defined in table X.
Table Za-32 provides 17 compounds Za-32.001 to Za-32.017 of formula B wherein R3 is SCF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
Table Za-33 provides 17 compounds Za-33.001 to Za-33.017 of formula B wherein R3 is SCF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X.
Table Za-34 provides 17 compounds Za-34.001 to Za-34.017 of formula B wherein R3 is SCF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X.
Table Za-35 provides 17 compounds Za-35.001 to Za-35.017 of formula B wherein R3 is SCF3, A is N, X is SO2, G3 is CH and R6, R7 are as defined in table X.
Table Za-36 provides 17 compounds Za-36.001 to Za-36.017 of formula B wherein R3 is SCF3, A is N, X is SO2, G3 is N and R6, R7 are as defined in table X.
Table Za-37 provides 17 compounds Za-37.001 to Za-37.017 of formula B wherein R3 is SOCF3, A is CH, X is S, G3 is CH and R6, R7 are as defined in table X.
Table Za-38 provides 17 compounds Za-38.001 to Za-38.017 of formula B wherein R3 is SOCF3, A is CH, X is S, G3 is N and R6, R7 are as defined in table X.
Table Za-39 provides 17 compounds Za-39.001 to Za-39.017 of formula B wherein R3 is SOCF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
Table Za-40 provides 17 compounds Za-40.001 to Za-40.017 of formula B wherein R3 is SOCF3, A is CH, X is SO, G3 is N and R6, R7 are as defined in table X. Table Za-41 provides 17 compounds Za-41 .001 to Za-41 .017 of formula B wherein R3 is SOCF3, A is CH, X is SO2, G3 is CH and F¾, R7 are as defined in table X.
Figure imgf000052_0001
CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
Figure imgf000052_0002
, , ,
Figure imgf000052_0003
N, X is S, G3 is N and R6, R7 are as defined in table X.
Figure imgf000052_0004
, , ,
Figure imgf000052_0005
N, X is SO, G3 is N and R6, R7 are as defined in table X.
Figure imgf000052_0006
N, X is SO2, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000052_0007
N, X is SO2, G3 is N and R6, R7 are as defined in table X.
Figure imgf000052_0008
CH, X is S, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000052_0009
, , ,
Table Za-51 provides 17 compounds Za-51 .001 to Za-51 .017 of formula B wherein R3 is SO2CF3, A is CH, X is SO, G3 is CH and R6, R7 are as defined in table X.
Figure imgf000052_0010
CH, X is SO, G3 is N and R6, R7 are as defined in table X.
Figure imgf000052_0011
, , ,
Figure imgf000052_0012
CH, X is SO2, G3 is N and R6, R7 are as defined in table X.
Table Za-55 provides 17 compounds Za-55.001 to Za-55.017 of formula B wherein R3 is SO2CF3, A is
N, X is S, G3 is CH and R6, R7 are as defined in table X. Table Za-56 provides 17 compounds Za-56.001 to Za-56.017 of formula B wherein R3 is SO2CF3, A is N, X is S, G3 is N and R6, R7 are as defined in table X.
Table Za-57 provides 17 compounds Za-57.001 to Za-57.017 of formula B wherein R3 is SO2CF3, A is N, X is SO, G3 is CH and R6, R7 are as defined in table X. Table Za-58 provides 17 compounds Za-58.001 to Za-58.017 of formula B wherein R3 is SO2CF3, A is N, X is SO, G3 is N and R6, R7 are as defined in table X.
Table Za-59 provides 17 compounds Za-59.001 to Za-59.017 of formula B wherein R3 is SO2CF3, A is N, X is SO2, G3 is CH and R6, R7 are as defined in table X.
Table Za-60 provides 17 compounds Za-60.001 to Za-60.017 of formula B wherein R3 is SO2CF3, A is N, X is SO2, G3 is N and R6, R7 are as defined in table X.
The tables Zb below illustrate further specific compounds of the invention.
Figure imgf000053_0001
Table Zb-1 provides 34 compounds Zb-1 .001 to Zb-1 .34 of formula C wherein R3 is CF3, A is CH, X is S and F¾, R7, Gi , G2 are as defined in table W.
Table W:
Substituent definitions of R6, R7, Gi and G2 for the compounds of formula C in tables Zb
Figure imgf000053_0002
Figure imgf000054_0001
Table Zb-2 provides 34 compounds Zb-2.001 to Zb-2.34 of formula C wherein R3 is CF3, A is CH, X is SO and R6, R7, Gi, G2 are as defined in table W.
Table Zb-3 provides 34 compounds Zb-3.001 to Zb-3.34 of formula C wherein R3 is CF3, A is CH, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
Table Zb-4 provides 34 compounds Zb-4.001 to Zb-4.34 of formula C wherein R3 is CF3, A is N, X is S and R6, R7, Gi , G2 are as defined in table W.
Table Zb- 5 provides 34 compounds Zb-5.001 to Zb-5.34 of formula C wherein R3 is CF3, A is N, X is SO and R6, R7, Gi, G2 are as defined in table W. Table Zb-6 provides 34 compounds Zb-6.001 to Zb-6.34 of formula C wherein R3 is CF3, A is N, X is SO2 and F¾, R7, Gi , G2 are as defined in table W. Table Zb- 7 provides 34 compounds Zb-7.001 to Zb-7.34 of formula C wherein R3 is CF2CF3, A is CH, X is S and F¾, R7, Gi , G2 are as defined in table W.
Table Zb-8 provides 34 compounds Zb-8.001 to Zb-8.34 of formula C wherein R3 is CF2CF3, A is CH, X is SO and R6, R7, Gi, G2 are as defined in table W.
Table Zb-9 provides 34 compounds Zb-9.001 to Zb-9.34 of formula C wherein R3 is CF2CF3, A is CH, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
Table Zb-10 provides 34 compounds Zb-10.001 to Zb-10.34 of formula C wherein R3 is CF2CF3, A is N, X is S and R6, R7, Gi, G2 are as defined in table W.
Table Zb-1 1 provides 34 compounds Zb-1 1 .001 to Zb-1 1 .34 of formula C wherein R3 is CF2CF3, A is N, X is SO and R6, R7, Gi , G2 are as defined in table W.
Table Zb-12 provides 34 compounds Zb-12.001 to Zb-12.34 of formula C wherein R3 is CF2CF3, A is N, X is SO2 and R6, R7, Gi , G2 are as defined in table W.
Table Zb-13 provides 34 compounds Zb-13.001 to Zb-13.34 of formula C wherein R3 is SCF3, A is CH, X is S and R6, R7, Gi , G2 are as defined in table W.
Table Zb-14 provides 34 compounds Zb-14.001 to Zb-14.34 of formula C wherein R3 is SCF3, A is CH, X is SO and Re, R7, Gi, G2 are as defined in table W.
Table Zb-15 provides 34 compounds Zb-15.001 to Zb-15.34 of formula C wherein R3 is SCF3, A is CH, X is SO2 and Re, R7, Gi , G2 are as defined in table W.
Table Zb-16 provides 34 compounds Zb-16.001 to Zb-16.34 of formula C wherein R3 is SCF3, A is N,
X is S and Re, R7, Gi , G2 are as defined in table W.
Table Zb-17 provides 34 compounds Zb-17.001 to Zb-17.34 of formula C wherein R3 is SCF3, A is N,
X is SO and Re, R7, Gi, G2 are as defined in table W.
Table Zb-18 provides 34 compounds Zb-18.001 to Zb-18.34 of formula C wherein R3 is SCF3, A is N,
X is SO2 and Re, R7, Gi , G2 are as defined in table W.
Table Zb-19 provides 34 compounds Zb-19.001 to Zb-19.34 of formula C wherein R3 is SOCF3, A is CH, X is S and Re, R7, Gi, G2 are as defined in table W.
Table Zb-20 provides 34 compounds Zb-20.001 to Zb-20.34 of formula C wherein R3 is SOCF3, A is CH, X is SO and Re, R7, Gi , G2 are as defined in table W.
Table Zb-21 provides 34 compounds Zb-21 .001 to Zb-21 .34 of formula C wherein R3 is SOCF3, A is CH, X is SO2 and Re, R7, Gi , G2 are as defined in table W. Table Zb-22 provides 34 compounds Zb-22.001 to Zb-22.34 of formula C wherein R3 is SOCF3, A is N, X is S and F¾, R7, Gi , G2 are as defined in table W.
Table Zb-23 provides 34 compounds Zb-23.001 to Zb-23.34 of formula C wherein R3 is SOCF3, A is N, X is SO and R6, R7, Gi, G2 are as defined in table W.
Table Zb-24 provides 34 compounds Zb-24.001 to Zb-24.34 of formula C wherein R3 is SOCF3, A is N, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
Table Zb-25 provides 34 compounds Zb-25.001 to Zb-25.34 of formula C wherein R3 is SO2CF3, A is CH, X is S and R6, R7, Gi, G2 are as defined in table W.
Table Zb-26 provides 34 compounds Zb-26.001 to Zb-26.34 of formula C wherein R3 is SO2CF3, A is CH, X is SO and R6, R7, Gi , G2 are as defined in table W.
Table Zb-27 provides 34 compounds Zb-27.001 to Zb-27.34 of formula C wherein R3 is SO2CF3, A is CH, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
Table Zb-28 provides 34 compounds Zb-28.001 to Zb-28.34 of formula C wherein R3 is SO2CF3, A is N, X is S and R6, R7, Gi, G2 are as defined in table W.
Table Zb-29 provides 34 compounds Zb-29.001 to Zb-29.34 of formula C wherein R3 is SO2CF3, A is N, X is SO and R6, R7, Gi, G2 are as defined in table W.
Table Zb-30 provides 34 compounds Zb-30.001 to Zb-30.34 of formula C wherein R3 is SO2CF3, A is N, X is SO2 and R6, R7, Gi, G2 are as defined in table W.
The compounds of formula I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. The active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina, nematodes or molluscs. The insecticidal, nematicidal, molluscicidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e. in mortality or destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, anti-feedant effect, and/or growth inhibition.
Examples of the abovementioned animal pests are:
from the order Acarina, for example,
Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp., Polyphagotarsone latus,
Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp.;
from the order Anoplura, for example,
Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;
from the order Coleoptera, for example,
Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.; from the order Diptera, for example,
Aedes spp., Anopheles spp, Antherigona soccata.Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;
from the order Hemiptera, for example,
Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp, Euschistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp. , Thyanta spp , Triatoma spp., Vatiga illudens;
Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis,
Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae , Unaspis citri, Zygina flammigera, Zyginidia scutellaris, ;
from the order Hymenoptera, for example,
Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplo- campa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;
from the order Isoptera, for example,
Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate
from the order Lepidoptera, for example,
Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Gra- pholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophora gossypi- ela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.;
from the order Mallophaga, for example,
Damalinea spp. and Trichodectes spp.; from the order Orthoptera, for example,
Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and Schistocerca spp.;
from the order Psocoptera, for example,
Liposcelis spp.;
from the order Siphonaptera, for example,
Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; from the order Thysanoptera, for example,
Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp;
from the order Thysanura, for example, Lepisma saccharina.
The active ingredients according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family and latex plants.
The compositions and/or methods of the present invention may be also used on any ornamental and/or vegetable crops, including flowers, shrubs, broad-leaved trees and evergreens.
For example the invention may be used on any of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g. B. elatior, B. semperfiorens, B. tubereux), Bougainvillea spp., Brachycome spp., Brassica spp. (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (/. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp., Beilis spp., Pelargonium spp. (P. peltatum, P. Zonale), Viola spp. (pansy), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp., Parthenocissus spp. (P. quinquefolia, P. tricuspidata), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (rose), Rudbeckia spp., Saintpaulia spp.,
Salvia spp., Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfmia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.
For example the invention may be used on any of the following vegetable species: Allium spp. (A. sativum, A. cepa, A. oschaninii, A. Porrum, A. ascalonicum, A. fistulosum), Anthriscus cerefolium, Apium graveolus, Asparagus officinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B. Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus, Cucumis spp. (C. sativus, C. meld), Cucurbita spp. (C. pepo, C. maxima), Cyanara spp. (C. scolymus, C. cardunculus), Daucus carota, Foeniculum vulgare, Hypericum spp., Lactuca sativa, Lycopersicon spp. (L esculentum, L lycopersicum), Mentha spp., Ocimum basilicum, Petroselinum crispum, Phaseolus spp. (P. vulgaris, P. coccineus), Pisum sativum, Raphanus sativus, Rheum rhaponticum, Rosemarinus spp., Salvia spp., Scorzonera hispanica, Solanum melongena, Spinacea oleracea, Valerianella spp. (V. locusta, V. eriocarpa) and Vicia faba.
Preferred ornamental species include African violet, Begonia, Dahlia, Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper, tomato and cucumber.
The active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and
Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops. The active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
The active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and
Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops. The active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
In a further aspect, the invention may also relate to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species;
Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes,
Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans,
Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp..
The compounds of the invention may also have activity against the molluscs. Examples of which include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus);
Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae Helicigona arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.
The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as d-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or
Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.
In the context of the present invention there are to be understood by d-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810). Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type
deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).
Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1 Ac toxin); Bollgard I® (cotton variety that expresses a Cry1 Ac toxin); Bollgard II® (cotton variety that expresses a Cry1 Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a Cry1 Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.
Further examples of such transgenic crops are:
1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer ( Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1 Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer ( Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'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 Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.
6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.
7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 c 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 CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain
Lepidoptera, include the European corn borer. Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fiir Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,
(http://bats.ch).
The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.
Crops also include those that have enhanced resistance to nematodes, such as the soybean cyst nematode.
Crops that are tolerance to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.
Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g.
WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).
Further areas of use of the compositions according to the invention are the protection of stored goods and store rooms and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animals and productive livestock against pests of the mentioned type.
The present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http://www.who.int/malaria/vector_control/irs/en/). In one embodiment, the method for controlling pests comprises applying the compositions of the invention to the target pests, to their locus or to a surface or substrate by brushing, rolling, spraying, spreading or dipping. By way of example, an IRS (indoor residual spraying) application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention. In another embodiment, it is contemplated to apply such compositions to a substrate such as non-woven or a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.
In one embodiment, the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or substrate. Such application may be made by brushing, rolling, spraying, spreading or dipping the pesticidal composition of the invention. By way of example, an IRS application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.
Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrylonitrile or the like. The polyesters are particularly suitable. The methods of textile treatment are known, e.g. WO 2008/151984, WO 2003/034823, US 5631072, WO 2005/64072, W02006/128870, EP 1724392, WO 2005113886 or WO 2007/090739.
Further areas of use of the compositions according to the invention are the field of tree injection/trunk treatment for all ornamental trees as well all sort of fruit and nut trees.
In the field of tree injection/trunk treatment, the compounds according to the present invention are especially suitable against wood-boring insects from the order Lepidoptera as mentioned above and from the order Coleoptera, especially against woodborers listed in the following tables A and B:
Table A. Examples of exotic woodborers of economic importance.
Figure imgf000065_0001
Table B. Examples of native woodborers of economic importance.
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
The present invention may be also used to control any insect pests that may be present in turfgrass, including for example beetles, caterpillars, fire ants, ground pearls, millipedes, sow bugs, mites, mole crickets, scales, mealybugs ticks, spittlebugs, southern chinch bugs and white grubs. The present invention may be used to control insect pests at various stages of their life cycle, including eggs, larvae, nymphs and adults.
In particular, the present invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g. masked chafer, C. lurida),
Rhizotrogus spp. (e.g. European chafer, R. majalis), Cotinus spp. (e.g. Green June beetle, C. nitida), Popillia spp. (e.g. Japanese beetle, P. japonica), Phyllophaga spp. (e.g. May/June beetle), Ataenius spp. (e.g. Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g. Asiatic garden beetle, M.
castanea) and Tomarus spp.), ground pearls ( Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana ) and leatherjackets (European crane fly, Tipula spp.).
The present invention may also be used to control insect pests of turfgrass that are thatch dwelling, including armyworms (such as fall armyworm Spodoptera frugiperda, and common armyworm Pseudaletia unipuncta), cutworms, billbugs ( Sphenophorus spp. , such as S. venatus verstitus and S. parvulus), and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis). The present invention may also be used to control insect pests of turfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southern chinch bugs, Blissus insulahs), Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug ( Propsapia bicincta), leafhoppers, cutworms ( Noctuidae family), and greenbugs. The present invention may also be used to control other pests of turfgrass such as red imported fire ants ( Solenopsis invicta) that create ant mounds in turf.
In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
Examples of such parasites are:
Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp. and Phtirus spp., Solenopotes spp..
Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,
Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp..
Of the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp..
Of the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..
Of the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..
Of the order Blattarida, for example Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp..
Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.. Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,
Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..
The compositions according to the invention are also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildings.
The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium
rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec.,Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes,
Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and bristletails such as Lepisma saccharina.
The compounds according to the invention can be used as pesticidal agents in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water- dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil- in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water- miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
The formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, A/,A/-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 ,1 -trichloroethane, 2- heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy- propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, /V-methyl-2- pyrrolidone and the like. Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface- active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosu coin ate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di- alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).
Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th Edition, Southern Illinois University, 2010.
The inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.
The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
Preferred formulations can have the following compositions (weight %):
Emulsifiable concentrates:
active ingredient: 1 to 95 %, preferably 60 to 90 %
surface-active agent: 1 to 30 %, preferably 5 to 20 %
liquid carrier: 1 to 80 %, preferably 1 to 35 %
Dusts:
active ingredient: 0.1 to 10 %, preferably 0.1 to 5 %
solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
Suspension concentrates:
active ingredient: 5 to 75 %, preferably 10 to 50 %
water: 94 to 24 %, preferably 88 to 30 %
surface-active agent: 1 to 40 %, preferably 2 to 30 %
Wettable powders:
active ingredient: 0.5 to 90 %, preferably 1 to 80 %
surface-active agent: 0.5 to 20 %, preferably 1 to 15 %
solid carrier: 5 to 95 %, preferably 15 to 90 %
Granules:
active ingredient: 0.1 to 30 %, preferably 0.1 to 15 %
solid carrier: 99.5 to 70 %, preferably 97 to 85 %
The following Examples further illustrate, but do not limit, the invention.
Figure imgf000073_0001
Figure imgf000074_0001
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
Figure imgf000074_0002
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
Figure imgf000074_0003
Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
Figure imgf000074_0004
Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Figure imgf000074_0005
Figure imgf000075_0001
The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
Figure imgf000075_0002
The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
Suspension concentrate
Figure imgf000075_0003
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Flowable concentrate for seed treatment
Figure imgf000075_0004
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Slow Release Capsule Suspension
28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51 .6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
Preparative Examples:
LCMS Methods:
Method 1 :
Spectra were recorded on a Mass Spectrometer from Agilent Technologies (6410 Triple Quadruple Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch, Capillary: 4.00 kV, Fragmentor: 100.00 V, Gas Temperature: 350 °C, Gas Flow: 1 1 L/min, Nebulizer Gas: 45 psi, Mass range: 1 10-1000 Da, DAD Wavelength range: 210-400 nm). Column: KINETEX EVO C18, length 50 mm, diameter 4.6 mm, particle size 2.6 pm. Column oven temperature 40 °C. Solvent gradient: A= Water with 0.1 % formic acid : Acetonitrile (95:5 v/v). B= Acetonitrile with 0.1 % formic acid. Gradient= 0 min 90% A, 10% B; 0.9-1 .8 min 0% A, 100% B, 2.2-2.5 min 90% A, 10% B. Flow rate 1 .8 mL/min.
Method 2:
Spectra were recorded on a Mass Spectrometer from Waters (Acquity SDS Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch, Capillary: 3.00 kV, Cone Voltage: 41 .00 V, Source temperature: 150 °C, Desolvation Gas Flow: 1000 L/Hr, Desolvation temperature: 500 °C, Gas Flow @Cone: 50 L/hr, Mass range: 1 10-800 Da, PDA wavelength range: 210- 400 nm. Column: Acquity UPLC HSS T3 C18, length 30 mm, diameter 2.1 mm, particle size 1 .8 pm. Column oven temperature 40 °C. Solvent gradient: A= Water with 0.1 % formic acid : Acetonitrile (95:5 v/v). B= Acetonitrile with 0.05% formic acid. Gradient= 0 min 90% A, 10% B; 0.2 min 50% A, 50% B; 0.7-1 .3 min 0% A, 100% B; 1 .4-1 .6 min 90% A, 10% B. Flow rate 0.8 mL/min.
Example H1 : Preparation of 2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-alpyridin-7-yl1-3-methyl- 6-(trifluoromethyl)imidazo[4,5-clpyridine (Compound P4, Table P)
Figure imgf000077_0001
Step 1 : Preparation of 2-chloro-5-ethylsulfanyl-pyridine-4-carboxylic acid.
Figure imgf000077_0002
A solution of 2-chloro-5-fluoro-pyridine-4-carboxylic acid (3 g, 17.090 mmol) in tetrahydrofurane (66 ml_) was cooled to 0°C, and treated portionwise at ~5°C with sodium ethanethiolate (3.774 g, 80%, 35.889 mmol). The thick mixture was shown by LC/MS to be complete after 1 h at RT. The mixture was cooled to ~15°C, and treated slowly with 20 ml_ of aqueous HCI 2N, and extracted with EtOAc (x2), and the combined organic phases washed with aqueous NhUCI, dried over Na2SC>4, filtered, and concentrated in vacuo. The crude product was purified by combiflash (silica gel, cyclohexane:THF 20- 100%,) to afford the title compound as a white solid.
1 H NMR (400 MHz, DMSO-d6) d ppm; 1 .26 (t, J=7.34 Hz, 3 H) 3.09 (q, J=7.34 Hz, 2 H) 7.74 (s, 1 H) 8.46 (s, 1 H) 13.95 - 14.29 (m, 1 H)
Step 2: Preparation of 2-chloro-5-ethylsulfanyl-N-[5-(methylamino)-2-(trifluoromethyl)-4- pyridyllpyridine-4-carboxamide To a 0 °C cooled solution of 2-chloro-5-ethylsulfanyl-pyridine-4-carboxylic acid (0.4 g, 1 .837 mmol) in dichloromethane (10 mL) and DMF (0.1 ml) was added oxalyl dichloride (0.32 mL, 3.675 mmol). The resulting mixture was stirred at room temperature for 2 hours and then concentrated in vacuo to remove volatiles to afford 2-chloro-5-ethylsulfanyl-pyridine-4-carbonyl chloride. This was used in the next step without further purification.
To a 0 °C cooled solution of N3-methyl-6-(trifluoromethyl)pyridine-3, 4-diamine (0.259 g, 1 .355 mmol, prepared as described in WO 2015000715), triethylamine (0.59 mL, 4.235 mmol) in tetrahydrofurane (30 mL) was added a solution of 2-chloro-5-ethylsulfanyl-pyridine-4-carbonyl chloride prepared as described above (0.4 g, 1 .694 mmol) in tetrahydrofurane (50 ml). The reaction mixture was stirred at room temperature for 2 hours and then diluted with water (20 ml). The aqueous layer was extracted with ethyl acetate (3x50 ml). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-chloro-5-ethylsulfanyl-N-[5-(methylamino)-2-(trifluoromethyl)-4- pyridyl]pyridine-4-carboxamide.
LCMS: (Method 1). Retention time 0.93 min, 391 (M+H)
Step 3: Preparation of 2-(2-chloro-5-ethylsulfanyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- clpyridine
Figure imgf000078_0001
A solution of 2-chloro-5-ethylsulfanyl-N-[5-(methylamino)-2-(trifluoromethyl)-4-pyridyl]pyridine-4- carboxamide (1 .0 g, 2.6 mmol) in acetic acid (10 ml_) was heated at 120°C for 12Hr. The reaction mixture was cooled to RT, concentrated under reduced pressure to remove some of the AcOH, and then neutralised with saturated sodium carbonate solution (20 ml_). The aqueous layer was extracted with ethyl acetate (3x20 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by combiflash (silica gel, 50% EtOAc- cyclohexane) to afford 2-(2-chloro-5-ethylsulfanyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- cjpyridine.
LCMS: (Method 1). Retention time 1 .46 min, 373.08 (M+H) Ή NMR (400MHz, CHLOROFORM-d) d = 9.00 (s, 1 H), 8.55 (s, 1 H), 8.18 - 8.15 (m, 1 H), 7.48 (s, 1 H), 3.88 - 3.85 (m, 3H), 2.88 (q, 2H), 1 .24 (t, 3H)
Step 4: Preparation of 2-(2-chloro-5-ethylsulfonyl-4-pyridyr)-3-methyl-6-(trifluoromethvDimidazo[4,5- clpyridine
Figure imgf000079_0001
To a solution of 2-(2-chloro-5-ethylsulfanyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (0.24 g, 0.6438 mmol) in dichloromethane (10 ml_) was added 3-chlorobenzenecarboperoxoic acid (0.3259 g, 1 .416 mmol). The reaction was stirred at rt for 2-3 h, monitored by TLC. The reaction mixture was quenched with 1 N NaOH solution, and the aqueous layer extracted with dichloromethane (3x20 ml). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by combiflash (silica gel, 40% EtOAc-cyclohexane) to afford 2-(2-chloro-5-ethylsulfonyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine.
LCMS: (Method 1). Retention time 1 .38 min, 405.03 (M+H)
Ή NMR (400MHz, CHLOROFORM-d) d = 9.15 (s, 1 H), 9.00 (s, 1 H), 8.13 - 8.10 (m, 1 H), 7.56 (s, 1 H), 3.82 (s, 3H), 3.39 (q, J=7.5 Hz, 2H), 1 .34 - 1 .28 (m, 3H).
Step 5: Preparation of 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4.5-clpyridin-2-yllpyridin-
2-amine
Figure imgf000079_0002
In a sealed vessel, 2-(2-chloro-5-ethylsulfonyl-4-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- cjpyridine (0.15 g, 0.3706 mmol) in tetrahydrofurane (1 .0 ml_) and ammonium hydroxide (1 .0 ml_) were heated at 1 10 °C for 1 -2 h. The reaction mixture was concentrated in vacuo and the crude product purified by chromatography to give 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin- 2-yl]pyridin-2-amine.
LCMS: (Method 1). Retention time 1 .21 min, 386.10 (M+H)
Ή NMR (400MHz, CHLOROFORM-d) d = 8.95 (s, 1 H), 8.77 (s, 1 H), 8.10 (s, 1 H), 6.56 (s, 1 H), 5.44 (br s, 2H), 3.81 (s, 3H), 3.24 (q, 2H), 1 .26 (t, 3H). Step 6: Preparation of 2-[6-ethylsulfonyl-2-(trifluoromethvDimidazo[1 ,2-alpyridin-7-yl1-3-methyl-6- (trifluoromethvDimidazo[4,5-clpyridine (Compound P4, Table PI
Figure imgf000080_0001
A solution of 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-2-amine (0.12 g, 0.31 14 mmol), 3-bromo-1 ,1 ,1 -trifluoroacetone (0.3033 g, 1 .557 mmol, 0.1649 ml_) and potassium carbonate (0.06455 g, 0.4670 mmol) in ethanol were placed in a microwave vial and heated in a microwave for 1 .5 h at 120 °C then at 140 °C for 30 min. The reaction mixture was concentrated in vacuo and the crude product diluted with water (10 ml_), extracted with ethyl acetate (3X20 ml). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by combiflash (silica gel, 40% EtOAc-cyclohexane) to afford 2-[6-ethylsulfonyl-2- (trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine.
LCMS: (Method 1). Retention time 0.98 min, 478.06 (M+H)
Ή NMR (400 MHz, DMSO-cfe) d ppm 1 .16 - 1 .21 (m, 3 H) 3.64 (q, 2 H) 3.85 (s, 3 H) 8.29 - 8.36 (m, 2 H) 8.91 (s, 1 H) 9.27 - 9.31 (m, 1 H) 9.51 (s, 1 H).
Example H2: Preparation of methyl 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5- clpyridin-2-yl1imidazo[1 .2-alpyridine-2-carboxylate ( Compound P1 1 , Table P)
Figure imgf000080_0002
In a microwave vial, 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-2- amine (0.5 g, 1 .297 mmol, prepared as in step 5, example H1) dissolved in acetonitrile (5 ml_)treated with methyl 3-bromo-2-oxo-propanoate (1 .174g, 6.487mmol, 0.69 ml_) and potassium carbonate (0.2690 g, 1 .946 mmol). The reaction mixture was subjected to microwave heating for 1 .5 Hr at 120 °C then at 140 °C for 30 min. The reaction mixture was concentrated under reduced pressure to remove all volatiles. The residue was diluted with water (10 ml_), and extracted with ethyl acetate (3X20 ml). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford methyl 6-ethylsulfonyl-7-[3- methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2-a]pyridine-2-carboxylate.
LCMS: (Method 1 ). Retention time 1 .24 min, 468.0 (M+H)
Ή NMR (400 MHz, CHLOROFORM-d) d ppm 1 .21 - 1 .40 (m, 3 H) 3.56 (d, J=7.46 Hz, 2 H) 3.75 - 3.95 (m, 3 H) 4.05 (s, 3 H) 7.87 (s, 1 H) 8.08 - 8.14 (m, 1 H) 8.48 (s, 1 H) 9.00 (s, 1 H) 9.09 (s, 1 H)
Example H3: Preparation of 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethvDimidazo[4,5-clpyridin-2- yllimidazoH ,2-alpyridine-2-carboxamide ( Compound P12, Table PI
Figure imgf000081_0001
(Compound P12, Table P)
A solution of 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2- a]pyridine-2-carboxylate (0.5 g, 1 .07 mmol) in 1 ,4-dioxane (3 ml_) was treated with ammonium hydroxide (30%, 6 ml_) in a microwave vial, and the mixture heated at 80 °C for 1 h. The reaction mixture was concentrated under reduced pressure to remove all volatiles and the residue purified by chromatography to afford 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2- yl]imidazo[1 ,2-a]pyridine-2-carboxamide.
LCMS: (Method 2). Retention time 0.79 min, 453.29 (M+H)
Example H4: Preparation of 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-clpyridin-2- yllimidazoH ,2-alpyridine-2-carbonitrile (Compound P2, Table P)
Figure imgf000081_0002
(Compound P2, Table P)
A solution of 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2- a]pyridine-2-carboxamide (100 mg, 0.221 mmol) in tetrahydrofurane (1 mL) was treated with bis(trifluoromethyl) carbonate (0.043 mL, 0.331 mmol) followed by pyridine (0.054 mL, 0.663 mmol), and the resulting mixture was stirred at RT. After 1 hour, the reaction mixture was diluted with cold water (1 OmL), then extracted with ethyl acetate (10mlX3), and the combined organic phases dried over sodium sulfate and concentrated in vacuo. The crude product was purified by chromatography to afford 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2-a]pyridine-2- carbonitrile.
LCMS (Method 2). Retention time 0.91 shows 435.33 (M+H) mass
1 H NMR (400 MHz, CHLOROFORM-d) d ppm 1 .40 - 1 .58 (m, 3 H) 3.56 (d, J=7.46 Hz, 2 H) 3.87 (s, 3 H) 7.87 (s, 1 H) 8.13 (s, 1 H) 8.38 (s, 1 H) 9.01 (s, 1 H) 9.08 (s, 1 H).
Example H5: Preparation of 2-(6-ethylsulfonylimidazo[1 .2-alpyridin-7-vD-3-methyl-6-
(trifluoromethvDimidazo[4,5-clpyridine ( Compound P8, Table PI
Figure imgf000082_0001
Table P)
In a microwave vial, 5-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]pyridin-2- amine (0.5 g, 1 .297 mmol) in acetonitrile (5 mL) was treated with chloroacetaldehyde in water (1 .018 g, 6.487 mmol, 0.8239 mL) and subjected to microwave heating for 1 .0 h at 1 10 °C. The reaction mixture was then concentrated in vacuo, and the residue diluted with water (30 ml), and extracted with ethyl acetate (3x30 ml). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford 2-(6- ethylsulfonylimidazo[1 ,2-a]pyridin-7-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine.
LCMS (Method 2). Retention time 0.81 , 410.28 ( M+H) mass
Ή NMR (400 MHz, CHLOROFORM-d) d ppm 1 .21 - 1 .38 (m, 3 H) 3.53 (d, J=7.46 Hz, 2 H) 3.86 (s, 3 H) 7.27 (s, 1 H) 7.83 (s, 1 H) 7.94 (s, 1 H) 7.98 (d,J=1 .22 Hz, 1 H) 8.12 (s, 1 H) 8.98 (s, 1 H) 9.08 (s, 1 H)
19F NMR (377 MHz, CHLOROFORM-d) d ppm -66.21 (s, 1 F)
Example H6: Preparation of 2-(3-bromo-6-ethylsulfonyl-imidazo[1 ,2-alpyridin-7-yl)-3-methyl-6-
(trifluoromethyl) imidazo[4,5-clpyridine ( Compound P5, Table P)
Figure imgf000082_0002
(Compound P5, Table P)
To a solution of 2-(6-ethylsulfonylimidazo[1 ,2-a]pyridin-7-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- c]pyridine (0.3 g, 0.7328 mmol) in N,N-dimethylformamide (6.5 mL) was added N-bromosuccinimide (0.1581 g, 0.8793 mmol). The reaction mixture was stirred at room temperature for 1 Hr, monitored by TLC. After completion, the reaction was quenched with water (10 mL), extracted with ethyl acetate (3X10 ml) and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography to afford 2-(3-bromo-6-ethylsulfonyl- imidazo[1 ,2-a]pyridin-7-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine.
LCMS. (Method 2). Retention time 0.88 min, 488.06 (M+H)
Ή NMR (400 MHz, DMSO-de) d ppm 1 .13 - 1 .27 (m, 3 H) 3.69 (q, 2 H) 3.85 (s, 3 H) 8.15 (s, 1 H) 8.28 - 8.33 (m, 2 H) 8.81 - 8.83 (m, 1 H) 9.28 (s, 1 H)
Table P: Prepared compounds with Analytical Data.
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
The following mixtures of the compounds of formula I with active ingredients are preferred (the abbreviation“TX” means“one compound selected from the group consisting of the compounds described in Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P of the present invention”): an adjuvant selected from the group of substances consisting of petroleum oils (alternative name)
(628) + TX, an acaricide selected from the group of substances consisting of 1 ,1 -bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1 -naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) +
TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) +
TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (lUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoximate (71) + TX, benzyl benzoate (lUPAC name) [CCN] + TX, bifenazate (74)
+ TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromo- cyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bromopropylate (94) +
TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (lUPAC name) (1 1 1) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbophenothion (947) + TX, CGA 50’439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulfide (971) + TX, chlorfenvinphos (131) + TX, chlorobenzilate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermetrin (201 ) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071) + TX, dimefox (1081) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dinopenton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxathion (1 102) + TX, diphenyl sulfone (lUPAC name)
(1 103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1 1 13) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1 121) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate-methyl (1 134) + TX, etoxazole (320) + TX, etrimfos (1 142) + TX, fenazaflor (1 147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1 157) + TX, fentrifanil (1 161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1 166) + TX, flubenzimine (1 167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1 174) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (lUPAC/Chemical Abstracts name) (1216) + TX, hexythiazox (441) + TX, iodomethane (lUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl 0-(methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, ivermectin
(alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530)
+ TX, methomyl (531) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556)
+ TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC- 512 (compound code) + TX, nifluridide (1309) + TX, nikkomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (711) +
TX, quintiofos (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) +
TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786)
+ TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name)
+ TX, thiocarboxime (1431) + TX, thiofanox (800) + TX, thiometon (801) + TX, thioquinox (1436)
+ TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441) + TX, triarathene (1443) +
TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347)
+ TX, an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX, an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy-1 H-pyridine-2-thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) + TX, fenaminosulf (1 144) + TX, formaldehyde (404) +
TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (lUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (61 1) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX, a biological agent selected from the group of substances consisting of Adoxophyes orana GV
(alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX,
Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea
(alternative name) (151 ) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491 ) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var.
acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp.
(alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX,
Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternative name) (742) + TX, Steinernema carpocapsae (alternative name) (742) + TX, Steinernema feltiae (alternative name) (742) + TX, Steinernema glaseri (alternative name) (742) + TX, Steinernema riobrave (alternative name) (742) + TX, Steinernema riobravis (alternative name) (742) + TX, Steinernema scapterisci (alternative name) (742) + TX, Steinernema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX, a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron
(alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX, an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (lUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (lUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (lUPAC name) (541) + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (lUPAC name) (285) + TX, (Z)-hexadec-11- enal (lUPAC name) (436) + TX, (Z)-hexadec-11 -en-1 -yl acetate (lUPAC name) (437) + TX, (Z)- hexadec-13-en-11 -yn-1 -yl acetate (lUPAC name) (438) + TX, (Z)-icos-13-en-10-one (lUPAC name) (448) + TX, (Z)-tetradec-7-en-1 -al (lUPAC name) (782) + TX, Z)-tetradec-9-en-1-ol (lUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (lUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (lUPAC name) (283) + TX, (9Z,11 E)-tetradeca-9,11 -dien-1 -yl acetate (lUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (lUPAC name) (781) + TX, 14-methyloctadec-1-ene (lUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (lUPAC name) (544) + TX, alpha-multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (lUPAC name) (286)
+ TX, dodec-9-en-1-yl acetate (lUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1 -yl acetate (lUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (lUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421) + TX, grandlure I
(alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2,13-dien-1-yl acetate (lUPAC name) (588) + TX, octadeca-3,13-dien-1-yl acetate (lUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-1 1 -en-1 -yl acetate (lUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure Bi (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX, an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, an insecticide selected from the group of substances consisting of 1 -dichloro-1 -nitroethane
(lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1 -dichloro-2,2-bis(4-ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 -bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1 -(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (lUPAC name) (1066) + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate (lUPAC/ Chemical Abstracts name)
(1 109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (lUPAC/Chemical Abstracts name) (935) + TX, 2- (4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate (lUPAC/ Chemical Abstracts name) (1084) + TX, 2-(4-chloro-3,5-xylyloxy)ethanol (lUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (lUPAC name) (984) + TX, 2-imidazolidone (lUPAC name) (1225) + TX, 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (lUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (lUPAC name) (1433) + TX, 3-bromo-1 -chloroprop-1 -ene (lUPAC name) (917) + TX, 3-methyl-1 -phenylpyrazol-5-yl dimethylcarbamate (lUPAC name) (1283) + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (lUPAC name) (1285) + TX, 5,5-dimethyl- 3-oxocyclohex-1 -enyl dimethylcarbamate (lUPAC name) (1085) + TX, abamectin (1) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion (alternative name) [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (lUPAC name) (861) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin (alternative name) [CCN] + TX, allyxycarb (866) + TX, alpha-cypermethrin (202) + TX, alpha- ecdysone (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, athidathion (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus thuringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (lUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta- cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, bioallethrin S-cyclopentenyl isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (lUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (914) + TX, bromocyclen (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX,
butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (lUPAC name) (111) + TX, camphechlor (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbon disulfide (lUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (lUPAC name) (946) + TX, carbophenothion (947) + TX, carbosulfan (119) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclen (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131) + TX, chlorfluazuron (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141) + TX, chlorphoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate (1006) +
TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (1011) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX,
cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, d- limonene (alternative name) [CCN] + TX, cf-tetramethrin (alternative name) (788) + TX, DAEP (1031) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-O (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dimpropyridaz + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050) + TX, dichlofenthion (1051) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5-methylpyrazol-3-yl phosphate (lUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimetilan (1086) + TX, dinex (1089) + TX, dinex-diclexine (1089) +
TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271) + TX, diofenolan (1099) + TX, dioxabenzofos (1 100) + TX, dioxacarb (1 101 ) + TX, dioxathion (1 102) + TX, disulfoton (278) + TX, dithicrofos (1 108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1 1 15) + TX, ecdysterone (alternative name) [CCN] + TX, El 1642 (development code) (1 1 18) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, EMPC (1 120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1 121) + TX, endrin (1 122) + TX, EPBP (1 123) + TX, EPN (297) + TX, epofenonane (1 124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, ethoate-methyl (1 134) + TX, ethoprophos (312) + TX, ethyl formate (lUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1 136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1 142) + TX, EXD (1 143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaflor (1 147) + TX, fenchlorphos (1 148) + TX, fenethacarb (1 149) + TX, fenfluthrin (1 150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1 153) + TX, fenoxycarb (340) + TX, fenpirithrin (1 155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1 158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg. No.: 272451 -65-7) + TX, flucofuron (1 168) + TX, flucycloxuron (366) + TX,
flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1 171) + TX, flumethrin (372) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, fonofos (1 191) + TX, formetanate (405) + TX, formetanate hydrochloride (405)
+ TX, formothion (1 192) + TX, formparanate (1 193) + TX, fosmethilan (1 194) + TX, fospirate (1 195) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furathiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (121 1) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX,
iodomethane (lUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl 0-(methoxy- aminothiophosphoryl)salicylate (lUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCNJ + TX, kelevan (1249) + TX, kinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimfos (1251) + TX, lufenuron (490) + TX, lythidathion (1253) + TX, m-cumenyl methylcarbamate (lUPAC name) (1014) + TX, magnesium phosphide (lUPAC name) (640) + TX, malathion (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarphon (1258) + TX, menazon (1260) + TX, mephosfolan (1261 ) + TX, mercurous chloride (513) + TX, mesulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (lUPAC/Chemical Abstracts name) (1268) + TX, methidathion (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methothrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (lUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (131 1 ) + TX, nitrilacarb (1313) +
TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (lUPAC name) (1057) + TX, 0,0-diethyl 0-4-methyl-2-oxo-2/-/-chromen-7-yl phosphorothioate (lUPAC name) (1074) + TX, 0,0-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (lUPAC name) (1075) + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate (lUPAC name) (1424) + TX, oleic acid (lUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penfluron (alternative name)
[CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (lUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, phenthoate (631) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (lUPAC name) (640) + TX, phoxim (642) + TX, phoxim-methyl (1340) + TX, pirimetaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (lUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofos (686) + TX, prothoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalphos (711) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381) + TX, R-1492
(development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (lUPAC/Chemical Abstracts name) (1399) + TX, sodium
hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (lUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) +
TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, terallethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, thiocarboxime (1431) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801) + TX, thionazin (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) +
TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121- 52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1 ] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/0921 15) + TX, fluxametamide (WO 2007/026965) + TX, epsilon-metofluthrin [240494-71 -7] + TX, epsilon-momfluorothrin [1065124-65-3] + TX,
fluazaindolizine [1254304-22-7] + TX, chloroprallethrin [399572-87-3] + TX, fluxametamide [928783- 29-3] + TX, cyhalodiamide [1262605-53-7] + TX, tioxazafen [330459-31 -9] + TX, broflanilide [1207727- 04-5] + TX, flufiprole [704886-18-0] + TX, cyclaniliprole [1031756-98-5] + TX, tetraniliprole [1229654- 66-3] + TX, guadipyr (described in WO2010/060231) + TX, cycloxaprid (described in WO
2005/077934) + TX, spiropidion + TX, Afidopyropen + TX, flupyrimin + TX, Momfluorothrin + TX, kappa-bifenthrin + TX, kappa-tefluthrin + TX, Dichloromezotiaz + TX, Tetrachloraniliprole + TX, benzpyrimoxan + TX a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX, pyriprole [394730-71 -3] + TX, a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX,
1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2-dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1 ,1 - dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid (lUPAC name) (1286)
+ TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541
(compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (1 18) + TX, carbon disulfide (945) + TX, carbosulfan (1 19) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051 ) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fen pyrad (alternative name) + TX, fensulfothion (1 158) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (lUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231 ) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaha composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX,
phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (lUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1 ] + TX, fluopyram + TX, a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX, a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutha sachalinensis extract (alternative name) (720) + TX, a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha- chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX,
bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) +
TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1 183) + TX, flupropadine hydrochloride (1 183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (lUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (lUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (lUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX, a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX, an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX, a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX, and biologically active compounds selected from the group consisting of ametoctradin [865318-97-4] + TX, amisulbrom [348635-87-0] + TX, azaconazole (60207-31 -0] + TX, benzovindiflupyr [1072957-71 - 1 ] + TX, bitertanol [70585-36-3] + TX, bromuconazole [1 16255-48-2] + TX, coumoxystrobin
[850881 -70-8] + TX, cyproconazole [94361 -06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [238410-1 1 -2] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [1 14369-43-6] + TX, fenpyrazamine [473798-59-3] + TX, fluquinconazole [136426- 54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21 -0] + TX, fluxapyroxad [907204-31 -3] + TX, fluopyram [658066-35-4] + TX, fenaminstrobin [366815-39-6] + TX, isofetamid [875915-78-9] +
TX, hexaconazole [79983-71 -4] + TX, imazalil [35554-44-0] + TX, imibenconazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08-1 ] + TX, isotianil [224049-04-1 ] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures described in
WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [1251 16-23-6] + TX, myclobutanil [88671 -89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30-4] + TX, penflufen [494793-67-8] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283-41 -4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1 ] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [1 12281 -77-3]
+ TX, triadimefon [43121 -43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] +
TX, triticonazole [131983-72-7] + TX, ancymidol [12771 -68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71 -9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221 -53-4] + TX, ethirimol [23947-60-6] + TX, dodemorph [1593-77-7] + TX, fenpropidine [67306-00-7] + TX, fenpropimorph [67564-91 -4] + TX, spiroxamine [1 18134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61 -2] + TX, mepanipyrim [1 10235-47-7] + TX, pyrimethanil [531 12-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341 -86-1 ] + TX, benalaxyl [71626-1 1 -4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1 ] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605- 21 -7] + TX, debacarb [62732-91 -6] + TX, fuberidazole [3878-19-1 ] + TX, thiabendazole [148-79-8] + TX, chlozolinate [84332-86-5] + TX, dichlozoline [24201 -58-9] + TX, iprodione [36734-19-7] +
TX, myclozoline [54864-61 -8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471 -44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691 -80-3] + TX, flutolanil [66332-96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814-41 -0] + TX, oxycarboxin [5259-88-1 ] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [1 12-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, dimoxystrobin [149961 -52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1 , 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1 ] + TX, trifloxystrobin [141517-21 -7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [1 17428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin [862588-1 1 -2] + TX, fluoxapiprolin [1360819-1 1 -9] +TX, ferbam [14484-64-1 ] + TX, mancozeb [8018-01 -7] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, propineb [12071 -83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1 ] + TX, captan [133-06-2] + TX, dichlofluanid [1085-98-9] + TX, fluoroimide [41205-21 -4] + TX, folpet [133-07-3 ] + TX, tolylfluanid [731 -27-1 ] + TX, bordeaux mixture [801 1 - 63-0] + TX, copperhydroxid [20427-59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [1317-39-1 ] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap [131 -72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos [26087-47-8] + TX, isoprothiolane [50512-35-1 ] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzo- lar-S-methyl [135158-54-2] + TX, anilazine [101 -05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01 -2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (Flumorph) [211867-47-9] + TX, dithianon [3347-22-6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [115852-48-7] + TX, fentin [668-34-8] + TX, ferimzone [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [2391 10-15-7] + TX, flusulfamide [106917-52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminium [39148-24-8] + TX, hymexazol [10004-44-1 ] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Cyazofamid) [120116-88-3] + TX, kasugamycin [6980-18- 3] + TX, methasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063- 05-6] + TX, phthalide [27355-22-2] + TX, , picarbutrazox [500207-04-5] + TX, polyoxins [1 1 1 13-80- 7] + TX, probenazole [27605-76-1 ] + TX, propamocarb [25606-41 -1 ] + TX, proquinazid [189278- 12-4] + TX, pydiflumetofen [1228284-64-7] + TX, pyrametostrobin [915410-70-7] + TX, pyroquilon [57369-32-1 ] + TX, pyriofenone [688046-61 -9] + TX, pyribencarb [799247-52-2] + TX, pyrisoxazole [847749-37-5] + TX, quinoxyfen [124495-18-7] + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX, Timorex Gold™ (plant extract containing tea tree oil from the Stockton Group) + TX, tebufloquin [376645-78-2] + TX, tiadinil [223580-51 -6] + TX, triazoxide [72459-58-6] + TX, tolprocarb [91 1499-62- 2] + TX, triclopyricarb [902760-40-1 ] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, valifenalate [283159-90-0] + TX, zoxamide (RH7281) [156052-68-5] + TX, mandipropamid [374726-62-2] + TX, isopyrazam [881685-58-1 ] + TX, phenamacril + TX, sedaxane [874967-67-6] + TX, trinexapac-ethyl [95266-40-3] + TX, 3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxylic acid (9-dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)- amide (disclosed in WO 2007/048556) + TX, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX,
[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]- 1 ,3,4,4a,5,6,6a,12,12a,12b- decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-1 1 -oxo-9-(3-pyridinyl)-2/-/,1 1 /-/naphtho[2,1 -b]pyrano[3,4- e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7] + TX and 1 ,3,5-trimethyl-N-(2-methyl-1 - oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1 -methoxy-1 -(trifluoromethyl)ethyl]phenyl]-1 H- pyrazole-4-carboxamide [926914-55-8] + TX; lancotrione [1486617-21 -3] + TX, florpyrauxifen [943832- SI -3] ] + TX, ipfentrifluconazole[1417782-08-1 ] + TX, mefentrifluconazole [1417782-03-6] + TX, quinofumelin [861647-84-9] + TX, chloroprallethrin [399572-87-3] + TX, cyhalodiamide [1262605-53- 7] ] + TX, fluazaindolizine [1254304-22-7] + TX, fluxametamide [928783-29-3] + TX, epsilon- metofluthrin [240494-71 -7] + TX, epsilon-momfluorothrin [1065124-65-3] + TX, pydiflumetofen
[1228284-64-7] + TX, kappa-bifenthrin [439680-76-9] + TX, broflanilide [1207727-04-5] + TX, dicloromezotiaz [1263629-39-5] + TX, dipymetitrone [161 14-35-5] + TX, pyraziflumid [942515-63-1 ] + TX, kappa-tefluthrin [391634-71 -2] + TX, fenpicoxamid [517875-34-2] + TX; fluindapyr [1383809-87-7] + TX; alpha-bromadiolone [28772-56-7] + TX; flupyrimin [1689566-03-7] + TX; benzpyrimoxan
[1449021 -97-9] + TX; acynonapyr [1332838-17-1 ] + TX; inpyrfluxam [1352994-67-2] + TX, isoflucypram [1255734-28-1 ] + TX; rescalure [64309-03-1 ] + TX; aminopyrifen [1531626-08-0] + TX; tyclopyrazoflor [1477919-27-9] + TX; and spiropidion [1229023-00-0] + TX; and microbials including: Acinetobacter Iwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) +
TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX,
Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp. + TX, Aureobasidium pullulans + TX, Azospirillum + TX, (MicroAZ® + TX, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®) + TX, Bacillus licheniformis strain 3086 (EcoGuard® + TX, Green Releaf®) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe® + TX, BioNem-WP® + TX, VOTiVO®) + TX, Bacillus firmus strain 1-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder®) + TX, Bacillus pumilus spp. + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain QST 2808 (Sonata® + TX, Ballad Plus®) + TX, Bacillus spahericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis strain QST 713 (CEASE® + TX, Serenade® + TX, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro® + TX, Rhizopro®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1 Ab + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis israelensis (BMP123® + TX, Aquabac® + TX, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bonide® + TX, Scutella WP® + TX, Turilav WP ® +
TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari® + TX, DiPel®) + TX, bacteria spp. (GROWMEND® + TX, GROWSWEET® + TX, Shootup®) + TX, bacteriophage of Clavipacter michiganensis (AgriPhage®) + TX, Bakflor® + TX, Beauveria bassiana (Beaugenic® + TX, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES® + TX, Mycotrol O® + TX, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz® + TX, Schweizer Beauveria® + TX, Melocont®) + TX, Beauveria spp. + TX, Botrytis cineria + TX,
Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp. + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp. + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX,
Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®) + TX, Cydia pomonella granulovirus (Madex® + TX, Madex Plus® + TX, Madex Max/ Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp. + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus
(Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi +
TX, Halomonas spp. + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, Isoflavone - formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp. + TX, Lagenidium giganteum (Laginex®) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertiki I®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®)
+ TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp. (AMykor® + TX, Root Maximizer®) + TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) + TX, BROS PLUS® + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces fumosoroseus (PFR-97® + TX, PreFeRal®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium
brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp. + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea +
TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX,
Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp. + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomons fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculate + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium
paroecandrum + TX, Pythium oligandrum (Polygandron® + TX, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal® + TX, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir®) + TX,
Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp. + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum- P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX,
Trichothecium spp. + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus ; and
Plant extracts including: pine oil (Retenol®) + TX, azadirachtin (Plasma Neem Oil® + TX, AzaGuard® + TX, MeemAzal® + TX, Molt-X® + TX, Botanical IGR (Neemazad® + TX, Neemix®) + TX, canola oil (Lilly Miller Vegol®) + TX, Chenopodium ambrosioides near ambrosioides (Requiem®) + TX, Chrysanthemum extract (Crisant®) + TX, extract of neem oil (Trilogy®) + TX, essentials oils of Labiatae (Botania®) + TX, extracts of clove rosemary peppermint and thyme oil (Garden insect killer®) + TX, Glycinebetaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil + TX, Nepeta cataria (Catnip oil) + TX, Nepeta catarina + TX, nicotine + TX, oregano oil (MossBuster®)
+ TX, Pedaliaceae oil (Nematon®) + TX, pyrethrum + TX, Quillaja saponaria (NemaQ®) + TX, Reynoutria sachalinensis (Regalia® + TX, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, soybean oil (Ortho ecosense®) + TX, tea tree oil (Timorex Gold®) + TX, thymus oil + TX, AGNIQUE® MMF + TX, BugOil® + TX, mixture of rosemary sesame pepermint thyme and cinnamon extracts (EF 300®) + TX, mixture of clove rosemary and peppermint extract (EF 400®) + TX, mixture of clove pepermint garlic oil and mint (Soil Shot®) + TX, kaolin (Screen®) + TX, storage glucam of brown algae (Laminarin®); and pheromones including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Codling Moth Pheromone (Paramount dispenser-(CM)/ Isomate C-Plus®) + TX, Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, Leafroller pheromone (3M MEC - LR Sprayable Pheromone®) + TX, Muscamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, Oriental Fruit Moth Pheromone (3M oriental fruit moth sprayable pheromone®) + TX, Peachtree Borer Pheromone (Isomate-P®) + TX, Tomato Pinworm Pheromone (3M Sprayable pheromone®) + TX, Entostat powder (extract from palm tree) (Exosex CM®) + TX, (E + TX,Z + TX,Z)- 3 + TX,8 + TX,1 1 Tetradecatrienyl acetate + TX, (Z + TX,Z + TX,E)-7 + TX,1 1 + TX,13- Hexadecatrienal + TX, (E + TX,Z)-7 + TX,9-Dodecadien-1 -yl acetate + TX, 2-Methyl-1 -butanol + TX, Calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, Lavandulyl senecioate; and
Macrobials including: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline® + TX, Andersoni-System®) + TX, Amblyseius californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii® + TX, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline® + TX, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis + TX, Aphidius matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®) + TX, Aphidoletes aphidimyza (Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Natupol Beehive®) + TX, Bombus terrestris (Beeline® + TX, Tripol®) + TX, Cephalonomia stephanoderis +
TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline®) + TX, Chrysoperla carnea
(Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica + TX, Dacnusa sibirica
(Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max® + TX, Encarline® + TX, En- Strip®) + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal® + TX, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar® + TX, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiella acarisuga (Spidend®) + TX, Feltiella acarisuga (Feltiline®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX,
Formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis
(HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield HB® + TX, Nemaseek® + TX, Terranem-Nam® + TX, Terranem® + TX, Larvanem® + TX, B-Green® + TX, NemAttack ® + TX, Nematop®) + TX, Heterorhabditis megidis (Nemasys H® + TX, BioNem H® + TX, Exhibitline hm® + TX, Larvanem-M®) + TX, Hippodamia convergens + TX, Hypoaspis aculeifer (Aculeifer-System® + TX, Entomite-A®) + TX, Hypoaspis miles (Hypoline m® + TX, Entomite-M®) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX,
Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar
(Natufly®) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N® + TX, Macroline c® + TX, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis
(NesidioBug® + TX, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I®
+ TX, Oriline i®) + TX, Orius laevigatus (Thripor-L® + TX, Oriline I®) + TX, Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex® + TX, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus +
TX, Psyttalia concolor (complex) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C® + TX, Millenium® + TX, BioNem C® + TX, NemAttack®
+ TX, Nemastar® + TX, Capsanem®) + TX, Steinernema feltiae (NemaShield® + TX, Nemasys F® + TX, BioNem F® + TX, Steinernema-System® + TX, NemAttack® + TX, Nemaplus® + TX, Exhibitline sf® + TX, Scia-rid® + TX, Entonem®) + TX, Steinernema kraussei (Nemasys L® + TX, BioNem L® + TX, Exhibitline srb®) + TX, Steinernema riobrave (BioVector® + TX, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator, and other biologicals including: abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, Copper Octanoate (Cueva®) + TX, Delta traps (Trapline d®) + TX, Erwinia amylovora (Harpin) (ProAct® + TX, Ni-HIBIT Gold CST®) +
TX, Ferri-phosphate (Ferramol®) + TX, Funnel traps (Trapline y®) + TX, Gallex® + TX, Grower's Secret® + TX, Homo-brassonolide + TX, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) + TX, MCP hail trap (Trapline f®) + TX, Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, BioGain® + TX, Aminomite® + TX, Zenox® + TX, Pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, potassium iodide + potassiumthiocyanate (Enzicur®) + TX, SuffOil-X® + TX, Spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper Control®) + TX, Sticky traps (Trapline YF® + TX, Rebell Amarillo®) + TX and Traps (Takitrapline y + b®) + TX, or a biologically active compound or agent selected from: Brofluthrinate + TX, Diflovidazine + TX, Flometoquin + TX, Fluhexafon + TX, Plutella xylostella Granulosis virus + TX, Cydia pomonella Granulosis virus + TX, Imicyafos + TX, Heliothis virescens Nucleopolyhedrovirus + TX, Heliothis punctigera Nucleopolyhedrovirus + TX, Helicoverpa zea Nucleopolyhedrovirus + TX, Spodoptera frugiperda Nucleopolyhedrovirus + TX, Plutella xylostella Nucleopolyhedrovirus + TX, p-cymene + TX, Pyflubumide + TX, Pyrafluprole + TX, QRD 420 + TX, QRD 452 + TX, QRD 460 + TX, Terpenoid blends + TX, Terpenoids + TX, Tetraniliprole + TX, and a-terpinene + TX; or an active substance referenced by a code + TX, such as code AE 1887196 (BSC-BX60309) + TX, code NNI-0745 GR + TX, code IKI-3106 + TX, code JT-L001 + TX, code ZNQ-08056 + TX, code IPPA152201 + TX, code HNPC-A9908 (CAS: [660411-21-2]) + TX, code HNPC-A2005 (CAS:
[860028-12-2]) + TX, code JS118 + TX, code ZJ0967 + TX, code ZJ2242 + TX, code JS7119 (CAS:
[929545-74-4]) + TX, code SN-1172 + TX, code HNPC-A9835 + TX, code HNPC-A9955 + TX, code HNPC-A3061 + TX, code Chuanhua 89-1 + TX, code IPP-10 + TX, code ZJ3265 + TX, code JS9117 + TX, code ZJ3757 + TX, code ZJ4042 + TX, code ZJ4014 + TX, code ITM-121 + TX, code DPX-RAB55 (DKI-2301) + TX, code NA-89 + TX, code MIE-1209 + TX, code MCI-8007 + TX, code BCS-CL73507 + TX, code S-1871 + TX, code DPX-RDS63 + TX,
or a biologically active compound selected from Quinofumelin + TX, mefentrifluconazol + TX, fenpicoxamid + TX, fluindapyr + TX, inpyrfluxam + TX or indiflumetpyr + TX, isoflucypram + TX, pyrapropoyne + TX, florylpicoxamid + TX, metyltetraprole + TX, ipflufenoquin + TX, pyridachlometyl + TX or chlopyridiflu + TX, tetrachlorantraniliprole + TX, tetrachloraniliprole + TX, Tyclopyrazoflor + TX, flupyrimin + TX or pyrifluramide + TX, benzpyrimoxan + TX, Benzosufyl + TX or oxazosulfyl + TX, etpyrafen + TX, acynonapyr + TX or pyrinonafen + TX, oxotrione + TX, bixlozone + TX or clofendizone + TX or dicloroxizone + TX, cyclopyranil + TX or pyrazocyclonil + TX or cyclopyrazonil + TX , alpha-bromadiolone + TX, code AKD-1193 + TX, Oxathiapiprolin + TX, Fluopyram + TX, Penflufen+ TX, Fluoxopyrosad + TX, fluoxapiprolin + TX, dimpropyridaz + TX, tetflupyrolimet + TX, beflubutamid-M + TX, isocycloseram + TX, Flupyradifurone + TX, tetflupyrolimet + TX, N-[(1 ,2 cis)-2- [2-fluoro-4-(trifluoromethyl)phenyl]cyclobutyl]-3-(trifluoromethyl)pyrazine-2-carboxamide + TX, 2- (trifluoromethyl)-N-[(2,3 cis)-2-(2,4,6-trifluorophenyl)oxetan-3-yl]benzamide + TX, 2,6-difluoro-N-[(2,3 cis)-2-(2,4,6-trifluorophenyl)oxetan-3-yl]benzamide + TX, N-[(1 ,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]- 2-(trifluoromethyl)benzamide + TX, N-[(1 ,2 cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2- (trifluoromethyl)pyridine-3-carboxamide + TX, N-[(1 ,2 cis)-2-(2,4-difluorophenyl)cyclobutyl]-2- (trifluoromethyl)benzamide + TX, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-1 -methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6- c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone (can be prepared according to the procedures described in WO 201 1/138281) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3-carbonitrile + TX, 4- (2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (can be prepared according to the procedures described in WO 2012/031061) + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3- trimethyl-indan-4-yl)-1 -methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881 -30-0 + TX, 3-(3,4-dichloro-1 ,2-thiazol-5- ylmethoxy)-1 ,2-benzothiazole 1 ,1 -dioxide (can be prepared according to the procedures described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1 -yl)quinolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3- quinolyl)oxy]phenyl]propan-2-ol (can be prepared according to the procedures described in WO 201 1/081 174) + TX, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (can be prepared according to the procedures described in WO 201 1 /081 174) + TX, oxathiapiprolin + TX
[1003318-67-9], tert-butyl N-[6-[[[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2- pyridyljcarbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/ 072999) + TX, 3- (difluoromethyl)-1 -methyl-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, 2,2,2-trifluoroethyl N-[2-methyl-1 - [[(4-methylbenzoyl)amino]methyl]propyl]carbamate + TX, (2RS)-2-[4-(4-chlorophenoxy)-a,a,a-trifluoro- o-tolyl]-1 -(1 H-1 ,2,4-triazol-1 -yl)propan-2-ol + TX, (2RS)-2-[4-(4-chlorophenoxy)-a,a,a-trifluoro-o-tolyl]- 3-methyl-1 -(1 H-1 ,2,4-triazol-1 -yl)butan-2-ol + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 , 1 -dimethyl- indan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine- 3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4- (4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (can be prepared according to the procedures described in WO 2007/031513) + TX, [2-[3-[2-[1 -[2-[3,5- bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro- phenyl] methanesulfonate (can be prepared according to the procedures described in WO
2012/025557) + TX, but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]- 2-pyridyl]carbamate (can be prepared according to the procedures described in WO 2010/000841) + TX, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1 ,2,4-triazole-3-thione (can be prepared according to the procedures described in WO 2010/146031) + TX, methyl N-[[5-[4-(2,4- dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4- (2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121 104) + TX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro-4-(2,6- difluorophenyl)-6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774) + TX, (R)-3-(difluoromethyl)-1 - methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 201 1/162397 ) + TX, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan- 4-yl)-1 -methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl- tetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072) + TX, 1 - methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1 -yl)phenoxy]methyl]phenyl]tetrazol-5-one (can be prepared according to the procedures described in WO 2014/051 165) + TX, (Z,2E)-5-[1 -(4- chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, (4- phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX, N-(5-chloro-2-isopropylbenzyl)- N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methylpyrazole-4-carboxamide [1255734-28-1 ] (can be prepared according to the procedures described in WO 2010/130767) + TX, 3-(difluoromethyl)-N-[(R)- 2,3-dihydro-1 ,1 ,3-trimethyl-1 H-inden-4-yl]-1 -methylpyrazole-4-carboxamide [1352994-67-2] + TX, N'- (2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2- yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)- N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl- N-methyl-formamidine + TX,
Figure imgf000107_0001
(fenpicoxamid [517875-34-2] (as described in WO
2003/035617)) + TX, (1 S)-2,2-bis(4-fluorophenyl)-1 -methylethyl N-{[3-(acetyloxy)-4-methoxy-2- pyridyl]carbonyl}-L-alaninate [1961312-55-9] + TX;(as described in WO 2016/122802) + TX, 2- (difluoromethyl)-N-(l ,1 ,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3- ethyl-1 ,1 -dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3- propyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3-isobutyl-1 ,1 -dimethyl-indan-4- yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3- carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, and spiropidion [1229023-00-0] + TX; and2-(difluoromethyl)-N-[(3R)-1 ,1 -dimethyl-3-propyl- indan-4-yl]pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and/or WO 2016/139189.
The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.
Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the lUPAC name, the lUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "develoment code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed.“CAS Reg. No” means the Chemical Abstracts Registry Number.
The active ingredient mixture of the compounds of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P with active ingredients described above comprises a compound selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 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 :750, or 2:750, or 4:750. Those mixing ratios are by weight.
The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
The mixtures comprising a compound of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and one or more active ingredients as described above can be applied, for example, in a single“ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a“tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula I selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P and the active ingredients as described above is not essential for working the present invention.
The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds I for the preparation of these compositions are also a subject of the invention.
The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.
A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.
The compounds of the invention and compositions thereof are also be suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the compound prior to planting, for example seed can be treated prior to sowing. Alternatively, the compound can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
The present invention also comprises seeds coated or treated with or containing a compound of formula I. The term "coated or treated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with a compound of formula I including those selected from Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P. Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula I including those selected from Tables Z-1 to Z-240, Za-1 - Za-60, Zb-1 - Zb-30 and Table P.
Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound formula I (including those selected from Tables Z-1 to Z-240, Za-1 - Za- 60, Zb-1 - Zb-30 and Table P) can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.
Biological Examples
Biological Example B1 : Activity against Bemisia tabaci (Cotton whitefly)
Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10'OOO ppm DMSO stock solutions. After drying the leaf discs were infested with adult white flies. The samples were checked for mortality 6 days after incubation.
The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P7, and P10.
Biological Example B2: Activity against Diabrotica balteata (Corn root worm) Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P1 , P5, P6, P7, P8, P9, and P10.
Biological Example B3: Activity against Euschistus herns (Neotropical Brown Stink Bug)
Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P5, P9, and P10.
Biological Example B4: Activity against Plutella xylostella (Diamond back moth)
24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10'OOO ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P1 , P4, P5, P6, and P7.
Biological Example B5: Activity against Plutella xylostella (Diamond back moth)
24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P9, and P10.
Biological Example B6: Activity against Mvzus persicae (Green peach aphid)
Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P1 , P7, P8, P9, and P10.
Biological Example B7: Activity against Mvzus persicae (Green peach aphid)
Roots of pea seedlings infested with an aphid population of mixed ages were placed directly into aqueous test solutions prepared from 10Ό00 DMSO stock solutions. The samples were assessed for mortality 6 days after placing seedlings into test solutions.
The following compounds resulted in at least 80% mortality at a test rate of 24 ppm: P4, P5, P7, P8, P9, and P10.
Biological Example B8: Activity against Plutella xylostella (Diamond back moth)
24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: P9, and P10.
Biological Example B9: Activity against Spodoptera littoralis (Egyptian cotton leaf worm)
Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.
The following compounds resulted in at least 80% control at an application rate of 200 ppm: P1 , P5, P6, P7, and P10.
Biological Example B10: Activity against Tetranvchus urticae (Two-spotted spider mite)
Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.
The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: P2.
Biological Example B11 : Activity against Heterodera schachtii (Juvenile mobility in vitro profiling in 96 well plate) Test solutions are prepared from 10Ό00 ppm DMSO stock solutions with a TECAN robot to achieve 20 pL of 500, 100, 50, 25, 12.5 and 6.25 ppm. For each concentration three replicates are produced. Per well, 80 pl_ nematode solution is added containing 100 to 150 freshly harvested second stage juveniles of Heterodera schachtii. The plates are covered and stored at room temperature in the dark and incubated for 48 h. Mobility of the exposed juveniles in a treated well is measured using an imaging tool and compared to an average of 12 untreated replicates.
The following compounds achieved at least 60% control at 100 ppm after 48 h: P7.
Biological Example B12: Activity against Nilaparvata lugens (Brown plant hopper)
Rice plants were treated with the diluted test solutions in a spray chamber. After drying plants were infested with ~20 N3 nymphs. 7 days after the treatment samples were assessed for mortality and growth regulation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 50 ppm: P7, P10.
Biological Example B13: Activity against Nilaparvata lugens (Brown plant hopper)
Rice plants were treated with the diluted test solutions in a spray chamber. After drying plants were infested with ~20 N3 nymphs. 7 days after treatment adults were removed and 15 days after the treatment samples were assessed for effect on F1 generation.
The following compounds gave an effect of at least 80% at an application rate of 50 ppm: P10.
Biological Example B14: Activity against Nilaparvata lugens (Brown plant hopper)
Rice plants cultivated in a nutritive solution were treated with the diluted test solutions into nourishing cultivation system. 1 day after application plants were infested with ~20 N3 nymphs. 7 days after infestation samples were assessed for mortality and growth regulation.
The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 12.5 ppm: P7, P10.

Claims

CLAIMS:
1 . A compound of formula (I)
Figure imgf000114_0002
wherein
A is CH or N;
X is S, SO or S02;
Ri is Ci-C4alkyl, or C3-C6cycloalkyl-Ci-C4alkyl;
R2 IS Ci-C6alkyl, Ci-C6haloalkyl, C3-C6cycloalkyl, C3-C6cycloalkyl substituted with cyano, Ci- C6cyanoalkyl, Ci-C4alkoxyCi-C4alkyl, halogen, cyano, Ci-C4haloalkoxy, Ci-C4alkoxy, aminocarbonyl, Ci-C4alkoxycarbonyl, Ci-C4alkylsulfanyl, Ci-C4alkylsulfinyl, and Ci-C4alkylsulfonyl, Ci- C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, and Ci-C4haloalkylsulfonyl;
n is 0, 1 or 2;
Q is a radical selected from the group consisting of formula Qi to CU
Figure imgf000114_0001
wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein
Xi is O or NR4, wherein R4 is Ci-C4alkyl;
X2 is O or NR5, wherein R5 is Ci-C4alkyl
R3 is halogen, Ci-C6haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl or Ci-C6haloalkoxy;
Gi is N or CH;
G2 and G3 are, independently from each other, N or CH; or
an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide of a compound of formula I.
2. A compound according to claim 1 , wherein
A is CH or N; X is S, SO or S02;
Ri is Ci-C3alkyl or C3-C6cycloalkyl-Ci-C2alkyl;
R2 IS Ci-C4alkyl, Ci-C4haloalkyl, C3-C4cycloalkyl, C3-C4cycloalkyl substituted with cyano, Ci- C2cyanoalkyl, Ci-C3alkoxyCi-C2alkyl, fluoro, chloro, bromo, cyano, Ci-C3haloalkoxy, Ci-C4alkoxy, aminocarbonyl, Ci-C2alkoxycarbonyl, Ci-C2alkylsulfanyl, Ci-C2alkylsulfinyl, Ci-C2alkylsulfonyl, Ci- C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl or Ci-C2haloalkylsulfonyl;
n is 0 or 1 ; and
Q is a radical selected from the group consisting of formula Qi , Q2 or C
Figure imgf000115_0001
wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein
Xi is NR4, wherein R4 is Ci-C2alkyl;
X2 is O or NR5, wherein R5 is Ci-C2alkyl
R3 is fluoro, chloro, bromo, Ci-C2haloalkyl, Ci-C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl, Ci- C2haloalkylsulfonyl or Ci-C2haloalkoxy;
Gi is N or CH; and
G3 is N or CH.
3. A compound according to claim 1 , wherein
A is CH or N;
X is S, SO or SO2;
Ri is ethyl, propyl, isopropyl or cyclopropylmethyl;
R2 IS Ci-C3alkyl, Ci-C2haloalkyl, cyclopropyl, cyclopropyl substituted with cyano, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, fluoro, chloro, bromo, cyano, Ci- C2haloalkoxy, Ci-C3alkoxy, aminocarbonyl, methoxycarbonyl, Ci-C2alkylsulfanyl, Ci-C2alkylsulfinyl, Ci- C2alkylsulfonyl, Ci-C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl or Ci-C2haloalkylsulfonyl;
n is 0 or 1 ; and
Q is a radical selected from the group consisting of formula Qi or C
Figure imgf000115_0002
wherein the arrow denotes the point of attachment to the ring incorporating the radical A; and wherein
Xi is NCH3;
X2 is NCH3;
R3 is bromo, trifluoromethyl, pentafluoroethyl, 1 ,1 -difluoroethyl, difluoromethyl, difluorochloromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, difluoromethylsulfanyl, difluoromethylsulfinyl, difluoromethylsulfony, difluoromethoxy, difluorobromomethoxy or
trifluoromethoxy; and
Gi is N or CH.
4. A compound of formula I according to claim 1 , represented by the compounds of formula 1-1
Figure imgf000116_0001
(1-1)
wherein A, X, Ri , R2, R3, n, Xi and Gi are as defined under formula I in claim 1 .
5. A compound according to claim 4, wherein
A is CH or N; X is S, SO or S02; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen, cyano, aminocarbonyl, or Ci-C2alkoxycarbonyl; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci- C4haloalkylsulfonyl; n is 0 or 1 ; Xi is O or NCH3; and Gi is N or CH.
6. A compound according to claim 4, wherein
A is CH or N; X is S or S02; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci-C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci- C2fluoroalkylsulfonyl; n is 0 or 1 ; Xi is O or NCH3; and Gi is N or CH.
7. A compound of formula I according to claim 1 , represented by the compounds of formula I-2
Figure imgf000116_0002
(I-2)
wherein A, X, Ri , R2, R3, n and G3 are as defined under formula I in claim 1 .
8. A compound according to claim 7, wherein
A is CH or N; X is S, SO or SO2; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci- C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; and G3 is N or CH.
9. A compound according to claim 7, wherein
A is CH or N; X is S, SO or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2haloalkyl, halogen or cyano; R3 is Ci- C2haloalkyl, Ci-C2haloalkylsulfanyl, Ci-C2haloalkylsulfinyl, or Ci-C2haloalkylsulfonyl; n is 0 or 1 ; and G3 is N or CH.
10. A compound of formula I according to claim 1 , represented by the compounds of formula I-3
Figure imgf000117_0001
(I-3)
wherein A, X, Ri , R2, R3, n, G2 and G3 are as defined under formula I in claim 1 .
1 1 . A compound according to claim 10, wherein
A is CH or N; X is S, SO or SO2; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci- C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; G2 is N and G3 is CH.
12. A compound according to claim 10, wherein
In another preferred group of compounds of formula i-3, A is CH or N; X is S, SO or SO2; Ri is Ci- C3alkyl; R2 is Ci-C4haloalkyl, halogen or cyano; R3 is Ci-C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci- C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; G2 is CH and G3 is N.
13. A compound of formula I according to claim 1 , represented by the compounds of formula i-4
Figure imgf000117_0002
(I-4)
wherein A, X, Ri , R2, R3, n, X2 and Gi are as defined under formula I in claim 1 .
14. A compound according to claim 13, wherein
A is CH or N; X is S, SO or SO2; Ri is Ci-C4alkyl; R2 is Ci-C4haloalkyl, halogen, cyano; R3 is Ci- C4haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, or Ci-C4haloalkylsulfonyl; n is 0 or 1 ; X2 is O or NCH3; and Gi is N or CH.
15. A compound according to claim 13, wherein
A is CH or N; X is S or SO2; Ri is Ci-C3alkyl; R2 is Ci-C2fluoroalkyl, halogen, cyano, aminocarbonyl, or methoxycarbonyl; R3 is Ci-C2fluoroalkyl, Ci-C2fluoroalkylsulfanyl, Ci-C2fluoroalkylsulfinyl, or Ci- C2fluoroalkylsulfonyl; n is 0 or 1 ; X2 is O or NCH3; and Gi is N or CH.
16. A compound according to claim 13, wherein Gi is CH, X2 is NMe and A is CH.
17. A compound of formula I according to claim 1 , selected from the group consisting of:
2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-1 -methyl-5- (trifluoromethyl)benzimidazole (compound P1);
6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2-a]pyridine-2- carbonitrile (compound P2);
2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-5-(trifluoromethyl)-1 ,3-benzoxazole (compound P3);
6-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-7-methyl-3-(trifluoromethyl)imidazo[4,5- c]pyridazine (compound P4);
2-(3-bromo-6-ethylsulfonyl-imidazo[1 ,2-a]pyridin-7-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5- c]pyridine (compound P5);
2-[6-ethylsulfonyl-2-(1 ,1 ,2,2,2-pentafluoroethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-b]pyridine (compound P6);
2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5- b] pyridine (compound P7);
2-(6-ethylsulfonylimidazo[1 ,2-a]pyridin-7-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (compound P8);
2-[6-ethylsulfonyl-2-(1 ,1 ,2,2,2-pentafluoroethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6- (trifluoromethyl)imidazo[4,5-c]pyridine (compound P9);
2-[6-ethylsulfonyl-2-(trifluoromethyl)imidazo[1 ,2-a]pyridin-7-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5- c]pyridine (compound P10);
methyl 6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2-a]pyridine- 2-carboxylate (compound P1 1); and
6-ethylsulfonyl-7-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]imidazo[1 ,2-a]pyridine-2- carboxamide (compound P12).
-1 I si s. A pesticidal composition, which comprises at least one compound of formula I as defined in any of claims 1 - 17 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
19. A method for controlling pests, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest, a pesticidally effective amount of a compound of formula I as defined in any of claims 1 - 17 or a composition according to claim 18.
20. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 18.
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Citations (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353191A2 (en) 1988-07-29 1990-01-31 Ciba-Geigy Ag DNA sequences encoding polypeptides having beta-1,3-glucanase activity
EP0367474A1 (en) 1988-11-01 1990-05-09 Mycogen Corporation Novel bacillus thuringiensis isolate denoted b.t. ps81gg, active against lepidopteran pests, and a gene encoding a lepidopteran-active toxin
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
WO1990013651A1 (en) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Bacterial genes
EP0401979A2 (en) 1989-05-18 1990-12-12 Mycogen Corporation Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1995033818A2 (en) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes for the synthesis of antipathogenic substances
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
US5631072A (en) 1995-03-10 1997-05-20 Avondale Incorporated Method and means for increasing efficacy and wash durability of insecticide treated fabric
WO2000015615A1 (en) 1998-09-15 2000-03-23 Syngenta Participations Ag Pyridine ketones useful as herbicides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2003000906A2 (en) 2001-06-22 2003-01-03 Syngenta Participations Ag Plant disease resistance genes
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003034823A1 (en) 2001-10-25 2003-05-01 Siamdutch Mosquito Netting Company Limited Treatment of fabric materials with an insecticide
WO2003035617A2 (en) 2001-10-23 2003-05-01 Dow Agrosciences Llc Patent Department Derivatives of uk-2a
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2005064072A2 (en) 2003-12-22 2005-07-14 Basf Aktiengesellschaft Composition for the impregnation of fibers, fabrics and nettings imparting a protective activity against pests
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2005077934A1 (en) 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, process for the production thereof, and pest controllers containing the same
WO2005113886A1 (en) 2004-05-12 2005-12-01 Basf Aktiengesellschaft Method for the treatment of flexible substrates
WO2005121104A1 (en) 2004-06-09 2005-12-22 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
EP1724392A2 (en) 2005-05-04 2006-11-22 Fritz Blanke Gmbh & Co. Kg Process for the microbicidal finishing of textile surfaces
WO2006128870A2 (en) 2005-06-03 2006-12-07 Basf Aktiengesellschaft Composition for the impregnation of fibers, fabrics and nettings imparting a protective activity against pests
WO2007026965A1 (en) 2005-09-02 2007-03-08 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and harmful organism-controlling agent
WO2007031513A1 (en) 2005-09-13 2007-03-22 Bayer Cropscience Ag Pesticide thiazolyloxy substituted phenylamidine derivatives
WO2007048556A1 (en) 2005-10-25 2007-05-03 Syngenta Participations Ag Heterocyclic amide derivatives useful as microbiocides
WO2007072999A1 (en) 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Pyrazinecarboxamide derivatives and plant disease controlling agents containing the same
WO2007090739A1 (en) 2006-02-03 2007-08-16 Basf Se Process for treating substrates
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008151984A1 (en) 2007-06-12 2008-12-18 Basf Se Aqueous formulation and process for the impregnation of non-living-materials imparting a protective activity against pests
WO2009010455A2 (en) 2007-07-13 2009-01-22 Addex Pharma S.A. Pyrazole derivatives as modulators of metabotropic glutamate receptors
WO2009131237A1 (en) 2008-04-21 2009-10-29 住友化学株式会社 Harmful arthropod control composition, and fused heterocyclic compound
WO2010000841A1 (en) 2008-07-04 2010-01-07 Bayer Cropscience Sa Fungicide hydroximoyl-tetrazole derivatives
WO2010060231A1 (en) 2008-11-25 2010-06-03 Qin Zhaohai Condensed amino nitroguanidine compounds, synthesis and use as botanical insecticides thereof
WO2010093059A1 (en) 2009-02-16 2010-08-19 住友化学株式会社 Method for producing phenylacetamide compound
WO2010125985A1 (en) 2009-04-28 2010-11-04 Sumitomo Chemical Company, Limited Fused heterocyclic compound and use thereof
WO2010130767A2 (en) 2009-05-15 2010-11-18 Bayer Cropscience Ag Fungicide pyrazole carboxamides derivatives
WO2010146031A2 (en) 2009-06-16 2010-12-23 Basf Se Fungicidal mixtures
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
WO2011138281A2 (en) 2010-05-06 2011-11-10 Bayer Cropscience Ag Process for the preparation of dithiine tetracarboxydiimides
WO2011162397A1 (en) 2010-06-24 2011-12-29 Sumitomo Chemical Company, Limited Plant disease control composition and method of controlling plant disease
WO2012020774A1 (en) 2010-08-10 2012-02-16 住友化学株式会社 Plant disease control composition and application for same
WO2012025557A1 (en) 2010-08-25 2012-03-01 Bayer Cropscience Ag Heteroarylpiperidine and -piperazine derivatives as fungicides
WO2012031061A2 (en) 2010-09-01 2012-03-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazoles and their mixtures
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012092115A1 (en) 2010-12-29 2012-07-05 E. I. Du Pont De Nemours And Company Mesoionic pyrido [1,2 -a] pyrimidine pesticides
WO2012133607A1 (en) 2011-03-31 2012-10-04 アステラス製薬株式会社 Pyrazole compound
WO2013024082A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-cyclyloxy-2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-ethyl}-1h-[1,2,4]triazole compounds
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
WO2014013842A1 (en) 2012-07-20 2014-01-23 住友化学株式会社 Composition for controlling plant disease and application therefor
WO2014051165A1 (en) 2012-09-28 2014-04-03 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
WO2014095675A1 (en) 2012-12-19 2014-06-26 Bayer Cropscience Ag Difluoromethyl-nicotinic-indanyl carboxamides as fungicides
WO2015000715A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
WO2016091731A1 (en) 2014-12-11 2016-06-16 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016107742A1 (en) 2014-12-29 2016-07-07 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016122802A1 (en) 2014-12-30 2016-08-04 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
WO2016139189A1 (en) 2015-03-05 2016-09-09 Bayer Cropscience Aktiengesellschaft Fungicidally active compound combinations
WO2017001314A1 (en) * 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2017077968A1 (en) 2015-11-05 2017-05-11 住友化学株式会社 Condensed heterocyclic compound
WO2017134066A1 (en) 2016-02-05 2017-08-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US20170260183A1 (en) 2014-12-02 2017-09-14 Bayer Cropscience Aktiengesellschaft Bicyclic compounds as pest control agents
WO2018052136A1 (en) 2016-09-15 2018-03-22 日産化学工業株式会社 Pest control agent composition and pest control method
JP2019112398A (en) 2017-12-22 2019-07-11 日本曹達株式会社 Fused heterocyclic compound and pest control agent
WO2019219689A1 (en) * 2018-05-18 2019-11-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
WO2019234160A1 (en) * 2018-06-06 2019-12-12 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent Citations (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0353191A2 (en) 1988-07-29 1990-01-31 Ciba-Geigy Ag DNA sequences encoding polypeptides having beta-1,3-glucanase activity
EP0367474A1 (en) 1988-11-01 1990-05-09 Mycogen Corporation Novel bacillus thuringiensis isolate denoted b.t. ps81gg, active against lepidopteran pests, and a gene encoding a lepidopteran-active toxin
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
WO1990013651A1 (en) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Bacterial genes
EP0401979A2 (en) 1989-05-18 1990-12-12 Mycogen Corporation Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1995033818A2 (en) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes for the synthesis of antipathogenic substances
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
US5631072A (en) 1995-03-10 1997-05-20 Avondale Incorporated Method and means for increasing efficacy and wash durability of insecticide treated fabric
WO2000015615A1 (en) 1998-09-15 2000-03-23 Syngenta Participations Ag Pyridine ketones useful as herbicides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2003000906A2 (en) 2001-06-22 2003-01-03 Syngenta Participations Ag Plant disease resistance genes
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003035617A2 (en) 2001-10-23 2003-05-01 Dow Agrosciences Llc Patent Department Derivatives of uk-2a
WO2003034823A1 (en) 2001-10-25 2003-05-01 Siamdutch Mosquito Netting Company Limited Treatment of fabric materials with an insecticide
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2005064072A2 (en) 2003-12-22 2005-07-14 Basf Aktiengesellschaft Composition for the impregnation of fibers, fabrics and nettings imparting a protective activity against pests
WO2005070917A1 (en) 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
WO2005077934A1 (en) 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, process for the production thereof, and pest controllers containing the same
WO2005113886A1 (en) 2004-05-12 2005-12-01 Basf Aktiengesellschaft Method for the treatment of flexible substrates
WO2005121104A1 (en) 2004-06-09 2005-12-22 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof
WO2006087343A1 (en) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi
EP1724392A2 (en) 2005-05-04 2006-11-22 Fritz Blanke Gmbh & Co. Kg Process for the microbicidal finishing of textile surfaces
WO2006128870A2 (en) 2005-06-03 2006-12-07 Basf Aktiengesellschaft Composition for the impregnation of fibers, fabrics and nettings imparting a protective activity against pests
WO2007026965A1 (en) 2005-09-02 2007-03-08 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and harmful organism-controlling agent
WO2007031513A1 (en) 2005-09-13 2007-03-22 Bayer Cropscience Ag Pesticide thiazolyloxy substituted phenylamidine derivatives
WO2007048556A1 (en) 2005-10-25 2007-05-03 Syngenta Participations Ag Heterocyclic amide derivatives useful as microbiocides
WO2007072999A1 (en) 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Pyrazinecarboxamide derivatives and plant disease controlling agents containing the same
WO2007090739A1 (en) 2006-02-03 2007-08-16 Basf Se Process for treating substrates
WO2007129454A1 (en) 2006-05-08 2007-11-15 Kumiai Chemical Industry Co., Ltd. 1,2-benzisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
WO2008151984A1 (en) 2007-06-12 2008-12-18 Basf Se Aqueous formulation and process for the impregnation of non-living-materials imparting a protective activity against pests
WO2009010455A2 (en) 2007-07-13 2009-01-22 Addex Pharma S.A. Pyrazole derivatives as modulators of metabotropic glutamate receptors
WO2009131237A1 (en) 2008-04-21 2009-10-29 住友化学株式会社 Harmful arthropod control composition, and fused heterocyclic compound
WO2010000841A1 (en) 2008-07-04 2010-01-07 Bayer Cropscience Sa Fungicide hydroximoyl-tetrazole derivatives
WO2010060231A1 (en) 2008-11-25 2010-06-03 Qin Zhaohai Condensed amino nitroguanidine compounds, synthesis and use as botanical insecticides thereof
WO2010093059A1 (en) 2009-02-16 2010-08-19 住友化学株式会社 Method for producing phenylacetamide compound
WO2010125985A1 (en) 2009-04-28 2010-11-04 Sumitomo Chemical Company, Limited Fused heterocyclic compound and use thereof
WO2010130767A2 (en) 2009-05-15 2010-11-18 Bayer Cropscience Ag Fungicide pyrazole carboxamides derivatives
WO2010146031A2 (en) 2009-06-16 2010-12-23 Basf Se Fungicidal mixtures
WO2011081174A1 (en) 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
WO2011138281A2 (en) 2010-05-06 2011-11-10 Bayer Cropscience Ag Process for the preparation of dithiine tetracarboxydiimides
WO2011162397A1 (en) 2010-06-24 2011-12-29 Sumitomo Chemical Company, Limited Plant disease control composition and method of controlling plant disease
WO2012020774A1 (en) 2010-08-10 2012-02-16 住友化学株式会社 Plant disease control composition and application for same
WO2012025557A1 (en) 2010-08-25 2012-03-01 Bayer Cropscience Ag Heteroarylpiperidine and -piperazine derivatives as fungicides
WO2012031061A2 (en) 2010-09-01 2012-03-08 E. I. Du Pont De Nemours And Company Fungicidal pyrazoles and their mixtures
WO2012084812A1 (en) 2010-12-20 2012-06-28 Isagro Ricerca S.R.L. Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions
WO2012092115A1 (en) 2010-12-29 2012-07-05 E. I. Du Pont De Nemours And Company Mesoionic pyrido [1,2 -a] pyrimidine pesticides
WO2012133607A1 (en) 2011-03-31 2012-10-04 アステラス製薬株式会社 Pyrazole compound
WO2013024082A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-cyclyloxy-2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-ethyl}-1h-[1,2,4]triazole compounds
WO2013162072A1 (en) 2012-04-27 2013-10-31 Sumitomo Chemical Company, Limited Tetrazolinone compounds and its use as pesticides
WO2014013842A1 (en) 2012-07-20 2014-01-23 住友化学株式会社 Composition for controlling plant disease and application therefor
WO2014051165A1 (en) 2012-09-28 2014-04-03 Sumitomo Chemical Company, Limited Tetrazolinone compounds and their use as pesticides
WO2014095675A1 (en) 2012-12-19 2014-06-26 Bayer Cropscience Ag Difluoromethyl-nicotinic-indanyl carboxamides as fungicides
WO2015000715A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
US20170260183A1 (en) 2014-12-02 2017-09-14 Bayer Cropscience Aktiengesellschaft Bicyclic compounds as pest control agents
WO2016091731A1 (en) 2014-12-11 2016-06-16 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016107742A1 (en) 2014-12-29 2016-07-07 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016122802A1 (en) 2014-12-30 2016-08-04 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
WO2016139189A1 (en) 2015-03-05 2016-09-09 Bayer Cropscience Aktiengesellschaft Fungicidally active compound combinations
WO2017001314A1 (en) * 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2017077968A1 (en) 2015-11-05 2017-05-11 住友化学株式会社 Condensed heterocyclic compound
WO2017134066A1 (en) 2016-02-05 2017-08-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2018052136A1 (en) 2016-09-15 2018-03-22 日産化学工業株式会社 Pest control agent composition and pest control method
JP2019112398A (en) 2017-12-22 2019-07-11 日本曹達株式会社 Fused heterocyclic compound and pest control agent
WO2019219689A1 (en) * 2018-05-18 2019-11-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
WO2019234160A1 (en) * 2018-06-06 2019-12-12 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

Non-Patent Citations (28)

* Cited by examiner, † Cited by third party
Title
"Compendium of Herbicide Adjuvants", 2010, ILLINOIS UNIVERSITY
"McCutcheon's Detergents and Emulsifiers Annual", 1981, MC PUBLISHING CORP.
"The Pesticide Manual - A World Compendium", THE BRITISH CROP PROTECTION COUNCIL
A. ALBINIS. PIETRA: "Heterocyclic N-oxides", 1991, CRC PRESS
ADV. SYNTH. CATAL., vol. 355, 2013, pages 1741 - 1747
ANGEW. CHEM. INT. ED., vol. 46, 2007, pages 7075 - 7078
CHEM. COMMUN., 1997, pages 351 - 352
CHEM. COMMUN., vol. 46, 2010, pages 925 - 927
CHEM. EUR. J., vol. 16, 2010, pages 1983 - 1991
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2211908-96-0
CHEMISTRY - A EUROPEAN JOURNAL, vol. 20, no. 39, 2014, pages 12584 - 12594
J. MED. CHEM., vol. 32, no. 12, 1989, pages 2561 - 73
J. MED. CHEM., vol. 56, no. 1, 2013, pages 84 - 96
J. ORG. CHEM., vol. 69, no. 19, 2004, pages 6504 - 6506
J. ORG. CHEM., vol. 71, 2006, pages 3332 - 3334
J. ORG. CHEM., vol. 78, 2013, pages 12494 - 12504
JOURNAL OF MEDICINAL CHEMISTRY, vol. 49, no. 12, 2006, pages 3614 - 3627
ORG. LETT.,, vol. 7, 2005, pages 4107 - 4110
ORG. PROCESS RES. DEV., vol. 21, no. 9, 2017, pages 1447 - 1451
ORGANIC LETTERS, vol. 13, no. 13, 2011, pages 3542 - 3545
PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS,, vol. 188, no. 12, 2013, pages 1835 - 1844
RSC ADVANCES,, vol. 5, no. 5, 2015, pages 3200 - 3205
SYNTHESIS, vol. 45, no. 11, 2013, pages 1489 - 1496
SYNTHESIS, vol. 47, 2015, pages 1413 - 1422
SYNTHESIS,, 2008, pages 3407 - 3410
TETRAHEDRON LETTERS, vol. 22, 1981, pages 3815 - 3818
TETRAHEDRON, vol. 61, no. 46, 2005, pages 10827 - 10852
U. J. MED. CHEM., vol. 22, no. 5, 1987, pages 457 - 62

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