WO2013037626A1 - Isothiazoline derivatives as insecticidal compounds - Google Patents

Isothiazoline derivatives as insecticidal compounds Download PDF

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Publication number
WO2013037626A1
WO2013037626A1 PCT/EP2012/066579 EP2012066579W WO2013037626A1 WO 2013037626 A1 WO2013037626 A1 WO 2013037626A1 EP 2012066579 W EP2012066579 W EP 2012066579W WO 2013037626 A1 WO2013037626 A1 WO 2013037626A1
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chloro
trifluoromethyl
hydrogen
chlorodifluoromethyl
difluoromethyl
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PCT/EP2012/066579
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French (fr)
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Jérôme Yves CASSAYRE
Myriem El Qacemi
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Syngenta Participations Ag
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=46727234&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2013037626(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to BR112014005683-8A priority Critical patent/BR112014005683B1/en
Priority to BR122018069466-1A priority patent/BR122018069466B1/en
Priority to EP17151894.7A priority patent/EP3190110B1/en
Priority to US14/344,123 priority patent/US9078444B2/en
Priority to EP12750777.0A priority patent/EP2755969B1/en
Priority to CN201280044478.3A priority patent/CN103842358A/en
Publication of WO2013037626A1 publication Critical patent/WO2013037626A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
    • C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
    • C07D291/04—Five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/04—Four-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to certain isothiazoline derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
  • isoxazoline derivatives with insecticidal properties are disclosed, for example, in EP 1,731,512.
  • new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.
  • P is P0, heterocyclyl or heterocyclyl substituted by one to five Z;
  • Y 1 , Y 2 , Y 3 and Y 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • G 1 is oxygen or sulfur
  • R 1 is hydrogen, Ci-Cgalkyl, CpCgalkoxy-, CpCgalkylcarbonyl-, or CpCgalkoxycarbonyl-;
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl-N(R 20 )- or aryl-N(R 20 )- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-N(R 20 )- or heterocyclyl-N(R 20 )- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one
  • G 2 is 0(R 13 ), N(R 14 )(R 15 ) or S(R 16 );
  • G 3 is N(R 17 )(R 18 ) or S(R 19 );
  • X 4 is Ci-Cghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ; each R 5 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, CpCgalkenyl, Cp
  • each R 8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, CpCghaloalkyl, CpCgcyanoalkyl, C 2 - Cgalkenyl, C 2 -Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, C 3 -Ciocycloalkyl, C 3 -Ciocycloalkyl-Cp C 4 alkylene, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, CpCghaloalkylsulfinyl-, CpCgalkylsulfonyl-, CpCghaloalkylsulfonyl-, CpCp
  • each R 9 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, C 2 -Cgalkenyl, C 2 - Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, Cp Cgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, CpCghaloalkylsulfinyl-, CpCgalkylsulfonyl-, Cp Cghaloalkylsulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 ; each R
  • each Z is independently halogen, substituted by one to five R 6 , nitro, Cp
  • Ci-Ci 2 haloalkylsulfinyl, hydroxyl or thiol Ci-Ci 2 haloalkylsulfinyl, hydroxyl or thiol
  • R 13 , R 16 and R 19 are independently C r C 4 alkyl
  • R 14 , R 15 , R 17 , and R 18 are independently hydrogen or C r C 4 alkyl
  • R 20 is hydrogen or C 1 -C4 alkyl
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers N-oxides and salts.
  • the compounds of the invention may contain one or more additional asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2-methyl-prop-l -yl or 2-methyl-prop-2- yl.
  • the alkyl groups are preferably C 1 -C6, more preferably C 1 -C4, most preferably C 1 -C3 alkyl groups.
  • alkyl moiety is said to be substituted
  • the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 -,
  • alkylene groups are preferably C 1 -C3, more preferably C 1 -C 2 , most preferably Ci alkylene groups.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkynyl groups.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl,
  • Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or l,2-dichloro-2-fluoro-vinyl.
  • Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 1 -chloro-prop-2-ynyl.
  • Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl.
  • the cycloalkyl groups are preferably C3-C8, more preferably C3-C6 cycloalkyl groups. Where a cycloalkyl moiety is said to be substituted, the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydroiuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1 , 1 -dioxo-thietanyl.
  • bicyclic groups examples include 2,3 -dihydro-benzo furanyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl.
  • a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Preferred values of P, Y 1 , Y 2 , Y 3 , Y 4 , G 1 , Z, R 1 , R 2 , X 4 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are, in any combination, as set out below.
  • P is P0, or a heterocycle selected from HI to H9
  • k 0, 1 or 2.
  • P is preferably H2 or H6.
  • P is P0.
  • P is P0.
  • P is a heterocycle, preferably selected form HI to H9, more preferably H2 or H6.
  • Y 1 , Y 2 , Y 3 and Y 4 are nitrogen, more preferably no more than one of Y 1 , Y 2 , Y 3 and Y 4 is nitrogen.
  • Y 1 is C-H or C-R 5 , most preferably Y 1 is C-H.
  • Y 2 is C-H or C-R 5 , most preferably Y 2 is C-H.
  • Y 3 is C-H or C-R 5 , most preferably Y 3 is C-H.
  • Y 4 is C-H or C-R 5 , most preferably Y 4 is C-R 5 .
  • Y 1 is C-R 5b , C-H or nitrogen
  • Y 2 and Y 3 are independently C-H or nitrogen
  • Y 1 is C-H
  • Y 2 is C-H or nitrogen
  • Y 3 is C-H or nitrogen
  • Y 4 is C-R 5 , wherein Y 2 and Y 3 are not both nitrogen.
  • Y 1 is C-H
  • Y 2 is C-H
  • Y 3 is C-H
  • Y 4 is C-R 5 .
  • G 1 is oxygen
  • R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 - Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbonyl-Ci-C 4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C 4 alkylen -Cgcycloalkyl-aminocarbony
  • R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 12 , or R 11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R 12 ; and each R 12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbonyl-Ci-C 4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C 4 alkylene, C 3 -Cgcycloalkyl-amino
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbonyl-Ci-C 4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C 4 alkylene, C 3 -Cgcycloalkyl-amino
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 - Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Cr
  • each aryl group is a phenyl group and each heterocyclyl group is selected from pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl.
  • R 2 is CpCgalkyl or d-Cgalkyl substituted by one to five R 6 , C 3 -Ci 0 cyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Cr
  • R 2 is CpCgalkyl or d-Cgalkyl substituted by one to five R 6 , C 3 -Ci 0 cyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Cr
  • R 2 is CpCgalkyl or Ci-Cgalkyl substituted by one to three halogen atoms, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, d- Cgalkylaminocarbonyl-methylene, Ci-Cghaloalkylaminocarbonyl-methylene, C3-Cgcycloalkyl- aminocarbony
  • R 2 is CpCealkyl or CpCealkyl substituted by one to five R 6 , for example ethyl-, butyl-, but-2-yl-, 3-bromo-propyl-, 2,2,2-trifluoro-ethyl-, 3,3,3- trifluoro-propyl-, 2-methoxy-ethyl-, and l-methoxy-prop-2-yl-.
  • R 2 is C3-Cgcycloalkyl or C3-Cgcycloalkyl substituted by one to five R 7 , for example cyclobutyl-, 2-fluoro-cyclopropyl and 2-methyl-cyclohex-l-yl-.
  • a group of preferred compounds are those wherein R 2 is aryl-Ci-C 2 alkylene- or aryl-Cr
  • R 8 for example phenyl-methyl-, 1 - phenyl-eth-l-yl-, 2-phenyl-eth-l-yl-, (3-chloro-phenyl)-methyl-, (2-fluoro-phenyl)-methyl-, (4-methoxy- phenyl)-methyl-, (2-trifluoromethyl-phenyl)-methyl-, and (2-trifluorometh
  • R 2 is heterocyclyl-Ci-C 2 alkylene- or heterocyclyl-Ci-C 2 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , for example (pyrid-2-yl)-methyl-, (pyrid-3-yl)-methyl-, (2-chloro-pyrid-5-yl)-methyl-, ( 1 -methyl- lH-imidazol-4-yl)- methyl-, (furan-2-yl)-methyl-, 2-(thiophen-2'-yl)-eth-l -yl-, 2-(indol-3'-yl)-eth-l-yl-, (lH-benzimidazol-2- yl)-methyl-, (oxetan-2-yl)-methyl-, (tetrahydrofuran-2-yl)-methyl-, 2-([l',3']dioxolan-2'
  • a group of preferred compounds are those wherein R 2 is heterocyclyl-Ci-C 2 alkylene- or heterocyclyl-Ci-C 2 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietany
  • a group of preferred compounds are those wherein R 2 is heteroaryl-Ci-C 2 alkylene- or heteroaryl- Ci-C 2 alkylene- wherein the heteroaryl moiety is substituted by one to five R 8 .
  • R 2 is aryl or aryl substituted by one to five R 8 , for example 2-chloro-phenyl-, 3-fluoro-phenyl-, 2-methyl-phenyl-, 2-chloro-6-methyl-phenyl-, 2- trifluoromethyl-phenyl-, and 2,4-dimethoxy-phenyl-.
  • R 2 is heterocyclyl or heterocyclyl substituted by one to five R 8 , for example 3-methyl-pyrid-2-yl-, l,3-dimethyl-lH-pyrazol-5-yl-, 4-methyl-thiazol-2- yl-, 5-methyl-thiadiazol-2-yl-, quinolin-2-yl-, quinolin-5-yl-, benzothiazol-6-yl-, 4-methyl-benzothiazol- 2-yl-, thietan-3-yl-, 1 -oxo-thietan-3 -yl-, 1,1 -dioxo-thietan-3 -yl-, and 3-methyl-thietan-3-yl-, more preferably R 2 is oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R 8 , most
  • a group of preferred compounds are those wherein R 2 is heterocyclyl- or heterocyclyl substituted by one to five R 8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl,
  • heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
  • a group of preferred compounds are those wherein R 2 is
  • Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene or C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, more preferably Ci-C 4 alkylaminocarbonyl-Ci-C4 alkylene, Ci-C 4 haloalkylaminocarbonyl-Ci-C4 alkylene, or C3-C 6 cycloalkyl-aminocarbonyl-Ci-C4 alkylene, most preferably Ci-C 4 alkylaminocarbonyl-
  • Ci-C4haloalkylaminocarbonyl-Ci-C 2 alkylene Ci-C4haloalkylaminocarbonyl-Ci-C 2 alkylene.
  • a group of preferred compounds are those wherein R 1 and R 2 together represent group A
  • G 2 and G 3 are as defined above, for example group Al, A2, A3 or A4
  • R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 are as defined above.
  • R 13 , R 17 , R 18 and R 19 are preferably Ci-C 4 alkyl, more preferably methyl or ethyl/
  • R 14 and R 15 are preferably hydrogen.
  • a group of preferred compounds are those wherein R 2 is group CI .
  • a group of preferred compounds are those wherein R 2 is group C2.
  • L is a bond, methylene or ethylene; one of A 1 and A 2 is S, SO or S0 2 and the other is -C(R 3a )R 3a ; R 3 is hydrogen or methyl; each R 3a is independently hydrogen or methyl; and preferably L is a bond, preferably R 3 and each R 3a is hydrogen; preferably A 1 is -C(R 4 )R 4 -, more preferably -CH 2 -; preferably A 2 is S, SO or S0 2 .
  • roup of compounds P is selected from PO and PI to P44 and R 2 is group CI or C2
  • X 4 is chlorodifluoromethyl or rifluoromethyl, most preferably trifluoromethyl.
  • R 4 is aryl or aryl substituted by one to five R 9 , more preferably aryl substituted by one to three R 9 , more preferably phenyl substituted by one to three R 9 .
  • R is group (B)
  • X 2 is C-X 6 or nitrogen (preferably C-X 6 );
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X 1 , X 3 and X 6 are not hydrogen; even more preferably R 4 is 3,5-dichlorophenyl-, 3-chloro-4-fluorophenyl-, 3-fluoro-4-chlorophenyl-, 3,4- dichlorophenyl-, 3-chloro-4-bromophenyl-, 3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-, 3,5- dichloro-4-iodophenyl-, 3,4,5-trifluorophenyl-, 3-chloro-5-bromophenyl-, 3 -chloro-5 -fluorophenyl-, 3- chloro-5 -(trifluoromethyl)phenyl-, 3 ,4-d
  • R 4 is 3,5-dichloro-phenyl. In one group of compounds R 4 is 3,5- dichloro-4-fluorophenyl-. In one group of compounds R 4 is 3,4,5-trichlorophenyl-. In one group of compounds R 4 is 3,5-bis(trifluoromethyl)phenyl.
  • each R 5 is independently halogen, cyano, nitro, NH 2 , CpCgalkyl, CpCghaloalkyl, C3- C 5 cycloalkyl, C3-C 5 halocycloalkyl, CpCgalkenyl, Ci-Cghaloalkenyl, CpCgalkoxy-, or CpCghaloalkoxy-, preferably halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C3-C 5 cycloalkyl, C3-C 5 halocycloalkyl, Ci-C 2 alkoxy, Ci-C 2 haloalkoxy; more preferably chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, flu
  • R 5 is chloro. In one group of compounds R 5 is bromo. In one group of compounds R 5 is methyl. In one group of compounds R 5 is halogen.
  • each R 6 is independently halogen, cyano, nitro, hydroxy, CpCgalkoxy-, Cp
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Cp Cgalkoxy-, CpCghaloalkoxy-, mercapto, Ci-Cgalkylthio-, CpCghaloalkylthio-, more preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy.
  • each R 7 is independently halogen or CpCgalkyl, more preferably each R 7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
  • each R 8 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, C2- Cgalkenyl, C2-Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Cp Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 , more preferably each R 8 is independently
  • each R 9 is independently halogen, CpCgalkyl, Ci-Cghaloalkyl, CpCgalkoxy-, Cp Cghaloalkoxy-, CpCgalkylthio-, or CpCghaloalkylthio-, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably bromo or chloro.
  • each R 10 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
  • R 11 is methyl, ethyl or trifluoroethyl.
  • each Z is independently halogen, cyano, CpC 4 alkyl, CpC 4 alkoxy, or CpC ihaloalkoxy, more preferably each Z is independently hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
  • G 1 , R 1 , R 2 , X 4 , R 4 and R 5 are as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for G 1 , R 1 , R 2 , X 4 , R 4 and R 5 are the same as the preferences set out
  • E2 the present invention provides compounds of formula (Ia-2)
  • G 1 , R 1 , R 2 , X 4 , and R 4 are as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for G 1 , R 1 , R 2 , X 4 and R 4 are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • G , R , R , X , and R are as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for G 1 , R 1 , R 2 , X 4 and R 4 are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • X , R and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for X 4 , R 4 , R 5 , and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • X and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for X 4 , R 4 and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • X and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof.
  • the preferences for X 4 , R 4 and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • Y 1 is C-R 5b , CH or nitrogen
  • Y 2 and Y 3 are independently CH or nitrogen;
  • R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C3-C 5 cycloalkyl, C3-
  • X 2 is C-X 6 or nitrogen
  • X 1 , X 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
  • X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
  • E8 provides compounds of formula (Ic) wherein R 4 , X 1 , X 2 , X 3 , X 4 and X 6 are as defined for the compounds of fomrula Ic and P is selected from PO and PI to P44; G 1 is oxygen; R 1 is hydrogen; R 2 is Al or A2; L is a bond, methylene or ethylene; one of A 1 and A 2 is S, SO or S0 2 and the other is -C(R 3a )R 3a -; R 3 is hydrogen or methyl; each R 3a is independently hydrogen or methyl; R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl- methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, prop
  • the present invention provides compounds of formula (Ic) wherein P is selected from P0 and PI to P44; G 1 is oxygen; R 1 is hydrogen; R 2 is Al or A2; R 3 and R 3a are hydrogen; R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl; R 11 is methyl, ethyl or trifluoroethyl; L is a bond; A 1 is -CH 2 -; A 2 is S, SO or S0 2 ; Y 1 is CH, Y 2 is CH, and Y 3 is CH; X 1 , X 3 and X 6 are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen; X 2 is C-X 6 ; X 4 is trifluoromethyl, or chlorodifluoromethyl.
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is Al or A2
  • R 3 and R 3a are hydrogen
  • X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are as defined for a compound of formula (I), G 1 is oxygen, and R is hydroxy, Ci-Ci 5 alkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof.
  • the preferences for X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
  • R is hydroxy, CpCealkoxy or chloro.
  • a further group of novel intermediates are compounds of formula (Int-II)
  • X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are as defined for a compound of formula (I), and X B is a leaving group such as halogen, CpCgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, CpCgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br “ , -N 2 + PF 6 " ), phosphonate esters (e.g. -OP(0)(OR) 3 ⁇ 4 wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride; or a salt or N-oxide thereof.
  • the preferences for X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
  • a further group of novel intermediates are compounds of formula (Int-III)
  • Y 1 , Y 2 , Y 3 and Y 4 are as defined for compounds of formula (I), Px is P as defined above, a leaving group, such as halogen, Ci-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Cp Cgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium ⁇ ,
  • - 16 - salts e.g. X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br “ , -N 2 + PF 6 " ), phosphonate esters (e.g. -OP(0)(OR) 2, wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci 5 alkoxy, or a salt or N-oxide thereof.
  • the preferences for Y 1 , Y 2 , Y 3 and Y 4 and the preferences at position Px when Px is P or heterocycle are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
  • a group of compounds of formula (Int-III) are compounds of formula (Int-IV)
  • Y , Y Y ⁇ Y 1 , R and R" are as defined for compounds of formula (I).
  • the preferences for Y , Y 2 , Y 3 , Y 4 , R 1 and R 2 are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
  • Y 1 , Y 2 , Y 3 and Y 4 are as defined for the compounds of formula (I), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for substituent P of compounds of formula I.
  • the preferences for Y 1 , Y 2 , Y 3 and Y 4 and Pn are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
  • a further group of novel intermediates are compounds of formula (Int-VI)
  • X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III),
  • Z 1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C 4 alkylene-, CpCgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio-, or a salt or N-oxide thereof.
  • Z 1 is preferably hydrogen, benzyl, halogen (preferably chloro) or cyano.
  • Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C 4 alkyl, C 1 -C4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • a further group of novel intermediates are compounds of formula (Int-VII)
  • X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III),
  • Z 1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C 4 alkylene-, CpCgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio-
  • Z 2 is hydrogen or hydroxyl or CpCgalkoxy- or CpCgalkylsulfonyloxy- or arylsulfonyloxy- or aryl-Ci-C 4 alkylene-or aryl.
  • Z 1 is preferably hydrogen, benzyl, halogen (preferably chloro) or cyano.
  • Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C 4 alkyl, C 1 -C4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • a further group of novel intermediates are compounds of formula (Int-VIII)
  • X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III), and Z 3 is thiol or optionally substituted aryl-Ci-Cgalkylsulfinyl-.
  • the preferences for X 4 , R 4 , Y 1 , Y 2 , Y 3 and Y 4 are the same as the preferences set out for the
  • Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C 4 alkyl, C 1 -C4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • compounds of formula I** are more biologically active than compounds of formula I*.
  • the invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to - l o -
  • the molar proportion of compound I** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90,
  • the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95,
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred.
  • Each compound disclosed in Tables 1P-120P and Tables 1Q to 240Q represents a disclosure of a compound according to the compound of formula I*, and a disclosure according to the compound of formula I**.
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
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  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is trifluoromethyl methoxy
  • Y 1 is CH
  • Y 2 is repeatedly r hydrogen CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is difluoromethyl cyano
  • Y 1 is CH
  • Y 2 is chloro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is trifluoromethyl nitro
  • Y 1 is CH
  • Y 2 is repeatedly n chloro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is difluoromethyl ethyl
  • Y 1 is CH
  • Y 2 is repeatedly ⁇ chloro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is

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Abstract

The present invention provides compounds of formula (I) wherein P is P0, heterocyclyl or heterocyclyl substituted by one to five Z formula (II); Y1, Y2, Y3 and Y4 are independently of each other C-H, C-R5, or nitrogen;G1is oxygen or sulfur; X4 is C1-C8 haloalkyl; R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; and R1, R2, R4, R5, R9 and Z are as defined in the claims. The invention also provides compositions comprising the compounds of formula (I), intermediates useful in the preparation of compounds of formula (I) and methods of using the compounds of formula (I) to control insects, acarines, nematodes or molluscs.

Description

ISOTHIAZOLINE DERIVATIVES AS INSECTICIDAL COMPOUNDS
The present invention relates to certain isothiazoline derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
Certain isoxazoline derivatives with insecticidal properties are disclosed, for example, in EP 1,731,512. However there is a continuing need to find new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.
It has now surprisingly been found that certain isothiazoline derivatives have highly potent insecticidal properties and show significantly improved bio-degradability compared to the corresponding isoxazoline analogues.
The present
Figure imgf000002_0001
wherein
P is P0, heterocyclyl or heterocyclyl substituted by one to five Z;
Figure imgf000002_0002
Y1, Y2, Y3 and Y4 are independently of each other C-H, C-R5, or nitrogen;
G1 is oxygen or sulfur;
R1 is hydrogen, Ci-Cgalkyl, CpCgalkoxy-, CpCgalkylcarbonyl-, or CpCgalkoxycarbonyl-;
R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl-N(R 20 )- or aryl-N(R 20 )- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-N(R 20 )- or heterocyclyl-N(R 20 )- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp
Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, Cp Cgalkylaminocarbonyl-, Ci-Cghaloalkylaminocarbonyl, C3-Cgcycloalkyl-aminocarbonyl, CpCealkyl-O- N=CH-, CrC6haloalkyl-0-N=CH-; or R1 and R2 together represent group A
Figure imgf000003_0001
G2 is 0(R13), N(R14)(R15) or S(R16);
G3 is N(R17)(R18) or S(R19);
X4 is Ci-Cghaloalkyl;
R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; each R5 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, CpCgalkenyl, Cp
Cghaloalkenyl, CpCgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, CpCgalkoxy-, CpCghaloalkoxy-, Cp Cgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-; or two R5 on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge; each R6 is independently halogen, cyano, nitro, hydroxy, amino, Ci-Cgalkylamino, (Ci-Cgalkyl)2amino, Ci-Cgalkylcarbonylamino, Ci-Cghaloalkylcarbonylamino, CpCgalkoxy-, CpCghaloalkoxy-, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, mercapto, Cp Cgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Cp Cghaloalkylsulfonyl-, aryl-CpC4alkylthio or aryl-CpC4alkylthio wherein the aryl moiety is substituted by one to five R10;
each R7 is independently halogen, CpCgalkyl, CpCgalkenyl, CpCgalkynyl, CpCgalkyl-0-N=, Cp Cghaloalkyl-0-N=; CpCgalkoxy, CpCgakoxycarbonyl;
each R8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, CpCghaloalkyl, CpCgcyanoalkyl, C2- Cgalkenyl, C2-Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, C3-Ciocycloalkyl, C3-Ciocycloalkyl-Cp C4alkylene, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, CpCghaloalkylsulfinyl-, CpCgalkylsulfonyl-, CpCghaloalkylsulfonyl-, Cp
Cgalkylaminosulfonyl, (CpCgalkyl)2aminosulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, heterocyclyl or heterocyclyl substituted by one to five R10, aryl-Cp C4alkylene or aryl-CpC4alkylene wherein the aryl moiety is substituted by one to five R10, heterocyclyl- CpC4alkylene or heterocyclyl-CpC4alkylene wherein the heterocyclyl moiety is substituted by one to five R10, aryloxy or aryloxy substituted by one to five R10, aryloxy-CpC4alkylene or aryloxy-CpC4alkylene wherein the aryl moiety is substituted by one to five R10;
each R9 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, C2-Cgalkenyl, C2- Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, Cp Cgalkylthio-, CpCghaloalkylthio-, CpCgalkylsulfinyl-, CpCghaloalkylsulfinyl-, CpCgalkylsulfonyl-, Cp Cghaloalkylsulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10; each R10 is independently halogen, cyano, nitro, Ci-C4alkyl, CpC ihaloalkyl, Ci-C4alkoxy-, or Cp C ihaloalkoxy-;
each Z is independently halogen,
Figure imgf000004_0001
substituted by one to five R6, nitro, Cp
Ci2alkoxy or
Figure imgf000004_0002
Ci-Ci2haloalkylsulfinyl,
Figure imgf000004_0003
hydroxyl or thiol;
R13, R16 and R19 are independently CrC4 alkyl;
R14, R15, R17, and R18 are independently hydrogen or CrC4 alkyl;
R20 is hydrogen or C1-C4 alkyl;
or a salt or N-oxide thereof.
The compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers N-oxides and salts. The compounds of the invention may contain one or more additional asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
Alkyl groups (either alone or as part of a larger group, such as alkoxy-, alkylthio-, alkylsulfinyl-, alkylsulfonyl-, alkylcarbonyl- or alkoxycarbonyl-) can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2-methyl-prop-l -yl or 2-methyl-prop-2- yl. The alkyl groups are preferably C1-C6, more preferably C1-C4, most preferably C1-C3 alkyl groups.
Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH2-,
-CH2-CH2-, -CH(CH3)-, -CH2-CH2-CH2-, -CH(CH3)-CH2-, or -CH(CH2CH3)-. The alkylene groups are preferably C1-C3, more preferably C1-C2, most preferably Ci alkylene groups.
Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl. The alkenyl groups are preferably
C2-C6, more preferably C2-C4, most preferably C2-C3 alkenyl groups.
Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl. The alkynyl groups are preferably C2-C6, more preferably C2-C4, most preferably C2-C3 alkynyl groups.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups (either alone or as part of a larger group, such as haloalkoxy-, haloalkylthio-, haloalkylsulfinyl- or haloalkylsulfonyl-) are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl,
chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.
Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or l,2-dichloro-2-fluoro-vinyl.
Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 1 -chloro-prop-2-ynyl. Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl. The cycloalkyl groups are preferably C3-C8, more preferably C3-C6 cycloalkyl groups. Where a cycloalkyl moiety is said to be substituted, the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Aryl groups (either alone or as part of a larger group, such as aryl-alkylene-) are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heteroaryl groups (either alone or as part of a larger group, such as heteroaryl-alkylene-) are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g. 1.2.4 triazoyl), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples of bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl. Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heterocyclyl groups or heterocyclic rings (either alone or as part of a larger group, such as heterocyclyl-alkylene-) are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues. Examples of monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydroiuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1 , 1 -dioxo-thietanyl. Examples of bicyclic groups include 2,3 -dihydro-benzo furanyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl. Where a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Preferred values of P, Y1, Y2, Y3, Y4, G1, Z, R1, R2, X4, R4, R5, R6, R7, R8, R9 and R10 are, in any combination, as set out below.
Preferably, P is P0, or a heterocycle selected from HI to H9
Figure imgf000006_0001
\=≡/-(Z)k \=≡T(Z)k \=≡ftz)k \=≡ftz)k
H 1 H2 H3 H4
Figure imgf000006_0002
H5 H6 H7 H8 H9
k is 0, 1 or 2.
When P is a heterocycle, P is preferably H2 or H6.
More preferably P is P0.
In one group of compounds P is P0. In another group of compounds P is a heterocycle, preferably selected form HI to H9, more preferably H2 or H6.
Preferably no more than two of Y1, Y2, Y3 and Y4 are nitrogen, more preferably no more than one of Y1, Y2, Y3 and Y4 is nitrogen.
Preferably Y1 is C-H or C-R5, most preferably Y1 is C-H.
Preferably Y2 is C-H or C-R5, most preferably Y2 is C-H.
Preferably Y3 is C-H or C-R5, most preferably Y3 is C-H.
Preferably Y4 is C-H or C-R5, most preferably Y4 is C-R5.
In one preferred group of compounds Y1 is C-R5b, C-H or nitrogen, Y2 and Y3 are independently C-H or nitrogen and Y4 is C-R5; wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y2 and Y3 are not both nitrogen, and wherein R5b when present forms a -CH=CH-CH=CH- bridge with R5.
In another preferred group of compounds Y1 is C-H, Y2 is C-H or nitrogen, Y3 is C-H or nitrogen and Y4 is C-R5, wherein Y2 and Y3 are not both nitrogen.
In another preferred group of compounds Y1 is C-H, Y2 is C-H, Y3 is C-H and Y4 is C-R5.
Preferably G1 is oxygen.
Preferably R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
Preferably, R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3- Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C4 alkylen -Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI
Figure imgf000006_0003
(Cl); ,
- 6 - wherein R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R12; and each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
More preferably R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI wherein each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl, 2,3-dihydro- benzofuranyl, benzo[l,3]dioxolanyl, and 2,3-dihydro-benzo[l,4]dioxinyl.
More preferably R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI, wherein each aryl group is a phenyl group and each heterocyclyl group is selected from 1,2,3 triazolyl, 1 ,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl.
More preferably still R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3- Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Cr
C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Cp
Cgalkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl- aminocarbonyl-Ci-C4 alkylene, or group CI, wherein each aryl group is a phenyl group and each heterocyclyl group is selected from pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl. More preferably still R2 is CpCgalkyl or d-Cgalkyl substituted by one to five R6, C3-Ci0cyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Cr
C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, tetrahydrofuranyl-Ci-C4alkylene- or tetrahydrofuranyl-Ci-C4alkylene- wherein the tetrahydroiuranyl moiety is substituted by one to five R8, imidazolyl-Ci-C4alkylene- or imidazolyl-Ci-C4alkylene- wherein the imidazolyl moiety is substituted by one to three R8, pyrazolyl-Ci-C4alkylene- or pyryazolyl-Ci-C4alkylene- wherein the pyrazolyl moiety is substituted by one to three R8, pyrrolyl-Ci-C4alkylene- or pyrrolyl-Ci-C4alkylene- wherein the pyrrolyl moiety is substituted by one to four R8, thiazolyl-Ci-C4alkylene- or thiazolyl-Ci-C4alkylene- wherein the thiazolyl moiety is substituted by one to four R8, oxetanyl- C1-C4 alkylene or oxetanyl-Ci-C4 alkylene wherein the oxetanyl moiety is substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo- thietanyl-Ci-C4 alkylene or dioxo-thietanyl-Ci-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp
Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI .
Even more preferably R2 is CpCgalkyl or d-Cgalkyl substituted by one to five R6, C3-Ci0cyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Cr
C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo-thietanyl-Ci-C4 alkylene or dioxo-thietanyl- C1-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp
Cghaloalkylaminocarbonyl-Ci-C4 alkylene, or C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI .
Yet even more preferably R2 is CpCgalkyl or Ci-Cgalkyl substituted by one to three halogen atoms, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Ci-C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, thietanyl, oxo-thietanyl, dioxo-thietanyl, d- Cgalkylaminocarbonyl-methylene, Ci-Cghaloalkylaminocarbonyl-methylene, C3-Cgcycloalkyl- aminocarbonyl-methylene, or group CI . - o -
A group of preferred compounds are those wherein R2 is CpCealkyl or CpCealkyl substituted by one to five R6, for example ethyl-, butyl-, but-2-yl-, 3-bromo-propyl-, 2,2,2-trifluoro-ethyl-, 3,3,3- trifluoro-propyl-, 2-methoxy-ethyl-, and l-methoxy-prop-2-yl-.
A group of preferred compounds are those wherein R2 is C3-Cgcycloalkyl or C3-Cgcycloalkyl substituted by one to five R7, for example cyclobutyl-, 2-fluoro-cyclopropyl and 2-methyl-cyclohex-l-yl-.
A group of preferred compounds are those wherein R2 is aryl-Ci-C2alkylene- or aryl-Cr
C2alkylene- wherein the aryl moiety is substituted by one to five R8, for example phenyl-methyl-, 1 - phenyl-eth-l-yl-, 2-phenyl-eth-l-yl-, (3-chloro-phenyl)-methyl-, (2-fluoro-phenyl)-methyl-, (4-methoxy- phenyl)-methyl-, (2-trifluoromethyl-phenyl)-methyl-, and (2-trifluoromethoxy-phenyl)-methyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl-Ci-C2alkylene- or heterocyclyl-Ci-C2alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, for example (pyrid-2-yl)-methyl-, (pyrid-3-yl)-methyl-, (2-chloro-pyrid-5-yl)-methyl-, ( 1 -methyl- lH-imidazol-4-yl)- methyl-, (furan-2-yl)-methyl-, 2-(thiophen-2'-yl)-eth-l -yl-, 2-(indol-3'-yl)-eth-l-yl-, (lH-benzimidazol-2- yl)-methyl-, (oxetan-2-yl)-methyl-, (tetrahydrofuran-2-yl)-methyl-, 2-([l',3']dioxolan-2'-yl)-eth-l-yl-, 2- (morpholin-4'-yl)-eth-l-yl-, 2-(benzo[l',3']dioxol-5'-yl)-eth-l-yl-, (2,3-dihydro-benzo[l,4]dioxin-6-yl)- methyl-, thietan-2-yl-methyl-, 1 -oxo-thietan-2-yl-methyl-, 1 , 1 -dioxo-thietan-2-yl-methyl-, thietan-3-yl- methyl-, l-oxo-thietan-3-yl-methyl-, l,l-dioxo-thietan-3-yl-methyl-, thietan-3-yl-ethyl-, 1 -oxo-thietan-3 - yl-ethyl-, and l,l-dioxo-thietan-3-yl-ethyl-, preferably thietan-2-yl-methyl-, 1 -oxo-thietan-2-yl-methyl-, 1 , 1 -dioxo-thietan-2-yl-methyl-, thietane-3 -yl-methyl-, 1 -oxo-thietan-3 -yl-methyl-, 1 , 1 -dioxo-thietan-3 -yl- methyl-, thietan-3-yl-ethyl-, 1 -oxo-thietan-3 -yl-ethyl-, and l,l-dioxo-thietan-3-yl-ethyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl-Ci-C2alkylene- or heterocyclyl-Ci-C2alkylene- wherein the heterocyclyl moiety is substituted by one to five R8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
A group of preferred compounds are those wherein R2 is heteroaryl-Ci-C2alkylene- or heteroaryl- Ci-C2alkylene- wherein the heteroaryl moiety is substituted by one to five R8.
A group of preferred compounds are those wherein R2 is aryl or aryl substituted by one to five R8, for example 2-chloro-phenyl-, 3-fluoro-phenyl-, 2-methyl-phenyl-, 2-chloro-6-methyl-phenyl-, 2- trifluoromethyl-phenyl-, and 2,4-dimethoxy-phenyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl or heterocyclyl substituted by one to five R8, for example 3-methyl-pyrid-2-yl-, l,3-dimethyl-lH-pyrazol-5-yl-, 4-methyl-thiazol-2- yl-, 5-methyl-thiadiazol-2-yl-, quinolin-2-yl-, quinolin-5-yl-, benzothiazol-6-yl-, 4-methyl-benzothiazol- 2-yl-, thietan-3-yl-, 1 -oxo-thietan-3 -yl-, 1,1 -dioxo-thietan-3 -yl-, and 3-methyl-thietan-3-yl-, more preferably R2 is oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R8, most preferably R2 is thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R8. It is particularly preferred that the oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl ring is linked via the 3 -position.
A group of preferred compounds are those wherein R2 is heterocyclyl- or heterocyclyl substituted by one to five R8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl,
tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
A group of preferred compounds are those wherein R2 is
Figure imgf000010_0001
alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, or C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, more preferably Ci-C4alkylaminocarbonyl-Ci-C4 alkylene, Ci-C4haloalkylaminocarbonyl-Ci-C4 alkylene, or C3-C6cycloalkyl-aminocarbonyl-Ci-C4 alkylene, most preferably Ci-C4alkylaminocarbonyl-
C1-C2 alkylene or Ci-C4haloalkylaminocarbonyl-Ci-C2 alkylene.
A group of preferred compounds are those wherein R1 and R2 together represent group A
Figure imgf000010_0002
wherein G2 and G3 are as defined above, for example group Al, A2, A3 or A4
Figure imgf000010_0003
wherein R13, R14, R15, R16, R17, R18 and R19 are as defined above.
R13, R17, R18 and R19 are preferably Ci-C4alkyl, more preferably methyl or ethyl/
R14 and R15 are preferably hydrogen.
A group of preferred compounds are those wherein R2 is group CI .
A group of preferred compounds are those wherein R2 is group C2.
Figure imgf000010_0004
wherein L is a bond, methylene or ethylene; one of A1 and A2 is S, SO or S02 and the other is -C(R3a)R3a ; R3 is hydrogen or methyl; each R3a is independently hydrogen or methyl; and preferably L is a bond, preferably R3 and each R3a is hydrogen; preferably A1 is -C(R4)R4-, more preferably -CH2-; preferably A2 is S, SO or S02.
In one roup of compounds P is selected from PO and PI to P44 and R2 is group CI or C2
Figure imgf000011_0001
Figure imgf000011_0002
# N O # N S - O .
Y O Y NH2 Ί Y O Y NH2 Y 0 Y S\
P42 P43 P44 Preferably X4 is chlorodifluoromethyl or rifluoromethyl, most preferably trifluoromethyl.
Preferably R4 is aryl or aryl substituted by one to five R9, more preferably aryl substituted by one to three R9, more preferably phenyl substituted by one to three R9. In one group of compounds R is group (B)
Figure imgf000012_0001
wherein X2 is C-X6 or nitrogen (preferably C-X6); X1, X3 and X6 are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X1, X3 and X6 are not hydrogen; even more preferably R4 is 3,5-dichlorophenyl-, 3-chloro-4-fluorophenyl-, 3-fluoro-4-chlorophenyl-, 3,4- dichlorophenyl-, 3-chloro-4-bromophenyl-, 3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-, 3,5- dichloro-4-iodophenyl-, 3,4,5-trifluorophenyl-, 3-chloro-5-bromophenyl-, 3 -chloro-5 -fluorophenyl-, 3- chloro-5 -(trifluoromethyl)phenyl-, 3 ,4-dichloro-5 -(trifluoromethyl)phenyl-, 3,5- bis(trifluoromethyl)phenyl-, 4-chloro-3,5-bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-, 2,6- dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)-4-pyridyl-, more preferably 3-chloro-5-bromophenyl-, 3- chloro-5-(trifluoromethyl)phenyl-, 3,5-dichloro-4-fluorophenyl-, 3,4,5-trichlorophenyl-, 3,5- bis(trifluoromethyl)phenyl-, 3-(trifluoromethyl)phenyl-, 2,6-dichloro-4-pyridyl-, 2,6-bis(trifluoromethyl)- 4-pyridyl-, 3,5-dichloro-4-bromophenyl-, 3-bromo-5-(trifluoromethyl)phenyl-, 3,5-dibromophenyl-, or 3,4-dichlorophenyl-, even more preferably 3,5-dichloro-phenyl, 3,5-dichloro-4-fluorophenyl-, 3,4,5- trichlorophenyl-, 3,5-bis(trifluoromethyl)phenyl-, most preferably R4 is 3,5-dichloro-phenyl.
In one group of compounds R4 is 3,5-dichloro-phenyl. In one group of compounds R4 is 3,5- dichloro-4-fluorophenyl-. In one group of compounds R4 is 3,4,5-trichlorophenyl-. In one group of compounds R4 is 3,5-bis(trifluoromethyl)phenyl.
Preferably each R5 is independently halogen, cyano, nitro, NH2, CpCgalkyl, CpCghaloalkyl, C3- C5cycloalkyl, C3-C5halocycloalkyl, CpCgalkenyl, Ci-Cghaloalkenyl, CpCgalkoxy-, or CpCghaloalkoxy-, preferably halogen, cyano, nitro, NH2, Ci-C2alkyl, Ci-C2haloalkyl, C3-C5cycloalkyl, C3-C5halocycloalkyl, Ci-C2alkoxy, Ci-C2haloalkoxy; more preferably chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, even more preferably R5 is chloro, bromo, fluoro, methyl or trifluoromethyl, most preferably methyl.
In one group of compounds R5 is chloro. In one group of compounds R5 is bromo. In one group of compounds R5 is methyl. In one group of compounds R5 is halogen.
Preferably each R6 is independently halogen, cyano, nitro, hydroxy, CpCgalkoxy-, Cp
Cghaloalkoxy-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, mercapto, CpCgalkylthio-, Cp
Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, CpCgalkylsulfonyl-, or CpCghaloalkylsulfonyl-, more preferably each R6 is independently halogen, cyano, nitro, hydroxy, Cp Cgalkoxy-, CpCghaloalkoxy-, mercapto, Ci-Cgalkylthio-, CpCghaloalkylthio-, more preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy.
Preferably each R7 is independently halogen or CpCgalkyl, more preferably each R7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
Preferably each R8 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, C2- Cgalkenyl, C2-Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Cp Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10, more preferably each R8 is independently halogen, cyano, nitro, CpCgalkyl, CpCghaloalkyl, CpCgalkoxy-, Cp Cghaloalkoxy-, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably bromo, chloro, fluoro, cyano or methyl.
Preferably each R9 is independently halogen, CpCgalkyl, Ci-Cghaloalkyl, CpCgalkoxy-, Cp Cghaloalkoxy-, CpCgalkylthio-, or CpCghaloalkylthio-, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably bromo or chloro.
Preferably each R10 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
Preferably R11 is methyl, ethyl or trifluoroethyl.
Preferably each Z is independently halogen, cyano, CpC4alkyl,
Figure imgf000013_0001
CpC4alkoxy, or CpC ihaloalkoxy, more preferably each Z is independently hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
In one embodiment formula (Ia-1)
Figure imgf000013_0002
wherein G1, R1, R2, X4, R4 and R5 are as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for G1, R1, R2, X4, R4 and R5 are the same as the preferences set out
corresponding substituents of compounds of the formula (I).
In one embodiment E2 the present invention provides compounds of formula (Ia-2)
Figure imgf000014_0001
wherein G1, R1, R2, X4, and R4 are as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for G1, R1, R2, X4 and R4 are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
In a further embodiment E3 the resent invention provides compounds of formula (Ia-3)
Figure imgf000014_0002
wherein G , R , R , X , and R are as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for G1, R1, R2, X4 and R4 are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
In a further embo ds of formula (Ib-1)
Figure imgf000014_0003
wherein X , R and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for X4, R4, R5, and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
In a further embodiment E5 the resent invention provides compounds of formula (Ib-2)
Figure imgf000014_0004
wherein X and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for X4, R4 and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
In a further embodiment E6 the present invention provides compounds of formula (Ib-3)
Figure imgf000015_0001
wherein X and R are as defined for compounds of formula (I) and Het is selected from HI to H9 as defined for compounds of formula (I); or a salt or N-oxide thereof. The preferences for X4, R4 and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
In a further embodiment E7 the present invention provides compounds of formula (Ic)
Figure imgf000015_0002
wherein
P is as defined for compounds of formula I including preferred definitions thereof;
Y1 is C-R5b, CH or nitrogen;
Y2 and Y3 are independently CH or nitrogen;
wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y2 and Y3 are not both nitrogen;
R5 is hydrogen, halogen, cyano, nitro, NH2, Ci-C2alkyl, Ci-C2haloalkyl, C3-C5cycloalkyl, C3-
C5halocycloalkyl, Ci-C2alkoxy, Ci-C2haloalkoxy;
R5b when present together with R5 forms a -CH=CH-CH=CH- bridge;
X2 is C-X6 or nitrogen;
X1, X3 and X6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X1, X3 and X6 are not hydrogen;
X4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
In a further embodiment E8 the present invention provides compounds of formula (Ic) wherein R4, X1, X2, X3, X4 and X6 are as defined for the compounds of fomrula Ic and P is selected from PO and PI to P44; G1 is oxygen; R1 is hydrogen; R2 is Al or A2; L is a bond, methylene or ethylene; one of A1 and A2 is S, SO or S02 and the other is -C(R3a)R3a-; R3 is hydrogen or methyl; each R3a is independently hydrogen or methyl; R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl- methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R12; each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy. In a further embodiment E9 the present invention provides compounds of formula (Ic) wherein P is selected from P0 and PI to P44; G1 is oxygen; R1 is hydrogen; R2 is Al or A2; R3 and R3a are hydrogen; R5 is chloro, bromo, fluoro, methyl, trifluoromethyl; R11 is methyl, ethyl or trifluoroethyl; L is a bond; A1 is -CH2-; A2 is S, SO or S02; Y1 is CH, Y2 is CH, and Y3 is CH; X1, X3 and X6 are independently hydrogen, halogen or trifluoromethyl, wherein at least two of X1, X3 and X6 are not hydrogen; X2 is C-X6; X4 is trifluoromethyl, or chlorodifluoromethyl.
Certain intermediates are novel and as such form further aspects of the invention.
One group of novel intermediates are compounds of formula (Int-I)
Figure imgf000016_0001
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for a compound of formula (I), G1 is oxygen, and R is hydroxy, Ci-Ci5alkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof. The preferences for X4, R4, Y1, Y2, Y3 and Y4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I). Preferably R is hydroxy, CpCealkoxy or chloro.
A further group of novel intermediates are compounds of formula (Int-II)
Figure imgf000016_0002
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for a compound of formula (I), and XB is a leaving group such as halogen, CpCgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, CpCgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride; or a salt or N-oxide thereof. The preferences for X4, R4, Y1, Y2, Y3 and Y4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
A further group of novel intermediates are compounds of formula (Int-III)
Figure imgf000016_0003
wherein Y1, Y2, Y3 and Y4 are as defined for compounds of formula (I), Px is P as defined above, a leaving group, such as halogen, Ci-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Cp Cgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium Λ ,
- 16 - salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2, wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof. The preferences for Y1, Y2, Y3 and Y4 and the preferences at position Px when Px is P or heterocycle are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
A group of compounds of formula (Int-III) are compounds of formula (Int-IV)
Figure imgf000017_0001
wherein Y , Y Y\ Y1, R and R" are as defined for compounds of formula (I). The preferences for Y , Y2, Y3, Y4, R1 and R2 are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
Another group of compounds of formula (Int-III) are compounds of formula (Int-V)
Figure imgf000017_0002
wherein Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for substituent P of compounds of formula I. The preferences for Y1, Y2, Y3 and Y4 and Pn are the same as the preferences set out for the corresponding substituents of a compound of formula (I).
A further group of novel intermediates are compounds of formula (Int-VI)
Figure imgf000017_0003
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III), Z1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C4alkylene-, CpCgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio-, or a salt or N-oxide thereof. The preferences for X4, R4, Y1, Y2, Y3 and Y4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I). Z1 is preferably hydrogen, benzyl, halogen (preferably chloro) or cyano. Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C4alkyl, C1-C4 haloalkyl, Ci-C4alkoxy or Ci-C4haloalkoxy. A further group of novel intermediates are compounds of formula (Int-VII)
Figure imgf000018_0001
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III), Z1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C4alkylene-, CpCgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio- and Z2 is hydrogen or hydroxyl or CpCgalkoxy- or CpCgalkylsulfonyloxy- or arylsulfonyloxy- or aryl-Ci-C4alkylene-or aryl. The preferences for X4, R4, Y1, Y2, Y3 and Y4 are the same as the preferences set out for the corresponding substituents of a compound of formula (I). Z1 is preferably hydrogen, benzyl, halogen (preferably chloro) or cyano. Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C4alkyl, C1-C4 haloalkyl, Ci-C4alkoxy or Ci-C4haloalkoxy.
A further group of novel intermediates are compounds of formula (Int-VIII)
Figure imgf000018_0002
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I), and Px is as defined for the compound of formula (Int-III), and Z3 is thiol or optionally substituted aryl-Ci-Cgalkylsulfinyl-. The preferences for X4, R4, Y1, Y2, Y3 and Y4 are the same as the preferences set out for the
corresponding substituents of a compound of formula (I). Aryl is preferably phenyl and is preferably optionally substituted by one or more groups selected from halogen, cyano, Ci-C4alkyl, C1-C4 haloalkyl, Ci-C4alkoxy or Ci-C4haloalkoxy.
Compounds of formula I include at least one chiral centre and may exist as compounds of
Figure imgf000018_0003
Generally compounds of formula I** are more biologically active than compounds of formula I*. The invention includes mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to - l o -
99: 1, e.g. 10:1 to 1 : 10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula I**, the molar proportion of compound I** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90,
95, 96, 97, 98, or at least 99%. Likewise, in enantiomerically (or epimerically) enriched mixture of formula I*, the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95,
96, 97, 98, or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred. Each compound disclosed in Tables 1P-120P and Tables 1Q to 240Q represents a disclosure of a compound according to the compound of formula I*, and a disclosure according to the compound of formula I**.
Table G
Group number R2
G.001 ethyl-
G.002 butyl-
G.003 but-2-yl-
G.004 3-bromo-propyl-
G.005 2,2,2-trifluoro-ethyl-
G.006 3,3,3 -trifluor o-propyl-
G.007 2-methoxy-ethyl-
G.008 1 -methoxy-prop-2-yl-
G.009 cyclobutyl-
G.010 2-methyl-cyclohex- 1 -yl-
G.011 phenyl-methyl-
G.012 1 -phenyl- eth- 1 -yl-
G.013 2-phenyl-eth- 1 -yl-
G.014 (3 -chloro-phenyl)-methyl-
G.015 (2-fluoro-phenyl)-methyl-
G.016 (4-methoxy-phenyl)-methyl-
G.017 (2-trifluoromethyl-phenyl)-methyl-
G.018 (2-trifluoromethoxy-phenyl)-methyl-
G.019 (pyrid-2-yl)-methyl-
G.020 (pyrid-3-yl)-methyl-
G.021 (2-chloro-pyrid-5-yl)-methyl-
G.022 (l-methyl-lH-imidazol-4-yl)-methyl-
G.023 (furan-2-yl)-methyl-
G.024 2-(thiophen-2'-yl)-eth- 1 -yl-
G.025 2-(indol-3'-yl)-eth-l-yl-
G.026 (lH-benzimidazol-2-yl)-methyl-
G.027 (oxetan-2-yl)-methyl-
G.028 (tetrahydrofuran-2-yl)-methyl-
G.029 2-([l',3']dioxolan-2'-yl)-eth-l-yl- Λ n
Group number R2
G.030 2-(morpholin-4'-yl)-eth-l -yl-
G.031 2-(benzo[l',3']dioxol-5'-yl)-eth-l -yl-
G.032 (2,3 -dihydro-benzo [ 1 ,4] dioxin-6-yl)-methyl-
G.033 2-chloro-phenyl-
G.034 3-fluoro-phenyl-
G.035 2-methyl-phenyl-
G.036 2-chloro-6-methyl-phenyl-
G.037 2-trifluoromethyl-phenyl-
G.038 2,4-dimethoxy-phenyl-
G.039 3 -methyl-pyrid-2-yl-
G.040 l,3-dimethyl-lH-pyrazol-5-yl-
G.041 4-methyl-thiazol-2-yl-
G.042 5-methyl-thiadiazol-2-yl-
G.043 quinolin-2-yl-
G.044 quinolin-5-yl-
G.045 benzothiazol-6-yl-
G.046 4-methyl-benzothiazol-2-yl-
G.047 thietan-3-yl-
G.048 1 -oxo-thietan-3-yl-
G.049 1 , 1 -dioxo-thietan-3-yl-
G.050 3 -methyl-thietan-3 -yl-
G.051 N-(2,2,2-Trifluoro-ethyl)-acetamide-2-yl
G.052 thietan-2-yl-methyl-
G.053 1 -oxo-thietan-2-yl-methyl-
G.054 1 , 1 -dioxo-thietan-2-yl-methyl-
G.055 thietan-3 -yl-methyl-
G.056 1 -oxo-thietan-3 -yl-methyl-
G.057 1 , 1 -dioxo-thietan-3 -yl-methyl-
G.058 thietan-3-yl-ethyl-
G.059 1 -oxo-thietan-3-yl-ethyl-
G.060 1 , 1 -dioxo-thietan-3-yl-ethyl-
G.061 2-fluoro-cyclopropyl
G.062 n-Butyl
G.063 2-Methoxy- 1 -methyl- ethyl
G.064 1 -Oxo-thietan-3 -yl
G.065 2-ethyl-isoxazolidin-3-one-4-yl
G.066 Dihydro-thiophen-2-one-3-yl
G.067 6-Ethoxycarbonyl-cyclohex-3-enyl
G.068 2-B enzylsulfanyl- ethyl
G.069 4-Methanesulfonyl-benzyl
G.070 Ν',Ν'-Dimethylamino- ethyl
G.071 sec-Butyl
G.072 Butan-l-ol-2-yl „Λ
Group number R2
G.073 2,2-Difluoro-ethyl
G.074 Ethynyl-cyclohexyl
G.075 2-Morpholin-4-yl-ethyl
G.076 3 -Pyrrolidin- 1 -yl-propyl
G.077 3 -Piperidin- 1 -yl-propyl
G.078 [3-(4-Chloro-phenyl)-isoxazol-5-yl]-methyl
G.079 Phenethyl
G.080 l,2,2,6,6-Pentamethyl-piperidin-4-yl
G.081 2-Phenoxy-ethyl
G.082 3-Chloro-benzyl
G.083 2-Acetylamino-ethyl
G.084 4-Pyrazol- 1 -yl-benzyl
G.085 2-Methylsulfanyl-ethyl
G.086 2-Piperidin- 1 -yl-benzyl
G.087 4-Phenoxy-benzyl
G.088 (6-Chloro-pyridin-3 -yl)-methyl
G.089 1 -Benzyl-pyrrolidin-3-yl
G.090 2-(4-Benzyl-piperazin- 1 -yl)-ethyl
G.091 Furan-2-yl-methyl
G.092 lH-Indazol-5-yl
G.093 4-Pyrrol- 1 -yl-phenyl
G.094 4-Piperidin- 1 -yl-phenyl
G.095 2-Methylsulfanyl-phenyl
G.096 4-Methyl-2-oxo-2H-chromen-7-yl
G.097 4-Dimethylsulfamoyl-phenyl
G.098 2,5-Dimethyl-2H-pyrazol-3-yl
G.099 5-Methylsulfanyl-lH-[l,2,4]triazol-3-yl
G.100 4-Hydroxy-6-methyl-pyrimidin-2-yl
G.101 Quinolin-2-yl
G.102 5-Methyl-3-phenyl-isoxazol-4-yl
G.103 9H-Purin-6-yl
G.104 5-Acetyl-4-methyl-thiazol-2-yl
G.105 4-Methyl-benzothiazol-2-yl
G.106 5-Methyl-[l,3,4]thiadiazol-2-yl
G.107 4,6-Dimethyl-2H-pyrazolo[3,4-b]pyridin-3-yl
G.108 3-(2,2,2-Trifluoro-ethoxyimino)-cyclobutyl
G.109 2-Thietan-3 -yl-ethyl
G.110 2-(l , 1 -Dioxo-thietan-3-yl)-ethyl
G. l l l 3-Oxo-2-(2,2,2-trifluoro-ethyl)-isoxazolidin-4-yl
\ o^
G.112 H „ Λ
Figure imgf000022_0001
Table P
XI, X2, X3 X4 R5 Yl, Y2, Y3
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0001 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0002 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0003 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0004 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0005 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0006 chloro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0007 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0008 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0009 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0010 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0011 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0012 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0013 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0014 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0015 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0016 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0017 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0018 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0019 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0020 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0021 chloro difluoromethyl methyl CH, Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0022 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0023 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0024 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0025 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0026 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0027 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0028 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0029 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0030 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0031 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0032 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0033 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0034 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0035 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0036 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0037 hydrogen chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0038 hydrogen chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0039 hydrogen chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0040 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0041 hydrogen chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0042 hydrogen chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0043 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0044 hydrogen chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0045 hydrogen chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0046 hydrogen chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0047 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0048 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
P.0049 X1 is chloro, X2 is C-F, X3 is difluoromethyl bromo Y1 is CH, Y2 is „„ hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0050 hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0051 hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0052 hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0053 hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0054 hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0055 hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0056 hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0057 hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0058 hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0059 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0060 hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0061 hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0062 hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0063 hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0064 hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0065 hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0066 hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0067 hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0068 hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0069 hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0070 hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0071 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0072 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0073 hydrogen chlorodifluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0074 hydrogen chlorodifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0075 hydrogen chlorodifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0076 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is CH „ Λ
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0077 hydrogen chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0078 hydrogen chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0079 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0080 hydrogen chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0081 hydrogen chlorodifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is
P.0082 hydrogen chlorodifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is
P.0083 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0084 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0085 hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0086 hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is
P.0087 hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0088 hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0089 hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0090 hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0091 hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0092 hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0093 hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0094 hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0095 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0096 hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0097 hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0098 hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0099 hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0100 hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0101 hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0102 hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0103 hydrogen trifluoromethyl hydrogen CH, Y3 is CH
P.0104 X1 is fluoro, X2 is C-Cl, X3 is trifluoromethyl methoxy Y1 is CH, Y2 is „r hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0105 hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0106 hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0107 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0108 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0109 hydrogen chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0110 hydrogen chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0111 hydrogen chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0112 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.01 13 hydrogen chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0114 hydrogen chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0115 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0116 hydrogen chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.01 17 hydrogen chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0118 hydrogen chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0119 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0120 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0121 hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0122 hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0123 hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0124 hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0125 hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0126 hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0127 hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0128 hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0129 hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0130 hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0131 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH „^
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0132 hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0133 hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0134 hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0135 hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0136 hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0137 hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0138 hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0139 hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0140 hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0141 hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0142 hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0143 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0144 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0145 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0146 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0147 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0148 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0149 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0150 chloro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0151 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0152 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0153 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0154 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0155 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0156 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0157 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0158 chloro difluoromethyl chloro CH, Y3 is CH
P.0159 X1 is chloro, X2 is C-Br, X3 is difluoromethyl cyano Y1 is CH, Y2 is chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0160 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0161 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0162 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0163 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0164 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0165 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0166 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0167 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0168 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0169 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0170 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0171 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0172 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0173 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0174 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0175 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0176 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0177 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0178 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0179 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.0180 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0181 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0182 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0183 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0184 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0185 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0186 chloro chlorodifluoromethyl fluoro CH, Y3 is CH „n
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0187 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0188 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0189 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0190 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0191 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0192 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0193 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0194 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0195 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0196 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0197 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0198 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0199 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0200 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0201 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0202 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0203 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0204 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0205 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0206 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0207 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0208 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0209 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0210 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0211 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0212 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0213 chloro trifluoromethyl methyl CH, Y3 is CH
P.0214 X1 is chloro, X2 is C-F, X3 is trifluoromethyl nitro Y1 is CH, Y2 is „n chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0215 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0216 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0217 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0218 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0219 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0220 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0221 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0222 chloro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0223 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0224 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0225 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0226 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0227 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0228 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0229 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0230 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0231 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0232 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0233 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0234 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0235 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0236 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0237 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0238 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0239 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0240 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0241 chloro trifluoromethyl bromo CH, Y3 is CH „Λ
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0242 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0243 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0244 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0245 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0246 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0247 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0248 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0249 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0250 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0251 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0252 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0253 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0254 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0255 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0256 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0257 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0258 chloro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0259 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0260 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0261 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0262 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0263 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0264 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0265 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0266 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0267 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0268 chloro difluoromethyl cyclopropyl CH, Y3 is CH
P.0269 X1 is chloro, X2 is C-I, X3 is difluoromethyl ethyl Y1 is CH, Y2 is „ Λ chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0270 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0271 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0272 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0273 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0274 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0275 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0276 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0277 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0278 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0279 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0280 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0281 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0282 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0283 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0284 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0285 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0286 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0287 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0288 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0289 fluoro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0290 fluoro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0291 fluoro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0292 fluoro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0293 fluoro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0294 fluoro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0295 fluoro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0296 fluoro chlorodifluoromethyl methoxy CH, Y3 is CH X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0297 fluoro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0298 fluoro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0299 fluoro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0300 fluoro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0301 fluoro difluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0302 fluoro difluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0303 fluoro difluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0304 fluoro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0305 fluoro difluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0306 fluoro difluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0307 fluoro difluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0308 fluoro difluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0309 fluoro difluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0310 fluoro difluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0311 fluoro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0312 fluoro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0313 fluoro trifluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0314 fluoro trifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0315 fluoro trifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0316 fluoro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0317 fluoro trifluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0318 fluoro trifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0319 fluoro trifluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0320 fluoro trifluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0321 fluoro trifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0322 fluoro trifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0323 fluoro trifluoromethyl trifluoromethoxy CH, Y3 is CH
P.0324 X1 is fluoro, X2 is C-F, X3 is trifluoromethyl trifluoromethyl Y1 is CH, Y2 is „„ fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0325 bromo chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0326 bromo chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0327 bromo chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0328 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0329 bromo chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0330 bromo chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0331 bromo chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0332 bromo chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0333 bromo chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0334 bromo chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0335 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0336 bromo chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0337 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0338 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0339 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0340 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0341 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0342 bromo difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0343 bromo difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0344 bromo difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0345 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0346 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0347 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0348 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0349 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0350 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0351 bromo trifluoromethyl cyano CH, Y3 is CH „„
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0352 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0353 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0354 bromo trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0355 bromo trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0356 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0357 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0358 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0359 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0360 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0361 bromo chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0362 bromo chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0363 bromo chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0364 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0365 bromo chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0366 bromo chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0367 bromo chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0368 bromo chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0369 bromo chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0370 bromo chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0371 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0372 bromo chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0373 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0374 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0375 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0376 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0377 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0378 bromo difluoromethyl fluoro CH, Y3 is CH
P.0379 X1 is chloro, X2 is CH, X3 is difluoromethyl hydrogen Y1 is CH, Y2 is „ r bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0380 bromo difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0381 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0382 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0383 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0384 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0385 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0386 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0387 bromo trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0388 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0389 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0390 bromo trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0391 bromo trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0392 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0393 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0394 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0395 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0396 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0397 bromo chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0398 bromo chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0399 bromo chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0400 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0401 bromo chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0402 bromo chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0403 bromo chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0404 bromo chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0405 bromo chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0406 bromo chlorodifluoromethyl nitro CH, Y3 is CH „ r
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0407 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0408 bromo chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0409 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0410 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0411 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0412 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0413 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0414 bromo difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0415 bromo difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0416 bromo difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0417 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0418 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0419 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0420 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0421 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0422 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0423 bromo trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0424 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0425 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0426 bromo trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0427 bromo trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0428 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0429 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0430 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0431 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0432 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0433 trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is CH
P.0434 X1 is chloro, X2 is C-Cl, X3 is chlorodifluoromethyl chloro Y1 is CH, Y2 is trifluoromethyl CH, Y" is CH
X1 is chloro, X2 is C-Cl, XJ is Y1 is CH, Y2 is
P.0435 trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, XJ is Y1 is CH, Y2 is
P.0436 trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0437 trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0438 trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0439 trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0440 trifluoromethyl chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0441 trifluoromethyl chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0442 trifluoromethyl chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0443 trifluoromethyl chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0444 trifluoromethyl chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0445 trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0446 trifluoromethyl difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0447 trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0448 trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0449 trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0450 trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0451 trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0452 trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0453 trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0454 trifluoromethyl difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0455 trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0456 trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0457 trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0458 trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0459 trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0460 trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0461 trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH X1 is chloro, X is C-Cl, X3 is Y1 is CH, Y2 is
P.0462 trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0463 trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0464 trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0465 trifluoromethyl trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0466 trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.0467 trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.0468 trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0469 X3 is trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0470 X3 is trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~ i*s CH, Y1 is CH, Y2 is
P.0471 X3 is trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~ i*s CH, Y1 is CH, Y2 is
P.0472 XI is trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0473 X3 is trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0474 X3 is trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0475 X3 is trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~ i*s CH, Y1 is CH, Y2 is
P.0476 X3 is trifluoromethyl chlorodifluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X is CH, Y1 is CH, Y2 is
P.0477 X3 is trifluoromethyl chlorodifluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X is CH, Y1 is CH, Y2 is
P.0478 X3 is trifluoromethyl chlorodifluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0479 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0480 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0481 X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~~ i's CH, Y1 is CH, Y2 is
P.0482 X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~~ i's CH, Y1 is CH, Y2 is
P.0483 X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0484 X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0485 X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0486 X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0487 X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
— X I is trifluoromethyl, X 7∑~~ i's CH, Y1 is CH, Y2 is
P.0488 X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
P.0489 X1 is trifluoromethyl, X2 is CH, difluoromethyl methyl Y1 is CH, Y2 is ΛΛ
Figure imgf000040_0001
λ η
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0517 X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0518 X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0519 X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0520 X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0521 X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0522 X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0523 X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0524 X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0525 X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0526 X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0527 X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0528 X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0529 X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0530 X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0531 X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0532 X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0533 X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0534 X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0535 X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0536 X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0537 X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0538 X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0539 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0540 X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0541 X3 is hydrogen chlorodifluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0542 X3 is hydrogen chlorodifluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0543 X3 is hydrogen chlorodifluoromethyl cyano CH, Y3 is CH
P.0544 X1 is trifluoromethyl, X2 is CH, chlorodifluoromethyl cyclopropyl Y1 is CH, Y2 is . ,
XJ is hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0545 X3 is hydrogen chlorodifluoromethyl ethyl CH, Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0546 X3 is hydrogen chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0547 XJ is hydrogen chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0548 X3 is hydrogen chlorodifluoromethyl methoxy CH, Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0549 X3 is hydrogen chlorodifluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0550 X1 is hydrogen chlorodifluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0551 X3 is hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0552 X3 is hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0553 X1 is hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0554 X3 is hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0555 X3 is hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0556 X1 is hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0557 X3 is hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0558 X3 is hydrogen difluoromethyl fluoro CH, Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0559 X3 is hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0560 X5 is hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0561 X3 is hydrogen difluoromethyl methyl CH, Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.0562 X3 is hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0563 X1 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0564 X3 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0565 X3 is hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0566 X1 is hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0567 X3 is hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0568 X3 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0569 X1 is hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0570 X3 is hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0571 X3 is hydrogen trifluoromethyl hydrogen CH, Y3 is CH X 1 is trifluoromethyl, X 2 is CH, Y1 is CH, Y2 is
P.0572 X3 is hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0573 X3 is hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0574 X3 is hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0575 X3 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.0576 X3 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0577 chloro chlorodifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0578 chloro chlorodifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0579 chloro chlorodifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0580 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0581 chloro chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0582 chloro chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0583 chloro chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0584 chloro chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0585 chloro chlorodifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0586 chloro chlorodifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0587 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0588 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0589 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0590 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0591 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0592 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0593 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0594 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0595 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0596 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0597 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0598 chloro difluoromethyl nitro CH, Y3 is CH
P.0599 X1 is chloro, X2 is N, X3 is difluoromethyl trifluoromethoxy Y1 is CH, Y2 is „„ chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0600 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0601 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0602 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0603 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0604 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0605 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0606 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0607 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0608 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0609 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0610 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0611 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0612 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0613 X3 is trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0614 X3 is trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0615 X3 is trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0616 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0617 X3 is trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0618 X3 is trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0619 X3 is trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0620 X3 is trifluoromethyl chlorodifluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0621 X3 is trifluoromethyl chlorodifluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0622 X3 is trifluoromethyl chlorodifluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0623 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0624 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0625 X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.0626 X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH Λ Λ
Figure imgf000045_0001
chloro Y' is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0655 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0656 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0657 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0658 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0659 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0660 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0661 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0662 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0663 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0664 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0665 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0666 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0667 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0668 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0669 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0670 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0671 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0672 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0673 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0674 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0675 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0676 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0677 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0678 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0679 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0680 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0681 chloro trifluoromethyl methyl Y3 is CH A r
X1 is chloro, X2 is CH, X3 is Y is N, Y2 is CH,
P.0682 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0683 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0684 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0685 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, XJ is Y1 is N, Y2 is CH,
P.0686 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0687 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0688 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0689 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0690 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0691 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0692 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0693 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0694 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0695 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0696 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0697 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0698 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0699 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0700 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0701 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0702 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0703 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0704 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0705 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0706 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0707 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0708 hydrogen difluoromethyl trifluoromethyl Y3 is CH
P.0709 X1 is chloro, X2 is C-F, X3 is trifluoromethyl bromo Y1 is N, Y2 is CH, hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0710 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.071 1 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0712 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0713 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0714 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is N, Y2 is CH,
P.0715 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X is C-F, X3 is Y1 is N, Y2 is CH,
P.0716 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0717 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0718 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is N, Y2 is CH,
P.0719 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is N, Y2 is CH,
P.0720 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0721 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0722 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0723 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0724 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0725 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0726 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0727 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0728 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0729 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0730 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0731 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0732 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0733 hydrogen difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0734 hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0735 hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y- is CH,
P.0736 hydrogen difluoromethyl cyclopropyl Y3 is CH „0
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0737 hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0738 hydrogen difluoroniethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0739 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X- is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0740 hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0741 hydrogen difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0742 hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0743 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0744 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0745 hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0746 hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0747 hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0748 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0749 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0750 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0751 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0752 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0753 hydrogen trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0754 hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0755 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0756 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0757 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0758 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0759 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0760 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0761 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0762 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0763 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
P.0764 X1 is chloro, X2 is C-Cl, X3 is chlorodifluoromethyl methoxy Y1 is N, Y2 is CH, Λ η hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0765 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0766 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0767 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0768 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0769 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0770 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0771 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0772 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0773 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0774 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0775 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0776 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0777 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0778 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0779 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0780 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0781 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0782 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0783 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0784 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0785 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0786 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0787 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0788 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0789 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0790 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0791 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH c n
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0792 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0793 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0794 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0795 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0796 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0797 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0798 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0799 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0800 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0801 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0802 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0803 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0804 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0805 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0806 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0807 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0808 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0809 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0810 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0811 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0812 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0813 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0814 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0815 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0816 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0817 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0818 chloro trifluoromethyl chloro Y3 is CH
P.0819 X1 is chloro, X2 is C-Br, X3 is trifluoromethyl cyano Y1 is N, Y2 is CH, Γ Λ chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0820 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
P.0821 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0822 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0823 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0824 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0825 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0826 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0827 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is CH,
Ρ.0828 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0829 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0830 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0831 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0832 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0833 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0834 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0835 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0836 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0837 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0838 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0839 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0840 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0841 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0842 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0843 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0844 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0845 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
Ρ.0846 chloro difluoromethyl fluoro Y3 is CH X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0847 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0848 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0849 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0850 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0851 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0852 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0853 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0854 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0855 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0856 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0857 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0858 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0859 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0860 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0861 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0862 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0863 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0864 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0865 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0866 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0867 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0868 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0869 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0870 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0871 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0872 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0873 chloro chlorodifluoromethyl methyl Y3 is CH
P.0874 X1 is chloro, X2 is C-Cl, X3 is chlorodifluoromethyl nitro Y1 is N, Y2 is CH, ^ chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0875 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0876 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0877 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0878 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0879 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0880 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0881 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0882 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0883 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0884 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0885 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0886 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0887 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0888 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0889 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0890 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0891 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0892 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0893 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0894 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0895 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0896 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0897 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0898 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0899 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.0900 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0901 chloro chlorodifluoromethyl bromo Y3 is CH Γ Λ
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0902 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0903 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0904 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0905 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0906 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0907 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0908 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0909 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0910 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0911 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0912 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0913 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0914 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0915 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0916 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0917 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0918 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0919 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0920 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0921 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0922 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0923 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0924 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0925 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0926 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0927 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
Ρ.0928 chloro trifluoromethyl cyclopropyl Y3 is CH
Ρ.0929 X1 is chloro, X2 is C-I, X3 is trifluoromethyl ethyl Y1 is N, Y2 is CH, Γ Γ chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0930 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0931 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0932 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0933 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0934 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0935 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0936 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0937 fluoro chlorodifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0938 fluoro chlorodifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0939 fluoro chlorodifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0940 fluoro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0941 fluoro chlorodifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0942 fluoro chlorodifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0943 fluoro chlorodifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0944 fluoro chlorodifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0945 fluoro chlorodifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0946 fluoro chlorodifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0947 fluoro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0948 fluoro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0949 fluoro difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0950 fluoro difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0951 fluoro difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0952 fluoro difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0953 fluoro difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0954 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0955 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0956 fluoro difluoromethyl methoxy Y3 is CH r r
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0957 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0958 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0959 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0960 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0961 fluoro trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0962 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0963 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0964 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0965 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0966 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0967 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0968 fluoro trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0969 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0970 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0971 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0972 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0973 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0974 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0975 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0976 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0977 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0978 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0979 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0980 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0981 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0982 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0983 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
P.0984 X1 is chloro, X2 is CH, X3 is chlorodifluoromethyl trifluoromethyl Y1 is N, Y2 is CH, „ bromo Y3 is CH
X1 is chloro, X is CH, X3 is Y1 is N, Y2 is CH,
P.0985 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0986 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X' is CH, X3 is Y1 is N, Y2 is CH,
P.0987 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0988 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0989 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X is CH, X3 is Y1 is N, Y2 is CH,
P.0990 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0991 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0992 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0993 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0994 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0995 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0996 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0997 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0998 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0999 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1000 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1001 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1002 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1003 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1004 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1005 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1006 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1007 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1008 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1009 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1010 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1011 bromo chlorodifluoromethyl cyano Y3 is CH ,n
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1012 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1013 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1014 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1015 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1016 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1017 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1018 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1019 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1020 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1021 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1022 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1023 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1024 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1025 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1026 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1027 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1028 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1029 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1030 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1031 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1032 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1033 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1034 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1035 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1036 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1037 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1038 bromo trifluoromethyl fluoro Y3 is CH
P.1039 X1 is chloro, X2 is CH, X3 is trifluoromethyl hydrogen Y1 is N, Y2 is CH, ^ bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1040 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1041 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1042 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1043 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1044 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1045 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1046 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1047 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1048 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1049 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1050 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1051 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1052 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1053 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1054 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1055 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1056 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1057 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1058 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1059 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1060 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1061 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1062 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1063 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1064 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1065 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1066 bromo difluoromethyl nitro Y3 is CH ^
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1067 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1068 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1069 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1070 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1071 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1072 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1073 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1074 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1075 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1076 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1077 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1078 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1079 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1080 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1081 trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1082 trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1083 trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1084 trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1085 trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1086 trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1087 trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1088 trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1089 trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1090 trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1091 trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1092 trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1093 trifluoromethyl difluoromethyl bromo Y3 is CH
P.1094 X1 is chloro, X2 is C-Cl, X3 is difluoromethyl chloro Y1 is N, Y2 is CH, trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1095 trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1096 trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1097 trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1098 trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1099 trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 100 trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 101 trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 102 trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 103 trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 104 trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 105 trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 106 trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 107 trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 108 trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 109 trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 10 trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P. l l l l trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 12 trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 13 trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 14 trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 15 trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is CH,
P.1 1 16 trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X is trifluoromethyl, X is CH, Y1 is N, Y2 is CH,
P.1 1 17 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 1 18 X' is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X is trifluoromethyl, X is CH, Y1 is N, Y2 is CH,
P.1 1 19 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 120 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X is trifluoromethyl, X is CH, Y1 is N, Y2 is CH,
P.1 121 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH ^„
Figure imgf000063_0001
X3 is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 150 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 151 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 152 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1153 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 154 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 155 X1 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 156 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 157 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 158 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 159 XJ is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 160 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 161 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 162 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 163 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 164 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 165 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 166 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 167 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 168 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 169 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 170 X1 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 171 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 172 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 173 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 174 X1 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 175 X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 176 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH r Λ
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 177 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 178 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 179 X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 180 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 181 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 182 X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 183 X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 184 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 185 X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 186 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 187 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 188 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 189 X3 is hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 190 X3 is hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 191 X3 is hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 192 X3 is hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 193 X3 is hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 194 X3 is hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 195 X3 is hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 196 X3 is hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 197 X3 is hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 198 X3 is hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1 199 X3 is hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1200 X3 is hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1201 X3 is hydrogen difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1202 X3 is hydrogen difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is CH,
P.1203 X3 is hydrogen difluoromethyl cyano Y3 is CH
P.1204 X1 is trifluoromethyl, X2 is CH, difluoromethyl cyclopropyl Y1 is N, Y2 is CH, rr
Figure imgf000066_0001
^
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1232 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1233 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1234 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1235 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1236 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1237 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1238 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1239 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1240 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1241 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1242 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1243 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1244 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1245 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1246 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1247 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1248 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1249 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1250 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1251 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1252 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1253 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1254 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1255 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1256 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1257 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1258 chloro trifluoromethyl nitro Y3 is CH
P.1259 X1 is chloro, X2 is N, X3 is trifluoromethyl trifluoromethoxy Y1 is N, Y2 is CH, chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1260 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1261 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1262 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1263 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1264 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1265 X1 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1266 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1267 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1268 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1269 X" is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1270 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1271 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1272 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1273 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1274 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1275 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1276 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1277 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1278 X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1279 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1280 X' is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1281 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1282 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1283 X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1284 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1285 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1286 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH ^n
X 1 is trifluoromethyl, X 2 is N, Y1 is N, Y2 is CH,
P.1287 X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1288 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1289 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1290 X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1291 X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1292 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1293 X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1294 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1295 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is CH,
P.1296 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1297 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1298 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1299 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1300 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1301 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1302 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1303 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1304 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1305 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1306 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1307 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1308 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1309 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1310 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1311 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1312 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1313 chloro difluoromethyl ethyl Y3 is CH
P.1314 X1 is chloro, X2 is CH, X3 is difluoromethyl fluoro Y1 is N, Y2 is N, chloro Y' is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1315 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1316 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1317 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1318 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1319 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1320 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1321 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1322 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1323 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1324 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1325 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1326 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1327 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1328 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1329 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1330 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1331 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1332 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1333 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1334 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1335 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1336 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1337 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1338 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1339 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1340 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1341 hydrogen chlorodifluoromethyl methyl Y3 is CH „Λ
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1342 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1343 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1344 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X" is C-F, X3 is Y1 is N, Y2 is N,
P.1345 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1346 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1347 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1348 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1349 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1350 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1351 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1352 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1353 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1354 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1355 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1356 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1357 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1358 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1359 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1360 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1361 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1362 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1363 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1364 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1365 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1366 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1367 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1368 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
P.1369 X1 is fluoro, X2 is C-Cl, X3 is chlorodifluoromethyl bromo Y1 is N, Y2 is N, 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1370 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1371 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1372 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1373 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1374 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1375 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1376 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1377 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1378 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1379 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1380 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1381 hydrogen difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1382 hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1383 hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1384 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1385 hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1386 hydrogen difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1387 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1388 hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1389 hydrogen difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1390 hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1391 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1392 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1393 hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1394 hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1395 hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1396 hydrogen trifluoromethyl cyclopropyl Y3 is CH X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1397 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1398 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X4 is Y1 is N, Y2 is N,
P.1399 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1400 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1401 hydrogen trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1402 hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1403 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1404 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1405 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1406 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1407 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1408 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1409 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1410 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.141 1 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1412 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1413 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1414 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1415 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1416 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1417 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1418 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1419 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1420 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1421 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1422 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1423 hydrogen difluoromethyl hydrogen Y3 is CH
P.1424 X1 is chloro, X2 is C-Cl, X3 is difluoromethyl methoxy Y1 is N, Y2 is N, ^ hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1425 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X is C-Cl, X3 is Y1 is N, Y2 is N,
P.1426 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X' is C-Cl, X3 is Y1 is N, Y2 is N,
P.1427 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1428 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1429 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1430 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1431 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1432 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1433 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1434 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1435 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1436 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1437 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1438 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1439 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1440 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1441 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1442 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1443 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1444 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1445 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1446 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1447 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1448 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1449 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1450 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1451 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH „
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1452 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1453 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1454 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1455 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1456 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1457 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1458 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1459 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1460 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1461 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1462 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1463 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1464 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1465 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1466 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1467 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1468 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1469 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1470 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1471 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1472 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1473 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1474 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1475 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is N, Y2 is N,
P.1476 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1477 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1478 chloro chlorodifluoromethyl chloro Y3 is CH
P.1479 X1 is chloro, X2 is C-F, X3 is chlorodifluoromethyl cyano Y1 is N, Y2 is N, chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1480 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1481 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1482 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1483 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1484 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1485 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1486 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1487 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1488 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1489 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1490 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1491 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1492 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1493 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1494 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1495 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1496 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1497 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1498 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1499 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1500 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1501 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1502 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1503 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1504 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1505 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1506 chloro trifluoromethyl fluoro Y3 is CH „^
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1507 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1508 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1509 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1510 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1511 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1512 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1513 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1514 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1515 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1516 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1517 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1518 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1519 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1520 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1521 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1522 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1523 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1524 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1525 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1526 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1527 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1528 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1529 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1530 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1531 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1532 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1533 chloro difluoromethyl methyl Y3 is CH
P.1534 X1 is chloro, X2 is C-Cl, X3 is difluoromethyl nitro Y1 is N, Y2 is N, chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1535 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1536 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1537 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1538 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1539 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1540 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1541 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1542 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1543 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1544 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1545 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1546 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1547 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1548 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1549 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1550 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1551 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1552 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1553 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1554 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1555 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1556 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1557 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1558 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1559 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1560 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1561 chloro difluoromethyl bromo Y3 is CH _,n
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1562 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1563 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1564 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1565 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1566 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1567 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1568 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1569 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1570 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1571 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1572 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1573 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1574 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1575 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1576 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1577 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1578 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1579 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1580 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1581 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1582 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1583 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1584 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1585 fluoro chlorodifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1586 fluoro chlorodifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1587 fluoro chlorodifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1588 fluoro chlorodifluoromethyl cyclopropyl Y3 is CH
P.1589 X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethyl ethyl Y1 is N, Y2 is N, fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1590 fluoro chlorodifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1591 fluoro chlorodifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1592 fluoro chlorodifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1593 fluoro chlorodifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1594 fluoro chlorodifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1595 fluoro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1596 fluoro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1597 fluoro difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1598 fluoro difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1599 fluoro difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1600 fluoro difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1601 fluoro difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1602 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1603 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1604 fluoro difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1605 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1606 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1607 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1608 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1609 fluoro trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1610 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1611 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1612 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1613 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1614 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1615 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1616 fluoro trifluoromethyl methoxy Y3 is CH η Λ
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1617 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1618 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1619 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1620 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1621 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1622 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1623 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1624 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1625 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1626 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1627 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1628 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1629 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1630 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1631 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1632 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1633 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1634 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1635 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1636 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1637 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1638 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1639 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1640 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1641 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1642 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1643 bromo difluoromethyl trifluoromethoxy Y3 is CH
P.1644 X1 is chloro, X2 is CH, X3 is difluoromethyl trifluoromethyl Y1 is N, Y2 is N, n Λ bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1645 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1646 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1647 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1648 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1649 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1650 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1651 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1652 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1653 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1654 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1655 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1656 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1657 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1658 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1659 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1660 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1661 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1662 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1663 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1664 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1665 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1666 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1667 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1668 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1669 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1670 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1671 bromo difluoromethyl cyano Y3 is CH n„
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1672 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1673 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1674 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1675 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1676 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1677 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1678 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1679 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1680 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1681 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1682 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1683 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1684 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1685 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1686 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1687 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1688 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1689 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1690 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1691 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1692 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1693 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1694 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1695 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1696 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1697 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1698 bromo chlorodifluoromethyl fluoro Y3 is CH
P.1699 X1 is chloro, X2 is CH, X3 is chlorodifluoromethyl hydrogen Y1 is N, Y2 is N, bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1700 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1701 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1702 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1703 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1704 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1705 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1706 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1707 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1708 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1709 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1710 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1711 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1712 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1713 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1714 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1715 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1716 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1717 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1718 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1719 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1720 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1721 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1722 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1723 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1724 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1725 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1726 bromo trifluoromethyl nitro Y3 is CH „ Λ
X1 is chloro, X is CH, X3 is Y1 is N, Y2 is N,
P.1727 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1728 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1729 trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1730 trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1731 trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1732 trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is N, Y2 is N,
P.1733 trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is N, Y2 is N,
P.1734 trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1735 trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1736 trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1737 trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1738 trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1739 trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1740 trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1741 trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1742 trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1743 trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1744 trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1745 trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1746 trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1747 trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1748 trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1749 trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1750 trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1751 trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1752 trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1753 trifluoromethyl trifluoromethyl bromo Y3 is CH
P.1754 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl chloro Y1 is N, Y2 is N, 0 ^ trifluoromethyl Y3 is CH
X1 is chloro, X" is C-Cl, X3 is Y1 is N, Y2 is N,
P.1755 trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1756 trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1757 trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1758 trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1759 trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1760 trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1761 trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1762 trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1763 trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is N, Y2 is N,
P.1764 trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1765 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1766 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1767 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1768 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1769 XI is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1770 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1771 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1772 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1773 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1774 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1775 XJ is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1776 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1777 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1778 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is CH, Y1 is N, Y2 is N,
P.1779 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1780 X1 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X" is CH, Y1 is N, Y2 is N,
P.1781 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH n^
Figure imgf000087_0001
0^
X3 is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1810 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1811 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1812 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1813 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1814 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1815 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1816 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1817 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1818 XJ is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1819 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1820 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1821 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1822 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1823 X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1824 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1825 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1826 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1827 X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1828 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1829 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1830 X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1831 XJ is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1832 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1833 X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1834 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1835 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1836 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH on
Figure imgf000089_0001
„n
X is hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1865 X3 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1866 X3 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1867 X3 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1868 X3 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1869 X3 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1870 X3 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1871 X3 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is N, Y2 is N,
P.1872 X3 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1873 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1874 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1875 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1876 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1877 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1878 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1879 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1880 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1881 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1882 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1883 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1884 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1885 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1886 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1887 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1888 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1889 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1890 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1891 chloro difluoromethyl hydrogen Y3 is CH nn
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1892 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1893 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1894 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1895 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1896 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1897 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1898 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1899 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1900 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1901 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1902 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1903 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1904 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1905 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1906 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1907 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1908 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1909 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1910 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1911 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1912 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1913 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1914 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1915 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1916 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1917 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1918 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
P.1919 X1 is trifluoromethyl, X2 is N, chlorodifluoromethyl trifluoromethoxy Y1 is N, Y2 is N, Λ 1
X* is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1920 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1921 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1922 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1923 X1 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1924 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1925 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1926 X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1927 X1 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1928 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1929 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1930 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1931 X1 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1932 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1933 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1934 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1935 X1 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1936 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1937 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1938 X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1939 X5 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1940 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1941 X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1942 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1943 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is ti-ifluoromethyl, X2 is N, Y1 is N, Y2 is N,
P.1944 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1945 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1946 chloro chlorodifluoromethyl chloro Y3 is CH n„
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1947 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1948 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1949 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1950 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1951 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1952 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1953 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1954 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1955 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1956 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1957 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1958 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1959 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1960 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1961 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1962 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1963 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1964 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1965 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1966 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1967 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1968 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1969 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1970 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1971 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1972 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1973 chloro trifluoromethyl ethyl Y3 is CH
P.1974 X1 is chloro, X2 is CH, X3 is trifluoromethyl fluoro Y1 is CH, Y2 is N,
Figure imgf000094_0001
η λ
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2002 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2003 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2004 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2005 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2006 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X" is C-F, X3 is Y1 is CH, Y2 is N,
P.2007 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is CH, Y2 is N,
P.2008 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2009 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2010 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.201 1 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is CH, Y2 is N,
P.2012 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2013 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2014 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2015 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X1 is C-F, X3 is Y1 is CH, Y2 is N,
P.2016 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2017 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2018 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2019 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2020 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2021 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2022 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2023 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2024 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2025 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2026 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2027 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2028 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
P.2029 X1 is fluoro, X2 is C-Cl, X3 is difluoromethyl bromo Y1 is CH, Y2 is N, hydrogen YJ is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2030 hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2031 hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, Xi is Y1 is CH, Y2 is N,
P.2032 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2033 hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2034 hydrogen difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2035 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2036 hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2037 hydrogen difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2038 hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2039 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2040 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2041 hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2042 hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2043 hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2044 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2045 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2046 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2047 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2048 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2049 hydrogen trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2050 hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2051 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2052 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2053 hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2054 hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2055 hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2056 hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH nr
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2057 hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2058 hydrogen chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2059 hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2060 hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2061 hydrogen chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2062 hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2063 hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2064 hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2065 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2066 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2067 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2068 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2069 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2070 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2071 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2072 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2073 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2074 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2075 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2076 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2077 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2078 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2079 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2080 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2081 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2082 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2083 hydrogen trifluoromethyl hydrogen Y3 is CH
P.2084 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl methoxy Y1 is CH, Y2 is N, hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2085 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2086 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2087 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2088 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2089 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2090 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2091 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2092 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2093 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2094 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2095 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2096 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2097 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2098 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2099 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2100 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2101 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2102 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2103 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2104 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2105 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2106 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2107 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2108 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2109 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2110 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2111 chloro difluoromethyl trifluoromethoxy Y3 is CH „n
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2112 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2113 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2114 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2115 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2116 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2117 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2118 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2119 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2120 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2121 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2122 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2123 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is N,
P.2124 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2125 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2126 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2127 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2128 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2129 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2130 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2131 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2132 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2133 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2134 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2135 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2136 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2137 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2138 chloro difluoromethyl chloro Y3 is CH
P.2139 X1 is chloro, X2 is C-F, X3 is difluoromethyl cyano Y1 is CH, Y2 is N, nn chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2140 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2141 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2142 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2143 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2144 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2145 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2146 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2147 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2148 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2149 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2150 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X is Y1 is CH, Y2 is N,
P.2151 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X is Y1 is CH, Y2 is N,
P.2152 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2153 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2154 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2155 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2156 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2157 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2158 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2159 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2160 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2161 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2162 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2163 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2164 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2165 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2166 chloro chlorodifluoromethyl fluoro Y3 is CH , ΛΛ
X1 is chloro, X" is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2167 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2168 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2169 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2170 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2171 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2172 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2173 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2174 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2175 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2176 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2177 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2178 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2179 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2180 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2181 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2182 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2183 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2184 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2185 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2186 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2187 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is N,
P.2188 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2189 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2190 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is N,
P.2191 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2192 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2193 chloro trifluoromethyl methyl Y3 is CH
P.2194 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl nitro Y1 is CH, Y2 is N, Λ η Λ chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2195 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2196 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2197 chloro chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2198 chloro chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2199 chloro chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2200 chloro chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2201 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2202 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2203 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2204 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2205 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2206 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2207 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2208 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2209 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2210 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2211 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2212 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2213 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2214 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2215 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2216 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2217 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2218 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2219 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2220 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2221 chloro trifluoromethyl bromo Y3 is CH
Figure imgf000103_0001
fluoro Y' is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2250 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2251 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2252 fluoro difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2253 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2254 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2255 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2256 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2257 fluoro trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2258 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2259 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2260 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2261 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2262 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2263 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2264 fluoro trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2265 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2266 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2267 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2268 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2269 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2270 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2271 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2272 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2273 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2274 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2275 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2276 bromo chlorodifluoromethyl methoxy Y3 is CH Λ n .
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2277 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2278 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2279 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2280 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2281 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2282 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2283 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2284 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2285 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2286 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y- is N,
P.2287 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2288 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2289 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2290 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2291 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2292 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2293 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2294 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2295 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2296 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2297 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2298 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is N,
P.2299 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2300 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2301 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2302 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2303 bromo trifluoromethyl trifluoromethoxy Y3 is CH
P.2304 X1 is chloro, X2 is CH, X3 is trifluoromethyl trifluoromethyl Y1 is CH, Y2 is N, Λ η Γ bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2305 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2306 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2307 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2308 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2309 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2310 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2311 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2312 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2313 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2314 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2315 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2316 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2317 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2318 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2319 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2320 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2321 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2322 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2323 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2324 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2325 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2326 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2327 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2328 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2329 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2330 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2331 bromo trifluoromethyl cyano Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2332 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2333 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2334 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2335 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2336 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2337 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2338 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2339 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2340 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2341 bromo chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2342 bromo chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2343 bromo chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2344 bromo chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2345 bromo chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2346 bromo chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2347 bromo chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2348 bromo chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2349 bromo chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2350 bromo chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2351 bromo chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2352 bromo chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2353 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2354 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2355 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2356 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2357 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2358 bromo difluoromethyl fluoro Y3 is CH
P.2359 X1 is chloro, X2 is CH, X3 is difluoromethyl hydrogen Y1 is CH, Y2 is N, , Λ„ bromo Y3 is CH
X1 is chloro, X is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2360 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2361 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X' is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2362 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2363 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2364 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2365 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2366 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2367 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2368 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2369 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2370 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2371 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2372 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2373 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2374 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2375 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
Ρ.2376 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2377 trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2378 trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2379 trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2380 trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2381 trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2382 trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2383 trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2384 trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2385 trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2386 trifluoromethyl chlorodifluoromethyl nitro Y3 is CH , ΛΟ
X1 is chloro, X" is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2387 trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2388 trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2389 trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is chloro, X" is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2390 trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2391 trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2392 trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2393 trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2394 trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2395 trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2396 trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2397 trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2398 trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2399 trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2400 trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2401 trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2402 trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2403 trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2404 trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2405 trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2406 trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2407 trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2408 trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
Ρ.2409 trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2410 trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.241 1 trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is N,
P.2412 trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2413 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
P.2414 X1 is trifluoromethyl, X2 is CH, chlorodifluoromethyl chloro Y1 is CH, Y2 is N, , ΛΛ
X3 is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2415 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X is trifluoromethyl, X is CH, Y1 is CH, Y2 is N,
P.2416 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
P.2417 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2418 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2419 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X is trifluoromethyl, X is CH, Y1 is CH, Y2 is N,
Ρ.2420 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2421 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2422 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2423 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X is trifluoromethyl, X is CH, Y1 is CH, Y2 is N,
Ρ.2424 XJ is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2425 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2426 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2427 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2428 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2429 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2430 X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2431 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2432 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2433 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2434 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2435 X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2436 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2437 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2438 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2439 X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2440 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2441 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH , , Λ
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2442 X1 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2443 X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2444 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2445 X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
Ρ.2446 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2447 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2448 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2449 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2450 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2451 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2452 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2453 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2454 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2455 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2456 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2457 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2458 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2459 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2460 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2461 X' is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2462 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2463 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2464 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2465 X' is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2466 X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2467 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2468 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
Ρ.2469 X1 is trifluoromethyl, X2 is CH, difluoromethyl methyl Y1 is CH, Y2 is N, , Λ ,
X3 is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2470 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2471 X1 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2472 X5 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2473 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
Ρ.2474 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2475 X1 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2476 X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2477 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2478 X1 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2479 X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2480 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
P.2481 X1 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2482 X1 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2483 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
Ρ.2484 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2485 X1 is hydrogen chlorodifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2486 X3 is hydrogen chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2487 X3 is hydrogen chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2488 X' is hydrogen chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2489 X3 is hydrogen chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Yz is N,
Ρ.2490 X3 is hydrogen chlorodifluoromethyl fluoro Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
P.2491 X3 is hydrogen chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2492 X' is hydrogen chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2493 X3 is hydrogen chlorodifluoromethyl methyl Y3 is CH
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is N,
Ρ.2494 X3 is hydrogen chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2495 X1 is hydrogen chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is N,
Ρ.2496 X3 is hydrogen chlorodifluoromethyl trifluoromethyl Y3 is CH , ,„
Figure imgf000113_0001
Λ Λ„ chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2525 chloro chlorodifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2526 chloro chlorodifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2527 chloro chlorodifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2528 chloro chlorodifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2529 chloro chlorodifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2530 chloro chlorodifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
P.2531 chloro chlorodifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2532 chloro chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2533 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2534 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2535 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2536 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2537 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2538 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2539 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2540 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
P.2541 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2542 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2543 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2544 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2545 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2546 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2547 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2548 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2549 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2550 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
P.2551 chloro trifluoromethyl hydrogen Y3 is CH , ,„
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2552 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X is N, X3 is Y1 is CH, Y2 is N,
Ρ.2553 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X' is N, X3 is Y1 is CH, Y2 is N,
Ρ.2554 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X' is N, X3 is Y1 is CH, Y2 is N,
Ρ.2555 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is N,
Ρ.2556 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2557 X3 is trifluoromethyl chlorodifluoromethyl bromo Y3 is CH
X is trifluoromethyl, X is N, Y1 is CH, Y2 is N,
Ρ.2558 X3 is trifluoromethyl chlorodifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2559 X3 is trifluoromethyl chlorodifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2560 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
P.2561 X3 is trifluoromethyl chlorodifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2562 X3 is trifluoromethyl chlorodifluoromethyl fluoro Y3 is CH
X is trifluoromethyl, X is N, Y1 is CH, Y2 is N,
Ρ.2563 X3 is trifluoromethyl chlorodifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2564 X3 is trifluoromethyl chlorodifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2565 X3 is trifluoromethyl chlorodifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2566 X3 is trifluoromethyl chlorodifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2567 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy Y3 is CH
X is trifluoromethyl, X is N, Y1 is CH, Y2 is N,
Ρ.2568 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2569 X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2570 X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
P.2571 X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2572 X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X is trifluoromethyl, X is N, Y1 is CH, Y2 is N,
Ρ.2573 X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2574 X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2575 X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2576 X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2577 X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X is trifluoromethyl, X is N, Y1 is CH, Y2 is N,
Ρ.2578 X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
Ρ.2579 X1 is trifluoromethyl, X2 is N, difluoromethyl trifluoromethoxy Y1 is CH, Y2 is N, Λ Λ r
X1 is trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X" is N, Y1 is CH, Y2 is N,
Ρ.2580 X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X" is N, Y1 is CH, Y2 is N,
P.2581 X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is N, Y1 is CH, Y2 is N,
Ρ.2582 X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2583 X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2584 X1 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2585 X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X" is N, Y1 is CH, Y2 is N,
Ρ.2586 X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is N, Y1 is CH, Y2 is N,
Ρ.2587 X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is N, Y1 is CH, Y2 is N,
Ρ.2588 X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2589 X1 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is N,
Ρ.2590 X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is trifluoromethyl, X" is N, Y1 is CH, Y2 is N,
P.2591 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X" is N, Y1 is CH, Y2 is N,
Ρ.2592 X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2593 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2594 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2595 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2596 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2597 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2598 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2599 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2600 chloro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2601 chloro chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2602 chloro chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2603 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2604 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2605 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Yl is CH, Y2 is
Ρ.2606 chloro difluoromethyl chloro CH, Y3 is N Λ Λ r
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2607 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2608 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2609 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2610 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2611 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2612 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2613 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2614 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2615 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2616 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2617 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2618 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2619 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2620 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2621 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2622 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2623 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2624 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2625 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2626 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2627 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
Ρ.2628 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2629 hydrogen chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2630 hydrogen chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2631 hydrogen chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2632 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2633 hydrogen chlorodifluoromethyl ethyl CH, Y3 is N
Ρ.2634 X1 is chloro, X2 is C-F, X3 is chlorodifluoromethyl fluoro Y1 is CH, Y2 is , ,„ hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2635 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2636 hydrogen chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2637 hydrogen chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2638 hydrogen chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2639 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2640 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2641 hydrogen difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2642 hydrogen difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2643 hydrogen difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2644 hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2645 hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2646 hydrogen difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2647 hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2648 hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2649 hydrogen difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2650 hydrogen difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2651 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2652 hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2653 hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2654 hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2655 hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2656 hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2657 hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2658 hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2659 hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2660 hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2661 hydrogen trifluoromethyl methyl CH, Y3 is N , , η
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2662 hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2663 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
Ρ.2664 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2665 hydrogen chlorodifluoromethyl bromo CH, Y3 is N
X1 is fluoro, X1 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2666 hydrogen chlorodifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2667 hydrogen chlorodifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2668 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2669 hydrogen chlorodifluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2670 hydrogen chlorodifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2671 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2672 hydrogen chlorodifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2673 hydrogen chlorodifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2674 hydrogen chlorodifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2675 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2676 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2677 hydrogen difluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2678 hydrogen difluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2679 hydrogen difluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2680 hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2681 hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2682 hydrogen difluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2683 hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2684 hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2685 hydrogen difluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2686 hydrogen difluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2687 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2688 hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
Ρ.2689 X1 is fluoro, X2 is C-Cl, X3 is trifluoromethyl bromo Y1 is CH, Y2 is Λ Λ η hydrogen CH, Y3 is N
X1 is fluoro, X- is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2690 hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2691 hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2692 hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2693 hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2694 hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2695 hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2696 hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2697 hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2698 hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2699 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2700 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2701 hydrogen chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2702 hydrogen chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2703 hydrogen chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2704 hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2705 hydrogen chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2706 hydrogen chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2707 hydrogen chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2708 hydrogen chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
Ρ.2709 hydrogen chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2710 hydrogen chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.271 1 hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2712 hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2713 hydrogen difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2714 hydrogen difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2715 hydrogen difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2716 hydrogen difluoromethyl cyclopropyl CH, Y3 is N ,
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2717 hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2718 hydrogen difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2719 hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X" is C-Cl, X3 is Y1 is CH, Y2 is
P.2720 hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2721 hydrogen difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2722 hydrogen difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2723 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2724 hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2725 hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2726 hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2727 hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2728 hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2729 hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2730 hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2731 hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2732 hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2733 hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2734 hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2735 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2736 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2737 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2738 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2739 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2740 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2741 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2742 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2743 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
P.2744 X1 is chloro, X2 is C-Br, X3 is chlorodifluoromethyl methoxy Y1 is CH, Y2 is Λ„ Λ chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2745 chloro chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2746 chloro chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2747 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2748 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2749 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2750 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2751 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2752 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2753 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2754 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2755 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2756 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2757 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2758 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2759 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2760 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2761 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2762 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2763 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2764 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2765 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2766 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2767 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2768 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2769 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2770 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2771 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N Λ
X1 is chloro, X2 is C-Br, X3 is Y1 is CH, Y2 is
P.2772 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2773 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2774 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2775 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2776 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2777 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2778 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2779 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2780 chloro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2781 chloro chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2782 chloro chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2783 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2784 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2785 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2786 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2787 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2788 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2789 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2790 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2791 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2792 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2793 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2794 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2795 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2796 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2797 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2798 chloro trifluoromethyl chloro CH, Y3 is N
P.2799 X1 is chloro, X2 is C-F, X3 is trifluoromethyl cyano Y1 is CH, Y2 is chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2800 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2801 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2802 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2803 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2804 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2805 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2806 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2807 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2808 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2809 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2810 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2811 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2812 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2813 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2814 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2815 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2816 chloro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2817 chloro chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2818 chloro chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2819 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2820 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2821 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2822 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2823 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2824 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2825 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2826 chloro difluoromethyl fluoro CH, Y3 is N Λ„ Λ
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2827 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2828 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2829 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2830 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2831 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2832 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2833 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2834 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2835 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2836 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2837 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2838 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2839 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2840 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2841 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2842 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2843 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.2844 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2845 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2846 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2847 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2848 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2849 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2850 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2851 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2852 chloro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2853 chloro chlorodifluoromethyl methyl CH, Y3 is N
P.2854 X1 is chloro, X2 is C-I, X3 is chlorodifluoromethyl nitro Y1 is CH, Y2 is Λ η Γ chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2855 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2856 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2857 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2858 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2859 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2860 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2861 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2862 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2863 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2864 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2865 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2866 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2867 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2868 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2869 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2870 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2871 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2872 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2873 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2874 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2875 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2876 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2877 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2878 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2879 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2880 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2881 fluoro chlorodifluoromethyl bromo CH, Y3 is N X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2882 fluoro chlorodifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2883 fluoro chlorodifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2884 fluoro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2885 fluoro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2886 fluoro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2887 fluoro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2888 fluoro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2889 fluoro chlorodifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2890 fluoro chlorodifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2891 fluoro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2892 fluoro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2893 fluoro difluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2894 fluoro difluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2895 fluoro difluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2896 fluoro difluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2897 fluoro difluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2898 fluoro difluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2899 fluoro difluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2900 fluoro difluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2901 fluoro difluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2902 fluoro difluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2903 fluoro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2904 fluoro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2905 fluoro trifluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2906 fluoro trifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2907 fluoro trifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2908 fluoro trifluoromethyl cyclopropyl CH, Y3 is N
P.2909 X1 is fluoro, X2 is C-F, X3 is trifluoromethyl ethyl Y1 is CH, Y2 is Λ fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2910 fluoro trifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2911 fluoro trifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2912 fluoro trifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2913 fluoro trifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2914 fluoro trifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2915 fluoro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2916 fluoro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2917 bromo chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2918 bromo chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2919 bromo chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2920 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2921 bromo chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2922 bromo chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2923 bromo chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2924 bromo chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2925 bromo chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2926 bromo chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2927 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2928 bromo chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2929 bromo difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2930 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2931 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2932 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2933 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2934 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2935 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2936 bromo difluoromethyl methoxy CH, Y3 is N X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2937 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2938 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2939 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2940 bromo difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2941 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2942 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2943 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2944 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2945 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2946 bromo trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2947 bromo trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2948 bromo trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2949 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2950 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2951 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2952 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2953 bromo chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2954 bromo chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2955 bromo chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2956 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2957 bromo chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2958 bromo chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2959 bromo chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2960 bromo chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2961 bromo chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2962 bromo chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2963 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
P.2964 X1 is chloro, X2 is CH, X3 is chlorodifluoromethyl trifluoromethyl Y1 is CH, Y2 is Λ .„ bromo CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2965 bromo difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2966 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2967 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2968 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2969 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2970 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2971 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2972 bromo difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2973 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2974 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2975 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2976 bromo difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2977 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2978 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2979 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2980 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2981 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2982 bromo trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2983 bromo trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2984 bromo trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2985 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2986 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2987 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2988 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2989 bromo chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2990 bromo chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Yl is CH, Y2 is
P.2991 bromo chlorodifluoromethyl cyano CH, Y3 is N X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2992 bromo chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2993 bromo chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2994 bromo chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2995 bromo chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2996 bromo chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2997 bromo chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2998 bromo chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2999 bromo chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3000 bromo chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3001 bromo difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3002 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3003 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3004 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3005 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3006 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3007 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3008 bromo difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3009 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3010 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3011 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3012 bromo difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3013 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3014 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3015 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3016 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3017 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3018 bromo trifluoromethyl fluoro CH, Y3 is N
P.3019 X1 is chloro, X2 is CH, X3 is trifluoromethyl hydrogen Y1 is CH, Y2 is , ,, , bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3020 bromo trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X is CH, X3 is Y1 is CH, Y2 is
P.3021 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X' is CH, X3 is Y1 is CH, Y2 is
P.3022 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3023 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3024 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3025 trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3026 trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3027 trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3028 trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3029 trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3030 trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3031 trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3032 trifluoromethyl chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3033 trifluoromethyl chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3034 trifluoromethyl chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3035 trifluoromethyl chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3036 trifluoromethyl chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3037 trifluoromethyl difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3038 trifluoromethyl difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3039 trifluoromethyl difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3040 trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3041 trifluoromethyl difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3042 trifluoromethyl difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3043 trifluoromethyl difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3044 trifluoromethyl difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3045 trifluoromethyl difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3046 trifluoromethyl difluoromethyl nitro CH, Y3 is N X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3047 trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3048 trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3049 trifluoromethyl trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3050 trifluoromethyl trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3051 trifluoromethyl trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3052 trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3053 trifluoromethyl trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3054 trifluoromethyl trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 is Y1 is CH, Y2 is
P.3055 trifluoromethyl trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is
P.3056 trifluoromethyl trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X* is Y1 is CH, Y2 is
P.3057 trifluoromethyl trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3058 trifluoromethyl trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3059 trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, Xs is Y1 is CH, Y2 is
P.3060 trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is CH, Y1 is CH, Y2 is
P.3061 X3 is trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3062 X3 is trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3063 X3 is trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3064 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3065 X3 is trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3066 X3 is trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is N
— X I is trifluoromethyl, X is CH, Y1 is CH, Y2 is
P.3067 X3 is trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3068 X1 is trifluoromethyl chlorodifluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3069 X3 is trifluoromethyl chlorodifluoromethyl methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3070 X3 is trifluoromethyl chlorodifluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3071 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3072 X3 is trifluoromethyl chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3073 X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is N
P.3074 X1 is trifluoromethyl, X2 is CH, difluoromethyl chloro Y1 is CH, Y2 is X3 is trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3075 X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3076 X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3077 X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3078 X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3079 X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3080 X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3081 X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3082 X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3083 X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3084 X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3085 X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3086 X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3087 X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3088 X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3089 X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3090 X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3091 X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3092 X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3093 X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3094 X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3095 X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3096 X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3097 X3 is trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3098 X3 is trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3099 X3 is trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3100 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3101 X3 is trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is N Λ„ Λ
Figure imgf000135_0001
Λ - Γ
X3 is trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3130 X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3131 X1 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3132 X5 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3133 X3 is hydrogen chlorodifluoromethyl bromo CH, Y3 is N
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3134 X3 is hydrogen chlorodifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3135 X1 is hydrogen chlorodifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3136 X3 is hydrogen chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3137 X3 is hydrogen chlorodifluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3138 X1 is hydrogen chlorodifluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3139 X3 is hydrogen chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3140 X3 is hydrogen chlorodifluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y- is
P.3141 X1 is hydrogen chlorodifluoromethyl methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3142 X1 is hydrogen chlorodifluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3143 X3 is hydrogen chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3144 X3 is hydrogen chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3145 X1 is hydrogen difluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3146 X3 is hydrogen difluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3147 X3 is hydrogen difluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3148 X1 is hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3149 X3 is hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Yz is
P.3150 X3 is hydrogen difluoromethyl fluoro CH, Y3 is N
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3151 X3 is hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3152 X1 is hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3153 X3 is hydrogen difluoromethyl methyl CH, Y3 is N
X is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3154 X3 is hydrogen difluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3155 X1 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3156 X3 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is N X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3157 X3 is hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3158 X3 is hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3159 X3 is hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3160 X3 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3161 X3 is hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3162 X3 is hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3163 X3 is hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is trifluoromethyl, X" is CH, Y1 is CH, Y2 is
P.3164 X3 is hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3165 X3 is hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3166 X3 is hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3167 X1 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is CH, Y1 is CH, Y2 is
P.3168 X3 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3169 chloro chlorodifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3170 chloro chlorodifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3171 chloro chlorodifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3172 chloro chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3173 chloro chlorodifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3174 chloro chlorodifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3175 chloro chlorodifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3176 chloro chlorodifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3177 chloro chlorodifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3178 chloro chlorodifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3179 chloro chlorodifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3180 chloro chlorodifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3181 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3182 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3183 chloro difluoromethyl cyano CH, Y3 is N
P.3184 X1 is chloro, X2 is N, X3 is difluoromethyl cyclopropyl Y1 is CH, Y2 is chloro CH, Y" is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3185 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3186 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3187 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3188 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3189 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is N, Xs is Y1 is CH, Y2 is
P.3190 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3191 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3192 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3193 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3194 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3195 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is N, Xs is Y1 is CH, Y2 is
P.3196 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is N, X* is Y1 is CH, Y2 is
P.3197 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3198 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3199 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3200 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3201 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3202 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3203 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3204 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3205 X3 is trifluoromethyl chlorodifluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3206 X3 is trifluoromethyl chlorodifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3207 X3 is trifluoromethyl chlorodifluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3208 X3 is trifluoromethyl chlorodifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3209 X3 is trifluoromethyl chlorodifluoromethyl ethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.3210 X3 is trifluoromethyl chlorodifluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is N, Y1 is CH, Y2 is
P.321 1 X1 is trifluoromethyl chlorodifluoromethyl hydrogen CH, Y3 is N 1 n
Figure imgf000139_0001
n
Figure imgf000140_0002
Figure imgf000140_0001
Table IP:
Table IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 2P:
Table 2P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 3P:
Table 3P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 4P:
Table 4P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 5P:
Table 5P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 6P:
Table 6P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 7P:
Table 7P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 8P:
Table 8P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 9P:
Table 9P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 10P:
Table 10P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.OlO, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table I IP:
Table 1 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 1, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 12P:
Table 12P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 13P:
Table 13P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 14P:
Table 14P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 15P:
Table 15P provides 3240 compounds of fomiula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 16P:
Table 16P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 17P:
Table 17P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 18P:
Table 18P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 19P:
Table 19P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 20P:
Table 20P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 2 IP:
Table 21P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 22P:
Table 22P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 23P:
Table 23P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 24P:
Table 24P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 25P:
Table 25P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 26P:
Table 26P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 27P:
Table 27P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 28P:
Table 28P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 29P:
Table 29P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 30P:
Table 30P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 3 IP:
Table 3 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 32P:
Table 32P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 33P:
Table 33P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 34P:
Table 34P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 35P:
Table 35P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 36P:
Table 36P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 37P:
Table 37P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 38P:
Table 38P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 39P:
Table 39P provides 3240 compounds of fomiula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 40P:
Table 40P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 4 IP:
Table 41P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 42P:
Table 42P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 43P:
Table 43P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 44P:
Table 44P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 45P:
Table 45P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 46P:
Table 46P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 47P:
Table 47P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 48P:
Table 48P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 49P:
Table 49P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 50P:
Table 50P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 5 IP:
Table 51P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 52P:
Table 52P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 53P:
Table 53P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 54P:
Table 54P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 55P:
Table 55P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R' is G.055, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 56P:
Table 56P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 57P:
Table 57P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 58P:
Table 58P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 59P:
Table 59P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 60P:
Table 60P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 6 IP:
Table 61P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 62P:
Table 62P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 63P:
Table 63P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 64P:
Table 64P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 65P:
Table 65P provides 3240 compounds of fomiula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 66P:
Table 66P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 67P:
Table 67P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 68P:
Table 68P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R is G.068, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 69P:
Table 69P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 70P:
Table 70P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R' is G.070, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 7 IP:
Table 71P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R is G.071, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 72P:
Table 72P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 73P:
Table 73P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 74P:
Table 74P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R is G.074, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 75P:
Table 75P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 76P:
Table 76P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 77P:
Table 77P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 78P:
Table 78P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 79P:
Table 79P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 80P:
Table 80P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 8 IP:
Table 81P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, " is G.081 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 82P:
Table 82P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 83P:
Table 83P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 84P:
Table 84P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 85P:
Table 85P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 86P:
Table 86P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 87P:
Table 87P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 88P:
Table 88P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 89P:
Table 89P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 90P:
Table 90P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 91P
Table 91P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 92P
Table 92P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 93P
Table 93P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 94P
Table 94P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 95P
Table 95P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 96P
Table 96P provides 3240 compounds of fonnula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 97P
Table 97P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 98P
Table 98P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 99P
Table 99P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 100P
Table 100P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 101 P
Table 101P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 102P
Table 102P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 103P
Table 103P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 104P Table 104P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 04, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 105P
Table 105P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 106P
Table 106P provides 3240 compounds of fonnula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 107P
Table 107P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 07, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 108P
Table 108P provides 3240 compounds of formula (I- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 109P
Table 109P provides 3240 compounds of fonnula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 09, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table H OP
Table H OP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.1 10, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 1 IP:
Table 11 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 1 1 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 12 P
Table 1 12P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 12, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 13 P
Table 1 13P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 13, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 14 P
Table 1 14P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 14, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 15 P
Table 1 15P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.1 15, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 16 P
Table 1 16P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 16, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table Q
XI , X2, X3 X4
Q.001 X1 is chloro, X2 is CH, X3 is chloro chlorodifluoromethyl
Q.002 X1 is chloro, X2 is CH, X3 is chloro difluoromethyl
Q.003 X1 is chloro, X2 is CH, X3 is chloro trifluoromethyl
Q.004 X1 is chloro, X2 is C-F, X3 is hydrogen chlorodifluoromethyl
Q.005 X1 is chloro, X2 is C-F, X' is hydrogen difluoromethyl
Q.006 X1 is chloro, X2 is C-F, X1 is hydrogen trifluoromethyl
Q.007 X1 is fluoro, X2 is C-Cl, X3 is hydrogen chlorodifluoromethyl
Q.008 X1 is fluoro, X2 is C-Cl, X3 is hydrogen difluoromethyl
Q.009 X1 is fluoro, X2 is C-Cl, X3 is hydrogen trifluoromethyl Q.010 X1 is chloro, X2 is C-Cl, X3 is hydrogen chlorodifluoromethyl
Q.011 X1 is chloro, X2 is C-Cl, X3 is hydrogen difluoromethyl
Q.012 X1 is chloro, X2 is C-Cl, X3 is hydrogen trifluoromethyl
Q.013 X1 is chloro, X2 is C-Br, X3 is chloro chlorodifluoromethyl
Q.014 X1 is chloro, X2 is C-Br, X3 is chloro difluoromethyl
Q.015 X1 is chloro, X2 is C-Br, X3 is chloro trifluoromethyl
Q.016 X1 is chloro, X2 is C-F, X3 is chloro chlorodifluoromethyl
Q.017 X1 is chloro, X2 is C-F, X3 is chloro difluoromethyl
Q.018 X1 is chloro, X2 is C-F, X3 is chloro trifluoromethyl
Q.019 X1 is chloro, X2 is C-Cl, X3 is chloro chlorodifluoromethyl
Q.020 X1 is chloro, X2 is C-Cl, X3 is chloro difluoromethyl
Q.021 X1 is chloro, X2 is C-Cl, X3 is chloro trifluoromethyl
Q.022 X1 is chloro, X2 is C-I, X3 is chloro chlorodifluoromethyl
Q.023 X1 is chloro, X2 is C-I, X3 is chloro difluoromethyl
Q.024 X1 is chloro, X2 is C-I, X3 is chloro trifluoromethyl
Q.025 X1 is fluoro, X2 is C-F, X3 is fluoro chlorodifluoromethyl
Q.026 X1 is fluoro, X2 is C-F, X3 is fluoro difluoromethyl
Q.027 X1 is fluoro, X2 is C-F, X3 is fluoro trifluoromethyl
Q.028 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.029 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.030 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.031 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.032 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.033 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.034 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.035 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.036 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.037 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl chlorodifluoromethyl
Q.038 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl difluoromethyl
Q.039 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl trifluoromethyl
Q.040 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl chlorodifluoromethyl
Q.041 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl difluoromethyl
Q.042 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl trifluoromethyl
Q.043 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl chlorodifluoromethyl
Q.044 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl difluoromethyl
Q.045 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl trifluoromethyl
Q.046 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen chlorodifluoromethyl Q.047 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen difluoromethyl
Q.048 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen trifluoromethyl
Q.049 X1 is chloro, X2 is N, X3 is chloro chlorodifluoromethyl
Q.050 X1 is chloro, X2 is N, X3 is chloro difluoromethyl
Q.051 X1 is chloro, X2 is N, X3 is chloro trifluoromethyl
Q.052 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl chlorodifluoromethyl
Q.053 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl difluoromethyl
Q.054 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl trifluoromethyl
Figure imgf000148_0001
Table 10:
Table 1 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3and X4 have the values listed in the table Q.
Table 20:
Table 2 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 30:
Table 3 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 40:
Table 4 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q.
Table 50:
Table 5 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 60:
Table 6 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3and X4 have the values listed in the table Q.
Table 70:
Table 7 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3and X4 have the values listed in the table Q.
Table 80:
Table 8 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3and X4 have the values listed in the table Q.
Table 90:
Table 9 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3and X4 have the values listed in the table Q.
Table 10O:
Table 10 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010, X1, X2, X3and X4 have the values listed in the table Q. - 14ο -
Table 110:
Table H Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.011, X1, X2, X3and X4 have the values listed in the table Q.
Table 120:
Table 12 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3and X4 have the values listed in the table Q.
Table 130:
Table 13 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3and X4 have the values listed in the table Q.
Table 140:
Table 14 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3and X4 have the values listed in the table Q.
Table 150:
Table 15 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3and X4 have the values listed in the table Q.
Table 160:
Table 16 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3and X4 have the values listed in the table Q.
Table 170:
Table 17 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3and X4 have the values listed in the table Q.
Table 180:
Table 18 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3and X4 have the values listed in the table Q.
Table 190:
Table 19 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3and X4 have the values listed in the table Q.
Table 200:
Table 20 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3and X4 have the values listed in the table Q.
Table 210:
Table 21 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, X1, X2, X3and X4 have the values listed in the table Q.
Table 220:
Table 22 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3and X4 have the values listed in the table Q.
Table 230:
Table 23 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3and X4 have the values listed in the table Q.
Table 240:
Table 24 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3and X4 have the values listed in the table Q.
Table 250:
Table 25 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3and X4 have the values listed in the table Q.
Table 260:
Table 26 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3and X4 have the values listed in the table Q.
Table 270:
Table 27 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3and X4 have the values listed in the table Q.
Table 280:
Table 28 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3and X4 have the values listed in the table Q. ^
Table 290:
Table 29 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3and X4 have the values listed in the table Q.
Table 30O:
Table 30 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3and X4 have the values listed in the table Q.
Table 310:
Table 31 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031, X1, X2, X3and X4 have the values listed in the table Q.
Table 320:
Table 32 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3and X4 have the values listed in the table Q.
Table 330:
Table 33 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3and X4 have the values listed in the table Q.
Table 340:
Table 34 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3and X4 have the values listed in the table Q.
Table 350:
Table 35 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X'and X4 have the values listed in the table Q.
Table 360:
Table 36 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3and X4 have the values listed in the table Q.
Table 370:
Table 37 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3and X4 have the values listed in the table Q.
Table 380:
Table 38 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3and X4 have the values listed in the table Q.
Table 390:
Table 39 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X'and X4 have the values listed in the table Q.
Table 40O:
Table 40 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3and X4 have the values listed in the table Q.
Table 410:
Table 41 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, X1, X2, X3and X4 have the values listed in the table Q.
Table 420:
Table 42 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3and X4 have the values listed in the table Q.
Table 430:
Table 43 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3and X4 have the values listed in the table Q.
Table 440:
Table 44 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3and X4 have the values listed in the table Q.
Table 450:
Table 45 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3and X4 have the values listed in the table Q.
Table 460:
Table 46 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3and X4 have the values listed in the table Q. Table 470:
Table 47 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3and X4 have the values listed in the table Q.
Table 480:
Table 48 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, X1, X2, X3and X4 have the values listed in the table Q.
Table 490:
Table 49 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3and X4 have the values listed in the table Q.
Table 500:
Table 50 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3and X4 have the values listed in the table Q.
Table 510:
Table 51 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3and X4 have the values listed in the table Q.
Table 520:
Table 52 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3and X4 have the values listed in the table Q.
Table 530:
Table 53 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3and X4 have the values listed in the table Q.
Table 540:
Table 54 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3and X4 have the values listed in the table Q.
Table 550:
Table 55 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3and X4 have the values listed in the table Q.
Table 560:
Table 56 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3and X4 have the values listed in the table Q.
Table 570:
Table 57 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3and X4 have the values listed in the table Q.
Table 580:
Table 58 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3and X4 have the values listed in the table Q.
Table 590:
Table 59 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3and X4 have the values listed in the table Q.
Table 600:
Table 60 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3and X4 have the values listed in the table Q.
Table 610:
Table 61 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3and X4 have the values listed in the table Q.
Table 620:
Table 62 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3and X4 have the values listed in the table Q.
Table 630:
Table 63 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3and X4 have the values listed in the table Q.
Table 640:
Table 64 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3and X4 have the values listed in the table Q. Table 650:
Table 65 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3and X4 have the values listed in the table Q.
Table 660:
Table 66 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3and X4 have the values listed in the table Q.
Table 670:
Table 67 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3and X4 have the values listed in the table Q.
Table 680:
Table 68 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3and X4 have the values listed in the table Q.
Table 690:
Table 69 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3and X4 have the values listed in the table Q.
Table 700:
Table 70 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3and X4 have the values listed in the table Q.
Table 710:
Table 71 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3and X4 have the values listed in the table Q.
Table 720:
Table 72 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3and X4 have the values listed in the table Q.
Table 730:
Table 73 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3and X4 have the values listed in the table Q.
Table 740:
Table 74 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3and X4 have the values listed in the table Q.
Table 750:
Table 75 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3and X4 have the values listed in the table Q.
Table 760:
Table 76 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3and X4 have the values listed in the table Q.
Table 770:
Table 77 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3and X4 have the values listed in the table Q.
Table 780:
Table 78 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3and X4 have the values listed in the table Q.
Table 790:
Table 79 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the table Q.
Table 800:
Table 80 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the table Q.
Table 810:
Table 81 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, X1, X2, X3and X4 have the values listed in the table Q.
Table 820:
Table 82 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3and X4 have the values listed in the table Q. Table 830:
Table 83 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3and X4 have the values listed in the table Q.
Table 840:
Table 84 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3and X4 have the values listed in the table Q.
Table 850:
Table 85 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the table Q.
Table 860:
Table 86 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the table Q.
Table 870:
Table 87 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3and X4 have the values listed in the table Q.
Table 880:
Table 88 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3and X4 have the values listed in the table Q.
Table 890:
Table 89 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the table Q.
Table 900:
Table 90 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3and X4 have the values listed in the table Q.
Table 910:
Table 91 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the table Q.
Table 92 0:
Table 92 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the table Q.
Table 93 0:
Table 93 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the table Q.
Table 94 0:
Table 94 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the table Q.
Table 95 0:
Table 95 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the table Q.
Table 96 0:
Table 96 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3and X4 have the values listed in the table Q.
Table 97 0:
Table 97 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the table Q.
Table 98 0:
Table 98 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the table Q.
Table 99 0:
Table 99 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the table Q.
Table 100 0:
Table 100 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3and X4 have the values listed in the table Q.
Table 101 0: Table 101 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 01, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 1020:
Table 02 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 030:
Table 03 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 03,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 040:
Table 04 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 050:
Table 05 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 05,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 060:
Table 06 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 070:
Table 07 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 080:
Table 08 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 090:
Table 09 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 100:
Table 10 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table l lQ:
Table H Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 ,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 120:
Table 12 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 130:
Table 13 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 140:
Table 14 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 150:
Table 15 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.115,
X1, X^ X3and X4 have the values listed in the tab e Q.
Table 160:
Table 116 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, X1, X2, X3and X4 have the values listed in the tab e Q.
Figure imgf000155_0001
Table 1170:
Table 117Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3and X4 have the values listed in the table Q.
Table 1180:
Table 118Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 119 0:
Table 119Q provides 54 compounds of fonnula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 120O:
Table 120Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q.
Table 121 0:
Table 121Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 1220:
Table 122Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3 nd X4 have the values listed in the table Q.
Table 1230:
Table 123Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3and X4 have the values listed in the table Q.
Table 1240:
Table 124Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3and X4 have the values listed in the table Q.
Table 1250:
Table 125Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3and X4 have the values listed in the table Q.
Table 1260:
Table 126Q provides 54 compounds of fonnula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol O, X1, X2, X3and X4 have the values listed in the table Q.
Table 1270:
Table 127Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.011, X1, X2, X3and X4 have the values listed in the table Q.
Table 1280:
Table 128Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3and X4 have the values listed in the table Q.
Table 129 0:
Table 129Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3and X4 have the values listed in the table Q.
Table 130O:
Table 130Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3and X4 have the values listed in the table Q.
Table 1310:
Table 131Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3and X4 have the values listed in the table Q. Table 320:
Table 32Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R is G.016,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 330:
Table 33Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 340:
Table 34Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, Rz is G.018, X1, X: X3and X4 have the values listed in the tab e Q.
Table 350:
Table 35Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 360:
Table 36Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 370:
Table 37Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021 , X1, X: X3and X4 have the values listed in the tab e Q.
Table 380:
Table 38Q provides 54 compounds of fonnula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 390:
Table 39Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 400:
Table 40Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X: X3and X4 have the values listed in the tab e Q.
Table 410:
Table 41 Q provides 54 compounds of fonnula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 420:
Table 42Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 430:
Table 43 Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X: X3and X4 have the values listed in the tab e Q.
Table 440:
Table 44Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 45 0:
Table 45Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 46 0:
Table 46Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 47 0:
Table 47Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031 ,
X1, x' X3and X4 have the values listed in the tab e Q.
Table 480:
Table 48Q provides 54 compounds of formula ( •C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 490:
Table 149Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3and X4 have the values listed in the tab e Q. Table 50 0:
Table 50Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 51 0:
Table 51 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 520:
Table 52Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X: X3and X4 have the values listed in the tab e Q.
Table 530:
Table 53Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 540:
Table 54Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 55 0:
Table 55Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X: X3and X4 have the values listed in the tab e Q.
Table 56 O:
Table 56Q provides 54 compounds of fonnula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 570:
Table 57Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 580:
Table 58Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X: X3and X4 have the values listed in the tab e Q.
Table 59 0:
Table 59Q provides 54 compounds of fonnula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 600:
Table 60Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 610:
Table 61 Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3and X4 have the values listed in the tab e Q.
Tableb 162 0:
Table 62Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 630:
Table 63 Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 64 0:
Table 64Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048,
X1, X: X3and X4 have the values listed in the tab e Q.
Table 65 0:
Table 65Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049,
X1, x' X3and X4 have the values listed in the tab e Q.
Table 660:
Table 166Q provides 54 compounds of formula ( •C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3and X4 have the values listed in the tab e Q.
Tablel67 0:
Table 167Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 1680: ^
Table 168Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3and X4 have the values listed in the table Q.
Table 1690:
Table 169Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3and X4 have the values listed in the table Q.
Table 170 0:
Table 170Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3and X4 have the values listed in the table Q.
Table 1710:
Table 171Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3and X4 have the values listed in the table Q.
Table 1720:
Table 172Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3and X4 have the values listed in the table Q.
Table 1730:
Table 173Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3and X4 have the values listed in the table Q.
Table 1740:
Table 174Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3and X4 have the values listed in the table Q.
Table 1750:
Table 175Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3and X4 have the values listed in the table Q.
Table 1760:
Table 176Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3and X4 have the values listed in the table Q.
Table 1770:
Table 177Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061 , X1, X2, X3and X4 have the values listed in the table Q.
Table 1780:
Table 178Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3and X4 have the values listed in the table Q.
Table 1790:
Table 179Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3and X4 have the values listed in the table Q.
Table 180 0:
Table 180Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3and X4 have the values listed in the table Q.
Table 181 0:
Table 181Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3and X4 have the values listed in the table Q.
Table 182 0:
Table 182Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3and X4 have the values listed in the table Q.
Table 1830:
Table 183Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3and X4 have the values listed in the table Q.
Table 1840:
Table 184Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3and X4 have the values listed in the table Q.
Table 1850:
Table 185Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3and X4 have the values listed in the table Q.
Table 186 0:
Table 186Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3and X4 have the values listed in the table Q. ,
Table 1870:
Table 187Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3and X4 have the values listed in the table Q.
Table 1880:
Table 188Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3and X4 have the values listed in the table Q.
Table 1890:
Table 189Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3and X4 have the values listed in the table Q.
Table 190 0:
Table 190Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3and X4 have the values listed in the table Q.
Table 1910:
Table 191Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3and X4 have the values listed in the table Q.
Table 192 0:
Table 192Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3and X4 have the values listed in the table Q.
Table 193 0:
Table 193Q provides 54 compounds of fonnula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3and X4 have the values listed in the table Q.
Table 1940:
Table 194Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3and X4 have the values listed in the table Q.
Table 1950:
Table 195Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the table Q.
Table I960:
Table 196Q provides 54 compounds of fonnula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the table Q.
Table 1970:
Table 197Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, X1, X2, X3and X4 have the values listed in the table Q.
Table 1980:
Table 198Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3and X4 have the values listed in the table Q.
Table 1990:
Table 199Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3and X4 have the values listed in the table Q.
Table 200Q:
Table 200Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3and X4 have the values listed in the table Q.
Table 2010:
Table 201Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the table Q.
Table 202O:
Table 202Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the table Q.
Table 2030:
Table 203Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3and X4 have the values listed in the table Q.
Table 204 0:
Table 204Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3and X4 have the values listed in the table Q. Table 205 0:
Table 205Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 206 0:
Table 206Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 207O:
Table 207Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 208O:
Table 208Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 209Q:
Table 209Q provides 54 compounds of fomiula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 210Q:
Table 210Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2110:
Table 211Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2120:
Table 212Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X'and X4 have the values listed in the tab e Q.
Table 2130:
Table 213Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 214 0:
Table 214Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 215 0:
Table 215Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2160:
Table 216Q provides 54 compounds of fomiula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 217 0:
Table 217Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 218 0:
Table 218Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2190:
Table 219Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 220 0:
Table 220Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2210:
Table 221 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 222 0:
Table 222Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3and X4 have the values listed in the tab e Q. Table 223 0:
Table 223Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 07, X1, X2, X3and X4 have the values listed in the table Q.
Table 224 0:
Table 224Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08, X1, X2, X3and X4 have the values listed in the table Q.
Table 225 0:
Table 225Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 09, X1, X2, X3and X4 have the values listed in the table Q.
Table 226 Q:
Table 226Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, X1, X2, X3and X4 have the values listed in the table Q.
Table 227 0:
Table 227Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , X1, X2, X3and X4 have the values listed in the table Q.
Table 2280:
Table 228Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3and X4 have the values listed in the table Q.
Table 229 0:
Table 229Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113, X1, X2, X3and X4 have the values listed in the table Q.
Table 2300:
Table 23 OQ provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114, X1, X2, X3and X4 have the values listed in the table Q.
Table 2310:
Table 231Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 15, X1, X2, X3and X4 have the values listed in the table Q.
Table 232 0:
Table 232Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 16, X1, X2, X3and X4 have the values listed in the table Q.
Table Het
Figure imgf000161_0001
Figure imgf000162_0001
Table 117P
Table 117P provides 3240 compounds of formula (I-D) wherein Het is Het.Ol and X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 118P
Table 118P provides 3240 compounds of formula (I-D) wherein Het is Het.02 and X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 119 P
Table 119P provides 3240 compounds of formula (I-D) wherein Het is Het.03 and X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 120 P
Table 120P provides 324 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the value
Figure imgf000162_0002
Table 233 Q
Table 233Q provides 54 compounds of fonnula (I-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.Ol and X1, X2, X'and X4 have the values listed in the table Q.
Table 2340
Table 234Q provides 54 compounds of formula (I-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.02 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2350
Table 235Q provides 54 compounds of formula (I-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.03, X1, X2, X3and X4 have the values listed in the table Q.
Table 2360
Table 236Q provides 54 compounds of formula (I-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.04, X1, X2, X3and X4 have the values listed in the table Q.
Figure imgf000162_0003
Table 2370 Table 237Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.01 , X1, X2, X3and X4 have the values listed in the table Q.
Table 2380
Table 238Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.02, X1, X2, X3and X4 have the values listed in the table Q.
Table 2390
Table 239Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.03, X1, X2, X3and X4 have the values listed in the table Q.
Table 240O
Table 240Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.04, X1, X2, X3and X4 have the values listed in the table Q.
Figure imgf000163_0002
Figure imgf000163_0001
Table 121P
Table 121P provides 3240 compounds of formula (II- A) wherein Gi is GOl and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 122P Table 122P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G02 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 123P
Table 123P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G03 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 124 P
Table 124P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G04 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 125P
Table 125P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G051 and X1, X2, X3, Y1, Y2, Y3, X4 and Pv5 have the values listed in the table P.
Table 126P
Table 126P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G06 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 127P
Table 127P provides 3240 compounds of formula II- A) wherein Gi is G07 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 128 P
Table 128P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G08 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 129P
Table 129P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G09 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 13 OP
Table 130P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G10 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 13 IP
Table 13 IP provides 3240 compounds of formula ΊΙ-Α) wherein Gi is GI 1 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 132 P
Table 132P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G12 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 133P
Table 133P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G13 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 134P
Table 134P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G14 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 135P
Table 135P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G15 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 136 P
Table 136P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G16 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 137 P
Table 137P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G17 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 138P
Table 138P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G18 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 139P
Table 139P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G19 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 140P
Table 140P provides 3240 compounds of formula ΊΙ-Α) wherein Gi is G20 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Figure imgf000165_0001
Table 141P
Table 4 IP provides 3240 compounds of formula (II-B) wherein Gi is G01 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 142P
Table 42P provides 3240 compounds of formula (II-B) wherein Gi is G02 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 143P
Table 43P provides 3240 compounds of formula (II-B) wherein Gi is G03 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 144 P
Table 44P provides 3240 compounds of formula (II-B) wherein Gi is G04 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 145P
Table 45P provides 3240 compounds of formula (II-B) wherein Gi is G051 and X1, X2, X3, Y1, Y2, Y3,
X4 and R5 have the values listed in the table P.
Table 146P
Table 46P provides 3240 compounds of formula (II-B) wherein Gi is G06 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 147P
Table 47P provides 3240 compounds of formula (II-B) wherein Gi is G07 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 148 P
Table 48P provides 3240 compounds of formula (II-B) wherein Gi is G08 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 149P
Table 49P provides 3240 compounds of formula (II-B) wherein Gi is G09 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 150P
Table 50P provides 3240 compounds of formula (II-B) wherein Gi is G10 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 151P
Table 5 IP provides 3240 compounds of formula (II-B) wherein Gi is GI 1 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 152 P
Table 52P provides 3240 compounds of formula (II-B) wherein Gi is G12 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 153P
Table 53P provides 3240 compounds of formula (II-B) wherein Gi is G13 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 154P
Table 54P provides 3240 compounds of formula (II-B) wherein Gi is G14 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 155P
Table 55P provides 3240 compounds of formula (II-B) wherein Gi is G15 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 156 P Table 156P provides 3240 compounds of formula (II-B) wherein Gi is G16 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 157 P
Table 157P provides 3240 compounds of formula (II-B) wherein Gi is G17 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 158P
Table 158P provides 3240 compounds of formula (II-B) wherein Gi is G18 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 159P
Table 159P provides 3240 compounds of formula (II-B) wherein Gi is G19 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 160P
Table 160P provides 3240 compounds of formula (II-B) wherein Gi is G20 and X1, X2, X3, Y1, Y2, Y3, X
Figure imgf000166_0001
(Il-C)
Table 161P
Table 16 IP provides 3240 compounds of formula II-C) wherein Gi is G01 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 162P
Table 162P provides 3240 compounds of formula II-C) wherein Gi is G02 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 163P
Table 163P provides 3240 compounds of formula II-C) wherein Gi is G03 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 164 P
Table 164P provides 3240 compounds of formula II-C) wherein Gi is G04 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 165P
Table 165P provides 3240 compounds of formula II-C) wherein Gi is G051 and X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 166P
Table 166P provides 3240 compounds of formula II-C) wherein Gi is G06 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 167P
Table 167P provides 3240 compounds of formula II-C) wherein Gi is G07 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 168 P
Table 168P provides 3240 compounds of formula II-C) wherein Gi is G08 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 169P
Table 169P provides 3240 compounds of formula II-C) wherein Gi is G09 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 170P
Table 170P provides 3240 compounds of formula II-C) wherein Gi is G10 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 171P
Table 17 IP provides 3240 compounds of formula II-C) wherein Gi is GI 1 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 172 P Table 172P provides 3240 compounds of formula II-C) wherein Gi is G12 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 173P
Table 173P provides 3240 compounds of formula II-C) wherein Gi is G13 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 174P
Table 174P provides 3240 compounds of formula II-C) wherein Gi is G14 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 175P
Table 175P provides 3240 compounds of formula II-C) wherein Gi is G15 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 176 P
Table 176P provides 3240 compounds of formula II-C) wherein Gi is G16 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 177 P
Table 177P provides 3240 compounds of formula II-C) wherein Gi is G17 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 178P
Table 178P provides 3240 compounds of formula II-C) wherein Gi is G18 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 179P
Table 179P provides 3240 compounds of formula II-C) wherein Gi is G19 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 180P
Table 180P provides 3240 compounds of formula II-C) wherein Gi is G20 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Figure imgf000167_0001
Table 18 IP
Table 18 IP provides 3240 compounds of formula II-D) wherein Gi is GOl and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 182P
Table 182P provides 3240 compounds of formula II-D) wherein Gi is G02 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 183P
Table 183P provides 3240 compounds of formula II-D) wherein Gi is G03 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 184 P
Table 184P provides 3240 compounds of formula II-D) wherein Gi is G04 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 185P
Table 185P provides 3240 compounds of formula II-D) wherein Gi is G051 and X1, X2, X3, Y1, Y2, Y3, X4 and Pv5 have the values listed in the table P.
Table 186P
Table 186P provides 3240 compounds of formula II-D) wherein Gi is G06 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P.
Table 187P
Table 187P provides 3240 compounds of formula II-D) wherein Gi is G07 and X1, X2, X3, Y1, Y2, Y3, X and Pv5 have the values listed in the table P. Table
Table 88P provides 3240 compounds of formula II-D) wherein Gi is G08 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 89P
Table 89P provides 3240 compounds of formula II-D) wherein Gi is G09 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 90P
Table 90P provides 3240 compounds of formula II-D) wherein Gi is G10 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 91P
Table 91P provides 3240 compounds of formula II-D) wherein Gi is GI 1 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 92 P
Table 92P provides 3240 compounds of formula II-D) wherein Gi is G12 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 93P
Table 93P provides 3240 compounds of formula II-D) wherein Gi is G13 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 94P
Table 94P provides 3240 compounds of formula II-D) wherein Gi is G14 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 95P
Table 95P provides 3240 compounds of formula II-D) wherein Gi is G15 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 96 P
Table 96P provides 3240 compounds of formula II-D) wherein Gi is G16 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 97 P
Table 97P provides 3240 compounds of formula II-D) wherein Gi is G17 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 98P
Table 98P provides 3240 compounds of formula II-D) wherein Gi is G18 and X1, X2, X3, Y1, Y2, Y3, X and R have the values listed in the table P.
Table 99P
Table 199P provides 3240 compounds of formula II-D) wherein Gi is G19 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 200P
Table 200P provides 3240 compounds of formula II-D) wherein Gi is G20 and X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Figure imgf000168_0001
Table 2410
Table 241Q provides 54 compounds of formula (II-E) wherein Gi is G01 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2420
Table 242Q provides 54 compounds of formula (II-E) wherein Gi is G02 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2430
Table 243Q provides 54 compounds of formula (II-E) wherein Gi is G03 and X1, X2, X3and X4 have the values listed in the table Q.
Table 244Q Λ ct
- loo -
Table 244Q provides 54 compounds of formula (II-E) wherein Gi is G04 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2450
Table 245Q provides 54 compounds of formula (II-E) wherein Gi is G05 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2460
Table 246Q provides 54 compounds of formula (II-E) wherein Gi is G06 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2470
Table 247Q provides 54 compounds of formula (II-E) wherein Gi is G07 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2480
Table 248Q provides 54 compounds of formula (II-E) wherein Gi is G08 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2490
Table 249Q provides 54 compounds of formula (II-E) wherein Gi is G09 and X1, X2, X3and X4 have the values listed in the table Q.
Table 250O
Table 250Q provides 54 compounds of formula (II-E) wherein Gi is G10 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2510
Table 251Q provides 54 compounds of formula (II-E) wherein Gi is GI 1 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2520
Table 252Q provides 54 compounds of formula (II-E) wherein Gi is G12 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2530
Table 253Q provides 54 compounds of formula (II-E) wherein Gi is G13 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2540
Table 254Q provides 54 compounds of formula (II-E) wherein Gi is G14 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2550
Table 255Q provides 54 compounds of formula (II-E) wherein Gi is G15 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2560
Table 256Q provides 54 compounds of formula (II-E) wherein Gi is G16 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2570
Table 257Q provides 54 compounds of formula (II-E) wherein Gi is G17 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2580
Table 258Q provides 54 compounds of formula (II-E) wherein Gi is G18 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2590
Table 259Q provides 54 compounds of formula (II-E) wherein Gi is G19 and X1, X2, X3and X4 have the values listed in the table Q.
Table 260O
Table 260Q provides 54 compounds of formula (II-E) wherein Gi is G20 and X1, X2, X3and X4 have the values listed in the table Q.
Figure imgf000170_0001
Table 2610
Table 261Q provides 54 compounds of formula (II-F) wherein Gi is G01 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2620
Table 262Q provides 54 compounds of formula (II-F) wherein Gi is G02 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2630
Table 263 Q provides 54 compounds of formula (II-F) wherein Gi is G03 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2640
Table 264Q provides 54 compounds of formula (II-F) wherein Gi is G04 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2650
Table 265Q provides 54 compounds of formula (II-F) wherein Gi is G05 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2660
Table 266Q provides 54 compounds of formula (II-F) wherein Gi is G06 and X1, X2, X3and X4 have the values listed in the table Q.
Table 267Q
Table 267Q provides 54 compounds of formula (II-F) wherein Gi is G07 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2680
Table 268Q provides 54 compounds of formula (II-F) wherein Gi is G08 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2690
Table 269Q provides 54 compounds of formula (II-F) wherein Gi is G09 and X1, X2, X3and X4 have the values listed in the table Q.
Table 270O
Table 270Q provides 54 compounds of formula (II-F) wherein Gi is G10 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2710
Table 271Q provides 54 compounds of formula (II-F) wherein Gi is GI 1 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2720
Table 272Q provides 54 compounds of formula (II-F) wherein Gi is G12 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2730
Table 273 Q provides 54 compounds of formula (II-F) wherein Gi is G13 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2740
Table 274Q provides 54 compounds of formula (II-F) wherein Gi is G14 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2750
Table 275Q provides 54 compounds of formula (II-F) wherein Gi is G15 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2760 j Q
Table 276Q provides 54 compounds of formula (II-F) wherein Gi is G16 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2770
Table 277Q provides 54 compounds of formula (II-F) wherein Gi is G17 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2780
Table 278Q provides 54 compounds of formula (II-F) wherein Gi is G18 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2790
Table 279Q provides 54 compounds of formula (II-F) wherein Gi is G19 and X1, X2, X3and X4 have the values listed in the table Q.
Table 280O
Table 28 OQ provides 54 compounds of formula (II-F) wherein Gi is G20 and X1, X2, X3and X4 have the values listed in the table Q.
Figure imgf000171_0001
Table 2810
Table 281 Q provides 54 compounds of formula (II-G) wherein Gi is G01 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2820
Table 282Q provides 54 compounds of formula (II-G) wherein Gi is G02 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2830
Table 283Q provides 54 compounds of formula (II-G) wherein Gi is G03 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2840
Table 284Q provides 54 compounds of formula (II-G) wherein Gi is G04 and X1, X2, X and X4 have the values listed in the table Q.
Table 2850
Table 285Q provides 54 compounds of formula (II-G) wherein Gi is G05 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2860
Table 286Q provides 54 compounds of formula (II-G) wherein Gi is G06 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2870
Table 287Q provides 54 compounds of formula (II-G) wherein Gi is G07 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2880
Table 288Q provides 54 compounds of formula (II-G) wherein Gi is G08 and X1, X2, X and X4 have the values listed in the table Q.
Table 2890
Table 289Q provides 54 compounds of formula (II-G) wherein Gi is G09 and X1, X2, X3and X4 have the values listed in the table Q.
Table 290O
Table 290Q provides 54 compounds of formula (II-G) wherein Gi is G10 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2910
Table 291Q provides 54 compounds of formula (II-G) wherein Gi is GI 1 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2920 j
Table 292Q provides 54 compounds of formula II-G) wherein Gi is G12 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2930
Table 293Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G13 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2940
Table 294Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G14 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2950
Table 295Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G15 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2960
Table 296Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G16 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2970
Table 297Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G17 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2980
Table 298Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G18 and X1, X2, X3and X4 have the values listed in the table Q.
Table 2990
Table 299Q provides 54 compounds of formula ΊΙ-G) wherein Gi is G19 and X1, X2, X3and X4 have the values listed in the table Q.
Table 3 OOP
Table 300Q provides 54 compounds of formula ;iI-G) wherein Gi is G20 and X1, X2, X3and X4 have the values listed in the table Q.
Figure imgf000172_0001
Table 3010
Table 301 Q provides 54 compounds of formula (II-H) wherein Gi is G01 and X1, X2, X3and X4 have the values listed in the table Q.
Table 302O
Table 302Q provides 54 compounds of formula (II-H) wherein Gi is G02 and X1, X2, X3and X4 have the values listed in the table Q.
Table 303O
Table 303Q provides 54 compounds of formula (II-H) wherein Gi is G03 and X1, X2, X3and X4 have the values listed in the table Q.
Table 304O
Table 304Q provides 54 compounds of formula (II-H) wherein Gi is G04 and X1, X2, X'and X4 have the values listed in the table Q.
Table 305O
Table 305Q provides 54 compounds of formula (II-H) wherein Gi is G05 and X1, X2, X3and X4 have the values listed in the table Q.
Table 306O
Table 306Q provides 54 compounds of formula (II-H) wherein Gi is G06 and X1, X2, X3and X4 have the values listed in the table Q.
Table 307O
Table 307Q provides 54 compounds of fomiula (II-H) wherein Gi is G07 and X1, X2, X and X4 have the values listed in the table Q.
Table 308O Table 308Q provides 54 compounds of formula II-H) wherein Gi is G08 and X1, X2, X3and X4 have the values listed in the table Q.
Table 309O
Table 309Q provides 54 compounds of formula II-H) wherein Gi is G09 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 310O
Table 3 10Q provides 54 compounds of formula II-H) wherein Gi is G10 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 HQ
Table 3 HQ provides 54 compounds of formula II-H) wherein Gi is GI 1 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 120
Table 3 12Q provides 54 compounds of formula II-H) wherein Gi is G12 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 130
Table 3 13Q provides 54 compounds of formula II-H) wherein Gi is G13 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 140
Table 3 14Q provides 54 compounds of formula II-H) wherein Gi is G14 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 150
Table 3 15Q provides 54 compounds of formula II-H) wherein Gi is G15 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 160
Table 3 16Q provides 54 compounds of formula II-H) wherein Gi is G16 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 170
Table 3 17Q provides 54 compounds of formula II-H) wherein Gi is G17 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 180
Table 3 18Q provides 54 compounds of formula II-H) wherein Gi is GI 8 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 3 190
Table 3 19Q provides 54 compounds of formula II-H) wherein Gi is G19 and X1, X2, X3and X4 have the values 1 isted in the table Q.
Table 320O
Table 320Q provides 54 compounds of formula II ■H) wherein Gi is G20 and X1, X2, X3and X4 have the values listed in the table Q.
Table S
Figure imgf000173_0001
Λ„„
S.015 bromo Y1 is N, Y2 is CH, Y3 is CH
S.016 fluoro Y1 is N, Y2 is CH, Y3 is CH
S.017 trifluoromethyl Y1 is N, Y2 is CH, Y3 is CH
S.018 methyl Y1 is N, Y2 is CH, Y3 is CH
S.019 ethyl Y1 is N, Y2 is CH, Y3 is CH
S.020 methoxy Y1 is N, Y2 is CH, Y3 is CH
S.021 nitro Y1 is N, Y2 is CH, Y3 is CH
S.022 trifluoromethoxy Y1 is N, Y2 is CH, Y3 is CH
S.023 cyano Y1 is N, Y2 is CH, Y3 is CH
S.024 cyclopropyl Y1 is N, Y2 is CH, Y3 is CH
S.025 hydrogen Y1 is N, Y2 is N, Y3 is CH
S.026 chloro Y1 is N, Y2 is N, Y3 is CH
S.027 bromo Y1 is N, Y2 is N, Y3 is CH
S.028 fluoro Y1 is N, Y2 is N, Y3 is CH
S.029 trifluoromethyl Y1 is N, Y2 is N, Y3 is CH
S.030 methyl Y1 is N, Y2 is N, Y3 is CH
S.031 ethyl Y1 is N, Y2 is N, Y3 is CH
S.032 methoxy Y1 is N, Y2 is N, Y3 is CH
S.033 nitro Y1 is N, Y2 is N, Y3 is CH
S.034 trifluoromethoxy Y1 is N, Y2 is N, Y3 is CH
S.035 cyano Y1 is N, Y2 is N, Y3 is CH
S.036 cyclopropyl Y1 is N, Y2 is N, Y3 is CH
S.037 hydrogen Y1 is CH, Y2 is N, Y3 is CH
S.038 chloro Y1 is CH, Y2 is N, Y3 is CH
S.039 bromo Y1 is CH, Y2 is N, Y3 is CH
S.040 fluoro Y1 is CH, Y2 is N, Y3 is CH
S.041 trifluoromethyl Y1 is CH, Y2 is N, Y3 is CH
S.042 methyl Y1 is CH, Y2 is N, Y3 is CH
S.043 ethyl Y1 is CH, Y2 is N, Y3 is CH
S.044 methoxy Y1 is CH, Y2 is N, Y3 is CH
S.045 nitro Y1 is CH, Y2 is N, Y3 is CH
S.046 trifluoromethoxy Y1 is CH, Y2 is N, Y3 is CH
S.047 cyano Y1 is CH, Y2 is N, Y3 is CH
S.048 cyclopropyl Y1 is CH, Y2 is N, Y3 is CH
S.049 hydrogen Y1 is CH, Y2 is CH, Y3 is N
S.050 chloro Y1 is CH, Y2 is CH, Y3 is N
S.051 bromo Y1 is CH, Y2 is CH, Y3 is N
S.052 fluoro Y1 is CH, Y2 is CH, Y3 is N
S.053 trifluoromethyl Y1 is CH, Y2 is CH, Y3 is N
S.054 methyl Y1 is CH, Y2 is CH, Y3 is N
S.055 ethyl Y1 is CH, Y2 is CH, Y3 is N
S.056 methoxy Y1 is CH, Y2 is CH, Y3 is N
S.0057 nitro Y1 is CH, Y2 is CH, Y3 is N
S.058 trifluoromethoxy Y1 is CH, Y2 is CH, Y3 is N
S.059 cyano Y1 is CH, Y2 is CH, Y3 is N
S.060 cyclopropyl Y1 is CH, Y2 is CH, Y3 is N
Figure imgf000175_0001
Y1, Y2, Υ3 and R5 have the values listed in the table S.
Table 2S
Table 2S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 3S
Table 3S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 4S
Table 4S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 5S
Table 5S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 6S
Table 6S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 7S
Table 7S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 8S
Table 8S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 9S
Table 9S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table IPS
Table 10S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table U S
Table 1 I S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 1, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 12S
Table 12S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 13S
Table 13S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 14S
Table 14S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 15S
Table 15S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 16S
Table 16S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, Y1, Y2, Y3 and R5 have the values listed in the table S. ^
Table 17S
Table 17S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 18S
Table 18S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 19S
Table 19S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 20S
Table 20S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 21 S
Table 21 S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021 , Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 22S
Table 22S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 23 S
Table 23S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 24S
Table 24S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 25 S
Table 25S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 26S
Table 26S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 27S
Table 27S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, Y1, Y2, Y1 and R5 have the values listed in the table S.
Table 28S
Table 28S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 29S
Table 29S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 30S
Table 30S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 3 I S
Table 3 I S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031 , Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 32S
Table 32S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 33 S
Table 33S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 34S
Table 34S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 35S Table 35S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 36S
Table 36S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 37S
Table 37S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 38S
Table 38S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, Y1, Y2, YJ and R5 have the values listed in the table S.
Table 39S
Table 39S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 40S
Table 40S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 41 S
Table 41 S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041 , Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 42S
Table 42S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 43 S
Table 43S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 44S
Table 44S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 45 S
Table 45S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 46S
Table 46S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 47S
Table 47S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 48S
Table 48S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 49S
Table 49S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 50S
Table 50S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 51 S
Table 51 S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051 , Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 52S
Table 52S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 53 S
Table 53S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, Y1, Y2, Y3 and R5 have the values listed in the table S. Table 54S
Table 54S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 55S
Table 55S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 56S
Table 56S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 57S
Table 57S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 58S
Table 58S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 59S
Table 59S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 60S
Table 60S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 61 S
Table 61 S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 62S
Table 62S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 63 S
Table 63S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 64S
Table 64S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 65 S
Table 65S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 66S
Table 66S provides 3240 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 67S
Table 67S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 68S
Table 68S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 69S
Table 69S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 70S
Table 70S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 71 S
Table 71 S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 72S - 1 /o -
Table 72S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 73 S
Table 73S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 74S
Table 74S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 75 S
Table 75S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 76S
Table 76S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 77S
Table 77S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 78S
Table 78S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 79S
Table 79S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 80S
Table 80S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 81 S
Table 81 S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 82S
Table 82S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 83 S
Table 83S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 84S
Table 84S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 85S
Table 85S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 86S
Table 86S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 87S
Table 87S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 88S
Table 88S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 89S
Table 89S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 90S
Table 90S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, Y1, Y2, Y3 and R5 have the values listed in the table S. Table 91 S
Table 91 S provides 60 compounds of formula (ΙΠ-Α) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 92S
Table 92S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 93 S
Table 93S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 94S
Table 94S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 95 S
Table 95S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 96S
Table 96S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 97S
Table 97S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 98S
Table 98S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 99S
Table 99S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 100S
Table 100S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 101 S
Table 101S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 102S
Table 102S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 132S
Table 103S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 104S
Table 104S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 105S
Table 105S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 106S
Table 106S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 107S
Table 107S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 108S
Table 108S provides 60 compounds of formula (III- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.108, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 109S Table 109S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table HQS
Table 110S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 1 1 1 S
Table 1 1 IS provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 112S
Table 112S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 12, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 1 13 S
Table 1 13S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 13, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 1 14S
Table 114S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 115S
Table 115S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.115, Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 1 16S
Table 1 16S provides 60 compounds of formula (III-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, Y1, Y2, Y3 and R5 have the values listed in the table S.
Figure imgf000181_0001
Table IT:
Table IT provides 116 compounds of formula (III-B) wherein G1 is oxygen, R1 is hydrogen, R has the values listed in Table G.
Figure imgf000181_0002
Table 1U:
Table 1U provides 116 compounds of formula (III-C) wherein G1 is oxygen, R1 is hydrogen, R2 has the values listed in Table G.
Figure imgf000181_0003
Table 117S
Table 117S provides 60 compounds of formula (III-D) wherein Het is Het.Ol, and Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 1 18S Table 118S provides 60 compounds of formula (III-D) wherein Het is Het.02 and Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 119S
Table 119S provides 60 compounds of formula (III-D) wherein Het is Het.03 and Y1, Y2, Y3 and R5 have the values listed in the table S.
Table 120S
Table 120S provides 60 compounds of formula (III-D) wherein Het is Het.04 and Y1, Y2, Y3 and R5 have the values listed in the table
Table IV
Table IV provides 4 compo as listed in Table Het.
Figure imgf000182_0001
Table 1W
Table 1 W provides 4 compounds of formula (III-F) wherein Het has the values listed in Table Het.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
Additional examples of insects from the family of Curculionidae. axe Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi, Anthonomus signatus, Anthonomus subfasciatus, and Anthonomus tenebrosus.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against Anthonomus grandis in cotton.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing soil pests.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing corn Diabrotica virgifera. 0
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing corn Diabrotica barberi.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing corn Diabrotica undecimpunctata howardi.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing wireworms, in particular Agriotes spp.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
Additional examples of Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing grubs, in particular white grubs.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
Additional examples of white grubs include Phyllophaga anxia, Phyllophaga crinite,
Phyllophaga subnitida, Diloboderus abderus.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing termites, e.g. on sugarcane.
Examples of termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes,
Globitermes. Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp.. - 1 ο3 -
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing cutworms, e.g. agrotis spp..
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing millipedes, e.g. Julus spp..
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing whitefly.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use in controlling and/or preventing Euschistus spp., particularly in soybean.
Examples of stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilar e), Piezodorus spp. (e.g. Piezodorus guildinu), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g. Eurygaster intergriceps, Eurygaster maura), Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinu, Halyomorpha halys. In one embodiment the stinkbug target is Nezara viridula, Piezodorus spp. , Acrosternum spp, Euchistus heros. - 1 o4 -
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against rice pests.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against stemborer, particularly in rice.
Examples of stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius,
Scirpophaga spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella
Sesamia sp, Sesamia inferens.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against leaffolder, particularly in rice.
Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against hoppers, particularly in rice.
Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against gallmidge, particularly in rice.
Examples of Gall midge include Orseolia sp, Orseolia oryzae.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against whorl maggot, particularly in rice.
Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against Rice bugs, particularly in rice.
Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against Black bugs, particularly in rice.
Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against plutella spp..
In one embodiment the invention provides a compound selected from Tables IP to 120P and 1Q to 240Q for use against Plutella xylostella, particularly in brassica crops.
The compounds of the invention may be made by a variety of methods as shown in the following Schemes. cheme 1
Figure imgf000186_0001
1) Compounds of formula (IX) wherein Rx is Ci-Ci5alkoxy can be prepared by reacting a compound of formula (VIII) with the vinyl compound of formula (VII) in the presence or not of a suitable solvent, for example NN-dimethylformamide, xylene, toluene, chlorobenzene or dichlorobenzene. The reaction can be performed under microwave heating preferably at temperatures up to 200°C and preferably under neat conditions using a large excess of the compound of formula VII (e.g. 40 equivalents). Vinyl compounds of formula (VII) are commercially available or can be made by methods known to a person skilled in the art. Compounds of formula (VIII) can be made by methods known to a person skilled in the art, as described in journal of Organic Chemistry (1981), 46(4), 771-775.
heme 2
Figure imgf000186_0002
(vi i) (χ) (xi)
2) Compounds of formula (XI) can be prepared by reacting a compound of formula (X) wherein X is a leaving group, for example a halogen, such as bromo, with a compound of formula (VII), using the same methods as described in 1).
Scheme 3
Figure imgf000186_0003
(vii) ( ii) (l)
3) Compounds of formula (I) can be prepared by reacting a compound of formula (XII) wherein P is as described for the compound I, with a compound of formula (VII), using the same methods as described in 1).
Scheme 4
Figure imgf000186_0004
4) Compounds of formula (I- A) can be prepared by reacting a compound of formula (XI) wherein X is a leaving group, for example a halogen, such as bromo, with carbon monoxide and an amine of formula (XIII), in the presence of a catalyst, such as palladium(II) diacetate, a ligand, such as a phosphine ligand, 1 fl ,
- l oo - such as tributylphosphine, and a base such as cesium carbonate, or diisopropylethylamine (Hunig's base). The reaction is carried out in a suitable solvent, such as toluene, at a temperature of from 50°C to 200°C, preferably from 100°C to 150°C, in particular at 1 15°C. The reaction is carried out at a pressure of from 50 to 200 bar, preferably from 100 to 150 bar, in particular at 120 bar.
Figure imgf000187_0001
(l-A) (l-A)
5) Compounds of formula (I- A) can be made by treatment of a compound of formula (XIV) with a compound of formula (XIII) and a dehydrating reagent. Alternatively, carboxylic acid (XIV) is transformed to an activated derivative, such as an acid chloride, for instance by treatment with thionyl chloride, or a mixed anhydride, for instance by treatment with ethyl chloroformate, and the activated derivative is reacted with a compound of formula (XIII), optionally in the presence of a base, and in a suitable solvent, such as, for instance, tetrahydrofuran. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
6) Alternatively, compounds of formula (I-A) can be made from a compound of formula (IX) wherein Rx is Ci-Ci5alkoxy by heating the ester and an amine of formula (XIII) together in a thermal process. Amines of formula (XIII) are known in the literature or can be prepared using methods known to a person skilled in the art.
7) Compounds of formula (XIV) can be made by treatment of a compound of formula (XI), wherein X is a halogen, for instance bromine, with a metallating agent, such as a metal, for instance magnesium, - I o / - or an organometallic compound, for instance butyllithium, followed by the treatment with carbon dioxide. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C. 8) Compounds of formula (XIV) can be made by hydrolysis of a compound of formula (IX), and Rx is Ci-Ci5alkyl, such as methyl or teri-butyl. For instance, in the case where Rx is methyl or ethyl, the hydrolysis can be done with water and a base, such as potassium hydroxide, in the absence or in the presence of a solvent, such as, for instance, tetrahydrofuran or methanol. In the case where Rx is, for example, teri-butyl, the hydrolysis is done in the presence of acid, such as trifluoroacetic acid or hydrochloric acid. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
9) Compounds of formula (IX) wherein Rx is Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XI) wherein X is a leaving group, for example a halogen, such as bromo, with carbon monoxide and an alcohol of formula Rx-OH, such as ethanol, in the presence of a catalyst, such as bis(triphenylphosphine)palladium(II) dichloride, and a base, such as pyridine, triethylamine, 4- (dimethylamino)-pyridine ("DMAP") or diisopropylethylamine (Hunig's base). The reaction is carried out at a temperature of from 50°C to 200°C, preferably from 100°C to 150°C, in particular at 1 15°C. The reaction is carried out at a pressure of from 50 to 200 bar, preferably from 100 to 150 bar, in particular at 120 bar.
Scheme 6
Figure imgf000188_0001
(IA)
10) Compounds of formula (IA), wherein Pn is an optionally substituted heterocycle, can be made, for example in the case where the heterocycle is attached via a nitrogen atom, by treatment of a compound (XI) wherein X is a halogen, such as fluorine, with a heterocyclic compound Pn-H and a suitable base, such as potassium carbonate. Alternatively, compounds of formula (IA), wherein Pn is an optionally substituted heterocycle, can be made, for example in the case where the heterocycle is attached via a carbon atom, by treatment of a compound (XI) wherein X is a halogen, such as bromine, with a heterocyclic compound Pn-M, wherein M is hydrogen or a metal, such as boron, magnesium or zinc, in which case M can be optionally substituted, with a base and a suitable catalyst, such as a palladium or a copper catalyst, in the presence of a suitable ligand for the catalyst, such as, for example, a diamine ligand, or a phosphine ligand. Such reactions are carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C. Sc
Figure imgf000189_0001
11) Compounds of formula (XVII) wherein P is as defined for compounds (I) and Z1 is hydrogen, halogen, cyano, Ci-Cgalkyl, aryl-Ci-C4alkylene-, CpCgalkylcarbonyl-, arylsulfonyl- or arylthio-, can be obtained by reacting an unsaturated ketone of formula (XV) wherein G1 is oxygen, with a sulfur nucleophile, such as thioacetic acid, hydrogen sulfide, sodium sulfide, ammonium sulfide, thiourea, benzylmercaptan, Sodium benzenethiosulfonate, sodium thiomethoxide or tert-butyl mercaptan as shown on Scheme 7. Such reactions can be performed optionally in the presence of a base, such as sodium hydroxide, sodium ethoxide, sodium methoxide, sodium tert-butoxide or potassium hydroxide.
Sometimes, such reations can also be performed in the presence of an acid, for example p-toluenesulfonic acid, hydrochloric acid, acetic acid, in a solvent, such as methanol, ethanol, NN-dimethylformamide, toluene, dichloromethane, ethyl acetate, acetonitrile or chlorobenzene or water, or mixtures thereof, at a temperature of from 0°C to 100°C, preferably from ambient temperature to 80°C. Such conditions are described, for example, in Journal of the American Chemical Society (1949), 71, 3554-5 or in
Tetrahedron: Asymmetry (2003), 14(1), 113-117 and Journal of Organic Chemistry (1996), 61, 1986.
12) Compounds of formula (XVI) wherein P is as defined for compounds (I) and Z3 is thiol or aryl substituted Ci-Cgalkylsulfinyl-, can be made by reaction of the ketone of formula (XV) with an amine, such as triphenylmethanesulfenamide. Such reactions are usually carried out in the presence of an acid or not, for example p-toluenesulfonic acid, hydrochloric acid, acetic acid, optionnally in the presence of a solvent, for example an alcohol, such as methanol or ethanol, or toluene, dichloromethane, water, or mixtures thereof. The reaction can be carried our in the presence or the absence of a dehydrating agent, such as anhydrous magnesium sulfate or molecular sieves. It can also be perfomed using a Dean Stark or Soxhlet apparatus that enables a constant removal of the water formed during the reaction. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature.
13) Compounds of formula (XVIII) wherein P is as defined for compounds (I) and Z2 is hydrogen or hydroxyl or CpCgalkoxy- or Ci-Cgalkylsulfonyloxy- or Ci-Cgarylsulfonyloxy- or aryl-Ci-C4alkylene-or aryl, can be made by reaction of the ketone of formula (XVII) with an amine, such as hydroxylamine hydrochloride, methoxylamine or ammonia. Such reactions are carried out in the presence of a base, for example an organic base, such as triethylamine or sodium acetate, or an inorganic base, such as sodium hydrogen carbonate, optionally in the presence of a solvent, for example an alcohol, such as methanol or ethanol, or water, or mixtures thereof. Such reactions can also be carried out in the presence of an acid or not, for example p-toluenesulfonic acid, hydrochloric acid, acetic acid, optionnally in the presence of a solvent, for example an alcohol, such as methanol or ethanol, or toluene, dichloromethane, water, or mixtures thereof. The reaction can be carried our in the presence or the absence of a dehydrating agent, such as anhydrous magnesium sulfate or molecular sieves. It can also be perfomed using a Dean Stark or Soxhlet apparatus that enables a constant removal of the water formed during the reaction. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature.
14) Compounds of formula (I) can be obtained by eye Using a compound of formula (XVI) wherein Z3 is thiol. Such reactions are usually carried out in the presence of an acid or not, for example p- toluenesulfonic acid, optionnally in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene.The reaction is carried out at a temperature of from 0°C to 200°C, preferably from 25°C to 100°C. Alternatively, compounds of formula (I) wherein P is as defined for compounds (I) can be obtained by cyclising a compound of formula (XVI) wherein Z3 is aryl substituted Ci-Cgalkylsulfinyl-. Such reactions are usually carried out in the presence of an acid or not, for example p-toluenesulfonic acid, trifluoroacetic acid or hydrochloric acid, optionnally in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene.The reaction is carried out at a temperature of from 0°C to 200°C, preferably from 25°C to 100°C. Such reactions usually involve first the deprotection of the thiol to give a compound of formula (XVI) wherein Z3 is thiol, followed by the cyclization.
15) Compounds of formula (I) can be obtained from compound of formula (XVIII) wherein Z1 is hydrogen or CpCgalkyl or aryl-Ci-C4alkylene-or CpCgalkylcarbonyl- or arylsulfonyl- or arylthio-, and Z2 is hydrogen or hydroxyl or CpCgalkoxy- or CpCgalkylsulfonyloxy- or CpCgarylsulfonyloxy- or aryl-Cr C4alkylene-or aryl. Such reactions usually involve the deprotection of Z1 and ofZ2 or of both groups. The
Figure imgf000190_0001
(XVIIIa) (XVI I lb) (XVI lie)
Depending on the nature of Z1 and Z2, the deprotection conditions are different and can be made by methods known to a person skilled in the art or as described in T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 564-566, 740-743.
16) Compounds of formula (I) can be obtained from compound of formula (XVIIIa) from an oxidation step. Such reactions are usually carried out in the presence of an oxidant, for example iodine, bromine, thionyl chloride, Bis(trifluoroacetoxy)iodobenzene; The reaction can be carried our in the presence of an acid or not, such as trifluoroacetic acid or acetic acid, optionnally in the presence of a solvent, for example dichloroethane, dimethylsulfoxide, NN-dimethylformamide, methanol, ethanol, toluene, dichloromethane, ethyl acetate or chlorobenzene.The reaction is carried out at a temperature of from 0°C to 200°C, preferably from 25°C to 100°C. Such transformations, including reaction conditions and suitable catalyst, are described in Journal of the Chemical Society, Perkin Transactions 1 : Organic and Bio-Organic Chemistry (1972-1999) (1985), (1), 153-7 and Organic Letters (2006), 8(21), 4811- 4813. Similarly, compounds of formula (I-I) wherein P is as defined for compounds (I) can be obtained from a compound of formula (XVIIIb) wherein Z1 is arylsulfonyl- or arylthio-, by an oxidation step, are described in Journal of Organic Chemistry (1990), 55(13), 4156-62.
17) Compounds of formula (I) can be obtained from compound of formula (XVIIIc) wherein Z2 is Cp Cgalkoxy-. Such reactions are usually carried out in the presence of a copper (I) reagent, such copper-3- methylsalicylate. The reaction can be carried out in the presence of a solvent, for example dichloroethane, dimethylsulfoxide, NN-dimethylformamide, methanol, ethanol, toluene, dichloromethane, ethyl acetate or chlorobenzene.The reaction is carried out at a temperature of from 0°C to 200°C, preferably from 25°C to 100°C, or under microwave heating conditions. Such transformations are described in Journal of the American Chemical Society (2011), 133, 6403-6410.
18) Alternatively, compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z1 is hydrogen. Such reactions are usually carried out in the presence chloramines, formed in situ from ammonia and chlorine or sodium hypochlorite or hypochlorous acid, optionally in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene. The reaction is carried out at a temperature of from -80°C to 40°C, preferably below - 40°C.
19) Alternatively, compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z1 is halogen, cyano, arylsulfonyl- or arylthio-. Such reactions are usually carried out in the presence ammonia, optionally in the presence of a solvent, for example dichloroethane,
tetrahydrofuran, methanol, ethanol, toluene, dichloromethane or chlorobenzene. The reaction is carried out at a temperature of from -80°C to 80°C.
20) Alternatively, compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z1 is aryl-Ci-C4alkylene. Such reactions are usually carried out in two steps- The first one involves the treatment of a compound of formula (XVII) wherein Z1 is aryl-Ci-C4alkylene by a suitable oxidant, such as sulfuryl chloride or chlorine, in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene, dichloromethane or chlorobenzene, to provide a compound of formula (XVII) wherein Z1 is chlorine. The second step then involves the treatment a compound of formula (XVII) wherein Z1 is chlorine by an ammonia source, such as ammonia or ammonium bromide in the presence of a base, in the presence of a solvent, for example dichloroethane, methanol, ethanol, toluene,
tetrahydrofuran, dichloromethane or chlorobenzene. Both steps are usually carried out at a temperature of from -80°C to 80°C. 21) Alternatively, compounds of formula (I) can be obtained directly from a compound of formula (XVII) wherein Z1 is hydrogen. Such reactions are usually carried out in the presence of a suitable nitrogen electrophile, such as Hydroxylamine-O-sulfonic acid. Such reactions are carried out in the presence of a base, for example an organic base, such as triethylamine or sodium acetate, or an inorganic base, such as sodium hydrogen carbonate, sodium hydroxide or potassium hydroxide optionally in the presence of a solvent, for example tetrahydrofuran, toluene, an alcohol, such as methanol or ethanol, or water, or mixtures thereof. The reaction is carried out at a temperature of from -80°C to 80°C.
Figure imgf000192_0001
Similarly to what is described from 11) to 16), compounds of (XI) wherein X is a leaving group, for example a halogen, such as bromo can be obtained.
Scheme 9
Figure imgf000192_0002
(xxv) (xxvi) (XXVI I)
Similarly to what is described from 11) to 16), compounds of formula (XXVII) wherein Rx is Cp Ci5alkoxy can be obtained.Unless otherwise indicated in the above descriptions reference to leaving groups includes leaving groups such as halogen, CpCgalkoxy, CpCgalkylsulfonyloxy, Cp
Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. the leaving group may be selected from -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 _) and phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl).
The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the compounsd of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies). The compounds of the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad- leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like. Compositions comprising the compound of formula I may be used on ornamental garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars. Compositions comprising the compound of formula I may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars.
Furthermore, the compounds of the invention may be effective against harmful insects, without substantially imposing any harmful side effects to cultivated plants. Application of the compounds of the invention may increase the harvest yields, and may improve the quality of the harvested material. The compounds of the invention may have favourable properties with respect to amount appled, residue formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents.
Examples of pest species which may be controlled by the compounds of formula (I) include: coleopterans, for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum,
Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis; lepidopterans, for example, Lymantria dispar, Malacosoma neustria), Pieris rapae,
Spodoptera litura, Mamestra brassicae, Chilo suppressalis), Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsa pomonella, Agrotisfucosa, Galleria mellonella, Plutella maculipennis, Heliothis virescens, Phyllocnistis citrella; hemipterans, for example, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki, Unaspis yanonensis, Myzus persicas, Aphis pomi, Aphis gossypii,
Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nezara spp., Trialeurodes vaporariorm, Psylla spp.; thysanopterans, for example, Thrips palmi, Franklinella occidental; orthopterans, for example, Blatella germanica, Periplaneta americana, Gryllotalpa Africana, Locusta migratoria migratoriodes ; isopterans, for example, Reticulitermes speratus, Coptotermes formosanus; dipterans, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis, Culex tritaeniorhynchus, Liriomyza trifolii; acari, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp. ; nematodes, for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp.. Examples of further pest species which may be controlled by the compounds of formula (I) include: from the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.; from the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp.,
Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici; from the class of the Bivalva, for example, Dreissena spp.; from the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.; from the order of the Coleoptera, for example,
Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator,
Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna
consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., PopilUa japonica, Premnotrypes spp., PsylUodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.; from the order of the Collembola, for example, Onychiurus armatus; from the order of the Dermaptera, for example, Forficula auricularia; from the order of the Diplopoda, for example, Blaniulus guttulatus; from the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp.,
Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example,
Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opistorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofii; ft may be furthermore possible to control protozoa, such as Eimeria; from the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp.,
Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta per sea, Rhodnius spp.,
Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp.,
Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,
Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, MonelUopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,
Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii; from the order of the
Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Mono- morium pharaonis, Vespa spp.; from the order of the Isopoda, for example, Armadillidium vulgar e, Oniscus asellus, Porcellio scaber; from the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.; from the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp.,
Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mods repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.; from the order of the
Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria; from the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example, Scutigerella immaculata; from the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.; from the order of the Thysanura, for example, Lepisma saccharina. The phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp.,
Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp.,
Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
In particular, the compounds of the invention may be used to control the following pest spcies:
Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafliopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton leafworm), Heliothis virescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locusta migratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp. (rootworms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplaneta americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the
Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermes formosanus, Λ nr
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Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulfureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes),
Rhodopholus spp. (banana burrowing nematodes), Tylenchulus spp.(citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabditis elegans (vinegar eelworm), Trichostrongylus spp. (gastro intestinal nematodes) and Deroceras reticulatum (slug).
The compound of formula I may be used for pest control on various plants, including soybean (e.g. in some cases 10-70g/ha), corn (e.g. in some cases 10-70g/ha), sugarcane (e.g. in some cases 20- 200g/ha), alfalfa (e.g. in some cases 10-70g/ha), brassicas (e.g. in some cases 10-50g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70g/ha), potatoes (including sweet potatoes) (e.g. in some cases 10- 70g/ha), cotton (e.g. in some cases 10-70g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g. in some cases 30-150g/ha), citrus (e.g. in some cases 60-200g/ha), almonds (e.g. in some cases 40-180g/ha), fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.) (e.g. in some cases 10-80g/ha), tea (e.g. in some cases 20-150g/ha), bulb vegetables (e.g. onion, leek etc.) (e.g. in some cases 30-90g/ha), grapes (e.g. in some cases 30-180g/ha), pome fruit (e.g. apples, pears etc.) (e.g. in some cases 30-180g/ha), and stone fruit (e.g. pears, plums etc.) (e.g. in some cases 30-180g/ha).
The compounds of the invention may be used for pest control on various plants, including soybean, corn, sugarcane, alfalfa, brassicas, oilseed rape (e.g. canola), potatoes (including sweet potatoes), cotton, rice, coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulb vegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples, pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.
The compounds of the invention may be used on soybean to control, for example, Elasmopalpus Ugnosellus, Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., aphids, Sternechus subsignatus, Formicidae, Agrotis ypsilon, Julus spp., Murgantia spp., Halyomorpha spp., Thyanta spp., Megascelis ssp., Procornitermes ssp., Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp., Neomegalotomus spp., Cerotoma trifurcata, PopilUa japonica, Edessa spp., Liogenys fuscus, Euschistus hews, stalk borer, Scaptocoris castanea, phyllophaga spp., Migdolus spp.,
Pseudoplusia includens, Anticarsia gemmatalis, Epinotia spp., Rachiplusia spp., Spodoptera spp., Bemisia tabaci, Tetranychus spp., Agriotes spp. , Euschistus spp.. The compounds of the invention are preferably used on soybean to control Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, PopilUa japonica, Euschistus hews, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Agriotes spp., Euschistus spp..
The compounds of the invention may be used on corn to control, for example, Euschistus hews,
Euschistus spp., Dichelops furcatus, Diloboderus abderus, Thyanta spp., Elasmopalpus Ugnosellus, Halyomorpha spp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, PopilUa japonica, Agrotis ypsilon, Diabrotica speciosa, aphids, Heteroptera, Procornitermes spp., Scaptocoris castanea, Formicidae, Julus ssp., Dalbulus maidis, Diabrotica virgifera, Diabrotica spp., Mods latipes, Bemisia tabaci, heliothis spp., Tetranychus spp., thrips spp., phyllophaga spp., Migdolus spp., scaptocoris spp., Liogenys fuscus, Spodoptera spp., Ostrinia spp., Sesamia spp., wireworms, Agriotes spp., Halotydeus destructor. The compounds of the invention are preferably used on corn to control Euschistus hews, Euschistus spp., Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Diabrotica speciosa, Diabrotica virgifera, Diabrotica spp., Tetranychus spp., Thrips spp., Phyllophaga spp., Migdolus spp., Scaptocoris spp., Agriotes spp..
The compounds of the invention may be used on sugar cane to control, for example,
Sphenophorus spp., termites, Migdolus spp., Diloboderus spp., Telchin licus, Diatrea saccharalis, Mahanarva spp., Mealybugs.
The compounds of the invention may be used on alfalfa to control, for example, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collops spp., Empoasca solana, Epitrix spp., Geocoris spp., Lygus hesperus, Lygus lineolaris, Spissistilus spp., Spodoptera spp., Aphids, Trichoplusia ni. The compounds of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix spp., Lygus hesperus, Lygus lineolaris, Trichoplusia ni.
The compounds of the invention may be used on brassicas to control, for example, Plutella xylostella, Pieris spp., Mamestra spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Spodoptera spp., Empoasca spp., thrips spp., Delia spp., Murgantia spp., Trialeurodes spp., Bemisia spp., Microtheca spp., Aphids. The compounds of the invention are preferably used on brassicas to control Plutella xylostella, Pieris spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp..
The compounds of the invention may be used on oil seed rape, e.g. canola, to control, for example, Meligethes spp., Ceutorhynchus napi, Halotydeus destructor, Psylloides spp..
The compounds of the invention may be used on potatoes, including sweet potatoes, to control, for example, Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladera matrida, Agriotes spp., Aphids, wireworms. The compounds of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Agriotes spp..
The compounds of the invention may be used on cotton to control, for example, Anthonomus grandis, Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp., Empoasca spp., Thrips spp., Bemisia tabaci, Trialeurodes spp., Aphids, Lygus spp., phyllophaga spp., Scaptocoris spp., Austroasca viridigrisea, Creontiades spp., Nezara spp., Piezodorus spp., Halotydeus destructor, Oxycaraenus hyalinipennis, Dysdercus cingulatus. The compounds of the invention are preferably used on cotton to control Anthonomus grandis, Tetranychus spp., Empoasca spp., thrips spp., Lygus spp., phyllophaga spp., Scaptocoris spp..
The compounds of the invention may be used on rice to control, for example, Leptocorisa spp.,
Cnaphalocrosis spp., Chilo spp., Scirpophaga spp., Lissorhoptrus spp., Oebalus pugnax, Scotinophara spp., Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix spp., Mealybugs, Sogatella furcifera, Nilaparvata lugens, Orseolia spp., Cnaphalocrocis no medinalis, Marasmia spp., Stenchaetothrips biformis, Thrips spp., Hydrellia philippina, Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Chilo suppressalis, Chilo auricilius, Chilo polychrysus, Sesamia inferens, Laodelphax striatellus, Nymphula depunctalis, Oulema oryzae, Stinkbugs. The compounds of the invention are preferably used on rice to control Leptocorisa spp., Lissorhoptrus spp., Oebalus pugnax, Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix spp., Sogatella furcifera, Stenchaetothrips biformis, Thrips spp., Hydrellia philippina, Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Chilo suppressalis, Chilo polychrysus, Oulema oryzae.
The compounds of the invention may be used on coffee to control, for example, Hypothenemus Hampei, Perileucoptera Coffeella, Tetranychus spp., Brevipalpus spp., Mealybugs. The compounds of the invention are preferably used on coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.
The compounds of the invention may be used on citrus to control, for example, Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., Thrips spp., Unaspis spp., Ceratitis capitata, Phyllocnistis spp., Aphids, Hardscales, Softscales, Mealybugs. The compounds of the invention are preferably used on citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., thrips spp., Phyllocnistis spp..
The compounds of the invention may be used on almonds to control, for example, Amyelois transitella, Tetranychus spp..
The compounds of the invention may be used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control, for example, Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp., Bemisia tabaci, Trialeurodes spp., Aphids, Paratrioza spp., Frankliniella occidentalis, Frankliniella spp., Anthonomus spp., Phyllotreta spp., Amrasca spp., Epilachna spp., Halyomorpha spp., Scirtothrips spp., Leucinodes spp., Neoleucinodes spp. Maruca spp., Fruit flies, Stinkbugs, Lepidopteras, Coleopteras. The compounds of the invention are preferably used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp., Paratrioza spp., Frankliniella occidentalis, Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp., Neoleucinodes spp..
The compounds of the invention may be used on tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp., Caloptilia theivora, Tetranychus spp..T e compounds of the invention are preferably used on tea to control Empoasca spp., Scirtothrips spp..
The compounds of the invention may be used on bulb vegetables, including onion, leek etc. to control, for example, Thrips spp., Spodoptera spp., heliothis spp.. The compounds of the invention are preferably used on bulb vegetables, including onion, leek etc. to control Thrips spp..
The compounds of the invention may be used on grapes to control, for example, Empoasca spp., Lobesia spp., Eupoecilia ambiguella, Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Eotetranychus WUlamettei, Erythroneura Elegantula, Scaphoides spp., Scelodonta strigicollis, Mealybugs. The compounds of the invention are preferably used on grapes to control Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Scaphoides spp..
The compounds of the invention may be used on pome fruit, including apples, pears etc., to control, for example, Cacopsylla spp., Psylla spp., Panonychus ulmi, Cydia pomonella, Lepidopteras, Aphids, Hardscales, Softscales. The compounds of the invention are preferably used on pome fruit, including apples, pears etc., to control Cacopsylla spp., Psylla spp., Panonychus ulmi.
The compounds of the invention may be used on stone fruit to control, for example, Grapholita molesta, Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp., Aphids, Hardscales, Softscales, Mealybugs. The compounds of the invention are preferably used on stone fruit to control Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp..
The compounds of the invention may be used on cereals to control, for example, Aphids, Stinkbugs, earthmites, Eurygaster integriceps, Zabrus tenebrioides, AnisopUa austriaca, Chaetocnema aridula, Phyllotreta spp., Oulema melanopus, Oscinella spp., Delia spp., Mayetiola spp., Contarinia spp., Cephus spp., Steneotarsonemus spp., Apamea spp..
In another embodiment compounds of formula I and mixtures of the invention may be used on rice to control Baliothrips biformis (Thrips), Chilo spp. (e.g. Chilo polychrysus (Dark headed striped borer), Chilo suppressalis (Rice stemborer), Chilo indicus (Paddy stem borer), Chilo polychrysus (Dark- headed rice borer), Chilo suppressalis (Stripe stem borer)), Cnaphalocrocis medinalis (Rice leaf folder), Dicladispa armigera (Hispa), Hydrellia philipina (Rice whorl-maggot), Laodelphax spp. (Smaller brown planthopper) (e.g. Laodelphax striatellus ), Lema oryzae (Rice leaf eetle), Leptocorsia acuta (Rice bug), Leptocorsia oratorius (rice bug), Lissorhoptrus oryzophilus (rice water weevil), Mythemina separata (armyworm), Nephottetix spp. (Green leafhopper ) (e.g. Nephotettix cincticeps, Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens), Nilaparvata lugens (Brown
Planthopper), Nymphula depunctalis (Rice caseworm), Orseolia oryzae (Rice Gall midge), Oulema oryzae (Rice leafbeetle), Scirpophaga incertulas (Yellow Stemborer), Scirpophaga innotata (White Stemborer), Scotinophara coarctata (Rice black bug), Sogaella frucifera (White-backed planthopper), Steneotarsonemus spinki.
The compounds of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.
The compounds of the invention may be used to control ornamental pests including: Ants
(Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets, Cutworms, Eastern tent caterpillars, Elm leaf beetles, European sawflies, Fall web worms, Flea beetles, ^QQ
Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beetles (adults), Lace bugs, Leaf- feeding caterpillars, Leafhoppers, Leafminers (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs, Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock moth larvae, Wasps, Broadmites, Brown softscales, California redscales (crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spider mites, Whiteflies
The compounds of the invention may be used to control turf pests including: Ants (Including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sod webworms, Sow bugs, Ticks (including species which transmit Lyme disease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult), Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult), Mole crickets (nymphs and young adults), Mole Crickets (mature adults), Chinch Bugs.
The compounds of formula (I) and mixture of the invention, in particular those in the tables above, may be used for soil applications, including as a seed application, to target at least the following: sucking pests such as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs, white flies (e.g. on cotton and vegetables), mites; on soil pests such as corn root worm, wireworms, white grubs, zabrus, termites (e.g. on sugar cane, soy, pasture), maggots, cabbage root fly, red legged earth mite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus, plutella (e.g. brassica), stem borers, leaf miners, flea beetle, Sternechus; on nematicides, such as Heterodera glycines (e.g. on soybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn), P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables), Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g. on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus (e.g. on cereals), thornei (e.g. on cereals).
The compounds of formula (I) and mixture of the invention, in particular those in the tables above may be used for seed applications at least on the following: soil grubs for corn, soybeans, sugarcane: Migdolus spp; Phyllophaga spp.; Diloboderus spp; Cyclocephala spp; Lyogenys fuscus; sugarcane weevils: Sphenophorus levis & Metamasius hemipterus; termites for soybeans, sugarcane, pasture, others: Heterotermes tenuis; Heterotermes longiceps; Cornitermes cumulans; Procornitermes triacifer ;
Neocapritermes opacus; Neocapritermes parvus; corn root worms for corn and potatoes: Diabrotica spp., seed Maggot: Delia platura; soil stinkbugs: Scaptocoris castanea; wireworms: Agriotes spp; Athous spp Hipnodes bicolor; Ctenicera destructor; Limonius canu; Limonius californicus; rice water weevil:
Lissorhoptrus oryzophilus; Red Legged earth mites: Halotydeus destructor.
The invention therefore provides a method of combating and/or controlling an animal pest, e.g. an invertebrate animal pest, which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I). In particular, the invention provides a method of combating and/or controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest, The compounds of formula (I) are preferably used against insects, acarines or nematodes.
The term "plant" as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names RoundupReady® and
LibertyLink®.
The compounds of the invention may be applied to plant parts. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
Compounds of formula I may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
The preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest 2Q2 yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds.
Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
Compounds of formula I may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like. Such pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3. A full list of Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of Sussex {see also, Crickmore et al. (1998) Microbiol. Mol. Biol. Rev. 62:807-813). Other pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome- inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. Further examples of such pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073. The methods for producing such transgenic plants are generally known to the person skilled in the art and some of which are commercially available such as Agrisure®CB (corn producing CrylAb), Agrisure®RW (corn producing mCry3A), Agrisure® Viptera (corn hybrids producing Vip3Aa); Agrisure300GT (corn hybrids producing CrylAb and mCry3A); YieldGard® (corn hybrids producing the CrylAb protein), YieldGard® Plus (corn hybrids producing CrylAb and Cry3Bbl), Genuity® SmartStax® (corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (corn hybrids producing CrylFa) and Herculex®RW (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]) ; NuCOTN®33B (cotton cultivars producing CrylAc), Bollgard®I (cotton cultivars producing CrylAc), Bollgard®!! (cotton cultivars producing CrylAc and Cry2Ab2) and VIPCOT® (cotton cultivars 2Q3 producing a Vip3Aa). Soybean Cyst Nematode resistance soybean (SCN® - Syngenta) and soybean with Aphid resistant trait (AMT®) are also of interest.
Further examples of such transgenic crops are:
1. Btll Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylA(b) toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
2. Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/ES/96/02.
6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry IF 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-l 150 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 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
Further examples of transgenic plants, and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto), HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or 2Q4 triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g. Optimum GAT®), plants stacked with STS® and Roundup Ready® or plants stacked with STS® and Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto). Of particular interest are soybean plants carrying trains conferring resistance to 2.4D (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto).
Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003,
(http://bats.ch).
Examples of cotton transgenic events include MON 531 / 757 / 1076 (Bollgard I ® - Monsanto), MON1445 (Roundup ready cotton ®- Monsanto), MON531 x MON1445 (Bollgard I + RR ®- Monsanto), MON15985 (Genuity Bollgard II cotton ®- Monsanto), MON88913 (Genuity RR FLEX cotton ®- Monsanto), MON15985 x MON1445 (Genuity Bollgard II + RR FELX cotton ®- Monsanto), MON15983 x MON88913 (Genuity Bollgard II + RR FLEX cotton ® - Monsanto), MON15985
(FibreMax Bollgard II Cotton ® - Monsanto), LL25 (FibreMax LL cotton ® - BCS Stoneville), GHB614 (FibreMax GlyTol cotton ®- BCS Stoneville), LL25 x MON15985 (FibreMax LL Bollgard II cotton ® - BCS Stoneville / Monsanto), GHB614 x LL25 (FibreMax LL GlyTol cotton ® - BCS Stoneville), GHB614 x LL25 x MON15985 (FibreMax RR GlyTol Bollgard II cotton ® - BCS Stoneville),
MON88913 x MON15985 (FibreMax LL GlyTol Bollgard II cotton ® - Monsanto), MON88913 (FibreMax RR Flex cotton ® - Monsanto), GHB119 + T304-40 (Twinlink ® - BCS Stoneville), GHB119 + T304-40 x LL25 x GHB614 (Twinlink LL GT ® - BCS Stoneville), 3006-210-23 x 281-24-236 (PhytoGen Widestrike Insect Protection ® - Dow), 3006-210-23 x 281-24-236 x MON88913 (PhytoGen Widestrike Insect Protection + RR FLEX - ® Dow / Monsanto), 3006-210-23 x 281-24-236 x MON1445 ((PhytoGen Widestrike Insect Protection + RR ® - Dow / Monsanto), MON1445 (PhytoGen Roundup Ready ® - Monsanto), MON88913 (PhytoGen Roundup Ready FLEX ® - Monsanto), COT102 x COT67B (Vipcot ® - Syngenta), COT102 x COT67B x MON88913 (Vipcot RR FLEX ® - Syngenta / Monsanto), 281-24-236 (Dow), 3006-210-23 (Dow), COT102 (Syngenta), COT67B (Syngenta), T304-40 (BCS Stoneville).
Examples of Soy transgenic events include MON87701 x MON89788 (Genuity Roundup ready 2 Yield soybeans® - Monsanto), MON89788 (Roundup Ready2Yield®, RR2Y® - Monsanto), MON87708 (Monsanto), 40-3-2 (Roundup Ready®, RRl® - Monsanto), MON87701 (Monsanto), DAS-68416 (Enlist Weed Control System® - Dow), DP356043 (Optimum GAT® - Pioneer), A5547-127 (LibertyLink soybean® - Bayercropscience), A2704-12 (Bayercropscience), GU262 (Bayercropscience), W62 W98 (Bayercropscience), CRV127 (Cultivance® - BASF / EMBRAPA) SYHT0H2 (WO2012/082548). 2Q5
Examples of Maize transgenic events include T25 (LibertyLink®, LL® - Bayerscropscience), DHT-1 (Dow), TCI 507 (Herculex I® - Dow), DAS59122-7 (Herculex RW® - Dow), TCI 507 + DAS59122-7 - Herculex Xtra® - Dow), TCI 507 x DAS-59122-7 x NK603 (Herculex Xtra + RR® - Dow), TC1507 x DAS-59122- x MON88017 x MON89034 (Genuity Smartstax corn®, Genuity
Smartstax RIB complete® - Monsanto / Dow), MON89034 x NK603 (Genuity VT double PRO® -
Monsanto), MON89034 + MON88017 (Genuity VT Triple PRO® - Monsanto), NK603 (Roundup Ready 2®, RR2® - Monsanto), MON810 (YieldGard BT®, Yieldgard cornborer® - Monsanto), MON810 x NK603 (YieldGard cornborer RR Corn 2® - Monasnto), MON810 x MON863 (YieldGard Plus® - Monsanto), MON863 x MON810 x NK603 (YieldGard Plus + RR Corn2® / YieldGard RR Maize® - Monsanto), MON863 x NK603 (YieldGard Rotworm + RR Corn 2® - Monsanto), MON863 (YieldBard RW® - Monsanto), MON89034 (YieldGard RW® - Monsanto), MON88017 (YieldGard VT RW® - Monsanto), MON810 + MON88017 (YieldGard VT Triple® - Monsanto), MON88017 + MON89034 (YieldGard VT Triple Pro® - Monsanto), Btl 1 + MIR604 + GA21 (Agrisure 3000® - Syngenta), Btl 1 + TC1507 + MIR604 + 5307 + GA21 (Syngenta), Btl 1 + TC1507 + MIR604 + DAS59122 + GA21 (Agrisure 3122® - Syngenta), BT11 (Agrisure CB® - Syngenta), GA21 - (Agrisure GT® - Syngenta), MIR604 (Agrisure RW® - Syngenta), Btl 1 + MIR162 (Agrisure TL VIP® - Syngenta), BT11 + MIR162 + GA21 (Agrisure Viptra 3110® - Syngenta), BT11 + MIR162 + MIR604 (Agrisure TM 3100® - Syngenta), Event3272 + BT11 + MIR604 + GA21 (Syngenta), BT11 + MIR1692 + MIR604 + GA21 (Agrisure Viptera 3111® - Syngenta), BT11 + MIR 162 + TC1507 + GA21 (Agrisure Viptera 3220® - Syngenta), BT11 + MIR162 + TC1507 + MIR604 + 5307 + GA21 (Agrisure Viptera 3222® - Syngenta), MIR162 (Syngenta), BT11 + GA21 + MIR162 + MIR604 + 5307 (Syngenta), 5307 (Syngenta).
In order to apply a compound of formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I). The composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from O.lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
When used in a seed dressing, a compound of formula (I) is generally used at a rate of O.OOOlg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
In another aspect the present invention provides a composition comprising a pesticidally effective amount of a compound of formula (I), in particular an insecticidal, acaricidal, nematicidal or
molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally . _ ,
- 206 - effective amount of a compound of formula (I) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
The compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro- emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
Dustable powders (DP) may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
Soluble powders (SP) may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water
dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
Wettable powders (WP) may be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).
Granules (GR) may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre- formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent). 2Q7
Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallization in a spray tank).
Emulsifiable concentrates (EC) or oil- in- water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg-Cio fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of formula (I) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs. An ME may be either an oil-in- water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in- water emulsion.
Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane). A compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non- pressurized, hand-actuated spray pumps. ΛΟ
- 2Uo -
A compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment. A compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
A composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
A compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-z' opropyl- and tri-wopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3-sulfate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates. 2Q9
Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);
alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Suitable suspending agents include hydrophilic colloids (such as polysaccharides,
polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
A compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water- soluble bag) in soil or an aqueous environment.
A compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
A compound of formula (I) may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of formula (I).
The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity. The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate. An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition.
Examples of suitable pesticides include the following (where "Tx" means a compound of formula (I), and in particular a compound selected from Tables IP to 120P and 1Q to 240Q which may result in a synergistic combination with the given active ingredient):
a) Pyrethroids, such as permethrin +Tx, cypermethrin+Tx, fenvalerate+Tx, esfenvalerate+Tx, deltamethrin+Tx, cyhalothrin+Tx (in particular lambda-cyhalothrin+Tx and gamma
cyhalothrin+Tx), bifenthrin+Tx, fenpropathrin+Tx, cyfluthrin+Tx, tefluthrin+Tx, fish safe pyrethroids+Tx (for example ethofenprox+Tx), natural pyrethrin+Tx, tetramethrin+Tx,
S-bioallethrin+Tx, fenfluthrin+Tx, prallethrin+Tx, acrinathirin+Tx, etofenprox +Tx or
5 -benzyl-3 -furylmethyl-(E)-( 1 R,3 S)-2,2-dimethyl- 3 -(2-oxothio lan-3 -ylidenemethyl)cyclopropane carboxylate+Tx;
b) Organophosphates, such as profenofos+Tx, sulprofos+Tx, acephate+Tx, methyl
parathion+Tx, azinphos-methyl+Tx, demeton-s-methy+Tx 1, heptenophos+Tx, thiometon+Tx, fenamiphos+Tx, monocrotophos+Tx, profenofos+Tx, triazophos+Tx, methamidophos+Tx, dimethoate+Tx, phosphamidon+Tx, malathion+Tx, chlorpyrifos+Tx, phosalone+Tx, terbufos+Tx, fensulfothion+Tx, fonofos+Tx, phorate+Tx, phoxim+Tx, pirimiphos-methyl+Tx, pirimiphos-ethyl+Tx, fenitrothion+Tx, fosthiazate+Tx or diazinon+Tx;
c) Carbamates (including aryl carbamates), such as pirimicarb+Tx, triazamate+Tx,
cloethocarb+Tx, carbofuran+Tx, furathiocarb+Tx, ethiofencarb+Tx, aldicarb+Tx, thiofurox+Tx, carbosulfan+Tx, bendiocarb+Tx, fenobucarb+Tx, propoxur+Tx, methomyl+Tx or oxamyl+Tx; d) Benzoyl ureas, such as diflubenzuron+Tx, triflumuron+Tx, hexaflumuron+Tx,
flufenoxuron+Tx, diafenthiuron+Tx, lufeneron+Tx, novaluron+Tx, noviflumuron+Tx or chlorfluazuron+Tx;
e) Organic tin compounds, such as cyhexatin+Tx, fenbutatin oxide+Tx or azocyclotin+Tx; f) Pyrazoles, such as tebufenpyrad+Tx, tolfenpyrad+Tx, ethiprole+Tx, pyriprole+Tx, fipronil+Tx, and fenpyroximate+Tx; g) Macrolides, such as avermectins or milbemycins, for example abamectin+Tx, emamectin benzoate+Tx, ivermectin+Tx, milbemycin+Tx, spinosad+Tx, azadirachtin+Tx, milbemectin+Tx, lepimectin+Tx or spinetoram+Tx;
h) Hormones+Tx or pheromones+Tx;
i) Organochlorine compounds, such as endosulfan+Tx (in particular alpha-endosulfan+Tx), benzene hexachloride+Tx, DDT+Tx, chlordane+Tx or dieldrin+Tx;
j) Amidines, such as chlordimeform+Tx or amitraz+Tx;
k) Fumigant agents, such as chloropicrin+Tx, dichloropropane+Tx, methyl bromide+Tx or metam+Tx;
1) Neonicotinoid compounds, such as imidacloprid+Tx, thiacloprid+Tx, acetamiprid+Tx, nitenpyram+Tx, dinotefuran+Tx, thiamethoxam+Tx, clothianidin+Tx, or nithiazine+Tx;
m) Diacylhydrazines+Tx, such as tebufenozide+Tx, chromafenozide+Tx or
methoxyfenozide+Tx;
n) Diphenyl ethers, such as diofenolan+Tx or pyriproxifen+Tx;
o) Pyrazo lines such as Indoxacarb+Tx or metaflumizone+Tx;
p) Ketoenols, such as Spirotetramat+Tx, spirodiclofen+Tx or spiromesifen+Tx;
q) Diamides, such as flubendiamide+Tx, chlorantraniliprole +Tx (Rynaxypyr®) or
cyantraniliprole+Tx;
r) Essential oils such as Bugoil® - (Plantlmpact); or
s) a comopund selected from buprofezine+Tx, flonicamid+Tx, acequinocy+Tx 1, bifenazate+Tx, cyenopyrafen+Tx, cyflumetofen+Tx, etoxazole+Tx, flometoquin+Tx, fluacrypyrim+Tx, fluensulfone+Tx, flufenerim+Tx, flupyradifuone+Tx, harpin+Tx, iodomethane+Tx,
dodecadienol+Tx, pyridaben+Tx, pyridalyl+Tx, pyrimidifen+Tx, flupyradifurone+Tx, 4-[(6- Chloro-pyridin-3-ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one (DE 102006015467), CAS: 915972-17-7 +Tx (WO 2006129714; WO2011/147953; WO2011/147952), CAS: 26914- 55-8 (WO 2007020986), chlorfenapyr+Tx, pymetrozine+Tx, sulfoxaflor+Tx and
pyrifluqinazon+Tx.
In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticide (combinations such as cartap +Tx) or hopper specific insecticides (combinations such as buprofezin +Tx) for use in rice may be employed. Alternatively insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, to give combinations such as clofentezine +Tx, flubenzimine +Tx, hexythiazox +Tx or tetradifon +Tx; acaricidal motilicides, to give combinations such as dicofol +Tx or propargite +Tx; acaricides, to give combinations such as bromopropylate +Tx or chlorobenzilate +Tx; or growth regulators, such as hydramethylnon +Tx, cyromazine +Tx, methoprene +Tx, chlorfluazuron +Tx or diflubenzuron +Tx).
Examples of fungicidal compounds and combinations which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2- methoxy-iminoacetamide (SSF-129) +Tx, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethyl- benzimidazole- 1 -sulfonamide +Tx, a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y
-butyro lactone +Tx, 4-chloro-2-cyano-N,N-dimethyl-5-/?-tolylimidazole-l -sulfonamide (IKF- 916, cyamidazosulfamid) +Tx, 3-5-dichloro-N-(3-chloro-l -ethyl- l-methyl-2-oxopropyl)-4- methylbenzamide (RH-7281, zoxamide) +Tx, N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3- carboxamide (MON65500) +Tx, N-(l-cyano-l,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)- propionamide (AC382042) +Tx, N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide +Tx, acibenzolar (CGA245704) (e.g. acibenzolar-S-methyl) +Tx, alanycarb +Tx, aldimorph +Tx, anilazine +Tx, azaconazole +Tx, azoxystrobin +Tx, benalaxyl +Tx, benomyl +Tx,
benthiavalicarb +Tx, biloxazol +Tx, bitertanol +Tx, bixafen +Tx, blasticidin S +Tx, boscalid +Tx, bromuconazole +Tx, bupirimate +Tx, captafol +Tx, captan +Tx, carbendazim +Tx, carbendazim +Tx, chlorhydrate +Tx, carboxin +Tx, carpropamid +Tx, carvone +Tx, CGA41396 +Tx, CGA41397 +Tx, chinomethionate +Tx, chlorothalonil +Tx, chlorozolinate +Tx, clozylacon +Tx, copper containing compounds to give combintations such as copper oxychloride +Tx, copper oxyquinolate +Tx, copper sulfate +Tx, copper tallate +Tx and Bordeaux mixture +Tx, cyclufenamid +Tx, cymoxanil +Tx, cyproconazole +Tx, cyprodinil +Tx, debacarb +Tx, di-2-pyridyl disulfide Ι,Γ-dioxide +Tx, dichlofluanid +Tx, diclomezine +Tx, dicloran +Tx, diethofencarb +Tx, difenoconazole +Tx, difenzoquat +Tx, diflumetorim +Tx,
C^O-di-zso-propyl-S-benzyl thiophosphate +Tx, dimefluazole +Tx, dimetconazole +Tx, dimethomorph +Tx, dimethirimol +Tx, diniconazole +Tx, dinocap +Tx, dithianon +Tx, dodecyl dimethyl ammonium chloride +Tx, dodemorph +Tx, dodine +Tx, doguadine +Tx, edifenphos +Tx, epoxiconazole +Tx, ethirimo +Tx 1, ethyl-(Z)-N-benzyl-N-([methyl(methyl- thioethylideneaminooxycarbonyl)amino]thio)- -alaninate +Tx, etridiazole +Tx, famoxadone +Tx, fenamidone (RPA407213) +Tx, fenarimol +Tx, fenbuconazole +Tx, fenfuram +Tx, fenhexamid (KBR2738) +Tx, fenpiclonil +Tx, fenpropidin +Tx, fenpropimorph +Tx, fentin acetate +Tx, fentin hydroxide +Tx, ferbam +Tx, ferimzone +Tx, fluazinam +Tx, fludioxonil +Tx, flumetover +Tx, fluopyram +Tx, fluoxastrobin +Tx, fluoroimide +Tx, fluquinconazole +Tx, flusilazole +Tx, flutolanil +Tx, flutriafol +Tx, fluxapyroxad +Tx, folpet +Tx, fuberidazole +Tx, furalaxyl +Tx, furametpyr +Tx, guazatine, +Tx hexaconazole +Tx, hydroxyisoxazole +Tx, hymexazole +Tx, imazalil +Tx, imibenconazole +Tx, iminoctadine +Tx, iminoctadine triacetate +Tx, ipconazole +Tx, iprobenfos +Tx, iprodione +Tx, iprovalicarb (SZX0722) +Tx, isopropanyl butyl carbamate +Tx, isoprothiolane +Tx, isopyrazam +Tx, kasugamycin +Tx, kresoxim-methyl +Tx, LY 186054 +Tx, LY211795 +Tx, LY248908 +Tx, mancozeb +Tx, mandipropamid +Tx, maneb +Tx, mefenoxam +Tx, metalaxyl +Tx, mepanipyrim +Tx, mepronil +Tx, metalaxyl +Tx, metconazole +Tx, metiram +Tx, metiram-zinc +Tx, metominostrobin +Tx, myclobutanil +Tx, neoasozin +Tx, nickel dimethyldithiocarbamate +Tx, nitrothal-z'sopropyl +Tx, nuarimol +Tx, ofurace +Tx, organomercury compounds, +Tx oxadixyl +Tx, oxasulfuron +Tx, oxolinic acid +Tx, oxpoconazole +Tx, oxycarboxin +Tx, pefurazoate +Tx, penconazole +Tx, pencycuron +Tx, penflufen +Tx, penthiopyrad +Tx, phenazin oxide +Tx, phosetyl-Al +Tx, phosphorus acids +Tx, phthalide +Tx, picoxystrobin (ZA1963) +Tx, polyoxinD +Tx, polyram +Tx, probenazole +Tx, prochloraz +Tx, procymidone +Tx, propamocarb +Tx, propiconazole +Tx, propineb +Tx, propionic acid +Tx, prothioconazole +Tx, pyrazophos +Tx, pyrifenox +Tx, pyrimethanil +Tx, pyraclostrobin +Tx, pyroquilon +Tx, pyroxyfur +Tx, pyrrolnitrin +Tx, quaternary ammonium compounds +Tx, quinomethionate +Tx, quinoxyfen +Tx, quintozene +Tx, sedaxane +Tx, sipconazole (F-155) +Tx, sodium pentachlorophenate +Tx, spiroxamine +Tx, streptomycin +Tx, sulfur +Tx, tebuconazole +Tx, tecloftalam +Tx, tecnazene +Tx, tetraconazole +Tx, thiabendazole +Tx, thifluzamid +Tx, 2-(thiocyanomethylthio)benzothiazole +Tx, thiophanate-methyl +Tx, thiram +Tx, timibenconazole +Tx, tolclofos-methyl +Tx, tolylfluanid +Tx, triadimefon +Tx, triadimenol +Tx, triazbutil +Tx, triazoxide +Tx, tricyclazole +Tx, tridemorph +Tx,
trifloxystrobin (CGA279202) +Tx, triforine +Tx, triflumizole +Tx, triticonazole +Tx, validamycin A +Tx, vapam +Tx, vinclozolin +Tx, zineb +Tx and ziram +Tx, N-[9- (dichloromethylene)- 1 ,2,3,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl]-3-(difluoromethyl)- 1 - methyl- lH-pyrazole-4-carboxamide [1072957-71-1] +Tx, l-methyl-3-difluoromethyl-lH- pyrazole-4-carboxylic acid (2-dichloromethylene-3 -ethyl- 1 -methyl- indan-4-yl)-amide +Tx, and 1 -methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy- 1 -methyl-ethyl] -amide +Tx.
The active ingredients combinations described above comprising a compound selected of the invention, in particulary from Tables IP to 90P and 1Q to 36Q and an active ingredient as described above are preferably combined in a mixing ratio of from 100: 1 to 1 :6000, especially from 50: 1 to 1 :50, more especially in a ratio of from 20: 1 to 1 :20, even more especially from 10: 1 to 1 : 10, very especially from 5 : 1 and 1 :5, special preference being given to a ratio of from 2: 1 to 1 :2, and a ratio of from 4: 1 to 2: 1 being likewise preferred, above all in a ratio of 1 : 1 , or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 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 understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
In addition, biological agents may be included in the composition of the invention e.g. Baciullus species such as Bacillus firmus+Tx, Bacillus cereus+Tx, Bacillus subtilis+Tx, and Pasteuria species such as Pasteuria penetrans +Tx and Pasteuria nishizawae+Tx. A suitable Bacillus firmus strain is strain CNCM 1-1582 which is commercially available as BioNem™. A suitable Bacillus cereus strain is strain CNCM 1-1562. Of both Bacillus strains more details can be found in US 6,406,690. Other biological organisms that may be included in the compositions of the invention are bacteria such as Streptomyces spp. such as S. avermitilis, and fungi such as Pochonia spp. such as P. chlamydosporia+Tx. Also of interest are Metarhizium spp. such as M. anisopliae+Tx; Pochonia spp. such as P. chlamydosporia+Tx.
The compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIX™.
Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.
The compounds of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots. The animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.
In a further aspect the invention provides a compound of the invention for use in a method of therapeutic treatment. In a further aspect the invention relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a compound of the invention. The administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body. In a further aspect the invention relates to a compound of the invention for controlling parasitic invertebrate pests in or on an animal. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal
In a further aspect, the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticidally effective amount of a compound of the invention to the environment in which an animal resides.
In a further aspect the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.
In a further aspect the invention provides a method of treating an animal suffering from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to a compound of the invention for use in treating an animal suffering from a parasitic invertebrate pest. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for treating an animal suffering from a parasitic invertebrate pest.
In a further aspect, the invention provides a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.
The compounds of the invention may be used alone or in combination with one or more other biologically active ingredients.
In one aspect the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a compound of the invention and component B is a compound as described below.
The compounds of the invention may be used in combination with anthelmintic agents. Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-444964 and EP-594291.
Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole,
mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, . Λ ,
- 216 - pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
The compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.
The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
The compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers W095/19363 or WO04/72086, particularly the compounds disclosed therein.
Other examples of such biologically active compounds that the compounds of the invention may be used in combination with include but are not restricted to the following:
Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S -methyl, demeton-S -methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos- methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.
Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) - (1 R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta - cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)- cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda- cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.
Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,
teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI- 220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, Buprofezine pyrimidifen, NC- 1111 , R- 195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.
Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamid, captafol, captan, carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid, fenpiclonil, fenpropidin,
fenpropimorph, fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin, fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl- aluminium, furalaxyl, furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, krsoxim- methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole,
metominostrobin/fenominostrobin, metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin.
Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
Bactericides: chlortetracycline, oxytetracycline, streptomycin. - 1 ο -
Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.
When used in combination with other active ingredients, the compounds of the invention are preferably used in combination with the following (where "Tx" means a compound of formula (I), and in particular a compound selected from Tables IP to 90P and 1Q to 36Q, which may result in a synergistic combination with the given active ingredient): imidacloprid + Tx, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, fipronil + Tx, ivermectin + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, milbemycin + Tx, cyromazine + Tx, thiamethoxam + Tx, pyriprole + Tx, deltamethrin + Tx, cefquinome + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, metaflumizone + Tx, moxidectin + Tx, methoprene (including S- methoprene) + Tx, clorsulon + Tx, pyrantel + Tx, amitraz + Tx, triclabendazole + Tx, avermectin + Tx, abamectin + Tx, emamectin + Tx, eprinomectin + Tx, doramectin + Tx, selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, fiubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx, levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Tx, triclabendazole + Tx, epsiprantel + Tx, fipronil + Tx, lufenuron + Tx, ecdysone + Tx or tebufenozide + Tx; more preferably, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, pyriprole + Tx, cefquinome + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Tx, pyrantel + Tx, eprinomectin + Tx, doramectin + Tx, selamectin + Tx, nemadectin + Tx, albendazole + Tx, cambendazole + Tx, fenbendazole + Tx, fiubendazole + Tx, mebendazole + Tx, oxfendazole + Tx, oxibendazole + Tx, parbendazole + Tx, tetramisole + Tx, levamisole + Tx, pyrantel pamoate + Tx, oxantel + Tx, morantel + Tx, triclabendazole + Tx, epsiprantel + Tx, lufenuron + Tx or ecdysone + Tx; even more preferably enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, pyriprole + Tx, cefquinome + Tx, florfenicol + Tx, buserelin + Tx, cefovecin + Tx, tulathromycin + Tx, ceftiour + Tx, selamectin + Tx, carprofen + Tx, moxidectin + Tx, clorsulon + Tx or pyrantel + Tx.
Examples of ratios of the compound of formula I to any mixing partner described herein include 100:1 to 1 :6000, 50:1 to 1 :50, 20:1 to 1 :20, even more especially from 10:1 to 1 :10, 5:1 to 1 :5, 2:1 to 1:2, 4: 1 to 2: 1 , 1 : 1 , or 5: 1 , or 5:2, or 5:3, or 5:4, or 4: 1 , or 4:2, or 4:3, or 3 : 1 , or 3 :2, or 2: 1 , or 1 :5, or 2:5, or 3 :5, or 4:5, or 1 :4, or 2:4, or 3 :4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 : 150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 : 1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
Of particular note is a combination where the additional active ingredient has a different site of action from the compound of formula I. In certain instances, a combination with at least one other parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a combination product of the invention may comprise a pesticidally effective amount of a compound of formula I and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action.
One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.
Thus a wide variety of salts of compounds of the invention (and active ingredients used in combination with the active ingredients of the invention) may be useful for control of invertebrate pests and animal parasites. Salts include acid-addition salts with inorganic or organic acids such as
hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
The compounds of the invention also include N-oxides. Accordingly, the invention comprises combinations of compounds of the invention including N-oxides and salts thereof and an additional active ingredient including N-oxides and salts thereof.
The compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone- vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
The compounds of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. 22Q
One method of application involves spraying a water dispersion or refined oil solution of the combination products. Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy. Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aerosol spray can. Such spray compositions can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propellants, foaming agents, etc. as the case may be. Of note is a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier. One embodiment of such a spray composition comprises a pesticidally effective amount of a compound of the invention and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Of note is a spray composition (and a method utilizing such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horse flies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and the like, including individually or in combinations.
The controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internal parasites that are parasitic to the inside of the body of the host animal (e.g., stomach, intestine, lung, veins, under the skin, lymphatic tissue). External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas. Internal parasites include heartworms, hookworms and helminths. The compounds of the invention may be particularly suitable for combating external parasitic pests. The compounds of the invention may be suitable for systemic and/or non- systemic control of infestation or infection by parasites on animals.
The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild, livestock and agricultural working animals. Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers and/or wool), cultured fish, honeybees. By combating parasites, fatalities and performance reduction (in terms of meat, milk, wool, skins, eggs, etc.) are reduced, so that applying the compounds of the invention allows more economic and simple husbandry of animals.
By controlling these pests it is intended to reduce deaths and improve performance (in the case of meat, milk, wool, hides, eggs, honey and the like) and health of the host animal. Also, controlling parasites may help to prevent the transmittance of infectious agents, the term "controlling" referring to the veterinary field, meaning that the active compounds are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels, e.g. the active compound is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation.
The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.
In an embodiment of this invention, the animal is preferably a vertebrate, and more preferably a mammal, avian or fish. In a particular embodiment, the animal subject is a mammal (including great apes, such as humans). Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Avians include Anatidae (swans, ducks and geese),
Columbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges, grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g., ostriches).
Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, Columbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaws and parrots raised for the pet or collector market, among others.
For purposes of the present invention, the term "fish" is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts. Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping. Examples of potential fish recipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.
Other animals are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the compounds of the invention to an animal to be protected include ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc. and protozoae, such as coccidia).
The disease or group of diseases described generally as helminthiasis is due to infection of an animal host with parasitic worms known as helminths. The term 'helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalent and serious economic problem with domesticated animals such as swine, sheep, horses, cattle, goats, dogs, cats and poultry. Among the helminths, the group of worms described as nematodes causes widespread and at times serious infection in various species of animals.
Nematodes that are contemplated to be treated by the compounds of the invention include, without limitation, the following genera: Acanthocheilonema, Aelurostrongylus, Ancylostoma,
Angiostrongylus , Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator,
Nematodirus, Oesophagostomum, Ostertagia, Oxyuris, Parqfilaria, Parascaris, Physaloptera,
Protostrongylus, Setaria, Spirocerca, Stephanofilaria, Strongy ides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.
Of the above, the most common genera of nematodes infecting the animals referred to above are Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum,
Oesophagostomum, Chabertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. Certain of these, such as Nematodirus, Cooperia and Oesophagostomum attack primarily the intestinal tract while others, such as Haemonchus and Ostertagia, are more prevalent in the stomach while others such as
Dictyocaulus are found in the lungs. Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.
Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Alaria, Fasciola, Nanophyetus, Opisthorchis ,
Paragonimus and Schistosoma.
Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.
The most common genera of parasites of the gastrointestinal tract of humans are
Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria, Trichuris and Enterobius. Other medically important genera of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Strongyloides and Trichinella.
Numerous other helminth genera and species are known to the art, and are also contemplated to be treated by the compounds of the invention. These are enumerated in great detail in Textbook of
Veterinary Clinical Parasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6thEdition of Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby, Williams and Wilkins Co., Baltimore, Md.
The compounds of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds in particular insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like). ^
Insect and acarine pests include, e.g., biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.
Adult flies include, e.g., the horn fly or Haematobia irritans, the horse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, the black fly or Simulium spp., the deer fly or Chrysops spp., the louse fly or Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic fly maggots include, e.g., the bot fly {Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp., the screwworm or Cochliomyia hominivorax, the cattle grub or Hypoderma spp., the fleeceworm and the Gastrophilus of horses.
Mosquitoes include, for example, Culex spp., Anopheles spp. and Aedes spp.
Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae; itch or scab mites such as Sarcoptidae spp. for example,
Salpharcoptes scalphabiei; mange mites such as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis; chiggers e.g., Trombiculidae spp. for example the North American chigger,
Trombiculalpha alphalfreddugesi.
Ticks include, e.g., soft-bodied ticks including Argasidae spp. for example Argalphas spp. and Ornithodoros spp.; hard-bodied ticks including Ixodidae spp., for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former Boophilus genera).
Lice include, e.g., sucking lice, e.g., Menopon spp.
and Bovicola spp.; biting lice, e.g., Haematopinus spp., Linognathus spp. and Solenopotes spp.
Fleas include, e.g., Ctenocephalides spp., such as dog flea {Ctenocephalides canis) and cat flea
(Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea {Pulex irritans).
True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimex lectularius); Triatominae spp. including triatomid bugs also known as kissing bugs; for example Rhodnius prolixus and Triatoma spp.
Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors. Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.
Numerous other parasitic invertebrate pests are known to the art, and are also contemplated to be treated by the compounds of the invention. These are enumerated in great detail in Medical and
Veterinary Entomology, D. S. Kettle, John Wiley AND Sons, New York and Toronto; Control of Arthropod Pests of Livestock: A Review of Technology, R. O. Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fla.
The compounds of the invention may also be effective against ectoparasites, e.g. insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like. These include e.g. flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp.
(blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca ^4
domestica (house fly), Morellia simplex (sweat fly), Tabanus spp. (horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis (nasal botfly), Culicoides spp. (midges), Hippobosca equine,
Gastrophilus intestinalis, Gastrophilus haemorrhoidalis and Gastrophilus nasalis; lice such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; keds such as Melophagus ovinus; and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites).
Examples of species of animal health pesets include those from the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; particular examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus; from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; particular examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; from the order of the Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., SimuUum spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,
Chrysops spp., Odagmia spp., Wilhelmia 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., Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora
erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, SimuUum reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis,
Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; particular examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp; from the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (e.g. Suppella longipalpd); from the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of multi host ticks) Ornithonyssus spp., Pneumonyssus spp., RailUetia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particular examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens,
Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; from the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., 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., Laminosioptes spp.; particular examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis,
Neotrombicula desaleri, Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi; Gasterophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius,
Ctenocephalides felis, Lucilia cuprina; examples of acari include Ornithodoros spp., Ixodes spp., Boophilus spp..
Treatments of the invention are by conventional means such as by enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed- through procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration; or by dermal application in the form of, for example, bathing or dipping, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of active-compound-comprising shaped articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.
When compounds of the invention are applied in combination with an additional biologically active ingredient, they may be administered separately e.g. as separate compositions. In this case, the biologically active ingredients may be administered simultaneously or sequentially. Alternatively, the biologically active ingredients may be components of one composition.
The compounds of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.
Typically a parasiticidal composition according to the present invention comprises a compound of the invention, optionally in combination with an additional biologically active ingredient, or N-oxides or salts thereof, with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration (e.g., oral or parenteral administration such as injection) and in accordance with standard practice. In addition, a suitable carrier is selected on the basis of compatibility with the one or more active ingredients in the composition, including such considerations as stability relative to pH and moisture content. Therefore of note are compounds of the invention for protecting an animal from an invertebrate parasitic pest comprising a parasitically effective amount of a compound of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.
For parenteral administration including intravenous, intramuscular and subcutaneous injection, the compounds of the invention can be formulated in suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and/or dispersing agents.
The compounds of the invention may also be formulated for bolus injection or continuous infusion. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g., a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art of pharmaceutical formulation.
Additionally, suspensions of the active compounds may be prepared in a lipophilic vehicle. Suitable lipophilic vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or materials such as liposomes.
Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran. Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose containers. Alternatively, the active ingredient may be in powder form for constitution with a suitable vehicle, e.g., sterile, pyrogen-free water, before use.
In addition to the formulations described supra, the compounds of the invention may also be formulated as a depot preparation. Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection. The compounds of the invention may be formulated for this route of administration with suitable polymeric or hydrophobic materials (for instance, in an emulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble derivative such as, without limitation, a sparingly soluble salt.
For administration by inhalation, the compounds of the invention can be delivered in the form of an aerosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide. In the case of a pressurized aerosol, the dosage unit may be controlled by providing a valve to deliver a metered amount. Capsules and cartridges of, for example, gelatin for use in an inhaler or insufflator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch.
The compounds of the invention may have favourable pharmacokinetic and pharmacodynamic properties providing systemic availability from oral administration and ingestion. Therefore after ingestion by the animal to be protected, parasiticidally effective concentrations of a compound of the invention in the bloodstream may protect the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore of note is a composition for protecting an animal from an invertebrate parasite pest in a form for oral administration (i.e. comprising, in addition to a parasiticidally effective amount of a compound of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).
For oral administration in the form of solutions (the most readily available form for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention and feed/water/lick blocks, the compounds of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g., magnesium stearate), disintegrating agents (e.g., cross-linked
polyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can be added. Pastes and gels often also contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.
In one embodiment a composition of the present invention is formulated into a chewable and/or edible product (e.g., a chewable treat or edible tablet). Such a product would ideally have a taste, texture and/or aroma favored by the animal to be protected so as to facilitate oral administration of the compounds of the invention.
If the parasiticidal compositions are in the form of feed concentrates, the carrier is typically selected from high-performance feed, feed cereals or protein concentrates. 0
- ZZo -
Such feed concentrate-containing compositions can, in addition to the parasiticidal active ingredients, comprise additives promoting animal health or growth, improving quality of meat from animals for slaughter or otherwise useful to animal husbandry.
These additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostats and hormones.
The compound of the invention may also be formulated in rectal compositions such as suppositories or retention enemas, using, e.g., conventional suppository bases such as cocoa butter or other glycerides.
The formulations for the method of this invention may include an antioxidant, such asBHT (butylated hydroxytoluene). The antioxidant is generally present in amounts of at 0.1- 5 percent (wt/vol). Some of the formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included. Common spreading agents used in these pour-on formulations include isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated C12-C18 fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides, silicone oils and dipropylene glycol methyl ether. The pour-on formulations for the method of this invention are prepared according to known techniques. Where the pour-on is a solution, the parasiticide/insecticide is mixed with the carrier or vehicle, using heat and stirring if required. Auxiliary or additional ingredients can be added to the mixture of active agent and carrier, or they can be mixed with the active agent prior to the addition of the carrier. Pour-on formulations in the form of emulsions or suspensions are similarly prepared using known techniques.
Other delivery systems for relatively hydrophobic pharmaceutical compounds may be employed.
Liposomes and emulsions are well-known examples of delivery vehicles or carriers for hydrophobic drugs. In addition, organic solvents such as dimethylsulfoxide may be used, if needed.
The rate of application required for effective parasitic invertebrate pest control (e.g. "pesticidally effective amount") will depend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. One skilled in the art can easily determine the pesticidally effective amount necessary for the desired level of parasitic invertebrate pest control.
In general for veterinary use, the compounds of the invention are administered in a pesticidally effective amount to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.
A pesticidally effective amount is the amount of active ingredient needed to achieve an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest. One skilled in the art will appreciate that the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular result can be determined through simple experimentation. For oral or parenteral administration to animals, a dose of the compositions of the present invention administered at suitable intervals typically ranges from about 0.01 mg/kg to aboutlOO mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.
Suitable intervals for the administration of the compositions of the present invention to animals range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i.e. administering the compounds to the animal once every month).
The following Examples illustrate, but do not limit, the invention.
The following abbreviations were used in this section: DMF: dimethylformamide; THF: tetrahydrofuran; EtOAc : ethyl acetate; s = singlet; bs = broad singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; M.p. = melting point; RT = retention time, [M+H]+ = molecular mass of the molecular cation, [M-H]" = molecular mass of the molecular anion.
The following abbreviations were used throughout this section: s = singlet; bs = broad singlet; d doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; RT = retention time; MH+ = molecular cation.
The invention is now described by way of non- limiting Examples.
Preparation Examples
The following preparation examples describe synthesis of compounds of formula I and intermediates thereof.
Exam le 1 : Preparation of tert-butyl 2-methyl-4-(2-oxo-l,3,4-oxathiazol-5-yl benzoate
Figure imgf000230_0001
a stirring solution of tert-butyl 4-carbamoyl-2-methyl-benzoate (10 g) in mixture of Toluene and Dioxane (3: 1, 240mL) was added potassium carbonate (5.88 g) then chlorocarbonylsulfenyl chloride (5.5mL). The mixture was heated at 100°C for 2 hours. The reaction mixture was allowed to cool to room temperature, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate) to give tert-butyl 2-methyl-4-(2-oxo-l,3,4-oxathiazol-5- yl)benzoate (11.12 g) as a solid. 'H-NMR (CDC13, 400 MHz): δ = 7.87-7.96 (m, 1 H), 7.79-7.87 (m, 2 H), 2.63 (s, 3 H), 1.56-1.64 ppm (m, 9 H).
Example 2: Preparation of tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll-2- methyl-benzoate
Figure imgf000231_0001
solution of tert-butyl 2-methyl-4-(2-oxo-l,3,4-oxathiazol-5-yl)benzoate (50 mg) in l,3-dichloro-5-[l- (trifluoromethyl)vinyl]benzene (5 mL, prepared according to WO 2005085216) was heated 190°C during 10 minutes in a microwave. The residue was purified by chromatography on silica gel (eluent:
cyclohexane / ethyl acetate) then on preparative HPLC to give tert-butyl 4-[5-(3,5-dichlorophenyl)-5- (trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate (18.5 mg) as a solid. 'H-NMR (CDC13, 400 MHz): δ = 7.86 (d, 1 H), 7.54-7.64 (m, 2 H), 7.41 (t, 1 H), 7.31 (s, 2 H), 4.23 (d, 1 H), 3.88 (d, 1 H), 2.61 (s, 3 H), 1.61 ppm (s, 9 H). Example 3: Preparation of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll-2-methyl- benzoic acid
Figure imgf000231_0002
To a solution of tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl- benzoatc (164 mg) in dichloromethanc (1.7 mL) was added trifluoroacetic acid (0.17 mL). The reaction mixture was stirred at room temperature for 6 hours then the solution was concentrated under vacuo. The residue was extracted with water and ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated to give 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3- yl]-2-methyi-benzoic acid (140 mg) as a white foam.
'H-NMR (CDCI3, 400 MHz): δ = 8.11 (d, 1 H), 7.59-7.71 (m, 2 H), 7.42 (t, 1 H), 7.30-7.34 (m, 2 H), 4.25 (d, 1 H), 3.90 (d, 1 H), 2.71 ppm (s, 3 H).
Example 4: Preparation of 3-Benzylsulfanyl-l-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4- trifluoro-butan- 1 - one
Figure imgf000231_0003
Benzylmercaptan (0.18 g) and a solution of sodium hydroxide (0.1 eq) were added to a solution of (E)- 1 - ^ 1
(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-l-one (0.5 g) in
tetrahydrofurane (11.4 niL). The solution was stirred at room temperature for 19 hours then heated at 80°C for 4 hours. Then, more benzylmercaptan (0.5 mL) was added and the solution was stirred at 80°C for 16 hours. More sodium hydroxide (20 mg) was added and after 90 minutes, the reaction was quenched by the addition of a saturated solution of sodium chloride, and then extracted with diethyl ether. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give 3-Benzylsulfanyl-l-(4-bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butan-l-one (276mg).
lH NMR (CDC13, 400MHz): δ = 7.65 (d, J=1.8 Hz, 1 H), 7.61 (d, J=8.1 Hz, 1 H), 7.52 - 7.55 (m, 2 H), 7.48 (dd, J=8.3, 2.0 Hz, 1 H), 7.34 (t, J=1.8 Hz, 1 H), 7.17 - 7.26 (m, 5 H), 3.87 - 3.94 (m, 1 H), 3.85 (d, .7=11.7 Hz, 1 H), 3.69 - 3.79 (m, 1 H), 3.63 (d, J=11.4 Hz, 1 H), 2.44 (s, 3 H). 19F NMR (CDC13, 376MHz): δ = -67.33 ppm_ Example 5: Preparation of tert-butyl 4-[3-benzylsulfanyl-3-(3,5-dichlorophenyl -4,4,4-trifluoro- butano l] -2-methyl-benzoate
Figure imgf000232_0001
Benzylmercaptan (1.5 eq.) and l-[3,5-bis(trifluoromethyl)phenyl]-3-[(lR,2R)-2- (dimethylamino)cyclohexyl]thiourea (0.01 eq.) were added to a solution of tert-butyl 4-[(E)-3-(3,5- dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoate (200 mg) in toluene (1.5 mL) at -40°C . The solution was stirred at -40°C for 6 hours then at room temperature for 17 hours. The reaction was quenched by the addition of a saturated solution of sodium chloride, and then extracted with ethylacetate. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give tert-butyl 4-[3-benzylsulfanyl-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-butanoyl]-2-methyl- benzoate (205 mg) as a mixture of two enantiomers.
Chiral HPLC analysis using a Waters UPLC - Hclass, DAD Detector Waters UPLC.
Column: Daicel CHIRALPAK® IB, 3μηι, 0.46cm x 10cm
Mobile phase: Heptane/iPrOH 95/05
Flow rate: l .O ml/min
Detection: 254nm
Sample concentration: lmg/mL in Hept/iPrOH 70/30
Injection: A \L eluting isomer: rt= 2.43 min, 14%
2nd eluting isomer: rt= 2.95 min, 85%
lU NMR (CHLOROFORM-d ,400MHz): δ= 7.83 (d, J=8.1 Hz, 1 H), 7.59 - 7.69 (m, 2 H), 7.51 - 7.57 (m, 2 H), 7.34 (t, J=1.8 Hz, 1 H), 7.14 - 7.29 (m, 5 H), 3.94 (d, J=16.9 Hz, 1 H), 3.84 (d, J=11.7 Hz, 1 H), 3.73 - 3.81 (m, 1 H), 3.64 (d, J=11.7 Hz, 1 H), 2.59 (s, 3 H), 1.61 ppm (s, 9 H).
Figure imgf000233_0001
Similarly, 5-[(3S)-3-benzylsulfanyl-4,4,4 rifluoro-3-(3,4,5-trichlorophenyl)butanoyl]-2-(l ,2,4-triazol-l - yl)benzonitrile could be prepared.
lH NMR (CDCI3,400MHz): δ= 8.96 (s, 1 H), 8.23 (s, 1 H), 8.11 - 8.18 (m, 2 H), 7.95 (d, J=8.8 Hz, 1 H), 7.65 (s, 2 H), 7.15 - 7.26 (m, 5 H), 3.93 (d, J=12.5 Hz, 1 H), 3.89 (d, J=17.2 Hz, 1 H), 3.74 (d, J=16.9 Hz, 1 H), 3.69 ppm (d, J=12.5 Hz, 1 H)
19H NMR (CDCI3,376MHz): δ= -67.03
Chiral HPLC analysis using a Waters UPLC (Alliance 2695)- Hclass, DAD Detector Waters UPLC (996).
Column: Daicel CHIRALPAK® IA, 3 μηι, 0.46cm x 10cm
Mobile phase: TBME/EtOH 98/02
Flow rate: 1 ml/min
Detection: 254nm
Sample concentration: lmg/mL in TBM
Injection: 2μΕ
1st eluting isomer: rt= 2.52 min; 80.5 %
2nd eluting isomer: rt= 3.24 min; 19.5 %
Example 6: Preparation of l-(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3- sulfanyl-butan- 1 - one
Figure imgf000233_0002
^
To (E)-l-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-but-2-en-l-one (2 g) was added thioacetic acid (6 eq.) under argon. The solution was stirred at room temperature then 2 drops of triethylamine were added. The solution was stirred at room temperature for 4 days.
The mixture was then diluted with ethyl acetate, washed with brine, then water. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 1 - (4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butan-l-one (382 mg). lU NMR (CDC13, 400MHz): δ = 7.77 (d, J=2.2 Hz, 1 H), 7.68 (d, J=8.4 Hz, 1 H), 7.58 - 7.63 (m, 1 H), 7.51 - 7.58 (m, 2 H), 7.35 (t, J=1.8 Hz, 1 H), 4.27 (d, J=18.7 Hz, 1 H), 3.94 (d, J=18.3 Hz, 1 H), 3.29 (s, 1 H), 2.48 ppm (s, 3 H). 19F NMR (CDC13, 376MHz): δ = -73.56 ppm
Another fraction contained Thioacetic acid 3-(4-bromo-3-methyl-phenyl)-l-(3,5-dichloro-phenyl)-3- oxo-l-trifluoromethyl-propyl ester (782 mg). lU NMR (CDC13, 400MHz): δ = 7.78 - 7.84 (m, 1 H), 7.62 - 7.69 (m, 2 H), 7.37 (s, 3 H), 5.16 (d, J=18.0 Hz, 1 H), 3.96 (d, J=18.3 Hz, 1 H), 2.48 (s, 3 H), 2.32 ppm (s, 3 H). 19F NMR (CDCI3, 376MHz): δ = -71.26 ppm
Example 7: Preparation of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-
Figure imgf000234_0001
To a solution of l-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butan- 1-one (382 mg) in a solution of potassium hydroxide (162mg in 8mL of water) was added a solution of Hydroxylamine-O-sulfonic acid (2 equiv.) in a solution of potassium hydroxide (243mg in 16mL of water). After stirring at room temperature for 30 minutes, the mixture was diluted with ethyl acetate, and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane) to give 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5- trifluoromethyl-4,5-dihydro-isothiazole (184mg).
lU NMR (CDCI3, 400MHz): δ = 7.64 (d, J=1.8 Hz, 1 H), 7.60 (d, J=8.4 Hz, 1 H), 7.39 - 7.44 (m, 2 H), 7.28 - 7.33 (m, 2 H), 4.19 (d, J=17.6 Hz, 1 H), 3.86 (d, J=17.6 Hz, 1 H), 2.46 ppm (s, 3 H). 19F NMR (CDCI3, 376MHz): δ = -74.76 ppm
Figure imgf000234_0002
Using the same sequence, 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3- yljbenzonitrile could be obtained, starting from 2-chloro-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2- enoyl]benzonitrile: lU NMR (CDCI3, 400MHz): δ = 7.90 (t, J=0.9 Hz, 1 H), 7.74 (d, J=0.7 Hz, 2 H), 7.43 (t, J=1.8 Hz, 1 H), 7.29 (d, J=l .l Hz, 2 H), 4.19 (d, J=17.6 Hz, 1 H), 3.86 (d, J=18.0 Hz, 1 H) ppm.
Example 8: Preparation of 4-[3-(3,5-Dichloro-phenyl -4,4,4-trifluoro-3-mercapto-butyryll-2-methyl- benzoic acid tert-butyl ester
Figure imgf000235_0001
To 4-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl ester (25 g) was added thioacetic acid (6 eq.) and triethylamine (200 μΕ) The solution was stirred at room temperature 2 drops of triethylamine were added. After stirring at room temperature for 24 hours, the mixture was poured in a mixture of water and ethyl acetate, extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl- benzoic acid tert-butyl ester (3.78g) lH NMR (CDC13, 400MHz): δ = 7.89 (d, J=8.8 Hz, 1 H), 7.72 - 7.79
(m, 2 H), 7.53 - 7.57 (m, 2 H), 7.35 (t, J=1.8 Hz, 1 H), 4.30 (d, J=18.3 Hz, 1 H), 3.97 (d, J=18.3 Hz, 1 H), 3.30 (s, 1 H), 2.59 - 2.65 (m, 3 H), 1.58 - 1.66 (m, 10 H), 1.56 ppm (s, 1 H).
19F NMR (CDCI3, 376MHz): δ = -73.58 ppm.
Another collected fractions contained 4-[3-Acetylsulfanyl-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro- butyryl]-2-methyl-benzoic acid tert-butyl ester (12.51 g).
lU NMR (CDCI3, 400MHz): δ = 7.84 - 7.91 (m, 1 H), 7.77 - 7.84 (m, 2 H), 7.38 (s, 3 H), 5.20 (d, J=18.3 Hz, 1 H), 4.00 (d, J=18.3 Hz, 1 H), 2.63 (s, 3 H), 2.28 - 2.36 (m, 3 H), 1.62 ppm (s, 9 H). 19F NMR (CDCI3, 376MHz): δ = -71.25 ppm
Example 9: Preparation of 4-[5-(3,5-Dichloro-phenyl -5-trifluoromethyl-4,5-dihydro-isothiazol-3-yll-2- methyl-benzoic acid tert-butyl ester
Figure imgf000236_0001
To a solution of 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester (1.875 g) in tetrahydrofuran (6 niL) was added a solution of Hydroxylamine-O-sulfonic acid (2 equiv.) in a solution of potassium hydroxide (1.2 g in 75 mL of water). After stirring at room temperature for 30 minutes, the mixture was quenched with a solution of hydrochloric acid (IN), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 4-[5-(3,5-Dichloro-phenyl)- 5-trifluoromethyl-4,5-dihydro-isothiazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (881 mg) lU NMR (CDC13, 400MHz): δ = 7.86 (d, J=8.4 Hz, 1 H), 7.56 - 7.63 (m, 2 H), 7.41 (t, J=1.8 Hz, 1 H),
7.29 - 7.33 (m, 2 H), 4.22 (d, J=17.6 Hz, 1 H), 3.88 (d, J=18.0 Hz, 1 H), 2.62 (s, 3 H), 1.62 ppm (s, 10 H). 19F NMR (CDCI3, 376MHz): δ = -74.73 ppm
Example 10: Preparation of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isothiazol-3-yll-2- methyl-benzoic acid butyl ester
Figure imgf000236_0002
solution of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro- isothiazole (166 mg) in n-butanol (3 mL) was added palladium acetate (0.1 equiv.), butyl-1- adamantylphophincataxium (0.3 equiv.) then tetramethylethylenediamine (TMEDA) (1 equiv.). The reactor was sealed and a carbon monoxide pressure (5 bars) was applied to the mixture. The reaction was stirred at 110°C for 18 hours. The mixture was then filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give 4-[5- (3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isothiazol-3-yl]-2-methyl-benzoic acid butyl ester (62mg).
lU NMR (CDCl3,400MHz): δ = 7.96 (d, J=8.1 Hz, 1 H), 7.59 - 7.64 (m, 2 H), 7.42 (t, J=1.8 Hz, 1 H), 7.31 (d, J=0.7 Hz, 2 H), 4.33 (t, J=6.6 Hz, 2 H), 4.23 (d, J=17.6 Hz, 1 H), 3.89 (d, J=17.6 Hz, 1 H), 2.65 (s, 3 H), 1.71 - 1.81 (m, 2 H), 1.35 - 1.63 (m, 2 H), 1.00 ppm (t, J=7.5 Hz, 3 H). 19F NMR (CDC13, 376MHz): δ = -74.73 ppm Example 1 1 : Preparation of 4-[3-(3,5-Dichloro-phenyl -4^^-trifluoro-3-mercapto-butyryll-2-methyl-N- thietan-3 -yl-benzamide
Figure imgf000237_0001
To 4-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4 rifluoro-but-2-enoyl]-2-methyl-N-thietan-3-yl-benzamide (500 mg) was added thioacetic acid (6 eq.) and triethylamine (4 μΕ). The solution was stirred under argon at room temperature for 41 hours. To this mixture was added a minimum of dichloromethane and then isolute. The suspension was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate) to give:
4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-N-thietan-3-yl-benzamide ( 493mg).
lU NMR (CDCl3,400MHz): δ = 7.69 - 7.81 (m, 2 H), 7.56 (s, 2 H), 7.44 - 7.51 (m, 1 H), 7.34 - 7.42 (m, 1 H), 6.20 (d, J=8.1 Hz, 1 H), 5.44 (q, J=8.1 Hz, 1 H), 4.29 (d, J=18.3 Hz, 1 H), 3.96 (d, J=18.7 Hz, 1 H), 3.45 - 3.55 (m, 2 H), 3.35 - 3.45 (m, 2 H), 3.29 (s, 1 H), 2.51 ppm (s, 3 H)' 19F NMR (CDC13, 376MHz): δ = -73.55 ppm
Example 12: Preparation of 2-Methyl-4-[4,4,4-trifluoro-3-mercapto-3-(3,4,5-trichloro-phenyl -butyryll- benzoic acid tert-but l ester
Figure imgf000237_0002
2-Methyl-4-[(E)-4,4,4-trifluoro-3-(3,4,5-trichloro-phenyl)-but-2-enoyl]-benzoic acid tert-butyl ester (
1.29 g) was added thioacetic acid (6 eq.) and triethylamine (12 μΕ). The solution was stirred under argon at room temperature for 24 hours. More thioacetic acid (1 mL) and triethylamine (1 drop) were added and the solution was stirred under argon at room temperature for 72 hours. To this mixture was added a minimum of dichloromethane and then isolute. The suspension was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 2-Methyl- 4-[4,4,4-trifluoro-3-mercapto-3-(3,4,5-trichloro-phenyl)-butyryl]-benzoic acid tert-butyl ester (573mg). lH NMR (CDCI3, 400MHz): δ = 7.89 (d, J=8.8 Hz, 1 H), 7.73 - 7.78 (m, 2 H), 7.69 (s, 2 H), 4.29 (d, J=18.3 Hz, 1 H), 3.99 (d, J=18.7 Hz, 1 H), 3.30 (s, 1 H), 2.63 (s, 3 H), 1.60 - 1.63 ppm (m, 9 H). 19F NMR (CDCI3, 376MHz): δ = -73.63 ppm Example 13: Preparation of 5-r3-(3,5-Dichloro-phenyl -4,4,4-trifluoro-3-mercapto-butyryll-2-
[l,2,41triazol-l - l-benzonitrile
Figure imgf000238_0001
To 5-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4 rifluoro-but-2-enoyl]-2-[l,2,4]triazol-l-yl-benzonitrile mg) was added thioacetic acid (6 eq.) and triethylamine (4 μΐ^). To dissolve the suspension more thioacetic acid (400 μΐ.) was added. The solution was stirred under argon at room temperature for 20 hours. To this mixture was added a minimum of dichloromethane and then isolute. The suspension was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 5-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-[l,2,4]triazol- 1 -yl-benzonitrile (108mg).
lH NMR (CDCI3, 400MHz): δ = 8.99 (s, 1 H), 8.39 (d, J=1.8 Hz, 1 H), 8.30 (dd, J=8.8, 2.2 Hz, 1 H), 8.23 - 8.26 (m, 1 H), 8.05 (d, J=8.8 Hz, 1 H), 7.54 - 7.60 (m, 2 H), 7.37 - 7.41 (m, 1 H), 4.30 (d, J=18.3 Hz, 1 H), 4.01 (d, J=18.3 Hz, 1 H), 3.22 ppm (s, 1 H). 19F NMR (CDC13, 376MHz): δ =-73.52 ppm
Example 14: Preparation of 4-[5-(3,5-Dichloro-phenyl -5-trifluoromethyl-4,5-dihydro-isothiazol-3-yll-2- meth l-N-thietan-3 -yl-benzamide
Figure imgf000238_0002
To a solution of 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-N-thietan-3-yl- benzamide (493 mg) dissolved in a minimum amount of tetrahydrofuran then was added Hydroxylamine- O-sulfonic acid (2 equiv.). Then a solution of potassium hydroxide (5.6 equiv.) in water (19 niL) was added dropwise. After stirring at room temperature for 30 minutes, the mixture was quenched with a solution of hydrochloric acid (IN), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The crude mixture was then redissolved in a minimum amount of tetrahydrofuran then was added Hydroxylamine-O-sulfonic acid (2 equiv.) Then a solution of potassium hydroxide (5.6 equiv.) in water - ο -
(19 mL) was added dropwise. After stirring at room temperature for 30 minutes, the mixture was quenched with a solution of hydrochloric acid (IN), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isothiazol-3-yl]-2- methyl-N-thietan-3-yl-benzamide (128 mg)
lU NMR (CDC13, 400MHz): δ = 7.56 - 7.62 (m, 2 H), 7.37 - 7.43 (m, 2 H), 7.31 (s, 2 H), 6.30 (d, J=8.1 Hz, 1 H), 4.21 (d, J=17.6 Hz, 1 H), 3.87 (d, J=17.6 Hz, 1 H), 3.45 - 3.54 (m, 2 H), 3.36 - 3.44 (m, 2 H), 2.44 - 2.52 ppm (m, 3 H). 19F NMR (CDC13, 376MHz): δ =-74.82 ppm
Similarly, 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydro— isothiazol-3-yl]-2-(l ,2,4-triazol-l- yl)benzonitrile (Bl) can be obtained.
lU NMR (CDCI3, 400MHz): δ = 8.89 (s, 1 H), 8.18 - 8.24 (m, 2 H), 8.16 (dd, J=8.6, 2.0 Hz, 1 H), 7.92 (d, J=8.8 Hz, 1 H), 7.44 (t, J=1.8 Hz, 1 H), 7.31 (d, J=0.7 Hz, 2 H), 4.24 (d, J=17.6 Hz, 1 H), 3.92 ppm (d, J=17.6 Hz, 1 H). 19F NMR (CDC13, 376MHz): δ =-74.88 ppm
Similarly, tert-butyl 2-methyl-4- [5-(3 ,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydro-isothiazol-3 - yljbenzoate can be obtained.
lU NMR (CDCI3, 400MHz): δ= 7.86 (d, J=8.4 Hz, 1 H), 7.54 - 7.63 (m, 2 H), 7.46 (s, 2 H), 4.22 (d, J=17.6 Hz, 1 H), 3.87 (d, J=17.6 Hz, 1 H), 2.61 (s, 3 H), 1.61 ppm (s, 9 H)
Example 15: Preparation of 2-Methyl-4-[4,4,4-trifluoro-3-mercapto-3-(3,4,5-trichloro-phenyl -butyryll-
Figure imgf000239_0001
A solution of 4-[3-Acetylsulfanyl-4,4,4-trifluoro-3-(3,4,5-trichloro-phenyl)-butyryl]-2-methyl-benzoic acid tert-butyl ester (1.33 g) in aniline (13 mL) was stirred at room temperature for 3 hours. The mixture was quenched with a solution of hydrochloric acid (IN), extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / dichloromethane) to give 2-Methyl-4-[4,4,4-trifluoro-3-mercapto-3-(3,4,5-trichloro-phenyl)-butyryl]- benzoic acid tert-butyl ester (950 mg).
lU NMR (CDCI3, 400MHz): δ = 7.89 (d, J=8.8 Hz, 1 H), 7.72 - 7.78 (m, 2 H), 7.69 (s, 2 H), 4.28 (d, J=18.7 Hz, 1 H), 3.98 (d, J=18.7 Hz, 1 H), 3.30 (s, 1 H), 2.63 (s, 3 H), 1.59 - 1.65 ppm (m, 9 H). Example 16: Preparation of 2-chloro-4-[5-(3,5-dichlorophenyl -5-(trifluoromethyl -4H-isothiazol-3- yl"|benzamide
Figure imgf000240_0001
To a solution of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzonitrile (50 mg) in toluene (1 mL) were added acetaldehyde oxime (3 eq.) then indium trichloride (0.05 eq.). The mixture was stirred at 120°C for 2 hours then it was allowed to cool to room temperature. The solution was diluted with ethyl acetate, then treated with ammonium hydroxide (2N). The mixture was washed two times with brine then the organic phase were collected and they were dried over magnesium sulfate, filtered and evaporated under vacuo to give 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H- isothiazol-3-yl]benzamide (50 mg).
lU NMR (CDC13, 400MHz): δ = 7.90 (d, J=8.1 Hz, 1 H), 7.84 (d, J=1.8 Hz, 1 H), 7.66 - 7.74 (m, 1 H), 7.37 - 7.46 (m, 1 H), 7.28 - 7.34 (m, 2 H), 6.40 (br. s., 1 H), 5.96 (br. s., 1 H), 4.19 (d, J=18.0 Hz, 1 H), 3.87 ppm (d, J=18.0 Hz, 1 H)
Example 17: Preparation of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll- N- E)-methoxyiminomethyllbenzamide (C3)
Figure imgf000240_0002
A solution of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzamide
(50mg) and Ν,Ν-Dimethylformamide dimethylacetal (1 mL) was refluxed under Argon for 30 min then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (0.48 mL) and a solution of O-methylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (0.43 mL) and acetic acid (0.43 mL) was added. The solution was stirred at rt for one hour. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated. Flash Chromatography eluting with Cyclohexane:EtOAc afforded 30 mg of the title compound.
'H-NMR (CDCI3, 400 MHz): δ = 9.21 (d, J=9.5 Hz, 1 H), 7.93 (d, J=8.4 Hz, 1 H), 7.85 - 7.89 (m, 1 H), 7.81 (d, J=9.5 Hz, 1 H), 7.74 (dd, J=8.1, 1.5 Hz, 1 H), 7.43 (t, J=1.8 Hz, 1 H), 7.29 - 7.33 (m, 2 H), 4.20 (d, J=17.6 Hz, 1 H), 3.93 (s, 3 H), 3.88 ppm (d, J=17.6 Hz, 1 H) 24Q
Example 18: Preparation of 4-[5-(3,5-dichlorophenyl -5-(trifluoromethyl -4H-isothiazol-3-yll-N-[(E - ethox iminomethyll-2-methyl-benzamide (C2)
Figure imgf000241_0001
A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide (200mg) and Ν,Ν-Dimethylformamide dimethylacetal (4 mL) was refluxed under Argon for one hour then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (2 mL) and a solution of O-ethylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (1.6 mL) and acetic acid (1.6 mL) was added. The solution was stirred at rt for 10 minutes. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated. Flash Chromatography eluting with
Cyclohexane:EtOAc afforded 237 mg of the title compound.
'H-NMR (CDCI3, 400 MHz): δ = 8.52 (d, J=9.5 Hz, 1 H), 7.79 (d, J=9.2 Hz, 1 H), 7.67 (d, J=5.5 Hz, 2 H), 7.56 (d, J=8.4 Hz, 1 H), 7.42 (t, J=1.7 Hz, 1 H), 7.31 (s, 2 H), 4.23 (d, J=17.6 Hz, 1 H), 4.16 (q, J=7.2 Hz, 2 H), 3.89 (d, J=18.0 Hz, 1 H), 2.56 (s, 3 H), 1.29 ppm (t, J=7.2 Hz, 3 H)
Example 19: Preparation of 4-[5-(3.5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll-N-[(E)- methox iminomethyll -2-methyl-benzamide (CI)
Figure imgf000241_0002
A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide
(200mg) and Ν,Ν-Dimethylformamide dimethylacetal (4 mL) was refluxed under argon for one hour then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (2 mL) and a solution of O-methylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (1.6 mL) and acetic acid (1.6 mL) was added. The solution was stirred at rt for 10 minutes. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated. Flash Chromatography eluting with
Cyclohexane:EtOAc afforded 243 mg of the title compound.
'H-NMR (CDCI3, 400 MHz) δ= 8.50 (d, J=9.9 Hz, 1 H), 7.79 (d, J=9.5 Hz, 1 H), 7.63 - 7.71 (m, 2 H), 7.55 (d, J=8.4 Hz, 1 H), 7.42 (s, 1 H), 7.31 (s, 2 H), 4.22 (d, J=17.6 Hz, 1 H), 3.91 (s, 3 H), 3.83 (d, 1 H), 2.56 ppm (s, 3 H).
Example 20: Preparation of 4-[5-(3.5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll-2-methyl- benzamide
Figure imgf000242_0001
A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid (1.65 g) was suspended in dichloromethane (16 mL). A catalytic amount of NN-dimethylformamide ("DMF") and oxalyl chloride (1.2 eq.) were added to the suspension. The reaction mixture was stirred at ambient temperature for 1.5 hour. The reaction mixture was concentrated and the residue dissolved in dry tetrahydrofuran (16 mL). To the solution was added a solution of ammonium hydroxide (8 mL, 25%). The reaction mixture was stirred at ambient temperature for two hours. It was then quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with a saturated solution of sodium hydrogenocarbonate, dried over magnesium sulfate and concentrated in vacuo. The crude residue was triturated with teii-butylmethylether then the precipitate was filtered and dried under vacuo to give the title compound (841 mg) as a solid. 'H-NMR (CDC13, 400 MHz): δ = 7.50 - 7.61 (m, 2 H), 7.39 - 7.50 (m, 1 H), 7.29 - 7.39 (m, 1 H), 7.14 - 7.27 (m, 2 H), 6.40 (br. s., 1 H), 6.05 (br. s., 1 H), 4.16 (m, J=17.4, 1 H), 3.74 - 3.91 (m, 1 H), 2.44 - 2.49 (m, 3 H). Example 21 : Compound Al : 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yll-N-(Ll-
Figure imgf000242_0002
To a stirred solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl- benzoic acid (100 mg) in dichloromethane (3.8 mL) was added triethylamine (0.065 mL) at ambient temperature. The solution was stirred under argon and the hydrochloride salt of thietan-3-ylamine (44 mg) was added. To this solution, 1 -hydroxyazabenzotriazole (35 mg) then l-(3-Dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (50 mg) were added. The solution was stirred for 24 hours at ambient temperature. The residue was extracted with ethyl acetate and a saturated solution of ammonium chloride. The organic extract was washed with water, dried over sodium sulfate and concentrated under vacuo. The crude residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate) to give 4- [5- (3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-(l,l-dioxothietan-3-yl)-2-methyl- benzamide (34 mg) as a white solid. 'H-NMR (CDCI3, 400 MHz): δ = 7.60-7.69 (m, 2 H), 7.40-7.50 (m, 2 H), 7.30-7.33 (m, 2 H), 6.48 (d, 1 H), 4.83-4.99 (m, 1 H), 4.56-4.71 (m, 2 H), 4.22 (d, 1 H), 3.99-4.07 (m, 2 H), 3.88 (d, 1 H), 2.51 ppm (s, 3 H).
Similarly, using the trifluoroacetate salt of 2-amino-N-(2,2,2-trifluoroethyl)acetamide
as an amine, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2- (2,2,2-trifluoroethylamino)ethyl]benzamide (compound A2) could be prepared. 'H-NMR (CDCI3, 400 MHz): δ = 7.63-7.69 (m, 1 H), 7.60 (d, 1 H), 7.48 (d, 1 H), 7.42 (t, 1 H), 7.29-7.34 (m, 2 H), 6.68 (br. s., 1 H 6.58 (s, 1 H), 4.16-4.26 (m, 3 H), 3.92-4.03 (m, 2 H), 3.88 (d, 1 H), 2.51 ppm (s, 3 H) .
Figure imgf000243_0001
Similarly, 2-methyl-N-(l-oxothietan-3-yl)-4-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol- 3-yl]benzamide (compound D3) could be prepared. ¾-NMR (DMSO-dg ,400MHz): δ = 8.93 (d, J=7.3 Hz, 1 H), 7.81 (s, 2 H), 7.69 - 7.79 (m, 2 H), 7.48 (d, J=7.7 Hz, 1 H), 4.51 - 4.64 (m, 1 H), 4.30 - 4.47 (m, 2 H 4.03 - 4.15 (m, 2 H), 3.15 - 3.29 (m, 2 H), 2.39 ppm (s, 3 H)
Figure imgf000243_0002
Similarly, 2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-4-[5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4H-isothiazol-3-yl]benzamide (compound Dl) could be prepared. 'H-NMR (CDCI3, 400 MHz): δ = 7.8-7.7 (m, 2 H), 7.52-7.46 (m, 3 H), 6.72 (m, 1 H), 6.61 (m, 1 H), 4.3 - 4.17 (m, 3 H), 4.05- 3.82 (m, 3 H), 2.51 ppm (s, 3 H)
Figure imgf000243_0003
Similarly, N-(l,l-dioxothietan-3-yl)-2-methyl-4-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H- isothiazol-3-yl]benzamide (compound D2) could be prepared. ¾-NMR (CDC13, 400 MHz): δ = 7.7-7.6 (m, 2 H), 7.45-7.51 (m, 3 H), 6.51 (m, 1 H), 5.0 - 4.75 (m, 1 H), 4.7 - 4.6 (m, 2 H), 4.30- 4.19 (m, 1 H), 4.1 - 4.0 (m, 2 H), 3.95 - 3.80 (m, 1 H), 2.52 ppm (s, 3 H)
Figure imgf000244_0001
Similarly, 4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide (compound A78) could be prepared. 'H-NMR (CDCI3, 400 MHz): δ = 7.64 (s, 1 H), 7.60 (d, J=8.1 Hz, 1 H), 7.51 (d, J=8.1 Hz, 1 H), 7.42 (t, J=1.7 Hz, 1 H), 7.29 - 7.34 (m, 2 H), 6.40 (d, J=3.7 Hz, 1 H), 4.94 - 5.06 (m, 1 H), 4.87 (dd, J=10.8, 3.9 Hz, 1 H), 4.22 (d,
J=17.6 Hz, 1 H), 4.06 (dd, J=10.8, 8.6 Hz, 1 H), 3.88 (d, J=17.6 Hz, 1 H), 3.57 - 3.78 (m, 2 H), 2.52 (s, 3 H), 1.20 - 1.32 ppm (m, 3 H).
Chiral HPLC analysis using a Waters UPLC- Hclass, DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IB, 3μηι, 0.46cm x 10cm
Mobile phase: Heptane/iPrOH 80/20
Flow rate: 1.0 ml/min
Detection: 313
Sample concentration: lmg/mL in Hept/iPrOH 50/50
Injection: 2μL
1st eluting isomer: rt= 4.23 min; 1.1 %
2nd eluting isomer: rt=5.66 min; 98.9 %
Figure imgf000244_0002
Similarly, 4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[(4R)-3- oxo-2-(2,2,2-trifluoroethyl)isoxazolidin-4-yl]benzamide (compound A79) could be prepared. 'H-NMR ^
(CDCI3, 400 MHz): δ =7.57 - 7.70 (m, 2 H), 7.51 (d, J=8.1 Hz, 1 H), 7.42 (t, J=1.8 Hz, 1 H), 7.29 - 7.34 (m, 2 H), 6.36 (d, J=4.0 Hz, 1 H), 5.00 - 5.09 (m, 1 H), 4.97 (dd, J=10.5, 4.6 Hz, 1 H), 4.06 - 4.33 (m, 4 H), 3.88 (d, J=17.6 Hz, 1 H), 2.52 ppm (s, 3 H).
Chiral HPLC analysis using a Waters UPLC- Hclass, DAD Detector Waters UPLC
Column: Column: Daicel CHIRALPAK® IB, 3μηι, 0.46cm x 10cm
Mobile phase: Heptane/iPrOH 80/20
Flow rate: l .O ml/min
Detection: 313
Sample concentration: lmg/mL in Hept/iPrOH 70/30
Injection: 4μΕ
1st eluting isomer: rt= 4.19 min; 0.9 %
2nd eluting isomer: rt=4.94 min; 99.1 %
Example 22: Preparation of 4-bromo-2-methyl-benzoic acid fert-butyl ester
Figure imgf000245_0001
4-Bromo-2-methyl-benzoic acid (commercially available) (50 g) was suspended in dichloromethane (500 mL). A catalytic amount of NN-dimethylformamide ("DMF") and oxalyl chloride (23 mL) were added to the suspension. The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated and the residue dissolved in dry tetrahydroiuran (800 mL). The solution was cooled to 2°C and added to a solution of potassium fert-butoxide (39.2 g) in dry tetrahydrofuran (300 mL) dropwise at 5-10°C. The reaction mixture was stirred at ambient temperature for 30 minutes and then poured onto a mixture of ice and water. The mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated to give 4-bromo-2-methyl-benzoic acid fert-butyl ester (65.3 g) as yellow oil.
'H-NMR (CDCI3, 400 MHz): δ = 7.70 (d, 1H), 7.40 (s, 1H), 7.35 (d, 1H), 2.58 (s, 3H), 1.60 (s, 9H).
Example 23: Preparation of tert-butyl 4-formyl-2-methyl-benzoate
Figure imgf000245_0002
To a solution of 4-bromo-2-methyl-benzoic acid tert-butyl ester (500 g, 1.8 mol) in tetrahydrofuran (5 L) was added n-butyl lithium (1.6 M solution, 1.4 L, 2.2 mol) at such a rate that the reaction temperature is between -95°C to -100°C. After completion of the addition, the reaction mixture was stirred for 30 min at -100°C and monitored by quenching the reaction mixture with water and following the product by TLC. After complete conversion, DMF (170 ml, 2.2 mol) was added to the reaction mixture and after 15 min the reaction mixture was quenched with ammonium chloride (sat. solution, 5 L). The organic layers were separated at room temperature and the aqueous layer was extracted with ethyl acetate (3x2 L). The combined organic layer was washed with water (3x 5 L), dried over sodium sulphate and concentrated to yield tert-butyl 4-formyl-2-methyl-benzoate (390 g, 96 % isolated yield, 75-78 % HPLC purity). The crude product was used as such without any further purification for the next step. 'H-NMR (CDCI3, 400 MHz): δ in ppm = 1.59 (s, 9H), 2.61 (s, 3H), 7.71 (d, 2H), 7.92 (d, 1H), 10.01 (s, 1H).
Example 24: Preparation of 4-tert-butoxycarbonyl-3-methyl-benzoic acid
Figure imgf000246_0001
To a solution of tert-bulyl 4-formyl-2-methyl-benzoate (390 g, -78 % purity, 1.8 mol) in DMF (2.0 L) was added oxone (270 g, 1.8 mol) over a period of 15 min at 10°C. After complete addition, the reaction mixture was warmed to room temperature and stirred for 12 h. After complete conversion of starting material, the reaction mixture was diluted with water at 10°C. The aqueous layer was extracted with ethyl acetate (2x 5 L), washed with water (3x 1L) dried over sodium sulphate and concentrated to yield a crude residue (217 g). Pure 4-tert-butoxycarbonyl-3-methyl-benzoic acid (115 g) was obtained by column chromatography with ethyl acetate (6 %) in hexane.
'H-NMR (DMSO dg, 400 MHz): δ in ppm = 1.55 (s, 9 H), 2.51 (s, 3H), 7.83 (m, 3H), 13.11 (br, OH).
Example 25: Preparation of tert-butyl 4-carbamoyl-2-methyl-benzoate
Figure imgf000246_0002
A solution of 4-tert-butoxycarbonyl-3-methyl-benzoic acid (40 g) was suspended in tetrahydrofuran (160 mL). This solution was cooled to -30C then N-methyl morpholine (18.7 mL) followed by
isobutylchloroformate (24.2 mL) were added. A white precipitate appeared. The solution was stirred for 8 hours then a solution of ammonium hydroxide (100 mL) was added. The reaction mixture was slowly allowed to warm to room temperature over 48 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated to give a solid which was further triturated with a mixture of dichloromethane/ethyl acetate, . . ,
- 246 - filtered, to give tert-butyl 4-carbamoyl-2-methyl-benzoate (29.9 g) as a white solid. 'H-NMR (CDC13, 400 MHz): 7.90 (d, 1H), 7.72 (s, 1H), 7.65 (d, 1H), 2.63 (s, 3H), 1.62 (s, 9H).
Example 26: Preparation of 2-(l ,2,4-triazol-l-yl -5-r(5S -5-(3,4,5-trichlorophenyl -5-(trifluoromethyl - 4H-isothiazol-3- llbenzonitrile (B2)
Figure imgf000247_0001
Sulfuryl chloride (5.97 mL) was slowly added to a solution of 5-[(3S)-3-benzylsulfanyl-4,4,4-trifluoro-3- (3,4,5-trichlorophenyl)butanoyl]-2-(l ,2,4-triazol-l-yl)benzonitrile (40.54 g) in dichloromethane (264 mL) at 0°C. The mixture was stirred at room temperature for two hours.
The solvent was then evaporated, then tetrahydrofuran (264 mL) was added and slowly ammonia in ethanol (48.6 mL, 7N in ethanol) was added at 0°C. The reaction was stirred for another hour then a hydrochloric acid (2N) solution was added. The mixture was extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated under vacuo. The crude residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give the desired compound as a mixture which was further purified using a preparative reverse phase HPLC to give with 2-(l ,2,4-triazol- l-yl)-5-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzonitrile (4.056 g) as a white solid.
1H NMR (CDC13 ,400MHz): δ = 8.90 (s, 1 H), 8.17 - 8.27 (m, 2 H), 8.10 - 8.17 (m, 1 H), 7.92 (d, J=8.8 Hz, 1 H), 7.46 (s, 2 H), 4.24 (d, J=17.6 Hz, 1 H), 3.90 ppm (d, J=17.6 Hz, 1 H).19H NMR
(CDCl3,376MHz): δ= -74.61
Chiral HPLC analysis using a Waters UPLC (Alliance 2695)- Hclass, DAD Detector Waters UPLC (996).
Column: Daicel CHIRALPAK® IA, 3 Dm, 0.46cm x 10cm
Mobile phase: Hept/EtOH/DEA 80/20/0.1%
Flow rate: 1 ml/min
Detection: 325nm
Sample concentration: lmg/mL in Heptan/ iPrOH 50/50
Injection: 2μΕ
1st eluting isomer: rt= 6.17 min; 83.2 %
2nd eluting isomer: rt= 9.09 min; 16.8 % Similarly, tert-butyl 4-[(5S)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl- benzoate could be obtained from tert-butyl 4-[(3S)-3-benzylsulfanyl-3-(3,5-dichlorophenyl)-4,4,4- trifluoro-butanoyl]-2-methyl-benzoate
Chiral HPLC analysis using a Waters UPLC- Hclass, DAD Detector Waters UPLC
Column: Daicel CHIRALPAK® IA, 3μηι, 0.46cm x 10cm
Mobile phase: Heptane/iPrOH 95/05
Flow rate: 1.0 ml/min
Detection: 318nm
Sample concentration: lmg/mL in Hept/iPrOH 50/50
Injection: 2μΙ.
1st eluting isomer: rt= 1.80 min; 98.6%
2nd eluting isomer: rt=2.33 min; 1.4% Exam le 27: Method for preparing compounds of the invention from a carboxylic acid
Figure imgf000248_0001
o a solution of the 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid (22 μιηοΐ) in dimethylacetamide (0.4 ml) was added successively a solution of an amine of formula HNPv6Pv7 (26 μιηοΐ), for example thietan-3-ylamine (preparation described in, for example,
WO 2007/080131) in the case of Compound No. A22 of Table A, in dimethylacetamide (0.11 ml), diisopropylethylamine (Hunig's Base) (0.030 ml), and a solution of bis(2-oxo-3-oxazolidinyl)phosphonic chloride ("BOP-C1") (11.2 mg) in dimethylacetamide (0.02 ml). The reaction mixture was stirred at 80°C for 16 hours. Then the reaction mixture was diluted with acetonitrile (0.6 ml) and a sample was used for LC-MS analysis. The remaining mixture was further diluted with acetonitrile / dimethylformamide (4: 1) (0.8 ml) and purified by HPLC. This method was used to prepare a number of compounds (Compound Nos. Al to A77 of Table A) in parallel. - 4ο -
Table A
Figure imgf000249_0001
Comp R1 R2 RT (min) [M+H]+ No.
A01 H (2,2,2-Trifluoro-ethylcarbamoyl)-methyl 1.97 572.23
A02 H 1 , 1 -Dioxo-thietan-3 -yl 1.91 537.14
A03 H 2,2,2-Trifluoro-ethyl 2.1 515.23
A04 H ethyl 2.02 461.23
A05 H butyl 2.18 489.27
A06 H 1 -methoxypropan-2-yl 2.06 505.25
A07 H 3,3,3 -trifluor oprop- 1 -yl 2.12 529.22
A08 H butan-2-yl 2.17 489.26
A09 H tetrahydrofuran-2-ylmethyl 2.04 517.24
A10 H benzyl 2.18 523.23
Al l H (2-fluorophenyl)-methyl 2.19 541.22
A12 H 1 -phenylethyl 2.23 537.25
A13 H (4-methoxyphenyl)-methyl 2.16 553.25
A14 H (6-chloro-3 -pyridyl)methyl 2.1 558.22
A15 H 3 -fluorophenyl 2.27 527.24
A16 H 2-pyridylmethyl 1.9 524.24
A17 H 2,5-dimethylpyrazol-3-yl 2.01 527.25
A18 H 4-methylthiazol-2-yl 2.21 530.2
A19 H 3 -Methyl-thietan-3 -yl 2.19 519.22
A20 H 2-methyl- 1 -methylsulfanyl-propan-2-yl 2.28 535.27
A21 H 1 -Oxo-thietan-3-yl 1.82 521.19
A22 H Thietan-3-yl 2.1 505.22
A23 H (lR,2R,4S)-N-methylnorbornan-2-yl 2.3 527.27
A24 H Cyclobutyl 2.13 487.27
A25 H N-methyl-2-methylsulfinyl-ethyl 1.77 523.19
A26 H 2-methylsulfanylethyl 2.09 507.26
A27 H tetrahydrothiophen-3 -yl 2.12 519.22
A28 H thietan-3 -ylmethyl 2.14 519.33 Comp R1 R2 RT (min) [M+H]+ No.
A29 H 3-(2,2,2-trifluoroethoxyimino)cyclobutyl 2.2 598.32
A30 H thietan-2-ylmethyl 2.16 519.3
A31 H (1,1 -dioxothietan-2-yl)methyl 1.93 551.31
A32 H 2-(thietan-3-yl)ethyl 2.18 533.35
A33 H 2-(l , 1 -dioxothietan-3-yl)ethyl 1.93 565.34
A34 H 2-fluoroethyl 2.01 479.29
A35 H prop-2-ynyl 2.03 471.32
A36 H propanyl 2.13 475.35
A37 H 2-oxotetrahydrothiophen-3 -yl 2.07 533.27
A38 H pyrimidin-2-yl 1.95 511.12
A39 H propan-2-yl 2.13 475.34
A40 H cyclobutylmethyl 2.25 501.36
A41 H 1 -oxidopyridin- 1 -ium-4-yl 1.82 526.32
A42 H 2,2-difluoroethyl 2.07 497.32
A43 H cyano 2.01 458.4
A44 H 4,5-dihydrothiazol-2-yl 2.02 518.31
A45 H 1 -cyanocyclopropyl 2.03 498.32
A46 H 2-methylpropan- 1 -yl 2.21 489.35
A47 H 4,6-dimethylpyrimidin-2-yl 2.09 538.85
A48 H pyrimidin-5-yl 2 511.31
A49 H 6-(diethylcarbamoyl)-2-pyridyl 2.24 609.38
A50 H indan-l-yl 2.31 549.31
A51 H 2-methoxyethyl 2.01 491.33
A52 H cyclopropyl 2.05 473.34
A53 H cyclopropylmethyl 2.15 487.33
A54 H 2-(l,3-dioxolan-2-yl)ethyl 2.03 533.34
A55 H 2,4-difluorophenyl 2.28 545.35
A56 H pyridin-2-yl 2.19 510.31
A57 H [4-(trifluoromethyl)phenyl]methyl 2.31 591.29
A58 H 4-(trifluoromethyl)phenyl 2.39 577.33
A59 H 4-fluorophenyl 2.26 527.32
A60 H 2-fluorophenyl 2.28 527.32
A61 H p-tolylmethyl 2.28 537.38
A62 H methyl 1.96 447.32 Comp R1 R2 RT (min) [M+H]+ No.
A63 H allyl 2.09 473.33
A64 H 4-methylphenyl 2.32 523.35
A65 H quinolin-8-yl 2.54 560.35
A66 H 4H-l,2,4-triazol-3-yl 2.23 501.35
A67 H cyclopentyl 2.1 505.34
A68 H 2-ethoxyethyl 2.18 499.33
A69 H cyclopent-3 -en- 1 -yl 1.73 550.34
A70 H 1 -(3 -pyridyl)cyclopropyl 2.08 517.36
A71 H pentan-3-yl 2.03 491.31
A72 H cis-2-fluorocyclopropyl 2.23 532.36
A73 H ( 1 E)- 1 -methoxyimino-2-methyl-propan-2-yl 2.06 546.37
A74 H 1 -methoxypiperidin-4-yl 2.02 560.39
A75 H ( 1 -methoxy-4-piperidyl)methyl 2.17 507.3
A76 H 2-chloroprop-2-en-l-yl 2.05 500.3
All H 3 , 3 -dichloroprop -2- en- 1 -yl 2.26 541.29
Corresponding LC/MS Method
MS ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer) Ionisation method: Electrospray
Polarity: positive ions
Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow
(L/Hr) 700
Mass range: 100 to 800 Da
DAD Wavelength range (nm): 210 to 400
LC Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water/Methanol 9:1,0.1% formic acid and Solvent B: Acetonitrile,0.1%> formic acid )
Time (minutes) A (%>) B (%>) Flow rate (ml/min)
0 100 0 0.75
2.5 0 100 0.75
2.8 0 100 0.75
3.0 100 0 0.75
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C. ^ ^
Biological Examples
Spodoptera littoralis (Egyptian cotton leafworm):
Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 LI larvae. The samples were checked for mortality, feeding behavior, and growth regulation 3 days after treatment (DAT).
The following compound gave at least 80% control of Spodoptera littoralis: A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, Al l, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A47, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A61, A62, A63, A64, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3, D1, D2, D3.
Heliothis virescens (Tobacco budworm):
Eggs (0-24 h old) were placed in 24-well microtiter plate on artificial diet and treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After an incubation period of 4 days, samples were checked for egg mortality, larval mortality, and growth regulation.
The following compound gave at least 80% control of Heliothis virescens: A01, A02, A03, A04, A05,
A06, A07, A08, A09, A10, Al 1, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24,
A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A61, A62, A63,
A64, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3,
D1, D2, D3.
Plutella xylostella (Diamond back moth):
24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (7-12 per well). After an incubation period of 6 days, samples were checked for larval mortality and growth regulation.
The following compound gave at least 80%> control of Plutella xylostella: A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, Al 1, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A62, A63, A64, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3, Dl, D2, D3. Diabrotica balteata (Corn root worm):
A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality and growth regulation.
The following compound gave at least 80% control of Diabrotica balteata: A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, Al l, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A61, A62, A63, A64, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3, Dl, D2, D3. Thrips tabaci (Onion thrips):
Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with a thrips population of mixed ages. After an incubation period of 7 days, samples were checked for mortality.
The following compounds gave at least 80% control of Thrips tabaci: A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, Al 1, A12, A13, A14, A15, A16, A17, A18, A19, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A38, A39, A40, A42, A43, A45, A46, A48, A50, A51, A52, A53, A54, A55, A56, A58, A59, A60, A62, A63, A64, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3, Dl, D2, D3. Tetranychus urticae (Two-spotted spider mite):
Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs are infested with mite populations of mixed ages. 8 days later, discs are checked for egg mortality, larval mortality, and adult mortality.
The following compound gave at least 80%> control of Tetranychus urticae: A01, A02, A03, A04, A05, A06, A07, A08, A09, A10, Al 1, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A42, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A57, A59, A60, A62, A63, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, Bl, B2, CI, C2, C3, Dl, D2, D3. Biological Examples showing increased safety profile:
Spodoptera Uttoralis (Egyptian cotton leafworm)
Cotton plants in the 5th leaf stage (around 5 weeks old) are treated in an automated turn table spray chamber. Plants are stored in the greenhouse length during the whole test period.
2,16 and optionally 10 days after treatment 4 leaves from each sample are excised, placed into 14cm plastic petri dishes on wet filter paper. The infestation of 10 L3-Spodoptera Uttoralis is made immediately afterwards. After an incubation period of 6 days the samples are checked for mortality. Test results:
Figure imgf000254_0002
Comparative tests
In the following series of experiments the compounds of the invention are compared with the corresponding isoxazoline analogues from the prior art on Spodoptera Uttoralis (Egyptian cotton leafworm) performed as described in the method above.
Comparative Table 1
In this comparison it can be seen that the structures of the two compounds are identical apart from the replacement of the oxygen atom with a sulphur atom in the isoxazoline moiety.
Com ound 1 -061 from EP1731512 Com ound A16 present invention
Figure imgf000254_0001
Compound Application Control after Control after Control after rate /ppm 2 days / % 10 days / % 16 days / %
Compound 1 -061 from 12.5 100 100 100
EP1731512
Compound A16 present 12.5 100 25 10 invention ^
Comparative Table 2
In this comparison it can be seen that the structures of the two compounds are identical apart from the replacement of the oxygen atom with a sulphur atom in the isoxazoline moiety.
Figure imgf000255_0001
Comparative Table 3
In this comparison it can be seen that the structures of the two compounds are identical apart from the replacement of the oxygen atom with a sulphur atom in the isoxazoline moiety.
Figure imgf000255_0002
Conclusions
Compounds that exhibit high control of pests at low application rates and that are readily bio-degradable are highly desirable for environmental safety reasons. The data shown above indicate that the compounds of the invention exhibit high pesticidal activity during the days immediately after application, with the activity significantly reduced after 10 to 16 days indicating that the compounds are bio-degrading. In contract, the close structural analogues from the prior art show little or no reduction in activity during the testing period, indicating that the compounds show no significant bio- degradation.
From the perspective of environmental safety the compounds of the invention are superior to those of the prior art and in addition retain a high level of pest control at low application rates. In the light of the structural similarities of the tested compounds, this significant difference in bio-degradability in favour of the compounds of the invention is completely unexpected and cannot be derived from what is known from the prior art.

Claims

Claims:
1. A compound of
Figure imgf000257_0001
wherein
P is PO, heterocyclyl or heterocyclyl substituted by one to five Z;
Figure imgf000257_0002
Y1, Y2, Y3 and Y4 are independently of each other C-H, C-R5, or nitrogen;
G1 is oxygen or sulfur;
R1 is hydrogen, Ci-Cgalkyl, CpCgalkoxy-, CpCgalkylcarbonyl-, or CpCgalkoxycarbonyl-;
R2 is Ci-Cgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl-N(R 20 )- or aryl-N(R 20 )- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-N(R 20 )- or heterocyclyl-N(R 20 )- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Cp
Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, Cp Cgalkylaminocarbonyl-, Ci-Cghaloalkylaminocarbonyl, C3-Cgcycloalkyl-aminocarbonyl, Ci-Cealkyl-O- N=CH-, CrC6haloalkyl-0-N=CH-;
or R1 and R2 together represent group A
Figure imgf000257_0003
G2 is 0(R13), N(R14)(R15) or S(R16);
G3 is N(R17)(R18) or S(R19);
X4 is Ci-Cghaloalkyl;
R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; each R5 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, CpCgalkenyl, Cp
Cghaloalkenyl, CpCgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, CpCgalkoxy-, CpCghaloalkoxy-, Cp Cgalkylthio-, CpCghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, CpCgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-; or two R5 on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge; each R6 is independently halogen, cyano, nitro, hydroxy, amino, Ci-Cgalkylamino, (Ci-Cgalkyl)2amino, Ci-Cgalkylcarbonylamino, Ci-Cghaloalkylcarbonylamino, CpCgalkoxy-, CpCghaloalkoxy-, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, mercapto, Cp Cgalkylthio-, CpCghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, CpCgalkylsulfonyl-, Cp Cghaloalkylsulfonyl-, aryl-Ci-C4alkylthio or aryl-Ci-C4alkylthio wherein the aryl moiety is substituted by one to five R10;
each R7 is independently halogen, CpCgalkyl, CpCgalkenyl, CpCgalkynyl,
Figure imgf000258_0001
Cp Cghaloalkyl-0-N=; CpCgalkoxy, CpCgakoxycarbonyl;
each R8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, Ci-Cghaloalkyl, CpCgcyanoalkyl, C2- Cgalkenyl, C2-Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, C3-Ciocycloalkyl, C3-Ciocycloalkyl-Cp C4alkylene, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, Cp
Cgalkylaminosulfonyl, (Ci-Cgalkyl)2aminosulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, heterocyclyl or heterocyclyl substituted by one to five R10, aryl-Cp C4alkylene or aryl-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10, heterocyclyl- Ci-C4alkylene or heterocyclyl-Ci-C4alkylene wherein the heterocyclyl moiety is substituted by one to five R10, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10;
each R9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C2-Cgalkenyl, C2- Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, CpCgalkoxy-, CpCghaloalkoxy-, mercapto, Cp Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, CpCgalkylsulfonyl-, Cp Cghaloalkylsulfonyl-, CpCgalkylcarbonyl-, CpCgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10;
each R10 is independently halogen, cyano, nitro, CpC4alkyl, CpC4haloalkyl, CpC4alkoxy-, or Cp C4haloalkoxy-;
each Z is independently halogen, CpCgalkyl or CpCgalkyl substituted by one to five R6, nitro, Cp Ci2alkoxy or CpCgalkoxy substituted by one to five R6, cyano,
Figure imgf000258_0002
CpCi2haloalkylsulfinyl, CpC^haloalkylsulfonyl, hydroxyl or thiol;
R13, R16 and R19 are independently CrC4 alkyl;
R14, R15, R17, and R18 are independently hydrogen or CrC4 alkyl;
R20 is hydrogen or C1-C4 alkyl;
or a salt or N-oxide thereof.
2. A compound according to claim 1 wherein Y1 is C-R5b, C-H or nitrogen, Y2 and Y3 are independently C-H or nitrogen and Y4 is C-R5; wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y and Y are not both nitrogen, and wherein R when present forms a -CH=CH-CH=CH- bridge with R5.
3. A compound according to claim 1 or claim 2 wherein G1 is oxygen.
4. A compound according to any one of claims 1 to 3, wherein P is P0 or a heterocycle selected from HI to
Figure imgf000259_0001
H1 H2 H3 H4
Figure imgf000259_0002
H5 H6 H7 H8 H9 k is 0, 1 or 2.
5. A compound according to any one of claims 1 to 4 wherein R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.
6. A compound according to any one of claims 1 to 5 wherein R is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-C r C4alkylene- or aryl-C i-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl- Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3- Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group CI
Figure imgf000259_0003
Ru is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R12;
each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy; wherein each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl, 2,3-dihydro- benzofuranyl, benzo[l,3]dioxolanyl, and 2,3-dihydro-benzo[l,4]dioxinyl.
7. A compound according to claim 6 wherein R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Ci-C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo-thietanyl-Ci-C4 alkylene or dioxo-thietanyl-Ci-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, or C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene or group CI
Figure imgf000260_0001
8. A compound according to any one of claims 1 to 7 wherein X is chlorodifluoromethyl or trifluoromethyl.
9. A compound according to any one of claims 1 to 8 wherein R4 is aryl or aryl substituted by one to five R9.
A compound according to claim 1 , wherein the compound of formula I is a compound of formula
Figure imgf000260_0002
wherein
Y1 is C-R5b, CH or nitrogen;
Y2 and Y3 are independently CH or nitrogen;
wherein no more than two of Y1, Y2 and Y3 are nitrogen and wherein Y2 and Y3 are not both nitrogen;
R5 is hydrogen, halogen, cyano, nitro, NH2, Ci-C2alkyl, Ci-C2haloalkyl, C3-C5cycloalkyl, C3-
C5halocycloalkyl, Ci-C2alkoxy, Ci-C2haloalkoxy;
R5b when present together with R5 forms a -CH=CH-CH=CH- bridge;
X2 is C-X6 or nitrogen;
X1, X3 and X6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X1, X3 and X6 are not hydrogen;
X4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
11. A compound of formula Int- 1
Figure imgf000261_0001
wherein X4, R4, Y1, Y2, Y3 and Y4, are as defined for a compound of formula (I) in any one of claims 1 to 10, G1 is oxygen, and R is hydroxy, Ci-Ci5alkoxy or halogen, or a salt or N-oxide thereof; or
a compound of formula Int-II
Figure imgf000261_0002
wherein X4, R4, Y1, Y2, Y3 and Y4, are as defined for a compound of formula (I) in any one of claims 1 to 10, and XB is a leaving group, or a salt or N-oxide thereof; or
a compound of formula Int-III
Figure imgf000261_0003
wherein Y1, Y2, Y3 and Y4, are as defined for compounds of formula (I) in any one of claims 1 to 10, Px is P0 as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof; or
a compound of formula (Int- VI)
Figure imgf000262_0001
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I) in any one of claims 1 to 10, and Px is as defined for the compound of formula (Int-III), Z1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C4alkylene-, Ci-Cgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio- or a salt or N-oxide thereof; or
a compound of formula (Int-VII)
Figure imgf000262_0002
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I) in any one of claims 1 to 10, and Px is as defined for the compound of formula (Int-III), Z1 is hydrogen, halogen, cyano, CpCgalkyl, optionally substituted aryl-Ci-C4alkylene-, Ci-Cgalkylcarbonyl-, optionally substituted arylsulfonyl- or optionally substituted arylthio-, and Z2 is hydrogen or hydroxyl or d-Cgalkoxy- or d- Cgalkylsulfonyloxy- or arylsulfonyloxy- or aryl-Ci-C4alkylene-or aryl or a salt or N-oxide thereof; or a compound of formula (Int-VIII)
Figure imgf000262_0003
wherein X4, R4, Y1, Y2, Y3 and Y4 are as defined for the compounds of formula (I) in any one of claims 1 to 10, and Px is as defined for the compound of formula (Int-III), and Z3 is thiol or optionally substituted aryl-Ci-Cgalkylsulfinyl- or a salt or N-oxide thereof.
12. A method of 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) as defined in any one of claims 1 to 10.
13. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 10.
14. An insecticidal, acaricidal, nematicidal or molluscicidal composition according to claim 13 comprising at least one additional compound having biological activity.
15. A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (I) as defined in any one of claims 1 to 10, and compound B is imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel,
triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013092943A1 (en) * 2011-12-23 2013-06-27 Basf Se Isothiazoline compounds for combating invertebrate pests
WO2014079935A1 (en) * 2012-11-21 2014-05-30 Syngenta Participations Ag Insecticidal compounds based on arylthioacetamide derivatives
WO2014202437A1 (en) * 2013-06-21 2014-12-24 Basf Se Suspension concentrate composition comprising isothiazoline insecticide and activated charcoal
WO2014202751A1 (en) 2013-06-21 2014-12-24 Basf Se Methods for controlling pests in soybean
WO2014206910A1 (en) * 2013-06-24 2014-12-31 Basf Se Bicyclyl-substituted isothiazoline compounds
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WO2015104422A1 (en) 2014-01-13 2015-07-16 Basf Se Dihydrothiophene compounds for controlling invertebrate pests
CN105473584A (en) * 2013-06-24 2016-04-06 梅里亚股份有限公司 Thiophene- or furan-substituted isothiazoline compounds as pesticides
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WO2023118434A1 (en) * 2021-12-22 2023-06-29 Globachem Nv Pesticidally active amide compounds

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* Cited by examiner, † Cited by third party
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Citations (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0357460A2 (en) 1988-09-02 1990-03-07 Sankyo Company Limited 13-Substituted milbemycin derivatives, their preparation and use
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
EP0382173A2 (en) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. PF 1022 substance, method of producing same and anthelmintic composition containing same
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0444964A1 (en) 1990-03-01 1991-09-04 Sankyo Company Limited Milbemycin ether derivatives, their preparation and their anthelmintic uses
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0503538A1 (en) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Medicinal composition containing an anthelmintic cyclic depsipeptide
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1993019053A1 (en) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Depsipeptide derivative, production thereof and use thereof
WO1993025543A2 (en) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines and enniatine derivates used to control endoparasites
EP0594291A1 (en) 1992-09-01 1994-04-27 Sankyo Company Limited Novel processes for the production of 13-ether derivatives of milbemycins, and novel intermediates therefor
WO1994015944A1 (en) 1993-01-18 1994-07-21 Pfizer Limited New antiparasitic agents related to the milbemycins and avermectins
WO1994019334A1 (en) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Pf1022 derivative, cyclic depsipeptide
EP0626375A1 (en) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides having endoparasiticidal activity
WO1995019363A1 (en) 1994-01-14 1995-07-20 Pfizer Inc. Antiparasitic pyrrolobenzoxazine compounds
WO1995022552A1 (en) 1994-02-16 1995-08-24 Pfizer Limited Antiparasitic agents
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1996011945A2 (en) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Cyclic depsipeptide sulfonylation, sulfenylation and phosphorylation process
WO1996015121A1 (en) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Use of dioxomorpholines to combat endoparasites, novel dioxomorpholines and process for their production
DE19520936A1 (en) 1995-06-08 1996-12-12 Bayer Ag Ectoparasiticides means
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003024222A1 (en) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2004072086A2 (en) 2003-02-14 2004-08-26 Pfizer Limited Antiparasitic terpene alkaloids
WO2005085216A1 (en) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
WO2006129714A1 (en) 2005-06-01 2006-12-07 Meiji Seika Kaisha, Ltd. Pest control agent
WO2007020986A1 (en) 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Substituted pyrazolecarboxylic acid anilide derivative or salt thereof, intermediate thereof, agent for agricultural and horticultural use, and use thereof
WO2007080131A2 (en) 2006-01-16 2007-07-19 Syngenta Participations Ag Anthranilamide derivatives and their use for the control of insects and acari
DE102006015467A1 (en) 2006-03-31 2007-10-04 Bayer Cropscience Ag New cyclic enamine ketone derivatives useful for controlling pests, especially insects
WO2007123855A2 (en) * 2006-04-20 2007-11-01 E. I. Du Pont De Nemours And Company Pyrazolines for controlling invertebrate pests
WO2009112275A1 (en) * 2008-03-14 2009-09-17 Bayer Cropscience Ag Pesticidal condensed - ring aryl compounds
WO2011066384A1 (en) 2009-11-24 2011-06-03 Dow Agrosciences Llc Aad-12 event 416, related transgenic soybean lines, and event-specific identification thereof
WO2011147953A1 (en) 2010-05-28 2011-12-01 Basf Se Pesticidal mixtures
WO2011147952A1 (en) 2010-05-28 2011-12-01 Basf Se Pesticidal mixtures
GB2481118A (en) * 2010-06-09 2011-12-14 Syngenta Participations Ag Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives
WO2012082548A2 (en) 2010-12-15 2012-06-21 Syngenta Participations Ag Soybean event syht0h2 and compositions and methods for detection thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4187099A (en) * 1977-11-16 1980-02-05 Monsanto Company 3-Aryl-4-isothiazolecarboxylic acid and 3-aryl-4-isoxazolecarboxylic acid derivatives and their use as herbicides
TWI411395B (en) * 2007-12-24 2013-10-11 Syngenta Participations Ag Insecticidal compounds
CA2858766A1 (en) * 2011-12-23 2013-06-27 Basf Se Isothiazoline compounds for combating invertebrate pests

Patent Citations (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0357460A2 (en) 1988-09-02 1990-03-07 Sankyo Company Limited 13-Substituted milbemycin derivatives, their preparation and use
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
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0382173A2 (en) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. PF 1022 substance, method of producing same and anthelmintic composition containing same
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0444964A1 (en) 1990-03-01 1991-09-04 Sankyo Company Limited Milbemycin ether derivatives, their preparation and their anthelmintic uses
EP0503538A1 (en) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Medicinal composition containing an anthelmintic cyclic depsipeptide
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
WO1993019053A1 (en) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Depsipeptide derivative, production thereof and use thereof
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1993025543A2 (en) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines and enniatine derivates used to control endoparasites
EP0594291A1 (en) 1992-09-01 1994-04-27 Sankyo Company Limited Novel processes for the production of 13-ether derivatives of milbemycins, and novel intermediates therefor
WO1994015944A1 (en) 1993-01-18 1994-07-21 Pfizer Limited New antiparasitic agents related to the milbemycins and avermectins
WO1994019334A1 (en) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Pf1022 derivative, cyclic depsipeptide
EP0626375A1 (en) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides having endoparasiticidal activity
WO1995019363A1 (en) 1994-01-14 1995-07-20 Pfizer Inc. Antiparasitic pyrrolobenzoxazine compounds
WO1995022552A1 (en) 1994-02-16 1995-08-24 Pfizer Limited Antiparasitic agents
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO1996011945A2 (en) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Cyclic depsipeptide sulfonylation, sulfenylation and phosphorylation process
WO1996015121A1 (en) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Use of dioxomorpholines to combat endoparasites, novel dioxomorpholines and process for their production
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
DE19520936A1 (en) 1995-06-08 1996-12-12 Bayer Ag Ectoparasiticides means
US7030295B2 (en) 2001-08-31 2006-04-18 Syngenta Participations Ag Modified Cry3A toxins and nucleic acid sequences coding therefor
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003024222A1 (en) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2004072086A2 (en) 2003-02-14 2004-08-26 Pfizer Limited Antiparasitic terpene alkaloids
EP1731512A1 (en) 2004-03-05 2006-12-13 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
WO2005085216A1 (en) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
WO2006129714A1 (en) 2005-06-01 2006-12-07 Meiji Seika Kaisha, Ltd. Pest control agent
WO2007020986A1 (en) 2005-08-12 2007-02-22 Nihon Nohyaku Co., Ltd. Substituted pyrazolecarboxylic acid anilide derivative or salt thereof, intermediate thereof, agent for agricultural and horticultural use, and use thereof
WO2007080131A2 (en) 2006-01-16 2007-07-19 Syngenta Participations Ag Anthranilamide derivatives and their use for the control of insects and acari
DE102006015467A1 (en) 2006-03-31 2007-10-04 Bayer Cropscience Ag New cyclic enamine ketone derivatives useful for controlling pests, especially insects
WO2007123855A2 (en) * 2006-04-20 2007-11-01 E. I. Du Pont De Nemours And Company Pyrazolines for controlling invertebrate pests
WO2009112275A1 (en) * 2008-03-14 2009-09-17 Bayer Cropscience Ag Pesticidal condensed - ring aryl compounds
WO2011066384A1 (en) 2009-11-24 2011-06-03 Dow Agrosciences Llc Aad-12 event 416, related transgenic soybean lines, and event-specific identification thereof
WO2011147953A1 (en) 2010-05-28 2011-12-01 Basf Se Pesticidal mixtures
WO2011147952A1 (en) 2010-05-28 2011-12-01 Basf Se Pesticidal mixtures
GB2481118A (en) * 2010-06-09 2011-12-14 Syngenta Participations Ag Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives
WO2012082548A2 (en) 2010-12-15 2012-06-21 Syngenta Participations Ag Soybean event syht0h2 and compositions and methods for detection thereof

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
"McCutcheon's Volume 2: Functional Materials", vol. 2, MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
CRICKMORE ET AL., MICROBIOL. MOL. BIOL REV., vol. 62, 1998, pages 807 - 813
D. S. KETTLE: "Medical and Veterinary Entomology", JOHN WILEY AND SONS
E. J. L. SOULSBY: "Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths", vol. 1, F. A. DAVIS CO.
HELMINTHS; ARTHROPODS; PROTOZOA; E. J. L. SOULSBY: "6thEdition of Monnig's Veterinary Helminthology and Entomology", WILLIAMS AND WILKINS CO.
JOURNAL OF ORGANIC CHEMISTRY, vol. 46, no. 4, 1981, pages 771 - 775
JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 13, 1990, pages 4156 - 62
JOURNAL OF ORGANIC CHEMISTRY, vol. 61, 1996, pages 1986
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, 2011, pages 6403 - 6410
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 71, 1949, pages 3554 - 5
JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, 1972, pages 153 - 7
ORGANIC LETTERS, vol. 8, no. 21, 2006, pages 4811 - 4813
R. O. DRUMMAND; J. E. GEORGE; S. E. KUNZ: "Control of Arthropod Pests of Livestock: A Review of Technology", CRC PRESS
T. W. GREEN; P. G. M. WUTS: "Protective Groups in Organic Synthesis", 1999, WILEY-INTERSCIENCE, pages: 564 - 566,740-
TETRAHEDRON: ASYMMETRY, vol. 14, no. 1, 2003, pages 113 - 117

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