EP1341780A2 - Substituted heterocyclic phthalic acid diamide arthropodicides - Google Patents
Substituted heterocyclic phthalic acid diamide arthropodicidesInfo
- Publication number
- EP1341780A2 EP1341780A2 EP01990065A EP01990065A EP1341780A2 EP 1341780 A2 EP1341780 A2 EP 1341780A2 EP 01990065 A EP01990065 A EP 01990065A EP 01990065 A EP01990065 A EP 01990065A EP 1341780 A2 EP1341780 A2 EP 1341780A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- ffl
- ffi
- ffi ffi
- hcj
- chf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 125000000623 heterocyclic group Chemical group 0.000 title description 10
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 555
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 486
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 377
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 129
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 114
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 81
- 229910052801 chlorine Inorganic materials 0.000 claims description 63
- 229910052794 bromium Inorganic materials 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- -1 C1-C4 alkoxyalkyi Chemical group 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical group 0.000 claims description 44
- 229910052740 iodine Inorganic materials 0.000 claims description 38
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 239000002917 insecticide Substances 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 239000005660 Abamectin Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
- 239000005950 Oxamyl Substances 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 6
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 5
- 108700003918 Bacillus Thuringiensis insecticidal crystal Proteins 0.000 claims description 5
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 5
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 5
- ANHSIWMPKXILBK-UHFFFAOYSA-N CC(C)C1(C(N)=O)C=CC=CC1C(N)=O Chemical compound CC(C)C1(C(N)=O)C=CC=CC1C(N)=O ANHSIWMPKXILBK-UHFFFAOYSA-N 0.000 claims description 5
- 239000005895 Esfenvalerate Substances 0.000 claims description 5
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 239000005906 Imidacloprid Substances 0.000 claims description 5
- 239000005907 Indoxacarb Substances 0.000 claims description 5
- 239000005916 Methomyl Substances 0.000 claims description 5
- 239000005925 Pymetrozine Substances 0.000 claims description 5
- 239000005927 Pyriproxyfen Substances 0.000 claims description 5
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 claims description 5
- 229950008167 abamectin Drugs 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229960002587 amitraz Drugs 0.000 claims description 5
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 5
- 229940097012 bacillus thuringiensis Drugs 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 5
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims description 5
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 5
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 5
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 229940056881 imidacloprid Drugs 0.000 claims description 5
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 5
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 claims description 5
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 claims description 5
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 5
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 4
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 4
- 239000005946 Cypermethrin Substances 0.000 claims description 4
- 239000005894 Emamectin Substances 0.000 claims description 4
- 239000005930 Spinosad Substances 0.000 claims description 4
- 239000005940 Thiacloprid Substances 0.000 claims description 4
- 239000005942 Triflumuron Substances 0.000 claims description 4
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 4
- 239000003124 biologic agent Substances 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229960001591 cyfluthrin Drugs 0.000 claims description 4
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 4
- 229960005424 cypermethrin Drugs 0.000 claims description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 claims description 4
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 230000001069 nematicidal effect Effects 0.000 claims description 4
- 239000005645 nematicide Substances 0.000 claims description 4
- 229940014213 spinosad Drugs 0.000 claims description 4
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 4
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 4
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 239000005888 Clothianidin Substances 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 3
- 230000000967 entomopathogenic effect Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 3
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 2
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims description 2
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 claims description 2
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims description 2
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 claims description 2
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims description 2
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 claims description 2
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005875 Acetamiprid Substances 0.000 claims description 2
- 239000005878 Azadirachtin Substances 0.000 claims description 2
- 239000005874 Bifenthrin Substances 0.000 claims description 2
- 239000005885 Buprofezin Substances 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005945 Chlorpyrifos-methyl Substances 0.000 claims description 2
- 239000005887 Chromafenozide Substances 0.000 claims description 2
- 239000005891 Cyromazine Substances 0.000 claims description 2
- 239000005892 Deltamethrin Substances 0.000 claims description 2
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 claims description 2
- 239000005893 Diflubenzuron Substances 0.000 claims description 2
- 239000005947 Dimethoate Substances 0.000 claims description 2
- 239000005897 Etoxazole Substances 0.000 claims description 2
- 239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 claims description 2
- 239000005656 Fenazaquin Substances 0.000 claims description 2
- 239000005898 Fenoxycarb Substances 0.000 claims description 2
- 239000005657 Fenpyroximate Substances 0.000 claims description 2
- 239000005900 Flonicamid Substances 0.000 claims description 2
- 239000005661 Hexythiazox Substances 0.000 claims description 2
- 239000005912 Lufenuron Substances 0.000 claims description 2
- 239000005949 Malathion Substances 0.000 claims description 2
- 239000005956 Metaldehyde Substances 0.000 claims description 2
- 239000005917 Methoxyfenozide Substances 0.000 claims description 2
- 239000005921 Phosmet Substances 0.000 claims description 2
- 239000005663 Pyridaben Substances 0.000 claims description 2
- 239000005926 Pyridalyl Substances 0.000 claims description 2
- 239000005937 Tebufenozide Substances 0.000 claims description 2
- 239000005658 Tebufenpyrad Substances 0.000 claims description 2
- 239000005938 Teflubenzuron Substances 0.000 claims description 2
- 239000005939 Tefluthrin Substances 0.000 claims description 2
- 239000005941 Thiamethoxam Substances 0.000 claims description 2
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims description 2
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims description 2
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims description 2
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 claims description 2
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 claims description 2
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 2
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 2
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims description 2
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 claims description 2
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 claims description 2
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 2
- 229950000775 cyromazine Drugs 0.000 claims description 2
- 229960002483 decamethrin Drugs 0.000 claims description 2
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 claims description 2
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims description 2
- 229940019503 diflubenzuron Drugs 0.000 claims description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 2
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 claims description 2
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 claims description 2
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 claims description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 2
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims description 2
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 claims description 2
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 claims description 2
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 claims description 2
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims description 2
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002949 juvenile hormone Chemical class 0.000 claims description 2
- 229930014550 juvenile hormone Chemical class 0.000 claims description 2
- 150000003633 juvenile hormone derivatives Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 2
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000521 lufenuron Drugs 0.000 claims description 2
- 229960000453 malathion Drugs 0.000 claims description 2
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 claims description 2
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 claims description 2
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 claims description 2
- 229930002897 methoprene Natural products 0.000 claims description 2
- 229950003442 methoprene Drugs 0.000 claims description 2
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 claims description 2
- 229960001952 metrifonate Drugs 0.000 claims description 2
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims description 2
- 230000001537 neural effect Effects 0.000 claims description 2
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 claims description 2
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 claims description 2
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 claims description 2
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 claims description 2
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 claims description 2
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 claims description 2
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 claims description 2
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 claims description 2
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 2
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 2
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 claims description 2
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 2
- 229940080817 rotenone Drugs 0.000 claims description 2
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 2
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005936 tau-Fluvalinate Substances 0.000 claims description 2
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 claims description 2
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims description 2
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 claims description 2
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims description 2
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 claims description 2
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 2
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 claims description 2
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 2
- 241000701447 unidentified baculovirus Species 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 239000005944 Chlorpyrifos Substances 0.000 claims 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims 1
- 229960000490 permethrin Drugs 0.000 claims 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 2203
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 370
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 140
- CLZAEVAEWSHALL-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoropropane Chemical compound F[C](F)C(F)(F)C(F)(F)F CLZAEVAEWSHALL-UHFFFAOYSA-N 0.000 description 82
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 238000012360 testing method Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000003085 diluting agent Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000012442 inert solvent Substances 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- 230000009418 agronomic effect Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 241000258937 Hemiptera Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 241000244206 Nematoda Species 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 6
- 230000037213 diet Effects 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 241000257226 Muscidae Species 0.000 description 5
- 241000256251 Spodoptera frugiperda Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 4
- 241000238421 Arthropoda Species 0.000 description 4
- 241000242722 Cestoda Species 0.000 description 4
- 241001635274 Cydia pomonella Species 0.000 description 4
- 241000237858 Gastropoda Species 0.000 description 4
- 241001000403 Herpetogramma licarsisalis Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 4
- 241000721621 Myzus persicae Species 0.000 description 4
- 241000721451 Pectinophora gossypiella Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 241000256247 Spodoptera exigua Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000339374 Thrips tabaci Species 0.000 description 4
- 241000255993 Trichoplusia ni Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001600408 Aphis gossypii Species 0.000 description 3
- 241000273311 Aphis spiraecola Species 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- 241000254127 Bemisia tabaci Species 0.000 description 3
- 241001035625 Dysdercus suturellus Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005899 Fipronil Substances 0.000 description 3
- 241001147381 Helicoverpa armigera Species 0.000 description 3
- 241000255967 Helicoverpa zea Species 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- 241000257303 Hymenoptera Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241001261104 Lobesia botrana Species 0.000 description 3
- 241000258912 Lygaeidae Species 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- 241000517307 Pediculus humanus Species 0.000 description 3
- 241001516577 Phylloxera Species 0.000 description 3
- 241000255969 Pieris brassicae Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000985245 Spodoptera litura Species 0.000 description 3
- 241001414989 Thysanoptera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000242541 Trematoda Species 0.000 description 3
- 241000256856 Vespidae Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229940013764 fipronil Drugs 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000001508 sulfur Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241000700606 Acanthocephala Species 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 2
- 241001014341 Acrosternum hilare Species 0.000 description 2
- 241001136249 Agriotes lineatus Species 0.000 description 2
- 241000238682 Amblyomma americanum Species 0.000 description 2
- 241000242266 Amphimallon majalis Species 0.000 description 2
- 241001259789 Amyelois transitella Species 0.000 description 2
- 241000663922 Anasa tristis Species 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241001151957 Aphis aurantii Species 0.000 description 2
- 241000271857 Aphis citricidus Species 0.000 description 2
- 241000952611 Aphis craccivora Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241001002470 Archips argyrospila Species 0.000 description 2
- 241001423656 Archips rosana Species 0.000 description 2
- 241001166626 Aulacorthum solani Species 0.000 description 2
- 241001302798 Bemisia argentifolii Species 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 241001631693 Blattella asahinai Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241001629132 Blissus leucopterus Species 0.000 description 2
- 241001113967 Bovicola ovis Species 0.000 description 2
- 241000987201 Brevipalpus californicus Species 0.000 description 2
- 241001425384 Cacopsylla pyricola Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241001338038 Camponotus chromaiodes Species 0.000 description 2
- 241001491934 Camponotus pennsylvanicus Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- 241001609899 Ceratophyllus gallinae Species 0.000 description 2
- 241001166081 Chelisoches morio Species 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- 241000258920 Chilopoda Species 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- 241000254137 Cicadidae Species 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241001509962 Coptotermes formosanus Species 0.000 description 2
- 241001114553 Coreidae Species 0.000 description 2
- 241001340508 Crambus Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- 241000258924 Ctenocephalides felis Species 0.000 description 2
- 241001127981 Demodicidae Species 0.000 description 2
- 241001480793 Dermacentor variabilis Species 0.000 description 2
- 241001124144 Dermaptera Species 0.000 description 2
- 241000489947 Diabrotica virgifera virgifera Species 0.000 description 2
- 241001205778 Dialeurodes citri Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001279823 Diuraphis noxia Species 0.000 description 2
- 241001517923 Douglasiidae Species 0.000 description 2
- 241001581006 Dysaphis plantaginea Species 0.000 description 2
- 241000353522 Earias insulana Species 0.000 description 2
- 241001572697 Earias vittella Species 0.000 description 2
- 241001549209 Echidnophaga gallinacea Species 0.000 description 2
- 241000995027 Empoasca fabae Species 0.000 description 2
- 241000086608 Empoasca vitis Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- 241000917107 Eriosoma lanigerum Species 0.000 description 2
- 241000927584 Frankliniella occidentalis Species 0.000 description 2
- 241001441330 Grapholita molesta Species 0.000 description 2
- 241001251909 Hyalopterus pruni Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241001058150 Icerya purchasi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000922049 Ixodes holocyclus Species 0.000 description 2
- 241000238703 Ixodes scapularis Species 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 241001638457 Lasius alienus Species 0.000 description 2
- 241000238866 Latrodectus mactans Species 0.000 description 2
- 241000500881 Lepisma Species 0.000 description 2
- 241001646976 Linepithema humile Species 0.000 description 2
- 241001113946 Linognathus vituli Species 0.000 description 2
- 241000272317 Lipaphis erysimi Species 0.000 description 2
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- 241000254022 Locusta migratoria Species 0.000 description 2
- 241000238865 Loxosceles reclusa Species 0.000 description 2
- 241000501345 Lygus lineolaris Species 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241000922538 Melanoplus sanguinipes Species 0.000 description 2
- 241000292449 Menacanthus stramineus Species 0.000 description 2
- 241001414825 Miridae Species 0.000 description 2
- 241000952627 Monomorium pharaonis Species 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 241000084931 Neohydatothrips variabilis Species 0.000 description 2
- 241000615716 Nephotettix nigropictus Species 0.000 description 2
- 241001671709 Nezara viridula Species 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- 241000256259 Noctuidae Species 0.000 description 2
- 241001446843 Oebalus pugnax Species 0.000 description 2
- 241000258913 Oncopeltus fasciatus Species 0.000 description 2
- 241001147398 Ostrinia nubilalis Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241000459456 Parapediasia teterrellus Species 0.000 description 2
- 241000051771 Paratrechina longicornis Species 0.000 description 2
- 241000320508 Pentatomidae Species 0.000 description 2
- 241000256682 Peregrinus maidis Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001510001 Periplaneta brunnea Species 0.000 description 2
- 241000227425 Pieris rapae crucivora Species 0.000 description 2
- 241000691880 Planococcus citri Species 0.000 description 2
- 241000254101 Popillia japonica Species 0.000 description 2
- 241000721694 Pseudatomoscelis seriatus Species 0.000 description 2
- 241000718000 Pulex irritans Species 0.000 description 2
- 241001509967 Reticulitermes flavipes Species 0.000 description 2
- 241001152954 Reticulitermes hesperus Species 0.000 description 2
- 241000167882 Rhopalosiphum maidis Species 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241001510236 Rhyparobia maderae Species 0.000 description 2
- 241000254030 Schistocerca americana Species 0.000 description 2
- 241000253973 Schistocerca gregaria Species 0.000 description 2
- 241000722027 Schizaphis graminum Species 0.000 description 2
- 241000545593 Scolytinae Species 0.000 description 2
- 241001157780 Scutigera coleoptrata Species 0.000 description 2
- 241000180219 Sitobion avenae Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 241000176086 Sogatella furcifera Species 0.000 description 2
- 241000517830 Solenopsis geminata Species 0.000 description 2
- 241000736128 Solenopsis invicta Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241001649248 Supella longipalpa Species 0.000 description 2
- 241000255628 Tabanidae Species 0.000 description 2
- 241001157793 Tapinoma sessile Species 0.000 description 2
- 241000255588 Tephritidae Species 0.000 description 2
- 241001374808 Tetramorium caespitum Species 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 241000028626 Thermobia domestica Species 0.000 description 2
- 241000663810 Tingidae Species 0.000 description 2
- 241000255901 Tortricidae Species 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 241001259048 Trichodectes canis Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 241001389006 Tuta absoluta Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000908414 Wasmannia auropunctata Species 0.000 description 2
- 241000353223 Xenopsylla cheopis Species 0.000 description 2
- 241001248766 Zonocyba pomaria Species 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- WPOOICLZIIBUBM-UHFFFAOYSA-H iron;iron(3+);methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Fe].[Fe+3].[Fe+3].C[As]([O-])([O-])=O.C[As]([O-])([O-])=O.C[As]([O-])([O-])=O WPOOICLZIIBUBM-UHFFFAOYSA-H 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- TZURDPUOLIGSAF-VCEOMORVSA-N (4S)-4-[[(2S)-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S)-2-aminopropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]acetyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylbutanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-3-carboxy-1-[[(2S,3R)-1-[[(2S)-3-carboxy-1-[[(2S)-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-oxopentanoic acid Chemical compound CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)CNC(=O)[C@H](CCSC)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)N)C(C)C)[C@@H](C)CC)C(C)C)C(C)C)[C@@H](C)CC)C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(O)=O TZURDPUOLIGSAF-VCEOMORVSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- IDPFMOHZZAETJC-UHFFFAOYSA-N 4-(5-iodopyridin-3-yl)-2-(2,2,2-trifluoroethoxy)isoindole-1,3-dione Chemical compound C=12C(=O)N(OCC(F)(F)F)C(=O)C2=CC=CC=1C1=CN=CC(I)=C1 IDPFMOHZZAETJC-UHFFFAOYSA-N 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- OJCXGRPKFISGAZ-UHFFFAOYSA-N 6-(2,2,2-trifluoroethoxy)pyridin-3-amine Chemical compound NC1=CC=C(OCC(F)(F)F)N=C1 OJCXGRPKFISGAZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241001516607 Adelges Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241000254124 Aleyrodidae Species 0.000 description 1
- 241000902876 Alticini Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001626719 Anoplocephala perfoliata Species 0.000 description 1
- 241000396431 Anthrenus scrophulariae Species 0.000 description 1
- 241000149536 Anthribidae Species 0.000 description 1
- 241000566651 Aphis forbesi Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241001507652 Aphrophoridae Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241001002469 Archips Species 0.000 description 1
- 241000244176 Ascaridida Species 0.000 description 1
- 241000220319 Athous Species 0.000 description 1
- 241000221377 Auricularia Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 241000701412 Baculoviridae Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000929635 Blissus Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000255625 Brachycera Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001643374 Brevipalpus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005741 Bromuconazole Substances 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- 244000068645 Carya illinoensis Species 0.000 description 1
- 241000134426 Ceratopogonidae Species 0.000 description 1
- 241001414824 Cercopidae Species 0.000 description 1
- 241001094931 Chaetosiphon fragaefolii Species 0.000 description 1
- 241000255930 Chironomidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001157805 Chloropidae Species 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241000191839 Chrysomya Species 0.000 description 1
- 241001124179 Chrysops Species 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- 241000008892 Cnaphalocrocis patnalis Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000720864 Coleophoridae Species 0.000 description 1
- 239000005752 Copper oxychloride Substances 0.000 description 1
- 241000677504 Corythucha Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001506147 Cryptotermes brevis Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 239000005755 Cyflufenamid Substances 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 241001090151 Cyrtopeltis Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241000131287 Dermestidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- 241000586568 Diaspidiotus perniciosus Species 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005762 Dimoxystrobin Substances 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- 241001380467 Ectobiidae Species 0.000 description 1
- 241001427543 Elateridae Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241000578375 Enoplida Species 0.000 description 1
- 241000554916 Epidermoptidae Species 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001619920 Euschistus servus Species 0.000 description 1
- 241000566572 Falco femoralis Species 0.000 description 1
- 239000005772 Famoxadone Substances 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 239000005774 Fenamidone Substances 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005785 Fluquinconazole Substances 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241001645378 Glycyphagidae Species 0.000 description 1
- 241000322637 Goniocotes Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241000578422 Graphosoma lineatum Species 0.000 description 1
- 241001243091 Gryllotalpa Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241000894055 Haematopinus eurysternus Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 241000255990 Helicoverpa Species 0.000 description 1
- 241001608644 Hippoboscidae Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241001497708 Incisitermes immigrans Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005796 Ipconazole Substances 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 241001495069 Ischnocera Species 0.000 description 1
- 241001149911 Isopoda Species 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005800 Kresoxim-methyl Substances 0.000 description 1
- 241000661779 Leptoglossus Species 0.000 description 1
- 241000683448 Limonius Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- 241001414662 Macrosteles fascifrons Species 0.000 description 1
- 241000168714 Magicicada septendecim Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 241001648788 Margarodidae Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241001415015 Melanoplus differentialis Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 241000254043 Melolonthinae Species 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- 241001414856 Membracidae Species 0.000 description 1
- 241000002163 Mesapamea fractilinea Species 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- 241000180212 Metopolophium Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 239000005811 Myclobutanil Substances 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- XFOXDUJCOHBXRC-UHFFFAOYSA-N N-Ethyl-N-methyl-4-(trifluoromethyl)-2-(3,4-dimethoxyphenyl)benzamide Chemical compound CCN(C)C(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(OC)C(OC)=C1 XFOXDUJCOHBXRC-UHFFFAOYSA-N 0.000 description 1
- 241000133259 Nasonovia Species 0.000 description 1
- 241000133263 Nasonovia ribisnigri Species 0.000 description 1
- 241000255932 Nematocera Species 0.000 description 1
- 241000359016 Nephotettix Species 0.000 description 1
- 241000257191 Oestridae Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241000975417 Oscinella frit Species 0.000 description 1
- 241001221709 Oxyurida Species 0.000 description 1
- 241000497111 Paralobesia viteana Species 0.000 description 1
- 241001143330 Paratrichodorus minor Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241001525654 Phyllocnistis citrella Species 0.000 description 1
- 241001465981 Phylloxeridae Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 241000219843 Pisum Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 241000736232 Prosimulium Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000722234 Pseudococcus Species 0.000 description 1
- 241001649231 Psoroptidae Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241001414857 Psyllidae Species 0.000 description 1
- 241001466030 Psylloidea Species 0.000 description 1
- 241000238704 Pyemotidae Species 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 239000005828 Pyrimethanil Substances 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 239000005831 Quinoxyfen Substances 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- 241000244200 Rhabditida Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000509418 Sarcoptidae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000343234 Scirtothrips citri Species 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 241000332477 Scutellonema bradys Species 0.000 description 1
- 241000131790 Scutigeromorpha Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 241000256103 Simuliidae Species 0.000 description 1
- 241000256108 Simulium <genus> Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 239000005837 Spiroxamine Substances 0.000 description 1
- 241000244042 Spirurida Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000243788 Strongylida Species 0.000 description 1
- 241000122938 Strongylus vulgaris Species 0.000 description 1
- 241000237361 Stylommatophora Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000883295 Symphyla Species 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000194622 Tagosodes orizicolus Species 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000488607 Tenuipalpidae Species 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 241000488577 Tetranychus mcdanieli Species 0.000 description 1
- 241000289813 Therioaphis trifolii Species 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 241000843170 Togo hemipterus Species 0.000 description 1
- 241000244030 Toxocara canis Species 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 239000005848 Tribasic copper sulfate Substances 0.000 description 1
- 241001220308 Trichodorus Species 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 241001414858 Trioza Species 0.000 description 1
- 239000005859 Triticonazole Substances 0.000 description 1
- 241000331598 Trombiculidae Species 0.000 description 1
- 241000261594 Tyrophagus longior Species 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 241001310905 Xylocopinae Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- CGIHPACLZJDCBQ-UHFFFAOYSA-N acibenzolar Chemical compound SC(=O)C1=CC=CC2=C1SN=N2 CGIHPACLZJDCBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-UHFFFAOYSA-N blasticidin-S Natural products O1C(C(O)=O)C(NC(=O)CC(N)CCN(C)C(N)=N)C=CC1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- RXDMAYSSBPYBFW-UHFFFAOYSA-N carpropamid Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(CC)C(C)C1(Cl)Cl RXDMAYSSBPYBFW-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- YEJGPFZQLRMXOI-PKEIRNPWSA-N diclocymet Chemical compound N#CC(C(C)(C)C)C(=O)N[C@H](C)C1=CC=C(Cl)C=C1Cl YEJGPFZQLRMXOI-PKEIRNPWSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- 229940004812 dicloran Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N dimethylglyoxal Natural products CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- 150000004844 dioxiranes Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 1
- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- NWUWYYSKZYIQAE-WMCAAGNKSA-N iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-WMCAAGNKSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 230000007758 mating behavior Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- NWUWYYSKZYIQAE-LBAUFKAWSA-N propan-2-yl n-[3-methyl-1-[[(1s)-1-(4-methylphenyl)ethyl]amino]-1-oxobutan-2-yl]carbamate Chemical compound CC(C)OC(=O)NC(C(C)C)C(=O)N[C@@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-LBAUFKAWSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- This invention relates to certain heterocyclic phthalic acid diamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.
- invetebrate pests The control of invetebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
- the control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.
- EP919542 discloses phthalic acid diamides of Formula i as insecticides
- Z 1 and Z 2 are O or S;
- R 1 , R 2 and R 3 are, among others, H, alkyl or substituted alkyl.
- WOO 1/02354 discloses phthalic acid diamides of Formula ii as insecticides
- Q is an optionally substituted hetero cycle containing O, S or ;
- Z 1 and Z 2 are O or S; and
- R 1 , R 2 and R 3 are, among others, H, alkyl or substituted alkyl.
- This invention pertains to compounds of Formula I and N-oxides and agriculturally suitable salts thereof
- J is selected from the group consisting of J-l, J-2, J-3, J-4, J-5, J-6, J-7 and J-8
- R 1 is H, Ci-C 6 alkyl, C 2 -C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
- R 2 is H or C ⁇ -C 6 alkyl
- R 3 is H; C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, or C 4 -C 8 cycloalkylalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , hydroxy, C1-C4 alkyl, C !
- R 4 group is attached to the phenyl ring at the 3-position or 6-position, and said R 4 is C r C4 alkyl, C r C 4 haloalkyl, halogen, CN, NO 2 , C !
- R 5 is H, Ci-C 4 alkyl, C r C 4 haloalkyl, or
- Y is N, CH, CF, CC1, CBr or Cl; each R 6 and R 7 is independently H, C ⁇ -Cg alkyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, halogen, CN, C 1 -C4 alkoxy, C1-C 4 haloalkoxy or C1-C 4 haloalkylthio;
- R 9 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl or C 3 -C6 haloalkynyl; provided R 7 and R 9 are not both H; R 10 is H or Cr-C- alkyl or C1-C haloalkyl; R 1 1 is H or -C4 alkyl; and n is 1 or 2.
- This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.
- This invention also pertains to a composition comprising a biologically effective amount of a compound of Formula I and an effective amount of at least one additional biologically active compound or agent.
- This invention also pertains to a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I (e.g., as a composition described herein).
- a biologically effective amount of a compound of Formula I e.g., as a composition described herein.
- This invention also relates to such method wherein the invertebrate pest or its environment is contacted with a biologically effective amount of a compound of Formula I or a composition comprising a compound of Formula I and a biologically effective amount of at least one additional compound or agent for controlling invertebrate pests.
- alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as methyl, ethyl, /.-propyl, t ' -propyl, or the different butyl, pentyl or hexyl isomers.
- Alkenyl can include straight-chain or branched alkenes such as 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl andhexenyl isomers.
- Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
- Alkynyl includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
- Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
- Alkoxy includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
- Alkoxyalkyi denotes alkoxy substitution on alkyl.
- alkoxyalkyi include CH 3 OCH2, CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
- Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
- Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
- Cycloalkylalkyi indicates an alkyl group substituted with a cycloalky group and includes, for example, cyclopropylmethyl, cyclobutylethyl, cyclopentylpropyl and cyclohexylmethyl.
- heteroaromatic ring denotes fully aromatic rings in which at least one ring atom is not carbon and can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heteroaromatic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the H ⁇ ckel rule is satisfied).
- the heteroaromatic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen.
- halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
- haloalkyl when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
- haloalkyl include F 3 C, CICH2, CF3CH2 and CF 3 CC1 2 .
- haloalkenyl “haloalkynyl”, “haloalkoxy”, and the like, are defined analogously to the term “haloalkyl”.
- haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
- haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
- C1-C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
- C 2 alkoxyalkyi designates CH 3 OCH 2
- C 3 alkoxyalkyi designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
- C4 alkoxyalkyi designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH 2 CH 2 OCH 2 and CH3CH2OCH2CH2.
- Stereoisomers of this invention can exist as one or more stereoisomers.
- the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
- the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds ofthe invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
- the present invention comprises of compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof.
- nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.
- tertiary amines can form N-oxides.
- the salts ofthe compounds ofthe invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, saHcylic, tartaric, 4-toluenesulfonic or valeric acids.
- inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, saHcylic, tartaric, 4-toluenesulfonic or valeric acids.
- the wavy line represents the rema ⁇ inder of the J group to which said R 5 moiety is attached.
- Preferred compounds for reasons of better activity, cost and/or ease of synthesis are: Preferred 1. Compounds of Formula I wherein V is N. Preferred 2. Compounds of Formula I wherein V is CH, CF, CC1 or CBr. Preferred 3. Compounds of Preferred 1 or Preferred 2 wherein
- R 1 and R 2 are both H
- R 3 is C r C 4 alkyl optionally substituted with halogen, CN, OCH 3 , S(O) p CH ; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is C r C 4 alkyl, C 1 -C 4 haloalkyl, halogen or CN; R 7 is H, CH 3 , CF 3 , OCHF 2 or halogen; and p is 0, 1 or 2.
- Preferred 4 Compounds of Preferred 3 wherein J is J-l;
- R 3 is C1-C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is
- R 4 is H, F, Cl, Br, I or CF 3 ;
- R6 is Cl or Br;
- R 7 is halogen or CF3.
- Preferred 5 Compounds of Preferred 4 wherein V is N;
- R 3 is methyl, ethyl, isopropyl or tertiary butyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is
- R 3 is C r C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is CH 3 , CL Br or l; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is Cl or Br
- R 9 is CF 3 , CHF 2 , CH 2 CF 3 , CF 2 CHF 2 .
- Preferred 7 Compounds of Preferred 3 wherein J is J-3; R 3 is C r C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is
- R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is Cl or Br; and
- R 7 is halogen or CF 3 .
- R 3 is C ! -C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is CH 3 , CL Br orl; a second R 4 is H, F, Cl, Br, I or CF ; R 6 is Cl or Br; and R 7 is CF 3 .
- Preferred 9. Compounds of Preferred 3 wherein J is J-5;
- R 3 is C r C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is
- R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is Cl or Br;
- R9 is CF 3 , CHF 2 , CH 2 CF 3 , CF 2 CHF 2 .
- Preferred 10 Compounds of Preferred 3 wherein J is J-6;
- R 3 is C r C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is
- R 3 is C r C 4 alkyl; one R 4 group is attached to the K-ring at the 2-position and said R 4 is CH3, Cl or Br; a second R 4 is H, F, Cl, Br, I or CF 3 ; R 6 is Cl or Br; R 7 is H, halogen or CF 3 .and R9 is H, CF 3 , CHF 2 , CH 2 CF 3 , CF 2 CHF 2 .
- R 3 is C r C 4 alkyl; one R 4 group is attached to the phenyl ring at the 3-position and said R 4 is CH 3 , CL Brorl; a second R 4 is H, F, Cl, Br, I or CF 3 ; R 6 is Cl or Br; R 7 is H, halogen or CF3.and R9 is H, CF 3 , CHF 2 , CH 2 CF 3 , CF 2 CHF 2 . Specifically preferred are compounds selected from the group consisting of:
- compositions ofthe present invention are those that comprise the above preferred compounds.
- J is selected from the group consisting of
- R 1 is H, C ⁇ -Cg alkyl, C 2 -C6 alkoxycarbonyl or C 2 -Cg alkylcarbonyl;
- R 2 is H or C r C 6 alkyl
- R 3 is H; Cj-Cg alkyl, C -C6 alkenyl, C 2 -Cg alkynyl, or C3-C 6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C4 alkyl, -C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, -C 4 alkylsulfmyl, C 1 -C4 alkylsulfonyl, C 2 -C6 alkoxycarbonyl, C 2 -Cg alkylcarbonyl, C3-C6 trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of Cj -C alkyl, C 2 -C4 alken
- each R 6 is independently Cj-Cg alkyl, C j -Cg haloalkyl, halogen, CN, C1-C4 alkoxy,
- R 7 is C1-C4 alkyl, C 2 -C alkenyl, C 2 -C4 alkynyl, C 3 -C6 cycloalkyl, -C4 haloalkyl, C 2 -C4 haloalkenyl, C 2 -C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C4 alkylthio, C1-C4 alkylsulfinyl, Cy C 4 alkylsulfonyl, C1-C4 alkylamino, C 2 -Cg dialkylamino, C 3 -C6 cycloalkylamino, C3-C6 (alkyl)cycloalkyla
- X is , CH, CF, CCl or CBr.
- Selection A Compounds of Formulal d wherein X is N.
- Selection B Compounds of Formulald wherein X is CH, CF, CC1 or CBr.
- Selection C The compounds of Selection A or Selection B wherein
- J is J-59;
- R 1 , R 2 andR 8 are all H;
- R 3 is C ⁇ -C 4 alkyl optionally substituted with halogen, CN, OCH 3 , S(O) p CH 3 ; one R 4 is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is CH3, CF 3 or halogen; and ' p is 0, 1 or 2.
- Selection D Compounds of Selection C wherein R 3 is C r C 4 alkyl; one R 4 is CH 3 , Cl orBr; a second R 4 is H, F, Cl, Br, I or CF ; R 6 is CF 3 ; and R 7 is Cl or Br.
- Selection E The compounds of Selection A or Selection B wherein
- R 1 and R 2 are both H
- R 3 is C r C 4 alkyl optionally substituted with halogen, CN, OCH 3 , S(O) p CH 3 ; one R 4 is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 9 is C 2 -Cg alkyl or Cj-Cg haloalkyl; and p is 0, lor 2.
- Selection F Compounds of Selection E wherein R 3 is C r C 4 alkyl; one R 4 is CH 3 , Cl orBr; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 9 is CF 3 , CHF 2 , CH 2 CF 3 , CF 2 CHF 2 ;
- R 7 is Cl or Br.
- Selection G The compounds of Selection A or Selection B wherein
- J is J-61;
- R 1 , R andR 8 are all H
- R 3 is C r C 4 alkyl optionally substituted with halogen, CN, OCH 3 , S(O) p CH 3 ; one R 4 is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is CH 3 , CF 3 or halogen; and p is 0, 1 or 2.
- Selection H Compounds of Selection G wherein
- R 3 is C r C 4 alkyl; one R 4 is CH 3 , Cl orBr; a second R 4 is H, F, Cl, Br, I or CF 3 ;
- R 6 is CF 3 ;
- R 7 is Cl or Br.
- Selection I The compounds of Selection A or Selection B wherein J is J-62;
- R 1 , R 2 and R 8 are all H;
- R 3 is C r C 4 alkyl optionally substituted with halogen, CN, OCH 3 , S(O) p CH ; one R 4 is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; a second R 4 is H, F, Cl, Br, I or CF 3 ; R 6 is CH 3 , CF 3 or halogen; and p is 0, 1 or 2.
- R 3 is C r C 4 alkyl; one R 4 is CH 3 , Cl or Br; a second R 4 is H, F, Cl, Br, I or CF 3 ; R 6 is CF 3 ; and R 7 is Cl or Br.
- compositions comprising a biologically effective amount of a compound of Formula Id and at least one additional component selected from the group consisting of surfactants, solid diluents and Hquid diluents. Also of note are said compositions further comprising at least one additional biologically active compound or agent. Selected compositions are those comprising the selected compounds above.
- Also of note is a method for controlling lepidopteran, homopteran and coleopteran insects comprising contacting the insects or their environment with a biologically effective amount of a compound of Formula Id, its N-oxide or an agriculturally suitable salt thereof.
- Selected methods are those comprising the selected compounds above.
- the compounds of Formula I can be prepared by one or more of the following methods and variations described in Schemes 1 and 2.
- the definitions of J, R 1 , R 2 , R 3 , R 4 and n in the compounds of Formulae 1-9 are as defined above in the Summary ofthe Invention.
- Phthalic acid diamides of formula lb and Ic can be made by the method described in Scheme 1. Heating a phthalic anhydride of formula 2 with an aminoheterocycle of Formula H 2 ⁇ -J in an inert solvent such as glacial acetic acid affords a phthalimide of Formula 3. Ring-opening of phthalimide 3 with an amine ofthe Formula HNR 2 R 3 in an inert solvent such as dioxane or tetrahydrofuran at room temperture or heating at reflux gives a phthalic acid diamide of formula lb. Alkylation of a compound of formula lb with a suitable alkylating agent (e.g.
- alkyl halide or an alkyl methane- or 4-toluene-sulfonate or acylating agent (e.g. an alkylchloroformate or acid chloride) in the presence of a base such as sodium hydride or H-butyl lithium in an inert solvent such as tefrahydrofuran or
- N,N-dimethylformamide affords a phthaHc acid diamide of formula Ic wherein R 1 is a substituent other than hydrogen.
- PhthaHc anhydrides of Formula 2 can be made by methods taught in/. Org. Chem., 1987, 52, 129, J. Am. Chem. Soc, 1929, 51, 1865, and/. Am. Chem. Soc, 1941, 63, 1542.
- Aminoheterocycles of formula H 2 ⁇ -J can be made by methods as described in Rodd's Chemistry of Organic Compounds: HeterocycHc Compounds, volume IN, parts C, F and IJ (1989), Comprehensive Heterocyclic Chemistry, volumes 2, 3,4,5 and 6 (1984) and Comprehensive Heterocyclic Chemistry II, volumes 3, 4, 5 and 6 (1996).
- Scheme 1
- Hthiation of a benzamide of Formula 7 with w-butyl lithium in an inert solvent such as tefrahydrofuran foUowed by reaction with a carbamoyl chloride chloride of Formula 8 provides a phthalic acid diamide of Formula I wherein R 2 is other than hydrogen.
- Reaction of a benzamide of Formula 7 with n-butyl lithium in an inert solvent such as tefrahydrofuran followed by reaction with an isocyanate of Formula 9 provides a phthalic acid diamide of Formula 1 wherein R 2 is hydrogen.
- Benzamides of Formulae 4 and 7 are readily made from the corresponding benzoic acids via a benzoyl chloride intermediate or by direct coupling of a benzoic acid and amine in the presence of a suitable acid/amine coupling agent such as 1,3- cHcyclohexylcarbodiimide or 1,1 '-carbonyldiimidazole in an inert solvent such as dichloromethane or N,N-&methylformamide.
- Benzoic acids are readily converted to the acid chlorides on treatment with thionyl chloride or oxalyl chloride in an inert solvent such as dichloromethane or toluene.
- the benzoyl chloride is subsequently coupled with an amine of formula H ⁇ R 2 R 3 or H ⁇ R 1 J in an inert solvent such as tefrahydrofuran or dichloromethane.
- An additional base such as tertiary amines, pyridine or polymer-bound bases may be used to neutralize the hydrochloric acid produced in the reaction.
- Step C Preparation of 3-iodo-N-(2.2.2-trifluoroethoxy)pyridin-5-yl phmalimide
- Step D Preparation of 3-Iodo-N - ⁇ -methyletfaylVN -[6-r2.2.2-trifluoroethoxyV3- pyrid yl]-!.2-benzenedicarboxamide and ⁇ -Iodo-N ⁇ -fl-me ylethylVN - ⁇ - (2.2.2-trifluoroethoxy)-3-pyridinyl]- 1.2-benzenedicarboxamide
- 3-iodo-N-(2,2,2-trifluoroethoxy)pyridin-5-yl phthalimide 0.5 g, 1.1 mmol
- isopropylamine 1.5 g, 25 mmol
- Step C Preparation of l-(2-chlorophenylV3-ftrifluoromethylVlH-pyra7:n1-5-arr ⁇ ine
- thionyl chloride (1.26 mL, 17.2 mmol, 5.0 equivalents)
- N,N-dimethylformamide 2 drops
- Step D Preparation of 2- [ 1 -( 2-ChlorophenylV 3 -ftrifluoromethyl)- lH-pyrazol-5-y 1] -4- iodo- lH-isoindole- 1.3(2H)-dione
- Step E Preparation of N 2 -[ 1 -(2-Chlorophenyl)-3- trifluoromethyl)- lH-pyrazol-5-yl]-
- the foUowing compounds of Tables 1 to 25 can be prepared.
- the foUowing abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, / ' -Pr is isopropyl, t-Bu is tertiary butyl, Ph is phenyl and C ⁇ is cyano.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Compounds of (I), and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling invertebrate pests (Formula) wherein J is selected from the group consisting of J-1, J-2, J-3, J-4, J-5, J-6, J-7 and J-8 (I) and R1, R2, R3, R4, R5, R7, R9 and n are as defined in the disclosure.Also disclosed are compositions for controlling an invertebrate pest comprising a biologically effective amount of a compound of (I) and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of (I) (e.g., as a composition described herein).
Description
SUBSTITUTED HETEROCYCLIC PHTHALIC ACID DIAMIDE ARTHROPODICIDES
BACKGROUND OF THE INVENTION This invention relates to certain heterocyclic phthalic acid diamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.
The control of invetebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action. EP919542 discloses phthalic acid diamides of Formula i as insecticides
wherein, inter alia,
Z1 and Z2 are O or S; and
R1, R2 and R3 are, among others, H, alkyl or substituted alkyl. WOO 1/02354 discloses phthalic acid diamides of Formula ii as insecticides
wherein, inter alia,
Q is an optionally substituted hetero cycle containing O, S or ; Z1 and Z2 are O or S; and R1, R2 and R3 are, among others, H, alkyl or substituted alkyl.
SUMMARY OF THE INVENTION
This invention pertains to compounds of Formula I and N-oxides and agriculturally suitable salts thereof
wherein
J is selected from the group consisting of J-l, J-2, J-3, J-4, J-5, J-6, J-7 and J-8
R1 is H, Ci-C6 alkyl, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
R2 is H or Cι-C6 alkyl;
R3 is H; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C8 cycloalkylalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkyl, C!-C4 alkoxy, C1-C4 haloalkoxy, C]-C4 alkylthio, C1-C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C^-C^ alkoxycarbonyl or C2-Cg alkylcarbonyl; one R4 group is attached to the phenyl ring at the 3-position or 6-position, and said R4 is CrC4 alkyl, CrC4 haloalkyl, halogen, CN, NO2, C!-C4 alkoxy, CrC4
haloalkoxy, -C4 alkylthio, -C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, or C1-C4 haloalkylsulfonyl; and an optional second R4 is H, C]_-C6 alkyl, C2-Cg alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C^-Cg haloalkyl, C2-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy,
C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C1-C4 alkoxyalkyl, C1-C4 hydroxyalkyl, C(O)R10, CO2R10, C^ RiORll, NR^RH, NCR^COR10, N(R )CO2R10 or C3-C6 trialkylsilyl;
R5 is H, Ci-C4 alkyl, CrC4 haloalkyl, or
Y is N, CH, CF, CC1, CBr or Cl; each R6 and R7 is independently H, C^-Cg alkyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, halogen, CN, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 haloalkylthio;
R9 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl or C3-C6 haloalkynyl; provided R7 and R9 are not both H; R10 is H or Cr-C- alkyl or C1-C haloalkyl; R11 is H or -C4 alkyl; and n is 1 or 2.
This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention also pertains to a composition comprising a biologically effective amount of a compound of Formula I and an effective amount of at least one additional biologically active compound or agent.
This invention also pertains to a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I (e.g., as a composition described herein). This invention also relates to such method wherein the invertebrate pest or its environment is contacted with a biologically effective amount of a compound of Formula I or a composition comprising a compound of Formula I and a biologically effective amount of at least one additional compound or agent for controlling invertebrate pests.
DETAILS OF THE INVENTION
In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as methyl, ethyl, /.-propyl, t'-propyl, or the different butyl, pentyl or hexyl isomers. "Alkenyl" can include straight-chain or branched alkenes such as 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl andhexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyi" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyi" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. "Cycloalkylalkyi" indicates an alkyl group substituted with a cycloalky group and includes, for example, cyclopropylmethyl, cyclobutylethyl, cyclopentylpropyl and cyclohexylmethyl. The term "heteroaromatic ring" denotes fully aromatic rings in which at least one ring atom is not carbon and can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heteroaromatic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the Hϋckel rule is satisfied). The heteroaromatic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, CICH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC≡CCHCl, CF3C≡C, CC13C≡C and FCH2C≡CCH2. Examples of "haloalkoxy" include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O.
The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 6. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyi designates CH3OCH2; C3 alkoxyalkyi designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyi designates the various isomers of an alkyl group substituted with an
alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula I contains a heteroaromatic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a group contains a substituent which can be hydrogen, for example R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds ofthe invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
The present invention comprises of compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPB A), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene Advances in Heterocyclic Chemistry, vol.43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in A dvances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Pres s .
The salts ofthe compounds ofthe invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric,
acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, saHcylic, tartaric, 4-toluenesulfonic or valeric acids.
Of note are compounds of Formula I wherein R5 is rVMrV
The wavy line represents the rema σinder of the J group to which said R5 moiety is attached.
Preferred compounds for reasons of better activity, cost and/or ease of synthesis are: Preferred 1. Compounds of Formula I wherein V is N. Preferred 2. Compounds of Formula I wherein V is CH, CF, CC1 or CBr. Preferred 3. Compounds of Preferred 1 or Preferred 2 wherein
R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH ; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3;
R6 is CrC4 alkyl, C1-C4 haloalkyl, halogen or CN; R7 is H, CH3, CF3, OCHF2 or halogen; and p is 0, 1 or 2. Preferred 4. Compounds of Preferred 3 wherein J is J-l;
R3 is C1-C4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is
CH3, Cl, Br orI; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and
R7 is halogen or CF3. Preferred 5. Compounds of Preferred 4 wherein V is N;
R3 is methyl, ethyl, isopropyl or tertiary butyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is
CH3 or I; R6 is Cl or Br; and R7 is Br, Cl or CF3. Preferred 6. Compounds of Preferred 3 wherein
J is J-2;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, CL Br or l; a second R4 is H, F, Cl, Br, I or CF3;
R6 is Cl or Br; and
R9 is CF3, CHF2, CH2CF3, CF2CHF2. Preferred 7. Compounds of Preferred 3 wherein J is J-3; R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is
CH3, CL Br orl; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and R7 is halogen or CF3.
Preferred 8. Compounds of Preferred 3 wherein J is J-4;
R3 is C!-C4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, CL Br orl; a second R4 is H, F, Cl, Br, I or CF ; R6 is Cl or Br; and R7 is CF3. Preferred 9. Compounds of Preferred 3 wherein J is J-5;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is
CH3, CL Br or l; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and
R9 is CF3, CHF2, CH2CF3, CF2CHF2. Preferred 10. Compounds of Preferred 3 wherein J is J-6;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is
CH3, CL Br orl; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and
R7 is halogen or CF3. Preferred 11. Compounds of Preferred 3 wherein J is J-7;
R3 is CrC4 alkyl; one R4 group is attached to the K-ring at the 2-position and said R4 is CH3, Cl or Br; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; R7 is H, halogen or CF3.and R9 is H, CF3, CHF2, CH2CF3, CF2CHF2.
Preferred 12. Compounds of Preferred 3 wherein J is J-8;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, CL Brorl; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; R7 is H, halogen or CF3.and R9 is H, CF3, CHF2, CH2CF3, CF2CHF2. Specifically preferred are compounds selected from the group consisting of:
N!-[ 1 -(3-chloro-2-pvridinyl)-3-(trifluoromethyl)- lH-pyrazol-5-y l]-3-methyl-N2-( 1 - methylethyl)- 1 ,2-benzenedicarboxamide,
N -[ 1 -(3-bromo- 1 -(3-chloro-2-pyridinyl)- lH-pyrazol-5-y l]-3-methyl-N2-( 1 - methylethyl)- 1 ,2-benzenedicarboxamide, N/-[l-(3-chloro-2-pvridmyl)-3-( fluoromethyl)-lH-ρyrazol-5-yl]-3-iodo-N2-(l- methylethyl)- 1 ,2-benzenedicarboxamide, and
Ni-[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-iodo-N2-(l- methylethyl)-l ,2-benzenedicarboxamide. The preferred compositions ofthe present invention are those that comprise the above preferred compounds.
The preferred methods of use are those involving the above preferred compounds. Of note are compounds of Formula Id and N-oxides and agriculturally suitable salts thereof
Id
wherein
J is selected from the group consisting of
J-59 J-60 J-61 J-62
R1 is H, C^-Cg alkyl, C2-C6 alkoxycarbonyl or C2-Cg alkylcarbonyl;
R2 is H or CrC6 alkyl;
R3 is H; Cj-Cg alkyl, C -C6 alkenyl, C2-Cg alkynyl, or C3-C6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkyl, -C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, -C4 alkylsulfmyl, C1-C4 alkylsulfonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylcarbonyl, C3-C6 trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of Cj -C alkyl, C2-C4 alkenyl, C2-C alkynyl, C3-C5 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloallcylamino, C -Cg (alJ-yl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylamino carbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; C^ alkoxy; Cι~C alkylamino; C2-C3 cUalkylamino; C3- C6 cycloalkylamino; C2-C6 alkoxycarbonyl or C2-Cg alkylcarbonyl;
eachR4 is independently H, Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3-C6 cycloalkyl, C^-Cg haloalkyl, C1-C4 alkoxyalkyi, CN, halogen, C1-C4 alkoxy, C!-C4 haloalkoxy, S(O)nR12, C^ hydroxyalkyl, C(O)R10, CHO, CO2R10, C(O)NR1θR11, NO2, NRlORll or N(Ru)CO2R10; each R6 is independently Cj-Cg alkyl, Cj-Cg haloalkyl, halogen, CN, C1-C4 alkoxy,
C1-C4 haloalkoxy or C1-C4 haloalkylthio; R7 is C1-C4 alkyl, C2-C alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, -C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, Cy C4 alkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, C -Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3- Cg trialkylsilyl; R8 is H, C^-Cg alkyl, C €6 haloalkyl, halogen, C1-C4 alkoxy or C1-C4 haloalkoxy; R9 is C2-C6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl or C3-C6 haloalkynyl; R10 is H or -C4 alkyl or C!-C4 haloalkyl; R11 is H OT C!-C4 alkyl; R12 is C!-C4 alkyl or Ci-C haloalkyl; n is 0, 1 or 2; and
X is , CH, CF, CCl or CBr. Of particular note are selected compounds of Formulald: Selection A. Compounds of Formulal d wherein X is N. Selection B. Compounds of Formulald wherein X is CH, CF, CC1 or CBr. Selection C. The compounds of Selection A or Selection B wherein
J is J-59;
R1, R2 andR8 are all H;
R3 is Cι-C4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH3; one R4 is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3 ;
R6 is CH3, CF3 or halogen; and ' p is 0, 1 or 2. Selection D. Compounds of Selection C wherein R3 is CrC4 alkyl; one R4 is CH3, Cl orBr; a second R4 is H, F, Cl, Br, I or CF ; R6 is CF3; and R7 is Cl or Br.
Selection E. The compounds of Selection A or Selection B wherein
J is J-60;
R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH3; one R4 is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3 ;
R9 is C2-Cg alkyl or Cj-Cg haloalkyl; and p is 0, lor 2. Selection F. Compounds of Selection E wherein R3 is CrC4 alkyl; one R4 is CH3, Cl orBr; a second R4 is H, F, Cl, Br, I or CF3;
R9 is CF3, CHF2, CH2CF3, CF2CHF2; and
R7 is Cl or Br. Selection G. The compounds of Selection A or Selection B wherein
J is J-61;
R1, R andR8 are all H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH3; one R4 is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3;
R6 is CH3, CF3 or halogen; and p is 0, 1 or 2. Selection H. Compounds of Selection G wherein
R3 is CrC4 alkyl; one R4 is CH3, Cl orBr; a second R4 is H, F, Cl, Br, I or CF3;
R6 is CF3; and
R7 is Cl or Br. Selection I. The compounds of Selection A or Selection B wherein J is J-62;
R1, R2 and R8 are all H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH ; one R4 is CH3, CF3, OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3; R6 is CH3, CF3 or halogen; and p is 0, 1 or 2. Selection J. Compounds of Selection I wherein
R3 is CrC4 alkyl;
one R4 is CH3, Cl or Br; a second R4 is H, F, Cl, Br, I or CF3; R6 is CF3; and R7 is Cl or Br. Also of note are compositions comprising a biologically effective amount of a compound of Formula Id and at least one additional component selected from the group consisting of surfactants, solid diluents and Hquid diluents. Also of note are said compositions further comprising at least one additional biologically active compound or agent. Selected compositions are those comprising the selected compounds above. Also of note is a method for controlling lepidopteran, homopteran and coleopteran insects comprising contacting the insects or their environment with a biologically effective amount of a compound of Formula Id, its N-oxide or an agriculturally suitable salt thereof. Selected methods are those comprising the selected compounds above.
The compounds of Formula I can be prepared by one or more of the following methods and variations described in Schemes 1 and 2. The definitions of J, R1, R2, R3, R4 and n in the compounds of Formulae 1-9 are as defined above in the Summary ofthe Invention.
Phthalic acid diamides of formula lb and Ic can be made by the method described in Scheme 1. Heating a phthalic anhydride of formula 2 with an aminoheterocycle of Formula H2Ν-J in an inert solvent such as glacial acetic acid affords a phthalimide of Formula 3. Ring-opening of phthalimide 3 with an amine ofthe Formula HNR2R3 in an inert solvent such as dioxane or tetrahydrofuran at room temperture or heating at reflux gives a phthalic acid diamide of formula lb. Alkylation of a compound of formula lb with a suitable alkylating agent (e.g. an alkyl halide or an alkyl methane- or 4-toluene-sulfonate) or acylating agent (e.g. an alkylchloroformate or acid chloride) in the presence of a base such as sodium hydride or H-butyl lithium in an inert solvent such as tefrahydrofuran or
N,N-dimethylformamide affords a phthaHc acid diamide of formula Ic wherein R1 is a substituent other than hydrogen. PhthaHc anhydrides of Formula 2 can be made by methods taught in/. Org. Chem., 1987, 52, 129, J. Am. Chem. Soc, 1929, 51, 1865, and/. Am. Chem. Soc, 1941, 63, 1542. Aminoheterocycles of formula H2Ν-J can be made by methods as described in Rodd's Chemistry of Organic Compounds: HeterocycHc Compounds, volume IN, parts C, F and IJ (1989), Comprehensive Heterocyclic Chemistry, volumes 2, 3,4,5 and 6 (1984) and Comprehensive Heterocyclic Chemistry II, volumes 3, 4, 5 and 6 (1996).
Scheme 1
lb Ic
Another method for making compounds of Formula I is summarized in Scheme 2. Lithiation of a benzamide of Formula 4 with «-butyl lithium in an inert solvent such as tefrahydrofuran followed by reaction with a carbamoyl chloride of Formula 5 provides a phthalic acid diamide of Formula I wherein R1 is other than hydrogen. Reaction of a benzamide of Formula 4 with «-butyl lithium in an inert solvent such as tefrahyclrofuran foHowed by reaction with an isocyanate of Formula 6 provides a phthaHc acid diamide of Formula I wherein R1 is hydrogen. Alternatively, Hthiation of a benzamide of Formula 7 with w-butyl lithium in an inert solvent such as tefrahydrofuran foUowed by reaction with a carbamoyl chloride chloride of Formula 8 provides a phthalic acid diamide of Formula I wherein R2 is other than hydrogen. Reaction of a benzamide of Formula 7 with n-butyl lithium in an inert solvent such as tefrahydrofuran followed by reaction with an isocyanate of Formula 9 provides a phthalic acid diamide of Formula 1 wherein R2 is hydrogen.
Benzamides of Formulae 4 and 7 are readily made from the corresponding benzoic acids via a benzoyl chloride intermediate or by direct coupling of a benzoic acid and amine in the presence of a suitable acid/amine coupling agent such as 1,3- cHcyclohexylcarbodiimide or 1,1 '-carbonyldiimidazole in an inert solvent such as dichloromethane or N,N-&methylformamide. Benzoic acids are readily converted to the acid chlorides on treatment with thionyl chloride or oxalyl chloride in an inert solvent such as dichloromethane or toluene. The benzoyl chloride is subsequently coupled with an amine of formula HΝR2 R3 or HΝ R1 J in an inert solvent such as tefrahydrofuran or
dichloromethane. An additional base such as tertiary amines, pyridine or polymer-bound bases may be used to neutralize the hydrochloric acid produced in the reaction.
Scheme 2
or or 0=C=N— R3 0=C=N — J
It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionaHties present in the intermediates. In these instances, the incorporation of protection and deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice ofthe protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I.
One skilled in the art will also recognize that compounds of Formula I and the intermediates described herein can be subjected to various electtophilic, nucleophiHc, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The foUowing Examples are, therefore, to be construed as merely illustrative and not limiting ofthe disclosure in any
way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. ^H NMR spectra are reported in ppm downfield from tetramethylsilane; s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets, dt is doublet of triplets, br s is broad singlet.
EXAMPLE 1 Step A: Preparation of 5-Nifro-2-(2.2.2-trifluoroethoxy)pyridine
To a solution of 2,2,2-trifluoroethanol (5 g, 50 mmol) stirring in 50 mL of tetrahydrofuran, sodium hydride (2 g of ca. 60% oil dispersion, ca. 50 mmol) was added portionwise with foaming and an exotherm. After formation of a solution and stirring at room temperature, 2-chloro-5-nitropyridine (5 g, 32 mmol) was added portionwise, accompanied by an exotherm. After stirring at room temperature overnight, the reaction mixture was partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of solvent in vacuo gave an orange oil. A solid was crystaLHzed from hexanes, filtered and dried to give 5 g of 5-nitro-2-(2,2,2-trifluoroemoxy)pyridine (used directly in the next step). 1HNMR (CDC13): 9.07 (s, IH), 8.45 (d, IH), 7.01 (d, IH), 4.9 (q, 2H) ppm. Step B: Preparation of 5-Ammo-2-(2.2.2-trifluoroethoxy)pyridine
To a solution of 5 g of 5-nifro-2-(2,2,2-trifluoroethoxy)pyridine in 75 mL of ethyl acetate, 0.5 g of 10% paUadium on carbon was added under nitrogen and the mixture was aUowed to shake on a paar hydrogenator under hydrogen at 3.1 X 105 Pa for 4 hours at room temperature. The reaction mixture was filtered through ceHte and the ceHte washed thoroughly with ethyl acetate. Evaporation of solvent in vacuo gave a dark oil. A soHd was triturated from hexane, filtered and dried to afford 3.3 g of 5-amino-2-(2,2,2- trifluoroethoxy)pyridine, isolated as a crude dark solid.
1H NMR (CDCfe): 7.60 (s, IH), 7.05 (d, IH), 6.70 (d, IH), 4.65 (q, 2H) 3.44 (br s, NH2) ppm.
Step C: Preparation of 3-iodo-N-(2.2.2-trifluoroethoxy)pyridin-5-yl phmalimide
A stirred solution of 3-iodophthaHc anhydride (1.3g, 4J mmol) and 5-amino-2-(2,2,2- trifluoroemoxy)pyridine (l.lg, 5.7 mmol) stirring in 15 mL of glacial acetic acid was heated at reflux for 3 hrs. The solvent was removed in vacuo and the remaining residue partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with aqueous sodium bicarbonate and brine and dried over magnesium sulfate. Evaporation of solvent in vacuo gave a solid residue which was suspended in hexanes and filtered to afford 2 g of 3-iodo-N-(2,2,2-trifluoroethoxy)pyridin-5-yl phtnalimide, isolated as a crude solid and used directly in the next step.
1H ΝMR (CDC13): 8.3 (s, IH), 8.2 (d, IH), 7.95 (d, IH), 7.75 (d, IH) 7.5 (t, IH), 7.01 (d, lH), 4.8 (q, 2H) ppm.
Step D: Preparation of 3-Iodo-N -α -methyletfaylVN -[6-r2.2.2-trifluoroethoxyV3- pyrid yl]-!.2-benzenedicarboxamide and ό-Iodo-N^-fl-me ylethylVN -^- (2.2.2-trifluoroethoxy)-3-pyridinyl]- 1.2-benzenedicarboxamide To a stirred solution of 3-iodo-N-(2,2,2-trifluoroethoxy)pyridin-5-yl phthalimide (0.5 g, 1.1 mmol) in 10 mL of 1 ,4-dioxane, isopropylamine (1.5 g, 25 mmol) was added and the reaction solution heated near reflux overnight. The reaction mixture was partitioned between 100 mL of ethyl acetate and 75 mL of water. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. Evaporation of solvent in vacuo gave a soHd residue which was chromatograghed on siHca gel to afford 27 mg of 3-iodo-N2-(l -methylethyl)-N -[6-(2,2,2-trifluoroethoxy)-3-ρvridinyl]- 1 ,2- benzenedicarboxamide [ p: 220-225 °C; iHΝMR φMSO-Dg): δ 10.25 (s, IH), 8.46 (s, IH), 8.2 (d, IH), 8.05 (d, IH), 8.0 (d, IH), 7.65 (d, IH), 7.25 (t, IH), 7.0 (d, IH), 4.96 (q, 2H), 3.95 (m, IH), 1.07 (d, 6H)] and 25 mg of 6-iodo-N2-(l-methylethyl)-N^-[6-(2,2,2- trifluoroethoxy)-3 -pyridinyl]- 1, 2-benzenedicarboxamide [mp: 200-203 °C; ΪHΝMR (DMSO-D6): δ 8.8 (s, IH), 8.4 (s, IH), 8.05 (d, IH), 7.85 (d, IH), 7.35 (d, IH), 7.05 (t, IH), 6.85 (d, IH), 6.35 (d, IH), 4J5 (q, 2H), 4.1 (m, IH), 1.1 (d, 6H)].
EXAMPLE 2 Step A: Preparation of l-(2-Chlorophenyl)-5-(2-furanyl)-3-(trifluoromethyl)-lH- pyrazole To a solution containing 4,4,4-triπuoro-l-(2-furyl)-l,3- butanedione (30.0 g, 146 mmol) in glacial acetic acid (65 mL) was added sodium acetate (12.1 g, 148 mmol). The mixture was cooled to about 25 °C, 2-chlorophenylhydrazine hydrochloride (25.6 g, 145 mmol) was added portionwise and, foΗowing a mild exotherm, the mixture was heated to 60 °C for 4 h, then cooled to 25 °C. The mixture was diluted with dichloromethane (400 mL) and the organic phase was washed with water (3x250 mL), saturated aqueous sodium carbonate (2x250 mL) and brine, then dried over magnesium sulfate and evaporated under reduced pressure to yield 43.2 g ofthe title compound as a brown oil. 1HΝMR (CDC13): δ 7.6 (m,5Η), 6.9 (IH), 5.7 (d, IH). Ste B: Preparation of l-(2-ChlorophenylV3-rtrifluoromethyl)-lH-pyrazole-5- carboxylic acid
To a suspension containing the title compound of Step A (43.2 g, 138 mmol) in acetonitrile (415 mL) was added sodium dihydrogenphosphate monohydrate (92.4 g, 669 mmol) over about 0.25 h. After stirring at room temperature for 0.5 h, the mixture was cooled to about 5 °C and a solution containing sodium chlorite (181 J g, 2.0 mmol) in 430 mL of water was added dropwise over 1 h while keeping the reaction temperature at less than 10 °C. [ Note: an aqueous sodium hydroxide scrubber was attached to scrub an evolving yeUow off-gas.] Following completion of addition the suspension was stirred at 5 °C for about 1 h, at 25 °C overnight, then acidified to pΗ = 1 by dropwise addition of
concentrated hydrochloric acid (150 mL), then extracted with ethyl acetate (1x500 mL, then 2x250 mL). The combined ethyl acetate extracts were added dropwise to an aqueous sodium metasufite solution (228.5 g in 1.05 L water) at a reaction temperature of less than 20 °C. The suspension was partitioned and the aqueous layer extracted with ethyl acetate (2x100 mL). The organic layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with hexane:diethyl ethert (99:1, 100 mL) to yield 32.9 g ofthe title compound as a soHd. 1HNMR (DMSO-D6): δ 13.9 (bs,lH), 7J(m,5H).
Step C: Preparation of l-(2-chlorophenylV3-ftrifluoromethylVlH-pyra7:n1-5-arrιine To a solution ofthe title compound of Step B (1.0 g, 3.44 mmol, 1.0 equivalent) in chloroform (20 mL), in a 50 mL round bottom flask was added thionyl chloride (1.26 mL, 17.2 mmol, 5.0 equivalents) and anhydrous N,N-dimethylformamide (2 drops). The resulting mixture was refluxed for 18 hours under a nitrogen atmosphere. After 18 hours the reaction was shown to be complete from an aliquot (0.5 mL) that was added to methanol (2 mL) and potassium carbonate and shaken for 5 minutes. No carboxyHc acid was detected from the aΗquot and only the methyl ester derivative was present (thin-layer chromatography (TLC) analysis R = 0.75, 1:1 ethyl acetate.-hexanes). The mixture was then concentrated under reduced pressure and dried in vacuo for 4 hours. The resulting pale yeUow oil was diluted with chloroform (30 mL) and transferred to a 100 mL round bottom flask. To the flask was added tefrabutylammonium bromide (3.0 mg, 0.01 mmol, 0.003 equivalents) at 0 °C foUowed by a solution of sodium azide (0.9 g, 13.8 mmol, 4.0 equiv) in water (5 mL). The mixture was stirred vigorously for 2 hours, after which the organic layer was separated and washed with water (2 x 20 mL), brine (20 mL), dried (Na2SO4), and filtered into a 100 mL round bottom flask. To the flask was added trifluoroacetic acid (0.69 mL, 8.94 mmol, 2.6 equivalents) and the mixture was stirred at reflux for 42 hours. To monitor the reaction, an aliquot (0.5 mL) was added to chloroform (1 mL) and washed with saturated sodium bicarbonate (2 mL). By TLC analysis after 6 h, both the acyl azide (R/ = 0.90, 2:1 ethyl acetate-.hexanes) and product (R/ = 0.45, 2:1 ethyl acetate-.hexanes) were present. The mixture was then allowed to cool, washed with saturated sodium bicarbonate (2 x 15 mL), dried (Na2SO4), and concentrated under reduced pressure. Column chromatography (2:1 ethyl acetate:hexanes) provided 0.68 g ofthe title compound as a pale yellow soΗd in an overaU yield of 76 %. The 1H NMR spectrum was consistant with the structure. ΗNMR (CDC13): δ 7.52-7.35 (4Η, m), 6.96 (IH, br), 6.60 (IH, s).
Step D: Preparation of 2- [ 1 -( 2-ChlorophenylV 3 -ftrifluoromethyl)- lH-pyrazol-5-y 1] -4- iodo- lH-isoindole- 1.3(2H)-dione
To a solution ofthe title compound of Step C (1J g, 6.51 mmol, 1.0 equivalent) in glacial acetic acid (9 mL) in a 75 mL sealed tube reaction vessel was added 3-iodophthaΗc anhydride (1.78 g, 6.51 mmol, 1.0 equivalent). The reaction vessel was sealed and heated at
130 °C for 6h, then allowed to cool to room temperature. The mixture was transferred to a 250 mL separatory funnel and water was added (50 mL), upon which a white precipitate formed. The product was extracted with ether (2 x 50 mL), and the combined extracts were washed with water (3 x 50 mL), brine (50 mL), dried a2SO4), and concentrated under reduced pressure to yield 2.46 g ofthe title compound as a white solid. This material was used in the next step without purification.
Step E: Preparation of N2-[ 1 -(2-Chlorophenyl)-3- trifluoromethyl)- lH-pyrazol-5-yl]-
3-iodo-N^-(l-methylethylVl .2-benzenedicarboxamide and N^-[l-(2- CMorophenyl)-3-(^trifluoromethyl)-lH-pyrazol-5-yl]-3-iodo-N -(l- methylethyl)- 1.2-benzenedicarboxamide
To the neat crude material from Step D (110 mg) in a 1.2 mL glass vial was added isopropyl amine (0.5 mL). After 2 minutes the reaction was complete by TLC. The isopropyl amine was removed to give a crude oil which was purified by preparative TLC (1:2 ethyl acetate-.hexanes) to afford 24 mg of N2-[l-(2-Chlorophenyl)-3-(trifluoromethyl)- lH-pyrazol-5-yl]-3-iodo-N -(l-methylethyl)-l,2-benzenedicarboxamide (yield 18%) (mp 234-235 °C); TLC analysis R/ = 0.32, (1:1 ethyl acetate :hexanes); 1HΝMR (CDC13): δ 7.88 (1Η, d), 7.66 (1Η, br), 7.57-7.52 (2Η, m), 7.50-7.43 (3H, m), 7.16-7.11 (2H, m), 5.98 (IH, bd), 4.10 (IH, m), 1.17 (6H, d); and 37 mg of N?-[l-(2-Chlorophenyl)-3-(trifluoromethyl)- lH-pyrazol-5-yl]-3-iodo-N2-(l-memylethyl)-l,2-benzenedicarboxamide (yield 29%); (mp 226-228 °C); TLC analysis R = 0.58, (1 : 1 ethyl acetate:hexanes) 1H ΝMR (CDC13): δ 8.94 (1Η, s), 7.93 (1Η, d), 7.78 (1Η, d), 7.63-7.47 (4Η, m), 7.17 (IH, t), 7.12 (IH, s), 6.63 (IH, bd), 4.07 (IH, m), 1.18 (6H, d).
By the procedures described herein together with methods known in the art, the foUowing compounds of Tables 1 to 25 can be prepared. The foUowing abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, /'-Pr is isopropyl, t-Bu is tertiary butyl, Ph is phenyl and CΝ is cyano.
Table 1
R4a R4° R7 R3 R6 R4a R4b R7 R3 ≠ R4a R4b R7 R3 R6
CH3 F CF3 Me Cl Cl F CF3 Me Cl Br F CF3 Me Cl
CH3 F CF3 Et Cl Cl F CF3 Et Cl Br F CF3 Et Cl
CH3 F CF3 i-Pr Cl Cl F CF3 i-Pr Cl Br F CF3 i-Pr Cl
CH3 F CF3 t-Bu Cl Cl F CF3 t-Bu Cl Br F CF3 t-Bu Cl
CH3 F CF3 Me Br Cl F CF3 Me Br Br F CF3 Me Br
CH3 F CF3 Et Br Cl F CF3 Et Br Br F CF3 Et Br
CH3 F CF3 i-Pr Br Cl F CF3 i-Pr Br Br F CF3 i-Pr Br
CH3 F CF3 t-Bu Br Cl F CF3 t-Bu Br Br F CF3 t-Bu Br
CH3 F Cl Me Cl Cl F Cl Me Cl Br F Cl Me Cl
CH3 F Cl Et Cl Cl F Cl Et Cl Br F Cl Et Cl
CH3 F Cl i-Pr Cl Cl F Cl i-Pr Cl Br F Cl i-Pr Cl
CH3 F Cl t-Bu Cl Cl F Cl t-Bu Cl Br F Cl t-Bu Cl
CH3 F Cl Me Br Cl F Cl Me Br Br F Cl Me Br
CH3 F Cl Et Br Cl F Cl Et Br Br F Cl Et Br
CH3 F Cl i-Pr Br Cl F Cl i-Pr Br Br F Cl i-Pr Br
CH3 F Cl t-Bu Br Cl F Cl t-Bu Br Br F Cl t-Bu Br
CH3 F Br Me Cl Cl F Br Me Cl Br F Br Me Cl
CH3 F Br Et Cl Cl F Br Et Cl Br F Br Et Cl
CH3 F Br i-Pr Cl Cl F Br i-Pr Cl Br F Br i-Pr Cl
CH3 F Br t-Bu Cl Cl F Br t-Bu Cl Br F Br t-Bu Cl
CH3 F Br Me Br Cl F Br Me Br Br F Br Me Br
CH3 F Br Et Br Cl F Br Et Br Br F Br Et Br
CH3 F Br i-Pr Br Cl F Br i-Pr Br Br F Br i-Pr Br
CH3 F Br t-Bu Br Cl F Br t-Bu Br Br F Br t-Bu Br
CH3 Cl CF3 Me Cl Cl Cl CF3 Me Cl Br Cl CF3 Me Cl
R4a R4b R7 R3 Rθ R4a R4b R7 R3 R6 R4a R4b R7 R3 R6
CH3 Cl CF3 • Et Cl Cl Cl CF Et Cl Br Cl CF3 Et Cl
CH3 01 CF3 i-Pr Cl Cl Cl CF3 i-Pr Cl Br Cl CF3 i-Pr Cl
CH3 01 CF3 t-Bu Cl 01 Cl CF3 t-Bu Cl Br Cl CF3 t-Bu Cl
CH3 Cl CF3 Me Br 01 Cl CF3 Me Br Br Cl CF3 Me Br
CH3 01 CF3 Et Br Cl Cl CF3 Et Br Br Cl CF3 Et Br
CH3 Cl CF3 i-Pr Br Cl Cl CF3 i-Pr Br Br Cl CF3 i-Pr Br
CH3 Cl CF3 t-Bu Br Cl Cl CF3 t-Bu Br Br Cl CF3 t-Bu Br
CH3 Cl Cl Me Cl Cl Cl Cl Me Cl Br Cl 01 Me Cl
CH3 Cl Cl Et Cl Cl Cl Cl Et Cl Br Cl 01 Et Cl
CH3 Cl Cl i-Pr Cl 01 Cl Cl i-Pr Cl Br Cl Cl i-Pr Cl
CH3 Cl Cl t-Bu 01 Cl Cl 01 t-Bu 01 Br 01 Cl t-Bu Cl
CH3 Cl Cl Me Br 01 Cl Cl Me Br Br 01 Cl Me Br
CH3 01 Cl Et Br Cl Cl Cl Et Br Br Cl Cl Et Br
CH3 Cl Cl i-Pr Br Cl Cl Cl i-Pr Br Br Cl Cl i-Pr Br
CH3 Cl Cl t-Bu Br Cl 01 Cl t-Bu Br Br 01 01 t-Bu Br
CH3 Cl Br Me Cl Cl Cl Br Me Cl Br 01 Br Me Cl
CH3 Cl Br Et 01 Cl Cl Br Et 01 Br 01 Br Et Cl
CH3 01 Br i-Pr Cl Cl Cl Br i-Pr Cl Br Cl Br i-Pr Cl
CH3 01 Br t-Bu 01 Cl Cl Br t-Bu Cl Br Cl Br t-Bu Cl
CH3 Cl Br Me Br 01 01 Br Me Br Br Cl Br Me Br
CH3 Cl Br Et Br Cl Cl Br Et Br Br Cl Br Et Br
CH3 Cl Br i-Pr Br Cl Cl Br i-Pr Br Br Cl Br i-Pr Br
CH3 Cl Br t-Bu Br Cl Cl Br t-Bu Br Br Cl Br t-Bu Br
CH3 Br CF3 Me Cl Cl Br CF3 Me Cl Br Br CF3 Me Cl
CH3 Br CF3 Et Cl Cl Br CF3 Et 01 Br Br CF3 Et Cl
CH3 Br CF3 i-Pr 01 Cl Br CF3 i-Pr Cl Br Br CF3 i-Pr 01
CH3 Br CF3 t-Bu 01 01 Br CF3 t-Bu Cl Br Br CF3 t-Bu Cl
CH3 Br CF3 Me Br Cl Br CF3 Me Br Br Br CF3 Me Br
CH3 Br CF3 Et Br Cl Br CF3 Et Br Br Br CF3 Et Br
CH3 Br CF3 i-Pr Br Cl Br CF3 i-Pr Br Br Br CF3 i-Pr Br
CH3 Br CF3 t-Bu Br 01 Br CF3 t-Bu Br Br Br CF3 t-Bu Br
CH3 Br Cl Me Cl Cl Br 01 Me Cl Br Br Cl Me Cl
CH3 Br Cl Et Cl Cl Br Cl Et Cl Br Br 01 Et Cl
CH3 Br Cl i-Pr Cl Cl Br Cl i-Pr Cl Br Br Cl i-Pr Cl
CH3 Br Cl t-Bu 01 Cl Br 01 t-Bu Cl Br Br Cl t-Bu Cl
CH3 Br Cl Me Br Cl H CF3 Me Cl Br Br Cl Me Br
CH3 Br Cl Et Br Cl H CF3 Et 01 Br Br Cl Et Br
i fi a co
& pq pq pq o 8 ed u Ul Ul
PQ PQ pq S pq pq pq pq pq pq pq PQ fi pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq pq
G G m m pq G G G G pq pq pq pq G G G G u pq pq pq pq pq pq a pq G G G G pq £ q Pq G G
Ul
CN ■* 8 8 8 8 8 8 u o υ u u ϋ O o o u pq pq pq pq pq pq fi pq G o G G U u q pq pq pq pq a pq pq e
% ffi ffi iff ffi w fi u
Hi f ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi u pq pq pq pq pq pq M pq pq pq pq pq
G G G G G G G G G G o U G G G G G G G G G G G G G G G G O G G G G G G G
G G ι-< U
P4 G G pq pq pq pq G G G G pq pq pq da G G G G pq pq pq pq G G G G pq pq pq pq G G
3 3 3 3 3 3
*& s a § 3 s s 3 3 i3 s 3 3 1 S 5 3 B * 5 a 5 3 55 3 a 3 a co
^ G G pq PQ pq pq pq O o 8 8 G 8 o o O Q o ϋ υ u u Ul pq pq pq pq pq pq pq pq 8
Ul Ul Ii U co tJ pq PQ & & q pq pq pq G G r~- co co co co
90 <I s 3 s s s s s s 3 3 3 3 ffi ffi D 8 3 3 3 3 3 3 ffi 3 3 3 3 3 3 3 ffi G 3 3 3 ffi ϋ" 3 3 o O
R4a R4b R7 R3 R6 R4a R4b R7 R3 R6 R4a R4b R7 R3 R6
CH CF3 CF3 t-Bu Cl Cl CF3 t-Bu Cl Br CF3 CF3 i-Bu Cl
CH3 CF3 CF Me Br Cl CF3 Me Br Br CF3 CF3 Me Br
CH3 CF3 CF3 Et Br Cl CF3 Et Br Br CF3 CF3 Et Br
CH3 CF3 CF3 i-Pr Br Cl CF3 i-Pr Br Br CF3 CF3 i-Pr Br
CH3 CF3 CF3 t-Bu Br Cl CF3 t-Bu Br Br CF3 CF3 t-Bu Br
CH3 CF3 01 Me Cl Cl Cl Me 01 Br CF3 Cl Me Cl
CH3 CF3 01 Et Cl Cl Cl Et Cl Br CF3 Cl Et 01
CH3 CF3 01 i-Pr Cl Cl Cl i-Pr Cl Br CF3 Cl i-Pr Cl
CH3 CF3 Cl t-Bu Cl Cl Cl t-Bu Cl Br CF3 Cl t-Bu 01
CH3 CF3 Cl Me Br Cl Cl Me Br Br CF3 Cl Me Br
CH3 CF3 Cl Et Br Cl Cl Et Br Br CF3 Cl Et Br
CH3 CF3 01 i-Pr Br Cl 01 i-Pr Br Br CF3 Cl i-Pr Br
CH3 CF3 Cl t-Bu Br Cl Cl t-Bu Br Br CF3 Cl t-Bu Br
CH3 CF3 Br Me Cl Cl Br Me Cl Br CF3 Br Me 01
CH3 CF3 Br Et Cl Cl Br Et Cl Br CF3 Br Et Cl
CH3 CF3 Br i-Pr Cl Cl Br i-Pr Cl Br CF3 Br i-Pr Cl
CH3 CF3 Br t-Bu Cl 01 Br t-Bu 01 Br CF3 Br t-Bu Cl
CH3 CF3 Br Me Br Cl Br Me Br Br CF3 Br Me Br
CH3 CF3 Br Et Br 01 Br Et Br Br CF3 Br Et Br
CH3 CF3 Br i-Pr Br 01 Br i-Pr Br Br CF3 Br i-Pr Br
CH3 CF3 Br t-Bu Br Cl Br t-Bu Br Br CF3 Br t-Bu Br
CH3 Cl Cl κ-Pr Cl Cl CF3 CF3 Me Cl I Cl CF3 Me 01
CH3 Cl 01 M-BU Cl Cl CF3 CF3 Et 01 I Cl CF3 Et Cl
CH3 Cl Cl s-Bu Cl Cl CF3 CF3 i-Pr Cl I Cl CF3 i-Pr Cl
CH3 Cl Cl i-Bu Cl Cl CF3 CF t-Bu Cl I 01 CF3 t-Bu Cl
CH3 H CF3 Me Cl Cl CF3 CF3 Me Br I Cl CF3 Me Br
CH3 H CF3 Et Cl Cl CF3 CF3 Et Br I 01 CF3 Et Br
CH3 H CF3 i-Pr Cl 01 CF3 CF3 i-Pr Br I Cl CF3 i-Pr Br
CH3 H CF3 t-Bu Cl 01 CF3 CF3 t-Bu Br I Cl CF3 t-Bu Br
CH3 H CF3 Me Br Cl CF3 Cl Me Cl I Cl 01 Me Cl
CH3 H CF3 Et Br Cl CF3 01 Et Cl I Cl 01 Et Cl
CH3 H CF3 i-Pr Br Cl CF3 01 i-Pr Cl I Cl Cl i-Pr 01
CH3 H CF3 t-Bu Br Cl CF3 Cl t-Bu Cl I Cl Cl t-Bu 01
CH3 H Cl Me Cl Cl CF3 Cl Me Br I 01 Cl Me Br
CH3 H Cl Et Cl Cl CF3 Cl Et Br I Cl Cl Et Br
CH3 H Cl i-Pr Cl Cl CF3 01 i-Pr Br I Cl Cl i-Pr Br
CH3 H Cl t-Bu Cl Cl CF3 Cl i-Bu Br I Cl Cl t-Bu Br
R4a R4b R7 R3 R6 R4a R4b R7 R3 R6 R4a R4b R7 R3 R6
CH3 H Cl Me Br Cl CF3 Br Me 01 I Cl Br Me Cl
CH3 H Cl Et Br Cl CF3 Br Et 01 I Cl Br Et Cl
CH3 H Cl i-Pr Br 01 CF3 Br i-Pr 01 I Cl Br i-Pr Cl
CH3 H Cl t-Bu Br Cl CF3 Br t-Bu 01 I Cl Br t-Bu Cl
CH3 H Br Me Cl Cl CF3 Br Me Br I Cl Br Me Br
CH3 H Br Et Cl Cl CF3 Br Et Br I Cl Br Et Br
CH3 H Br i-Pr Cl Cl CF3 Br i-Pr Br I Cl Br i-Pr Br
CH3 H Br t-Bu Cl Cl CF3 Br t-Bu Br I Cl Br t-Bu Br
CH3 H Br Me Br 01 01 01 «-Pr 01 I H CF3 Me Cl
CH3 H Br Et Br 01 Cl Cl «-Bu 01 I H CF3 Et Cl
CH3 H Br i-Pr Br Cl Cl Cl s-Bu Cl I H CF3 i-Pr Cl
CH3 H Br t-Bu Br 01 Cl 01 i-Bu Cl I H CF3 t-Bu Cl
Table 2
R3 R4a R4b R7 R6 R3 R4a R4° R7 R6
Et 3-Me H OCHF2 F Et 3-C1 H OCHF2 F i-Pr 3-Me H CF3 F i-Pr 3-C1 H CF3 F t-Bu 3-Me H C2F5 F t-Bu 3-C1 H C2F5 F propargyl 3-Me H C2F5 F propargyl 3-C1 H C2F5 F c-propyl 3-Me H CF3 F c-propyl 3-C1 H CF3 F i-Pr 3-Me H Me F i-Pr 3-C1 H Me F t-Bu 3-Me 5-Br CN F t-Bu 3-C1 5-Br CN F
Me 3-Me H CF3 Cl Me 3-01 H CF3 Cl
Et 3-Me 5-Me OCF3 Cl Et 3-C1 5-Me OCF3 Cl i-Pr 3-Me H OCF3 Cl i-Pr 3-C1 H OCF3 Cl t-Bu 3-Me 5-C1 Br Cl t-Bu 3-C1 5-Cl Br Cl
Me 3-Me H Br Cl Me 3-C1 H Br Cl
Et 3-Me H Cl Cl Et 3-01 H Cl Cl i-Pr 3-Me 5-Br Cl Cl i-Pr 3-01 5-Br 01 Cl t-Bu 3-Me H I Cl t-Bu 3-C1 H I Cl propargyl 3-Me H CF3 Cl propargyl 3-C1 H CF3 Cl c-propyl 3-Me H OCF3 Cl c-propyl 3-01 H OCF3 Cl i-Pr 3-Me 5-C1 CF3 Cl i-Pr 3-C1 5-Cl CF3 Cl t-Bu 3-Me H SCF3 Cl t-Bu 3-C1 H SCF3 Cl
Me 3-Me 5-C1 SCHF2 Cl Me 3-C1 5-Cl SCHF2 Cl
Et 3-Me H OCHF2 01 Et 3-C1 H OCHF2 Cl i-Pr 3-Me H CF3 Cl i-Pr 3-C1 H CF3 Cl i-Bu 3-Me H C F5 Cl i-Bu 3-C1 H C2F5 Cl propargyl 3-Me H C2F5 Cl propargyl 3-C1 H C2F5 01 c-propyl 3-Me H CF3 Cl c-propyl 3-C1 H CF3 Cl i-Pr 3-Me H Me Cl i-Pr 3-C1 H Me Cl t-Bu 3-Me 5-Br CN Cl t-Bu 3-C1 5-Br CN Cl
Me 3-Me H CF3 CF3 Me 3-C1 H CF3 CF3
Et 3-Me 5-Me OCF3 CF3 Et 3-C1 5-Me OCF3 CF3 i-Pr 3-Me H OCF3 CF3 i-Pr 3-C1 H OCF3 CF3 t-Bu 3-Me 5-Cl Br CF3 t-Bu 3-C1 5-Cl Br CF3
Me 3-Me H Br CF3 Me 3-C1 H Br CF3
Et 3-Me H 01 CF3 Et 3-C1 H 01 CF3 i-Pr 3-Me 5-Br 01 CF3 i-Pr 3-C1 5-Br Cl CF3 t-Bu 3-Me H I CF3 i-Bu 3-C1 H I CF3 propargyl 3-Me H CF3 CF3 propargyl 3-01 H CF3 CF3 c-propyl 3-Me H OCF3 CF3 c-propyl 3-01 H OCF3 CF3
0) O ^ ^ I O O O Ϊ <Ϊ 1) D 1) Λ ^ ^ ^ ^ ^ ^ ^ O O C^ O O 1)
Ul IΛ - ffi ffi ffi ffi ffi ffi ffi BP ffi ffi ffi ffi ffi ffi ό ffi ό ffi ffi ffi ώ ffi ffi t^ ffi ^ ffi tid ffi ffi ffi ffi ffi ffi ffi o 1%
TI J TI Tj TI H w 6 B W W W d Cd Cd td Cd dd W W W Cd Cd Cd Cd Cd rø 9 9 9 9 9 oτj o τι 9 .9 te to
I J
0 O^ Os C O
O n O O O O O O Q Q O O O Q Q Q Q O O O O O O O O O Q Q O O n O O O O O n p Ii P
ffi ^ ffi ffi ffl ffi ffi ^ ffi ffi & ffi ffi ffi ffi ffi ffi ,!-) ffi Q ft
CO CΛ CO O O O O Λ Λ O co Ω O O ,—, _
Ω Ω Q Ω Ω Ω Ω o s ΩΩ t? κ9 ΩΩ ΩΩ Ω o o Ω HH o o o O o o o Q O O - iu. _fl d n n G ijj J T3 TI ft o to to t to to to to to "*" υ. i-n to to
^ ^ ^ ^ l1 ^ )-d t3d ω ω rø ω rø w ω ω rø ω ω rø rø ω w rø rø w ω 9 9 9 9 9 9 9 9 9 9 s
CN r~- r~- k fc fc fc tn fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc O U o CJ o CJ o υ o u J o tN r- IN
<r> fc f c r- r- a c f fc fc fc fc fc co c
H fc CJ 8 & & U o 5 & 8 8 fc f
00 o o o o U 8c 8 8 CJ O O α CJ O α u α u ffi- f J 3 3 3 3 o u a a CJ a 3 CJ a CJ o O o α. o o o 3 O 3
t ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi a ffi tn a ffi ffi ffi ffi ffi ffl ffi ffi ffl ffl ffl
CJ O O o α O u o o o CJ c_> o J CJ o CJ J CJ o o CJ u J J CJ CJ CJ CJ CJ J CJ J J
Pi vά vό vό vό vό vά vό vά vά vό vό vό vά vό vό vά vά vά so vά vέ vό vό vό vά vό vό vά vό
3
5 1 a 3
5 3 a 3
5 3 a s 3 3 a s 3 3 1 a 3 3 3 3 a 5 3 a s 3 3 1 a s 3 a 5
CN
^ fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc G G G G G G υ G G G G
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi a ffi ffi iff ffi « a ffi ffi ffi ffi ffi ffl ffi ffi ffl ffl ffl
% a a
r~- fό
90 3 3 3 3 3 fc N 3 a 5 3 a 3 3 3 a o s 3 pq a s 3
3 1 a 5 a 5 3 a 5 pq a 5 pq a 5
O
i i 1 1 i 1 i t i i 1 1 1 1 ft P
ffi ffi ffi ffi in ffi « ffi ffi ffi a ffi ffi ffi ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi a ffi ffi ffi ffi ffl ffl a a ffl ffi ffi ffi β
9 9 9 9
rø ω Cd rø W Cd Cd ω rø rø Cd Cd rø &? Cd Cd Cd O o O o o o o o O O O O o o o o O π o o ft 1 to
Cd
3 5 cf 3 5 5! cf 3 « 5 ss cf 3 5 8 δ 3 5 5! cf δ 3 $ cf δ 3 5 f δ 3 5 8 cf δ I!* t-o
3 5 S f I
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffi ffi ffi ffi \
V a a a a o o o o co
O O o
Q o o o o o o o
9 9 O O o o to o
'TJ TJ -> 9- 9 9 9 9 9 TI TI J TJ TJ υ. > cn 9 9 9 9 ft to 1 to to to to to t 9 o*
§ § §
w ω ω BP ff ω rø ff rø W Bp 6? ω &? ω &? BP Q o Q o Q Ω Ω Q O O G Ω G Q o o Q O Q Ω ft
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ft c^ α> α> α> c^ cι> o cD θ c^ CD C^ Q ^ cD ^ ci) CD θ) Cϋ ι> c c^ ci) c^ c c^ I pa
K H)JM-_( Hμi-I MhlMH MJ-MH MHHM
MM MM MM MM MM ft
TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ Tf TJ TJ TJ TJ TI Ti Ti Ti TJ rø rø rø rø Cd rø rø rø rø w i-t w i-i i rø-t i rø-t rø i-l rø i-l I w ON t oo
rt CD g" i-f <-»■ ffi Sj hf ** ffi £" f-f <-*■ ffi rø r
3 2 rø ø ø rø
3 sp r
3 π ^ O g' t- ^ CD g* ι_ "- CD rt i " l ω
O O O O O O O O O Q O Q Q Q O O O O O O O O O Q Q Q Q O O O Q O O O O O ft
I P
TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø t-O OJ t- '- OJ J U) l-O OJ OJ - l- !-ό t- OJ J t-O OJ OJ OJ OJ ft
*-*.
5 δ 3 5 s cf δ 3 5 £ 1 δ 3 5 8 δ 3 5 3 cf δ 3 5 s 3 δ 5 £ cf δ 3 5 8 cf 3 δ 5 ω cf ω
3 * ft
ON ON ^ ON ON ON ON ON ON ON ON ON ON ON ON ON ON Os ON ON i * 1 i i 1 1 1 k 1 i i & 1 i i 1 i i ft 1 p.
n o o o O o O O o o O o O o o o o o o o o n o o o o O ffi ffl ffi ffl in ffi ffi ffl a ffi I fts
ft
TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ T TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ
O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J ft t
VO
5 8 δ ω
3 5 8 δ 3 5 5! 1 3 5 s 1 δ 3 5 3 cf δ 3 5 S? cf δ 3 5 CD 3 δ 5 cf δ 3 5 ω cf δ 3 5
ON ON ON ON 3 π π o ό o O O ό o a ό ό 6 π ό ό ό ό ό o O ό ό ό ό ό π ό ό o ό o r> π n
O o Ω Q o Q Ω Q Ω Q Q Q o Ω Ω o O Q Q Q O o Q Q Q O o ffi ffl ffl ffi ffi ffi ffl ffi ffi ffi ^
TJ TJ T TJ TJ Tl TJ TJ Tl TJ TJ TJ TJ Tl TJ TJ TJ TJ TJ T TJ TJ TJ TJ TJ Tl TJ
O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J ft
Cd £? rø rø 3 ør
3 3 3 w ι"-I1 rt CD j-! i-r <^ £- ι-t rø W
3 l-f rt ffi 3 ?! '-i CD S' l-f c+ ffi S- ^
3 1 3 'I l- ffi £; I P?..
ffi CD CD ffi ffi ffi ffi ffi ffi CD ffi ffi CD ffi CD ffi CD CD ffi CD ffi CD CD CD CD ffi CD CD CD CD ffi ffi CD CD CD CD ffi '
n O O O Q Q O O Q Q Q Q j O O Q Q O O O Q O O O Q O Ci O O O O O Ci O O o ft
-j -J: ^ --j .-j --- --j --4 to to to to to to to to -J
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ^ ^ ^ ^ ^ ft
O
ώ £ ϊ ι-1 s rt | CD ώ pj ϊ H s " CD gώl ϊ H s CO i 33. 5 i-f ι rtS CD ώ β ϊ Hf | rt5 ffi ώ ϊ i- s rt i ffi pώ; S H S rt ι CD ώ S >^ s " CD ^ >-t rt CD g* I -M
ON C^ ON ON ON ON ^ ON ON ON ^ ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON I^ IM
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω I
O O O O O O O O O O O Q Q O Q Q Q O O Q Q O O Ci O Ci O O O O O O Ci O n o ft
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ^ ^ ^ ^ ^ ft
O o o o O O o o O o O o O o o o o o o o O o o o o o o o o o o o O o o a
9 9 9 9 9 w w ω rø M Cd Bf Cd Cd ω Cd Cd rø Cd W Cd d Cd B? Bf Cd Cd rø Cd W Cd B? Bf ω ω ør ω
UJ
cf δ 3 5 ES δ 3 5 E 1 δ 3 5 ES 1 δ 3 5 cl δ 3 5 ES 1 5 ES δ 3 5 ES δ 3 S ES 1 δ 3 5 ES f c
1Λ ό ό ό ό o ό ό ό ό ό ό ό ό ό ό ό ό ό o ό O ό ό ό ό ό ό ό ό ό ό ό
O o o Ω o o o o Q Ω Ω Q Q Ω Ω Q Q Q Ω Q Q Q Ω Q Q Q Ω O Ω Q Q Q Q Ω O
^^ o a a a O
O o o o o o o o o o ό O
O ό t O O o O o
§ 9 § ° O O o o o o o
2 TJ TJ ^
Ul Ul Ul 9 9 9 9 -4 9 9 9 9 o to to to to 8 -4 -o to to to 8 to to to to E to
9 9 9 9 9 rø Cd rø ω W BP Bf Bf B? rø &? Bf Bf Bf Bf BP Bf BP Bf w Bf Bf ω Bf rø Bf Bf Bf Bf Bf rø w ^
i ώff HyJ E C*
O** ON 0\ cl c cl cf f % CD % CD % CD cf cf cl cl cf I II
O O Ω Ω O Q O O O O O O O O O Q O O O Q O O O O O Q O ft a I a I co co co
<"> v C O co co O s o oJ O oJ OJ OJ OJ O O A J toO
OJ t° TJ >°
TJ TJ T TJ Tj to Tl l Tj
TJ TJ TJ Ω TJ G --4 -4 -4 -4 TJ m Ul Ul Ul OJ J OJ O TJl Ω TJ OJ
-4 -4 -J 811 t 8 to 8 to R
TJ OJ Q TJ QJ O TJ TJ J TJ TJ TJ J TJ TJ J TJ J J TJ TJ TJ J OJ OJ OJ OO J OJ OJ OJ OJ OJ OJ OJ J OJ OJ OJ OJ OJ OJ OJ OJ O 9J O 9J O 9J O 9J O 9J OJ ft ' to
ώ S ES ώ V-
TJ ES g ø t ™
& rø TJ «v
3 ω t? r Λ 3 H ES w 5 rø J W § ij Aj W |! ff «-► c? iff ►? «• I «*»
CTv ON O\ ^ ON i-^ ON ON O ^ ON a ON ON (^ >\ ON O ON O ON ON a ON C3 ON o o o o o o o o o o o o o o o o Ω d o o o o o o o Ω Ω ft
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
9 TJ TJ ^ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ i™^
O 9J O 9J O 9J O 9J O 9J O 9J 9J OJ OJ OJ OJ J J OJ J OJ J OJ OJ OJ J OJ OJ
t^ ON ON ON ON ON O\ ON ON ON ON ON ON t- i C3N O\ l-)N l^ ON ON ON ON ON ON ON |i_| g ffi ffi ffi ffi ffi ffi ffi CD CD ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi 2 ffi ^ ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi L
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi
I I o? o? o9 tj9
ES & » W
-? g3 sp rø cf Cd r
3 J ø ώ i ES ώ J ES ώ J ^ rø i ES | t! J ES : rø j ES ft
O^ ON O O ON C^ O O O Ch O O^ QN ON ON O ON ON O ON O O ON ^ O ON ON ffi CD CD CD CD ffi CD CD CD CD ffi ffi CD CD ffi ffi CD CD CD ffi CD
W s
o O
25 2.
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ^ ^ ^ ^ ^ ^ ^ ft
ffl ffl ffl ffl ffl ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Q Ω Ω
-fc
CD c| i- CD ci i-r " Λ j- -.% ** O j-; i^ ^ C c ^ ffi J ii rt t) ci i-r *+ ffi ci HT ** ffi cl K 1
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
\
9 .0 .0 .θ o co o co 0 0 0 0 ^ ^ ^ ^ g 0 g o ft
^ ^ ^ ^ rø rø rø rø ^ rø l Ul Ul t^ J OJ O J J OJ OJ J - to7 -to7 t-o7 to7 to^ torø t.o^ to^ ^ ^ ^
O O O O Q Q Q O Q Q Q Q Q O Q O Q π Ω Ω Ω v O O Q Q O O Q Tj Tj Tj Tj Tj Tj Tj Ii'd
τJ ES ^ ώ i ES rø τJ ES rø i ES | rø rø cf δ3 5 ES cf δ3 SJ rø Cd ø
3 -V r f sp ES ω 3 $ ft
ON \ ON ON ON ON CJN ON ON ON ON ON CJN ON ON N ON ON (-^ ON ON ON ON N ON ON ON ON ON I-3 ON ON ON N ON N ON !,___.
^ ^ ^ fe ; έ: |: έ: t: i: i: i: |: i: 4: 4: έ: 4: i: i: 4: ^ έ: : i: t: : ^ i: i: ^ 4: i: l: i: i: ^ β
W
£ o o o ~ J. <A-.. a o o o ' a• a' O CO CO CO co co co O y t-p Oy i ' o OJ O OJ OJ O o o A, tO O O o to to to O O O
-ή -ή - -^H rϊJ ϊJ HrJ rll -._. Tj TJ TJ TJ Ω Ω S o O O O
Tl O Tl ^ S O
Tl TJ TI Ui Ui Ui Ui OJ J OJ 9J 3 OJ 3 OτJι 3 TJ T Ω Ω Ω Ω o n Ω ° o ω to τ t τ1 to τ Tl Tj J TJ Tl J 3 OJ to to Mto to tito ϋtoϋto 8 a
TJ TJ TJ rø rø rø rø rø ϋd Cd Cd rø rø rø rø Cd rø rø rø rø rø Cd Cd rø rø rø Cd Cd Cd rø ϋd Cd rø rø Cd o o
s s s Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω
U\
δ S $ E δ 5 ES δ S ES δ 5 ES δ g E δ §; ft
O O O O O O O O O O O O Q O O O Q O O O O O O O O O O O O O O O O O O O O ^
IW
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 9 I
ø έ r? I-TJ E rtS 1 CD? C dd 1-1J ES t CD p « ι-tJ E rtS [S ffi tp!l ι-fJ E " ^ CD cώ! i-tj E^ ^ffi cώi EP rø CD ώ cl ι-tj ES CD cώi i- E ^CD cώj i-tJ S^^ ffii cώl ft1 N Os ON C l C l ON ON ON N ON ON (-^ ON I-JN C-^ ON ON N ON ON Oi aN ON ON ON ON ON I«^ k k k ft
O CD kCD CkD kCD kCD Ck CkD CkD Ok CkD CkD Ok kCD kCD k kCD kCD CkD kCD CkD kCD k CD kCD kO CkD kCD kQ kCD kCD kO CD CD CD CD I p
Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi \
s tos ts ta to g to β to i s * s * * ? ? ?
to to to t to %
τι TJ TJ TJ TJ TJ TJ ^ O O O O O O O O O O O O O O O O O O O O O O O O O O O O O
Mcj Mcj Mcj Mj Mcj * j Mcj Mcj Mcj j Mcj Mcj Mcj j Mcj Mcj Mcj cj Mcj *τj hcj hcj hj Mcj hcj cj hcj Mcj Mcj hcj ft ON
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Q Ω Ω Ω Ω Ω Ω Ω Ω Ω oo
ON ώ jff H¥J E rS* l eι> fώff i-t
ON ON ON ON ON ON ON C^ ON ON ON ON ON ON t^ ON ON ON O\ ON ON ON ON ON ON ON ON C_)N ON t3N ON ON ON ON ON ON ON ft
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω I
Ω Ω Ω Ω Ω Ω Ω Ω ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi l^ co
Ω O
TJ TJ TJ TJ TJ TJ TJ Tj TJ pj TJ TJ *Ti Tl *τcj Tl Tj pj TJ Tj TJ TJ TJ Tj Tj TJ Tj Tj Tj TJ TJ TJ pj TJ Tj TI Tj ON
Ω ι-M Ωfc Ωι-H Ωfc ΩhH Ωfc Ωfc Ωfc ΩH-l Ωfc Ωfc Ωι-H Ωι^ Ωι--H Ωfc Ωfc Ωfc Ωfc Ω!-H Ωfc Ωfc Ωfc Ωfc Ω Ω Ω
ώ g4a R4b EZ R6 X ώ fjt R * EZ R6 X
Me 6-Me Cl OCF3 F CH Me 6-C1 Cl 0CF3 F CH
Et 6-Me Cl 0CF3 F CH Et 6-01 Cl OCF3 F CH i-Pr 6-Me Cl 0CF3 F CH i-Pr 6-C1 Cl 0CF3 F CH t-Bu 6-Me Cl OCF3 F CH t-Bu 6-C1 01 0CF3 F CH
Me 6-Me Cl SCF3 F CH Me 6-C1 Cl SCF3 F CH
Et 6-Me Cl SCF3 F CH Et 6-C1 Cl SCF3 F CH i-Pr 6-Me Cl SCF3 F CH i-Pr 6-C1 01 SCF3 F CH t-Bu 6-Me Cl SCF3 F CH t-Bu 6-C1 Cl SCF3 F CH
Me 6-Me Cl C2F5 F CH Me 6-C1 Cl C2F5 F CH
Et 6-Me 01 C2F5 F CH Et 6-C1 Cl C2F5 F CH i-Pr 6-Me 01 C2F5 F CH i-Pr 6-01 Cl C2F5 F CH t-Bu 6-Me Cl C2F5 F CH t-Bu 6-01 Cl C2F5 F CH
Me 6-Me Cl n-C3F7 F CH Me 6-C1 Cl n-C3F7 F CH
Et 6-Me Cl κ-C3F7 F CH Et 6-C1 Cl «-C3F7 F CH i-Pr 6-Me Cl Λ-C3F7 F CH i-Pr 6-C1 Cl «-C3F7 F CH t-Bu 6-Me Cl «-C3F7 F CH i-Bu 6-C1 Cl «-C3F7 F CH
Me 6-Me Cl i-C3F7 F CH Me 6-C1 Cl i-C3F7 F CH
Et 6-Me Cl t-C3F7 F CH Et 6-C1 Cl i-C3F7 F CH i-Pr 6-Me Cl i-C3F7 F CH i-Pr 6-C1 Cl i-C3F7 F CH t-Bu 6-Me Cl t-C3F7 F CH t-Bu 6-C1 Cl i-C3F7 F CH
Me 6-Me Cl CN F CH Me 6-01 Cl CN F CH
Et 6-Me Cl CN F CH Et 6-C1 01 CN F CH t-Pr 6-Me Cl CN F CH i-Pr 6-C1 Cl CN F CH t-Bu 6-Me 01 CN F CH t-Bu 6-C1 Cl CN F CH
Me 6-Me Cl OCHF2 Cl CH Me 6-01 Cl OCHF2 01 CH
Et 6-Me Cl OCHF2 Cl CH Et 6-C1 Cl OCHF2 Cl CH i-Pr 6-Me 01 OCHF2 Cl CH i-Pr 6-C1 Cl OCHF2 Cl CH t-Bu 6-Me Cl OCHF2 Cl CH i-Bu 6-C1 Cl OCHF2 Cl CH
Me 6-Me Cl SCHF2 Cl CH Me 6-01 Cl SCHF2 Cl CH
Et 6-Me Cl SCHF2 Cl CH Et 6-01 Cl SCHF2 01 CH i-Pr 6-Me Cl SCHF2 Cl CH i-Pr 6-C1 Cl SCHF2 Cl CH t-Bu 6-Me Cl SCHF2 Cl CH t-Bu 6-C1 Cl SCHF2 Cl CH
Me 6-Me Cl OCF3 Cl CH Me 6-C1 Cl OCF3 01 CH
Et 6-Me Cl OCF3 Cl CH Et 6-01 Cl OCF3 Cl CH i-Pr 6-Me 01 OCF3 Cl CH i-Pr 6-01 Cl OCF3 Cl CH f-Bu 6-Me 01 OCF3 Cl CH r-Bu 6-C1 Cl OCF3 Cl CH
Me 6-Me Cl SCF3 Cl CH Me 6-C1 01 SCF3 Cl CH
ON g I!*
CD
CD ffi ffi ffi ffi ffi
0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ' O~' 'Q~> 'Q^ 'O~l 'O~' 'O~> 'O~' O 'O^ 'O^ ^O 'Q^ 'Ω~l 'O~l 'O~1 O 'O~' 'O^ l ;!^§
O O c o co o co oo oo co o O O O to O Q Q
Ul Ui OJ J §111. to8.to8to 8.to8to Itogtogtogs ss *$$$$ £§§$§§§§*
C i-dl Cl-dt Ci-dt røi-t røi-l Ci-dt røi-l Ci-dt C>-td C>-dt røi-i Cl-dl Ci-dl røl-t rø»-t røi-t Cl-dt røi-l O O O O O O O O O O O O O O O O O O O ft
Ωfc Ωι-M Ωι-H ΩI-H Ωfc Ωfc Ωι-H Ωfc Ωfc ΩH-l Ωfc Ωι-H Ωfc Ωι-H Ωfc Ωι-H Ωι-1-l Ωι-H Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω \X J oo rt CD £_f ι-t rt CD c! i- rt CD d r-T rt ffi ci K D B 3f E^ 8 Cd ø ø
3 E? r
3 *! g3 EP r C ώi >-fJ td CD c &i ά> ES ft
Q P Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q O QO QO O O O O O O O O O O O O O O O O ft
P
O O O O O O O O O O Q O O Q O O O Q O O O Q O O O O O O O O O O O O O O O ft
--. .-. O
Ul Ul
rø w w rø w w rø M w rø ω w ω ω w rø ω ω o o o Q O Q Q o o Q Q ON
Ω fc Ω|_| Ωfc Ω|-H Ωι-M Ωfc Ωfc Ωι-M Ωfc Ωfc Ωι-H Ωfc Ωfc Ωfc Ωfc fc Ωfc Ωfc Ωfc Ωfc Ωfc fc ι-H fc ι-H fc ι^
R R4a R4b sZ R6 X ώ P S4.. Z 6 X i-Pr 6-Me Cl C2F5 Br CH i-Pr 6-C1 Cl C2F5 Br CH t-Bu 6-Me Cl C2F5 Br CH t-Bu 6-C1 Cl C2F5 Br CH
Me 6-Me 01 Λ-C3F7 Br CH Me 6-C1 Cl «-C3F7 Br CH
Et 6-Me Cl «-C3F7 Br CH Et 6-C1 Cl «-C3F7 Br CH i-Pr 6-Me Cl "-C3F7 Br CH i-Pr 6-C1 Cl «-C3F7 Br CH t-Bu 6-Me 01 «-C3F7 Br CH i-Bu 6-C1 Cl «-C3F7 Br CH
Me 6-Me 01 '-C3F7 Br CH Me 6-C1 Cl i-C3F7 Br CH
Et 6-Me 01 i-C3F7 Br CH Et 6-01 Cl i-C3F7 Br CH i-Pr 6-Me Cl i-C3F7 Br CH i-Pr 6-C1 Cl i-C3F7 Br CH i-Bu 6-Me Cl i-C3F7 Br CH t-Bu 6-C1 Cl i-C3F7 Br CH
Me 6-Me Cl CN Br CH Me 6-C1 Cl CN Br CH
Et 6-Me Cl CN Br CH Et 6-C1 Cl CN Br CH i-Pr 6-Me Cl CN Br CH i-Pr 6-01 Cl CN Br CH i-Bu 6-Me 01 CN Br CH t-Bu 6-C1 Cl CN Br CH
Me 6-Me α OCHF2 CF3 CH Me 6-01 Cl OCHF2 CF3 CH
Et 6-Me Cl OCHF2 CF3 CH Et 6-01 Cl OCHF2 CF3 CH i-Pr 6-Me Cl OCHF2 CF3 CH i-Pr 6-C1 Cl OCHF2 CF3 CH t-Bu 6-Me Cl OCHF2 CF3 CH t-Bu 6-01 Cl OCHF2 CF3 CH
Me 6-Me Cl SCHF2 CF3 CH Me 6-01 Cl SCHF2 CF3 CH
Et 6-Me Cl SCHF2 CF3 CH Et 6-01 01 SCHF2 CF3 CH i-Pr 6-Me Cl SCHF2 CF3 CH i-Pr 6-01 01 SCHF2 CF3 CH i-Bu 6-Me Cl SCHF2 CF3 CH t-Bu 6-C1 Cl SCHF2 CF3 CH
Me 6-Me Cl OCF3 CF3 CH Me 6-C1 Cl OCF3 CF3 CH
Et 6-Me Cl OCF3 CF3 CH Et 6-C1 Cl OCF3 CF3 CH i-Pr 6-Me Cl OCF3 CF3 CH i-Pr 6-C1 Cl OCF3 CF3 CH t-Bu 6-Me Cl OCF3 CF3 CH t-Bu 6-C1 Cl OCF3 CF3 CH
Me 6-Me Cl SCF3 CF3 CH Me 6-C1 Cl SCF3 CF3 CH
Et 6-Me Cl SCF3 CF3 CH Et 6-C1 Cl SCF3 CF3 CH i-Pr 6-Me Cl SCF3 CF3 CH i-Pr 6-C1 Cl SCF3 CF3 CH i-Bu 6-Me Cl SCF3 CF3 CH t-Bu 6-C1 Cl SCF3 CF3 CH
Me 6-Me Cl C2F5 CF3 CH Me 6-C1 Cl C2F5 CF3 CH
Et 6-Me Cl C2F5 CF3 CH Et 6-C1 Cl C2F5 CF3 CH i-Pr 6-Me Cl C2F5 CF3 CH i-Pr 6-C1 Cl C2F5 CF3 CH t-Bu 6-Me Cl C2F5 CF3 CH t-Bu 6-C1 Cl C2F5 CF3 CH
Me 6-Me Cl «-C3F7 CF3 CH Me 6-01 Cl n-C3F7 CF3 CH
Et 6-Me Cl H-C3F7 CF3 CH Et 6-01 01 «-C3F7 CF3 CH i-Pr 6-Me Cl «-C3F7 CF3 CH i-Pr 6-01 01 «-C3F7 CF3 CH
ON ON ON ffi ffi CD
CD CD ffi ffi ffi CD ffi ffi ffi I Ift P ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffl ffl ffl ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
hcj hcj hcj hcj Mcj Mcj hcj hcj Mcj hcj hcj hcj hcj Mcj Mcj hcj hcJ hcj hcJ hcj hcj Mcj McJ hcj hcj Mcj McJ Mcj hcj hcj hcj J OJ J 9J O 9J O 9J 9J O 9J O 9J ft
Mcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj cj hcj 9 9 9 hcj hcj hcj Mcj Mcj hcj hcj hcj 9 9 9 9 9 9 9 9 9 9 9 IX
4ϊ. o ro jff δι- ErtS lD* jώff ,-rj E <-*■ l o? gffl'
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ' i- I
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O ΩO ΩQ ΩO ΩO ΩO ΩO ΩO 9 9 O O O Ω Ω o Ω Ω O Q O O ft I ffl ffl ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffi ffi ffl ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω ft a a i. ( O VJ O S.1 O SI O tJ Co co oo co O O O —J co c~o c~o c~o O- O- O- O-
O i OJl OO OJJ OO OJJ OO OJJ io.Ji O OJ O O OJ to to to to Ω Ω Ω O Ω
Tl J TJ l cl Tl Tl Tl u, rø ^ TTJJ ft -4 -4 -4 -4 -J -4 -4 -4 * 3- & & J? 3333333 to ato ato 4to to 8to 8to 8to 88 s s s « o -s o O oJ O oJ O oJ
hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj Mcj hcj hcj Mcj TJ J hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj
OJ OJ OJ OJ OJ OJ OJ OJ OJ ft
TJ Tl TI TJ Tj TJ TJ g g g g g g g g g g g g g g g g g g g g g g g 99 Ω a si a tu IX
giff; δ Jff i-fj "E ^ ffi g^ δi-r E C! crøi τj ES i «-> gώ^ δi-f E ^D cώi J ES ^ CO HTj E rt i ffi? pj ^ πf E "S ^ ffi δ 1-1j E rtS ^ ffi g ι-T ^* ffi 1
OJ O! ON
C kD CkD CkD
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi I c
TJ O O Q O Q O Q P Q O Q O O Q Q O Q Q O O O Q Q O TJ TJ TJ TJ )!^
θ O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O o θ O ik-< ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ^ rø ^ ^ 1^
CD δ μfJ
ON σN ON σN σN ON σN σN σ σN N σN O σ σ O ON ON N σ N σN σN σN ON σN ON σN N O ON ON ON σ σN IMH
Q Q Q Q G Q Q Q Q Q Q Q G Q Q Q Q Q Ω Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q l^
lssss| -4|-4|-4|-4 -4 -4l-4|-4 |||||| ||J| tO|tO|tO|tO
Tj Q O Q Q O Q Q Q Q O O Q Q Q O Q Q O Q O Q Q O Q O Q Q Q Q Ti Ti Tj Tj
O ffi o Oo Oo Oo Oo Oo Oo Oo Oo Oo Oo Oo Oo Oo o Oo Oo o Oo oO Oo Oo Oo Oo o oO oO Oo oO Oo Oo Oo ny oy θy Oy ιi«x^
? R4a E4.. R7 R6 X M R4? R4b RZ R6 X.
Et 3-Me H OCHF2 F CH Et 3-C1 H OCHF2 F CH i-Pr 3-Me H OCHF2 F CH i-Pr 3-C1 H OCHF2 F CH t-Bu 3-Me H OCHF2 F CH t-Bu 3-C1 H OCHF2 F CH
Me 3-Me H SCHF2 F CH Me 3-01 H SCHF2 F CH
Et 3-Me H SCHF2 F CH Et 3-C1 H SCHF2 F CH i-Pr 3-Me H SCHF2 F CH i-Pr 3-C1 H SCHF2 F CH t-Bu 3-Me H SCHF2 F CH t-Bu 3-01 H SCHF2 F CH
Me 3-Me H OCF3 F CH Me 3-01 H OCF3 F CH
Et 3-Me H OCF3 F CH Et 3-C1 H OCF3 F CH i-Pr 3-Me H OCF3 F CH i-Pr 3-C1 H OCF3 F CH t-Bu 3-Me H OCF3 F CH t-Bu 3-C1 H OCF3 F CH
Me 3-Me H SCF3 F CH Me 3-C1 H SCF3 F CH
Et 3-Me H SCF3 F CH Et 3-C1 H SCF3 F CH i-Pr 3-Me H SCF3 F CH i-Pr 3-01 H SCF3 F CH t-Bu 3-Me H SCF3 F CH t-Bu 3-01 H SCF3 F CH
Me 3-Me H C2F5 F CH Me 3-C1 H C2F5 F CH
Et 3-Me H C2F5 F CH Et 3-C1 H C2F5 F CH i-Pr 3-Me H C2F5 F CH i-Pr 3-C1 H C2F5 F CH i-Bu 3-Me H C2F5 F CH t-Bu 3-C1 H C2F5 F CH
Me 3-Me H «-C3F7 F CH Me 3-C1 H n-C3F7 F CH
Et 3-Me H «-C3F7 F CH Et 3-01 H «-C3F7 F CH i-Pr 3-Me H K-C3F-7 F CH i-Pr 3-01 H «-C3F7 F CH t-Bu 3-Me H «-C3F7 F CH i-Bu 3-C1 H n-C3F7 F CH
Me 3-Me H i-C3F7 F CH Me 3-C1 H i-C3F7 F CH
Et 3-Me H i-C3F7 F CH Et 3-01 H i-C3F7 F CH i-Pr 3-Me H i-C3F7 F CH i-Pr 3-01 H i-C3F7 F CH t-Bu 3-Me H i-C3F7 F CH i-Bu 3-01 H i-C3F7 F CH
Me 3-Me H CN F CH Me 3-C1 H CN F CH
Et 3-Me H CN F CH Et 3-C1 H CN F CH i-Pr 3-Me H CN F CH i-Pr 3-C1 H CN F CH t-Bu 3-Me H CN F CH t-Bu 3-C1 H CN F CH
Me 3-Me H OCHF2 Cl CH Me 3-C1 H OCHF2 Cl CH
Et 3-Me H OCHF2 Cl CH Et 3-C1 H OCHF2 Cl CH i-Pr 3-Me H OCHF2 Cl CH i-Pr 3-C1 H OCHF2 Cl CH t-Bu 3-Me H OCHF2 Cl CH t-Bu 3-C1 H OCHF2 Cl CH
Me 3-Me H SCHF2 Cl CH Me 3-01 H SCHF2 CI CH
Et 3-Me H SCHF 01 CH Et 3-C1 H SCHF2 01 CH
CJ Q CJ O CJ CJ U O CJ Q U O O U O CJ O O CJ U O CJ CJ O CJ O O CJ O C O U O a O
9 fcl 5 f ^-> 'r <lJ ---» 4 E:3 <U w & pq a ^ pp ^ a ^ p? ^ W ^ <9 S W (? s a n χι 3 3 3 3 3 333 333 3 333 33 3 3533 3 33335 3 33 33 3 33
^| G G G G G G G G G G G G G G G G G G G G G G G G G G ^ pq pq pq -3 pq pq fi pq (S
CN CN cN CN cN CN CN CN
s a 8 O 8O 8O 8O 8co 8co 8co o 88080
ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffl ffi ffi ffi ffl ffi
t- ^" c co co co co co co co co co co co co co co co co co co co co co co co co co co co c co co co co co co co
_T rfc _τ -fc -H (fc .T -fc ^ o a.-_, jfvr4 ø 3p. ^> a.1__ .ρHr; ø3? ^o a.-_ f.!-| eP? ^ω a-ι-> o
5335355 co co co co co co co 8 8 8 8 8 8 8
B fi
o 8o 8o β-"β"6co,
*jTI"JI fc i-HM
MM MM MM MM MM MM MM
fcl CJ CJ CJ CJ 9 J U J O O O J J CJ CJ CJ CJ o o o o α α o u o CJ CJ O CJ CJ O O CJ CJ co c co cn co co co
3 fc pp ^ a ^ a ^ ^ ^ a ^ pp ^ ^ a ^ p? ^ a P? s a ? (? S S i? ^ s 5
XI 8 8 8 8 8 8 8 5 8 5 5 8 8 8 8 5 3 5 8 8 8 8 5 5 8 5 8 8 8 5 5 8 8 8 5 8 vo co co co co co co co co co co co co co co co
^I rg ffl m ffl fS fS m rg S ffl ffl m m m
r O CO O CO ^ ^ ^ ^ |iJ h fo fc li ii l rfJ L_ _ ^ CN cN cN CN cN CN CN CN
' θ c co co cΛ θ O O 9 9 CJ . O . cj O O O O O O ε; *_, u. s; S 8 O 8O OB BO Bco 8co 8co Bco S1-' Bv-, &k-' R' ' BWJ 6J B
r- ^' co co co co cn co ro ro co co co co co co co co co co co co co co c^ a fe p? s a f pp ^ a f f? s f ρ? ^ f q ^ p? ^ a f o
R E4.. R4b EZ R6 X R3 R4a R4b sZ ≠ X
Me 3-Me H C2F5 CF3 CH Me 3-C1 H C F5 CF3 CH
Et 3-Me H C2F5 CF3 CH Et 3-C1 H C2 5 CF3 CH i-Pr 3-Me H C2F5 CF3 CH i-Pr 3-C1 H C2F5 CF3 CH i-Bu 3-Me H C2F5 CF3 CH i-Bu 3-C1 H C2F5 CF3 CH
Me 3-Me H «-C3F7 CF3 CH Me 3-C1 H κ-C3F7 CF3 CH
Et 3-Me H «-C3F7 CF3 CH Et 3-01 H «-C3F7 CF3 CH i-Pr 3-Me H «-C3F7 CF3 CH i-Pr 3-C1 H «-C3F7 CF3 CH t-Bu 3-Me H «-C3F7 CF3 CH i-Bu 3-C1 H «-C3F7 CF3 CH
Me 3-Me H i-C3F7 CF3 CH Me 3-01 H i-C3F7 CF3 CH
Et 3-Me H i-C3F7 CF3 CH Et 3-C1 H i-C3F7 CF3 CH i-Pr 3-Me H i-C3F7 CF3 CH i-Pr 3-01 H i-C3F7 CF3 CH i-Bu 3-Me H i-C3F7 CF3 CH i-Bu 3-C1 H i-C3F7 CF3 CH
Me 3-Me H CN CF3 CH Me 3-01 H CN CF3 CH
Et 3-Me H CN CF3 CH Et 3-C1 H CN CF3 CH i-Pr 3-Me H CN CF3 CH i-Pr 3-C1 H CN CF3 CH i-Bu 3-Me H CN CF3 CH t-Bu 3-01 H CN CF3 CH Tab le 4
R4a R4b R7 R3 R6 R4a R4b R7 R R6 R4a R b R7 R3 R6
CH3 F CF3 Me Cl 01 F CF3 Me Cl Br F CF3 Me Cl
CH3 F CF3 Et 01 Cl F CF3 Et 01 Br F CF3 Et Cl
CH3 F CF3 i-Pr Cl Cl F CF3 i-Pr 01 Br F CF3 i-Pr Cl
CH3 F CF3 t-Bu Cl Cl F CF3 t-Bu Cl Br F CF3 t-Bu 01
CH3 F CF3 Me Br Cl F CF3 Me Br Br F CF3 Me Br
CH3 F CF3 Et Br Cl F CF3 Et Br Br F CF3 Et Br
CH3 F CF3 i-Pr Br Cl F CF3 i-Pr Br Br F CF3 i-Pr Br
CH3 F CF3 i-Bu Br 01 F CF3 i-Bu Br Br F CF3 t-Bu Br
g4a R4b S7 Ei R6 g4a 24b s R ≠ g4a R4b sZ R3 R6
CH3 F Cl Me 01 Cl F 01 Me Cl Br F 01 Me 01
CH3 F Cl Et Cl 01 F 01 Et 01 Br F Cl Et 01
CH3 F Cl i-Pr Cl 01 F Cl i-Pr Cl Br F Cl i-Pr 01
CH3 F Cl i-Bu 01 Cl F Cl i-Bu Cl Br F Cl i-Bu 01
CH3 F Cl Me Br Cl F Cl Me Br Br F Cl Me Br
CH3 F Cl Et Br Cl F Cl Et Br Br F Cl Et Br
CH3 F Cl i-Pr Br Cl F Cl i-Pr Br Br F Cl i-Pr Br
CH3 F Cl i-Bu Br Cl F Cl t-Bu Br Br F Cl i-Bu Br
CH3 F Br Me Cl Cl F Br Me Cl Br F Br Me 01
CH3 F Br Et Cl Cl F Br Et Cl Br F Br Et Cl
CH3 F Br i-Pr Cl Cl F Br i-Pr Cl Br F Br i-Pr Cl
CH3 F Br i-Bu Cl Cl F Br t-Bu Cl Br F Br i-Bu Cl
CH3 F Br Me Br Cl F Br Me Br Br F Br Me Br
CH3 F Br Et Br Cl F Br Et Br Br F Br Et Br
CH3 F Br i-Pr Br Cl F Br i-Pr Br Br F Br i-Pr Br
CH3 F Br t-Bu Br Cl F Br t-Bu Br Br F Br t-Bu Br
CH3 01 CF3 Me Cl Cl Cl CF3 Me Cl Br Cl CF3 Me Cl
CH3 Cl CF3 Et Cl Cl Cl CF3 Et Cl Br Cl CF3 Et Cl
CH3 Cl CF3 i-Pr Cl Cl Cl CF3 i-Pr Cl Br Cl CF3 i-Pr Cl
CH3 Cl CF3 i-Bu Cl Cl Cl CF3 t-Bu Cl Br Cl CF3 i-Bu 01
CH3 Cl CF3 Me Br Cl Cl CF3 Me Br Br Cl CF3 Me Br
CH3 Cl CF3 Et Br Cl Cl CF3 Et Br Br Cl CF3 Et Br
CH3 Cl CF3 i-Pr Br Cl Cl CF3 i-Pr Br Br Cl CF3 i-Pr Br
CH3 01 CF3 i-Bu Br Cl Cl CF3 i-Bu Br Br 01 CF3 i-Bu Br
CH3 Cl Cl Me Cl Cl Cl Cl Me Cl Br 01 Cl Me Cl
CH3 Cl Cl Et Cl Cl Cl Cl Et 01 Br 01 Cl Et Cl
CH3 Cl Cl i-Pr Cl Cl Cl Cl i-Pr Cl Br Cl Cl i-Pr Cl
CH3 Cl Cl t-Bu Cl 01 Cl 01 i-Bu Cl Br Cl Cl t-Bu Cl
CH3 01 Cl Me Br Cl Cl 01 Me Br Br Cl Cl Me Br
CH Cl Cl Et Br Cl 01 Cl Et Br Br 01 01 Et Br
CH3 Cl Cl i-Pr Br Cl Cl Cl i-Pr Br Br Cl Cl i-Pr Br
CH3 Cl Cl i-Bu Br Cl Cl Cl i-Bu Br Br Cl Cl i-Bu Br
CH3 Cl Br Me Cl 01 Cl Br Me Cl Br Cl Br Me Cl
CH3 Cl Br Et Cl Cl Cl Br Et Cl Br Cl Br Et Cl
CH3 Cl Br i-Pr Cl Cl Cl Br i-Pr Cl Br Cl Br i-Pr Cl
CH3 Cl Br t-Bu Cl Cl Cl Br i-Bu Cl Br Cl Br t-Bu Cl
CH3 Cl Br Me Br Cl 01 Br Me Br Br Cl Br Me Br
Ω v j TJ TJ TJ TJ TJ J Tj TJ Cd Cd Cd Cd Cd OJ OJ OJ OJ OJ OJ OJ OJ M i-t T T i-t ω # ω Ω Ω Ω Ω Ω Ω Ω Ω ø
O gJ OgJ OgJ OgJ OgJ OgJ OgJ OgJ ^w r ^w ι-t ft > r I
C?D t!i Tj ø Irø OJ o O d ι^ rø i-t C i-dl rø i-t ffl i-l o o o o W i-t ffl C i-t i-t ffl i-t Ω Ω Ω rø rø Cd
T3 ι-t Ω Ω Ω w w ω ω Ω Ω Ω Ω w w ω ft ON
O O O O O O O O O O O O O O Q Ω O O O O O O O O O O O O O O O O O O O ft ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi w ffi ffi ffi ffi ffi ffi ffi ω Cd Cd Cd Cd r Cd Cd ι-t ι-t ø ffl Cd Cd Cd
T o o o rø rø rø rø rø rø Ω Ω Ω Ω o O O O
rø C S crøi i-t E ^CD ct5di i-fj ES tC?D δ 3 5 ES 3 δ 5 B cf I E? ES δ 3 5 ES cf δ 3 5 ES cf δ 3 5 ES cf w S rø Irø
3 I UJ w E? Ω Ω Ω S? -V E? ω Q o rø w w ω Ω Ω Ω Ω Q o o Q w ffl ffl Q Q ffl Cd Cd i-l ι-t i-l ft
C Hdt fflι-| ffli-t fflι-t fflι-| Ci-dt fflι-t fflι-t fflH C>-td ffl i-t ffl i-t ffl i-l ffl ι-t ffl ι-t ffl i-t C i-dt ffl i-t ffl l-t ffl ι-t ffl ι-t l-dt ffl ι-| ffli-t fflι-l ffl>-t fflι-t ffl>-t fflι-i ffli-t fflι-t ffl!-t ffl>-t Cι-td fflι-t fflι-t fflι-t ft i 05
Cd Cd ffl
Cd ø ffl Cd f r rø rø Cd rø rø rø Cd T ι-t ►t H H ι-t T ffl d
T C i-d d t ι-t ffl i-l ffl ι-t ffl T C l-td o o ft l§
IΛ t-
G l U|
© O pq ώ pq pq CJ G G G fi ώ U pq pq G G G G Ul pq pq pq G G G G Ul Ul pq pq pq to G G G G fi pq
3 3 3 3 3 3
H U fcl 5 3 1 a 5 pq a S 3 a α. s « •*?-. 1 a § i a 3 a $ ! 1 a 5 3 a •-- 3 a fc 0 CJ 0 CJ 0 O pq pq pq a U pq ffl pq pq 8 8 8 8 fc 0 8 8 8 u 0 0 0 υ 0 CJ J pq a pq pq fi pq fc 4 8 8 0 8 8 8 8 8 8 8 fc 8 8 8 8 8 8 8 cf 0 8 8 b 8
U u< Ul Ul fc pq pq pq pq pq fi pq pq pq pq pq pq pq pq pq pq pq pq pq ώ pq pq pq pq pq pq a pq pq pq pq pq Pq pq pq pq
U Ul Ul fc pq pq pq pq pq pq G G G G pq pq pq G G G G pq pq pq pq J G G G Ul U pq pq pq fi G G G G pq pq
3 3 3 3 3 3 fc 5 3 a s 3 3 a f? 3 a s 3 3 a 5 3 a $ 3 a s 3 3 1 a $ 3 a $ 3 a
.0 f ffl U U U u U fc fl pq pq pq pq pq pq pq pq pq pq pq cd 1 fc 0 O O O CJ J O CJ CJ O O O CJ O 0 0 CJ 0 0 0 0 CJ 0 CJ J O 0 O O 0 O CJ J O J O fc G G pq fc pq pq G G G Ul
O pq pq pq pq G G G u,
CJ pq pq pq G CJ G G Ul pq pq pq pq CJ G G J a pq
3 3 3 fcl s 3 3 3 a S 3 a s 3 3 a s 3 1 a s 3 3 a 5 pq 1 a s 3 3 3 a 5 3 a 5 3 1 a u, fcl 0 0 CJ 0 CJ O pq pq pq pq a pq pq pq 8 8 δ δ s δ 8 8 0 CJ 0 CJ J 0 0 O pq pq pq (3 pq pq δ 8 8 8 8 8 8 8 fc
%\ 8 8 8 8 8 8 8 8 8 8 8 8 δ 8 t- rό cd 1 co f 5 5 5 8 ffi .f '
P 5 5 fl 8 5 5 5 5 5 5 5 8 ffi 5 fif 8 fif
90 8 5 5 5 5 5fi
5 5 5 5 8 ffi 8 ffi 5 5 5 3 3 3 3 o
R4a R4b R7 R R6 R4a R4b R7 R R6 R4a R4b R7 R3 R6
CH CF3 Br t-Bu Br Cl I Br t-Bu Br Br CF3 Br t-Bu Br
CH3 01 Cl «-Pr Cl Cl CF3 CF3 Me 01 I Cl CF3 Me Cl
CH3 Cl 01 R-BU Cl Cl CF3 CF3 Et Cl I Cl CF3 Et Cl
CH3 Cl 01 •Ϊ-BU Cl Cl CF3 CF3 i-Pr Cl I Cl CF3 i-Pr Cl
CH3 Cl Cl i-Bu Cl Cl CF3 CF3 t-Bu Cl I Cl CF3 t-Bu Cl
CH3 H CF3 Me Cl Cl CF3 CF3 Me Br I 01 CF3 Me Br
CH3 H CF3 Et Cl 01 CF3 CF3 Et Br I 01 CF3 Et Br
CH3 H CF3 i-Pr Cl Cl CF3 CF3 i-Pr Br I Cl CF3 i-Pr Br
CH3 H CF3 t-Bu Cl 01 CF3 CF3 i-Bu Br I Cl CF3 i-Bu Br
CH3 H CF3 Me Br Cl CF3 Cl Me Cl I Cl 01 Me Cl
CH3 H CF3 Et Br Cl CF3 Cl Et 01 I Cl Cl Et Cl
CH3 H CF i-Pr Br 01 CF3 Cl i-Pr Cl I Cl Cl i-Pr Cl
CH3 H CF3 t-Bu Br Cl CF3 Cl t-Bu Cl I Cl Cl i-Bu Cl
CH3 H Cl Me Cl Cl CF3 01 Me Br I Cl Cl Me Br
CH3' H Cl Et Cl Cl CF3 Cl Et Br I Cl Cl Et Br
CH3 H Cl i-Pr Cl 01 CF3 Cl i-Pr Br I Cl 01 i-Pr Br
CH3 H 01 i-Bu Cl 01 CF3 Cl i-Bu Br I Cl 01 i-Bu Br
CH3 H Cl Me Br Cl CF3 Br Me Cl I Cl Br Me Cl
CH3 H Cl Et Br Cl CF3 Br Et 01 I Cl Br Et 01
CH3 H 01 i-Pr Br Cl CF3 Br i-Pr 01 I Cl Br i-Pr Cl
CH3 H Cl i-Bu Br Cl CF3 Br t-Bu Cl I 01 Br i-Bu Cl
CH3 H Br Me Cl Cl CF3 Br Me Br I 01 Br Me Br
CH3 H Br Et 01 Cl CF3 Br Et Br I 01 Br Et Br
CH3 H Br i-Pr Cl Cl CF Br i-Pr Br I 01 Br i-Pr Br
CH3 H Br i-Bu Cl Cl CF3 Br i-Bu Br I Cl Br t-Bu Br
CH3 H Br Me Br Cl Cl Cl «-Pr Cl I H CF3 Me Cl
CH3 H Br Et Br Cl Cl Cl «-Bu Cl I H CF3 Et Cl
CH H Br i-Pr Br Cl Cl Cl j-Bu Cl I H CF3 i-Pr 01
CH3 H Br t-Bu Br Cl Cl 01 i-Bu Cl I H CF3 i-Bu Cl
Table 5
i-rJ E rtS i CfD ∑ ώ3 i-J o
Ui Ui M ffl g ffl tid ffl ffi ffi ffi ffi ffi ffi (-} ffi ffi ffi tjj ffi ffl ffi g ffi rø ffi ffi ffi ffl ffi ffi ffi n ffi ffi ffi (id I gs c T
9 Tl o ft
<*»
rø cd ffl 9 9 9 9 9 9 9 9 9 TJ TJ TJ TJ Tl TJ cj TJ TJ TJ 9 Ω Ω <~> Q Ω Ω Ω O O O O O Q O ft
O O O O O O O O O O O O O Ω Ω Ω Ω O O O Q Q O O O O Q Q Q O O O O O O O O ft I p
ffi EC ffi td ffi ffi ffi ffl ffl ffl ^ ^ ^ ^ W ffi ^ ffi ^ ffi hrj ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi V1 P ϊ? T
ffl ffl ffl 9 rø Ω røo g g g g g g g g g g g g g g g g g Q Q o Ω Ω Ω Ω O O O O O O Ω ft
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON i & i 1 * s i i 1 i 1 i 1 c i cf i 1 t f c 1 i 1 t *» *1 Ul Ui in ffl ffl ffl a ffi ffl ffi ffi ffi ffi a ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl Ω ffl o ffl ffl ffl ffl ffl ffl o \ o co 00 00 to o ° o o o 00 o o o o o o o o t o o o 00 o
Tj TJ to to 8 § to o Ui Ui Ul U to 8 cf 9 to
TJ to 8 Ul to 9 to 8 to 8 d j to to 8 to 8 9 9 C l 9 9 9 9 9 9 9 9 9 Q Q Ui 9 EP ft
Tj Tj Tj Tj Tj TJ TJ Tj Tj Tj TJ TJ Tj TJ Tj J TJ TJ TJ TJ Cd ffl Cd Cd Cd Cd i-l ffl ffl Cd ffl • ffl Cd ffl Cd Cd ffl ffl ft
CΛ t ) δ 3 5 ES 3 δ EV ES cf g3 5 ES δ 3 5 ES 1 δ 3 EV ES cf δ 3 5 i
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON Irø ό ό ό ό ό O o ό ό ό ό ό o ό ό ό ό ό ό ό ό ό ό ό ό ό ό ό ό ό ό ό 1 fa
Ui Ui Ui Ui Ui ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Cd ffl ffl ffl ffl ffl ffl 1 ff ffl ffl ffl 1 o l Cd ffl ffi o \
Tj TJ TJ j J TJ TJ TJ Tj Tj TJ Tj Tj Tj Tj Tj TJ Tj Tj TJ ffl ffl Cd Cd ffl £ Cd BP ffl ffl Cd £P ffl lff ffl ■I ffl ffl ft
1 i 1 t 1 ft
* i * 1 f * 1 i 1? & i 1 i & 1
ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl « ffi ffi ffi ffi ffi ffl ffl ffi a ffl ffl w ffi ffi ffl ffl ffl ffi ffi ffl ffi ffi \ a a
O o o o o o o co co O O o o o o s 3 o o o o o O O O to o t° 9 9 9 9 8 o o
9 9 9 9 o t 8 to to τ to § o o ft to 8 to to ϋ to 8 9 S S
ffl Cd lff Cd Cd ffl Cd Cd ffl C flf Cd Cd
4i. "
ES cf δ 3 EV ES δ 3 E? ES cf δ 3 S ES f 3 δ 5 ES δ 7
3 5 ES c ffif δ 3 5 ES cf 5 ES f δ 3 E? ES δ 3 5 ES Irø
Irø ό ό ό ό ό ό ό ό ό ό ό ό o ό ό o ό ό ό ό ό ό ό 6 ό ό ό ό ό ό ό ό 1 so
ffl ffl ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffl ffl ffi ffi ffi ffl ffl ffi ffi ffi ffl ffl ffi ffi ffi ffl ffi ffi \
Cd ffl ffl Cd BP flf Cd ffl ffl Cd ffl flf Cd ffl BP BP ffl ffl ffl Cd ffl B? Cd Cd $ B? ffl ffl B? o o o o O o ft
fc
|O
tJ ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi
fcl u o o u u o o u o o o u u o u u o u u o o o o o u α o o o o u o α o o v vo vo vo ό ό ,ό ό , vό ,ό ό vό ό ^ ^ vo vo ό o vo vό vό o vό vo vo o o o vo o
3 3 3 3 fcl 5 pq s « £ 3 3 pq s « * pq a +-» f ,fc •§ W * P? s « * pq W * .T -fc 3
P? a ? p? S w pq S «
fc
CN CN CN CN cN CN CN CN CN
OJ js ft g £ g g g g g g 8 8 8 8 8 8 8 ^ ^ ^ ^ τ r ^ - - - - S f^ S s ^l u u o o o S B o o o ^ ^ ^ ^ υ c cj cj 9 9 9 9 9 u O CJ CJ u o
O O O O co co co co R •- -~ o o
%l ffl ffi ffi ffi ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl O
cd i tϋ u ω ω ω ω ij ω cj ω tii ω ω pi\ vό vo v vo vo vo vo vo vo o vό o vo vo vo vo vo vo vό vό vo vo vo vo vo vo v vo vό vό vo vo vo vo vό t-
3 3 3 3 3 3 3 fcl s pq w * pq pq pq .T
Λ i. w f 2 S * W Pn pq I q M l P .T -C
W Pn pq q
•A ^ S w S p .5£ w -T
O
Cd ø ffl rø Cd rø Cd
3 E? r
3 E? 3 & ι-f E *^S CD e ffl rø i Ti § ώ τJ E ^ ώ J E §. ffl τj w Cd
3 5 E δ ft
δ δ g s u δ [rø. ffi ffi ffi ffi ffi ffi P
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω |
W-4 -4 -4 -4 -4f f JJJJJJJj
Ω Ω Ω Ω Ω Ω Ω Ω ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ft
ON
_ 3r i 'Iyj a 1- »l δ g' ι-rj E<S' ^C δ cj HJ E rtS ^ ffi δi δ HΓ E "S ^ CD δ c! HJΓ E "S ffi δ g HJΓ E rtS ^ ffi δ j- i-fJ s CD δ 3" τ ι-Jr E «-S•■ Λ δ ci ιιj S^* ffi δ c ft
ON ON ON ON ON ON ON ON ON ON ON ON ON C^ ON I^ ON ON ON ON ON ON ON ON ON aN C3N ON ON ON ON ON ON ON ON ON ON |hri
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω l
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft co co co co O O O O a a a a oo co co oo o o 3 to @ to g to a to g to g to ς to §j § § § §^ ^ ^ ^ ^& ^ & 5 ?o?o?o?ti?t]9o? to to ^ to to to s ^
Ω Ω Ω Ω Ω Ω Ω Ω ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ cl >τl >τl >τl '7ι:l hτl >τl >τl ft
S (l ror! ilj ErtS (i?ll fflc
l Ift
o o o o o o o o o o o o o o o o o o o o o o o o o o Q Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω PI
o O O O O oo co oo oo O O O O O O O Q O O O O o π o o » 2 2 g o o o o
* g> OgJ OgJ l OgJ OgJ .rø -rø - Mrø .Mrø S rø g rø S rø S rø § "^ § -^t § ""^ § ^ξ Tjξ Tj^ TJ^ TJ^ hcj^ Tj^ TJ^ Tj ^Ni U^l ^ Ul U^l O9J O9J 9J O9J O9J O9J O9J O9J ft to to to io to to to to ffl II ω ii ω ii ω ii c 1d W 1 ffl 1 C >td ω 1 ω ii ω H c 1d C 1d o —. o!— o ι-ι o!-- oι-- oι- oι-ι oι— o i— o ,— o i— o i— o H- oI— o I— o I— o i— o I— o i— o ι— o i— o i— o i— o I— | |rø-4,
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON |hrJ
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω I
O O O O O O O O O O O O O O O O O O O O Q O O O O O O O O Q Ω Ω Ω Ω Ω Ω Ω β c go O § O O§ O§ ' Ϊ9 S9 S9 r9^ SΩ SΩ SΩ SΩ g g g § tg X ξX ξX ^X ^^ ^^ ^^ ^^ tgO tgO tgO tgO CQΛ OQO OQO Q O O O O ft I ON J o oTj oojj oJj v-- ^rø- ^rø ^røj -^rø ^rø ^rø ^rø ^rø. -røJ -rø4 -rø4 -rø4 -røJ -4rø -rø4 -rø4 ^
W ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl W O O O O O O O O O O O Q Q Q Q Q Q Q Q O O O O O ft
rø ω
3 i-Tj E rtS & ffi cffli Kj E^S tfD' cWi j E^S ^D ffli j rø Cd ø Cd rø fl ? ffl J rø
3 ffl
3 E? r
^ f
3 E? ES I J
3 ES ft
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON I-^ ON ON ON ON ON ON ON ON I- ON ON ON ON ON ON ON ON ON ON ; ^; ^ ^; 2 |; Ift
O O O O Q O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O
\%
TJ Tj Tj Tj TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ cj TJ lff II lff ffl ffl ffl Cd Cd Cd Cd ffl Cd ffl Cd ffl Cd Cd Cd ffl ffl lrø
rø ffl ø Cd g" Hf E cS* . ffi? δ ci i-lj ES ^D δ ci τi-fJ ES iC|D δ S τj rø; i CO: w rø ø Cd
3 E? r
3 i-Tj ^« |D δ 3 E? Cd J
3 E? r
3 ES ft
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON aN ON ON ON ON ON ON ON ON
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft I
O O O O Q O O O O O O Q O Q O O O O O O O O O O O O O O O O O O O O O O O ft l&
O O O O
■S § S Q Q Q § § § 8 I 88 Ω 8 Ω Ω 8 I a s s 9 11111 •§ ■§ -S -S § I 8 ft tO tO tO tO o tO tO tO — —4 -4 — 4 -4 -4 —4 -4 g g g g g g g g g g &j cs cd ω cd cd cd cd w w cd d d w w ω ω cd c irø
R3 g4a R4b R6. EZ M R R4b 6 EZ i-Pr 6-Me Cl C2F5 CF3 i-Pr 6-C1 Cl C2F5 CF3 t-Bu 6-Me Cl C2F5 CF3 t-Bu 6-C1 Cl C2F5 CF3
Me 6-Me 01 «-C3F7 CF3 Me 6-C1 Cl «-C3F7 CF3
Et 6-Me 01 «-C3F7 CF Et 6-C1 Cl «-C3F7 CF3 i-Pr 6-Me Cl H-C3F7 CF3 i-Pr 6-C1 01 «-C3F7 CF3 i-Bu 6-Me Cl «-C3F7 CF3 i-Bu 6-01 01 «-C3F7 CF3
Me 6-Me Cl i-C3F7 CF3 Me 6-C1 Cl i-C3F7 CF3
Et 6-Me 01 i-C3F7 CF3 Et 6-C1 Cl i-C3F7 CF3 i-Pr 6-Me Cl i-C3F7 CF3 i-Pr 6-C1 Cl i-C3F7 CF3 i-Bu 6-Me Cl i-C3F7 CF3 i-Bu 6-01 Cl i-C3F7 CF3
Me 6-Me Cl CN CF3 Me 6-C1 Cl CN CF3
Et 6-Me Cl CN CF3 Et 6-C1 Cl CN CF3 i-Pr 6-Me Cl CN CF3 i-Pr 6-C1 Cl CN CF3 i-Bu 6-Me Cl CN CF3 i-Bu 6-01 Cl CN CF3 Tab le 6
R3 R4a R4b R7 R6 X R3 R4a R4b R7 R6 X
Me 6-Me H OCHF2 F CH Me 6-C1 H OCHF2 F CH
Et 6-Me H OCHF2 F CH Et 6-01 H OCHF2 F CH i-Pr 6-Me H OCHF2 F CH i-Pr 6-C1 H OCHF2 F CH i-Bu 6-Me H OCHF2 F CH t-Bu 6-C1 H OCHF2 F CH
Me 6-Me H SCHF2 F CH Me 6-C1 H SCHF2 F CH
Et 6-Me H SCHF2 F CH Et 6-C1 H SCHF2 F CH i-Pr 6-Me H SCHF2 F CH i-Pr 6-C1 H SCHF2 F CH i-Bu 6-Me H SCHF2 F CH i-Bu 6-01 H SCHF2 F CH
Me 6-Me H OCF3 F CH Me 6-01 H OCF3 F CH
Et 6-Me H OCF3 F CH Et 6-01 H OCF3 F CH
EP rø ffl ι-1j E rtS
Os Os Os Os Os OS Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os k k k k k k k k k k k k k k k k k k k k k k k k k k k ft I P. I
£ co co oo
£ Ω o Ω t Ω tf
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj Mcj Mcj hcj hcj \ f^
Ω Ω Ω Ω Ω Ω 9 Ω Ω Ω Ω Ω 9 9 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω i o
5? ES ^ CD wj ilJ ES t? ffll ilJ ES ^ ø CD ώl rø r ffl 3 πfJ E "S" ^ CD ffl }2f ^ *lf E ÷S+ Ω ffl r- j ES jS Effl- HJ* E "S" CD rffl- T μyj E^ D «ffl- μj ft I W
Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os C^ ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON Ihri
O O O Q Q Q Q Ω Ω Ω Ω Ω Ω Ω Ω Ω o o o o o o o o o o o o o o o o o o o o o g-
I hcj ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl Cr
O O O O O O O Q Q Ω Ω Ω Ω Ω Ω rø rø τj τj τj τj Tj τj τj τj τj τj τi τj τj τj hcj hcj τj τj τj τj |rø-.
R3 R4a R4b R7 ≠ X R3 R4a R4b R7 R6 X t-Bu 6-Me H SCF3 Cl CH i-Bu 6-C1 H SCF3 Cl CH
Me 6-Me H C2F5 01 CH Me 6-C1 H C2F5 Cl CH
Et 6-Me H C2F5 Cl CH Et 6-01 H C2F5 Cl CH i-Pr 6-Me H C F5 Cl CH i-Pr 6-C1 H C2F5 01 CH t-Bu 6-Me H C2F5 01 CH i-Bu 6-C1 H C2F5 Cl CH
Me 6-Me H «-C3F7 01 CH Me 6-C1 H «-C3F7 Cl CH
Et 6-Me H «-C3F7 Cl CH Et 6-01 H «-C3F7 Cl CH i-Pr 6-Me H "-C3F-7 Cl CH i-Pr 6-C1 H κ-C3F7 Cl CH i-Bu 6-Me H «-C3F7 Cl CH i-Bu 6-C1 H «-C3F7 Cl CH
Me 6-Me H i-C3F7 Cl CH Me 6-01 H i-C3F7 Cl CH
Et 6-Me H i-C3F7 Cl CH Et 6-01 H i-C3F7 Cl CH i-Pr 6-Me H i-C3F7 Cl CH i-Pr 6-C1 H i-C3F7 Cl CH i-Bu 6-Me H i-C3F7 Cl CH i-Bu 6-01 H i-C3F7 Cl CH
Me 6-Me H CN Cl CH Me 6-C1 H CN Cl CH
Et 6-Me H CN Cl CH Et 6-C1 H CN Cl CH i-Pr 6-Me H CN Cl CH i-Pr 6-C1 H CN Cl CH i-Bu 6-Me H CN Cl CH i-Bu 6-01 H CN Cl CH
Me 6-Me H OCHF2 Br CH Me 6-C1 H OCHF2 Br CH
Et 6-Me H OCHF2 Br CH Et 6-C1 H OCHF2 Br CH i-Pr 6-Me H OCHF2 Br CH i-Pr 6-C1 H OCHF2 Br CH i-Bu 6-Me H OCHF2 Br CH i-Bu 6-C1 H OCHF2 Br CH
Me 6-Me H SCHF2 Br CH Me 6-C1 H SCHF2 Br CH
Et 6-Me H SCHF2 Br CH Et 6-01 H SCHF2 Br CH i-Pr 6-Me H SCHF2 Br CH i-Pr 6-C1 H SCHF2 Br CH t-Bu 6-Me H SCHF2 Br CH i-Bu 6-C1 H SCHF2 Br CH
Me 6-Me H OCF3 Br CH Me 6-C1 H OCF3 Br CH
Et 6-Me H OCF3 Br CH Et 6-C1 H OCF3 Br CH i-Pr 6-Me H OCF3 Br CH i-Pr 6-C1 H OCF3 Br CH t-Bu 6-Me H OCF3 Br CH i-Bu 6-C1 H OCF3 Br CH
Me 6-Me H SCF Br CH Me 6-C1 H SCF3 Br CH
Et 6-Me H SCF3 Br CH Et 6-C1 H SCF3 Br CH i-Pr 6-Me H SCF3 Br CH i-Pr 6-C1 H SCF3 Br CH i-Bu 6-Me H SCF3 Br CH i-Bu 6-C1 H SCF3 Br CH
Me 6-Me H C2F5 Br CH Me 6-C1 H C2F5 Br CH
Et 6-Me H C2F5 Br CH Et 6-C1 H C2 5 Br CH i-Pr 6-Me H C2F5 Br CH i-Pr 6-01 H C2F5 Br CH i-Bu 6-Me H C2F5 Br CH i-Bu 6-C1 H C2F5 Br CH
CN t- IΛ t- χι 3555655533 55555533555555555553555555 ffl ^I m m m p q m p-l pq pq pQ pq pq fc fc fc fc fc fc fc fc cf fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc U CJ O O U CJ O CJ CJ CJ CJ O U O O CJ CJ O O O O O O
H J α.
**J ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi
fcl ϋ O O O CJ CJ o o υ u o o O CJ O CJ O O CJ O O CJ CJ o o J o g o g g o O CJ vo vo vo vo vo vo vo vo vo vo vo 9o 9 C vό co i j-. ( 3 3 fcl ^ <-> a ^ .r1 p .2? ^ <ύ a — f JH p __ 3 ?? ^ a 4j <ι> ._> H 3 pq 2 w * .T pq S S ft p? a ^ P pq W P pq ■a +•* ft pq S s « P -2 3
P?
CN
VO ι 3555335555 55 55585535555 55 55 555 8 55 55
Pil ffl pq pq m pq pq pq pq pq pq fc fc fc fc fc fc fc fc fc fc fc fc fc co co fc f g g u cj o g g o cj cj o υ u fc ft fc fc fc c f fc
CJ g o o o 8 8 c 8 8 δ δ r- t— • t— ■ t— r— t— c— c— c fc fc fc fc fc fc ,-,. .^ CN CN CN CN N CN CN CN „ „ „ fc f co co co <r> v> v~ι in r- r- r- r- f fc fc fc fcl o o o o o o o o o o σ o S S S g & S S S δ δ δ δ δ fc fc fc fc cf fc, fc c o g O CN CN
O C co O O O O o o u
-D 1 "^j ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi
Q o ω ω c ω cij ω ω j ^ ω ω o o ω ω tϋ o o <D ^ ω <u < ω ( τj t-
.H fcl
3 u, 3 3 3 ω 3 Ui 3 (0 fcl ? ω 4 Ji s
S M $ pq ft P? * pq * 3 S W $ pq w 5: 3 s & °? s a % mi ^ ω a M o
B R4 R4b EZ R6 X E2 £4a R4b s7 X
Et 6-Me H i-C3F7 CF3 CH Et 6-C1 H i-C3F7 CF3 CH i-Pr 6-Me H i-C3F7 CF3 CH i-Pr 6-C1 H i-C3F7 CF3 CH t-Bu 6-Me H i-C3F7 CF3 CH i-Bu 6-C1 H i-C3F7 CF3 CH
Me 6-Me H CN CF3 CH Me 6-C1 H CN CF3 CH
Et 6-Me H CN CF3 CH Et 6-01 H CN CF3 CH i-Pr 6-Me H CN CF3 CH i-Pr 6-01 H CN CF3 CH i-Bu 6-Me H CN CF3 CH i-Bu 6-C1 H CN CF3 CH
Me 6-Me Cl OCHF2 F CH Me 6-C1 Cl OCHF2 F CH
Et 6-Me Cl OCHF2 F CH Et 6-01 Cl OCHF2 F CH i-Pr 6-Me Cl OCHF2 F CH i-Pr 6-C1 Cl OCHF2 F CH t-Bu 6-Me Cl OCHF2 F CH i-Bu 6-C1 Cl OCHF2 F CH
Me 6-Me Cl SCHF2 F CH Me 6-C1 Cl SCHF2 F CH
Et 6-Me Cl SCHF2 F CH Et 6-01 Cl SCHF2 F CH i-Pr 6-Me Cl SCHF2 F CH i-Pr 6-C1 Cl SCHF2 F CH i-Bu 6-Me Cl SCHF2 F CH i-Bu 6-01 Cl SCHF2 F CH
Me 6-Me 01 OCF3 F CH Me 6-C1 01 OCF3 F CH
Et 6-Me Cl OCF3 F CH Et 6-C1 Cl OCF3 F CH i-Pr 6-Me Cl OCF3 F CH i-Pr 6-C1 Cl OCF3 F CH i-Bu 6-Me Cl OCF3 F CH t-Bu 6-C1 Cl OCF3 F CH
Me 6-Me Cl SCF3 F CH Me 6-C1 Cl SCF3 F CH
Et 6-Me Cl SCF3 F CH Et 6-01 Cl SCF3 F CH i-Pr 6-Me Cl SCF3 F CH i-Pr 6-C1 Cl SCF3 F CH i-Bu 6-Me Cl SCF3 F CH i-Bu 6-01 Cl SCF3 F CH
Me 6-Me Cl C2F5 F CH Me 6-01 Cl C2F5 F CH
Et 6-Me 01 C2F5 F CH Et 6-01 Cl C2F5 F CH i-Pr 6-Me Cl C2F5 F CH i-Pr 6-01 Cl C2F5 F CH i-Bu 6-Me Cl C2F5 F CH i-Bu 6-01 Cl C2F5 F CH
Me 6-Me Cl κ-C3F F CH Me 6-C1 Cl κ-C3F7 F CH
Et 6-Me Cl n-C3F7 F CH Et 6-C1 01 «-C3F7 F CH i-Pr 6-Me Cl «-C3F7 F CH i-Pr 6-01 01 «-C3F7 F CH i-Bu 6-Me Cl «-C3F7 F CH i-Bu 6-01 01 «-C3F7 F CH
Me 6-Me Cl i-C3F7 F CH Me 6-01 Cl i-C3F7 F CH
Et 6-Me Cl i-C3F7 F CH Et 6-01 Cl i-C3F7 F CH i-Pr 6-Me Cl i-C3F7 F CH i-Pr 6-01 01 i-C3F7 F CH i-Bu 6-Me Cl i-C3F7 F CH i-Bu 6-C1 Cl i-C3F7 F CH
Me 6-Me Cl CN F CH Me 6-C1 Cl CN F CH
Et 6-Me Cl CN F CH Et 6-C1 01 CN F CH
s2 R4? R4b EZ R6. X s2 R4a R4b EZ E6. X i-Pr 6-Me Cl CN F CH i-Pr 6-C1 Cl CN F CH i-Bu 6-Me Cl CN F CH i-Bu 6-C1 Cl CN F CH
Me 6-Me Cl OCHF2 Cl CH Me 6-01 Cl OCHF2 01 CH
Et 6-Me Cl OCHF2 Cl CH Et 6-C1 Cl OCHF2 Cl CH i-Pr 6-Me 01 OCHF2 Cl CH i-Pr 6-C1 Cl OCHF2 Cl CH i-Bu 6-Me Cl OCHF2 Cl CH i-Bu 6-C1 Cl OCHF2 Cl CH
Me 6-Me Cl SCHF2 Cl CH Me 6-C1 Cl SCHF2 Cl CH
Et 6-Me Cl SCHF2 Cl CH Et 6-C1 Cl SCHF2 01 CH i-Pr 6-Me Cl SCHF2 Cl CH i-Pr 6-C1 Cl SCHF2 Cl CH i-Bu 6-Me Cl SCHF2 01 CH i-Bu 6-01 Cl SCHF2 Cl CH
Me 6-Me Cl OCF3 Cl CH Me 6-C1 01 OCF3 Cl CH
Et 6-Me Cl OCF3 01 CH Et 6-C1 Cl OCF3 Cl CH i-Pr 6-Me Cl OCF3 Cl CH i-Pr 6-C1 Cl OCF3 Cl CH i-Bu 6-Me Cl OCF3 Cl CH i-Bu 6-01 Cl OCF3 Cl CH
Me 6-Me 01 SCF3 Cl CH Me 6-C1 Cl SCF3 Cl CH
Et 6-Me Cl SCF3 Cl CH Et 6-C1 Cl SCF3 Cl CH i-Pr 6-Me Cl SCF3 Cl CH i-Pr 6-C1 01 SCF3 Cl CH t-Bu 6-Me Cl SCF3 Cl CH i-Bu 6-01 Cl SCF3 Cl CH
Me 6-Me Cl C F5 Cl CH Me 6-C1 Cl C2F5 Cl CH
Et 6-Me Cl C2F5 Cl CH Et 6-C1 Cl C F5 Cl CH i-Pr 6-Me Cl C2F5 Cl CH i-Pr 6-01 Cl C2F5 Cl CH i-Bu 6-Me Cl C2F5 Cl CH i-Bu 6-01 Cl C2F5 Cl CH
Me 6-Me Cl κ-C3F7 Cl CH Me 6-01 Cl «-C F7 01 CH
Et 6-Me 01 «-C3F7 01 CH Et 6-C1 Cl «-C3F7 01 CH i-Pr 6-Me Cl «-C3F7 Cl CH i-Pr 6-C1 Cl «-C3F7 01 CH i-Bu 6-Me Cl «-C3F7 Cl CH i-Bu 6-C1 Cl «-C3F7 Cl CH
Me 6-Me Cl i-C3F7 Cl CH Me 6-C1 Cl i-C3F7 Cl CH
Et 6-Me Cl i-C3F7 Cl CH Et 6-C1 Cl i-C3F7 Cl CH i-Pr 6-Me 01 i-C3F7 Cl CH i-Pr 6-C1 01 i-C3F7 Cl CH i-Bu 6-Me 01 i-C3F7 Cl CH i-Bu 6-C1 Cl i-C3F7 Cl CH
Me 6-Me 01 CN Cl CH Me 6-C1 Cl CN Cl CH
Et 6-Me Cl CN Cl CH Et 6-C1 Cl CN Cl CH i-Pr 6-Me Cl CN Cl CH i-Pr 6-C1 Cl CN Cl CH i-Bu 6-Me Cl CN Cl CH i-Bu 6-C1 Cl CN Cl CH
Me 6-Me Cl OCHF2 Br CH Me 6-C1 Cl OCHF2 Br CH
Et 6-Me Cl OCHF2 Br CH Et 6-01 01 OCHF2 Br CH i-Pr 6-Me Cl OCHF2 Br CH i-Pr 6-01 01 OCHF Br CH
Cd rø Cd ø fl
3 3 E? r E? ør H 5 ES ώ EP w E f
3 EP ES g Cd
3 E? " w. (I J ro HJ " ES ffi U w rø ES w
3 ft t N ON ON ON ON \ ON ON O\ ON ON ON ON I-^ ON ON ON N ON ON ON ON C7N C^ ON ON ON ON ON ON ON N ON \ ON ON ON ft
O CD CD CD CD CD CD O O CD CD CD CD CD CD C CD CD CD CD O CD CD CD CD CD CD CD O O O CD CD CD I
O O O O O O O O O O Q Q O O O O Q Q O O Q Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O O O O O O r#
t
Tj TJ TJ TI TJ j Tj Tl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Cd ffl Cd ffl ffl ffl ffl Cd ffl ffl ffl
'1 >1 >1 H 1 H >1 1 >1 H M H > i1 H lt i-l H 1 |-t H l1 i-l i1 > >1 i1 >1 >-t
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 9 9 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ON
Cd ø flf EP ør E? rø ffl 3 rø rø ci E? r W E? w
3 ffl J ES ø
3 ω EP rø r ffl Irø.
3 ω E? rø Cd
3 |ι_rj l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l l
O O O O O O O O Q O Q O Q O O Q Q O O O Q Q Q O Q Q O O Q Q O O O O Q I^
O O O O O O O O O O Q Ω Ω Ω Ω Ω ^ Ω Ω Ω Ω Ω Ω Ω O O Ω Ω O Q Ω O O Q O O O l O 00 OO 00 O O O O co oo co co
O O O O O O O O Ω Ω .9 .9.9.9 o o l O i. to0 to0 to0, to0π 5c "o-. 5o --5o. 5o—-o.. 5c—o5 O O O O n n n n X
% ES ffi, ffi, ffi, ffi, ffi, ffi, * z z * % ^J <&Tj ^J ^TJ .rø- i :/rø, ^ :rø, ^ ? ? ? ? cj? o7 ft o to to to to to to to -4 -4 --1 —4 -? ? ? J to to M to to to rø
g g g g g g g g Cd W Cd ffl W ffl ffl W Cd Cd ffl W Cd Cd Cd ffl W W W Cd Cd W W W Cd Cd ffl Cd W ft
μ Ω-J, ΩJ--l ffiΩ Ω-( Ωi-r Ωl<
Cd 15 ES ø w
3 E? rø δ 3 5 ES cf δ r ø ø Cd r
3 5 ffl Cd
3 EP r
3 E? r
3 E? ø
3 i ES δ rø rø ft
ft
CD CD CD CD CD O Cli CD CD CD CD CD CD O CD C O CD O CD CD O CD O CD O CD Cfc CD CD C^ I
ffi ffi ffi ffi ffi ffi ffl K ffl ffl ffl ffl ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
ft
hcj hcj hcj hj h^ Mj^ i^ Mcj MjrJ hcj hcj hcj Mcj 9 9 9 9 9 o TJ o TJ o TJ o Tj Q hcj Q hcj O hcj O hcj
O 9J OJ O 9J O 9J O 9J OJ O 9J O 9J 9J O 9J O 9J 9J O 9J ft
hcj hcj hcj hcj hcj hcj hcj Mcj hcj Mcj hcj hcj 9 Θ Q S 8 S a a a a a a a a a a a a a a a a a a a IX
ON
3 ffl E? t E rS & CD ø ώ i TiJ ES S ro HJ rt ES ffl ro pi E? rø Cd
3 rø ES Cd rø
3 ffl 3 E? ES δ 3 5 ES cf ( ffli S H ES tl ft
Os Os Os Os Os ON ON ON Os Os Os Os Os Os Os Os Os Os Os ON ON ON ON o o o Q O o π o O O Q O O o o O 9 o o o o o o o o ό ό ό O Q Q Ω o o o o ft
ffl ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω β
CO O O O O Q O
Tj hcJ TJ hή Tj ώ ώ ώ
O OJJ 1O.J1 1O.J1 tOiJl t-J .to* .tol .toΥ*
Mx HH h
^.cj hcj hcj hcj hcj hj hcj M hcj hcj hcj h Hcj Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IX
i ι ft ft ft ft ft ft ft ft ft ft P P Pι ft ft ft ft P ft G G g o G G o o c o o o o o o o i^il O O O CJ O O O O O CJ CJ O O CJ CJ CJ O O cj CJ CJ O O O CJ CJ O U O CJ O CJ CJ O CJ ffl ^| fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ζj ζj j G G G G G G G G G G G G
H CJ α. t- r-
Ό < <n CN f fc fc fc c fc r- fc r- fc r- r- r o co co co m fc fc fc f - r- CN - CCNN _CN _ CCNN c cNN .CN .CN .CN co co co co c fc fc fc h r fcl fc c co co co co co co At As J J J i CJ r i o υ C rs tj π π r F δ 8 8 δ δ δ δ δ ^
CJ J u J O O CJ o J
R » 5 5 \ \% W\ S S' s
O y Oy yO yO vj oo oc c o-' o*-' o o*-' co o o
-o 1 fcl ffi ffi ffi ffl ffi ffl ffi ffi ffi ffi ffi ffi ffl ffi ffi ffl ffl ffi ffi
CJ O O CJ CJ O O O O O O CJ O O O O O CJ O O O O O O O U U O CJ O J fc! vό ' vo vo vo vb vo vo 9 vό 9 O ό VO vo VO O *ό VO O VO O O vo fcl £ $ a j 3 3 3 3 3 ω 3 _T 3 o — H 3 pq £ w ft pq w * P? .S -T
2 p * P? pq 3 2 pq * pq S w p? s a ft pq t
^i fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc l O O O O O O O O O O CJ O O O O O tf ft CJ
CJ o o o o o o o o CJ CJ o o CJ J o o
CJ CJ J u CJ CJ CJ J J J CJ CJ CJ J CJ u
^| fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc O O O O O O O O O O O O O O CJ O O
r— t— • t— - t— t— . r-— r— CN CN CN CN cN CN CN CN r ftf1 ft rT* ft rT1 fc ft ft fc fc fc fc fc fc co c c c co co co co j^j As
M U O O .^> N -CN -cN ςj- ' CJ' CJ' CJ' CJ' CJ' CJ' U U U
CO CO CO C J Vj vJ i i i i i i i i u H O XO HO KO &co 5co- -coi -coi O C> O O i- .. B i~: o
t-
Cό hM1 vo o o o v v ό o o vo v ό v o o o vo o vό o o ό ό o v o o vo v vό ^
^ ft ffl ^ ft ^ ^ a ft p? ft p? ^ a ft a ft ffl ^ a ft ffl ^ a ft ^ a $ P? iS o
τ ι-ri E"S iff; δj_i J ES CD δ iJ. ES D δpS τi-lJ E'^S CD δ{_i τι1J ErS^ D -δø ιιJ rS tJ gδ >ιj ES n δS ,lJ ES β δι3 μt ES ffi§ Cδ ,1J ft o OJ OJ O OJ J J OJ oJ OJ OJ J J OJ o J OJ OJ ,._ OJ k k k k k k k k k k k k k k k k k k k k k k k
■is x
- %4 -4 -4 ^^^^^^^^33333 tO 3tO 3tO 3tO tO %tO %tO %tO % * -<4 — J -4 -4 -J -J -4 -4 ft j j j j j cj j i Ti i i^ j j l i Tj j j j Ti j j j Q Q Q Q Q Q Q Q Q Q Q Q Irø^ o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o ,-, ffi ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω l
OO ι-rJ ErtS ^D τ >-?j E <S i? co δ g^ τι-rj ErtS ^cD δ pj τi-tj E^S ci?D δ j- τ i-rJ E^S ffi δ ø τ i-rJ E^S ?cιD δ jr HΓJ E <■S* ^ « 5- i-J E ^S+ ^ CD δ g^ >-rj E **^ « g" HF 1 <■«
OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ QN C^ O C^ ON O C^ ^ O ON ^ O ON ON I ri Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lέ"
TJ hή TJ o^ Ul Ul Ul OJ OJ OJ OJ OJ OJ OJ OJ .rø .rø -rø κrø rø rø rø rø T' Tl rø T' TJ Tl TJ TJ ui ,
-4 -4 -4 tO tO tO tO t J t tO -4 -4 -4 -4 -J -4 -4 -4
TJ TJ TJ Tj TJ Tl Tj Tj TJ hrj Tj hcJ hcJ hcj hrJ TJ hcl hcJ TJ hrJ TJ Tj Tj Q Q Q Q Q O O O O O |1*. o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o ,-, ffl ffi ffl ffi ffl ffi ffi ffl ffi^ ffi ffi ffl ffi ffl ffi ffi^ ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 1
5 G
u
cl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi
fcl o o o o O O O O O CJ O O O O O O O O O O CJ O CJ O CJ O O O U O O o O O J O co co o co co co co co co co co co co co co co co co co co co co co co co co co
3 i- 3 j. u< 3 +- p. 3 3 3 .T 3 4 P? pq £ 3 pq p ft ffl S w -** ft ffl S H pq S « ft pq * pq S « P? k-5 -T ω ft «
3 2 fc
ON vo ,. MM MM *T" MM H* HH MM MM H ι HM χι 5 5 5 5 5 5
5 5 5 5
^I fc fc fc fc fc fc fc fc fc f Q Q Q r G G G G G G G G G G G G g G G G G G g
** y-MjI|
t- cό "' co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co H
_ o -_ι H -3 t --. i-ι J? t-) --ι J-ι 3 <_) --, Jι -ι J-1 ■? ω -_» JH ϊ3 ω .__, JH 3 <-> -_, JH .? fc ^ ^ ft ffl ^ ft ffl ^ ft a ft ^ a ft ffl | a ft fti a ft o? | ft ffl ^ ft o
R3 R4a R4b R7 R6 X R R4a R4b R7 R6 X
Me 3-Me H CN Cl CH Me 3-Cl H CN Cl CH
Et 3-Me H CN Cl CH Et 3-Cl H CN Cl CH i-Pr 3-Me H CN Cl CH i-Pr 3-Cl H CN Cl CH i-Bu 3-Me H CN Cl CH i-Bu 3-Cl H CN Cl CH
Me 3-Me H OCHF2 Br CH Me 3-Cl H OCHF2 Br CH
Et 3-Me H OCHF2 Br CH Et 3-Cl H OCHF2 Br CH i-Pr 3-Me H OCHF2 Br CH i-Pr 3-Cl H OCHF2 Br CH i-Bu 3-Me H OCHF2 Br CH i-Bu 3-Cl H OCHF2 Br CH
Me 3-Me H SCHF2 Br CH Me 3-Cl H SCHF2 Br CH
Et 3-Me H SCHF2 Br CH Et 3-Cl H SCHF2 Br CH i-Pr 3-Me H SCHF2 Br CH i-Pr 3-Cl H SCHF2 Br CH i-Bu 3-Me H SCHF2 Br CH i-Bu 3-Cl H SCHF2 Br CH
Me 3-Me H OCF3 Br CH Me 3-Cl H OCF3 Br CH
Et 3-Me H OCF3 Br CH Et 3-Cl H OCF3 Br CH i-Pr 3-Me H OCF3 Br CH i-Pr 3-Cl H OCF3 Br CH i-Bu 3-Me H OCF3 Br CH i-Bu 3-Cl H OCF3 Br CH
Me 3-Me H SCF3 Br CH Me 3-Cl H SCF3 Br CH
Et 3-Me H SCF3 Br CH Et 3-Cl H SCF3 Br CH i-Pr 3-Me H SCF3 Br CH i-Pr 3-Cl H SCF3 Br CH i-Bu 3-Me H SCF3 Br CH i-Bu 3-Cl H SCF3 Br CH
Me 3-Me H C2F5 Br CH Me 3-Cl H C2F5 Br CH
Et 3-Me H C2F5 Br CH Et 3-Cl H C2F5 Br CH i-Pr 3-Me H C2F5 Br CH i-Pr 3-Cl H C2F5 Br CH i-Bu 3-Me H C2F5 Br CH i-Bu 3-Cl H C2F5 Br CH
Me 3-Me H κ-C3F7 Br CH Me 3-Cl H «-C3F7 Br CH
Et 3-Me H «-C3F7 Br CH Et 3-Cl H «-C3F7 Br CH i-Pr 3-Me H «-C3F7 Br CH i-Pr 3-Cl H «-C3F7 Br CH i-Bu 3-Me H R-C3F7 Br CH i-Bu 3-Cl H «-C3F7 Br CH
Me 3-Me H i-C3F7 Br CH Me 3-Cl H i-C3F7 Br CH
Et 3-Me H i-C3F7 Br CH Et 3-Cl H i-C3F7 Br CH i-Pr 3-Me H i-C3F7 Br CH i-Pr 3-Cl H i-C3F7 Br CH i-Bu 3-Me H i-C3F7 Br CH i-Bu 3-Cl H 1-C3F7 Br CH
Me 3-Me H CN Br CH Me 3-Cl H CN Br CH
Et 3-Me H CN Br CH Et 3-Cl H CN Br CH i-Pr 3-Me H CN Br CH i-Pr 3-Cl H CN Br CH i-Bu 3-Me H CN Br CH i-Bu 3-Cl H CN Br CH
Me 3-Me H OCHF2 CF3 CH Me 3-Cl H OCHF2 CF3 CH
U ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi o O O O o o o o o O O U U O U U g o o o o o o o o o o o o o o co t cn co o o 3 tu ι 3 ω 3 3 3 fcl a £ 3 3 3
P? * pq >s -T j . U ft M W % P? S W * P? S w * ffl W ft pq ft ffl
O
XI 3 355 55 555 555 5555 8 55 55555555555 fcl 8 δ δ δ cf 8 8 fc δ δ δ ft ft ft g δ δ δ δ δ δ δ δ δ δ δ δ δ δ δ δ δ δ δ
.. (D D θ <iJ ω ω cu ω ω cij ω o o D <- ϋ o <D tι> ω t- "' co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co fcl s ft ft ffl « £ - lf ffl ^y -aT
S f ft *. ^ ^ a ft f? _aτ Λfti p ^ *a. ft ffl ^ .T -ftt! p? ^ a ft ffl o
Ω HH ΩHH ΩHH ΩHH ΩH ΩHH ΩHH ΩHM ΩHH ΩHH ΩHW ΩHH ΩHH ΩHH ΩHH ΩHH OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ
C H-J« hcj hcj hcj hcj hcj hcj hcj hcj Mcj hcj hcj hcj hcj hcj hcj Mcj hcj hcj hcj hcj hcj hcj hcj hcj I j ^ j^
Q Q w ^ w ffl ^ w w ^ ffl• w ** w o '— Q-* ^ o o ■— o Q ■— '-' O9J O9J O9J O9J O9J O9J O9J 9 I -J
CD
CJ CJ hrj TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ I .^ - *~' I o"*
O QJ OQJ ^ω ^w ^ffl ^ω ^ω ^ω ^ffl ffl ^ Q^ Q,-^ Q'—^ o ^ Ω^ o'— ^ O9J O9J OJ O9J O9J O9J O9J O9J ft ' "^
rt CD ø ii ""•■ CD pj i-F ^ CD j!; Hf «-*• ffi i-r ^* ffi i- D ø CO l Cti
Ω Ω ^ ^ w ffl Ω Ω Ω Ω ∞ ^ ^ ^ Ω Ω Ω Ω ^ ^ ∞ ^ Ω Ω Ω Ω ft
R4a R4b R7 R R6 R4a R4b R7 R3 R6 R4a R4b R7 R R6
CH3 01 CF3 i-Pr 01 Cl Cl CF3 i-Pr Cl Br Cl CF3 i-Pr Cl
CH3 Cl CF3 i-Bu Cl Cl Cl CF3 i-Bu Cl Br Cl CF i-Bu Cl
CH3 01 CF3 Me Br Cl Cl CF3 Me Br Br Cl CF3 Me Br
CH3 Cl CF3 Et Br Cl Cl CF3 Et Br Br Cl CF3 Et Br
CH3 Cl CF3 i-Pr Br Cl Cl CF3 i-Pr Br Br Cl CF3 i-Pr Br
CH3 Cl CF3 t-Bu Br Cl Cl CF3 i-Bu Br Br Cl CF3 i-Bu Br
CH3 Cl Cl Me Cl Cl Cl 01 Me Cl Br Cl Cl Me 01
CH3 01 Cl Et Cl Cl Cl 01 Et Cl Br Cl Cl Et 01
CH3 Cl Cl i-Pr Cl Cl Cl 01 i-Pr Cl Br Cl Cl i-Pr Cl
CH3 Cl Cl i-Bu Cl Cl Cl Cl i-Bu Cl Br Cl Cl i-Bu Cl
CH3 Cl Cl Me Br Cl Cl Cl Me Br Br Cl Cl Me Br
CH3 Cl Cl Et Br Cl Cl Cl Et Br Br Cl Cl Et Br
CH3 01 Cl i-Pr Br Cl Cl 01 i-Pr Br Br Cl 01 i-Pr Br
CH3 Cl Cl i-Bu Br Cl Cl Cl i-Bu Br Br 01 01 i-Bu Br
CH3 Cl Br Me Cl Cl Cl Br Me Cl Br Cl Br Me Cl
CH3 01 Br Et Cl Cl Cl Br Et 01 Br Cl Br Et Cl
CH3 Cl Br i-Pr Cl 01 Cl Br i-Pr 01 Br Cl Br i-Pr Cl
CH3 Cl Br i-Bu Cl 01 01 Br i-Bu 01 Br Cl Br i-Bu Cl
CH3 Cl Br Me Br Cl 01 Br Me Br Br Cl Br Me Br
CH 01 Br Et Br Cl Cl Br Et Br Br Cl Br Et Br
CH3 01 Br i-Pr Br Cl Cl Br i-Pr Br Br Cl Br i-Pr Br
CH3 01 Br i-Bu Br Cl Cl Br i-Bu Br Br Cl Br i-Bu Br
CH3 Br CF3 Me Cl Cl Br CF3 Me Cl Br Br CF3 Me 01
CH3 Br CF3 Et Cl Cl Br CF3 Et Cl Br Br CF3 Et 01
CH3 Br CF3 i-Pr Cl Cl Br CF3 i-Pr Cl Br Br CF3 i-Pr Cl
CH3 Br CF3 i-Bu Cl Cl Br CF3 i-Bu Cl Br Br CF3 i-Bu Cl
CH3 Br CF3 Me Br Cl Br CF3 Me Br Br Br CF3 Me Br
CH3 Br CF3 Et Br Cl Br CF3 Et Br Br Br CF3 Et Br
CH3 Br CF3 i-Pr Br Cl Br CF3 i-Pr Br Br Br CF3 i-Pr Br
CH3 Br CF3 i-Bu Br Cl Br CF3 i-Bu Br Br Br CF3 i-Bu Br
CH3 Br 01 Me Cl Cl Br Cl Me Cl Br Br Cl Me Cl
CH3 Br Cl Et Cl Cl Br Cl Et Cl Br Br Cl Et Cl
CH3 Br Cl i-Pr Cl Cl Br Cl i-Pr Cl Br Br Cl i-Pr Cl
CH3 Br Cl i-Bu Cl Cl Br Cl i-Bu Cl Br Br Cl i-Bu Cl
CH3 Br Cl Me Br Cl H CF3 Me Cl Br Br Cl Me Br
CH3 Br Cl Et Br Cl H CF3 Et Cl Br Br Cl Et Br
CH3 Br Cl i-Pr Br Cl H CF3 i-Pr Cl Br Br Cl i-Pr Br
R4a R4b R7 R3 R6 R4a R4b R7 R3 R6 R4a R4b R7 R3 R6
CH3 Br Cl i-Bu Br Cl H CF3 i-Bu Cl Br Br Cl i-Bu Br
CH3 Br Br Me Cl Cl H CF3 Me Br Br Br Br Me Cl
CH3 Br Br Et Cl Cl H CF3 Et Br Br Br Br Et Cl
CH3 Br Br i-Pr Cl Cl H CF3 i-Pr Br Br Br Br i-Pr Cl
CH3 Br Br i-Bu Cl Cl H CF3 i-Bu Br Br Br Br i-Bu 01
CH3 Br Br Me Br Cl H 01 Me 01 Br Br Br Me Br
CH3 Br Br Et Br Cl H 01 Et Cl Br Br Br Et Br
CH3 Br Br i-Pr Br Cl H 01 i-Pr 01 Br Br Br i-Pr Br
CH3 Br Br i-Bu Br Cl H Cl i-Bu 01 Br Br Br i-Bu Br
CH3 CF3 Me Cl Cl H Cl Me Br Br CF3 Me Cl
CH3 CF3 Et Cl Cl H Cl Et Br Br CF3 Et Cl
CH3 CF3 i-Pr Cl Cl H Cl i-Pr Br Br CF3 i-Pr Cl
CH3 CF3 i-Bu Cl Cl H Cl i-Bu Br Br CF3 i-Bu Cl
CH3 CF3 Me Br Cl H Br Me Cl Br CF3 Me Br
CH3 CF3 Et Br Cl H Br Et 01 Br CF3 Et Br
CH3 CF3 i-Pr Br Cl H Br i-Pr ' 01 Br CF3 i-Pr Br
CH3 CF3 i-Bu Br Cl H Br i-Bu Cl Br CF3 i-Bu Br
CH3 Cl Me Cl Cl H Br Me Br Br Cl Me Cl
CH3 Cl Et Cl 01 H Br Et Br Br Cl Et Cl
CH3 Cl i-Pr Cl 01 H Br i-Pr Br Br 01 i-Pr Cl
CH3 Cl i-Bu Cl 01 H Br i-Bu Br Br Cl i-Bu 01
CH3 Cl Me Br 01 Br Cl Me Br Br Cl Me Br
CH3 Cl Et Br Cl Br Cl Et Br Br Cl Et Br
CH3 Cl i-Pr Br Cl Br Cl i-Pr Br Br Cl i-Pr Br
CH3 Cl i-Bu Br Cl Br 01 i-Bu Br Br 01 i-Bu Br
CH3 Br Me Cl 01 Br Br Me Cl Br Br Me Cl
CH3 Br Et Cl Cl Br Br Et Cl Br Br Et Cl
CH3 Br i-Pr Cl Cl Bi; Br i-Pr Cl Br Br i-Pr Cl
CH3 Br i-Bu 01 Cl Br Br i-Bu Cl Br Br i-Bu Cl
CH3 Br Me Br Cl Br Br Me Br Br Br Me Br
CH3 Br Et Br 01 Br Br Et Br Br Br Et Br
CH3 Br i-Pr Br Cl Br Br i-Pr Br Br Br i-Pr Br
CH3 Br i-Bu Br Cl Br Br i-Bu Br Br Br i-Bu Br
CH3 CF3 CF3 Me Cl Cl I CF3 Me Cl Br CF3 CF3 Me Cl
CH3 CF3 CF3 Et Cl Cl I CF3 Et Cl Br CF3 CF3 Et 01
CH3 CF3 CF3 i-Pr Cl Cl I CF3 i-Pr Cl Br CF3 CF3 i-Pr Cl
CH CF3 CF3 i-Bu Cl Cl I CF3 i-Bu Cl Br CF3 CF3 i-Bu Cl
IΛ t- li li
© Pi m m ffl to G G G G pq m to to o o G G to q ffl m G G G G ffl ffl ffl ffl G G G ffl ffl ffl ffl ffl 3 3 3 3 3
H CJ fc a $ a 3 α. 3 1 a ft* 3 a ft § 5 3 a 3
5 3 a ft* 3 a S 3 a S 3 a s 3
3 fc δ δ δ δ o o o o o o o to ffl ffl ffl pq to to ffl δ δ δ δ δ δ δ δ o o o o o o o o δ δ δ δ 8 fc δ 8 δ δ δ 8 fc 8 δ δ δ δ δ fc 8 δ δ o o o o o o o o o o o o
3 l fc to ffl pq ffl pq lff pq ffl ffl ffl ffl ffl pq ffl ffl ffl to ffl ffl ffl li
P-! pq ffl ffl ffl G G G ffl to to ffl G G G G ffl ffl to ffl G G G G ffl pq ffl pq G o G G to ffl ffl ffl
3 3 3 fc 1 a S 3 a 5 3 a ξ 3 pq a 3
S 3 1 a s 3
3 a ft* 3 a s 3
3 a s 3
3 1 a s 3
3 tr- fc δ δ δ δ o o o o o o o o to ffl ffl ffl ffl ffl ffl m 8 fc δ δ δ δ fc o δ δ o o o o o o o o
% δ δ δ δ δ 8 fc δ 8 fc δ 8 δ δ δ δ δ δ fc o o u o o u o o o o o o o υ υ o o o o o o o o υ o o o υ g
3 3 3 3 s 3 3 3 3 3 fc a ft pq a pq a ξ 3
3 a 3 a g pq f q
— - t K *P $ a 5 p a 5 « 1 a * *<•». 3 o fc δ δ δ δ o o o o o o o ffl ffl ffl pq ffl ffl ffl ffl G G O G δ 8 fc δ 8 δ δ δ δ o υ o o co
^ δ δ δ δ 8 δ δ δ δ δ fc o δ δ δ δ δ δ fc 8 δ δ G G G G ffl ffi tn ffi a c a a ffl ffi ffi ffi t- cd fc 3 3 3 3 3 ffl 8 3 3 3 3 3 8 ffl 3 3 3 8 ffl 3 3 3 3 3 3 3 3 3 3 3 3 8 ffi 3 8 ffi ffl 8 ffi 8 3 3 o
R4a R4b R7 R3 R6 R4a R4b R7 R3 R6 R4a R4b R7 R3 R6
CH3 H 01 Et Br Cl CF3 Br Et Cl I Cl Br Et Cl
CH3 H Cl i-Pr Br 01 CF Br i-Pr Cl I Cl Br i-Pr Cl
CH3 H Cl i-Bu Br 01 CF3 Br i-Bu Cl I Cl Br i-Bu Cl
CH3 H Br Me Cl Cl CF3 Br Me Br I Cl Br Me Br
CH3 H Br Et 01 Cl CF3 Br Et Br I Cl Br Et Br
CH3 H Br i-Pr Cl Cl CF3 Br i-Pr Br I Cl Br i-Pr Br
CH3 H Br i-Bu Cl Cl CF3 Br i-Bu Br I Cl Br i-Bu Br
CH3 H Br Me Br Cl Cl Cl n-Vr Cl I H CF3 Me Cl
CH3 H Br Et Br Cl Cl Cl M-BU 01 I H CF3 Et Cl
CH3 H Br i-Pr Br 01 Cl 01 s-Bu Cl I H CF3 i-Pr Cl
CH3 H Br i-Bu Br Cl Cl 01 i-Bu Cl I H CF3 i-Bu Cl
Table 8
R3 R4a R4b R7 R6 R3 R4a R4b R7 R6
Et 3-Me H OCHF2 F Et 3-Cl H OCHF2 F i-Pr 3-Me H CF3 F i-Pr 3-Cl H CF3 F i-Bu 3-Me H C2F5 F i-Bu 3-Cl H C2F5 F propargyl 3-Me H C2F5 F propargyl 3-Cl H C2F5 F c-propyl 3-Me H CF3 F c-propyl 3-Cl H CF3 F i-Pr 3-Me H Me F i-Pr 3-Cl H Me F i-Bu 3-Me 5-Br CN F i-Bu 3-Cl 5-Br CN F
Me 3-Me H CF3 Cl Me 3-Cl H CF3 Cl
Et 3-Me 5-Me OCF3 Cl Et 3-Cl 5-Me OCF3 Cl i-Pr 3-Me H OCF3 Cl i-Pr 3-Cl H OCF3 01 i-Bu 3-Me 5-Cl Br Cl i-Bu 3-Cl 5-Cl Br Cl
Me 3-Me H Br Cl Me 3-Cl H Br Cl
Et 3-Me H Cl Cl Et 3-Cl H 01 Cl i-Pr 3-Me 5-Br Cl Cl i-Pr 3-Cl 5-Br 01 Cl i-Bu 3-Me H I Cl i-Bu 3-Cl H I Cl propargyl 3-Me H CF3 Cl propargyl 3-Cl H CF3 Cl c-propyl 3-Me H OCF3 Cl c-propyl 3-Cl H OCF3 01 i-Pr 3-Me 5-Cl CF3 Cl i-Pr 3-Cl 5-Cl CF3 Cl t-Bu 3-Me H SCF3 Cl t-Bu 3-Cl H SCF3 Cl
Me 3-Me 5-Cl SCHF2 Cl Me 3-Cl 5-Cl SCHF2 01
Et 3-Me H OCHF2 Cl Et 3-Cl H OCHF2 01 i-Pr 3-Me H CF3 Cl i-Pr 3-Cl H CF3 Cl i-Bu 3-Me H C2F5 Cl i-Bu 3-Cl H C2F5 01 propargyl 3-Me H C2F5 Cl propargyl 3-Cl H C2F5 Cl c-propyl 3-Me H CF3 Cl c-propyl 3-Cl H CF3 Cl i-Pr 3-Me H Me Cl i-Pr 3-Cl H Me Cl i-Bu 3-Me 5-Br CN Cl i-Bu 3-Cl 5-Br CN 01
Me 3-Me H CF3 CF3 Me 3-Cl H CF3 CF3
Et 3-Me 5-Me OCF3 CF3 Et 3-Cl 5-Me OCF3 CF3 i-Pr 3-Me H OCF3 CF3 i-Pr 3-Cl H OCF3 CF3 i-Bu 3-Me 5-Cl Br CF3 i-Bu 3-Cl 5-Cl Br CF3
Me 3-Me H Br CF3 Me 3-Cl H Br CF3
Et 3-Me H Cl CF3 Et 3-Cl H Cl CF3 i-Pr 3-Me 5-Br Cl CF3 i-Pr 3-Cl 5-Br Cl CF3 i-Bu 3-Me H I CF3 i-Bu 3-Cl H I CF3 propargyl 3-Me H CF3 CF3 propargyl 3-Cl H CF3 CF3 c-propyl 3-Me H OCF3 CF3 c-propyl 3-Cl H OCF3 CF3
Ul Ul ϊ Ui u> » ffi t ffi a a ffl ffi flf ffi ffi ffi a ffi ffi o in Q ffi ffi ffi Cd ffi ffi Q fif 1 ffi ffi ffi ffi ffi f to a fi o ffi o %
J TJ TJ Tj TJ j TJ w Cd flf Cd Cd Cd Cd lff Cd Cd Cd Cd Cd Cd Cd
•I 11 ffl W Cd ffl w O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J O 9J ft
-J oo
ON ON ON ON ON ON rø ό CJ ό ό δ δ ό ό δ ό ό ό 6 ό ό ό ό ό ό ό ό δ ό ό ό δ δ ό ό ό δ ό ό δ δ δ δ ^
Ul Ul Ul Ui Ul Ul Ui Ul ffi ffi ffi ffi ffl i ffi 1 ff ffl ffi ffi ffl ffi ffi fif 1 o ffi Ω ffi ffi flf ffi ffi o ffi ffi ffl ffi ffi iff ffi ffi ffi ffi o
TJ J TJ TJ TJ J TJ w ffl ω ffl Cd ω W ffl Cd -t « ω T ω ffl ffl κ ω ffl Cd i ffl
O 9J O 9J O 9J O 9J 9J O 9J O 9J O 9J O 9J O 9J ft
ffl m m pq ffl m m pq m ffl pq pq pq pq m CN cN CN cN CN cN CN O O|O|CΛ|∞|∞|W-g§ f ffff
U fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc
3 ! fcl O O o o o o o o o o o o o o o o o o o o o o o o o o o o o o u u o vo o vό o o o ό v vo vo v ό vό o ό vo vό ό o vo v o o vo vo vo vό O vo
3 3 3 fc ^ a ft ffl ^ a ft ffl ^ ft ffl a ft ffl a ft f? W tf p? pq ft pq « f rS i ^ I pq t pq ft ffl ffl 3
O fcl G G G G G G G G G G G G υ G G G G G G G m pEj pq ffl ffl ffl ffl ffl m m m pq m pq pq ffl
CN CN CN CN cN CN CN cN
■a S § S S & & & & f f I r & δ δ s s § g g g | g | | § § § § g § g s
c i ιS .s ,s ,a ,S ιS ιS ιS 'S ιS .S ιS ι≤ .≤ .--i ,£ ιS i--" vo vo vo vo vό vo vo vo vό vo vo vo vό vo vo vo vo vo vo vo vo vo vό vo vo vό vo vo vo vo vo vo vό vσ vo vo t-
3 i 3 3 fcl to ξ ft ffl ft i f O ff ^ ffl ft fl ? ω a — tf J-i p ϊp3 s a -j_» ft• 3 l m ω i ft i 3
5 a -t ffl ft ffl ft I a 3 ft ffl o
R3 R4a R4b R7 R6 R3 R4a R * R7 R6
Et 6-Me H C2F5 Br Et 6-C1 H C2F5 Br i-Pr 6-Me H C2F5 Br i-Pr 6-C1 H C2F5 Br i-Bu 6-Me H C2F5 Br i-Bu 6-C1 H C2F5 Br
Me 6-Me H /.-C3F7 Br Me 6-01 H «-C3F7 Br
Et 6-Me H «-C3F7 Br Et 6-C1 H «-C3F7 Br i-Pr 6-Me H «-C3F7 Br i-Pr 6-C1 H «-C3F7 Br i-Bu 6-Me H «-C3F7 Br i-Bu 6-C1 H n-C F7 Br
Me 6-Me H i-C3F7 Br Me 6-C1 H i-C3F7 Br
Et 6-Me H i-C3F7 Br Et 6-C1 H i-C3F7 Br i-Pr 6-Me H i-C3F7 Br i-Pr 6-C1 H i-C3F7 Br i-Bu 6-Me H i-C3F7 Br i-Bu 6-C1 H i-C3F7 Br
Me 6-Me H CN Br Me 6-01 H CN Br
Et 6-Me H CN Br Et 6-C1 H CN Br i-Pr 6-Me H CN Br i-Pr 6-C1 H CN Br i-Bu 6-Me H CN Br i-Bu 6-C1 H CN Br
Me 6-Me H OCHF2 CF3 Me 6-C1 H OCHF2 CF3
Et 6-Me H OCHF2 CF3 Et 6-C1 H OCHF2 CF3 i-Pr 6-Me H OCHF2 CF3 i-Pr 6-C1 H OCHF2 CF3 i-Bu 6-Me H OCHF2 CF3 i-Bu 6-C1 H OCHF2 CF3
Me 6-Me H SCHF2 CF3 Me 6-C1 H SCHF2 CF3
Et 6-Me H SCHF2 CF3 Et 6-C1 H SCHF2 CF3 i-Pr 6-Me H SCHF2 CF3 i-Pr 6-01 H SCHF2 CF3 i-Bu 6-Me H SCHF2 CF3 i-Bu 6-C1 H SCHF2 CF3
Me 6-Me H OCF3 CF3 Me 6-C1 H OCF3 CF3
Et 6-Me H OCF3 CF3 Et 6-C1 H OCF3 CF3 i-Pr 6-Me H OCF3 CF3 i-Pr 6-C1 H OCF3 CF3 i-Bu 6-Me H OCF3 CF3 t-Bu 6-C1 H OCF3 CF3
Me 6-Me H SCF3 CF3 Me 6-C1 H SCF3 CF3
Et 6-Me H SCF3 CF3 Et 6-01 H SCF3 CF3 i-Pr 6-Me H SCF3 CF3 i-Pr 6-01 H SCF3 CF3 i-Bu 6-Me H SCF3 CF3 i-Bu 6-C1 H SCF3 CF3
Me 6-Me H C2F5 CF3 Me 6-C1 H C F5 CF3
Et 6-Me H C2F5 CF3 Et 6-C1 H C2F5 CF3 i-Pr 6-Me H C2F5 CF3 i-Pr 6-C1 H C2F5 CF3 i-Bu 6-Me H C2F5 CF3 i-Bu 6-C1 H C2F5 CF3
Me 6-Me H n-C3F7 CF3 Me 6-C1 H n-C3F7 CF3
Et 6-Me H «-C3F7 CF3 Et 6-01 H «-C3F7 CF3
O O O O O O O O O O O O O O O O O O O O O O O Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ft
0 0 O O θ ^ OΛ O ON t3 Λ O\ O OΛ C3 O O O O CΛ ON O ^ OΛ ON C^ O -Λ θN
O O O O O Q O O Q Q Q Q O O O Q Q O O O Q Q O O O O O O O O O O O O O O O I Ift cs
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi β
TJ TJ Tj Tj TJ TJ hcj Tj TJ TJ TJ TJ hcj TJ hcJ hcJ hcJ hrJ hcJ TJ hcJ hrJ hcJ Tj TJ TI TJ hcJ TJ TJ TJ TJ TJ TI
OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft ON
ON O ON;ON ^;ON OΛi^ O CDN C^ t-Ti OΛ OiΛ ON ON OΛ ^iON OΛ ^iC^^ i j
O O O O O O O O O O Q Q O O O O O Q O O Q O Q Q O O O O O O O O O ft
g g g g s Ω aΩ s l 9 Ω aΩ QΩ QΩ QO QO Ω cΩ cΩl 0Ω 0Ω 0Ω 0Ω o o o o o
O 9J OJ 9J O 9J 9J O 9J O 9J O 9J . g g g s g g 8 S S § § § «g ft torø .torø .torø .torø torø torø torø torø rø
O O O O O O O O O O O Q Q Q O O O O O O O O O O O O O O O O O O τj Tj Tj Tj Tj |c*
ffl EP ES g w ø J ES &> w J rø ffl rø ør Cd rø Cd ..
3 'I 3 ff
3 E T? r l
3 T 3 E? Cd
3 E? ør ω E? ES ϋ 2 3 '-i 3 3 E T? 3
δ ό δ ό ό ό δ δ ό δ δ δ δ Q ό ό δ δ δ ό ό δ δ δ ό δ ό δ δ δ δ ό ό ό έ'
O O O O O O O O O O O Q O Q Q O O O O O O O O O O O O O O O O O O O O O O ^ & a a a a o o o Q .0.0. . ι ι .δ c) ιS' 1S> -? .<? S « S S S a S S h rι f) fι χ* i! *S5SS « § g $ s s $ S I 5 J 5 j? 11 to 1to 1to 1to to 1.to11to to 1 a s s a | R.
O O O O O O O O O O O Q Q O O O Q O O O O O O O O O O O O O O O Tj Ti Tj Tj Ti l ,
fcl m ffl m ffl to ffl ffl ffl ffl m m m m ffl m m m m m ffl m m m ffl ffl ffl ffl ffl m m m ffl fc fc fc fc o o o o
ffl
H fcl CJ 0 0 O 0 ∞ ∞ ∞ ∞ o o o o vl ζΛ ∞ u u u u k k κ x; -~ -^ -^ -~ O O O O α. j o o o o o o o o o o o o o o o o o o o o o o o o o o υ o o o o o o o o o
3 I fcl g o o o o o υ o g g o o o o o o υ o o o g g o o g g g g g g g g g g g o vo o o vo vo o vo vo vo o ό ό vό vό vό ό vo o v vo vo vό vo vo v v o o o o o o vo vo vo
fcl I pq ft
S w °? ft f9 a ft ffl a ft cp
" - oo
a a a a s a s s s & δ & & & & & & -S
o o o o o o o g o o o g o o g g g o o o o o g o g g o o o υ o o o o o g sι fi ιS fi S fi S ιS ιS s a a s -. ι2 a S ι2 S δ ι2 s a iH S ι2 5 £ ιS a iH iS a a S ι2 12
t-
o
R3 R4a g4b sZ ≠ ώ g4a R4b EZ R
Et 6-Me 01 SCHF2 CF3 Et 6-C1 Cl SCHF2 CF3 i-Pr 6-Me Cl SCHF2 CF3 i-Pr 6-C1 Cl SCHF2 CF3 i-Bu 6-Me Cl SCHF2 CF3 i-Bu 6-C1 Cl SCHF2 CF3
Me 6-Me Cl OCF3 CF3 Me 6-C1 01 0CF3 CF3
Et 6-Me Cl 0CF3 CF3 Et 6-C1 Cl 0CF3 CF3 i-Pr 6-Me Cl 0CF3 CF3 i-Pr 6-C1 Cl 0CF3 CF3 i-Bu 6-Me Cl 0CF3 CF3 i-Bu 6-C1 Cl 0CF3 CF3
Me 6-Me Cl SCF3 CF3 Me 6-C1 Cl SCF3 CF3
Et 6-Me Cl SCF3 CF3 Et 6-C1 Cl SCF3 CF3 i-Pr 6-Me Cl SCF3 CF3 i-Pr 6-C1 Cl SCF3 CF3 i-Bu 6-Me Cl SCF3 CF3 i-Bu 6-C1 Cl SCF3 CF3
Me 6-Me Cl C2F5 CF3 Me 6-C1 01 C2 5 CF3
Et 6-Me Cl C2F5 CF3 Et 6-C1 Cl C2F5 CF3 i-Pr 6-Me Cl C2F5 CF3 i-Pr 6-C1 Cl C2F5 CF3 i-Bu 6-Me Cl C2F5 CF3 i-Bu 6-C1 Cl C2F5 CF3
Me 6-Me Cl H-C3F7 CF3 Me 6-C1 Cl «-C3F7 CF3
Et 6-Me Cl K-C3F-7 CF3 Et 6-C1 Cl «-C3F7 CF3 i-Pr 6-Me Cl «-C3F7 CF3 i-Pr 6-01 01 «-C3F7 CF3 i-Bu 6-Me 01 «-C3F7 CF3 i-Bu 6-01 01 n-C3F7 CF3
Me 6-Me 01 i-C3F7 CF3 Me 6-C1 Cl i-C3F7 CF3
Et 6-Me Cl i-C3F7 CF3 Et 6-C1 Cl i-C3F7 CF3 i-Pr 6-Me Cl i-C3F7 CF3 i-Pr 6-01 Cl i-C3F7 CF3 i-Bu 6-Me 01 i-C3F7 CF3 i-Bu 6-C1 Cl i-C3F7 CF3
Me 6-Me 01 CN CF3 Me 6-C1 Cl CN CF3
Et 6-Me 01 CN CF Et 6-C1 Cl CN CF3 i-Pr 6-Me Cl CN CF3 i-Pr 6-01 Cl CN CF3 i-Bu 6-Me Cl CN CF3 i-Bu 6-01 Cl CN CF3
55 fc fc
ft, ft c r-
ε- -Λ
"^1 ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffi ffi ffi ffi ffi ffi ffl ffi ffl ffi
t- ό $ μ l 3 vo 3v 3o 3vo 3o 3vo 3vo 3o 3o 3vo 3v v3o 3v v3o 3 3vo 3vo 3vo v3o v3o 3v 3 3vo 3vo 3vo
90
CN
© fc ^ S ft pp a ft ffl ^ a ft pp ^ a ft pp ^ ft p ^ s pp ^ o
MM MM MM MM MM MM MM MM MM MM 5 55 5 5 5555 55 G G G G G G G G
>n fc fc fc fe r£, CL. r£. r£. 1--. .
& ? ? ? ? §• §■ s δ
"^| ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl
fcl o u o o o o o o o o o u u u u o o o u u o u o o u o u o o o u o o u o u
VO o vo VO VO VO vo vo vo vό vo o vo o o vo v vo vo vo vo o v o o vo vo vo o VO VO VO O
3 3 3 cl 5: 3 - s® to - ft 5 ffl ^ a ft 3 o f ffl pq ft ffl ft ffl a ft ffl ^ a ft 3 S W 5: 3 s - a-T £ ft ffl * to
OO HrH HM τ"i MM H HM MM MM MM MM MM MM χι
55 55 5 5 555 56 5
^ fc fc fc fc fc fc Fj fj G G G G G G G G G G G G G G G G G G G G G G G G G G G G
t— t— CN CN CN CN CN CN CN CN t — - c— r — r— t — r- - r— r—
CO CO CO CO ^ θ rθ <n ιn «n <n fc fc fc fc r£. r£J r . r£. t_ 1_ ftϊ •Λ o-Λ o o o o G O GO GO OG 8 8co 8& 8co δ O δO δO δO cδo δco δco δco Oft,Oft) Oft,fOt.& i s ■
-. & s ~t & ι ε; & i Y T" E; & *■-•» &&&55
fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ω <u tu ω ω c <iJ θ (iJ o ω o cD ω u ω r- (4 3 VO 3VO 3VO 3VO 3VO 3VO V3O 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO V3 3VO V3O 3VO 3VO. V 3O 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO 3VO
3 f a ft o? a ft p a ft pp a to 41 JH ^ l cl ft p? a ft fl ffl ^ a ft pp ^t-> f a ftJH ffl3 ^-) al ft ffl5 ^t- a*- o
i g4a R4b E7 ≠ X S3. g4a R E7 R6 X i-Bu 6-Me H CN a CH i-Bu 6-C1 H CN Cl CH
Me 6-Me H OCHF2 Br CH Me 6-C1 H OCHF2 Br CH
Et 6-Me H OCHF2 Br CH Et 6-C1 H OCHF2 Br CH i-Pr 6-Me H OCHF2 Br CH i-Pr 6-C1 H OCHF2 Br CH i-Bu 6-Me H OCHF2 Br CH i-Bu 6-01 H OCHF2 Br CH
Me 6-Me H SCHF2 Br CH Me 6-01 H SCHF2 Br CH
Et 6-Me H SCHF2 Br CH Et 6-01 H SCHF2 Br CH i-Pr 6-Me H SCHF2 Br CH i-Pr 6-01 H SCHF2 Br CH i-Bu 6-Me H SCHF2 Br CH i-Bu 6-C1 H SCHF2 Br CH
Me 6-Me H OCF3 Br CH Me 6-C1 H OCF3 Br CH
Et 6-Me H OCF3 Br CH Et 6-01 H OCF3 Br CH i-Pr 6-Me H OCF3 Br CH i-Pr 6-01 H OCF3 Br CH i-Bu 6-Me H OCF3 Br CH i-Bu 6-01 H OCF3 Br CH
Me 6-Me H SCF3 Br CH Me 6-C1 H SCF3 Br CH
Et 6-Me H SCF3 Br CH Et 6-C1 H SCF3 Br CH i-Pr 6-Me H SCF3 Br CH i-Pr 6-01 H SCF3 Br CH i-Bu 6-Me H SCF3 Br CH i-Bu 6-01 H SCF3 Br CH
Me 6-Me H C2F5 Br CH Me 6-C1 H C2F5 Br CH
Et 6-Me H C2F5 Br CH Et 6-C1 H C2 5 Br CH i-Pr 6-Me H C2F5 Br CH i-Pr 6-01 H C2 5 Br CH i-Bu 6-Me H C2F5 Br CH i-Bu 6-01 H C2F5 Br CH
Me 6-Me H n- -^Εη Br CH Me 6-C1 H «-C3F7 Br CH
Et 6-Me H «-C3F7 Br CH Et 6-C1 H H-C3F7 Br CH i-Pr 6-Me H «-C3F7 Br CH i-Pr 6-C1 H H-C F7 Br CH i-Bu 6-Me H «-C3F7 Br CH i-Bu 6-C1 H κ-C3F7 Br CH
Me 6-Me H i-C3F7 Br CH Me 6-01 H i-C3F7 Br CH
Et 6-Me H i-C3F7 Br CH Et 6-01 H i-C3F7 Br CH i-Pr 6-Me H i-C3F7 Br CH i-Pr 6-C1 H i-C3F7 Br CH i-Bu 6-Me H i-C3F7 Br CH i-Bu 6-C1 H i-C3F7 Br CH
Me 6-Me H CN Br CH Me 6-C1 H CN Br CH
Et 6-Me H CN Br CH Et 6-C1 H CN Br CH i-Pr 6-Me H CN Br CH i-Pr 6-C1 H CN Br CH i-Bu 6-Me H CN Br CH i-Bu 6-C1 H CN Br CH
Me 6-Me H OCHF2 CF3 CH Me 6-C1 H OCHF2 CF3 CH
Et 6-Me H OCHF2 CF3 CH Et 6-C1 H OCHF2 CF3 CH i-Pr 6-Me H OCHF2 CF3 CH i-Pr 6-C1 H OCHF2 CF3 CH i-Bu 6-Me H OCHF2 CF3 CH i-Bu 6-C1 H OCHF2 CF3 CH
δ τj ES ?t δ τJ ES j? δ J S lUft
π i u g g π § § u i i; § § r § g r § § ? § r π?
Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffl ffi ffi ffi ffi ffi ffi 1%
9 fc 9fc Ωfc Ωfc Ωfc Ωfc Ωfc 9fc 9fc Ωfc 9fc Ωfc 99 9 9 99 ffi ffi ffi 9 9 9 9 9 9 9 9 9 9 99 9 999 IX oo cf ffl TJ ES tf w E? rø
E? ES cf δ rø
3 EV ω E? ES 3 w J E rtS Ift
O ON ON ON ON Os Os Os Os Os ON ON ON ON ON ON ON ON O Os Os O
O
Ω O Ω O O O Q Q Ω Ω Ω o o Ω Ω Ω O o o o o o o ft I P»
Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi r*
-. oo oo oo oo O O O O ~. a 9 Ω Q o I J
9 0 O O O O O OJ J S OJ to O J O OJ J to O toO toO J o-. O OO OO O o O Oo OW' CW. OyJ' Cy'
^ Tj Tj TJ TJ j TJ j Tj Tj to . to % to 5. to t Sj to S to tg -4 -4 -4 -4 Ui j hrj hd Tj to _ T Tj Tj Tj hrj y M rø Ξ S B S Ift -4 -4 -4 -4 to to to to
O 9J O 9J 9J O 9J O 9J 9J O 9J ft
fc Ω fcΩ fcΩ 9fc Ωfc Ωfc 9fc 9fc Ωfc 9fc Ωfc 9fc ffi ffi ffi ffi ffl ffi ffl ffl ffl ffl 999999999999 999 *
O O O O O O Q O O O Q O O O O O O Q Q O Q O O O O O O O O O O O O O O O O Irø.
oo oo O O O O 00 O 00 00 O O O O
9 9 9 Q 9 9 Ω M Ω Ω ffi Ω ffl Ω Ω ffl ΩJ Ω ffi Ω ≥! - Ωz;
O O O O O Q O O Q O Q O O O hrj hrJ Tj hή hrl hrJ TJ hd TJ htf Ti Tj Tj TJ h^ ft
9 9 9 9999 999 9 999 99 99 9 999 9 999 9 9 9 99 99 9 9 99 IX
rø j|! δ j S .? δ 5 ES ! δ J ES j^ ø
C ø ^ " C ø ^ ^ O δ 3 TJ r ø ^ ^ C0 ^ E^ ,(? øro δ^ E^S .af>? ø h^ r* C0 ø tJι r* C0 r^ C0 ^i '^ ' ON 0\ ON O
O O O O O O O O O O Q O O O O O O Q Q O Q Q O O O O O O O O Q Q O O O O ft
O O O O O O O O O O O O O O O O O O O O Q O O O O O O O O O O O O O O O O ft l&
553333 ... .6! a a a a § -g -g -s « £ £ •§ £ .5.5.§ .5 ° β ° P2> to to to to to to to to ^J ^4 »-J
O O O Q Q Q O O O Q O O Q hή hrJ hrJ TJ Tj hrJ Tj hcJ hrJ hcJ Tj TJ Tj Tj hd hcj h^
9 fc Ωfc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc ffi ffl ffl ffl ffi ffi ffi ffl ffi ffi ffi ffi ffl ffi 'x
E? rø Cd r Cd J
3 iiJ E rtS CD fl E? d ø f rø C
3 EP Θ Cd
3 E? ø
3 ES Cd rø-r' E "S g g3 E? rø
3 i §D dώ τ i-rj ES !C?D øc Hfj ft I *>
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi CD ffi ffi CD CD ffi ffi CD CD CD CD CD CD ffi ffi ffi ffi ffi ffi ffi ffi CD ffi ffi I BJ O O O O O O O O O O O O O O O O O O O Ω O Q Q O O O O O O O O O O O O O B co co co co O O O O to co
■ to to to to Q rø
TJ TJ TJ TJ TJ TJ I —4
Ugl U'Sl - USl SJ OδJ OδJ δJ OδJ OδJ OδJ OSJ . togrø .toSrø .toSrø .toirø toi rø toi rø toi rø toi rø aaa a-S røi≤ rø^ rø^ røέ røέ røέ røέ rø Ul Ul Ul Ui OJ OJ
ω ω ω ω ffl ω ω ω ω ω ω ω ffl ω ω ω ffl ffl ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9
5 ι-T E "S i§ ffi δ g" τ lif E <■S* ^ ffi δ g' δ^ ElS- ^ffi δ g' iτiJ E <S- l ffi! j-. i-rJ E <-S•■ ^ ffi δ τ ι-JT E "S ^ ffi δ ø ι-ιJ E "S ^ ffi δ p; 1-fj ES* >? ffi δ j=; % ,-T <-+ ffi pj ii ' ^
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON αN O αN ON ON ON ON ON ON ON ON ON ON ON ON ON IhrJ i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i \ri
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω l
O O O O O O O O O Q Q Q O CJ O Q O Q Ω Ω Ω Ω Ω Ω Ω Ω O Q O O O O O O O O Q
• USl 'USl U
-Sl OδJ OδJ R
w w ω w w ω ω w ffl ω w ffl w w ffl w w ω ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
R3 R4a R^ EZ B6. X S3. g4a R4b RZ ≠ X i-Bu 6-Me Cl C2F5 Br CH i-Bu 6-01 Cl C2F5 Br CH
Me 6-Me 01 «-C3F7 Br CH Me 6-C1 Cl «-C3F7 Br CH
Et 6-Me Cl «-C3F7 Br CH Et 6-C1 Cl «-C3F7 Br CH i-Pr 6-Me Cl «-C3F7 Br CH i-Pr 6-C1 Cl «-C3F7 Br CH i-Bu 6-Me Cl «-C3F7 Br CH i-Bu 6-01 Cl «-C3F7 Br CH
Me 6-Me Cl i-C3F7 Br CH Me 6-C1 01 i-C3F7 Br CH
Et 6-Me Cl i-C3F7 Br CH Et 6-C1 Cl i-C3F7 Br CH i-Pr 6-Me 01 i-C3F7 Br CH i-Pr 6-C1 Cl i-C3F7 Br CH i-Bu 6-Me Cl i-C3F7 Br CH i-Bu 6-C1 Cl i-C3F7 Br CH
Me 6-Me 01 CN Br CH Me 6-01 Cl CN Br CH
Et 6-Me Cl CN Br CH Et 6-01 Cl CN Br CH i-Pr 6-Me Cl CN Br CH i-Pr 6-01 Cl CN Br CH i-Bu 6-Me Cl CN Br CH i-Bu 6-C1 Cl CN Br CH
Me 6-Me Cl OCHF2 CF3 CH Me 6-C1 Cl OCHF2 CF3 CH
Et 6-Me Cl OCHF2 CF3 CH Et 6-01 01 OCHF2 CF3 CH i-Pr 6-Me Cl OCHF2 CF3 CH i-Pr 6-C1 Cl OCHF2 CF3 CH i-Bu 6-Me Cl OCHF2 CF3 CH i-Bu 6-01 Cl OCHF2 CF3 CH
Me 6-Me Cl SCHF2 CF3 CH Me 6-01 Cl SCHF2 CF3 CH
Et 6-Me Cl SCHF2 CF3 CH Et 6-C1 Cl SCHF2 CF3 CH i-Pr 6-Me Cl SCHF2 CF3 CH i-Pr 6-C1 Cl SCHF2 CF3 CH i-Bu 6-Me Cl SCHF2 CF3 CH i-Bu 6-C1 Cl SCHF2 CF3 CH
Me 6-Me Cl OCF3 CF3 CH Me 6-C1 01 OCF3 CF3 CH
Et 6-Me Cl OCF3 CF3 CH Et 6-C1 Cl OCF3 CF3 CH i-Pr 6-Me 01 OCF3 CF3 CH i-Pr 6-C1 Cl OCF3 CF3 CH i-Bu 6-Me Cl OCF3 CF3 CH i-Bu 6-C1 01 OCF3 CF3 CH
Me 6-Me Cl SCF3 CF3 CH Me 6-C1 Cl SCF3 CF3 CH
Et 6-Me Cl SCF3 CF3 CH Et 6-01 Cl SCF3 CF3 CH i-Pr 6-Me Cl SCF3 CF3 CH i-Pr 6-C1 Cl SCF3 CF3 CH i-Bu 6-Me Cl SCF3 CF3 CH i-Bu 6-C1 Cl SCF3 CF3 CH
Me 6-Me Cl C2F5 CF3 CH Me 6-C1 Cl C2F5 CF3 CH
Et 6-Me Cl C2F5 CF3 CH Et 6-01 Cl C2F5 CF3 CH i-Pr 6-Me Cl C2F5 CF3 CH i-Pr 6-C1 Cl C2F5 CF3 CH i-Bu 6-Me Cl C2F5 CF3 CH i-Bu 6-C1 Cl C2F5 CF3 CH
Me 6-Me Cl «-C3F7 CF3 CH Me 6-C1 Cl n-C^F-j CF3 CH
Et 6-Me Cl «-C3F7 CF3 CH Et 6-01 Cl «-C3F7 CF3 CH i-Pr 6-Me Cl H-C3F7 CF3 CH i-Pr 6-C1 Cl W-C3F-7 CF3 CH i-Bu 6-Me Cl «-C3F7 CF3 CH i-Bu 6-C1 Cl n-C3F7 CF3 CH
ft
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi K ffi ffi iπ. Ω Ω Ω Ω Ω Ω Ω Ω ft
hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hj hcj hcj Mj hcj hcj hcj TJ TJ TJ TJ TJ Tj TJ TJ 9 9 hcj TJ TJ TJ TI Tj ft
O O hcj hcj hcj hcj hcj hcj hcj hςj hcj Mcj Mcj hcj hcj hcj hcj hcj hcj hcj hcj hcj n O
TJ n TJ TJ TJ n Γ> O
TJ TJ TJ Tj Ω ffi Ω ffi Ω Ω 9 9 9 9 IX o J ffi d ffl TJ ES if CD ffl ø ft I-T E rtS D
s s Os O\ Os Os Os Os Os Os Os Os Os Os Os Os Os Os s s Os Os Os \ Os Os Os Q Q o o o o Q Q Q O O O O O Q Q Q Q O O O O O O O O O Q O O O O O O ft I P ffi ffl ffi ffl ffi ffi ffi ffi ffi ffi ffi ffl ffl ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω Ω Ω
o o o o ,9 o o o o O O S2 .Λ ?-. ?-. O y Oy Oy Og .ξ .S. 55 5Q5 0 0o 0 0o o o o o o o
^ TJ TJ TJ TJ hrj rJ hcJ TJ ft -4 -4 -4 -4 -4 -4 — J -4 Ul U %l Ul Ul O 9J 9J O 9J 9J 9J 9J O 9J 9J .rø .rø - grø . Irø 1rø 1rø Srø Srø s 9 ■^ "^ Tj TJ TJ Tj to to to to to to to to -4 -4 -4 -J
Mrj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj Mcj hcj hcj hcj hcj Mcj hcj hcj Mcj hcj hcj hcj Hcj Mcj Mcj ft
h Ocj O hcj hOcj O Hcj hQcj Q hcj O hcj hOcj O hcj O hcj O hcj O hcj O hcj O hcj O hcj O hcj O hcj hcj hj hcj hcj hcj hcj hcj hcj Hcj Mcj hcj rø ffl- Ωffl Ωffl Ωffl 9 9 9 9 '
R3 g4 R4b E7 R6 X R3. P R4b 7 R6 X
Et 6-Me H CN F CF Et 6-C1 H CN F CF i-Pr 6-Me H CN F CF i-Pr 6-C1 H CN F CF i-Bu 6-Me H CN F CF i-Bu 6-C1 H CN F CF
Me 6-Me H OCHF2 01 CC1 Me 6-01 H OCHF2 Cl CC1
Et 6-Me H OCHF2 Cl CC1 Et 6-01 H OCHF2 Cl CC1 i-Pr 6-Me H OCHF2 Cl CC1 i-Pr 6-C1 H OCHF2 Cl CC1 i-Bu 6-Me H OCHF2 Cl CC1 i-Bu 6-C1 H OCHF2 01 CC1
Me 6-Me H SCHF2 Cl CC1 Me 6-01 H SCHF2 Cl CC1
Et 6-Me H SCHF2 Cl CC1 Et 6-C1 H SCHF2 Cl CC1 i-Pr 6-Me H SCHF2 Cl CC1 i-Pr 6-C1 H SCHF2 Cl CC1 i-Bu 6-Me H SCHF2 Cl CC1 i-Bu 6-C1 H SCHF2 01 CC1
Me 6-Me H OCF3 01 CC1 Me 6-C1 H OCF3 01 CC1
Et 6-Me H OCF3 Cl CC1 Et 6-C1 H OCF3 Cl CC1 i-Pr 6-Me H OCF3 Cl CC1 i-Pr 6-01 H OCF3 Cl CC1 i-Bu 6-Me H OCF3 Cl CC1 i-Bu 6-01 H OCF3 Cl CC1
Me 6-Me H SCF3 01 CC1 Me 6-C1 H SCF3 Cl CC1
Et 6-Me H SCF3 Cl CC1 Et 6-C1 H SCF3 Cl CC1 i-Pr 6-Me H SCF3 01 CC1 i-Pr 6-C1 H SCF3 Cl CC1 i-Bu 6-Me H SCF3 Cl CC1 i-Bu 6-01 H SCF3 Cl CC1
Me 6-Me H C F5 Cl CC1 Me 6-C1 H C2F5 01 CC1
Et 6-Me H C2F5 Cl CC1 Et 6-C1 H C2F5 Cl CC1 i-Pr 6-Me H C2F5 Cl CC1 i-Pr 6-01 H C2F5 Cl CC1 i-Bu 6-Me H C2F5 Cl CC1 i-Bu 6-01 H C2F5 Cl CC1
Me 6-Me H «-C F7 Cl CC1 Me 6-C1 H n-C3F7 Cl CC1
Et 6-Me H «-C3F7 Cl CC1 Et 6-C1 H «-C3F7 01 CC1 i-Pr 6-Me H Λ-C3F7 Cl CC1 i-Pr 6-C1 H «-C3F7 01 CC1 i-Bu 6-Me H κ-C3F7 Cl CC1 i-Bu 6-01 H «-C3F7 Cl CC1
Me 6-Me H i-C3F7 Cl CC1 Me 6-01 H i-C3F7 Cl CC1
Et 6-Me H i-C3F7 Cl CC1 Et 6-C1 H i-C3F7 ' Cl CC1 i-Pr 6-Me H i-C3F7 Cl CC1 i-Pr 6-C1 H i-C3F7 01 CC1 i-Bu 6-Me H i-C3F7 Cl CC1 i-Bu 6-C1 H i-C3F7 01 CC1
Me 6-Me H CN Cl CC1 Me 6-C1 H CN 01 CC1
Et 6-Me H CN Cl CC1 Et 6-C1 H CN 01 CC1 i-Pr 6-Me H CN Cl CC1 i-Pr 6-C1 H CN 01 CC1 i-Bu 6-Me H CN Cl CC1 i-Bu 6-C1 H CN Cl CC1
II ft fc ft fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ft fc fc fc G G G t- 3 1 fcl 3 6 3 5 5 5 5 flf 8 5 5 5 5 5 5 6 5 iff S 5 5 5 ffl
$ 8 5 8 8 5 ffl 8 o
R4a R4b R9 R3 R6 R4a R4b R9 3 ≠
CH3 01 CF3 Me Br Cl CF2CHF2 Me Cl
CH3 Cl CF3 Et Br 01 CF2CHF2 Et Cl
CH3 Cl CF3 i-Pr Br 01 CF2CHF2 i-Pr 01
CH3 01 CF3 i-Bu Br Cl CF2CHF2 i-Bu Cl
CH3 Cl CH2CF3 Me Cl Cl CF2CHF2 Me Br
CH3 Cl CH2CF3 Et Cl Cl CF2CHF2 Et Br
CH3 Cl CH2CF3 i-Pr Cl Cl CF2CHF2 i-Pr Br
CH3 Cl CH2CF3 i-Bu Cl 01 CF2CHF2 i-Bu Br
CH3 01 CH2CF3 Me Br 01 CF3 CF3 Me Cl
CH3 Cl CH2CF3 Et Br Cl CF3 CF3 Et Cl
CH3 Cl CH2CF3 i-Pr Br Cl CF3 CF3 i-Pr Cl
CH3 Cl CH2CF3 i-Bu Br Cl CF3 CF3 i-Bu Cl
CH3 Cl CF2CHF2 Me Cl 01 CF3 CF3 Me Br
CH Cl CF2CHF2 Et Cl 01 CF3 CF3 Et Br
CH3 Cl CF2CHF2 i-Pr Cl Cl CF3 CF3 i-Pr Br
CH3 Cl CF2CHF2 i-Bu Cl Cl CF3 CF3 i-Bu Br
CH3 Cl CF2CHF2 Me Br Cl CF3 CH2CF3 Me Cl
CH3 Cl CF2CHF2 Et Br Cl CF3 CH2CF3 Et Cl
CH3 Cl CF2CHF2 i-Pr Br Cl CF3 CH2CF3 i-Pr Cl
CH3 Cl CF2CHF2 i-Bu Br Cl CF3 CH2CF3 i-Bu Cl
CH3 Br CF3 Me Cl Cl CF3 CH2CF3 Me Br
CH3 Br CF3 Et Cl 01 CF3 CH2CF3 Et Br
CH3 Br CF3 i-Pr Cl Cl CF3 CH2CF3 i-Pr Br
CH3 Br CF3 i-Bu Cl Cl CF3 CH2CF3 i-Bu Br
CH3 Br CF3 Me Br 01 CF3 CF2CHF2 Me 01
CH3 Br CF3 Et Br Cl CF3 CF2CHF2 Et Cl
CH3 Br CF3 i-Pr Br Cl CF3 CF2CHF2 i-Pr Cl
CH3 Br CF3 i-Bu Br Cl CF3 CF2CHF2 i-Bu 01
CH3 Br CH2CF3 Me Cl Cl CF3 CF2CHF2 Me Br
CH3 Br CH2CF3 Et Cl Cl CF3 CF2CHF2 Et Br
CH3 Br CH2CF3 i-Pr Cl Cl CF3 CF2CHF2 i-Pr Br
CH3 Br CH2CF3 i-Bu Cl 01 CF3 CF2CHF2 i-Bu Br
CH3 Br CH2CF3 Me Br Cl Cl CH2CF3 ra-Pr Cl
CH3 Br CH2CF3 Et Br Cl Cl CH2CF3 n-Bu Cl
CH3 Br CH2CF3 i-Pr Br Cl Cl CH2CF3 ,γ-Bu Cl
CH3 Br CH2CF3 i-Bu Br Cl Cl CH2CF3 i-Bu Cl
CH3 Br CF2CHF2 Me Cl Br F CF3 Me Cl
9 9 9 fc 9 fc 9 fc 9 fc 9 fc 9 fc Ω fc Ωfc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9 9 9 9 9 ft 1 P>
9 9 TJ Tj Tj TJ w H C1d ffl Cd ffl 1 ω d
&
w Cd O O O W W ffl ffl Ω Ω Ω Ω lff ffl ffl ff Ω Ω Ω Ω ffl &p ffl ffl Ω Ω Ω Ω Cd
■I ω w Cd Q o Q ft I ON
VO -4
O O O O O O O O O O O Q O Q TJ Mcj hcj hcj Mcj Mcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj β
9 9 9 o rø o rø 9 9 I Irø vo
E "S tffi? ά (Sϊ τKj S^ ffiιI fe 3 τ HJ E "S C f rø DI fl
3 i CDl δ e τKj ffl CιiDl δ e τKj M !D: δ _i røi ErS* lffi. Cd l
3 E? rø ω rø ff
3 3 3 * » ft
ffl w Ω Ω Ω Ω w κ κ ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω Ω ω ω w w Ω Ω Ω Ω rø ι-t ffl 1 rø H ffl 1 O Ω Ω ft
o o o o o o o O o 99 9 99 9 9999 9 99999 99 9999 ft 1 p.
rø Tl Tl rø Tl Tl Tl TJ rø Tl rø TJ Tl Tl TJ o o O Ω 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 \
δ δ 3 5 ES cf δ TJ
3 ES cf ffl 3 5 ES cf δ 3 5 ES f c δ 3 5 ft
υυ
hi i-i i-H ffl ffl ffl W W W ffl W ffl ffl ffl ffl ffl ffl W ffl ffl ffl W ffl ffl ffl ffl W O O Q O Q O Q O O O ft
(-)
Q Q rø ft
5? s Cd fd J ffl §
3 E? rø CD øe CD! od T iiJ rø ff rø rø Cd rø
3l 3 ! C§D- ø ffl TJ E rtS CD ø ffl I T-TJ E rtS CD ro E? rø
3 w rø ft
Ω Ω Ω EP S? SP w o o o o w w w w Ω Ω Ω Ω ffl ω w ω Ω Ω Ω Ω w I1 iw1 w1 w» of-= oh-= ofc ofc wi1 wi1 Ift
O O O O O O O Q Q Q O O O Q O O Q O O Q O Q Q O O O O O O O O O O O O O O | Ift S->
W W W Cd O O O O Q O O O O Q O O Q O Q O Q O O Q Q O Q τι τι τj τj hι. τι rø τι rø 1% O O Q rø rø Ti TJ 9 O O y O O O O to to to to n Q Q hcj hcj hcj hrj hcj hrj hcj hcj to _ Ω to _. to-. to-..9fc .9fc .9fc O Cl to to to tofif to ffi
Tj TJ TJ T Q Q Q Q to ffi π Q to ffi to ffi O O TJ TJ Tl Ω.- Tj Ω Ω rø Ω rø Ω TJ h ø
O rø n oi hoi hoi hoi hoi hoi hoi hoi thoi S S I r vo
Tl to to to to to 8 to 8 to 8 to 8333 rø rø S S S S S S rø to to to to to to to t
E? rø ffl j ES [f δ τJ ES if δ i ES if δ J ES g ft
Ω Ω ^ ffl ffl ffl Ω Ω Ω Ω 5s ω ro o o o o ω W ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω Ω EP ft
VO VO ro cd ro ro ro ro cd ffl ffl ffl ffl ffl d
1 ii 1 H ffl ii ffl ii ffl 1 ffl ffl ffl ffl ffl ffl ffl ffl Cd Cd C
II Cd Cd ffl Cd ffl Cd ffl ffl ffl Cd Cd I Itf
TJ TJ TJ TJ TJ rø rø rø rø rø TJ TJ TJ rø TJ TJ
\% o Q Q Ω Q Q Ω f Ω Ω i rø Ωrø rø Ωrø Ωrø Ωrø Ωrø Ωrø VW Ω VMΩJ VMΩJ Ω .J VΩ ffi i πfi .-J ff . to toi to ffi to ff too tto t to to to to o to ff to ffi to 9 to 9 t .o9 n Q Q Q Q 9 to o t o to to to to to .ffl .ffl .ffl .ffi .ffi ^ o TJ o r 9 9 9 I Irø vo rø rø rø rø rø r Ωø r Qø Ω 9 r 9 9 ø 9 9 9 Ω ø
TJ 9J 9 9 9 9 9 9 Tj TJ TI TJ TJ ΩTj Ω r to to toTJ toTJ toTJ toTJ to] toJ O 9J OJ . OøJ
ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl O O O W W W ffl O ft
IΛ t-
© ^ S Si fcjll G O G G ffl to ffl ffl G G G G to ffl ffl ffl G G G G ffl ffl ffl ffl G G G G Si Si ffl to m m G G G G ffl
Hi U s 3 3 3 a. Pi\ a 3 1 a S *!--. 3 1 a ft* pq a s 3 3 3 ft* 3 a ft* i a s 3 3 1 a S 3 3 1 a s 3 3
fj δ δ δ δ δ δ 8 fc δ a ffl a ffl ffl a a ffl ffi ffi in a a ta a a ffi a ffi !u a ffi a ta G G G G
3 1 cl m lff ffl ffl ffl ffl ffl to o o o o o o o o o o o o o o o o o o o o o o o o f 5 ffl 8 5 ffl 8 o fcl S li ffl ffl ffl ffl o o o o o ffl ffl ffl ffl G o G G ffl ffl ffl ffl G G G G ffl ffl ffl to G G G G
II m ffl m ffl m ffl ffl ffl a a a a a a ffl in a ffi a ffl a a ffi a ffi a a a a a a a fc fc fc fc
t- fcl o o o o 5 5 5 5 ffl 8 5 5 5 8 ffl § 8 ffi 5 5 5 3 ffi 8 3 3 3 ffi 8 8 ffi 5 5 ffl 8 5 ffl 8 5 5
© o
9 9 9 9 Ω Ω Ω Ω Ω Ω Ω Ω 9 9 9 9 9 9 9 9 Ω Ω Ω Ω Ω Ω Ω Ω 9 9 lft
ffi ffi ffi ffi ffl H? H? H? H? H? H? H? H? H? ffl ffl ffl ffl W ffl rø rø rø rø rø rø rø rø rø rø rø ft
O O O O O Q O Q Q Q O Q O O Q O O Q O Q O O O O O O O O O S TJ STJ STJ STJ STJ raTJ STJ Sτ_ ατ_ raT] HTSJ ST] raTJ lτ-S_ Sτ_ HτS_ ώT] HTJ HTS_ tTS] BT_ raT] STJ πT αTJ ShJ STJ STJ ST. SJ ΞJ ftI *I to to to to to to to to to to to to to to to to to to to to to to to to to to to to to
f rø Cd
3fl E? rø Cd TJ w Cd ø
3 3 3 ft ι-T E «*S CD H ro- T rø Cd s E? r ffl rø
3 E? fl E? rø Irø.
3 T 3 f
w ω w w w w w ω Q o W ffl w w O Q o ω ω w ro o Q O o ω ω ω lrø O o o o o Q Q θ Q o Q 9 9 9 9 9 Ω Ω Ω Ω Ω ° Ω o 9 9 lft
ffi ffi ffi ffi Tj hd TJ TJ TJ Tj rø Tj Q O Q R
Q Q Q Ω Q Q Q Q Q Ω Q Q Q Ω Q Q Q Q D Q Q Q Q Q D Q Q Q 9 „
S Tj H Tj S Tj H TJ S TJ α TJ S TJ ώ τj ώιτj ώτj raτj raιτj Hhι3 ώhcj Shι ώτι Hrø hrj τj rø τi τj ιτj rø h!_ τj h!- τι τj τj τj Kι or. J tO IO iO tO rO tO iO tO tO tO iO O tO tO tO tO tO tO tO tO tO tO tO tO tO W
p! " CD ø " C ø 1-r D £; " CD g* •* ffi H * (0
ffl ffl ffl ffl H? H? ffl » Ω Ω Ω Ω ω ω ffl ffl Ω Ω Ω Ω ω w M W Ω Ω Ω ω ffl ffl ft
Table 11
l P R4b S_. R_. g4a R4b ? R6
Me 3-Me H CF3 F Me 3-Cl H CF3 F
Et 3-Me 5-Me CHF2 F Et 3-Cl 5-Me CHF2 F i-Pr 3-Me H CHF2 F i-Pr 3-Cl H CHF2 F i-Bu 3-Me 5-Cl CH2CF3 F i-Bu 3-Cl 5-Cl CH2CF3 F
Me 3-Me H CH2CF3 F Me 3-Cl H CH2CF3 F
Et 3-Me H CF2CHF2 F Et 3-Cl H CF2CHF2 F i-Pr 3-Me 5-Br CF2CHF2 F i-Pr 3-Cl 5-Br CF2CHF2 F i-Bu 3-Me H Et F i-Bu 3-Cl H Et F propargyl 3-Me H CF3 F propargyl 3-Cl H CF3 F c-propyl 3-Me H CHF2 F c-propyl 3-Cl H CHF2 F i-Pr 3-Me 5-Cl CF3 F i-Pr 3-Cl 5-Cl CF3 F t-Bu 3-Me H «-C3F7 F t-Bu 3-Cl H «-C3F7 F
Me 3-Me 5-Cl i-C3F7 F Me 3-Cl 5-Cl i-C3F7 F
Et 3-Me H i-Pr F Et 3-Cl H i-Pr F i-Pr 3-Me H CF3 F i-Pr 3-Cl H CF3 F i-Bu 3-Me H . C2F5 F i-Bu 3-Cl H C2F5 F propargyl 3-Me H C2F5 F propargyl 3-Cl H C2F5 F c-propyl 3-Me H CF3 F c-propyl 3-Cl H CF3 F i-Pr . 3-Me H «-Pr F i-Pr 3-Cl H rc-Pr F i-Bu 3-Me 5-Br CH2CH2C1 F i-Bu 3-Cl 5-Br CH2CH2C1 F
Me 3-Me H CF3 Cl Me 3-Cl H CF3 Cl
Et 3-Me 5-Me CHF2 Cl Et 3-Cl 5-Me CHF2 Cl i-Pr 3-Me H CHF2 Cl i-Pr 3-Cl H CHF2 Cl i-Bu 3-Me 5-Cl CH2CF3 Cl i-Bu 3-Cl 5-Cl CH2CF3 Cl
Me 3-Me H CH2CF3 Cl Me 3-Cl H CH2CF3 Cl
Et 3-Me H CF2CHF2 Cl Et 3-Cl H CF2CHF2 Cl i-Pr 3-Me 5-Br CF2CHF2 Cl i-Pr 3-Cl 5-Br CF2CHF2 Cl i-Bu 3-Me H Et Cl f-Bu 3-Cl H Et Cl
U ffl ffl 9 ffl o ffl ffl ffl ffl ffl ffl ffl ffl S ffl P ffl ffl ^ ffl ffl ffl P ffl 9 ffl ffl ffl ffl ffl ffl ^ ffl ^ ffl 8
3 I fcl o o o o o o o o o o o o o o o o o o o o o o o o o υ o o o o o o o o o co co co co o co co co co co co co
P4
co o
_ O CO
^ e1 o o o o o o o o o o o p δ δ δ δ δ ft ft δ δ δ δ δ δ δ δ δ δ δ δ δ ffl ffl ffl ffl
Pil S
*J ffl ffl 9 ffi 9 ffi ffl ffl ffl ffl ffl T ffi S ffi 9 ffi ffi ffi ffl ffi 9 ffl 9 ffi ffi ffi ffi ffi ffl ρ9 ffi S ffi 9
t
C D CD D D O O ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi CD CD CD CD CD CD CD CD f ffi f CD c ffif c ffif iff f f CD f ffi I fa
VΛ |W ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ro ffi ffi ffi ffi ffi ffi j-, ffi ffl ffl ffl td ffi I
rø τj rø rø τj rø rø rø rø rø τj rø rø hrj τj hrj hrj τj hi hrj τj τj IωI ω 1 1w IωI 1ro 1ω1 ω 1 1w1 1ω1 1ro1 ω 11 iwt IwI iωt iωt l O ON
4-.
ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ro ffl ffl ffi ffi iff ffi ^ fif ω ffi
II r#
rø ES f ro rø cro τ H,j rø ■■* CgD -roj røHr E^ iCfD gro" τ HTj E <■S*■ i ffif i¬
C gD έro! rø>- ErtS fCD rώ_ τ HTj E^ iC?D rtffl τ ifj E rtS (ifI ffl rø t ed
3 T 3 ""« 3 i 3 3 ^ ■"« ft
k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k \
o l J o U o S J o . J T Ω Ω Ω Ω - *J -%J -* TJ 4 -* TJ 4 -* rø 4 -* TI Ui 4 %%%% $ $ $ $-3 Ω3 Ω3 Ω Ω ?b i b b to% to% to%# r to *ø w rø o o o o r Tj w <•- T__ OJ o o
TJ ø j TJ T hcjl h Trj! hrj TJ
-4 —J — J -4 —J -4 -4
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø rø ft o". rø Ht
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lfa
J-. J~ i- i. i- O O
,9. O ,9 £ 9 9 w w røJ røJ^ , ^9 TJ O 9J ό rj O TJJ O ό TJJ O ό røJ ^ t u % 3 ώ3 £ r u % ώ r u %r % ui I røI £ rø 1 £ rø 1 E IIp όO 9TJ' όO 9TJ oO 9TJ όO 9TJ ? E? ? S * 5? * rø .9rø .rø .9rø ^w *w s * , 9 , %9 , %9 , ^9 <-^£< <-^£, I Irøvo
-4 -4 -4 -J -4 -J -J to to to to hrj Tj Tj Tj hj hcj -J -4 -4 -4 -J — J
o o o o o o o o o o Ω Ω Ω Ω Ω Ω ^ ^ ^ Ω ^ ^ Ω Ω ^ Ω rø rø rø rø rø rø rø rø rø rø ft
R3. R4a K* s_. R6. E3. g4a R4b s2 s i-Bu 6-Me H i-C3F7 Cl i-Bu 6-C1 H i-C3F7 Cl
Me 6-Me H Et Cl Me 6-C1 H Et Cl
Et 6-Me H Et 01 Et 6-C1 H Et Cl i-Pr 6-Me H Et Cl i-Pr 6-C1 H Et Cl i-Bu 6-Me H Et Cl t-Bu 6-C1 H Et Cl
Me 6-Me H CHF2 Br Me 6-C1 H CHF2 Br
Et 6-Me H CHF2 Br Et 6-01 H CHF2 Br i-Pr 6-Me H CHF2 Br i-Pr 6-C1 H CHF2 Br i-Bu 6-Me H CHF2 Br i-Bu 6-C1 H CHF2 Br
Me 6-Me H «-Pr Br Me 6-01 H «-Pr Br
Et 6-Me H «-Pr Br Et 6-C1 H «-Pr Br i-Pr 6-Me H «-Pr Br i-Pr 6-C1 H κ-Pr Br i-Bu 6-Me H »-Pr Br i-Bu 6-C1 H n-Pr Br
Me 6-Me H CF3 Br Me 6-C1 H CF3 Br
Et 6-Me H CF3 Br Et 6-01 H CF3 Br i-Pr 6-Me H CF3 Br i-Pr 6-C1 H CF3 Br i-Bu 6-Me H CF3 Br i-Bu 6-C1 H CF3 Br
Me 6-Me H i-Pr Br Me 6-01 H i-Pr Br
Et 6-Me H i-Pr Br Et 6-C1 H i-Pr Br i-Pr 6-Me H i-Pr Br i-Pr 6-01 H i-Pr Br i-Bu 6-Me H i-Pr Br i-Bu 6-C1 H i-Pr Br
Me 6-Me H C2F5 Br Me 6-C1 H C2F5 Br
Et 6-Me H C2F5 Br Et 6-01 H C2F5 Br i-Pr 6-Me H C2F5 Br i-Pr 6-C1 H C2F5 Br i-Bu 6-Me H C2F5 Br i-Bu 6-C1 H C2F5 Br
Me 6-Me H JI-C3F7 Br Me 6-C1 H n-C3F Br
Et 6-Me H «-C3F7 Br Et 6-C1 H «-C3F7 Br i-Pr 6-Me H «-C3F7 Br i-Pr 6-C1 H «-C3F7 Br i-Bu 6-Me H «-C3F7 Br i-Bu 6-C1 H «-C3F7 Br
Me 6-Me H i-C3F7 Br Me 6-01 H i-C3F7 Br
Et 6-Me H i-C3F7 Br Et 6-C1 H i-C3F7 Br i-Pr 6-Me H i-C3F7 Br i-Pr 6-C1 H i-C3F7 Br i-Bu 6-Me H i-C3F7 Br i-Bu 6-C1 H i-C3F7 Br
Me 6-Me H Et Br Me 6-C1 H Et Br
Et 6-Me H Et Br Et 6-C1 H Et Br i-Pr 6-Me H Et Br i-Pr 6-C1 H Et Br i-Bu 6-Me H Et Br i-Bu 6-C1 H Et Br
ω
3 3 rø i CD- _W? ιT-1j r*d Cgll ctϋ! KTj E ^ CD gw rø E rtS (ifI' 2Wj rø H E «■S♦ ^ ffi gffl rfj "ES (tfI?' d ø ffl ø ffi ffl
3 E? r r
3 E? r
3 5? ø f ft
ON ON θN ιO J\ ^ σN > Λ N αN ^ θN O> σN Λ OΛ θN σN O> ON O> σN N ^ O O> 0\ t-^ ON θ\ ft D l> D <r5 r5 CD C^ C^ CD n) Ci5 CD <!D C^ CD O C^ Ct D O C CD D O I 3
Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl Irø.
£
TJ rø TJ TJ rø TJ TJ Tj rø rø rø rø rø rø rø rø TJ rø rø TJ TJ TJ TJ TJ Tj TJ TJ TJ TJ TJ Tj TJ TJ TJ TJ Tj TJ Ϊ7 OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ o
-4 g CD δ ø rø i- ES f CD δ ø rø I-T E <-S•■ i ffif δ rø E f δ Z; S
o o o σN σ^ σN ON O^ ON σN N ι-Λ ^ ON O^ N O o^ O σN N O ON σ σN ON O o σ^ ON σ σ tON σ^ ^ ON
O O O O Q Q O O O Q Q Q O CJ O Q O Q O Q O O O Q O O Q O O O O O Q Q O O O ft I 50
Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi *.
E?
TJ Tj rø TJ Tj TJ TJ TJ rø rø o rø TJ TJ TJ TJ TJ TJ hcj TJ TJ TJ hcj Tj hcj TJ TJ Tj hcj TJ Tj TJ TJ hcj TJ TJ vX OJ OJ OJ OJ OJ J J " OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ l uN
R2 R R4b R.. ≠ E g4a R4b R.. ≠
Et 6-Me Cl K-Pr F Et 6-C1 01 «-Pr F i-Pr 6-Me Cl n-Pr F i-Pr 6-C1 Cl «-Pr F i-Bu 6-Me Cl n-Pr F i-Bu 6-01 Cl n-Pr F
Me 6-Me Cl CF3 F. Me 6-C1 Cl CF3 F
Et 6-Me Cl CF3 F Et 6-C1 Cl CF3 F i-Pr 6-Me Cl CF3 F i-Pr 6-C1 Cl CF3 F i-Bu 6-Me Cl CF3 F i-Bu 6-C1 Cl CF3 F
Me 6-Me Cl i-Pr . , F Me 6-01 Cl i-Pr F
Et 6-Me Cl i-Pr F Et 6-01 Cl i-Pr F i-Pr 6-Me Cl i-Pr F i-Pr 6-01 Cl i-Pr F i-Bu 6-Me Cl i-Pr F t-Bu 6-C1 Cl i-Pr F
Me 6-Me 01 C2F5 F Me 6-01 Cl C2F5 F
Et 6-Me 01 C2F5 F Et 6-C1 Cl C2F5 F i-Pr 6-Me Cl C2F5 F i-Pr 6-C1 Cl C2F5 F i-Bu 6-Me Cl C2F5 F i-Bu 6-01 01 C2F5 F
Me 6-Me Cl «-C3F7 F Me 6-C1 01 «-C3F7 F
Et 6-Me Cl «-C3F7 F Et 6-C1 Cl n-C3F7 F i-Pr 6-Me Cl «-C3F7 F i-Pr 6-C1 Cl «-C3F7 F i-Bu 6-Me Cl «-C3F7 F i-Bu 6-C1 Cl «-C3F7 F
Me 6-Me Cl i-C3F7 F Me 6-C1 Cl i-C3F7 F
Et 6-Me Cl i-C3F7 F Et 6-C1 Cl i-C3F7 F i-Pr 6-Me Cl i-C3F7 F i-Pr 6-C1 Cl i-C3F7 F i-Bu 6-Me Cl i-C3F7 F i-Bu 6-C1 Cl i-C3F7 F
Me 6-Me Cl Et F Me 6-01 Cl Et F
Et 6-Me Cl Et F Et 6-01 Cl Et F i-Pr 6-Me Cl Et F i-Pr 6-C1 Cl Et F i-Bu 6-Me Cl Et .. F t-Bu 6-C1 Cl Et F
Me 6-Me Cl CHF2 Cl Me 6-C1 Cl CHF2 Cl
Et 6-Me Cl CHF2 Cl Et 6-C1 Cl CHF2 Cl i-Pr 6-Me Cl CHF2 01 i-Pr 6-C1 Cl CHF2 Cl i-Bu 6-Me Cl CHF2 01 i-Bu 6-C1 Cl CHF2 Cl
Me 6-Me Cl H-Pr . ci Me 6-01 Cl n-Pr Cl
Et 6-Me Cl n-Pr Cl Et 6-01 01 «-Pr Cl i-Pr 6-Me Cl «-Pr CI i-Pr 6-C1 Cl n-Pr CI i-Bu 6-Me Cl H-Pr 01 i-Bu 6-C1 01 n-Pr Cl
Me 6-Me Cl CF3 Cl Me 6-01 01 CF3 Cl
Et 6-Me Cl CF3 Cl Et 6-C1 Cl CF3 Cl
fcl G G G G G G G G G G G G G G G G G G G G G G m m m m m m m ffl ffl ffl ffl P^ m
3 I fcl o o O O O O O O O O o o o o o o
VO VO vό o o l gl gl gl ol ol oi o ■ o ■ g I g 1 o l gl ol ol ol ol ol vό vό vό vό vό vό vό vό vό vό vo VO vo VO vό vό vό vό vo vό vό vό vό vό vo vό vo vό vό vό vό vό vό
3 3 a 5 s pq ft ffl u5 "Hi ft ϋ - ffl? ώ I H _T A 3 fl - ft.l ffl5 j! a« * ft - 3 f ffl? a ^ *ai (ftfr f5 -. 3 3 fl a ft p? pq S ft ? ffl 2 pq ft ffl q
D fcl G G G G G G G G G O G G G G G G G G G G G ffl ffl m m m ffl m m m ffl ffl m m m
r— t— t — — 1 — r — r—
CO CO Si Si CN CN CN CN f fc fc fc fc r^ i^ ^ ^ ft ft ft ft ft ft ft ft ,. fcl c -H
Ei R R
^| o G G G G G G G G G G G G G G G G G G G G G G G G G G G G G O G G G G G
t- ό
90
CN
© fcl S s S p a S a S | $ s S p| a g | | a S a ft a o
B g4 R4b E2 BS E R^a g4b R9 R6 i-Bu 6-Me Cl i-Pr Br i-Bu 6-C1 Cl i-Pr Br
Me 6-Me CI C2F5 Br Me 6-CI CI C2F5 Br
Et 6-Me Cl C2F5 Br Et 6-C1 Cl C2F5 Br i-Pr 6-Me Cl C2?5 Br i-Pr 6-CI Cl C2F5 Br i-Bu 6-Me Cl C2F5 Br i-Bu 6-CI Cl C2F5 Br
Me 6-Me Cl n-C3F7 Br Me 6-CI 01 n-C3F7 Br
Et 6-Me Cl «-C3F7 Br Et 6-CI Cl n-C3F7 Br i-Pr 6-Me Cl n-C3F7 Br i-Pr 6-CI Cl n-C3F7 Br i-Bu 6-Me Cl n-C3F7 Br i-Bu 6-CI Cl n-C3F7 Br
Me 6-Me Cl i-C3F7 Br Me 6-CI Cl i-C3F7 Br
Et 6-Me Cl i-C3F7 Br Et 6-CI Cl i-C3F7 Br i-Pr 6-Me Cl i-C3F7 Br i-Pr 6-CI Cl i-C3F7 Br i-Bu 6-Me Cl i-C3F7 Br t-Bu 6-CI Cl i-C3F7 Br
Me 6-Me 01 Et Br Me 6-01 Cl Et Br
Et 6-Me 01 Et Br Et 6-CI Cl Et Br i-Pr 6-Me 01 Et Br i-Pr 6-01 01 Et Br i-Bu 6-Me 01 Et Br i-Bu 6-01 Cl Et Br
Me 6-Me 01 CHF2 CF3 Me 6-01 Cl CHF2 CF3
Et 6-Me 01 CHF2 CF3 Et 6-CI Cl CHF2 CF3 i-Pr 6-Me 01 CHF2 CF3 i-Pr 6-CI Cl CHF2 CF3 i-Bu 6-Me Cl CHF2 CF3 i-Bu 6-CI Cl CHF2 CF3
Me 6-Me Cl n-Pr CF3 Me 6-CI Cl n-Pr CF3
Et 6-Me Cl n-Pr CF3 Et 6-01 01 n-Pr CF3 i-Pr 6-Me Cl n-Pr CF3 i-Pr 6-CI Cl n-Pr CF3 i-Bu 6-Me Cl n-Pr CF3 i-Bu 6-01 Cl n-Pr CF3
Me 6-Me Cl CF3 CF3 Me 6-CI Cl CF3 CF3
Et 6-Me 01 CF3 " CF3 Et 6-01 Cl CF3 CF3 i-Pr 6-Me 01 CF3 CF3 i-Pr 6-01 Cl CF3 CF3 i-Bu 6-Me 01 CF3 CF3 ' i-Bu 6-01 Cl CF3 CF3
Me 6-Me 01 i-Pr CF3 Me 6-CI Cl i-Pr CF3
Et 6-Me 01 i-Pr CF3 Et 6-CI CI i-Pr CF3 i-Pr 6-Me 01 i-Pr "CF3 i-Pr 6-CI Cl i-Pr CF3 i-Bu 6-Me 01 i-Pr CF3 i-Bu 6-01 Cl i-Pr CF3
Me 6-Me Cl C2F5 CF3 Me 6-01 Cl C2F5 CF3
Et 6-Me 01 C2F5 CF3 Et 6-01 Cl C2F5 CF3 i-Pr 6-Me 01 C2F5 CF3 i-Pr 6-CI Cl C2F5 CF3 i-Bu 6-Me Cl C2F5 CF3 i-Bu 6-01 Cl C2F5 CF3
E? w
CD δ e T i-fJ w CD δ e % r T" ø rø Ift
Pi
^ Ω Ω Ω Ω Ω Ω Ω Ω 0 0 0 lft
9 9 9 9 9 99 99 99 99 9 ix
O Tj Orø QTj Orø OTj QTj Πrø rø Qrø Orø Drø OTj I YM^.
HM *^M MM H^ "T^ HH H™^ *^ ^M HM ^^ ^^ ^^ HH ^^ ^^ »^ H H ^^ ^^ H^ HM H^ HH HH MM MM MM ^^ MM MM ^M ^\ MM
CN t- IΛ χι 5 5 5 5 5 5 5 5 5 8 5 3 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 t-
VO
© ^j fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ft υ o υ υ υ o g o o υ o o o o o υ o o CO ffl
H CJ t— r— r- t— c— r— t— r— tn ιn ιn ιn i h h H. [iι lL l [ CN CN CN CN α. fcl ft ft - ft, - ftN., ft, ft, To co To T T T o ,*S CN C o o o g g cj cj cj w a £ £ ^ ^ ^ ^ ft ft ft ^ ft ft ft J f7N
■~ o g o g K K ε. -~ 8 8 8 8 κ s c S: O -A -~ -~ - CJ
fc fc fc fc fc fc fc fc fc fc fc HM fc fc fc fc fc fc fc fc fc
31 o o o o o o o o o o o O O O O O O O O O O O O O O O O O o o o
*ό VO VO VO VO VO VO VO VO V VO VO VO vo fcl ft pp ^ ft ffl ^ ft ffl ^ s ft ffl ^ _T * ω 4i ti 3 pq .T fc a ft « § a pq S "Hi
_-» pq ffl S «
CN 5: S s « % p
HH *^M MM ^^H HH HM HM HM ^ι HM H^ MM MM ^^ *^M MM HM MM HM μ^H ^^» ^ HH *^H '"M MM MM ^^^ ^r4 MM MM p*M ^^H HH l1M H^
XI 5 G 5"5 5 5 5 5 5 5 5 5 5 5 G 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 vo ^| fc fc fc fc fc fc fc fc fc fc fc fc fc b ft ft ft g g g g g g g g^ g u g g g g g g r— c— t— • -—• [— r— t— t— rJ? rJ? , „"? ft. ft. ft. ft- ft. ft ft ft CN CN CN CN L -. -- v> fc| ft ft ft ft ft ft ft ft ft ft CN, ft CN,
•~ -~ •- g o ε. ε. ε; ε- ••— •-» ••— •-»
*°yl I| fc fc ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi fc si iS iS iS iS iS Ji iS iS iS iS iS fi -i iS S iS iS iS iS iS S iS iS iS iS iS iS -J ώ
"^' vo vo vo vo vo vo vo vo vo vo vo vo No vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vό vo t- ό
90 nd J ^3 I s ^3 I a s I s ^3 s ^ «? I s I's ^' I a I s
CN
© o
3 R4a R4b 12 ≠ X E. R a R^ B2 R6 X i-Bu 6-Me H C2F5 Cl CH i-Bu 6-CI H C2F5 Cl CH
Me 6-Me H n-C3F7 Cl CH Me 6-CI H n-C3F7 Cl CH
Et 6-Me H «-C3F7 Cl CH Et 6-CI H n-C3F7 Cl CH i-Pr 6-Me H n-C3F7 Cl CH i-Pr 6-01 H n-C3F7 Cl CH i-Bu 6-Me H n-C3F7 Cl CH i-Bu 6-01 H n-C3F7 Cl CH
Me 6-Me H i-C3F7 Cl CH Me 6-CI H i-C3F7 Cl CH
Et 6-Me H i-C3F7 Cl CH Et 6-CI H i-C3F7 Cl CH i-Pr 6-Me H i-C3F7 Cl CH i-Pr 6-CI H i-C3F7 Cl CH i-Bu 6-Me H i-C3F7 Cl CH i-Bu 6-CI H i-C3F7 CI CH
Me 6-Me H Et 01 CH Me 6-01 H Et Cl CH
Et 6-Me H Et 01 CH Et 6-01 H Et Cl CH i-Pr 6-Me H Et 01 CH i-Pr 6-CI H Et Cl CH i-Bu 6-Me H Et 01 CH i-Bu 6-01 H Et Cl CH
Me 6-Me H CHF2 Br CH Me 6-01 H CHF2 Br CH
Et 6-Me H CHF2 Br CH Et 6-01 H CHF2 Br CH i-Pr 6-Me H CHF2 Br CH i-Pr 6-01 H CHF2 Br CH i-Bu 6-Me H CHF2 Br CH i-Bu 6-CI H CHF2 Br CH
Me 6-Me H n-Pr Br CH Me 6-CI H «-Pr Br CH
Et 6-Me H n-Pr Br CH Et 6-CI H n-Pr Br CH i-Pr 6-Me H n-Pr Br CH i-Pr 6-CI H n-Pr Br CH i-Bu 6-Me H n-Pr Br CH i-Bu 6-CI H «-Pr Br CH
Me 6-Me H CF3 Br CH Me 6-CI H CF3 Br CH
Et 6-Me H CF3 Br CH Et 6-01 H CF3 Br CH i-Pr 6-Me H CF3 Br CH i-Pr 6-01 H CF3 Br CH t-Bu 6-Me H CF3 Br CH i-Bu 6-CI H CF3 Br CH
Me 6-Me H i-Pr Br CH Me 6-CI H i-Pr Br CH
Et 6-Me H i-Pr Br CH Et 6-01 H i-Pr Br CH i-Pr 6-Me H i-Pr Br CH i-Pr 6-01 H i-Pr Br CH t-Bu 6-Me H i-Pr Br CH t-Bu 6-01 H i-Pr Br CH
Me 6-Me H C2F5 Br CH Me 6-01 H C2F5 Br CH
Et 6-Me H C2F5 Br CH Et 6-01 H C2F5 Br CH i-Pr 6-Me H C2F5 Br • CH i-Pr 6-01 H C2F5 Br CH i-Bu 6-Me H C2F5 Br CH i-Bu 6-01 H C2F5 Br CH
Me 6-Me H n-C3F7 Br CH Me 6-01 H n-C3F7 Br CH
Et 6-Me H »-C3F7 Br CH Et 6-01 H n-C3F7 Br CH i-Pr 6-Me H n-C3F7 Br CH i-Pr 6-01 H n-C3F7 Br CH i-Bu 6-Me H n-C3F7 Br CH t-Bu 6-01 H n-C3F7 Br CH
R3- g4a Rfb R£ ≠ X S3. R4a R4b R9 R6 X
Me 6-Me H i-C3F7 Br CH Me 6-CI H i-C3F7 Br CH
Et 6-Me H i-C3F7 Br CH Et 6-CI H i-C3F7 Br CH i-Pr 6-Me H i-C3F7 Br CH i-Pr 6-01 H i-C3F7 Br CH i-Bu 6-Me H i-C3F7 Br CH t-Bu 6-CI H '-C3F7 Br CH
Me 6-Me H Et Br CH Me 6-CI H Et Br CH
Et 6-Me H Et Br CH Et 6-CI H Et Br CH i-Pr 6-Me H Et Br CH i-Pr 6-CI H Et Br CH i-Bu 6-Me H Et Br CH i-Bu 6-CI H Et Br CH
Me 6-Me H CHF2 CF3 CH Me 6-CI H CHF2 CF3 CH
Et 6-Me H CHF2 CF3 CH Et 6-CI H CHF2 CF3 CH i-Pr 6-Me H CHF2 CF3 CH i-Pr 6-CI H CHF2 CF3 CH i-Bu 6-Me H CHF2 CF3 CH i-Bu 6-CI H CHF2 CF3 CH
Me 6-Me H n-Pr CF3 CH Me 6-CI H n-Pr CF3 CH
Et 6-Me H n-Pr CF3 CH Et 6-01 H n-Pr CF3 CH i-Pr 6-Me H n-Pr CF3 CH i-Pr 6-CI H n-Pr CF3 CH i-Bu 6-Me H n-Pr CF3 CH i-Bu 6-CI H n-Pr CF3 CH
Me 6-Me H CF3 CF3 CH Me 6-01 H CF3 CF3 CH
Et 6-Me H CF3 CF3 CH Et 6-CI H CF3 CF3 CH i-Pr 6-Me H CF3 CF3 CH i-Pr 6-01 H CF3 CF3 CH i-Bu 6-Me H CF3 CF3 CH i-Bu 6-01 H CF3 CF3 CH
Me 6-Me H i-Pr CF3 CH Me 6-01 H i-Pr CF3 CH
Et 6-Me H i-Pr CF3 CH Et 6-CI H i-Pr CF3 CH i-Pr 6-Me H i-Pr CF3 CH i-Pr 6-CI H i-Pr CF3 CH i-Bu 6-Me H i-Pr CF3 CH i-Bu 6-CI H i-Pr CF3 CH
Me 6-Me H C2F5 CF3 CH Me 6-CI H C2F5 CF3 CH
Et 6-Me H C2F5 CF3 CH Et 6-CI H C2F5 CF3 CH i-Pr 6-Me H C2F5 CF3 CH i-Pr 6-CI H C2F5 CF3 CH i-Bu 6-Me H C2F5 CF3 CH i-Bu 6-CI H C2F5 CF3 CH
Me 6-Me H n-C3F7 CF3 CH' Me 6-CI H n-C3F7 CF3 CH
Et 6-Me H n-C3F7 CF3 CH Et 6-CI H n-C3F7 CF3 CH i-Pr 6-Me H Λ-C3F7 CF3 CH i-Pr 6-CI H n-C3F7 CF3 CH i-Bu 6-Me H ' n-C3F7 CF3 CH i-Bu 6-CI H n-C3F7 CF3 CH
Me 6-Me H i-C3F7 CF3 CH Me 6-CI H i-C3F7 CF3 CH
Et 6-Me H i-C3F7 CF3 CH Et 6-CI H i-C3F7 CF3 CH i-Pr 6-Me H i-C3F7 CF3 CH i-Pr 6-CI H i-C3F7 CF3 CH i-Bu 6-Me H i-C3F7 CF3 CH i-Bu 6-01 H i-C3F7 CF3 CH
Me 6-Me H Et CF3 CH Me 6-CI H Et CF3 CH
si g4a Ed-l ? E_. X g4a St* -. R_. X
Et 6-Me H Et CF3 CH Et 6-CI H Et CF3 CH i-Pr 6-Me H Et CF3 CH i-Pr 6-CI H Et CF3 CH i-Bu 6-Me H Et CF3 CH i-Bu 6-01 H Et CF3 CH
Me 6-Me Cl CHF2 F CH Me 6-CI 01 CHF2 F CH
Et 6-Me Cl CHF2 F CH Et 6-CI 01 CHF2 F CH i-Pr 6-Me Cl CHF2 F CH i-Pr 6-01 01 CHF2 F CH i-Bu 6-Me Cl CHF2 F CH i-Bu 6-CI Cl CHF2 F CH
Me 6-Me Cl n-Pr F CH Me 6-CI Cl n-Pr F CH
Et 6-Me 01 n-Pr F CH Et 6-CI Cl n-Pr F CH i-Pr 6-Me 01 π-Pr F CH i-Pr 6-CI Cl n-?r F CH i-Bu 6-Me Cl n-Pr F CH t-Bu 6-CI Cl n-Pr F CH
Me 6-Me Cl CF3 F CH Me 6-CI Cl CF3 F CH
Et 6-Me Cl CF3 F CH Et 6-CI Cl CF3, F CH i-Pr 6-Me Cl CF3 F CH i-Pr 6-CI Cl CF3 F CH i-Bu 6-Me Cl CF3 F CH i-Bu 6-CI Cl CF3 F CH
Me 6-Me Cl i-Pr F CH Me 6-CI Cl i-Pr F CH
Et 6-Me Cl i-Pr F CH Et 6-01 01 i-Pr F CH i-Pr 6-Me Cl i-Pr F CH i-Pr 6-CI Cl i-Pr F CH i-Bu 6-Me Cl i-Pr F CH i-Bu 6-CI Cl i-Pr F CH
Me 6-Me Cl C2F5 F CH Me 6-CI Cl C2F5 F CH
Et 6-Me Cl C2F5 F CH Et 6-CI Cl C2F5 F CH i-Pr 6-Me Cl C2F5 F CH i-Pr 6-CI Cl C2F5 F CH i-Bu 6-Me 01 C2F5 F CH i-Bu 6-CI Cl C2 5 F CH
Me 6-Me Cl n-C3F7 F CH Me 6-01 Cl n-C3F7 F CH
Et 6-Me 01 n-C3F7 F CH Et 6-01 Cl n-C3F7 F CH i-Pr 6-Me Cl «-C3F7 F CH i-Pr 6-01 Cl n-C3F7 F CH i-Bu 6-Me 01 n-C3F7 F CH i-Bu 6-CI 01 n-C3F7 F CH
Me 6-Me Cl -C3F7 F CH Me 6-01 Cl i-C3F7 F CH
Et 6-Me Cl i-C3F7 F CH Et 6-01 Cl i-C3F7 F CH i-Pr 6-Me Cl i-C3F7 F CH i-Pr 6-01 Cl i-C3F7 F CH i-Bu 6-Me Cl i-C3F7 F CH i-Bu 6-01 Cl i-C3F7 F CH
Me 6-Me Cl ' Et F - CH Me 6-CI Cl Et F CH
Et 6-Me Cl Et F CH Et 6-CI Cl Et F CH i-Pr 6-Me Cl Et F CH i-Pr 6-01 Cl Et F CH i-Bu 6-Me Cl Et F CH i-Bu 6-CI Cl Et F CH
Me 6-Me 01 CHF2 01 CH Me 6-01 Cl CHF2 Cl CH
Et 6-Me Cl CHF2 Cl CH Et 6-CI Cl CHF2 Cl CH
El g4a g4b &_. X R3 g4a R4b E2 ≠ X i-Pr 6-Me Cl CHF2 01 CH i-Pr 6-CI Cl CHF2 Cl CH t-Bu 6-Me Cl CHF2 01 CH i-Bu 6-CI 01 CHF2 Cl CH
Me 6-Me Cl n-Pr 01 CH Me 6-CI 01 n-Pr Cl CH
Et 6-Me Cl n-Pr Cl CH Et 6-CI 01 n-Pr Cl CH i-Pr 6-Me Cl n-Pr Cl CH i-Pr 6-01 Cl n-Pr Cl CH i-Bu 6-Me Cl n-Pr Cl CH i-Bu 6-CI Cl n-Pr Cl CH
Me 6-Me Cl CF3 Cl CH Me 6-CI Cl CF3 Cl CH
Et 6-Me Cl CF3 Cl CH Et 6-CI Cl CF3 Cl CH i-Pr 6-Me 01 CF3 Cl CH i-Pr 6-CI Cl CF3 Cl CH i-Bu 6-Me Cl CF3 Cl CH i-Bu 6-CI Cl CF3 Cl CH
Me 6-Me Cl i-Pr Cl CH Me 6-CI Cl i-Pr 01 CH
Et 6-Me Cl i-Pr Cl CH Et 6-CI Cl i-Pr 01 CH i-Pr 6-Me Cl i-Pr Cl CH i-Pr 6-CI Cl i-Pr 01 CH i-Bu 6-Me Cl i-Pr Cl CH i-Bu 6-CI Cl i-Pr 01 CH
Me 6-Me Cl C2F5 Cl CH Me 6-CI Cl C2 5 01 CH
Et 6-Me Cl C2 5 Cl CH Et 6-CI 01 C2F5 Cl CH i-Pr 6-Me Cl C2F5 Cl CH i-Pr 6-CI Cl C2F5 Cl CH i-Bu 6-Me Cl C2F5 Cl CH i-Bu 6-01 01 C2F5 Cl CH
Me 6-Me Cl n-C3F7 Cl CH Me 6-01 Cl n-C3F7 Cl CH
Et 6-Me Cl n-C3F7 Cl CH Et 6-CI 01 "-C3 7 Cl CH i-Pr 6-Me Cl , n-C3F7 Cl CH i-Pr 6-CI Cl «-C3F7 Cl CH i-Bu 6-Me Cl n-C3F7 Cl CH i-Bu 6-01 01 "-C3 7 Cl CH
Me 6-Me Cl i-C3F7 01 CH Me 6-01 01 i-C3F7 Cl CH
Et 6-Me 01 i-C3F7 01 CH Et 6-01 Cl i-C3F7 Cl CH i-Pr 6-Me Cl i-C3F7 Cl CH i-Pr 6-CI Cl i-C3F7 Cl CH i-Bu 6-Me Cl i-C3F7 Cl CH i-Bu 6-01 Cl i-C3F7 Cl CH
Me 6-Me Cl Et Cl CH Me 6-01 Cl Et Cl CH
Et 6-Me Cl Et Cl CH Et 6-01 Cl Et Cl CH i-Pr 6-Me Cl Et Cl CH i-Pr 6-01 Cl Et Cl CH i-Bu 6-Me 01 Et 01 CH i-Bu 6-01 Cl Et Cl CH
Me 6-Me Cl CHF2 Br CH Me 6-01 Cl CHF2 Br CH
Et 6-Me Cl ' CHF2 Br CH Et 6-01 Cl CHF2 Br CH i-Pr 6-Me Cl CHF2 Br CH i-Pr 6-CI Cl CHF2 Br CH i-Bu 6-Me Cl CHF2 Br CH i-Bu 6-CI Cl CHF2 Br CH
Me 6-Me Cl n-Pr Br CH Me 6-CI Cl n-Pr Br CH
Et 6-Me Cl n-Pr Br CH Et 6-CI Cl n-Pr Br CH i-Pr 6-Me Cl n-Pr Br CH i-Pr 6-CI 01 n-Pr Br CH
δ β røι-1' ErtS ^CD S τJ ES s f?> ffl 3 δ i-T E^ it? ffl rø rø $ $ ES ώ H? ES ώ J ES §£ ffl J ES ffl
3 5 ES f δ ft
Os OS Os OS Os Os Os Os Os Os Os Os Os Os Os s θs s s Os s Os Os θs Os s Os Os s s s θs θs s Os k CD kCD kCD kO kCD kD kD kCD kCD kCD kCD kCD kD k CD kCD kCD kCD kCD kD kCD kCD kCD kCD kD kCD kCD kCD kCD kCD kCD kCD kCD kCD kCD kCD kD k ft CD
O O O O O O O O Q Q Q Q Q Q Ω Ω O Q Q Ω O O Q O Q Q O Q Q Q O O O
\%
Ω Ω Ω Ω Si a a a J rø ør y HH. OJ J OJ oJ o O ,o to O ? hcj t to O 333 i v- Ω Ω <"J vθ hcj r TI J M TcjJ « hrj o E? ft vo to to g to § to 8 w TJ Tj rø TJ j Tj rø ft
—J -J -4 -J -4 rø -øJ -4 -4
TJ TJ TJ rø rø TJ TJ hcj rø TJ rø Tj ω ffl ffl cd ϋd rø cd ffl ro ro td ro ro cd ro ffl ro cd ffl ffl ffl ffl ffl ffl ro lrø-.
999 Ω 9 9 9 9 Ω ffl 99 9 9 9 9 9 9 9 9 9 9 9 9 Ω 9 Ω9 999999999 ι ro E? rø « E? W I fJ iro røi-t' E^ if! ro rø' ES ! ro τj ES ^ ro rø' ES i! ro . ES ^ ro rø' rø fi f fi C il ^ C a" •■♦ ffi j? πf ** ffi *i *+ CO & H f c ffi ffl 3 3 ES ω rø.
3 σ 0 --^ σ O O σ^ 0^ σ σ^ σ σ^ O O^ O O O ^ σ σ^ σ ^
• ' ' ' * ' ' ' -L- - - -i.. ^. -L-
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω | Iftpo
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O O O O O O O O O O O O O O Q Q Q O Q Q Q O Q O
%
k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k ft
ffl ffl ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffi ffi ffi ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω
o ~. v a r rø rø 9 9 9 9 ? O ø rø ,Q A. to O to O to o to o
U rø Tl rø V , TJ Tj rø l U 8 § € @ E ES ES ES <° ? J? o o o o to to rø Tl Ui Ui E? E? ft -4
rø TI rø rø rø rø ft
9 9 9 9 9 9 9 9 9 9 ffl ffl tn ffl ffi ffi ffi ffl ffi ffi ffi ffl IX
S ώ ζ ES f ro rø ES if ro ^ ES lff ES sf o ω ffl
3 EP r rø ES ffl rø ES ffl rø' ES rø
3 3 rø rø ft
Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os o o o o o π o π o o o o o o o o o o o o o o o o o o o o o o o o o o o o o ft
ffl ffl ffl K K K ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω & o a a a
7- O O O Ω Ω r rø TJ W W o o o o o o O O to o to t to t? E? E? T Tl ø rø rø rø Irøvo to t to to ^ørt -ørJ - rø4 -4ør r rø r rø rø rø rø E? E? i
-øJ 1 - rø E? s? J -øJ
rø TJ rø Tj ^ O O O O O O O Q O Q Q Q Q Q Q Q Q Q Q Q ft I ON
Ω rø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffl Ωffi Ωffi Ωffi Ωffi Ωffl ffi ffi ffi IX
w r
3 ω E? E ^S ffi^ Cro ,T E nif ro Ϊ^ E ΛlJ Sro ^ζ ES n^ ro '^ ES Λ^ 3ro 'røl' ES C^ ero; HTj E<^ Ci? Cd ø Iø
3 rø ø r.
3 ω r
0\ Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os O\ Os Os s O Os Os Os Os Os Os s Os Os s Os Os s s PL ffi ffi ffi CD ffi CD ffi ffi ffi ffi CD CD CD CD ffi CD CD CD CD ffi CD CD. CD CD CD CD ffi CD ffi CD D ffi ffi ffi ffi ffi ffi
Irø.
&
to o-1
1 ft
o o Q Ω Ω Ω Ω Ω Ω ^ Ω Ω Ω ^ ^ ^ ^ ^ ^ Ω Ω rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø Ift
_^ θN θN OΛ O θ θ\ ^ ON σN I-^ OΛ θN θΛ ON θN θΛ θN θ ^ ON θ σN θN θN θ θ θN ^ N θN σN θΛ θN σ σ θN
O O O O O O Q Ω Ω Ω Ω Ω Ω O Q Q O Q Q O O O O O Q O O Q O O Ω O O O O O O ft P
K K HH HH ffi ffi ffi W H HM HH H HH ffi
§ .g -§tf VO
<*] «*J % ^ -§ .§ 55555 j 9 * § ^ g ' *g * g s B B B **J *-4 ^4 *-J «*J *-j -J -^J
o o o o o o Q Ω Ω Ω Ω Ω
O O O O O O O O O O O O O O O O O O O O O O Π O O O O O O O O O O O O O O O O O Q Q O O O Q O O O O Ω θ y rø rø rø rø y y rø rø τj y y y j lX
R R4a R4b R9 R6 X R3 .4a R4b R9 Rθ X i-Pr 6-Me H n-C3F7 Cl CC1 i-Pr 6-CI H n-C3F7 01 CC1 i-Bu 6-Me H n-C3F7 Cl CC1 i-Bu 6-01 H n-C3F7 Cl CC1
Me 6-Me H i-C3F7 Cl CC1 Me 6-CI H i-C3F7 Cl CC1
Et 6-Me H i-C3F7 Cl CC1 Et 6-CI H i-C3F7 Cl CC1 i-Pr 6-Me H i-C3F7 Cl CC1 i-Pr 6-CI H i-C3F7 01 CC1 i-Bu 6-Me H i-C3F7 Cl CC1 i-Bu 6-CI H i-C3F7 Cl CC1
Me 6-Me H Et Cl CC1 Me 6-01 H Et Cl CC1
Et 6-Me H Et Cl CC1 Et 6-01 H Et Cl CC1 i-Pr 6-Me H Et Cl CC1 i-Pr 6-CI H Et Cl CC1 i-Bu 6-Me H Et Cl CC1 i-Bu 6-01 H Et Cl CC1
Table 13
R4a R4b R7 R R6 R4a R4b R7 R3 R6 R4a R4b R7 R R6
CH3 F CF3 Me 01 01 F CF3 Me Cl Br F CF3 Me Cl
CH3 F CF3 Et Cl 01 F CF3 Et Cl Br F CF3 Et Cl
CH3 F CF3 i-Pr Cl Cl F CF3 i-Pr Cl Br F CF3 i-Pr Cl
CH3 F CF3 i-Bu Cl Cl F CF3 t-Bu Cl Br F CF3 i-Bu Cl
CH3 F CF3 Me Br Cl F CF3 Me Br Br F CF3 Me Br
CH3 F CF3 Et Br Cl F CF3 Et Br Br F CF3 Et Br
CH3 F CF3 i-Pr Br Cl F CF i-Pr Br Br F CF3 i-Pr Br
CH3 F CF3 i-Bu Br Cl F CF3 i-Bu Br Br F CF3 i-Bu Br
CH3 F Cl Me Cl 01 F Cl Me Cl Br F Cl Me Cl
CH3 F Cl Et Cl Cl F Cl Et Cl Br F Cl Et Cl
CH3 F Cl i-Pr Cl 01 F Cl i-Pr Cl Br F Cl i-Pr Cl
CH3 F Cl i-Bu 01 Cl F Cl i-Bu Cl Br F Cl i-Bu Cl
CH3 F Cl Me Br Cl F Cl Me Br Br F Cl Me Br
CH3 F Cl Et Br Cl F Cl Et Br Br F Cl Et Br
IΛ t-
S
© Pi ffl to G G G G m m m ffl G G G G to to ffl ffl G G G G ffl to m ffl G G G G ffl m ffl ffl G G ffl 3 3
H fc s 3 ffl CJ a 5 3 a s 3 3
3 a $ 3 1 a s 3 1 a 3
5 3 a 3
5 3 a 3
S 3 a 3
5 3 1 a ft co fc G G ffl pq ffl ffl m m ffl ffl υ fc δ δ δ δ δ δ fc 8 o o o o o o υ o m m m ffl m ffl m m δ δ fc fc fc fc fc fc fc fc fc fc
% o o o o o g o g o o o o o o o o g g o o ffl ffl cα Si Si S Si fc ffl to ffl ffl ffl ffl ffl m ffl ffl ffl ffl to to to ffl ffl ffl m ffl pq ffl ffl ffl to ffl ffl to ffl ffl ffl ffl ffl ffl to m o . i! ffl ffl G G G G m ffl ffl ffl G g G G to m m ffl G G G G m ffl ffl ffl G G G G ffl ffl m to G G
CN fc G G ffl ffl ffl ffl m ffl ffl pq δ δ 8 fc fc 8 fc 8 δ δ S o o o o o pq ffl ffl m m ffl ffl m δ δ fc fc fc fc fc fc fc fc ft fc o O o o o o o o o o o o o o o o ffl pq cα fc o o u o o o o o o o o o o o o o o o o υ o o o o o o o o o o o
3 3 fc 3 1 a 3
5 3 a 3
S pq a 3
5 3 a s 3 3 a s 3 3 to s pq J. a 3
5 pq 1 a s 3
3 1 to co fc G o ffl ffl ffl ffl to m ffl ffl fc g 8 fc δ fc g δ δ δ δ o o o o o o ffl ffl m ffl ffl ffl ffl ffl δ δ fj fc fc fc fc fc fc fc fc fc fc o o o o o o o o o o υ o o o υ o o O o o m m t- 3 1 co co co co fcl ffl 8 5 5 5 5 5 5 5 5 5 5 ffl 8 8 ffl 5 5 5 5 5 5 8 ffl ffl 8 5 ffl 8 ffl 8 8 ffl 5 5 5 5 5 5 ffl 8 5 ffl 8 ffl 8 5 o
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 ft 1
O o O O O o o o 9 9 9 9 9 9 9 9 Cd Cd ffl Cd o Cd ι-t r ω ω o O o o o O O 9 9 9 9 9 ft δ 3 E? ES cf δ 3 5 ES cf δ 3 5 ES cf δ 3 E? ES cf δ 3 5 ES cf 3 δ 5 ES f δ 3 5 ES f δ 3 S ES f 3 δ S ES cf 3 δ ft
O o o o O o o O o O o O O o o O O O o O o o O O O O o o o o o O O o o O o ft ro Cd ro ro ffl ffl ffl ffl flf ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Cd Cd Cd Cd ffl ffl Cd Cd Cd
O O O o Cd Cd ro Cd Cd W Cd Cd O o o o o o o O 9 9 9 9 9 9 9 9 O Q O O 9 9 9 9 9 t ft
ω Cd ro Cd Cd W Cd Cd Ω Q Ω O EP Cd w Cd ii Q Ω Q Q Cd w Cd ffl o Ω Q Q o Ω Q Ω EP Cd ffl ω O ft ffl ffl ω ω w ω ω w EP ffl Cd Cd fl w EP ffl Cd ω Cd
T f T W B? ω ω ffl •I B? ro w ffl Cd ω Cd ω ffl w ffl ω ffl ft
BP BP ffl Cd r Cd BP ffl w lff d Cd ι-» o ii ffl C
T $ Cd ffl ffl ω ro ro Cd
T %
O O O O O O O O 9 9 9 9 9 9 9 9 Cd ω Cd Cd EP ro Cd ffl O o o O o o O O 9 9 9 9 9 ^
fc 9 fc c J O9 f J O9 fc J O9 c fc J O9f J O9 fc J O9 fc J O9J
O9J O9J O9J O9J O9J O9J O9J ftI P
K Ω "^ Ω^^ Ω Ω^^ O9J O9J O9J O9J O9J O9J O9J O9 O9J O9J O9J O9J O9J O9J O9J O9J O9J O9J O9J 9J O9J O9J O9 9 , ._ .-. M « ,1 >_ I lftάr1 ω 9 Ω H- ΩH- ΩHI ΩH1 511j ω II ω 11 ω 11 ω 11 ω II ω 11 ω H-t Ω >-* Ω-' Ωh-, Ω,-α Ω>- Ωh-' Ω>-J Ω>-' θ9J O9J O9J O9J O9J O9J O9J O9J ^ffl ffl ^ ω ffl• ffl■ ffl ffl T ffl 1 |1rø-41
C gD 3 δ3 3ro rø11 δ3 δ i-i E^S fCD δ rø ES f δ ø rø E "S■ f CD δ ø τ HtJ E ^ ffig δ ø δ E "S i ffif δ ø δ H ES f & δ ø δ ι-r E <-*■ j ffi δ ø δ >1 rtE C§J: ft I "
Ω Ω Ω Ω Ω κ ffl ffl ffl Ω Ω Ω Ω Ep ffl EP EP Ω Ω Ω Ω ω ffl ffl ffl Ω Ω Ω Ω w B? ffl ffl Ω Ω Ω Ω ft
0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ft
O ΩJ OΩJ OΩJ OΩJ OQJ M M M M M M M M M „ M H M M M M M M M M HI I-H W H HW 1 Hi H, l-, H, H, | *! l fl t
O ΩJ O9J O9J O9J O9J ff1-1 ffl l"> ffl -1 f ^ ffl ^ ffl ^ ffl -* ffl o ^ o^ o- o- o- o- o- o- O9J O9J 9J O9J O9J 9J O9J O9J ffl1-1 ffl -• ffl -« ffl -1 ffl -1 ffl -1 ffl "« ffl -i |li;;-dJ J g CD ώ rø 11 ES fi CD øffl ^ H E *S+ f CO øro rø H ES+ f CO ffl ^ E "^S f ffi ffl rø i-T E "^S ^ ffi øffl rø ES tf CO øffl rø ES f CO ffl ø rø Ht E rtS if ffi øro rø ι-r E «■S+ if ffi ft ' **>
H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? ffl ffl ffl Ω Ω Ω ° ft
HH i-H Hi ι-ι >-H ro ro ro ro ro ro ro ro ro ro ro ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Cd ffl ffl ffl ro ro r-
Ω "— ^ Ω^^ Ω"-^ Ω Ω^^ o9j o9j o9J O9J O9J O9J 9J O9J O9J O9J O9J O9J O9J 9J O9J 9J O9J 9J O9J O9O9J O9J O9J O9J - - ft l άr*
O 9J OJ O9J OJ OJ ffl ^ H?» H ^? H ^? H? H ^? H?• H?• Ω — Ω — Ω ^ Ω ^ Ω ^ ^ Ω ^ Ω ^ O9J 9J O9J 9J 9J O9J OJ O9J ffl ^ H? H? H? H? H? ω ^ s Tj l I?d -4, CO pj > ffl Ω Ω
g4a R4b EZ El R6 g R44aa R4b R7 R3 R6 R4a R4T> R7 R R6
CH H CF3 Et Cl Cl CF CF Et Br Cl CF3 Et Br
CH3 H CF3 i-Pr 01 Cl CF3 CF i-Pr Br Cl CF3 i-Pr Br
CH3 H CF3 i-Bu Cl 01 CF CF3 i-Bu Br 01 CF3 i-Bu Br
CH3 H CF3 Me Br Cl CF3 Cl Me Cl Cl Cl Me Cl
CH3 H CF3 Et Br Cl CF3 Cl Et Cl Cl 01 Et Cl
CH3 H CF3 i-Pr Br 01 CF3 Cl i-Pr 01 01 Cl i-Pr Cl
CH3 H CF3 i-Bu Br 01 CF Cl i-Bu Cl Cl Cl i-Bu Cl
CH3 H Cl Me 01 01 CF3 Cl Me Br Cl Cl Me Br
CH3 H Cl Et Cl Cl CF3 Cl Et Br Cl Cl Et Br
CH3 H Cl i-Pr Cl Cl CF Cl i-Pr Br 01 Cl i-Pr Br
CH3 H Cl i-Bu Cl Cl CF3 01 i-Bu Br Cl Cl i-Bu Br
CH3 H Cl Me Br Cl CF3 Br Me Cl Cl Br Me Cl
CH3 H Cl Et Br Cl CF3 Br Et Cl Cl Br Et Cl
CH3 H Cl i-Pr Br Cl CF3 Br i-Pr Cl Cl Br i-Pr Cl
CH3 H Cl i-Bu Br 01 CF3 Br i-Bu Cl Cl Br i-Bu Cl
CH3 H Br Me Cl 01 CF3 Br Me Br Cl Br Me Br
CH3 H Br Et Cl Cl CF3 Br Et Br 01 Br Et Br
CH3 H Br i-Pr Cl Cl CF3 Br i-Pr Br 01 Br i-Pr Br
CH3 H Br i-Bu Cl 01 CF3 Br i-Bu Br 01 Br i-Bu Br
CH3 H Br Me Br Cl 01 01 n-Pr Cl H CF3 Me Cl
CH3 H Br Et Br Cl Cl Cl n-Bu 01 H CF3 Et Cl
CH3 H Br i-Pr Br Cl Cl Cl s-Bu Cl H CF3 i-Pr Cl
CH3 H Br i-Bu Br Cl 01 01 i-Bu Cl H CF3 i-Bu Cl
Table 14
fi! R4a E4b R7 R6 El R4a R4b EZ E6.
Me 3-Me H CF3 F Me 3-Cl H CF3 F
Et 3-Me 5-Me OCF3 F Et 3-Cl 5-Me 0CF3 F
ffl ffl ffl Q ffl o ffl ffl ffl ro ffl ffl o ffl ffl T* ffl ffl ffl ffl ffl ffl Q ffl Q ffl ffl ffl to ffl ffl ό ffl ffl ω fc
ω ffl ffl ro ω ω Cd ω Cd ω Cd Cd B? ω Cd EP 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Q Ift ts>
5 ES cf § i 1rø OJ
Irø
O ό 6 6 ό ό ό ό ό ό ό ό o ό ό ό O ό ό ό ό ό ό ό O ό ό ό ό ό ό 1 p
ffl ffl ffl Ω ffl o ffl ffl ffl ro ι-t ffl ffl o ffl ffl to ffl ffl ffl ffl ffl ffi Ω ffl O ffi ffl ffl to ffl ffl ό ffl Ϊ ffi ro fc
E? Cd Cd BP EP Cd κ ω ω W W E? Cd Cd d W 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Ω Ift
t-h k CD
W HM MM *^M "^M ^^ MM ^^ MM HM MM *^ H^ MM MM μ*M *^ MM MM HH HM MM HM MM Hπ MM MM MM MM ^^ HM MM W . 'l ^^ MM r^^ l It*d ». fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc td ft i cy
<— • 51 .2 S S oo oo oo oo O O O O t -4 -J -4 -4 -J -4 -4 -J to to to to to to to to
0N 0Λ ^ 0N 0N 0 0N 0N σN 0N 0N 0N O\ 0Λ 0N σN 0 0Λ 0N 0N 0N σN σN 0N S N 0N σN σN 0N 0N 0N 0N OJ OJ OJ OJ JHH l l l l l l l t l l l l l l l l l l l l l l l l l l l l l l l l l l l l l JiΥ
Q Q Q Q Q D Q Q Q Q Q Q Q Q G Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q l
Q n n n $ ^ $ h h h Si Si Si Si ^ ^ ^ ^ ^ ^ ^ ^ Q Ω Ω Ω Ω Ω Ω Ω n ^ Ω t
% « ^ w^ ^ -% •% •«, j j? j S S 55 S S S 55 .a € s. s ^ ^ ? Ift to -4 — 4 — J -4 —J -J -4 -4 to to to to to to to to
•— rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø ør rø W 11 W it W ii W ii | Irø O
R R4a R4b R7 R6 R3 R4a R4b R7 R6
Et 6-Me H OCHF2 Cl Et 6-CI H OCHF2 Cl i-Pr 6-Me H OCHF2 Cl i-Pr 6-CI H OCHF2 Cl i-Bu 6-Me H OCHF2 01 i-Bu 6-CI H OCHF2 Cl
Me 6-Me H SCHF2 Cl Me 6-CI H SCHF2 Cl
Et 6-Me H SCHF2 Cl Et 6-CI H SCHF2 Cl i-Pr 6-Me H SCHF2 Cl i-Pr 6-CI H SCHF2 01 i-Bu 6-Me H SCHF2 Cl i-Bu 6-CI H SCHF2 Cl
Me 6-Me H OCF3 Cl Me 6-CI H OCF3 Cl
Et 6-Me H OCF3 Cl Et 6-CI H OCF3 Cl i-Pr 6-Me H OCF3 Cl i-Pr 6-CI H OCF3 Cl i-Bu 6-Me H OCF3 01 i-Bu 6-CI H OCF3 01
Me 6-Me H SCF3 Cl Me 6-CI H SCF3 01
Et 6-Me H SCF3 Cl Et 6-CI H SCF3 Cl i-Pr 6-Me H SCF3 01 i-Pr 6-CI H SCF3 Cl i-Bu 6-Me H SCF3 Cl i-Bu 6-CI H SCF3 Cl
Me 6-Me H C2F5 Cl Me 6-CI H C2F5 Cl
Et 6-Me H C2F5 Cl Et 6-CI H C F5 Cl i-Pr 6-Me H C F5 Cl i-Pr 6-CI H C2F5 Cl t-Bu 6-Me H C2F5 Cl i-Bu 6-CI H C2F5 Cl
Me 6-Me H n-C3F7 Cl Me 6-01 H n-C3F7 Cl
Et 6-Me H n-C3F7 01 Et 6-CI H n-C3F7 Cl i-Pr 6-Me H n-C3F7 Cl i-Pr 6-CI H n-C3F7 Cl i-Bu 6-Me H n-C3F7 Cl i-Bu 6-CI H n-C3F7 Cl
Me 6-Me H i-C3F7 Cl Me 6-CI H i-C3F7 Cl
Et 6-Me H i-C3F7 Cl Et 6-01 H i-C3F7 Cl i-Pr 6-Me H i-C3F7 Cl i-Pr 6-CI H i-C3F7 Cl i-Bu 6-Me H i-C3F7 Cl i-Bu 6-CI H i-C3F7 Cl
Me 6-Me H CN Cl Me 6-CI H CN Cl
Et 6-Me H CN Cl Et 6-01 H CN Cl i-Pr 6-Me H CN Cl i-Pr 6-CI H CN Cl i-Bu 6-Me H CN Cl i-Bu 6-CI H CN Cl
Me 6-Me H OCHF2 Br Me 6-CI H OCHF2 Br
Et 6-Me H OCHF2 Br Et 6-CI H OCHF2 Br i-Pr 6-Me H OCHF2 Br i-Pr 6-CI H OCHF2 Br i-Bu 6-Me H OCHF2 Br i-Bu 6-CI H OCHF2 Br
Me 6-Me H SCHF2 Br Me 6-CI H SCHF2 Br
Et 6-Me H SCHF2 Br Et 6-CI H SCHF2 Br
•5? W ώ j ES f ώ g ES f ώ E? W
3 ffl E? rø Cd
3 E? rø Cd rø
3 gD δ δ E "S f CD Ja røK ES tfCD δ Jfj δ ι-r ft I J
ON ON ON ON ON ON ON ON ON ON ON ON ON V. Os Os Os Os Os OS Os Os Os Os Os fD CD Λ Ϊ Ϊ C^ CD O CD CB CD C O C CD Λ ls c^ rt fD O cϊ fD β CD O CD O Λ fD fD ϊ CD CD CD I ft p
p-l ^M HH W ffi ffi ffi ffi ffi W ffi Irø.
&
o o o oo oo oo oo O O O O v J-. ai ai a■
§ 88 O OJ OOJ OOJ ,9J OOJ OOJ O
TJ TI TI TJ hcj to8to8to8to8to8to8to to88838
t- 9o o9J O9J O9J O9J 9J O9J O9J iJ9o o9J O9J ffl1-1 ffl -1 ffl| ffl -* ffl ^ ffl -• -ffl1 ffl ", ffl -« ffl' ffl -• ffl -1 ffl ^ w ^ "w* ffl Cd ro Cd
1 ro Cd Cd
1 ro Cd Cd ro 1 1 ft ON
VO
O Q Q O Q Q O O Q O O O O ft
ffi ffl ffl ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffl ffi ffl ffl ffi ffi ffi ffi PL
O oo ΓoN
TJ hrj TJ TJ TJ TJ TJ TJ rø TJ hcj ro cd cd cd cd cd cd cd ro ro ro cd ro ro rø ro ffl ffl ro ro cd ro cd ro ro ro ft
3 ro' δ Ht E 1S- CD ∞ g- i E <■* if ffi or ø T nfJ <t W■*d dd or r o δ ES if or
3 e 3 EP ø
$ ør ϊ ES f r
3 Λ jj T πfJ E «"S*■ C gD Cd
3 E? rø ώ pg,
ON ON ON ON ON ft
O Clϊ Cι5 0 G> O CΪ D Cl> Ct lϊ CΪ Ct C^ O Ct CD C CD O Cl> O O CD Cl> C^ I 3
O O O O O O Q Q Q O O Q O O O O K ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ft
00 00 00 _ --. _ oo oo oo oo O O O O -•. a a o3 o3 R 8 8 R 9 9 9 9 Ω Ω Ω Ω o o o o ^ < r- o 00 OO 00 O to n o
Tj TJ 9 TJ 3 TJ 3 hrj 3 Tj 3 Tj 3 % % % % % % % % * * * * '? ? * * * OJ rj τι rø Tl o TJ o rø f rø ϊ r> o TJ Ui rø rø Ift to to to to to to to to -4
Tj hcj Mcj hcj hcj hcj hcj hcj hcj hcj hcj ^ hcj O hcj O Mcj Q Tj O hcj O Hij O Mcj O Tj O Tj Π hcj Q hcj Π hcj Π hcj O hcj O hcj O hcj O hcj O hcj ^ hcj o c hc 3j o u hcj π y hcj
OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft υ o δ g" δ t-f E •*S ^ « δ a δ ii E "S o^ ero δii ES ^D »ro δ HT E <ιS- i «f —ro rø i-t' rø W W
3 ør H Cd
3 δ π E *^S i CfD gώ* rø μ-f E "S• i^D ώ ? δ μf E "S Oif cro. ft1 J
Q Q O O Q Q n O O O O O O O Q Q Q O O I Ift p
O O O O O Q O O Q O |ι5 K |ιj iιj >ι| !ι3 |ιj ]ιj a κ |ιj a ffi ffl ft
8 O .5J5 OJ5 OJ. o8J55 "-"
TJ TJ TJ TJ TJ hcj hrj TJ hcj TJ TJ TJ hrj ^ hcj O hcj O O Hcj O hjj O Mcj O Mcj O Mcj O hcj O Tj O Tj O hcj Q hcj O hrj O hcj O hcj O hcj O hcj O hcj Q Tj Q hcj Q Tj
OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft
ro E? rø « ø Cd rø Cd rø Cd r rø or .
3 3 E? r
3 3 3 ø 3 rø S ø Cd δf rffl* aδ s 3δs δi!--r! E^ iSffi 3 tδi δi ι-t E^S lffiM'1 rø
O^ N σN σN ON O O σ^ ON ON O ON O σ^ o σN O^ σ σ^ σN O σN σ σN O^ o^ σ^ o o^ σN σN O ON
Cϊ O CD C^ C O O CΪ CD CΪ CD Ϊϊ Clϊ C O CΪ CD CΪ CΪ O CB cϊ CΪ CD D C CD
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø ft u
C gD δ ø δ E i CfD δ p; δ i-f E rtS f CD
ft 1 °J
O ON O C^ OΛ ON Λ ON ON ^ σN O CJN ON CΛ O αN ON ON αN OΛ i-Λ ON αN ON OΛ C^
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lέ"
O O O O O O Q O O O O O O O Q O O O Q O O O O O O O O O O O O O O O O O o ft
rø-Ugt U'gl U'gl U'Si OδJ OδJ OδJ OaJ δJ OδJ O _ ^^ δJ OStolrø toirø toSrø toSrø tolrø tolrø r tlrø tolrøaaaarø rø rø øirø rø rø rø U -4 -4 -4 -4 -4 -J -4 -4'Sl U'Si'Ugl U'Sl ^ R.
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø rø ft
r. t- IΛ t- ^1 o o o o o o o o o o to ffl ffl m ffl to to m ffl ffl ffl ffl ffl m q lff ffl m m flf ffl m r-. m ffl
fc r- r- r- fc fc r- fc r- t- r— CN CN CN CN cN cN cN CN fc fc fc fc fc fc fc fc fc [__, ___ , o co co co co o o in i i i i fc fc fc fc rf. ffl & a a a a a h h h ft ft
H ^ U o o G G G a a ft ft ^, ft, tf, ft co To co co 70 u u o o G CJ S K ft
% g g o o g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g g
3 I o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
ϋl o o o o o o o o ffl q ffl ffl m m m ffl ffl ffl m m m ffl q ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl
tjo o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
3 I
t-
3 3 3 3 3 3 3 s. a ft ffl ft fflo? ^ a ft o ffl? a _- ft. 3 ffl a ft ffl to ft ffl a ft ffl 2 a * ffl s a ft ffl ■J, o
δ E tf δ δ ES f δ δ E ^ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ ES if δ δ Irø.
k ffi kffi kffi ffik %ffi %ffi %ffi %ffi CD %ffi ffi ffik %ffi. kD CD %ffi %ffi %ffi ffik %CD kffi %ffi ffik %ffi CkD kffi %ffi ffi %ff ffk ffi fkfi %ffi CkD kffi kCD Ck •f- i i D P
O O O O O O Q O Q O O O O O O O O O O O O O O O O O Q O Q O Q O O Q O O O
\%
§ §
rø g δ rø ES f ør S if δ rø ES j δ rø E if TJ ES i δ ør W
W ? rø w
3 rø rø Cd
3 5 Ift
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON O ON ON ON ON ON ON ON ON ON ON ON ON 0\ ON ON ON ON o o o O o O O O O O O o O O O o O O o o O o O o o O O O O O o ft
o o o O O O o O o O o O o O o O O o O O o O O o O o O o o o O O PS
ffl ffl lff ffl ffl ffl
R4a R EZ R6 I.! g4a R4b EZ R6 i-Bu 6-Me Cl CN CF3 i-Bu 6-CI Cl CN CF3
Table 15
R g4a R4b sZ R6. X R R4a R4b Z R6 X
Me 6-Me H OCHF2 F CH Me 6-CI H OCHF2 F CH
Et 6-Me H OCHF2 F CH Et 6-CI H OCHF2 F CH i-Pr 6-Me H OCHF2 F CH i-Pr 6-CI H OCHF2 F CH i-Bu 6-Me H OCHF2 F CH i-Bu 6-CI H OCHF2 F CH
Me 6-Me H SCHF2 F CH Me 6-CI H SCHF2 F CH
Et 6-Me H SCHF2 F CH Et 6-01 H SCHF2 F CH i-Pr 6-Me H SCHF2 F CH i-Pr 6-CI H SCHF2 F CH i-Bu 6-Me H SCHF2 F CH i-Bu 6-CI H SCHF2 F CH
Me 6-Me H OCF3 F CH Me 6-CI H OCF3 F CH
Et 6-Me H OCF3 F CH Et 6-CI H OCF3 F CH i-Pr 6-Me H OCF3 F CH i-Pr 6-CI H OCF3 F CH i-Bu 6-Me H OCF3 F CH i-Bu 6-01 H OCF3 F CH
Me 6-Me H SCF3 F CH Me 6-CI H SCF3 F CH
Et 6-Me H SCF3 F CH Et 6-CI H SCF3 F CH i-Pr 6-Me H SCF3 F CH i-Pr 6-01 H SCF3 F CH i-Bu 6-Me H SCF3 F CH i-Bu 6-CI H SCF3 F CH
Me 6-Me H C2F5 F CH Me 6-CI H C2F5 F CH
Et 6-Me H C2F5 F CH Et 6-CI H C2F5 F CH i-Pr 6-Me H C2F5 F CH i-Pr 6-CI H C2F5 F CH i-Bu 6-Me H C2F5 F CH i-Bu 6-CI H C2F5 F CH
Me 6-Me H n-C3F7 F CH Me 6-CI H n-C3F7 F CH
Et 6-Me H n-C3F7 F CH Et 6-CI H n-C3F7 F CH i-Pr 6-Me H B-C3F7 F CH i-Pr 6-CI H n-C3F7 F CH
iffif δ δ i-r S " f CD cδ ft1
k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k i ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Irøj-;
! * o o o O O O O to to o i . J oo oo oo oo O O O O 8 g « S S S S 8 n O SO Oh OS O O O O
Tj TJ Tj Tj TJ TJ rø Tj Ui U $i _> _} 533555„a_?. to5.toBlJto .to to to8toSto8 a a a a.s * ■£ € § R
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø ft
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 ιx
Uθ
1.1 ^ δ δHi ffl" ffig ή røHi ErtS fffi δ^ διι E"S fffi δiS røH E" iffi δrt δH E"S ifffi δ|S δHr E"S iffi δβ δHr E"S fffi δrt røHi E"S fffi δs2 røi-ι E Cg δ^ lι rø.
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lp
Irø
1
«. a a a a
• -§0 ■-§4 •-§4 «-§4 •-§4 ■-§4 •-§4 •-§4 §§§§ I § 33 j § 5 J 1 to 1to 1to 1to to 1to 1to 1to 1 a a a a 1 -41 -J -4 -41 -J *
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø rø ft
Ω fc Ωfc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9cf 9fc 9fc 9fc 9fc 9fc 9fc 9fc fc 9fc fc 9fc fc IX
, "^__) I1 ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl
3 I o o o o o o o o o o o υ o o o o o o o o o o o o o o o o o o o o o o o vo vo vo vo vo vo vo vo vo vo vo vo vό vo vo vo vo vo vo vό vό vo vo vo vo vo vo vo vo vo vo vo vo vo vo
1A ffl *
VO
χι 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 s o 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3
H^| m ffl m ffl m m ffl m m ffl m m m ffl ffl ffl m ffl ffl m m ffl m ffl m ffl m m m q ffl ffl
a δ δ δ δ
* "*°** I ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi
rø I ffiJ Cro røT' E
ON CT, ON ON ON ON ON O t_^ ON ON ON C_N O N ON O i-^ ON ON O ON ON ON ON ON ON ON O O^ k k k k k k k k k k k k k k P f CkD fifk k ffi CkD k k k k k k ffik k ffi k ffi k ffi k k k k k k k k k ϊL D fi
Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl ffi ffi II
OO oo O O O O
_ Q O Q O Q o O oo oo oo oo O O O O oo oo oo oo O O O
Ω Ω Ω o o o o o o n n O t^ . -Z! __. § t to
-Z rø hcj rø rø rø rø Tj
TJ TJ rø rø Ω Ω O O Q Ω O O O
TJ ΩTJ ΩTj Ωrø TJ ΩTJ ΩTJ ΩTJ to to to to t -4 --3 -4 -4 -4 -4 -J u t to % to % to % to % to % to % to % f
Tj Tj h- hcj Tj hcj hcj hcj Hcj H-Cj H-J Tj H__j Mcj hcj hcj hcj hrj hcj hcj hcj hcj hjj h-j hcj hcj Hcj HjH. M^ Hj γ} .
9 Ω Ω 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 IX
-J
Tj g δ δ ES f δ δ ES if δ δ ES if δ δ ES f δ δ ES if δ δ ES f δ δ ES f δ δ ES f δ δ ES lft
Os OS Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os OS Os Os Os OS Os Os Os Os Os Os Os Os Os Os Os OS
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω l
Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl Irø
£
fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc
R3 R4a R4 R7 R6 X R3 R4a R4b R7 R6 X i-Pr 6-Me Cl SCHF2 F CH i-Pr 6-CI Cl SCHF2 F CH i-Bu 6-Me 01 SCHF2 F CH i-Bu 6-CI Cl SCHF2 F CH
Me 6-Me Cl OCF3 F CH Me 6-CI 01 0CF3 F CH
Et 6-Me Cl 0CF3 F CH Et 6-CI Cl 0CF3 F CH i-Pr 6-Me Cl 0CF3 F CH i-Pr 6-CI Cl 0CF3 F CH i-Bu 6-Me Cl 0CF3 F CH i-Bu 6-CI Cl 0CF3 F CH
Me 6-Me Cl SCF3 F CH Me 6-CI Cl SCF3 F CH
Et 6-Me Cl SCF3 F CH Et 6-CI Cl SCF3 F CH i-Pr 6-Me Cl SCF3 F CH i-Pr 6-CI Cl SCF3 F CH i-Bu 6-Me Cl SCF3 F CH i-Bu 6-01 Cl SCF3 F CH
Me 6-Me 01 C2F5 F CH Me 6-01 Cl C2F5 F CH
Et 6-Me 01 C2F5 F CH Et 6-01 Cl C2F5 F CH i-Pr 6-Me Cl C2F5 F CH i-Pr 6-01 Cl C2F5 F CH i-Bu 6-Me Cl C2F5 F CH i-Bu 6-CI Cl C2F5 F CH
Me 6-Me 01 n-C3F7 F CH Me 6-01 Cl n-C3F7 F CH
Et 6-Me 01 n-C3F7 F CH Et 6-CI Cl n-C3F7 F CH i-Pr 6-Me Cl n-C3F7 F CH i-Pr 6-CI Cl n-C3F7 F CH i-Bu 6-Me Cl n-C3F7 F CH i-Bu 6-CI 01 n-C3F7 F CH
Me 6-Me 01 i-C3F7 F CH Me 6-CI 01 i-C3F7 F CH
Et 6-Me Cl i-C3F7 F CH Et 6-01 Cl i-C3F7 F CH i-Pr 6-Me Cl i-C3F7 F CH i-Pr 6-CI Cl i-C3F7 F CH i-Bu 6-Me Cl i-C3F7 F CH i-Bu 6-CI Cl i-C3F7 F CH
Me 6-Me Cl CN F CH Me 6-01 Cl CN F CH
Et 6-Me Cl CN F CH Et 6-CI 01 CN F CH i-Pr 6-Me 01 CN F CH i-Pr 6-CI 01 CN F CH i-Bu 6-Me 01 CN F CH i-Bu 6-01 Cl CN F CH
Me 6-Me Cl OCHF2 01 CH Me 6-CI Cl OCHF2 Cl CH
Et 6-Me 01 OCHF2 01 CH Et 6-CI Cl OCHF2 Cl CH i-Pr 6-Me Cl OCHF2 01 CH i-Pr 6-CI Cl OCHF2 Cl CH i-Bu 6-Me Cl OCHF2 Cl CH i-Bu 6-01 Cl OCHF2 01 CH
Me 6-Me Cl SCHF2 Cl CH Me 6-CI Cl SCHF2 01 CH
Et 6-Me 01 SCHF2 01 CH Et 6-CI Cl SCHF2 01 CH i-Pr 6-Me Cl SCHF2 Cl CH i-Pr 6-CI Cl SCHF2 Cl CH i-Bu 6-Me Cl SCHF2 Cl CH i-Bu 6-01 Cl SCHF2 Cl CH
Me 6-Me Cl OCF3 Cl CH Me 6-CI Cl OCF3 Cl CH
Et 6-Me 01 OCF3 Cl CH Et 6-01 Cl OCF3 Cl CH i-Pr 6-Me Cl OCF3 Cl CH i-Pr 6-01 Cl OCF3 Cl CH
Cd ø Cd tS fif ώ 5? w rø pi fl irø.
3 r ιι E r 3 E? f
3 δ ES ^ δ δ ES ^ δ δ ES i^ δ δ ES ^ δ δ E iS δ δ E iS δ f
O O O O O O O O O O O O O Q O O O O O Q Q Q O O O Q O O Q Q Q O O O O O O 1 I% or
oo o o o o oo oo oo oo O O O O *?*. *?•. a a a a __ oo oo ,9 o o 1 I O oo 00 oo 00
Ω ^ Ω Ω ^ Ω o O o o o O O to O O to to to
H. 9 9 9 ! ! ! ! ! ! ! ! § § § ,9 ■ ' i i hcj ^ Tj Tj rø TJ TJ
TJ rø hcj TJ r rø
TJ TJ ui Ui Ui Ui ø rø rø rø to to to to to to to to -4 -J. -J -4 —4 -J 9 ft
-4 -J ω w ω w ω ω ffl ffl ω w ω ω w w ω ω o o o o o o o o o o o o o o o o o o o o o |rø s s s s s s s s s a s s s s s s s s s ^ g ffl δ δ ES δ δ ES δ j ES δ g s δ g ES ^ δ j ES δ j ES δ ^ ES δ l^
O ^ c3s ^ cj. O O\ c>i ^ ^ o> ON ON O> -^ O -^ o> ^ ^ ON ON ON ON ON O^
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lp
O O O O O O O O O O O O O O O O O Q O O O O O O O Ω Ω ° O O O O O θ |ft
OJ OJ OδJ OδJ OδJ Oδ OδJ Oδ .lrø .irø .irø to to to
ω ro ω ro ω ffl ω ro ω ω ro ω cd w ro w o o o o o o o o o o o o o o o o o o o o o lrø
p Ω-l fcΩ fcΩ Ωfc fc9 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ix
| CDι p roi rø H' ES _? E? ør
N N OΛ OΛ OΛ O CD O CT> O
O O O O O O O O O O O Q Ω Ω I . CI CI Ω OJ OJ O O Ω Ω Ω Ω <^ (^ (^ 0 0 ("J 0 OI C OJ
%
i. o o 00 OO 00 00
OJ to o hcj to o Tj to ■ ' to ' rø TJ TJ o o ør Ui Ui Ui Ui OJ OJ rø rø —J
Tj hcJ hcJ TJ TJ TJ Tj hcj TJ TJ TJ TJ TJ Tj O TJ OTJ OTJ QTJ QTj QTJ OTJ OJ OJ OJ OJ OJ OJ OJ ro w w w w w w w w w w w C 1d ffl 11 ffl 11 C 11d I Irø
S MM MM MM MM HH HH MM )__H HH HH HH HH HH HH HH ffi ffi ffi Θ Θ 9 9 9 9 9 9 9 9 S 9 S S 999 S S S S S S S S i
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON o o O o O o o O o O o O O O o O O o O o o O O o O O o O O o o o |ft
o o O o o O O O o o O O O o O O o O o O O o o O O o O O O O O O O n a _ _ _- __. __. r_. _-. _-, -, - <-N (-, cΛ O O O O ξ J-. t?0 ξ0 ξ0 ξ0 & Q 0 Q &_. c Qv Qoo O Q QO O Q O g ( g-N ( g-N, C §- §C> Ω Q Ω Ω rl ^i ^ rø u. i . υ. j o oj o oj o oj j ^ ^ ^ ^rø ^rø ^ ^ jrø 9 9 § 9 0 0 0 O 0 O O to1 to" to5 to1
Tj Tj hcj hcj t_j ι_j ι__. ι__ι ^ri ^ j hJ I I t-Λ LΛ Λ Ift
^J ^J *■*-. ^ϊ ^J -J -»J ^J
Tj Tj Tj Tj hcj hcj hcj hcj Mcj Mcj hcj Tj hcj Tj hcj hcj Tj Tj hcj Tj Tj rø Hi roH roi-i ffll ffli-l ci-dt ci-dt cHd roi ro'-t cld roH ci-dt roi-i iro-t iro-l llrøO.N
9 9 9 9 9 9 9 9 9 9 Ω Ω Ω Ω Ω Ω s s s s 8 S S 38 8398 S 3 S 8888 I*
ON ON ON ON
1 i ft
& i i i i 1 i i i i ffi ffl ffl ffl ffl ffi ffl a ffl a ffl ffl ffl ffl ffi a a ffi in ffi ffi ffi ffi ffi ffi ffi Ω o Q o Q o Ω O o
% a a a a o o 0
00 00 00
O O O to O to O to o o o o o oo 00 oo 0 O o O o o O a a a
O o o o o o
Tl J? TJ TJ rø TJ 4 -J ør rø rø rø TJ 9 9 9 9 9 9 9 9 9 o o o
9 ό rø r TJ TJ TJ ft - -4 -4 -4 -J to 8 to 8 to % to % to % 9 9 ør to % to to 8 9 -4 - rø4 -4 -4ø -4 -4
TJ rø Tl rø rø TJ Tl TJ TJ rø TJ Tj TJ TJ rø rø rø rø rø TJ Tj rø Tl TJ TJ Tj 9 9 9 9 9 9 9 9 9 9 9 ft
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 X
ES 1 δ 3 5 ES 1 δ 3 5 ES δ 3 5 ES δ 3 to ES cf δ 3 to ES cf
ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON ON rø ό ό Q Ω Q ό ό ό ό Q Q Q Ω ό Q ό ό Ω Ω Ω Ω ό ό ό ό Ω Ω Ω Q ό ό ό
ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi o o o o o o o O o o o
a a a a o o o to o o o o o o 00
O 00 00 00 O o o a a o O O o O to t O O o o o o O o
TJ Tl rø % rø 9 9 9 9 9 9 9 9 9 j 9 o o o
9 9 9 9 ό rø rø T % Tj rø rø rø TJ ft -J rø rø -4 -4 t to to % to to 8 t 8 t 8 t 8 -4 rø -4 -4 rø
-4 -4
rø Tl TJ rø rø Tl rø rø TJ rø rø Tj rø Tj Tj Tj TJ Tl rø rø rø rø rø Tl Tj rø 9 9 9 9 9 9 9 9 9 9 9 ft
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9
O -JN θ> θN ^ ^ ON C_ O> ON -3 σN θN C_N σN ON σN θN O -JN θΛ OΛ -^ δ s § ft c CfD c CfD c CfD c CD CD C15 CD O CD O CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD I 3
Irø.
§
*. --. a a a a
9 9 9 o o o o n n (. J to rø rø rø rø rø rø rø rø rø Ui
-4 -4 -J -J -4 -4 -4 -4 ? IIII oo oo oo oo O O O O P IJIJ to to.toI.toItolto8to 8tolas9s R O O O Q Q O O O Q O Q O Q O O Q Q O Ω (~> 0 0 <^ ("j 0 Ω <"j (^ ("j l rø J Tj Tj TJ Ift o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o n o o o ci o Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø IX
4 t^ δ Ht
CJN ON ON A ON ^ ON ON N C_N N ON -^ C_N ON ^ ON O ON ON O> ON C3N C_N OA ON ON ON ON
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω |ft
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ft
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø ft o O oO oO oO oQ Ωo o^ Oo oO Qo oO oQ Oo oQ oO oQ oΩ oO oO oQ oO oO oO oO oO oO oO o oO oO o πy oy oy oy oy y ιi-ιi
s ^ ø ffi ffi s g m [r
2 2 2 . ffi ffi g 4 ffi ffi 3
Irø ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl fe
o o o o . . . a a a a -. _ _-_ _ oo 00 00 00
Ω Ω Ω Ω o o Ω Ω .9.9.9 ^. i. J- j-, 0 0 0 0 O O O O oo oo oo oo O O O O
Ω .9 .9 ,9 o to. to. to.
§ g ffi E * ≥! s ≥! % % % % % :rø :rø :rø :rø o to to to Ui Ui Ui Ul a Q Q Q 88 Q to 8to 8to 8to 8to to 1to 8to 8 a R
O O Q O TJ rø Mcj Mcj Mcj Mcj Tj hcj hcj hcj hcj hcj Tj Tj hcj hcj hcj Tj Tj hcj Tj hcj Tj Mcj Mcj hcj hcj hcj hcj C3 Ift
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Ω 9 9 9 9 9 S IX
4i- υ
C ød T H?J ES+ & ffi Cd rø Cd i- ES 3 ^ ES 2 ώ ^ ES 2 ώ E røS Cd r o
3 E? ø r
3 EP w ώ £ ES 0or rø E I hi' rtS ffi ffli Irø OJ
O O O O O Q Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ift
ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi \%
O O o o
8888 a s Ift o to to to
O O Q Q hrJ hd TJ TJ TJ TJ hrJ hcJ TJ TJ Tj Tj TJ TJ Tj TJ rø rø rø rø rø rø rø rø rø rø rø rø rø TJ TJ rø Ω |ft
ffi ffi ffi ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Ω
^ ffl ffl ffl ffl ffi ffi ffl ft ft ft ft ft ft ft ft fc Λ fc fc Λ fc fc ft fc ft ft ft ft ft ft fc ft fc ft ft
3 I o o o o o o o o o o o I O I O t O I O I O I O I O I O I O I O I O I O I O I O I O I O I O I O 1 o υ co co co co co co co co co co co O co co co co co co co co co co o co c co co co co co co
* 3 3 3 w ffl ffl ffl I *H ^3 ω J__ w * 3 ffl S « ft p? f_!M p? a ft fl ϊ3 3 3 | t f s « * ffl °P S w ft ffl
χι 3 5 5 53 53 3 5 3 3 5 5 55 55 5 5 3 3 55555555335 5 5 53
^i G G G G G G G G G G G G G G G G G G G G G G G G G G G G m m m m ffl m ffl m
• . a a a & n s ff ff * <? * z z 2 a a a a a a a
^ fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc
t- "' co co o co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co
o
MM hp HM MM HH 5 O 8 8 O δ δ δ ^ o
8" 8" 88 s 0"0
^ ffl ffl ffl ffl ffl ffi ffi ffi ffl ffl ffl fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc
3 I i o o o o 9 9 J O O O O O O O J o o o o o o o o o o o o o o o o o
f_;| ffl ffl ffl ffl ffl ffl ffl ffl ffl m ffl ffl ffl m m ffl m m ffl m ffl ffl ffl 8 δ 8 8 δ 8 δ δ 8 δ δ δ
co co co co co co co ιn <n ιn ιn tt rj— i^ r— [i r— Hi1 1^ ^ 1J_, LI_ __ y 8 O 8O 8O 8O ftO PON1 PO ft cN ftcN, ftCN., ftCN., n CJn r-Jo ^ " r÷O l ^ r VO r "co r ^ Vi ^ CJ o o o o θ ε. V ε. ε; V ε; *»-* *-* •«-* **-* w 5 s ^ δ^ βy O gyO SyO ΘyO Boo gco goo βo &n β βo ffci -s
t- "' co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co co
^ i a ._- ft Jr* p Jx?1 ^ <-> a.__ ft Jr1 ffl 5 ^ ω a-i ft-t ffl 3 ^ o a ,__ ft JH p? <L> a .__ ft JH p 3? <u ffl ι_J ( |g? _. .a*. 1fc 13 |_! «B i--r i59 -. S« ^f ffl-l? ^ o
3 g4a R4b sZ E6. X R_. g4a R___ EZ ≠ X i-Pr 3-Me H SCF3 CF3 CH i-Pr 3-Cl H SCF3 CF3 CH t-Bu 3-Me H SCF3 CF3 CH t-Bu 3-Cl H SCF3 CF3 CH
Me 3-Me H C2F5 CF3 CH Me 3-Cl H C2F5 CF3 CH
Et 3-Me H C2 5 CF3 CH Et 3-Cl H C2F5 CF3 CH i-Pr 3-Me H C2F5 CF3 CH i-Pr 3-Cl H C2F5 CF3 CH i-Bu 3-Me H C2F5 CF3 CH i-Bu 3-Cl H C2F5 CF3 CH
Me 3-Me H n-C3F7 CF3 CH Me 3-Cl H «-C3F7 CF3 CH
Et 3-Me H "-C3F7 CF3 CH Et 3-Cl H n-C3F7 CF3 CH i-Pr 3-Me H n-C3F7 CF3 CH i-Pr 3-Cl H -C3F7 CF3 CH i-Bu 3-Me H n-C3F7 CF3 CH i-Bu 3-Cl H n-C3F7 CF3 CH
Me 3-Me H i-C3F7 CF3 CH Me 3-Cl H i-C3F7 CF3 CH
Et 3-Me H i-C3F7 CF3 CH Et 3-Cl H i-C3F7 CF3 CH i-Pr 3-Me H i-C3F7 CF3 CH i-Pr 3-Cl H i-C3F7 CF3 CH i-Bu 3-Me H i-C3F7 CF3 CH i-Bu 3-Cl H i-C3F7 CF3 CH
Me 3-Me H CN CF3 CH Me 3-Cl H CN CF3 CH
Et 3-Me H CN CF3 CH Et 3-Cl H CN CF3 CH i-Pr 3-Me H CN CF3 CH i-Pr 3-Cl H CN CF3 CH i-Bu 3-Me H CN CF3 CH i-Bu 3-Cl H CN CF3 CH Tabl e l6
Rf R4b 2 3 R_. g4a R4b R9 R R R.. CH3 F CF3 Me Cl Cl Br CH2CF3 M Mee Br CH3 F CF3 Et Cl Cl Br CH2CF3 E Ett Br CH3 F CF3 i-Pr Cl 01 Br CH2CF3 ii--PPrr Br CH3 F CF3 i-Bu 01 Cl Br CH2CF3 ii--BBuu Br CH3 F CF3 Me Br Cl Br CF2CHF2 Me 01 CH3 F CF3 Et Br Cl Br CF2CHF2 Et Cl CH3 F CF3 i-Pr Br Cl Br CF2CHF2 i-Pr Cl CH3 F CF3 i-Bu Br 01 Br CF2CHF2 i-Bu Cl
co cn cN
°k\ 3 3 5 _s o EH δ δ δ δ δ δ cN 8 ft c o δ 8 f δ δ 8 cf δ
8 N δ 5 _t! 5 5 5 _3 _£ o fl 5 o EH δ δ δ δ δ δ δ δ δ 8 δ δ 5 5 3 3 5 5 5 f 5 δ δ δ δ δ δ δ ft o l m ffl m ffl fc o δ δ δ fc 8 δ δ δ
3 | o o o o o o o o o o o υ υ o o o υ o o o o o o o U o o o υ o rø-
^1 G G G G i i li ffl ffl ffl ffl G G G G ffl ffl ffl to G G G G li li l ffl ffl m ffl G G G G l to ffl ffl ffl G G G G
3 3 3 3 3 3
Pi\ a s 3
3 a 3
5 3 a 5 3 a ft 3 a 5 3 a f? 3 a f? 3 a s 3 3 1 ft* 3
U fc fc fc fc fc fc ft fc ft ft ft fc fc fc fc fc o o o o o o o o o o o o o o o o o o o
t- 3 I
^1 3 5 5 8 ffl 8 ffl l 8 ff 8 ffi 8 ffl 8 ffl 8 ffl ffi 8 ffi 8 ffi 8 ffl 8 ffl 8 ffl 8 8 ffl 5 ffi 8 ffl 8 5 ffl 8 8 ffl 5 5 5 5 5 5 8 ffl 3 3 5 3 5 5
o
R4a R4b 9 R δ R4a R4b R9 R3 R6
CH3 Cl CF2CHF2 Et Br 01 CF3 CH2CF3 Et Cl
CH Cl CF2CHF2 i-Pr Br Cl CF3 CH2CF3 i-Pr Cl
CH3 Cl CF2CHF2 i-Bu Br Cl CF3 CH2CF3 i-Bu Cl
CH3 Br CF3 Me Cl Cl CF3 CH2CF3 Me Br
CH3 Br CF3 Et Cl Cl CF3 CH2CF3 Et Br
CH3 Br CF3 i-Pr Cl Cl CF3 CH2CF3 i-Pr Br
CH3 Br CF3 i-Bu 01 Cl CF3 CH2CF3 i-Bu Br
CH3 Br CF3 Me Br Cl CF3 CF2CHF2 Me Cl
CH3 Br CF3 Et Br Cl CF3 CF2CHF2 Et Cl
CH3 Br CF3 i-Pr Br 01 CF3 CF2CHF2 i-Pr Cl
CH3 Br CF3 i-Bu Br Cl CF3 CF2CHF2 i-Bu Cl
CH3 Br CH2CF3 Me Cl Cl CF3 CF2CHF2 Me Br
CH3 Br CH2CF Et Cl Cl CF3 CF2CHF2 Et Br
CH3 Br CH2CF3 i-Pr Cl Cl CF3 CF2CHF2 i-Pr Br
CH3 Br CH2CF3 i-Bu Cl Cl CF3 CF2CHF2 i-Bu Br
CH3 Br CH2CF3 Me Br Cl Cl CH2CF3 n-Pr Cl
CH3 Br CH2CF3 Et Br Cl Cl CH2CF3 n-Bu 01
CH3 Br CH2CF3 i-Pr Br Cl Cl CH2CF3 j-Bu Cl
CH3 Br CH2CF3 i-Bu Br Cl Cl CH2CF3 i-Bu Cl
CH3 Br CF2CHF2 Me Cl Br F CF3 Me Cl
CH3 Br CF2CHF Et Cl Br F CF3 Et Cl
CH3 Br CF2CHF2 i-Pr Cl Br F CF3 i-Pr 01
CH3 Br CF2CHF2 i-Bu Cl Br F CF3 i-Bu Cl
CH3 Br CF2CHF2 Me Br Br F CF3 Me Br
CH3 Br CF2CHF2 Et Br Br F CF3 Et Br
CH3 Br CF2CHF2 i-Pr Br Br F CF3 i-Pr Br
CH3 Br CF2CHF2 i-Bu Br Br F CF3 i-Bu Br
CH3 CF3 Me Cl Br F CH2CF3 Me Cl
CH3 CF3 Et Cl Br F CH2CF3 Et 01
CH3 CF3 i-Pr Cl Br F CH2CF3 i-Pr Cl
CH3 CF3 i-Bu Cl Br F CH2CF3 i-Bu Cl
CH3 CF Me Br Br F CH2CF3 Me Br
CH3 CF3 Et Br Br F CH2CF3 Et Br
CH3 CF3 i-Pr Br Br F CH2CF3 i-Pr Br
CH3 CF3 i-Bu Br Br F CH2CF3 i-Bu Br
CH3 CH2CF3 Me Cl Br F CF2CHF2 Me 01
CH3 CH2CF3 Et 01 Br F CF2CHF2 Et Cl
o O o ffi ffi ffl Ωffl Ω ffl Ω ffl 8 S S 9 fa s ffi ffi ffi s 8 8 8 ffi1 9 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 9 9 9 9 I ft p
O O rø Ω o r rø o TJ Q TJ Q ø Tj 9 9 rø rø rø ør rø rø rø 9 9 9 9 9 9 9 9 ft
E rtS C 2D ώ & δ ι-t w £ δ ES ro E "S ffD ø ro δ E "S cf δ 3 5 ft
Cd Cd W Ω o o o ω w ro ro o o o o w ro ro ω o O O Ω £? W Cd Cd o Q O W W W W Ω O Ift 4_. vo
Cd W Cd Cd Cd Cd Cd Cd Cd ffl
11 II ffl II ffl 1 ffl 1 ffl 11 ffl II ffl W ffl Cd ffl II ffl ffl Cd ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ω ω Cd I 1ft s->
Cd ffl W Cd w w ro O O O O O O O O O O O O O O O O O O O O O O O Q Tj Tj Tj TJ TJ Tl n
9 9 9 τ_ τι j Tj Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø Tj TJ
O CI to to to to to to to to
TJ hrj Q Q Q to ffi -to.W toffi ιtoffi ιtoffi 1toffi ιt5o* ttoffi Ω Ω Ω Tj Ω TJ Ω Tj Ω TI Ωør Ω ^, ^ 1^-. 1^-. ^ ^.
9 I Irø vo t3 Tj iτ_ Tj Tj hcj Tj TJ Tj ta 9 ta 9 ta 9 ta 9 ta 9 ta to 3 to E. to t 8 to8 to8 to8 1 OJ OJ OJ OJ OJ OJ OJ OJ to to to to to to rø rø 2 £ώ τj rtt5 (2I pro! τj w cf
ro ro ro Ω Ω Ω Ω ω ro ω ffl Ω Ω Ω Ω ω ω ω w Ω Ω Ω Ω ω ω ω ω Ω Ω Ω Ω ω ω ω ω Ω Ω ft
t- t-
T o ffl.\l ffl -- o o o o ffl ffl ffl m G G G G m i-l ffl m G G G G m m m c-3 G G G G ι-3 ffl m ffl g o o ffl
H 3 3 3 3 3 J ft ' 3 w * ffl S a * ffl S ffl ft ffl w ft ffl I a * 3
•i ffl * J. ffl ffl ft _ 32 I ω w ft 3 ff t i l w f
.. .T W WO WO Λ Λ W Gfc Gfc fcG fcG Gfc Gfc Gfc Gfc
m li m li m l m li m li m li m m m m ffl m m m m m m
3 I ffl li ffl li ffl ffl Si ffl ffl ffl ffl ffl ffl m m ffl m m m m m m m m ffl ffl ffl ffl ffl m m m ffl ffl ffl ffl ffl m m o
IT)
^ rø G o o G G G G G to to ffl ffl G G G G ffl m to ffl , G G G G m m ffl ffl G G G G r-. m m
3 li 3 3 3 3 3 3 3
HHI ffl ft ω ffl ffl a ft ffl ffl ft ffl ffl ft ffl q ft 3 ffl « ϊ. 3
S ffl ffl w ft ffl W ft 3 ffl ffl ft
ft. 8 fc t o f
l co _ δ u o o o ft ft ft ft ft ft ft ft ft ft ft fc fc fc fc fc fc fc fc o o o o o g o
t- 3 I ro
-H ffi ffi ffi ffi ffi G G o o o o o o o o o o o o o o o o o o o o o o o o o o o o 90
-t
CN
© o
9 fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc O Q Q Q Q O O O O Q Q O O Q Q O O O O O O O O O O O O O I ft p
fc fc fc fc fc fc fc fc ffl HP ffl ffl Cd ffl ffl ω ω w 1 w 1 w 1 ro 1 o fc o o o o o o o o o o o o o o o
\%
O C id w i w ω o o o o o o o O (-5 C 1d W ω ω Ω Ω Ω Ω W w ffl ffl Ω Ω Ω Ω ffl ffl W ffl Ω Ω Ω Ω Ω Ω Ω ft . o o o o o o o o Ω ω ω ω ro ro ffl ffl Cd ffl ffl ffl ffl ro ro ro ro ro ro ro ro ro ro ro ffl ffl ffl ffl ffl Ift
I 3
ffi Orø TOJ rø Tj TJ J TI TJ TJ !"Tj TJ TJ TJ TJ TJ hrj TJ J
O9J OJ OJ OJ OJ OJ O 9 hcj J O9 TJ T J π
Ω Tj Ω TJ Ω r o o TJ Tj Ti TJ fi to 9 to 9 to to toø
.f o o to 9 to 9
TJ o TJ O 9 ff
Tj i toi to ffi to 8 N 8i t 88> to 8 to 8 Ω 9 9 9 9 OJ Ω Ω Ω Ω Ω o Ω Ω y Oy Oy ^o3 *o *
— ff TJ ffi — TJ ffi T_ iff o y O O 0o ^
I rø vo
TJ ^ i T_ ffi T] Tj o Mcj Tj Tj Mcj ø 9 9 9 to to to to to to to to OJ rø Ω r 9 to % to % to % to %
2 ώ $ ES ffl r
3 _? ES 2 ω w ff rø ES 2 ro δ ES 2
3 & l J? ω E? E <-S!• ffi to w Cd
3 EP rø Cd ø
3 E? Ift
o W wi l w l w Cd O o o Ω ε? ω ro w o o Ω O ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω O fc C 1d C 1d C 1d W 1 ft
O 8J O8J O8J OSJ O8J O8J 9 Ω Ω Ω Ω Ω Ω Ω 888 S 8 8 8 8 S 88 S 8 8 8888 S 88 8 a |ft
ffl ffl ffl ffl ffl ffl ro rø rø rø rø rø rø rø rø rø rø rø rø rø rø ffl ffl ffi ffi ffl ffi ffl ffi ffi ffi ffi ffl ffi ffi ffi ft
Ω Ω Ω Ω Ω Ω Ω Ω o o o o o o o Ω S Ω^ Ωffi Ωffi Ωffl Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ωffi Ω Ω Ω Ωfi Ω Ω Ω Ω ^ ^ to^ to^ t^ t ^ to^ to^ ffi ffi ffi ffi ffi iff ffi
I Irø vo to to to ^ to NJ to to w to to tO r to toffitoffitoffitof toffitoffitoffitoffi o ^ gg gtg gq ofg otg oq Qtg^rø^rø .^rø^rø^rø^rø^rø to to to to to to to to
M C2D δ s H E "S (iI? δ -S Hf E^ ! gδ* Hi ErtS iffi? δ ø δ ES ! C?D δ ? H E rtS (iI δ _s il ErtS iCD δ £ H E i C?D δ e Ht E rtS ^ CD δ ? J rtES IftU
H? H? Ω Ω Ω Ω H? H ι? HS Ω Ω Ω Ep H? H? H? Ω Ω Ω Ω £? H? H? H? Ω Ω Ω Ω H H H? S, Ω Ω Ω ft Λ t
8 S O8J O8J O8J O8J Ω Ω Ω Ω Ω Ω Ω Ω 8 O8J O8J O8J O8J 8 8 8 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω P ft2
rø rø rø rø rø rø rø rø O Q Q Q O O O ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Irø.
Ω Ω Ω Ω Ω Ω Ω Ω V G Q Q Q Q Q Q Q Q Q Q β ; ^ Ω Ω ι_ Ω «._ Ω ... Ω .. Ω ._ Ω ._
Q Q Q Q Q Q Q Q Q ^ tj t | Irø vo to g to^ to^ tog to^ to^ tog to^ tog to^ iog to^ tog iog to§ to^ to^ to^ to^ tog tog tog Ω ώ Ωώ Ωώ Ωώ Ωώ Ωώ ώ ώ orø orø orø rø orø orø orø to to to to to to to to
E+ ^ύ δ Ht E'^S ^CD δ j- δ H E "S^ ^ CD g' Hf E^S^ i^CT δ rt H^ E^S ^D δ j- Hf E *^S ^D δ μj "E ^ ( δ S H ES t^T δ ci πf E "S CD «- μf E <^S l l I 11rø OJ
w w Q Q Q Q ω ω ro ro o o Q w ro ro ω Q o o ω w ω ro Q Q o o ω ω ro ro o o o
Pi\ fc ft fc fc fc fc fc fc fc fc fc
m m ffl m m m m m m ffi ffi ffi ffi tl a 1 ffi G a « «9 in ffi ffi G
•/-) «-. <n
% m
fficogcoffico
3 ft
^1 a 5 3 a s 3
3 1 & o
P. s
k ffi ffik CkD kffi kffi ffik kffi ffik CkD CkD CkD kffi kffi kffi CkD ffik CkD ffik ffi ffik ffi ffik ffi ffi ffi ffi CD ffi CD CD ffi CD ffi ffi D CD CD I Ift 3
ffi ffi ro ffi ffi 0 ffi ffi t!a ffi ffi ffi ffi ffi ffi ό ffi ffi ffi ffi ro ffi ffi ό ffi 2 ffi w ffi ffi ffi ffi ffi ffi ό !
9
Q Q Q Q 9J 9 9 9 9 9 Ω 9 Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø rø rø |ft ϊ
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω o o I 1ft 3
ffi ffi ro ffi ffi 0 ffl g; ffi tJrj if ffi ffi ffi ffi fif (-) ffi fif ffi ro ffi ffi 0 ffi §; ffi trj ffi ffi ffi ffi ffi ffi
1 i-l ft 1 f 1 ni ft 1 o 1%
C kD kD CkD ffik kffi ffik CkD kCD ffik CkD CkD kffi ffik kffi CkD ffik CkD kffi ffik kCD kffi kffi ffik kffi kffi kffi ffik kffi ffik CkD kffi ffik kffi kffi ffik ffik kffi I Ift 3
ffl ffl ffi ffl ffi ffi ώ ffl ffl ffl ffi ffi ffi ό ffi 6 ffi ffi ffi ώ ffi ffi ό ffi 2 ffi ro ffi ffi ffi ffi ffi ffi ό ffi ό ffi Irø
rø rø rø rø rø rø ω ω w ffl W ffl W ffl ffl W ffl w w w ffl ffl ffl ω w ω .9 9.9.9.9.9 9.9 9 9 9 l^ ON
O O O O O O Q O Q Ω OΩ ΩΩ ΩΩ ΩΩ ΩΩ ΩΩ Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 9 Ω Ω Ω Ω Ω Ω ft
ffi ffi ffi ffi ffi ffi trj ffi ffi ffi ffi ffi ffi ffi H rM H y W rH Q ffi g ffi t S ffi ffi \%
rø rø τj hrj rø rø ro ro ro ro ro ro ro ro ro ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl 9 . 9. 9. 9. 9. 9. rø 9 9 9 9 9 Ift
*U fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ft fc o o o o o o o o o IΛ t- r- r- f- r- r- r- ft ιγ r - r r ' fc r- r-
© fc ft Hi fc HH fc f^i μ-t m μ_ι μn f, ft, ft, ft. CO fc fc c ft ft ft ft ft ft ft ft t CO CO CO o CO f CO fc CO ffl Η E. a o υ o o CN CN CN CN o CJ CJ ri rV o o a S π o π og π og gπ o ^ « ^ « ^ « ^ s 8o 8o
H CJ ft fj S HM H HH HH HH MH HH H HH H HH W
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
14 vo vό vό vo vo vo vό vό vo vό vό vo vό vό vό vό vό vo vό vό vό vό vό vo vό vό vό vό vo vό
VO ^J fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ςj ςj ζj ςj ςJ ζ Q
ft. tT fcr fcT fcr ft ft ft ft h (? h « h m h m ^ £ £ ϊ ϊ s *t ** « & fe fe fe ft l
ON. ft. ft s ft s_r &_? ε. ε; ε. εt •-* •-- •— •*--
^ ffi ffl ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffl ffi ffl ffi ffi ffi ffi ffi ffl ffi ffi ffl ffi ffl ffl ffl
t- ro
-fc cS |2 .a-T ft(fc ^rS __! a*. -ftfc c^!? i__ o ^ ft ft a ft ffl ^ a ft p? a ft ^ i a ft ^ a ft ø? a ft ffl ^ a
ø
3 w rø r
3 ω E? W Cd
3 K TJ £ rt ( &t ? ro ø W Cd M r 3 rø ES ^ ro rø ES < 3 w ? w ro
3 EP E <-S!- I ffi ro
3 to » δ pa,
ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl Irø
* is ϊs JS
Ht HT HT Hf oJ OJ OJ OJ ^ ^ S ^ .o* . to* . to* . t* ^ ^ ^ ^ < rø- ^ ^ t-tf ^ VO t HH ^ hrj ^ hi ^ hn . ^~J . ^~J . o*r.J .~" H H H H C*> I VC
■— 3 -4 — J —J —J — J — 4 — J
ro ω w ω ro ro ω ω ω ω ro ro ro ro ro ro o o o o o o o o o o o o o o o o o o o o o | i
δ Cj δ i-r E rtS ^ CD C Hf ElS- iffi δ £r i-f E <-S► i ffi δ PJ I-1 E-+ |D δ pj Hf E rtS i CD δ cϊ δ 1 ES i CD δ Hf E -S+ i <B p; 1 ES i C δ nf E <■S* i ffi δ ø | I I:rø.
3 T 3 T
N _ N ON OΛ O j ON O θN ON OΛ O _N t-^ N σN N ON ON 3N O \ σN N ON σ^ |HH
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IP
Irø fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc I_ CP
πf S'
w w ω ω ω ω ro ro w ω ω w ro ro w ω o o o o o o o o o o o o o o o o o o o o Q irø O,N
u HH HH HH HH H HH H4 HH HH ffi ffi HH H HM
li o o o o o o o o o o o O O o o g υ υ o o o o o o o o o o o o o o o o vo vo vo vo vo vo vo vo vo vo vo vo vo vo
3 3 3 3 lά ^ ft p? ^ ft ffl ^ a ^ m ^ w ft ffl « ft ffl ft ffl ft ffl s « a ffl ffl ft ffl
OO
m m m m m m ffl ffl m m m ffl fto fto uft fto fto oft fto fto oft- ftu fto fto o o o o o o o o
%l M fcM
M g4a R4b R_! R6 B g4a R4 E2 EΪ:
Et 6-Me H «-C3F7 CF3 Et 6-CI H JI-C3F7 CF3 i-Pr 6-Me H «-C3F7 CF3 i-Pr 6-CI H «-C3F7 CF3 t-Bu 6-Me H n-C3F7 CF3 t-Bu 6-CI H «-C3F7 CF3
Me 6-Me H t-C3F7 CF3 Me 6-CI H 1-C3F7 CF3
Et 6-Me H '•-C3F7 CF3 Et 6-CI H i-C3F7 CF3 i-Pr 6-Me H Ϊ-C3F7 CF3 i-Pr 6-CI H f-C3F7 CF3 t-Bu 6-Me H I-C3F7 CF3 t-Bu 6-CI H /-C3F7 CF3
Me 6-Me H Et CF3 Me 6-CI H Et CF3
Et 6-Me H Et CF3 Et 6-CI H Et CF3 i-Pr 6-Me H Et CF3 i-Pr 6-CI H Et CF t-Bu 6-Me H Et CF3 t-Bu 6-CI H Et CF3
Me 6-Me Cl CHF2 F Me 6-CI Cl CHF2 F
Et 6-Me Cl CHF2 F Et 6-CI Cl CHF2 F i-Pr 6-Me Cl CHF2 F /-Pr 6-CI Cl CHF2 F t-Bu 6-Me Cl CHF2 F t-Bu 6-CI Cl CHF2 F
Me 6-Me Cl n-Pr F Me 6-CI Cl «-Pr F
Et 6-Me Cl «-Pr F Et 6-CI Cl n-Pr F i-Pr 6-Me Cl n-Pr F f-Pr 6-CI Cl n-Pr F t-Bu 6-Me Cl n-Pr F t-Bu 6-CI Cl n-Pr F
Me 6-Me Cl CF3 F Me 6-CI Cl CF3 F
Et 6-Me Cl CF3 F Et 6-CI Cl CF3 F t-Pr 6-Me Cl CF3 F i-Pr 6-CI Cl CF3 F t-Bu 6-Me Cl CF3 F t-Bu 6-CI Cl CF3 F
Me 6-Me Cl i-Pr F Me 6-CI Cl t-Pr F
Et 6-Me Cl i-Pr F Et 6-CI Cl f-Pr F z'-Pr 6-Me Cl i-Pr F f-Pr 6-CI Cl i-Pr F t-Bu 6-Me Cl i-Pr F t-Bu 6-CI Cl i-Pr F
Me 6-Me Cl C2F5 F Me 6-CI Cl C2F5 F-
Et 6-Me Cl C2F5 F Et 6-CI Cl C2F5 F i-Pr 6-Me Cl C2F5 F i-Pr 6-CI Cl C2F5 F t-Bu 6-Me Cl C2F5 F t-Bu 6-CI Cl C2 5 F
Me 6-Me Cl n-C3F7 F Me 6-CI Cl n-C3F7 F
Et 6-Me Cl «-C3F7 F Et 6-CI Cl «-C3F7 F i-Pr 6-Me Cl /1-C3F7 F i-Pr 6-CI Cl n-C3F7 F t-Bu 6-Me Cl 71-C3F7 F t-Bu 6-CI Cl n-C3F7 F
Me 6-Me Cl 1-C3F7 F Me 6-CI Cl -C3F7 F
Et 6-Me Cl 1-C3F7 F Et 6-CI Cl 1-C3F7 F
H, EιS- ifif ro a* i-f E -+ 2 ffi ώ g^ H| ErtS 2c ώ g Hi Ert3 ϊffi ro ø ι-r ErtS ϊ?ffi gffl* πr E -S+ i «, w jr i-p E <■S+ i «. ro _. HT £^ CD EP rø cf ω 3 p ft
ffi2 ffi2 ffi2 2ffi ffi2 ffi2 ffi2 2ffi ffi2 ffi2 ' H'
O O O O O O O O O Q O O O Q Q Q Q O Q O O O O O Q O Q Q O O O O O O O O Jft
s s B 111111 5 S 55 -9 -Q 55 II I I 8 I 8 s B s B K,
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø ft
ON
δ-f ES+ i?fp δ g' δnt E^S' t?D δ g^ δH E^S iCD δ p δK ES i^| δ £ δ Ht E^S i| gδT δ >_ E «-S*■ i C?D δ j=T δ π E ^S C-|D δ δ E "S" j CD jδ- δ π E^S CiD δ πf ft I **»
0 0N ^ 0Λ ^ _Λ 0 0\ C_Λ -Λ _Λ σN . _^ _Λ 0\ ^ C^ IMM
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IP O O O O O O O O O O Q O Q O O Q Q Q Q O O Q Q Q Q O |FT
rø w i HiH.
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø rø ft
Cd rø ES s? Cd rø rø Cd W Cd
3 E? W ω ø T 3 E? W ω 3 E? W
3 ω E? r
3 w W
3 3 ω 3 S 5? 2 δ f ft
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o Irø.
to 8 to 8 to 8 to 8B B B Bέ TJέ TJέ røέ TjA Tj
-α -4 -4 -4 -JA rø4 Tl -1 -4έ rø o
—4 gn rS g 55553333 I I to 8 to 8. to8. to8 B R,
O 9 .Jj L O9Ji t O9iJi i O9-Ji ffll 1ffl ffl 1 ffl 1 ffl 1 Tffl ffl T ffl 1 ffl 1 ffl 1 1ffl ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 ffl 1 1ffl 1ffl 1ffl 1ffl
δ δ .S §? δ ES .^ E 2 ώ ES 2 ώ ' g 2 ώ ES 2 ώ ES 2 ro δ ES 2 OT E rø g^ l-1 rt ffi g l-r rt ffi g l1 ^ ffi p] l-r '^ ffi £ l1 ^ ffi ø l1 r* ffi 3 '1 -* ffi !_l IH -÷ ffi ci l D ci 1 J
O O O O O O O O O Q Q Q Q Q Q Q O O O Q Q O O O O O O O Q Ω O Q Q O O O O Irø
Ω Ω Ω Ω a a a a o o o ~. Ω Ω Ω Ω to o t too t too t too ^ ^ rø rø rø rø rø rø n on u n ^ ^ ^ ^ oj o o-i o Ht Ht Hi Hi
-4 -J -J — - -J -J -4 -J to to to to
OJ OJ OJ OJ c 1d ffl1 ro1 ro1 1ro ro1 ro1 ro1 ro1 ro1 ro1 ro1 ro1 ro1 ro1 ffl1 ro1 ffl1 c1d ffl1 ffl1 ffl1 ffl1 ffl1 ffl1 ffl1 ro1 ro1 ro1 c1d ro1 ro1 Ω Ift
ro rø ro
3 E? ES 2 CD δ S δ? W ω rø i proj HT E^S 2ffi ώj. E? W Irø
3 δ ^ 3 0 ro HI t "+ ^ ff J
0\ ON O> N O> OΛ OΛ O\ N ON O σΛ ^ Λ CJ ON C- θN θ> θN ^ O\ θN N σN σN ON ft
CD CD CD O CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD CD P
O Q Q O O Q O O O O Q O Q O O O O O O O O O O O O O O Q ft
TJ TJ TJ TJ rø TJ hcj TJ TJ TJ hrj hcj hcj hcj Tj Tj hcj o h Tj o h-j o hcj J OJ OJ OJ OJ OJ O 9J O 9J O 9 cj o hcj o hcj o Tj o hcj o J OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ ft
ON.
Cd rø
3 E? w r Cd
3 EP ø
3 E? ør W Cd δ ES 2 .d δ .S 2 [J.
3* δ ES 2 δ 3
Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Ihri
I I t ! I I I I I I I I I 1 I I I I I I I I I I I 1 I I
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω lp
O O Q O Q Q O O Q Q Q Q Ω 0 0 Ω Ω 0 0 Ω 0 Ω Ω 0 0 0 0 0 |ft
iij TJ Tl TJ TJ rø rø TJ TJ TJ rø rø TJ TJ rø rø TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ
OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ OJ J OJ OJ O 9J Ift
k k k k k k k k k k k k k k k k k k Irø
CD CD CD CD CD CD CD CD CD fD CD CD CD CD CD CD CD CD kCD kCD kCD kCD kCD kCD kCD kCD kCD kCD fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc \
S i fcnn HfciH fc MM fc
Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os s Os OS Os
.' .' , .' .
2 CD 2CD 2CD C2D 2CD 2CD C2D 2CD C2D C2D CD CD ffi 2 ffi2 ffi2 ffi2 2ffi CD C2D ffi2 2ffi 2ffi ffi2 C2D ffi2 ffi2 ffi2 C2D ffi2 C2D ffi2 ffi2 2ffi I Ift P
ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Irø.
W O O O O O O O O O O O O O O O O O O Q O O O O O O O O O O O O O Tj Tj Tj rø Ift
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 IX
ON
2 CD δ 3" ι_f E -S* i ffi øδ Hf E rtS ^ ffi ø i- E^S jffi øδ δ E ^S i? CO δ ø δ nf E "S i ffi δ J E "*S (iI δ pi E rtS Ci2D δ pi ES l! δ w E "S* 2 ffi | I^ "jJ
C_S O O ON ON ON ON O ON
O O O O O O Q O O
[IJ ffi S 3-l P-l Jl3 ffi -l t- ffi ffi II) ffi ► ffiK I |rø$ a a o o o o Ω Ω Ω Ω o ^ ^ ^ ^ rø rø rø rø rø rø rø rø ^ ^ t^ -J? ^ ^ ^ i^ o oj oj oj ^ ? ? ? rø rø ^ rø rt '- rt- '- 1^
-4 -4 -4 -4 -4 -J -4 -4 ffl Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø ft
f 9c Ωfc 9fc fc9 9fc fc9 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc f9c f9c 9fc fc IX
R3 R4a R4b R9 R6 X R3 R4a R4b R9 R6 X
Et 6-Me H CHF2 Br CH Et 6-CI H CHF2 Br CH i-Pr 6-Me H CHF2 Br CH i-Pr 6-CI H CHF2 Br CH t-Bu 6-Me H CHF2 Br CH t-Bu 6-CI H CHF2 Br CH
Me 6-Me H n-Pr Br CH Me 6-CI H n-Pr Br CH
Et 6-Me H n-Pr Br CH Et 6-CI H n-Pr Br CH i-Pr 6-Me H n-Pr Br CH i-Pr 6-CI H n-Pr Br CH t-Bu 6-Me H n-Pr Br CH i-Bu 6-CI H n-Pr Br CH
Me 6-Me H CF3 Br CH Me 6-CI H CF3 Br CH
Et 6-Me H CF3 Br CH Et 6-CI H CF3 Br CH i-Pr 6-Me H CF3 Br CH i-Pr 6-CI H CF3 Br CH t-Bu 6-Me H CF3 Br CH t-Bu 6-CI H CF3 Br CH
Me 6-Me H i-Pr Br CH Me 6-CI H i-Pr Br CH
Et 6-Me H i-Pr Br CH Et 6-CI H i-Pr Br CH i-Pr 6-Me H i-Pr Br CH i-Pr 6-CI H i-Pr Br CH t-Bu 6-Me H i-Pr Br CH i-Bu 6-CI H i-Pr Br CH
Me 6-Me H C2F5 Br CH Me 6-CI H C2F5 Br CH
Et 6-Me H C2F5 Br CH Et 6-CI H C2F5 Br CH i-Pr 6-Me H C2F5 Br CH i-Pr 6-CI H C2F5 Br CH t-Bu 6-Me H C2F5 Br CH t-Bu 6-CI H C2F5 Br CH
Me 6-Me H n-C3F7 Br CH Me 6-CI H n-C3F7 Br CH
Et 6-Me H n-C3F7 Br CH Et 6-CI H n-C3F7 Br CH i-Pr 6-Me H n-C3F7 Br CH i-Pr 6-CI H n-C3F7 Br CH t-Bu 6-Me H n-C3F7 Br CH t-Bu 6-CI H n-C3F7 Br CH
Me 6-Me H i-C3F7 Br CH Me 6-CI H i-C3F7 Br CH
Et 6-Me H i-C3F7 Br CH Et 6-CI H i-C3F7 Br CH i-Pr 6-Me H i-C3F7 Br CH i-Pr 6-CI H i-C3F7 Br CH t-Bu 6-Me H i-C3F7 Br CH t-Bu 6-CI H i-C3F7 Br CH
Me 6-Me H Et Br CH Me 6-CI H Et Br CH
Et 6-Me H Et Br CH Et 6-CI H Et Br CH i-Pr 6-Me H Et Br CH i-Pr 6-CI H Et Br CH t-Bu 6-Me H Et Br CH i-Bu 6-CI H Et Br CH
Me 6-Me H CHF2 CF3 CH Me 6-CI H CHF2 CF3 CH
Et 6-Me H CHF2 CF3 CH Et 6-CI H CHF2 CF3 CH i-Pr 6-Me H CHF2 CF3 CH i-Pr 6-CI H CHF2 CF3 CH t-Bu 6-Me H CHF2 CF3 CH i-Bu 6-CI H CHF2 CF3 CH
Me 6-Me H n-Pr CF3 CH Me 6-CI H n-Pr CF3 CH
Et 6-Me H n-Pr CF3 CH Et 6-CI H n-Pr CF3 CH
k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k k I Ift P
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi fc
O O Ω Ω
TJ TJ rø rø W rø rø rø O O o o O O O O ι? to1 to' to1 r ? rø• T- ~. o rø rø rø Tl l rø to % to % to to rø rø ^J tTl. L£Tl. T-J orøn orø rø ø rø rø TJ rø I | vo T n on orøn -4 -4 -4 -4
hri hcj TJ TJ *τj Tj Tj hcj Hcj Tj 9 9 9 9 T oJ o Tj 9 9 Tj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj hcj TJ hcj hcj hcj ft
a a a a a 8 s s s s 8 8 a 8 8 8 8 8 88888888 8 8 8 88 888 ι
W Cd 2 ff Cd
3 E E -S+ i 3 E? ES C &D p ffl] rø rø δ 3 5 ES δ 3 5 o\ CΛ Φ Os Os Os Os ON ON ON ON Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os Os |HM o o o Ω Ω O Q O Ω Q O O O o o o o O Q Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IP
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ft
a a a
Tj hcj TJ g S S ES ES o o o o o o o o OJ OJ OJ ø y y Ω Ω rø rø rø E y Ω r y ft ÷j ft to 8 to 8 to to 8 E rø rø Tj TJ
-α - rø4 -4 -4 -4 -J rø rø ^ ^ ^ ^ rø rø rø rø Ω
j hcj hcj rø rø rø Tl Tl rø TJ rø
ffi ffi ffi 8 8 a e Θ a a 8 8 a a 8 a a a a a a a a a a a a a a a a a a a a a a ix
CN t- IΛ t- χι 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3
©
CO ffl ^| fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ft O O O O O O g O O
H CJ ft
JH <n r- f r- fc r- t- r- r- fc f t ft ft ft fc fc fc fc fc c
CO fc CO fc CO ftO S +-i
ΛI c u f fc l ^ ^ fe fe fe & ft ft ft ft Hr ft ft' ft' ft fi fi
U U O o o ft ε. W W W 8 8 G 8 ά ά έ ά 8 8 8 8 -λ 3
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
-f /J| G l Gl Gl Gl o o o o o o o o o o υ o o o 1 O I O I O I O I O I O I O I O I O I O I O I O I O I O I O I O I O I fcl NO VO o vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo vo
VO χι 333353333333333333 353333335333333333
^| fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc fc ζ_ι ςj ζ_) ζ_) (j O Cj O
L^ -r -^ -^ ft. ft. ft. ft. ft^ ft- ft^ ft~ \ & * " * * * s ft o o ft o ft o δ ε; δ ε. ε. δ R $ -A & -A δ -A -A to to to to £ £ £ ξ ξ ξ ξ δ δ δ δ S S S
^| G G G G G G o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
. - to to to to to to to to to to to to to to to to to to to O to to to to to to to to to to to to to to to to t- v v v v o o vo v vo vo vo vo o v ' vo vo o o vo o o vo v vo v v v
Cό -H 90 -t o j. J-ι 3 (B 4-, H 3 (u J-. SH
CN
© •a 3 ffl I a <0 H ft ffl S M ft ffl I a _ι ft J-< ffl ^ <0 1 J
S S ft ffl a ft ffl a $ ffl s ® ^ ^ a ft ffl ^ a ft o
CD ^ Hf r+ D H t-,- g" μ "■ CD j- Hf ^ CD g^ πf ^ C j- μ " CD Ht ^ CD p- nf *"*• CP πf ^ CD ' ^ 0s 0s 0s 0s s 0s Os 0s 0s θs 0S θs \ Os 0s 0s 0s S Os 0s 0s 0s Os Os 0s Os 0s 0s OS Os 0s Os 0S θs Os θS θs n__j
2 ffi ffi ffi 2ffi iffi 2ffi ffi 2ffi ffi ffi ffi ffi-ffi ffi ffi ffi ffi ffi ffi |ffi;CD ffi ffi ffi ffi iffi ffi iCD ffi ffi CD iffi ffi ϊCD ffi ffi ffi β^
O Hi OH- OH- OH- OH- OH- OH- OH- OH- OHi QH- QH- QH- OH- QH- OH- QH- QH- QH- OH- O^ OH- OH- OH- OH- OH- OH- QH- OH- OH- OH- OH- OH- OHi OH- OH- oH- l|ftgp
Tl % on o ■§n §n § on § I 55I 5O 9J O QJ O QJ O qJ "-t T I M ^ 8 ^ 8 ^ 8 ø B RI B - - - 14 - 1-rø -rø -rø -rø , t ■Λ§υ •§> ■&*, ut
ι ro ιω ω ιcd ιcd ιω ιcd cιd wι ιω ωι w wι wι ωι ιcd ιω cιd ιω wι ω oW oHi oW o^ o^ oHi ofc oW oW oW o!-i oι-_ o!-- o!-_ oκ-- ι-- IlrøO
9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 IX
ON OO
§ ώ hj S ώ hj g ώ hj S ώ ζ ^
CD g' μ.J' ^ g* (-^ "■ & J K rt (t j- μ <"+ CD *_f «"* CD j- πf ^ p) μ^ ^ D ,- H * CD j- μf " Oi ' w ^ C_ . O O> <-^ ON O\ OA O\ C^ ON ^ OS _ . C^ C_J\ 0^
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω IP O O O O O O O O O Q Q Q O Q O O Q O O O O O O O O O Q O O O O O O O |FT
I Tl o "8n - oSn - oSn o -Sn 5 I 5I 5I 5I O 5J 5OJ JO?J O 5J I ι Iτ Iι Iι t 8J t 8J t 8J lN 8-J » B » » - -4
9 ffl ffl9 ffi9 ffi9 ffl9 9ffl 9flf ffl9 9ffl 9ffl ffl9 9lff 9fc 9ffl 9fc 9ffl 9fc 9ffi 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9ffl 9fc 9ffl 9fc 9ffl 9ffl 9ffl fl9f 9fc 9ffl 9fc ι
ώ g4a R4b E2 ≠ X R.. g4a R 9 R_. X
Et 6-Me Cl n-C3F7 Br CH Et 6-CI Cl n-C F7 Br CH i-Pr 6-Me Cl n-C3F7 Br CH i-Pr 6-CI Cl n-C3F7 Br CH t-Bu 6-Me Cl n-C3F7 Br CH i-Bu 6-CI Cl n-C3F7 Br CH
Me 6-Me Cl i-C F7 Br CH Me 6-CI Cl i-C3F7 Br CH
Et 6-Me Cl i-C3F7 Br CH Et 6-CI Cl i-C3F7 Br CH i-Pr 6-Me Cl i-C3F7 Br CH i-Pr 6-CI Cl i-C3F7 Br CH i-Bu 6-Me Cl i-C3F7 Br CH i-Bu 6-CI Cl Z-C3F7 Br CH
Me 6-Me Cl Et Br CH Me 6-CI Cl Et Br CH
Et 6-Me Cl Et Br CH Et 6-CI Cl Et Br CH i-Pr 6-Me Cl Et Br CH i-Pr 6-CI Cl Et Br CH t-Bu 6-Me Cl Et Br CH t-Bu 6-CI Cl Et Br CH
Me 6-Me Cl CHF2 CF3 CH Me 6-CI Cl CHF2 CF3 CH
Et 6-Me Cl CHF2 CF3 CH Et 6-CI Cl CHF2 CF3 CH i-Pr 6-Me Cl CHF2 CF3 CH i-Pr 6-CI Cl CHF2 CF3 CH t-Bu 6-Me Cl CHF2 CF3 CH t-Bu 6-CI Cl CHF2 CF3 CH
Me 6-Me Cl n-Pr CF3 CH Me 6-CI Cl n-Pr CF3 CH
Et 6-Me Cl n-Pr CF3 CH Et 6-CI Cl n-Pr CF3 CH i-Pr 6-Me Cl n-Pr CF3 CH i-Pr 6-CI Cl n-Pr CF3 CH i-Bu 6-Me Cl n-Pr CF3 CH i-Bu 6-CI Cl n-Pr CF3 CH
Me 6-Me Cl CF3 CF3 CH Me 6-CI Cl CF3 CF3 CH
Et 6-Me Cl CF3 CF3 CH Et 6-CI Cl CF3 CF3 CH i-Pr 6-Me Cl CF3 CF3 CH i-Pr 6-CI Cl CF3 CF3 CH i-Bu 6-Me Cl CF3 CF3 CH i-Bu 6-CI Cl CF3 CF3 CH
Me 6-Me Cl i-Pr CF3 CH Me 6-CI Cl i-Pr CF3 CH
Et 6-Me Cl i-Pr CF3 CH Et 6-CI Cl z-Pr CF3 CH i-Pr 6-Me Cl i-Pr CF3 CH i-Pr 6-CI Cl i-Pr CF3 CH t-Bu 6-Me Cl i-Pr CF3 CH t-Bu 6-CI Cl i-Pr CF3 CH
Me 6-Me Cl C2F5 CF3 CH Me 6-CI Cl C2F5 CF3 CH
Et 6-Me Cl C2F5 CF3 CH Et 6-CI Cl C2F5 CF3 CH i-Pr 6-Me Cl C2F5 CF3 CH i-Pr 6-CI Cl C2F5 CF3 CH t-Bu 6-Me Cl C2 5 CF3 CH i-Bu 6-CI Cl C2F5 CF3 CH
Me 6-Me Cl n-C3F7 CF3 CH Me 6-CI Cl n-C3F7 CF3 CH
Et 6-Me Cl n-C3F7 CF3 CH Et 6-CI Cl n-C3F7 CF3 CH i-Pr 6-Me Cl n-C3F7 CF3 CH i-Pr 6-CI Cl n-C3F7 CF3 CH t-Bu 6-Me Cl n-C3F7 CF3 CH i-Bu 6-CI Cl n-C3F7 CF3 CH
Me 6-Me Cl i-C3F7 CF3 CH Me 6-CI Cl i-C3F7 CF3 CH
Et 6-Me Cl i-C3F7 CF3 CH Et 6-CI Cl i-C3F7 CF3 CH
ES 2 ώ ES 2 ώ ES 2 ro
E? CD g^ H p* cD g^ Hr " ffi ø i-r W Cd
3 g rt C2D Sώ l" ES C2 øώ ES 2 yώ .,-ςr -* 2 ώ δ hf E rtS (21 ώ fi rf | lftω
ON O\ ON ON ON ON O ^ ON ON ON ON ^ ON C3. a\ ON aN ON k P ffi ffi CkD kfif ffik ffik ffik ffik ffik ffi ffik %CD %ffi %ffi %ffi ϋffi ffi k k k k k k k k k k k k k k k k k k k k ϊL
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω \
ft
hrj hcj TJ TJ TJ Tj TJ TJ Tj TJ TJ Tj TJ Tj hcJ Tj Tj TJ Tj TJ TJ TJ TJ TJ TJ rø Tj TJ TJ TJ TJ TJ TJ Tj TJ TJ OJ OJ OJ OJ OJ OJ I Ift Os
hrj hj Hj Hj hrj hcj Mcj Tj hcj Mcj Tj Hrj Hjj Mcj Hjrt Hrj Hj Hrj HH Mcj Q hcj Q hcj Tj O hcj O hcj Q rø 99 a 888 88 i* o δ ► E^S ^D δ ∑3 δ E rtS t CD δ -i δ >1 ES t CD δi δ i-r E^S iClD øδ δ ML ES CD ø tJd δ Ht E "S 2 ffi ø w Hf E rtS t ffi ro ø E t øώ Hi E^ ^ffi δ lft o*. Os Os O Os Os Os Os Os Os Os Os Os Os Os
O o o o o o o o o o o o o o o I Ift p ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi Ω Ω Ω Ω Ω Ω !
TJ TJ Tj TJ TJ TJ TJ Tj TJ Tj Tj TJ rø rø rø Tj rø Ω rø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωrø Ωh-j ΩrJ Ωhrl ΩTJ ΩTj ΩTJ Ωffi 9ffi 9ffi 9ffi 9ffi 8 *
IΛ t- vji ft O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O
^' O o o o o o o υ o o o o o o o o o o υ o o o o o υ o o o o o o o o
© ffl P^| fc O O O O O O O O O O O O O O
H CJ ft r- in «n fc fc fc f in in r^ r- r- c fc c fc fc fc cf fc I— r- ft fc r- t— fc
^ι « g e § g fc fc fc fc f s ε. ε. u U U ft ft ft CN CN
CJ J O CJ o o υ O o ft W W W
«:
ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffi ffl ffl ffl ffl ffl ffl ffl
o o o O o o o υ υ o o o o o o o O υ o O O O o o o o vo VO o VO VO O VO VO VO o v vo VO VO o o vo vo vo vo vo ό vό
- ^_ ι ^3 ^o a^ ftπ m3 ^ω a^ ftι ^ |o a^ ftι ffl3 ^<u a ft^ ^3 <u a_ fth ffl3 ^<u a^ ftι ffl o aJι ftSH ffl3 ^(o aw ftiH ffl3 tr- ftO G oG Go Go Go Go Go Go Go Go Go Go Go Go Go Go Go Go Go Go Gυ Go Go Go Go Go Go Gυ Go Go Go Go
^| ft G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G c— r— r— r— r— r-- t— - r— i° r,1 .-^ .^ fc fc. fc ft fc fc ft fc
fcl
.. to to to to t-
« ^> ζf ^ to a.i_. _ftiH m »__! ^ to _H> *ftH ^ •_? | to j_» fti ffl ζ? ^ to -H» ft*H ^ "__! to a -π» _fti-< ffl ^ to a-w ^ft** ffl ^ ^ to a_» fti-' p s to a ,._» ft ffl !=f o
Table 18
R9 is CHF2 R9 is CH CF3 R9 is CFoCHFτ
R3 R4a R4b R6 R3 R4a R4b R6 R3 R4a R4b R6
Me CH3 H Cl Me CH3 H Cl Me CH3 H Cl
Et CH3 H Cl Et CH3 H Cl Et CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl i-Bu CH3 H Cl i-Bu CH3 H Cl t-Bu CH3 H Cl
Me CH3 H Br Me CH3 H Br Me CH3 H Br
Et CH3 H Br Et CH3 H Br Et CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br t-Bu CH3 H Br i-Bu CH3 H Br i-Bu CH3 H Br
Me CH3 F Cl Me CH3 F Cl Me CH3 F Cl
Et CH3 F Cl Et CH3 F Cl Et CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl i-Bu CH3 F Cl t-Bu CH3 F Cl i-Bu CH3 F Cl
Me CH3 F Br Me CH3 F Br Me CH3 F Br
Et CH3 F Br Et CH3 F Br Et CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br i-Bu CH3 F Br i-Bu CH3 F Br i-Bu CH3 F Br
Me CH3 Cl Cl Me CH3 Cl Cl Me CH3 Cl Cl
Et CH3 Cl Cl Et CH3 Cl Cl Et CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl i-Bu CH3 Cl Cl i-Bu CH3 Cl Cl t-Bu CH3 Cl Cl
Me CH3 Cl Br Me CH3 Cl Br Me CH3 Cl Br
Et CH3 Cl Br Et CH3 Cl Br Et CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br i-Bu CH3 Cl Br i-Bu CH3 Cl Br i-Bu CH3 Cl Br
Me CH3 Br Cl Me CH3 Br Cl Me CH3 Br Cl
Et CH3 Br Cl Et CH3 Br Cl Et CH3 Br
Cl
3 3 fc 5 a a ft 5 a 3 3 3 3 ft 3 1 a ft 3 1 a ft 3 a ft 3 a 3 ft PQ a ft s a 3 ft 3
3 3 3 3
Cλ.1 ft 3 1 a 5 3 a 5 a 3 ft ffl
— - 1 a ft 3 a ft •— - 3 1 a 3 ft PQ a s 3 3 a 3 ft 3 3
c G G m to ffl ffl G G G G ffl ffl ffl ffl G G G G ffl m m ffl o o o o o o o to to to ffl G
δ δ δ 8 δ 8 fc δ 8 fc o G G G fc fc fc fc fc fc ft ft G
3 ffl 8 3 ffl 8 3 3 3 3 5 ffl 8 8 ffl 5 5 5 o o o o o υ o o o
3 3 3 3 3 3
fi 3 a 3
§ p w 5 ffl fc ε. *P 3 a s 3 a 3
5 3
E H* 2iffi δ cl ^ C2D δ y ι_C E "S* [ ffi p 3δj T ES i? πT ErtS iC?D pj E 1S- i ffi δ £ 32 δ 1 rø Cd ι 3 w 3 w W
3 |-ι 0 w rø 5 ft
ro ω o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o lft I 1rø vo
Ω
T hCJ Hτj Hj HJ M^ Hι Hτ Hc H-j OJ OJ OJ OJ OJ OJ OJ OJ ffl ffl ffl ffl ffl ffl ffl ffl ffi ffi ffi ffi ffi ffi ffi ffi o o Irø.
Ito
o o o o o Q ffl W ffl W Q O o o w ω ω ω o Q Ω Ω w ro ro w o o o o ro 1 ro1 ro1 ro1 o o Irø
45-
O O O Q Q W ffl W ffl Q Q Q Q ffl ffl ffl ffl Q O Q ffl ffl ffl W O Q O Q ffl W ffl ffl Q O |rd
_ rø <+ 2 G δ ø δ ES i2 CD δ ø δ E "S^ i? CD δ ø δ ES i CD δ ø δ ES i CD δ p) δ I-T E "^S i CD δ pj δ E "S+ i ffi δ ø δ ES Ci?D δ _j δ i-f E "S+ t ffi δ ?! δ i-t ft '
Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω 5, 5, 5, H? Ω Ω ft
3 3 c" l ft ffl W ffl a ft ffl 3 3 ffl w ft ffl w ft .3 o 3 w ft ffl .-T fc 3
W ffl
1-.I G G li li li pq ffl m m G G G G ffl ffl ffl (-3 G G G G m m m m G G G G ffl ffl ffl ffl
fc fc fc fc fc G G G G G G G G m m m m M ffl M ffl
f ffl f ffl ffl ffl ffl ffl ffl ffl ffl ffl ffl l
« fl ffl ffl fl ff ffl ffl ffl ffl ffl ffl ffl ffl ffl flf ffl ffl ffl
^| G G ι_3 m m m G G G G m ι-3 m m G G G G m m ^ m G G G G m m m m
fc fc fc fc fc fc G G G G G G G G m m m m m m M M
m m m ffl ffl ffl ffl ffl m m ffl ffl m ffl ffl m m ffl m m ffl m m m ffl m ffl m m ffl
ft J_JHM 3 '-a' to a -π* * _fti"< 5ffl "-r _to! .a*-H.j *ft-j 5ffl ,_r -|to! a«-___. ^ft_iM ^ffl '-* 3 to a _■__ ft fc ffl i-* _ toB a - .T.__ ft fc *-. p ^? 3 _ ω_i a * ,ι_.- ft rfc *-< p r?r 3 _to3 a .-T f & rg
Table 19
R9 is CHF2 R9 is CHoCF3 R9 is CFoCHF
R R4a R4b Rθ Sf! g4a R4b ≠ R R4a R4 R-!
Me CH3 H Cl Me CH3 H Cl Me CH3 H Cl
Et CH3 H Cl Et CH3 H Cl Et CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl i-Bu CH3 H Cl t-Bu CH3 H Cl i-Bu CH3 H Cl
Me CH3 H Br Me CH3 H Br Me CH3 H Br
Et CH3 H Br Et CH3 H Br Et CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br i-Bu CH3 H Br t-Bu CH3 H Br t-Bu CH3 H Br
Me CH3 F Cl Me CH3 F Cl Me CH3 F Cl
Et CH3 F Cl Et CH3 F Cl Et CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl i-Bu CH3 F Cl i-Bu CH3 F Cl i-Bu CH3 F Cl
Me CH3 F Br Me CH3 F Br Me CH3 F Br
Et CH3 F Br Et CH3 F Br Et CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br i-Bu CH3 F Br i-Bu CH3 F Br t-Bu CH3 F Br
Me CH3 Cl Cl Me CH3 Cl Cl Me CH3 Cl Cl
Et CH3 Cl Cl Et CH3 Cl Cl Et CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl t-Bu CH3 Cl Cl t-Bu CH3 Cl Cl t-Bu CH3 Cl Cl
Me CH3 Cl Br Me CH3 Cl Br Me CH3 Cl Br
Et CH3 Cl Br Et CH3 Cl Br Et CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br i-Bu CH3 Cl Br t-Bu CH3 Cl Br t-Bu CH3 Cl Br
Me CH3 Br Cl Me CH3 Br Cl Me CH3 Br Cl
Et CH3 Br Cl Et CH3 Br Cl Et CH3 Br Cl i-Pr CH3 Br Cl i-Pr CH3 Br Cl i-Pr CH3
Br Cl
to to to to G G
G G G G G G
3 3 ffl 3 a 3 3
5 3 3 a 3 ft 3 3 a 3
5 3 3 a ft s 3 a 5 3 3 to 5 3 3 a s 5 3 a s 4 3 a
4 G ffl ffl to to G G G G ffl ffl ffl to G G G G ffl ffl m ffl ffl ffl ffl ffl G G G G ffl to ffl ffl G G
3 3 3 3 3 3 3
3 3 a ft •-— 3 3 a 3
5 3 3 a $ 3 3 a ft 3 3 a ft 3 3 a ft 3 3 a 5 3 3 a 3 ft 3 3 a
G ffl to ffl* ffl G G G ffl ffl Q ffl G G G G to to ffl to G G G G to ffl to ffl G G G G G c oo δ G f in ffi fl i ffi ffi ffi ffl ffl ffl to fc f fc o δ δ 8 fc δ c o δ G G G G fc fc 5 in fl f ff
3 | i G G G o G G G σ G G G G G G G G G G G G G G o G G G G G G G G G G ffl to
3 3 3 3 3 3
14 3 3 a ft — - 3 3 a δ 3 3 a 5 3 3 a ft p 3 a ft 3 3
3 3 W $ 3 3 a 3
5 fc 3
3 R pp 3 to
PHI G ffl m ffl ffl G G G G to m ffl ffl G G G G m to m m G o G ffl PQ ffl ffl G G G G G G
Cd rø W Cd r
3 3 5 w ES s T? ø
3 t? w Cd
3 3 δ T CD δ δ *% ES . tfD δ c δ ES l f
3 3i Ti-r ^ ffi? δi δ 1 ES 2D J-j tlO
ro cd cd cd cd cd cd ffl ffl cd cd cd ro ro ro ro ro cd ro ω ro ro ro ro ro ro ffl W ffl
_? S? _? !_? !-? _? _P S:, Ω Ω Ω Ω Ω Ω Ω Ω rø TJ Tj
ffl ffl ffl W O O O O W Cd W W O O O O W W W W O O O O ffl W W W O lrø
0 ro δr E rtS i ffi< Cd rø Cd
3 EP 3 E? rø ø
3 ω E? W
3 ω Ei? r κ rø W Cd
3 E? W ro
3 Irø.
3 T 3 H 3 n 3 "
ro ffl ro ro ro ro ro ffl ffl c rø vo
1 1 1 ro1 1 1 ro1 1 1 ro1 ro1 ro1 1ro 1 1 ffl1 ffl1 1d ro1 ro1 1ro c1d ro1 ro1 ro1 c1d c1d 1ro ro1 p|^- o ffl 1 HH H HH HH HH HH HH HH Cd ω W ω ro ro W ro Q O O O Q O O Tj hH hrJ TJ h^ vo
w ω ω ro o o o Q ω ω ω ω o o o o ro ro ro ω o o o Q ro ro w ffl o |rø
δ ES i δ ES δ ES t| δ ES i| ES | δ ES i| δ ES i δ |! rø.
3 H 3 'I
9 Ω Ω Ω w w ω w 5) W w ω Ω Ω Ω Ω ω w ω ω Ω Ω Ω Ω 5J Sj S3 5, Ω lft
rø 2 CD δ ø δ E ^S 2 CD δ ø δ Hi E -S+ 2 ffi δ a" δ i-f E -S+ ffi2 δ cj δ H| E rtS i? CD δ Jr δ i-f E -S+ t ffi? δ ø δ Hi W Irø
3 •"*
■9 fc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc Ωfc Ωfc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc 9fc
ffl W Q O O O Q Q O O Tj Tj Tj TJ Tj TJ TJ TJ ffi ffi ffi ffi ffi ffi ffi ffi
Q Q ^ ^ Q Q Q Q ^ ^ Q Q Q Q SP ff S ffl Ω Ω Ω Ω ft ON
Ω Ω -? w ω κ Ω Ω Ω Ω w κ -? -? Ω Ω Ω Ω w -? H? Ω Ω Ω Ω ft
t rts 2ffi ώ H^ E^S iffi ro 0 1 E "S 2ffi m 0 ώ ώ St rø >-, ro 0 ES 2 0ro δ l ES 2 ro ES 2^ E3 2ff Hώ ES 2 ro ;ς w
3 T_| " ffi 0 H^ l- ffi pj Ht ^ i 3 i Tf Λ (( S if ' «
ω 1 ω 1 O Ω Ω ff !-r !-ri 9 9 Ω Ω ω H? H7t H? Ω Ω Ω Ω H? H? H? H? Ω Ω Ω Ω H? H? H? H? Ω Ω ft
O O O O Ω Ω Ω Ω O Ω Ω Ω Ω Ω OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ OaJ i Ift Irø
9
Ω Ω Ω Ω Ω Ω ffi ffi ffi ffi ffi ffi ffi ffi Iffi
O9J O9J O9J O9J O9J O9J O9J O9J O H- O H- O H- O H- O I— O 1— I Ift jy' |feJ
Ω Ω ^ -? ^ H? Ω Ω Ω Ω H H? H? H? HV H? H? Hy Ω Ω Ω Ω H? H H? H? Ω Ω Ω Ω H H H H Ω Ω ft
E π÷ i2ffi δ a" E "S+ ffi δ ø δ Hf E 1S- ffi δ pi δ HI E rt ^ CD δ -j Hr E-SH- iffi δ » if "E i2 β δ pj Ht E <-S* ^ ffi Zj i-T E -* ffi! δ - 3T ^ E rtS i ffi δ _ 3; 'l ft I OJ
Ω H? H? H H Ω Ω Ω Ω H ffl H? H? H H? ffl _? Ω Ω Ω Ω -? H H? t Ω Ω Ω Ω H? ffl W Hf Ω Ω lft
w ro ij δl-r E-SH- ^CD firo τlJ' E1S- ffi2 aώ" % if s "+ ffi gώ' nT E^S iC? gro' Hr E-SH- ffi ώ I ^ 1U rtw tH _fflT % Hf -+ 2 ffi ώ g" H^ E 1- ^ ffi ro δ ft
H? E? Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω ft rø
_0 vo
Ω
W C T 1d J
1 J rø Tj Ti Ω Ω Ω rø rø rø rø w 1 ffl ffl1 ffl1 ffl ffl Cd
1 ffl1 1 1 1 Tj Tj rø rø TJ Tj rø TJ
OJ OJ OJ OJ OJ OJ OJ OJ ffi ffi ffi ffl ffl ffl PL
o o μ— i o o H-* o μ—t o h—t o o i o H-* o H-* ro ro μ-{ ω ω o o o o ω μ-t ω μ-t ω ^t ω Η o μ—t o μ— - o μ— ι o ω μ-t ω H ω μ-t ro μ-t o μ— ι o μ-^ o μ— ι o μ—t ω ω μ-t i I C OJN
rø c &o 0 dd 0 Cd Cd rø rø-ι' E "S* t fif? p r
3 ι 3 ω ι ro; πT rtES C2D £ό^ rtES i fl)' £ώ δ ii E rt i CD' ro 4 U E rtS (it' ro 1-1 W W w
3 EP o
3 to ft
W ro o θ O O O Q Q O O Q Q Q O O O O O Q O O O O O O O O O O O θ |ft jrø
VO
Iffl po τi hH θ o o o 9 9 9 9 9 9 9 t
H ι? Hι? Hι? Sι) rø rø rø rø rø rø rø rø Ω ^ Ω^ Iftσ'fej
v^ θ Q Ω Ω κ ω w w Ω Ω Ω Ω κ ω ω ω Ω Ω Ω Ω w w ω ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω lft
E 1S- iffi δ g' if E "SH" i ffi δ HI E <■S* ffii δ 1 If E rtS i tH δ rt if E rtS 2 (I δ if ^ 11 ^ Λ (2I δ _j δ Hf E "* ffii δ pj i E rtS ^ ffi δ g" δ Hf E C5* ^ ffi Zj | ft I OJ
cd cd cd w cd w w ffl ω ω o o o o o o o o o o o o o o o o o o o o o o o o o o lft
Q- Ω >— rø rø rø rø rø rø rø rø OQJ OQJ O9J OQJ OQJ OJ O9J O9J ffl ffl ffl ffi ffi ffi ffl ffi rø rø rø rø rø rø rø rø ι-i '-ι | Ift α*
Ω Ω HF H ffl ffl Ω Ω Ω Ω Ω Ω Ω Ω H^ ffl ^ ffl Ω Ω Ω Ω Hf ffl ffl ^ Ω Ω Ω Ω ∞ ∞ ^ ∞ Ω Ω lft
ffl δ ES s? δ δ ES i? δ δ ES .? δ δ ES 2 δ δ ES 2 δ δ ES 2 δ δ ES ; δ ft
ffl ffl cd ffl cd ffl ffl ffl ffl cd cd ro ro ffl cd ffl ffl ffl ro cd cd cd ro ro ro ro ro ro ro ro Ift rø
1
O O O O O O O O TJ TJ TJ TJ TJ TJ TJ TJ ro ro ro ro ffl ffl PL .■--
W 1 1Cd C1d Cld Ofc Ofc O^ Ofc Wl C1d C1d Cld Ofc Ofc Ofc Ofc Cld C1d C1d ffll Ofc Ofc OH OHi C1d C1d W W OHi Oi--- l|røO.
Cd E? rø _? s? rø Cd rø ES 3 ω rø rø ffl EP rø Cd δ ES 2 δ δ ES |2 δ δ |!
3 3 T 3 ι ft
Cd Cd Cd ffl ffl Cd Cd Cd Cd Cd ϋd Cd Cd Cd Cd ffl Cd Cd ffl ffl ffl ffl Cd
cd ro ro ro ro w ro w Ω Ω Ω Ω Ω Ω Ω
53 ffl ffl ffl Ω Ω Ω Ω ω ω ω ω Ω Ω Ω Ω w ω ω ω Ω Ω Ω Ω ω ω ω ω Ω Ω ft
ro ro ro ro ro ro ro ro ro ro ro ro or ro cd ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro | Ift 3
9 9 9 9 9 9 .9 .9 » ffl ffl W « W W « Ω Ω Ω Ω Ω Ω fe
ffl ffl ffl ffl Ω Ω Ω Ω w ω ω ω Ω Ω Ω Ω ω ω ω 5:l Ω Ω Ω Ω w w w w Ω Ω ft
a a a a a O 8J a 8 a O aJ 8 a a a a a 8 a a a 8 8 a a a 8 a
ro ω ω O O o o o O O O rø rø Tj TJ TJ
1 rø TJ rø ffl ffi ffi ffi ffi ffi ffi ffi
O O O ro Cd Cd ro Q O O O ro ro Cd ffl O O O O ffl ffl ffl H? Q Ω Ω O ft
Cd Cd ϊ? O Ω O o Cd SF W ω O Ω O Ω ffl « ffl Q Ω O O t? ro Cd Cd o Ω o Ω ro Cd Cd Cd O ft
to ES cf δ 3 to ES δ 3 5 ES cf δ 3 5 ES cf δ 3 5 ES f c δ 3 to ES δ 3 5 ES cf δ 3 to ES 1 δ 3 5 ES δ 3 ft
o Q Q Cd Cd r
H? ro Ω Ω O w o or Cd Cd ω ffl w Ω O Q O Cd Cd Cd Cd Q o Cd Cd Cd W O ft
Ω O H? ω ω H? o o o ω W W εp ffl ω w ffl o Ω o o H? ω ω ffl Q O ω w w 2 O ft
G G G G G m ffl m m o o
g fc fc fc fc fc fc fc fc O
o m ffl ffl ffl ffl ffl ffl ffl PQ ffl
3 wd j 2 a H 3 a 5 ffl a ft p ft % J 1 ^ ω a -H- 3 3 3 3 ffl ft ffl S w ft ffl 3 w ft ffl w
pi| f-. m m m o o o o ffl m m fδ G G G G ffl ffl ffl to 0 0 0 ϋ to to to to U 0 a U co co co co co co co co _ _ _ι _
VO S l G ft ft ft ft ft ft ft ft ffl ffl ffl ffl
OO ffil δ δ δ δ δ s δ 5 u u υ ϋ h h υ
3 I __ -_ -_ rt
PHI •^■.i G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G m m
ffl l
^i H^ G G G H^ m m S G G G G m m m m G G G G m ffl m m G G G G G G G G G G
SI ^| ffi ffi ffi ffi ffi ^ g ^ g g g g g r3 ^ ^ rg s m ffl ffl ft ft ft ft G o ft ft ft ft ffl ffl t- cό
PHI fcl O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O ffl ffl
o ^ ffl ra ft ffl ^ a ft c? ^ a ft ffl a ft ffl 3 s ^ ^ ^ fe ^ s ^ P s ^ p? 3 s
3 3 ftl 3 3 to s 3
3 3 a 3 ft PQ 3 a s 3
3 3 a 3
5 3 3 a ft 3 3 a 3
5 3 3 a s 3
3
3 3 3 3 3 3 3 3 °JI 3 3 to 5 3 3 a ft pp 3 a 5 3 3 a ft pp 3 to 5 ffl t
— - 3 a f 3 3 to ft p
fc fc fc fc fc o o o o o o o o
ffl ffl m ffl ffl ffl ffl m ffl ffl ffl ffl m
3 3 3 3
3 3 a 5 3 3 a s 3 3 a s 3
Table 22
R9 is CHF2 R9 is CH CF R9 is CF CHF
R R4a R4b R6 R3 R4a R4b R6 R R4a R4b R6
Me CH3 H Cl Me CH3 H Cl Me CH3 H Cl
Et CH3 H Cl Et CH3 H Cl Et CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl i-Pr CH3 H Cl t-Bu CH3 H Cl i-Bu CH3 H Cl i-Bu CH3 H Cl
Me CH3 H Br Me CH3 H Br Me CH3 H Br
Et CH3 H Br Et CH3 H Br Et CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br i-Pr CH3 H Br t-Bu CH3 H Br i-Bu CH3 H Br i-Bu CH3 H Br
Me CH3 F Cl Me, CH3 F Cl Me CH3 F Cl
Et CH3 F Cl Et CH3 F Cl Et CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl i-Pr CH3 F Cl t-Bu CH3 F Cl t-Bu CH3 F Cl t-Bu CH3 F Cl
Me CH3 F Br Me CH3 F Br Me CH3 F Br
Et CH3 F Br Et CH3 F Br Et CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br i-Pr CH3 F Br t-Bu CH3 F Br i-Bu CH3 F Br i-Bu CH3 F Br
Me CH3 Cl Cl Me CH3 Cl Cl Me CH3 Cl Cl
Et CH3 Cl Cl Et CH3 Cl Cl Et CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl i-Pr CH3 Cl Cl t-Bu CH3 Cl Cl t-Bu CH3 Cl Cl i-Bu CH3 Cl Cl
Me CH3 Cl Br Me CH3 Cl Br Me CH3 Cl Br
Et CH3 Cl Br Et CH3 Cl Br Et CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br i-Pr CH3 Cl Br t-Bu CH3 Cl Br i-Bu CH3 Cl Br i-Bu CH3 Cl Br
Me CH3 Br Cl Me CH3 Br Cl Me CH3 Br Cl
Et CH3 Br Cl Et CH3 Br Cl Et CH3 Br
Cl
^1 l Si l
G G ffl to m m G G G G ffl m m i-I G G G G m m ^ m rø ffl ffl ffl G G G G m to to to U
.CNI ffl co co co co
5 f m m flf fc fc i ffi ffi ffi ffi ffi ffi ^ffi
H % m m fl fc fc fcco fcco fcco fcco ff
O O O O O O O J CNI ft a 3 I
PHI 14 3335533553333335533533 O O O O O O O O O U O o
3 3 3 3 4 ft 3 ffl 3 w ft ffl w ft A ffl -A w ft 4 a ft ffl S ft ft ffl w ft ffl p £ pf ft ; a ft ffl ^
P4 O ffl ffl ffl m G G G G rø m pq m o o o o m m m ffl ffl ffl to to G G G G m ll H, m m m G
s< ! | £? | --. w .T f J. ^ ,3 | -^ a ( i? ""* a ^ -S ir?S -|__ a*. f-t! fr?S |_l_ s*. -,fc ^^ _a a *^ ^^ _|) a « ( * ^ 5 _i a s ά ^ _^!
^i G m m m iS G G G G m m m m G G G G m m m m G G G G o G o G m w m fS o
co co co co co co co co _, -_- _-, -_. ffl f | fLj flj ^ [lj |l( J * 3 *
SI 14 ffl ffl ffl ffl ffl ^ [lj o o o o o o o fc fc fc fc fc fc fc fc ςj
t- 3 I .co co co co co co co co co co o co
Pi\ 14 δ S S' B' S' 5' B' 5' S 5' S' B' 5' 5 if δ" B B" δ if δ if S if if i D ϋ ϋ ϋ ϋ a ϋ ϋ ϋ o l\ ft, m5 tD aii ft_H p3ρ (u a^ ft< pρ (u a^ ftj- p_5p o aii ft< fflJ-_ aj aii ftJH ffl^ ftJr< jp3?. ffl5 'p3 M ft pp ^ ft 3
IΛ t- ^i G G m m m a G G G G ffl m m pH G G G G G G G G ^ a m m G G G G m m m ffl
CNI ffl
H cf fc fc fc fc fc fc CJ ^ll δ δ δ δ δ δ δ δ ^ fc fc fc fc fc fc fc rj ft ft[ tl G G G o G o G m
14 σ o o o o o o o o o o o o o o o o o m ffl S fi m m ffl fi m
3 3 3 3 3 ii 3
14 tf ffl w ft ffl ffl ft 3 ) 3 ffl 3 ffl ft ffl S to ft ω -u A ffl ffl ft ffl a ft ffl W ft ffl ^ a ft* m 3 5 <->
^i G G m m ffl ffl G G G G m' m ffl & G G G G & m m m G G G G ffl m m p-i G G G G G
fcl -S -H -H Hi Hi Hi Hi Hi Hi Hi ii li li lH li CO CO CO CO CO CO CO CO _ _i _i __< o ol ^| o o ffl ffl ffl ffl lff ffl ffl ffl m ffl m ffl ι-| M ι-| >--| ι-ι ι-ι « « ft ft ft ft ft
CN ffll
3 I __< ι [
PHI "^ G o G G G G G o o G G o G G G G G G o o G o G G G G G G G G G G G G ffl
SI JH ! a ϊ ξ. 3 H & a ** ξ Jr. ^ 3 ! & δ *÷ ^ f. H 3 & a I a I s I s ^ Ή 33 ΛHI 3 3 3s I
^i o m m ffl ffl G G G G m m ffl ffl G m ffl m ffl G G m m ffl a G
δ ør
3 ES δ 3 ES c δ 3 5 ES cf δ 3 to ES cf δ 3 to ES cf Cd
3 ES cf 3 δ to ES cf 3 δ to Ift
Cd ffl ffl Cd O O O Q Cd Cd Cd s? O O O O Cd ro ro ro Q O o Cd ffl Cd Cd O Ift
Cd
3 ϊ ES cf 3 δ 5 ES 3 δ 5 ES c ffi S
3 δ 5 ES cf ffli
3 5 ES cf 3 δ 5 ES 3 δ δ ES cf 3 δ to Ift
ffl Cd Cd
ffl Cd ffl ffl o O Ω ffl « ffl HS o Ω ω ffl Ω 9 Q Q ω ffl ffl ffl ft 1 Os
ro
3 s ES cf δ 3 HP ES c 1 5 ES δ 3 to ES δ 3 5 ES δ 3 5 ES cf δ 3 to ES cf δ 3 5 Ift
EP w Cd 0__ E W lff
3 E? ffl CD w δ ES 2 CD pwj Ht w " f2fi ι 3 EP W
3 ffl EP W
a a Ω ffi Ω ffi Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω ffl Ω flf Ω ffl Ω Ω fc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc Ωfc
ffl ffl flf O O O O O O O O Tj Tj Tj Tj Tj rø rø ffi ffi ffi ffi ffi ffi ffi ffi
Ω Ω Ω S? S? E? E? o o o o w 1 ro w1 ro1 o*-= o o o w ω w ro o o o o PL ON
O o w w w ffl Ω Ω Ω ∞ ^ ^ S' Ω Ω Ω ^ ^ ^ ^ Ω Ω Ω Ω lft
o o o o o o o o o Ω Ω ffl ffl ffl ffl
Ω Ω Ω rø rø rø rø o o o o
o o o ω ω ω ω o o o o o o o o w w ω ro o o o Ω E? EP - ι? Ω Ω Ω Ω ω M W W Ω |ft
÷j S I td ÷j g s Cd
3 EP w I w 3 E ι? ES g δ S 2 ro δ ES 2 ro δ ffl
3 δ |-ι ES 2 Cd W irø.
3 0 2 ro δ E
3 3 T 3 3 "I cf Cd
Ω Ω Ω 5) 5, ι? ι? Ω Ω Ω Ω ^ ^ ^ S ff S< S( S:) Ω Ω Ω Ω 5- ιϊ) 5- 5' Ω Ω Ω Ω 5- 5' -ϊ, _? Ω ft I
ES l?> ro ES 2 ES l' ro ES ιf' ro ES 2 ro ES 2 ro ES 2 ώ ES 2 ro ES 2 ro |rø
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω a a a a a a a a a a a a a a a a a a a a
ffl ffl ffl ffl ffl ffl ffl ffl Tj hrj TI Tl Tl Tl Tl TJ HI ro td c cd
Ω Ω Ω _? δ- E? E? Ω Ω Ω Ω S:, 5:( ω ω ω ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl ffl ffl Ω ft
a m m m G G G G G G G G m a ffl to ϋ ϋ ϋ ϋ to to to to ϋ o
8 δ δ δ δ δ δ δ δ fc fc fc fc fc fc fc fc G o G G G G o o m m
o o o o o o o o m m m ffl m m ffl m m ffl m m m m m ffl m m
* p-.- 1 p 3pr &^u .a* ___*> £ft -ϊ-1 3p rρr & ω a * ,w* ft & ,__-« c 3 ■-» & ω .a*J_*» ft_r^ 3M μ_r & s *___*_> Jftr. 3m &3 to ^ .* -__*» ^z 3ρp &3 to .^* ,__*_, ^ Jr. m 3 &3 ω s-_-_. ft_ fci-ι rρr _ to*_ «a -__> ft ,!M 3p M?r _ toa a .j_>
^l ffl m m ffl o o o o m m m m o G G o m m ffl ffl o o o o m m m m
fc rj G o G ft ft
CO l J*. 3 <]_ ._. JH _2 1) ._, 3 tU -j jH 3 » ι_ • ? -> .__, < 3 *1 3 3 5 ( jl
^ pQ ^ a ft ^ ^ a ft ffl a ft ffl ^ a ft pp a ft ? a ft pρ a ft ffl ft pp p p ^ a
^| G f-. ffl m ffl G G G G m m m ffl G G G G ffl m ffl m G G G G m m m m G G G G G G
^'flfll 8 ffi ffi ffi ffi ffi ffi ffi ffi m ffl m ffl ffl m m m δ δ δ δ δ δ ^ t- l t4 g o o o o o o g g g o o o o o o g g o g g o o o o g g g g g o o o m m
o 3 -a J- "=" Si "^ -l jH S dj SH *-i t _1 _H 3 t_> - _H π' O jl JH 3 (J l
S t? s a ^ ^ a ^ ^ s ^ h | s ^ (? | a f f? a f (? | a , (? | a ^ i]? | a
ro ro cd ro ro ro ro ro ro ro ro ro c W W Cd ffl
1 1 1 1 1 1 1 1 1 1 1 1 1d 1 1 c 1d c1d ffl1 ffl1 ro1 ro1 ro1 ro1 c1d ffl1 ro1 ro1 I Ift 3 ft
Ω
_? _? _? _? _? _? _? _? Ω Ω Ω Ω Ω Ω Ω Ω rø rø rø rø rø Ift Ito
ro 1 ro1 ro1 ω o o Q o ω ω w ro o o Q o ro 1 « ffl ffl Ω Ω Ω Ω w w w ffl Ω lft
ro 1 c1d ro1 c1d ro1 c1d
ffl ffl ffl ffl Ω Ω Ω Ω ffl ffl W H? Ω Ω Ω Ω -? H? -? -? Ω Ω Ω Ω HS H? ιf , _? Ω lft
δ g* if E -+ δ iC" E IS 2 ffi J_So* E «-S*• 2 ffi gd" E -S+ ff2 £ 3_" T <E-S*■ ffit? p 3-dj i *-f* "ES C2D pάjι |!
3 T
3 T 3 -i i I
Ω Ω Ω Ω H? -? H? H? HV ι? H? H? Ω Ω Ω Ω Hf H? ^ H? Ω Ω Ω Ω H? H? HV ffl Ω |ft
ES ^ ES rf δ δ w Cd
0 Er W Cd
3 ES Cd
3 EP w cf δ δ ES l li«..
3 T 3 T
O ^ ^ ffl ffl Ω Ω Ω Ω π ffl ffl W Ω Ω Ω Ω ω ro ω ω Ω Ω Ω Ω ft
O O W W Cd Cd Ω Ω o o Cd ro ro ro Ω Ω Ω w ω w w Ω Ω Ω Ω Ift
ES cf 3 δ δ ES cf 1 to ES cf 3 δ
ro ro ro ft #.ltos
Cd ffl o Ω Ω Q ω w Cd ffl o O o o w ro Cd Cd o O Cd SP W Cd O o Q Ω Cd flf ffl Cd O O ft
δ ES cf δ 3 5 ES cf δ 3 S ES cf δ 3 5 ES δ 3 to ft
o O o O O o o O o o o a a 8 8 8 a a 8 8 8 a 8 a a 8 8 a a 8 8 8 8 ft P
VO o Q o Q Ω Ω ffi ffi ffi ffi ffi fif ffi ffi 9 9 9 9 9 9 9 9 ft -4 cr'iorj
ES δ 3 δ ES cf i 5 ES δ 3 δ ES 1 3 to ES cf δ 3 5 ES cf 3 5 ES cf δ 3 5 ES 1 3 ffl 5 ES δ 3 to ft
o Ω SF s? cd E? Q o o Ω 5* ffl flf ω Cd Cd Cd O Q Ω Q W H? ε? s? Q Ω Ω Ω Cd ffl w H? Q O ft
W W O O O O Q O O O O Q Q O O Q Q O O O Q O O O O O O O O O O O O O θ |ft rø VO
Cd or Q TJ TJ TJ
1 Tj Tj Tj Tj W Cd Cd ro o Cd Cd Cd O TJ Ω Ω y Ω y Ω y Ω Ω Ω
1 1 r y w y ffi ffi ffi ffi ffi ffi w ilto
Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω 5, ^ 53 -? Ω Ω Ω Ω 5, S, S, 53 Ω Ω Ω Ω EP S3 -* 1 * 5, Ω Ω Ω Ω ι? -? lft
ES l«.
o o o Q Q ro ro ffl W Q Q O Q ffl ω ro w o o o o w w ω ω o o Q o w ffl ω ro o lrø-.
ES l? ω rø ES l ffl rø ES ^ w rø !3 l? ffl rø ES ^ rø rø ES l ffl rø
Cd ffl W W W W W W W ffl O Q O Q O O O Q O O O O O O O O O O O O O O O O O o
Q Q Mc M.j Mrj MrJ hEJ hr. hH MiH. Q Q Q Q Q Q Q
Ω Ω _? £? E? E? Ω Ω Ω Ω Ω Ω Ω Ω _? _? E? ^ Ω Ω Ω Ω _? _? 5' E? Ω Ω Ω Ω S' S' 5) _? Ω Ω ft
cd ffl ffl ffl ffl ro ro ro ro ro ro ro cd cd ro ro ro ro cd ro ro ro Cd ffl ϋd Cd ffl Cd Cd Cd
O O O O O O O O hrl hrJ Tl hcl hrJ hcJ TJ Tl Cd Cd Cd Cd Cd Cd
ι H? ι? ιp Ω Ω Ω H? -? ιp H? Ω Ω Ω Ω H? ^ ι? H? Ω Ω Ω Ω ω H H? H? Ω Ω |ft
δ δ E ^ δ E ^ δ E ^ δ δ E i? δ δ ES i2 δ ES t| δ ES ^ δ ft
ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ffl ffl cd ffl cd ffl cd ffl ffl cd ffl ft | 1rø VO O ro ro ro ro ro ro ffl ffl O O O O O O O O TJ TJ TJ TJ TJ TJ VO ft
HS -? H? _? Ω Ω Ω Ω ιi* -? -? -? Ω Ω Ω Ω HS H? ι? -? Ω Ω Ω Ω Hp H? _? Hp Ω Ω |ft
g ώ* δ ι_r E <-5>■ ^ CD yw πt E^S ffi2 aώ" ► * E -S+ «2 ώ s' lf iS- ffi2 gώ' δl-r EcS+ 2ffi gώ* i^* E <-S>■ 2D ^ώ δHr E-SH- ffi2 aώ- ,-r l ι l!w
or ro ro ro ro cd ro ro or ro ro ro ro ro ro ro ro ffl ro cd ro ro ro
9 9 9 9 9 9 9 ffl s* _? ffl ffl ffl ffl
Ed Sf 53 S) 9 9 Ω Ω S< EP 5' H? 9 Ω Ω Ω 5' S, 5' 5' Ω Ω Ω Ω 5< 5- 5' S, Ω Ω ft
δ ES ϋ δ δ ES i? δ δ ES 2 δ δ W Cd W Cd
3 rø 3 δ ES i? δ δ ES 2 | ft!
o o o ro Cd s? 6? Ω Ω Ω Ω -? H? H? H? Ω Ω Ω Ω H? H? Cd Cd Ω Ω Ω Ω ft
o o o w ffl ffl ffl Ω Ω Ω Ω Sr, w ω ω Ω Ω Ω Ω ω ω ω w Ω Ω Ω Ω ft
o o O O O o O o o o 8 8 8 8 a a 8 a 8 a a a a a 8 a a 8 a a a 8 8 a a I 1ft 3 o ffi ffi ffi 9 9 9 9 9 9 9 9 -^ Cd Cd ω Cd ffl & | ,lto%
ro ro Q o Q O ffl ffl ω H? O O O O ro s? ε? &? O O Q ffl ffl Cd Cd Ω o o o ro W Cd Cd Ω ft
S ES δ 3 S ES 1 δ 3 5 ES δ 3 5 ES cf δ 3 5 ES cf 3 δ 5 ES cf δ 3 HP ES cf
t o
o o Ω Cd ro ro ro o o o o ro ffl Cd Cd Cd ro 1 ro ffl Ω O O Q Cd Cd Cd Cd Ω O O O Cd ro Cd Cd ft
5 ES cf δ 3 5 ES 1 δ 3 to ES cf 3 δ 5 ES cf δ ^-ι.
3 to ES cf δ 3 to ES cf δ 3 ϊ ES 1 δ 3 to ES cf δ 3 5 ES cf δ 3 Ift
o Q Q Cd Cd Cd J? O o Q Ω ω w w Cd ffl ro Ω O Q w W ffl Cd Q Q o ro Cd ω ω o Ift
G G G G m ^ ffl to G G
fc fc fc fc fc fc fc fc J O
m m ffl ffl m ffl m ffl m m
3 3 3 3 3 3
•Ed I w ft
•A ffl -A ft ffl w ft ffl w ft w ft A ffl VA W ft ffl W ft 3 3 a 3
$ 3 3 a
^i G m m m m rt g r. r! -H m m m ffl g g g ffl ffl ffl ffl G G G G m ffl ffl to o υ o o o o col fc fc fc fc fc fc fc fc li li li li
CN f ffl ffl o %\ ffl fl δ δ δ δ δ δ δ δ u ° ° ϋ h h
CN 3
3 I _H li li li 14 O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O ffl ffl
co i J5 tu +i jH -. ω •__ J1 J*. ω ' •_- .IT1 J". ) *_ jH _*_ ω ._- .H **_ > - J- 3 o *_ jH *"? «" ,3 .3 "5 <> _ι
^ π ^ ^ ρp ^ ^ fe pp H s ^ s fe p 3 s ft ffl ^ a ft ffl ft pp ft pp ρ ffl | a
p.| m G G G G (-3 m (-3 ffl G G G G (-. ffl ffl ffl G G G G (-3 m ffl m G G G G G G G G G G
C I co co co co co co co co
I e-. ffl ffi ffi ffi ffi g ^ g g g g ^ ^ ^ ^ ^ m ^ ^ rS ^ fc fc fc fc o g ft ft ft ft ffl m t- cό 3 I ov
PH! 14 G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G G m ffl
o I Λ CD .* H-*I iz-ι 3 jr & ω .* +-> J .Jrr.1 3 u. & » * j-ii J ^r.* 3 __. & ω J_> J _r-< _ fr? tU i JH 5 <_I J_.
^ p? ^ ft p ^ ft p ^ ft o? ^ a ft a ft ffl | a ΛJH T ft ffl J ω ^B a _ ■r_- . J ftfr1 ._* <-) .__ ."-< _-. to .- ffl a ft pp a
R9 is CHF2 R is CH2E3 R9 is CF 2C 2
R3 R4a R4b R6 R3 R4a R4b ≠ R3 R4a R4b R6 t-Bu Br Br Cl t-Bu Br F Cl t-Bu Br Cl Cl
Me Br Br Br Me Br F Br Me Br Cl Br
Et Br Br Br Et Br F Br Et Br Cl Br i-Pr Br Br Br f-Pr Br F Br i-Pr Br Cl Br t-Bu Br Br Br t-Bu Br F Br t-Bu Br Cl Br
Me Br Cl Me Br Cl Cl Me Br Br Cl
Et Br Cl Et Br Cl Cl Et Br Br Cl i-Pr Br Cl i-Pr Br Cl Cl i-Pr Br Br Cl t-Bu Br Cl t-Bu Br Cl Cl t-Bu Br Br Cl
Me Br Br Me Br Cl Br Me Br Br Br
Et Br Br Et Br Cl Br Et Br Br Br i-Pr Br Br i-Pr Br Cl Br i-Pr Br Br Br t-Bu Br Br t-Bu Br Cl Br t-Bu Br Br Br
Me Br F Cl Me Br I Cl Me Br CF3 Cl
Et Br F Cl Et Br I Cl Et Br CF3 Cl i-Pr Br F Cl ∑-Pr Br I Cl i-Pr Br CF3 Cl t-Bu Br F Cl t-Bu Br I Cl t-Bu Br CF3 Cl
Me Br F Br Me Br I Br Me Br CF3 Br
Et Br F Br Et Br I Br Et Br CF3 Br i-Pr Br F Br z'-Pr Br I Br i-Pr Br CF3 Br t-Bu Br F Br t-Bu Br I Br t-Bu Br CF3 Br
Me Br Cl Cl Me Br Br Cl Me Br Cl
Et Br Cl Cl Et Br Br Cl Et Br Cl i-Pr Br Cl Cl -Pr Br Br Cl t-Pr Br Cl t-Bu Br Cl Cl t-Bu Br Br Cl t-Bu Br Cl
Me Br Cl Br Me Br Br Br Me Br Br
Et Br Cl Br Et Br Br Br Et Br Br i-Pr Br Cl Br i-Pr Br Br Br /-Pr Br Br t-Bu Br Cl Br
t-Bu Br Br Br t-Bu Br Br
Formulation/Utility
Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties ofthe active ingredient, mode of application and
environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including micro emulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and farther formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release ofthe active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.
Weight Percent
Active mgredient Diluent Surfactant
Water-Dispersible and Water-soluble 5-90 0-94 1-15 Granules, Tablets and Powders.
Suspensions, Emulsions, Solutions 5-50 40-95 0-15 (including Emulsifiable Concentrates)
Dusts 1-25 70-99 0-5
Granules and Pellets 0.01-99 5-99.99 0-15
High Strength Compositions 90-99 0-10 0-2
Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, Hgni sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxy- ethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium
sulfate. Liquid diluents include, for example, water, N5N-dimethylformamide, dimethyl sulfoxide. N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol. benzyl and tefrahydrofurfuryl alcohol.
Solutions, clucling emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grmding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and PCT Publication WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
For further information regarding the art of formulation, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings ofthe 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A.
Example A Wettable Powder
Compound 6 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium Hgninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% .
Example B Granule
Compound 6 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
Example C Extruded Pellet
Compound 6 25.0% anhydrous sodium sulfate 10.0% crude calcium Hgninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
Example D Emulsifiable Concentrate Compound 6 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.
Compounds of this invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity conttolling a spectrum of agronomic and non- agronomic invertebrate pests. (In the context of this disclosure "invertebrate pest control" means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or other damage caused by the pest; related expressions are defined analogously.) As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, milhpedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" includes all ofthe helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests. Compounds of this invention display activity against economically important agronomic, forest, greenhouse, nursery, ornamentals, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests. These include larvae ofthe order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodopterafugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hύbner), black cutworm (Agrotis ipsilon Hufnagel), cabbage looper (Trichoplusia ni
Hϊibner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer (Ostrinia nubilalis Hύbner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms, seed worms, and fruit worms in the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)); and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults ofthe order Blattodea including cockroaches from the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius)); fohar feeding larvae and adults ofthe order Coleoptera including weevils from the families Anthribidae, Bruchidae, and Curcuhonidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers in the family ChrysomeUdae (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky)); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family
Tenebrionidae. In addition it includes: adults and larvae ofthe order Dermaptera including earwigs from the family Forf culidae (e.g., European earwig (Forflcula auricularia Linnaeus), black earwig (Chelisoches morio Fabricius)); adults and nymphs ofthe orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoasca spp.) from the family Cicadellidae, planthoppers from the families Fulgoroidae and Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g., Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugs from the family Cercopidae squash bugs from the family Coreidae, and red bugs and cotton stainers from the family Pyrrhocoridae. Also included are adults and larvae ofthe order
Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other fohar feeding mites and mites important in human and animal health, i.e. dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scab and itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M. differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.)); adults and immatures ofthe order Diptera including leafminers, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinellafrit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F.femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp., Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera; adults and immatures ofthe order Thysanoptera including onion thrips (Thrips tabaci Lindeman) and other fohar feeding thrips; insect pests ofthe order Hymenoptera including ants (e.g., red carpenter ant (Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant (Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant
(Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Fδrster), odorous house ant (Tapinoma sessile Say)), bees (mclucling carpenter bees), hornets, yellow jackets and wasps; insect pests ofthe order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite
(Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; insect pests ofthe order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard);
insect pests ofthe order Mallophaga and including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch), dog biting louse (Trichodectes canis De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus ewγsternus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack man and animals; insect pests ofthe order Siphonopteramcluding the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas afflicting mammals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus). Activity also includes members ofthe Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members ofthe orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e. all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofllaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).
Compounds ofthe invention show particularly high activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hύbner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoverpa annigera Hύbner (American bollworm), Helicoverpa zea Boddie (corn earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermύller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafininer), Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hύbner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpiUar), Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hύbner (cabbage
looper) and Tuta absoluta Meyrick (tomato leafminer)). Compounds of he invention also have commercially significant activity on members from the order Homoptera mcluding: Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphonfragaefolii Cockerell (strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Suker (peach-potato aphid, green peach aphid), Nasonovia rϊbisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry- oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii
Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris
(potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus Stal (rice leafhopper), Nilaparvata lugens Stal (brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatellafurcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAtee white apple leafhopper, Erythroneoura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotu perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla). These compounds also have activity on members from the order Hemiptera including: Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schaffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolarius Pahsot de Beauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Pahsot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus Dallas
(large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper). Other insect orders controlled by compounds ofthe invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothrips citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle),
Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms ofthe genera Agriotes, Athous or Limonius).
Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones. feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility. Thus compositions ofthe present invention can further comprise a biologically effective amount of at least one additional biologically active compound or agent. Examples of such biologically active compounds or agents with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlo yrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, peivmethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, ttalomethrin, trichlorfon and triflumuron; fungicides such as acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux m ture • (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dicl oro-N-(3-chloro-l-ethyl-l-methyl-2-oxopropyl)-4- methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (S)-3,5-dihydro-5-me yl-2-(methylmio)-5-phenyl-3-(phenylammo)-4H-imiαa^
(RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide,
fluazinam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metomino- sfrobin fenominostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis mcluding ssp. aizawai and kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
A general reference for these agricultural protectants is The Pesticide Manual, 12th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2000.
Of note are combinations of a compound of Formula 1 d with the biologically active compounds above.
Preferred insecticides and acaricides for mixing with compounds of this invention include pyrethroids such as cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid, neuronal sodium channel blockers such as indoxacarb, insecticidal macrocychc lactones such as spinosad, abamectin, avermectin and emamectin; γ-aminobutyric acid (GABA) antagonists such as endosulfan, ethiprole and fipronil; insecticidal ureas such as flufenoxuron and triflumuron, juvenile hormone mimics such as diofenolan and pyriproxyfen; pymetrozine; and amitraz. Preferred biological agents for mixing with compounds of this invention include Bacillus thuringiensis and Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members ofthe family Baculoviridae as well as entomophagous fungi. Of note are combinations of a compound of Formula Id with the preferred insecticides and acaricides above. Most preferred mi-xtures include a rrnxture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with beta-cyfluthrin; a rrnxture of a compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a
compound of this invention with thiacloprid; a ntixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with ethiprole; a rnixture of a compound of this invention with fipronil; a mixture of a compound of this invention with flufenoxuron; a nmture of a compound of this invention with pyriproxyfen; a mixture of a compound of this invention with pymetrozine; a rn ture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta endotoxin. In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions ofthe present invention can further comprise an biologically effective amount of at least one additional invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus ofthe plant with a biologically effective amount of a compound of invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.
Invertebrate pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more ofthe compounds of this invention, in an effective amount, to the environment ofthe pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of fohar- and soil-inhabiting invertebrates and protection of agronomic and/or nonagronomic crops, comprising contacting the invertebrates or their environment with a biologically effective amount of one or more of the compounds of the invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and an effective amount of at least one additional biologically active compound or agent. A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound ofthe invention can be apphed to the plant foliage or the soil. Compounds of this invention are effective in dehvery through plant uptake by contacting the plant with a composition comprising a compound of this invention apphed as a soil drench of a hquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Other methods of contact include apphcation of a compound or a composition ofthe invention by direct and residual sprays, aerial sprays, seed coats, micrpencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.
The compounds of this invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01-5% active ingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetable flour are effective in controlling soil insects at very low apphcation rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact.
The compounds of this invention can be applied in their pure state, but most often apphcation will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of apphcation involves spraying a water dispersion or refined oil solution ofthe compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
The rate of apphcation required for effective control (i.e. "biologically effective amount") will depend on such factors as the species of invertebrate to be controlled, the pest's hfe cycle, hfe stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, apphcation rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0J mg/square meter may be sufficient or as much as 150 mg/square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control. The following TESTS demonstrate the control efficacy of compounds of this invention on specific pests. "Control efficacy" represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-B for compound descriptions. The following abbreviations are used in the Index Tables which follow: Me is methyl, t'-Pr is isopropyl, Ph is phenyl. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.
INDEX TABLE A
Compound R R4 R7 X Y m.p. °C
1 (Ex. 1) t-Pr 3-1 OCH2CF3 CH CH N 220-225
2 (Ex. 1) i-Pr 6-1 OCH2CF3 CH CH N 200-203
3 i-Pr 3-Me OCH2CF3 CH CH N 205-210
4 i-Pr 6-Me OCH2CF3 CH CH N 193-196
INDEX TABLE B
Compound R3 R4 Q X Y Z m.p. °C
5 i-Pr 3-1 Ph N CH CMe 193-194
6 i-Pr 6-1 NPh N CH CMe 216-218
7 i-Pr 3-1 NMe N CH CMe 220-222
8 i-Pr 6-1 NMe N CH CMe 233-234
9 i-Pr 3-1 NMe N CH C-cyclopropyl 222-224
10 i-Pr 6-1 NMe N CH C-cyclopropyl 215-217 ll(Ex. 2) i-Pr 6-1 N(2-ClPh) N CH CCF3 234-235
12 (Ex. 2) i-Pr 3-1 N(2-ClPh) N CH CCF3 226-228
BIOLOGICAL EXAMPLES OF THE INVENTION
TEST A For evaluating control of diamondback moth (Plutella xylostella) the test unit consisted of a small open container with a 12-14-day-old radish plant inside. This was pre-infested with 10-15 neonate larvae on a piece of insect diet by use of a core sampler to remove a plug from a sheet of hardened insect diet having many larvae growing on it and transfer the plug containing larvae and diet to the test unit. The larvae moved onto the test plant as the diet plug dried out.
Test compounds were formulated using a solution containing 10% acetone, 90% water and 300 ppm X-77® Spreader Lo-Foam Formula non-ionic surfactant containing alkylarylpolyoxyethylene, free fatty acids, glycols and isopropanol (Loveland Industries, Inc.), unless otherwise indicated. The formulated compounds were apphed in 1 mL of hquid through a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems Co.) positioned 1.27 cm (0.5 inches) above the top of each test unit. All experimental compounds in this screen were sprayed at 50 ppm and rephcated three times. After spraying ofthe formulated test compound, each test unit was allowed to dry for 1 hour and then a black, screened cap was placed on top. The test units were held for 6 days in a growth chamber at 25 °C and 70% relative humidity. Plant feeding damage was then visually assessed.
Ofthe compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 3, 4, 6, 7, 9, 10.
TEST B
For evaluating control of fall armyworm (Spodoptera frugiperda) the test unit consisted of a small open container with a 4-5-day-old corn (maize) plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.
Test compounds were formulated and sprayed at 50 ppm as described for Test A. The apphcations were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.
Ofthe compounds tested, the foUowing provided exceUent levels of plant protection (10% or less feeding damage): 1, 9.
TEST C
For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of a small open container with a 6-7 day old cotton plant inside. This was pre-infested with
8 2-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A. Test compounds were formulated and sprayed at 50 ppm as described for Test A. The apphcations were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.
Ofthe compounds tested, the foUowing provided exceUent levels of plant protection (10% or less feeding damage): 1, 3, 7, 9.
Claims
CLAIMS What is claimed is: 1. A compound of Formula I and N-oxides and agriculturally suitable salts thereof
wherein
J is selected from the group consisting of J-l, J-2, J-3, J-4, J-5, J-6, J-7 and J-8
R1 is H, Cι-C6 alkyl, C2-Cg alkoxycarbonyl or C2-Cg alkylcarbonyl;
R2 is H or CrC6 alkyl;
R is H; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C8 cycloalkylalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CΝ, ΝO2, hydroxy, C1-C4 alkyl, -C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-Cg alkoxycarbonyl or C2-Cg alkylcarbonyl; one R4 group is attached to the phenyl ring at the 3-position or 6-position, and said R4 is C1-C4 alkyl, C1-C haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, or C1-C4 haloalkylsulfonyl; and an optional second R4 is H, Cj-Cg alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cg cycloalkyl, Cι-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio,
C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-Cg cycloalkylamino, C1-C4 alkoxyalkyi, C1-C4 hydroxyalkyl, C(O)R10 ! CO2R10, C(O)NR10Rn, NR^R11, NfRi^CORi^ N^i^COaR10 or C3-C,5 trialkylsilyl; R5 is H, CrC4 alkyl, CrC4 haloalkyl, or
V is N, CH, CF, CC1, CBr or CI; each R6 and R7 is independently H, C^Cg alkyl, C3-Cg cycloalkyl, Cι-C6 haloalkyl, halogen, CN, C1-C4 alkoxy, Ci -C4 haloalkoxy or C1-C4 haloalkylthio; R9 is H, CrC6 alkyl, CrC6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl or C3-Cg haloalkynyl; provided R7 and R9 are not both H; R10 is H or -C4 alkyl or -C4 haloalkyl; R11 is H or C!-C4 alkyl; and n is 1 or 2.
2. The compound of Claim 1 wherein V is N.
3. The compound of Claim 1 wherein V is CH, CF, CC1 or CBr.
4. The compound of Claim 2 or Claim 3 wherein R1 and R2 are both H;
R3 is -C4 alkyl optionally substituted with halogen, CN, OCH3, S(O)pCH3; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH , CF3,
OCF3, OCHF2, S(O)pCF3, S(O)pCHF2, CN or halogen; a second R4 is H, F, Cl, Br, I or CF3; R6 is C1-C4 alkyl, C1-C4 haloalkyl, halogen or CN; R7 is H, CH3, CF3, OCHF2 or halogen; and p is 0, 1 or 2.
5. The compound of Claim 4 wherein J is J-l;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH , Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and
R7 is halogen or CF3.
6. The compound of Claim 5 wherein V is N;
R3 is methyl, ethyl, isopropyl or tertiary butyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3 or I;
R6 is Cl or Br; and R7 is Br, Cl or CF3.
7. The compound of Claim 6 selected from the group consisting of: N/-[l-(3-chloro-2-ρvridmyl)-3-(trifluorome1hyl)-lH-pvrazol-5-yl]-3-methyl-N^ methylethyl)- 1 ,2-benzenedicarboxamide,
N -[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-methyl-N2-(l- methylethyl)- 1 ,2-benzenedicarboxamide,
N -[l-(3-chloro-2-ρyriα yl)-3-(1rifluoromethyl)-lH-pyrazol-5-yl]-3-iodo-N2-(l- methylethyl)-l ,2-benzenedicarboxamide, and N^[l-(3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazol-5-yl]-3-iodo-N2-(l- methylethyl)- 1 ,2-benzenedicarboxamide.
8. The compound of Claim 4 wherein J is J-2;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CΗ3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3;
R6 is Cl or Br; and
R9 is CF3, CHF2, CH2CF3, CF2CHF2.
9. The compound of Claim 4 wherein
J is J-3; R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; and
R7 is halogen or CF .
10. The compound of Claim 4 wherein
J is J-4;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3;
R6 is Cl or Br; and
R7 is CF3.
11. The compound of Claim 4 wherein
J is J-5;
R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3;
R6 is Cl or Br; and
R9 is CF3, CHF2, CH2CF3, CF2CHF2.
12. The compound of Claim 4 wherein J is J-6; R3 is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3;
R6 is Cl or Br; and R7 is halogen or CF3.
13. The compound of Claim 4 wherein J is J-7;
R3 is CrC4 alkyl; one R4 group is attached to the K-ring at the 2-position and said R4 is CH3, Cl or Br; a second R4 is H, F, Cl, Br, I or CF3 ;
R6 is Cl or Br: R7 is H, halogen or CF3.and
R9 is H, CF3, CHF2, CH2CF3, CF2CHF2.
14. The compound of Claim 4 wherein J is J-8; R is CrC4 alkyl; one R4 group is attached to the phenyl ring at the 3-position and said R4 is CH3, Cl, Br or I; a second R4 is H, F, Cl, Br, I or CF3; R6 is Cl or Br; R7 is H, halogen or CF3.and
R9 is H, CF3, CHF2, CH2CF3, CF2CHF2.
15. A composition for confrolling an invertebrate pest comprising a biologically effective amount of a compound of Claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid dUuent or a liquid dnuent.
16. The composition of Claim 15 further comprising an effective amount of at least one additional biologically active compound or agent.
17. The composition of Claim 16 wherein at least one additional biologically active compound or agent is selected from arthropodicides ofthe group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocychc lactones, γ-aminobutyric acid (GAB A) antagonists, insecticidal ureas and juvenile hormone mimics.
18. The composition of Claim 16 wherein at least one additional biologicaUy active compound or agent is selected from insecticide, nematocide, acaricide or biological agents in the group consisting of abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clotMartidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronU, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, p imicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tbiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, fralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad; Bacillus thuringiensis i, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
19. The composition of Claim 18 wherein at least one additional biologicaUy active compound or agent is selected from insecticide, nematocide, acaricide or biological agents in the group consisting of cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate, fralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronU, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.
20. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 1 or a composition of Claim 17.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25463600P | 2000-12-11 | 2000-12-11 | |
US254636P | 2000-12-11 | ||
US32401201P | 2001-09-21 | 2001-09-21 | |
US324012P | 2001-09-21 | ||
PCT/US2001/047572 WO2002048137A2 (en) | 2000-12-11 | 2001-12-05 | Substituted heterocyclic phthalic acid diamide arthropodicides |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1341780A2 true EP1341780A2 (en) | 2003-09-10 |
Family
ID=26944169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01990065A Withdrawn EP1341780A2 (en) | 2000-12-11 | 2001-12-05 | Substituted heterocyclic phthalic acid diamide arthropodicides |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1341780A2 (en) |
JP (1) | JP2004515547A (en) |
AU (1) | AU2002228938A1 (en) |
WO (1) | WO2002048137A2 (en) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003011028A1 (en) * | 2001-08-01 | 2003-02-13 | Nissan Chemical Industries, Ltd. | Substituted amides and pest controllers |
US7038057B2 (en) | 2001-08-13 | 2006-05-02 | E.I. Du Pont De Nemours And Company | Substituted 1H-dihydropyrazoles, their preparation and use |
EP1944304B1 (en) * | 2001-08-13 | 2012-11-28 | E.I. Du Pont De Nemours And Company | Substituted 1h-dihydropyrazoles, their preparation and use |
KR20090120014A (en) | 2003-12-12 | 2009-11-23 | 바이엘 크롭사이언스 아게 | Synergistic insecticidal mixture |
GB0422556D0 (en) | 2004-10-11 | 2004-11-10 | Syngenta Participations Ag | Novel insecticides |
WO2006055922A2 (en) * | 2004-11-18 | 2006-05-26 | E.I. Dupont De Nemours And Company | Anthranilamide insecticides |
DE102004055582A1 (en) * | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-heterocyclic-phthalic |
JP5424874B2 (en) | 2006-06-22 | 2014-02-26 | ビーエーエスエフ ソシエタス・ヨーロピア | Malononitrile compound |
MX2009002219A (en) | 2006-09-14 | 2009-04-17 | Basf Se | Pesticide composition. |
CA2667112C (en) | 2006-11-10 | 2015-08-11 | Basf Se | Crystalline modification of fipronil |
BRPI0718717A2 (en) | 2006-11-10 | 2013-11-26 | Basf Se | CRYSTALLINE II MODIFICATION OF PHYRONYL, SOLID PHYRONYL, PROCESS TO PREPARE CRYSTALLINE II MODIFICATION, SYNERGISTIC PESTICIDE OR PARASITICIDE MIXTURE, PESTICIDE OR PARASITITICAL COMPOSITION, USE OF CRYSTALINE II MODULATION, OR MYSTERIOUS COMPOUND, FIDRONI PEST, TO PROTECT A PLANT FROM INFESTATION AND PEST ATTACK, TO PROTECT SEED, AND TO TREAT, CONTROL, PREVENT OR PROTECT ANIMALS FROM INFESTATION OR INFECTION BY PARASITES, USE OF CRYSTALLINE II MODIFICATION, OR SOLID FIPRONYL, OR SOLID , OR COMPOSITION, AND PROCESS FOR PREPARING A COMPOSITION TO TREAT, CONTROL, PREVENT OR PROTECT ANIMALS AGAINST INFESTATION OR PARASITE INFECTION |
UA110598C2 (en) | 2006-11-10 | 2016-01-25 | Басф Се | METHOD OF OBTAINING CRYSTAL MODIFICATION OF FIPRONIL |
BRPI0718715B8 (en) | 2006-11-10 | 2021-03-23 | Basf Se | crystalline modification of fipronil containing co-crystallized acetone, solid fipronil, processes for preparing crystalline modifications iv, v and i, pesticidal or parasiticidal mixture and pesticidal or parasiticidal composition |
CN101562969B (en) | 2006-11-30 | 2013-12-25 | 巴斯夫欧洲公司 | Agrochemical formulations comprising 1-vinyl-2-pyrrolidinone co-polymers |
CA2668928A1 (en) | 2006-11-30 | 2008-06-05 | Basf Se | Agrochemical formulations comprising co-polymers based on diisocyanates |
JP5323714B2 (en) | 2006-11-30 | 2013-10-23 | ビーエーエスエフ ソシエタス・ヨーロピア | Agrochemical formulation containing N-vinylamide copolymer |
BRPI0721054A2 (en) | 2006-12-01 | 2014-07-29 | Syngenta Participations Ag | INSECTICIDES |
EP2258177A3 (en) | 2006-12-15 | 2011-11-09 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
CN101019548B (en) * | 2007-03-23 | 2010-05-19 | 陈美英 | Preparation process and usage of liquid insect repellant |
BRPI0809575B8 (en) | 2007-04-12 | 2019-08-20 | Basf Se | pesticide mixtures, methods for protecting plants against attack or infestation by insects, mites or nematodes, and for protecting seed, use of a mixture, and pesticidal or parasiticidal composition |
KR20100015796A (en) | 2007-04-23 | 2010-02-12 | 바스프 에스이 | Plant productivity enhancement by combining chemical agents with transgenic modifications |
EP3150068B1 (en) | 2007-08-16 | 2019-10-09 | Basf Se | Seed treatment compositions and methods |
EP2500340A1 (en) | 2008-01-25 | 2012-09-19 | Syngenta Participations AG. | 2-Cyanophenyl Sulfonamide Derivatives Useful as Pesticides |
JP6434048B2 (en) * | 2014-04-02 | 2018-12-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Heterocyclic compounds as pesticides |
CN107864983A (en) * | 2017-11-29 | 2018-04-03 | 孙铭岐 | A kind of biological pesticide for preventing and treating rice pest |
CN108432817A (en) * | 2018-04-22 | 2018-08-24 | 陈太师 | A kind of acaricide and preparation method thereof |
CN116376504A (en) * | 2023-03-17 | 2023-07-04 | 西安工程大学 | Method for preparing functional materials from waste PET bottles |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3305569A1 (en) * | 1983-02-18 | 1984-08-23 | Bayer Ag, 5090 Leverkusen | BISCARBOXAMIDES FOR THE FIGHT AGAINST DISEASES AND METHOD FOR THE PRODUCTION THEREOF |
TW515786B (en) * | 1997-11-25 | 2003-01-01 | Nihon Nohyaku Co Ltd | Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides |
AR030154A1 (en) * | 1999-07-05 | 2003-08-13 | Nihon Nohyaku Co Ltd | DERIVED FROM FTALAMIDE, DERIVED FROM HETEROCICLIC AMINE USEFUL AS INTERMEDIARY FOR THE PRODUCTION OF THE SAME, AGROHORTICALLY INSECTICIDE AND METHOD TO USE SUCH INSECTICIDE |
TR200200773T2 (en) * | 1999-09-24 | 2002-06-21 | Nihon Nohyaku Co., Ltd | Aromatic diamide derivatives, salts, chemical farming / horticulture |
CZ20022111A3 (en) * | 1999-12-22 | 2002-10-16 | Nihon Nohyaku Co., Ltd. | Aromatic diamide derivative, agricultural and horticultural chemical substance, and use thereof |
TWI282786B (en) * | 2000-04-28 | 2007-06-21 | Nihon Nohyaku Co Ltd | A process for preparing 2-halogenobenzoic acids |
-
2001
- 2001-12-05 WO PCT/US2001/047572 patent/WO2002048137A2/en not_active Application Discontinuation
- 2001-12-05 JP JP2002549668A patent/JP2004515547A/en not_active Withdrawn
- 2001-12-05 AU AU2002228938A patent/AU2002228938A1/en not_active Abandoned
- 2001-12-05 EP EP01990065A patent/EP1341780A2/en not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO0248137A3 * |
Also Published As
Publication number | Publication date |
---|---|
AU2002228938A1 (en) | 2002-06-24 |
WO2002048137A2 (en) | 2002-06-20 |
WO2002048137A3 (en) | 2003-06-05 |
JP2004515547A (en) | 2004-05-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1417204B1 (en) | Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests | |
AU2003212811B2 (en) | Quinazoline(di) ones for invertebrate pest control | |
EP1423379B1 (en) | Ortho-substituted aryl amides for controlling invertebrate pests | |
US7541377B2 (en) | Substituted anthranilamides for controlling invertebrate pests | |
EP1373210B1 (en) | Heterocyclic diamide invertebrate pest control agents | |
EP1341780A2 (en) | Substituted heterocyclic phthalic acid diamide arthropodicides | |
AU2003212811A1 (en) | Quinazoline(di) ones for invertebrate pest control | |
AU2002331706A1 (en) | Ortho-substituted aryl amides for controlling invertebrate pests | |
WO2003106427A2 (en) | Pyrazolecarboxamide insecticides | |
AU2002326748A1 (en) | Substituted anthranilamides for controlling invertebrate pests | |
US20040110777A1 (en) | Quinazolinones and pyridinylpyrimidinones for controlling invertebrate pests | |
AU2002343512A1 (en) | Iminobenzoxazines, iminobenzthiazines and iminoquinazolines for controlling invertebrate pests | |
EP1435785A1 (en) | Iminobenzoxazines, iminobenzothiazines and iminoquinazolines for controlling invertebrate pests | |
US20040259913A1 (en) | Diamide invertebrate pest control agents | |
EP1511385B1 (en) | Insecticidal amides with nitrogen-containing benzo-fused bicyclic ring systems | |
WO2002032856A9 (en) | Insecticidal 1,8-naphthalenedicarboxamides | |
US20040063738A1 (en) | Substituted heterocyclic phthalic acid diamide arthropodicides | |
US20040053786A1 (en) | Insecticidal 1,8-naphthalenedicarboxamides | |
AU2003202966A1 (en) | Diamide invertebrate pest control agents |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20030512 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR |
|
AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
RBV | Designated contracting states (corrected) |
Designated state(s): DE ES FR IT |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20060726 |