OA16898A - Pesticidal compositions and processes related thereto. - Google Patents
Pesticidal compositions and processes related thereto. Download PDFInfo
- Publication number
- OA16898A OA16898A OA1201400180 OA16898A OA 16898 A OA16898 A OA 16898A OA 1201400180 OA1201400180 OA 1201400180 OA 16898 A OA16898 A OA 16898A
- Authority
- OA
- OAPI
- Prior art keywords
- substituted
- unsubstituted
- methyl
- sodium
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title claims description 142
- 230000000361 pesticidal Effects 0.000 title description 2
- -1 CH2Ci Chemical group 0.000 claims description 230
- 150000001875 compounds Chemical class 0.000 claims description 208
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 169
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 229910052801 chlorine Inorganic materials 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 229910052740 iodine Inorganic materials 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 239000011734 sodium Substances 0.000 claims description 33
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 29
- 229910052684 Cerium Inorganic materials 0.000 claims description 29
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 241000196324 Embryophyta Species 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000001495 ethyl group Chemical compound [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 18
- 239000011591 potassium Substances 0.000 claims description 17
- 229910052700 potassium Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims description 16
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 238000007792 addition Methods 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 125000005842 heteroatoms Chemical group 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- JNPZQRQPIHJYNM-UHFFFAOYSA-N Carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 claims description 6
- BERDEBHAJNAUOM-UHFFFAOYSA-N Copper(I) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 6
- 239000005946 Cypermethrin Substances 0.000 claims description 6
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 claims description 6
- 229940088597 Hormone Drugs 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000006013 carbendazim Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005556 hormone Substances 0.000 claims description 6
- 239000002169 Metam Substances 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N carbodiimide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003462 sulfoxides Chemical compound 0.000 claims description 5
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 claims description 4
- XMGQYMWWDOXHJM-JTQLQIEISA-N (4R)-limonene derivatives Chemical compound [H][C@]1(CCC(C)=CC1)C(C)=C XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine 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 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- RECUKUPTGUEGMW-UHFFFAOYSA-N Carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 4
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 claims description 4
- ISFMXVMWEWLJGJ-NZBPQXDJSA-N Curcumenol Chemical compound CC1=C[C@](O2)(O)C(=C(C)C)C[C@@]22[C@@H](C)CC[C@H]21 ISFMXVMWEWLJGJ-NZBPQXDJSA-N 0.000 claims description 4
- IATBEFPCSHFQJS-UHFFFAOYSA-N Demephion Chemical compound COP(=S)(OC)OCCSC IATBEFPCSHFQJS-UHFFFAOYSA-N 0.000 claims description 4
- GRPRVIYRYGLIJU-UHFFFAOYSA-N Demeton Chemical compound CCOP(=O)(OCC)SCCSCC GRPRVIYRYGLIJU-UHFFFAOYSA-N 0.000 claims description 4
- DFBKLUNHFCTMDC-PICURKEMSA-N Dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 claims description 4
- 239000005630 Diquat Substances 0.000 claims description 4
- CXEGAUYXQAKHKJ-FYOMLGFFSA-N Emamectin 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-FYOMLGFFSA-N 0.000 claims description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 4
- RMFNNCGOSPBBAD-MDWZMJQESA-N Formetanate Chemical compound CNC(=O)OC1=CC=CC(\N=C\N(C)C)=C1 RMFNNCGOSPBBAD-MDWZMJQESA-N 0.000 claims description 4
- 241000256602 Isoptera Species 0.000 claims description 4
- QANMHLXAZMSUEX-UHFFFAOYSA-N Kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 claims description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N Mercury(II) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 4
- ZYEMGPIYFIJGTP-UHFFFAOYSA-N Methyl eugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 claims description 4
- LVPGGWVHPIAEMC-UHFFFAOYSA-L Morfamquat Chemical compound [Cl-].[Cl-].CC1COCC(C)N1C(=O)C[N+]1=CC=C(C=2C=C[N+](CC(=O)N3C(COCC3C)C)=CC=2)C=C1 LVPGGWVHPIAEMC-UHFFFAOYSA-L 0.000 claims description 4
- HYVABZIGRDEKCD-UHFFFAOYSA-N N6-(delta2-Isopentenyl)adenine Natural products CC(C)=CCNC1=NC=NC2=C1N=CN2 HYVABZIGRDEKCD-UHFFFAOYSA-N 0.000 claims description 4
- MBRLOUHOWLUMFF-UHFFFAOYSA-N Osthol Chemical compound C1=CC(=O)OC2=C(CC=C(C)C)C(OC)=CC=C21 MBRLOUHOWLUMFF-UHFFFAOYSA-N 0.000 claims description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N Pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 4
- 229960005235 Piperonyl Butoxide Drugs 0.000 claims description 4
- JUVIOZPCNVVQFO-HBGVWJBISA-N Rotenone Natural products O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 claims description 4
- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 claims description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 claims description 4
- 229960001901 bioallethrin Drugs 0.000 claims description 4
- FMTFEIJHMMQUJI-DFKXKMKHSA-N cinerin I Chemical compound C1C(=O)C(C\C=C/C)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C FMTFEIJHMMQUJI-DFKXKMKHSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 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 claims description 4
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
- 229960003761 propamidine Drugs 0.000 claims description 4
- 239000005871 repellent Substances 0.000 claims description 4
- 230000002940 repellent Effects 0.000 claims description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N γ-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-GCMPRSNUSA-N 0.000 claims description 4
- COVZYZSDYWQREU-UHFFFAOYSA-N 1,4-Butanediol, dimethanesulfonate Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 3
- JDEKUYKSOCTBJT-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-methyl-4-oxopyridazine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=NN1C1=CC=C(Cl)C=C1 JDEKUYKSOCTBJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005631 2,4-D Substances 0.000 claims description 3
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 3
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims description 3
- PJISLFCKHOHLLP-UHFFFAOYSA-N 2-diethoxyphosphorylsulfanyl-N,N-diethylethanamine Chemical compound CCOP(=O)(OCC)SCCN(CC)CC PJISLFCKHOHLLP-UHFFFAOYSA-N 0.000 claims description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 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 3
- 239000005504 Dicamba Substances 0.000 claims description 3
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005562 Glyphosate Substances 0.000 claims description 3
- VOEYXMAFNDNNED-UHFFFAOYSA-N Metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 claims description 3
- STUSTWKEFDQFFZ-UHFFFAOYSA-N N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
- 229960002715 Nicotine Drugs 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 3
- 229930015196 nicotine Natural products 0.000 claims description 3
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 claims description 3
- IKVXBIIHQGXQRQ-ZDUSSCGKSA-N propan-2-yl (2S)-2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N([C@@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-ZDUSSCGKSA-N 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-(4S)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 claims description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 claims description 2
- KAATUXNTWXVJKI-GGPKGHCWSA-N (1R)-trans-(alphaS)-cypermethrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-GGPKGHCWSA-N 0.000 claims description 2
- DSSYKIVIOFKYAU-XVKPBYJWSA-N (1S,4R)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1C[C@@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-XVKPBYJWSA-N 0.000 claims description 2
- YATDSXRLIUJOQN-SVRRBLITSA-N (2,3,4,5,6-pentafluorophenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=C(F)C(F)=C1F YATDSXRLIUJOQN-SVRRBLITSA-N 0.000 claims description 2
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(E)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 claims description 2
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 claims description 2
- PTKVPQXEKZOPNA-UHFFFAOYSA-N (2,4-dinitro-6-octan-2-ylphenyl) methylsulfanylformate Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)SC PTKVPQXEKZOPNA-UHFFFAOYSA-N 0.000 claims description 2
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- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 claims description 2
- CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 claims description 2
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 claims description 2
- DLAPIMGBBDILHJ-UHFFFAOYSA-N dimethoxy-(3-methyl-4-methylsulfinylphenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C(S(C)=O)C(C)=C1 DLAPIMGBBDILHJ-UHFFFAOYSA-N 0.000 claims description 2
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- NEHGWVYDSJWTJK-YIXHJXPBSA-N ethyl (E)-4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoate Chemical compound C1=CC(OC(C)/C=C/C(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 NEHGWVYDSJWTJK-YIXHJXPBSA-N 0.000 claims description 2
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- NSWAMPCUPHPTTC-UHFFFAOYSA-N ethyl 2-[(4-chloro-6-methoxypyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 2
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- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- IXJOSTZEBSTPAG-UHFFFAOYSA-N methasulfocarb Chemical compound CNC(=O)SC1=CC=C(OS(C)(=O)=O)C=C1 IXJOSTZEBSTPAG-UHFFFAOYSA-N 0.000 claims description 2
- FWJLFUVWQAXWLE-UHFFFAOYSA-N methometon Chemical compound COCCCNC1=NC(NCCCOC)=NC(OC)=N1 FWJLFUVWQAXWLE-UHFFFAOYSA-N 0.000 claims description 2
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- 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
- KZAUOCCYDRDERY-UITAMQMPSA-N methyl (1Z)-2-(dimethylamino)-N-(methylcarbamoyloxy)-2-oxoethanimidothioate Chemical compound CNC(=O)O\N=C(/SC)C(=O)N(C)C KZAUOCCYDRDERY-UITAMQMPSA-N 0.000 claims description 2
- RBNIGDFIUWJJEV-LLVKDONJSA-N methyl (2R)-2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-LLVKDONJSA-N 0.000 claims description 2
- MFSWTRQUCLNFOM-SECBINFHSA-N methyl (2R)-2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 claims description 2
- CBLVUXPPNHUKDE-QBFSEMIESA-N methyl (5Z)-2,2-dimethyl-4,6-dioxo-5-[1-(prop-2-enoxyamino)butylidene]cyclohexane-1-carboxylate Chemical compound C=CCONC(/CCC)=C1/C(=O)CC(C)(C)C(C(=O)OC)C1=O CBLVUXPPNHUKDE-QBFSEMIESA-N 0.000 claims description 2
- VMNULHCTRPXWFJ-JGZWBZMZSA-N methyl (Z)-2-[2-[[(E)-[(E)-4-(4-chlorophenyl)but-3-en-2-ylidene]amino]oxymethyl]phenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(/C(=O)OC)C1=CC=CC=C1CO\N=C(/C)\C=C\C1=CC=C(Cl)C=C1 VMNULHCTRPXWFJ-JGZWBZMZSA-N 0.000 claims description 2
- JVSNVPQGCMNILW-UHFFFAOYSA-N methyl 2,7-dichloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC(Cl)=CC=C3C2=C1 JVSNVPQGCMNILW-UHFFFAOYSA-N 0.000 claims description 2
- JUCNGUOYQGHBJC-UHFFFAOYSA-N methyl 2-(2,4,5-trichlorophenoxy)acetate Chemical group COC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl JUCNGUOYQGHBJC-UHFFFAOYSA-N 0.000 claims description 2
- YTAXYXOJOYIQQO-UHFFFAOYSA-N methyl 2-(2,4,5-trichlorophenoxy)propanoate Chemical compound COC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl YTAXYXOJOYIQQO-UHFFFAOYSA-N 0.000 claims description 2
- HWIGZMADSFQMOI-UHFFFAOYSA-N methyl 2-(2,4-dichlorophenoxy)acetate Chemical group COC(=O)COC1=CC=C(Cl)C=C1Cl HWIGZMADSFQMOI-UHFFFAOYSA-N 0.000 claims description 2
- VWERIRLJUWTNDA-UHFFFAOYSA-N methyl 2-(4-chloro-2-methylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(Cl)C=C1C VWERIRLJUWTNDA-UHFFFAOYSA-N 0.000 claims description 2
- PMJRLYSMEOLBIU-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)quinoline-3-carboxylate Chemical compound COC(=O)C1=CC2=CC=CC=C2N=C1C1=NC(C)(C(C)C)C(=O)N1 PMJRLYSMEOLBIU-UHFFFAOYSA-N 0.000 claims description 2
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 claims description 2
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 claims description 2
- IAUMNRCGDHLAMJ-UHFFFAOYSA-N methyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IAUMNRCGDHLAMJ-UHFFFAOYSA-N 0.000 claims description 2
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 claims description 2
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims description 2
- ZINJLDJMHCUBIP-UHFFFAOYSA-N methyl 2-[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]carbamoylsulfamoyl]benzoate Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims description 2
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 claims description 2
- DFYPVJHFCVSDEV-UHFFFAOYSA-N methyl 2-chloro-9H-fluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)C3=CC=CC=C3C2=C1 DFYPVJHFCVSDEV-UHFFFAOYSA-N 0.000 claims description 2
- AWSBKDYHGOOSML-UHFFFAOYSA-N methyl 3,6-dichloro-2-methoxybenzoate Chemical group COC(=O)C1=C(Cl)C=CC(Cl)=C1OC AWSBKDYHGOOSML-UHFFFAOYSA-N 0.000 claims description 2
- DTSSCQVCVYZGSI-UHFFFAOYSA-N methyl 3-amino-2,5-dichlorobenzoate Chemical group COC(=O)C1=CC(Cl)=CC(N)=C1Cl DTSSCQVCVYZGSI-UHFFFAOYSA-N 0.000 claims description 2
- FWDQLSHRVKQKBS-UHFFFAOYSA-N methyl 4-(4-chloro-2-methylphenoxy)butanoate Chemical compound COC(=O)CCCOC1=CC=C(Cl)C=C1C FWDQLSHRVKQKBS-UHFFFAOYSA-N 0.000 claims description 2
- XSKZXGDFSCCXQX-UHFFFAOYSA-N methyl 4-[(3-methoxy-4-methyl-5-oxo-1,2,4-triazole-1-carbonyl)sulfamoyl]-5-methylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 claims description 2
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims description 2
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- DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3aR,4aS,8aR,8bS)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 claims description 2
- SGUSXTMVKMPQKI-UHFFFAOYSA-M sodium;2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)F SGUSXTMVKMPQKI-UHFFFAOYSA-M 0.000 claims description 2
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 claims description 2
- DPMABEYFRYKAHD-UHFFFAOYSA-M sodium;2,3,6-trichlorobenzoate Chemical compound [Na+].[O-]C(=O)C1=C(Cl)C=CC(Cl)=C1Cl DPMABEYFRYKAHD-UHFFFAOYSA-M 0.000 claims description 2
- PPRNMFDWJLACKG-UHFFFAOYSA-N sodium;2-(2,2-dimethylpropanoyl)inden-2-ide-1,3-dione Chemical compound [Na+].C1=CC=C2C(=O)[C-](C(=O)C(C)(C)C)C(=O)C2=C1 PPRNMFDWJLACKG-UHFFFAOYSA-N 0.000 claims description 2
- YPWJVPXHSDMPQB-UHFFFAOYSA-M sodium;2-(2,3,6-trichlorophenyl)acetate Chemical compound [Na+].[O-]C(=O)CC1=C(Cl)C=CC(Cl)=C1Cl YPWJVPXHSDMPQB-UHFFFAOYSA-M 0.000 claims description 2
- KXVMKVOQCMSZSZ-UHFFFAOYSA-M sodium;2-(2,4,5-trichlorophenoxy)acetate Chemical compound [Na+].[O-]C(=O)COC1=CC(Cl)=C(Cl)C=C1Cl KXVMKVOQCMSZSZ-UHFFFAOYSA-M 0.000 claims description 2
- KISFEBPWFCGRGN-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl KISFEBPWFCGRGN-UHFFFAOYSA-M 0.000 claims description 2
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 claims description 2
- DHJHUXNTNSRSEX-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1C DHJHUXNTNSRSEX-UHFFFAOYSA-M 0.000 claims description 2
- NAGWPMWBTLVULC-UHFFFAOYSA-M sodium;2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)quinoline-3-carboxylate Chemical compound [Na+].N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C([O-])=O NAGWPMWBTLVULC-UHFFFAOYSA-M 0.000 claims description 2
- CLHHSSXFXYAXDB-UHFFFAOYSA-M sodium;2-(naphthalen-1-ylcarbamoyl)benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 CLHHSSXFXYAXDB-UHFFFAOYSA-M 0.000 claims description 2
- CJRHMRPCBSJKBI-UHFFFAOYSA-M sodium;2-[(5-bromo-6-oxo-1-phenylpyridazin-4-yl)amino]-2-oxoacetate Chemical compound [Na+].O=C1C(Br)=C(NC(=O)C(=O)[O-])C=NN1C1=CC=CC=C1 CJRHMRPCBSJKBI-UHFFFAOYSA-M 0.000 claims description 2
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(E)-N-[(3,5-difluorophenyl)carbamoylamino]-C-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 claims description 2
- XKKTVIWAHIWFAN-UHFFFAOYSA-M sodium;2-[2-[2-(dodecylamino)ethylamino]ethylamino]acetate Chemical compound [Na+].CCCCCCCCCCCCNCCNCCNCC([O-])=O XKKTVIWAHIWFAN-UHFFFAOYSA-M 0.000 claims description 2
- LRWSMDCIWRLZIX-UHFFFAOYSA-M sodium;2-butan-2-yl-4,6-dinitrophenolate Chemical compound [Na+].CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1[O-] LRWSMDCIWRLZIX-UHFFFAOYSA-M 0.000 claims description 2
- JQYJSVBNPUHHKB-UHFFFAOYSA-M sodium;2-methyl-4,6-dinitrophenolate Chemical compound [Na+].CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1[O-] JQYJSVBNPUHHKB-UHFFFAOYSA-M 0.000 claims description 2
- HLZCHRAMVPCKDU-UHFFFAOYSA-M sodium;3,6-dichloro-2-methoxybenzoate Chemical compound [Na+].COC1=C(Cl)C=CC(Cl)=C1C([O-])=O HLZCHRAMVPCKDU-UHFFFAOYSA-M 0.000 claims description 2
- KQSJSRIUULBTSE-UHFFFAOYSA-M sodium;3-(3-ethylcyclopentyl)propanoate Chemical compound [Na+].CCC1CCC(CCC([O-])=O)C1 KQSJSRIUULBTSE-UHFFFAOYSA-M 0.000 claims description 2
- WMWBBXKLYSGKDY-UHFFFAOYSA-M sodium;3-amino-2,5-dichlorobenzoate Chemical compound [Na+].NC1=CC(Cl)=CC(C([O-])=O)=C1Cl WMWBBXKLYSGKDY-UHFFFAOYSA-M 0.000 claims description 2
- PPKIJAQKBAYNNL-UHFFFAOYSA-M sodium;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl PPKIJAQKBAYNNL-UHFFFAOYSA-M 0.000 claims description 2
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 claims description 2
- CWTLTFQJQXGTTP-UHFFFAOYSA-M sodium;N'-(2-iodophenyl)sulfonyl-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamimidate Chemical compound [Na+].COC1=NC(C)=NC(NC(=O)[N-]S(=O)(=O)C=2C(=CC=CC=2)I)=N1 CWTLTFQJQXGTTP-UHFFFAOYSA-M 0.000 claims description 2
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;N-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 claims description 2
- YPMAQKXGDCKXPE-WCCKRBBISA-M sodium;[(3S)-3-amino-3-carboxypropyl]-methylphosphinate Chemical compound [Na+].CP([O-])(=O)CC[C@H](N)C(O)=O YPMAQKXGDCKXPE-WCCKRBBISA-M 0.000 claims description 2
- CRHGSCXKJPJNAB-UHFFFAOYSA-M sodium;[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl]-methylsulfonylazanide Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(/[O-])=N/S(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CRHGSCXKJPJNAB-UHFFFAOYSA-M 0.000 claims description 2
- PEXLHWBDBQUUOG-UHFFFAOYSA-N sodium;methyl N-(4-aminophenyl)sulfonylcarbamate Chemical compound [Na+].COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 PEXLHWBDBQUUOG-UHFFFAOYSA-N 0.000 claims description 2
- IRZFQKXEKAODTJ-UHFFFAOYSA-M sodium;propan-2-yloxymethanedithioate Chemical compound [Na+].CC(C)OC([S-])=S IRZFQKXEKAODTJ-UHFFFAOYSA-M 0.000 claims description 2
- 229940014213 spinosad Drugs 0.000 claims description 2
- 239000003206 sterilizing agent Substances 0.000 claims description 2
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- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Chemical compound CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 claims description 2
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 2
- 229950008316 sulfiram Drugs 0.000 claims description 2
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 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
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 claims description 2
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 claims description 2
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 claims description 2
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- 150000008117 polysulfides Polymers 0.000 description 1
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Inorganic materials [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- OFCQYQOZASISIU-OGFXRTJISA-M potassium;(2R)-2-(4-chloro-2-methylphenoxy)propanoate Chemical compound [K+].[O-]C(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C OFCQYQOZASISIU-OGFXRTJISA-M 0.000 description 1
- NUUZKOFSZIWYSC-UHFFFAOYSA-M potassium;2-(4-chlorophenyl)-3-ethyl-5-oxopyridazine-4-carboxylate Chemical compound [K+].CCC1=C(C([O-])=O)C(=O)C=NN1C1=CC=C(Cl)C=C1 NUUZKOFSZIWYSC-UHFFFAOYSA-M 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- DQRQIQZHRCRSDB-UHFFFAOYSA-M potassium;N-methylcarbamodithioate Chemical compound [K+].CNC([S-])=S DQRQIQZHRCRSDB-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- RCIGDGBXEMECGY-UHFFFAOYSA-N pyridin-3-ylhydrazine Chemical compound NNC1=CC=CN=C1 RCIGDGBXEMECGY-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- ZAXLKOUOBYJMHS-QNBHOGDNSA-N scilliroside Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@H]4[C@@]([C@]3(CC2)O)(C)C[C@H](C2=C[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC[C@@]24C)OC(=O)C)C=CC(=O)OC=1 ZAXLKOUOBYJMHS-QNBHOGDNSA-N 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- TURJLPVZRPWSJO-UHFFFAOYSA-N sodium;2-(2,2-diphenylacetyl)inden-2-ide-1,3-dione Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)[C-]1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 TURJLPVZRPWSJO-UHFFFAOYSA-N 0.000 description 1
- XWAFIZUTHLRWBE-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1Cl XWAFIZUTHLRWBE-UHFFFAOYSA-M 0.000 description 1
- RTWIRLHWLMNVCC-UHFFFAOYSA-M sodium;2-[2-[[2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoylamino]propanoate Chemical compound [Na+].[O-]C(=O)C(C)NC(=O)C(C)NC(=O)C(N)CCP(C)(O)=O RTWIRLHWLMNVCC-UHFFFAOYSA-M 0.000 description 1
- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- OPYWMHIOONXUTL-UHFFFAOYSA-N tert-butyl N-(1-pyridin-3-ylpyrazol-4-yl)carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=NN1C1=CC=CN=C1 OPYWMHIOONXUTL-UHFFFAOYSA-N 0.000 description 1
- GFMSOEBIQWLNDS-UHFFFAOYSA-N tert-butyl N-(3-chloro-1-pyridin-3-ylpyrazol-4-yl)-N-(2-methoxyethyl)carbamate Chemical compound N1=C(Cl)C(N(C(=O)OC(C)(C)C)CCOC)=CN1C1=CC=CN=C1 GFMSOEBIQWLNDS-UHFFFAOYSA-N 0.000 description 1
- MLBAPDINMZNHOI-UHFFFAOYSA-N tert-butyl N-(3-chloro-1-pyridin-3-ylpyrazol-4-yl)-N-(cyanomethyl)carbamate Chemical compound N1=C(Cl)C(N(CC#N)C(=O)OC(C)(C)C)=CN1C1=CC=CN=C1 MLBAPDINMZNHOI-UHFFFAOYSA-N 0.000 description 1
- HXVXAVBCAKSDAP-UHFFFAOYSA-N tert-butyl N-(3-chloro-1-pyridin-3-ylpyrazol-4-yl)-N-ethylcarbamate Chemical compound N1=C(Cl)C(N(C(=O)OC(C)(C)C)CC)=CN1C1=CC=CN=C1 HXVXAVBCAKSDAP-UHFFFAOYSA-N 0.000 description 1
- GXHXSMHAUIZOSW-UHFFFAOYSA-N tert-butyl N-[1-(5-fluoropyridin-3-yl)pyrazol-4-yl]carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=NN1C1=CN=CC(F)=C1 GXHXSMHAUIZOSW-UHFFFAOYSA-N 0.000 description 1
- JZWVRXMFGDUSQX-UHFFFAOYSA-N tert-butyl N-[3-cyclopropyl-1-(5-fluoropyridin-3-yl)pyrazol-4-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CN(C=2C=C(F)C=NC=2)N=C1C1CC1 JZWVRXMFGDUSQX-UHFFFAOYSA-N 0.000 description 1
- XKEFJJMCMSUAFM-UHFFFAOYSA-N tert-butyl N-[3-ethenyl-1-(5-fluoropyridin-3-yl)pyrazol-4-yl]-N-methylcarbamate Chemical compound N1=C(C=C)C(N(C(=O)OC(C)(C)C)C)=CN1C1=CN=CC(F)=C1 XKEFJJMCMSUAFM-UHFFFAOYSA-N 0.000 description 1
- QBYJUXIVKGTROX-UHFFFAOYSA-N tert-butyl N-ethyl-N-(1-pyridin-3-ylpyrazol-4-yl)carbamate Chemical compound C1=C(N(C(=O)OC(C)(C)C)CC)C=NN1C1=CC=CN=C1 QBYJUXIVKGTROX-UHFFFAOYSA-N 0.000 description 1
- JOQDKLONOSELJX-UHFFFAOYSA-N tert-butyl N-methyl-N-(3-methyl-1-pyridin-3-ylpyrazol-4-yl)carbamate Chemical compound N1=C(C)C(N(C(=O)OC(C)(C)C)C)=CN1C1=CC=CN=C1 JOQDKLONOSELJX-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- BPJYAXCTOHRFDQ-UHFFFAOYSA-L tetracopper;2,4,6-trioxido-1,3,5,2,4,6-trioxatriarsinane;diacetate Chemical compound [Cu+2].[Cu+2].[Cu+2].[Cu+2].CC([O-])=O.CC([O-])=O.[O-][As]1O[As]([O-])O[As]([O-])O1.[O-][As]1O[As]([O-])O[As]([O-])O1 BPJYAXCTOHRFDQ-UHFFFAOYSA-L 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 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
- 150000003556 thioamides Chemical class 0.000 description 1
- BSNQHVPRAPQLSW-UHFFFAOYSA-N thiolane-3-carboxylic acid Chemical compound OC(=O)C1CCSC1 BSNQHVPRAPQLSW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-M triacetate(1-) Chemical compound CC(=O)CC(=O)CC([O-])=O ILJSQTXMGCGYMG-UHFFFAOYSA-M 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-FIBGUPNXSA-N trideuterio(iodo)methane Chemical compound [2H]C([2H])([2H])I INQOMBQAUSQDDS-FIBGUPNXSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- MLFGIRNMAOXTHS-UHFFFAOYSA-N tris(2-methylaziridin-1-yl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC1CN1P(=S)(N1C(C1)C)N1C(C)C1 MLFGIRNMAOXTHS-UHFFFAOYSA-N 0.000 description 1
- ICESBGJHRQHALQ-UHFFFAOYSA-K trisodium;(carboxymethylamino)methyl-hydroxyphosphinate;2-[[hydroxy(oxido)phosphoryl]methylamino]acetate Chemical compound [Na+].[Na+].[Na+].OC(=O)CNCP(O)([O-])=O.OC(=O)CNCP([O-])([O-])=O ICESBGJHRQHALQ-UHFFFAOYSA-K 0.000 description 1
- 230000021037 unidirectional conjugation Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
Abstract
This document discloses molecules having the following formula (1) and processes related thereto.
Description
PESTICIDAL COMPOSITIONS AND PROCESSES RELATED THERETO
CROSS-REFERENCE TO RELATED APPLICATIONS
This Application claims priority from U.S. provlslonal application 61/551585 filed on October 26, 2011. The entire content of this provlslonal application is hereby incorporated by reference Into this Application.
FIELD OF THE DISCLOSURE
This disclosure is reiated to the field of processes to produce molécules that are useful as pesticides (e.g., acaricides, Insecticides, mollusdcides, and nematicides), such molécules, and processes of using such molécules to control pests.
BACKGROUND
Pests cause millions of human deaths around the world each year. Furthermore, there are more than ten thousand species of pests that cause losses in agriculture. The world-wide agriculture! losses amount to billions of U.S. dollars each year.
Termites cause damage to ail klnds of private and public structures. The world-wide termite damage losses amount to billions of U.S. dollars each year.
Stored food pests eat and adulterate stored food. The world-wide stored food losses amount to billions of U.S. dollars each year, but more importantly, deprive people of needed food.
There is an acute need for new pesticides. Certain pests are deveioping résistance to pesticides In current use. Hundreds of pest species are résistant to one or more pesticides. The development of résistance to some of the oider pesticides, such as DDT, the carbamates, and the organophosphates, is well known. But résistance has even developed to some of the newer pesticides.
Therefore, for many reasons, including the above reasons, a need exists for new pesticides.
DEFINITIONS
The examples given In the définitions are generally non-exhaustive and must not be construed as limiting the Invention disclosed in this document. It Is understood that a substituent shouid corn pi y with chemical bonding rules and steric compatibility constraints in relation to the particular molécule to which it is attached.
Alkenyl means an acydic, unsaturated (at least one carbon-carbon double bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, vlnyi, allyl, butenyl, pentenyl, and hexenyl.
Alkenyloxy* means an alkenyl further consisting of a carbon-oxygen single bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy.
“Alkoxy means an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, Isopropoxy, butoxy, Isobutoxy, and tert-butoxy.
“Alkyl means an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, (C3)alkyl which represents n-propyl and isopropyl), (C4)alky1 which represents n-butyl, seobutyl, Isobutyl, and tert-butyl.
“Alkynyl means an acyclic, unsaturated (at least one carbon-carbon triple bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, ethynyl, propargyl, butynyl, and pentynyl.
Alkynyloxy means an alkynyl further consisting of a carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy.
Aryl means a cyclic, aromatic substituent consisting of hydrogen and carbon, for example, phenyl, naphthyl, and biphenyl.
“(CM-Cy) where the subscripts “x and “y are Integers such as 1,2, or 3, means the range of carbon atoms for a substituent - for example, (CrC4)alkyl means methyl, ethyl, n-propyl, Isopropyl, n-butyl, seo-butyl, Isobutyl, and tert-butyl, each Individually.
Cycloalkenyl* means a monocyclic or polycyclic, unsaturated (at least one carbon-carbon double bond) substituent consisting of carbon and hydrogen, for example, cyclobutenyl, cyclopentenyl, cyclohexenyl, norbomenyl, bicyclo[2.2.2]octenyt, tetrahydronaphthyl, hexahydronaphthyl, and octahydronaphthyl.
“Cycloalkenyloxy means a cycloalkenyl further consisting of a carbon-oxygen single bond, for example, cyclobutenyloxy, cyclopentenyloxy, norbomenyloxy, and bicyclo[2.2.2]octenyloxy.
Cycloalkyl* means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl, cyclopentyl, norbomyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.
Cycloalkoxy” means a cycloalkyl further consisting of a carbon-oxygen single bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbomyloxy, and bicyclo[2.2.2]octyloxy.
“Halo means fluoro, chloro, bromo, and lodo.
Haloalkoxy means an alkoxy further consisting of, from one to the maximum possible number of Identical or different, halos, for example, fluoromethoxy, trifluoromethoxy, 2,2difluoropropoxy, chloromethoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.
Haloalkyl means an alkyl further consisting of, from one to the maximum possible number of, Identical or different, halos, for example, fluoromethyi, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl, and 1,1,2,2-tetrafluoroethyl.
Heterocyclyl means a cyclic substituent that may be fully saturated, partially unsaturated, or fully unsaturated, where the cyclic structure contains at ieast one carbon and at least one heteroatom, where said heteroatom Is nitrogen, sulfur, or oxygen. In the case of sulfur, that atom can be In other oxidation states such as a sulfoxide and sulfone. Examples of aromatic heterocyclyls include, but are not limited to, benzofuranyl, benzolsothlazolyl, benzoisoxazolyl, benzoxazolyl, benzothlenyl, benzothîazoiyl, dnnolinyl, furanyl, Imidazolyl, indazolyl, Îndolyî, isolndolyl, isoquînolinyl, îsothiazolyl, Isoxazolyl, oxadiazolyl, oxazolinyl, oxazoiyl, phthalazinyl, pyrazinyl, pyrazoiinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyî, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, and triazolyl. Examples of fully saturated heterocyclyls Include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothieny! and tetrahydropyranyl. Examples of partially unsaturated heterocyclyls Include, but are not limited to, 1,2,3,4-tetrahydroquinolinyl, 4,5dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-[1,3,4]oxadiazoiyl. Additional examples Include the following thietanyl
O thietanyl-dioxide.
DETAILED DESCRIPTION
This document discloses molécules having the following formula (‘Formula One’):
R6 wherein (a) A is either
attachment bond
attachment bond (b) R1 Is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted Cj-Ce alkenyl, substituted or unsubstituted C^Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted Cy-Cio cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C^ aryl, substituted or unsubstituted heterocydyl, OR9, C(=X1 )R9, C(=X1 )OR9, C(=X1 )N(R9)2, N(R9)21 N(R9)C(=X1 )R9, S(O)nR9, S(O)nOR9, S(O)„N(R9)2, or R9S(O)nR9, wherein each said R1, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCg alkyl, Cî-Ce alkenyl, CrCg haloalkyl, CrCg haloalkenyl, CrCg haloalkyloxy, C2-Cg haloalkenyloxy, C3-C10 cycloalkyl, Qj-Cw cycloalkenyi, C3-C10 halocycloaikyl, C3-C10 halocycloalkenyl, OR9, S(O)nOR9, Cg-C^ aryl, or CrCw heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);
(c) R2 Is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted CrCg alkyl, substituted or unsubstituted CrCg alkenyl, substituted or unsubstituted CrCg alkoxy, substituted or unsubstituted CrCg alkenyloxy, substituted or unsubstituted CyC10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyi, substituted or unsubstituted Cg-Cæ aryl, substituted or unsubstituted C1-C20 heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, or R9S(O)nR9, wherein each said R2, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCg alkyl, CrCg alkenyl, CrCg haloaikyl, C2-C9 haloaikenyl, Ci-Cg haloalkyloxy, CrCe haloalkenyloxy, CrC10 cycloalkyl, CrCi0 cycloalkenyi, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, OR9, S(O)oOR9, Cg-C^ aryl, or CpC^ heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);
(d) R3 is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted Ci-Cg alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted Ci-Cg alkoxy, substituted or unsubstituted Ci-Ct alkenyloxy, substituted or unsubstituted CrC10 cycloalkyl, substituted or unsubstituted CrC10 cycloalkenyi, substituted or unsubstituted Cg-C» aryl, substituted or unsubstituted CpC» heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, orR9S(0)nR9, wherein each said R3, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCg alkyl, CrCg alkenyl, CrCg haloalkyl, CrCg haloalkenyl, Ci-Cg haloalkyloxy, CrCg haloalkenyloxy, C3-C10 cycloalkyl, CrC10 cycloalkenyi, CrC10 halocycloalkyl, CrCio halocycloalkenyl, OR9, S(O)nOR9, Cg-C^ aryl, or CrC^ heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);
(e) when A Is (1) A1 then A1 Is either (a)
A11 attachment bond to carbon
Ail where R4 Is H, NO2, substituted or unsubstituted Ct-Cg alkyl, substituted or unsubstituted CrCg alkenyl, substituted or unsubstituted Ci-Cg alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted CrC10 cycloalkenyl, substituted or unsubstituted Cg-C» aryl, substituted or unsubstituted C1-C20 heterocyclyl, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, S(O)„OR9, orR9S(O)„R9, wherein each said R4, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, Cf-Cg alkyl, C^-Cg alkenyl, C«-Cg haloalkyl. C^Cg haloalkenyl, Ci-Cg haloalkyloxy, CrCg haloalkenyioxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3C10 halocycloalkyl, Cj-Cto halocycloalkenyl, OR9, S(O)„OR9, Cg-C» aryl, or CpC» heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9). or (b) A12
attachment bond to nitrogen (2) A2 then R4 is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted CfCg alkyl, substituted or unsubstituted C2-Cs alkenyl. substituted or unsubstituted CrCg alkoxy,
substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C» aryl, substituted or unsubstituted CpC» heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)21 N(R9)C(=X1)R9, SR9, S(O)nOR9, orR9S(O)nR9, wherein each said R4, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, CrCe haloalkyl, CrCe haloalkenyl, CrCe haioalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3C10 halocycloalkyl, C3-C10 halocydoalkenyl, OR9, S(O)nOR9, Ce-Cw aryl, or C1-C20 heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);
(f) R5 Is H, F, Cl, Br, I, CN, NO21 substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted CrC10 cycloalkenyl, substituted or unsubstituted Ce-C^aryl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, or R9S(O)nR9, wherein each said R5, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, CrCe haloalkyl, CrCe haloalkenyl, Ci-Ce haioalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, Ca-Cw halocycloalkyl, Ca-Cw halocydoalkenyl, OR9, S(O)nOR9, or Ce-C» aryl, (each of which that can be substituted, may optionally be substituted with R9);
(g) (1) when A is A1 then R6 is R11, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted Ci-Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cydoalkyl, substituted or unsubstituted C3-C10 cydoalkenyl, substituted or unsubstituted Ce-Cm aryl, substituted or unsubstituted C,-^ heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, R9S(O)nR9, C,-Ce alkyl Ce-C^ aryl (wherein the alkyl and aryl can independently be substituted or unsubstituted), C(=X2)R9, C(=X1 )X2R9, R9X2C(=X1)R9, R9X2R9, C(=O)(C1-C6 alkyl)S(O)n(CrCe alkyl), C(=O)(CrCe alkyl)C(=O)O(CrCe alkyl), (C,-Ce aikyl)OC(=O)(Ce-C20 aryl), (CrCe alkyl)OC(=O)(Ci-Ce alkyl), Ci-Ce alkyl-(Ca-Ci0 cyclohaloalkyl), or (Ci-Ce alkenyl)C(=O)O(Ci-Ce alkyl), or R9X2C(=X1 )X2R9, wherein each said R6 (except R11 ), which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, C,-Ce alkyi, CrCe alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, CrCe haloalkyloxy, CrCe haloalkenyloxy, C3-C1Q cycloalkyl, C3-C,o cycloalkenyl, C3C10 halocycloalkyl, C3-C1Q halocycloalkenyl, OR9, S(O)nOR9, Ce-C^ aryl, or CpC» heterocyclyl, R9aryl, (each of which that can be substituted, may optionally be substituted with R9), optionally R6 (except R11) and R8 can be connected In a cyclic arrangement, where optionally such arrangement can hâve one or more heteroatoms selected from O, S, or, N, In the cyclic structure connecting R6 and R8, and (2) when A is A2 then R6 is R11, H, substituted or unsubstituted Ci-Ce alkyi, substituted or unsubstituted C2-Ce alkenyl, substituted or unsubstituted C,-Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C,o cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Cg-C^ aryl, substituted or unsubstituted Ci-C^ heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, R9S(O)nR9, C,-Ce alkyi Ce-C™ aryl (wherein the alkyi and aryl can Independently be substituted or unsubstituted), C(=X2)R9, C(=X1)X2R9, R9X2C(=X1)R9, R9X2R9, C(=O)(C,-Ce alkyl)S(O)n(C,-Ce alkyi), 0(=0)(0,-0,, alkyl)C(=O)O(Ci-Ce alkyi), (C,-Ce alkyliOCisOJtCe-Cîo aryl), (C,-Ce alkyl)OC(=O)(C,-Ce alkyi), Ο,-Οβ alkyl-(C3-C,o cydohaloalkyl), or (C,-Ce alkenyl)C(=O)O(C,-Ce alkyi), or R9X2C(=X1)X2R9, wherein each said R6 (except R11), which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, N02, C,-Ce alkyi, CrCe alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, C,-Ce haloalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3C,o halocycloalkyl, C3-C10 halocycloalkenyl, 0R9, S(O)nOR9, Ce-Cjo aryl, or CpCa heterocyclyl, R9aryl, (each of which that can be substituted, may optionally be substituted with R9), optionally R6 (except R11) and R8 can be connected in a cyclic arrangement, where optionally such arrangement can hâve one or more heteroatoms selected from O, S, or N, In the cyclic structure connecting R6 and R8;
(h) R7 is O, S, NR9, or NOR9;
(i) R8 Is substituted or unsubstituted C,-Ce alkyi, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted C,-Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C,o cycloalkenyl, substituted or unsubstituted Ce-C» aryl, substituted or unsubstituted Ci-C» heterocyclyl 0R9,
OR9S(O)nR9, C(=X1)R9, C(=X1)OR9, R9C(=X1)OR9, R9X2C(=X1)R9X2R9, C(=X1)N(R9)2,
N(R9)2, N(R9)(R9S(O)nR9), N(R9)C(-X1)R9, SR9, S(O)nOR9, R9S(O)nR9, or R9S(O)n(NZ)R9, wherein each said R8, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, CrCe haioalkyl, CrCe haloalkenyl, C,-C6 haloalkytoxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3-C10 halocycloalkyl, CrC10 halocycloalkenyl, N(R9JS(O)nR9, oxo, OR9, S(O)nOR9, R9S(O)nR9, S(O)nR9, Ce-Ca aryl, or Ci-Cm heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);
(J) R9 Is (each Independently) H, CN, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted Ci-Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-CM aryl, substituted or unsubstituted CpC» heterocyclyl, substituted or unsubstituted S(O)nCi-Ce alkyl, substituted or unsubstituted N(C1-C6alkyl)2.
wherein each said R9, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, Cf-Ce alkyl, CrCe alkenyl, CrCe haioalkyl, CrCe haloalkenyl, CpCe haloalkytoxy, CrCe haloalkenyloxy, CrC10 cycloalkyl, Cs-Cw cycloalkenyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, OCpCe alkyl, OCrCe haioalkyl, S(O)nCi-Cealkyl, S(O)nOCrCe alkyl, Ce-C^ aryl, or Cf-C^heterocyclyl;
(k) nisO, 1,or2;
(l) X Is N or CRni where Rni is H, F, Cl, Br, I, CN, NO2l substituted or unsubstituted C,Ce alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C8-CM aryl, substituted or unsubstituted Cj-C^ heterocyclyl. OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)21 N(R9)C(=X1)R9, SR9, S(O)nR9, S(O)nOR9, orR9S(O)nR9, wherein each said Rni which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, Ci-Ce alkyl, CrCe alkenyl, Ci-Ce haioalkyl, CrCe haloalkenyl, CrCe haloalkytoxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, OR9, S(O)nOR9, Ce-Cw aryl, or Ci-C20 heterocyclyl, (each of which that 9 can be substituted, may optionally be substituted with R9);
(m) X1 is (each independently) O or S;
(η) X2 Is (each Independently) O, S, =NR9, or =NOR9;
(ο) Z Is CN, NO2, CrCe alky!(R9), C(=X1 )N(R9)2;
(p) R111s Qi(C=C)R12, wherein Qt Is a bond, substituted or unsubstituted Ct - Cç alkyl, substituted or unsubstituted C^Cg alkenyl, substituted or unsubstituted C2-Cg alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-Ct0 cycloalkoxy, substituted or unsubstituted CrC0alkylOR9, substituted or unsubstituted Ct-CgalkylS(O)nR9, substituted or unsubstituted CrC0alkylS(O)n(=NR9), substituted or unsubstituted Ct-CgalkylN(R9) (where (C=C) is attached directly to the N by a bond), substituted or unsubstituted Ct-CgalkylN(R9)2, substituted or unsubstituted CrCg alkenyloxy, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted C0-CealkylC(=R7)C0-Ce alkylR9, substituted or unsubstituted Co-Ce alkylC(=R7)OR9, substituted or unsubstituted Ct-Cg alkylOCo-C# alkylC(=R7)R9, substituted or unsubstituted Ct-Cg alkylN(R9)(C(=R7)R9), substituted or unsubstituted Ct-CealkylN(R9)(C(=R7)OR9)1 substituted or unsubstituted Co-Ce alkyl C(=R7)Co-Cg alkylN(R9) (where (C=C) Is attached directly to the N by a bond), substituted or unsubstituted Co-CealkylC(=R7)Co-Cg alkylN(R9)2, OR9, S(O)nR9, N(R9)R9, substituted or unsubstituted Cg-C^ aryl, substituted or unsubstituted Ci-C» heterocyclyl, wherein each said Qt, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CfC0 alkyl, C2-Cç alkenyl, C^Cg alkynyl, Ct-Cg haloalkyl, Ct-C® haloalkenyl, CrCg haloalkyloxy, CrCe haloalkenyloxy, C3-Cl0 cycloalkyl, Qj-Cto cycloalkenyl, C3C10 halocycloaikyl, C3-C10 halocycloalkenyl, OR9, SR9, S(O)nR9, S(O)nOR9, Cg-C» aryl, or 0,-C^ heterocyclyl, R9aryl, CrCcalkylOR9, Ct-CBalkylS(O)nR9, (each of which that can be substituted, may optionally be substituted with R9) optionally Qt and RS can be connected In a cyclîc arrangement, where optionally such arrangement can hâve one or more heteroatoms selected from O, S, or N, In the cyclic structure connecting Qt and RS;
(q) R12 is Qt (except where Qt is a bond), F, Ci, Br, I, Si(R9)3 (where each R9 is independently selected), or R9; and (r) with the following provisos (1 ) that R6 and R8 cannot both be C(=O)CH3, (2) that when A1 1s A11 then R6 and R8 together do not form fused ring Systems, (3) that R6 and R8 are not linked in a cyclic arrangement with only -CH2-, (4) that when A Is A2 then R5 is not C(=O)OH, (5) that when A is A2 and R6 is H then R8 Is not a -(CrCe alkyl)-O-(substituted aryl), and (6) that when A 1s A2 then R6 Is not -(Cialkyl)(substituted aryl).
tn another embodiment of this invention A Is A1.
tn another embodiment of this invention A Is A2.
In another embodiment of this invention R1 is H.
In another embodiment of this invention R2 is H.
In another embodiment of this invention R3 is selected from H, or substituted or unsubstituted CrCe alkyl.
In another embodiment of this invention R3 Is selected from H or CH3.
tn another embodiment of the invention when A Is A1 then A1 is A11.
in another embodiment of the Invention when A Is A1, and A11s A11, then R4 Is selected from H, or substituted or unsubstituted CrCe alkyl, or substituted or unsubstituted Ce-C» aryl.
In another embodiment of the Invention when A Is A1, and A1 Is A11 then R4 Is selected from CH3, CH(CH3)2, or phenyl.
In another embodiment of the Invention when A is A1, and A1 is A12, then R4 is CH3.
In another embodiment of this invention when A Is A2 then R4 is selected from H, or substituted or unsubstituted Ci-Ce alkyl, substituted or unsubstituted C2-Ce alkenyl, substituted or unsubstituted Co-Cjo cycloalkyl, substituted or unsubstituted Ce-Cw aryl, wherein each said R4, which is substituted, has one or more substituents selected from F, Cl, Br, or I.
tn another embodiment of this invention when A is A2 then R4 is H or CrCe alkyl.
ln another embodiment of this invention when A is A2 then R4 is H, CH3, CH2CH3, CH=CH2, cyclopropyl, CH2CI, CF3, or phenyl.
ln another embodiment of this invention when A is A2 then R4 is Cl.
ln another embodiment of this invention R5 is H, F, Cl, Br, I, or substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkoxy.
In another embodiment of this invention R5 is H, OCH2CH3, F, Cl, Br, orCH3.
ln another embodiment of this invention, when A is A1 then R6 is substituted or unsubstituted CrCe alkyl.
ln another embodiment of this invention when A is A2 then R6 is selected from is substituted or unsubstituted CrCe aikyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, C(=X1)R9, C(=X1)X2R9, R9X2R9, C(=O)(C3-Ce alkyl)S(O)n(CrCe alkyl), (CrCe alkyl)OC(=O)(C6-C20 aryl), (CrCe 318^)00(=0)(0,-^ alkyl), or R9X2C(=X1)X2R9.
ln another embodiment of this invention when A is A2 then R6 and R8 are connected in a cyclic arrangement, where optionally such arrangement can hâve one or more heteroatoms selected from O, S, or, N, in the cyclic structure connecting R6 and R8.
ln another embodiment of this invention R6 is CrCe alkyl, or CrCe alkyl-phenyl.
In another embodiment of this invention R6 is H, CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, CH2phenyl, CH2CH(CH3)2, CH2cyclopropyl, C(=O)CH2CH2SCH3, C(=O)OC(CH3)3, CH2CH=CH2, C(=O)OCH2CH31 C(=O)CH(CH3)CH2SCH31 cyclopropyl, CD31 CH2OC(=O)phenyl, C(=O)CH3, C(=O)CH(CH3)2, CH2OC(=O)CH(CH3)2, CH2OC(=O)CH3i C(=O)phenyl1 CH2OCH3, CH2OC(=O)CH2OCH2CH3, CH2CH2OCH3, CH2OC(=O)OCH(CH3)2, ch2ch2och2och31 CH2CH2OCH3, CH2CH2OC(=O)CH3, ch2cn.
ln another embodiment of this invention R6 Is methyl or ethyl.
ln another embodiment of this invention R7 is O or S.
ln another embodiment of this invention R8 is selected from substituted or unsubstituted Cr C6 alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CyCio cycloalkyl, substituted or unsubstituted Ce-Cw aryl, substituted or unsubstituted CrC^ heterocyclyl, R9C(=X1)OR9, SR9, S(O)„OR9, R9S(O)nR9, or R9S(O)n(NZ)R9.
ln another embodiment of this invention R8 is CHiCHsJCH^CHs, CHiCH^, C(CH3)2CH2SCH3, CH2CH2SCH3i CH2CF3i CH2CH2C(=D)OCH3, N(H)(CH2CH2SCH3), OCH2CH2SCH3, CH(CH2SCH3)(CH2phenyl), thiazolyl, oxazolyl, Isothiazolyl, substituted-furanyl, CH3, C(CH3)3, phenyl, CH2CH2OCH3, pyridyï, CH2CH(CH3)SCH3, OC(CH3)31 C(CH3)2CH2SCH3,
CH(CH3)CH(CH3)SCH3. CH(CH3)CF3, CHjCHrthienyl, CH(CH3)SCF31CH2CH2C1, CH2CH2CH2CF3, CH2CH2S(=O)CH3, CH(CH3)CH2S(=O)CH3> CH2CH2S(=O)2CH3, CH(CH3)CHÎS(=O)ÎCH3. NCH2CH31 N(H)(CH2CH2CH3), C(CH3)=C(H)(CH3), N(H)(CH2CH=CH2), CH2CH(CF3)SCH3l CH(CF3)CH2SCH3, thletanyl, CH2CH(CF3)2, CH2CH2CF(OCF3)CF3i CH2CH2CF(CF3)CF3, CF(CH3)2, CH(CH3)phenyl-CI, CH(CH3)phenyl-F, CH(CH3)phenyl-OCF31 CH2N(CH3)(S(=O)2N(CH3)2, CH(CH3)OCH2CH2SCH3, CH(CH3)OCH2CH2OCH3, OCH3, CH(CH3)SCH31 CH2SCH3, N(H)CH3, CH(Br)CH2Br, CHjCHjSCHïCHîCFa, CHïCHjSH, CHîCHîSCÎphenylh, CH2N(CH3)S(O)2CH3> CH(SCH3)(C(=O)CH2SCH3), CH2S(O)CH3, CH2CH(cyclopropyl)SCH3, or CH(CH3)CH2SCD3.
In another embodiment of this invention R8 is selected from (substituted or unsubstituted CrCg alkyl)-S(O)n-(substituted or unsubstituted CrCs alkyl) wherein said substituents on said substituted alkyts are selected from F, Cl, Br, I, CN, NO2, N(R9)S(O)nR9, OR9, S(O)„OR9, R9S(O)nR9, S(O)nR9, Cg-C2o aryl, or CrC» heterocyclyl, (each of which that can be substituted, may optionaliy be substituted with R9).
In another embodiment of this invention X is CR^ where Rn1 Is H or halo.
In another embodiment of this Invention X Is CR^ where Rn1 is H or F.
In another embodiment of this Invention X1 is O.
In another embodiment of this Invention X2 is O.
In another embodiment of this invention R11 is substituted or unsubstituted CpCg aikylC=CR12.
In another embodiment of this Invention R111s CH2C=CH.
In another embodiment R11 is preferably CH2C=CH and R8 Is preferably (substituted or unsubstituted Ci-Cg alkyl)-S(O)n-(substituted or unsubstituted CrCg alkyl) wherein said substituents on said substituted alkyls are selected from F, Cl, Br, I.
In another embodiment R11 is preferably CH2C=CH and R8 Is preferably (unsubstituted Cr Cg alkyi)-S(O)n-(substituted C^Cg alkyl) wherein said substituents on said substituted alkyls are selected from F, Cl, Br, I.
In another embodiment R11 is preferably CH2C^CH and R8 is preferably (unsubstituted Cr C2 alkyl)-S(O)n-(substituted CrQj alkyl) wherein said substituents on said substituted alkyls are F.
The moiecules of Formula One will generally hâve a molecular mass of about 100 Daltons to about 1200 Daltons. However, it is generally preferred If the molecular mass Is from about 120 13
Daltons to about 900 Daltons, and it is even more generally preferred if the molecular mass is from about 140 Daltons to about 600 Daltons.
The following schemes illustrate approaches to generatïng aminopyrazoles. In step a of
Scheme I, treatment of a 3-acetopyridine or a 5-acetopyrimldine of Formula II, wherein R1, R2, R3 and X are as previously defined, with carbon disulfide and iodomethane in the presence of a base such as sodium hydride and in a solvent such as dimethyl sulfoxide provides the compound of Formula III. In step b of Scheme I, the compound of Formula III can be treated with an amine or amine hydrochloride, In the presence of a base, such as triethylamine, in a solvent such as ethyl 10 alcohol to afford the compound of Formula IV, wherein R1, R2, R3, R6 and X are as previously defined. The compound of Formula IV can be transformed into the aminopyrazoie of Formula Va where R5 = H as in step c of Scheme I and as in Peruncheralathan, S. et al. J. Org. Chem. 2005, 70, 9644-9647, by reaction with a hydrazine, such as methylhydrazlne, in a polar protic solvent such as ethyl alcohol.
Scheme I
Il III iv
Va
Another approach to aminopyrazoles is lllustrated In Scheme II. In step a, the nitrile of 14
Formula VI wherein X, R1, R2 and R3 are as previously defined and R5 Is hydrogen, Is condensed as in Dhananjay, B. Rendre et al. J. Het Chem 2008,45, (5), 1281-86 with hydrazine of Formula VII, such as methylhydrazine to give a mixture of aminopyrazoles of Formula Vb, wherein R5 and R6 = H, both of whose components were Isolated.
Scheme II
VI VII Vb
Préparation of aminopyrazoles such as those of Formula Xlla Is demonstrated in Scheme III. The compound of Formula X in step a and as In Cristau, Henri-Jean et al. Eur. J. Org. Chem. 2004,695-709 can be prepared through the N-arylation of a pyrazole of Formula IX with an appropriate aryl halide of Formula Villa where Q Is bromo in the presence of a base such as césium carbonate, a copper catalyst such as copper (ii) oxide and a ligand such as salicylaldoxime In a polar aprotic solvent such as acetonitrile. Compounds of Formula IX, as shown in Scheme III, wherein R4 = Cl and R5 = H, can be prepared as In Pelcman, B. et al\NO 2007/045868 A1. Nitration of the pyridylpyrazole of Formula X as in step b of Scheme III and as In Khan, Misbanul Ain et al. J. Heterocyclic Chem. 1981,18,9-14 by reaction with nitric acid and sulfuric acid gave compounds of Formula Xia. Réduction of the nitro functionality of compounds of Formula Xla In the presence of hydrogen with a catalyst such as 5% Pd/C In a polar aprotic solvent such as tetrahydrofuran gave the amine of Formula Xlla, as shown in step c in Scheme III. Réduction of the nitro functionality of compounds of Formula Xla, wherein R1, R2, R3, R4 and X are as previously defined and R5 s H, in the presence of hydrogen with a catalyst such as 10% Pd/C in a polar protic solvent such as éthanol gave the amine of Formula Xlla, wherein R5 = H, as well as the amine of Formula Xlla, wherein R5 = OEt, as shown in step d of Scheme III. Compounds of Formula Xla, wherein R1, R2, R3, R5 and X are as previously defined and R4 = Cl, can be reduced in the presence of a redudng agent such as iron in a mixture of polar protic solvents such as acetic acid, water, and éthanol to give amines of Formula Xlla, wherein R1, R2, R3, R5 and X are as previously defined R4 = CI, as shown in step e of Scheme III. Compounds of Formula Xla, wherein R1, R2,
R3, R5 and X are as previously defined and R4 = Cl, can be aliowed to react under Suzuki coupling conditions with a boronic acid such as phenylboronic acid In the presence of a catalyst such as palladium tetrakîs, a base such as 2M aqueous potassium carbonate, and in a mixed solvent system such as éthanol and toluene to provide cross-coupled pyrazoles of Formula Xlb, as shown 5 In step f of Scheme ill.
Scheme III
X
In step a of Scheme IV, the compounds of Formula Xllb can be treated with triethylorthoformate and an add such as trifluoroacetic acid. Subséquent addition of a reducing agent such as sodium borohydride in a polar protic solvent such as éthanol gave a compound of
Formula Xllla, wherein R6 = methyl.
In step b of Scheme IV, the compound of Formula XIIb can be treated with acetone in a solvent such as Isopropyl acetate, an acid such as trifluoroacetlc add and sodium triacetoxyborohydride to give compounds of Formula Xliia, wherein R6 = Isopropyl.
In step c of Scheme IV, the compounds of Formula XIIb can be acylated with an add chloride such as acetyl chloride In a polar aprotic solvent such as dichloromethane using the conditions described In Scheme V. Réduction of the amide with a redudng agent such as lithium alumlnum hydride in a polar aprotic solvent such tetrahydrofuran gives compounds of Formula Xllla, wherein R6 = ethyl.
Alternatively, In step dof Scheme IV, the compounds of Formula Xlib can be treated with benzotriazole and an aldéhyde In éthanol followed by réduction using, for example, sodium borohydride, to afford compounds of Formula Xllla. In step e of Scheme IV, the compounds of Formula Xllb can be treated with an aldéhyde such as propionaldéhyde and sodium triacetoxyborohydride In a polar aprotic solvent such as dichloromethane to give compounds of Formula Xllla, wherein R6 = propyl. As in step f, acylation of compounds of Formula Xllla in Scheme IV using the conditions described In Scheme IX affords compounds of Formula la, wherein R1, R2, R3, R4, R5, R6, R8 and X are as previously defined.
Scheme IV
R'
Xllb
Xllla
R.
Rla ln step a of Scheme V, the compounds of Formula Vc, wherein R1, R2, R3, R4, R5 and R6 and X are as previously defined, can be treated with an acid chloride of Formula XIV, In the presence of a base such as triethylamine or Ν,Ν-dimethylaminopyridine ln a polar aprotic solvent such as dichloroethane (DCE) to yield compounds of Formula ib, wherein R8 Is as previously defined. Additionally, when R6 - H the 2° amide may be subsequentiy alkylated ln step b of Scheme V with an alkyl halide such as lodoethane, In the presence of a base such as sodium hydride and a polar aprotic solvent such as Ν,Ν-dimethylformamide (DMF) to yield the desired compounds of Formula Ib. The acid chlorides used ln the acylation reactions herein are either commerdally a va i labié or can be synthesized by those skilled In the art.
Scheme V
ln step a of Scheme VI and as in Sammelson et al. Bioorg. Med. Chem. 2004,12,33453355, the aminopyrazoles of Formula Vd, wherein R1, R2, R3, R4, R6 and X are as previously defined and R5 = H, can be halogenated with a halogen source such as N-chiorosuccinimide or Nbromosuccinlmide In a polar aprotic solvent such as acetonitriie to provide the R5-substituted pyrazole. ln step b, acylation of this compound using the conditions described In Scheme V affords the compound of Formula le, wherein R1, R2, R3, R4, R5, R6, R8 and X are as previously defined.
Scheme VI
In step a of Scheme VII, ureas and carbamates are made from the amlnopyrazoles of Formula Ve. Compounds of Formula Ve, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined are allowed to react with phosgene to provide the intermediate carbamoyi chloride which Is 5 subsequently treated with an amine, as shown in step b, or alcohol, as shown In step c, respectively, to generate a urea of Formula Id or a carbamate of Formula le, respectively, wherein R9 Is as previously defined.
In step a of Scheme VIII, compounds of Formula Xllc, wherein X, R1, R2, R3, R4 and R5 are as previously defined, can be treated with di-fert-butyi dicarbonate (BOC2O) and a base such as 19 triethylamine In a polar aprotic solvent such as dichloromethane (DCM) to yield compounds of Formula XVIa. Treatment of the carbamate functionality with an alkyl halide such as lodomethane or Boc-anhydride In the presence of a base such as sodium hydride and in a polar aprotic solvent such as DMF yields carbamates of Formula XVII, as shown in step b of Scheme VIII, wherein R6 is as previously defined, except where R6 is hydrogen. The Boc-group can be removed under conditions that are well-known In the art, such as under acidic conditions such as trifluoroacetic acid (TFA) in a polar aprotic solvent iike dichloromethane to give compounds of Formula XI llb as in step c.
Scheme VIII
In steps a, b and c of Scheme IX, compounds of Formula Xi ! le, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be treated with a compound of Formula XVIII, wherein R8 Is as previously defined and R10 Is either OH, OR9 or O(C=O)OR9, to yield compounds of Formula Id. When R10 = OH, compounds of Formula XI Ile can be converted to compounds of Formula id in the presence of a coupling reagent such as 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride (EDC-HCI) and a base such as Ν,Ν-dimethylaminopyridine (DMAP) in a polar aprotic solvent such as dichloroethane (DCE), as shown in step a. When R10 = OR9, compounds of Formula Xlllc can be converted to compounds of Formula Id in the presence of
2,3.4,6.7,8-hexahydro-l A7-pyrimido[1,2-aJpyrimidine In a polar aprotic solvent such as 1,4-dioxane under elevated température, as shown in step b. When R10 = O(C=O)OR9, compounds of Formula Xlilc can be converted to compounds of Formula Id In a polar aprotic solvent such as dichloromethane (DCM), as shown in step c. Acylation of amldes of Formula Id, when R6 = H, with 5 an acid chloride In the presence of a base such as diisopropyl ethylamine In a polar aprotic solvent such as dichloroethane (DCE) ylelds Imides of Formula le, as shown In step d. Furthermore, alkylation of amides of Formula Id, when R6 = H, with an alkyl halide in the presence of a base such as sodium hydride in a polar aprotic solvent such as N,N-dimethylformamide (DMF) ylelds alkylated amides of Formula le, as shown In step e. Halogénation of compounds of Formula id, 10 wherein R1, R2, R3, R4, R6, R8 and X are as prevîousiy defined and R5 - H, with a halogen source such as N-bromosucclnimide in a polar aprotic solvent such as DCE or a halogen source such as Mchlorosuccinimlde in a polar aprotic solvent such as DCE or acetonitrile or a halogen source such as Selectfluor® In a mixture of polar aprotic solvents such as acetonitrile and DMF give halogenated pyrazoles of Formula le, wherein R5 = halogen, as shown in step f of Scheme IX. 15 Amides of Formula Id can be converted to thioamides of Formula If In the presence of a thionating agent such as Lawesson's reagent in a polar aprotic solvent such as dichloroethane (DCE), as shown In step g.
Scheme IX
le
If
In step a of Scheme X, compounds of Formula Xllld, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be treated with compounds of Formula XIX, wherein R8 is as previously defined, In a polar aprotic solvent such as dichloroethane (DCE) to yield compounds of Formula XX. Additionally, when R6 = H and R8 contains a halogen, compounds of Formula XX can be treated with a base, such as sodium hydride, in a polar aprotic solvent, such as THF, to yield compounds of Formula XXI, where m is an integer selected from 1,2,3,4, 5, or 6, as shown in step b of Scheme X.
Scheme X
b
Oxidation of the sulfide to the sulfoxide or sulfone Is accomplished as In Scheme XI where (~S~) can be any sulfide previously defined within the scope of R8 of this Invention. The sulfide of
Formula XXIIa, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, Is treated with an oxldant such as sodium perborate tetrahydrate In a polar protic solvent such as glacial acetlc acid to give the sulfoxlde of Formula XXIII as In step a of Scheme XI. Alternative^, the sulfide of Formula XXIIa can be oxidized with an oxidant such as hydrogen peroxide In a polar protic solvent 10 such as hexafluoroisopropanol to give the sulfoxide of Formula XXIII as in step dof Scheme XI.
The sulfoxlde of Formula XXIII can be further oxidized to the sulfone of Formula XXIV by sodium perborate tetrahydrate in a polar protic solvent such as glacial acetic acid as In step c of Scheme XI. Altematively, the sulfone of Formula XXIV can be generated In a one-step procedure from the sulfide of Formula XXIIa by using the aforementioned conditions with >2 équivalents of sodium 15 perborate tetrahydrate, as in step b of Scheme XI.
Scheme XI
XXIV
Oxidation of the sulfide to the sulfoximine is accomplished as In Scheme XII where (~S~) can be any sulfide previously defined within the scope of R8 of this invention. The sulfide of Formula XXI Ib, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, is oxidized as In step a with lodobenzene dîacetate In the presence of cyanamide in a polar aprotic solvent such as methylene chloride (DCM) to give the sulfilimine of the Formula XXV. The sulfilimine of Formula XXV may be 10 further oxidized to the sulfoximine of Formula XXVI with an oxidant such as metaChloroperoxybenzolc acid (“mCPBA) in the presence of a base such as potassium carbonate in a protic polar solvent System such as éthanol and water as in step b of Scheme XII.
Scheme XII
r5 r3 xxv
XXIIb r3
XXVI lodination of the pyrazole of Formula Xb as in step a of Scheme XIII and as in Potapov, A.
et al. Russ. J. Org. Chem. 2006,42,1368-1373 was accomplished by reaction with an lodinating agent such as iodine In the presence of acids such as iodic acid and sulfuric acid In a polar protic solvent such as acetic acid gives compounds of Formula XXVII. In step b of Scheme XIII and as In Wang, D. et al. Adv. Synth. Catal. 2009, 351,1722-1726, amlnopyrazoles of Formula Xille can be prepared from lodopyrazoles of Formula XXVII through cross coupling reactions with an appropriate amine In the presence of a base such as césium carbonate, a copper catalyst such as copper (I) bromide, and a ligand such as 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone In a polar aprotic solvent such as DMSO.
Scheme XIII
XI Ile
In step a of the Scheme XIV, compounds of the formula XXIX, wherein R4 is Cl, R5 Is H and X* represents Ci', can be prepared according to the methods described In Acta. Pharm. Suec. 22, 147-156 (1985) by Tolf, Bo-Ragnar and Dahlbom, R. In a similar manner, compounds of the Formula XXIX, wherein R4 is Br, X represents Bf and R5 Is as defined previously, can be prepared by treating compounds of the Formula XXVIII with hydrogen gas in the presence of a métal catalyst such as 5% Pd on alumina and a solution of 50% aqueous HBr in a solvent such as éthanol. Alternativeiy, In step a of Scheme XIV, compounds of the Formula XXIX, wherein R4 is Cl or Br, X* represents CI or Bf and R5 Is as defined previously, can be prepared by treating compounds of the Formula XXVIII, wherein R5 is as defined previously, with a hydrosilane such as triethyl silane In the presence of a métal catalyst such as 5% Pd on alumina and an acid such as HCI or HBr, respectively, In a solvent such as éthanol.
In step b of the Scheme XIV, compounds of the Formula XXX, wherein R4 Is Cl or Br and R5 is as defined previously, can be prepared by treating the compounds of the Formula XXIX, wherein R4 Is Ci or Br, Xrepresents CI* or Bf and R5 Is as defined previously, with di-fert-butyl dicarbonate (BocîO) In the presence of a mixture of solvents such as THF and water and a base such as sodium bicarbonate.
In step c of the Scheme XIV, compounds of the Formula XVIa, wherein X, R1, R2, R3 and
R5 are as defined previously and R4 is Cl or Br can be obtained by treating compounds of the Formula XXX, wherein R4 Is Cl or Br and R5 is as defined previously, with compounds of the Formula Vlllb, wherein X, R1, R2 and R3 are as defined previously and Q Is bromo or iodo, in the presence of a catalytic amount of copper sait such as CuCI2, an ethane-1,2-diamlne dérivative such 5 as N\N2-dimethylethane-1,2-diamlne and a base such as K3PO4 in a polar aprotic solvent such as acetonitriie at a suitable température.
The Boc-group of compounds of Formula XVIa can be removed under conditions that are well-known in the art such as under addic conditions such as TFA in a polar aprotic solvent such as dichloromethane to give compounds of Formula Xlld, as shown in step dof Scheme XIV.
Scheme XIV
r3
XXVIII
XVIa
Bromopyrazoles of Formula XXXI, wherein R1, R2, R3, R5, R8 and X are as previously defined, can be allowed to react under Suzuki coupling conditions with a boronic ester such as vinylboronlc acid plnacol ester or cyclopropylboronlc acid pinacol ester in the presence of a catalyst such as palladium tetrakis, a base such as 2 M aqueous potassium carbonate, and In a mixed 5 solvent system such as éthanol and toluene to provide compounds of Formula XXXII, as shown in step a of Scheme XV.
Scheme XV
XXXI
XXXII
The vinyl group of compounds of Formula XXXIII, wherein R1, R2, R3, R5, R6, R8 and X are as previously defined, can be reduced in the presence of hydrogen with a catalyst such as 10% Pd/C in a polar protic solvent such methanol to give compounds of Formula XXXIV, as shown in step a of Scheme XVI. Oxldation of the vinyl group of compounds of Formula XXXIII using an 15 oxldant such as osmium tetroxide in the presence of sodium periodate in mixture of a polar protic solvent such as water and a polar aprotic solvent such as THF gave compounds of Formula XXXV, as shown in step b of Scheme XVI. Réduction of the aldéhyde of compounds of Formula XXXV, as shown In step c of Scheme XVI, with a redudng agent such as sodium borohydrlde in a polar protic solvent such as methanol gave the corresponding alcohol of Formula XXXVI. Treatment of compounds of Formula XXXVI with a chlorinating agent such as thionyl chloride in a polar aprotic solvent such as dichloromethane gave compounds of Formula XXXVII, as shown In step dof Scheme XVI.
Scheme XVI
Rj
XXXIII
b
XXXV
XXXVII
In step a of Scheme XVII, an □.□-unsaturated acid XXXVIII can be treated with a nucieophile such as sodium thiomethoxide In a polar protic solvent such as methanol to give acid XXXIX.
In Step a of the Scheme XVIII, treatment of the compounds of Formula Ig, where A Is A2, R7 Is O and R8 Is tert-butoxy with a reagent such as propargyl bromide In the presence of a base such as sodium hydride and In a polar aprotic solvent such as DMF yields compounds of Formula Ih, wherein R6 = R11.
Scheme XVIII
Ih
Ig
Sulfonamide compounds of Formula li, wherein (-N) can be any amine defined within the scope of R8 of this invention, can be prepared through steps a, b, and c illustrated in Scheme XIX. In step a, acylation of compounds of Formula Xlllf according to methods described in Scheme IX affords compounds of Formula XXXX, wherein R1, R2, R3, R4, R5, R9, X, and where R6 = R11 are as previously defined. Removal of the Boc group of compounds of Formula XXXX, depicted In step b, can be achieved using the conditions described in Scheme XIV to give compounds of Formula XXXXI, wherein R1, R2, R3, R4, R5, R9, X, and where R6 = R11 are as previously defined. Compounds of Formula XXXXI can be treated with sulfonyl chlorides of Formula XXXXII such as methanesulfonyl chloride in the presence of a base such as diisopropylethylamine In a polar aprotic solvent such as dichloromethane to give compounds of Formula li, as shown in step c of Scheme XIX
Scheme XIX
XIHf xxxx
XXXXII
EXAMPLES
The examples are for illustration purposes and are not to be construed as limiting the invention disclosed in this document to oniy the embodiments disclosed in these examples.
Starting materiais, reagents, and solvents that were obtained from commercial sources were used without further purification. Anhydrous solvents were purchased as Sure/Seal™ from Aldrich and were used as received. Melting points were obtained on a Thomas Hoover Unimelt 10 caplllary melting point apparatus or an OptiMelt Automated Melting Point System from Stanford Research Systems and are uncorrected. Molécules are given their known names, named according to naming programs within ISIS Draw, ChemDraw or ACD Name Pro. If such programs are unable to name a molécule, the molécule Is named using conventional naming rules. Ail NMR shifts are In ppm (δ) and were recorded at 300,400 or 600 MHz unless otherwise stated.
Example 1, Step 1: Préparation of 3,3-bls-methylsulfanyl-1-pyrldln-3-y!-propenone
To a room-temperature suspension of sodium hydride (NaH, 60% suspension In minerai oil; 4.13 g, 86 mmol) in dry dimethyl sulfoxide (DMSO. 60 mL) under an atmosphère of nitrogen (N2) was added 3-acetylpyridine (5.00 g, 41.3 mmol) dropwise over 30 minutes (min). The mixture was stirred for an additional 30 minutes at the same température. Carbon disulfide (CS2; 3.27 g, 43 mmol) was added dropwise with vigorous stirring followed by lodomethane (12.21 g, 86 mmol) dropwise over a period of 45 min. Stirring was continued for an additional 18 hours (h) under N2. The reaction was quenched with cold water (H2O, 50 mL). The dark solid was filtered and washed with ice-cold ethyl alcohol (EtOH) until the washlngs were colorless. The off-white solid product was dried under vacuum at 60 *C to provide 3,3-bis-methylsulfanyl-1-pyridin-3-yl-propenone as a brown solid (4.8 g, 51 %): 1H NMR (300 MHz, CDCI3) □ 9.13 (d, J = 1.8 Hz, 1H), 8.72 (dd, J = 4.8,
1.6 Hz. 1H), 8.23 (ddd, J = 7.9, 2, 2 Hz, 1H), 7.40 (dd, J = 7.9,4.8 Hz, 1 H). 6.73 (s, 1H), 2.58 (d, J = 9.4 Hz, 6H); MS m/z 226.2 (M+1 ).
1-(5-fluoropyrldin-3-yl)-3,3-bis(methylthio)prop-2-en-1-one was prepared as described in Example 1, Step 1: mp 150-152 ’C; 1H NMR (400 MHz, CDCI3) δ 8.93 (t, J = 1.6 Hz, 1 H), 8.58(d, J = 2.8 Hz, 1 H),7.94 (ddd, J = 8.9, 2.8, 1.7 Hz, 1H)„ 6.69 (s, 1 H). 2.60 (s, 3H), 2,57 (s, 3H).
Example 1, Step 2: Préparation of (Z)-3-methyiamlno-3-methylsulfanyl-1-pyridin-3-ylpropenone
A solution of 3,3-bis-methylsulfanyl-1-pyridin-3-yl-propenone (18.6 g, 82.5 mmol) In absolute alcohol (400 mL) under N2 was treated with methylamine hydrochloride (27.86 g, 412 mmol) followed by triethylamine (Et3N; 58.5 mL, 412 mmol). The mixture was heated to reflux for 3 h, cooled to room température and concentrated under reduced pressure. The solid residue was dissolved In ethyl acetate (EtOAc; 150 mL). The solution was washed with H2O (2 x 50 mL) and brine (50 mL), dried over Na2SO«, concentrated under reduced pressure and purified by silica gel chromatography eluting with 10% EtOAc In petroleum ether to yield (Z)-3-methylamino-3methylsuifanyl-1-pyridin-3-yl-propenone as a pale yellow solid (8.6 g, 50%): 1H NMR (300 MHz,
CDCIj) □ 11.8 (brs, 1H), 9.06 (s, 1H); 8.67 (d, J- 3.9 Hz, 1H). 8.26 (d, J= 8.0 Hz 1H), 7.46 (dd, J
- 7.6,4.9 Hz 1H), 5.62 (s, 1H), 3.10 (d, J - 5.2 Hz, 3H), 2.52 (s, 3H); MS (m/z) 209.2 [M+1 ].
(Z)-3-(ethylamlno}-3(methylthlo)-1-(pyridin-3-yl)prop-2-en-1-one was prepared as described in Example 1, Step 2: Ή NMR (400 MHz, CDCI3) δ 11.81 (bs, 1 H). 9.04 (dd, J = 2.2, 0.7 Hz, 1H), 8.64 (dd, J= 4.8,1.7 Hz, 1H), 8.29-7.98 (m, 1H), 7.35 (ddd, J = 7.9,4.8, 0.9 Hz, 1H), 3.45 (q, J- 7.2,
5.6 Hz, 2H), 2.50 (s, 3H), 1.35 (t, J= 7.2 Hz, 3H).
(Z)-3-(cyclopropylmethyl)amlno-3(methylthlo)-1-(pyridin-3-yl)prop-2-en-1-one was prepared as described In Example 1, Step 2:1H NMR (400 MHz, CDCI3) δ 9.00 (s, 1 H), 9.05 (dd, J =2.2, 0.7 Hz, 1H), 8.64 (dd, J- 4.8,1.7 Hz, 1H), 8.16 (dt, J = 7.9, 2.0 Hz, 1H), 7.35 (ddd, J =7.9, 4.8, 0.8 Hz, 1 H), 5.62 (s, 1 H), 3.27 (dd, J = 7.0, 5.5 Hz, 2H), 2.50 (s, 3H), 1.20 -1.07 (m, 1 H), 0.73 - 0.49 (m, 2H), 0.41-0.17 (m,2H).
Example 1, Step 3; Préparation of methyl-(2-methyl-5-pyrldin-3-pyrazol-3-yl)-amine
A solution of (Z)-3-methylamlno-3-methylsulfanyl-1-pyridin-3-yl-propenone (3.00 g, 14 mmol) and methylhydrazine (729 mg, 15.4 mmol) ln absolute EtOH (64 mL) was stirred at reflux for 18 h under N2, cooled to room température and evaporated under reduced pressure. The residue was dissolved In EtOAc (50 mL), and the organic layer was washed with H2O (2 x 30 mL) and brine (30 mL), dried over Na2SO4l concentrated under reduced pressure and purified using silica gel chromatography eluting with a gradient of 0-1% EtOH In EtOAc to yield two regloisomers ln a 1:2 ratio, with the major regloisomer as a brown solid (1.0 g, 27%): 1H NMR (300 MHz, CDCI3) □ 8.97 (d, J = 1.3 Hz, 1 H), 8.51 (dd, J = 3.6,1.0 Hz, 1 H), 8.07 (ddd, J = 5.9,1.4,1.4 Hz, 1 H), 7.30 (dd, J =
5.9, 3.6 Hz, 1H), 5.82 (s, 1H), 3.69 (s, 3H), 2.93 (s, 3H); MS (m/z) 188.6 [M+1j.
1-Ethyl-N-methyl-3-(pyridin-3-yl)-1H-pyrazol-5-amlne was prepared as described ln Example 1,
Step 3: ESIMS m/z 204 ([M+2H]).
N-ethyl-1-methyl-3-(pyridin-3-yl)-1/7-pyrazol-5-amine was prepared as described In Example 1, Step 3: ESIMS m/z 203 ([M+H]).
N-methyl-1-phenyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine was prepared as described In Example 1, Step 3: ESIMS m/z 252 ([M+2H]).
N-(cyclopropylmethyl)-1-methyl-3-(pyridîn-3-yl)-1H-pyrazol-5-amine was prepared as described In Example 1, Step 3: ESIMS m/z 230 ([M+2H]).
1-lsopropyl-N-methyl-3-pyridîn-3-yl)-1H-pyrazol-5-amlne was prepared as described In Example 1, Step 3: Ή NMR (300 MHz, CDCI3) δ 8.53 (s, 1 H), 8.06 - 7.90 (m, J = 7.2 Hz, 2H), 7.13 (dd, J = 7.9,
5.6 Hz, 1H), 5.33 (s, 1H), 3.70 (bs, 1H), 3.65 (dt, J~ 13.2, 6.6 Hz, 1H), 2.31 (s, 3H), 0.88 (d, 6.6
Hz, 6H); ESIMS 217 ([M+H]).
3-(5-Fluoropyridin-3-yl)-N, 1-dimethyl-1H-pyrazol-5-amine was prepared as described In Example 1, Step 3: Ή NMR (300 MHz, CDCI3) δ 8.28 (s, 1H), 7.87 (t, J= 1.3 Hz, 1H), 7.60 (m, 1 H). 6.66 (s, 1H), 5.28 (bs, 2H), 3.12 (s. 3H), 2.34 (s, 3H); ESIMS m/z 206 ([M+H])
Example 2: Préparation of (4-chloro-2-methyl-5-pyridln-3-yl-2H-pyrazol-3-y!)-methyl-amlne .H
Cl
A mixture of methyl-(2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-amine (0.35 g, 1.8 mmol) and Nchlorosuccinimide (0.273 g, 2 mmol) was combined In acetonitrile (3 mL), stirred at room température for 30 minutes, concentrated under reduced pressure and purified using silica gel chromatography eluting with a gradient of EtOAc In hexanes to yield the title compound as a yellow oil (0.096 g, 23%): IR (thin film) 1581.6 cm·1; 1H NMR (400 MHz, CDCI3) □ 9.12 (d, 1.5 Hz, 1H),
8.57 (dd, J = 4.8,1.3 Hz, 1 H), 8.15 (ddd, J = 7.8, 2.0, 2.0 Hz, 1 H), 7.33 (dd, J = 8.1, 5.1 Hz, 1 H),
3.80 (s, 3H), 2.91 (d, J= 5.8 Hz, 3H); ESIMS (m/z) 225.6 [M+2J.
The reaction also gave 4-chloro-2-methyl-5-pyridin-3-yl-2H-pyrazol-3-y!amine as a green gum (0.046 g, 13%): IR (thin film) 1720.5 cm'1.; Ή NMR (CDCI3,400 MHz) DD9.13 (brs, 1H), 8.57 (br s, 1H), 8.16 (dt, J = 8.0, 2.0 Hz, 1H), 7.33 (dd, J= 7.8,4.8 Hz, 1H), 3.76 (s, 3H); ESIMS (m/z) 207.0 [M-1].
Example 3: Préparation of 2,N-dlmethyl-N-(2-methyl-5-pyrldln-3-yl-2H-pyrazol-3-yl)-3methylsulfanyl-propionamide (Compound 1)
To a solution of methyl-(2-methyi-5-pyridin-3-yl-2H-pyrazol-3-yl)-amine (150 mg, 0.8 mmol) under N2 In Ice-cold dichloroethane (DCE; 2 mL) was added dropwise via pipette a solution of 2-methyl-3methyisulfanyl-proplonylchloride (146 mg, 0.9 mmoi) In DCE (1.5 mL). After stirring for 10 minutes (min), a solution of 4-N,N-dîmethylamlnopyridine (DMAP; 107 mg, 0.9 mmol) In DCE (2 mL) was added dropwise. The Ice bath was removed after 30 min, and the mixture was stirred at room température for 90 min and then at reflux for 14 h. The mixture was concentrated under reduced pressure and was purified by silica gel chromatography eluting with a gradient of EtOAc in hexane. The product, 2,N-dimethyl-N-(2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-3-methylsulfanylpropionamide, was isolated as a yellow semi-solid (44 mg, 24%): 1H NMR (400 MHz, CDCI3) □ 9.00 (s, 1H), 8.58 (s, 1H). 8.08 (brd. J= 7.0 Hz, 1H), 7.35 (brdd, J- 7.3,4.8 Hz, 1H), 6.58 (brs,
0.5 H). 6.49(brs, 0.5 H), 3.89-3.79 (m, 3H), 3.25 (s, 3H), 2.96-2.80 (m, 1H), 2.42-2.40 (m, 1H), 2.02-1.99 (m, 3H), 2.62 (m, 1 H). 1.15 (d, J = 6.0 Hz, 3H); MS (m/z) 305.0 [M+1J.
Compounds 2-6,9-10,12,18 - 21, 24 - 33, 477, 487, 509, 520, 556-557, 562-568 were made from the appropriate amines In accordance with the procedures dîsclosed In Example 3.
Example 4: Préparation of 1-methyi-1-(2-methyi-5-pyridln-3-yI-2H-pyrazoi-3-yI)-3-(2methylsulfanyl-ethyl)-urea (Compound 7)
To a solution of methyl-(2-methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-amine (150 mg, 0.8 mmol) in icecold DCE (2 mL) under N2 was added a solution of phosgene In toluene (20%, 0.43 mL, 0.88 mmol). The ice bath was removed after 30 min, and the mixture was stirred at room température for 1 h and at reflux for 2 h. The mixture was cooled to room température and then more phosgene (0.86 mL, 1.76 mmol) was added. The mixture was stirred at reflux for 90 mtn and then cooled in an Ice bath. To this was added a solution of 2-methylthloethylamine (80 mg, 0.88 mmol) in DCE (2 mL). The ice bath was removed after 10 min, and the reaction mixture was stirred at reflux for 14 h, cooled, and diluted with DCE (30 mL). The diluted reaction mixture was washed with saturated NaHCOa (20 mL), dried over MgSO<, adsorbed onto silica gel and purified using silica gel chromatography eluting with a gradient of methanoi in dichioromethane to afford 1-methyl-1-(2methyl-5-pyridin-3-yl-2H-pyrazol-3-yl)-3-(2-methylsulfanyl-ethyl)-urea as a yellow gum (14 mg, 6%): ’H NMR (400 MHz, CDCI3) □ 8.99 (d, J = 1.5 Hz, 1 H), 8.57 (dd, J - 4.8,1.5 Hz, 1 H), 8.08 (ddd, J =
8.1,2.1, 2.1 Hz, 1 H), 7.34 (dd, J = 7.9, 4.8 Hz, 1 H), 6.52 (s, 1 H), 4.88 (br t, J = 5.5 Hz, 1 H), 3.80 (s, 3H), 3.41 (q, J- 6.3 Hz, 2H), 3.24 (s, 3H), 2.61 (t, J= 6.3, 2H), 2.06 (s, 3H); ESIMS (m/z) 292.2 [M+2].
Compound 8 was made In accordance with the procedures disclosed in Example 4 using
2-(methylthio)ethanol in place of 2-methylthloethylamine.
Example 5: Préparation of 1-methyl-5-(pyrldln-3-yl)-1H-pyrazoi-3-amine and 1-methyl-3(pyrldln-3-yl)-1 H-pyrazol-5-amlne
To éthanol (8.53 mi) was added 3-oxo-3-(pyridin-3-yl)propanenitrile (0.82 g, 5.61 mmol) and methylhydrazine (0.25 g, 5.61 mmol) and stirred at reflux for 2 hours. The reaction was cooled to room température and concentrated to dryness. The crude material was purified by silica gel chromatography by eluting with 0-20% MeOH / dichloromethane to yield two products - 1-methyl-5(pyridin-3-yl)-1H-pyrazol-3-amine (0.060 g; 6.14%): 1H NMR (300 MHz, CDCI3) □ 8.72 (s. 1H). 8.53 (d, 1H), 7.76-7.63 (m, 1H), 7.43-7.33 (m, 1H), 5.75 (s, 1H), 3.76-3.57 (m, 5H) and 1-methy!-3(pyridin-3-yl)-1H-pyrazol-5-amine (0.150 g. 15.35%): Ή NMR (300 MHz, CDCI3) δ 8.88 (s. 1H), 8.48 (d. 1H), 7.99 (d. 1H), 7.38-7.07 (m, 1H), 585 (s, 1H), 3.80-3.59 (m, 5H).
Example 6, Step 1: Préparation of 3-pyrazol-1-yl-pyridlne
To a solution of 3-bromopyridine (5 g, 0.031 mol) In 50 ml of acetonitriie were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxlme (0.867 g, 0.006 mol) under N2 atmosphère. The reaction mass was refluxed for 24 hrs at 80 °C. The réaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43 %): 1H NMR (400 MHz, CDCI3) □ 8.99 (d, J= 2.8 Hz, 1 H), 8.48 (dd, J- 4.8,1.2 Hz, 1H), 8.11 - 8.08 (m, 1 H), 7.99 (d, J = 1.2 Hz, 1 H), 7.78 (d, J = 1.2 Hz, 1 H). 7.38 - 7.35 (m. 1 H), 6.53 (t, J - 1.2 Hz. 1 H): MS (m/z) 146 [M+1].
3-(3-chloro-1H-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 1: mp 98-106 *C; 1H NMR (400 MHz, CDCI3) δ 8.93 (d, J - 2.6 Hz. 1H), 8.57 (dd, J= 4.8,1.4 Hz. 1H), 8.03 (ddd. J = 8.3. 2.7,
1.5 Hz. 1 H), 7.90 (d, J = 2.5 Hz. 1 H), 7.42 (ddd. J = 8.3, 4.8, 0.7 Hz, 1 H), 6.46 (d, J = 2.5 Hz, 1 H);
13C (DMSO-cfe) 148,142,140,136,131,126,125,108.
2- methyl-3-(3-methyl-1H-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 1:1H NMR (400 MHz, CDQ3) δ 8.53 (d, J = 4.7 Hz, 1H), 7.67 (d, J= 7.9 Hz, 1H), 7.54 (t, J= 8.0 Hz, 1H), 7.27 7.19 (m, 1H), 6.27 (d, J - 1.4 Hz, 1H), 2.53 (s, 3H), 2.38 (s, 3H).
3- (3-(Trifluoromethyl)-1H-pyrazol-1-yl)pyridine was prepared from the appropriate starting materials as described in Example 6, Step 1.: mp 59.0-61.0 ’C; 1H NMR (400 MHz, CDCI3) δ 9.00 (s, 1H), 8.70 - 8.59 (m, 1H), 8.11 (ddd, J = 8.3, 2.7,1.5 Hz, 1 H), 8.05 - 7.98 (m, 1 H), 7.46 (dd, J= 8.3,4.8 Hz, 1H), 6.79 (d. J- 2.4 Hz, 1 H); EIMS m/z213.
3-Fluoro-5-(3-methyMH-pyrazol-1-yl)pyridine was prepared from the appropriate starting materials as described in Example 6, Step 1 : mp 70.0-72.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.76 - 8.73 (m, 1 H). 8.37 - 8.33 (m, 1H), 7.88-7.85 (m, 1H), 7.84 - 7.79 (m, 1H), 6.34 - 6.29 (m, 1 H), 2.37 (s, 3H); EIMS m/z 177.
3-(3-Chloro-1H-pyrazol-1-yl)-5-fluoropyrîdine was prepared from the appropriate starting materials as described in Example 6, Step 1: mp 77.0-82.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.75 (d, J = 1.8 Hz, 1H), 8.43 (d, J- 2.3 Hz, 1H), 7.92 (d, J- 2.6 Hz, 1H), 7.84 (dt, J = 9.3, 2.4 Hz, 1H), 6.48 (d, J~
2.6 Hz, 1H); EIMS m/z 198.
3-(3-methyl-1H-pyrazol-1-yl)pyridine was prepared as described ln Example 6, Step 1:
3H NMR (400 MHz, CDCI3) δ 8.94 (bs, 1 H). 8.51 (d, J- 3.9 Hz, 1H), 8.02 (ddd, J- 8.3, 2.6,1.5 Hz, 1H), 7.90-7.79 (m, 1H), 7.39 (dd, J= 8.2, 5.1 Hz, 1H). 6.30 (d, J - 2.4 Hz. 1H), 2.39 (s, 3H).
3-(5-methyl-1H-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 1:1H NMR (400 MHz, CDQ3) δ 8.77 (d, J = 2.5 Hz, 1 H), 8.65 (dd, J = 4.8,1.5 Hz, 1 H), 7.84 (ddd, J = 8.2,2.5,1.5 Hz, 1 H), 7.63 (d, J - 1.6 Hz, 1 H), 7.44 (ddd, J = 8.2,4.8, 0.7 Hz, 1 H), 6.225 (dd, J = 1.6, 0.7 Hz, 1 H), 2.40 (s, 3H).
Example 6, Step 2: Préparation of 3-(4-nltro-pyrazoM-yl)-pyrldlne
N=\
U N
3-Pyrazol-1-yl-pyridine (2 g, 0.032 mol) was dissolved In concentrated H2SO4 (32 mL 0.598 mmol.) and cooled to -5 °C using an ice bath. To the reaction mass, a 1:1 mixture of concentrated HNO3 (30 mL, 0.673 mmol) and concentrated H2SO4(30ml, 15 Vol.) was added dropwise over a period of 30 min. Cooling was discontinued and the reaction mixture was stirred at room température overnight. After the reaction was complété, the mixture was poured overcrushed ice and neutralized with saturated NaHCO3, filtered, washed with water and dried to fumish the nitro pyrazole as pale yellow solid (1.8 g, 68%): ’H NMR (400 MHz, DMSO-de) □ 9.03 (d, J - 2.8 Hz, 1H): 8.70 (dd, J= 4.8,1.6 Hz, 1H), 8.69 (s, 1H), 8.33 (s, 1H), 8.11 - 8.08 (m, 1H), 7.51 (dd, J= 8.4,
4.8 Hz, 1H); MS (m/z) 191 [M+1],
3-(3-chloro-4-nitro-1H-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 2: mp 139-142 *C, ’H NMR (400 MHz, CDCI3) δ 9.01 (d, J= 2.0 Hz, 1H), 8.73 (d, J= 4.9 Hz, 2H), 8.08 (ddd, J= 8.3,
2.5,1.3 Hz, 1 H), 7.52 (dd, J = 8.3, 4.8 Hz, 1 H), EIMS m/z 224.
3-(5-methyl-4-nitro-lH-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 2: ’H NMR (400 MHz, CDCi3) δ 8.81 - 8.71 (m, 2H), 8.32 (s, 1H). 7.83 (ddd, J = 8.2, 2.5,1.6 Hz, 1H), 7.54 (dd, J =
8.2, 4.8 Hz, 1H), 2.72(s, 3H).
2- methyl-3-(3-methyl-4-nitro-1H-pyrazol-1-yl}pyridÎne was prepared as In Example 6, Step 2: ’H NMR (400 MHz, de-DMSO) δ 14.01 (s, 1H), 9.37 (d, J= 4.0 Hz, 1H), 8.69 (t, J= 17.3 Hz, 1H), 8.21 (dd. J = 7.7,4.8 Hz, 1H). 2.29 (s, 3H), 2.20 (s, 3H); .’3C 154,150,146,135,134.9,134.8,134.3, 122, 21,14; EIMS m/z 218.
3- (3-methyl-4-nitro-1H-pyrazol-1-yl)pyridine was prepared as in Example 6, Step 2: mp 122 -124 •C; ’H NMR (400 MHz, CDCi3) δ 9.01 (d, J- 2.5 Hz, 1H), 8.77-8.56 (m. 2H), 8.07 (ddd, J - 8.3,
2.7,1.5 Hz, 1 H), 7.56 - 7.37 (m, 1 H), 2.66 (s, 3H); EIMS m/z 208.
3-Fluoro-5-(3-methyl-4-nitro-1H-pyrazol-1-y!)pyridine was prepared from the appropriate starting material as described in Example 6, Step 2: mp 90.0-92.0 °C; 1H NMR (400 MHz, CDCI3) δ 8.82 (d, J = 2.0 Hz, 1H), 8.69 (s, 1 H), 8.54 (d, J = 2.5 Hz, 1 H). 7.89 (dt, J= 8.9,2.4 Hz. 1H), 2.66 (s, 3H); EIMS m/z 222.
3-(4-Nitro-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine was prepared from the appropriate starting material as described in Example 6, Step 2: mp 121.0-123.0 ’C; 1H NMR (400 MHz, CDCI3) δ 9.04 (d, J= 2.5 Hz, 1H). 8.79 (s, 1 H), 8.77 (d, J= 0.9 Hz, 1H), 8.13 (ddd, J = 8.3,2.7,1.4 Hz, 1 H), 7.55 (dt, J = 10.8, 5.4 Hz, 1 H); EIMS m/z 258.
3-(3-Chloro-4-nitro-1H-pyrazol-1-y!)-5-fluoropyridine was prepared from the appropriate starting material as described in Example 6, Step 2: mp 109.5-111.0 *C; 1H NMR (400 MHz, CDCI3) δ 8.83 (d, J = 2.1 Hz, 1H), 8.75 (s, 1H), 8.60 (d, J =2.4 Hz, 1H), 7.89 (dt, J = 8.6,2.4 Hz, 1H); EIMS m/z 242.
3-(3-Bromo-4-nitro-1H-pyrazol-1-yl)pyridine was prepared from the appropriate starting material as described in Example 6, Step 2: mp 139.0-141.0 °C; 1H NMR (400 MHz, CDCI3) δ 9.01 (d, J= 2.5 Hz, 1H), 8.73 (dd, J = 4.7,1.1 Hz, 1 H), 8.71 (s, 1 H), 8.15 - 8.00 (m, 1H), 7.52 (dd, J = 8.3, 4.8 Hz, 1H); ESIMS m/z 271 ((M+2f).
Example 6, Step 3: Préparation of 1-pyrldln-3-yl-1H-pyrazol-4-y!amlne
To a solution of 3-(4-nltro-pyrazol-1-yl)-pyridine (1.8 g, 0.009 mol) in dry THF (18 ml) was added 5% Pd/C (180 mg) under nitrogen atmosphère. The mixture was then stirred under hydrogen atmosphère until the reaction was complété. The reaction mixture was filtered through a pad of celite, and concentrated to dryness to give an Impure dark brown solid (1.76 g): 1H NMR (400 MHz, DMSO-de) □ 8.89 (dd, J = 2.8. 0.4 Hz, 1 H); 8.48 (dd, J = 4.8,1.2 Hz, 1 H), 7.99 - 7.96 (m, 1 H), 7.54 (d, J = 1.2 Hz, 1H), 7.45 (d, J = 0.4 Hz, 1H), 7.38-7.35 (m, 1H). 4.81 (bs 1H); ESIMS (m/z) 161 [M+1J.
5-methy!-1-(pyridin-3-y!)-1H-pyrazol-4-amine was prepared as in Example 6, Step 3: 1H NMR (400 MHz, CD Cl 3) δ 8.74 (d, J = 2.3 Hz, 1H), 8.63-8.50 (m, 1H), 7.81 (ddd. J - 8.2, 2.5,1.5 Hz, 1H), 7.46-7.33 (m, 2H), 2.64 (bs, 1H),, 2.29 (s, 3H); 13C(DMSO-cfe) 147,144,137, 133, 130, 129,124, 123,10; EIMSm/z174
3-methyl-1-(pyrimidin-5-yl)-1/+pyrazol-4-amine was prepared as In Example 6, Step 3: mp 211-215 eC; 1H NMR (400 MHz, CDCI3) δ 9.10-8.87 (m, 3H), 7.51 (s, 1H), 3.24 (bs, 2H), 2.29 (s, 3H);
ESI MS m/z 176 ([M+H]).
3-chloro-1-(pyrimidin-5-yl)-1H-pyrazol-4-amine was prepared as In Example 6, Step 3: mp 146-148 •C; Ή NMR (400 MHz, CDCI3) δ 9.07 (s, 1H), 9.02 (s, 2H), 7.52 (s, 1 H), 3.45 (s, 2H); ESIMS m/z 196 ([M+H]).
Example 7: Préparation of methyl-(1-pyrldln-3-yl-1H-pyrazol-4-yl)-amlne
Method A:
To a 25 ml round bottom flask containing 1-pyridin-3-yl-1H-pyrazol-4-ylamlne (1.76 g, 0.011 mol) In éthanol (26,4 ml) was added benzotriazole (1.31 g, 0.011 mol). The réaction was cooled to 0°C 10°C and formaldéhyde (0.36 mL, 0.0121 mol) was added slowly and kept for 30 min at this température. The réaction was filtered and concentrated to dryness. The crude material (2.56 g,
0.009 mol) was dissolved in dry tetrahydrofuran (25.6 mL), cooled to 0°C and sodium borohydride (0.326 g, 0.00882 mol.) was added over 15 min. The reaction was warmed to room température and stirred for 2 hours. The reaction was poured into water and extracted using dichloromethane, the organic layer was dried over anhydrous Na2SO« and concentrated to dryness. Purified the crude material by silica gel chromatography eluting with 20% methanol / chloroform to afford the desired product as a brown solid (0.610 g, 32 %): 1H NMR (400 MHz, de-DMSO) □ 8.92 (d, J- 2.4 Hz, 1H), 8.47 (dd, J-4.8, 1.6 Hz, 1H), 8.01 - 7.98 (m, 1H). 7.45 (s. 1H), 7.30 (s, 1H), 7.37 (dd, J = 8.0, 4.4 Hz, 1H), 2.84 (s, 3H); ESIMS m/z 175 ([M+1]).
Method B:
1-pyridin-3-yl-1H-pyrazol-4-ylamine (1.0 g, 6.2 mmol) was dissolved In triethyî orthoformate (5 ml, 30 mmol) and to that was added trifluoroacetic acid (3-4 drops). The reaction mixture was refluxed at 120*C for 3 hours and was then concentrated. The crude was dissolved In éthanol (5 ml), cooled to 0eC and treated with sodium borohydride (0.6 g, 15.7 mmol). After warming to room température, the mixture was refluxed for 3 hours. The mixture was concentrated and the residue was suspended between water and diethyl ether. The diethyl ether layer was separated and concentrated to dryness. The crude material was purifîed by silica gel chromatography, eluting with
5% methanol / chloroform to afford the desired product as a pale yellow solid (0.3 g, 27%): mp 65 67 eC; ’H NMR (300 MHz, CDCI3) δ 8.91 (bs, 1H), 8.46 (d, J= 4.5 Hz, 1H). 7.99 (d, J= 8.3 Hz, 1H), 7.43 (s, 1H), 7.41 (s, 1H), 7.36 (dd, J= 8.3, 4.7 Hz, 1H), 2.86 (d, J = 12.4 Hz, 3H); ESIMS m/z 175 ([M+1]).
Example 8: Préparation of ethy!-(1-pyridln-3-y!-1H-pyrazol-4-yl)-amlne
Method A:
To 1-pyridin-3-yl-1H-pyrazol-4-ytamine (0.5 g, 3.12 mmol) In dichloromethane (5 ml) was added acetyl chloride (0.28 g, 3.75 mmol) followed by DMAP (0.57 g, 4.68 mmol) and stirred at room température for 3 hours. The reaction mixture was concentrated and purifîed by silica gel column chromatography. The recovered material was dissolved in tetrahydrofuran (5ml) and lithium alumlnum hydride (0.23 g, 6.25 mmol) was added and stirred at room température for 12 hours.
The reaction was quenched with saturated NazSO^ and filtered through celite. The filtrate was collected and concentrated to dryness. The crude material was purifîed by silica gel column chromatography eluting with 0-5% methanol / chloroform and resubjected to silica gel chromatography, eluting with 0-100% ethyl acetate / hexanes) to give the desired product (0.080 g, 14%): 1H NMR (400 MHz, CDCI3) δ 8.90 (d, J = 2.7 Hz, 1H), 8.46 (dd, J = 4.7,1.3 Hz, 1H), 7.98 (ddd, J = 8.3,2.6,1.5 Hz, 1 H), 7.41 (dt, J = 13.3,6.6 Hz, 2H), 7.36 (ddd, J = 8.3, 4.7, 0.7 Hz, 1 H),
3.10 (q, J = 7.1 Hz, 2H), 1.27 (t, 3H).
Method B:
To a solution of tert-butyl ethyl(1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (3.4 9,11.79 mmol) In dichloromethane (4.54 ml) was added trifluoroacetic add (9 ml), and the reaction mixture was stirred for 1 hourat room température. Toluene was added and the reaction was concentrated to near dryness. The réaction was poured into a separatory funnel and carefully quenched with saturated aqueous NaHCOj and extracted with dichloroethane. The organic layer was dried (M9SO4), filtered and concentrated to dryness. The crude product was purified by silica 9e! chromatography (0-10% MeOH / dichloromethane) to 9ive the desired product as a pale yellow oil (2.10 9, 95%): 1H NMR (400 MHz, CDCI3) δ 8.90 (dd, J= 1.8,0.8 Hz, 1H), 8.51 - 8.39 (m, 1H), 7.97 (ddt, J = 8.3, 2.7,1.3 Hz, 1 H), 7.41 (d, J = 0.8 Hz, 2H), 7.38 - 7.30 (m, 1 H), 3.21 - 2.93 (m, 2H), 1.34-1.19 (m, 3H).
3-chloro-N-ethyl-1-(pyridin-3-y1)-1H-pyrazol-4-amine was prepared as described in Example 8, Method B: Ή NMR (400 MHz, CDCI3) δ 8.87 (d, J = 2.5 Hz, 1H), 8.47 (dd, J - 4.7,1.2 Hz, 1H),
7.96 (ddd, J = 8.4,2.6,1.4 Hz, 1 H), 7.38 - 7.32 (m, 2H), 3.11 (q. J = 7.1 Hz, 2H), 2.97 (bs, 1H), 1.31 (t, J =7.1 Hz, 3H).
3-chloro-N-methyl-1-(pyridin-3-y!)-1H-pyrazol-4-amine was prepared as In Example 8, Method B: mp 108-118 C; Ή NMR (400 MHz, CDCI3) δ 8.88 (d, J= 2.4 Hz, 1H), 8.48 (dd, J = 4.7,1.4 Hz, 1H),
7.96 (ddd, J = 8.3,2.7,1.4 Hz, 1 H), 7.41 - 7.29 (m, 2H), 2.87 (s, 3H); EIMS m/z 208.
N, 3-dimethyl-1-(pyridin-3-yl)-1H-pyrazoi-4-amine was prepared as in Example 8, Method B: 1H NMR (400 MHz, CDCI3) δ 9.03 - 8.73 (m, 1H), 8.41 (dd, J= 4.7,1.4 Hz, 1H), 7.95 (ddd, J = 8.4, 2.7,
1.4 Hz, 1H), 7.42 - 7.27 (m, 2H), 2.85 (s, 4H), 2.25 (s, 3H); EIMS m/z 189
3-chloro-N-(cylopropylmethyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared as in Example 8, Method B: ’H NMR (400 MHz, CDCI3) δ 8.86 (d, J= 2.5 Hz, 1H), 8.47 (dd, J = 4.7,1.4 Hz, 1 H), 8.03-7.89 (m, 1 H). 7.40-7.29 (m, 2H), 3.21 (s, 1H), 2.91 (d, J- 4.4 Hz, 2H), 1.18-1.02 (m, 1H),
O. 65 - 0.45 (m, 2H), 0.41 - 0.12 (m, 2H).
3-chloro-/V-propyl-1-(pyridin-3-yl)-1H-pyrazol-4-amïne was prepared as In Example 8, Method B: 1H NMR (400 MHz, CDCI3) δ 8.86 (d, J-2.6 Hz, 1 H). 8.47 (dd, J = 4.7,1.4 Hz, 1H), 8.01 - 7.89 (m, 1 H), 7.42 - 7.27 (m, 2H), 3.23 - 2.84 (m, 3H), 1.77 - 1.59 (m, 2H), 1.03 (t, J = 7.4 Hz, 3H).
1-(5-Fluoropyridin-3-yl)-/V,3-dÎmethyl-1H-pyrazol-4-amine was prepared from the appropriate Boo· amine as described in Example 8, Method B: mp 142.0-143.5 ’C; Ή NMR (400 MHz, CDCI3) δ 8.67 (s, 1H), 8.26 (d, J= 2.3 Hz, 1H), 7.73 (dt, J- 10.0, 2.4 Hz, 1H), 7.27 (s, 1 H), 2.92- 2.81 (m, 4H), 2.24 (s, 3H); ESIMS m/z 207 ([M+H]*).
N-ethyl-1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-amine was prepared from the appropriate Boo-amine as described in Example 8, Method B: mp 85.0-86.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.66 (s, 1H), 8.25 (d, 2.5 Hz, 1H), 7.72 (dt, J= 10.0, 2.3 Hz, 1H), 7.27 (s, 1H), 3.07 (q, J= 7.1
Hz, 2H), 2.71 (s, 1H), 2.25 (s, 3H), 1.30 (t, J- 7.1 Hz, 3H); ESIMSm/z221 ([M+H]*).
3-Methyl-N-propyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from the appropriate Bocamlne as described In Example 8, Method B: mp 65.0-67.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.86 (d, J = 2.4 Hz, 1 H), 8.40 (dd, J - 4.7,1.4 Hz, 1 H), 7.94 (ddd, J = 8.3,2.7,1.5 Hz, 1 H), 7.35 - 7.28 (m, 2H), 3.00 (t, J = 7.1 Hz, 2H), 2.26 (s, 3H), 1.76 -1.58 (m, 2H), 1.03 (t, J = 7.4 Hz, 3H); ESIMS m/z 217 ([M+H]*).
N-(cyclopropylmethyl)-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from the appropriate Boc-amine as described In Example 8, Method B: mp 73.0-75.0 °C; 1H NMR (400 MHz, CDCI3) δ 8.86 (d, J = 2.4 Hz, 1 H), 8.40 (dd, J = 4.7,1.3 Hz, 1 H), 7.94 (ddd, J - 8.3, 2.6,1.5 Hz, 1 H), 7.35 - 7.28 (m, 2H), 2.87 (d, J = 6.9 Hz, 2H), 2.75 (s, 1 H), 2.28 (s, 3H), 1.22 - 1.05 (m, 1 H),
0.63 - 0.56 (m, 2H), 0.26 (q, J = 4.7 Hz, 2H); ESIMS m/z 229 ([M+H]*).
N4sopropyl-3-methyl-1-(pyridin-3-yl)-1 W-pyrazol-4-amine was prepared from the appropriate Bocamine as described In Example 8, Method B: IR (thin film) 3303 cm’1; 1H NMR (400 MHz, CDCI3) δ
8.86 (d, J= 2.3 Hz, 1H), 8.41 (dd, J- 4.7,1.4 Hz, 1H), 7.94(ddd, J = 8.3, 2.7,1.5Hz, 1H), 7.367.28 (m, 2H), 3,30 (hept, J = 6.3 Hz, 1H), 2.25 (s, 3H), 1.24 (d, J = 6.3 Hz, 6H); EIMS m/z 216.
5-Ethoxy-1-(5-fluoropyridin-3-yl)-N,3-dimethyl-1H-pyrazol-4-amlne was prepared from the appropriate Boc-amine as described In Example 8, Method B: IR (thln film) 3340 cm'1; 'H NMR (400 MHz. CDCI3) δ 8.91 (s, 1 H), 8.31 (d, J= 2.5 Hz, 1H), 7.88-7.80 (m, 1H), 4.24 (q, J= 7.1 Hz, 2H), 2.79 (s, 3H), 2.24 (s, 3H), 1.36 (t, J= 7.1 Hz, 3H); EIMS m/z 250.
5-Bromo-A/-methyt-1-(pyridin-3-yt)-1H-pyrazol-4-amine was prepared from the appropriate Bocamine as described In Example 8, Method B: mp 77.0-79.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.90 (d, J = 2.0 Hz, 1 H), 8.63 (d, J = 3.9 Hz, 1 H), 7.93 (ddd, J = 8.2, 2.4,1.5 Hz, 1 H), 7.51 (s, 1 H), 7.43 (dd, J = 8.2,4.8 Hz, 1 H), 4.49 (s, 1 H), 2.91 (s, 3H); ESIMS m/z 255 ([M+2]*).
5-Fluoro-A/,3-dimethyt-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from the appropriate Bocamine as described in Example 8, Method B: 1H NMR (400 MHz, CDCI3) δ 8.91 (t, J- 2.1 Hz, 1H), 8.50 (dd, J= 4.8,1.5 Hz, 1H), 7.93 (ddt, J= 8.3,2.8,1.5 Hz, 1H), 7.37 (ddd, J= 8.3,4.8, 0.7 Hz, 1H), 2.86 (d, J - 1.6 Hz, 3H), 2.43 (s, 2H), 2.24 (s, 3H); EIMS m/z 206.
5-Bromo-A/,3-dimethyt-1-(pyridîn-3-yt)-1H-pyrazol-4-amine was prepared from the appropriate Bocamine as described in Example 8, Method B: 1H NMR (400 MHz, CDCI3) δ 8.86 (dd, J- 2.5, 0.5 Hz, 1H), 8.59 (dd, J = 4.8,1.5 Hz, 1 H), 7.88 (ddd, J- 8.2,2.6,1.5 Hz, 1H), 7.40 (ddd, J= 8.2, 4.8,
0.7 Hz, 1H). 2.85 (s, 3H), 2.69 (s, 1H). 2.35 (s, 3H); ESIMS m/z 268 ([M+H]*).
5-Chloro-N,3-dimethyt-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from the appropriate Bocamine as described In Example 8, Method B: 1H NMR (400 MHz, CDCI3) δ 8.87 (d, J~ 2.3 Hz, 1H), 8.59 (dd, J= 4.8,1.3 Hz, 1H), 7.90 (ddd, J = 8.2,2.6,1.5 Hz, 1H), 7.40 (ddd, J~ 8.2, 4.8, 0.6 Hz, 1H), 2.87 (s, 3H), 2.45 - 2.19 (m, 4H); EIMS m/z 223.
3-Chloro-1-(5-fluoropyridin-3-yl)-A/-methyl-1H-pyrazol-4-amine was prepared from the appropriate Boc-amine as described in Example 8, Method B: mp 117.5-119.0 *C; ’H NMR (400 MHz, CDCI3) δ 8.68 (d, J = 1.1 Hz. 1H), 8.33 (d, J= 2.5 Hz, 1H), 7.75 (dt, 9.6,2.4 Hz, 1H), 7.31 (s. 1H), 3.14 (s, 1H), 2.87 (s, 3H); ESIMS m/z 227 ([Mf ).
3-Chloro-A/-ethyl-1-(5-fluoropyridÎn-3-yt)-1H-pyrazol-4-amine amine was prepared from the appropriate Boc-amine as described in Example 8, Method B: ’H NMR (400 MHz, CDCI3) δ 8.70-
8.63 (m, 1 H), 8.32 (d, J = 2.4 Hz, 1 H), 7.74 (dt, J - 9.7,2.4 Hz, 1 H), 7.31 (s, 1 H). 3.11 (q, J = 7.2
Hz, 2H). 1.31 (t, J = 7.1 Hz, 3H).
1- (5-Fluoropyridin-3-yl)-N-methyl-3-vinyl-1H-pyrazol-4-amine was prepared from the appropriate Boc-amine as described in Example 8, Method B: 105.0-107.0 ’C; 1H NMR (400 MHz, CDCi3) δ
8.72 (s, 1 H), 8.31 (d, J = 2.5 Hz, 1 H), 7.81 (dt, J = 9.8, 2.4 Hz, 1 H), 7.33 (s, 1 H), 6.75 (dd, J = 18.0,
11.6 Hz, 1H), 5.83 (dd, J- 18.0,1.1 Hz, 1H), 5.46(dd, J= 11,6,1.1 Hz, 1H), 2.86 (s, 3H); ESIMS m/z 219 ([M+H]*).
3-Cyclopropyl-1-(5-fluoropyridin-3-yl)-N-methyl-1H-pyrazol-4-amine was prepared from the appropriate Boc-amine as described in Example 8, Method B: mp 118.0-119.5 *C‘, 1H NMR (400 MHz, CDCi3) δ 8.66 - 8.58 (m, 1H), 8.23 (d, J =2.5 Hz, 1H), 7.75-7.68 (m, 1H), 7.25 (s, 1H), 3.09 (s, 1H), 2.86 (s, 3H), 1.78 -1.63 (m, 1H), 0.99 - 0.90 (m, 4H); ESIMS m/z 233 ([M+H]*).
3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from the appropriate Boc-amine as described in Example 8, Method B: mp 137.9-139.9 C; 1H NMR (400 MHz, CDCI3) δ 8.84 (d, J= 2.4 Hz, 1 H). 8.50 (dd, J = 4.7,1.4 Hz, 1H), 7.95 (ddd, J = 8.3, 2.7,1.5 Hz, 1 H), 7.52 (s, 1H), 7.37 (ddd, J= 8.4,4.7,0.7 Hz, 1H), 3.18 (s, 2H); ESIMS m/z 196 ([M+H]*).
2- ((3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amino)acetonitrile was prepared from tert-butyl (3chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(cyanomethyl)carbamate as In Example 8, Method B: mp 141-143 ’C; 1H NMR (300 MHz, CDCI3) δ 8.91 (d, J- 2.7 Hz, 1H), 8.54 (dd, J- 5.1,1.8 Hz, 1H),
7.97 (m, 1 H). 7.62 (s, 1H), 7.38 (dd, J = 12.0, 7.5 Hz, 1H), 4.97 (d, J = 6.9 Hz, 2H), 3.52 (m, 1H); El MS m/z 235 ([M+1]*).
N-3-dimethyl-1-(pyrimidin-5-yl)-1H-pyrazol-4-amine was prepared as In Example 8, Method B: mp 139-143 ’C; 1H NMR (400 MHz, CDCI3) δ 9.02 (s, 2H), 9.00 (s, 1H), 7.30 (s, 1H), 2.87 (d, J = 11.5 Hz, 3H), 2.27 (s, 3H); ESIMS m/z 190 ([M+H]).
3- chloro-N-methyl-1-(pyrimidin-5-yl)1-1H-pyrazol-4-amine was prepared as in Example 8, Method B: mp 111-114 ’C; 1H NMR (400 MHz, CDCI3) δ 9.09 - 9.04 (m, 1H), 9.02 (s, 2H), 7.30 (s, 1H), 3.14 (bs, 1H), 2.88 (s, 3H); ESIMS m/z 196 ([M+H]).
1-(5-Fluoro-3-pyridyl)-3-methyl-N-(trideuteriomethyl)pyrazol-4-amine was prepared from compound 380 using the procedure as described in Example 8, method B: mp 146-148 °C; ’H NMR (400 MHz, CDCh) δ 8.67 (s, 1H), 8.25 (d, J= 2.5 Hz, 1H), 7.73 (dt, J= 10.0, 2.3 Hz, 1H), 7.27 (s, 1H), 2.87 (s, 1 H), 2.24 (s, 3H); ESIMS m/z 210 ([M+H]*); IR (Thin film) 1599 cm’1.
3-Chloro-1-(3-pyridyl)-N-(trideuteriomethyl)pyrazoi-4-amine was prepared from compound 381 using the procedure as described in Example 8, method B: mp 104-106 °C; ’H NMR (400 MHz, CDCI3) δ 8.87 (d, J = 1.9 Hz, 1 H), 8.47 (d, J = 4.7 Hz, 1 H), 8.00 - 7.90 (m, 1 H), 7.40 - 7.30 (m, 2H),
3.10 (s, 1H); ESIMS m/z 212 ([M+H]*); IR (Thin film) 1579 cm·1.
3-Chloro-N-(cyclopropylmethyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from compound 361 using the procedure as described in Example 8, method B: mp 82-83 °C; ’H NMR (400 MHz, CDCI3) δ 8.86 (d, J= 2.5 Hz, 1H), 8.47 (dd, 4.7,1.3 Hz, 1H), 7.95 (ddd, J~ 8.4,2.7,1.5 Hz, 1 H), 7.38 - 7.32 (m, 2H), 3.22 (s, 1 H), 2.90 (d, J = 6.9 Hz, 2H), 1.23 -1.06 (m, 1 H), 0.65 - 0.53 (m, 2H), 0.31 - 0.19 (m, 2H).; ESIMS m/z 249 ([M+H]*);
3-Chloro-N-propyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared from compound 360 using the procedure as described in Example 8, method B: mp 92-94 °C; ’H NMR (400 MHz, CDCI3) δ 8.86 (d, J= 2.6 Hz, 1H), 8.47 (dd, J= 4.7,1.4 Hz, 1H), 7.95 (ddd, J = 8.3,2.7,1.5 Hz, 1H), 7.35 (ddd, J = 8.4, 4.7, 0.6 Hz, 1H), 7.33 (s, 1H), 3.22 - 2.94 (m, 3H), 1.75 -1.52 (m, 2H), 1.02 (t, J= 7.4 Hz, 3H); ESIMS m/z 237 <[M+H]*).
Example 9: Préparation of lsopropyl-(1-pyrldln-3-yl-1H-pyrazol-4-yl)-amlne
1-pyridin-3-yi-1H-pyrazol-4-ylamine (0.6 g, 3.7 mmol) was dissolved in Isopropyl acetate (8.5 ml). To the mixture, acetone (0.261 g, 4.5 mmol), trifluoroacetic acid (0.855 g, 7.5 mmol) and sodium triacetoxyborohydride (0.945 g, 4.5 mmol) were added. The réaction was stirred under nitrogen at room température for 4.5 hours and then quenched with 10% sodium hydroxide solution until the 47 pH reached - 9. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulfate and concentrated to dryness. The crude material was purified by silica gel chromatography (gradient elution of 5% methanol / dichloromethane) to give the title compound as an off white solid (0.35 g, 46%): mp 105 - 107 ’C; 1H NMR (300 MHz, CDCI3) δ 8.82 (d, J- 2.2 Hz, 1H), 8.63 (dd, J- 4.8,1.5 Hz, 1H), 8.13 (d, J= 1.8 Hz, 1H), 8.03 (d, J= 2.7 Hz, 1H), 7.94 - 7.77 (m, 1H). 7.38 (dt, J= 15.2, 7.6 Hz, 1H), 6.99 (t, 1H), 3.72 (m, 1H), 1.30 (t, J = 10.0 Hz,6H). ESIMS 214 m/z (M+1).
Example 10: Préparation of propyl-(1-pyiïdln-3-yl-1H-pyrazol-4-yl-amine
To 1-pyridin-3-yl-1H-pyrazol-4-ylamine (0.5 g, 3.12 mmol) In dichloromethane (5 ml) was added propionaldéhyde (0.18 g, 3.12 mmol) and sodium triacetoxy borohydride (0.99 g, 4.68 mmol) and stirred at room température for 16 hours. The reaction was taken up In dichloromethane and was washed with water and brine. The organic layer was dried (MgSOi), filtered and concentrated to dryness. The crude material was purified by silica gel chromatography eluting with 0-5% MeOH / Dichloromethane and resubjected In 0-100% ethylacetate / hexanes) to give the title compound as a dark oil (0.05 g, 7%): 1H NMR (300 MHz, CDCI3) δ 8.92 (d, J = 2.6 Hz, 1H), 8.48 (dd, J= 4.7,1.4 Hz, 1 H), 8.00 (ddd, J = 8.3,2.7,1.5 Hz, 1 H), 7.47 - 7.40 (m, 2H), 7.37 (dd, J = 8.3,4.7 Hz, 1 H), 3.04 (t, J = 7.1 Hz, 3H), 1.92 -1.46 (m, 2H), 1.03 (t, J = 7.4 Hz, 3H).
Example 11: Préparation of N-methyl-N-(1-pyrldln-3-yMH-pyrazol-4-y1)-lsobutyramide (Compound 42)
A solution of isobutyryl chloride (0.138 g, 1.3 mmol) in dichioroethane (1 mL) was pipetted at a dropwise rate into an Ice-cold suspension of methyl-(1-pyridin-3-yl-1H-pyrazoi-4-yl)-amine (0.15 g,
0.86 mmol) In dichioroethane (5 mL), stirred for 10 minutes and then treated at a dropwise rate with a solution of 4-W,W-dimethylaminopyridine (0.11 g. 0.9 mmol) in dichioroethane (1.5 mL). The cooling bath was removed after 30 minutes, stirred under nitrogen at room température for 14 hours, diluted with dichioroethane (40 mL), washed with water (30 mL), brine (10 mL), dried over MgSO< and purified by reversed phase column chromatography to give a yellowish gum (0.114 g, 54%) ’H NMR (300 MHz, CDCI3) δ 9.01-8.93(m, 1H), 8.67 (s, 0.4H), 8.61 (d, J = 4.2 Hz, 0.6H), 8.54 (d, 0.4H), 8.08-8.02 (m, 1H), 7.96 (s, 0.6H), 7.80 (s, 0.4H), 7.70 (s. 0.6H), 7.47-7.37 (m, 1 H), 3.49 (s, 1.2H), 3.26 (s, 2.8H), 3.06-2.98 (m, 0.4H), 2.86 - 2.70 (m, 0.6H), 1.25 (d, J= 6.1 Hz, 2.4H), 1.09 (d, J = 6.6 Hz. 3.6H). ESiMS m/z 245 ([M+1 ]).
Compounds 32 - 41, 43 - 52, 54 - 56, 59-61, 66, 73 - 75, 77 - 79, 82 - 85, 93 - 100, 113,117-129,131-134,139-140,142-144,148,160,163,173-175,184-186,197-198, 202, 208, 215-217,252-253, 277, 282 - 285, 287 - 290, 314 - 316, 347, 350-351, 353 - 355, 365 - 367,370, 388, 395, 399 - 403,407, 409,415 - 418, 444*449,452 - 454, 462 - 463, 465, 467 469, 496 - 498,506 - 507, 512, 525 - 527, 569,577, 581, 591 and 592 were made from the appropriate amines in accordance with the procedures disclosed in Example 11.
Example 12: Préparation of 4l4l4-trifluoro-2-methyi-N-(1-(pyridln-3-yl)-1W-pyrazol-4yl)butanamlde (Compound 65)
To a solution of 1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.150 g, 0.93 mmol) In dichioroethane (1.8 mi) was added 4,4,4-trifluoro-2-methylbirtanolc add (0.14 g, 0.93 mmol) and 4-N.Ndîmethylaminopyridine (0.23 g, 1.87 mmol) followed by 1-(3-dlmethylamlnopropyl)-3ethylcarbodïimlde hydrochloride (0.36 g, 1.87 mmol). The reaction stirred at room température overnight. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography eluting with 0-5% MeOH / dichloromethane to give a white solid (0.15 g, 55%); mp 140-145eC; ’H NMR (400 MHz, CDCl3) δ 9.00 (d, J= 2.4 Hz, 1H), 8.62 - 8.47 (m, 2H), 8.01 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.68 (s, 1 H). 7.53 (bs. 1 H). 7.40 (ddd, J= 8.3, 4.8, 0.6 Hz, 1H), 2.92 - 2.61 (m, 2H), 2.32 - 2.05 (m, 1 H), 1.38 (d, J = 6.6 Hz, 3H); ESIMS m/z 300 ([M+2]).
Compounds 53, 58, 62-63, 72, 76, 80 - 81,107 -108,136 -138,147,151 -159,164168,176-179,187-196, 201, 203 - 207, 209 - 214, 220, 224 - 249, 251, 259 - 275, 286, 292296, 303 - 313, 323 - 326, 341 - 344, 356 - 359, 371, 378 - 379, 382,384, 419 - 426, 439 -443, 455, 458 - 461, 464, 466, 476, 486, 490 - 493, 505, 508, 517, 528 - 529, 536 - 537, 539- 541, 544 - 545, 549 - 554, 572 - 577, 578, 579 and 580 were prepared from the appropriate amines in accordance with the procedures disclosed In Example 12.
Example 13: Préparation of tert-butyi 1-(pyrldln-3-yl)-1H-pyrazol-4-yIcarbamate (Compound 57)
Method A:
To a solution of 1-(pyridin-3-yi)-1H-pyrazol-4-amine (3 g, 18.73 mmol) In dichloromethane (33.4 ml) was added triethylamine (3.13 ml, 7.68 mmol) and BOC-anhydride (4.5 g, 20.60 mmol). The resulting solution was stirred at room température overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic portion was dried (MgSO«), filtered and concentrated to dryness. The crude product was purified by silica gel chromatography eluting with 0-100% ethyl acetate / hexanes to yield a white solid (2.0 g, 41 %); mp 108 - 112 eC; ’H NMR (400 MHz, CDCI3) δ 9.02 (d, J =2.2 Hz, 1H), 8.51 (t, J= 8.7 Hz, 1H), 8.37 (s, 1H), 8.30 (s, 1H), 7.98 (ddd, J =8.3, 2.4,
1.3 Hz, 1H), 7.68 (s, 1H), 7.36 (dd, J= 8.2,4.8 Hz, 1H), 1.52 (s, 9H); ESIMS m/z 261 ([M+1]).
Compounds 64 and 130 were prepared in accordance with the procedures disclosed in
Example 13, Method A.
Method B:
To a solution of 1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.1 g, 0.624 mmol) and di-tert-butyl dicarbonate (0.161 ml, 0.693 mmol) In tetrahydrofuran (1.690 ml) and water (0.566 ml) was added dropwise saturated aqueous sodium bicarbonate (0.572 ml, 0.667 mmol). The reaction was stined at room température ovemight. The reaction was diluted with water and extracted with ethyl acetate. The combined organic phases were concentrate to give tert-butyl 1 -<pyridin-3-yl)-1 Hpyrazol-4-ylcarbamate (135 mg, 0.519 mmol, 63 %), for which the analytical data was consistent with that reported In Example 13, Method A.
Compounds 150,172, 223, and 317 were prepared in accordance with the procedures disciosed in Example 13, Method B. Compounds 172 and 317 were also prepared In accordance with the procedures disciosed In Example 17. These compounds, as well as, certain other compounds, were made by alternative methods further illustrating certain embodiments.
Example 14: Préparation of tert-butyl methy1(1-(pyrldin-3-y1)-1H-pyrazol-4-yl)carbamate (Compound 67)
To a solution of tert-butyl 1-(pyridin-3-yl)-1H-pyrazol-4-ylcarbamate (1.6 g, 6.15 mmol) in DMF (30.7 ml) at O'C was added sodium hydride (0.34 g, 8.61 mmol, 60% dispersion In minerai oil) In one portion and the suspension was stirred for 30 minutes. The Ice bath was removed and stirred for an additional 30 minutes, lodomethane (0.46 ml, 7.38 mmol) was added in one portion and stirred ovemight at room température. Water and ethyl acetate were added and the resulting biphasic mixture was separated. The aqueous layer was extracted one time with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO<), filtered and concentrated to dryness. The crude product was purified by silica gel chromatography eluting with 0-35% ethyl acetate / hexanes to yield a light yellow seml-solid (0.85 g, 50%): IR (KBr) 1703 cm'1; 1H NMR(400 MHz. CDCl3) δ 8.98 (s. 1H), 8.52 (d, J = 3.8 Hz. 1H), 8.32 (s, 0.5H), 8.13 - 7.97 (m, 1H), 7.84 (s,
0.5H), 7.74 (s, 1H). 7.39 (dd, 8.0, 4.8 Hz, 1H), 3.30 (s, 3H), 1.56 (s, 9H); ESIMS m/z 275 ([M+H]).
Compounds 68, 86 - 92,105-106,114-116,141,149,161 -162,199 - 200, 254, 258, 291, 332, 352, 360 - 361, 380 - 381, 414,430 - 431, 450, 457, 474 - 475,485, 488, 510 · 511, 515, 523, and 590 were prepared from the appropriate amldes in accordance with the procedures dîsclosed In Example 14.
Tert-butyl methyl(3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate was prepared as In Example 14:1H NMR (400 MHz, CDCI3) δ 8.91 (d, J = 2.5 Hz, 1 H), 8.51 (dd, J = 4.7,1.3 Hz, 1 H), 8.00 (ddd, J= 8.3, 2.4,1.4 Hz, 1H), 7.83 (s, 1H), 7.38 (dd, J= 8.3, 4.7 Hz. 1H), 3.20 (s, 3H), 2.22 (s, 3H), 1.60 -1.30 (m, 9H).
Example 15: Préparation of N-ethyl-N-(1-methyl-3-(pyrldin-3-yl)-1H-pyrazol-5yl)lsobutyramlde (Compound 23)
To a solution of N-(1-methyl-3-(pyridÎne-3-yl)-1H-pyrazol-5-yl)isobutyramide (0.08 g, 0.33 mmol) In DMF (0.66 ml) at 0*C was added sodium hydride (0.016 g, 0.39 mmol, 60% dispersion in minerai oil) In one portion and the suspension was stirred for 30 minutes. The Ice bath was removed and stirred for an additional 30 minutes, lodoethane (0.06 g, 0.39 mmol) was added In one portion and stirred ovemight at room température. Water and ethyl acetate were added and the resulting biphasic mixture was separated. The aqueous layer was extracted one time with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSOx), filtered and concentrated to dryness. The crude product was purified by silica gel chromatography to give the title compound as a clear oil (27.5 mg, 30%): 1H NMR (300 MHz, CDCI3) δ 9.00 (bs, 1H), 8.57 (s, 1H), 8.09 (dd, J =
7.9 Hz, 1H), 7.34 (dd, 1H), 6.48 (s, 1H), 4.00 (m, 1H), 3.76 (s, 3H), 3.36 (m, 1H), 2.33 (m, 1H), 1.17 52 (t, J = 7.1 Hz, 3H), 1.08 (t, J - 6.7 Hz, 6H); ESIMS m/z 273 (M+H).
Compound 22 was prepared in accordance with the procedures disclosed in Example 15.
Example 16: Préparation of 5-bromo-1H-pyrazol-4-amlne, HBr
Br
HN N
A mixture of 4-nitro-1H-pyrazole (10 g, 88 mmoi) and 5% palladium on AI2O3 (1 g) In a mixture of éthanol (150 mL) and 50% aqueous HBr (50 mL) was shaken in a Par apparatus under hydrogen (10 psi) for 36 h. The mixture was filtered and the catalyst washed with éthanol. The filtrate was concentrated in vacuo to give a white solid. This solid was suspended in 10 mL of éthanol. After swlrling the flask for 5 min, ether was added to complété the crystallization. The solid was filtered, was washed with ether and dried under high vacuum to afford 5-bromo-1H-pyrazo!-4-amine, HBr (18.1 g, 84 % yield) as a white solid: mp 248 “C dec; 1H NMR (400 MHz, DMSO-de) δ 11.47 (s, 1H), 10.00 (s, 1H), 7.79 (s, 1H).
Example 17: Préparation of fert-butyl (3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)carbamate (Compound 172)
Example 17, Step 1: Préparation of 3-chloro-1H-pyrazol-4-amlne hydrochloride
H2N
Into a 2 L three-necked round bottom flask affixed with an overhead stirrer, a température probe, an addition funnel, and a nitrogen inlet were added éthanol (600 mL) and 4-nitro-1H-pyrazo!e (50.6 g, 447 mmol). To this solution was added, ln one portion, conc. HCl (368 mL) (note: rapid exotherm from 15 °C to 39 oc) and the resulting mixture was purged with nitrogen for 5 minutes. Palladium on alumlna (5%w/w) (2,6 g, Alfa, black solid) was added to the mixture and stirred at room température while triethylsilane (208 g, 1789 mmol) was added drop-wise over 4 h. The réaction, which started to slowly exotherm from 35 oc to 55 °C over 2.0 h, was stirred for a total of 16 h and vacuum filtered through a plug of Celite* to give a biphasic mixture. The mixture was transferred to a separatory funnel, the bottom aqueous layer was collected and rotary evaporated (60 °C, 50 mmHg) to dryness with the aid of acetonitrile (3 x 350 mL). The resulting yellow solid was suspended in acetonitrile (150 mL) and allowed to stand for 2 h at room température foilowed by 1 h at 0 °C ln the refrigerator. The solids were filtered and washed with acetonitrile (100 mL) to afford the titled compound 3-chloro-1H-pyrazol-4-amine hydrochloride (84 g, 97% yield, 80% purity) as a white solid: mp 190-193 C; 1H NMR (400 MHz, DMSO-de) δ 10.46 -10.24 ( bs, 2H), 8.03 (s,
0.54H), 7.75 (s, 0.46H), 5.95 (bs, 1H)); 13C-NMR (101 MHz, DMSO) δ 128.24,125.97,116.71.
Example 17, Step 2: Préparation of tert-butyl (3-chloro-1H-pyrazo!-4-yl)carbamate
Into a 2 L round bottom flask was added 3-chloro-1H-pyrazol-4-amine hydrochloride (100 g, 649 mmol) and THF (500 mL). To this mixture were added dl-fert-butyldicarbonate (156 g, 714 mmol) foilowed by sodium bicarbonate (120 g, 1429 mmol) and water (50.0 ml). The mixture was stirred for 16 h, diluted with water (500 mL) and ethyl acetate (500 mL) and transferred to a separatory funnel. This gave three layers; bottom- a white gelatinous predpitate, middle- light yellow aqueous, top- auburn organic. The phases were separated collecting the white gelatinous predpitate and the aqueous layer together. The aqueous was extracted with ethyl acetate (2 x 200 mL) and the ethyl acetate extracts were combined, washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered and rotary evaporated to give an auburn thick oil (160 g.). The thick oil was suspended ln hexane (1000 mL) and stirred at 55 OC for 2 h. This gave a light brown suspension. The mixture was cooled to 0 °C and the solid collected by vacuum filtration and rinsed with hexane (2x10 mL). The sample was air dried to constant mass to afford (3-chloro-1H-pyrazol-4-yl)carbamate (102.97 g, 72% yield, 80% purity) as a light brown solid: mp 137-138 *C; 1H NMR (400 MHz, CDCI3) δ 10.69 (s, 1H), 7.91 (s, 1H), 1.52 (s, 9H).
Example 17, Step 3: Préparation of tert-butyl (3-chloro-1-(pyrldin-3-y1)-1H-pyrazol-4yl)carbamate (Compound 172)
To a dry 2 L round bottom flask equipped with mechanical stirrer, nitrogen inlet, thermometer, and reflux condenser was charged the 34odopyridine (113.0 g, 551 mmol), (3-chloro-1H-pyrazol-4yljcarbamate (100 g, 459 mmol), potassium phosphate (powdered in a mortar and pestfe) (195g, 919 mmol), and copper chloride (3.09,22.97 mmol). Acetonitrile (1 L) followed by N\lfdimethylethane-l^-diamine were added and the mixture was heated to 81 ‘C for 4 hours. The mixture was cooied to room température and filtered through a bed of Celite®. The fiitrate was transferred to a 4 L Erlenmeyer flask equipped with mechanical stirrer and diluted with water until the total volume was about 4 L. The mixture was stirred for 30 minutes at room température and the resulting solid was collected by vacuum filtration. The solid was washed with water and washed with water and oven dried for several days In vacuo at 40 °C to a constant weight to give tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (117.8 g, 87% yield, 80% purity) as a tan solid: mp 140-143 °C; 1H NMR (400 MHz, CDCI3) δ 8.96 (s, 1H), 8.53 (dd, J = 4.7,1.2 Hz, 1H), 8.36 (s, 1 H), 7.98 (ddd, J = 8.3, 2.7,1.4 Hz, 1 H), 7.38 (dd, J = 8.3, 4.8 Hz, 1 H), 6.37 (s, 1 H), 1.54 (s, 9H); ESIMS (m/z) 338 ([M-t-Bu]*), 220 ([M-O-t-BuDCompound 172 was also prepared in accordance with the procedures disclosed In Example 13. Compound 317 was prepared in accordance with the procedures disclosed In Example 17 from tert-butyl (3-bromo-1H-pyrazol-4-yl)carbamate and also in accordance with the procedures disclosed In Example 13.
Example 18: Préparation of 3-(3-methyl-1H-pyrazol-1-yl)pyridlne and 3-(5-methy1-1H-pyrazol55
1-yl)pyrldlne
To a solution of 3-methyl-1H-pyrazole (10.99 g, 134 mmol) in Ν,Ν-dimethylformamlde (100 ml) at 0 eC was added sodium hydride (3.71 g, 154 mmol, 60% dispersion). The reaction was stirred at 0 ’C for 2 hours. 3-Fiuoropyridine (10.0 g, 103 mmol) was added, and the réaction was stirred at 100 ’C ovemight. The reaction was cooled to room température and water was added slowly. The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, concentrated and chromatographed (0-100% ethyl acetate / hexanes) to afford 3-(3-methyl-1Hpyrazoi-1-yl)pyridine (8.4g, 52.77 mmoi, 51.2 %) and 3-(5-methyl-1H-pyrazol-1-yl)pyridine (1.0 g, 6%). Analytical data of both products Is consistent with that reported under Example 6, Step 1.
3-(3-Bromo-1H-pyrazol-1-yl)pyridÎne was prepared from 3-fluoropyridine and 3-bromopyrazole, which was made as In W02008130021, as described Example 18: mp 89.5-92.5 ’C; ’H NMR (400 MHz, CDCi3) δ 8.94 (d, J- 2.4 Hz, 1H), 8.62 - 8.49 (m, 1H), 8.03 (ddd, J- 8.3, 2.7,1.4 Hz, 1H),
7.87 (d, J= 2.5 Hz, 1H). 7.42 (dd, J- 8.2,4.7 Hz, 1H), 6.54 (d, J= 2.5 Hz, 1H); ESIMS m/z 224 ([M]*)·
Example 19, Préparation of 3-chloro-1-(5-fluoropyridln-3-yl)-1H-pyrazol-4-amlne
Cl
NH2
To a stirred solution of 5-chioro-1H-pyrazol-4-amlne, HCl (2 g, 12.99 mmol) and césium carbonate (8.89 g, 27.3 mmol) in DMF (13 mL) was added 3,5-dîfluoropyridine (1.794 g, 15.58 mmol) and the mixture heated at 70 ’C for 12 h. The mixture was cooled to room température and filtered. The solids were washed with copious amount of ethyl acetate. The filtrâtes was washed with brine, dried over anhydrous MgSO< and concentrated in vacuo to give a brown solid. This solid was dissolved In ethyl acetate and the resulting solution was saturated with hexanes to precipitate 3chloro-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-amlne (2.31g, 10.32 mmol, 79 % yield) as a brown solid: Ή NMR (400 MHz, DMSO-de) δ 8.89 - 8.82 (m, 1H), 8.45 (d, J = 2.5 Hz, 1 H), 8.07 (d, J =
10.4 Hz, 1H), 7.94 (s, 1H), 4.51 (s, 2H); EIMS (m/z) 213 <(M+1]+).
3-Bromo-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-amine was prepared from the corresponding pyrazole as described In Example 19: mp 164-165 *C; ’H NMR (400 MHz, CDCI3) δ 8.65 (d, J = 1.7 Hz, 1 H), 8.36 (d, J= 2.5 Hz, 1H), 7.76 (dd, J= 5.9, 3.6 Hz, 1H), 7.48 (s, 1H), 3.22 (s, 2H). ’3C NMR (101 MHz, CDCI3) δ 160.87, 158.30,135.36,135.13,134.39,134.35,131.16,123.31,114.02, 112.77,112.54; EIMS (m/z) 258 <[M+1]+).
Example 20: Préparation of 1-(5-fluoropyridln-3-yl)-3-methyl-1H-pyrazoi-4-amlne
To a solution of 3-fluoro-5-(3-methyl-4-nitro-1H-pyrazol-1-y1)pyridine (3.133 g, 14.10 mmol) in éthanol (28.2 ml) was added ethyl acetate until ail of the starting material went Into solution. The solution was degassed and 10% palladium on carbon (0.750 g, 0.705 mmol) was added and the reaction was stirred In a parr hydrogenator at 40 psi for 3 hours. The solution was filtered through celite with ethyl acetate and concentrated to give 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4amine (2.000 g, 10.41 mmol, 73.8 %) as a brown solid: mp 136.0-138.0 ’C; ’H NMR (400 MHz, CDCI3) δ 8.67 - 8.59 (m, 1H), 8.27 (d, J = 2.5 Hz, 1H), 7.73 (dt, J = 9.9, 2.3 Hz, 1 H), 7.45 (s, 1H), 3.01 (s, 2H), 2.28 (s, 3H); EIMS m/z 192.
1-(Pyridin-3-yl)-3-(trifluoromethyl)-1H-pyrazol-4-amine was prepared from the appropriate nitropyrazole as described In Example 20: mp 112.5-115.0 “C; ’H NMR (400 MHz, CDCI3) δ 8.89 (d, J= 2.4 Hz, 1H), 8.57 (dd, J = 4.7,1.4 Hz, 1H), 8.03 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.56 (d, J =
0.7 Hz, 1H), 7.41 (ddd, J = 8.3, 4.8,0.7 Hz, 1H), 3.47 - 3.31 (m, 2H); EIMS m/z 228.
Example 21: Préparation of 3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-amlne
To 3-(3-chloro-4-nÎtro-1H-pyrazol-1-yt)pyridine (0.95 g, 4,23 mmol) In acetîc acid (8.46 mL), éthanol (8.46 mL) and water (4.23 mL) was added Iran powder (1.18 g, 21.15 mmol) and the reaction was stirred at room température for 30 minutes. To this was added carefully 2 Μ KOH and extracted with ethyl acetate. The ethyt acetate layers were combined, dried (MgSO<), filtered and concentrated to dryness. The crude matériel was purified by silica gel chromatography (0-10% methanol / dichloromethane) to give the desired product as a white solid (0.66 g, 80%): 1H NMR (400 MHz, CDCI3) δ 8.84 (d, J =2.6 Hz, 1H), 8.49 (dd, J = 4.7,1.4 Hz, 1H), 7.95 (ddd, J = 8.3, 2.7,
1.5 Hz, 1H), 7.53 (s, 1 H), 7.37 (ddd, J= 8.4,4.7,0.6 Hz, 1 H), 3.17 (bs, 2H).
3-methyt-1-(2-methylpyridin-3-yt)-1H-pyrazol-4-amlne was prepared as described ln Example 21: 1H NMR (400 MHz, CDCI3) δ 8.48 (dd, J= 4.8,1.6 Hz, 1H), 7.62 (dd. J= 8.0,1.6 Hz, 1 H). 7.23 7.18 (m, 2H), 2.91 (bs, 2H), 2.55 (s, 3H), 2.28 (s, 3H); EIMS m/z 188.
3-Phenyl-1-(pyridïn-3-yt)-1H-pyrazol-4-amlne was prepared from the appropriate nitropyrazole as described in Example 21: IR (thin film) 3324 cm'1; 1H NMR (400 MHz, CDCI3) δ 8.94 (d, J =2.2 Hz, 1H), 8.47 (dd, J- 4.7,1.4 Hz, 1 H), 8.07 (ddd, J= 8.3, 2.7,1.5 Hz, 1 H). 7.87 - 7.80 (m, 2H), 7.60 (s, 1 H), 7.50 - 7.44 (m, 2H), 7.40 - 7.34 (m, 2H), 3.86 (s, 2H): EIMS m/z 236.
3-Chloro-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-amlne was prepared from the appropriate nitropyrazole as described ln Example 21: mp 149.0-151.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.65 (d, J = 1.6 Hz, 1 H), 8.35 (d, J - 2.4 Hz, 1 H), 7.75 (dt, J = 9.5, 2.4 Hz, 1 H), 7.51 (s, 1 H), 3.21 (s, 2H); ESIMS m/z 213 ([M]*).
3-Bromo-1-(pyridin-3-yl)-1H-pyrazoi-4-amlne was prepared from the appropriate nitropyrazole as described în Example 21: mp 143,0-146.0 °C; 1H NMR (400 MHz, CDCI3) δ 8.85 (d, J = 2.4 Hz,
H), 8.50 (dd, J = 4.7,1.4 Hz, 1 H), 7.96 (ddd, J = 8.3,2.7,1.5 Hz, 1 H), 7.49 (s, 1 H), 7.37 (ddd, J =
8.4, 4.7, 0.7 Hz, 1H), 3.21 (s, 2H); ESIMS m/z 241 ([M+2]*).
Exemple 22: Préparation of fert-butyl (5-methy1-1-(pyrldin-3-yl)-1H-pyrazoi-4-yl)carbamate (Compound 281)
To a solution of (E)-fert-buty! 1-(dimethylamino)-3-oxobut-1-en-2-ylcarbamate (0.59 g, 2.58 mmol) In éthanol (2.5 mL) was added 3-hydrazinylpyridine, 2HCI (0.470 g, 2.58 mmol). The reaction mixture was stirred at ambient température for 16 hours. The reaction mixture was concentrated and purified using silica gel chromatography (0-100 % ethyl acetate / hexanes) to yield the title compound as an orange foam (0.235 g, 30%): IR (thin film) 3268, 2978 and 1698 cm'1; 1H NMR (400 MHz, CDCI3) δ 8.75 (dd, J= 2.5, 0.5 Hz, 1H), 8.62 (dd, J= 4.8,1.5 Hz, 1H), 7.82 (ddd, J = 8.2, 2.6, 1.5 Hz, 1H), 7.78 (s, 1H), 7.43 (ddd, J= 8.1, 4.8, 0.6 Hz, 1H), 6.04 (s, 1H), 2.29 (s, 3H), 1.52 (s, 9H); ESIMS m/z 275 ([M+H]*), 273 ([M-H]*).
Example 23: Préparation of fert-butyl 1-(5-fluoropyridin-3-y1)-3-methy1-1H-pyrazoi-4ylcarbamate (Compound 111) and fert-butyl 5-ethoxy-1-(5-fluoropyrldîn-3-y1)-3-methyl-1Hpyrazol-4-ylcarbamate (Compound 112)
To a solution of 3-fluoro-5-(3-methyl-4-nitro-1H-pyrazol-1-yl)pyridÎne (3.133 g, 14.10 mmol) In éthanol (28.2 ml) was added ethyl acetate until ail of the starting material went into solution. The solution was degassed and 10% palladium on carbon (0.750 g, 0.705 mmol) was added and the reaction was stirred in a parr hydrogenator at 40 psi for 3 hours. The solution was filtered through celite with ethyl acetate and the solvent was removed under reduced pressure. The residue was dissolved In tetrahydrofuran (32.0 ml) and water (9.61 ml). Di-fert-butyl dicarbonate (2.52 g, 11.55 mmol) was added followed by saturated aqueous sodium bicarbonate (9.54 ml, 11.45 mmol). The reaction was stirred at room température overnight, diiuted with water and extracted with ethyl acetate. The combined organic phases were concentrated and chromatographed (0-100% ethyl acetate / hexanes) to give fert-butyl 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-ylcarbamate (1.673 g, 5.72 mmol, 41.0 %) as a yellow solid and the fert-butyî 5-ethoxy-1-(5-fluoropyridin-3-yl)-3methyl-1H-pyrazol-4-ylcarbamate (0.250 g, 0.74 mmol, 5.2 %) as a brown oil:
fert-Butyl 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-ylcarbamate (Compound 111): mp 131.5133.0 °C; ’H NMR (400 MHz, CDCI3) δ 8.75 (s, 1H), 8.32 (d, J = 2.5 Hz, 1H), 8.28 (s, 1H), 7.77 (dt, J =9.7, 2.4 Hz, 1H), 6.15 (s. 1H), 2.29 (s. 3H), 1,54 (s. 9H); ESIMS m/z 293 ([M+H]*).
fert-Butyl 5-ethoxy-1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-ylcarbamate (Compound 112): IR (thin film) 1698 cm·’; ’H NMR (400 MHz, CDCI3) δ 8.88 (s, 1H), 8.34 (d, J = 2.5 Hz, 1H), 7.83 (d, J = 9.9 Hz, 1H), 5.99 (s, 1H), 4.37 (q, J = 7.0 Hz, 2H), 2.17 (s, 3H), 1.50 (s, 9H), 1.37 (t, J = 7.1 Hz, 3H); ESIMS m/z 337 ([M+H]*).
Example 24: Préparation of Bis iert-t-buty! (1-(pyrldln-3-yl)-1H-pyrazol-4-yl)carbamate (Compound 595)
To a solution of fert-butyl (1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (2.00 g, 7.68 mmol) In dry THF (21.95 mL) at 0 “C was added 60% sodium hydride (0.33 g, 8.45 mmol) In one portion and stîræd at that température for 30 minutes. To this was then added Boc-Anhydride (1.84 g, 8.45 mmol) in one portion and stirred for 5 minutes at 0 ’C. The water bath was removed and the reaction was warmed to room température and stirred at additional 30 minutes. The reaction was quenched with water and extracted with ethyl acetate. The ethyl acetate layers were combined, dried (MgSO«), filtered and concentrated to dryness. The crude material was purified by silica gel chromatography (0-100% ethyl acetate / hexanes) to give the desired product as a white solid (2.0 g, 72%): ’H NMR (400 MHz, CDCI3) δ 9.12 - 8.86 (m, 1H), 8.55 (dd. J= 4.7,1.4 Hz, 1H), 8.04 (ddd, J = 8.3, 2.7,1.5 Hz, 1 H), 8.01 (d, J = 0.5 Hz, 1 H), 7.84 - 7.65 (m, 1 H), 7.41 (ddd, J = 8.3,4.8, 0.7 Hz, 1H), 1.51 (s, 18H).
Example 25: Préparation of 3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-amine (Compound 516)
To tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (2 g, 6.79 mmol) in dichloromethane (6.79 ml) was added trifluoroacetic acid (6.79 ml) and the mixture was left stirring at room température for 2 hours. Toluene (12 mL) was added and the reaction was concentrated to near dryness. The mixture was poured into a separatory funnel containing saturated aqueous sodium blcarbonated and was extracted with dichloromethane. The combined organic layers were concentrated to give 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.954g, 4.90 mmol, 72,2 %) as a white solid: mp 137.9-139.9 °C; ’H NMR (400 MHz, CDCI3) δ 8.84 (d, J = 2.4 Hz, 1 H), 8.50 (dd, J =
4.7,1.4 Hz, 1 H), 7.95 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.52 (s, 1H), 7.37(ddd, J= 8.4, 4.7, 0.7 Hz, 1H), 3.18 (s, 2H); ESIMS m/z 196 ([M+H]*).
Example 26: Préparation of N-allyl-1-(5-fluoropyridln-3-yl}-3-methyl-1H-pyrazoi-4-amlne hydrochloride
To a solution of terf-butyl allyl(1-(5-fluoropyridin-3-yi)-3-methyi-1H-pyrazol-4-yi)carbamate (908 mg,
2.73 mmol) In dioxane (5 mL) was added HCl {1M in ether) {13.65 mL, 13.65 mmol) and the mixture stirred at room température for 48 h. The resulting white soiid was filtered, washed with ether and dried under vacuum to give N-allyi-1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-amine, HCl {688 mg, 94 % yield) as a white solid: mp 189-190 ’C; Ή NMR (400 MHz, CDCI3) δ 8.79 - 8.68 {m, 1H), 8.32-8.26{m, 1H), 8.23{s, 1H), 7.98-7.86{m, 1H), 5.86-5.68 (m, 1 H), 5.28-5.17 {m, 1 H). 5.17-5.03 (m, 1H), 3.59 (d, J = 6.2 Hz, 2H), 2.11 (s, 3H); EIMS (m/z) 233 ([M+1J+).
N-Allyi-3-chloro-1-(pyTidin-3-yl)-1H-pyrazol-4-amine, HCl was prepared as described In Example 26 from terf-butyl allyi(3-chloro-1-(pyridin-3-yi)-1H-pyrazoi-4-yl)carbamate: mp 172-174 *C; Ή NMR (400 MHz, CDCI3) δ 9.20 (d, 2.5 Hz, 1 H). 8.65 {dd, J = 5.3,1.1 Hz, 1H), 8.61 (ddd, J - 8.6, 2.5,
1.1 Hz, 1H), 8.24 (s, 1 H), 7.93 (dd, J-8.6,5.3 Hz, 1H), 3.66 {dt, J-5.5,1.3 Hz, 2H); EiMS (m/z) 235 ([M+1 ]+).
N-Allyl-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, HCl was prepared as described in Example 26 from fert-butyl ally1(3-methyi-1-(pyridin-3-yl)-1H-pyrazol-4-yi): mp 195-197 *C; ’H NMR {400 MHz, DMSO-de) δ 9.12 (d, J = 2.4 Hz, 1 H), 8.58 (dd, J = 5.0,1.2 Hz, 1 H), 8.48 (s, 1 H), 8.43 (d. J = 9.7 Hz, 1H), 7.77 (dd. J = 8.4, 5.0 Hz, 1H), 6.04 - 5.92 (m, 1H), 5.44 {dd, J = 17.2,1.4 Hz, 1H), 5.32 {d, J - 9.4 Hz, 1H), 3.81 {d, J- 6.2 Hz, 2H); EIMS (m/z) 249 ([M-1J+).
3-Bromo-1-(5-fluoropyridin-3-yl)-N-methyl-1H-pyrazol-4-amine, HCl was prepared as described in Example 26 from terf-butyl 3-bromo-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl{methyl)carbamate: mp 167-168 ’C; 1H NMR (400 MHz, CDCI3) δ 8.93 (s, 1H), 8.50 {d, J= 2.5 Hz, 1H), 8.23 {s, 1H), 8.14 {dt, J = 10.4, 2.3 Hz, 1H), 2.73 {s, 3H).
3-Bromo-N-methyl-1-(pyridin-3-yi)-lH-pyrazol-4-amine, HCl was prepared as described In Example 26 from terf-butyl (3-bromo-1-(pyTidin-3-yi)-1H-pyrazol-4-yi)(methyl)carbamate {160 mg, 0.45 mmol) ln dioxane (1 mL) was added 4M HCl: mp. 226-228 ’C; Ή NMR (400 MHz, DMSO-de) δ 9.26 - 9.06 (d, J = 2.6 Hz, 1H), 8.69-8.54 (m, 1H), 8.54 - 8.39 (d, J= 8.0 Hz. 1H), 8.33 - 8.14 (s, 1H), 7.90 7.72 (m, 1H), 2.82 - 2.67 (s, 3H); EIMS (m/z) 253 ([M+1]+), 255 ([M+2HJ+).
3-Bromo-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amlne, HCl was prepared as described In Example 26 from 3-bromo-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, HCl: mp 216-217 ’C; ’H NMR (400 MHz, DMSO-de) δ 10.66 - 10.05 (s. 3H), 9.28 - 9.20 (d, J= 2.5 Hz, 1H), 8.74 - 8.67 (m, 1H), 8.67 8.56 (m, 3H), 7.96 - 7.84 (m, 1H), 3.21 - 3.14 (m, 2H), 1.29-1.22 (m, 3H); EIMS (m/z) 267 ([M+1]+).
3-Chloro-N-(2-methoxyethyl)-1-(pyridln-3-yl)-1H-pyrazol-4-amine, HCl was prepared as described ln Example 26 from tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(2-methoxyethyl)carbamate, HCl: mp 157-158 *C;’H NMR (400 MHz, DMSO) δ 9.22 - 9.14 (d, J= 2.5 Hz, 1 H), 8.70 - 8.65 (s. 1H), 8.65 - 8.59 (m, 1H), 8.38 - 8.33 (m, 1H). 8.00 - 7.89 (m. 1H). 3.59 - 3.50 (t, J = 5.8 Hz, 2H), 3.32 - 3.27 (s, 3H), 3.22 - 3.14 (m, 2H); EIMS (m/z) 253 ([M+1 ]+).
Example 27: Préparation of 3-chloro-A/-ethy1-1-(pyridln-3-y1)-1H-pyrazol-4-amlne hydrochloride
Cl
Into a 500 mL three-necked round bottom flask equipped with a magnetic stlr bar was added a solution of tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(ethyl)carbamate (21 g, 65.1 mmol) in
1.4-dioxane (35 mL). This pale yellow solution was placed Into an ice bath and cooled to 1 °C. A solution of 4M HCl in dioxane (65 mL, 260 mmol) was added in one portion. After stirring for 20 minutes, the Ice bath was removed and the suspension was stined further at amblent température for 16 hours. The reaction was diluted with 200 mL of ethyl ether and the solid was filtered and washed with ether and placed in a vacuum oven at 40 ocfor 18 hours. The title compound was isolated as a pale yellow solid (18.2 g, 95%): ’H NMR (400 MHz, MeOD) δ 9.52 (d, J = 2.5 Hz, 1H).
9.17 (s, 1 H), 9.14 (ddd, J- 8.7,2.5,1.1 Hz, 1H), 8.93 (ddd, J= 5.7,1.1,0.6 Hz, 1H), 8.31 (ddd, J8.7, 5.7, 0.5 Hz, 1 H), 3.58 (q, J = 7.3 Hz, 2H), 1.48 (t, J = 7.3 Hz, 3H); ESIMS m/z 223 ([M+H]*).
3-Chioro-N-methyl-1-(pyridin-3-yl)-1H-pyrazole-4-amine, 2HCI was prepared as described in Example 27:1H NMR (400 MHz, MeOD) δ 9.28 (d, J= 2.5 Hz, 1H), 8.86 (ddd, J = 8.7, 2.5,1.2 Hz, 1 H), 8.79 - 8.75 (m, 1 H), 8.62 (s, 1 H), 8.19 (ddd, J = 8.7, 5.6,0.5 Hz, 1 H), 3.06 (s, 3H); 13C NMR (101 MHz, MeOD) δ 141.42,139.58,137.76,134.58,134.11,129.33,127.55,122.14,35.62); ESIMS m/z 209 ([M+H]*).
Example 28: Préparation of 3-(4-nltro-3-pheny!-1H-pyrazol-1-yl)pyrldlne
To a suspension of phenylboronic acid (0.546 g, 4.47 mmol) in toluene (6.63 ml) was added 3-(3chloro-4-nitro-1H-pyrazol-1-yl)pyridine (0.335 g, 1.492 mmol) foilowed by éthanol (3.31 ml) and 2 M aqueous potassium carbonate (1.492 ml, 2.98 mmol). The solution was degassed by applying vacuum and then purglng with nitrogen (3 times). To the reaction mixture was added palladium tetrakis (0.086 g, 0.075 mmol) and the flask was heated at 110 ’C under nitrogen for 16 hours. The aqueous layer was removed and the organic layer was concentrated. The crude product was purified via silica gel chromatography (0-100% ethyl acetate / hexanes) to give 3-(4-nltro-3-phenyl1H-pyrazol-1-yl)pyridine (499 mg, 1.874 mmol, 80 %) as a yellow solid: mp 144.0-146.0 °C; 1H NMR (400 MHz, CDCI3) δ 9.09 (d, J= 2.3 Hz, 1H), 8.82 (s, 1H), 8.71 (dd, J= 4.8,1.4 Hz, 1H), 8.16 (ddd, J= 8.3, 2.7,1.5 Hz, 1H), 7.82 - 7.74 (m, 2H), 7.55 - 7.48 (m, 4H); EIMS m/z 266.
Example 29: Préparation of 5-bromo-1-(pyrldln-3-yl)-1H-pyrazol-4-yl(methyl)carbamate (Compound 110)
To fert-butyl methyl(1 -(pyridin-3-yl)-1 H-pyrazol-4-yl)carbamate (0.200 g, 0.729 mmol) in dichloroethane (3.65 ml) was added 1-bromopyrrolidine-2,5-dione (0.260 g, 1.456 mmol) and the reaction was stirred overnight at 50’C. The reaction was concentrated, diluted with dichloromethane, and washed with water and saturated aqueous sodium thiosulfate. The organic phase was concentrated to give tert-butyl 5-bromo-1-(pyridin-3-yl)-1H-pyrazoi-4yl(methyl)carbamate (256 mg, 0.725 mmol, 99 %) as a brown oil: iR (thin film) 1697 cm'1; ’H NMR (400 MHz, CDCI3) 5 8.89 (s, 1H), 8.68 (d, J- 4.1 Hz, 1H), 7.93 (ddd, J-8.2,2.5,1.5 Hz, 1H), 7.69 (s, 1H), 7.46 (dd, J- 8.1, 4.8 Hz, 1H), 3.22 (s, 3H), 1.44 (s, 9H); ESIMS m/z 352 ([M-H]').
Example 30: Préparation of Bis fert-t-butyl (5-chloro-1-(pyrldln-3-yl)-1W-pyrazol-4yi)carbamate (Compound 109)
To bis f-butyi (1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (1.30 g, 3.61 mmol) In acetonitrile (21.22 mL) was added N-chlorosuccinimlde (0.96 g, 7.21 mmol) and the reaction was stirred at 45 ’C for 48 hours. The reaction was cooled to room température and poured into water and extracted with dichloromethane. The dichloromethane layers were combined, poured through a phase separator to remove water and concentrated to dryness. The crude material was purified by silica gel chromatography (0-60% ethyl acetate / hexanes) to give the desired product as a yellow solid (0.90 g, 63%): mp 109-115 ’C; ’H NMR (400 MHz, CDCI3) δ 8.90 (d, J- 2.3 Hz, 1H), 8.68 (dd, J- 4.8,
1.5 Hz, 1H), 7.94 (ddd, J- 8.2, 2.5,1.5 Hz, 1H), 7.70 (s, 1H), 7.47 (dtd, J = 11.0, 5.6, 5.5, 4.8 Hz, 1H), 1.49 (s, 18H); ESIMS m/z 395 ([M+H]*).
fert-Butyl (5-chloro-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(methyl)carbamate was prepared from the appropriate pyrazole In dichloroethane as the solvent as described In Example 30: ESIMS m/z 324 ([M+H]*).
Compounds 110 (see also procedure In Example 29) and 146 were prepared from the appropriate pyrazoles using N-bromosucdnimide In accordance with the procedures dîsclosed in Example 30.
fert-Butyl 5-bromo-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-yl(methyl)carbamate was prepared from the appropriate pyrazole in dichloroethane as described in Example 30: 1H NMR (400 MHz, CDCI3) δ 8.88 (d, J= 2.3 Hz, IH), 8.69 - 8.60 (m. 1H), 7.96 - 7.86 (m, IH), 7.48 - 7.39 (m, 1H), 3.18 (s, 3H), 2.26 (s, 3H), 1.60-1.36 (m, 9H); ESIMS m/z 368 ([M+H]*).
Exemple 31: Préparation of bis tert-butyl (5-fluoro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)carbamate (Compound 135)
To a solution of bis tert-t-butyl (1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (0.075 g, 0.208 mmol) in DMF (0.416 mi) and acetonitrile (0.416 ml) was added Selecfluor® (0.184 g, 0.520 mmol). The reaction was stirred at room température for one week. The reaction was concentrated, saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate. The combined organic phases were concentrated and chromatographed (0-100% ethyl acetate / hexanes) to give bis tert-butyl (5-fluoro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)carbamate (16 mg, 0.042 mmol, 20.32 %) as an off-white solid: ’H NMR (400 MHz, CDCI3) δ 8.97 (t, J= 2.0 Hz, IH), 8.61 (dd, J = 4.8,1.4 Hz, 1 H), 7.99 (ddt, J = 8.3, 2.6,1.3 Hz, 1 H), 7.57 (d, J = 2.5 Hz, 1 H), 7.44 (ddd, J 8.3,4.8, 0.6 Hz, 1H), 1.50 (s, 18H); ESIMS m/z 379 ([M+H]*).
tert-Butyl (5-fluoro-3-methy!-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(methyl)carbamate was prepared as described in Example 31:1H NMR (400 MHz, CDCI3) δ 8.94 (s, 1H), 8.57 (d, J - 4.2 Hz, 1H), 7.96 (d, J = 7.7 Hz, 1 H), 7.41 (dd, J = 7.9, 4.7 Hz, 1 H), 3.17 (s, 3H), 2.23 (s, 3H), 1.58 - 1.40 (m, 9H); ESIMS m/z 307 ([M+H]*).
Example 32: Préparation of N-cyclopropyl-3-methyl-1-(pyridln-3-yl)-1H-pyrazoi-4-amlne
Example 32, Step 1: Préparation of 3-(4-lodo-3-methyl-1H-pyrazoi-1-yl)pyr!dine
To a mixture of 3-(3-methyl-1H-pyrazol-1-yl)pyridine (6.7 g, 42.1 mmol), lodic acid (2.96 g, 16,84 mmol), and diiodine (8.55 g, 33.7 mmol) in acetic acid (60.1 ml) was added concentrated sulfur acid (3,74 ml, 21.04 mmol), The reaction mixture heated to 70 *C for 30 minutes, The réaction mixture was poured onto Ice with sodium thiosulfate and was extracted with diethyl ether. The combined 15 organic phases were washed with saturated aqueous sodium bicarbonate. The organic phases were then dried with magnésium sulfate, filtered and concentrated in vacuo. The solid residue was dissolved in dichloromethane, applied to a 80g silica gel column, and eluted with 0-80% acetone in hexanes to afford 3-(4-iodo-3-methyl-1H-pyrazol-1-yl)pyridine (11.3 g, 35.7 mmol, 85 %) as a whlte solid: mp 131 ’C; 1H NMR (400 MHz, CDCI3) δ 8.95 - 8.85 (m, 1H), 8.52 (dd, J » 4.8,1.4 Hz, 1H), 20 8.00 - 7.94 (m, 1H), 7.91 (s, 1H), 7,38 (ddd, J - 8.3,4.8,0.7 Hz, 1H), 2.34 (s, 3H): EIMS m/z 285.
Example 32, Step 2: Préparation of N-cyciopropyl-3-methyl-1-(pyrldln-3-yl)-1H-pyrazol-4amlne
To a solution of 3-(4-lodo-3-methyl-1/7-pyrazol-1-yl)pyridine (2.0 g, 7.02 mmol) In dimethylsulfoxida (7.02 ml) was added 1 -(5,6,7,8-tetrahydroquînolin-8-yl)ethanone (0.246 g, 1.403 mmol), cyclopropanamlne (0.486 ml, 7.02 mmol), césium carbonate (6.86 g, 21.05 mmol) and copperfl) bromide (0.101 g, 0.702 mmol). The reaction mixture was stirred at 35 “C for 2 days. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organics were washed with brine, concentrated and chromatographed (0-100% ethyl acetate / hexanes) to give Ncyclopropyl-3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (269 mg, 1.255 mmol, 17.90 %) as a yellowsolid: mp 104.0-107.0 eC; Ή NMR (400 MHz, CDCI3) Ô 8.89 (dd, J= 2.7,0.5 Hz, 1H), 8.41 (dd, J= 4.7,1.4 Hz, 1 H), 7.96 (ddd, J= 8.3, 2.7,1.5 Hz, 1H), 7.51 (s, 1 H). 7.33 (ddd, J = 8.3, 4.7,
0.7 Hz, 1H), 3.42 (s, 1H), 2.53 - 2.42 (m, 1 H), 2.22 (s, 3H), 0.72 - 0.65 (m, 2H), 0.60 - 0.53 (m, 2H);
ESIMSm/e215 ([M+H]*).
3-Methyl-N-(3-(methylthio)propyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared as described In Example 32: IR (thin film) 3298 cm*1; ’H NMR (400 MHz, CDCI3) Ô 8.87 (d, J = 2.3 Hz, 1H), 8.40 (dd, J = 4.7,1.4 Hz, 1 H), 7.93 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.35 (s, 1H), 7.34-7.29 (m, 1H), 3.16 (t, J- 6.8 Hz, 2H), 2.89 (s, 1H), 2.64 (t. J= 7.0 Hz, 2H), 2.25 (s, 3H), 2.13 (s, 3H), 1.95 (p, J- 6.9 Hz, 2H); ESIMS m/z 263 ([M+H]*).
3-Methyl-N-(2-methyl-3-(methylthio)propyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine was prepared as described in Example 32: IR (thin film) 3325 cm·’; ’H NMR (400 MHz, CDCI3) Ô 8.86 (d, J - 2.5 Hz, 1 H), 8.40 (dd, J = 4.7,1.2 Hz, 1 H), 7.93 (ddd, J = 8.3, 2.7.1.5 Hz, 1 H), 7.35 (s, 1 H), 7.32 (ddd, J = 8.3,4.7,0.5 Hz, 1H), 3.12 (dd, J - 11.5, 6.1 Hz, 1H), 2.94 (dd, J = 11.9, 6.6 Hz, 1H), 2.62 (dd, J =
12.9, 6.9 Hz, 1H). 2.52 (dd, J~ 12.9, 6.2 Hz, 1H), 2.26 (s, 3H), 2.14 (s. 3H). 2.12 - 2.02 (m, 1H),
1.11 (d, J = 6.8 Hz, 3H); EIMS m/z 276.
Example 33: Préparation of tert-butyl (3-cyclopropyl-1-(5-fIuoropyrldin-3-yl)-1H-pyrazol-4yl)carbamate (Compound 434) and tert-butyl (1-(5-fluoropyrldin-3-yl)-1W-pyrazoi-4yl)carbamate (Compound 489)
To a suspension of 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.087 g, 6.47 mmol) In toluene (13.69 ml) was added tert-butyl (3-bromo-1-(5-fluoropyridin-3-yl)-1H-pyrazoi-4-yl)carbamate (1.1 g, 3.08 mmol) followed by éthanol (6.84 ml) and 2 M aqueous potassium carbonate (3.08 mL, 6.16 mmol). The solution was degassed by applying vacuum and then purging with nitrogen (3 times). To the reaction mixture was added palladium tetrakis (0.178 g, 0.154 mmol) and the flask was heated at 100 ’C under nitrogen for 36 hours. Water (5 mL) was added and the mixture was extracted with ethyl acetate. The combined organlcs were concentrated and chromatographed (ΟΙ 00% ethyl acetate / hexanes) to give tert-butyl (3-cyclopropyl-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4yljcarbamate (705 mg, 2,215 mmol, 71.9 % yield) as a yellow solid and tert-butyl (1 -(5-fluoropyridin3-yl)-1H-pyrazol-4-yl)carbamate (242 mg, 0.870 mmol, 28.2 % yield) as a yellow solid. tert-Butyl (3-cyclopropyl-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)carbamate: mp 156.5-158.0; ’H NMR (400 MHz, CDCI3) Ô 8.73 (s, 1 H), 8.30 (d, J= 2.5 Hz, 1H), 8.27 (s, 1H), 7.76 (dt, J= 9.8, 2.4 Hz, 1H), 6.43 (s, 1H). 1.55 (s, 9H), 1.01-0.91 (m, 4H); ESiMS m/r 319 ([M+H]+). (1-(5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl)carbamate: mp 121.9-123.0 *C; Ή NMR (300 MHz, CDCI3) δ 8.78 (s, 1H), 8.37 (s, 1H), 8.28 (s, 1H), 7.81 (d, J= 9.6 Hz, 1 H), 7.59 (s, 1H). 6.44 (s, 1H). 1.53 (s, 9H). ESIMS m/z 278 ([M]*).
Compounds 340 and 404 were prepared as described in Example 33.
Example 34: Préparation of tert-butyl (3-ethyl-1-(5-fluoropyridin-3-yl)-1H-pyrazoi-4yi)(methyl)carbamate (Compound 408)
To a N2-purged solution of tert-butyl (1-(5-fluoropyridin-3-yl)-3-vinyl-1H-pyrazol-4yl)(methyl)carbamate (0.730 g, 2.293 mmol) in methanol (15.29 ml) was added 10% palladium on carbon (0.036 g, 0.339 mmol). The réaction was purged with hydrogen and run under 80 psi of hydrogen at room température for 60 hours. The reaction gave less than 20% conversion. The reaction mixture was filtered through celite, concentrated, and redissolved in ethyl acetate (4 mL) and transferred to a bomb. The reaction was heated at 50 *C at 600 psi of hydrogen for 20 hours. The reaction was only 50% complote. Methanol (1 mL) and 10% palladium on carbon (36 mg) were added, and the reaction was heated at 80 °C at 650 psi of hydrogen for 20 hours. The réaction was filtered through celite and concentrated to give tert-butyl (3-ethyl-1-(5-fluoropyridin-3-yl)-1 H-pyrazol-
4-yl)(methyl)carbamate (616 mg, 1.923 mmol, 84 % yield) as yellow oil: IR (thin film) 1692 cm'1; 1H NMR (300 MHz. CDCI3) δ 8.71 (t, J= 1.4 Hz. 1H), 8.35 (d, J= 2.6 Hz, 1 H), 7.83 (dt, J= 9.5, 2.3 Hz, 2H), 3.18 (s, 3H), 2.65 (q, J= 7.5 Hz, 2H), 1.44 (s, 9H), 1.25 (t, J = 7.1 Hz, 3H); EIMS m/z 320.
Example 35: Préparation of N-(1-(5-f1uoropyrldln-3-yl)-3-formyl-1H-pyrazol-4yl)lsobutyramlde (Compound 560)
To a solution of N-(1-(5-fluoropyridin-3-yl)-3-vinyl-1H-pyrazol-4-y!)isobutyramide (0.706 g, 2.57 mmol) In tetrahydrofuran (12.87 ml) and water (12.87 ml) was added osmium tetroxide (0.164 ml,
0.026 mmol). After 10 minutes at room température, sodium periodate (1.101 g, 5.15 mmol) was added In portions over 3 minutes and the resulting solution was stirred at room température. After 18 hours, the solution was poured into 10 mL water and was extracted with 3 x 10 mL dichloromethane. The combined organic layers were dried, concentrated and chromatographed (0' 70
100% ethyl acetate / hexanes) to give N-(1-(5-fluoropyridin-3-yl)-3-formyl-1H-pyrazol-4yl)lsobutyramide (828 mg, 2.288 mmol, 88 % yield) as a yellow solid: mp 140.0-142.0 eC; ’H NMR (300 MHz. CDCi3) δ 10.12 (s, 1H), 9.14 (s, 1H), 8.90 (d, J-2.0 Hz, 1H), 8.82 (s, 1 H). 8.51 (d, J =
2.5 Hz, 1H), 7.92(dt, J-9.2, 2.4Hz, 1H), 2.85 (dt, J= 13.8,8.9 Hz, 1H), 1.31 (d, J = 8.9 Hz, 8H); ESIMS m/z 277 ([M+H]*).
Compound 369 was prepared in accordance with the procedures disclosed In Example 35.
Example 36: Préparation of N-(1-(5-fluoropyrldin-3-yl)-3-(hydroxymethyl)-1W-pyrazol-4yl)lsobutyramlde (Compound 435) and N-(1-(5-fluoropyrldln-3-yl)-1H-pyrazol-4yl)lsobutyramlde (Compound 436)
To a solution of /V-(1-(5-fluoropyridin-3-yl)-3-formyl-lH-pyrazol-4-yl)isobutyramide (0.315 g, 1.140 mmol) in methanol (5.70 mi) at 0 *C was added sodium borohydride (0.088 g, 2.280 mmol). The reaction was stirred at 0 ’C for 2 hours, and room température for 20 hours. 0.5 M HCl was added, the reaction was neutrallzed with saturated aqueous sodium bicarbonate, and the mixture was extracted with dichloromethane. The organic phases were concentrated and chromatographed (ΟΙ 00% ethyl acetate / hexanes) to give N-(1-(5-fluoropyridin-3-yl)-3-(hydroxymethyl)-1H-pyrazol-4yl)isobutyramide (180 mg, 0.847 mmol, 58.7 %) as a white solid and A/-(1-(5-fluoropyridin-3-yl)-1Hpyrazoi-4-yl)isobutyramide (9 mg, 0.038 mmol, 3.18 %) as a white solid.
A/-(1-(5-Fluoropyridin-3-yl)-3-(hydroxymethyl)-1H-pyrazol-4-yl)isobutyramlde: mp 144.0-148.0 ‘C; 1H NMR (400 MHz, CDCi3) δ 8.74 (d, J = 1.1 Hz, 1H), 8.84 (s, 1 H), 8.37 - 8.29 (m, 2H), 7.74 (dt, J =
9.5, 2.3 Hz, 1H), 4.95 (d, J = 3.0 Hz, 2H), 3,21 - 3,08 (m, 1H), 2.83 - 2.48 (m, 1 H). 1.28 (d, J = 8.9 Hz, 6H); ESIMS m/z 279 ([M+H]*).
N-(1-{5-Fluoropyridin-3-yl)-1H-pyrazol-4-yl)isobutyramide: IR (thin film) 1659 cm'1; 1H NMR (400 MHz, CDCI3) δ 8.79 (d, J= 1.2 Hz, 1 H). 8.60 (s, 1H), 8.38 (d, J= 2.5 Hz, 1 H). 7.81 (dt, J= 9.5,2.3
Hz, 1H), 7.68 (s, 1H), 7.54 (s, 1H), 2.63 - 2.51 (m, 1H), 1.28 (d. J = 6.9 Hz, 6H); ESIMS m/z 249 ([M+H]*).
Example 37: Préparation of N-(3-(chloromethyl)-1-(5-fluoropyrldln-3-yl)-1H-pyrazol-4yl)lsobutyramide (Compound 561)
To a solution of N-(1-(5-fluoropyridin-3-yl)-3-(hydroxymethyl)-1H-pyrazol-4-yl)isobutyramide (0.100 g, 0.359 mmol) In dichloromethane ( 3.59 ml) was added thlonyl chloride (0.157 ml, 2.151 mmol). The reaction was stirred at room température for 2 hours. Saturated aqueous sodium bicarbonate was added, and the mixture was extracted with dichloromethane. The combined organic phases were washed with brine and concentrated to give /V-(3-(chloromethyl)-1-(5-fluoropyridin-3-yl)-1/7pyrazol-4-yl)isobutyramide (100 mg, 0.337 mmol, 94 % yield) as a white solid: mp 172.0-177.0 ’C; 1H NMR (400 MHz, CDCI3) δ 8.79 (s, 1 H), 8.67 (s, 1H), 8.40 (s, 1H), 7.80 (dt, J- 9.4, 2.3 Hz, 1H), 7.42 (s, 1 H), 4.77 (s, 2H), 2.63 (hept, J= 6.9 Hz, 1H), 1.30 (d, J- 6.9 Hz, 6H); ESIMS m/z 298 ([M+H]*).
Example 38: Préparation of /V-(3-chioro-1-(pyrldln-3-yl)-lH-pyrazo!-4-yl)-/V-ethyl-2methoxyacetamlde (Compound 512) (see also Example 11)
To a solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amïnet 2HCI (0.130 g, 0.502 mmoi) and in DCM (2.508 ml) was added N-ethyl-N-isopropylpropan-2-amine (0.257 ml, 1.505 mmol) followed by 2-methoxyacety! chloride (0.109 g, 1.003 mmol) and the reaction mixture was stirred at ambient température for 16 hours. The reaction was quenched by the addition of saturated sodium bicarbonate. The organic layer was extracted with DCM. The organic layer was dried over sodium sulfate, filtered, concentrated and purified using silica gel chromatography (0-100% ethyl acetate / hexanes) to yield the title compound as a pale yellow oil (0,12 g, 77%): IR (thîn film) 3514, 3091, 2978,1676 cm*1; 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J= 2.4 Hz, 1H), 8.63 (d, J~3.8 Hz, 1H), 8.09 - 8.03 (m, 1H), 7.99 (s, 1H), 7.47 (dd, J = 8.3, 4.8 Hz, 1H), 3.88 (s, 2H), 3.77 - 3.65 (m, 2H), 3.40 (s, 3H), 1.18 (t, J = 7.2 Hz, 3H); ESIMS m/z 295 ([M+H]*).
Compounds 71,478,481,483 - 484, and 543 were prepared ln accordance with the procedures disclosed ln Example 38.
Example 39: Préparation of N-(3-chloro-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2methyl-3-(methy1thio)butanamlde (Compound 182) and (Z)-N-(3-chloro-1-(5-fluoropyr|dln-3yl)-1H-pyrazol-4-yl)-N-ethyl-2-methylbut-2-enamlde (Compound 183)
To a solution 2-methyl-3-(methylthio)butanoic acid (0.154 g, 1.039 mmoi) ln dichloromethane (1 mL) at room température was added 1 drop of dimethylformamide. Oxaiyl dichloride (0.178 ml, 2.078 mmol) was added dropwise and the reaction was stirred at room température overnight. The solvent was removed under reduced pressure. The residue was redlssolved In dichloromethane (1 mL) and the solvent was removed under reduced pressure. The residue was redlssolved ln dichloromethane (0.5 mL) and the solution was added to a solution of 3-chloro-N-ethyL1-(5fluoropyridin-3-yi)-1H-pyrazol-4-amine (0.100 g. 0.416 mmol) and 4-dimethylaminopyridine (0.254 g, 2.078 mmol) ln dichloromethane (1.5 mL) and stirred at room température overnight. The solvent was removed under reduced pressure and the residue was purify by chromatography (0-100% ethyl acetate / hexanes) to give N-(3-chloro-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyb2methyt-3-(methytthlo)butanamlde (34 mg, 0.092 mmol, 22.06 %) as a faint yellow oil and (Z)-A/-(3ch1oro-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-y!)-A/-ethyl-2-methytbut-2-enamide (38 mg, 0.118 mmol,
28.3 % yield) as a yellow oil.
A/-(3-Chloro-1 -(5-fluoropyrldin-3-yl)-1 H-pyrazol-4-yl)-N-ethyl-2-methyl-3-(methylthio)butanamide: IR (thin film) 1633 cm*1; 1H NMR (400 MHz, CDCI3) δ 8.79 (d, J = 2.0 Hz, 0.66H), 8.77 (d, J - 2.0 Hz, 0.33H), 8.50 (d, J= 2.6 Hz, 0.33H), 8.49 (d, J= 2.5 Hz, 0.66H), 8.08 (s, 0.66H), 7.95 (s, 0.33H),
7.92 - 7.81 (m, 1H), 4.03 - 3.46 (m, 2H), 3.03 - 2.78 (m, 1H), 2.59 - 2.33 (m, 1H), 2.04 (s, 2H), 2.02 (s, 1 H), 1.32 (d, J = 6.7 Hz, 1 H), 1.27 (d, J - 6.2 Hz, 1 H), 1.23 (d, J = 6.9 Hz, 2H), 1.18 -1.12 (m, 5H); ESIMS m/z 371 ([Mf).
(Z)-N-(3-Chloro-1 -(5-fluoropyridin-3-yl)-1H-pyrazol-4-y!)-N-ethy!-2-methy!but-2-enamide: 1H NMR (400 MHz, CDCI3) δ 8.73 (d, J- 2.0 Hz, 1H), 8.46 (d, J= 2.4 Hz, 1H), 7.87 (d, J~ 4.9 Hz, 1H), 7.84 (dt, J = 9.2, 2.4 Hz, 1 H), 5.93 - 5.76 (m, 1 H), 3.73 (q, J = 7.1 Hz, 2H), 1.72 (s. 3H), 1.58 (dd, J =
6.9, 0.9 Hz, 3H), 1.17 (t, J= 7.1 Hz, 3H); ESIMS m/z 323 ([M]*).
Compounds 70,180 - 181, 389 - 392, 397 - 398,405 - 406, 427 - 429, 432, 456, 482, 521 -522, 532 - 534, 555, and 589 were prepared from the corresponding Intermediates and starting materials in accordance with the procedures disclosed In Example 39.
Example 40: Préparation of N-(3-chloro-1-(pyrldln-3-y1)-1W-pyrazol-4-y1)-N-methyl-2(methylthio)acetamide (Compound 337)
Cl Q S—
To an Ice cold solution of 2-(methytthio)acetic acid (0.092 g, 0.863 mmol) In DCM (2 mL) was added N-ethyl-N-isopropytpropan-2-amlne (0.111 g, 0.863 mmol) followed by isobutyl chloroformate (0.099 mi, 0.767 mmol). Stirring was contînued for 10 minutes. Next, the mixed anhydride was added to a solution of 3-chloro-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.08 g, 0.383 mmol) in DCM (0.66 mL) and the reaction mixture was stirred at ambient température for 2 hours. The reaction mixture was concentrated and purified using reverse phase C-18 coiumn chromatography (0-100% CH3CN / H2O) to yieid the title compound as a pale yellowoil (0.075 g, 66%): ’H NMR (400 MHz. CDCf3) δ 8.95 (d, J= 2.5 Hz. 1H). 8.62 (dd, J = 4.8,1.4 Hz. 1H). 8.13 (s, 1H), 8.04 (ddd, J = 8.3,2.7.1.4 Hz, 1 H), 7.50 - 7.43 (m, 1H), 3.26 (s, 3H), 3.12 (s, 2H), 2.24 (s, 3H); ”C NMR (101 MHz, CDCI3) δ 170.00,148.61,140.15,140.03,135.68,126.56,126.42, 125.33,124.15, 37.16, 34.94,16.22: ESIMS m/z 297 ([M+H]*).
Compounds 335,336, and 542 were prepared In accordance with the procedures disclosed In Example 40.
Example 41, Préparation of N-(3-ch!oro-1-(pyridin-3-yl)-1H-pyrazoi-4-yl)-N-ethyl-2-methyl-3oxobutanamlde (Compound 499)
To a solution of 3-chforo-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, HCi (259 mg, 1 mmol) and ethyl 2-methyl-3-oxobutanoate (144 mg, 1.000 mmol) In dioxane (1 mL) was added 2,3,4,6,7,8hexahydro-1H-pyrimido[1,2-a]pyrimidine (181 mg, 1.30 mmol) and the mixture was heated in a microwave (CEM Discover) at 150 'Cfor 1.5 h, with extemal IR-sensor température monitoring from the bottom of the vessel. LCMS (ELSD) Indicated a 40% conversion to the desired product. The mixture was diluted with ethyl acetate (50 ML) and saturated aqueous NfyCi (15 mL), and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (20 mL) and the combined organic phase was washed with brine, dried overMgSO« and concentrated in vacuo to give an oily residue. This residue was purified on silica gel eluting with mixtures of ethyl acetate and hexanes to give N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2-methyl-3oxobutanamide (37 mg, 11 % yield, 96% purity) as a coloriées oil: ’H NMR (400 MHz, CDCI3) δ 9.02 - 8.92 (dd, J = 2.6, 0.8 Hz, 1 H), 8.68 - 8.60 (dd, J = 4.8,1.5 Hz, 1 H), 8.09 - 7.98 (m, 1 H), 7.96 -
7.87 (s, 1 H), 3.87 - 3.58 (d. J = 3.0 Hz, 2H), 3.49 - 3.38 (m, 1H), 2.16 - 2.08 (s, 3H), 1.39 -1.32 (d.
J = 7.0 Hz, 3H), 1.22-1.13 (m, 3H); EIMS (m/z) 321 ([M+1]*), 319 ([Μ-1Γ).
Example 42: Préparation of N-(3-ch1oro-1-(pyrldln-3-yl)-1H-pyrazo1-4-yl)-Nethylcyclopropanecarboxamlde (Compound 538)
To a solution of 3-chloro-N-ethy!-1-(pyridin-3-yl)-1H-pyrazol-4-amine monohydrochloride (0.10 g, 0.0.38 mmol) In dichloroethane (0.75 ml) was added cyclopropanecarboxylic acid (0.03 g, 0.38 mmol) and 4-N,N-dimethy!amlnopyridine (0.14 g, 1.15 mmol) followed by 1-(3dimethylaminopropy!)-3-ethylcarbodiimide hydrochloride (0.14 g, 0,77 mmol). The reaction was stirred at room température ovemight. The reaction mixture was concentrated to dryness and the crude product was purified by reverse phase silica gel chromatography eluting with 0-50% acetonitrile / water to give a white solid (0.03 g, 25%); mp 111-119 C; 1H NMR (400 MHz, CDCI3) δ
8.98 (d, J = 2.5 Hz, 1H), 8.63 - 8.59 (m, 1H), 8.06 (ddd, J = 8.3,2.6,1.4 Hz, 1 H), 8.01 (s, 1H), 7.46 (dd, J= 8.3, 4.7 Hz, 1H), 3.73 (q, J = 7.2 Hz, 2H), 1.46 (ddd, J= 12.6, 8.1, 4.7 Hz, 1H), 1.16 (t, J = 7.2 Hz, 3H), 1.04 (t, J = 3.7 Hz, 2H), 0.71 (dd, J = 7.7, 3.0 Hz, 2H); ESIMS m/z 291 ([M+H]).
Compounds 69, 516, 524, 546, 558 - 559, 582-588, 593, and 594 were prepared from the appropriate acids in accordance with the procedures disclosed In Exemple 42.
Example 43: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazo1-4-yl)-2-methyl-3(methylthIo)-N-(3-(methylthlo)propanoyl)propanamlde (Compound 407)
To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-(methylthio)propanamide (0.216 g, 0.728 mmol) in DCE (2.91 ml) in a 10 mL vial was added 2-methyl-3-(methylthio)propanoyl chloride (0.244 g, 1.601 mmol). The vial was capped and placed in a Biotage Initiator microwave reactor for 3 hours at 100 ’C, with external IR-sensor température monitoring from the side of the vessel. The crude mixture was concentrated and purified using reverse phase C-18 column chromatography (ΟΙ 00% acetonitrile / water) to yield the title compound as a pale yellow oil (67 mg, 22%): IR (thln film) 2916 and 1714 cm'1; Ή NMR (300 MHz, CDCI3) δ 8.96 - 8.92 (d, J-2.7 Hz, 1 H), 8.64 - 8.59 (dd, J= 4.9,1.4 Hz, 1H), 8.07 - 7.99 (m, 2H), 7.50-7.40 (dd, J- 8.4,4.8 Hz, 1H), 3.39 - 3.28 (m, 1H), 3.10-2.99 (td, J= 7.2, 3.9 Hz, 2H), 2.96 - 2.86 (dd, J= 13.2, 8.7 Hz, 1H), 2.86 - 2.79 (t, J-
7.3 Hz, 2H), 2.58 - 2.48 (dd, J = 13.1, 5.8 Hz, 1 H), 2.14 - 2.12 (s, 3H), 2.09 - 2.06 (s, 3H), 1.30 1.26 (d, J- 6.9 Hz, 3H); ESIMS m/z 413 ([M+H]*).
Compounds 383,410,433,437,451,470, 530 and 531 were prepared ln accordance with the procedures disclosed in Example 43.
Example 44: Préparation of A/-[3-chloro-1-(3-pyrldyi)pyrazol-4-yl]-2,2-dideuterlo-N-ethyl-3methylsulfanyi-propanamide (Compound 393)
To a 7 mL vial was added 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (111 mg, 0.5 mmol),
2,2-dideuterio-3-methylsulfanyl-propanoic acid (58.0 mg, 0.475 mmol) and followed by DCM (Volume: 2 mL). The solution was stirred at 0 ’C. Then the solution of DCC (0.500 mL, 0.500 mmol, 1.0M in DCM) was added. The solution was allowed to warm up to 25 °C slowly and stirred at 25 °C ovemight. White precipitate formed during the reaction. The crude reaction mixture was filtered through a cotton plug and purified by silica gel chromatography (0-100% EtOAc / hexane) to giveN-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2,2-dideuterio-N-ethyl-3-methylsulfanyl-propanamide (97 mg, 0.297 mmol, 59.4 % yield) as a colorless oil: 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J- 2.4 Hz,
H), 8.63 (dd, J- 4.6, 0.9 Hz, 1 H). 8.06 (ddd, J = 8.4,2.7,1.4 Hz, 1H), 7.98 (s, 1H), 7.52 - 7.40 (m,
H), 3.72 (q, J= 7.2 Hz, 2H), 2.78 (s, 2H), 2.06 (s, 3H), 1.17 (t, J - 7.2 Hz, 3H); ESIMS m/z 327 ([M+H]*); IR (Thin film) 1652 cm*1.
Compounds 394, 396, and 471 - 473 were prepared from the corresponding intermediates and starting materials In accordance with the procedures disclosed in Example 44.
Example 45: Préparation of 1-ethyl-3-(3-methyl-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)urea (Compound 145)
To a solution of 3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amlne (0.1 g, 0.574 mmol) in DCM (5.74 mi) was added ethyl Isocyanate (0.041 g, 0.574 mmol) and the reaction mixture was stirred at ambient 15 température for 40 minutes. The reaction mixture had tumed from a clear solution to a suspension with white solid material. The reaction mixture was concentrated and purifîed using silica gel chromatography (0-20% MeOH / DCM) to yield the title compound as a white solid (0.135 g, 95%): mp 197-200 °C; 1H NMR (400 MHz, CDCI3) δ 8.94 (d, J- 2.3 Hz, 1H), 8.48 - 8.37 (m, 1H), 8.32 (s, 1 H), 7.94 (d, J = 8.3 Hz, 1 H), 7.52 (br s, 1 H), 7.41 - 7.25 (m, 1 H), 5.79 (br s, 1 H), 3.33 - 3.23 (m, 20 2H), 2.29 (d, J - 2.9 Hz, 3H), 1.16 (dd, J = 8.7, 5.7 Hz, 3H); ESIMS m/z 246 ([M+H]*), 244 ([M-H]).
Compounds 169 - 171,221 - 222, 255 - 257, 278 - 280,297 - 302, 318 - 322, 334, 345,
348, 375-377, 385-387, and 411 -413 were prepared In accordance with the procedures disclosed In Example 45.
Example 46: Préparation of 3-butyt-1-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-1-ethylurea (Compound 500)
To a solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, 2HCI (0.130 g, 0.502 mmol) in DCE (1.25 ml) was added N-ethyl-N-lsopropylpropane-2-amine (0.21 mL, 1.255 mmol) followed by 1-isocyanatobutane (0.109 g, 1.104 mmol) and the reaction mixture was stirred at ambient température for 16 hours. The reaction mixture was concentrated and purified using silica gel chromatography (0-20% MeOH / DCM) to yield the title compound as a beige solid (0.131 g, 77%): IR (thin film) 3326,2959, 2931,1648 cm·1; Ή NMR (400 MHz, CDCI3) δ 8.95 (s, 1H), 8.62 (d, J = 4.0 Hz, 1H). 8.08-8.01 (m, 1H), 7.97 (s, 1H), 7.46 (dd, J= 8.3,4.7 Hz, 1 H), 4.42-4.32 (m, 1 H),
3.74 - 3.61 (m, 2H), 3.27 - 3.15 (m, 2H), 1.49 -1.37 (m, 2H), 1.37 -1.22 (m, 2H), 1.19 -1.12 (m, 3H), 0.94 - 0.84 (m, 3H); ESIMS m/z 322 ([M+H]*).
Compounds 479 - 480,501 - 504, 513, 518 and 519 were prepared according to Example
46.
Example 47: Préparation of 1-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)imldazolldln-2-one (Compound 374)
Cl O
KnH îj
N
To a solution of 1-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-(2-chloroethyl)urea (0.1 g, 0.333 mmol) in THF (6.66 ml) was added sodium hydride (8.00 mg, 0.333 mmol) and the reaction mixture was stirred at ambient température for 30 minutes. The reaction was quenched by the addition of a solution of saturated ammonium chloride and the product was extracted with ethyl acetate (2x). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The product was a beige solid which was pure and did not need any further purification (63 mg, 72%): mp 16779
170 °C; 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.2 Hz, 1 H), 8.56 (dd, J = 4.7,1.4 Hz, 1 H), 8.33 (s, 1 H), 7.99 (ddd, J = 8.3, 2.7,1.4 Hz, 1 H), 7.40 (ddd, J= 8.3,4.8,0.7 Hz, 1H), 5.00 (s, 1 H), 4.14 4.07 (m, 2H), 3.68 - 3.58 (m, 2H); ESIMS m/z 264 ([M+H]*).
Compound 349 was prepared in accordance with the procedures disclosed in Example 47.
Example 48: Préparation of S-tert-butyl (3-chloro-1-(pyridln-3-y1)-1H-pyrazol-4yl)(ethyl)carbamothloate (Compound 514)
To a solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, 2HCI (0.13 g, 0.502 mmol) in DCM (2.508 ml) was added W-ethyl-N-isopropylpropan-2-amine (0.257 ml, 1.505 mmol) followed by
S-terf-butyl carbonochloridothioate (0.153 g, 1.003 mmol). The reaction mixture was stirred at ambient température for 16 hours. The reaction was quenched by the addition of saturated sodium bicarbonate. The organic layer was extracted with DCM. The organic layer was dried over sodium sulfate, filtered, concentrated and purified using silica gel column chromatography (0-100% ethyl acetate / hexanes) to yield the title compound as a whlte solid (132 mg, 78%): mp 91-93 °C; 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.5 Hz, 1H), 8.60 (dd, J - 4.7,1.4 Hz, 1H), 8.08 - 8.03 (m,
1 H), 7.97 (s, 1H), 7.47 - 7.41 (m, 1H), 3.69 (q, J = 7.2 Hz, 2H), 1.47 (s, 9H), 1.21 - 1.13 (m, 3H);
ESIMS m/z 339 ([M+H]*).
Compounds 333,338, 339, 346,368 and 373 were prepared in accordance with the procedures disclosed in Example 48.
Example 49: Préparation of N-(3-chloro-1-(pyridin-3-y1)-1H-pyrazol-4-yl)-N-ethy1-2-methyl-3(methio)propanethloamlde (Compound 364)
To a mîcrowave reaction vessel was added N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-2methy1-3-(methîo)propanannide (0.07 g, 0.22 mmol) in dichioroethane (1.87 mL) and Lawesson’s reagent (0.05 g, 0.12 mmol). The vessel was capped and heated in a Biotage Initlator microwave reactor for 15 minutes at 130 °C, with extemal IR-sensor température monitoring from the side of the vessel. The réaction was concentrated to dryness and the crude material was purified by silica gel chromatography (0-80% acetonitrile / water) to give the desired product as a yellow oil (0.33 g, 44%); IR (thin film) 1436 cm’1; Ή NMR (400 MHz, CDCI3) δ 8.97 (d, J= 2.5 Hz, 1H), 8.77 - 8.52 (m, 1H), 8.11 - 7.89 (m, 2H), 7.60 - 7.38 (m, 1H), 4.62 (bs, 1H), 4.02 (bs, 1H), 3.21 - 2.46 (m, 3H), 2.01 (s, 3H), 1.35 -1.15 (m, 6H); ESIMS m/z 355 ([M+H]*).
Compounds 372,438 and 548 were prepared In accordance with the procedures disclosed in Example 49.
Example 50: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-N-ethy1-4,4,4trlfluoro-3-(methylsulf1ny1)butanamlde (Compound 570)
To a 20 mL viai was added N-tS-chloro-l-Îpyridin-S-ylJ-IH-pyrazoi^yO-N-ethyM^Atrifluoro-S(methylthio)butanamide (82 mg, 0.209 mmol) and hexafluoroisopropanol (1.5 mL). Hydrogen peroxide (0.054 mL, 0.626 mmol, 35% solution In water) was added in one portion and the solution was stirred at room température. After 3 hours the reaction was quenched with saturated sodium sulfite solution and extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over sodium sulfate, concentrated and purified by chromatography (0-10% MeOH / DCM) to give N-(3 chloro-1-{pyridin-3-yl)-1H-pyrazol-4-y1)-N-ethyl-4>4l4-trifluoro-3-(methylsulfinyl) butanamide (76 mg, 0.186 mmol, 89 % yield) as white semi-solid: ’H NMR (400 MHz, CDCI3) δ 8.98 (d, J= 2.3 Hz, 1H),
8.63 (td, J- 4.8,2.4 Hz, 1H), 8.14-8.01 (m, 2H), 7.46 (ddd, J - 8.3,4.8,0.7 Hz, 1H), 4.26 (dd, J =
17.2, 8.4 Hz, 1 H), 3.89 - 3.61 (m, 2H), 3.01 (dd, J - 17.6, 8.2 Hz, 1 H), 2.77 (s, 2H), 2.48 (dd, J -
17.7,3.3 Hz, 1H), 1.19 (t, J = 7.2 Hz, 3H) (only one Isomer shown); ESIMS m/z 409 ([M+H]*); IR (Thin film) 1652 cm'1.
Compound 571 was prepared from the corresponding intermediates and starting materials In accordance with the procedures disclosed in Example 50.
Example 51: Préparation of N-(3-chloro-1-(pyridln-3-y1)-1H-pyrazol-4-yl)-N-ethyl-3(methylsulfinyl)propanamlde (Compound 362)
To N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methylthlo)propanamide (0.08 g, 0.24 mmol) in glacial acetic acid (0.82 mL) was added sodium perborate tetrahydrate (0.05 g,, 0.25 mmol), and the mixture was heated at 60 °C for 1 hour. The reaction mixture was carefuliy poured Into a separatory funnel containing saturated aqueous NaHCO3 resulting in gas évolution. When the gas évolution had ceased, ethyl acetate was added and the layers were separated. The aqueous layer was extracted twice with ethyl acetate, and ail the organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (0-10% methanol / dichloromethane) to give the desired product as a ciear oil (0.03 g, 40%): IR (thin film) 1655 cm'1; ’H NMR (400 MHz, CDCb) δ 8.95 (t, J = 9.2 Hz, 1 H), 8.63 (dd, J = 4.7,1.4 Hz, 1 H), 8.20 - 7.86 (m, 2H), 7.59 - 7.33 (m, 1 H), 3.73 (ddt, J = 20.5,13.4, 6.8 Hz, 2H), 3.23 - 3.06 (m, 1H), 2.94 - 2.81 (m, 1H), 2.74 - 2.62 (m, 2H), 2.59 (s, 3H), 1.25 -1.07 (m, 3H); ESIMS m/z 341 ([M+H]*).
Compounds 101 -102,218, 328,330, and 494 were prepared from the appropriate sulfides in accordance with the procedures dîsclosed In Example 51.
Example 52: Préparation of N-(3-chloro-1-(pyrldin-3-y1)-1H-pyrazo!-4-y1)-N-ethyl-3(methylsulfonyl)propanamide (Compound 363)
To N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methylthIo)propanamlde (0.08 g, 0.25 mmol) In glacial acetic acid (0.85 mL) was added sodium perborate tetrahydrate (0.11 g, 0.52 mmol), and the mixture was heated at 60 °C for 1 hour. The reaction mixture was carefully poured Into a separatory funnel containing saturated aqueous NaHCO3 resulting in gas évolution. When the gas évolution had ceased, ethyl acetate was added and the layers were separated. The aqueous layer was extracted twice with ethyl acetate, and ail the organic layers were combined, dried over MgSOx, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0 to 10% methanol / dichloromethane) to give the desired product as a clear oil (0.04, 47%): (thln film) 1661 cm-1; 1H NMR (400 MHz, CDCI3) δ 8.95 (t, J = 11.5 Hz, 1 H), 8.64 (dd, J = 4.8,1.4 Hz, 1 H), 8.17 - 7.96 (m, 2H), 7.59 - 7.39 (m, 1 H), 3.73 (d, J =7.0 Hz, 2H), 3.44 (dd, J= 22.5,15.7 Hz, 2H), 2.96 (s, 3H), 2.71 (t, J =6.9 Hz, 2H), 1.18 (dd, J = 8.8, 5.5 Hz, 3H); ESIMS m/z 357 ([M+H]*).
Compounds 103,104, 219, 329,331 and 495 were prepared from the appropriate sulfides In accordance with the procedures dîsclosed In Example 52.
Exemple 53: Préparation of N-(3-methyt-1-(3-fluoropyrldin-5-yl)-1H-pyrazol-4-y1)N-ethyl-2methyl-(3-oxldo-D4-suifanylldenecyanamlde)(methyl)propanamlde (Compound 250)
To a solution of N-ethyl-N-(1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-yl)-2-methyl-3(methylthio)propanamide (0.30 g, 0.89 mmol) ln dichloromethane (3.57 mL) at 0 ’C was added cyanamide (0.07 g, 1.78 mmol) and iodobenzenediacetate (0.31 g, 0.98 mmol) and subsequently stirred at room température for 1 hour. The reaction was concentrated to dryness and the crude material was purified by silîca gel column chromatography (10% methanol / ethyl acetate) to give the desired sulfilamine as a light yellow solid (0.28 g, 85%). To a solution of 70% mCPBA (0.25 g, 1.13 mmol) ln éthanol (4.19 mL) at 0 ’C was added a solution of potassium carbonate (0.31 g, 2.26 10 mmol) in water (4.19 mL) and stirred for 20 minutes after which a solution of sulfilamine (0.28 g, 0.75 mmol) ln éthanol (4.19 mL) was added ln one portion. The reaction was stirred for 1 hour at 0 ’C. The excess mCPBA was quenched with 10% sodium thiosulfite and the reaction was concentrated to dryness. The residue was purified by silica gel chromatography (0-10% methanol / dichloromethane) to give the desired product as a clear oil (0.16 g, 56%): IR (thin film) 1649 cm'1;
’H NMR (400 MHz, CDCIa) δ 8.80 (dd, J = 43.8,10.1 Hz, 1H), 8.51 - 8.36(m, 1H), 8.11 (d, J- 38.7 Hz, 1H), 7.96 - 7.77 (m, 1 H), 4.32 - 3.92 (m, 2H), 3.49 - 3.11 (m, 6H), 2.32 (s, 3H), 1.27-1.05 (m, 6H); ESIMS m/z 393 ([M+H]*).
Example 54: Préparation of N-ethy!-4,4,4-trlfluoro-3-methoxy-N-(3-methyl-1-(pyrldln-3-yl)-1H· 20 pyrazol-4-yl)-3-(trifluoromethyl)butanamlde (Compound 276)
To a solution of N-ethyl-4,4,4-trifluoro-3-hydroxy-N-(3-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-325 (trifluoromethyl)butanamide (184 mg, 0.448 mmol) ln DMF (3 mL) stirring at 0 ’C was added sodium hydride (26.9 mg, 0.673 mmol). The solution was stirred at 0 ’C for 0.5 hour. Then iodomethane (0.034 mL, 0.538 mmol) was added and Ice bath was removed and the mixture was 84 stirred at 25 °C ovemight. Reaction was worked up by slow addition of water and further diluted with 20 mL of water, then extracted with 4x20 mL of EtOAc. The combined organic layers were washed with water, dried over Na2SO< and concentrated. Silica Gel chromatography (0-100% EtOAc / hexa ne) gave N-ethyl-4,4,4-trifluoro-3-methoxy-/V-(3-methyl-1-(pyridin-3-yl)-1H-pyrazoi-4yi)-3-(trifluoromethyl)butanamide (52 mg, 0.123 mmol, 27.3 % yield) as a white solid: mp » 83-86 °C; 'H NMR (400 MHz, CDCI3) δ 8.94 (d, J- 2.5 Hz, 1H), 8.59 (dd, J = 4.7,1.3 Hz, 1H), 8.01 (ddd, J- 8.3,2.7,1.5 Hz, 1 H). 7.85 (s, 1H), 7.44 (ddd, J = 8.3,4.8, 0.6 Hz, 1H), 4.00 (brs, 1 H). 3.73 (s, 3H), 3.39 (brs, 1 H), 2.86 (s, 2H), 2.26 (s, 3H), 1.16 (t, J= 7.1 Hz, 3H); ESIMS m/z 425 ([M+H]*); IR (Thin film) 1664 cm-1.
Compound 327 was prepared from the corresponding Intermediates and starting materials In accordance with the procedures disciosed In Example 54.
Example 55, Step 1 : Préparation of N-(2-((te/t-butyldimethy1sliy1)oxy)ethyl)-N-{3-chloro-1(pyridln-3-yi)-1H-pyrazol-4-yl)-2-methyl-3-(methy1thlo)propanamlde
A solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-methyl-3-(methylthlo)propanamide (0.150 g, 0.483 mmol) in Ν,Ν-dimethylformamide (2.413 ml) was cooled to 0 *C. Sodium hydride (0.039 g, 0.965 mmol, 60% dispersion) was added at and the reaction was stirred at 0 °C for 30 minutes. (2-Bromoethoxy)(tert-butyl)dimethylsilane (0.231 g, 0.965 mmol) was added, the ice bath was removed, and the reaction was stirred at room température for 2 hours. The reaction was heated at 65 °C for 1.5 hours and then cooled to room température. Brine was added and the mixture was extracted with dichloromethane. The combined organic phases were concentrated and chromatographed (0-100% ethyl acetate / hexanes) to give N-(2-((tert-butyldimethylsilyl)oxy)ethyl)N-(3-chloro-1-(pyridin-3-yl)-1 H-pyrazol-4-yl)-2-methyl-3-(methylthio)propanamide (0.120g, 0.243 mmol, 50.4 %) as an orange oil: IR (thin film) 1669 cm‘1; 1H NMR (400 MHz, CDCI3) δ 8.88 (d, J~
2.5 Hz, 1H), 8.55 (dd, J- 4.7,1.4 Hz, 1H), 8.05 (s, 1H). 7.98 (ddd, J = 8.3, 2.6,1.4 Hz, 1H), 7.41 (ddd, J= 8.4, 4.8, 0.5 Hz, 1H), 4.35-3.06 (m. 4H), 2.86-2.73 (m, 1H). 2.73-2.59 (m, 1H), 2.41 (dd, J= 12.8, 5.7 Hz, 1 H), 1.94 (s, 3H). 1.11 (d, J= 6.7 Hz, 3H), 0.80 (s, 9H), 0.00 (s, 3H), -0.01 (s, 3H); ESIMS m/z 470 ([M+H]*).
Example 55, Step 2: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-N-(2· hydroxyethyl)-2-methyl-3*(methytthlo)propanamlde (Compound 535)
To a solution of N-(2-((tert-butyidimethyisilyi)oxy)ethyl)-N-(3-chloro-1-(pyridin-3-yl)-1/-/-pyrazol-4-yl)-
2-methy1-3-(methy1thio)propanamide (0.180 g, 0.384 mmol) In tetrahydrofuran (1.54 ml) was added tetrabutylammonium fluoride (0.201 g, 0.767 mmol) and the reaction was stirred at room température for 2 hours. Brine was added and the mixture was extracted with ethyl acetate. The combined organic phases were concentrated and chromatographed (0-100% water / acetonitrile) to give N-(3-chloro-1 -( pyrid in-3-y1)-1 H-pyrazol-4-yl)-N-(2-hydroxyethyl)-2-methyl-3(methylthio)propanamide as a white oil (0.081g, 0.217 mmol, 56.5 %): IR (thin film) 3423,1654 cm' 1; 1H NMR (400 MHz, CDCI3) δ 9.00 (d, J= 2.5 Hz, 1H), 8.62 (dd, J = 4.7,1.2 Hz, 1H), 8.25 (s. 1H), 8.07 (ddd, J = 8.3,2.4,1.3 Hz, 1 H), 7.47 (dd, J - 8.3,4.7 Hz, 1H), 4.47 - 3.70 (m, 3H), 3.65 - 3.09 (m, 2H), 2.91 - 2.68 (m, 2H). 2.48 (dd. J= 12.4, 5.0 Hz, 1H), 2.01 (s, 3H). 1.18 (d, J - 6.5 Hz, 3H); ESIMS m/z 356 ([M+H]*).
Example 56: Préparation of 2-(N-(3-chloro-1-(pyridln-3-yl)-1H-pyrazol-4-yl)-2-methyl-3(methylthio)propanamido)ethyl acetate (Compound 547)
ο
Το a solution of N-(3-chloro-1-(pyridin-3-y1)-1H-pyrazol-4-y!)-N-(2-hydroxyethyt)-2-methyl-3(methylthio)propanamide (0.045 g, 0.127 mmol) in dichloromethane (1,27 ml) was added N,Ndimethytpyridin-4-amlne (0.023 g, 0.190 mmoi) and triethylamine (0.019 g, 0.190 mmol) followed by acetyl chloride (0.015 g, 0.190 mmol). The reaction was stirred at room température overnight. Water was added and the mixture was extracted with dichloromethane. The combined organic phases were concentrated and chromatographed (0-100% ethyl acetate / hexanes) to give 2-(N-(3chloro-1-(pyridin-3-yl)-1H-pyrazol-4-y!)-2-methyt-3-(methyfthio)propanamido)ethy1 acetate as a yellow oil (0.015 g, 0.034 mmol, 26.8 %): IR (thin film) 1739,1669 cm’1; 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J= 2.3 Hz, 1H), 8.64 (dd, J= 4.7,1.4 Hz, 1H), 8.15 (s, 1H), 8.04 (ddd, J= 8.3, 2.7,1.4 Hz, 1 H), 7.47 (ddd, J= 8.3, 4.8, 0.7 Hz, 1 H), 4.50-3.40 (m, 4H), 2.84 (dd, J = 12.7, 8.9 Hz, 1H), 2.78-2.63 (m, 1H), 2.46 (dd, J= 12.7,5.4 Hz, 1H), 2.03 (s, 3H), 2.01 (s, 3H), 1.16 (d, J-6.6 Hz, 3H); ESIMS m/z 398 ([M+H]*).
Example 57: Préparation of 2,2-dideuterio-3-methyisulfanyl-propanolc acid
To a 100 mL round bottom flask was added 3-(methylthio)propanoic add (3 g, 24.96 mmol), followed by D2O (23 mL) and KOD (8.53 mL, 100 mmol) (40% wt solution In D2O), the solution was heated to reflux overnight. NMR showed ca. 95% D at alpha-position. The reaction was cooled down and quenched with concentrated HCl until pH<2. White precipitate appeared In aqueous layer upon acidifying. Reaction mixture was extracted with 3 x 50 mL EtOAc, the combined organic layers were dried over Na2SO4, concentrated In vacuo to almost dryness. 100 mL hexane was added and the solution was concentrated again to give 2,2-dideuterio-3-methytsulfany!-propanoic add as a colorless oil (2.539 g, 20.78 mmol, 83%): IR (Thln film) 3430,1704 cm'1; 1H NMR (400
MHz, CDCI3) δ 2.76 (s, 2H), 2,14 (s, 3H); ’3C NMR (101 MHz, CDCI3) δ 178.28, 38.14-28.55(m),
28.55,15.51; EIMS nVz 122..
2-Deuterio-2-methy!-3-methy!sulfanyl-propanolc acid was prepared as described in Exampie 57 to afford a colorless oil (3.62 g, 26.8 mmol, 60.9 %): IR (Thin film) 2975,1701 cm'1; ’H NMR (400 MHz, CDCi3) δ 11.39 -10.41 (brs, 1 H), 2.88 - 2.79 (d, J -13.3 Hz, 1 H), 2.61 - 2.53 (d, J -13.3 Hz, 1H), 2.16 - 2.09 (s, 3H), 1.32 -1.25 (s, 3H); ’3C NMR (101 MHz, CDCI3) δ 181.74, 39.74 - 39.02 (m), 37.16,16.50,16.03; EIMS m/z 135.
Example 58: Préparation of 2-methyl-3-(trldeuteriomethylsuifany1)propanolc acid
To a 50 mL round bottom flask was added 3-mercapto-2-methyipropanoic acid (5 g, 41.6 mmoi), followed by MeOH (15 mL), the solution was stirred at 25 °C. Potassium hydroxide (5.14 g, 92 mmol) was added slowly as the réaction is exothermic. Iodomethane-d3 (6.63 g, 45.8 mmol) was added slowly and then the reaction mixture was heated at 65 ’C ovemight. The reaction was worked up by addition of 2 N HCl until the mixture was acidic. It was then extracted with EtOAc (4x50 mL) and the combined organic layers were dried over Na2SO«, concentrated and purified with flash chromatography, eluted with 0-80% EtOAc / hexane to give 2-methyl-3(trideuteriomethylsulfany!)propanoic acid (4.534 g, 33.0 mmoi, 79 %) as colorless oil: IR (Thin film) 3446, 1704 cm*’; Ή NMR (400 MHz, CDCi3) δ2.84 (dd, J= 13.0, 7.1 Hz, 1H), 2.80 - 2.66 (m, 1H), 2.57 (dd, J - 13.0,6.6 Hz, 1 H). 1.30 (d, J- 7.0 Hz, 3H); EIMS m/z 137.
Example 59: Préparation of 2-hydroxy-3-(methylthlo)propanolc acid
Sodium methanethlolate (4.50 g, 64.2 mmol) was added at 25 ’C to a solution of 3-chloro-2hydroxypropanolc acid (2 g, 16.06 mmol) In MeOH (120 mL). The reaction mixture was heated at reflux for 8 hours, then cooled to 25 °C. The precipitate was removed by filtration and the filtrate was evaporated. The residue was acidified to pH 2 with 2 N MCI, extracted with EtOAc (3 x 30 mL), combined organic layers were dried with Na2SO4, concentrated to give 2-hydroxy-3(methyithio)propanolc acid as a white solid, (1.898 g, 13.94 mmol, 87 % yield): mp 55-59 °C; IR (Thin film) 2927,1698cm·1; 1H NMR (400 MHz, CDCI3) δ 6.33 (s, 3H), 4.48 (dd, J = 6.3,4.2 Hz, 1H), 3.02 (dd, J-14.2, 4.2 Hz, 1H), 2.90 (dd, J = 14.2, 6.3 Hz, 1H), 2.20 (s, 3H); EIMS m/z 136.
Example 60: Préparation of 2-methoxy-3-(methylthlo)propanolc acid
To a stirred solution of sodium hydride (0.176 g, 4.41 mmol) in DMF (5 mL) was added a solution of
2-hydroxy-3-(methylthio)propanoic acid (0.25 g, 1.836 mmol) In 1 mL DMF at 25 °C and stirred for 10 min. Vigorous bubbling was observed upon addition of NaH. Then iodomethane (0.126 mL, 2.020 mmol) was added and the solution was stirred at 25 °C ovemight. The reaction was quenched by addition of 2 N HCl, extracted with 3 x 10 mL of EtOAc, the combined organic layers were washed with water (2 x 20 mL), concentrated and purifîed by column chromatography, eluted with 0-100% EtOAc / hexane, gave 2-methoxy-3-(methylthio)propanolc acid (126 mg, 0.839 mmol,
45.7 % yield) as colorless oil: Ή NMR (400 MHz, CDCI3) δ 9.10 (s, 1H), 4.03 (dd, J = 6.9, 4.4 Hz, 1 H), 3.51 (s, 3H), 2.98 - 2.93 (m, 1 H), 2.86 (dd, J ~ 14.1, 6.9 Hz, 1 H), 2.21 (s, 3H); EIMS m/z 150.
Example 61: Préparation of 2-(acetylthlomethyl)-3,3,3-tr1fluoropropanolc acid
O O
To a 50 mL round bottom flask was added 2-(trifluoromethyl)acrylic acid (6 g, 42.8 mmol), followed by thioacetic acid (4.59 mi, 64.3 mmol). The reaction was slightly exothermlc. The mixture was then stirred at 25 °C overnight. NMR showed some starting material (-30%). One more equiv of thioacetic add was added and the mixture was heated at 95 °C for 1 hour, then allowed to cool to room température. Mixture was purified by vacuum distillation at 2.1-2.5 mm Hg, fraction distilled at 80-85 °C was mostly thioacetic add, fraction distilled at 100-110 °C was almost pure product, contaminated by a nonpolar impurity (byTLC). Itwas again purified by flash chromatography (020% MeOH / DCM), to give 2-(acetylthiomethyl)-3,3,3-trifluoropropanoic add (7,78 g, 36.0 mmol, 84 % yield) as colorless oil, which solidified under high vacuum to give a white solid: mp 28-30 °C; 1H NMR (400 MHz, CDCI3) δ 7.52 (brs, 1H), 3.44 (dt, J = 7.5, 3.5 Hz, 2H), 3.20 (dd, J -14.9,11.1 Hz, 1H), 2.38 (s, 3H); 13C NMR (101 MHz, CDCI3) δ 194.79,171.14,123.44 (q. J - 281.6 Hz), 50.47 (q, J = 27.9 Hz), 30.44, 24.69 (q, J = 2.6 Hz); ieF NMR (376 MHz, CDCI3) δ -67.82.
Example 62: Préparation of 3,3,3-trlfluoro-2-(methylthiomethyl)propanolcadd
O
CF3
To a solution of 2-(acetylthiomethyl)-3,3,3-trifluoropropanolc add (649 mg, 3 mmol) in MeOH (5 mL) stirring at 25 °C was added pellets of potassium hydroxide (421 mg, 7.50 mmol) in four portions over 5 minutes. Reaction was exothermlc. Then Mel was added in once, the reaction mixture was then heated at 65 °C for 18 hours. The reaction was then cooled down and quenched with 2N HCl until addic, and the aqueous layer extracted with chloroform (4 x 20 mL). Combined organic layer was dried, concentrated In vacuo, purified with flash chromatography (0-20% MeOH / DCM), to give 3,3,3-trifluoro-2-(methylthÎomethyl)propanoic add (410 mg, 2.179 mmol, 72.6 % yield) as a light yellow oil: Ή NMR (400 MHz, CDCI3) δ 10.95 (s, 1H), 3.49 - 3.37 (m, 1H), 3.02 (dd, J = 13.8,10.8 Hz, 1H), 2.90 (dd, J = 13.8,4.0 Hz, 1H), 2.18 (s, 3H); 13C NMR (101 MHz, CDCI3) δ 172.04 (q, J = 2.8 Hz), 123.55 (q, J = 281.2 Hz), 50.89 (q, J = 27.5 Hz), 29.62 (q, J = 2.3 Hz), 15.85; 19F NMR (376 MHz, CDC13) δ -67.98.
Example 63: Préparation of 3-(methylthlo)pentanoic acid
S,S-dimethyl carbonodithioate (1.467 g, 12.00 mmol) was added with vigorous stirring to a solution of (E)-pent-2-enoic acid (2.002 g, 20 mmol) In 30% KOH solution (prepared from potassium hydroxide (3.87 g, 69 mmol) and Water (10 mL)). The reaction mixture was slowly heated to 90eC over a period of 20-30 min. Heating was continued for 3 hours before the reaction was cooled down to 25 °C and quenched slowly with HCl. The mixture was then extracted with DCM (3 x 30 mL), combined organic layer dried and concentrated to give 3-(methylthio)pentanoic acid (2.7g, 18.22 mmol, 91 % yield) as light orange oil: IR (Thin film) 2975,1701 cm'1; 1H NMR (400 MHz, CDCI3) δ
2.92 (qd, J = 7.3, 5.6 Hz, 1 H), 2.63 (d, J =7.2 Hz, 2H), 2.08 (s, 3H), 1.75 - 1.51 (m, 2H), 1.03 (t, J =
7.4 Hz, 3H); 13C NMR (101 MHz, CDCI3) δ 178.14, 43.95, 39.78, 27.04,12.95, 11.29; EIMS m/z 148.
4-methyl-3-(methylthio)pentanoic add was prepared as described In Example 63 and Isolated as a colorless oil: IR (Thin film) 2960,1704 cm1; 1H NMR (400 MHz, CDCI3) δ 2.88 (ddd, J= 9.1,5.4,
4.7 Hz, 1H), 2.68 (dd, J= 16.0, 5.5 Hz, 1H), 2.55 (dd, J= 16.0, 9.1 Hz, 1H), 2.13 (s, 3H), 2.01 1.90 (m, 1 H), 1.03 (d, J = 6.8 Hz, 3H), 0.99 (d, J = 6.8 Hz, 3H); EIMS m/z 162.
Example 64: Préparation of ethyl 1-(hydroxymethyl)cyciopropanecarboxylate
O
A 1M solution of lithium aiuminum tri-fert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,T-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23 *C. The resulting solution was heated to 65 eC and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSOj), filtered, and concentrated to dryness to give the desired product as a pale yellow oîl (4.60, 91%): 1H NMR (300 MHz, CDCI3) δ 4.16 (q. J= 7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J = 7, 4 Hz, 2H).
Example 65: Préparation of ethyl 1-((methylsulfonyloxy)methyl)cyclopropanecarboxylate
O
Triethylamine (5.57 mL, 40.00 mmol) and methanesulfonyl chloride (2.85 mL, 36.60 mmol) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (4.80 g, 33.30 mmol) ln dichloromethane (83 mL) at 23 ’C. The resulting bright yellow solution was stirred at 23 ’C for 20 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a brown oil (6.92 g, 94%): 1H NMR (300 MHz, CDCI3) δ 4.33 (s. 2H). 4.16 (q, J7 Hz, 2H), 3.08 (s, 3H), 1.43 (dd, J= 7, 4 Hz, 2H), 1.26 (t, J = 7 Hz, 3H), 1.04 (dd, J- 7,4 Hz, 2H).
Example 66: Préparation of ethyl 1*(methylthlomethyl)cyclopropanecarboxylate
O
Sodium methanethiolate (4.36 g, 62.30 mmol) was added to a stirred solution of ethyl 1((methylsulfonyloxy)methyl) cyclopropanecarboxylate (6.92 g, 31.10 mmol) in N,Ndlmethylformamlde (62.30 mL) at 23 ’C. The resulting brown suspension was stirred at 23 ’C for 18 h. The réaction mixture was diluted with water and extracted with diethyl ether. The combined organic layers were dried (MgSO4), filtered, and concentrated by rotary évaporation to afford the title compound as a brown oil (5.43 g, 100%): 1H NMR (300 MHz, CDCI3) δ 4.14 (q, J= 7 Hz, 2H),
2.63 (s, 2H), 2.16 (s, 3H), 1.31 (dd, J =7,4 Hz, 2H), 1.25 (t, J = 7 Hz, 3H), 0.89 (dd, J = 7,4 Hz, 2H).
Example 67: Préparation of 1*(methylthlomethyl)cyclopropanecarboxyllc acid
O
A 50% solution of sodium hydroxide (12.63 mL, 243 mmol) was added to a stirred solution of ethyl
1-(methylthiomethyl)cyclopropanecarboxy1ate (5.43 g, 31.20 mmol) in absolute éthanol (62.30 mL) at 23 ’C. The resulting solution was stirred at 23 °C for 20 h. The reaction mixture was diluted with a 0.5 M solution of sodium hydroxide and washed with dichloromethane. The aqueous layer was acidified to pH=>1 with concentrated hydrochloric acid and extracted with dichloromethane. The combined organic layers were dried (Na2SO«), filtered, and concentrated and concentrated to dryness to give the desired product as a light brown oil (2.10 g, 46%): 1H NMR (300 MHz, CDCI3) δ 2.82 (s, 2H), 2.17 (s, 3H), 1.41 (dd, J = 7,4 Hz, 2H), 0.99 (dd, J =7,4 Hz, 2H).
Example 68: Préparation of 2,2-dlmethyl-3-(methylthlo)propanolc acid
O
OH
2,2-Dimethyl-3-(methylthio)propanolc add can be prepared as demonstrated in the literature (reference Musker, W. K.; et al. J. Org. Chem. 1996, 51,1026-1029). Sodium methanethiolate (1.0 g, 14 mmol, 2.0 equiv) was added to a stirred solution of 3-chloro-2,2-dimethylpropanoic add (1.0 g, 7.2 mmol, 1.0 equiv) in N,N-dimethylformamide (3.7 mL) at 0 *C. The resulting brown suspension was allowed to warm to 23 0C and stirred for 24 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (300 mL) and washed with diethyl ether (3 x 75 mL), The aqueous layer was addified to ρΗ®»1 with concentrated hydrochloric acid and extracted with diethyl ether (3 x 75 mL). The combined organic layers were dried (sodium sulfate), gravity filtered, and concentrated to afford a coloriess oil (1.2 g, 99% crude yield), 1H NMR (300 MHz, CDCh) δ 2.76 (s, 2H), 2.16 (s, 3H), 1.30 (s, 6H).
Example 69: Préparation of 4,4,4-trlfluoro-3-(methylthlo)butanolc acid
O SMe
HO'^^CFa
To a 100 mL round bottom flask was added (E)-4,4,4-trifluorobut-2-enoic acid (8 g, 57.1 mmol) and Methanol (24 mL), the solution was stirred In a water bath, then sodium methanethiolate (10.01 g, 143 mmol) was added In three portions. Vîgorous bubblîng was observed, the mixture was stirred at 25 °C ovemight, NMR showed no more starting material. To the reaction mixture was added 2 N HCI until acidic. The mixture was extracted with chloroform (5 x 50 mL), combined organic layer was dried over Na2SO4, concentrated In vacuo and further dried under high vacuum until there was no weight loss to give 4,4,4-trifluoro-3-(methylthio)butanoic acid (10.68 g, 56.8 mmol, 99 % yield) as a colorless oil: 1H NMR (400 MHz, CDCI3) δ 10.88 (s, 1 H), 3.53 (dqd, 10.5, 8.3,4.0 Hz, 1H),
2.96 (dd, J= 16.9,4.0Hz, 1H), 2.65 (dd, J~ 16.9,10.4 Hz, 1H), 2.29 (s, 3H); 13C NMR(101 MHz,
CDCI3) δ 175.78 (s), 126.61 (q. JC-f= 278.8 Hz), 44.99 (q, Jcf = 30.3Hz), 34.12 (d, 1.7 Hz),
15.95 (s); EIMS m/z 162.
Example 70; Préparation of 3-methyl-3-methylsulfany1-butyrlc acid
3-methyl-3-methytsulfanyl-butyric acid was made using the procedures disclosed in J.Chem Soc Perkin 1,1992, 10,1215-21.
Example 71: Préparation of 3-methylsulfanyl-butyrlc acid
3-Methylsulfanyl-butyric acid was made using the procedures disclosed In Synthetic Comm.,1985, 15(7), 623-32.
Example 72: Préparation of tetrahydro-thlophene-3-carboxyllc acid
O
Tetrahydro-thiophene-3-carboxylic acid was made using the procedures disclosed In Heterocycles,
2007. 74, 397-409.
Example 73: Préparation of 2-methyl-3-methylsulfanyl-butyrlc acid
2-Methyl-3-methylsulfanyl-butyric acid was made as described In J.Chem Soc Perkin 1,1992,10, 1215-21.
Example 74: Préparation of (1S,2S)-2-(methylthlo)cyclopropanecarboxyllcacld
O
(1 S,2S)-2-(Methylthio)cyciopropanecarboxylic acid was made using the procedures disclosed In
Synthetic Comm., 2003, 33 (5); 801-807.
Example 75: Préparation of 2-(2-(methylthlo)ethoxy)propanolcacld ο
2-(2-(Methylthio)ethoxy)propanoic acid was made as described in WO 2007/064316 A1.
Example 76: Préparation of 2-((tetrahydrofuran-3-yl)oxy)propanolc acid
2-((Tetrahydrofuran-3-yl)oxy)propanoic acid was made as described ln WO 2007/064316 A1.
Example 77; Préparation of tert-butyl 1-(5-fluoropyrldln-3-yl)-3-methyl-1H-pyrazol-4-yl(prop-
2-ynyl)carbamate (Compound 601)
To an Ice cold solution of tert-buty! 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-ylcarbamate (1200 mg, 4.11 mmol) ln dry Ν,Ν-dimethylformamide (DMF; 4 mL) under nitrogen was added 60% wt sodium hydride (197 mg, 4.93 mmol) and the mixture stirred for 10 minutes (min). 3-Bromoprop-
1-yne (733 mg, 6.16 mmol) was then added and the mixture was stirred for additional 0.5 hour (h) at 0 - 5 ’C. The mixture was allowed to warm to ambient température and then stirred for additional 3 h. The brown reaction mixture was poured into saturated aqueous ammonium chloride (NH4CI; 20 mL), and diluted with ethyl acetate (EtOAc; 50 mL). The organic phase was separated and the aqueous phase extracted with EtOAc (20 mL). The combined organic phase was washed with brine, dried over anhydrous magnésium sulfate (MgSO4j, filtered, and concentrated in vacuo to give a brown oil. This oil was purified on silica gel eluting with mixtures of hexanes and EtOAc to give the title compound as a light yellow solid (1103 mg, 81%): mp 81-82 'C; ’H NMR (400 MHz, CDCI3) δ 8.73 (s, 1H), 8.37 (d, J =2.5 Hz, 1H), 7.99 (s, 1 H), 7.83 (dt, J= 9.5, 2.2 Hz, 1H), 4.31 (s, 2H), 2.29 (t, J = 2.4 Hz, 1H), 2.27 (s, 3H), 1.45 (s, 9H); ESIMS m/z 229.84 ([M]*).
Compounds 596 and 606 were prepared In accordance with the procedure disclosed in Example 77 from the corresponding amine.
Example 78: Préparation of 1-(5-fluoropyridin-3-yl)-3-methyl-N-(prop-2-ynyl)-1W-pyrazol-4amine, hydrochloride
F Λ N >~NH.HCI VS
To a solution of fert-butyl 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazoi-4-yl(prop-2-ynyl)carbamate (1.03 g, 3.11 mmol) in dioxane (5 mL) was added 4 molar (M) hydrogen chloride (HCl; 3.9 mL, 15.5 mmol) In diethyl ether (Et2O). The mixture was stirred at room température for 48 h and the resulting white solid was fiitered, washed with Et2O and dried under vacuum to give the title compound as a white solid (741 mg, 89%): mp 167-168 ’C; ’H NMR (400 MHz, DMSO de) δ 8.92 8.85 (m, 1 H), 8.42 (d. J = 2.5 Hz, 1 H). 8.15 (s, 1 H), 8.12 - 8.02 (m, 1 H), 3.85 (d, J = 2.5 Hz, 2H), 3.27-3.19 (m, 1H), 2.22 (s, 3H); ESIMS m/z230.4 ([M]*).
3-Chloro-N-(prop-2-ynyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine, hydrochloride was prepared In accordance with the procedure disclosed In Example 78 from Compound 606: mp 180—182 *C; ’H NMR (400 MHz, CDCI3) δ 9.22 (d, J= 2.5 Hz, 1H), 8.67 (dd, J= 5.3,1.0 Hz, 1H), 8.64 (ddd, J =
8.6, 2.6,1.2 Hz, 1 H), 8.32 (s, 1 H), 7.96 (dd, J = 8.6, 5.3 Hz, 1 H), 3.81 (d, J = 2.4 Hz, 2H), 3.15 (t, J = 2.4 Hz, 1H); ESIMS m/z234 ([M+2]*).
3-Methyl-N-(prop-2-yn-1-yl)-1-(pyridin-3-y1)-1H-pyrazol-4-amine, hydrochloride was prepared in accordance with the procedure disclosed in Example 78 from Compound 596: mp 161-163 °C; ’H NMR (400 MHz, DMSO-de) δ 8.46 (s, 1H), 8.05 (s, 1H), 7.83 (d, J= 5.9 Hz, 1H), 7.57 (s, 1H), 7.29 (dd, J- 8.8, 5.6 Hz, 1H), 3.27 (d, J- 2.5 Hz, 2H), 3.21 (t. J = 1.2Hz, 1H), 1.52 (s, 3H); EIMS m/z
213.1 ([M]+).
Example 79: Préparation of N-(1-(5-fluoropyrldln-3-yl)-3-methyl-1H-pyrazol-4-yl)-3(methylthlo)-N-(prop-2-ynyl)propanamide (Compound 605)
To a stirred solution of 1-(5-fluoropyridin-3-yl)-3-methyl-/V-(prop-2-yn-1-yl)-1H-pyrazol-4-amine, HCl (100 mg, 0.38 mmol) and N.N-dimethylpyridin-4-amine (DMAP; 115 mg, 0.94 mmol) In CH2CI2 (DCM; 2 mL) was added 2-methyl-3-(methylthio)propanoyl chloride (69 mg, 0.45 mmol), and the mixture stirred at room température for 24 h. The mixture was concentrated in vacuo to give a brown oil which was purified on silica gel eluting with mixtures of EtOAc and hexanes to give the title compound as a colorless oil (80 mg, 61%): 1H NMR (400 MHz, CDCI3) δ 8.76 (d, J= 1.6 Hz, 1 H). 8.44 (d, J - 2.5 Hz, 1H), 8.05 (s, 1H), 7.86 (dt, 9.3, 2.3 Hz,1H), 4.45 (s, 2H), 2.79 (t, J= 7.3 Hz, 2H), 2.43 (t, J = 7.3 Hz, 2H), 2.30 (s, 3H), 2.25 (t, J- 2.5 Hz, 1 H), 2.06 (s, 3H); ESIMS m/z 333.6 (IM+H]+).
Compounds 598, 599, 600, 602,603,607,608 and 610 were prepared in accordance with the procedure disclosed in Example 79 from the corresponding amines.
Example 80: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1 H-pyrazol-4-yl)-4,4,4-trlfluoro-3(methylthlo)-N-(prop-2-yn-1-yl)butanamide (Compound 613)
To a 7 mL vlal was added 3-chloro-N-(prop-2-yn-1-yl)-1-(pyridin-3-yl)-1H-pyrazol-4-amine (140 mg, 0.6 mmol), N,N-dimethytpyridin-4-amine (249 mg, 2.040 mmol), N1-((ethynmino)methylene)-N3,N3dimethylpropane-1,3-diamlne hydrochloride (276 mg, 1.440 mmol) followed by 4,4,4-trifluoro-3(methylthio)butanoic acid (158 mg, 0.840 mmol) and DCE (1.2 mL). The solution was stirred at 25 °C for 18 hours, the crude réaction mixture was concentrated and purified with silica gel chromatography (0-100% EtOAc / hexane) to give the title compound as a brown oil (237 mg, 0.588 mmol, 98%): (IR thin film) 1674 cm'1; 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J= 2.6 Hz, 1H), 8.64 (dd, J= 4.7,1.3 Hz, 1H), 8.13 (s, 1H), 8.07 (ddd, J = 8.3,2.7,1.5 Hz, 1H), 7.48 (ddd, J= 8.3,4.8, 0.5 Hz, 1H). 4.39 (s, 2H), 3.76 (dqd, J = 17.2, 8.6, 3.6 Hz, 1H), 2.67 (dd, J= 16.6, 3.6 Hz, 1H), 2.46 (dd, J= 16.5, 9.9 Hz. 1H), 2.29 (d, J =2.5 Hz, 4H); ESIMS m/z 403 ([M+H]*).
tert-Butyl (2-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(prop-2-yn-1-yl)amino)-2oxoethyt)(methyi)carbamate was prepared as described in Example 80: IR (thin film) 1696 cm'1; 1H NMR (400 MHz, CDCI3) δ 8.96 (bs, 1H), 8.63 (dd, J = 4.9 Hz, 1H), 8.21 - 7.86 (m, 2H). 7.46 (dd. J =
8.3, 4.8 Hz, 1H), 4.65 - 4.30 (m. 2H).4.02 - 3.70 (bs, 2H), 3.06 - 2.79 (m, 3H). 2.25(bs, 1H), 1.44(s, 9H); ESIMS m/z 404 ([M+H]*).
Compounds 597,604,609, 614-616,619,624,626, and 627 were prepared in accordance with the procedure disclosed In Example 80. Compound 625 was prepared from Compound 624 using the methodology described In US 20120053146 A1.
Example 81: Préparation of 3-chloro-N-(prop-2-ynyl)-1-(pyridin-3-yl)-1H-pyrazol-4-amlne
Cl
NH
To a solution of tert-butyl (3-chloro-1-(pyridin-3-yt)-1H-pyrazol-4-yl)(prop-2-yn-1-yl)carbamate (2.2 g, 6.61 mmol) In dichloromethane (DCM; 8.3 ml) was added 2,2,2-trifluoroacetic acid (12.06 g, 106 mmol) and the réaction mixture was stirred at ambient température for 1 h. The reaction was quenched by the addition of saturated sodium bicarbonate (NaHCO3). The organic layer was extracted with DCM (2 x 20 mL). The organic layers were combined and dried over sodium sulfate (NajSQi), filtered and concentrated to afford the title compound as a belge solid (1.5 g, 6.12 mmol, 93%): ’H NMR (400 MHz, CDCI3) δ 8.89 (d, J = 2.3 Hz, 1H), 8.50 (dd, J = 4.7,1.4 Hz, 1H), 8.01 -
7.93 (m, 1 H), 7.54 (s, 1 H), 7.37 (ddd, J = 8.3, 4.8, 0.7 Hz, 1 H), 3.90 (s, 2H), 3.38 (s, 1 H), 2.44 2.09 (m, 1 H); ESIMS m/z 233 ([M+H]*).
Example 82: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-2-(methylthlo)-N(prop-2-yn-1-yl)propanamlde (Compound 611)
To a solution of 2-(methylthio)propanoic acid (0.36 g, 3.00 mmol) in DCM (3 mL) was added oxalyl dichloride (0.29 ml, 3.31 mmol) followed by one drop of DMF. The reaction mixture was stirred for 30 min before ail of the solvent was evaporated. The resulting residue was dissolved In DCM (2 mL) and the solution was added to a pre-stirred solution of 3-chloro-N-(ProP2-yn-1-yl)-1-(pyridin-3yi)-1H-pyrazol-4-amine (0.35 g, 1.50 mmol) and W-ethyl-N-isopropylpropan-2-amine (0.57 ml, 3.31 mmol) In DCM (5.5 mL). The reaction mixture was stirred at ambient température for 16 h. The reaction mixture was concentrated and the residue was purified using silica gel chromatography (ΟΙ 00% EtOAc / hexanes) to afford the title compound as a yellow oil (432 mg, 1.23 mmol, 85%): ’H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.5 Hz, 1 H), 8.66 - 8.60 (m, 1 H), 8.25 (s, 1 H), 8.08 - 8.01 (m, 1 H), 7.49 - 7.42 (m, 1 H), 4.86 (s, 1 H), 4.29 - 3.97 (m, 1 H), 3.31 (d, J = 6.5 Hz, 1 H), 2.30 - 2.24 (m, 1H), 2.09 (s, 3H), 1.46 (d, J = 6.9 Hz, 3H); ’3C NMR (101 MHz, CDCI3) δ 171.30,148.66,140.71, 140.18,135.71,127.87,126.35, 124.11,122.12, 78.53, 72.92, 53.39, 37.97,16.42, 11.07; ESIMS m/z 335 ([M+H]*).
Compounds 612 and 622 were prepared In accordance with the procedure disclosed in Example 82.
100
Example 83: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-2-(methylsulflnyl)-N(prop-2-yn-1-yl)propanamlde (Compound 617)
To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-(methylthio)-N-(prop-2-yn-1yljpropanamide (0.1 g, 0.30 mmol) In hexafluoroisoproanol (2.0 ml) was added hydrogen peroxide (35 wt %, 0.08 ml, 0.90 mmol) and the reaction mixture was stirred vigorously at ambient température. The reaction was complété after 1 h. The reaction was quenched with saturated sodium sulfite solution and the organic layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over Na2SO4( filtered and concentrated. The residue was purified using silica gel chromatography (0-20% methanol (MeOH) / DCM) to afford the title compound as an offwhite foam (82 mg, 0.21 mmol, 78 %): 1H NMR (400 MHz, CDCI3) δ 8.98 (s, 1H), 8.65 (d, J= 4.6 Hz, 1 H). 8.23 (s, 1 H), 8.11 - 7.97 (m, 1 H), 7.51 - 7.41 (m, 1 H), 4.88 (br s, 1 H), 4.14 (br s, 1 H), 2.64 (s, 1.2H), 2.55 (s, 1.8H), 2.33 - 2.27 (m. 1 H), 1.47 (d, J = 6.8 Hz, 3H), 1.42 (br s, 1 H); 13C NMR (101 MHz, CDCI3) δ 168.11, 148.95,148.78,140.45,140.33,140.20,135.56,126.54,124.10, 121.68, 121,58, 121.48, 77.69, 73.49, 38.60; ESIMS m/z 351 <[M+H]*>Example 84: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-2-{methylsulfonyl)-N(prop-2-yn-1-yl)propanamlde (Compound 618)
To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-(methylthio)-N-(prop-2-yn-1yljpropanamide (0.10 g, 0.30 mmol) and acetic add (2.0 ml) was added sodium perborate
101 tetrahydrate (0.11 g, 0.74 mmol) and the vial was heated to 65 ’C for 2 h. The reaction mixture was cooled to amblent température and neutralized with saturated NaHCO3. The aqueous layer was extracted with EtOAc (3x). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified using silica gel chromatography (0-20% MeOH / DCM) to afford the title compound as a yellow foam (84 mg, 0.21 mmol, 73%): ’H NMR (400 MHz, CDCI3) δ 9.00 (s, 1H), 8.65 (s, 1H), 8.29 (s, 1H), 8.03 (d, J - 8.0 Hz, 1H), 7.54 - 7.39 (m, 1H), 4.89 (d, J -
16.9 Hz, 1H), 4.20 - 4.08 (m, 1H), 4.07 - 3.92 (m, 1H), 3.01 (s, 3H), 2.34 - 2.29 (m, 1H), 1.67 (d, J = 7.0 Hz, 3H); ’3C NMR (101 MHz, CDCI3) δ 166.97, 166.90, 148.77,140.43,140.24, 135.58, 129.36, 126.64, 124.14, 121.34, 73.80, 60.91, 38.78, 36.29,13.97; ESIMS m/z 367 ([M+H]*).
Compounds 620 and 621 were prepared in accordance with the procedure disclosed ln Example 84.
Example 85: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazoi-4-yl)-2-(methylamlno)-N(prop-2-yn-1-yl)acetamide
To a solution of tert-butyl (2-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(prop-2-yn-1-yl)amino)-2oxoethyf)(methyl)carbamate (0.47 g, 1.16 mmol) ln DCM (1.16 ml) was added 2,2,2-trifluoroacetic add (1.16 ml) and the réaction mixture was stirred at ambient température for 1 h. To the mixture was added toluene and then the reaction was concentrated to dryness. The oil was redissolved in DCM and saturated NaHCO3 solution was added. The phases were separated and the aqueous phase was extracted with DCM. The organic layers were combined, the solvent evaporated, and the residue purified using silica gel chromatography (0-15% MeOH / DCM) to afford the title compound as yellow oil (0.258 g, 0.849 mmol, 73%): IR (thln film) 1696 cm ’; ’H NMR (400 MHz, CDCI3) δ 8.98 (d, J= 2.6 Hz, 1H), 8.64 (dd, J= 4.7,1.3 Hz, 1H), 8.19 (s, 1H), 8.06 (ddd, J - 8.3,
2.6,1.4 Hz, 1H), 7.47 (dd, J = 8.3, 4.7 Hz, 1H), 4.48 (s, 2H), 3.49 (s, 2H), 2.49 (s, 3H), 2.28 (t, J =
2.5 Hz, 1H); ESIMS m/z 304 ([M+H]*).
102
Example 86: Préparation of N-(3-chloro-1-(pyrldln-3-yl)-1H-pyrazol-4-yl)-2-(Nmethy!methytsulfonamldo)-N-(prop-2-yn-1-y1)acetamlde (Compound 623)
To a solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-(methylamino)-N-(prop-2-yn-1yl)acetamide (0.100 g, 0.329 mmol) in DCM (0.65 ml) was added methanesulfonyl chloride (0.057 g, 0.494 mmol) followed by diisopropylethylamine (0.11 ml, 0.658 mmol) and the reaction was stirred at room température for 24 h. The reaction mixture was poured Into a solution of saturated NaHCO3 and subsequently extracted with DCM. The organic layers were combined and concentrated, and the residue was purified using silica gel chromatography (50-100% EtOAc / hexanes) to afford the title compound as a yellow solid (0.091 g, 0.238 mmol, 72%): (IR thin film) 1678 cm·’; ’H NMR (400 MHz. CDCI3) δ 8.97 (d, J- 2.6 Hz, 1H), 8.65 (dd. J= 4.8,1.3 Hz. 1H).
8.15 (s. 1 H), 8.04 (ddd, J - 8.3, 2.7,1.4 Hz, 1 H), 7.48 (dd. J = 8.4, 4.7 Hz, 1 H), 3.77 (hept, J = 6.9 Hz. 2H), 3.05 (s, 2H), 3.01 (s, 3H), 2.87 (s, 3H), 2.31 (t, J= 2.5 Hz. 1H); ESIMS m/z 382 ([M+H]*).
Example 87: Préparation of 3-((3,3,3-trifluoropropyt)thlo)propanolc acid
3-Mercaptopropanoic acid (3.2 g, 30.1 mmol) was dissolved in MeOH (20 mL) and stirred at RT. Powdered potassium hydroxide (3.72 g, 68.3 mmol) was added to the solution, followed by 3bromo-1,1,1-trifluoropropane (8.14 g, 34.7 mmol). The solution was then stirred at 65 *C for 3 h and then it was quenched with 1N HCl until the pH of the solution was acidic. The mixture was extracted with DCM (3 x 30 mL), the combined organic phases were dried, concentrated and purified by silica
103 gel chromatography (0-50% EtOAc / hexane) to give 3-((3,3,3-trifluoropropyl)thio)propanoic acid (5.5 g, 27.2 mmol, 90 % yield) as colorless oil mixed with some white suspension: IR (Thln film) 2936,1708 cm*1; ’H NMR (300 MHz, CDCl3) δ 2.86 - 2.78 (m, 2H), 2.78 - 2.58 (m, 4H), 2.52 - 2.25 (m, 2H); EIMS m/z 202.
Example 88: Préparation of A/-(3-methyl-1-(pyridln-3-yl)-1H-pyrazol-4-yl)-A/-(prop-2-yn-1-yl)-3((3,3,3-trifluoropropyl)thio)propanamlde (Compound 627)
ln a 4mL vial was added 3-methyl-N-(prop-2-yn-1-yl)-1-(pyridin-3-yl)-1H-pyrazol-4-amlne hydrochloride (120 mg, 0.482 mmol) and DMAP (59 mg, 0.482 mmol) with dry Et2O ( 1.6 mL). The solution was stirred at room température for 1 h. Then additional DMAP (200 mg, 1.639 mmol) was added. The solution was cooled to 0 °C under N2 and dicyclohexylcarbodiimide (DCC; 239 mg, 1.158 mmol) was added. The solution was allowed to warm up to room température slowly and stirred overnight. White precipitate formed during the reaction. The crude reaction mixture was filtered and purified by silica gel chromatography (0-90% EtOAc / hexane) to give N-(3-methyl-1(pyridin-3-yl)-1H-pyrazol-4-yl)-N-(prop-2-yn-1-yl)-3-((313,3-trifluoropropyl)thio)propanamide (113 mg, 0.269 mmol, 55.7 % yield) as a yellow viscous oil: IR (Thin film) 3293,1663 cm’1; *H NMR (400 MHz, CDCI3) δ 8.96 (d, J= 2.6 Hz, 1 H). 8.58 (dd, J = 4.8,1.5 Hz, 1H), 8.04 (ddd, J - 8.3, 2.7,1.5 Hz, 1 H), 8.01 (s, 1 H), 7.44 (dd, J = 8.3, 4.9 Hz, 1 H), 4.45 (s, 2H), 2.84 (t, J = 7.1 Hz, 2H), 2.72 2.60 (m, 2H), 2.44 (t, J = 7.1 Hz, 2H). 2.41 - 2.32 (m, 2H), 2.31 (s, 3H), 2.26 (t, J - 2.4 Hz, 1 H); ESIMS m/z 397 ([M+H]*).
Example A: Bioassays ON Green Peach Aphid (“GPA) (Myzus perslcae) (MYZUPE).
GPA Is the most signifîcant aphid pest of peach trees, causing decreased growth, shriveling of the leaves, and the death of various tissues. It Is also hazardous because It acts as a vector for the transport of plant viruses, such as potato virus Y and potato leafroll virus to members of the
104 nightshade/potato family Solanaceae, and various mosaic viruses to many other food crops. GPA attacks such plants as broccoli, burdock, cabbage, carrot, cauliflower, daikon, eggplant, green beans, lettuce, macadamia, papaya, peppers, sweet potatoes, tomatoes, watercress, and zucchini, among other plants. GPA also attacks many omamental crops such as carnation, chrysanthemum, flowering white cabbage, polnsettia, and roses. GPA has developed résistance to many pesticides.
Certain molécules disclosed in this document were tested against GPA using procedures described ln the following example, ln the reporting of the results, “Table 3: GPA (MYZUPE) and sweetpotato whltefly-crawler (BEMITA) Rating Table' was used (See Table Section).
Cabbage seedlings grown in 3-lnch pots, with 2-3 small (3-5 cm) true leaves, were used as test substrate. The seedlings were infested with 20-50 GPA (wingless adult and nymph stages) one day prior to chemical application. Four pots with individual seedlings were used for each treatment. Test compounds (2 mg) were dissolved ln 2 mL of acetone/methanol (1:1 ) solvent, forming stock solutions of 1000 ppm test compound. The stock solutions were diluted 5X with 0.025% Tween 20 in H2O to obtain the solution at 200 ppm test compound. A hand-held aspirator-type sprayer was used for spraying a solution to both sides of cabbage leaves until runoff. Reference plants (solvent check) were sprayed with the diluent only containing 20% by volume of acetone/methanol (1:1) solvent. Treated plants were held in a holding room for three days at approximately 25 *C and ambient relative humidity (RH) prior to grading. Evaluation was conducted by counting the number of live aphids per plant under a microscope. Percent Control was measured by using Abbott's correction formula (W.S. Abbott, Ά Method of Computing the Effectiveness of an Insecticide J. Econ. Entomol. 18 (1925), pp.265-267) as follows.
Corrected % Control = 100*(X-Y)/X where
X = No. of live aphids on solvent check plants and
Y = No. of live aphids on treated plants
The results are indicated ln the table entitled “Table 4. Biological Data for GPA (MYZUPE) and sweetpotato whltefly-crawler (BEMITA)” (See Table Section).
Example B: Insecticidal test for sweetpotato whltefly-crawler (Bemlsla tabac!) (BEMITA) ln follar spray assay
Cotton plants grown in 3-lnch pots, with 1 small (3-5 cm) true leaf, were used as test substrate. The plants were placed in a room with whitefly adults. Adults were allowed to deposit
105 eggs for 2-3 days. After a 2-3 day egg-laying period, plants were taken from the adult whitefly room. Adults were blown off leaves using a hand-held Deviibiss sprayer (23 psi). Plants with egg Infestation (100-300 eggs per plant) were placed in a holding room for 5-6 days at 82 °F and 50% RH for egg hatch and crawler stage to develop. Four cotton plants were used for each treatment. Compounds (2 mg) were dissolved in 1 mL of acetone solvent, forming stock solutions of 2000 ppm. The stock solutions were diluted 10X with 0.025% Tween 20 in H2O to obtain a test solution at 200 ppm. A hand-held Deviibiss sprayer was used for spraying a solution to both sides of cotton leaf until runoff. Reference plants (solvent check) were sprayed with the diluent oniy. Treated plants were held in a holding room for 8-9 days at approximately 82*F and 50% RH prior to grading. Evaluation was conducted by counting the number of live nymphs per plant under a microscope. Insecticidal activity was measured by using Abbott's correction formula and presented in “Table 4. Biological Data for GPA (MYZUPE) and sweetpotato whltefly-crawler (BEMITA)* (see column BEMITA):
Corrected % Control = 100 ‘ (X - Y) / X where X = No. of live nymphs on solvent check plants
Y = No. of live nymphs on treated plants
PESTICIDALLY ACCEPTABLE ACID ADDITION SALTS, SALT DERIVATIVES, SOLVATES, ESTER DERIVATIVES, POLYMORPHS, ISOTOPES AND RADIONUCLIDES
Molécules of Formula One may be formulated Into pesticidally acceptable acid addition salts. By way of a non-limiting example, an amine fonction can form salts with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric, lactic, giuconic, ascorbic, maleic, aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic, hydroxymethanesulfonic, and hydroxyethanesulfonic acids. Additionally, bywayof a non-limiting example, an acid fonction can form salts including those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exampies of preferred cations include sodium, potassium, and magnésium.
Molécules of Formula One may be formulated into sait dérivatives. By way of a non-limiting example, a sait dérivative can be prepared by contacting a free base with a sufficient amount of the desired acid to produce a sait. A free base may be regenerated by treating the sait with a suitable dilute aqueous base solution such as dilute aqueous sodium hydroxide (NaOH), potassium carbonate, ammonia, and sodium bicarbonate. As an example, in many cases, a pesticide, such as
2,4-D, is made more water-soluble by converting it to its dimethylamine sait..
106
Molécules of Formula One may be formulated Into stable complexes with a solvent, such that the complex remains intact after the non-complexed solvent is removed. These complexes are often referred to as solvatés. However, it is particularly désirable to form stable hydrates with water as the solvent.
Molécules of Formula One may be made into ester dérivatives. These ester dérivatives can then be applied in the same manner as the invention disclosed in this document is applied.
Molécules of Formula One may be made as various crystal polymorphs. Polymorphism Is important in the development of agrochemicals since different crystal polymorphs or structures of the same molécule can hâve vastly different physical properties and biological performances.
Molécules of Formula One may be made with different Isotopes. Of particular Importance are molécules having 2H (also known as deuterium) in place of 1H.
Molécules of Formula One may be made with different radionuclides. Of particular importance are molécules having 1*C.
STEREOISOMERS
Molécules of Formula One may exist as one or more stereoisomers. Thus, certain molécules can be produced as racemic mixtures. It will be appreciated by those skilled In the art that one stereoisomer may be more active than the other stereoisomers. Individual stereoisomers may be obtained by known sélective synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional résolution procedures. Certain molécules disclosed in this document can exist as two or more Isomers. The various Isomers include géométrie Isomère, diastereomere, and enantiomere. Thus, the molécules disclosed In this document Include géométrie isomère, racemic mixtures, individual stereoisomers, and optically active mixtures. It will be appreciated by those skilled in the art that one Isomer may be more active than the othere. The structures disclosed In the présent disclosure are drawn in only one géométrie form for clarity, but are intended to represent ail géométrie forms of the molécule.
COMBINATIONS
Molécules of Formula One may also be used In combination (such as, in a compositional mixture, or a slmultaneous or sequential application) with one or more compounds having acariddal, algicidal, avicldal, bactericidal, fungiddal, herbiddal, insecticidal, mollusdddal, nematiddal, rodentiddal, or viruddal properties. Additionally, the molécules of Formula One may
107 also be used In combination (such as, In a compositional mixture, or a simultaneous or séquentiel application) with compounds that are antifeedants, bird repellents, chemosterilants, herbicide safeners, insect attractants, Insect repellents, mammal repellents, mating disrupters, plant activators, plant growth regulators, or synergists. Examples of such compounds in the above groups that may be used with the Molécules of Formula One are - (3-ethoxypropy!)mercury bromide, 1,2-dichloropropane, 1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol, 2(octylthlo)ethanol, 2,3,5-tri-lodobenzolc acid, 2,3,6-TBA, 2,3,6-TBA-dimethylammonium, 2,3,6-TBAlithium, 2,3,6-TBA-potassium, 2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2ethylhexyl, 2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl, 2,4,5-T-butyl,
2.4.5- T-isobutyl, 2,4,5-T-lsoctyl, 2,4,5-T-isopropyl, 2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,
2.4.5- T-triethylammonium, 2,4,5-T-trolamine, 2,4-D, 2,4-D-2-butoxypropyl, 2,4-D-2-ethy!hexy1,2,4D-3-butoxypropyl, 2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethy!ammonium, 2,4-DBIsoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-diethylammonium, 2,4D-dimethy!ammonium, 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,
2.4- D-hepty!ammonium, 2,4-D-isobutyl, 2,4-D-lsoctyl, 2,4-D-lsopropyl, 2,4-D-isopropylammonium,
2.4- D-lithlum, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl,
2.4- D-sodlum, 2,4-D-tefuryl, 2,4-D-tetradecylammonlum, 2,4-D-triethylammonium, 2,4-D-tris(2hydroxypropyljammonium, 2,4-D-trolamlne, 2iP, 2-methoxyethylmercury chloride, 2-phenyl phénol,
3.4- DA, 3,4-DB, 3,4-DP, 4-amlnopyridine, 4-CPA, 4-CPA-potassium, 4-CPA-sodium, 4-CPB, 4CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyqulnoline sulfate, 8-phenylmercurioxyqulnoline, abamectin, abscisic add, ACC, acephate, acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole, acibenzolar, adbenzolar-S-methyl, acifluorfen, acifluorfen-methyi, adfluorfen-sodium, adonifen, acrep, acrinathrin, acroleln, acrylonitrile, acypetacs, acypetacscopper, acypetacs-zlnc, alachlor, alanycarb, albendazole, aldicarb, aldimorph, aldoxycarb, aldrin, allethrin, allidn, allidochlor, allosamidin, alloxydim, alloxydlm-sodium, ally! alcohol, allyxycarb, alorac, a/pha-cypermethrin, a/pha-endosulfan, ametoctradin, ametridione, ametryn, amlbuzin, amlcarbazone, amicarthïazol, amidithion, amidoflumet, amldosulfuron, aminocarb, amlnocyclopyrachlor, aminocyclopyrachlor-methyî, aminocydopyrachlor-potasslum, aminopyralid, amlnopyralid-potassium, amlnopyralid-tris^-hydroxypropyljammonium, amlprofos-methyî, amiprophos, amlsulbrom, amiton, amlton oxalate, amltraz, amltrole, ammonium sulfamate, ammonium α-naphthaleneacetate, amobam, ampropylfos, anabastne, ancymidol, anilazine, anilofos, anisuron, anthraqulnone, antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam, asulam-potassium, asulam-sodium, athîdathîon, atraton, atrazine, aureofungin, aviglycine, aviglycine hydrochloride, azaconazole, azadîrachtln, azafenidin, azamethiphos, azimsulfuron,
108 azinphos-ethyl, azinphos-methyl, aziprotryne, azithiram, azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban, barium hexafluorosilicate, barium polysulfide, barthrin, BCPC, beflubutamid, benalaxyl, benalaxyl-M, benazolin, benazolin-dimethylammonium, benazolin-ethyl, benazolin-potassium, bencarbazone, bendothlaz, bendiocarb, benfluralin, benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos, benquinox, bensulfuron, bensulfuronmethyl, bensulide, bensultap, bentaluron, bentazone, bentazone-sodium, benthlavalicarb, benthiavalicarb-isopropyl, benthiazole, bentranll, benzadox, benzadox-ammonium, benzalkonium chloride, benzamacril, benzamacril-isobutyl, benzamorf, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid, benzoximate, benzoylprop, benzoylprop-ethyl, benzthiazuron, benzyl benzoate, benzyladenine, berberine, berberine chloride, beia-cyfluthrin, bete-cypermethrin, bethoxazin, bîcyclopyrone, bifenazate, bifenox, bifenthrin, bifujunzhi, bilanafos, bilanafos-sodium, binapacryl, bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin, bloresmethrin, biphenyl, bisazir, bismerthiazol, bispyribac, bispyribac-sodium, bistrifluron, bitertanol, bithionol, bixafen, blasticidin-S, borax, Bordeaux mixture, boric acid, boscaiid, brassinolide, brassinolide-ethyl, brevlcomln, brodifacoum, brofenvalerate, brofluthrinate, bromacil, bromadllithlum, bromadl-sodium, bromadlolone, bromethalin, bromethrin, bromfenvlnfos, bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT, bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil, bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxynil octanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol, bucarpolate, bufencarb, buminafos, buplrimate, buprofezin, Burgundy mixture, busulfan, butacarb, butachlor, butafenacil, butamifos, butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron, butocarboxim, butonate, butopyronoxyl, butoxycarboxlm, butralin, butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos, cafenstrole, caldum arsenate, caldum chlorate, caldum cyanamide, caldum polysulfide, calvinphos, cambendichlor, camphechlor, camphor, captafoi, captan, carbamorph, carbanolate, carbaryl, carbasulam, carbendazim, carbendazim benzenesulfonate, carbendazim sulfite, carbetamide, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartap hydrochloride, carvacrol, carvone, CDEA, celloddin, CEPC, ceralure, Cheshunt mixture, chlnomethlonat, chitosan, chlobenthiazone, chlomethoxyfen, chloralose, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chloramine phosphorus, chloramphenicol, chloraniformethan, chloranil, chloranocryl, chlorantraniiiprole, chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenslde, chlorbenzuron, chlorbicyden, chlorbromuron, chlorbufam, chlordane, chlordecone, chlordimeform, chiordimeform hydrochloride, chlorempenthrin,
109 chlorethoxyfos, chloreturon, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole, chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide, chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren, chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequat chloride, chlomidine, chlomitrofen, chlorobenzilate, chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron, chloroneb, chlorophacinone, chlorophacinone-sodium, chloroplcrin, chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron, chloroxynll, chlorphonium, chlorphonium chloride, chlorphoxim, chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifosmethyl, chlorquinox, chlorsulfuron, chlorthal, chlorthal-dîmethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos, chlozolinate, choline chloride, chromafenozide, cinerin I, cinerin II, cinerins, clnidonethyl, cinmethylin, cinosulfuron, dobutide, clsanilide, dsmethrin, clethodim, dimbazole, diodinate, clodinafop, dodinafop-propargyl, cloethocarb, clofencet, clofencet-potassium, dofentezine, clofibric add, dofop, dofop-isobutyl, ciomazone, domeprop, doprop, cloproxydîm, dopyralid, dopyralidmethyl, dopyralid-olamine, dopyralid-potassium, dopyralid-tris(2-hydroxyprapyl)ammonium, cloquintocet, doquintocet-mexyt, cloransulam, cloransulam-methyl, closanteI, dothianidin, clotrimazole, doxyfonac, doxyfonac-sodium, CMA, codlelure, colophonate, copper acetate, copper acetoarsenite, copper arsenate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl, coumlthoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol, crimidine, crotamiton, crotoxyphos, crufomate, cryoiite, cue-lure, cufraneb, cumyluron, cuprobam, cuprous oxide, curcumenol, cyanamide, cyanatryn, cyanazine, cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyazofamid, cybutryne, cydafuramid, cydanilide, cyclethrin, cycloate, cycloheximide, cycloprate, cydoprothrin, cyclosulfamuron, cydoxydim, cycluron, cyenopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalofop, cyhalofopbutyl, cyhalothrin, cyhexatin, cymiazole, cymiazoie hydrochloride, cymoxanîl, cyometrinil, cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin, cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid, cyprosulfamide, cyromazine, cythioate, daimuron, dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide, dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT, debacarb, decafentin, decarbofuran, dehydroacetic add, delachlor, deltamethrin, demephion, demephion-O, demephionS, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyisulphon, desmedipham, desmetryn, d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos, diatomaceous earth, diazinon, dibutyl phthalate, dibutyi sucdnate, dicamba, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-dioiamine, dicamba
110 isopropylammonium, dicamba-methyl, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicapthon, dichlobenil, dîchlofenthion, dichlofluanid, dichlone, dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl, dichlormate, dichlormid, dîchlorophen, dichlorprop, dichlorprop-2-ethylhexyl, dichlorprop-butotyl, didilorprop-dimethylammonium, dichlorprop-ethyfammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P, dichlorprop-P-2ethylhexyl, dichlorprop-P-dimethylammonium, dichlorprop-potassium, dichlorprop-sodium, dichlorvos, dichlozoline, dîclobutrazol, diclocymet, didofop, diclofop-methyl, diclomezine, diclomezine-sodium, dicloran, diclosulam, dicofol, dicoumarol, dlcresyl, dicrotophos, dicyclanil, dlcyclonon, dieldrin, dienochlor, diethamquat, diethamquat dichloride, diethatyl, diethatyi-ethyl, diethofencarb, dietholate, diethyl pyrocarbonate, diethyltoluamide, dlfenacoum, difenoconazole, difenopenten, difenopenten-ethyl, difenoxuron, difenzoquat, dîfenzoquat metilsulfate, dîfethialone, diflovidazin, dîflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dîflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin, dimefox, dîmefuron, dimepiperate, dîmetachlone, dimetan, dimethacarb, dimethachlor, dimethametryn, dimethenamid, dimethenamidP, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon, dimoxystrobin, dinex, dinex-diclexlne, dingjunezuo, diniconazole, diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinoseb acetate, dinosebammonium, dinoseb-diolamine, dinoseb-sodium, dinoseb-trolamlne, dinosulfon, dinotefuran, dinoterb, dinoterb acetate, dinoterbon, dlofenolan, dioxabenzofos, dioxacarb, dioxathion, diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone, diphenylamine, dipropalln, dipropetryn, dipyrithione, diquat, diquat dibromide, disparture, disul, disulfiram, disulfoton, disulsodium, ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, dîuron, d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicin hydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure, doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone, edîfenphos, eglînazlne, eglinazine-ethyl, emamectin, emamectin benzoate, EMPC, empenthrin, endosulfan, endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, endothion, endrin, enestroburin, EPN, epocholeone, epofenonane, epoxtconazole, eprinomectîn, epronaz, EPTC, erbon, ergocalciferol, erlujixiancaoan, esdépalléthrine, esfenvalerate, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethametsulfuron, ethametsulfuronmethyl, ethaprochlor, ethephon, ethidimuron, ethiofencarb, ethiolate, ethion, ethiozîn, ethiprole, ethlrimol, ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos, ethoxyfen, ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate, ethyl formate, ethyl α-naphthaleneacetate, ethyl-DDD,
111 ethylene, ethylene dibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury 2,3dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etinofen, etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos, eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf, fenamiphos, fenapanll, fenarimol, fenasulam, fenazaflor, fenazaquln, fenbuconazole, fenbutatin oxide, fenchlorazole, fenchlorazole-ethyl, fenchlorphos, fenclorim, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitropan, fenitrothion, fenjuntong, fenobucarb, fenoprop, fenoprop-3-butoxypropyl, fenopropbutometyl, fenoprop-butotyl, fenoprop-butyl, fenoprop-lsoctyl, fenoprop-methyl, fenoproppotassium, fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fenridazon, fenridazon-potassium, fenridazonpropyl, fenson, fensulfothlon, fenteracol, fenthiaprop, fenthiaprop-ethyl, fenthion, fenthlon-ethyl, fentin, fentin acetate, fentin chloride, fentin hydroxide, fentrazamide, fentrifanil, fenuron, fenuron TCA, fenvalerate, ferbam, ferimzone, ferrous sulfate, fïpronil, flamprop, flamprop-lsopropyl, flamprop-M, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, flocoumafen, flometoquin, flonicamid, florasulam, fluacrypyrim, fluazifop, fluazifop-butyl, fluazifopmethyl, fluazîfop-P, fluazifop-P-butyl, fluazinam, fluazolate, fluazuron, flubendîamide, flubenzimine, flucarbazone, flucarbazone-sodîum, flucetosulfuron, fluchloralin, flucofuron, flucydoxuron, flucythrinate, fludioxonil, fluenetîl, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxuron, flufenprox, flufenpyr, flufenpyr-ethyl, flufiprole, flumethrin, flumetover, flumetralin, flumetsulam, flumezin, flumlclorac, flumiclorac-pentyl, flumioxazîn, flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram, fluorbenslde, fluoridamid, fluoroacetamide, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluoroimide, fluoromidine, fluoronitrofen, fluothluron, fluotrimazole, fluoxastrobln, flupoxam, flupropadl, flupropadine, flupropanate, flupropanate-sodium, flupyradifurone, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluquinconazole, flurazole, flurenol, flurenol-butyl, flurenol-methyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurprimidol, flursulamid, flurtamone, flusilazole, flusulfamide, fluthiacet, fluthlacet-methyl, flutianll, flutolanil, flutriafol, fluvalinate, fluxapyroxad, fluxofenim, folpet, fomesafen, fomesafen-sodium, fonofos, foramsulfuron, forchlorfenuron, formaldéhyde, formetanate, formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosamine, fosamine-ammonlum, fosetyl, fosetyl-aluminium, fosmethilan, fosplrate, fosthlazate, fosthletan, frontalin, fuberidazole, fucaojing, fucaoml, funaihecaoling, fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr, furathiocarb, furcarbanil, furconazole, furconazole-cis, furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen, gamma-cyhalothrin, gamma112
HCH, genit, gibberellic acid, gibberelllns, gliftor, glufoslnate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosInate-P-sodium, glyodin, glyoxime, glyphosate, glyphosatediammonlum, glyphosate-dimethylammonium, glyphosate-lsopropylammonlum, glyphosatemonoammonium, glyphosate-potasslum, glyphosate-sesquisodium, glyphosate-trimesium, glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatine acétates, halacrinate, halfenprox, halofenozide, halosafen, halosulfuron, halosulfuron-methyf, haloxydine, haloxyfop, haloxyfop-etotyl, ha loxyfop-m ethyl, haloxyfop-P, haloxyfop-P-etotyl, haloxyfop-P-methyl, haloxyfop· sodium, HCH, hemel, hempa, HEOD, heptachlor, heptenophos, heptopargil, heteraphos, hexachloroacetone, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexaflurate, hexalure, hexamlde, hexazinone, hexylthiofos, hexythiazox, HHDN, holosulf, huancalwo, huangcaoling, huanjunzuo, hydramethylnon, hydrargaphen, hydrated lime, hydrogen cyanide, hydroprene, hymexazol, hyquincarb, IAA, IBA, îcandin, Imazalil, Imazalil nitrate, imazali! sulfate, imazamethabenz, îmazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, Imazapyr-isopropylammonium, imazaquin, imazaquinammonium, Imazaquin-methyl, imazaquin-sodium, Imazethapyr, imazethapyr-ammonium, Imazosulfuron, imibenconazole, imlcyafos, imidadoprid, imidaclothlz, iminoctadine, iminodadine triacetate, iminoctadine trialbesiiate, imiprothrin, inabenfide, Indanofan, indaziflam, indoxacarb, inezin, iodobonil, iodocarb, iodomethane, iodosulfuron, iodosulfuron-methyf, iodosulfuron-methylsodium, iofensulfuron, iofensulfuron-sodium, ioxynil, loxynii odanoate, ioxynil-lithium, ioxynilsodium, ipazine, Ipconazole, ipfencarbazone, iprobenfos, iprodione, iprovalicarb, Iprymidam, ipsdienol, ipsenoi, IPSP, isamidofos, isazofos, isobenzan, isocarbamid, Isocarbophos, Isodl, Isodrin, Isofenphos, Isofenphos-methyf, isolan, isomethiozin, isonoruron, Isopolinate, isoprocarb, isopropalin, isoprothlolane, isoproturon, Isopyrazam, isopyrimol, isothioate, isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl, isoxaflutole, isoxapyrifop, isoxathlon, ivermedin, izopamfos, Japonilure, japothrins, jasmolin I, jasmolin li, jasmonic acid, jiahuangchongzong, jiajizengxiaolin, jiaxlangjunzhi, jîecaowan, jiecaoxl, jodfenphos, juvénile hormone I, juvénile hormone ü, juvénile hormone III, kadethrin, karbutilate, karetazan, karetazanpotassium, kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan, ketosplradox, ketosplradox-potassium, kinetin, kînoprene, kresoxim-methyl, kuicaoxi, lactofen, lambdacyhalothrin, iatilure, lead arsenate, lenadl, lepimectin, ieptophos, lindane, lineatin, linuron, lirimfos, litlure, looplure, iufenuron, Ivdingjunzhi, Ivxiancaolin, lythldathion, MAA, malathlon, maleic hydrazide, malonoben, maltodextrin, ΜΑΜΑ, mancopper, mancozeb, mandipropamid, maneb, matrine, mazidox, MCPA, MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPAdimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA113 isopropyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil, mecarbam, mecarblnzld, mecarphon, mecoprop, mecoprop-2-ethylhexyl, mecoprop-dimethylanimonium, mecoprop-dioiamlne, mecoprop-ethadyl, mecoprop-lsoctyl, mecoprop-m ethyl, mecoprop-P, mecoprop-P-2-ethylhexyl, mecoprop-P-dimethylammonium, mecoprop-P-lsobutyl, mecoproppotassium, mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform, medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr, mefenpyr-diethyl, mefluidide, mefluidide-diolamine, mefluidide-potassium, megatomoic acid, menazon, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride, mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride, mercuric oxide, mercurous chloride, merphos, mesoprazîne, mesosulfuron, mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamlfop, metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron, metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron, methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole, methfuroxam, methldathion, methiobencarb, methiocarb, methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos, methometon, methomyl, methoprene, methoprotryne, methoquin-butyl, methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methyl apholate, methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate, methylacetophos, methylchloroform, methyldymron, methylene chloride, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide, methylneodecanamlde, metiram, metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb, metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone, metribuzin, metsuifovax, metsulfuron, metsulfuron-methyl, mevinphos, mexacarbate, mieshuan, miibemectin, milbemydn oxlme, miineb, mipafox, mirex, MNAF, moguchun, molinate, molosuitap, monalide, monisouron, monochloroacetic acid, monocrotophos, monolinuron, monosulfuron, monosulfuron-ester, monuron, monuron TCA, morfamquat, morfamquat dichloride, moroxydine, moroxydine hydrochloride, morphothion, morzid, moxidectin, MSMA, muscalure, myclobutanil, myclozolin, N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos, naled, naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthoxyacetîc acids, naproanilide, napropamîde, naptalam, naptalam-sodium, natamycin, neburon, niclosamide, niclosamide-olamine, nicosulfuron, nicotine, nifluridide, nipyraclofen, nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nltrothal-isopropyl, norbormide, norflurazon, nomicotine, noruron, novaluron, noviflumuron, nuarimol, OCH, octachlorodipropyl ether, octhiiinone, ofurace, omethoate, orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron, oryctalure, orysastrobin,
114 oryzalin, osthol, ostramone, oxabetrinil, oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon, oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone, oxinecopper, oxolinic acid, oxpoconazole, oxpoconazole fumarate, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyfluorfen, oxymatrine, oxytetracycline, oxytetracycline hydrochloride, paclobutrazol, palchongding, para-dichlorobenzene, parafluron, paraquat, paraquat dichloride, paraquat dimetîlsulfate, parathlon, parathion-methyl, parinol, pebulate, pefurazoate, pelargonlc acid, penconazole, pencycuron, pendimethalin, penflufen, penfluron, penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, pentmethrin, pentoxazone, perfluldone, permethrin, pethoxamld, phenamacril, phenazlne oxide, phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenothrin, phenproxide, phenthoate, phenylmercuriurea, phenylmercury acetate, phenylmercury chloride, phenylmercury dérivative of pyrocatechol, phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim, phosalone, phosdiphen, phosfolan, phosfolan-methyl, phosglycin, phosmet, phosnichlor, phosphamldon, phosphlne, phosphocarb, phosphorus, phostin, phoxim, phoxim-methyi, phthalide, picloram, picloram-2-ethylhexyl, plcloram-lsoctyl, plcloram-methyl, plcloram-olamine, picloram-potassium, pidoram-triethylammonium, plcloram-tris(2-hydroxypropyl)ammonîum, picolinafen, picoxystrobin, pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide, piperonyl cyclonene, piperophos, plproctanyl, plproctanyl bromide, piprotal, pirimetaphos, pirimlcarb, pirimioxyphos, pirimîphos-ethyl, plrimlphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim, polyoxorimzinc, polythialan, potassium arsenite, potassium azide, potassium cyanate, potassium gibberellate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, potassium anaphthaleneacetate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, pretilachlor, primidophos, primisulfuron, primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese, proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol, profluralîn, profluthrin, profoxydim, proglinazine, proglinazine-ethyl, prohexadione, prohexadione-caldum, prohydrojasmon, promacyl, promecarb, prometon, prometryn, promurit, propachlor, propamidine, propamidine dihydrochloride, propamocarb, propamocarb hydrochloride, propanil, propaphos, propaquizafop, propargite, proparthrin, propazine, propetamphos, propham, propïconazole, propineb, propisochlor, propoxur, propoxycarbazone, propoxycarbazone-sodium, propyi isome, propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin, prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothlocarb hydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute, proxan, proxan-sodium, prynachlor, pydanon, pymetrozine, pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufen-ethyl, pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobln, pyrasulfotole, pyrazolynate, pyrazophos, pyrazosulfuron, pyrazosulfuron-ethyl,
115 pyrazothlon, pyrazoxyfen, pyresmethrin, pyrethrin 1, pyrethrin II, pyrethrins, pyribambenz-lsopropyl, pyribambenz-propyl, pyribencarb, pyribenzoxim, pyributicarb, pyricior, pyridaben, pyridafol, pyridalyl, pyridaphenthion, pyridate, pyridinïtrii, pyrifenox, pyrifluquinazon, pyriftalid, pyrimethanil, pyrimidifen, pyriminobac, pyrimlnobac-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole, pyripropanol, pyriproxyfen, pyrithiobac, pyrithiobac-sodium, pyrolan, pyroquilon, pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia, qulnacetol, quinacetol sulfate, qulnalphos, qulnalphos-methyl, quinazamid, qulnclorac, quinconazole, quinmerac, quinodamine, quinonamld, qulnothion, quinoxyfen, quintiofos, quintozene, qulzalofop, quizalofop-ethyl, quizalofop-P, quIzalofop-P-ethyl, quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide, rebemide, resmethrin, rhodethanil, rhodojaponin-lll, ribavirin, rimsulfuron, rotenone, ryania, saflufenacil, saijunmao, saisentong, salicylanilide, sanguinarine, santonin, schradan, scilliroside, sebuthylazine, secbumeton, sedaxane, selamectîn, semlamitraz, semlamltraz chloride, sesamex, sesamolin, sethoxydim, shuangjiaancaolin, siduron, siglure, silafluofen, silatrane, silica gel, sllthiofam, slmazlne, slmeconazole, simeton, sîmetryn, sintofen, SMA, S-metolachlor, sodium arsenlte, sodium azide, sodium chlorate, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium orthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide, sodium thiocyanate, sodium a-naphthaleneacetate, sophamide, spinetoram, spinosad, spirodiciofen, splromesifen, spirotetramat, spiroxamlne, streptomycin, streptomycin sesquisulfate, strychnine, sulcatol, sulcofuron, sulcofuron-sodium, sulcotrione, sulfallate, sulfentrazone, sulfiram, sulfluramid, sulfometuron, sulfometuron-methyl, sulfosulfuron, sulfotep, suifoxaflor, sulfoxide, sulfoxime, sulfur, suifuric acid, sulfuryl fluoride, sulglycapin, sulprofos, sultropen, swep, fau-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium, TCA-calctum, TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE, tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebuplrîmfos, tebutam, tebuthiuron, tecioftalam, tecnazene, tecoram, teflubenzuron, tefluthrin, tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydîm, terallethrin, terbadl, terbucarb, terbuchlor, terbufos, terbumeton, terbuthylazlne, terbutryn, tetcyciacis, tetrachioroethane, tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin, tetramethylfluthrin, tetramlne, tetranadin, tetrasul, thallium sulfate, thenylchlor, theta-cypermethrin, thiabendazole, thiacloprid, thiadifluor, thiamethoxam, thiapronil, thiazafluron, thiazopyr, thlcrofos, thicyofen, thldiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thlfensulfuron-methyl, thifluzamide, thlobencarb, thlocarboxlme, thiochlorfenphîm, thiocyclam, thiocydam hydrochloride, thiocyclam oxalate, thiodiazole-copper, thlodicarb, thlofanox, thiofluoximate, thlohempa, thiomersal, thiometon, thionazin, thiophanate, thiophanate-methyl, thioquinox, thiosemicarbazide, thiosultap, thiosultap-dîammonium, thiosultap-disodîum, thiosultap
116 monosodium, thiotepa, thiram, thuringiensin, tiadinil, tiaojiean, tiocarbazil, tiodorim, tioxymid, tirpate, tolclofos-methyl, tolfenpyrad, tolylfluanid, tolylmercury acetate, topeamezone, tralkoxydim, tralocythrin, tralomethrin, tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol, triadimefon, triadimenol, triafamone, tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulfuron, triazamate, triazbutil, triaziflam, triazophos, triazoxide, tribenuron, tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamlde, trichlorfon, trichlormetaphos-3, trichloronat, triclopyr, triclopyr-butotyl, tridopyr-ethyl, triclopyr-triethylammonium, tricydazole, tridemorph, tridiphane, trietazine, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron, trifloxysulfuron-sodium, triflumizole, triflumuron, trifluralin, triflusulfuron, triflusulfuron-methyl, trifop, trifop-methyl, trifopsime, triforine, trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, trinexapac-ethyl, triprene, tripropindan, triptolide, tritac, triticonazole, tritosulfuron, trunc-call, unîconazole, uniconazole-P, urbacide, uredepa, valerate, validamycln, valifenalate, valone, vamidothion, vangard, vaniliprole, vemolate, vindozolin, warfarin, warfarin-potassium, warfarin-sodium, xïaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols, xylylcarb, yishijing, zarilamid, zeatin, zengxlaoan, zetacypermethrin, zinc naphthenate, zinc phosphide, zinc thlazole, zineb, ziram, zolaprofos, zoxamide, zuomihuanglong, α-chlorohydrin, a-ecdysone, a-multistriatin, and α-naphthaleneacetic add. For more Information consult the “Compendium of Pesticide Commdn Names located at http://www. ala nwood. net/pesticides/i ndex. html. Also consult “The Pesticide Manual 14th Edition, edited by C D S Tomlin, copyright 2006 by British Crop Production Council, or its prior or more recent éditions.
BIOPESTICIDES
Molécules of Formula One may also be used In combination (such as in a compositional mixture, or a simultaneous or sequential application) with one or more biopesticides. The term “biopesticide Is used for microbial biological pest control agents that are applied in a similar manner to chemical pesticides. Commonly these are bacterial, but there are also examples of fungal control agents, Induding Trichoderma spp. and Ampelomyces quisqualis (a control agent for grape powdery mildew). Bacillus subtilis are used to control plant pathogens. Weeds and rodents hâve also been controlled with microbial agents. One well-known Insecticide example Is Bacillus thuringiensis, a bacterial disease of Lepidoptera, Coleoptera, and Diptera. Because it has little effect on other organisme, lt Is considered more environmentally friendly than synthetic pesticides. Biological insecticides include products based on:
1. entomopathogenic fungi (e.g. Metarhizium anisopliae):
2. entomopathogenic nematodes (e.g. Steinemema feltiae)·, and
117
3. entomopathogenic viruses (e.g. Cydia pomonella granulovirus).
Other examples of entomopathogenic organlsms Include, but are not limited to, baculoviruses, bacteria and other prokaryotic organisons, fungl, protozoa and Microsproridia. Biologically derived insecticides Include, but not limited to, rotenone, veratridine, as well as microbial toxins; Insect tolérant or résistant plant varieties; and organisme modified by recombinant DNA technology to either produce insecticides or to convey an insect résistant property to the genetically modified organism. ln one embodiment, the molécules of Formula One may be used with one or more biopesticides In the area of seed treatments and soil amendments. The Manual of Biocontrol Agents gives a review of the available biological insecticide (and other biology-based control) products. Copping LG. (ed.) (2004). The Manual of BiocontrolAgents (formerly the Biopesticide Manual) 3rd Edition. British Crop Production Coundl (BCPC), Famham, Surrey UK.
OTHER ACTIVE COMPOUNDS
Molécules of Formula One may also be used in combination (such as ln a compositional mixture, or a simultaneous or sequential application) with one or more ofthe following:
1. 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;
2. 3-(4’-chloro-2,4-dimethyl[1,1 '-blphenyl]-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4,5]dec-3-en-2one;
3. 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5W)'furanone;
4. 4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-furanone;
5. 3-chloro-N2-[(1 S)-1-methyl-2-(methylsulfonyl)ethyl]-N1 -[2-methyl-4-[1,2,2,2-tetrafluoro-1(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide;
6. 2-cyano-/V-ethyl-4-fluoro-3-methoxy-benenesulfonamide;
7. 2-cyano-/V-ethyl-3-methoxy-benzenesulfonamide;
8. 2-cyano-3-dîfluoromethoxy-/V-ethyl-4-fluoro-benzenesulfonamide;
9. 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide;
10. 2-cyano-6-fluoro-3-methoxy-N,N-dîmethyl-benzenesulfonamide;
11. 2-cyano-N-ethyl-6-fluoro-3-methoxy-/V-methyl-benzenesulfonamlde;
12. 2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfon-amide;
13. 3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazoie-4-carboxamide;
14. N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-a,a,a-trifluoro-p-tolyl) hydrazone;
118
15. N-ethyl-2.2-dichloro-1 -methylcyclopropane-carboxamlde-2-(2,6-dichloro-a,a,a-trifluoro-ptolyl) hydrazone nicotine;
16. 0-{(E-)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl])S-methyl thiocarbonate;
17. (E)-N1-[(2-chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;
18. 1 -(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imldazo[1 ,2-a]pyridin-
5-ol;
19. 4-[4-chlorophenyl-(2-butylidine-hydrazono)methyl)]phenyl mesylate; and
20. N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-{2,6-dichloro-a/pha,a/pha,a/phatrifluoro-p-tolyl)hydrazone.
SYNERGISTIC MIXTURES
Molécules of Formula One may be used with certain active compounds to form synergistîc mixtures where the mode of action of such compounds compared to the mode of action of the molécules of Formula One are the same, similar, or different. Examples of modes of action Include, but are not limited to: acetylcholinesterase inhibitor; sodium channel modulator; chitin biosynthesis Inhibitor; GABA and glutamate-gated chloride channel antagonist; GABA and glutamate-gated chloride channel agonist; acétylcholine receptor agonist; acétylcholine receptor antagonist; MET I inhibitor; Mg-stîmulated ATPase Inhibitor; nicotinic acétylcholine receptor; Midgut membrane disrupter; oxidative phosphorylation disrupter, and ryanodine receptor (RyRs). Generally, weight ratios of the molécules of Formula One in a synergistîc mixture with another compound are from about 10:1 to about 1:10, In another embodiment from about 5:1 to about 1:5, and in another embodiment from about 3:1, and in another embodiment about 1:1.
FORMULATIONS
A pesticide is rarely suitabie for application in its pure form. It is usually necessary to add other substances so that the pesticide can be used at the required concentration and in an appropriate form, permitting ease of application, handling, transportation, storage, and maximum pesticide activity. Thus, pesticides are formulated into, for example, baits, concentrated émulsions, dusts, emulslfiable concentrâtes, fumigants, gels, granules, microencapsulations, seed treatments, suspension concentrâtes, suspoemulsions, tablets, water soluble lîquids, water dispersible granules or dry flowables, wettable powders, and ultra low volume solutions. For further information on
119 formulation types see “Catalogue of Pesticide Formulation Types and International Coding System
Technical Monograph n’2, 5th Edition by CropLife International (2002).
Pesticides are applied most often as aqueous suspensions or émulsions prepared from concentrated formulations of such pesticides. Such water-soluble, water-suspendable, or emulsifiable formulations are either solids, usually known as wettable powders, or water dispersible granules, or liquids usually known as emulsifiable concentrâtes, or aqueous suspensions. Wettable powders, which may be compacted to form water dispersible granules, comprise an intimate mixture of the pesticide, a carrier, and surfactants. The concentration of the pesticide is usually from about 10% to about 90% by weight. The carrier is usually selected from among the attapulgite clays, the montmorillonite ciays, the diatomaceous earths, or the purified silicates. Effective surfactants, comprising from about 0.5% to about 10% of the wettable powder, are found among sulfonated lignins, condensed naphthalenesulfonates, naphthalenesulfonates, alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phénols.
Emulsifiable concentrâtes of pesticides comprise a convenient concentration of a pesticide, such as from about 50 to about 500 grams per liter of liquid dissolved in a carrier that Is either a water miscible solvent or a mixture of water-lmmiscible organic solvent and emulsifiers. Useful organic solvents include aromatlcs, especially xylenes and petroleum fractions, espedally the highboiiing naphthalenlc and otefÎnic portions of petroleum such as heavy aromatic naphtha. Other organic solvents may also be used, such as the terpenic solvents including rosin dérivatives, aliphatic ketones such as cyclohexanone, and complex alcohois such as 2-ethoxyethanol. Suitable emulsifiers for emulsifiable concentrâtes are selected from conventional anlonîc and non-ionic surfactants.
Aqueous suspensions comprise suspensions of water-insoluble pesticides dispersed in an aqueous carrier at a concentration in the range from about 5% to about 50% by weight. Suspensions are prepared by finely grinding the pesticide and vigorously mlxing it into a carrier comprised of water and surfactants. Ingrédients, such as inorganic salts and synthetic or naturel gums may also be added, to increase the density and viscosity of the aqueous carrier. It is often most effective to grind and mlx the pesticide at the same time by preparing the aqueous mixture and homogenlzîng It in an implement such as a sand mili, bail mlli, or piston-type homogenizer.
Pesticides may also be applied as granular compositions that are particularly usefui for applications to the soi). Granular compositions usualiy contain from about 0.5% to about 10% by weight of the pesticide, dispersed in a carrier that comprises ciay or a similar substance. Such compositions are usualiy prepared by dissolving the pesticide in a suitable solvent and applying it to 120 a granular carrier which has been pre-formed tothe appropriate partide slze, In the range of from about 0.5 to about 3 mm. Such compositions may also be formulated by making a dough or paste of the carrier and compound and crushlng and drying to obtaîn the desired granular partide slze.
Dusts containing a pesticide are prepared by Intimately mixing the pesticide In powdered form with a suitable dusty agriculture) carrier, such as kaolin day, ground volcanlc rock, and the like, Dusts can suitably contain from about 1% to about 10% of the pesticide. They can be applied as a seed dressing or as a foliage application with a dust blower machine.
It Is equally pradical to apply a pesticide In the form of a solution in an appropriate organic solvent, usually petroleum oil, such as the spray olls, which are widely used In agricultural chemistry.
Pestlddes can also be applied In the form of an aérosol composition. In such compositions the pestldde is dissolved or dispersed In a carrier, which Is a pressure-generating propellant mixture. The aérosol composition is packaged In a container from which the mixture is dispensed through an atomizing valve.
Pestidde baits are formed when the pesticide Is mixed with food or an attractant or both. When the pests eat the bait they also consume the pesticide. Baits may take the form of granules, gels, flowabie powders, liquids, or solids. They can be used In pest harborages.
Fumigants are pesticides that hâve a relatively high vapor pressure and hence can exist as a gas in suffirent concentrations to kill pests in soil or endosed spaces. The toxidty of the fumigant Is proportional to its concentration and the exposure time. They are characterized by a good capacîty for diffusion and act by penetrating the pest's resplratory system or being absorbed through the pest's cutide. Fumigants are applied to control stored product pests under gas proof sheets, in gas sealed rooms or buildings or In spécial chambers.
Pestlddes can be microencapsulated by suspending the pestidde partides or droplets in plastic polymers of various types. By altering the chemistry of the polymer or by changing factors in the processing, microcapsules can be formed of various sizes, soiubility, wall thicknesses, and degrees of penetrability. These factors govem the speed with which the active ingrédient within Is released, which in tum, affects the resldual performance, speed of action, and odorof the product.
Oil solution concentrâtes are made by dissolvlng pestidde In a solvent that will hold the pesticide in solution. Oil solutions of a pesticide usually provide faster knockdown and klil of pests than other formulations due to the solvents themselves having pestiddal action and the dissolution of the waxy covering of the Integument increasing the speed of uptake of the pesticide. Other
121 advantages of oil solutions Include better storage stability, better pénétration of crevices, and better adhesion to greasy surfaces.
Another embodiment is an oil-in-water émulsion, wherein the émulsion comprises oily globules which are each provided with a lamellar liquid crystal coating and are dispersed ln an aqueous phase, wherein each oily globule comprises at least one compound which is agriculturally active, and is Indîvidually coated with a monolamellar or oligolamellar layer comprising: (1) at least one non-lonlc lipophilie surface-active agent, (2) at least one non-ionic hydrophilic surface-active agent and (3) at least one ionic surface-active agent, wherein the globules having a mean particle diameter of less than 800 nanometers. Further information on the embodiment is disclosed ln U.S. patent publication 20070027034 published February 1,2007, having Patent Application serial number 11/495,228. For ease of use, this embodiment will be referred to as OIWE.
For further Information consult Insect Pest Management 2nd Edition by D. Dent, copyright CAB International (2000). Additionally, for more detailed information consult Handbook of Pest Control - The Behavior, Life History, and Control of Household Pests by Arnold Mallis, 9th Edition, copyright 2004 by GIE Media Inc.
OTHER FORMULATION COMPONENTS
Generally, when the molécules disclosed in Formula One are used in a formulation, such formulation can also contain other components. These components Include, but are not Iimited to, (this is a non-exhaustive and non-mutually exclusive list) wetters, spreaders, stickers, pénétrants, buffers, sequestering agents, drift réduction agents, compatibility agents, anti-foam agents, deaning agents, and emulsifiers. A few components are described forthwith.
A wetting agent is a substance that when added to a liquid increases the spreading or pénétration power of the liquid by reducing the Interfacial tension between the liquid and the surface on which it Is spreading. Wetting agents are used for two main fonctions ln agrochemical formulations: during processing and manufacture to Increase the rate of wetting of powders in water to make concentrâtes for soluble liquide or suspension concentrâtes; and during mixing of a product with water ln a spray tank to reduce the wetting time of wettable powders and to Improve the pénétration of water Into water-dispersibie granules. Examples of wetting agents used ln wettable powder, suspension concentrate, and water-dispersibie granule formulations are: sodium lauryl sulfate; sodium dioctyl sulfosuccinate; alkyl phénol ethoxylates; and aiiphatic alcohol ethoxylates.
122
A dispersing agent Is a substance which adsorbs onto the surface of particles and helps to preserve the state of dispersion of the particles and prevents them from reaggregating. Dispersing agents are added to agrochemical formulations to fadlitate dispersion and suspension during manufacture, and to ensure the particles redisperse into water In a spray tank. They are wideiy used In wettable powders, suspension concentrâtes and water-dispersible granules. Surfactants that are used as dispersing agents hâve the ability to adsorb strongly onto a particle surface and provide a charged or steric barder to reaggregation of partides. The most commonly used surfactants are anionlc, non-lonlc, or mixtures of the two types. For wettable powder formulations, the most common dispersing agents are sodium lignosulfonates. For suspension concentrâtes, very good adsorption and stabilization are obtained using polyelectrolytes, such as sodium naphthalene suifonate formaldéhyde condensâtes. Tristyrylphenol ethoxyiate phosphate esters are also used. Non-ionics such as alkylarylethylene oxide condensâtes and EO-PO block copolymers are sometimes combined with anlonlcs as dispersing agents for suspension concentrâtes. In recent years, new types of very high molecular weight polymeric surfactants hâve been developed as dispersing agents. These hâve very long hydrophobie ‘backbones* and a large number of ethylene oxide chains forming the ’teeth’ of a ’comb’ surfactant. These high molecular weight poiymers can give very good long-term stability to suspension concentrâtes because the hydrophobie backbones hâve many anchoring points onto the particle surfaces. Examples of dispersing agents used in agrochemical formulations are: sodium lignosulfonates; sodium naphthalene suifonate formaldéhyde condensâtes; tristyrylphénol ethoxyiate phosphate esters; aliphatic alcohol ethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graft copolymers.
An emulsifying agent is a substance which stabilizes a suspension of droplets of one liquid phase In another liquid phase. Without the emulsifying agent the two liquids would separate into two immiscible liquid phases. The most commonly used emulsifier blends contain alkylphenol or aliphatic alcohol with twelve or more ethylene oxide units and the oii-soluble calcium sait of dodecylbenzenesulfonic acid. A range of hydrophile-iipophile balance (HLB') values from 8 to 18 will normally provide good stable émulsions. Emulsion stability can sometimes be Improved by the addition of a small amount of an EO-PO block copolymer surfactant.
A solubilizing agent is a surfactant which will form mlcelles In water at concentrations above the critical micelle concentration. The mlcelles are then able to dissolve or solubilize water-insoluble materials Inside the hydrophobie part of the micelle. The types of surfactants usually used for soiubîlization are non-ionics, sorbitan monooleates, sorbitan monooleate ethoxylates, and methyl oieate esters.
123
Surfactants are sometimes used, either alone or with other additives such as minerai or vegetable oils as adjuvants to spray-tank mixes to Improve the biological performance of the pesticide on the target. The types of surfactants used for bioenhancement dépend generaily on the nature and mode of action of the pesticide. However, they are often non-lonics such as: alkyl ethoxylates; linear aliphatic alcohol ethoxylates; aliphatîc amine ethoxylates.
A carrier or diluent in an agricultural formulation is a material added to the pesticide to give a product of the required strength. Carriers are usualiy materials with high absorptîve capacities, while diluents are usualiy materials with low absorptîve capacities. Carriers and diiuents are used in the formulation of dusts, wettable powders, granules and water-dispersible granules.
Organic solvents are used mainiy in the formulation of emulsîfiable concentrâtes, oiHnwater émulsions, suspoemulsions, and ultra low volume formulations, and to a lesser extent, granular formulations. Sometimes mixtures of solvents are used. The first main groups of solvents are aliphatîc paraffinic oils such as kerosene or refined paraffine. The second main group (and the most common) comprises the aromatic solvents such as xylene and higher molecular weight fractions of C9 and C10 aromatic solvents. Chlorinated hydrocarbons are useful as cosolvents to prevent crystallization of pesticides when the formulation Is emulsified into water. Alcohols are sometimes used as cosolvents to increase solvent power. Other solvents may include vegetable oils, seed oils, and esters of vegetable and seed oils.
Thickeners or gelling agents are used mainiy In the formulation of suspension concentrâtes, émulsions and suspoemulsions to modify the rheology or flow properties of the liquid and to prevent séparation and settling of the dispersed particles or droplets. Thickening, gelling, and anti-settiing agents generaily fall into two categories, namely water-insoluble parti eu la te s and water-soluble polymers. It Is possible to produce suspension concentrate formulations using clays and silicas. Examples of these types of materials, include, but are not limited to, montmoriilonite, bentonite, magnésium aluminum silicate, and attapulgite. Water-soluble polysaccharides hâve been used as thickening-geliing agents for many years. The types of polysaccharides most commonly used are natural extracts of seeds and seaweeds or are synthetic dérivatives of cellulose. Examples of these types of materials include, but are not limited to, guar gum; locust bean gum; carrageenam; alglnates; methyl cellulose; sodium carboxymethyl cellulose (SCMC); hydroxyethyl cellulose (HEC). Other types of anti-settiing agents are based on modified starches, polyacrylates, polyvinyl alcohol and polyethylene oxide. Another good anti-settiing agent is xanthan gum.
Microorganisms can cause spoilage of formulated products. Therefore préservation agents are used to eliminate or reduce their effect. Examples of such agents include, but are not limited to: propionic acid and its sodium sait; sorbic acid and its sodium or potassium salts; benzoic acid and 124
Its sodium sait; p-hydroxybenzoic acid sodium sait; methyl p-hydroxybenzoate; and 1,2benzisothiazolin-3-one (BIT).
The presence of surfactants often causes water-based formulations to foam during mixing operations ln production and ln application through a spray tank, ln order to reduce the tendency to foam, antl-foam agents are often added either during the production stage or before fîlling Into bottles. Generally, there are two types of anti-foam agents, namely silicones and non-silicones. Silicones are usually aqueous émulsions of dimethyl polysîloxane, while the non-silicone anti-foam agents are water-lnsoluble oils, such as octanol and nonanol, orsilica. ln both cases, the fonction of the antl-foam agent Is to displace the surfactant from the alr-water Interface.
‘Green agents (e.g., adjuvants, surfactants, solvents) can reduce the overall environmental footprint of crop protection formulations. Green agents are biodégradable and generally derived from naturel and/or sustainable sources, e.g. plant and animai sources. Spécifie examples are: vegetable oils, seed oils, and esters thereof, also alkoxytated aikyl polyglucosides.
For further information, see Chemistry and Technology of Agrochemical Formulations edited by D.A. Knowles, copyright 1998 by Kluwer Academie Pubiishers. Also see insecticides ln Agriculture and Environment - Retrospects and Prospects by A.S. Perry, I. Yamamoto, I. Ishaaya, and R. Perry, copyright 1998 by Springer-Verlag.
PESTS ln general, the molécules of Formula One may be used to control pests e.g. beetles, earwlgs, cockroaches, files, aphids, scales, whiteflies, ieafhoppers, ants, wasps, termites, moths, butterflies, lice, grasshoppers, locusts, crickets, fleas, thrips, bristletails, mites, ticks, nematodes, and symphylans.
ln another embodiment, the molécules of Formula One may be used to control pests in the Phyla Nematoda and/or Arthropode.
ln another embodiment, the molécules of Formula One may be used to controi pests in the Subphyla Chellcerata, Myrlapoda, and/or Hexapoda.
ln another embodiment, the molécules of Formula One may be used to control pests in the Classes of Arachnlda, Symphyla, and/or Insecta.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Anoplura. A non-exhaustive list of particular généra Includes, but Is not limited to, Haematopinus spp., Hoplopleura spp., Unognathus spp., Pediculus spp., and Polyplax spp. A non
125 exhaustive list of particular species Includes, but is not limited to, Haematopinus asini, Haematoplnus suis, Unognathus setosus, Unognathus ovillus, Pediculus humanus capitis, Pediculus humanus humanus, and Pthirus pubis.
In another embodiment, the molécules of Formula One may be used to control pests In the 5 Order Coleoptera. A non-exhaustive list of particular généra includes, but Is not limited to, Acanthosceiides spp., Agriotes spp., Anthonomus spp., Apion spp., Apogonia spp., Aulacophora spp., Bruchus spp., Cerostema spp., Cerotoma spp., Ceutorhynchus spp., Chaetocnema spp., Colaspls spp., Ctenicera spp., Curculio spp., Cyclocephala spp., Diabrotica spp., Hypera spp., Ips spp., Lyctus spp., Megascelis spp., Meligethes spp., Otiorhynchus spp., Pantomorus spp.,
Phyllophaga spp., Phyllotreta spp., Rhizotrogus spp., Rhynchites spp., Rhynchophorus spp., Sco/ytus spp., Sphenophorus spp., Sitophilus spp., and Tribolium spp. A non-exhaustive list of particular species Includes, but Is not limited to, Acanthosceiides obtectus, Agrilus planipennis, Anoplophora glabripennis, Anthonomus grandis, Ataenius spretulus, Atomaria linearis, Bothynoderes punctiventris, Bruchus plsorum, Callosobruchus maculatus, Carpophilus hemipterus,
Cassida vittata, Cerotoma trifurcata, Ceutorhynchus assimilis, Ceutorhynchus napi, Conoderus scalaris, Conoderus stigmosus, Conotrachelus nénuphar, Cotinis nitida, Crioceris asparagi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptolestes turcicus, Cylindrocopturus adspersus, Deporaus marginatus, Dermestes larda ri us, Dermestes maculatus, Epilachna varivestis, Faustinus cubae, Hylobius pales, Hypera postica, Hypothenemus hampe!, Lasioderma semcome,
Leptinotarsa decemlineata, Uogenys fuscus, Uogenys suturalis, Ussorhoptrus oryzophilus, Maecolaspisjoliveti, Melanotus communia, Meligethes aeneus, Melolontha melolontha, Oberea brevis, Oberea linearis, Oryctes rhinocéros, Oryzaephilus mercator, Oryzaephilus surinamensls, Ouléma melanopus, Ouléma oryzae, Phyllophaga cuyabana, Popillia japonica, Prostephanus truncatus, Rhyzopertha dominica,, Sitona lineatus, Sitophilus granarius, Sitophilus oryzae,
Sitophilus zeamais, Stegobium panlceum, Tribolium castaneum, Tribolium confusum, Trogoderma variabile, and Zabrus tenebrioides.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Dermaptera.
In another embodiment, the molécules of Formula One may be used to control pests of the
Order Blattarla. A non-exhaustive list of particular spedes indudes, but is not limited to, Blattella germanica, Blatta orientalis, Parcoblatta pennsylvanlca, Periplaneta americana, Periplaneta australaslae, Periplaneta brunnea, Periplaneta fuliginosa, Pycnoscelus surinamensls, and Supelia longïpalpa.
126 ln another embodiment, the molécules of Formula One may be used to control pests of the Order Dlptera. A non-exhaustive list of particular généra Includes, but is not Iimited to, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Bactrocera spp., Ceratitis spp., Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineura spp., Délia spp., Drosophile spp., Fannia spp., Hylemyia spp., Llriomyza spp., Musca spp., Phorbia spp., Tabanus spp., and Tipula spp. A non-exhaustive list of particular species includes, but Is not Iimited to, Agromyza frontella, Anastrepha suspensa, Anastrepha ludens, Anastrepha obliqa, Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera invadens, Bactrocera zonata, Ceratitis capitata, Dasineura brasslcae, Délia platura, Fannia canicularis, Fannia scalaris, Gasterophilus intestinalis, Graclllia perseae, Haematobia irritans, Hypoderma Hneatum, Liriomyza brassicae, Melophagus ovinus, Musca autumnalis, Musca domestica, Oestrus ovis, Oscinella frit, Pegomya betae, Psila rosae, Rhagoletis cerasi, Rhagoletis pomonella, Rhagoletis mendax, Sitodiplosls mosellana, and Stomoxys cal titra ns.
ln another embodiment, the moiecules of Formula One may be used to control pests of the Order Hemlptera. A non-exhaustive list of particular généra Includes, but Is not Iimited to, Adelges spp., Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Ceroplastes spp., Chlonaspis spp., Chrysomphalus spp., Coccus spp., Empoasca spp., Lepidosaphes spp., Lagynotomus spp., Lygus spp., Macrosiphum spp., Nephotettix spp., Nezara spp., Philaenus spp., Phytocoris spp., Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopaloslphum spp., Saissetia spp., Therîoaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes spp., Triatoma spp. and Unaspis spp. A non-exhaustive list of particular species includes, but is not Iimited to, Acrostemum hilare, Acyrthosiphon pisum, Aleyrodes proletella, Aleurodicus dispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula, Aonidiella aurantii, Aphis gossypii, Aphis glycines, Aphis pomi, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Blissus leucopterus, Brachycorynella asparagi, Brevennia rehi, Brevicoryne brassicae, Calocoris norvegicus, Ceroplastes rubens, Clmex hemipterus, Cimex lectularius, Dagbertus fasciatus, Dichelops furcatus, Diuraphis noxia, Diaphorina citri, Dysaphis plantaginea, Dysdercus suturellus, Edessa meditabunda, Eriosoma lanigerum, Eurygaster maura, Euschistus héros, Euschistus servus, Helopeltis antonii, Helopeltis theivora, Icerya purchasl, Idioscopus nitidulus, Laodelphax striatellus, Leptocorisa oratorius, Leptocorisa varicornis, Lygus hesperus, Maconellicoccus hirsutus, Macrosiphum euphorblae, Macrosiphum granarium, Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frîmbiolata, Metopolophïum dirhodum, Midis longicornis, Myzus persicae, Nephotettix cindipes, Neurocolpus longirostris, Nezara viridula, Nilaparvata lugens, Parlatoria pergandii, Parlatoria ziziphi, Peregrinus maidis. Phylloxéra vitifoliae, Physokermes piceae,, Phytocoris californicus, Phytocoris relativus,
127
Piezodorus guildinii, Poecilocapsus lineatus, Psallus vaccînlcola, Pseudacysta perseae, Pseudococcus brevipes, Quadraspidiotus pamlciosus, Rhopalosîphum maidis, Rhopalosiphum padi, Saissetia oleae, Scaptocon's castanea, Schizaphis graminum, Sitobion avenae, Sogatella furcifera, Trialeurodesvaporariorum, Trialeurodes abutiloneus, Unaspis yanonensis, and Zulia entrernana.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Hymenoptera. A non-exhaustive list of particular généra Includes, but is not limited to, Acromyrmex spp., Atta spp., Camponotus spp., Diprion spp., Formica spp., Monomorium spp., Neodiprion spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp., Vespula spp., and Xy/ocopa spp. A non-exhaustive list of particular species Includes, but is not limited to, Athalia rosae, Atta taxana, Iridomyrmex humilis, Monomorium minimum, Monomorium pharaonis, Solenopsis Invicta, Solenopsis geminata, Solenopsis molesta, Solenopsis richtery, Solenopsis xyfoni, and Tapinoma sessile.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Isoptera. A non-exhaustive list of particular généra includes, but is not limited to, Coptotermes spp., Comitermes spp., Cryptotermes spp., Heterotermes spp., Kalotermes spp., Incisitermes spp., Macrotermes spp., Marginitermes spp., Microcerotermes spp., Procomîtermes spp., Reticulitermes spp., Schedorhinotermes spp., and Zootermopsls spp. A non-exhaustive list of particular species includes, but Is not limited to, Coptotermes curvignathus, Coptotermes frenchi, Coptotermes formosanus, Heterotermes aureus, Microtermes obesl, Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes haganl, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis, and Reticulitermes virginicus.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Lepldoptera. A non-exhaustive list of particular généra Includes, but is not limited to, Adoxophyes spp., Agrotis spp., Argyrotaenia spp., Cacoecia spp., Caloptilia spp., Chilo spp., Chrysodeixis spp., Colias spp., Crambus spp., Diaphania spp., Diatraea spp., Earias spp., Ephestia spp., Epimecis spp., Feltia spp., Gortyna spp., Helicoverpa spp., Heliothls spp., Indarbela spp., Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Peridroma spp., Phyllonorycter spp., Pseudaletia spp., Sesamia spp., Spodoptera spp., Synanthedon spp., and Yponomeuta spp. A non-exhaustive list of particular species Includes, but is not limited to, Achaea janata, Adoxophyes orana, Agrotis Ipsilon, Alabama argillacea, Amorbia cuneana, Amyelols transitella, Anacamptodes defectaria, Anarsia lineatella, Anomis sabulifera, Anticarsia gemmatalis, Archips argyrospila, Archips rosana, Argyrotaenia citrana. Autographe gamma, Bonagota cranaodes, Borbo cinnara, 128
Bucculatrix thurberiella, Cepue reticulana, Carposina niponensis, Chlumetia transversa, Choristoneura rosaceana, Cnaphalocrocis medinalis, Conopomorpha cramerella, Cossus cossus, Cydia caryana, Cydia funebrana, Cydia molesta, Cydia nlgricana, Cydia pomonella, Darna diducta, Diatraea saccharalis, Diatraea grandiosella, Ean'as insulena, Earias vittella, Ecdytolopha aurantianum, Elasmopalpus lignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehnlella, Epinotia aporema, Epiphyas postvittana, Erionota thrax, Eupoecilia amblguella, Euxoa auxiliaris, Grapholita molesta, Hedylepta Indicata, Helicoverpa armlgera, Helicoverpa zea, Heliothls virescens, Hellula undalis, Keiferia lycopersicella, Leuclnodes orbonalis, Leucoptera coffeella, Leucoptera malifolieila, Lobe sia botrana, Loxagrotis albicosta, Lymantrla dispar, Lyonetia clerkella, Mahasena corbetti, Mamestra brassicae, Maruca testulalis, Metisa plana, Mythimna unipuncta, Neoleuclnodes elegantalis, Nymphula depunctalis, Operophtera brumata, Ostrinla nubilalis, Oxydia vesulia, Pandemls cerasana, Pandemis heparana, Papilio demodocus, Pectinophora gossypiella, Peridroma saucia, Perileucoptera coffeella, Phthorimaea operculella, Phyllocnistis citrella, Pieris rapae, Plathypena scabra, Plodia interpunctella, Plutella xylostella, Polychrosls viteana, Prays endocarpe, Prays oleae, Pseudaletia unipuncta, Pseudoplusia includens, Rachiplusia nu, Sclrpophaga Incertulas, Sesamia inferens, Sesamla nonagrioldes, Setora nitens, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera eridania, Thecla basilldes, Tineola bisselliella, Trlchoplusla ni, Tuta absoluta, Zeuzera coffeae, and Zeuzera pyrina.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Mallophaga. A non-exhaustive list of particular généra Includes, but is not limited to, Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., and Trichodectes spp. A non-exhaustive list of particular species includes, but is not limited to, Bovicola bovis, Bovicola caprae, Bovicola ovis, Chelopistes meleagridis, Goniodes dissimilis, Goniodes glgas, Menacanthus stramineus, Menopon gallinae, and Trichodectes canis.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Orthoptera. A non-exhaustive list of particular généra includes, but Is not limited to, Melanoplus spp., and Pterophylla spp. A non-exhaustive list of particular species includes, but Is not limited to, Anabrus simplex, Gryllotalpa africana, Gryllotalpa australis, Gryllotalpa brachyptera, Gryllotalpa hexadactyla, Locusta mlgratoria, Microcentrum retinerve, Schistocerca gregaria, and Scudderia furcata.
In another embodiment, the molécules of Formula One may be used to control pests of the Order SIphonaptera. A non-exhaustive list of particular species includes, but is not limited to,
129
Ceratophyllus gallinae, Ceratophyllus niger, Ctenocephalîdes canis, Ctenocephalîdes felis, and
Pulex Irritans.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Thysanoptera. A non-exhaustive list of particular généra Includes, but is not limited to, Caliothrips spp., Frankliniella spp., Sclrtothrips spp„ and Thrips spp. A non-exhaustive list of particular sp. Includes, but is not limited to, Frankliniella fusca, Frankliniella occîdentalis, Frankliniella schultzel, Frankliniella Williams!, Heliothrips haemorrhoidalis, Rhiplphorothrips cruentatus, Sclrtothrips citri, Scirtothrips dorsalis, and Taenlothrips rhopalantennalis, Thrips hawaiiensls, Thrips nigropilosus, Thrips orientalis, Thrips tabac!.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Thysanura. A non-exhaustive list of particular généra Includes, but Is not limited to, Lepisma spp. and Thermobia spp.
In another embodiment, the molécules of Formula One may be used to control pests of the Order Acarlna. A non-exhaustive list of particular généra includes, but Is not limited to, Acarus spp., Aculops spp., Boophilus spp., Demodex spp., Dermacentor spp., Epitrimerus spp., Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp., Rhizoglyphus spp., and Tetranychus spp. A non-exhaustive list of particular species includes, but is not limited to, Acarapis woodi, Acarus siro, Acerla mangiferae, Aculops lycoperslci, Aculus pelekassl, Aculus schlechtendall, Amblyomma americanum, Brevipalpus obovatus, Brevipalpus phoenicîs, Dermacentor variabilis, Dermatophagoldes pteronyssinus, Eotetranychus carpinl, Notœdres cati, Oligonychus coffeae, Oligonychus ilicis, Panonychus citri, Panonychus ulml, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Rhipîcephalus sanguineus. Sarcoptes scabiel, Tegdophus perseaflorae, Tetranychus urtlcae, and Varroa destructor.
In another embodiment, the molécules of Formula One may be used to control pest of the Order Symphyla. A non-exhaustive list of particular sp. Includes, but Is not limited to, Scutigerella immaculata.
In another embodiment, the molécules of Formula One may be used to control pests of the Phylum Nematoda. A non-exhaustive list of particular généra Includes, but Is not limited to, Aphelencholdes spp., Belonolalmus spp., Criconemella spp., Ditylenchus spp., Heterodera spp., Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Pratylenchus spp., and Radopholus spp. A non-exhaustive list of particular sp. Includes, but Is not limited to, Dirofilaria immitis, Heterodera zeae, Meloidogyne incognita, Meloidogyne javanica, Onchocerca volvulus, Radophdus similis, and Rotylenchulus renlformls.
130
For additional Information consult “Handbook of Pest Control-The Behavior, Life History, AND CONTROL OF HOUSEHOLD PESTS* by Arnold Mallis, 9th Edition, copyright 2004 by GIE Media Inc.
APPLICATIONS
Molécules of Formula One are generally used in amounts from about 0.01 grams per hectare to about 5000 grams per hectare to provide control. Amounts from about 0.1 grams per hectare to about 500 grams per hectare are generally preferred, and amounts from about 1 g ram per hectare to about 50 grams per hectare are generally more preferred.
The area to which a molécule of Formula One Is applied can be any area inhabited (or maybe inhabited, ortraversed by) a pest, for example: where crops, trees, fruits, cereals, fodder species, vines, turf and omamental plants, are growing: where domesticated animais are residing; the interior or exterior surfaces of buildings (such as places where grains are stored), the materials of construction used in building (such as impregnated wood), and the soi! around buildings.
Particular crop areas to use a molécule of Formula One include areas where apples, corn, sunflowers, cotton, soybeans, canola, wheat, rice, sorghum, barley, oats, potatoes, oranges, alfalfa, lettuce, strawberries, tomatoes, peppers, cru ci fers, pears, tobacco, almonds, sugar beets, beans and other valuable crops are growing or the seeds thereof are golng to be planted. It is also advantageous to use ammonium sulfate with a molécule of Formula One when growing various . plants. .
Controlling pests generally means that pest populations, pest activity, or both, are reduced in an area. This can corne about when: pest populations are repulsed from an area; when pests are incapacitated in or around an area; or pests are exterminated, in whole, or in part, in or around an area. Of course, a combination of these results can occur. Generally, pest populations, activity, or 25 both are desirably reduced more than fifty percent, preferably more than 90 percent. Generally, the area is not in or on a human; consequently, the locus is generally a non-human area.
The molécules of Formula One may be used In mixtures, applied simultaneously or sequentially, alone or with other compounds to enhance plant vîgor (e.g. to grow a better root System, to better withstand stressful growing conditions), Such other compounds are, for example, 30 compounds that modulate plant ethylene receptors, most notably 1-methylcyclopropene (also known as 1-MCP). Furthermore, such molécules may be used during times when pest activity is low, such as before the plants that are growing begin to produce valuable agricultural commodities. Such times include the early planting season when pest pressure Is usually low.
131
The molécules of Formula One can be applied to the foliar and fruiting portions of plants to control pests. The molécules will either corne in direct contact with the pest, or the pest will consume the pesticide when eating leaf, fruit mass, or extracting sap, that contains the pesticide. The molécules of Formula One can also be applied to the soil, and when applied in this manner, root and stem feeding pests can be controlled. The roots can absorb a molécule taking it up into the foliar portions of the plant to control above ground chewing and sap feeding pests.
Generally, with baits, the baits are placed in the ground where, for example, termites can corne into contact with, and/or be attracted to, the bait. Baits can also be applied to a surface of a building, (horizontal, vertical, or slant surface) where, for exemple, ants, termites, cockroaches, and files, can corne into contact with, and/or be attracted to, the bait. Baits can comprise a molécule of Formula One.
The molécules of Formula One can be encapsulated inside, or placed on the surface of a capsule. The size of the capsules can range from nanometer size (about 100-900 nanometers in diameter) to mlcrometer size (about 10-900 microns in diameter).
Because of the unique abiiity of the eggs of some pests to resist certain pesticides, repeated applications of the molécules of Formula One may be désirable to control newly emerged larvae.
Systemic movement of pesticides In plants may be utilized to control pests on one portion of the plant by applylng (for example by spraying an area) the molécules of Formula One to a different portion of the plant. For example, control of foliar-feeding Insects can be achieved by drip irrigation or furrow application, by treating the soil with for example pre- or post-planting soil drench, or by treating the seeds of a plant before planting.
Seed treatment can be applied to ail types of seeds, including those from which plants genetically modified to express spedalized traits will germinate. Représentative examples Include those expressing proteins toxlc to Invertebrate pests, such as Bacillus thuringiensis or other Insecticidal toxins, those expressing herbicide résistance, such as “Roundup Ready seed, or those with stacked foreign genes expressing insecticidal toxins, herbicide résistance, nutritionenhancement, drought résistance, or any other bénéficiai traits. Furthermore, such seed treatments with the molécules of Formula One may further enhance the abiiity of a plant to better withstand stressful growing conditions. This results in a healthier, more vlgorous plant, which can lead to higher yields at harvest time. Generally, about 1 gram of the molécules of Formula One to about 500 grams per 100,000 seeds is expected to provide good benefits, amounts from about 10 grams
132 to about 100 grams per 100,000 seeds is expected to provide better benefits, and amounts from about 25 grams to about 75 grams per 100,000 seeds is expected to provide even better benefits.
It should be readily apparent that the molécules of Formula One may be used on, ln, or around plants geneticaily modified to express specialized traits, such as Bacillus thuringiensis or other insecticidal toxins, or those expressing herbicide résistance, or those with ‘stacked’ foreign genes expressing Insecticidal toxins, herbicide résistance, nutrition-enhancement, or any other bénéficiai traits.
The molécules of Formula One may be used for controlling endoparasites and ectoparasites in the veterinary medicine sector or in the field of non-human animal keeping. The molécules of Formula One are applied, such as by oral administration in the form of, for example, tablets, capsules, drinks, granules, by dermal application In the form of, for example, dipplng, spraying, pouring on, spotting on, and dusting, and by parentéral administration ln the form of, for example, an Injection.
The molécules of Formula One may also be employed advantageously in livestock keeping, for example, cattle, sheep, plgs, chickens, and geese. They may also be employed advantageously In pets such as, horses, dogs, and cats. Particular pests to control would be fleas and ticks that are bothersome to such animais. Suitable formulations are administered orally to the animais with the drinking water or feed. The dosages and formulations that are suitable dépend on the species.
The molécules of Formula One may also be used for controlling parasitic worms, especialiy of the Intestine, in the animais listed above.
The molécules of Formula One may also be employed ln therapeutic methods for human health care. Such methods Inciude, but are limited to, oral administration In the form of, for example, tablets, capsules, drinks, granules, and by dermal application.
Pests around the worid hâve been migrating to new environments (for such pest) and thereafter becoming a new Invasive species in such new environment. The molécules of Formula One may also be used on such new Invasive species to control them In such new environment.
The molécules of Formula One may also be used ln an area where plants, such as crops, are growing (e.g. pre-planting, planting, pre-harvestîng) and where there are low levels (even no actual presence) of pests that can commerclally damage such plants. The use of such molécules ln such area is to benefit the plants being grown In the area. Such benefits, may Inciude, but are not limited to, Improving the health of a plant, improvlng the yield of a plant (e.g. increased biomass and/or increased content of valuable ingrédients), improving the vigor of a plant (e.g. improved plant growth and/or greener leaves), improving the quality of a plant (e.g. improved content or
133 composition of certain ingrédients), and Improving the tolérance to abiotic and/or biotic stress of the plant.
Before a pesticide can be used or sold commercially, such pesticide undergoes lengthy évaluation processes by various govemmental authorities (local, régional, state, national, and international). Voluminous data requirements are specified by regulatory authorities and must be addressed through data génération and submission by the product registrant or by a third party on the product reglstrant’s behalf, often using a computer with a connection to the Worid Wide Web. These govemmental authorities then review such data and if a détermination of safety is concluded, provide the potential user or seller with product registration approval. Thereafter, in that locality where the product registration is granted and supported, such user or seller may use or sell such pesticide.
A molécule according to Formula One can be tested to détermine its efficacy against pests. Furthermore, mode of action studies can be conducted to détermine if said molécule has a different mode of action than other pesticides. Thereafter, such acquired data can be dissemïnated. such as by the Internet, to third parties.
The headings In this document are for convenlence only and must not be used to Interpret any portion hereof.
TABLE SECTION
Table 1: Compound number, appearance, and structure
Compound No. | Appearance | Structure |
134
Compound No. | Appearance | Structure |
1 | Yellow Gum | /c,l3o N—N $ zCH3 U C= |
2 | Yellow Solid | zCH’o [j ch3 c“3 |
3 | Yellow Gum | zCI,3o N-N « zCHj M·?1’ |
135
Compound No. | Appearance | Structure |
4 | Yellow Oil | CH, rvtX c«> |
5 | Yellow Oil | CH, |
6 | Yellow Gum | zCHïo \=^ CH, |
136
Compound No. | Appearance | Structure |
7 | Yellow Gum | CH, VL ___ CH, |
8 | Yellow Gum | CH, iMAf» CH, |
9 | Beige Gum | CH, N-/ \\ . Z C,!J Y ΓΥγ i Cl CHî |
137
Compound No. | Appearance | Structure |
10 | Colorless Gum | /CIl3o |
12 | Colorless Glass | CH, NZ ° \cHs N=^ Br ch5 |
18 | Brown Oil | c,,j |
138
Compound No. | Appearance | Structure |
19 | Yellow Oil | h3c py-V/ Clh |
20 | Yellow Oil | h3c ’ \, N 0 ___ \\ .chj X CH CH’ CH, |
21 | Yellow Oil | h3c \-N N5^ ch3 |
139
Compound No. | Appearance | Structure |
22 | Clear Oil | cHj fl Ί /—ch3 < h3c i\r |
23 | Clear Oil | /C”3 CH U OHl ^I>-Oh3 M h>c |
24 | Hjc' \ h3c |
140
Compound No. | Appearance | Structure |
25 | 5. H3C N | |
26 | CH3 ,,iC HjC HjC | |
27 | h3c |
141
Compound No. | Appearance | Structure |
28 | HjC V-K H,C | |
29 | h3c ~\Jl h3c | |
30 | [ HjC \jT h3cT Γ1 H3c |
142
Compound No. | Appearance | Structure |
31 | Ppl-, ÎHp | |
32 | Gold Syrup | Γγ^λ(2''' Ah, c»3 |
33 | Brown Solid | 0 N=\ /-CH, σ<>. |
143
Compound No. | Appearance | Structure |
34 | Off White Solid | CH> or |
35 | Off White Solid | 0 CH, W-CH, CH> cy |
36 | Off White Solid | aO-br |
144
Compound No. | Appearance | Structure |
37 | White Solid | |
38 | Off White Solid | H3C— O cr |
39 | White Solid | H3C-S n_P σΝ>Γ |
145
Compound No. | Appearance | Structure |
40 | Pale Yellow Solid | J, —N N O |
41 | Brown Thick Mass | |
42 | Pale Yellow Seml Solid | C> CH, ΟΓ |
146
Compound No. | Appearance | Structure |
43 | Pale Yellow Solid | 0 (fY CH3fV |
44 | White Solid | H3C—S rx P U br |
45 | Brown Thick Mass | o ch3 M™, CH’ CT |
147
Compound No. | Appearance | Structure |
46 | Pale Yellow Thick Mass | H3C Nc=\ /—CH3 L. JJ O ch3 N |
47 | Pale Yellow Thick Mass | h3c —CH3 h3c—s |
48 | Pale Green Thick Mass | H3C--L w H3C—s |
148
Compound No. | Appearance | Structure |
49 | Pale Yellow Solid | O N=\ /“CH, |
50 | Brown Thick Mass | h3c-—, |
51 | Pale Yellow Thick Mass | H3C—S n°H CH3 Or |
149
Compound No. | Appearance | Structure |
52 | Tan Solid | O ___ Q· e,„ N |
53 | White Solid | r. ZCHî V_z~~s hh>c ch, (J |
54 | Clear Oil | r. ZCHj 0, ___</ ch, O |
150
Compound No. | Appearance | Structure |
55 | White Semi Solid | V /CH3 CH’ (J N |
56 | Brown Solid | |
57 | White Solid | HaÇ CH, V XcH, /-V σΝ>ί |
151
Compound No. | Appearance | Structure |
58 | Clear Oil | .cn3 /CH’ H C H j i J N |
59 | White Solid | CH,0 /CH3 |
60 | White Solid | CH, O ^-<CH3 ch3 U |
152
Compound No. | Appearance | Structure |
61 | Light Yellow Solid | CH3 o /Η3 pR (J N |
62 | Clear Oil | H1c ÇH, Q” |
63 | Light Yellow Solid | CH, U N |
153
Compound No. | Appearance | Structure |
64 | White Solid | H3C. CH3 ch3O V 3 X y/-™' O ^br |
65 | White Solid | n-M' CHj (J N |
66 | White Semi Solid | s—ch3 H / a«' N |
154
Compound No. | Appearance | Structure |
67 | Yellow Semi Solid | o HVHj W /~ch3 >-o/ 1 |
68 | Clear Oil | h3c ch3 Cl o. Y—ch3 N |
69 | Dark Brown Oil | P o /__Zs^ Q ™, |
155
Compound No. | Appearance | Structure |
70 | Viscous Pale Yellow Oil | Cl o s V |
71 | White Solid | Cl 0 σ.) |
72 | White Semi Solid | ch3 σ y ' |
156
Compound No. | Appearance | Structure |
73 | White Semi Solid | £«3 0 ch Q |
74 | Clear Oil | σ ‘”· ?Γ |
75 | White Semi Solid | CH ~ /CH’ £h3O __ s z \ CHî Cr ?r |
157
Compound No. | Appearance | Structure |
76 | Clear Oil | ch3 CH3 Q ÇHj_s Z ch= Q “ TT |
77 | White Solid | ci o rC.KH‘ CH, IJ ?r |
78 | White Solid | Pl o /»> (J |
158
Compound No. | Appearance | Structure |
79 | White Solid | d Q /CH’ H CH, O N |
80 | White Solid | zch3 S ci ο \ / Ά c»3 cY “ |
81 | White Solid |
159
Compound No. | Appearance | Structure |
82 | White Solid | F F U |
83 | White Solid | F F H CH j (J |
84 | White Solid | H C H 3 (J |
160
Compound No. | Appearance | Structure |
85 | Off-White Solid | ch3 o zCH3 XJ N |
86 | Yellow Solid | ,p>* σ o |
87 | Yellow Solid | ch3 |
161
Compound No. | Appearance | Structure |
88 | White Solid | F / qn - cb- |
89 | White Solid | N |
90 | Clear Oil | CH, o V’ U X<ACH’ |
162
Compound No. | Appearance | Structure |
91 | Faint Yellow Oil | F 7 V O ,CHJ Q .... Y |
92 | Faint Yellow Oil | F F QN - - |
93 | White Solid | Jh’V/CH3 U |
163
Compound No. | Appearance | Structure |
94 | Clear Oil | 'ί'γ·'’ σ'7. |
95 | Clear Oil | „„ CH, vy |
96 | Yellow Solid | CH Λ y CHJ / h3 o y >T |
164
Compound No. | Appea rance | Structure |
97 | YellowOil | CH n /CH» yXJvT'8 CH’ zÿj HjC |
98 | Yellow Oil | ΓΠ ^^3 r=T V~‘ PT H-. H’c |
99 | Yellow Solid | o rv /CHj y~^~s τίι //—N a |
165
Compound No. | Appearance | Structure |
100 | Clear Oil | M zch> ctf* |
101 | Clear Oil | ch3 ÇH3 0 y--S( σ .> ’ N |
102 | Clear Oil | /H, N |
166
Compound No. | Appearance | Structure |
103 | Clear Oil | CHj /C,,3V^F° |
104 | Faint Yellow Oiî | ch3 Ï”3 Ντ=Α 7 \ O J, /)—N CH, σ j |
105 | Off-White Solid | .CII3 O /CHî N=( IT |
167
Compound No. | Appearance | Structure |
106 | Faint Yeîlow Oil | Cl |
107 | White Solid | A w ch, (a ?r ch3 |
108 | Clear Oil | ch3 sz ci cn3C \ CH3 (7 |
168
Compound No. | Appearance | Structure |
109 | Yellow Solid | tt 'h o^~vh’ Cl O y_CHj HjC |
110 | Brown Oil | o HjV' N- RR’ n 1 k CHî |
111 | Yellow Solid | rCR |
169
Compound No. | Appearance | Structure |
112 | Brown Oil | CH, |
113 | Yellow Oil | O /CH3 rv iï η Λ CH, |
114 | Brown Oil | rC ff™· w·· N Z CH, |
170
Compound No. | Appearance | Structure |
115 | Light Brown Solid | “V' ’ΎΎ |
116 | Yellow Solid | |
117 | Yellow Oil | CfT'- '· NT |
171
Compound No. | Appearance | Structure |
118 | Brown Oil | crr - “ br |
119 | Brown Oil | ch, q z ch3 yy~~s N Z CHj |
120 | Brown Oil | CH, o CH, N=Z W'8 'ϊΎΤ^1’ ch> CH j |
172
Compound No. | Appearance | Structure |
121 | Off-White Solid | Ph ο z c|h y/'5 CHi |
122 | Faint Yellow Solid | PH3 o rtX CH, û “· |
123 | Clear Oil | Ph o /cth |
173
Compound No. | Appearance | Structure |
124 | Yellow Solid | Ph O /C»3 T j |
125 | White Solid | ,CH3 O 4x Γ'γ<γΝ'<Ζ \ CHj H’C |
126 | Yellow Oil | CHî O ^CHj CH, cx„, |
174
Compound No. | Appea rance | Structure |
127 | YellowOil | CHj o .CH3 Œ ^CH3 |
128 | Néon Yellow Oil | CHj q z ch3 >-/en » |
129 | Néon Yellow Oil | pH3 q /Hj rOn en - |
175
Compound No. | Appearance | Structure |
130 | Pink Solid | θ,Ύ |
131 | Red Oil | CHS o /H, Q Y- N |
132 | Yellow Oil | Y'' çY |
176
Compound No. | Appearance | Structure |
133 | Yellow Oil | P o U |
134 | Clear Oil | P o |
135 | Off-White Solid | „ σ >·>., H3C CHj |
177
Compound No. | Appearance | Structure |
136 | Yellow Oil | />0 ’V/’ XX 1 |
137 | Yellow Oil | /ch’<\Vs /CH’ sYq θ'» >c |
138 | Yellow Oil |
178
Compound No. | Appearance | Structure |
139 | Faint Yeilow Oil | N |
140 | Faint Yellow | rC Kc’’ N |
141 | Light Yellow Solid | h3c ch3 9«3 0. V-CH, ,J:R; Ci |
179
Compound No. | Appearance | Structure |
142 | Clear Oil | ci o s/CH> ch3 HîC |
143 | Coloriess Oil | ch3 N |
144 | Colorless Oil | ch3 ^br |
180
Compound No. | Appearance | Structure |
145 | White Solid | /CH^\\ /—CH3 c |
146 | Gray Oil | crr- |
147 | Colorfess Oil | F /Hj ' F θ' N |
181
Compound No. | Appearance | Structure |
148 | White Solid | /CH’ % /CH’ CH’ cy |
149 | Yellow Solid | h3c ch3 yK Y |
150 | White Solid | P OHVH’ r( >-^CH3 W N |
182
Compound No. | Appea rance | Structure |
151 | Clear Oil | CH, 0 CH, N |
152 | Clear Oil | PH,O Λ O CH' |
153 | White Solid | CH, 0 __/ Q ™· |
183
Compound No. | Appearance | Structure |
154 | Faint Orange Oil | Pbo _Λ 'CH, F O e», |
155 | Clear Oil | c«,o /«> [^ÛAh’C CHj >c |
156 | Clear Oil | CM Hî<\ zCHj /h>q y./ Ντ \ Z--\ CHj çr „/ |
184
Compound No. | Appearance | Structure |
157 | Clear Oil | CH H3\ zCH3 ,chjo \__/ yy |
158 | Clear OU | Z—Zf θ' / ' |
159 | Clear Oil | Ζ-Λ σ,Γ”·F |
185
Compound No. | Appearance | Structure |
160 | White Solid | P 0, /CH> Aa N |
161 | Brown Oil | a yAXAA N |
162 | Light Brown Solid | P oVH’ rC |
186
Compound No. | Appearance | Structure |
163 | White Solid | ci n U V/CH1 Ά CHJ V H’c |
164 | White Solid | __P o Hî\__s/CHî 'ΥΎ^ < «JC N |
165 | White Solid | CH ,CHÎ N |
187
Compound No. | Appearance | Structure |
166 | Yellow Oil | CH, σ Y |
167 | Grey Oil | P 0 /c 3 r< V7’ 'ΎΥ~Π V 3C |
168 | Faint Purple Oil | Ύ) |
188
Compound No. | Appearance | Structure |
169 | White Solid | vyr N |
170 | White Solid | ch3 ÇH3 o / σ .Γ ^br |
171 | White Solid | ch3 ch3 o --/ ^br |
189
Compound No. | Appearance | Structure |
172 | White Solid | H3C ru Cl O 3 \/CH’ rC YXc‘ (J TF |
173 | White Solid | P o rLX3 \ CH3 l J N |
174 | Clear Oil | P O /»> YY N |
190
Compound No. | Appearance | Structure |
175 | White Solid | Γ °\ γχ .... |
176 | Yellow Oil | ci 0 /CHî r< o c· |
177 | White Solid | P 0 'O |
191
Compound No. | Appearance | Structure |
178 | Yellow Oil | r-CVX' |
179 | White Solid | yCI <λ— 7P \ CH, XX |
180 | Yellow Solid | Ci F / °\ Z*F CHj liy HsC |
192
Compound No. | Appearance | Structure |
181 | Faint Yellow Oil | Cl Hî<\ /*Hj cil, j |
182 | Faint Yellow Oil | Cl « sZCHj R >c |
183 | Yellow Oil | h3c /' Q-h CH) h>c |
193
Compound No. | Appearance | Structure |
184 | Colorless Oil | ,CH3 CHj 0 y--S br |
185 | White Solid | CHj Ç«3 o ,—5 F K 'CHj ίΓ |
186 | White Solid | CHp. CH3 y#' ·: br |
194
Compound No. | Appearance | Structure |
187 | Yellow Solid | Γχχ<γΟ~Ν\ ch, F H>c |
188 | Yellow Oil | CHj o __7 |
189 | Yellow Oil | CHj Q ÇH3 s/CHî CH, H’C |
195
Compound No. | Appearance | Structure |
190 | Yellow Oil | P1’ o Λ-chj xA> |
191 | Yellow Oil | ru ,cn3 f ’Vy- * C br |
192 | Yellow Oil | /’W1'1 xA |
196
Compound No. | Appearance | Structure |
193 | Yellow Solid | /· °«/— yy “· TT |
194 | White Solid | /CH>°X r Λ O “'· |
195 | White Solid | w5-’ |
197
Compound No. | Appearance | Structure |
196 | Tan Solid | CH, L ci |
197 | White Solid | CH, rvW CH, |
198 | Tan Solid | /η3 N=\ V) CrJ” |
198
Compound No. | Appearance | Structure |
199 | Gold Solid | HjC CH, % X-CH, XX >c |
200 | Yellow Oil | XX'X· σ |
201 | Gold Oil | o çh3 ch3 r\_H r^XX'ÎÎ CHj L x « N |
199
Compound No. | Appearance | Structure |
202 | White Seml Solid | (J h3c> N |
203 | Yellow Oil | rCp-· |
204 | Yellow 011 | H » C r u οΎ “ rr |
200
Compound No. | Appearance | Structure |
205 | Yellow Oil | AND Enantïomer < J HjC N |
206 | Yellow Oil | rCW’ σΡ N |
207 | White Solid | JJ V/~ Λ N |
201
Compound No. | Appearance | Structure |
208 | White Solid | Q br |
209 | Yellow Oil | ^br |
210 | Yellow Oil | 0 0 /CH’ rC^s QN ^bT |
202
Compound No. | Appearance | Structure |
211 | Yellow Oil | p o s/CHî N |
212 | Yellow Oil | N |
213 | Yellow Oil | F o Çr “ |
203
Compound No. | Appearance | Structure |
214 | Yellow Oil | /Cl V/-À - |
215 | Clear Oil | ch3 |
216 | Cream Colored Solid | /h3 CHp y--S XX H5rcH’ |
204
Compound No. | Appearance | Structure |
217 | Clear Oil | CH, / 3 CHft /—S . γ. N CH 3 |
218 | Clear Oil | /CHj i—s rfH?° XX'O |
219 | Clear Oil | zCH3 YY Xr |
205
Compound No. | Appearance | Structure |
220 | Yellow Oil | F F cn3 0 ,-J/ 'x/b |
221 | While Solid | O TT |
222 | While Solid | rO-Z’ Q^ AA |
206
Compound No. | Appearance | Structure |
223 | White Solid | yP4·· u NT |
224 | Coloriess Oil | F F cH3° \/h 3 Q o„, TT |
225 | Light Yellow Oil | z CH3O z ch3 σ4.«· |
207
Compound No. | Appearance | Structure |
226 | White Solid | ch3 0' Q CH, |
227 | White Solid | ξ F ,CHJ0 Q e„. br |
228 | Colorless Oil | F F PH, ο °Xr ÎJ |
208
Compound No. | Appearance | Structure |
229 | Colorless Oil | F 9. Q ... \ |
230 | Colorless Oil | CH, n r r<M· CH, Q cn- br |
231 | Colorless Oil | CH, ûr >r |
209
Compound No. | Appearance | Structure |
232 | White Solid | Cr ™· N |
233 | White Solid | F_/ PHJO J N V—-Nv 'C |
234 | White Solid | σ “ |
210
Compound
No.
Appearance
Structure
235
Colorless Oil
211
Compound No. | Appearance | Structure |
238 | Colorless Oil | \ F f-Az CHÎO Y CH, >->-s H,C |
239 | Colorless Oil | CH,O CH, «3C |
240 | White Solid | PH, o OA |
212
Compound No. | Appearance | Structure |
241 | Colorie ss Oil | /CHî0 σΡ |
242 | Coloriess Oil | F Z,,3°\ z—A/v F |
243 | Coloriess Oil |
213
Compound No. | Appea rance | Structure |
244 | Whîte Solid | CH3 n ï? CH’ ILJ h3c |
245 | White Solid | IL χ h3c br |
246 | Coloriess Oil | σΧ |
214
Compound No. | Appearance | Structure |
247 | White Solid | Ά CHJ0 <chj < A h3c |
248 | Colorless Oil | RXn, rr > < R HjC fT |
249 | White Solid | CH3 n ox < HjC |
215
Compound No. | Appea rance | Structure |
250 | Clear Oil | /Hî°a ch. TJ ,c |
251 | Brown Oil | Y' rr |
252 | Off White Solid | Pr Q /c 3 S B TJ N |
216
Compound No. | Appearance | Structure |
253 | Off White Solid | CHj Br 0 y--S —N CH, |
254 | Brown Solid | |
255 | White Solid | _ Cl Ov j---J u |
217
Compound No. | Appearance | Structure |
256 | White Solid | Cl Ov ,—CH, n |
257 | White Solid | CH, rnA (y br |
258 | Brown Oil | (A |
218
Compound No. | Appearance | Structure |
259 | White Solid | /CHî°v V /CHî 3 |
260 | Colorless Oil | CII3O zch3 h3c |
261 | White Solid | ch30 |
219
Compound No. | Appearance | Structure |
262 | White Solid | f-A/F /CHîO < H3C |
263 | Colorless Oil | A'A IL J II3C |
264 | Colorless Oil | F ÇHj 0 ~A/^T'F |
220
Compound No. | Appearance | Structure |
265 | White Solid | CH, H,C |
266 | Colortess Semi-Solîd | CH· IL X h,c |
267 | Colortess Oil |
221
Compound No. | Appearance | Structure |
268 | White Solid | PHjo p 'cil, >c |
269 | White Solid | the |
270 | White Solid | Phn F όΌ |
222
Compound No. | Appearance | Structure |
271 | Colorless Oil | |
272 | White Solid | XX |
273 | Colorless Oil | χΎ CH> H’C |
223
Compound No. | Appearance | Structure |
274 | Colorless Oil | F r Ύ Cil, V >c |
275 | White Solid | ’kL Λ». n^=< c‘ ”>c |
276 | White Solid | ÇH3 O / \\ rr0'> Jx-f Hjc f |
224
Compound No. | Appearance | Structure |
277 | Brown Amorphous Solid | /H3 Br 0 y—S ï p—H ch3 CH) |
278 | White Solid | Clip. /-CH3 Yf Q 3 br |
279 | White Solid | ch3 /Hp\\ y a |
225
Compound No. | Appea rance | Structure |
280 | White Solid | n/' Q 1 |
281 | Orange Foam | CHj HîC\ J Xo br |
282 | Colorless Oil | zch3 JJ Xch2 ^br |
226
Compound No. | Appearance | Structure |
283 | Colorless Oil | zch3 Cl 04 /—s σ |
284 | Colorless Oil | Cl Ov CH, V v«· |
285 | Clear Oil | CH3 /H, (J o^~CH1 |
227
Compound No. | Appearance | Structure |
286 | Yellow Oil | P..o WH < h3c |
287 | Yellow Oil | ch3 ch3 z---- σ .K· ° ch3 |
288 | Yellow Oil | /-V1 σ^λν --CHj |
228
Compound No. | Appearance | Structure |
289 | Dark Yellow Oil | ch3 /Hj ch3 |
290 | Yellow Oil | ch3 zch3 ch3 |
291 | Clear Oil | h3c Cl CH3C—y—ch3 dr σΡΡ TT |
229
Compound No. | Appearance | Structure |
292 | Tan Solid | |
293 | Clear Oil | |
294 | Yellow Oil | CHj H Ί éii, cn3 |
230
Compound No. | Appearance | Structure |
295 | White Seml- Solid | ch3 ιχΥΥι i °Y? Π Ί CHj ch3 '—! |
296 | Colorless Oil | F F CI O J N σ x». N |
297 | White Solid | Br O i—CH, H U iX |
231
Compound No. | Appearance | Structure |
298 | White Solid | ch3 U TT |
299 | White Solid | CH, n/ O K |
300 | White Solid | Cl 0 r— C H 3 O ?r |
232
Compound No. | Appearance | Structure |
301 | White Solid | ch3 σ |
302 | White Solid | ___// H2 CI c> ,—y A' u br |
303 | Coloriess Oil | f-A/F /cl <\ AL/™3 A N |
233
Compound No. | Appearance | Structure |
304 | Light Yellow Oil | Cl O CHj H3C |
305 | White Solid | Cl ov cÆT br |
306 | Grey Solid | FJF C' 0 < HjC bT |
234
Compound No. | Appearance | Structure |
307 | Colorless Oil | tQ |
308 | Colorless Oil | |
309 | Colorless Oil | fv > -S» IL Λ h3c br f |
235
Compound No. | Appearance | Structure |
310 | Lîght Yellow Semi-Solid | |
311 | Colorless Oil | H’c |
312 | White Solid | F p o —N V— K a a |
236
Compound No. | Appearance | Structure |
313 | Light Yellow Solid | R-cri. |
314 | Faint Yellow Oil | CH3 0 CH3 yx~·' N |
315 | Faint Yellow Oil | ch3 o zch3 N |
237
Compound No. | Appearance | Structure |
316 | Faint Yellow Solid | ch3 o yJ-Y Y |
317 | White Solid | u N |
318 | Brown Solid | CH3 Cl O ----' h TJ |
238
Compound No. | Appearance | Structure |
319 | Brown Solid | Cl °\ /— hr |
320 | Yellow Solid | Cl C) y—CH, |
321 | Yellow Solid | ch3 Cl o. j----f AA hr |
239
Compound No. | Appea rance | Structure |
322 | Yellow Solid | CH, Cl °\ /— N |
323 | Coloriess Oil | CH, 0 Q o„ rr |
324 | White Solid | CH, o H’\ «’c |
240
Compound No. | Appearance | Structure |
325 | White Solid | CHJ0 Λ Wn < HjC |
326 | Colorless Oil | h3ç P ο V V-/-™, σ<=> bT |
327 | White Solid | CH, „ H3C |
241
Compound No. | Appearance | Structure |
328 | White Foam | CHj Çl O t— s Q |
329 | White Foam | /CHj Or “ |
330 | White Foam | ZCH3 Ç1 O i—s OLHO a / |
242
Compound No. | Appearance | Structure |
331 | White Foam | /CHj rCXr° cr ‘ N |
332 | Clear Yellow Oil | H,C ÇH3 Cl 0 'Y—ch3 fT F |
333 | Clear Oil | Cl n îPz |
243
Compound No. | Appearance | Structure |
334 | Light Brown Solid | Cl 0 /— C H 3 u N |
335 | White Solid | Cl 0 ~ rô-r \ CH3 Cr N |
336 | White Solid | α ο zCH= Z~° CH, Q “ N |
244
Compound No. | Appearance | Structure |
337 | Paie Yellow Oil | Cl o X V/S~CH’ u |
338 | Clear Oil | Xf < H3C |
339 | Clear Oil | F F ci ο V / *θ f fp ) < h3c br |
245
Compound No. | Appearance | Structure |
340 | White Solid | P 0 ’V’ P >p-CH’ TJ N |
341 | Yellow Oil | ΓΗ CHj yCH3O \__g/ N |
342 | Yellow Oil | rn C H3 z CHîq __v 3 σ”Ρ *Τ |
246
Compound No. | Appearance | Structure |
343 | Yellow Oil | rCV-f' |
344 | Yellow Oil | pHJO __/ yyr br |
345 | Yellow Solid | Cl ov ch3 H-H rr |
247
Compound No. | Appearance | Structure |
346 | White Solid | KX’ h>c |
347 | Pale Yellow Oil | pi 0 < Y HjC |
348 | Brown Solid | Cl CI O y---' Λη J. /)—N en >r |
248
Compound No. | Appea rance | Structure |
349 | Beige Solid | Ch 3 Q |
350 | Coloriess Oil | ch3 'On “ |
351 | White Solid | rCH», c- |
249
Compound No. | Appearance | Structure |
352 | Yellow Solid | X °/VH1 TT |
353 | Yellow Oil | ’S n ,<*> 'O— |
354 | Yellow Oil | X O ,CH' rZZT· F'sv/^N^;iA CH3 N |
250
Compound No. | Appearance | Structure |
355 | Yellow Solid | rp-r ’VV’kX'I CH, IJ CHs |
356 | Yellow Oil | R* 'yy-X, |
357 | Yellow Oil | h2q NS CHj R Or ci |
251
Compound No. | Appearance | Structure |
358 | Off-White Solid | |
359 | Off White Solid | tT TT |
360 | White Solid | rCAA CH3 |
252
Compound No. | Appearance | Structure |
361 | Tan Solid | HjC chσ’<? |
362 | Clear Oil | σ N |
363 | Clear Oil |
253
Compound No. | Appearance | Structure |
364 | Yellow Oil | N |
365 | Yellow Oil | •t/-7’ ' CHj |
366 | Yellow Oil | ci o /CHj |
254
Compound No. | Appearance | Structure |
367 | Clear Oil | Cl 0 A CH3 |
368 | White Solid | Cl ~ /CHî P Q s- _/ A |
369 | Light Brown Oil | 5 ?\ ’kc ! KAch· U 1 ^br |
255
Compound No. | Appearance | Structure |
370 | Colorless Gum | h3c zCH3 |
371 | Colorless Gum | zch3 Br O Λ'' S x y Λ |
372 | Yellow Oil | Y Y' YY Y |
256
Compound No. | Appearance | Structure |
373 | White Solid | σΧ |
374 | Belge Solid | Cl 0 |
375 | White Solid | ÇH3 O y--CH3 nA_/h XJ N |
257
Compound No. | Appearance | Structure |
376 | White Solid | CH, ÇH3 o |
377 | White Solid | xY' |
378 | White Solid | , Y. xch3 iip «3C |
258
Compound No. | Appearance | Structure |
379 | White Solid | σ P |
380 | White Solid | ’xyY N |
381 | White Solid | P oH’VHî ΟΥ Z |
259
Compound No. | Appearance | Structure |
382 | Clear Oil | \ F r0-·^ |
383 | Pale Yellow Oil | α o zCH’ u -5·° k |
384 | Colorless Oil | ch3 0 __/CHj σ ’«· N |
260
Compound No. | Appearance | Structure |
385 | White Solid | ΎΎ CH1 |
386 | White Solid | CH3 çh3 o --/ |
387 | White Solid | PH,,, ργΎ |
261
Compound No. | Appearance | Structure |
388 | White Solid | N-/HlV/~Dr O “ br |
389 | Colorless Oil | V1 /> Q î<V HjC N |
390 | Off-White Solid | D rC'Kr^'” |
262
Compound No. | Appearance | Structure |
391 | Colorless Oil | P <\ CHj Çr - |
392 | Colorless Oil | p o. rOr CH, U CHi br |
393 | Colorless Oil |
263
Compound No. | Appearance | Structure |
394 | Coloriess Oil | IL HjC N |
395 | Pink Solid | C |
396 | Coloriess Oil | cr-y<' « |
264
Compound No. | Appearance | Structure |
397 | Coloriess Oil | CH Ph o J Q Z” ^br |
398 | White Solid | ru zC1,3 rCR” V CHj ^br |
399 | White Solid | __Λ CH3 CH, u br |
265
Compound No. | Appearance | Structure |
400 | Yellow Oil | CH, CH, z-Y^s CH, u o^vs ch3 |
401 | Yellow Oil | ch3 zch3 ch3 |
402 | Yellow Oil | ch3 ch3 rC^-Cs CHj U --T0 ch3 |
26«
Compound No. | Appearance | Structure |
403 | Yellow Oil | CHj /Η3 σψ HjC |
404 | Yellow Solid | H2\ O Λη“· H CH5 U N |
405 | Colorless Oil | σα>· |
267
Compound No. | Appearance | Structure |
406 | Colorless Oil | P o /CHj rOrC a X bl |
407 | Pale Yellow Oil | < CHj |
408 | Yellow Oil | XJ CH> ^br |
268
Compound No. | Appearance | Structure |
409 | White Solid | 0 |
410 | Orange Oil | XY' o CHj |
411 | Beige Solid | Y |
269
Compound No. | Appearance | Structure |
412 | White Solid | N |
413 | White Solid | r-a .b N |
414 | Yellow Oil | Λ H VH1 Q N |
270
Compound No. | Appearance | Structure |
415 | Off-White Solid | Y Y'' σΤγ ï ch3 |
416 | YellowOil | h3c > Q zC»3 γγ XX CH· Y |
417 | Yellow Oil | h3c ) O ZC»3 γ\_>Ύ wA., CHj |
271
Compound No. | Appearance | Structure |
418 | Yellow Solid | H3C rt Vf CH, U CH3 |
419 | Yellow Oil | HjC H C \ « 3\ zCHî xy |
420 | Yellow Oil | h3c \ CH, rb^ xy ci br |
272
Compound No. | Appearance | Structure |
421 | Light Yellow Oil | |
422 | Light Yellow Oil | jT R < R HjC N |
423 | Light Yellow Oil | 0 P«3 o __Z-CH, xr |
273
Compound No. | Appearance | Structure |
424 | Tan Solid | 'όΆ> yr |
425 | Coloriess Oil | Cl 0 F-C |
426 | Coloriess Oil | __ci o F-J— V H1C |
274
Compound No. | Appearance | Structure |
427 | Yellow Oil | __ M »z |
428 | Yellow Oil | r/n V ’c |
429 | Yellow Oil | / 9χ sX5· u J |
275
Compound No. | Appearance | Structure |
430 | Light Yellow Oil | Cl o n_?w·· /A'A I CH c e |
431 | White Solid | cyz ^~cHi |
432 | Yellow Oil | rC V~c,,j AA |
276
Compound No. | Appearance | Structure |
433 | Yellow Oil | Cl o /CHî Q >-· N |
434 | White Solid | Γ> h3c ch3 TT |
435 | White Solid | HO / ° ï JL/CHj kaJx/S i TJ CHi N |
277
Compound No. | Appearance | Structure |
436 | White Solid | XJ “ |
437 | Yellow Oil | Cl o /CHî Yn ch> u oY’ CHj |
438 | Yellow Oil | / s /«’ ζνΆ ch= Q · rr |
278
Compound No. | Appearance | Structure |
439 | White Solid | |
440 | White Solid | PH3 Q £H3 Q - |
441 | Yellow Solid | Ρ«3 θν c ΎΎ |
279
Compound No. | Appearance | Structure |
442 | White Solid | CH3 0 'ïA br |
443 | White Solid | /CHj °l Q |
444 | Brown Solid | H W’ n-^V'N^~N\ < c,,> bT |
280
Compound No. | Appearance | Structure |
445 | Brown Solid | 9> /h, ?'=\ L/7 M C,|J |
446 | Yellow Solid | /CH’O cilj ÎTP'N'^\11J c,'> |
447 | Dark Oil | /Cl O CHj )Γν'Ν'^'γΗ5 c· |
281
Compound No. | Appearance | Structure |
448 | Brown Solid | /CHj q H κγ (ΓΥ'Νχ^~'\Η3 CH5 TT |
449 | Tan Solid | /Cl q chj |
450 | White Oil | χΧΛ'-'·''· x™· ch3 |
282
Compound No. | Appearance | Structure |
451 | Yellow Oil | X an ’ |
452 | Colorless Oil | Br q /CH> σ “ br |
453 | White Solid | Br o ^CH, CHj Q 5 N |
283
Compound No. | Appearance | Structure |
454 | White Solid | Br 0 CH3 1 H CH, σ c- |
455 | Colorless Gum | F F Br O y—V Q-id V„, |
456 | Yellow Oil | P °x a - br |
284
Compound No. | Appearance | Structure |
457 | White Oil | YdrV···'· u k ZZ^CHj O |
458 | White Solid | AND Enantiomer /Hj Βγ O Λ.....ι S ï \\__Δ N |
459 | Colorless Oil | H3C zCH3 Br 0 2—s cr Vh- N |
285
Compound No. | Appearance | Structure |
460 | White Solid | Br Q. S—CH3 cd |
461 | Coloriess Gum | F F Br O y n; CH3 cr - |
462 | White Solid | ch3 AF σ .Γ |
286
Compound No. | Appearance | Structure |
463 | White Solid | fH3 Br O y--S ΐ z>—n; ch3 αχ br |
464 | Colorless Gum | F F |
465 | White Solid | XW’ Q XJ ’ |
287
Compound No. | Appearance | Structure |
466 | White Solid | AND Enantîomer zch3 Br O *··.>< s N |
467 | Colorless Gum | h3c zch3 |
468 | Light Yellow Solid | Br C> S—CH 3 cT C |
288
Compound No. | Appearance | Structure |
469 | White Solid | Br O. S—CH, (pis |
470 | Light Yellow Oil | Cl o /CHî P |
471 | Light Yellow Oil | Q N |
289
Compound No. | Appearance | Structure |
472 | Light Yellow Oil | AyJ |
473 | Light Purple Solid | /’V7’ N |
474 | Yellow Oil | Q Sc' hr ch3 |
290
Compound No. | Appearance | Structure |
475 | Light Yellow Oil | c y Ich3 ch3 |
476 | White Solid | Br Ov S—CH i cA~-· |
477 | Off-White Solid | Ch 3 0 n-n /-ch3 Il CH3 |
291
Compound No. | Appearance | Structure |
478 | Clear Oil | o H=C |
479 | Belge Solid | Cl Sv y--CH3 A N |
480 | White Solid | XX (X IX |
292
Compound No. | Appearance | Structure |
481 | Light Yellow Oil | Cl Cl O t----< N^\ /--' qy> |
482 | Beige Solid | rY° CH’ U y |
483 | Clear Viscous Oil | P 0 HîVHî J A /—CH 3 < h3c |
293
Compound No. | Appearance | Structure |
484 | Clear Viscous Oil | h3ç ch3 r\ A Ά h’c |
485 | White Oil | ci o AAs/’ Q S N 0A/°\zch^ |
486 | Off White Solid | rC A' N |
294
Compound No. | Appearance | Structure |
487 | Off-White Gum | fl CH’ |
488 | Light Yellow Solid | HjC CH3 a a )^ch5 cZ ' o / h3c |
489 | Yellow Solid | HjC CH3 V A»’ y=\ 7-° U N |
295
Compound No. | Appearance | Structure |
490 | Light Yellow Oil | F r JP· Q 3 |
491 | Light Yellow Oil | x A“’ σχ |
492 | White Solid | Cl o .CH 3 ^br |
296
Compound No. | Appearance | Structure |
493 | Light Orange Oii | q \ zch3 |
494 | Yellow Oil | P o’V/CH’ X % σΧ |
495 | Clear Oil | a oHî<\JyCHî c/r |
297
Compound No. | Appearance | Structure |
496 | Light Yellow Oil | côOo / h3c |
497 | Light Yellow Oil | C. O CH, rôXhr O / h3c |
496 | Light Yellow Oil | Cl ot CH, 0 / H3c |
298
Compound No. | Appearance | Structure |
499 | Coloriess Oil | H,C Cr «Γ ’ |
500 | Beige Solid | y--CH3 Cl O y---f Q-P N |
501 | White Solid | ch3 Cl O y---< |
299
Compound No. | Appearance | Structure |
502 | Thick Yellow Oil | CHj br |
503 | Beige Solid | h3c ch3 YF br |
504 | Beige Solid | h3c ch3 rv >-F br |
300
Compound No. | Appearance | Structure |
505 | Colorless Gum | Br 0 |
506 | Clear Colorless Oil | CH, Cl n / R >_/~s |
507 | Clear Colorless Oil | Q f |
301
Compound No. | Appearance | Structure |
508 | Clear Colorless Oil | P ç/’V/3 |
509 | Pale Yellow Gum | ^CH, 0.__ CHj ' 'cH, |
510 | Yellow Oil | P 0 î7 X... h3c |
302
Compound No. | Appearance | Structure |
511 | White Oil | P o Y o—ch3 |
512 | Pale Yellow Oil | ox |
513 | Thick Clear Oil | ^CH3 ?yX~æ ox |
303
Compound No. | Appearance | Structure |
514 | White Solid | P o “’V’ FA »>c |
515 | White Oil | Cl o K_rS^'CHj °> HjC |
516 | Dark Brown Oil | Cr “ yr |
304
Compound No. | Appearance | Structure |
517 | White Solid | Cl o __/F ^br |
518 | White Solid | S-CHj cT br |
519 | White Solid | S—CHj Cl O y---f bT |
305
Compound No. | Appearance | Structure |
520 | Brown Gum | h3c / Q. CH, U >-< ~ JL/Xx ch3 iîYt^ ch’ |
521 | Beige Solid | cl o YXX CHj x y |
522 | White Solid | ÆX-' ,ΧΥ CH3 U Y |
306
Compound No. | Appearance | Structure |
523 | Yellow Solid | F HVHi rC >-°XcHï U |
524 | Light Brown Solid | P O ,υΟττ ΓΎ H’c «5c |
525 | Faint Yellow Solid | / q /CH> r( yz-s FT |
307
Compound No. | Appearance | Structure |
526 | Faint Yellow Solid | / °v ZCHj r( Ws CH, i j ’ hr |
527 | Yellow Oil | CH, XJ CH’ hr |
528 | Light Brown Oil | JyA' 'YX AT |
308
Compound No. | Appearance | Structure |
529 | Faint Yellow Solid | lZ CH, NZ p?5 XX “ |
530 | Clear Oil | CHj |
531 | Yellow Oil | F F Xk” σΥ A CHj |
309
Compound No. | Appearance | Structure |
532 | White Solid | Cl o Q ? hZ |
533 | Orange Oil | P1 o rC M~CHJ „Z |
534 | Red Oil | ci o σΑ |
310
Compound No. | Appearance | Structure |
535 | White Oil | nŸrV·''· σ d |
536 | White Solid | |
537 | Clear Oil | F F P ° |
311
Compound No. | Appearance | Structure |
538 | White Solid | Υ,γ σΑ> |
539 | ClearOil | σΑ |
540 | Clear Oil | A σΑ |
312
Compound No. | Appearance | Structure |
541 | Light Yellow Oil | <^»3 À σΤ / HjC |
542 | Colorless Oil | y W' ûT v-., |
543 | White Solid | Cl o /CH3 C J CHi br |
313
Compound No. | Appearance | Structure |
544 | White Solid | J \ ys—CH3 Q |
545 | White Fluffy Solid | CHj br |
546 | Brown Solid | ci Q \ Br Cr “ br |
314
Compound No. | Appearance | Structure |
547 | Yellow Oil | σ HiCd o |
548 | White- Yellow Oïl | |
549 | Colorless Oil | CH 3 Cl o \ /CHj Q ™, br |
315
Compound No. | Appearance | Structure |
550 | Colorless Oil | CH, j' vAchj bT |
551 | Colorless Oil | 7 vX.''· |
552 | Colorless Oil | F \F ç\ 0 /Hj σA ‘ |
316
Compound No. | Appearance | Structure |
553 | Colorless Oil | Cl o F\ ch3 Q br |
554 | Colorless Oil | ..... |
555 | Yellow Oil | Cl o A/ J S—N F ex N |
317
Compound No. | Appearance | Structure |
556 | Pale Yellow Gum | h3c rLK, 'ch, ''ch, N |
557 | Pale Yellow Gum | H3C ch3 n-\ /h3 ( J |
558 | Faint Yellow OU | F o _zS |
318
Compound No. | Appearance | Structure |
559 | Faint Yellow Oil | σΧ bT J |
560 | Yellow Solid | rL K/5 ch3 V |
561 | White Solid |
319
Compound No. | Appearance | Structure |
562 | Brown Gum | H3C \-CH3 ΝΓ*\—i/™3 It 7 OZ Y-s N \ ch3 |
563 | Pale Yellow Gum | JLCHj Îi ίΓ CHî |
564 | Pale Yellow Gum | ÇH3 o iï η '—ch3 ch3 |
320
Compound No. | Appearance | Structure |
565 | Pale Yellow Gum | ch3 Χ’γRR |
566 | Pale Yellow Gum | CHj ÇHj(> / RK (R R br |
567 | Off-White Solid | CH, n ! 3 Q n-\ Λ /CH3 c«>CHl |
321
Compound No. | Appearance | Structure |
568 | Pale Yellow Gum | ChjOv \zUbH '“Λ || CHj CHj |
569 | Colorless Oil | Cl o \ .CH, H>c |
570 | White Seml- Solid | f-Vf P o A zCHî σΑ> ° ÎZ 3 |
322
Compound No. | Appearance | Structure |
571 | White Seml- Solid | ci q ch3 |
572 | Colorless Oil | F P °\ Q· « N |
573 | Coloriess Oil | F .CI θ\ cTy... ' |
323
Compound No. | Appearance | Structure |
574 | Colorless Oil | F pl F ^Y CHJ |
575 | Colorless Oil | F P °\ AX |
576 | Colorless Oil | CH, h3Y/ 3 Cl p ^S/CH3 Q e», |
324
Compound No. | Appearance | Structure |
577 | Coloriess Oil | ci 0 A zCHj N |
578 | Coloriess Oil | y_cll, V ,,jC |
579 | Coloriess Oil | P O CH3 ’i' AVXijC Xch3 O HîC N |
325
Compound No. | Appea rance | Structure |
580 | Coloriées Oil | Cl 0 CHj ü J CHj HjC TT |
581 | Colorless Solid | P O X nX kyyV^cH, (kr |
582 | Clear Oil | ri / ° NZ σηΪ N |
326
Compound No. | Appearance | Structure |
583 | Brown Oil | P Ov _ |
584 | Dark Yellow Oil | [Γ'Υ'-γ ÎC |
585 | White Solid | ci 0 V »’c |
327
Compound No. | Appearance | Structure |
586 | Yellow Solid | /Cl ° H3<v N |
587 | Purple Solid | Cl o HjC O N |
588 | Dark Yellow Oil | Q ». br |
328
Compound No. | Appearance | Structure |
589 | Colorless Solid | H3C /C1 o \ , X N |
590 | Brown Solid | HjC CH, C! 0 XCH3 |
591 | Light Yellow Solid | ch3 cX |
329
Compound No. | Appearance | Structure |
592 | Brown Oil | ζγ·' Q J N |
593 | Brown Oil | O =», N |
594 | Faint Yellow Solid | Ντ=( —/ v_J Çr C1IJ w |
330
Compound No. | Appearance | Structure |
595 | White Solid | o. V n=\ K<ACH’ U R°A h3c |
596 | Brown Solid | HjC CHj CHj 0 Y— CHj OR -CH br |
597 | Colorless Oil | /‘Vxp Qr |
331
Compound No. | Appearance | Structure |
598 | Colorless OU | /Hj CHj 0 y--S σ |
599 | Colorless Oil | CHj O y--S ï CH’ G |
600 | White Solid | CHj o CHj V 1/ CHj N |
601 | Yellow Solid | HjC CH, CHp ^CH, |
332
Compound No. | Appearance | Structure |
602 | Colorless Oil | zCHj /—s xr |
603 | Light Brown Solid | dX F Λ \ CHj |
604 | Brown Gum | =CI, U br |
605 | Light Brown Oil | rCKs |
333
Compound No. | Appearance | Structure |
606 | Light Brown Oil | p V‘ rc XXe”’ |
607 | Colorless Oil | CH j |
608 | Colorless Oil | CH3 Cl O y--S ___C”3 rr^^c” |
609 | Colorless Oil |
334
Compound No. | Appearance | Structure |
610 | Yellow Solid | Cl <5 CH3 c/P |
611 | Yellow Oil | ci o c»> & J |
612 | Belge Solid | J y-/-™’ σΡ |
613 | Brown Oil | F-V U -™ rr |
335
Compound No. | Appearance | Structure |
614 | Colorless Oil | Cl O V,CH, Cr -ch |
615 | Colorless Oil | F |
616 | White Solid | σ'Τ'· HC |
617 | Off-White Foam | rO-P ch3 (y j |
336
Compound No. | Appearance | Structure |
618 | Yellow Foam | rY' σΤ |
619 | White Solid | c'T N HC7 |
620 | Pale Yellow Oil | p o ’V Y |
621 | Pale Yellow Oil | σΥ |
337
Compound No. | Appearance | Structure |
622 | Yellow Oil | |
623 | Yellow Solid | F cF |
624 | White Solid | |
625 | Colortess Oil | HC' |
338
Compound No. | Appearance | Structure |
626 | Light Yellow Oil | ^>CH |
627 | Yellow Viscous Oil | CHj |
Table 2: Compound number and analytlcal data
Compound No. | MP* | IR6 | Mass | ’H NMR | ”C NMR |
596 | 73- 75 | ESIMS m/z 312.2 ([M+1D | ’H NMR (300 MHz, DMSO-cfe) δ 9.04 (d, J =2.4 Hz, 1 H), 8.60 (s, 1H), 8.49 (dd, J =4.7,1.4 Hz, 1H), 8.17 (ddd, J = 8.4,2.7,1.4 Hz, |
339
Compound No. | MP* | IRh | Mass | 1H NMR | 13C NMR |
1H), 7.52 (ddd, J = 8.4,4.7,0.6 Hz, 1H), 4.30 (d, J = 2.1 Hz, 2H), 3.23 (s,1H), 2.18 (s, 3H), 1.39 (s, 6H). | |||||
597 | ESIMS m/z 337 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.5 Hz, 1H), 8.59 (dd, J =4.7,1.3 Hz, 1H), 8.05 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 8.01 (s, 1H), 7.44 (ddd, J =8.3, 4.8,0.4 Hz, 1H), 4.44 (s, 2H), 2.61 2.43 (m, 2H), 2.432.33 (m, 2H), 2.30 (s. 3H), 2.26 (t, J = 2.5 Hz, 1H). | i3C NMR (101 MHz, CDCI3) δ 170.37,148.49, 148.04,140.21, 136.04,126.23, 125,26,124.16, 124.01,78.59, 72.69, 38.69, 29.57, 29.26, 26.69,11.14 | ||
598 | ESIMS m/z 315.1 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.4 Hz, 1H), 8.58 (dd, J = 4.7,1.4 Hz, 1H), 8.04 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 8.01 (s, 1H), 7.43 (ddd, J= 8.3, 4.8,0.5 Hz, IH), 4.45 (s, 2H), 2.79 (t, J =7.3 Hz, 2H), | 13CNMR(101 MHz, CD Cl 3) δ 171.73,148.71, 147.93,140.17, 136.09,128.15, 125.41,124.55, 123.99, 78.85, 72.51, 38.35, 33.80, 29.57, 15.96,11.20 |
340
Compound No. | MP* | IR6 | Mass | 1HNMR | 13C NMR |
2.45 (t, J =7.3 Hz, 2H), 2.31 (s, 3H), 2.24 (t, J =2.5 Hz, 1H), 2.06 (s, 3H). | |||||
599 | ESIMS m/z 283 ([M-SMe+H]*) | Ή NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.5 Hz, 1H), 8.58 (dd, J =4.7,1.4 Hz, 1H), 8.04 (ddd, J = 6.9, 2.7,1.5 Hz, 2H), 7.48-7.38 (m, 1H), 4.47 (bs, 2H), 2.88 (dd,J=12.7, 9.2 Hz, 1H), 2.77 (s, 1H), 2.44 (dd, J = 12.8, 5.1 Hz, 1H), 2.34 (s, 3H), 2.24 (s, 1H). 2.01 (s, 3H), 1.14 (d, J = 6.7 Hz, 3H). | |||
600 | 89- 90 | ESIMS m/z 283.5 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.96 (d. J = 2.5 Hz, 1H), 8.57 (dd, J = 4.7,1.3 Hz, 1H), 8.04 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 8.00 (s, 1H), 7.43 (dd, J =8.3, 4.8 Hz, 1H), 4.43 (bs, 2H), 2.60 (dt, J = 13.5,6.8 Hz, 1H), | 13C NMR (101 MHz, CDCI3) δ 177.64,148.89, 148.85,147.83, 140.13,136.13, 126.06,125.08, 125.02,123.97, 79.12, 72.41, 38.23, 31.05, 19.52,11.16. |
341
Compound No. | MP* | IRb | Mass | Ή NMR | ”C NMR |
2.29 (s, 3H), 2.23 (t. J =2.5 Hz, 1 H), 1.08 (d, J =6.7 Hz. 6H). | |||||
601 | 81- 82 | ESIMS m/z 329.8 ([M-HD | ’H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 8.37 (d, J = 2.5 Hz, 1H), 7.99 (s, 1 H). 7.83 (dt, J = 9.5, 2.2 Hz, 1H), 4.31 (s, 2H), 2.29 (t, J = 2.4 Hz, 1H), 2.27 (s, 3H), 1.45 (s, 9H). | ||
602 | ESIMS m/z 347.5 ([M+H]*) | ’H NMR (400 MHz, CDCI3) δ 8.77 (d, J = 1.7 Hz, 1H), 8.43 (d, J = 2.5 Hz, 1H), 8.05 (s, 1H), 7.86 (dt, J =9.4, 2.3 Hz. 1H). 4.49 (s, 2H). 2.88 (dd, J =12.8. 9.4 Hz. 1 H), 2.74 (s, 1H). 2.45 (dd, J = 12.9,5.0 Hz,1H), 2.34 (s, 3H), 2.24 (t, J =2.5 Hz, 1H), 2.02 (s, 3H). 1.14 (d, J =6.8 Hz, 3H). | |||
603 | 99- | ESIMS | NMR (400 MHz, CDCI3) δ 8.77 (d, J |
342
Compound No. | MP1 | IR* | Mass | 1HNMR | 13C NMR |
100 | m/z 299.5 ([M-HD | = 1.5 Hz, 1H), 6.43 (d, J= 2.5 Hz, 1H), 6.01 (s, 1H), 7.66 (dt, J =9.4, 2.3 Hz, 1H), 4.43 (s, 2H), 2.57 (dt, J =13.5, 6.7 Hz, 1 H), 2.29 (s, 3H), 2.23 (t, J = 2.5 Hz, 1 H), 1.06 (d, J =6.7 Hz, 6H). | |||
604 | ESIMS m/z 353.6 ([M]*) | 1H NMR (400 MHz, CDCI3) δ 6.77 (d, J = 1.9 Hz, 1H), 6.44 (t, J =4.4 Hz, 1H), 6.03 (s, 1 H), 7.67 (dt, J =9.3, 2.4 Hz, 1H), 4.44 (s, 2H), 2.56 - 2.42 (m, 2H), 2.36 (dd, J =12.7, 5.5 Hz, 2H), 2.30 (s, 3H), 2.27 (s, 1H). | 13CNMR (101 MHz, CDCI3) δ 170.26,149.03, 136.33,136.26, 136.05,135.42, 135.29,126.49, 125.46,124.59, 113.46, 76.51, 72.61, 36.62, 26.73,11.13. | ||
605 | ESIMS m/i 333.69 ([M+H]*) | Ή NMR (400 MHz, CDCI3) δ 6.76 (d, J = 1.6 Hz, IH), 6.44 (d, J =2.5 Hz, 1H), 6.05 (s, 1H), 7.66 (dt, J =9.3, 2.3 Hz,1H), 4.45 (s, 2H), 2.79 (t, J= 7.3 Hz, 2H), 2.43 (t, J- |
343
Compound No. | MP* | 1Rb | Mass | 1HNMR | 15C NMR |
7.3 Hz, 2H), 2.30 (s, 3H), 2.25 (t. J = 2.5 Hz, 1H), 2,06 (s, 3H) | |||||
606 | ESIMS m/z 276.8 ([M-t-Bu]*) | ’HNMR (400 MHz, CDCI3) δ 8.94 (d, J = 2.5 Hz, 1H), 8.58 (dd, J =4.7,1.3 Hz, 1H), 8.07 (s, 1H), 8.05-7.92 (m, 1H), 7.42 (dd, J =8.3, 4.8 Hz, 1H), 4.36 (s, 2H), 2.29 (t, J =2.4 Hz, 1 H), 1.46 (s, 9H). | 13C NMR (101 MHz, CDCI3) δ 170.97,154.09, 148.02,139.81, 136.83,135.90, 133.69,133.53, 126.02,124.26, 123.96, 81.33, 60.31, 28.08. | ||
607 | ESIMS m/z 335.1 ([M+H]*) | ’H NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.5 Hz, 1H), 8.64 (dd, J =4.7,1.3 Hz, 1H), 8.12 (s, 1 H), 8.06 (ddd, J =8.4, 2.7,1.4 Hz, 1H), 7.47 (dd, J =8.3, 4.8 Hz, 1 H), 4.48 (s, 2H), 2.81 (t. A = 7.4 Hz, 2H), 2.50 (t, J = 7.4 Hz, 2H), 2.27 (t, J =2.5 Hz, 1H), 2.08 (s, 3H). | 13C NMR (101 MHz, CDCI3) δ 175.54,148.75, 140.82,140.16, 135.66,126.41, 124.12,122.68, 78.61,77.33, 77.02, 76.70, 72.86, 37.83, 37.22,18.11, 16.54. | ||
608 | ESIMS | 1H NMR (400 MHz, | 13C NMR (101 |
344
Compound No. | MP* | IR* | Mass | Ή NMR | «C NMR |
m/z 349.1 ([M+H]*) | CDCB) δ 8.97 (d, J = 2.5 Hz, 1H), 8.64 (dd, J = 4.7,1.3 Hz, 1H), 8.16 (s, 1 H), 8.05 (ddd, J = 8.3, 2.7,1.4 Hz, 1H), 7.47 (dd, J = 8.3, 4.8 Hz, 1H), 5.30 (s, 2H), 2.87 (dd, J = 12.8, 8.8 Hz, 1H), 2.75 (d, J = 6.3 Hz, 1H), 2.49 (dd, J = 12,9, 5.4 Hz, 1 H), 2.26 (t, J = 2.5 Hz, 1H), 2.03 (s, 3H), 1.18 (d, J = 6.7 Hz, 3H). | MHz, CDCb) δ 171.42,148.77, 140.68,140.10, 135.65,127.00, 126.48,124.14, 122.73, 78.58, 72.91, 37.82, 33.86,29.41, 15.92. | |||
609 | ESIMS m/z 357.1 ([M+H]*) | ’H NMR (400 MHz, CDCB) δ 8.97 (d, J = 2.5 Hz, 1 H), 8.65 (dd, J =4.7,1.3 Hz, 1H), 8.22 (s, 1 H) 8.12 (s, 1 H), 7.48 (dd, J =7.5, 3.9 Hz, 1H), 4.46 (s, 2H), 2.61 - 2.35 (m, 4H), 2.29 (dd, J =4.7, 2.4 Hz, 1H). | ’3C NMR (101 MHz, CDCB) δ 170.10, 148.90, 140.16,139.27, 126.82,126.57, 124.14, 123.89, 122.29, 78.32, 73.09, 72.50, 38.13, 36.29, 26.71. | ||
610 | 98- 99 | ESIMS m/z 303.1 | ’HNMR (400 MHz, CDCb) δ 8.96 (d, J = 2.6 Hz, 1H), 8.63 |
345
Compound No. | MP* | IR* | Mass | Ή NMR | ”C NMR |
([M+H]*) | (dd, J-4.7,1.2 Hz, 1H), 8.09 (s, 1H), 8.06 (ddd, J =8.3, 2.7,1.5 Hz, 1H), 7.46 (dd, J =8.4, 4.8 Hz, 1H), 4.40 (m, 2H), 2.76-2.44 (m, 1H), 2.24 (t, J = 2.4 Hz, 1H), 1.57 (s, 1H), 1.11 (d, J = 6.7 Hz, 6H). | ||||
611 | ESIMS m/z 335 ([M+H]*) | ’H NMR (400 MHz, CDCIa) δ 8.97 (d, J = 2.5 Hz, 1 H), 8.66 -8.60 (m, 1H), 8.25 (s, 1H), 8.08-8.01 (m, 1H), 7.49-7.42 (m, 1H), 4.86 (s, 1H), 4.29-3.97 (m, 1H), 3.31 (d, J6.5 Hz, 1H), 2.302.24 (m, 1 H), 2.09 (s, 3H), 1.46 (d,J = 6.9 Hz, 3H). | 13C NMR (101 MHz, CDCI3) δ 171.30,148.66, 140.71,140.18, 135.71,127.87, 126.35,124.11, 122.12, 78.53, 72.92, 53.39, 37.97,16.42, 11.07. | ||
612 | 65- 68 | ESIMS m/z 321 ([M+H]*) | ’H NMR (400 MHz, CDCIj) δ 8.96 (s, 1H), 8.63 (d, J = 4.2 Hz, 1H), 8.21 (s, 1H), 8.09-8.00 (m, 1H), 7.50-7.43 (m, 1H), 4.53 (brs, | ”CNMR (101 MHz, CDCIa) δ 169.20,148.57, 140.58,140.10, 127.82,126.47, 122.27, 99.98, 78.37, |
346
Compound No. | MP1 | IRfc | Mass | 1H NMR | 1ÏC NMR |
2H), 3.12 (s, 2H), 2.28 (t, J =2.5 Hz, 1H), 2.23 (s, 3H). | 77.23,73.07, 37.90, 35.01, 15.96. | ||||
613 | 1674 | ESIMS m/z 403 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.6 Hz, 1H), 8.64 (dd, J =4.7,1.3 Hz, 1H). 8.13 (s. 1H). 8.07 (ddd, J =8.3, 2.7,1.5 Hz, 1H), 7.48 (ddd, J =8.3, 4.8, 0.5 Hz, 1H), 4.39 (s, 2H), 3.76 (dqd. J= 17.2,8.6, 3.6 Hz, 1H), 2.67 (dd, J =16.6, 3.6 Hz, 1H), 2.46 (dd, J = 16.5, 9.9 Hz, 1H), 2.29 (d, J =2.5 Hz, 4H). | ||
614 | 1671 | ESIMS m/z 353 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.5 Hz, 1H), 8.64 (dd, J = 4.7.1.4 Hz, 1H), 8.12 (s. 1 H). 8.07 (ddd, J =8.3, 2.7,1.4 Hz, 1H), 7.47 (ddd, J =8.3, 4.8, 0.4 Hz, 1 H), 4.47 (s, 2H), 2.482.35 (m. 2H), 2.35- |
347
Compound No. | MP* | IRh | Mass | ’HNMR | C NMR |
2.16 (m,3H), 1.60 (t, J= 18.4 Hz, 3H). | |||||
615 | 1676 | ESIMS m/z 407 ([M+H]*) | Ή NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.5 Hz, 1H), 8.65 (dd, J =4.7.1.2 Hz, 1H), 8.13 (s, 1 H), 8.07 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.48 (dd, J = 8.3, 4.7 Hz, 1H), 4.47 (s, 2H), 2.58 - 2.39 (m, 4H), 2.29 (t. J = 2.5 Hz,1H). | ||
616 | 1662 | ESIMS m/z 377 ([M+H]*) | 1H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.5 Hz, 1H), 8.64 (dd, J =4.7.1.1 Hz, 1H), 8.17 (s, 1H), 8.06 (ddd, J =8.3, 2.7,1.4 Hz, 1H), 7.47 (dd, J = 8.3, 4.7 Hz, 1H), 4.924.10 (m, 2H), 3.06 (ddd, J = 7.7, 6.2, 4.3 Hz, 1H), 2.45 (s, 1 H), 2.44 (d,J = 2.4 Hz, 1 H), 2.27 (t, J = 2.5 Hz, 1H), 2.11 (s, 3H), 1.971.85 (m, 1H), 0.96 |
348
Compound No. | MP* | IRb | Mass | ’H NMR | ”C NMR |
(d. J-6.7 Hz, 3H), 0.88 (d, J =6.8 Hz, 3H). | |||||
617 | ESIMS m/z 351 ([Μ+ΗΓ) | ’H NMR (400 MHz, CDCI3) δ 8.98 (s, 1H), 8.65 (d,J = 4.6 Hz, 1H), 8.23 (s, 1H), 8.11-7.97 (m, 1H), 7.51-7.41 (m, 1H), 4.88 (br s, 1H), 4.14 (br s, 1H), 2.64 (s, 1.2H), 2.55 (s, 1.8H), 2.33 -2.27 (m, 1H), 1.47 (d, J =6.8 Hz, 3H), 1,42 (brs). | ’3C NMR (101 MHz, CDCh) δ 168.11,148.95, 148.78,140.45, 140.33,140.20, 135.56, 126.54, 124.10, 121.68, 121.58,121.48, 77.69, 73.49, 38.60. | ||
618 | ESIMS m/z 367 ([M+H]*) | ’H NMR (400 MHz, CDCh) δ 9.00 (s, 1H), 8.65 (s, 1H), 8.29 (s, 1H), 8.03 (d, J =8.0 Hz, 1H), 7.54-7.39 (m, 1H), 4.89 (d, J = 16.9 Hz, 1H), 4.20-4.08 (m, 1H), 4.07-3.92 (m, 1H), 3.01 (s, 3H), 2.34 - 2.29 (m, 1 H), 1.67 (d, J = 7.0 Hz, 3H). | ’3C NMR (101 MHz, CDCI3) δ 166.97,166.90, 148.77,140.43, 140.24,135.58, 129.36, 126.64, 124.14,121.34, 73.80, 60.91, 38.78, 36.29, 13.97. | ||
619 | 109- | 1665 | ESIMS | ’H NMR (400 |
349
Compound No. | MP* | IR6 | Mass | ’HNMR | ”C NMR |
112 | m/z 375.5 ([M+H]*) | MHz, CDCI3) δ 8.97 (s, 1H). 8.64 (d. J = 4.2 Hz, 1H), 8.14 (s, 1H), 8.07 (ddd, J =8.3,2.6,1.4 Hz, 1H), 7.47 (dd,J = 8.3,4.7 Hz, 1H), 4.45 (s, 2H), 2.63- 2.46 (m, 3H), 2.27 (t, J = 2.5 Hz, 1H), 2.14 (s, 3H), 0.900.73 (m, 1H), 0.660.57 (m, 1H), 0.570.44 (m, 1H), 0.420.35 (m, 1 H), 0.35- 0.23 (m,1H). | |||
620 | 1673 | ESIMS m/z 337 ([M+H]*) | ’HNMR (300 MHz, CDCI3) δ 8.97 (d, J = 2.6 Hz, 1H), 8.64 (dd, J = 4.8,1.4 Hz, 1H), 8.23 (s, 1H), 8.03 (ddd, J = 8.4, 2.7,1.5 Hz, 1H), 7.46 (dd, J = 8.4, 4.7 Hz, 1H), 4.52 (brs, 2H), 3.68 (br s, 2H), 2.78 (s, 3H), 2.29 (t, J = 2.5 Hz, 1H). | ||
621 | 1667 | ESIMS m/z 353 | Ή NMR (300 MHz, CDCI3) δ 8.98 (d, J |
350
Compound No. | MP* | IR* | Mass | ’H NMR | ”C NMR |
([M+H]*) | = 2.7 Hz, 1 H), 8.64 (d, J = 4.8 Hz, 1H), 8.28 (d, J = 1.0 Hz, 1H), 8.03 (dt, J = 8.4,1.3 Hz, 1H), 7.46 (dd, J = 8.3, 4.8 Hz, 1H), 4.88 (brS, 2H). 3.97 (br s. 2H), 3.20 (s, 3H), 2.31 (dt, J = 2.4, 1.3 Hz, 1H). | ||||
622 | 1749, 1666 | ESIMS m/z 409 ([M+H]*) | ’H NMR (300 MHz, CDCI3)5 9.01 (s, 1H). 8.61 (s, 1H), 8.28 (s, 1H). 8.128.05 (m, 1H), 7.487.41 (m, 1H), 6.09 (s, 0.5H), 4.10 (s, 1H), 3.58 (s, 0.5H), 3.37 (s, 0.5H), 3.27 (s, 1.5H), 2.30 (d, J = 1.4 Hz, 1H), 2.24 (s, 3H), 2.20 (s, 3H), 1.61 (s. 1H) | ||
623 | 1678 | ESIMS m/z 332 ([M+H]*) | ’H NMR (400 MHz, CDCI3) δ 8.97 (d, J = 2.6 Hz, 1 H), 8.65 (dd, J =4.8,1.3 Hz, 1H), 8..15(s, 1H), 8.04 (ddd, J =8.3, 2.7,1.4 Hz, 1 H), |
351
Compound No. | MP* | IRb | Mass | 1H NMR | 1ÏC NMR |
7.48 (dd, J =8.4, 4.7 Hz, 1H), 3.77 (hept, J =6.9 Hz, 2H). 3.05 (s, 2H), 3.01 (s, 3H), 2.87 (s, 3H), 2.31 (t, J~ 2.5 Hz, 1H). | |||||
624 | 68- 70 | ESIMS m/z 563.2 ([M+1])* | Ή NMR (400 MHz, CDCI3) δ 8.94 (dd, J =4.9, 2.7 Hz, 1H), 8.65 (dd, J = 4.8,1.5 Hz, 1H), 8.07 - 7.98 (m, 1H), 7.94 (s, 1H), 7.2-7.5 (m. 16H), 4.44(m, 2H). 2.64 (t, J-7 Λ Hz, 2H). 2.52 (t, J =7.3 Hz, 2H), 2.22 (s. 1H). | ||
625 | 3254, 3039, 2555, 1685 | ESIMS m/z 321.1 ([M+1f), 319.1 ([M-1D | 1H NMR (400 MHz, CDCIa) δ 9.01 8.92 (m, 1H), 8.64 (d, J =5.9 Hz, 1H), 8.11 (s. 1 H), 8.06 (ddd, J =8.3, 2.7, 1.5 Hz, 1H), 7.47 (dd, J =8.3,4.8 Hz, 1H), 4.56 (m, 1 H), 2.93 (dt, J =8.5, 6.6 Hz, 2H), 2.54 (t, J =6.7 Hz, 2H), |
352
Compound No. | MP' | IRb | Mass | ’HNMR | 1SC NMR |
2.27 (t, J =2.5 Hz, 1 H), 1.71 (dt, J = 11.6, 8.4 Hz, 2H). | |||||
626 | 3299, 1672 | ESIMS m/z 417.2 ([M+H]*) HRMS-FAB (m/z) [M+H]* calcd for C17H17CIF3N4OS4 17.0758; found, 417.0754 | 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J - 2.7 Hz, 1H), 8.64 (dd, J = 4.8,1.4 Hz, 1H), 8.12 (s, 1 H), 8.06 (ddd, J = 8.3, 2.7,1.5 Hz, 1H), 7.47 (dd, J =8.5, 4.8 Hz, 1H), 4.47 (s. 2H). 2.86 (t. J = 7.2 Hz, 2H), 2.74 2.61 (m, 2H), 2.50 (t, J =7.2 Hz, 2H), 2.45 - 2.29 (m, 2H), 2.28 (t, J = 2.5 Hz, 1H). | ||
627 | 3293, 1663 | ESIMS m/e 397.3 ([M+H]*) HRMS-FAB (m/z) [M+H]* calcd for CiaHa)F3N4OS, 397.1304; found, 397.1322 | 1H NMR (400 MHz, CDCI3) δ 8.96 (d, J = 2.6 Hz, 1 H), 8.58 (dd, J =4.8,1.5 Hz, 1H), 8.04 (ddd, J = 8.3, 2.7, 1.5 Hz, 1H), 8.01 (s, 1H), 7.44 (dd, J =8.3, 4.9 Hz. 1H), 4.45 (s, 2H), 2.84 (t, J = 7.1 Hz, 2H), 2.72 2.60 (m, 2H), 2.44 |
353
Compound No. | MP* | IR6 | Mass | ’HNMR | 13C NMR |
(t, J = 7.1 Hz, 2H), 2.41 - 2.32 (m, 2H), 2.31 (s, 3H), 2.26 (t. J =2.4 Hz, 1H). |
• CO b (Thin Film; cm'1)
Table 3: GPA (MYZUPE) and sweetpotato whltefly-crawler (BEMITA) Rating Table
% Control (or Mortality) | Rating |
80-100 | A |
More than 0 - Less than 80 | B |
Not Tested | C |
No activity noticed In this bioassay | D |
Table 4. Blologlcal Data for GPA (MYZUPE) and sweetpotato whltefly-crawler (BEMITA)
Compound No. | MYZUPE % Ctrl @ 200 ppm | BEMITA % Ctrl @ 200 ppm |
596 | A | A |
597 | A | B |
598 | A | B |
599 | A | B |
600 | A | B |
354
Compound No. | MYZUPE % Ctrl @ 200 ppm | BEMITA % Ctrl @ 200 ppm |
601 | A | A |
602 | A | A |
603 | A | A |
604 | A | A |
605 | A | A |
606 | A | A |
607 | A | A |
608 | A | A |
609 | A | A |
610 | A | A |
611 | A | A |
612 | A | A |
613 | A | A |
614 | A | A |
615 | B | A |
616 | C | C |
617 | C | C |
618 | C | C |
619 | A | A |
620 | A | A |
621 | A | A |
622 | A | A |
623 | A | A |
355
Compound No. | MYZUPE % Ctrl @ 200 ppm | BEMITA % Ctrl @ 200 ppm |
624 | C | C |
625 | C | C |
626 | A | A |
627 | A | A |
356
Claims (62)
- WE CLAIM1. A composition comprising a molécule according toFormula OneR65 wherein (a) A is either attachment bond (b) R1 Is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted Cj-Ce alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C^ aryl, substituted or unsubstituted CpC^15 heterocyclyl, OR9, C(=X1 )R9, C(=X1 }OR9, C(=X1 }N(R9)21 N(R9)21 N(R9)C(=X1 )R9, SR9, S(O)nOR9, S(O)nN(R9)21 or R9S(O)nR9,357 wherein each said R1, which is substituted, has one or more substituents selected from F, Cl, Br, i, CN, NO2, CrCe alkyl, C^-Ce alkenyl, CrCe haloalkyl, CrCe haloalkenyl, CrCe haioalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3-C10 halocycloalkyl, C3-C10 halocydoalkenyl, OR9, S(O)nOR9, Ce-C» aryl, or CrC» heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);(c) R2 Is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted Cj-Cîo cycloalkenyl, substituted or unsubstituted Ce-C» aryl, substituted or unsubstituted CrC^ heterocydyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, or R9S(O)nR9, wherein each said R2, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, CrCe haloalkyl, CrCfl haloalkenyl, CrCe haioalkyloxy, CrCe haloalkenyloxy, CrC10 cycloalkyl, C3-C10 cydoalkenyl, CrCw halocydoalkyl, C3-C10 halocydoalkenyl, OR9, S(O)nOR9, Ce-Qn aryl, or CrC» heterocydyl, (each of which that can be substituted, may optionally be substituted with R9);(d) R3 is H, F, Cl, Br, i, CN, NO2, substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted CrCe alkenyloxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cydoalkenyl, substituted or unsubstituted Ce-C^ aryl, substituted or unsubstituted C1-C20 heterocydyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1 )R9, SR9, S(O)nOR9, or R9S(O)nR9, wherein each said R3, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, C2-Ce alkenyl, CrCe haloalkyl, CrCe haloalkenyl, CrCe haioalkyloxy, CrCe haloalkenyloxy, CrC10 cydoalkyl, C3-C10 cydoalkenyl, CrC10 halocydoalkyl, C3-C1Q halocydoalkenyl, OR9, S(O)nOR9, Ce-C» aryl, or CrC» heterocydyl, (each of which that can be substituted, may optïonaliy be substituted with R9);(e) when A is (1) A1 then A1 is either358 (a) A11 attachment bond to carbon attachment bond to nitrogenAil where R4 Is H, NO2, substituted or unsubstituted CpCe alkyl, substituted or unsubstituted CrCo alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-Ca) aryl, substituted or unsubstituted C1-C20 heterocyclyl, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)21 N(R9)C(=X1)R9, S(O)nOR9, orR9S(O)„R9, wherein each said R4, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CpCe alkyl, QrCe alkenyl, Ci-Ce haloalkyl, Cj-Ce haloalkenyl, CrCe haloalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, CrC10 cycloalkenyl, Cr C10 halocycloaikyl, C3-C10 halocycloalkenyl, OR9, S(O)nOR9, Ce-C^ aryl, or C^Ca heterocyclyl, (each of which that can be substituted, may optionaily be substituted with R9), (b) A12 attachment bond to nitrogen attachment bond to carbonA12 where R4 is a CrCe alkyl, or (2) A2 then R4 is H, F, Cl, Br, I, CN, NO2, substituted or unsubstituted Cr Ce alkyl, substituted or unsubstituted CrC6 alkenyl, substituted or unsubstituted Ci-Ce alkoxy,359 substituted or unsubstituted CrCe alkenyioxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C^ aryl, substituted or unsubstituted heterocyclyl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1 )R9, SR9, S(O)nOR9, or R9S(O)nR9, wherein each said R4, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, CrCe haloalkyl, C2-Ce haloalkenyl, CrCe haloalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3C10 halocycloalkyl, C3-C10 halocycloalkenyl, OR9, S(O)nOR9, Οβ-Ο» aryl, or Ci-Cm heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);(f) R5 Is H, F, Cl, Br, i, CN, NO2, substituted or unsubstituted CpCg alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted CrCe alkoxy, substituted or unsubstituted CrCe alkenyioxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C» aryl, OR9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nOR9, orR9S(O)nR9, wherein each said R5, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, CrCe haloalkyloxy, CrCe haloalkenyloxy, C3-C10 cycloalkyl, C3-C10 cycloalkenyl, C3-C10 halocycloalkyl, C3-C10 halocycloalkenyl, OR9, S(O)nOR9, or Ce-Ca) aryl, (each of which that can be substituted, may optionally be substituted with R9);(g) (1) when A is A1 then R6 Is R11, and (2) when A is A2 then R6 is R11 ;(h) R7 Is O, S, NR9, or NOR9;(i) R8 is substituted or unsubstituted CrCe alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted C^Cg alkoxy, substituted or unsubstituted CrCe alkenyioxy, substituted or unsubstituted C3-Ci0 cycloalkyl, substituted or unsubstituted CrCio cycloalkenyl, substituted or unsubstituted Ce-C» aryl, substituted or unsubstituted CrC» heterocyclyl OR9,360OR9S(O)nR9, C(=X1)R9, C{=X1)OR9, R9C(=X1)OR9, R9X2C(=X1)R9X2R9, C(=X1)N(R9)2,N(R9)2, N(R9)(R9S(O)nR9), N(R9)C(=X1)R9, SR9, S(O)nOR9, R9S(O)nR9, or R9S(O)n(NZ)R9, wherein each said R8, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCe alkyl, CrCe alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, C,-Ce haloalkyloxy, CrCe haloalkenytoxy, C3-C10 cycioalkyl, C3-C10 cycloalkenyl, C3-C10 halocycloaikyl, CrCio halocycloalkenyl, N(R9)S(O)nR9, oxo, OR9, S(O)nOR9, R9S(O)nR9, S(O)nR9, Ce-Ca aryl, or C,-C« heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);0) R9 is (each Independently) H, CN, substituted or unsubstituted C,-Ce alkyl, substituted or unsubstituted CrCe alkenyl, substituted or unsubstituted C,-Ce alkoxy, substituted or unsubstituted CrCe aikenyloxy, substituted or unsubstituted CrC10 cycioalkyl, substituted or unsubstituted C3-C10 cycloalkenyl, substituted or unsubstituted Ce-C« aryl, substituted or unsubstituted C,-C« heterocyclyl, 8(0),,0,-06 alkyl, N(C,-Cealkyl)2, wherein each said R9, which is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NÜ2, C,-Ce alkyl, C2-Ce alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, 0,-Ce haloalkyloxy, CrCe haloalkenytoxy, CrC,0 cycioalkyl, C3-C,0 cycloalkenyl, CrC,0 halocycloaikyl, C3-C10 halocycloalkenyl, OC,-Ce alkyl, OC,-Ce haloalkyl, S(O)„C,-Cealkyl, S(O)nOC,-Ce aikyî, Ce-C« aryl, or C,-C« heterocyclyl;(k) nisO, 1,or2;(l) X Is N or CRn, where Rn, Is H, F, Cl, Br, I, CN, N02, substituted or unsubstituted C,Ce alkyl, substituted or unsubstituted C2-Ce alkenyl, substituted or unsubstituted 0,-Ce alkoxy, substituted or unsubstituted C2-Ce aikenyloxy, substituted or unsubstituted C3-C10 cycioalkyl, substituted or unsubstituted C3-C,o cycloalkenyl, substituted or unsubstituted Ce-C^ aryl, substituted or unsubstituted C,-C« heterocyclyl, 0R9, C(=X1)R9, C(=X1)OR9, C(=X1)N(R9)2, N(R9)2, N(R9)C(=X1)R9, SR9, S(O)nR9, S(O)nOR9, or R9S(O)nR9, wherein each said Rn, which is substituted, has one or more substituents selected from F, Ci, Br, I, CN, NO2, C,-Ce alkyl, C2-Ce alkenyl, C,-Ce haloalkyl, CrCe haloalkenyl, C,-Ce haloalkyloxy, CrCe haloalkenytoxy, CrC10 cycioalkyl, CrC,0 cycloalkenyl, CrC10 halocycloaikyl, C3-C ,o halocycloalkenyl, 0R9, S(O)nOR9, Ce-C« aryl, or 0,-0« heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9);361 (m) X1 is (each Independently) O or S;(η) X2 Is (each independently) O, S, =NR9, or =NOR9;(o) Z Is CN, NO2, Ci-Cg alkyl(R9), C(=X1 )N(R9)2;(p) R11 is Qi(C=C)R12, wherein Qi is a bond, substituted or unsubstituted Ci - Ce alkyl, substituted or unsubstituted CrCg alkenyl, substituted or unsubstituted CrCg alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted CrC10 cycloalkoxy, substituted or unsubstituted CrCealkylOR9, substituted or unsubstituted CrCgalkylS(O)nR9, substituted or unsubstituted CrCgalkylS(O)n(=NR9), substituted or unsubstituted CrCgalkylN^) (where (CsC) is attached directly to the N by a bond), substituted or unsubstituted CrCgalkylN(R9)2, substituted or unsubstituted CrCg alkenyloxy, substituted or unsubstituted Qj-C^ cycloalkenyl, substituted or unsubstituted Co-CealkylC(=R7)Co-Ce alkylR9, substituted or unsubstituted Co-Cg alkylC(=R7)OR9, substituted or unsubstituted CpCg alkylOCo-Cg alkylC(=R7)R9, substituted or unsubstituted CpCg alkylN(R9)(C(=R7)R9), substituted or unsubstituted C,-CealkylN(R9)(C(=R7)OR9), substituted or unsubstituted Co-Cg alkyl C(=R7)Co-Cg alkylN(R9) (where (CeC) is attached directly to the N by a bond), substituted or unsubstituted C0-C6alkylC(=R7)C0-Ce alkylN(R9)2, OR9, S(O)nR9, N(R9)R9, substituted or unsubstituted Cg-C^ aryl, or substituted or unsubstituted CpC» heterocyclyl, wherein each said Q1, which Is substituted, has one or more substituents selected from F, Cl, Br, I, CN, NO2, CrCg alkyl, C^-Cg alkenyl, CrCg alkynyl, CrCg haloalkyl, C2-Cg haloalkenyl, CrCg haloalkyloxy, CrCg haloalkenyloxy, CrC10 cycloalkyl, C3-C10 cycloalkenyl, C3C10 halocycloalkyl, CrC10 halocycloalkenyl, OR9, SR9, S(O)nR9, S(O)nOR9, Cg-C» aryl, CpC^ heterocyclyl, R9aryl, CrCgalkylOR9, and Ci-CgalkylStO)^, (each of which that can be substituted, may optionally be substituted with R9) optionally Q« and R8 can be connected in a cyclic arrangement, where optionally such arrangement can hâve one or more heteroatoms selected from O, S, or N, In the cyclic structure connecting Qi and R8;(q) R12 is Q1 (except where Q1 is a bond), F, Cl, Br, I, Si(R9)3 (where each R9 Is Independently selected), or R9;362 (r) with the following proviso that when A Is A2 then R5 Is not C(=O)OH.
- 2. A composition according to claim 1 wherein said molécule said A Is A1.
- 3. A composition according to claim 1 wherein said molécule said A Is A2.
- 4. A composition according to claim 1 wherein said molécule said R11s H.
- 5. A composition according to claim 1 wherein said molécule said R2 Is H.
- 6. A composition according to claim 1 wherein said molécule said R3 Is selected from H, or substituted or unsubstituted CrCe alkyl.
- 7. A composition according to claim 1 wherein said molécule said R3 Is selected from H or CH3.
- 8. A composition according to claim 1 wherein said molécule when said A Is A1 then A1 Is A11.
- 9. A composition according to claim 1 wherein said molécule when said A is A1, and A1 Is A11, then R41s selected from H, or substituted or unsubstituted Ci-Ce alkyl, or substituted or unsubstituted Ce-Cw aryl.
- 10. A composition according to daim 1 wherein said molécule when said when A Is A1, and A1 Is A11 then R4 Is selected from CH3, CH(CH3)2i or phenyl.
- 11. A composition a ccording to claim 1 wherein said molécule when said when A Is A1, and A1 Is A12, then R4 Is CH3.363
- 12. A composition according to claim 1 wherein said molécule when said A Is A2 then R4 Is selected from H, substituted or unsubstïtuted CrCe alkyl, substituted or unsubstltuted CrCe alkenyl, substituted or unsubstltuted C3-C10 cycioalkyl, substituted or unsubstïtuted Ce-C^ aryl, wherein each said R4, which is substituted, has one or more substituents selected from F, Cl, Br, orI.
- 13. A composition according to claim 1 wherein said molécule when said A Is A2 then R4 is H or CpCe alkyl.
- 14. A composition according to claim 1 wherein said molécule when said A is A2 then R4 is H, CH3, CH2CH31 CH=CH2, cyclopropyl, CH2Ci, CF3, or phenyl.
- 15. A composition according to claim 1 wherein said molécule when said A Is A2 then R4 Is Ci.
- 16. A composition according to claim 1 wherein said molécule said R5 is selected from H, F, Ci, Br, I, substituted or unsubstltuted CrCe alkyl, substituted or unsubstïtuted CrCe alkoxy,
- 17. A composition according to claim 1 wherein said molécule said R5 is selected from H, OCH2CH3, F, Cl, Br, or CH3.
- 18. A composition according to claim 1 wherein said molécule said R11 is CH2C^CH and R8 Is (substituted or unsubstïtuted CrCe alkyl)-S(O)n-(substituted or unsubstïtuted CrCe alkyl) wherein said substituents on said substituted alkyls are selected from F, Cl, Br, I.
- 19. A composition according to claim 1 wherein said molécule said R11 is CH2CeCH and R8 Is (unsubstïtuted CrCe alkyl)-S(O)n-(substituted CrCe alkyl) wherein sald substituents on said substituted alkyls are selected from F, Cl, Br, I.
- 20. A composition according to claim 1 wherein said molécule said R11 is CH2C=CH and R8 is (unsubstïtuted C1-C2 alkyl)-S(O)n-(substituted CrC3 alkyl) wherein sald substituents on said substituted alkyls are F.364
- 21. A composition according to claim 1 wherein said molécule said R11 Is substituted or unsubstituted Ci-C3 alkylC^CH.
- 22. A composition according to claim 1 wherein said molécule said R11 Is substituted or unsubstituted CrC2 alkylC^CH.
- 23. A composition according to claim 1 wherein said molécule said R11 Is substituted or unsubstituted CH2C=CH.
- 24. A composition according to claim 1 wherein said molécule said R7 Is O or S.
- 25. A composition according to claim 1 wherein said molécule said R8 Is selected from substituted or unsubstituted CrCe alkyl, substituted or unsubstituted C2-Ce alkenyl, substituted or unsubstituted Co-Cjo cycloalkyl, substituted or unsubstituted Ce-C» aryl, substituted or unsubstituted 0,-0^ heterocyclyl, R9C(=X1)OR9, SR9, S(O)nOR9, R9S(O)„R9, or R9S(O)n(NZ)R9.
- 26. A composition according to claim 1 wherein said molécule said R8 is CH(CH3)CH2SCH3, CH(CH3)2, CfCHahCHiSCHa, CH2CH2SCH3. CH2CF3, CH2CH2C(=O)OCH3, N(H)(CH2CH2SCH3), OCHaCHaSCHs, CH(CH2SCH3)(CH2phenyl), thiazolyl, oxazolyl, Isothiazoiyl, substituted-furanyl, CH3, C(CH3)31 phenyl, CH2CH2OCH3, pyridyl, CH2CH(CH3)SCH3, OC(CH3)3, C(CH3)2CH2SCH3, CH(CH3)CH(CH3)SCH3, CH(CH3)CF3, CH2CH2-thlenyl, CH(CH3)SCF3,CH2CH2CI, CH2CH2CH2CF3, CH2CH2S(=O)CH3, CH(CH3)CH2S(=O)CH3, CH2CH2S(=O)2CH3, CH(CH3)CH2S(=O)2CH3, NCH2CH3, N(H)(CH2CH2CH3), C(CH3)=C(H)(CH3), N(H)(CH2CH=CH2), CH2CH(CF3)SCH3, CHtCFsJCHîSCHa. thletanyl, CH2CH(CF3)2, CH2CH2CF(OCF3)CF3, CH2CH2CF(CF3)CF31 CF(CH3)2, CH(CH3)phenyl-CI, CH(CH3)phenyl-F, CH(CH3)phenyl-OCF31 CH2N(CH3)(S(=O)2N(CH3)2, CH(CH3)OCH2CH2SCH3, CH(CH3)OCH2CH2OCH3, OCH3, CH(CH3)SCH3, CH2SCH3, N(H)CH3, CH(Br)CH2Br, CHîCHîSCHîCHîCFs, CHjCHjSH, CH2CH2SC(phenyl)3, CH2N(CH3)S(O)2CH3, CH(SCH3)(C(=O)CH2SCH3), CH2S(O)CH3. CH2CH(cyclopropyl)SCH3, or CHtCHaïCHîSCDa.
- 27. A composition according to claim 1 wherein said molécule said R8 Is selected from (substituted or unsubstituted CrCe alkyl)-S(O)n-(substituted or unsubstituted CrCe alkyl) wherein365 said substituents on said substituted alkyls are selected from F, Cl, Br, I, CN, NO21 N(R9)S(O)nR9, OR9, S(O)nOR9, R9S(O)nR9, S(O)nR9, Cb-Cm aryl, or Ci-Cm heterocyclyl, (each of which that can be substituted, may optionally be substituted with R9).5
- 28. A composition according to claim 1 wherein said molécule said X is CRni where Rm Is H or halo.
- 29. A composition according to claim 1 wherein said molécule said X Is CRn1 where Rm is H orF.
- 30. A composition according to claim 1 wherein said molécule said X1 orX2 or both are O.
- 31. A composition according to claim 1 wherein said molécule has one of the following structures
596 HjC CH, 597 --cA CJ N 366367368369370614 ci Οχ F\ ch3 Çf 615 F Çr 616 «,c-yCH> P O \ .CH, 'F w lie' 617 / V-Xc· aï5X“' 371618 /' \\ Xe· yZ~\ ° CII> U / 619 P V zC,tî (A/ ’ 620 Q P o \\__ —< X >—CHj σ y 621 d-A αχ 372622 N HC-X 623 p xw· pO-·' ° oe N HC 624 R? θ M J 625 Æ N HCZ 373 - 32. A composition according to claim 1 further comprising:(a) one or more compounds having acariddal, algicidal, avicidal, bacteriddal, fungicidal,5 herbiddal, Insectiddal, molluscicidal, nematicidal, rodenticidal, or virucidal properties; or (b) one or more compounds that are antifeedants, bird repellents, chemosterilants, herbidde safeners, Insect attractants, Insect repellents, mammal repellents, matîng disrupters, plant activators, plant growth regulators, or synerglsts; or (c) both (a) and (b).
- 33. A composition according to claim 1 wherein further comprising one or more compounds selededfrom: (3-ethoxypropyl)mercury bromide, 1,2-dichloropropane, 1,3-dichloropropene, 1methylcyclopropene, 1-naphthd, 2-(odylthio)ethanol, 2,3,5-tri-lodobenzoic add, 2,3,6-TBA, 2,3,6TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium, 2,3,6-TBA-sodium, 2,4,5-T,15 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl, 2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl,2.4.5- T-butotyt, 2,4,5-T-butyl, 2,4,5-T-lsobutyl, 2,4,5-T-lsodyl, 2,4,5-T-isopropyl, 2,4,5-T-methyl,2.4.5- T-pentyl, 2,4,5-T-sodium, 2,4,5-T-triethylammonlum, 2,4,5-T-trolamine, 2,4-D, 2.4-D-2butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropylI 2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl,3742,4-DB-dimethylammonium, 2,4-DB-lsoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl, 2,4D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonÎum, 2,4-D-dîolamlne, 2,4-Ddodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl, 2,4-D-heptyiammonlum, 2,4-D-lsobutyl, 2,4-DIsoctyl. 2,4-D-lsopropyl, 2,4-D-lsopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl, 2,4D-octyl, 2,4-D-pentyl, 2,4-D-potasslum, 2,4-D-propyl, 2,4-D-sodium, 2,4-D-tefuryl, 2,4-Dtetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonlum, 2,4-Dtrolamine, 2iP, 2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP, 4amlnopyridine, 4-CPA, 4-CPA-potassium, 4-CPA-sodium, 4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate, 8-phenylmercurioxyqulnoline, abamectin, abscisic add, ACC, acephate, acequlnocyl, acetamlprid, acethion, acetochlor, acetophos, acetoprole, adbenzolar, acibenzolar-S-methyt, adfluorfen, adfluorfen-methyt, adfluorfen-sodium, adonifen, acrep, acrinathrin, acroleln, acrylonîtrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor, alanycarb, albendazole, aldicarb, aldimorph, aldoxycarb, aldrin, allethrin, allidn, allidochlor, allosamidin, alloxydim, alloxydim-sodium, allyl alcohol, allyxycarb, alorac, a/pha-cypermethrin, a/pha-endosulfan, ametoctradin, ametridione, ametryn, amibuzin, amicarbazone, amlcarthlazol, amldithion, amidoflumet, amldosulfuron, aminocarb, aminocyclopyrachlor, amlnocyclopyrachlormethyt, aminocyclopyrachlor-potasslum, amlnopyralid, amlnopyralid-potasslum, amlnopyralid-tris(2hydroxypropy!)ammonium, amlprofos-methyl, amlprophos, amisulbrom, amiton, amiton oxalate, amitraz, amitrole, ammonium sulfamate, ammonium α-naphthaleneacetate, amobam, ampropylfos, anabastne, ancymldol, anilazine, anilofos, anisuron, anthraquinone, antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam, asulam-potassium, asulam-sodium, athidathlon, atraton, atrazine, aureofungin, aviglycine, aviglycine hydrochloride, azaconazole, azadirachtin, azafenidin, azamethiphos, azimsulfuron, azinphos-ethyt, azinphos-methyl, aziprotryne, azithlram, azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban, barium hexafluorosilicate, barium polysulfide, barthrin, BCPC, beflubutamld, benalaxyl, benalaxyl-M, benazolin, benazolindimethylammonium, benazolin-ethyl, benazolin-potassium, bencarbazone, bendothiaz, bendiocarb, benfluralin, benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos, benquinox, bensulfuron, bensulfuron-methyt, bensulide, bensultap, bentaluron, bentazone, bentazone-sodium, benthlavalicarb, benthiavalicarb-lsopropyl, benthiazole, bentranil, benzadox, benzadox-ammonium, benzalkonium chloride, benzamacril, benzamacril-lsobutyl, benzamorf, benzfendizone, benzipram, benzoblcyclon, benzofenap, benzofluor, benzohydroxamlc add, benzoximate, benzoylprop, benzoylprop-ethyl, benzthiazuron, benzyl benzoate, benzytadenine, berberine, berberine chloride, bata-cyfluthrin, fcefa-cypermethrin, bethoxazln, bicydopyrone, bifenazate, bifenox, bifenthrin, bifujunzhi, bilanafos, btlanafos-sodium, blnapacryl, bingqingxiao, bioallethrin, bioethanomethrin,375 blopermethrln, bioresmethrin, bîphenyl, bisazir, bismerthiazol, bispyribac, bispyribac-sodium, bistrifluron, bltertanol, bithionol, bixafen, blasticîdin-S, borax, Bordeaux mixture, boric add, boscalid, brassinolide, brassinolide-ethyl, brevicomin, brodifacoum, brofenvalerate, brofluthrinate, bromacil, bromadl-lithium, bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos, bromoacetamide, bromobonil, bromobutide, bromocyden, bromo-DDT, bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil, bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxynil octanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol, bucarpolate, bufencarb, buminafos, buplrimate, buprofezin, Burgundy mixture, busulfan, butacarb, butachlor, butafenacil, butamifos, butathiofos, butenachlor, butethrin, buthldazole, buthiobate, buthiuron, butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin, butroxydim, buturon, butylamlne, butylate, cacodylic add, cadusafos, cafenstrole, calcium arsenate, calcium chlorate, caldum cyanamide, calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor, captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam, carbendazim, carbendazim benzenesulfonate, carbendazim sulfite, carbetamlde, carbofuran, carbon disulfide, carbon tetrachloride, carbophenothion, carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carfentrazone-ethyl, carpropamld, caria p, cariap hydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure, Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone, chlomethoxyfen, chloralose, chloramben, chlorambenammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chloramine phosphores, chloramphenicol, chloraniformethan, chloranil, chloranocryl, chlorantraniliprole, chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside, chlorbenzuron, chlorblcyclen, chlorbromuron, chlorbufam, chlordane, chlordecone, chlordimeform, chlordimeform hydrochloride, chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac, chlorfenacammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole, chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide, chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren, chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chlorldazon, chlorlmuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequat chloride, chlomldlne, chlomitrofen, chlorobenzilate, chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethîuron, chloroneb, chlorophacinone, chlorophadnone-sodium, chloropicrin, chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron, chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim, chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, chlorthlamld, chlorthiophos, chlozolinate, choline chloride, chromafenozlde, cinerin I, cinerin II, cinerins, clnidon-ethyl, cinmethylin, cinosulfuron, ciobutide, dsanilide, ci s m et h ri n, clethodlm, climbazole, cîiodinate,376 clodinafop, dodinafop-propargyl, cloethocarb, clofencet, dofencet-potasslum, clofentezine, clofibric acid, clofop, clofop-isobutyl, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, clopyralidmethyl, dopyralid-olamine, clopyralid-potassium, clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet, doqulntocet-mexyl, cloransulam, cloransulam-methyl, closantel, clothianidin, clotrimazole, doxyfonac, doxyfonac-sodium, CMA, codlelure, colophonate, copper acetate, copper acetoarsenlte, copper arsenate, copper carbonate, baslc, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl, coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazlne, cresol, crimidine, crotamiton, crotoxyphos, crufomate, cryolite, cue-lure, cufraneb, cumyluron, cuprobam, cuprous oxide, curcumenol, cyanamlde, cyanatryn, cyanazine, cyanofenphos, cyanophos, cyanthoate, cyantraniiiprole, cyazofamid, cybutryne, cyclafuramid, cydanilide, cyclethrin, cycloate, cyclohexlmide, cycloprate, cycloprothrin, cyclosulfamuron, cydoxydim, cycluron, cyenopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalofop, cyhalofopbutyl, cyhalothrin, cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil, cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin, cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid, cyprosulfamide, cyromazlne, cythioate, daimuron, dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide, dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT, debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor, deltamethrin, demephion, demephion-O, demephionS, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyt, demeton-S-methylsulphon, desmedipham, desmetryn, d-fanshiluquebingjuzhl, diafenthiuron, dialifos, di-allate, diamldafos, diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succlnate, dicamba, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicambaIsopropylammonlum, dicamba-methyl, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone, dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl, dichlormate, dichlormid, dichlorophen, dichlorprop, dichlorprop-2-ethylhexyl, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P, dichlorprop-P-2ethylhexyl, dichlorprop-P-dimethylammonium, dichlorprop-potassium, dlchlorprop-sodium, dichlorvos, dichlozoline, dlclobutrazol, didocymet, didofop, didofop-methyl, diclomezine, diclomezine-sodium, dicloran, diclosulam, dicofol, dicoumarol, dicresyl, dicrotophos, dicydanil, dicydonon, dieldrin, dienochlor, diethamquat, diethamquat dichloride, diethatyl, diethatyl-ethyl, dîethofencarb, dietholate, diethyl pyrocarbonate, diethyltoluamide, difenacoum, difenoconazole, dlfenopenten, difenopenten-ethyl, difenoxuron, difenzoquat, difenzoquat metilsulfate, difethialone,377 diflovidazin, diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium, diflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin, dimefox, dimefuron, dimepiperate, dimetachlone, dimetan, dimethacarb, dimethachlor, dimethametryn, dimethenamid, dimethenamidP, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon, dimoxystrobin, dinex, dinex-diclexîne, dingjunezuo, diniconazole, diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinoseb acetate, dinosebammonium, dinoseb-diolamine, dinoseb-sodium, dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate, dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathïon, diphaclnone, diphaclnone-sodium, diphenamid, diphenyl sulfone, diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquat dibromide, disparlure, disul, disulfiram, disulfoton, disulsodium, ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron, d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodidn hydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure, doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone, edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate, EMPC, empenthrin, endosulfan, endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, endothion, endrin, enestroburin, EPN, epocholeone, epofenonane, epoxiconazole, eprinomectin, epronaz, EPTC, erbon, ergo cal ci ferai, erlujixiancaoan, esdépalléthrine, esfenvalerate, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethametsulfuron, ethametsulfuronmethyl, ethaprochlor, ethephon, ethidimuron, ethiofencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol, ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos, ethoxyfen, ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate, ethyl formate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylene dibromide, ethylene dichloride, ethylene oxide, ethylidn, ethylmercury 2,3dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etinofen, etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos, eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosuif, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole, fenbutatin oxide, fenchlorazole, fenchlorazole-ethyl, fenchlorphos, fenclorim, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitropan, fenitrothion, fenjuntong, fenobucarb, fenoprop, fenoprop-3-butoxypropyl, fenopropbutometyl, fenoprop-butotyl, fenoprop-butyl, fenoprop-isoctyl, fenoprop-methyl, fenoproppotassium, fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fenridazon, fenridazon-potassium, fenridazon378 propyl, fenson, fensulfothion, fenteracol, fenthiaprop, fenthlaprop-ethyl, fenthion, fenthlon-ethyl, fentin, fentin acetate, fentin chloride, fentin hydroxide, fentrazamide, fentrifanll, fenuron, fenuron TCA, fenvalerate, ferbam, ferimzone, ferrous sulfate, fipronîl, flamprop, flamprop-isopropyl, flamprop-M, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, flocoumafen, flometoquin, flonicamid, florasulam, fluacrypyrim, fluazifop, fluazifop-butyl, fluazifopmethyl, fluazifop-P, fluazifop-P-butyl, fluazinam, fluazolate, fluazuron, flubendiamide, flubenzlmine, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil, fluenetil, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxuron, flufenprox, flufenpyr, flufenpyr-ethyl, flufiprole, flumethrin, flumetover, flumetralin, flumetsulam, flumezin, flumidorac, flumiclorac-pentyl, flumioxazin, flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram, fluorbenside, fluoridamld, fluoroacetamide, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluoroimide, fluoromldine, fluoronitrofen, fluothluron, fluotrimazole, fluoxastrobin, flupoxam, flupropadl, flupropadine, flupropanate, flupropanate-sodium, flupyradifurone, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluqulnconazole, flurazole, flurenol, flurenol-butyl, flurenol-methyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurprimidol, flursulamid, flurtamone, flusilazole, flusulfamide, fluthiacet, fluthiacet-methyl, flutianil, flutolanil, flutriafol, fluvalinate, fluxapyroxad, fluxofenim, folpet, fomesafen, fomesafen-sodium, fonofos, foramsulfuron, forchlorfenuron, formaldéhyde, formetanate, formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosamine, fosamine-ammonium, fosetyl, fosetyl-aluminium, fosmethilan, fospirate, fosthlazate, fosthietan, frontalin, fuberidazole, fucaojing, fucaomi, funaihecaoling, fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr, furathiocarb, furcarbanll, furconazole, furconazole-cis, furethrin, furfural, furilazole, furmecydox, furophanate, furyloxyfen, gamma-cyhalothrin, gammaHCH, genît, gibberellic add, gibberellins, gliftor, glufoslnate, glufoslnate-ammonlum, glufosInate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime, glyphosate, glyphosatediammonium, glyphosate-dimethylammonium, glyphosate-lsopropylammonium, glyphosatemonoammonium, glyphosate-potassïum, glyphosate-sesqulsodium, glyphosate-trimeslum, glyphosine, gossyplure, grandiure, griseofulvin, guazatine, guazatine acétates, halacrinate, halfenprox, halofenozide, halosafen, halosulfuron, halosulfuron-methyl, haloxydine, haloxyfop, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-etotyl, haloxyfop-P-methyl, haloxyfopsodium, HCH, hemel, hempa, HEOD, heptachlor, heptenophos, heptopargil, heterophos, hexachloroacetone, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexaflurate, hexaiure, hexamide, hexazinone, hexylthiofos, hexythlazox, HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo, hydramethylnon, hydrargaphen, hydrated lime,379 hydrogen cyanide, hydroprene, hymexazol, hyquincarb, IAA, IB A, icaridin, imazalil, imazalil nitrate, imazalii sulfate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, Imazapyr, imazapyr-isopropylammonium, imazaquln, imazaquînammonlum, imazaquin-methyl, imazaquin-sodium, Imazethapyr, imazethapyr-ammonium, Imazosulfuron, Imibenconazoie, imicyafos, imidadoprid, Imidaciothiz, imlnoctadine, iminoctadine triacetate, Imlnoctadine trialbesilate, Imiprothrin, inabenfide, indanofan, indaziflam, Indoxacarb, Inezin, lodobonil, iodocarb, iodomethane, lodosulfuron, lodosulfuron-methyl, lodosulfuron-methylsodlum, lofensuifuron, iofensulfuron-sodium, ioxynii, loxynil octanoate, ioxynil-iithium, loxynilsodium, ipazîne, Ipconazoie, ipfencarbazone, Iprobenfos, iprodione, Iprovalicarb, iprymidam, ipsdienol, Ipsenol, IPSP, Isamidofos, Isazofos, isobenzan, Isocarbamid, Isocarbophos, isocil, Isodrin, isofenphos, isofenphos-methyl, isolan, Isomethiozln, isonoruron, Isopolinate, isoprocarb, Isopropalin, Isoprothiolane, lsoproturon, Isopyrazam, Isopyrimol, isothioate, Isotianil, Isouron, Isovaledîone, Isoxaben, Isoxachlortole, Isoxadifen, isoxadifen-ethyl, isoxaflutole, Isoxapyrifop, isoxathion, ivermectln, Izopamfos, japonllure, japothrins, jasmolin I, jasmoiin II, jasmonlc add, Jiahuangchongzong, jiajizengxiaoiin, jiaxiangjunzhi, Jiecaowan, jiecaoxi, Jodfenphos, juvénile hormone I, Juvénile hormone II, juvénile hormone III, kadethrin, karbutilate, karetazan, karetazanpotassium, kasugamycin, kasugamydn hydrochloride, kejunlin, keievan, ketospiradox, ketosplradox-potasslum, kinetin, klnoprene, kresoxlm-methyl, kulcaoxl, lactofen, lambdacyhalothrin, latilure, lead arsenate, lenacil, lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure, looplure, lufenuron, Ivdingjunzhi, Ivxiancaoiin, lythidathion, MAA, malathion, maleic hydrazide, malonoben, maltodextrin, ΜΑΜΑ, mancopper, mancozeb, mandipropamid, maneb, matrine, mazidox, MCPA, MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPAdimethylammonium, MCPA-diolamlne, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPAisopropyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thloethyl, MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenii, mecarbam, mecarblnzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl, mecoprop-P-dimethylammonlum, mecoprop-P-lsobutyl, mecoproppotassium, mecoprop-P-potasslum, mecoprop-sodium, mecoprop-trolamlne, medimeform, medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr, mefenpyr-diethyl, mefluldide, mefluidide-diolamlne, mefluidide-potasslum, megatomolc acid, menazon, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride, meplquat pentaborate, mepronil, meptyldinocap, mercuric chloride, mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron, mesosuifuron-methyl, mesotrione, mesulfen, mesulfenfos,380 metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop, metamitron, metam-potasslum, metam-sodium, metazachlor, metazosulfuron, metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron, methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole, methfuroxam, methldathîon, methlobencarb,5 methlocarb, methiopyrisulfuron, methlotepa, methiozolin, methiuron, methocrotophos, methometon, methomyl, methoprene, methoprotryne, methoquin-butyl, methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methyl apholate, methyl bromlde, methyl eugenol, methyl lodide, methyl isothiocyanate, methylacetophos, methylchloroform, methyldymron, methylene chloride, methyl mercury benzoate, methylmercury dicyandiamide, methylmercury10 pentachlorophenoxide, methylneodecanamide, metiram, metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb, metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone, metribuzîn, metsulfovax, metsulfuron, metsulfuron-methyl, mevlnphos, mexacarbate, mleshuan, milbemectin, milbemycin oxlme, mllneb, mipafox, mirex, MNAF, moguchun, mollnate, molosultap, monalide, monlsoüron, monochloroacetic acid, monocrotophos, monolinuron,15 monosulfuron, monosulfuron-ester, monuron, monuron TCA, morfamquat, morfamquat dichloride, moroxydine, moroxydine hydrochloride, morphothlon, morzid, moxidectin, MSMA, muscalure, myclobutanil, myclozolin, N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos, naled, naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthoxyacetic acids, naproanilide, napropamide, naptalam, naptalam-sodium, natamycin, neburon, niclosamide, niclosamide-olamine, 20 nicosulfuron, nicotine, nlfluridide, nipyraclofen, nitenpyram, nithiazlne, nitralin, nitrapyrin, nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrothal-isopropyl, norbormlde, norflurazon, nomicotine, noruron, novaluron, novîflumuron, nuarimol, OCH, octachlorodipropyl ether, octhillnone, ofurace, omethoate, orbencarb, orfralure, ortho-dlchlorobenzene, orthosulfamuron, oryctalure, orysastrobln, oryzalin, osthol, ostramone, oxabetrinil, oxadiargyl. oxadiazon, oxadixyl, oxamate, oxamyl,25 oxapyrazon, oxapyrazon-dimolamlne, oxapyrazon-sodium, oxasulfuron, oxaziclomefone, oxlnecopper, oxolinlc acid, oxpoconazole, oxpoconazole fumarate, oxycarboxln, oxydemeton-methyl, oxydeprofos, oxydlsulfoton, oxyfluorfen, oxymatrine, oxytetracycline, oxytetracycllne hydrochloride, paclobutrazol, palchongding, para-dichlorobenzene, parafluron, paraquat, paraquat dichloride, paraquat dimetilsulfate, parathion, parathion-methyl, parinol, pebulate, pefurazoate, pelargonic30 acid, penconazole, pencycuron, pendlmethalin, penflufen, penfluron, penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, pentmethrin, pentoxazone, perfluidone, permethrin, pethoxamid, phenamacril, phenazine oxide, phenisopham, phenkapton, phenmedipham, phenmedlpham-ethyl, phenobenzuron, phenothrin, phenproxlde, phenthoate, phenylmercuriurea, phenylmercury acetate, phenylmercury chloride, phenylmercury dérivative of381 pyrocatechol, phenylmercury nitrate, phenylmercury salicylate, phorate, phosacetim, phosalone, phosdiphen, phosfolan, phosfolan-methyl, phosglycin, phosmet, phosnlchlor, phosphamldon, phosphine, phosphocarb, phosphorus, phostin, phoxim, phoxim-methyl, phthalide, pi cio ram, pic!oram-2-ethylhexyl, pldoram-isoctyl, pidoram-methyl, picloram-olamine, pidoram-potassium, picloram-triethylammonium, pidoram-tris(2-hydroxypropyi)ammonium, picolinafen, picoxystrobïn, pindone, pindone-sodium, plnoxaden, plperalin, piperonyl butoxlde, piperonyl cydonene, piperophos, plproctanyl, piproctanyl bromide, piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyi, pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim, polyoxorimzinc, polythialan, potassium arsenite, potassium azide, potassium cyanate, potassium gibberellate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, potassium anaphthaleneacetate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, pretilachlor, primidophos, primisulfuron, primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese, proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol, profluralin, profluthrin, profoxydim, proglinazîne, proglinazine-ethyl, prohexadione, prohexadione-caldum, prohydrojasmon, promacyl, promecarb, prometon, prometryn, promurit, propachlor, propamidine, propamidine dihydrochloride, propamocarb, propamocarb hydrochloride, propanil, propaphos, propaqulzafop, propargite, proparthrin, propazine, propetamphos, propham, propiconazole, propineb, propisochlor, propoxur, propoxycarbazone, propoxycarbazone-sodium, propyl Isome, propyrisulfuron, propyzamide, proquinazid, prosuier, prosulfalin, prosulfocarb, prosulfuron, prothldathion, prothiocarb, prothiocarb hydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute, proxan, proxan-sodium, prynachlor, pydanon, pymetrozine, pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufen-ethyl, pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobln, pyrasulfotole, pyrazolynate, pyrazophos, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrin I, pyrethrîn II, pyrethrîns, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb, pyribenzoxim, pyributïcarb, pyriclor, pyridaben, pyridafol, pyridalyl, pyridaphenthion, pyridate, pyridinltril, pyrifenox, pyrifluqulnazon, pyriftalid, pyrimethanil, pyrimldifen, pyriminobac, pyrimlnobac-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole, pyripropanol, pyriproxyfen, pyrithiobac, pyrithlobac-sodium, pyrolan, pyroquilon, pyroxasulfone, pyroxsulam, pyroxychior, pyroxyfur, quassia, quinacetol, quinacetol sulfate, quinalphos, quinalphos-methyl, quinazamid, quinclorac, quinconazole, quinmerac, quinodamine, quinonamld, quinothion, quinoxyfen, qulntiofos, quintozene, quizalofop, quizalofop-ethyl, quizalofop-P, quizaiofop-P-ethyl, quizalofop-P-tefuryl, quwenzhl, quylngding, rabenzazole, rafoxanide, rebemïde, resmethrin, rhodethanil, rhodojaponln-lll, ribavirin, rimsulfuron, rotenone, ryania, saflufenadl, saijunmao, saisentong, salicylanilide, sanguinarine, santonin, schradan,382 sciiliroside, sebuthylazine, secbumeton, sedaxane, selamectin, semiamitraz, semiamitraz chloride, sesamex, sesamolin, sethoxydim, shuangjiaancaolin, siduron, siglure, silafluofen, sïlatrane, sïlica gel, silthiofam, simazlne, simeconazole, simelon, simetryn, sintofen, SMA, S-metolachlor, sodium arsenlte, sodium azide, sodium chlorate, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium orthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide, sodium thiocyanate, sodium a-naphthaleneacetate, sophamide, spinetoram, spinosad, spirodiclofen, spiromeslfen, spirotetramat, spiroxamine, streptomycin, streptomycin sesquisulfate, strychnine, sulcatol, sulcofuron, sulcofuron-sodium, sulcotrione, sulfatlate, sulfentrazone, sulfiram, sulfluramld, sulfometuron, sulfometuron-methyl, suifosulfuron, sulfotep, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin, sulprofos, sultropen, swep, teu-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium, TCA-calcIum, TCA-ethadyl, TCA-magnesium, TCA-sodium, TDÈ, tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron, tecloftalam, tecnazene, te coram, teflubenzuron, tefluthrin, tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydim, terallethrin, terbadl, terbucarb, terbuchlor, terbufos, terbumeton, terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane, tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin, tetramethylfluthrin, tetramine, tetranactin, tetrasul, thallium sulfate, thenyichlor, theta-cypermethrin, thlabendazole, thiacloprid, thiadifluor, thiamethoxam, thlapronil, thiazafluron, thlazopyr, thicrofos, thicyofen, thidîazîmin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thlfensulfuron-methyl, thlfluzamlde, thiobencarb, thiocarboxlme, thiochlorfenphim, thlocyclam, thiocyclam hydrochloride, thlocyclam oxalate, thiodiazole-copper, thiodicarb, thiofanox, thlofluoximate, thlohempa, thiomersal, thiometon, thionazin, thlophanate, thlophanate-methyl, thioqulnox, thiosemicarbazide, thiosultap, thiosultap-diammonium, thlosultap-disodium, thlosultapmonosodium, thiotepa, thiram, thuringiensln, tladinil, tlaojiean, tiocarbazil, tioclorim, tioxymid, tirpate, tolclofos-methyl, tolfenpyrad, tolylfluanld, tolylmercury acetate, topramezone, tralkoxydim, tralocythrin, tralomethrin, tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol, triadîmefon, triadimenol, triafamone, tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulfuron, triazamate, triazbutil, triazîflam, triazophos, triazoxide, tribenuron, tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamlde, trichlorfon, trichlormetaphos-3, trichloronat, triclopyr, triclopyr-butotyl, trlclopyr-ethyl, triclopyrtriethylammonium, tricyclazole, tridemorph, tridiphane, trietazlne, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron, trifloxysulfuron-sodium, triflumizole, triflumuron, trifluralîn, triflusulfuron, triflusulfuron-methyl, trifop, trifop-methyl, trifopsîme, triforine, trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, trinexapac-ethyl, triprene, trlproplndan, triptolide, tritac, triticonazole, tritosulfuron, trunc-call, uniconazole, unlconazole-P,383 urbaclde, uredepa, valerate, validamycin, valifenalate, valone, vamidothion, vangard, vaniliprole, vemolate, vinclozolin, warfarin, warfarin-potassium, warfarin-sodium, xiaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols, xylylcarb, yishijing, zarilamid, zeatin, zengxiaoan, zetacypermethrin, zinc naphthenate, zinc phosphlde, zinc thiazole, zîneb, ziram, zolaprofos, zoxamide, zuomihuanglong, α-chlorohydrin, a-ecdysone, a-multistrîatin, and α-naphthaleneacetic acid.
- 34. A composition according to claim 1 further comprising an agriculturally acceptable carrier.
- 35. A composition according to claim 1 wherein said molécule is In the form of a pesticidally acceptable acid addition sait.
- 36. A composition according to claim 1 wherein said molécule is In the form of a sait dérivative.
- 37. A composition according to claim 1 wherein said molécule Is In the form a hydrate.
- 38. A composition according to claim 1 wherein said molécule is a resolved stereoisomer.
- 39. A composition according to ciaim 1 wherein said molécule is in the form a crystal polymorph.
- 40. A composition according to claim 1 wherein said molécule has a 2H in place of 1H.
- 41. A composition according to claim 1 wherein said molécule has a 14C in place of a 12C.
- 42. A composition according to claim 1 further comprising a biopestidde.
- 43. A composition according to claim 1 further comprising one or more of the following compounds:(a) 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]deo-3-en-2-one;384 (b) 3-(4’-chloro-2,4-dimethyl[1,1 '-bïphenyl]-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4,5Jdec-3en-2-one;(c) 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5H)-furanone;(d) 4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-furanone;(e) 3-chloro-N2-[(1S)-1-methyl-2-(methylsuifonyl)ethyl]-N1-[2-methyl-4-[1,2,2,ètetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide;(f) 2-cyano-N-ethyt-4-fluoro-3-methoxy-benenesulfonamide;(g) 2-cyano-N-ethyl-3-methoxy-benzenesulfonamïde;(h) 2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonarnide;(i) 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide;Q) 2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide;(k) 2-cyano-N-ethyt-6-fluoro-3-rnethoxy-N-methy1-benzenesulfonamide;(l) 2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfon-amide;(m) 3-(difluoromethyl)-N-[2-(3,3-dÎmethylbutyl)phenyl]-1-methyl-1H-pyrazole-4carboxamide;(n) N-ethyl-212-dimelhylproplonamide-2-(2,6-dichloro-a,a,a-trifluoro-p-tolyl) hydrazone;385 (o) /V-ethyl-2,2-dichloro-1-methylcycloprOpane-carboxamide-2-(2,6-dichIoro-a,a,atrifluoro-p-toîyl) hydrazone nicotine;(p) 0-{(E-)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]) S-methyl thiocarbonate;(q) (E)-N1-[(2-chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;(r) 1 -(6-chloropyridin-3-ylmethyl)-7-methyl-8-nÎtro-1,2,3,5,6,7-hexahydro-imidazo[1 ,2a]pyridin-5-ol;(s) 4-[4-chlorophenyl-(2-butylÎdÎne-hydrazono)methyl)]phenyl mesylate; and (t) N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloroa/pha,a/pha,a/p/ja-trifluoro-p-tolyl)hydrazone.
- 44. A composition according to claim 1 further comprising a compound having one or more of the following modes of action: acetylcholînesterase inhibltor; sodium channel modulator; chitin biosynthesis inhibitor; GABA and glutamate-gated chloride channel antagonist; GABA and glutamate-gated chloride channel agonist; acétylcholine receptor agonist; acétylcholine receptor antagonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinic acétylcholine receptor; Midgut membrane disrupter; oxidative phosphorylation disrupter, and ryanodine receptor (RyRs).
- 45. A composition according to claim 1 further comprising a seed.
- 46. A composition according to claim 1 further comprising a seed that has been genetically modified to express one or more specialized traits.
- 47. A composition according to claim 1 wherein said composition Is encapsulated Inside, or placed on the surface of, a capsule.386
- 48. A composition according to daim 1 wherein said composition Is encapsulated inside, or placed on the surface of, a capsule, wherein said capsule has a diameter of about 100-900 nanometers or about 10-900 microns.
- 49. A process comprising applying a composition according to daim 1, to an area to control a pest, In an amount sufficient to control such pest.
- 50. A process according to daim 49 wherein said pest Is seleded from beetles, earwigs, cockroaches, flies. aphlds, scales, whîteflies, ieafhoppers, ants, wasps, termites, moths, butterflies, lice, grasshoppers, locusts, crickets, fleas, thrips, bristletails, mites, ticks, nematodes, and symphylans.
- 51. A process according to daim 49 wherein said pest is from the Phyla Nematoda or Arthropode.
- 52. A process according to daim 49 wherein said pest Is from the Subphyla Chelicerata, Myriapoda, or Hexapoda,
- 53. A process according to daim 49 wherein said pest Is from the Class of Arachnida, Symphyla, or Inseda.
- 54. A process according to daim 49 wherein said pest is from the Order Anoplura, Order Coleoptera, Order Dermaptera, Order Blattaria, Order Diptera, Order Hemlptera, Order Hymenoptera, Order Isoptera, Order Lepidoptera, Order Mallophaga, Order Orthoptera, Order Siphonaptera, Order Thysanoptera, Order Thysanura, Order Acarina, or Order Symphyla.
- 55. A process according to daim 49 wherein said pest is MYZUPE or BEMITA.
- 56. A process according to claim 49 wherein said amount Is from about 0.01 grams per hedare to about 5000 grams per hedare.387
- 57. A process according to claim 49 wherein said amount Is from about 0.1 grams per hectare to about 500 grams per hectare.
- 58. A process according to claim 49 wherein said amount 1s from about 1 gram per hectare to about 50 grams per hectare.
- 59. A process according to claim 49 wherein said area Is an area where apples, corn, cotton, soybeans, canola, wheat, rice, sorghum, barley, oats, potatoes, oranges, alfalfa, lettuce, strawberries, tomatoes, peppers, crucifers, pears, tobacco, almonds, sugar beets, or beans, are growing, or the seeds thereof are going to be planted.
- 60. A process according to claim 49 further comprising applying said composition to a genetically modified plant that has been geneticaliy modified to express one or more specialized traits.
- 61. A process according to daim 49 where said composition further comprise ammonium sulfate.
- 62. A process comprising applying a composition according to claim 1 to a plant to enhance the plant’s health, yield, vigor, quality, or tolérance, at a time when pest activity Is low.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US61/551,585 | 2011-10-26 |
Publications (1)
Publication Number | Publication Date |
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OA16898A true OA16898A (en) | 2016-01-18 |
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