JP5487123B2 - 農薬 - Google Patents
農薬 Download PDFInfo
- Publication number
- JP5487123B2 JP5487123B2 JP2010549765A JP2010549765A JP5487123B2 JP 5487123 B2 JP5487123 B2 JP 5487123B2 JP 2010549765 A JP2010549765 A JP 2010549765A JP 2010549765 A JP2010549765 A JP 2010549765A JP 5487123 B2 JP5487123 B2 JP 5487123B2
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- JP
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- Prior art keywords
- alkyl
- spp
- compound
- haloalkyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000575 pesticide Substances 0.000 title claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 98
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 241000607479 Yersinia pestis Species 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 37
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 30
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 241000244206 Nematoda Species 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 241000238421 Arthropoda Species 0.000 claims description 2
- 229920002101 Chitin Polymers 0.000 claims description 2
- 229940127437 Chloride Channel Antagonists Drugs 0.000 claims description 2
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 2
- 108010052164 Sodium Channels Proteins 0.000 claims description 2
- 102000018674 Sodium Channels Human genes 0.000 claims description 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims description 2
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003467 chloride channel stimulating agent Substances 0.000 claims description 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 2
- 229930195712 glutamate Natural products 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 230000010627 oxidative phosphorylation Effects 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 229940121819 ATPase inhibitor Drugs 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- -1 heptenyl Chemical group 0.000 description 211
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 93
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 40
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 36
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 35
- 125000003545 alkoxy group Chemical group 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 27
- 238000009472 formulation Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 description 23
- 125000000000 cycloalkoxy group Chemical group 0.000 description 23
- 241000254173 Coleoptera Species 0.000 description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
- 125000003302 alkenyloxy group Chemical group 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 22
- 125000005366 cycloalkylthio group Chemical group 0.000 description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 21
- 125000005133 alkynyloxy group Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 20
- 125000005108 alkenylthio group Chemical group 0.000 description 20
- 125000004414 alkyl thio group Chemical group 0.000 description 20
- 125000005109 alkynylthio group Chemical group 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 241000254171 Curculionidae Species 0.000 description 19
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 18
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 241001124076 Aphididae Species 0.000 description 16
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
- 241000256602 Isoptera Species 0.000 description 16
- 239000004094 surface-active agent Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000007796 conventional method Methods 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 241000894007 species Species 0.000 description 15
- 241000258937 Hemiptera Species 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 12
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000012267 brine Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 241000255925 Diptera Species 0.000 description 9
- 235000013305 food Nutrition 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241001674048 Phthiraptera Species 0.000 description 7
- 239000003905 agrochemical Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000257303 Hymenoptera Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VGLQBNXOFWGYIU-UHFFFAOYSA-N N=S(=O)C#N Chemical compound N=S(=O)C#N VGLQBNXOFWGYIU-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- SDEFOCWEOKCRJR-UHFFFAOYSA-N imino-methyl-oxo-[1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-$l^{6}-sulfane Chemical compound CS(=O)(=N)C(C)C1=CC=C(C(F)(F)F)N=C1 SDEFOCWEOKCRJR-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 241001674044 Blattodea Species 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000003880 polar aprotic solvent Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 125000005555 sulfoximide group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 4
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- XQOSHWPKADMSKX-UHFFFAOYSA-N C(#N)N=[SH2]=O Chemical compound C(#N)N=[SH2]=O XQOSHWPKADMSKX-UHFFFAOYSA-N 0.000 description 4
- 241000723377 Coffea Species 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 241000353522 Earias insulana Species 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(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-NSHGMRRFSA-N 0.000 description 2
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
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- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ZLVSYODPTJZFMK-UHFFFAOYSA-M sodium 4-hydroxybenzoate Chemical compound [Na+].OC1=CC=C(C([O-])=O)C=C1 ZLVSYODPTJZFMK-UHFFFAOYSA-M 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- 235000013024 sodium fluoride Nutrition 0.000 description 1
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- 239000004328 sodium tetraborate Substances 0.000 description 1
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- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
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- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 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 description 1
- CTPKSRZFJSJGML-UHFFFAOYSA-N sulfiram Chemical compound CCN(CC)C(=S)SC(=S)N(CC)CC CTPKSRZFJSJGML-UHFFFAOYSA-N 0.000 description 1
- 229950008316 sulfiram Drugs 0.000 description 1
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- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
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- 235000013616 tea Nutrition 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AUZONCFQVSMFAP-UHFFFAOYSA-N tetraethylthiuram disulfide Natural products CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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Description
本出願は、2008年3月3日出願の米国特許仮出願第61/067,874号の利益を主張する。
置換基について示す例は、(ハロを除き)非網羅的であり、本明細書において開示される本発明を限定すると解釈されてはならない。
[式中、
(a)R1は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(b)R2は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR2とR5はまた、4、5又は6員環を形成してもよく;
(c)R3は、F、Cl、Br、I、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル、C(=O)C1〜C6アルキル、C(=O)C1〜C6アリール又はC0〜C8アルキル−C(=O)OR8であり、その各々(H、F、Cl、Br、Iを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール(前記アリールは、F、Cl、Br、I又はC1〜C8アルコキシから選択される1又はそれ以上の置換基で置換されてもよい)、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(d)R4は、F、Cl、Br、I、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル、C(=O)C1〜C6アルキル、C(=O)C1〜C6アリール又はC0〜C8アルキル−C(=O)OR8であり、その各々(H、F、Cl、Br、Iを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール(前記アリールは、F、Cl、Br、I又はC1〜C8アルコキシから選択される1又はそれ以上の置換基で置換されてもよい)、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(e)R5は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C3〜C8シクロアルキル、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR2とR5はまた、4、5又は6員環を形成してもよく、R5とR6はまた、3、4、5又は6員環を形成してもよく;
(f)R6は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C3〜C8シクロアルキル、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR2とR5はまた、4、5又は6員環を形成してもよく、R5とR6はまた、3、4、5又は6員環を形成してもよく;
(g)nは0〜4であり;
(h)Xは、NR8、O又はSであり;
(i)Jは、N又はCR7であり;
(j)R7は、H、F、Cl、Br、I、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(H、F、Cl、Br、Iを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(k)R8は、H、OH、OC(=O)C1〜C6アルキル、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C3〜C8シクロアルキル、C3〜C8ハロシクロアルキル、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール(前記アリールは、F、Cl、Br、I又はC1〜C8アルコキシから選択される1又はそれ以上の置換基で置換されてもよい)、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(l)R9は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR9とR10はまた、4、5又は6員環を形成してもよく;並びに
(m)R10は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR9とR10はまた、4、5又は6員環を形成してもよい]
を有する。
(a)R1は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(b)R2は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR2とR5はまた、4、5又は6員環を形成してもよく;
(c)R3は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(d)R4は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(e)R5は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR2とR5はまた、4、5又は6員環を形成してもよく、R5とR6はまた、3、4、5又は6員環を形成してもよく;
(f)R6は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、H、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR5とR6はまた、3、4、5又は6員環を形成してもよく;
(g)nは0〜4であり;
(h)Xは、NR8、O又はSであり;
(i)Jは、N又はCR7であり;
(j)R7は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ、ヘテロシクリル又はC0〜C8アルキル−C(=O)OR8であり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル、NR9R10及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(k)R8は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく;
(l)R9は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR9とR10はまた、4、5又は6員環を形成してもよく;並びに
(m)R10は、C2〜C8アルケニル、C2〜C8アルケニルオキシ、C2〜C8アルケニルチオ、C1〜C8アルコキシ、C1〜C8アルキル、C1〜C8アルキルチオ、C2〜C8アルキニル、C2〜C8アルキニルオキシ、C2〜C8アルキニルチオ、アリール、C3〜C8シクロアルケニル、C3〜C8シクロアルケニルオキシ、C3〜C8シクロアルケニルチオ、C3〜C8シクロアルキル、C3〜C8シクロアルコキシ、C3〜C8シクロアルキルチオ又はヘテロシクリルであり、その各々は、独立して以下の置換基:F、Cl、Br、I、CN、NO2、C1〜C6アルキル、C2〜C6アルケニル、C2〜C6アルキニル、C1〜C6アルコキシ、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C6ハロアルキルチオ、S(=O)n1C1〜C6アルキル(式中、n1=0〜2)、S(=O)n1C1〜C6ハロアルキル(式中、n1=0〜2)、OSO2C1〜C6ハロアルキル、C(=O)OC1〜C6アルキル、C(=O)C1〜C6アルキル、C(=O)C1〜C6ハロアルキル、アリール、C1〜C6ヒドロキシアルキル及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR9とR10はまた、4、5又は6員環を形成してもよい。
スキームA
スキームB
スキームC
スキームD
スキームE
スキームF
スキームG
略語のリスト
テトラヒドロフラン THF
N,N−ジメチルホルムアミド DMF
エレクトロスプレーイオン化質量分析法 ESIMS
相対湿度 RH
N−[(4−クロロフェニル)(メチル)オキシド−λ4−スルファニリデン]−N’−[4−(トリフルオロメチル)フェニル]尿素(1)の調製
1−クロロ−4−(メチルスルホンイミドイル)ベンゼン(0.37g、1.9mmol)を室温でCH2Cl2(16mL)に溶解した。この溶液に、発泡を生じさせる鉱油中の60%水素化ナトリウム(68mg、1.7mmol)を添加した。発泡がおさまったとき、4−トリフルオロメチルフェニルイソシアネート(0.42g、1.9mmol)を添加し、混合物を室温で2時間撹拌した。その後ブライン(10mL)で反応をクエンチングし、混合物を酢酸エチル(3×10mL)で抽出した。有機抽出物を合わせ、乾燥して(MgSO4)、ろ過し、減圧下で濃縮して、N−[(4−クロロフェニル)(メチル)オキシド−λ4−スルファニリデン]−N’−[4−(トリフルオロメチル)フェニル]尿素(1)を白色固体として得た(0.466g、76%):融点131〜134℃;1H NMR(300 MHz,CDCl3)δ7.95(d,J=8.7 Hz,2H),7.59(d,J=8.4 Hz,2H),7.52(s,4H),3.39(s,3H);ESIMS m/z 376([M]+).
N−[(4−クロロフェニル)(メチル)オキシド−λ4−スルファニリデン]−N’−[4−クロロ−3−(トリフルオロメチル)フェニル]尿素(2)の調製
N−[(4−クロロフェニル)(メチル)オキシド−λ4−スルファニリデン]−N’−[4−クロロ−3−(トリフルオロメチル)フェニル]尿素(2)を、実施例1で述べた手順に従って1−クロロ−4−(メチルスルホンイミドイル)ベンゼンから合成した。化合物を無色のオイルとして単離した(0.319g、54%):1H NMR(300 MHz,CDCl3)δ7.95(d,J=9.0 Hz,2H),7.77(br s,1H),7.59(d,J=8.7 Hz,2H),7.54(br s,1H),7.36(d,J=8.7 Hz,1H),3.36(s,3H);ESIMS m/z 410([M]+).
N−(クロロアセチル)−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)尿素(3)の調製
工程A.N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)尿素の調製
アセトニトリル(500mL)中のメチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデンシアナミド(100g、0.36mol)の強く撹拌した溶液に、温度を40℃未満に維持する速度で濃硫酸(25mL)を滴下した。(最初は少し外部冷却が必要であった。)添加が完了すれば、反応混合物(この時点では混濁、多少の分離したオイルを伴う)を、出発物質が消費されるまで周囲温度でさらに1時間撹拌した。その後混合物を5℃に冷却し、溶液がpH紙で中性になるまで50%NaOHを滴下した(発熱性)。生じた固体をろ過し、ろ液を分液漏斗に移した。層を分離し、有機層をブラインで洗浄して、乾燥し(MgSO4)、ろ過して、減圧下で濃縮し、N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)尿素を白色固体として得た(99.4g、93%):ESIMS m/z 296([M+H]+)。
無水ベンゼン(50mL)中のN−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)尿素(2.0g、6.78mmol)及び塩化クロロアセチル(0.92g、8.14mmol)の懸濁液をN2下で2時間加熱還流した。反応混合物を氷水浴で外部から冷却し、ヘキサン(100mL)を添加して生成物を沈殿させた。反応混合物をさらに15分間撹拌し、固体を吸引ろ過によって収集して、エーテルで洗浄し、N−(クロロアセチル)−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)尿素(3)を白色固体として得た(1.37g、54%):融点178〜179℃;1H NMR(300MHz,DMSO−d6)δ(2つのジアステレオマーの1:1混合物)10.4(s,NH),8.9(m,1H),8.3(m,1H),8.0(m,1H),5.1(q,1H),4.5(s,2H),3.4(s,3H),1.8(d,3H);ESIMS m/z 372([M+H]+).
N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−N’−ピリジン−3−イルチオ尿素(4)の調製
工程A.5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジンの調製
0℃のCH2Cl2(300mL)中のメチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデンシアナミド(5g、18mmol)の撹拌溶液に無水トリフルオロ酢酸(7.5mL、54mmol)を添加した。出発物質が完全に消費されるまで混合物を25℃で反応させた。反応混合物を減圧下で濃縮し、メタノール(125mL)に溶解して、炭酸カリウム(12.5g、90mmol)で処理した。出発物質が消費されるまで混合物を25℃で撹拌した。粗反応混合物をろ過し、濃縮して、クロマトグラフィー(アセトン−ヘキサン)によって精製し、5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジンを白色固体として得た(3.5g、77%):ESIMS m/z 253[M+H]+)。
磁気撹拌機を備えた50mL丸底フラスコにおいて、5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジン(0.200g、0.793mmol)を25℃でTHF(4.17mL)及びDMF(0.83mL)に溶解した。次に、3−イソチオシアナトピリジン(0.132mL、1.11mmol)を反応フラスコに添加した。添加後、反応物を80℃に12時間加温した。反応の完了時に、混合物を酢酸エチルとブラインで希釈した。層を分離し、水層を酢酸エチルで抽出した。有機抽出物を合わせ、ブラインで洗浄して、乾燥し(Na2SO4)、ろ過して、減圧下で濃縮した。粗物質を、アセトニトリル−水混合物で溶出する逆相HPLCを用いて精製し、N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−N’−ピリジン−3−イルチオ尿素(4)を白色固体として得た(0.191g、62%):融点92〜94℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.82&8.76(s,1H),8.5(m,2H),8.07(m,2H),7.74(m,1H),7.30(m,1H),5.89&5.61(m,1H),3.55&3.35(s,3H),1.94&1.85(m,3H);ESIMS m/z 389([M+H]+).
N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)チオ尿素(22)の調製
化合物9(0.100g、0.187mmol)を、攪拌しながら25℃で20%ピペリジン/DMF(2mL)に溶解した。反応の完了時に、混合物を減圧下で濃縮した。粗物質を、アセトニトリル−水混合物で溶出する逆相HPLCを用いて精製し、N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)チオ尿素(22)をオフホワイト色の固体として得た(0.043g、74%):融点145〜147℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.86(s,1H),8.10(m,1H),7.76(m,1H),6.09&5.94(m,1H),3.52&3.24(s,3H),1.93&1.83(d,J=7.3Hz,3H);ESIMS m/z 312([M+H]+).
N,N−ジメチル−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)チオ尿素(23)の調製
工程A.N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−1H−イミダゾール−1−カルボチオアミドの調製
5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジン(2.1g、8.3mmol)を室温でアセトニトリル(17mL)に溶解した。この混合物にチオカルボニルジイミダゾール(3g、17mmol)を一度に添加した。混合物を80℃に12時間加熱した。次に混合物をろ過してすべての固体を除去し、ろ液を減圧下で濃縮した。残留物をCH2Cl2に再溶解して、ブラインで洗浄した。有機抽出物を合わせ、乾燥して(Na2SO4)、ろ過し、減圧下で濃縮して、N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−1H−イミダゾール−1−カルボチオアミドを褐色のオイルとして得て(2.78g、93%)、それをさらに精製することなく使用した:ESIMS m/z 363[M+H]+)。
N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−1H−イミダゾール−1−カルボチオアミド(0.088g、0.243mmol)を室温で撹拌しながらアセトニトリル(0.486mL)に溶解した。次に混合物を氷浴で冷却した。この冷却した溶液に水中の40%ジメチルアミン(0.031mL、0.243mmol)を添加した。反応が完了すれば、いかなる固体も混合物からろ過して除去し、ろ液を減圧下で濃縮した。残存する粗物質を酢酸エチルに再溶解し、1N HCl及びブラインで洗浄した。次に有機層を乾燥し(Na2SO4)、ろ過して、減圧下で濃縮し、N,N−ジメチル−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)チオ尿素(23)を黄色オイルとして得た(0.044g、54%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.83(s,1H),8.08(m,1H),7.74(m,1H),5.97&5.73(m,1H),3.52&3.41(s,3H),3.34&3.25(s,3H),3.26&3.03(s,3H),1.92&1.81(d,J=7.3Hz,3H);ESIMS m/z 340([M+H]+).
9H−フルオレン−9−イルメチル[(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)アミノ]カルボノチオイルカルバメート(28)の調製
9H−フルオレン−9−イルメチル[(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)アミノ]カルボノチオイルカルバメート(28)を、実施例4で述べた手順に従って対応するスルホキシミドから合成した。化合物を明黄色の泡として単離した(14.6g、100%):融点92〜97℃;1H NMR(300 MHz,DMSO−d6)δ11.18(s,1H),8.93(s,1H),8.29(d,J=7.9 Hz,1H),7.98(d,J=8.2 Hz,1H),7.91(d,J=7.6 Hz,2H),7.83(d,J=7.2 Hz,2H),7.43(t,J=7.2 Hz,2H),7.34(dt,J=1.3,6.3 Hz,2H),5.21(d,J=2.3 Hz,2H),4.33−4.24(m,3H),3.66(s,3H);ESIMS m/z 520([M+H]+).
N−(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)チオ尿素(29)の調製
N−(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)チオ尿素(29)を、実施例5で述べた手順に従って化合物28から合成した。化合物を白色固体として単離した(8.18g、92%):融点107〜109℃;1H NMR(300 MHz,CDCl3)δ8.82(s,1H),8.11(d,J=7.6 Hz,1H),7.76(d,J=7.9 Hz,1H),6.36(br s,1H),6.19(br s,1H),5.52(d,J=13.5 Hz,1H),5.06(d,J=13.5 Hz,1H),3.39(s,3H);ESIMS m/z 340([M+H]+).
9H−フルオレン−9−イルメチル{[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]アミノ}カルボノチオイルカルバメート(30)の調製
9H−フルオレン−9−イルメチル{[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]アミノ}カルボノチオイルカルバメート(30)を、実施例4で述べた手順に従って対応するスルホキシミドから合成した。化合物を明黄色の泡として単離した(14.8g、92%):融点98〜101℃;1H NMR(300 MHz,DMSO−d6)δ11.15(s,1H),8.56(d,J=2.3 Hz,1H),8.05(dd,J=2.3,8.2 Hz,1H),7.90(d,J=7.6 Hz,2H),7.84(d,J=7.6 Hz,2H),7.59(d,J=8.2 Hz,1H),7.44(t,J=7.1 Hz,2H),7.34(dt,J=1.0,7.6 Hz,2H),5.09(s,2H),4.32−4.26(m,3H),3.61(s,3H);ESIMS m/z 486([M+H]+).
N−[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]チオ尿素(31)の調製
N−[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]チオ尿素(31)を、実施例5で述べた手順に従って化合物30から合成した。化合物を明橙色固体として単離した(4.96g、62%):融点155〜158℃;1H NMR(300 MHz,DMSO−d6)δ8.51(d,J=2.3 Hz,1H),8.12(br s,1H),7.79(m,2H),7.61(d,J=8.2 Hz,1H),5.21(s,2H),3.36(s,3H);ESIMS m/z 264([M+H]+).
9H−フルオレン−9−イルメチル({メチル[1−(6−メチルピリジン−3−イル)エチル]オキシド−λ4−スルファニリデン}アミノ)カルボノチオイルカルバメート(32)の調製
9H−フルオレン−9−イルメチル({メチル[1−(6−メチルピリジン−3−イル)エチル]オキシド−λ4−スルファニリデン}アミノ)カルボノチオイルカルバメート(32)を、実施例4で述べた手順に従って対応するスルホキシミドから合成した。化合物を黄褐色の泡として単離した(2.61g、54%):融点101〜106℃;1H NMR(400 MHz,CDCl3)δ8.59(dd,J=2.3,5.5 Hz,1H),8.30(d,J=14.1 Hz,1H),8.06(dd,J=2.3,8.2 Hz,0.5H),7.85(dd,J=2.5,8.1 Hz,0.5H),7.78(d,J=7.3 Hz,2H),7.59(d,J=7.6 Hz,2H),7.42(t,J=7.6 Hz,2H),7.33(t,J=7.6 Hz,2H),7.23(d,J=8.3 Hz,0.5H),7.20(d,J=8.1 Hz,0.5H),5.16(q,J=7.1 Hz,0.5H),4.71(q,J=7.1 Hz,0.5H),4.51−4.43(m,2H),4.26−4.23(m,1H),3.34(s,3H),2.59(s,1.5H),2.56(s,1.5H),1.93(d,J=7.1 Hz,1.5H),1.87(d,J=7.1 Hz,1.5H);ESIMS m/z 480([M+H]+).
N−{メチル[1−(6−メチルピリジン−3−イル)エチル]オキシド−λ4−スルファニリデン}−チオ尿素(33)の調製
N−{メチル[1−(6−メチルピリジン−3−イル)エチル]オキシド−λ4−スルファニリデン}−チオ尿素(33)を、実施例5で述べた手順に従って化合物32から合成した。化合物を黄褐色固体として単離した(0.78g、57%):融点137〜140℃;1H NMR(400 MHz,DMSO−d6)δ8.57(d,J=1.8 Hz,1H),8.00(d,J=11.4 Hz,1H),7.91−7.83(m,2H),7.30(t,J=8.0 Hz,1H),5.28(q,J=7.1 Hz,1H),3.36(s,1.5H),3.34(s,1.5H),2.48(s,1.5H),2.48(s,1.5H),1.73(d,J=6.3 Hz,1.5H),1.72(d,J=6.6 Hz,1.5H);ESIMS m/z 258([M+H]+).
9H−フルオレン−9−イルメチル[(メチル(オキシド){1−[4−(トリフルオロメチル)フェニル]−エチル}−λ4−スルファニリデン}アミノ)カルボノチオイルカルバメート(34)の調製
9H−フルオレン−9−イルメチル[(メチル(オキシド){1−[4−(トリフルオロメチル)フェニル]−エチル}−λ4−スルファニリデン)アミノ)カルボノチオイルカルバメート(34)を、実施例4で述べた手順に従って対応するスルホキシミドから合成した。化合物を黄色の泡として単離した(4.19g、99%):融点86〜93℃;1H NMR(400 MHz,CDCl3)δ8.29(br s,0.5H),8.24(br s,0.5H),7.80−7.75(m,3.5H),7.65(d,J=8.3 Hz,1H),7.60−7.58(m,2.5H),7.44−7.38(m,2.5H),7.35−7.29(m,2.5H),5.32(q,J=7.3 Hz,0.5H),4.86(q,J=6.8 Hz,0.5H),4.52−4.44(m,2H),4.26−4.23(m,1H),3.32(s,1.5H),3.32(s,1.5H),1.94(d,J=7.1 Hz,1.5H),1.88(d,J=7.3 Hz,1.5H);ESIMS m/z 533([M+H]+).
N−(メチル(オキシド){1−[4−(トリフルオロメチル)フェニル]エチル}−λ4−スルファニリデン)チオ尿素(35)の調製
N−(メチル(オキシド){1−[4−(トリフルオロメチル)フェニル]エチル}−λ4−スルファニリデン)チオ尿素(35)を、実施例5で述べた手順に従って化合物34から合成した。化合物を白色固体として単離した(1.62g、67%):融点166〜168℃;1H NMR(400 MHz,DMSO−d6)δ8.04(d,J=13.6 Hz,1H),7.90(dd,J=2.3,19.2 Hz,1H),7.80−7.75(m,4H),5.49−5.44(m,1H),3.37(s,1.5H),3.34(s,1.5H),1.76(d,J=7.3 Hz,1.5H),1.74(d,J=8.1 Hz,1.5H);ESIMS m/z 311([M+H]+).
N−[2−(6−クロロピリジン−3−イル)−1−オキシドテトラヒドロ−1H−1λ4−チエン−1−イリデン]チオ尿素(36)の調製
工程A.9H−フルオレン−9−イルメチル[[2−(6−クロロピリジン−3−イル)−1−オキシドテトラヒドロ−1H−1λ4−チエン−1−イリデン]アミノ]カルボノチオイルカルバメートの調製
9H−フルオレン−9−イルメチル[[2−(6−クロロピリジン−3−イル)−1−オキシドテトラヒドロ−1H−1λ4−チエン−1−イリデン]アミノ]カルボノチオイルカルバメートを、実施例4で述べた手順に従って対応するスルホキシミドから合成した。化合物を白色抗体として単離した(4.4g、99%):融点86〜95℃;ESIMS m/z 512[M+H]+)。
N−[2−(6−クロロピリジン−3−イル)−1−オキシドテトラヒドロ−1H−1λ4−チエン−1−イリデン]チオ尿素(36)を、実施例5で述べた手順に従って9H−フルオレン−9−イルメチル[[2−(6−クロロピリジン−3−イル)−1−オキシドテトラヒドロ−1H−1λ4−チエン−1−イリデン]アミノ]カルボノチオイルカルバメートから合成した。化合物をオフホワイト色の固体として単離した(0.51g、20%):融点168〜172℃;1H NMR(300MHz,アセトン−d6)δ(2つのジアステレオマーの2:1混合物)8.50(d,J=2.2 Hz,1H),8.43(d,J=2.5 Hz,1H),7.96(dd,J=8.5,2.5 Hz,1H),7.86(dd,J=6.6,1.1 Hz,1H),7.68(br d,J=20.3 Hz,2H),7.51(d,J=8.5 Hz,1H),7.47(d,J=6.6 Hz,1H),5.14(dd,J=11.8,7.4 Hz,2H),4.60(m,2H),4.26(m,2H),2.20−2.65(m,8H);ESIMS m/z 290([M+H]+).
メチル4−({[(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アミノ]カルボノチオイル}アミノ)−4−オキソブタノエート(37)の調製
クロロコハク酸メチル(0.099mL、0.803mmol)を、攪拌しながら25℃でアセトン(2.7mL)に溶解した。この溶液にアセトン(4mL)中の化合物22(0.250g、0.803mmol)を添加した。次に、トリエチルアミン(0.112mL、0.803mmol)を反応混合物に添加し、それを45℃に6時間加温した。温次にかい溶液をろ過し、残留物を温かいアセトンで洗浄した。ろ液を減圧下で濃縮して、メチル4−({[(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アミノ]カルボノチオイル}アミノ)−4−オキソブタノエート(37)を黄色固体として得た(0.342g、>99%):融点131〜133℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.81(m,1H),8.39&8.23(m,1H),7.78(m,1H),5.32&5.10(q,J=7.1 Hz,1H),3.71(m,2H),3.46(m,3H),3.11(m,2H),2.67(m,3H),1.97&1.92(d,J=7.1 Hz,3H);ESIMS m/z 426([M+H]+).
N’’−ヒドロキシ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(38)の調製
メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデンシアナミド(0.200g、0.721mmol)を室温でエタノール(2.7mL)に溶解した。別のフラスコにおいて、塩酸ヒドロキシルアミン(0.099g、1.44mmol)及びNa2CO3(0.229g、2.16mmol)を水(0.9mL)に溶解し、その後反応混合物に添加して、それを8時間加熱還流した。反応の完了時に、溶媒を減圧下で除去した。残留物に水を添加し、減圧ろ過によって固体を収集して、N’’−ヒドロキシ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(38)を白色粉末として得た(0.070g、31%):融点157〜159℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.79(s,1H),8.06(m,1H),7.74(m,1H),5.11&4.98(m,1H),4.52(br s,1H),4.44(br s,1H),3.09&2.96(s,3H),1.89&1.86(d,J=7.3 Hz,3H);ESIMS m/z 311([M−H]−).
N−[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(39)の調製
N−[[(6−クロロピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(39)を、実施例17で述べた手順に従って対応するN−シアノスルホキシミンから合成した。化合物を白色固体として単離した(0.184g、54%):融点156〜158℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.40(s,1H),7.81(m,1H),7.42(m,1H),4.75(m,2H),3.10&3.01(s,3H);ESIMS m/z 263([M+H]+)
N−[[1−(6−クロロピリジン−3−イル)−2−シクロプロピルエチル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(40)の調製
N−[[1−(6−クロロピリジン−3−イル)−2−シクロプロピルエチル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(40)を、実施例17で述べた手順に従って対応するN−シアノスルホキシミンから合成した。化合物を明黄色半固体として単離した(0.142g、34%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.47(s,1H),7.91(m,1H),7.41(m,1H),3.04&2.94(s,3H),2.43&2.31(m,1H),2.00(m,2H),0.45(m,3H),0.14(m,2H);ESIMS m/z 317([M+H]+).
N−[[(3E)−4−クロロ−1−(6−クロロピリジン−3−イル)ブト−3−エニル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(41)の調製
N−[[(3E)−4−クロロ−1−(6−クロロピリジン−3−イル)ブト−3−エニル](メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(41)を、実施例17で述べた手順に従って対応するN−シアノスルホキシミンから合成した。化合物を明黄色半固体として単離した(0.182g、50%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.42(m,1H),7.83(m,1H),7.43(m,1H),6.07(m,1H),5.64(m,1H),4.58&4.49(m,2H),3.22(m,1H),3.05&2.94(s,3H);ESIMS m/z 337([M+H]+).
N’’−ヒドロキシ−N−(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)グアニジン(42)の調製
N’’−ヒドロキシ−N−(メチル(オキシド){[6−(トリフルオロメチル)ピリジン−3−イル]メチル}−λ4−スルファニリデン)グアニジン(42)を、実施例17で述べた手順に従って対応するN−シアノスルホキシミンから合成した。化合物を白色固体として単離した(0.188g、56%):融点118〜120℃;1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.74(s,1H),8.04(m,1H),7.77(m,1H),4.34(s,2H),3.14&2.91(s,3H);ESIMS m/z 297([M+H]+).
N−[{2−シクロプロピル−1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}(メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(43)の調製
N−[{2−シクロプロピル−1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}(メチル)オキシド−λ4−スルファニリデン]−N’’−ヒドロキシグアニジン(43)を、実施例17で述べた手順に従って対応するN−シアノスルホキシミンから合成した。化合物を褐色半固体として単離した(0.323g、51%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.82(m,1H),8.13(m,1H),7.76(m,1H),3.06&2.96(s,3H),2.48&2.36(m,1H),1.97(m,2H),0.45(m,3H),0.15(m,2H);ESIMS m/z 351([M+H]+).
N’’−(アセチルオキシ)−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(44)の調製
化合物38(0.300g、0.967mmol)を25℃で氷酢酸(48mL)に溶解した。この溶液に無水酢酸(0.100mL、1.06mmol)を添加した。混合物をN2下に室温で1時間撹拌した。次に混合物を飽和NaHCO3水溶液に緩やかに注ぎ入れた。ひとたびpH6〜7に達すれば、溶液をCH2Cl2で抽出した。有機抽出物を合わせ、ブラインで洗浄して、乾燥し(Na2SO4)、減圧下で濃縮して、N’’−(アセチルオキシ)−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(44)を白色半固体として得た(0.038g、13%):1H NMR(400 MHz,CDCl3)δ8.81(s,1H),8.13(m,1H),7.77(m,1H),4.88(q,J=7.1 Hz,1H),3.14(s,3H),2.49(s,3H),1.97(d,J=7.1 Hz,3H);ESIMS m/z 353([M+H]+).
N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(45)の調製
化合物38(0.300g、0.967mmol)を室温で氷酢酸(48mL)に溶解した。この溶液に無水酢酸(0.100mL、1.06mmol)を添加した。混合物をN2下に室温で1時間撹拌した。次に、5%Pd/C(2g、0.967mmol)を添加し、混合物を水素化した(30psi)。Pd/CをCelite(登録商標)のパッドでろ過し、ろ液を飽和NaHCO3水溶液に緩やかに注ぎ入れた。ひとたびpH>7に達すれば、溶液をCH2Cl2で抽出した。有機抽出物を合わせ、ブラインで洗浄して、乾燥し(Na2SO4)、減圧下で濃縮して、N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(45)を粗黄色オイルとして得た(0.111g、39%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.82(s,1H),8.10(m,1H),7.74(m,1H),5.39&5.27(q,J=7.3 Hz,1H),3.19&3.00(s,3H),1.90&1.85(d,J=7.1 Hz,3H);ESIMS m/z 295([M+H]+).
N’’−[4−(クロロベンジル)オキシ]−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(46)の調製
NaH(鉱油中の60%分散、0.026g、0.644mmol)をTHF(1.6mL)に懸濁し、0℃に冷却した。化合物38(0.200g、0.644mmol)を添加し、15分後に、THF(1mL)に溶解した4−クロロベンジルクロリド(0.104g、0.644mmol)を反応混合物に滴下した。混合物を飽和NH4Cl水溶液でクエンチングし、酢酸エチルで希釈した。層を分離し、有機層を飽和NH4Cl水溶液及びブラインで洗浄した。その後有機層を減圧下で濃縮した。粗物質を、アセトニトリル−水混合物で溶出する逆相HPLCを用いて精製し、N’’−[4−(クロロベンジル)オキシ]−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(46)を黄褐色半固体として得た(0.012g、4%):1H NMR(400MHz,CD3OD)δ(ジアステレオマーの混合物)8.58(m,1H),7.97(m,1H),7.70(m,1H),7.30(m,2H),7.20(m,2H),4.89(m,1H),4.74(s,2H),2.89&2.82(s,3H),1.68&1.64(d,J=7.3 Hz,3H):ESIMS m/z 435([M+H]+).
N’’−メトキシ−N−メチル−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(63)の調製
炭酸カリウム(0.044g、0.322mmol)を室温でアセトニトリル(0.644mL)に懸濁した。この混合物に化合物38(0.100g、0.322mmol)を添加した。溶液を室温で30分間撹拌した後、ヨウ化メチル(0.020mL、0.322mmol)を添加した。添加の完了後、反応物を一晩撹拌した。混合物をろ過し、減圧下で濃縮して、N’’−メトキシ−N−メチル−N’−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)グアニジン(63)を黄色半固体として得た(0.215g、>99%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)9.05(s,1H),8.41(m,1H),7.81(m,1H),6.31&6.20(q,J=7.1 Hz,1H),3.87&3.83(s,3H),3.70(s,3H),3.47&3.36(s,3H),1.97&1.95(m,3H);ESIMS m/z 339([M+H]+).
N−[[(3E)−4−クロロ−1−(6−クロロピリジン−3−イル)ブト−3−エニル](メチル)オキシド−λ4−スルファニリデン]−N’’−イソプロポキシグアニジン(64)の調製
N−[[(3E)−4−クロロ−1−(6−クロロピリジン−3−イル)ブト−3−エニル](メチル)オキシド−λ4−スルファニリデン]−N’’−イソプロポキシグアニジン(64)を、実施例25で述べた手順に従って化合物41から合成した。化合物を金色半固体として単離した(0.080g、44%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.37(s,1H),7.82(m,1H),7.44(m,1H),6.05(m,1H),5.65(m,1H),4.53&4.44(m,2H),4.10(m,1H),3.20(m,1H),3.09&2.93(s,3H),1.22(m,3H),0.86(m,3H);ESIMS m/z 379([M+H]+).
2,2,2−トリフルオロ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アセトアミド(65)の調製
5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジン(0.075g、0.297mmol)を25℃でピリジン(0.24mL)に溶解した。次に、無水トリフルオロ酢酸(0.471mL、2.58mmol)を反応混合物に添加し、それを2時間撹拌した。混合物を酢酸エチルで希釈し、5%クエン酸、ブライン及び飽和NaHCO3水溶液で洗浄した。有機層を乾燥し(MgSO4)、減圧下で濃縮して、2,2,2−トリフルオロ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アセトアミド(65)を黄色のオイルとして得た(43mg、42%):1H NMR(400MHz,CDCl3)δ(ジアステレオマーの混合物)8.80(m,1H),8.10(m,1H),7.82(m,1H),4.90(m,1H),3.32&3.21(s,3H),2.01&1.95(d,J=7.3 Hz,3H);ESIMS m/z 347([M+H]+).
2,2−ジフルオロ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アセトアミド(66)の調製
N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)−1H−イミダゾール−1−カルボチオアミド(300mg、0.83mmol)をアセトニトリル(10mL)に溶解し、0℃に冷却した。攪拌しながら、シリンジを介してヒドラジン(水中の64〜65%溶液、30.8μL、31.9mg、0.64mmol)を添加した。10分後、混合物を飽和NH4Cl水溶液(100mL)に注ぎ入れ、それをCHCl3(100mL)で1回抽出した。有機相を、水相がわずかに酸性になるまで飽和NH4Cl水溶液のいくつかのアリコートで洗浄し、その後乾燥した(Na2SO4)。ろ過後、無水ジフルオロ酢酸(154μL、216mg、1.24mmol)を有機相に滴下し、次のそれを25℃で20分間撹拌した。減圧下で溶媒を除去した。粗濃縮物は、粗反応混合物のLC−MS分析によれば不安定なジフルオロアセチルセミカルバジド及びジフルオロアセトアミドを主たる生成物として含んだ。混合物を飽和NaHCO3水溶液に緩やかに添加し、CHCl3(3×50mL)で抽出した。合わせた有機抽出物を、飽和NH4Cl水溶液(50mLアリコートずつ、中性になるまで)で洗浄して、乾燥し(Na2SO4)、減圧下で濃縮した。化合物を逆相クロマトグラフィー(水−アセトニトリル勾配)によって精製し、2,2−ジフルオロ−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)アセトアミド(66)を黄色がかったオイルとして得た(38mg、13%):1H−NMR(400 MHz,CDCl3):δ8.79(d,J=2.1 Hz,0.33H),8.74(d,J=2.1 Hz,0.67H),8.09(dd,J=8.2 Hz,J=2.1 Hz,0.33H),8.04(dd,J=8.2 Hz,J=2.1 Hz,0.67H),7.79(d,J=8.2 Hz,0.33H),7.76(d,J=8.2 Hz,0.67H),5.83(t,J=54.5 Hz,0.33H),5.73(t,J=54.5 Hz,0.67H),4.95(q,J=7.2 Hz,0.33H),4.91(q,J=7.2 Hz,0.67H),3.28(s,2H),3.14(s,1H),1.97(d,J=7.2 Hz,2H),1.89(d,J=7.2 Hz,1H);ESIMS m/z 331([M+H]+)
2,2−ジメチル−N−(メチル(オキシド){1−[6−(トリフルオロメチル)ピリジン−3−イル]エチル}−λ4−スルファニリデン)プロパンアミド(67)の調製
ピリジン(1mL)及び無水ピバル酸(244mg、1.31mmol、1.1当量)中の5−[1−(メチルスルホンイミドイル)エチル]−2−(トリフルオロメチル)ピリジン(300mg、1.19mmol)を90℃で1時間撹拌した。ヒューニッヒ塩基(2滴)を添加し、混合物を2時間加熱還流した。溶媒を減圧下で除去し、残留物をカラムクロマトグラフィー(メタノール−塩化メチレン勾配)によって精製した。生成物を白色からオフホワイト色の粉末として得た(125mg、31%):1H NMR(400MHz,CDCl3):δ8.78(d,J=1.9 Hz,0.6H),8.74(d,J=1.9 Hz,0.4H),8.07(dd,J=8.1 Hz,J=2.1 Hz,0.6H),8.01(dd,J=8.1 Hz,J=2.1 Hz,0.4H),7.76(d,J=8.2 Hz,1H),7.71(d,J=8.2 Hz,0.4H),5.03(q,J=7.2 Hz,0.6H),4.97(q,J=7.2 Hz,0.4H),3.20(s,1.2H),3.01(s,1.8H),1.90(d,J=7.2 Hz,1.2H),1.80(d,J=7.2 Hz,1.8H),1.22(s,5.4H),1.07(s,3.6H);ESIMS m/z 337([M+H]+).
殺虫効果試験
化合物1〜67を、以下で述べる手順を用いてモモアカアブラムシ(green peach aphid)に対して試験した。
2〜3枚の小さな(3〜5cm)の本葉を有する、3インチの鉢で成長させたキャベツ実生を試験基質として使用した。薬剤施用の1〜2日前に実生を20〜50匹のモモアカアブラムシ(無翅成体及び若虫)に感染させた。各々の処理について4つの実生を使用した。化合物(2mg)をアセトン−メタノール(1:1)溶媒2mLに溶解し、1000ppmの原液を形成した。この原液をH2O中の0.025%Tween 20で5倍に希釈して、200ppmの溶液を得た。携帯型Devilbissアスピレーター噴霧器を用いて、溶液を、キャベツの葉の両面に流れ落ちるまで噴霧した。標準植物(溶媒検査)には希釈剤だけを噴霧した。処理した植物を約23℃、40%RHで3日間保持室に置いた後、選別した。評価は、顕微鏡下で植物当たりの生存アブラムシの数を数えることによって実施した。殺虫活性は、Abbottの補正式を用いることによって測定した:
補正した防除%=100×(X−Y)/X
[式中、X=溶媒検査植物上の生存アブラムシの数
Y=処理植物上の生存アブラムシの数]
本発明において開示する化合物は、農薬上許容される酸付加塩の形態であり得る。
本発明において開示する一部の化合物は、1又はそれ以上の立体異性体として存在し得る。様々な立体異性体は、幾何異性体、ジアステレオマー及びエナンチオマーを含む。それ故、本発明において開示する化合物は、ラセミ混合物、個々の立体異性体及び光学的に活性な混合物を包含する。
もう1つの実施形態では、本明細書で開示する本発明は、害虫を防除するために使用できる。
本明細書で開示する本発明と組み合わせて有益に使用できる農薬の一部は、以下を含むが、これらに限定されない:
1,2ジクロロプロパン、1,3ジクロロプロペン、
アバメクチン、アセフェート、アセキノシル、アセタミプリド、アセチオン、アセトプロール、アクリナトリン、アクリロニトリル、アラニカルブ、アルジカルブ、アルドキシカルブ、アルドリン、アレスリン、アロサミジン、アリキシカルブ、α−シペルメトリン、α−エクジソン、α−エンドスルファン、AKD−1022、アミジチオン、アミドフルメト、アミノカルブ、アミトン、アミトラズ、アナバシン、三酸化ヒ素(arsenous oxide)、アチダチオン、アザジラクチン、アザメチホス、アジンホスエチル、アジンホスメチル、アゾベンゼン、アゾシクロチン、アゾトエート、
バチルス・チューリンゲンシス(Bacillus thuringiensis)、ヘキサフルオロケイ酸バリウム、バルトリン、ベンクロチアズ、ベンジオカルブ、ベンフラカルブ、ベノミル、ベノキサホス、ベンスルタップ、ベンゾキシメート、安息香酸ベンジル、β−シフルトリン、β−シペルメトリン、ビフェナゼート、ビフェントリン、ビナパクリル、ビオアレトリン、ビオエタノメトリン、ビオペルメトリン、ビストリフルロン、ボラックス、ホウ酸、ブロムフェンビンホス、ブロモ−DDT、ブロモシクレン、ブロモホス、ブロモホスエチル、ブロモプロピレート、ブフェンカルブ、ブプロフェジン、ブタカルブ、ブタチオホス、ブトカルボキシム、ブトネート、ブトキシカルボキシム、
カズサホス、ヒ酸カルシウム、多硫化カルシウム、カンフェクロル、カルバノレート、カルバリル、カルボフラン、二硫化炭素、四塩化炭素、カルボフェノチオン、カルボスルファン、カルタップ、キノメチオネート、クロラントラニリプロール、クロルベンシド、クロルビシクレン、クロルデン、クロルデコン、クロルジメホルム、クロルエトキシホス、クロルフェナピル、クロルフェネトール、クロルフェンソン、クロルフェンスルフィド、クロルフェンビンホス、クロルフルアズロン、クロルメホス、クロルベンジレート、3−(4−クロロ−2,6−ジメチルフェニル)−4−ヒドロキシ−8−オキサ−1−アザスピロ[4,5]デク−3−エン−2−オン、3−(4’−クロロ−2,4−ジメチル[1,1’−ビフェニル]−3−イル)−4−ヒドロキシ−8−オキサ−1−アザスピロ[4,5]デク−3−エン−2−オン、4−[[(6−クロロ−3−ピリジニル)メチル]メチルアミノ]−2(5H)−フラノン、4−[[(6−クロロ−3−ピリジニル)メチル]シクロプロピルアミノ]−2(5H)−フラノン、3−クロロ−N2−[(1S)−1−メチル−2−(メチルスルホニル)エチル]−N1−[2−メチル−4−[1,2,2,2−テトラフルオロ−1−(トリフルオロメチル)エチル]フェニル]−1,2−ベンゼンジカルボキサミド、クロロホルム、クロロメブホルム、クロロメチウロン、クロロピクリン、クロロプロピレート、クロルホキシム、クロルプラゾホス、クロルピリホス、クロルピリホス−メチル、クロルチオホス、クロマフェノジド、シネリンI、シネリンII、シスメトリン、クロエトカルブ、クロフェンテジン、クロサンテル、クロチアニジン、アセト亜ヒ酸銅、ヒ酸銅、ナフテン酸銅、オレイン酸銅、クマホス、クミトエート、クロタミトン、クロトキシホス、クルエンタレンA及びB、クルホメート、クリオライト、シアノフェンホス、シアノホス、シアントエート、シアントラニリプロール、シクレトリン、シクロプロトリン、シエノピラフェン、シフルメトフェン、シフルトリン、シハロトリン、シヘキサチン、シペルメトリン、シフェノトリン、シロマジン、シチオエート、2−シアノ−N−エチル−4−フルオロ−3−メトキシ−ベンゼンスルホンアミド、2−シアノ−N−エチル−3−メトキシ−ベンゼンスルホンアミド、2−シアノ−3−ジフルオロメトキシ−N−エチル−4−フルオロ−ベンゼンスルホンアミド、2−シアノ−3−フルオロメトキシ−N−エチル−ベンゼンスルホンアミド、2−シアノ−6−フルオロ−3−メトキシ−N,N−ジメチル−ベンゼンスルホンアミド、2−シアノ−N−エチル−6−フルオロ−3−メトキシ−N−メチル−ベンゼンスルホンアミド、2−シアノ−3−ジフルオロメトキシ−N,N−ジメチル−ベンゼンスルホンアミド、
D−リモネン、ダゾメット、DBCP、DCIP、DDT、デカルボフラン、デルタメトリン、デメフィオン、デメフィオンO、デメフィオンS、デメトン、デメトンメチル、デメトンO、デメトンOメチル、デメトンS、デメトンSメチル、デメトンSメチルスルホン、ジアフェンチウロン、ジアリホス、ジアミダホス、ダイアジノン、ジカプトン、ジクロフェンチオン、ジクロフルアニド、ジクロルボス、ジコホル、ジクレシル、ジクロトホス、ジシクラニル、ディルドリン、ジエノクロル、ジフロビダジン、ジフルベンズロン、3−(ジフルオロメチル)−N−[2−(3,3−ジメチルブチル)フェニル]−1−メチル−1H−ピラゾール−4−カルボキサミドジロル、ジメフルトリン、ジメホックス、ジメタン、ジメトエート、ジメトリン、ジメチルビンホス、ジメチラン、ジネックス、ジノブトン、ジノカップ、ジノカップ4、ジノカップ6、ジノクトン、ジノペントン、ジノプロップ、ジノサム、ジノスルホン、ジノテフラン、ジノテルボン、ジオフェノラン、ジオキサベンゾホス、ジオキサカルブ、ジオキサチオン、ジフェニルスルホン、ジスルフィラム、ジスルホトン、ジチクロホス、DNOC、ドフェナピン、ドラメクチン、
エクジステロン、エマメクチン、EMPC、エムペントリン、エンドスルファン、エンドチオン、エンドリン、EPN、エポフェノナン、エプリノメクチン、エスフェンバレレート、エタホス、エチオフェンカルブ、エチオン、エチプロール、エトエートメチル、エトプロホス、エチル−DDD、ギ酸エチル、二臭化エチレン、二塩化エチレン、エチレンオキシド、エトフェンプロックス、エトキサゾール、エトリムホス、EXD、
F1050、ファムフール、フェナミホス、フェナザフロル、フェナザキン、酸化フェンブタスズ、フェンクロルホス、フェネタカルブ、フェンフルトリン、フェニトロチオン、フェノブカルブ、フェノチオカルブ、フェノキサクリム、フェノキシカルブ、フェンピリトリン、フェンプロパトリン、フェンピロキシメート、フェンソン、フェンスルホチオン、フェンチオン、フェンチオンエチル、フェントリファニル、フェンバレレート、フィプロニル、FKI−1033、フロニカミド、フルアクリピリム、フルアズロン、フルベンジアミド、フルベンジミン、フルコフロン、フルシクロクスロン、フルシトリネート、フルエネチル、フルフェネリム、フルフェノクスロン、フルフェンプロックス、フルメトリン、フルオルベンシド、フルバリネート、ホノホス、ホルメタネート、ホルモチオン、ホルムパラネート、ホスメチラン、ホスピレート、ホスチアゼート、ホスチエタン、ホスチエタン、フラチオカルブ、フレトリン、フルフラール、
γ−シハロトリン、γ−HCH、
ハルフェンプロックス、ハロフェノジド、HCH、HEOD、ヘプタクロール、ヘプテノホス、ヘテロホス、ヘキサフルムロン、ヘキシチアゾクス、HHDN、ヒドラメチルノン、シアン化水素、ハイドロプレン、ヒキンカルブ、
イミシアホス、イミダクロプリド、イミプロトリン、インドキサカルブ、IPSP、イサミドホス、イソベンザン、イソカルボホス、イソドリン、イソフェンホス、イソプロカルブ、イソプロチオラン、イソチオエート、イソキサチオン、イベルメクチン、
ジャスモリンI、ジャスモリンII、ヨードフェンホス、幼若ホルモンI、幼若ホルモンII、幼若ホルモンIII、JS118、
ケレバン、キノプレン、
λ−シハロトリン、ヒ酸鉛、レピメクチン、レプトホス、リンデン、リリムホス、ルフェヌロン、リチダチオン、
マラチオン、マロノベン、マジドックス、メカルバム、メカルホン、メナゾン、メホスホラン、塩化第一水銀、メスルフェン、メスルフェンホス、メタフルミゾン、メタム、メタクリホス、メタミドホス、メチダチオン、メチオカルブ、メトクロトホス、メソミル、メトプレン、メトキシクロル、メトキシフェノジド、臭化メチル、メチルイソチオシアネート、メチルクロロホルム、塩化メチレン、メトフルトリン、メトルカルブ、メトキサジアゾン、メビンホス、メキサカルベート、ミルベメクチン、ミルベマイシンオキシム、ミパホックス、マイレックス、MNAF、モノクロトホス、モルホチオン、モキシデクチン、
ナフタロホス、ナレド、ナフタレン、N−エチル−2,2−ジメチルプロピオンアミド−2−(2,6−ジクロロ−α,α,α−トリフルオロ−p−トリル)ヒドラゾン、N−エチル−2,2−ジクロロ−1−メチルシクロプロパン−カルボキサミド−2−(2,6−ジクロロ−α,α,α−トリフルオロ−p−トリル)ヒドラゾン、ニコチン、ニフルリジド、ニッコマイシン、ニテンピラム、ニチアジン、ニトリラカルブ、ノバルロン、ノビフルムロン、
オメトエート、オキサミル、オキシジメトンメチル、オキシデプロホス、オキシジスルホトン、
パラジクロロベンゼン、パラチオン、パラチオンメチル、ペンフルロン、ペンタクロロフェノール、ペルメトリン、フェンカプトン、フェノトリン、フェントエート、ホレート、ホサロン、ホスホラン、ホスメット、ホスニクロル、ホスファミドン、ホスフィン、ホスホカルブ、ホキシム、ホキシムメチル、ピリメタホス、ピリミカルブ、ピリミホスエチル、ピリミホスメチル、亜ヒ酸カリウム、チオシアン酸カリウム、pp’DDT、プラレトリン、プレコセンI、プレコセンII、プレコセンIII、プリミドホス、プロクロノール、プロフェノホス、プロフルトリン、プロマシル、プロメカルブ、プロパホス、プロパルギット、プロペタムホス、プロポクスル、プロチダチオン、プロチオホス、プロトエート、プロトリフェンブト、ピラクロホス、ピラフルプロール、ピラゾホス、ピレスメトリン、ピレトリンI、ピレトリンII、ピリダベン、ピリダリル、ピリダフェンチオン、ピリフルキナゾン、ピリミジフェン、ピリミテート、ピリプロール、ピリプロキシフェン、
Qcid、クアシア、キナルホス、キナルホス、キナルホスメチル、キノチオン、クアンチフィエス(quantifies)、
ラフォキサニド、レスメトリン、ロテノン、リアニア、
サバジラ、シュラーダン、セラメクチン、シラフルオフェン、亜ヒ酸ナトリウム、フッ化ナトリウム、ヘキサフルオロケイ酸ナトリウム、チオシアン酸ナトリウム、ソファミッド、スピネトラム、スピノサド、スピロジクロフェン、スピロメシフェン、スピロテトラマット、スルコフロン、スルフィラム、スルフルラミド、スルホテップ、スルホキサフロール、硫黄、フッ化スルフリル、スルプロホス、
τ-フルバリネート、タジムカルブ、TDE、テブフェノジド、テブフェンピラド、テブピリムホス、テフルベンズロン、テフルトリン、テメホス、TEPP、テラレトリン、テルブホス、テトラクロロエタン、テトラクロロビンホス、テトラジホン、テトラメトリン、テトラナクチン、テトラスル、θシペルメトリン、チアクロプリド、チアメトキサム、チクロホス、チオカルボキシム、チオシクラム、チオジカルブ、チオファノックス、チオメトン、チオナジン、チオキノックス、チオスルタップ、チューリンギエンシン、トルフェンピラド、トラロメトリン、トランスフルトリン、トランスペルメトリン、トリアラセン、トリアザメート、トリアゾホス、トリクロルホン、トリクロルメタホス3、トリクロロナート、トリフェノホス、トリフルムロン、トリメタカルブ、トリプレン、
バミドチオン、バミドチオン、バニリプロール、バニリプロール、
XDE−208、XMC、キシリルカルブ、
ζ−シペルメトリン及びゾラプロホス。
本明細書で開示する本発明は、混合物中の化合物の作用機構が同じ、類似である又は異なる協力作用性混合物を形成するために他の化合物、例えば「混合物」の表題の下で言及されているものと共に使用することができる。
農薬は、その純粋な形態で施用に適することはまれである。通常は、農薬が必要な濃度及び適切な形態で使用でき、施用、取扱い、輸送、保存及び最大農薬活性を容易にするように他の物質を添加する必要がある。それ故、農薬は、例えば餌、乳濁剤(concentrated emulsions)、粉剤、乳剤(emulsifiable concentrates)、くん蒸剤、ゲル、粒剤、マイクロカプセル剤、種子処理、懸濁製剤、サスポエマルション製剤、錠剤、水溶性液剤、顆粒水和剤又はドライフロアブル、水和剤及び微量散布液剤(ultra low volume solutions)に製剤される。
1287550167924_46
付加物の中に見出される。
一般に、本明細書で開示する本発明が製剤中で使用される場合、そのような製剤は他の成分も含有し得る。これらの成分は(これは非網羅的及び非相互排他的なリストである)、湿展剤、展着剤、固着剤、浸透剤、緩衝剤、金属イオン封鎖剤(sequestering agents)、ドリフト低減剤、親和性改善物質、消泡剤、洗浄剤及び乳化剤を含むが、これらに限定されない。
害虫の存在場所に施用される農薬の実際の量は決定的に重要ではなく、当業者によって容易に決定され得る。一般に、1ヘクタール当たり約0.01グラムの農薬から1ヘクタール当たり約5000グラムまでの農薬の濃度が良好な防除を提供すると予想される。
Claims (14)
- 以下の式(I):
[式中、
(a)R1は、ピリジルであり、前記ピリジルは、以下の置換基:F、Cl、Br、I、C1〜C6アルキル、またはC1〜C6ハロアルキルの一つで置換されてもよく;
(b)R2は、C 1〜C8アルキルであり;
(c)R3は、C 1〜C8アルキル、アリール、C 3〜C8シクロアルキル、H、ヘテロシクリル、C(=O)C1〜C6アルキル、C(=O)C1〜C6アリール又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、C 1〜C6ハロアルコキシ、C(=O)OC1〜C6アルキル、及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(d)R4は、C 1〜C8アルキル、アリール、C 3〜C8シクロアルキル、H、ヘテロシクリル、C(=O)C1〜C6アルキル、C(=O)C1〜C6アリール又はC0〜C8アルキル−C(=O)OR8であり、その各々(Hを除く)は、独立して以下の置換基:F、Cl、Br、I、C 1〜C6ハロアルコキシ、C(=O)OC1〜C6アルキル、及びヘテロシクリルの1又はそれ以上で置換されてもよく、そしてR3とR4はまた、4、5又は6員環を形成してもよく;
(e)R5は、C 1〜C8アルキル、またはHであり;
(f)R6は、C 1〜C8アルキル、またはHであり;
(g)nは1〜4であり;
(h)Xは、Sであり;
(i)Jは、Nであり;および
(k)R8は、C 1〜C8アルキルであり、前記アルキルは、アリールで置換されてもよい。]
を有する化合物。 - 請求項1に記載の化合物の農薬上許容される酸付加塩である化合物。
- 請求項1に記載の化合物を含有する溶媒和物。
- 害虫を防除すべき場所に、請求項1に記載の化合物を施用することを含むプロセス。
- 線形動物門(Phylum Nematoda)又は節足動物門(Phylum Arthropoda)の害虫を防除すべき場所に、請求項1に記載の化合物を施用することを含むプロセス。
- 少なくとも1つの他の農薬と請求項1に記載の化合物との混合物を含有する害虫を防除するための組成物。
- 少なくとも1つの除草剤、少なくとも1つの殺菌剤又は少なくとも1つの除草剤及び殺菌剤と請求項1に記載の化合物との混合物を含有する害虫を防除するための組成物。
- 以下の品目:アセチルコリンエステラーゼ阻害剤;ナトリウムチャネル調節剤;キチン生合成阻害剤;GABA依存性塩素イオンチャネルアンタゴニスト;GABA及びグルタミン酸依存性塩素イオンチャネルアゴニスト;アセチルコリン受容体アゴニスト;MET I阻害剤;Mg刺激性ATPアーゼ阻害剤;ニコチン性アセチルコリン受容体;中腸膜破壊剤;又は酸化的リン酸化撹乱剤の少なくとも1つと共に請求項1に記載の化合物を含有する害虫を防除するための組成物。
- 請求項1に記載の化合物を種子に施用するプロセス。
- 1又はそれ以上の特殊な形質を発現するように遺伝的に形質転換された種子に請求項1に記載の化合物を施用するプロセス。
- 1又はそれ以上の特殊な形質を発現するように遺伝的に形質転換された遺伝的形質転換植物に請求項1に記載の化合物を施用するプロセス。
- 請求項1に記載の化合物を動物(但し、ヒトを除く)に経口的に投与する又は適用するプロセス。
-
[式中、R1、R2、R3、R4、R5及びR6は請求項1で規定されたとおりである]を反応させて、請求項1に記載の化合物を生成することを含むプロセス。 - 以下の式:
を有する化合物。
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US61/067,874 | 2008-03-03 | ||
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- 2009-03-02 AR ARP090100737A patent/AR070740A1/es unknown
- 2009-03-03 CL CL2009000499A patent/CL2009000499A1/es unknown
- 2009-03-03 UY UY031688A patent/UY31688A1/es not_active Application Discontinuation
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2010
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- 2010-09-01 CO CO10108108A patent/CO6310993A2/es active IP Right Grant
- 2010-12-07 US US12/962,114 patent/US8178685B2/en active Active
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2011
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Also Published As
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CL2009000499A1 (es) | 2010-04-16 |
US20090221424A1 (en) | 2009-09-03 |
US8178685B2 (en) | 2012-05-15 |
CO6310993A2 (es) | 2011-08-22 |
US20110077160A1 (en) | 2011-03-31 |
EP2268615A1 (en) | 2011-01-05 |
JP2011515342A (ja) | 2011-05-19 |
NZ587572A (en) | 2012-04-27 |
WO2009111309A1 (en) | 2009-09-11 |
UY31688A1 (es) | 2009-09-30 |
ZA201006066B (en) | 2011-10-26 |
TWI434651B (zh) | 2014-04-21 |
ES2593116T3 (es) | 2016-12-05 |
CA2717069C (en) | 2013-08-20 |
AU2009222174B2 (en) | 2013-02-28 |
BRPI0909036A8 (pt) | 2018-10-23 |
AR070740A1 (es) | 2010-04-28 |
TW200942174A (en) | 2009-10-16 |
AU2009222174A1 (en) | 2009-09-11 |
US20120225782A1 (en) | 2012-09-06 |
CN102015634B (zh) | 2014-02-12 |
CA2717069A1 (en) | 2009-09-11 |
US8445689B2 (en) | 2013-05-21 |
CN102015634A (zh) | 2011-04-13 |
HK1156595A1 (en) | 2012-06-15 |
KR20100127255A (ko) | 2010-12-03 |
EP2268615B1 (en) | 2016-08-17 |
BRPI0909036A2 (pt) | 2018-05-22 |
MX2010009748A (es) | 2010-11-30 |
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