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Novel Analogues of a-Terthienyl, Thienyl 1, 3, 4-Thia(oxa)diazoles as Potential Photoactivated Insecticides: Synthesis and Bioactivity 被引量：1

Novel Analogues of a-Terthienyl, Thienyl 1, 3, 4-Thia(oxa)diazoles as Potential Photoactivated Insecticides: Synthesis and Bioactivity
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摘要 Novel 1, 3, 4-thia(oxa)diazoles containing thienyl groups were synthesized. Analogous to the naturally-occurring compound, a-terthienyl, they can be photosensitized by ultraviolet light and showed phototoxicities against the 2nd instar larvae of southern armyworm (Pseudaletia separata Walker), they also showed photocleavage action to pBR322 DNA.
作者 LiGangLIU YuFangXU XuHongQIAN QingChunHUANG
机构地区 InstituteofPesticides＆Pharmaceuticals ShanghaiKeyLabofChemicalBiology StateKeyLaboratoryofFineChemicals
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第1期7-10,共4页 中国化学快报（英文版）
关键词 THIADIAZOLES OXADIAZOLES a-terthienyl phototoxic. Thiadiazoles, oxadiazoles, a-terthienyl, phototoxic.
分类号 O626.12 [理学—有机化学] TQ453.2 [化学工程—农药化工]
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  • 10[10]Data of 2, 5-bis(5-bromothiophen-2-yl)-1, 3, 4-thiadiazole 3: mp 229-231°C; MS m/z 406 (M+); 1H NMR (CDCl3, δppm) 7.28 (d, 1H, J=3.79Hz, H-4), 7.11 (d, 1H, J=3.79Hz, H-3). Data of 2, 5-bis(5-iodothiophen-2-yl)-1, 3, 4-thiadiazole 5: mp 252-254°C; MS m/z 502 (M+); 1H NMR (CDCl3, δppm) 7.29 (d, 1H, J=3.94Hz, H-4), 7.11 (d, 1H, J=3.94Hz, H-3). Data of 2, 5-bis(5-iodothiophen-2-yl)-1, 3, 4-oxadiazole 6: mp 193-194(C; MS m/z 486 (M+); 1H NMR (CDCl3, δppm) 7.45 (d, 1H, J=3.82Hz, H-4), 7.34 (d, 1H, J=3.82Hz, H-3). Data of 2, 5-bis(5-methylthiophen-2-yl)-1, 3, 4-thiadiazole 7: mp 179-180°C ; MS m/z 278 (M+); 1H NMR (Acetone-d6, δppm) 7.52 (d, 1H, J=3.57Hz, H-3), 6.94 (d, 1H, J=3.57Hz, H-4), 2.56 (s, 3H, CH3). Data of 2, 5-bis(5-methylthiophen-2-yl)-1, 3, 4-oxadiazole 8: mp 131-132°C; MS m/z 262 (M+); 1H NMR (Acetone-d6, δppm) 7.65 (d, 1H, J=3.57Hz, H-3), 6.98 (d, 1H, J=3.57Hz, H-4), 2.57 (s, 3H, CH3). Data of 2-(5-nitrothiophen- 2-yl)-5-(thiophen-2-yl)-1, 3, 4-thiadiazole 9: mp 262-264°C; MS m/z 295 (M+); 1H NMR (CDCl3, δppm) 7.94 (d, 1H, J=4.29Hz, H-4), 7.64 (d, 1H, J=3.64Hz, H-5), 7.58 (d, 1H, J=4.29Hz, H-3), 7.45 (d, 1H, J=4.25Hz, H-3), 7.18 (t, 1H, J=3.64Hz, J=4.25Hz, H-4). Data of 2-(5-nitro thiophen-2-yl)-5-(thiophen-2-yl)-1, 3, 4-oxadiazole 10: mp 227-229(C; MS m/z 279 (M+); 1H NMR (Acetone-d6, δppm) 7.98 (d, 1H, J=4.4Hz, H-4), 7.64 (dd, 1H, J=3.57Hz, J=1.1Hz, H-5), 7.58 (d, 1H, J=4.4Hz, H-3), 7.45 (dd, 1H, J=4.95Hz, J=1.1Hz, H-3), 7.18 (t, 1H, J=3.57Hz, J=4.95Hz, H-4).

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Chinese Chemical Letters
2004年 第1期

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