Synthesis, Crystal Structure, and Herbicidal Activities of 2-Cyanoacrylates Containing 1,3,4-Thiadiazole Moieties  

作　　者：王婷婷 苗文科 吴姗姗 邴贵芳 张欣 秦振芳 于海波 秦雪 方建新 

机构地区：[1]State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

出　　处：《Chinese Journal of Chemistry》2011年第5期959-967,共9页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China （NNSFC） （No. 20772068） and the National Key Project of Scientific and Technical Supporting Programs Funded by Ministry of Science ＆ Technology of China （No. 2006BAE01A01-5）.

摘　　要：Three series of novel 2-cyanoacrylates 7a--7f, 9a-9f, 10a--10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II （PS II） electron transportation. Their structures were clearly verified by lH NMR, 13C NMR, elemental analysis （or HRMS analysis） and single-crystal X-ray diffraction analysis. Bioassay showed that a suitable group at the 3-position of acrylates was essential for high herbicidal activ- ity. In particular, compound 7e showed the best herbicidal activities and gave 100% inhibitory activity against rape and amaranth pigweed at a dose of 1.5 kg/ha. Introduction of substituent with higher polarity such as sulfinyl or sulfonyl to the 5-position of 1,3,4-thiadiazole decreased herbicidal activities.Three series of novel 2-cyanoacrylates 7a--7f, 9a-9f, 10a--10f containing 1,3,4-thiadiazole ring moieties were synthesized as herbicidal inhibitors of photosystem II （PS II） electron transportation. Their structures were clearly verified by lH NMR, 13C NMR, elemental analysis （or HRMS analysis） and single-crystal X-ray diffraction analysis. Bioassay showed that a suitable group at the 3-position of acrylates was essential for high herbicidal activ- ity. In particular, compound 7e showed the best herbicidal activities and gave 100% inhibitory activity against rape and amaranth pigweed at a dose of 1.5 kg/ha. Introduction of substituent with higher polarity such as sulfinyl or sulfonyl to the 5-position of 1,3,4-thiadiazole decreased herbicidal activities.

关 键 词：2-cyanoacrylate 1 3 4-THIADIAZOLE inhibitors of photosystem II electron transportation herbicidal activity SYNTHESIS 

分 类 号：O614.121[理学—无机化学] TQ433.436[理学—化学]