文献类型：期刊文献

英文题名：Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles

作者：Shi, W; Qian, XH; Zhang, R; Song, GH

机构：[1]Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China;[2]E China Univ Sci & Technol, Inst Pesticides & Pharmaceut, Shanghai 200237, Peoples R China

年份：2001

卷号：49

期号：1

起止页码：124

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000166695100022)】；

语种：英文

外文关键词：2,5-disubstituted-1,3,4-oxadiazoles; insect growth regulatory activity; armyworm; QSAR

摘要：Fourteen new 2,5-disubstituted-1,3,4-oxadiazoles, namely (i) six 2- [2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropyl] -5-substituted-1,3,4-oxadiazoles and (ii) eight 2-substituted-phenoxymethyl-5-substituted-aryl-1,3,4-oxadiazoles, were synthesized and evaluated for their insect growth regulatory activity against second-instar larvae of armyworm (Pseudaletia separata Walker). Two of these compounds (7 and 8) showed good insecticidal activities, with LC50 values of 14.33 and 15.85 mug/mL, respectively. Steric parameters (e.g., the molecular length d and the ratio of the nonpolar surface area and polar surface area V-1/V-2) and semiempirical quantum parameters (e.g., the molecular total energy E-t and the lowest unoccupied molecular orbital energy E-LUMO and so on) of these compounds, as well as those of six other 2,5-disubstituted-1,3,4-oxadiazoles reported, were acquired by the molecular modeling method and the PM3-SCF-MO method, respectively. With the help of the synthons' activity contribution method based on the Free-Wilson approach in its Fujita-Ban variant, quantitative structure-activity relationships were studied by regressing half-lethal concentrations against the above parameters.