Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives  

作　　者：Jixiang Chen Xiuhai Gan Chongfen Yi Shaobo Wang Yuyuan Yang Fangcheng He Deyu Hu Baoan Song 

机构地区：[1]State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bio- engineering, Ministry of Education, Center for Research and Develop-ment of Fine Chemicals, Guizhou University, Guiyang 550025, China

出　　处：《Chinese Journal of Chemistry》2018年第10期939-944,共6页中国化学（英文版）

基　　金：This work was financially supported by the National Key Re- search Development Program of China （2018YFD0200100） and the National Natural Science Foundation of China （No. 21672044） and Subsidy Project for Outstanding Key Laboratory of Guizhou Prov- ince in China （20154004）.

摘　　要：Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchufus semipenetruns in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48 h in vitro, with LC50 values of 13.4±1.8, 11.7±2.5, 13.7±2.4 and 13.31.1 mg.L-1, respectively, which were obviously superior to fosthiazate （49.1±2.8 mg.L-1） and avermectin （26.6±2.3 mg.L-1）. Compound 23. can effectively control the citrus nema- tode disease caused by T. semipenetruns at 200 mg.L-1 in vivo with （68±3）% inhibitory effect, which was even better than that of avermectin （（63±2）%）. The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships （3D-QSARs） were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro （LC50：9.8±1.4 mg.L-1） and in vivo （（70±5）%）. These results demonstrated that compound 33 can be considered as a potential nematicide.Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchufus semipenetruns in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48 h in vitro, with LC50 values of 13.4±1.8, 11.7±2.5, 13.7±2.4 and 13.31.1 mg.L-1, respectively, which were obviously superior to fosthiazate （49.1±2.8 mg.L-1） and avermectin （26.6±2.3 mg.L-1）. Compound 23. can effectively control the citrus nema- tode disease caused by T. semipenetruns at 200 mg.L-1 in vivo with （68±3）% inhibitory effect, which was even better than that of avermectin （（63±2）%）. The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships （3D-QSARs） were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro （LC50：9.8±1.4 mg.L-1） and in vivo （（70±5）%）. These results demonstrated that compound 33 can be considered as a potential nematicide.

关 键 词：1 3 4-oxadiazole/thiadiazole thioether derivatives nematicidal activity CYCLIZATION structure-activity relationships molecular modeling 

分 类 号：TQ450.11[化学工程—农药化工] O636.1[理学—高分子化学]