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

被引：25

作者：

Chen, Jixiang ^{[1
]}

Gan, Xiuhai ^{[1
]}

Yi, Chongfen ^{[1
]}

Wang, Shaobo ^{[1
]}

Yang, Yuyuan ^{[1
]}

He, Fangcheng ^{[1
]}

Hu, Deyu ^{[1
]}

Song, Baoan ^{[1
]}

机构：

[1] Guizhou Univ, Ctr Res & Dev Fine Chem, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, State Key Lab Breeding Base Green Pesticide & Agr, Guiyang 550025, Guizhou, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2018年 / 36卷 / 10期

基金：

中国国家自然科学基金;

关键词：

1,3,4-oxadiazole; thiadiazole; thioether derivatives; nematicidal activity; cyclization; structure-activity relationships; molecular modeling; TYLENCHULUS-SEMIPENETRANS; ANTIBACTERIAL ACTIVITIES; MELOIDOGYNE-INCOGNITA; INSECTICIDAL ACTIVITY; BIOLOGICAL-ACTIVITIES; CITRUS NEMATODE; BACTERIAL WILT; MOIETY; ANALOGS; DESIGN;

D O I：

10.1002/cjoc.201800282

中图分类号：

O6 [化学];

学科分类号：

0703 ;

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 Tylenchulus semipenetransin vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48h in vitro, with LC50 values of 13.4 +/- 1.8, 11.7 +/- 2.5, 13.7 +/- 2.4 and 13.3 +/- 1.1mgL(-1), respectively, which were obviously superior to fosthiazate (49.1 +/- 2.8mgL(-1)) and avermectin (26.6 +/- 2.3mgL(-1)). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200mgL(-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 +/- 1.4mgL(-1)) and in vivo ((70 +/- 5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.

引用

页码：939 / 944

页数：6

共 35 条

[1] 1,3,4-Oxadiazoles: An emerging scaffold to target growth factors, enzymes and kinases as anticancer agents [J].