Syntheses and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles

被引：37

作者：

Shi, W

Qian, XH ^{[1
]}

Song, GH

Zhang, R

Li, RP

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

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 106卷 / 02期

基金：

中国国家自然科学基金;

关键词：

fluoroaryl; 1,3,4-oxadiazoles; cis/trans isomers; one step reaction; insecticidal activity; armyworm;

D O I：

10.1016/S0022-1139(00)00323-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two 2-fluorophenyl-5-substitued cyclopropyl-1,3,4-oxadiazoles (IIIa-b) with cis/trans isomers were synthesized from the corresponding hydrazide (Ia) and aroyl chlorides by two-step reactions. Six asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-aryl-1,3,4-oxadiazoles (IIIc- h) were obtained by one step reaction of 2,4-dichloro-5-fluorobenzoic acid hydrazide (Ic) with the corresponding aromatic carboxylic acid in the presence of phosphorus oxychloride under reflux. However, the similar reaction of 4-fluorophenoxyacetic acid hydrazide (Ib) with 2,4-dichloro-5-fluorobenzoic acid failed to yield the desired asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-(fluorophenoxymethyl)-1,3,4-oxadiazole, and the resulting product was characterized as symmetric al 2,5-bis(2,4-dichloro-5-fluorophenyl) -1,3,4-oxadiazole (DCFPO). A possible reaction mechanism is suggested. Insecticidal activities of these nine new compounds against armyworms (Pseudaletia separata Walker) were determined. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：173 / 179

页数：7