TY - JOUR
T1 - Syntheses and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles
AU - Shi, Wei
AU - Qian, Xuhong
AU - Song, Gonghua
AU - Zhang, Rong
AU - Li, Rongpo
PY - 2000/12
Y1 - 2000/12
N2 - 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 symmetrical 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.
AB - 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 symmetrical 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.
KW - 1,3,4-Oxadiazoles
KW - Armyworm
KW - Cis/trans isomers
KW - Fluoroaryl
KW - Insecticidal activity
KW - One step reaction
UR - https://www.scopus.com/pages/publications/0006249377
U2 - 10.1016/S0022-1139(00)00323-7
DO - 10.1016/S0022-1139(00)00323-7
M3 - 文章
AN - SCOPUS:0006249377
SN - 0022-1139
VL - 106
SP - 173
EP - 179
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
IS - 2
ER -