Synthesis and Herbicidal Activity of O,O-Dialkyl(phenyl)-N-{1-[(6-chloropyridin-3-yl)methyl]-4-cyano-1H-1,2,3-triazol-5-yl}-1-amino-1-substitutedbenzyl-phosphonates

Abstract

A series of novel α-amino phosphonate derivatives containing both pyridine and 1,2,3-triazole moieties 4 were synthesized via a multi-step reaction. First, the condensation of 5-amino-1-[(6-chloropyridin-3-yl) methyl]-4-cyano-1H-1,2,3-triazole with various aromatic aldehydes in the presence of magnesium perchlorate afforded imines 3 in moderate yields; second, imines 3 reacted with dialkyl phosphites or triphenyl phosphite to give the title compounds 4 in moderate to good yields. Their structures were elucidated by spectroscopic data (IR, 1H NMR, 31P NMR, ESI-MS) and elemental analysis. The preliminary bioassay (in vitro) indicated that some of the title compounds 4 possessed moderate herbicidal activities against dicotyledonous plants (Brassica campestris L) at a concentration of 100 mg/L. However, compounds 4 did not exhibit herbicidal activities against Brassica campestris L at a concentration of 10 mg/L.Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.GRAPHICAL ABSTRACT