Stereoselective synthesis and biological activities of O-(E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethyleneamino-O-ethyl-O-arylphosphorothioates

To find novel lead compounds having high insecticidal activity, a series of phosphorothioate derivatives containing 1,2,3-triazole and pyridine rings were synthesized by the reaction of 1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone oxime with phosphorochloridothioates. Their structures were confirmed by IR, 1H NMR, 31P NMR, mass spectrometry, and elemental analyses. The structure of 6c was determined by single crystal X-ray diffraction, which is thermodynamically stable E isomer. The results of preliminary bioassay indicate that some title compounds possess insecticidal activity to some extent. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:15–20, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20367