Shi De-Qing, Zhu Xiao-Fei, Song Yuan-Zhi
Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Spectrochim Acta A Mol Biomol Spectrosc. 2008 Dec 1;71(3):1011-20. doi: 10.1016/j.saa.2008.02.045. Epub 2008 Mar 18.
The title compound, O-(E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethyleneamino-O-ethyl-O-phenylphosphorothioate, has been synthesized via the condensation reaction of 1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone oxime and O-ethyl-O-phenylphosphorochloridothioate in the presence of NaOH powder in refluxing EtOH. Its structure was characterized by (1)H NMR, FTIR, Raman, elemental analysis and X-ray single crystal diffraction. The results of preliminary bioassays indicated that the title compound displays good insecticidal activity. Density functional (DFT) calculations have been carried out for the title compound by using the Becke-Lee-Yang-Parr's three-parameter hybrid functional (B3LYP) method at 6-31G and 6-31G basis sets. The calculated results show that the predicted geometry can well reproduce the structural parameters. The vibrational wave numbers of the title compound were calculated at same level. Predicted vibrational frequencies have been assigned and compared with experimental IR and Raman spectra and they are supported each other.
标题化合物O-(E)-1-{1-[(6-氯吡啶-3-基)甲基]-5-甲基-1H-1,2,3-三唑-4-基}乙烯氨基-O-乙基-O-苯基硫代磷酸酯，是通过1-{1-[(6-氯吡啶-3-基)甲基]-5-甲基-1H-1,2,3-三唑-4-基}乙酮肟与O-乙基-O-苯基硫代磷酰氯在氢氧化钠粉末存在下于回流乙醇中发生缩合反应合成的。其结构通过(1)H NMR、FTIR、拉曼光谱、元素分析和X射线单晶衍射进行了表征。初步生物测定结果表明，该标题化合物具有良好的杀虫活性。使用Becke-Lee-Yang-Parr三参数混合泛函（B3LYP）方法在6-31G和6-31G基组水平上对标题化合物进行了密度泛函（DFT）计算。计算结果表明，预测的几何结构能够很好地再现结构参数。在相同水平上计算了标题化合物的振动波数。对预测的振动频率进行了归属，并与实验红外光谱和拉曼光谱进行了比较，二者相互印证。
