Synthesis, Biological Activities and DFT Calculation of a-Aminophosphonate Containing Cyclopropane Moiety
Xing-Hai Liu
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China ; State-Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin 300071, P.R. China
Jian-Quan Weng
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China
Cheng-Xia Tan
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P.R. China
Li Pan
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin 300071, P.R. China
Bao-Lei Wang
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin 300071, P.R. China
Zheng-Ming Li
State-Key Laboratory of Elemento-Organic Chemistry, National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin 300071, P.R. China
Corresponding Author(s) : Xing-Hai Liu
xhliu@zjut.edu.cn; nkzml@vip.163.com
Asian Journal of Chemistry,
Vol. 23 No. 9 (2011): Vol 23 Issue 9
Five new a-aminophosphonate derivatives containing cyclopropane moiety have been synthesized via conventional and microwave irradiation methods under solvent- and catalysis-free condition. The structures of the a-aminophosphonate compounds have been confirmed by 1H NMR, 31P NMR, FT-IR, EI-MS and FTICR-MS studies. Their herbicidal activities were evaluated in vivo and in vitro. The results showed some compounds were found to exhibit moderate herbicidal activities against Brassica campestris at 100 and 10 ppm. Theoretical calculation of 2c was carried out with B3LYP/6-31G (d,p). The full geometry optimization was carried out using 6-31G(d,p) basis set and the structure-activity relationship was also studied by frontier orbital energy.
