Synthesis, crystal structure, insecticidal activity and DFT study on the geometry and vibration of O-(E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethyleneamino-O-ethyl-O-phenylphosphorothioate.
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.
Shi
De-Qing
DQ
Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China. chshidq@mail.ccnu.edu.cn
Zhu
Xiao-Fei
XF
Song
Yuan-Zhi
YZ
D000691:Anabasine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001042:Aphids; D018360:Crystallography, X-Ray; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063086:Organothiophosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D040102:Tetranychidae; D013816:Thermodynamics; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D007306:Insecticides; C539278:O-(E)-1-(1-((6-chloropyridin-3-yl)methyl)-5-methyl-1H-1,2,3-triazol-4-yl)ethyleneamino-O-ethyl-O-phenylphosphorothioate; D063086:Organothiophosphates; D011725:Pyridines; D014230:Triazoles; D000691:Anabasine