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m-Methylphenyl N-methylcarbamate 유도체들의 살충활성 메카니즘
박승희,남상길,성낙도 충남대학교 농업과학연구소 1995 농업과학연구 Vol.22 No.2
A Series of meta and para-substituted phenyl N-methylcarbamate derivatives were synthesized and influence of substituents(X) on the molecular orbital(MO) quantities of carbonyl group, carbamylation reaction center, and insecticidal activities(pI_50) were discussed quantitatively. From these findings, the most stable streo conformer(Z) shows that the planer phenyl group occupies vertical(θ=90˚) position on the plane of the N-methylcarbamyl group. The carbamylation mechanism was proposed that the carbamylation process of acetylcholinesterase(ACh.E) by m-methyl substituted phenyl N-methylcarbamate derivatives proceeds via hyperconjugation of m-methyl group and carbonyl oxygene protonation, theromodynamically control reaction with acidic site of ACh.E.