Studies On Bioactivity And Quantivitative Structure Activity Relationship Of N-phenylcarbamate Compounds

During Synthesizing Celangulins, a compound determined as Methyl N-phenylcarbamate was discovered accidentally which had strong knocking down activity against Mythimma separata. So far, N-phenylcarbamate compounds mostly were used as fungicide and herbicide, never a one used as insecticide. The systemic study on the quantiviative relationship of between activity and structure of N-phenylcarbamate compounds has not been carried out. This study was proceeded on synthesizing a series of N-phenylcarbamate compounds, bioassaying activities against several insect, fungius and weed targets and focused on 2D-QSAR and 3D-QSAR of compounds. The results are given as follows:1. Synthesized N-phenylcarbamate compounds exhibited obvious activities against Mythimma separata and Tetranychus viennensis.Of these compounds, 2,4-dinitryl N-phenylcarbamate was most effective, and had a LDso of 0.47 u g/larva2. The bioactivities of butyl N-phenylcarbamate against Mythimma separata had contact poison, no stomach and fumigant poison. The compound had a mortality of 86.6% against Plutella xylostella larval at the concentration of 25mg/ml by means of topical application. The compound also had a high activity against Mythimma separata with a mortality of 100% at the concentration of 0.1 mg/ml by means of residual film, or with a mortality of 97.3% at the concentration of 1.0 mg/ml by means of spray. Butyl N-phenylcarbamate was no obvious activity against Musca domestica Stitophilus zeamais Agrotis ypsilon Pieris brassicae Barathra brassicaeL Musca domestica Brevicoryne brassicae and Myzuspersicae.3. The elongation of root and sprout ofAmaranthus retroflexus and Polypogon fugax was inhibited significantly by the synthesized 20 compounds, but the germination of the tested seeds was not affected. 2-amyl N-phenylcarbamate had the strongest herbicidal activity against Amaranthus retroflexus with an ECso of 6.6 mg/L.4. Synthesized 20 compounds had obvious fungicidal activity against Glomerella Cingulata. Of these, 2-amyl N-phenylcarbamate was the strongest; its EC50was 17.12 mg/L.5. Single-variant regression analysis showed the bioactivities of N-phenylcarbamate compounds against insects fungi and weeds existed pertinence with aliment water parameter tridimensional parameter and electric parameter, ofwhich aliment water parameter was the most important factor; The smaller of aliment water parameter, the stronger of activity.6. Hansch equation also showed the bioactivities of N-phenylcarbamate compounds against insects fungi and weeds existed pertinence with reservation-time and tridimensional parameter, of which the reservation-time was the most important factor; the shorter of reservation-time, this is to say the bigger of polarity, the stronger of activity.7. The analysis of 3D-QSAR shows the bioactivities against weeds and fungi exist linearity correlation with ligand-receptor interaction-energy and furthermore approved that the sites of the real receptors should lies in hydrogen-bond offerorl, 3 active sites and hydrogen-bond receptor N atom of amine in 2 sites.