Synthesis And Primary Biological Activity Of N-nitro-n,n'-diphenyl Urea Derivatives

N-nitro-N,N'-diphenyl Urea Derivatives are double efficiency compounds which have the plant growth regulating activity and fungicidal activity. In order to enlarge the screening range and look for higher activity and more efficiency compounds, we synthesized 12 compounds of N-nitro-N,N'-diphenyl Urea Derivatives by one pot way method. Excepting compounds D and F other synthesized compounds were not reported before. The structures of obtained compounds were identified by ~1HNMR, infra-red spectrum and elementary analysis. And the structures are showed below:The N-nitro-N,N'-diphenyl Urea were obtained by one pot way based on N-nitro-2,4,6-trichloroaniline using triphosgene as acylating agent. The synthesis technological conditions were discussed.The plant growth regulating activity and the herbicidal activity of the compounds were tested by plate method. The result indicated that: when in higher consistency, the compounds had inhibitory function to the plant; however, in lower consistency, the compounds showed some growth regulating function to the plant. And the synthesized compounds had an inhibitory function to the rhizome of amaranth.The CoMFA method was accepted to the compounds based on the herbicidal activity to amaranth. And the quantum chemistry calculation of the compounds was studied. The results suggests that the weeding activity of the compounds became higher when the smaller capacity electronegative functional group was introduced to the 3-position or the bigger capacity electropositive functional group was leaded in the 4-position of the benzene substituent which was on the right of urea-bridge.The fungicidal activities of the compounds A-I were tested by agar dilution method. The results suggest that those compounds had some fungicidal activities to testing germ. The compounds' inhibitory effect to Rhizoctonia solani was superior to the other two bacterias.The PM3 method in Gussian03 package was accepted to do the quantum chemistrycalculation based on the fungicidal activities datas of compounds A-I to Rhizoctonia solani. And the potential active sites were discussed. The results indicated that the special structure of urea-bridge in the compounds was the chemical fundamentals of fungicidal activity.