Synthesis, Biological Activities And3D-QSAR Of N-nitro-N-phenyl Amide Derivatives

Amide herbicides are widely used all over the world because of their good selectivity and high efficacy, and this kind of pharmacy is easily degraded in plants, and harmless to mammals. In order to find the herbicide with high activity and low toxicity, we synthesized32kinds of N-nitro-N-(2,4,6-trisubstituted phenyl)-phenoxy acetamides and N-ntro-N-(2,4,6-trisubstituted phenyl)-furan glyoxamides by splicing the activity substructures together. Then, herbicidal and plant growth regulating activities of them were evaluated. On the base of that, we studied the herbicidal3D-QSAR. And the role of the target enzyme of the compounds was also researched.The main contents of this paper include the following aspects:Nitrifying the2,4,6-trisubstituted aniline to the N-nitro-2,4,6-tri-substituted aniline as an active substructure, the phenoxy acetyl chloride or furan aldehydes chloride as the other active substructure respectively. Ethyl acetate as solvent, triethylamine or sodium hydride as the acid binding agent respectively, we synthesized the target compounds includes23N-nitro-N-(2,4,6-trisubstituted)-phenoxy acetamides and9N-nitro-N-(2,4,6-tri-substituted phenyl)-furan glyoxamides. The structures of the target compounds were characterized by IR and H NMR.We tested the inhibitory activity of the target compounds aim at the root and hypocotyl of S. sudanenses and A. albus. And the promoting effect of the target compounds aim at the root and hypocotyl of rice and rapeseed were also tested. On the whole, the inhibitory activity of N-nitro-N-(2,4,6-trisubstituted)-phenoxy acetamides is much more better than N-nitro-N-(2,4,6-trisubstituted phenyl)-furan glyoxamides, and for S. sudanenses the inhibitory activity on hypocotyl is better man root. While for A. albus, it is just in contrast with S. sudanenses. At the concentration of0.1mg/L, both of the two series of the compounds can promote the growth of rice and rapeseed, with the increasing of the concentration, it will show inhibitory effect.We extracted the ALS enzyme from corn seedling, and tested the inhibitory activity of the target compounds aim at this enzyme. Our research shows that the IC50of N-nitro-N-(2,4,6-tri-substituted)-phenoxy acetamides is almost greater man100mg/L, while at the concentration of200mg/L, the inhibition rate of N-nitro-N-(2,4,6-tri-substituted phenyl)-ruran glyoxamides is lower than30%. As a result of that, we can not say that the target of the compounds is the ALS, it needs to be researched deeper.We studied the3D-QSAR on N-nitro-N-(2,4,6-tri-substituted)-phenoxy acetamides with their herbicidal activity. The model established was confidence and had a certain predictive ability.