Synthesis and biological activities of 4-(phenazine-1-carboloxyl)cinnamic acid esters and N-phenazine-1-carboxyl-N′-(substituted)-cinnamyl ethylenediamins

The phenazine-1-carboxylic acid was modified by esterification and nucleophilic substitution of acyl from different substituted cinnamic acid, two series of phenazine-1-carboxylate derivatives containing cinnamic acid segments 5a - 5f and phenazine-1-formamide derivatives 10a - 10r were synthesized. The structures of these derivatives were confirmed by ¹H NMR, ¹³C NMR and high resolution mass spectrometry. The fungicidal activity and herbicidal activitiy of the target compounds were determined by mycelium growth rate method and culture dish method. The results of fungicidal activity assay showed that most phenazine-1-carboxylate derivatives had good inhibitory effect on Pyricularia oryzae at the concentration of 0.20 mmol/L, and the inhibitory rate of compound 5a was 78.37%, it was slightly lower than phenazine-1-carboxylic acid (86.91%). The results of herbicidal activity assay showed that the inhibition rates of 10b , 10e and 10f on the root length of rape were more than 80%, and the inhibitory effect of 10e on rape was similar to that of butachlor at the concentration of 0.50 mmol/L. The target compound synthesized in this paper not only has certain fungicidal activity, but also has good herbicidal activity, the herbicidal activity of some target compounds is similar to that of control agents, this study provides a new idea for the structural modification of phenazine-1-carboxylic acid.