Research Ferrocenyl 1,2,4-triazole Mannich Base Derivatives Were Synthesized And Performance

First,4-amino-5-ferrocenyl-4#-1,2,4-triazole-3-thiol(4)was synthesized, using ferrocene carboxylic acid as the starting material, through four steps:esterification; hydrazide;into salt; cyclization.The reaction conditions of the synthesis of4was optimizated on the basis of existing research, and the new melting point and1H NMR and HRMS was determined.Five kinds of Schiff bases derivatives5(a-e)were synthesized at first time, using4reacted with cinnamyl aldehyde;2-furan aldehyde;2-pyridine aldehyde;p-fluorobe-nzaldehyde and p-chlo-robenzaldehyde, respectively. Fifteen kinds of Mannich bases derivatives6(a-e)-(1-5) were synthesized at first time, using Schiff derivatives reacted with morpholine,N-methyl piperazine or piperazine, respectively. These newly compounds were characterized by melting point, IR and1H NMR.Second, the biological activity of the target compound Schiff bases derivatives5(a-e)and Mannich bases derivatives6(a-e)-(1-5)were explored:1.The plant growth regulatory activity: the cell division activity was explored with the method of cucumber cotyledon test, at a concentration of10mg/L, all the compounds showed certain promoting activities except6a-1, the promoting activities are mostly for A grade, the promoting effect of the compound6e-1reached as high as92.9%, the compounds possess good cell division activity; the auxin activity was explored with the method of wheat malt sheath, at a concentration of10mg/L,6b-2,6b-3showed a certain inhibition effect, others showed a certain promoting activity,5a and6b-3is for B grade, others showed promoting effect for C or D grade.2.Herbicidal activity (Inhibition of the root growth of Rape):at a concentration of10mg/L, excepted the compounds6b-3and6e-3showed promoting activity, others almost showed good herbicidal activity,6a-2showed the best inhibitory activity, the inhibition rate reached as high as99.50%.3.The activity of inhibition CDC25B of15kinds of Mannich bases derivatives was screend, the experimental results showed that there are14kinds showed good inhibitory activity, and12kinds of them showed inhibition rate is higher than98%.Third, electrochemical activity study of the target compound Schiff bases derivatives5(a-e):Graphene modified glassy carbon electrode as working electrode, Britton-Robison buffer solution to regulate pH, with the method of cyclic voltammetry, how the influence of pH on the electrochemical behavior of the compound5(a-e)was studied, the results showed that when pH=2or3, the compound5(a-d) process good reversibility. Under optimal pH conditions, how the influence of sweep speed and concentration on the electrochemical behavior of the compound5(a-d)was studied.The results demonstrated that oxidation peak current(Ipc)showed good linear relationship with the scanning speed and the electrochemical behavior of compounds5(a-d)was a adsorption-diffusion controlled reversible process. When the concentration equal to10-3、0.5×10-3、10-4、0.5×10-4and10-5mol/L, it had a good linear relationship with oxidation peak current, and the minimum detectability was10-5mol/L.The result provides the value for reference when the compound5(a-d) was used as the pesticide in agriculture.