Synthesis Of Guanidoethyl N-arylcarbamate Hydrochlorides,Ferrocenylethanone Imino N-arylcarbamates And Their Bioactivity Research

Active substructures combination is widely used in the new pesticide research. In our research, the substructures such as urethane group, guanidyl, ferrocenyl and ketoimine were used as basic structure units, and urethane group were respectively combined with guanidyl, ferrocenyl and ketoimine to form guanidoethyl N-arylcarbamate hydrochlorides (1) and ferrocenylethanone imino N-arylcarbamates (2), and 35 new compounds that had never been reported were synthesized (their structures as show in Fig.1). The structures of all the target compounds have been demonstrated by FT-IR and 1H NMR, and the structures of some of the target compounds have also been demonstrated by 13C NMR,19F NMR and MS, the results show that all the synthesized compounds are our desired compounds.Under the guidance of "pesticides guidelines for laboratory bioactivity tests-part 1: petri dish test for herbicide bioactivity", the herbicide bioactivity of the two classes target compounds were tested. Monocotyledons plants such as rice and barnyard grass (or zea mexicana) and dicotyledonous plants such as brassica napus and amaranthus albus were used as experimental plants. According to the test results, it can be concluded that guanidoethyl N-arylcarbamates played a good inhibition effect on the growth of the four experimental plants’ roots. The IC50 figures can be seen as useful parameters which can indicate the inhibition to the experimental plants’ roots, the IC50 figures for brassica napus range from 3.57 mg/L to 494.03 mg/L, and there are 9 compounds, the IC50 figures of which are below 50 mg/L; the IC50 figures for amaranthus albus range from 5.95 mg/L to 67.75 mg/L, and there are 18 compounds, the IC50 figures of which are below 50 mg/L; the IC50 figures for rice range from 25.99 mg/L to 391.73 mg/L, and there are 5 compounds, the IC50 figures of which are below 50 mg/L; the IC50 figures for zea mexicana are all above 50 mg/L and the minimum is 54.05 mg/L.To some extent, ferrocenylethanone imino N-arylcarbamates also play apparent inhibition effect on the growth of the experimental plants’ roots, the IC50 figures for rice range from 11.66 mg/L to 2007 mg/L, and there are 3 compounds, the IC50 figures of which are below 50 mg/L; the IC50 figures for barnyard grass range from 51.03 mg/L to 437.5 mg/L; the IC50 figures for amaranthus albus range from 49.75 mg/L to 141.5 mg/L; the IC50 figures for brassica napus range from 238.0 mg/L to 2251 mg/L.According to the two serials of compounds’ inhibition figures against the growth of brassica napus’ roots and amaranthus albus’ roots, the quantitative structure-activity relationship (3D-QSAR) analysis of the two serials target compounds was carried out by the way of comparative molecular field analysis (CoMFA), and the CoMFA models also were established.In the CoMFA model corresponding to brassica napus, cross-validated q2 value and non-cross-validated R2 value were respectively 0.608 and 0.869, and the contributions of steric and electrostatic fields to bioactivity were respectively 68.2% and 31.8%; In the CoMFA model corresponding to amaranthus albus, cross-validated q2 value and non-cross-validated R2 value were respectively 0.471 and 0.851, and the contributions of steric and electrostatic fields to bioactivity were respectively 52.1% and 47.9%.