Synthesis And Biological Activities Of α-aminophosphonate Derivatives Containing N-heterocycles

In order to search for efficient and low toxicity pesticidal lead compounds, we designed and synthesized four series of new compounds by bringing 1,2,3-triazole,1,2,3-thiadiazole,pyrimidine or 1,2,4-triazolo[1,5-a]pyrimidine moieties intoα-amino-phosphonatesanalogue framework according to the principle of bioactive substructure and bioisoteric relationships. Their structures of the target compounds have been confirmed by ¹H NMR, and elemental analyses. Some of them were also determined by MS, IR spectroscopy,³¹P NMR or X-ray crystallography. Their structures are listed as follows:(1)O,O'-dialkyl(orphenyl)-N-{3-[(6-chloropyridin-3-yl)methyl]-5-cyano-3H-1,2,3-triazol-4 -yl}-1-amino (substitutedphenyl) methyl phosphonates(2) O,O'-diethyl-N-(4-methyl-1,2,3-thiadiazole-5-carbonyl)-1-amino-1-substituted phenyl methyl phosphonates(3) O,O'-dialkyl(or phenyl) [2-(4,6-dimethoxypyrimidin-2-yIoxy)phenyl]-N-(substituted phenyl)-1-amino-methyl phosphonates (4) O,O'-dialkyl N-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yloxy)benzoyl]-1 -amino-(substitutedphenyl) methyl phosphonatesThe preliminary biological activities of the new compounds mentioned were evaluated. The results showed that some of them exhibited some extents of herbicidal activities.