Synthesis And Biological Activities Of N-heterocyclic Compounds Containing α-aminophosphonate Moieties

Aminophosphonic acids and their esters are the phosphorus analogues of natural amino acids. their.derivatives, one of the focuses in the research and development of agrochemicals, have been found to show wide biological activities and are widely used as insecticides, fungicides, herbicides and pharmaceuticals.With the aim to find out novel herbicide lead compounds, we designed and synthesized two series of new compounds containing N- heterocycles by bringing a-amino phosphonate moiety into carboxamide framework according to the principle of combination of bioactive substructure and bioisoteric relationships. We also designed and synthesized one series of new compounds by bringingα-aminophosphonate moiety into aryloxyphenoxypropionates framework containing 4,6- dimethoxypyrimidine. We also designed and synthesized one series of new compounds by bringing pyrazol and thiazole moieties intoα-amino phosphonate framework via the Mannich type reaction catalysed by Lewis acid. Their structures are listed as follows:(1) O,O'-Diethy {1-[Chlorothiazolyl(or chloropyridinyl)]methyl-5-methyl-1H-1,2,3-triazol-4-yl carbonyl }-1-amino-substituted benzyl phosphonate I-6(12 compounds)(2) O,O'-Dialkyl (2,4-dimethyl thiazole-5-yl carbonyl)-1-amino-substituted benzyl phosphonateⅡ-3 (9 compounds)(3) O,O'-Dialkyl {2-[4-(4,6-dimethoxy pyrimidin-2-yl oxy) phenoxy]-2-substituted acetyl }-1-amino-substituted benzyl phosphonateⅢ-4 (17 compounds) (4) O,O'-Dialkyl (phenyl) N-[5-(ethoxycarbonyl)-4-methylthiazol-2-yl]- (1-phenyl-3 -substituted-5 -substituted-1H-pyrazol-4-yl)-1-aminomethylphosphonateⅣ-4 (10 compounds)Their structures of the target compounds have been confirmed by H NMR, EI-MS, IR spectroscopy and elemental analyses. Some of them were also determined by ¹³C NMR,³¹PNMR.In addition, the preliminary biological activities of the new compounds mentioned were evaluated. The results showed that some of them exhibited certain herbicidal activities.