Fifteen N-(substituted phenyl)-halogeno-o-hydroxybenzylamines were synthesized through halogeno-salicylaldehyde condensation with aromatic amines and reduction with NaBH4, respectively, and fourteen compounds of them are novel. The structures of all the compounds have been confirmed by 1H NMR, IR, MS techniques and elemental analysis. The result of preliminary bioassay showed that the title compounds had 100% inhibitory rate against Monilia albican at 0.05% mass concentration and a favorable extent of antibacterial activities against Escherichia coli and Staphylococcus aureus. This kind of com-pounds have obvious specificity antibacterial activities against different bacteria and they would be a good choice of antibacterial compounds against fungi. The analysis of structure-activity relationship showed that the antibacterial activities of title compounds were enhanced by the halogen groups but reduced by strong electron-donating and electron-withdrawing groups of the arylamine rings, such as NO2, OCH3. The types and numbers of halogen atoms on the hydroxyphenyl rings had impact on the antibacterial activities of title compounds, and 5-bromo-compounds had better antibacterial activities against Escherichia coli than 5-chloro and 3,5-dibromo-compounds.

Key words: N-(substituted phenyl)-halogeno-o-hydroxybenzylamine, synthesis, characterization, antibacterial activity, structure-activity relationship