Synthesis of biologically active phenoxy derivatives of substituted benzothiazole organophosphates

The reaction of S‐(phenyl benzothiazolyl‐2)phosphorodichloridothioate/phosphorodichloridodithioate with 2 mol of phenol/4‐chlorophenol/4‐nitrophenol in the presence of stoichiometric amounts of triethylamine in dry THF/CH₂Cl₂ has afforded a series of the corresponding organophosphate phenoxy derivatives ( 1a , 1b , 2a , 2b , and 3a , 3b ). Plausible structures have been proposed on the basis of elemental analysis, IR, ¹H NMR, ³¹P NMR, and mass spectral studies. The antibacterial activity of these organophosphate phenoxy derivatives has been evaluated against pathogenic bacteria Staphylococcus aureus (+ve) and Escherichia coli (−ve). The antifungal activity of these organophosphate phenoxy derivatives has been evaluated against pathogenic fungi Aspergillus niger and Fusarium oxysporium. The results indicate that organophosphate phenoxy derivatives are found more active than the parent compounds. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:84–88, 2010; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20582