Synthesis and antimicrobial activity of 2,10-dichloro-6-substituted-4,8-dinitro-12H- dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides/sulfides

Novel 2,10-dichloro-6-substituted-4,8-dinitro-12H-dibenzo[d,g][1,3,2]dioxap hosphocin 6-oxides (4a-h) were synthesized by reacting 5,5'-dichloro-3,3'-d initro-2,2'-dihydroxydiphenylmethane (2) with different aryl phosphorodichl oridates (3a-g) or bis(2-chloroethyl)phosphoramidic dichloride (3h) in the presence of triethylamine at 55-60 degreesC, and the compounds 4i-I were pr epared by reacting the 2,6,10-trichloro-4,8-dinitro-12H-dibenzo[d,g][1,3,2] dioxaphosphocin 6-sulfide (5) in situ with substituted phenols and thiophen ol 5 was prepared by condensing 2 with thiophosphoryl chloride. IR, H-1, C- 13, P-31 NMR, and mass spectra supported all the proposed structures. Sever al title compounds exhibited significant activity in the assays against the bacteria Bacillus subtilis and Escherichia coli and fungi Curvularia lunat a and Aspergillus niger. (C) 2001 John Wiley & Sons, Inc.