SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 2-SUBSTITUTED-2,3-DIHYDRO-5-THIOPHENOXY-1H-1,3,2-BENZODIAZAPHOSPHOLE 2-OXIDES

Several 2-aryloxy-2,3-dihydro-5-thiophenoxy-1N-1,3,2-benzodiazaphosphole 2-oxides 3a-c, trichloromethyl-2.3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide (3d), and 2-chloroethoxy-2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide (3e), and 2-alkylcarbamato-2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxides 6have been synthesized from reactions of equimolar quantities of 4-thiophenoxy-1,2-phenylenediamine (1) with various aryl or alkyl phosphorodichloridates 2a-c,e, trichloromethylphosphonc dichloride (2d), and dichlorophosphinyl carbamates 5a-e at 50-65 degrees C in dry toluene in the presence of triethylamine. Substituted ureas of the type RR'P(O)NHC(O)NHR" 8a,b were obtained via a reaction of 1 with chlorides 7a,b of arylcarbamidophosphoric acids. Oxidation of a few of the title compounds with H2O2 in acetic acid gave the corresponding sulfones 9a-d. IR, H-1 NMR, C-13 NMR, P-31 NMR, and mass spectral analyses, were collected and analyzed and supported ail structures. Some compounds were screened for antifungal activity against Curvularia lunata and Aspergillus niger and for antibacterial activity against Bacillus subtilis and Klebsiella pneumoniae. Several of the agents exhibited significant activity in the assays.