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

Abstract

Several 2-aryloxy-2,3-dihydro-5-thiophenoxy-1H−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-benzodizaphosphole 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, trichloromethyl-phosphonc dichloride (2d), and dichlorophosphinyl carbamates 5a-e at 50–65 °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 arylcar-bamidophosphoric acids. Oxidation of a few of the title compounds with H2O2 in acetic acid gave the corresponding sulfones 9a-d. IR, 1H NMR, 13CNMR,31PNMR, and mass spectral analyses, were collected and analyzed and supported all structures. Some compounds were screened for antifungal activity against Curvularia lunara and Aspergillus niger and for antibacterial activity against Bacillus subtilis and Klebsiella pneumoniae. Several of the agents exhibited significant activity in the assays.