Synthesis and antibacterial activity of 2-alkylcarbamato/trichloromethyl/chloroethoxy/aryloxy-1,2,3,4-tetrahydro-1,3,2-benzodiazaphosphorine 2-oxides

Several 2-trichloromethyl/2-chloroethoxy/2-aryloxy-1,2,3,4-tetrahydro-1,3,2 -benzodiazaphosphorine 2-oxides (4a-d), and 2-alkyl/alkenyl/alkynylcarbamat o 2-oxides (7a-f) have been synthesized from reactions of equimolar quantit ies of 2-aminobenzylamine (2) with various aryl or alkyl phosphorodichlorid ates (3b-d), trichloromethylphosphonic dichloride (3a) and dichlorophosphin yl carbamates (6a-f) at 40-50 degrees C in dry toluene in the presence of t riethylamine. IR, H-1, C-13, P-31 NMR and mass spectral analyses were colle cted and analyzed and supported all structures. The title compounds weve sc reened for antibacterial activity against Bacillus subtilis and Escherichia coli. Several of the agents exhibited significant activity in the assays. (C) 2000 John Wiley & Sons, Inc.