Synthesis and antimicrobial activity of 2-substituted-6-chloro-8-nitro-4-trichloromethyl-4H-1,3,2-benzodioxaphosphorin 2-oxides

A series of 2-aryloxy/2-arylthio-6-chloro-8-nitro-4-trichloromethyl-4H-1,3, 2-benzodioxaphosphorin 2-oxides 3 have been synthesized by reacting 2- (2,2 ,2-trichloro-1-hydroxyethyl)-4-chloro-6-nitrophenol 1 with different arylph osphorodichloridates 2 in the presence of triethylamine at 70-80 degreesC. Some of these compounds are prepared by reacting the monochloride, 2-chloro -6-chloro-8-nitro-4-trichloromethyl-4H-1, 3, 2-benzodioxaphosphorin 2-oxide 4, in situ with substituted phenol and thiols 5. The monochloride is prepa red by condensing 2- (2,2,2-trichloro-1-hydroxyethyl)-4-chloro-6-nitropheno l with phosphorus oxychloride. IR, H-1, C-13 and P-31 NMR and mass spectral data have been discussed. Some of these compounds have been screened for t heir antibacterial and antifungal activities.