The reaction of perchlorophenyl carbonochloridodithioate 1 with 1, 2-phenylene diamine 2a or 1, 4-phenylene diamine 2b dissolved in DMF produced the aminophenylamino dithiocarbamate derivatives 3a, 3b. Aminophenylamino dithiocarbamate derivatives 3a, 3b, benzaldehyde 4a, and triphenyl phosphite 5, along with LiClO4 acting as a Lewis acid catalyst, were added to form α-aminophosphonate derivatives 6a, 6b. The interaction of cyanuric chloride 7 with 1, 2-phenylene diamine 2a or 1, 3-phenylene diamine 2c dissolved in acetone produced new 2, 4-diaminophenylaminotriazine derivatives 8a, 8b. In contrast, a one-pot reaction using the produced 2, 4-diaminophenylaminotriazine derivatives 8a, 8b, benzaldehyde 4a or m-chlorobenzaldehyde 4b, and triphenylphosphite 5 ,along with LiClO4 acting as a Lewis acid catalyst resulted in the synthesis of α-aminophosphonate derivatives 9a, 9b, 10a, 10b. All of the generated compounds' chemical structures were ascertained using the FT-IR, 1H-NMR, 13C-NMR, 31P-NMR, and mass spectroscopic techniques. Each synthesized compound was tested in vitro for its biological effectiveness against gram-positive bacteria, gram-negative bacteria, and fungi pathogens. Most synthesized compounds exhibited moderate to good antibacterial activity.