A series of novel 4-thiazolidinones (2–21) incorporating 2-(2,4,5-trichlorophenoxy)propanamide was synthesised. Reaction of 2-(2,4,5-trichlorophenoxy)propanohydrazide (1) with the corresponding carbonyl compounds afforded 2-(2,4,5-trichlorophenoxy)propanehydrazide hydrazones (2–11) which upon reaction with thioglycolic acid revealed 4-thiazolidinone derivatives (12–21). Structure elucidation of the synthesised compounds was done based on analytical and spectral data. The newly synthesised compounds were evaluated for their antimicrobial activity. Compounds 13 and 17 showed the equipotent activity with MIC value 6.25 lg ml-1 compared with chloramphenicol as reference drug. Docking studies of the promising compounds was done on MurB using Dock6.4 docking program to study their observed activity.