A series of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles were synthesized starting from 3-(2,4-dichloro-5-fluorophenyl)-4H-1,2,4-triazole-3-thiol. The newly synthesized compounds were characterized by IR, 1H NMR, mass and elemental analysis. Some of the synthesized compounds were tested for their anti-inflammatory, analgesic and antimicrobial activities. Compounds 8c, 8d and 8h exhibited excellent anti-inflammatory activity whereas compounds 8d, 8e and 8h showed excellent analgesic activity. Compounds 8a, 8c-e, and 8h exhibited good antibacterial activity and compounds 8c, 8e and 8h showed good antifungal activity.