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New fluorinated 1,2,4-triazin-4-ones  2 – 24  have been prepared using straightforward approaches. The reaction of 4-amino-3-mercapto-6-(trifluoromethyl)-1,2,4-triazin-5(4 H )-one ( 2 ) with aromatic aldehydes produced 4-((4-substitutedbenzylidene)amino)-3-mercapto-6-(trifluoromethyl)-1,2,4-triazin-5(4 H )-ones ( 5–9 ), which were cyclized by thioglycolic acid to give 2-(4-subsitiutedphenyl)-3-(3-mercapto-5-oxo-6-(trifluoromethyl)-1,2,4-triazin-4(5 H )-yl)thiazolidin-4-ones ( 10–14 ). 7-Methyl-3-(trifluoromethyl)-4 H -[1, 3, 4]thiadiazolo[2,3- c ][1, 2, 4]triazin-4-one ( 4 ) was synthesized by the condensation of  2  with acetaldehyde or by reaction with cyano compounds, followed by self-cyclization in dry benzene. Cyclization of compound  2  by reaction with aromatic acids yielded 7-substitutedphenyl-3-(trifluoromethyl)-4 H -[1, 3, 4]thiadiazolo[2,3-c][1, 2, 4]triazin-4-ones ( 15–19 ). Reaction of compound  2  with cyanamide produced 1-(4-oxo-3-(trifluoromethyl)-4 H -[1, 3, 4]thiadiazolo[2,3-c][1, 2, 4]triazin-7-yl)guanidine ( 20 ). Alkylation of compound  2  with phenacyl bromide produced 4-amino-3-((2-oxo-2-phenylethyl)thio)-6-(trifluoromethyl)-1,2,4-triazin-5(4 H )-one ( 21 ) which upon heating in the same media furnished 7-phenyl-3-(trifluoromethyl)-4 H ,8 H -[1, 2, 4]triazino[3,4-b][1, 3, 4]thiadiazin-4-one ( 22 ). The reaction of Schiff′s bases  5  or  6  with phenacyl bromide gave 8-benzoyl-7-(4-halophenyl)-3-(trifluoromethyl)-4 H ,8 H -[1, 2, 4]triazino[3,4-b][1, 3, 4]thiadiazin-4-ones ( 23–24 ). All of the newly synthesized compounds were characterized by spectral measurements and elemental analysis. The biological evaluation was also described. All compounds were screened for antibacterial, antifungal, and anti-biofilm activities. The findings confirm that the fluorinated 1,2,4-triazin-4-ones appear to be promising compounds as antibacterial, antifungal, and anti-biofilm agents.

Synthesis, reactivity, antimicrobial, and anti-biofilm evaluation of fluorinated 4-amino-3-mercapto-1,2,4-triazin-5(4 H )-one and their derivatives