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A series of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety were synthesised and their antimicrobial activities were evaluated. All the target compounds were characterised by  1 H NMR,  13 C NMR, ESI-MS, IR and elemental analyses. The single crystal structure of 3-((5-((2-fluorobenzyl)thio)-4-phenyl-4 H -1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-one ( VIIi ) was also determined. The preliminary bioassays indicated that some of the target compounds possessed good antimicrobial activities. For example, 3-((4-phenyl-5-((4-(trifluoromethyl)benzyl)thio)-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-one ( VIIs ) exhibited the best inhibitory effect against  Xanthomonas oryzae  pv.  oryzae and Xanthomonas axonopodis  pv.  citri  with the half-effective concentration (EC 50 ) values of 47.6 μg mL −1  and 22.1 μg mL −1 , respectively, which were superior to the commercial bactericide, bismerthiazol. Meanwhile, 3-((5-((4-chlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3 H )-one ( VIIh ) exhibited better fungicidal activities against  Pellicularia sasakii  and  Colletotrichum capsici  at the concentration of 50 μg mL −1 , in comparison with the commercial fungicide, hymexazol.

Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety