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Design, synthesis, and antimicrobial evaluation of novel 1,2,4-triazole thioether derivatives with a 1,3,4-thiadiazole skeleton

Summary

Scientists created 17 new chemical compounds that can fight harmful fungi and bacteria that damage plants. One of these compounds, called 9d, proved to be even more effective than existing commercial pesticides at fighting plant diseases. Tests on kiwifruit showed that this new compound could protect and treat bacterial infections better than currently available treatments. These new compounds could help protect crops and reduce reliance on older pesticides.

Background

1,2,4-triazole and 1,3,4-thiadiazole are nitrogen-containing heterocyclic compounds with diverse biological activities including antibacterial and antifungal properties. These compounds have been extensively studied for agricultural and pharmaceutical applications. Natural products like gallic acid serve as valuable scaffolds for structural modification to develop novel antimicrobial agents.

Objective

To design and synthesize 17 novel 1,2,4-triazole thioether derivatives containing a 1,3,4-thiadiazole skeleton based on gallic acid. To evaluate their antifungal and antibacterial activities against plant pathogens and compare their efficacy with commercial fungicides and bactericides.

Results

Compound 9d demonstrated significantly superior antifungal activity with EC50 values of 9.25 μg/mL against TSM and 14.95 μg/mL against MSD, outperforming pyrimethanil. Compound 9d exhibited strong antibacterial activity against PSA with EC50 of 9.34 μg/mL, superior to thiodiazole copper (81.74 μg/mL). In vivo studies showed 59.39% curative and 79.33% protective activities at 200 μg/mL against PSA.

Conclusion

Novel 1,2,4-triazole thioether derivatives with 1,3,4-thiadiazole skeletons show promising antifungal and antibacterial activities against plant pathogens, with compound 9d demonstrating superior efficacy compared to commercial fungicides and bactericides. Molecular docking studies revealed that compound 9d interacts with FtsZ protein through hydrogen bonding with specific amino acid residues. These compounds represent viable alternatives for managing fungal and bacterial threats to plants.
  • Published in:RSC Advances,
  • Study Type:Experimental Research,
  • Source: PMID: 40778099
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