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An Efficient Microwave Synthesis of 3-Acyl-5-bromoindole Derivatives for Controlling Monilinia fructicola and Botrytis cinerea

Summary

Scientists created new chemical compounds based on indole molecules that can effectively kill two harmful fungi that destroy fruit crops. These compounds were made using microwave heating, which is faster and more efficient than traditional methods. Tests showed that some of these new compounds work even better than commercial fungicides at killing these fungi, and they may work by blocking an important energy-producing process in the fungal cells.

Background

Indole-containing molecules possess multiple biological applications and represent a promising alternative for controlling phytopathogens that threaten crop quality and food safety. Monilinia fructicola and Botrytis cinerea are among the most destructive fungal pathogens in agriculture, causing significant economic losses and developing resistance to conventional fungicides. The indole scaffold, particularly with bromine substitution, shows potential antifungal properties.

Objective

This study aimed to synthesize eleven 3-acyl-5-bromoindole derivatives through microwave-assisted Friedel-Crafts acylation and evaluate their antifungal capacity against M. fructicola and B. cinerea. Molecular docking studies on succinate dehydrogenase (SDH) were performed to explore potential mechanisms of action.

Results

Compounds A, B, G, and L inhibited M. fructicola growth, while only A and J showed activity against B. cinerea. Compound A achieved the lowest EC50 value against B. cinerea (12.17 µg/mL), surpassing commercial fungicides. Acylation derivatives improved conidial germination inhibition, with compound L achieving 81% inhibition in M. fructicola and compound J achieving 63% in B. cinerea. Molecular docking showed compounds A, B, and G exhibited favorable binding energies with SDH.

Conclusion

The microwave-assisted synthesis successfully produced novel 3-acyl-5-bromoindole derivatives with promising antifungal activity. Compounds A, B, G, J, and L represent promising candidates for future development of novel agrochemicals to combat plant pathogens, demonstrating both mycelial inhibition and conidial germination suppression capabilities.
  • Published in:International Journal of Molecular Sciences,
  • Study Type:Experimental Research,
  • Source: PMID: 41009710, DOI: 10.3390/ijms26189148
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