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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 structures that can kill harmful fungi that destroy fruit crops. These compounds were made more efficiently using microwave heating and tested against two major crop pathogens that cause billions of dollars in losses annually. The most promising compound (A) proved even more effective than commercial fungicides at stopping fungal growth and spore germination. This research could lead to better, safer alternatives for protecting crops from fungal diseases.

Background

Indole-containing molecules have multiple biological applications and represent a promising alternative for controlling phytopathogens affecting fruit quality. Fruit rot diseases caused by filamentous fungi such as Monilinia fructicola and Botrytis cinerea cause significant annual crop losses and have developed resistance to conventional fungicides. Bromoindole derivatives have shown potential antifungal properties in agricultural contexts.

Objective

To synthesize eleven 3-acyl-5-bromoindole derivatives using microwave-assisted Friedel-Crafts acylation and evaluate their antifungal capacity against Monilinia fructicola and Botrytis cinerea through in vitro assays and molecular docking studies on succinate dehydrogenase (SDH).

Results

Compounds A, B, G, and L inhibited M. fructicola growth, while A and J showed activity against B. cinerea. Compound A achieved the lowest EC50 value (7.91 µg/mL) against M. fructicola and 12.17 µg/mL against B. cinerea, outperforming commercial fungicides. Acylation improved conidial germination inhibition, with compound L achieving 81% inhibition for M. fructicola. Molecular docking showed compounds A, B, and G had favorable binding energies with SDH.

Conclusion

Compounds A, B, G, J, and L show promise as novel agrochemicals for controlling phytopathogenic fungi. Compound A demonstrated remarkable antifungal activity against both pathogens, while derivatives improved conidial inhibition. These findings suggest potential for developing effective alternatives to conventional fungicides with resistance management benefits.
  • Published in:International Journal of Molecular Sciences,
  • Study Type:Experimental Research,
  • Source: 10.3390/ijms26189148, PMID: 41009710
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