Synthesis and Chemometrics of Thymol and Carvacrol Derivatives as Larvicides against Aedes aegypti

• Main Authors: Viviane Barros Silva, Daniele Lima Travassos, Angelita Nepel, Andersson Barison, Emmanoel Vilaça Costa, Luciana Scotti, Marcus Tulius Scotti, rancisco Jaime Bezerra Mendonça-Junior, Roseli La Corte dos Santos, Sócrates Cabral de Holanda Cavalcanti
• Format: Article
• Language: English
• Published: Tehran University of Medical Sciences 2017-06-01
• Series: Journal of Arthropod-Borne Diseases
• Subjects: Chemometry; SAR; Dengue; Thymol derivatives; Carvacrol derivatives
• Online Access: https://jad.tums.ac.ir/index.php/jad/article/view/598

Background: Thymol and carvacrol have previously demonstrated larvicidal activity against Aedes aegypti (Diptera: Culicidae). In view of this fact, it was of our interest to obtain synthetic derivatives and evaluate their larvicidal ac­tivity on Ae. aegypti larvae. Methods: Structural modifications were performed on thymol and carvacrol in an effort to understand the functional groups necessary for modulating their activities and to lead possibly to more effective larvae control agents. The derivatives were further subjected to SAR and computational studies (molecular modeling and chemometric tools (CPCA and PCA)) to extract structural information regarding their larvicidal properties. Field collected and Rocke­feller populations of Ae. aegypti were used. Results: Carvacrol and thymol exhibited LC50 of 51 and 58ppm for field collected larvae, respectively. Carvacrol derivatives exhibited LC50 ranging from 39 to 169ppm, while thymol derivatives exhibited LC50 ranging from 18 to 465ppm. Substitution of the acidic proton of carvacrol by esters, ethers, and acetic acid resulted in either mainte­nance or reduction of potency. Conclusion: Thymol derivatives were, to a certain extent, more efficient larvicides against Ae. aegypti than carvacrol derivatives, particularly to Rockefeller larvae. The chemometrics tools applied in this study showed that the inde­pendent variables indicate a mixed profile. Nevertheless, hydrophobic interactions increased the larvicidal activity.