Pest management science · 2026
Design, synthesis, and potential mechanism of novel carvone derivatives with dual fumigant and repellent activities.
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Yu Xiao, Cheng Yanqin, Ji Zhiqin, Wei Shaopeng
Аннотация
BACKGROUND: Conventional fumigants and repellents face challenges such as environmental toxicity, pesticide resistance, and neurotoxicity, necessitating the development of eco-friendly alternatives.
RESULTS: A series of 41 carvone derivatives (3a-3k, 5a-5l, 6a-6r) were successfully synthesized and characterized by proton (1H) nuclear magnetic resonance (NMR), carbon-13 (13C) NMR, and high-resolution mass spectrometry (HRMS). Bioactivity assays revealed significant fumigant and repellent efficacy of the target compounds. At 150 μL L-1, compounds 3h, 3i, and 3j achieved 100% fumigant mortality against Tribolium castaneum adults, comparable to ethyl formate. At 26.54 μg cm-2, compounds 3h and 5a exhibited a repellency rate of 100%, outperforming N,N-diethyl-m-toluamide (DEET, 92.0%). Structure-activity relationship (SAR) analysis highlighted the critical role of α-methyl substitution in carboxylic esters and matched stereochemistry (S/S or R/R) in enhancing activity. Preliminary mechanistic studies demonstrated that compound 3h significantly inhibits acetylcholinesterase (AChE) and ATPase. Molecular docking further revealed that compound 3h binds to the AChE active site via hydrogen bonding and hydrophobic interactions.
CONCLUSION: This study successfully identified a class of dual-functional carvone derivatives with robust fumigant and repellent properties, and preliminary mechanistic insights were established. These findings provide valuable lead compounds and a theoretical foundation for the development of next-generation fumigants and repellents. © 2026 Society of Chemical Industry.
RESULTS: A series of 41 carvone derivatives (3a-3k, 5a-5l, 6a-6r) were successfully synthesized and characterized by proton (1H) nuclear magnetic resonance (NMR), carbon-13 (13C) NMR, and high-resolution mass spectrometry (HRMS). Bioactivity assays revealed significant fumigant and repellent efficacy of the target compounds. At 150 μL L-1, compounds 3h, 3i, and 3j achieved 100% fumigant mortality against Tribolium castaneum adults, comparable to ethyl formate. At 26.54 μg cm-2, compounds 3h and 5a exhibited a repellency rate of 100%, outperforming N,N-diethyl-m-toluamide (DEET, 92.0%). Structure-activity relationship (SAR) analysis highlighted the critical role of α-methyl substitution in carboxylic esters and matched stereochemistry (S/S or R/R) in enhancing activity. Preliminary mechanistic studies demonstrated that compound 3h significantly inhibits acetylcholinesterase (AChE) and ATPase. Molecular docking further revealed that compound 3h binds to the AChE active site via hydrogen bonding and hydrophobic interactions.
CONCLUSION: This study successfully identified a class of dual-functional carvone derivatives with robust fumigant and repellent properties, and preliminary mechanistic insights were established. These findings provide valuable lead compounds and a theoretical foundation for the development of next-generation fumigants and repellents. © 2026 Society of Chemical Industry.