Regioselective Claisen–Schmidt Adduct of 2-Undecanone from Houttuynia cordata Thunb as Insecticide/Repellent against Solenopsis invicta and Repositioning Plant Fungicides against Colletotrichum fragariae

Kurmanbayeva A. Ospanov M. Tamang P. Shah F.M. Ali A. Ibrahim Z.M.A. Cantrell C.L. Dinara S. Datkhayev U. Khan I.A. Ibrahim M.A.
August 2023 Multidisciplinary Digital Publishing Institute (MDPI)

Molecules
2023 #28 Issue 16

The U.S. Department of Agriculture (USDA) has established research programs to fight the phytopathogen Colletotrichum fragariae and the invasive red imported fire ant, Solenopsis invicta. C. fragariae is known to cause anthracnose disease in fruits and vegetables, while S. invicta is known for its aggressive behavior and painful stings and for being the cause of significant damage to crops, as well as harm to humans and animals. Many plants have been studied for potential activity against C. fragariae and S. invicta. Among the studied plants, Houttuynia cordata Thunb has been shown to contain 2-undecanone, which h is known for its antifungal activity against Colletotrichum gloesporioides. Based on the mean amount of sand removed, 2-undecanone showed significant repellency at 62.5 µg/g, similar to DEET (N,N-diethyl-meta-toluamide), against S. invicta. The 2-Undecanone with an LC₅₀ of 44.59 µg/g showed toxicity against S. invicta workers. However, neither H. cordata extract nor 2-undecanone had shown activity against C. fragariae despite their known activity against C. gloesporioides, which in turn motivates us in repositioning 2-undecanone as a selected candidate for a Claisen–Schmidt condensation that enables access to several analogs (2a–f). Among the prepared analogs, (E)-1-(3-methylbenzo[b]thiophen-2-yl)dodec-1-en-3-one (2b) and (E)-1-(5-bromothiophen-2-yl)dodec-1-en-3-one (2f) showed promising activity against C. fragariae, revealing a distinctive structural activity relationship (SAR). The generated analogs revealed a clear regioselectivity pattern through forming the C=C alkene bond at position C-1. These data open the window for further lead optimization and product development in the context of managing C. fragariae and S. invicta.

2-undecanone , Claisen condensation , Colletotrichum fragariae , Houttuynia cordata Thunb , Solenopsis invicta

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National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, 38677, MS, United States
Department of Organization, Management and Economics of Pharmacy and Clinical Pharmacy, School of Pharmacy, S.D. Asfendiyarov Kazakh National Medical University, Almaty, 050012, Kazakhstan
USDA-ARS, Natural Products Utilization Research Unit, University, 38677, MS, United States
General Studies, University of Mississippi, University, 38677, MS, United States
The National Academy of Science, Republic of Kazakhstan, Almaty, 050010, Kazakhstan

National Center for Natural Products Research
Department of Organization
USDA-ARS
General Studies
The National Academy of Science

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