Cantharidin-Based Verbenone Derivatives as a Novel Insecticide against Plutella xylostella: Design, Synthesis, Insecticidal Activity Evaluation, and 3D QSAR Study

Kwanshik Lee, Hossam Nada, Minkyoung Kim, Hyejun Park, Kiho Lee, Dongho Seo, Kyeong Lee, Yongseok Choi

Research output: Contribution to journalArticlepeer-review

Abstract

The diamondback moth is a detrimental insect pest of brassicaceous crops which was among the first crop insects to be reported as DDT resistant. It has since proven to be significantly resistant to nearly every synthetic insecticide used in the field in many crucifer-producing regions. Due to insecticide control failures in some parts of the world, economically viable crucifer production is now all but impossible. As a result, there has been an increasing effort to identify new compounds with strong pesticidal activity. Cantharidin is one such compound that has been shown to be highly effective against a variety of insect pests. However, its chemical synthesis and potential toxicity to non-target organisms have been a major source of concern. Herein, using rational design approaches, a new series of cantharidin-based verbenone derivatives were synthesized and evaluated for their insecticidal activities against the diamondback moth. Among different compounds screened, compounds 6a, 6h, 6i, and 6q emerged as the most potent compounds exhibiting 100% mortality at a concentration of 100 mg/L after four days. These compounds demonstrated a good anti-feeding effect against the diamondback moth on cabbage leaves. Subsequently, a 3D QSAR study was carried out to identify the key structural features of the synthesized compounds and their correlation with insecticidal activity.

Original languageEnglish
Article number1272
JournalBiomolecules
Volume13
Issue number8
DOIs
Publication statusPublished - 2023 Aug

Bibliographical note

Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (2018R1A5A2023127) and (No. 2023R1A2C3004599) and the BK21 FOUR program funded by the Ministry of Education of Korea through NRF. This research was also supported by a Korea University Grant (K2220661).

Publisher Copyright:
© 2023 by the authors.

Keywords

  • 3D QSAR
  • cantharidin
  • diamondback moth
  • insecticide
  • synthesis
  • verbenone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

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