Synthesis of pyripyropene derivatives and their pest-control efficacy

• Goto Kimihiko

  Agricultural & Veterinary Research Labs., Agricultural & Veterinary Division, Meiji Seika Pharma Co., Ltd.

• Horikoshi Ryo

  Agricultural & Veterinary Research Labs., Agricultural & Veterinary Division, Meiji Seika Pharma Co., Ltd.

• Nakamura Satoshi

  Agricultural & Veterinary Research Labs., Agricultural & Veterinary Division, Meiji Seika Pharma Co., Ltd.

• Mitomi Masaaki

  Agricultural & Veterinary Research Labs., Agricultural & Veterinary Division, Meiji Seika Pharma Co., Ltd.

• Oyama Kazuhiko

  Agricultural & Veterinary Research Labs., Agricultural & Veterinary Division, Meiji Seika Pharma Co., Ltd.

• Hirose Tomoyasu

  Graduate School of Infection Control Sciences, Kitasato Institute for Life Sciences, Kitasato University

• Sunazuka Toshiaki

  Graduate School of Infection Control Sciences, Kitasato Institute for Life Sciences, Kitasato University

• Ōmura Satoshi

  Graduate School of Infection Control Sciences, Kitasato Institute for Life Sciences, Kitasato University

Abstract

Pyripyropene A (PP-A), a secondary metabolite produced by filamentous fungi, shows insecticidal activity against agricultural insect pests. Synthesized PP derivatives also show a narrow insecticidal spectrum but high insecticidal activities against such sucking pests. PP-A has a low eco-toxicological impact and satisfies a prerequisite for next-generation insecticides. We investigated the effects of conversion of the 3-pyridyl and α-pyrone rings to other rings, as well as the effects of esterification, dehydration, and oxidization at the C-13 position in natural PP analogues, on the insecticidal activity and spectrum. The conversions of the 3-pyridyl and α-pyrone rings markedly reduced the insecticidal activity with a minimal impact on the spectrum, indicative of an important role for these rings in insecticidal activity. Some derivatives with modified structures at the C-13 position showed a higher inhibitory effect on the motility of canine heartworms and mosquito vectors than did PP-A, suggesting their utility as filaria control drugs.

Journal

• Journal of Pesticide Science

  Journal of Pesticide Science 44 (4), 255-263, 2019-11-20

  Pesticide Science Society of Japan

Keywords

• pyripyropene
• chemical conversion
• insecticidal
• microfilaria
• mosquito

Details

• CRID: 1390282752371544960
• NII Article ID: 130007748678
• NII Book ID: AA11818622
• DOI: 10.1584/jpestics.d19-032
• ISSN: 13490923
• ISSN: 03851559
• ISSN: 1348589X
• NDL BIB ID: 030091971
• Web Site: http://id.ndl.go.jp/bib/030091971
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030091971
• Web Site: https://www.jstage.jst.go.jp/article/jpestics/44/4/44_D19-032/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed