Synthesis of pyripyropene derivatives and their pest-control efficacy.

Journal of pesticide science (2019-11-30)
Kimihiko Goto, Ryo Horikoshi, Satoshi Nakamura, Masaaki Mitomi, Kazuhiko Oyama, Tomoyasu Hirose, Toshiaki Sunazuka, Satoshi Ōmura
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Chlorfenapyr, PESTANAL®, analytical standard

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