First Discovery of Insecticidal Activity of 9,9鈥?Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure鈥揂ctivity Relationship

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• 作者：Tuti Wukirsari ; Hisashi Nishiwaki ; Ayaka Hasebe ; Yoshihiro Shuto ; Satoshi Yamauchi
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2013
• 出版时间：May 8, 2013
• 年：2013
• 卷：61
• 期：18
• 页码：4318-4325
• 全文大小：300K
• 年卷期：v.61,no.18(May 8, 2013)
• ISSN：1520-5118

文摘

The insecticidal activity of (-)-(8R,8鈥?i>R)-3,3鈥?dimethoxy-9,9鈥?epoxylignane-4,4鈥?diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8鈥?i>R)-stereoisomer. In the course of research into structure鈥揳ctivity relationships involving 30 newly synthesized (8R,8鈥?i>R)-derivatives, 5-fold higher activity (ED₅₀ = 0.91 nmol/fly) was observed for (鈭?-(8R,8鈥?i>R)-3,3鈥?4-trimethoxy-9,9鈥?epoxylignan-4鈥?ol (21) than for the naturally occurring compound (1). The activity of 1 was weaker than that of (鈭?-(8R,8鈥?i>R)-dihydroguaiaretic acid ((鈭?-DGA) (4); however, compound 21 showed almost the same level of activity as 4.

Keywords:

lignan; 9,9鈥?epoxylignane; 3,4-divanillyltetrahydrofuran; dihydroguaiaretic acid; structure鈭抋ctivity relationship (SAR)