Antifeedant and Termiticidal Activities of 6-Alkoxycoumarins and Related Analogs Against Coptotermes formosanus Shiraki

作者：Adfa Morina; Hattori Yosuke; Yoshimura Tsuyoshi; Komura Kenichi; Koketsu Mamoru^*

来源：Journal of Chemical Ecology, 2011, 37(6): 598-606.

DOI：10.1007/s10886-011-9968-6

• 6-alkoxycoumarins
• Coptotermes formosanus Shiraki
• 6-(2-pentynyloxy)coumarin
• 6-isobutoxycoumarin
• Antifeedant
• Termiticidal

We synthesized 23 6-alkoxycoumarin derivatives, 20 of which are novel compounds. The structures of all compounds were confirmed by NMR, MS, and elemental analysis, and their antifeedant and termiticidal activities against Coptotermes formosanus Shiraki were examined. In a no-choice test, 6-(2-pentynyloxy)coumarin (2v), 6-(2-butynyloxy)coumarin (2u), 6-(2-octynyloxy)coumarin (2w), and 6-methoxycoumarin (2a), demonstrated high termiticidal activity at a concentration of 10 mu mol. At a concentration of 5 mu mol, 6-(2-butynyloxy)coumarin (2u) produced the highest mortality among the compounds tested. On the other hand, all of the 6-alkoxycoumarins showed antifeedant activity at both concentrations, except 6-octadecyloxycoumarin (2j) that was inactive at 5 mu mol. Among the 23 compounds and the control, 6-ethoxycoumarin (2b), 6-isopropoxycoumarin (2d), and 6-isobutoxycoumarin (2f) exhibited the highest antifeedant activity with no mass loss (0.00%) at a concentration of 10 mu mol. Our findings indicate that the presence of alkenyloxy and alkynyloxy groups was important for the termiticidal activity, while the incorporation of alkoxy groups with longer alkyl chains tended to reduce both the termiticidal and antifeedant activities. Furthermore, short chain alkoxy and arylalkoxy-substituted analogs showed good antifeedant activity, but methoxy groups on the benzene ring had a negative effect.

• 出版日期2011-6