Structure-activity relationship for the insect antifeedant activity of benzofuran derivatives

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 5, 1999, Pages 840-846

  Morimoto, Masanori ^a   Urakawa, Masamitsu ^a   Fujitaka, Tatsuo ^a   Komai, Koichiro ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

2,3 dihydrobenzofuran; Insect antifeedant; Spodoptera litura; Structure activity relationship

Indexed keywords

EID: 0012513316     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.840     Document Type: Article

References (16)

1. Allan, R. D., Correll, R. L., and Wells, R. J., A new class of qui-nones from certain members of the family Cyperaceae. Tetrahedron Lett., 4669-4672 (1969).
2. i5quinones from Cyperus species. Tetrahedron Lett., 3-5 (1973).
3. Toong, Y. C., Schooley D. A., and Baker, F. C., Isolation of insect juvenile hormone III from a plant. Nature, 333, 170-171 (1998).
4. Dadang, Ohsawa, K., Kato, S., and Yamamoto, I., Insecticidal compound in tuber of Cyperus rotundus L. against the diamon-dback moth larvae. J. Pesticide Sci., 21, 444-446 (1996).
5. Morimoto, M., Fujii, Y., and Komai, K., Antifeedants in Cyper-aceae: Coumaran and Quinones from Cyperus spp. Phytochemistry, in press (1999).
6. Yamaguchi, S., Takai, M., Hanazome, I., Okada, Y., and Kawase, Y., Synthesis and structural studies of remirol. Bull. Chem. Soc. Jpn., 60, 3603-3605 (1987).
7. Tokuda, M., Miura, N., Yoshioka, K., Karasawa, T., Fujita, H., and Suginome, H., Convenient isoprenylation of aldehydes and ketones: Synthesis of (±)-ipsdienol and (±)-ipsenol. Synthesis, 1086-1088 (1993).
8. Yamaguchi, S., Kondo, S., Shimokawa, K., Inoue, O., Sannmomiya, M., and Kawase, Y., The synthesis of racemic fomannoxin, anodendroic acid, and 5-acetyl-2-[l-(hydrox-ymethyl)vinyl]-2,3-dihydroxybenzofuran. Bull. Chem. Soc. Jpn., 55, 2500-2503 (1982).
9. Horie, T., Kobayashi, T., Kawamura, Y., Yoshida, I., Tominaga, H., and Yamashita, K., Studies of the selective O-alkylation and dealkylation of flavonoids. XVIII. A convenient method for synthesizing 3,5,6,7-tetrahydroxyflavones. Bull. Chem. Soc. Jpn., 68, 2033-2041 (1995).
10. Escoubas, P., Lajide, L., and Mizutani, J., An improved leaf-disk antifeedant bioassay and its application for the screening of Hokkaido plants. Entomol. Exp. Appl., 66, 99-107 (1993).
11. Bonner, W. A., and DeGraw Jr., J. I., Ketones from “white snakeroot” Eupatorium urticaefolium. Tetrahedron, 18, 1295-1309 (1962).
12. Isman, M. B., Proksch, P., and Yan, J.-Y., Insecticidal chro-menes from the Asteraceae: structure-activity relations. Entomol. Exp. Appl., 43, 87-93 (1987).
13. Yano, K. and Tanaka, N., Antifeedant activity toward larvae of Pieris rapae crucivora of aromatic carbonyl compounds related to capillin isolated from Artemisia capillaris. Biosci. Biotechnol. Biochem., 59, 1130-1132 (1995).
14. Ueno, H., Miyoshi, H., Inoue, M., Niidome, Y., and Iwamura, H., Structural factors of rotenone required for inhibition of various NADH-ubiquinone oxidoreductases. Biochim. Biophys. Acta, 1276, 195-202 (1996).
15. Lane, G. A., Biggs, D. R., Russell, G. B., Sutherland, O. R. W., Williams, E. M., Maindonald, J. H., and Donnell, D. J., Isoflavonoid feeding deterrents for Costelytra zealandica structure-activity relationships. J. Chem. Ecol., 11, 1713-1735 (1985).
16. Klocke, J. A., Balandrin, M. F., Barnby, M. A., and Yamasaki, R. B., Limonoids, phenolics, and furanocoumarins as insect an-tifeedants, repellents, and growth inhibitory compounds. ACS Symposium Series, vol. 387, American Chemical Society, Washington DC, pp. 136-149 (1989)