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Bioscience, Biotechnology, and Biochemistry Volume 70, 2006 - Issue 3
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Original Articles

Synthesis and Anti-Juvenile Hormone Activity of Ethyl 4-(2-Aryloxyhexyloxy)benzoates

Kenjiro FURUTALaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
,
Hiromitsu SHIRAHASHILaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
,
Haruna YAMASHITALaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
,
Kiyo ASHIBELaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
&
Eiichi KUWANOLaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu University
Pages 746-748 | Received 05 Oct 2005, Accepted 07 Nov 2005, Published online: 22 May 2014

  • 1) Riddiford, L. M., Cellular and molecular actions of juvenile hormone 1. General considerations and premetamorphic actions. Adv. Insect Physiol., 24, 213–274 (1994).
  • 2) Staal, G. B., Anti juvenile hormone agents. Ann. Rev. Entomol., 31, 391–429 (1986).
  • 3) Staal, G. B., Insect control with growth regulation interfering with the endocrine system. Entomol. Exp. Appl., 31, 15–23 (1982).
  • 4) Kiguchi, K., Mori, T., and Akai, H., Effects of anti-juvenile hormone “ETB” on the development and metamorphosis of the silkworm, Bombyx mori. J. Insect Physiol., 30, 499–506 (1984).
  • 5) Riddiford, L. M., Roseland, C. R., Thalberg, S., and Curtis, A. T., Actions of two juvenile hormone antagonists on lepidopteran epidermis. J. Insect Physiol., 29, 281–286 (1983).
  • 6) Ishiguro, H., Fujita, N., Kim, I.-H., Shiotsuki, T., and Kuwano, E., Ethyl 4-[2-(6-methyl-3-pyridyloxy)butyloxy]benzoate, a novel anti-juvenile hormone agent. Biosci. Biotechnol. Biochem., 67, 2045–2047 (2003).
  • 7) Fujita, N., Furuta, K., Shirahashi, H., Hong, S., Shiotsuki, T., and Kuwano, E., Synthesis and anti-juvenile hormone activity of ethyl 4-[2-(6-methyl-3-pyridyloxy)alkyloxy]benzoates. J. Pesticide Sci., 30, 192–198 (2005).
  • 8) Yoshida, T., Shiotsuki, T., and Kuwano, E., Synthesis and precocious metamorphosis-inducing activity of 3-(1-alkenyl)pyridines. J. Pesticide Sci., 25, 253–258 (2000).
  • 9) Compound 5: 1H-NMR (400 MHz, CDCl3, TMS) δ: 0.92 (3H, t, J=7.1 Hz), 1.38 (3H, t, J=7.2 Hz), 1.39–1.55 (4H, m), 1.80–1.84 (2H, m), 4.09–4.20 (2H, m), 4.33 (2H, q, J=7.2 Hz), 4.56–4.61 (1H, m), 6.89 (2H, d, J=8.7 Hz), 6.91–6.97 (2H, m), 7.24–7.31 (3H, m), 7.97 (2H, d, J=8.7 Hz). Anal. Found: C, 73.60; H, 7.62%. Calcd. for C21H26O4: C, 73.66; H, 7.65%.

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