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Bioscience, Biotechnology, and Biochemistry Volume 67, 2003 - Issue 9
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Original Articles

Ethyl 4-[2-(6-Methyl-3-pyridyloxy)butyloxy]benzoate, a Novel Anti-juvenile Hormone Agent

Hanae ISHIGUROLaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu UniversityFukuoka 812-8581, Japan
,
Norihiro FUJITALaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu UniversityFukuoka 812-8581, Japan
,
In-Hae KIMLaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu UniversityFukuoka 812-8581, Japan
,
Takahiro SHIOTSUKILaboratory of Insect Growth Regulation, Developmental Biology Department, National Institute of Agrobiological SciencesTsukuba, Ibaraki 305-8634, Japan
&
Eiichi KUWANOLaboratory of Pesticide Chemistry, Department of Applied Genetics and Pest Management, Faculty of Agriculture, Kyushu UniversityFukuoka 812-8581, Japan
Pages 2045-2047 | Received 23 Apr 2003, Accepted 23 May 2003, 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 regulators 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) Kim, I.-H., Ishiguro, H., and Kuwano, E., 2-Methyl-5-pyridyl 2-(substituted-phenoxy)ethyl ethers with precocious metamorphosis-inducing activity. J. Pesticide Sci., 26, 390-392 (2001).
  • 6) Compound 2: 1H-NMR (400 MHz, CDCl3, TMS) δ: 1.06 (3H, t, J=7.3 Hz), 1.37 (3H, t, J=7.2 Hz), 1.84-1.88 (2H, m), 2.50 (3H, s), 4.12-4.21 (2H, m), 4.34 (2H, q, J=7.2 Hz), 4.50-4.53 (1H, m), 6.90 (2H, d, J=8.5 Hz), 7.07 (1H, d, J=8.4 Hz), 7.20 (1H, d, d, J=2.9, 8.4 Hz), 7.98 (2H, d, J=8.5 Hz), 8.26 (1H, d, J=2.9 Hz). Anal. Found: C, 69.28; H, 7.10; N; 4.33%. Calcd. for C19H23NO4: C, 69.30; H, 6.99; N; 4.26%.
  • 7) Kim, I.-H., and Kuwano, E., Synthesis and structure-activity relationships of 6-methyl-3-pyridyl ethers as anti-juvenile hormone agents. J. Fac. Agr., Kyushu Univ., 47, 395-405 (2003).
  • 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) Kuwano, E., Hisano, T., Sonoda, M., and Eto, M., Effects of methoprene and 20-hydroxyecdysone on the precocious metamorphosis induced by 1,5-disubstituted imidazoles. Biosci. Biotechnol. Biochem., 58, 1309-1310 (1994).
  • 10) Ohashi, M., Tsusue, M., and Kiguchi, K., Juvenile hormone control of larval colouration in the silkworm, Bombyx mori: Characterization and determination of epidermal brown colour induced by the hormone. Insect Biochem., 13, 123-127 (1983).

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