Synthesis and anti-juvenile hormone activity of ethyl 4-(2-aryloxyhexyloxy) benzoates

• Published in: Bioscience, biotechnology, and biochemistry Vol. 70; no. 3; pp. 746 - 748
• Main Authors: Furuta, K.(Kyushu Univ., Fukuoka (Japan). Faculty of Agriculture), Shirahashi, H, Yamashita, H, Ashibe, K, Kuwano, E
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.03.2006; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: Animals; ANTAGONISTAS DE LAS HORMONAS; ANTAGONISTE D'HORMONE; anti-juvenile hormone; AROMATIC COMPOUNDS; Benzoates - chemical synthesis; Benzoates - chemistry; Benzoates - pharmacology; Biological and medical sciences; Bombyx - drug effects; Bombyx - growth & development; Bombyx - metabolism; CHEMICAL SYNTHESIS; COMPOSE AROMATIQUE; COMPUESTOS AROMATICOS; Fundamental and applied biological sciences. Psychology; HORMONAS JUVENILES; HORMONE ANTAGONISTS; HORMONE JUVENILE; JUVENILE HORMONES; Juvenile Hormones - antagonists & inhibitors; Larva - drug effects; Larva - growth & development; Larva - metabolism; Molecular Structure; Oxidation-Reduction; precocious metamorphosis; silkworm; SINTESIS QUIMICA; Structure-Activity Relationship; SYNTHESE CHIMIQUE; Benzoate; anti-juvenile hormone; silkworm; precocious metamorphosis; Juvenile hormone
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.70.746

A series of ethyl 4-(2-aryloxyhexyloxy)benzoates was prepared and tested for their activity to induce precocious metamorphosis in larvae of the silkworm. Phenyl analog 5 showed activity comparable to that of the 6methyl-3-pyridyl analog reported as a novel anti-JH agent. The activity of 5 could be fully counteracted by methoprene, a JH agonist. The ethoxycarbonyl group of 5 was essential for its activity.