title: Synthesis of 27-oxo, 27-hydroxymilbemycins A3 and A4 and novel 27-alkoxymilbemycins A3 and A4 from milbemycins A3 and A4 and their acaricidal activities.
abstract: 27-Oxomilbemycins A3 and A4 and 27-hydroxymilbemycins A3 and A4 were identified as metabolites in soil metabolism studies of milbemycins A3 and A4. Chemical derivation methods were developed to synthesize 27-oxomilbemycins A3 and A4 and 27-hydroxymilbemycins A3 and A4 from milbemycins A3 and A4. In addition, 27-alkoxymilbemycin derivatives were also synthesized from the same precursors. Some of the synthesized compounds displayed satisfactory acaricidal activity against the organophosphorus-sensitive two-spotted spider mite (Tetranychus urticae), but did not have superior activity to corresponding milbemycins A3 and A4.
authors.affiliation: Agroscience Research Laboratories, Crop Protection Company, Sankyo Co., Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, Japan. tukiya@yasu.sankyo.co.jp
authors.forename: Takahiro
authors.initials: T
authors.lastname: Tsukiyama
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Tsukamoto
authors.forename: Hitomi
authors.initials: H
authors.lastname: Suemoto
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Okamoto
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Tamagawa
authors.forename: Ayako
authors.initials: A
authors.lastname: Kinoshita
authors.forename: Reiji
authors.initials: R
authors.lastname: Ichinose
authors.forename: Kazuo
authors.initials: K
authors.lastname: Sato
mesh_terms: D000871:Anthelmintics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D040102:Tetranychidae / Q000187:drug effects
chemical_list: C476257:27-hydroxymilbemycin A3; C476258:27-hydroxymilbemycin A4; C476255:27-oxomilbemycin A3; C476256:27-oxomilbemycin A4; D000871:Anthelmintics; D018942:Macrolides