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.
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.
Tsukiyama
Takahiro
T
Agroscience Research Laboratories, Crop Protection Company, Sankyo Co., Ltd., 1041 Yasu, Yasu-cho, Yasu-gun, Shiga 520-2342, Japan. tukiya@yasu.sankyo.co.jp
Tsukamoto
Yoshihisa
Y
Suemoto
Hitomi
H
Okamoto
Yoshihiro
Y
Tamagawa
Yasushi
Y
Kinoshita
Ayako
A
Ichinose
Reiji
R
Sato
Kazuo
K
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
C476257:27-hydroxymilbemycin A3; C476258:27-hydroxymilbemycin A4; C476255:27-oxomilbemycin A3; C476256:27-oxomilbemycin A4; D000871:Anthelmintics; D018942:Macrolides