Synthesis and Fungicidal Activity of Macroiactams and Macrolactones with an Oxime Ether Side Chain

摘要

Three series of novel macroiactams and macrolactones - 12-alkoxyimino-tetradecanlactam,12-alkoxyiminopentadecanlactam,and 12-alkoxyiminodecanlactone derivatives (7A,7B,and 7C) - were synthesized from corresponding 12-oxomacrolactams and 12-oxomacrolactone.Their structures were confirmed by ~1H NMR and elemental analysis.The Zand E isomers of 7A and 7B were separated,and their configurations were determined by ~1H NMR.These compounds showed fair to excellent fungicidal activities against Rhizoctonia solani Kiihn.It is interesting that the Z and E isomers of most of the compounds have quite different fungicidal activities.The fact that the compounds have a gradual increase of fungicidal activity in the order of 7A,7C,and 7B indicated that the macrocyclic derivatives with a hydrogen-bonding acceptor (=N-0-) and a hydrogen-bonding donor (-CONH-) on the ring,and a three methylenes distance (CH2CH2CH2) between these two functional groups,exhibited the best fungicidal activity.The bioassay also showed that 7B not only has good fungicidal activity but also may have a broad spectrum of fungicidal activities.