Synthesis and fungicidal activity of macrolactams and macrolactones with an oxime ether side chain.
Three series of novel macrolactams 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 Z and 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 Kühn. 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-O-) 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.
Huang
Jia-Xing
JX
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing, People's Republic of China.
Jia
Yue-Mei
YM
Liang
Xiao-Mei
XM
Zhu
Wei-Juan
WJ
Zhang
Jian-Jun
JJ
Dong
Yan-Hong
YH
Yuan
Hui-Zu
HZ
Qi
Shu-Hua
SH
Wu
Jin-Ping
JP
Chen
Fu-Heng
FH
Wang
Dao-Quan
DQ
D005659:Fungicides, Industrial / Q000494:pharmacology*; D006860:Hydrogen Bonding; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000494:pharmacology*; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010091:Oximes / Q000737:chemistry*; D012232:Rhizoctonia / Q000187:drug effects; D013329:Structure-Activity Relationship
D005659:Fungicides, Industrial; D047029:Lactams, Macrocyclic; D007783:Lactones; D047028:Macrocyclic Compounds; D010091:Oximes