Synthesis and insecticidal activity of spinosyn analogs functionally altered at the 2′-, 3′- and 4′-positions of the rhamnose moiety

被引:10
作者
Creemer, LC
Kirst, HA
Paschal, JW
Worden, TV
机构
[1] Elanco Anim Hlth, Res & Dev, Greenfield, IN 46140 USA
[2] Lilly Corp Ctr, Lilly Res Labs, Indianapolis, IN 46285 USA
[3] Dow Agrosci Discovery & Field Res, Indianapolis, IN 46268 USA
关键词
D O I
10.7164/antibiotics.53.171
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
In an effort to increase the insecticidal activity of the spinosyn family of naturally occurring macrolides, the 2'-, 3'- and 4'-O-desmethyl-O-acetyl analogs and the 2'-, 3'-, and 4'-O-desmethoxy analogs have been synthesized. These analogs were prepared synthetically from the minor spinosyn factors H, J, K, L and Q either via direct acylation of the corresponding factor or deoxygenation of an intermediate xanthate. The acylated analogs were all more potent insecticides against Heliothis vivescens larvae than their respective parent factors, but not as potent as spinosyns A or D. The deoxy analogs were also more potent insecticides than their respective parent factors. The 2'-desmethoxy analogs showed, for the first time, analogs with insecticidal potency against H. virescens greater than that of spinosyns A and D, indicating that polarity is not well tolerated in the rhamnose moiety of spinosyn A.
引用
收藏
页码:171 / 178
页数:8
相关论文
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