Discovery of cyantraniliprole, a potent and selective anthranilic diamide ryanodine receptor activator with cross-spectrum insecticidal activity
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- 作者：Thomas P. Selby ; George P. Lahm ; Thomas M. Stevenson ; Kenneth A. Hughes ; Daniel Cordova ; I. Billy Annan ; James D. Barry ; Eric A. Benner ; Martin J. Currie ; Thomas F. Pahutski
- 关键词：Ryanodine receptor ; Anthranilic diamides ; Chlorantraniliprole ; Cyantraniliprole ; Calcium channels
- 刊名：Bioorganic and Medicinal Chemistry Letters
- 出版年：1 December, 2013
- 年：2013
- 卷：23
- 期：23
- 页码：6341-6345
- 全文大小：846 K
文摘
Anthranilic diamides are an exceptionally active class of insect control chemistry that selectively activates insect ryanodine receptors causing mortality from uncontrolled release of calcium ion stores in muscle cells. Work in this area led to the successful commercialization of chlorantraniliprole for control of Lepidoptera and other insect pests at very low application rates. In search of lower log P analogs with improved plant systemic properties, exploration of cyano-substituted anthranilic diamides culminated in the discovery of a second product candidate, cyantraniliprole, having excellent activity against a wide range of pests from multiple insect orders. Here we report on the chemistry, biology and structure-activity trends for a series of cyanoanthranilic diamides from which cyantraniliprole was selected for commercial development.