Submitted to: Encyclopedia of Agrochemicals
Publication Type: Book / Chapter
Publication Acceptance Date: 12/18/2000
Publication Date: 1/15/2003
Interpretive Summary: This is a book chapter for the Encyclopedia of Agrochemicals edited by J. R.Plimmer, D. W. Gammon, N. N. Ragsdale, and T. Roberts. This manuscript presents the discovery of a novel class of herbicide based on a natural product structure, its use and the potential for developing more natural products-based pesticides.
Technical Abstract: Cinmethylin is an oxabicycloheptane derivative that is structurally similar to the natural monoterpene 1,4-cineole. This herbicide, and a number of structural analogues, has been developed over several decades, starting from the fortuitous discovery of herbicidally active derivatives of glycerol-3-phosphate being investigated as potential insecticides. Cinmethylin was developed as a preplant incorporated or preemergence herbicide for the control of grass weeds. The natural monoterpene 1,4-cineole and the synthetic herbicide analog cinmethylin affect the ability of plants to make asparagine. However, in vitro assays of asparagine synthetase demonstrate that the cinmethylin molecule does not inhibit this target site directly, but that it must be metabolized into its 1,4- cineole derivative to inhibit of asparagine synthetase.