1. Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden.
- Author
-
Muehlebach M, Boeger M, Cederbaum F, Cornes D, Friedmann AA, Glock J, Niderman T, Stoller A, and Wagner T
- Subjects
- Crystallography, X-Ray, Drug Discovery, Herbicides chemical synthesis, Herbicides pharmacology, Heterocyclic Compounds, 2-Ring chemical synthesis, Heterocyclic Compounds, 2-Ring pharmacology, Hydrazines chemical synthesis, Molecular Conformation, Structure-Activity Relationship, Aza Compounds chemistry, Edible Grain growth & development, Herbicides chemistry, Heterocyclic Compounds, 2-Ring chemistry, Hydrazines chemistry, Spiro Compounds chemistry
- Abstract
Derivatives of the new class of 3-hydroxy-4-phenyl-5-oxo-pyrazolines were optimized towards both herbicidal activity on key annual grass weed species and selectivity in small grain cereal crops. The generic structure can be separated into three parts for the analysis of the structure-activity relationships, namely the aryl, the dione with its prodrug forms and the hydrazine moiety. Each area appears to play distinct and different roles in overall expression of biological performance which is further beneficially influenced by adjuvant response and safener action. Pinoxaden 6, a novel graminicide for use in wheat and barley incorporating a [1,4,5]oxadiazepane ring, eventually emerged as a development candidate from the discovery and optimization process.
- Published
- 2009
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