title: Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden.
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.
authors.affiliation: Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse, CH-4332 Stein, Switzerland. michel.muehlebach@syngenta.com
authors.forename: Michel
authors.initials: M
authors.lastname: Muehlebach
authors.forename: Manfred
authors.initials: M
authors.lastname: Boeger
authors.forename: Fredrik
authors.initials: F
authors.lastname: Cederbaum
authors.forename: Derek
authors.initials: D
authors.lastname: Cornes
authors.forename: Adrian A
authors.initials: AA
authors.lastname: Friedmann
authors.forename: Jutta
authors.initials: J
authors.lastname: Glock
authors.forename: Thierry
authors.initials: T
authors.lastname: Niderman
authors.forename: André
authors.initials: A
authors.lastname: Stoller
authors.forename: Trixie
authors.initials: T
authors.lastname: Wagner
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D055808:Drug Discovery; D002523:Edible Grain / Q000254:growth & development; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D001372:Aza Compounds; D006540:Herbicides; D006574:Heterocyclic Compounds, 2-Ring; D006834:Hydrazines; D013141:Spiro Compounds; C029424:hydrazine; C542519:pinoxaden