Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden.
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.
Muehlebach
Michel
M
Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse, CH-4332 Stein, Switzerland. michel.muehlebach@syngenta.com
Boeger
Manfred
M
Cederbaum
Fredrik
F
Cornes
Derek
D
Friedmann
Adrian A
AA
Glock
Jutta
J
Niderman
Thierry
T
Stoller
André
A
Wagner
Trixie
T
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
D001372:Aza Compounds; D006540:Herbicides; D006574:Heterocyclic Compounds, 2-Ring; D006834:Hydrazines; D013141:Spiro Compounds; C029424:hydrazine; C542519:pinoxaden