title: Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: chemistry and biology of the cereal herbicide pinoxaden.
abstract: BACKGROUND
  Pinoxaden is a new cereal herbicide that provides outstanding levels of post-emergence activity against a broad spectrum of grass weed species for worldwide selective use in both wheat and barley.
  
  
  RESULTS
  Factors influencing activity and tolerance to pinoxaden were in part linked to distinct structural parts of the active ingredient. Three complementary contributions that decisively impact upon the herbicidal potency against grasses were identified: a preferred 2,6-diethyl-4-methyl aromatic substitution pattern, a dione area suitable for proherbicide formation and beneficial adjuvant effects. The uptake and translocation pattern of pinoxaden when coapplied with its tailored adjuvant were analysed by autoradiography, indicating extensive and rapid penetration, followed by effective distribution throughout the plant. Crop injury reduction on incorporation of the [1,4,5]oxadiazepane ring into the aryldione template was reinforced with safener technology. Comparative studies on the behaviour of pinoxaden applied either alone or in combination with the safener cloquintocet-mexyl demonstrated that addition of the safener resulted in significant enhancement of metabolic degradation in wheat and barley, providing excellent crop tolerance and a substantial selectivity margin without adverse effects on weed control.
  
  
  CONCLUSIONS
  The biological potential of pinoxaden and its active principle pinoxaden dione in terms of grass weed control and tolerance in cereals was fully exploited by inclusion of the safener cloquintocet-mexyl in the formulation in combination with a specific and tailor-made tank-mix adjuvant based on methylated rape seed oil.
authors.affiliation: Syngenta Crop Protection Münchwilen AG, Stein, Switzerland. michel.muehlebach@syngenta.com
authors.forename: Michel
authors.initials: M
authors.lastname: Muehlebach
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: Gavin
authors.initials: G
authors.lastname: Hall
authors.forename: Adriano F
authors.initials: AF
authors.lastname: Indolese
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Kloer
authors.forename: Gael
authors.initials: G
authors.lastname: Le Goupil
authors.forename: Thomas
authors.initials: T
authors.lastname: Maetzke
authors.forename: Hans
authors.initials: H
authors.lastname: Meier
authors.forename: Rudolf
authors.initials: R
authors.lastname: Schneider
authors.forename: André
authors.initials: A
authors.lastname: Stoller
authors.forename: Henry
authors.initials: H
authors.lastname: Szczepanski
authors.forename: Sebastian
authors.initials: S
authors.lastname: Wendeborn
authors.forename: Hansjuerg
authors.initials: H
authors.lastname: Widmer
mesh_terms: D000277:Adjuvants, Pharmaceutic / Q000737:chemistry / Q000494:pharmacology; D001345:Autoradiography; D018360:Crystallography, X-Ray; D053209:Herbicide Resistance; D006540:Herbicides / Q000737:chemistry* / Q000494:pharmacology; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry* / Q000494:pharmacology; D057685:Plant Weeds / Q000187:drug effects; D006109:Poaceae / Q000187:drug effects*; D011804:Quinolines / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D058728:Weed Control
chemical_list: D000277:Adjuvants, Pharmaceutic; D006540:Herbicides; D006574:Heterocyclic Compounds, 2-Ring; D011804:Quinolines; C514515:cloquintocet-mexyl; C542519:pinoxaden