title: The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides.
abstract: The evolution of the insecticidal pyrazoline moiety that was originally discovered in 1972 has led to the discovery of a new crop insecticide, indoxacarb, which is the first commercialized pyrazoline-type sodium-channel blocker. Both monocyclic and fused-tricyclic pyrazolines and pyridazines, as well as structurally related semicarbazones were examined prior to the discovery of analogous tricyclic oxadiazines which had similarly high activity as well as favorable environmental dissipation rates and low toxicity to non-target organisms. The eventual leading candidate, DPX-JW062, was originally obtained as a racemic molecule, but a chiral synthesis was developed which produces material that is 50% ee in the insecticidal (+)-S-enantiomer (DPX-MP062, indoxacarb).
authors.affiliation: DuPont Crop Protection Products, Stine-Haskell Research Center, PO Box 30, Newark, DE 19714, USA. stephen.f.mccann@usa.dupont.com
authors.forename: S F
authors.initials: SF
authors.lastname: McCann
authors.forename: G D
authors.initials: GD
authors.lastname: Annis
authors.forename: R
authors.initials: R
authors.lastname: Shapiro
authors.forename: D W
authors.initials: DW
authors.lastname: Piotrowski
authors.forename: G P
authors.initials: GP
authors.lastname: Lahm
authors.forename: J K
authors.initials: JK
authors.lastname: Long
authors.forename: K C
authors.initials: KC
authors.lastname: Lee
authors.forename: M M
authors.initials: MM
authors.lastname: Hughes
authors.forename: B J
authors.initials: BJ
authors.lastname: Myers
authors.forename: S M
authors.initials: SM
authors.lastname: Griswold
authors.forename: B M
authors.initials: BM
authors.lastname: Reeves
authors.forename: R W
authors.initials: RW
authors.lastname: March
authors.forename: P L
authors.initials: PL
authors.lastname: Sharpe
authors.forename: P
authors.initials: P
authors.lastname: Lowder
authors.forename: W E
authors.initials: WE
authors.lastname: Barnette
authors.forename: K D
authors.initials: KD
authors.lastname: Wing
mesh_terms: D000818:Animals; D001673:Biodegradation, Environmental; D018360:Crystallography, X-Ray; D006540:Herbicides / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D007536:Isomerism; D007915:Lepidoptera / Q000187:drug effects; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D011724:Pyridazines / Q000737:chemistry; D012664:Semicarbazones / Q000032:analysis; D013329:Structure-Activity Relationship; D014227:Triazines
chemical_list: D006540:Herbicides; D007306:Insecticides; D010078:Oxazines; D011724:Pyridazines; D012664:Semicarbazones; D014227:Triazines; C401104:indoxacarb