title: Discovery of cyantraniliprole, a potent and selective anthranilic diamide ryanodine receptor activator with cross-spectrum insecticidal activity.
abstract: Anthranilic diamides are an exceptionally active class of insect control chemistry that selectively activates insect ryanodine receptors causing mortality from uncontrolled release of calcium ion stores in muscle cells. Work in this area led to the successful commercialization of chlorantraniliprole for control of Lepidoptera and other insect pests at very low application rates. In search of lower logP analogs with improved plant systemic properties, exploration of cyano-substituted anthranilic diamides culminated in the discovery of a second product candidate, cyantraniliprole, having excellent activity against a wide range of pests from multiple insect orders. Here we report on the chemistry, biology and structure-activity trends for a series of cyanoanthranilic diamides from which cyantraniliprole was selected for commercial development.
authors.affiliation: DuPont Crop Protection, Stine-Haskell Research Center, 1094 Elkton Road, Newark, DE 19711, USA. Electronic address: thomas.p.selby@usa.dupont.com.
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Selby
authors.forename: George P
authors.initials: GP
authors.lastname: Lahm
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Stevenson
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Hughes
authors.forename: Daniel
authors.initials: D
authors.lastname: Cordova
authors.forename: I Billy
authors.initials: IB
authors.lastname: Annan
authors.forename: James D
authors.initials: JD
authors.lastname: Barry
authors.forename: Eric A
authors.initials: EA
authors.lastname: Benner
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Currie
authors.forename: Thomas F
authors.initials: TF
authors.lastname: Pahutski
mesh_terms: D000818:Animals; D001042:Aphids; D015220:Calcium Channels / Q000737:chemistry*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry*; D007915:Lepidoptera; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D019837:Ryanodine Receptor Calcium Release Channel / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D015220:Calcium Channels; D007306:Insecticides; D011720:Pyrazoles; D019837:Ryanodine Receptor Calcium Release Channel; D062367:ortho-Aminobenzoates; C558219:cyantraniliprole
keywords: Anthranilic diamides; Calcium channels; Chlorantraniliprole; Cyantraniliprole; Ryanodine receptor