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Bioorg Med Chem Lett ; 23(23): 6341-5, 2013 Dec 01.
Article in English | MEDLINE | ID: mdl-24135728

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.


Subject(s)
Calcium Channels/chemistry , Insecticides/chemistry , Pyrazoles/chemistry , Ryanodine Receptor Calcium Release Channel/metabolism , ortho-Aminobenzoates/chemistry , Animals , Aphids , Insecticides/chemical synthesis , Lepidoptera , Molecular Structure , Pyrazoles/chemical synthesis , Ryanodine Receptor Calcium Release Channel/chemistry , Structure-Activity Relationship , ortho-Aminobenzoates/chemical synthesis
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