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The discovery of indoxacarb: oxadiazines as a new class of pyrazoline‐type insecticides
Author(s) -
McCann Stephen F,
Annis Gary D,
Shapiro Rafael,
Piotrowski David W,
Lahm George P,
Long Jeffery K,
Lee Kevin C,
Hughes Margaret M,
Myers Brian J,
Griswold Sandra M,
Reeves Bonita M,
March Robert W,
Sharpe Paula L,
Lowder Patrick,
Barnette William E,
Wing Keith D
Publication year - 2001
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o
Subject(s) - indoxacarb , pyrazoline , chemistry , stereochemistry , enantiomer , tricyclic , moiety , combinatorial chemistry , pesticide , biology , organic chemistry , agronomy
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). © 2001 Society of Chemical Industry