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The discovery of dinotefuran: a novel neonicotinoid
Author(s) -
Wakita Takeo,
Kinoshita Katsutoshi,
Yamada Eiichi,
Yasui Naoko,
Kawahara Nobuyuki,
Naoi Atsuko,
Nakaya Michihiko,
Ebihara Koichi,
Matsuno Hirozumi,
Kodaka Kenji
Publication year - 2003
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/ps.727
Subject(s) - neonicotinoid , moiety , ring (chemistry) , chemistry , toxicology , organic chemistry , biology , pesticide , imidacloprid , ecology
Dinotefuran (MTI‐446: ( RS )‐1‐methyl‐2‐nitro‐3‐(tetrahydro‐3‐furylmethyl)guanidine) is a new neonicotinoid commercialized by Mitsui Chemicals. Research led to this novel neonicotinoid by the removal of the chloropyridine or chlorothiazole ring that had been considered as indispensable for neonicotinoides. The research advanced as follows; (1) selection of acetylcholine for the lead compound, (2) recognition of the insecticidal advantages of 3‐methoxypropyl compounds, (3) synthesis of (±)‐tetrahydro‐3‐furylmethyl compounds by cyclization of the 3‐methoxypropyl moiety. It resulted in dinotefuran which has a (±)‐tetrahydro‐3‐furylmethyl moiety instead of a halogenated aromatic heterocyclic ring, and belongs to the third‐generation neonicotinoids (sub‐class: furanicotinyl compounds). Copyright © 2003 Society of Chemical Industry