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The discovery of dinotefuran: a novel neonicotinoid

2003; Wiley; Volume: 59; Issue: 9 Linguagem: Inglês

10.1002/ps.727

1526-4998

Takeo Wakita, Katsutoshi Kinoshita, Eiichi Yamada, Naoko Yasui, Nobuyuki Kawahara, Atsuko Naoi, Michihiko Nakaya, Koichi Ebihara, Hirozumi Matsuno, Kenji Kodaka,

Insect Pest Control Strategies

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).