title: The discovery of dinotefuran: a novel neonicotinoid.
abstract: 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).
authors.affiliation: Life Science Laboratory, Mitsui Chemicals, Inc., 1144 Togo, Mobara, Chiba 297-0017, Japan. takeo.wakita@mitsui-chem.co.jp
authors.forename: Takeo
authors.initials: T
authors.lastname: Wakita
authors.forename: Katsutoshi
authors.initials: K
authors.lastname: Kinoshita
authors.forename: Eiichi
authors.initials: E
authors.lastname: Yamada
authors.forename: Naoko
authors.initials: N
authors.lastname: Yasui
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Kawahara
authors.forename: Atsuko
authors.initials: A
authors.lastname: Naoi
authors.forename: Michihiko
authors.initials: M
authors.lastname: Nakaya
authors.forename: Koichi
authors.initials: K
authors.lastname: Ebihara
authors.forename: Hirozumi
authors.initials: H
authors.lastname: Matsuno
authors.forename: Kenji
authors.initials: K
authors.lastname: Kodaka
mesh_terms: D000109:Acetylcholine / Q000031:analogs & derivatives / Q000737:chemistry; D000818:Animals; D001681:Biological Assay; D006146:Guanidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D006430:Hemiptera / Q000187:drug effects; D007306:Insecticides / Q000494:pharmacology*; D015394:Molecular Structure; D000073943:Neonicotinoids; D009538:Nicotine / Q000031:analogs & derivatives; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D018411:Spodoptera / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D006146:Guanidines; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; C465368:dinotefuran; D009538:Nicotine; D000109:Acetylcholine