The discovery of dinotefuran: a novel neonicotinoid.
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).
Wakita
Takeo
T
Life Science Laboratory, Mitsui Chemicals, Inc., 1144 Togo, Mobara, Chiba 297-0017, Japan. takeo.wakita@mitsui-chem.co.jp
Kinoshita
Katsutoshi
K
Yamada
Eiichi
E
Yasui
Naoko
N
Kawahara
Nobuyuki
N
Naoi
Atsuko
A
Nakaya
Michihiko
M
Ebihara
Koichi
K
Matsuno
Hirozumi
H
Kodaka
Kenji
K
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
D006146:Guanidines; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; C465368:dinotefuran; D009538:Nicotine; D000109:Acetylcholine