Discovery of broflanilide, a novel insecticide.

Broflanilide (1), discovered by Mitsui Chemicals Agro, Inc., has a unique chemical structure characterized as a meta-diamide and exhibits high activity against various pests, including Lepidopteran, Coleopteran, and Thysanopteran pests. Because broflanilide has a novel mode of action, the Insecticide Resistance Action Committee (IRAC) categorized it as a member of a new group: Group 30. The meta-diamide structure was generated via drastic structural modification of a lead compound, flubendiamide (2), and the subsequent structural optimization of meta-diamides on each of its three benzene rings led to the discovery of broflanilide. In the present study, the details of the generation of meta-diamides from the lead compound and the structural optimization of meta-diamides are described.

Molecular design of dinotefuran with unique insecticidal properties.

Dinotefuran, (RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine, is a neonicotinoid insecticide developed by Mitsui Chemicals Agro. Dinotefuran provides a tetrahydrofuran (THF) moiety distinct from other neonicotinoids with a chloropyridine or chlorothiazole ring, which is considered to be an essential structural element for the neonicotinoid action. The molecular design strategy based on acetylcholine ester moiety as a lead structure has successfully led to the discovery of dinotefuran with the cyclic ether THF functional group. The unique chemical and excellent biological properties and favorable toxicological profile make dinotefuran available for pest management in wide range of crops with a variety of application methods.

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).