Flonicamid

Morita, M., Ueda, T., Yoneda, T., Koyanagi, T., and Haga, T., Flonicamid, a novel insecticide with a rapid inhibitory effect on aphid feeding, Pest Manag. Sci., 63, 969,2007... 

Selective Feeding Blockers (Pymetrozine, Flonicamid) 1091 Table 30.1.1 Key inventions related to the chemical class of the pyridine azomethines. 

Selective Feeding Blockers (Pymetrozine, Flonicamid) 109S... 

Flonicamid (12 developmental codes IKI-220, F1785) is a selective systemic aphicide discovered by Ishihara Sangyo Kaisha, Ltd. This compound belongs to... 

Flonicamid (12) was first synthesized in 1994 [38]. Starting from the commercially available 4-(trifluoromethyl)nicotinic acid (new synthetic methods for its production have recently been described [39, 48-51]) flonicamid (12) can be synthesized in only two steps [38] (Scheme 30.1.3). An alternative route involving l,3,5-tricyanomethylhexyhydro-l,3,5-triazine (19) as source of amino-acetonitrile has also been used to prepare larger amounts of 12 [52]. 

The physicochemical properties of flonicamid (12) (Table 30.1.8) [36, 37] (e.g., low log P, high water solubility) favor systemic and translaminar activity. Flonicamid (12) has little tendency to persist due to its fast degradation, and its moderate soil mobility is negated by rapid metabolism and mineralization. 

Although the structure of flonicamid (12) has some similarity to the neonicotinoids it does not bind to the nicotinic acetylcholine receptor as directly compared with nicotine and imidacloprid [37, 53]. However, flonicamid (12) is active on the A-type potassium channel currents. The current hypothesis is that flonicamid blockade of the A-type potassium channel in the presynaptic terminal underlies its lethal effect in insects. The loss of the A-type potassium rectifying current would lead to the disruption of controlled neurotransmitter release [53]. 

Like pymetrozine (1), flonicamid (12) has a very favorable toxicological, environmental and ecotoxic profile (Table 30.1.10) and has no major negative impact on beneficial insects and mites such as Bomhyx mori, Apis mellifera, Harmonia axyri-dis and Phytoseiulus persimilis [36, 37]. 

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