Synthesis of the Insecticide Prothrin and Its Analogues from Biomass-Derived 5-(Chloromethyl)furfural

Abstract

Prothrin, a synthetic pyrethroid insecticide, was synthesized from the biomass-derived platform chemical 5-(chloromethyl)furfural in six steps and overall 65% yield. Two structural analogues of prothrin were also prepared following the same synthetic approach. Preliminary testing of these furan-based pyrethroids against the yellow fever mosquito Aedes aegypti indicates promising insecticidal activities.

Synthesis and insecticidal activity of novel pyrimidine derivatives containing urea pharmacophore against Aedes aegypti

“…Bioassays were conducted following standard protocols . Test compounds were initially diluted in DMSO or ethanol, as appropriate, to make 100 µg µL −1 stock solutions.…”

5‐(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass

“…Finally, CMF has also been used as the synthetic core of value‐added products in the agrochemical and pharmaceuticals markets, including δ‐aminolevulinic acid ( 5 ; natural herbicide and photodynamic therapy drug), ranitidine ( 6 ; drug to control gastric reflux, sold over the counter as Zantac), prothrin ( 7 ; synthetic pyrethroid insecticide), and furan fatty acids ( 8 ; dietary antioxidants and anti‐inflammatory compounds) . The efficient and green synthesis of value‐added co‐products is a strategy to leverage business models organized around low‐margin, high‐volume products such as biofuels or even paper …”

Chemical Composition and Mosquitocidal Activity of n-Hexane and Methanolic Extracts from Euphorbia anacampseros var. tmolea: An Endemic Species of Turkey against Aedes aegypti

“…Adult and larval mosquito bioassay screening against natural products has been previously described [21,22]. In the larval assay, concentrations of 1, 0.5, 0.25 and 0.1 µg/µL are screened against 1 st instar ORL1952 larvae.…”