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Furan-based pyrethroids against the yellow fever mosquito Aedes aegypti

21 May 2014
5-(Chloromethyl)furfural against Yellow fever mosquito, Aedes aegypti 5-(Chloromethyl)furfural against Yellow fever mosquito, Aedes aegypti (Image: DalinYebo)
Synthesis of the Insecticide Prothrin from 5-(Chloromethyl)furfural (CMF)

J Agric Food Chem. 2014 Jan 3.[1]: 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.

CMF is made in a one-step reaction under mild conditons from C6-sugars (e.g. D-fructose, D-glucose, sucrose etc.) or polysaccharides such as cellulose[2].

References:

[1] J Agric Food Chem. 2014 Jan 3

[2] Example: Highly efficient dehydration of carbohydrates to 5-(chloromethyl)furfural (CMF), 5-(hydroxymethyl)furfural (HMF) and levulinic acid by biphasic continuous flow processing, Green Chemistry, Issue 5, 2011 (For our clients: Download publication and supporting information here).

Also see:

Nematicides

Biomass to Pharmaceuticals

From Biomass to Medicines

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