Fluvalinate is a synthetic

pyrethroid A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and '' C. coccineum''). Pyrethroids are used as commercial and household insecticides. I ...

chemical compound contained as an active agent in the products Apistan, Klartan, and Minadox, that is an acaricide (specifically, a

miticide Acaricides are pesticides that kill members of the arachnid subclass ''Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termino ...

), commonly used to control ''Varroa'' mites in

honey bee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current cosm ...

colonies, infestations that constitute a significant disease of such insects. Fluvalinate is a stable, nonvolatile, viscous, heavy oil (technical) soluble in organic solvents. Although the compound may be found in drones, a study has found

honey Honey is a sweet and viscous substance made by several bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of plants (primar ...

samples virtually absent of fluvalinate, on account of its affinity to

beeswax Beeswax (''cera alba'') is a natural wax produced by honey bees of the genus ''Apis''. The wax is formed into scales by eight wax-producing glands in the abdominal segments of worker bees, which discard it in or at the hive. The hive work ...

Stereoisomerism

Fluvalinate is synthesized from

racemic In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

valine RS)-valine the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%. ''Tau''-fluvalinate (τ-fluvalinate) is the trivial name for (2''R'')-fluvalinate. The C atom in the valinate structure is in (''R'')-

absolute configuration Absolute configuration refers to the spatial arrangement of atoms within a chiral molecular entity (or group) and its resultant stereochemical description. Absolute configuration is typically relevant in organic molecules, where carbon is bonde ...

, while the second chiral atom is a mixture of (''R'')- and (''S'')-configurations:

References

External links

EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability
* * Pyrethroids Chloroarenes Trifluoromethyl compounds Nitriles Phenol ethers Cyanohydrin esters {{antiinfective-drug-stub

Stereoisomerism

See also

References

Further reading

External links