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 ''Chrysanthemum coccineum, C. coccineum''). Pyrethroids are used as commercial and hou ...
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 mainland Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the ...
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 species of 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 pl ...
samples virtually absent of fluvalinate, on account of its affinity to
beeswax
Bee hive wax complex
Beeswax (also known as 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 o ...
.
CHS Health Classification
Fluvalinate is considered an acute toxic, Health hazard and environmental hazard by ECHA (
European Chemicals Agency
The European Chemicals Agency (ECHA; ) is an agency of the European Union working for the safe use of chemicals. It manages the technical and administrative aspects of the implementation of the European Union regulation called Registration, E ...
).
The chemical is fatal if inhaled and is extremally toxic to aquatic life. If not fatal the effects are permanent and has multiple long lasting effects.
Stereoisomerism
Fluvalinate is synthesized from
racemic
In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) 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 r ...
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
In chemistry, absolute configuration refers to the spatial arrangement of atoms within a molecular entity (or Functional group, group) that is chirality (chemistry), chiral, and its resultant stereochemical description. Absolute configuration is ...
, while the second chiral atom is a mixture of (''R'')- and (''S'')-configurations:
See also
*
Diseases of the honey bee
Diseases of the honey bee or abnormal hive conditions include:
Pests and parasites
''Varroa'' mites
''Varroa destructor'' and ''V. jacobsoni'' are parasite, parasitic mites that feed on the fat bodies of adult, pupal and larval bees. When ...
References
Further reading
*
External links
EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability*
*
ECHA
{{insecticides
Pyrethroids
Chloroarenes
Trifluoromethyl compounds
Nitriles
Phenol ethers
Cyanohydrin esters