Fluvalinate[1] is a synthetic pyrethroid chemical compound contained as an active agent in the products Apistan,[2] Klartan, and Minadox, that is an acaricide (specifically, a miticide), commonly used to control Varroa mites in honey bee colonies,[citation needed] infestations that constitute a significant disease of such insects.
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| ECHA InfoCard | 100.233.047 |
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| Formula | C26H22ClF3N2O3 |
| Molar mass | 502.92 g·mol−1 |
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Fluvalinate is a stable, nonvolatile,[3] viscous, heavy oil (technical) soluble in organic solvents.[4] Although the compound may be found in drones, a study has found honey samples virtually absent of fluvalinate, on account of its affinity to beeswax.[5][better source needed]
Stereoisomerism
Fluvalinate is synthesized from racemic valine [(RS)-valine], the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%.[6]
-Fluvalinat_Structural_Formula_V1.svg) (R,R)-configuration | -Fluvalinat_Structural_Formula_V1.svg) (S,S)-configuration |
-Fluvalinat_Structural_Formula_V1.svg) (S,R)-configuration | -Fluvalinat_Structural_Formula_V1.svg) (R,S)-configuration |
Tau-fluvalinate (τ-fluvalinate) is the trivial name for (2R)-fluvalinate. The C atom in the valinate structure is in (R)-absolute configuration, while the second chiral atom is a mixture of (R)- and (S)-configurations:[4]
| (R,R)-configuration | (R,S)-configuration |
See also
References
Further reading
- Bessin R (2016). "Varroa Mites Infesting Honey Bee Colonies [Insect & Pest Info, Home & Health Pests, ENTFACT-608, April 2016 revision]". North Lexington, KY: University of Kentucky, Department of Entomology. Retrieved 28 August 2016.
Apistan is a product available that will kill the mites and cause the mites to drop from the bees. … Apistan strips, which contain the miticide fluvalinate, are available from most large beekeeping suppliers and can be used both for detection and treatment of varroa infestations.
External links
- EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability
- Tau-fluvalinate in the Pesticide Properties DataBase (PPDB)
- Fluvalinate in the Pesticide Properties DataBase (PPDB)