Fluvalinate

Last updated
Fluvalinate
Fluvalinat Structural Formula V3.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATCvet code
Identifiers
  • [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.233.047 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C26H22ClF3N2O3
Molar mass 502.92 g·mol−1
3D model (JSmol)
  • CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
  • InChI=1S/C26H22ClF3N2O3/c1-16(2)24(32-22-12-11-18(14-21(22)27)26(28,29)30)25(33)35-23(15-31)17-7-6-10-20(13-17)34-19-8-4-3-5-9-19/h3-14,16,23-24,32H,1-2H3 X mark.svgN
  • Key:INISTDXBRIBGOC-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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.

Contents

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 ]

CHS Health Classification

Fluvalinate is considered an acute toxic, Health hazard and environmental hazard by ECHA (European Chemicals Agency).

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 valine [(RS)-valine], the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%. [6]

Fluvalinate stereoisomers
(R,R)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(S,S)-Fluvalinat Structural Formula V1.svg
(S,S)-configuration
(S,R)-Fluvalinat Structural Formula V1.svg
(S,R)-configuration
(R,S)-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]

τ-Fluvalinate diastereomers
(R,R)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(R,S)-Fluvalinat Structural Formula V1.svg
(R,S)-configuration

See also

Related Research Articles

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, industrial buildings, for vector control, and control of insect parasites of animals and humans.

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

<span class="mw-page-title-main">Fenvalerate</span> Chemical compound

Fenvalerate is a synthetic pyrethroid insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha configuration, known as esfenvalerate, is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.

<i>Varroa destructor</i> Species of mite

Varroa destructor, the Varroa mite, is an external parasitic mite that attacks and feeds on honey bees and is one of the most damaging honey bee pests in the world. A significant mite infestation leads to the death of a honey bee colony, usually in the late autumn through early spring. Without management for Varroa mite, honey bee colonies typically collapse within 2 to 3 years in temperate climates. These mites can infest Apis mellifera, the western honey bee, and Apis cerana, the Asian honey bee. Due to very similar physical characteristics, this species was thought to be the closely related Varroa jacobsoni prior to 2000, but they were found to be two separate species after DNA analysis.

<span class="mw-page-title-main">Acaricide</span> Agent that kills members of the arachnid subclass Acari

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.

<i>Varroa</i> Genus of mites

Varroa is a genus of parasitic mesostigmatan mites associated with honey bees, placed in its own family, Varroidae. The genus was named for Marcus Terentius Varro, a Roman scholar and beekeeper. The condition of a honeybee colony being infested with Varroa mites is called varroosis.

<span class="mw-page-title-main">Acephate</span> Chemical compound

Acephate is an organophosphate foliar and soil insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended use rate. It is used primarily for control of aphids, including resistant species, in vegetables and in horticulture. It also controls leaf miners, caterpillars, sawflies, thrips, and spider mites in the previously stated crops as well as turf, and forestry. By direct application to mounds, it is effective in destroying imported fire ants.

<span class="mw-page-title-main">Clothianidin</span> Chemical compound

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.

<span class="mw-page-title-main">Coumaphos</span> Chemical compound

Coumaphos is a nonvolatile, fat-soluble phosphorothioate with ectoparasiticide properties: it kills insects and mites. It is well known by a variety of brand names as a dip or wash, used on farm and domestic animals to control ticks, mites, flies and fleas.

<span class="mw-page-title-main">Beekeeping in the United States</span> Commercial beekeeping in the United States

Commercial Beekeeping in the United States dates back to the 1860s.

<span class="mw-page-title-main">Beekeeping in New Zealand</span>

Beekeeping in New Zealand is reported to have commenced in 1839 with the importing of two skep hives by Mary Bumby, a missionary. It has since become an established industry as well a hobby activity.

<span class="mw-page-title-main">Colony collapse disorder</span> Aspect of apiculture

Colony collapse disorder (CCD) is an abnormal phenomenon that occurs when the majority of worker bees in a honey bee colony disappear, leaving behind a queen, plenty of food, and a few nurse bees to care for the remaining immature bees. While such disappearances have occurred sporadically throughout the history of apiculture, and have been known by various names, the syndrome was renamed colony collapse disorder in early 2007 in conjunction with a drastic rise in reports of disappearances of western honey bee colonies in North America. Beekeepers in most European countries had observed a similar phenomenon since 1998, especially in Southern and Western Europe; the Northern Ireland Assembly received reports of a decline greater than 50%. The phenomenon became more global when it affected some Asian and African countries as well. From 1990 to 2021, the United Nation's FAO calculated that the worldwide number of honeybee colonies increased 47%, reaching 102 million.

<span class="mw-page-title-main">Acetamiprid</span> Chemical compound

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

<span class="mw-page-title-main">Varroa sensitive hygiene</span> Type of animal behavior

Varroa sensitive hygiene (VSH) is a behavioral trait of honey bees (Apis mellifera) in which bees detect and remove bee pupae that are infested by the parasitic mite Varroa destructor. V. destructor is considered to be the most dangerous pest problem for honey bees worldwide. VSH activity results in significant resistance to the mites.

<span class="mw-page-title-main">Mevinphos</span> Chemical compound

Mevinphos is a toxic organophosphate insecticide that acts as an acetylcholinesterase inhibitor to control insects in a wide range of crops. It was most commonly used for the control of chewing and sucking insects, as well as spider mites. Common synonym names are duraphos, fosdrin, menite, mevinfos, mevinox, phosdrin, and phosdrine. It is not allowed in the EU anymore.

<span class="mw-page-title-main">Thiacloprid</span> Chemical compound

Thiacloprid is an insecticide of the neonicotinoid class. Its mechanism of action is similar to other neonicotinoids and involves disruption of the insect's nervous system by stimulating nicotinic acetylcholine receptors. Thiacloprid was developed by Bayer CropScience for use on agricultural crops to control of a variety of sucking and chewing insects, primarily aphids and whiteflies.

<span class="mw-page-title-main">Flumethrin</span> Chemical compound

Flumethrin is a pyrethroid insecticide. It is used externally in veterinary medicine against parasitic insects and ticks on cattle, sheep, goats, horses, and dogs, and the treatment of parasitic mites in honeybee colonies.

<span class="mw-page-title-main">Fenpropathrin</span> Chemical compound

Fenpropathrin, or fenopropathrin, is a widely used pyrethroid insecticide in agriculture and household. Fenpropathrin is an ingestion and contact synthetic pyrethroid. Its mode of action is similar to other natural (pyrethrum) and synthetic pyrethroids where in they interfere with the kinetics of voltage gated sodium channels causing paralysis and death of the pest. Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980. Like other pyrethroids with an α-cyano group, fenpropathrin also belongs to the termed type II pyrethroids. Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves. Application rates of fenpropathrin in agriculture according to US environmental protection agency (EPA) varies by crop but is not to exceed 0.4 lb ai/acre.

<i>Slow bee paralysis virus</i> Species of virus

Slow bee paralysis virus (SBPV) is a virus discovered in England in 1974 that infects honeybees, bumblebees, and silkworms through Varroa destructor mite infestations. The virus causes paralysis in the front two pairs of legs of adult bees eventually killing its hosts. The virus is in the iflaviridae family of viruses. Infection by iflaviridae viruses is among the leading cause of death of honeybee colonies. As bees and silkworms are of great economic and biological importance, the virus is the subject of ongoing research.

References

  1. "Fluvalinate - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2023-11-03.
  2. "Apistan: Varroa Control". Vita Bee Health. 2023-06-28. Retrieved 2023-11-03.
  3. "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017
  4. 1 2 "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017
  5. MAF Biosecurity New Zealand (2001), A Review of Treatment Options for Control of Varroa Mite in New Zealand [HortResearch Client Report No. 2001/249] (PDF), archived from the original (PDF) on 2016-09-11, retrieved 28 August 2016, This report was commissioned by MAF to aid in internal decision making only. This report in no way constitutes MAF's advice to beekeepers and is useful only as background information.
  6. Whitacre DM (2012). Reviews of environmental contamination and toxicology. Springer. p. 125. ISBN   978-1-4614-3280-7.

Further reading