Coumaphos

Last updated
Coumaphos
Coumaphos-Structural Formula V.1.svg
Coumaphos 3D spacefill.png
Names
Preferred IUPAC name
O-(3-Chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl phosphorothioate
Other names
3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone
Coumaphos, Meldane, Asuntol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.260 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3 Yes check.svgY
    Key: BXNANOICGRISHX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3
    Key: BXNANOICGRISHX-UHFFFAOYAO
  • S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2
Properties
C14H16ClO5PS
Molar mass 362.77 g/mol
Pharmacology
QP53AF08 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1]

It is also used to control Varroa mites in honey bee colonies, though in many areas it is falling out of favor as the mites develop resistance and as the residual toxicity effects are becoming better understood. [2] [3]

In Australia, its registration as suited to home veterinary use was cancelled by the Australian Pesticides and Veterinary Medicines Authority in June 2004 after the manufacturer failed to show it was safe for use on pets. [4]

The compound has been linked to neurological problems in bees, and may be a factor in colony collapse. [5]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. [6]

Related Research Articles

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

Chlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

<span class="mw-page-title-main">VG (nerve agent)</span> Chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.

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

Varroa destructor, the Varroa mite is an external parasitic mite that attacks and feeds on the honey bees Apis cerana and Apis mellifera. The disease caused by the mites is called varroosis.

<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.

<span class="mw-page-title-main">Aldicarb</span> Chemical compound (insecticide)

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure.

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

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity to the GABAA receptors of insects, than to those of mammals, and to its action on GluCl channels, which do not exist in mammals. As of 2017, there did not appear to be significant resistance among fleas to fipronil.

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

Varroa jacobsoni is a species of mite that parasitises Apis cerana. The more damaging Varroa destructor was previously included under the name V. jacobsoni, but the two species can be separated on the basis of the DNA sequence of the cytochrome oxidase I gene in the mitochondrial DNA.

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

Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.

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

Calcium arsenate is the inorganic compound with the formula Ca3(AsO4)2. A colourless salt, it was originally used as a pesticide and as a germicide. It is highly soluble in water, in contrast to lead arsenate, which makes it more toxic. The minerals rauenthalite Ca3(AsO4)2·10H2O and phaunouxite Ca3(AsO4)2·11H2O are hydrates of calcium arsenate.

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

Dioxathion, systematically known as p-dioxane-2,3-diyl ethyl phosphorodithioate, is an organophosphate pesticide. It is used as an insecticide on livestock and as an acaricide on citrus fruits, deciduous fruits and nuts.

<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. However, studies published in 2012 show that neonicotinoid dust released at planting time may persist in nearby fields for several years and be taken up into non-target plants, which are then foraged by bees and other insects.

<span class="mw-page-title-main">Fluvalinate</span>

Fluvalinate is a synthetic pyrethroid chemical compound contained as an active agent in the products Apistan, Klartan, and Minadox, that is an acaricide, commonly used to control Varroa mites in honey bee colonies, infestations that constitute a significant disease of such insects.

<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.

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

Crimidine is a convulsant poison used as a rodenticide. Crimidine was originally known by its product name, Castrix. It was originally produced in the 1940s by the conglomerate, IG Farben. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. It is also no longer used in the United States as a rodenticide, but is still used to this day in other countries.

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

Azinphos-ethyl was a broad-spectrum organophosphate insecticide.

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

Oxamyl is a chemical used as a pesticide that comes in two forms: granulated and liquid. The granulated form has been banned in the United States. It is commonly sold under the trade name Vydate.

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

Chlormequat is an organic compound with the formula ClCH
2
CH
2
N(CH
3
)+
3
that is used as a plant growth regulator. It is typically sold as the chloride salt, chlormequat chloride (C5H13Cl2N), a colorless hygroscopic crystalline substance that is soluble in water and ethanol. It is an alkylating agent and a quaternary ammonium salt. Chlormequat is one of the onium-type growth regulators.

References

  1. "Asuntol - Cattle, Goat, Sheep - anti lice, fleas, sucking flies and mite". vetcontact.com.
  2. "A Review of Treatment Options for Control of Varroa Mite in New Zealand". biosecurity.govt.nz. Archived from the original on 2017-02-26. Retrieved 2008-08-28.
  3. Johnson, Reed M.; Ellis, Marion D.; Mullin, Christopher A.; Frazier, Maryann (2010). "Pesticides and honey bee toxicity – USA" (PDF). Apidologie. 41 (3): 312. doi:10.1051/apido/2010018. S2CID   12927448.
  4. "Coumaphos Review". www.apvma.gov.au. Archived from the original on August 29, 2008.
  5. "Neonicotinoid pesticides 'damage brains of bees'". BBC News. 27 March 2013.
  6. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.{{cite journal}}: Cite journal requires |journal= (help)