Temefos

Last updated
Temefos
Temefos.svg
Temefos 3D.png
Names
Preferred IUPAC name
O-[4-({4-[(Dimethoxyphosphorothioyl)oxy]phenyl}sulfanyl)phenyl] O,O-dimethyl phosphorothioate
Other names
[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-
dimethoxy-sulfanylidene-phosphorane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.175 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH Temefos
PubChem CID
UNII
  • InChI=1S/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3 Yes check.svgY
    Key: WWJZWCUNLNYYAU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3
    Key: WWJZWCUNLNYYAU-UHFFFAOYAC
  • S=P(OC)(OC)Oc2ccc(Sc1ccc(OP(=S)(OC)OC)cc1)cc2
Properties
C16H20O6P2S3
Molar mass 466.46 g·mol−1
Appearancewhite, crystalline solid [1]
Density 1.32 g cm−3
Melting point 30 °C (86 °F; 303 K)
Boiling point 120–125 [1]  °C (248–257 °F; 393–398 K) (decomposes)
insoluble [1]
Vapor pressure 0.00000007 mmHg (20°C) [1]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
15 mg/m3 [1]
REL (Recommended)
TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp) [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Temefos or temephos (trade name Abate) is an organophosphate larvicide used to treat water infested with disease-carrying insects [2] including mosquitoes, midges, and black fly larvae.

Contents

As with other organophosphates, temephos affects the central nervous system through inhibition of cholinesterase. In larvae, this results in death before reaching the adult stage.

In the developing world where the vector-borne disease dengue fever is endemic, temephos is widely used and applied by both private and public pest control in areas of standing water where the Aedes aegypti mosquito breeds in order to reduce the population of this disease-carrying insect. [3] Temephos is also used in the Guinea worm eradication program to kill water fleas that carry guinea worm larvae.

Resistance to temephos by A. aegypti has been seen in Brazil. The Brazilian Aedes aegypti resistance monitoring program detected temephos resistance in A. aegypti populations from several localities in the country in 1999 (Funasa 2000, Lima et al. 2003). In 1999, mosquitoes from the city of Rio de Janeiro were already resistant to temephos. [4]

Related Research Articles

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Yellow fever is a viral disease of typically short duration. In most cases, symptoms include fever, chills, loss of appetite, nausea, muscle pains – particularly in the back – and headaches. Symptoms typically improve within five days. In about 15% of people, within a day of improving the fever comes back, abdominal pain occurs, and liver damage begins causing yellow skin. If this occurs, the risk of bleeding and kidney problems is increased.

<span class="mw-page-title-main">Mosquito</span> Family of flies

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<i>Aedes albopictus</i> Species of mosquito

Aedes albopictus, from the mosquito (Culicidae) family, also known as the (Asian) tiger mosquito or forest mosquito, is a mosquito native to the tropical and subtropical areas of Southeast Asia. In the past few centuries, however, this species has spread to many countries through the transport of goods and international travel. It is characterized by the white bands on its legs and body.

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

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

<i>Wolbachia</i> Genus of bacteria in the Alphaproteobacteria class

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Aedes aegypti, the yellow fever mosquito, is a mosquito that can spread dengue fever, chikungunya, Zika fever, Mayaro and yellow fever viruses, and other disease agents. The mosquito can be recognized by black and white markings on its legs and a marking in the form of a lyre on the upper surface of its thorax. This mosquito originated in Africa, but is now found in tropical, subtropical and temperate regions throughout the world.

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<span class="mw-page-title-main">Larvicide</span> Insecticide against the larval stage

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

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

Disulfoton is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is manufactured under the name Di-Syston by Bayer CropScience. Disulfoton in its pure form is a colorless oil but the technical product used in vegetable fields is dark and yellowish with a sulfur odor. Disulfoton is processed as a liquid into carrier granules, these granules are mixed with fertilizer and clay to be made into a spike, designed to be driven into the ground. The pesticide is absorbed over time by the roots and translocated to all parts of the plant. The pesticide acts as a cholinesterase inhibitor and gives long lasting control.

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<span class="mw-page-title-main">Genetically modified insect</span> Insect that has been genetically modified

A genetically modified (GM) insect is an insect that has been genetically modified, either through mutagenesis, or more precise processes of transgenesis, or cisgenesis. Motivations for using GM insects include biological research purposes and genetic pest management. Genetic pest management capitalizes on recent advances in biotechnology and the growing repertoire of sequenced genomes in order to control pest populations, including insects. Insect genomes can be found in genetic databases such as NCBI, and databases more specific to insects such as FlyBase, VectorBase, and BeetleBase. There is an ongoing initiative started in 2011 to sequence the genomes of 5,000 insects and other arthropods called the i5k. Some Lepidoptera have been genetically modified in nature by the wasp bracovirus.

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

Mevinphos is an organophosphate insecticide that acts as an acetylcholinesterase inhibitor to control insects in a wide range of crops. It is 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.

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A lethal ovitrap is a device which attracts gravid female container-breeding mosquitoes and kills them. The traps halt the insect's life cycle by killing adult insects and stopping reproduction. The original use of ovitraps was to monitor the spread and density of Aedes and other container-breeding mosquito populations by collecting eggs which could be counted, or hatched to identify the types of insects. Since its conception, researchers found that adding lethal substances to the ovitraps could control the populations of these targeted species. These traps are called lethal ovitraps. They primarily target Aedes aegypti and Aedes albopictus mosquitoes, which are the main vectors of dengue fever, Zika virus, west Nile virus, yellow fever, and chikungunya.

Oxitec is a UK-based, US-owned biotechnology company that develops genetically modified insects in order to improve public health and food security through insect control. The genetically engineered insects are biological insecticides. Disease-carrying insects are controlled without the use of insecticides. The company claims that its method of population control is more effective than insecticides and more environmentally friendly.

Toxorhynchites (Toxorhynchites) splendens is a species of non-hematophagous mosquito belonging to the genus Toxorhynchites. It is widely used as a predator to control dengue mosquitoes.

References

  1. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0589". National Institute for Occupational Safety and Health (NIOSH).
  2. Abate Product Information
  3. New York Times article covering its application in Africa
  4. Lima JB, Da-Cunha MP, Da Silva RC, et al. (2003). "Resistance of Aedes aegypti to organophosphates in several municipalities in the State of Rio de Janeiro and Espírito Santo, Brazil". Am. J. Trop. Med. Hyg. 68 (3): 329–33. PMID   12685640.

Bibliography