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Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Added doi. | Use this bot. | #UCB_Other
 
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{{cs1 config|name-list-style=vanc}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 414541346
| Watchedfields = changed
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|ImageFile=Temefos.svg
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| verifiedrevid = 444215306
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|ImageFile2=Temefos 3D.png
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| ImageFile=Temefos.svg
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|ImageSize=300px
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| ImageFile2=Temefos 3D.png
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|ImageSize2=300px
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| ImageSize=300px
|IUPACName=''O'',''O'',''O′'',''O′''-Tetramethyl ''O'',''O''′-sulfanediylbis(1,4-phenylene) diphosphorothioate
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| ImageSize2=300px
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|OtherNames=[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-<br>dimethoxy-sulfanylidene-phosphorane
| PIN=''O''-[4-({4-[(Dimethoxyphosphorothioyl)oxy]phenyl}sulfanyl)phenyl] ''O'',''O''-dimethyl phosphorothioate
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|Section1= {{Chembox Identifiers
⚫
| OtherNames=[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-<br />dimethoxy-sulfanylidene-phosphorane
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ONP3ME32DL
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5199
| ChemSpiderID = 5199
| 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
| 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
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WWJZWCUNLNYYAU-UHFFFAOYSA-N
| StdInChIKey = WWJZWCUNLNYYAU-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=3383-96-8
| CASNo=3383-96-8
| PubChem=5392
| PubChem=5392
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1355821
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06062
| KEGG = D06062
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| SMILES = S=P(OC)(OC)Oc2ccc(Sc1ccc(OP(=S)(OC)OC)cc1)cc2
| ChEBI = 38954
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| MeSHName=Temefos
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| SMILES = S=P(OC)(OC)Oc2ccc(Sc1ccc(OP(=S)(OC)OC)cc1)cc2
⚫
| MeSHName=Temefos
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
|C=16|H=20|O=6|P=2|S=3
| C=16 | H=20 | O=6 | P=2 | S=3
| Appearance=
| Appearance= white, crystalline solid<ref name=PGCH/>
| Density=1.32 g cm<sup>-3</sup>
| Density=1.32 g cm<sup>−3</sup>
| MeltingPtC=30
| MeltingPtC=30
| BoilingPtC=120-125<ref name=PGCH/>
| BoilingPt=
| BoilingPt_notes = (decomposes)
| Solubility=
| Solubility= insoluble<ref name=PGCH/>
| VaporPressure = 0.00000007 mmHg (20°C)<ref name=PGCH/>
}}
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| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
| PEL = 15 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0589}}</ref>
| IDLH = N.D.<ref name=PGCH/>
| REL = TWA 10 mg/m<sup>3</sup> (total) TWA 5 mg/m<sup>3</sup> (resp)<ref name=PGCH/>
}}
}}
}}
}}


'''Temefos''' or '''Temephos''' (trade name '''Abate''') is an [[organophosphate]] [[larvicide]] used to treat water infested with disease-carrying [[insects]]<ref>[http://www.basfpublichealth.com/products/abate.html Abate Product Information]</ref> including [[mosquito]]es, [[midge]]s, and [[black fly]] [[larva]]e.
'''Temefos''' or '''temephos''' (trade name '''Abate''') is an [[organophosphate]] [[larvicide]] used to treat water infested with disease-carrying [[insects]]<ref>[http://www.basfpublichealth.com/products/abate.html Abate Product Information]</ref> including [[mosquito]]es, [[midge]]s, and [[black fly]] [[larva]]e.


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.
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 (epidemiology)|vector]]-borne disease [[dengue fever]] is [[Endemic (epidemiology)|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.<ref>[http://nytimes.com/2006/03/26/international/africa/26worm.html?pagewanted=all ''New York Times'' article covering its application in Africa]</ref> Temephos is also used in the [[Guinea Worm]] [[Eradication of infectious diseases|Eradication]] program to kill water fleas that carry guinea worm larvae.
In the [[developing world]] where the [[Vector (epidemiology)|vector]]-borne disease [[dengue fever]] is [[Endemic (epidemiology)|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.<ref>[https://nytimes.com/2006/03/26/international/africa/26worm.html?pagewanted=all ''New York Times'' article covering its application in Africa]</ref> Temephos is also used in the [[Guinea worm eradication]] program to kill [[Cladocera|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.<ref>{{cite journal |author=Lima JB, Da-Cunha MP, Da Silva RC, ''et al.'' |title=Resistance of Aedes aegypti to organophosphates in several municipalities in the State of Rio de Janeiro and Espírito Santo, Brazil |journal=Am. J. Trop. Med. Hyg. |volume=68 |issue=3 |pages=329–33 |year=2003 |pmid=12685640 |doi=}}</ref>
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.<ref>{{cite journal |vauthors=Lima JB, Da-Cunha MP, Da Silva RC, etal |title=Resistance of Aedes aegypti to organophosphates in several municipalities in the State of Rio de Janeiro and Espírito Santo, Brazil |journal=Am. J. Trop. Med. Hyg. |volume=68 |issue=3 |pages=329–33 |year=2003 |doi=10.4269/ajtmh.2003.68.329 |pmid=12685640 }}</ref>

Despite the use of Temephos to stop the spread of the dengue virus in parts of Mexico and Central America, its multiple serotypes have kept spreading farther to the north. In the United States, where it is produced, the chemical has not received approval for human consumption <ref> Devine, G.J., & Furlong, M.J., (2007), Insecticide Use: Contexts and Ecological Consequences, Agriculture and Human Values, 24: 281-306. </ref>. Furthermore, studies that were not sponsored by the Temephos industry have reported sub-lethal animal toxicity <ref> USEPA (2008a) [http://www.epa.gov/oppsrrd1/REDs/temephos_red.htm Temephos RED (Reregistration Eligibility Decision)]. Washington, DC, US Environmental Protection Agency </ref> <ref> Anadu, D.I., Anaso, H.U., & Onyeko, O.N.D., (1996), Acute toxicity of the insect larvicide abate (temephos) on the fish tilapia melanopleura and the dragonfly larvae neurocordelia virginiensis, Journal of Environmental Science and Health, Part B, 31(6): 1363-1375.</ref> <ref> Sparling, D.W., Lowe, T.P., & Pinkney, A.E., (1997), Toxicity of Abate to Green Frog Tadpoles, Bulletin of Environmental Contamination and Toxicology, 58: 475-481.</ref> and genotoxicity <ref> Aiub CAF, Coelho ECA, Sodre E, Pinto LFR & Felzenszwalb I, Genotoxic evaluation of the organophosphorous pesticide temephos, Genet. Mol. Res, 2002;1: 159-166.</ref>. There is also extensive documentation showing that the Aedes aegypti’s resistance to the chemical has increased over the years <ref> Braga IA, Lima JBP, da Silva Soares S, & Valle D. (2004) Aedes aegypti Resistance to Temephos during 2001 in Several Municipalities in the States of Rio de Janeiro, Sergipe, and Alagoas, Brazil, Mem. Inst. Oswaldo Cruz, Rio de Janeiro, 99(2): 199-203.</ref> <ref> Chen CD, Nazni WA, Lee HL, & Sofian-Azirun M, (2005), Susceptibility of Aedes aegypti and Aedes albopictus to temephos in four study sites in Kuala Lumpur City Center and Selangor State, Malaysia, Tropical Biomedicine, 22(2): 207-216. </ref> <ref> Jirakanjanakit B, Saengtharatip S, Rongnoparut P, Duchon S, Bellec C, & Yoksan S, (2007), Trend of Temephos Resistance in Aedes aegypti Mosquitoes in Thailand during 2003-2005, Environmental Entomology, 36(3): 506-511.</ref> <ref> Lima JBP, da Cunha MP, da Silva Junior RC, Galardo AKR, da Silva Soares S, Braga IA, Ramos RP, & Valle, D, (2003), Resistance of Aedes aegypti to organophosphates in several municipalities in the state of Rio de Janeiro and Espõ´rito Santo, Brazil. Am. J. Trop. Med. Hyg., 68: 329-333.</ref> Rodriguez, M. M., Bisset, J., de Fernandez, D.M., Lauzan, L., & Soca, A., (2001), Detection of insecticide resistance in Aedes aegypti (Diptera: Culicidae) from Cuba and Venezuela. J. Med. Entomol. 38: 623-628. <ref>. These factors, combined with “the variable coverage and consistency of many government initiated programmes using temephos for dengue control,” put to question its lack of impact on human health and the effectiveness of its use as an adequate means of vector control <ref>Andersson, Neil; Nava Aguilera, Elizabeth; Harris, Eva; Arostegui, Jorge; Barrera Ríos, Luis. Camino verde: a randomised controlled cluster trial to reduce dengue risk in southern Mexico through evidence-based community mobilisation. Unpublished document.</ref>


==References==
==References==
{{reflist}}
{{Reflist}}


==External links==
==External links==
* [http://www.cdc.gov/niosh/npg/npgd0589.html NIOSH Pocket Guide to Chemical Hazards]
* [https://www.cdc.gov/niosh/npg/npgd0589.html NIOSH Pocket Guide to Chemical Hazards]
* [http://www.cdc.gov/niosh/ipcsneng/neng0199.html International Chemical Safety Cards]
* [https://www.cdc.gov/niosh/ipcsneng/neng0199.html International Chemical Safety Cards]
* [http://www.basfpublichealth.com/products/abate.html Official product site]
* [http://www.basfpublichealth.com/products/abate.html Official product site]
* {{PPDB|618}}


== Bibliography ==
{{insecticides}}
* Dejous C & Elouard J.M (1977) [http://horizon.documentation.ird.fr/exl-doc/pleins_textes/cahiers/hydrobio/18237.pdf Action de l'abate sur les invertébérs aquatiques ; cinétique de décrochement à court et moyen terme] (in French).
{{Cholinergics}}


{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}
{{Authority control}}

[[Category:Acetylcholinesterase inhibitors]]
[[Category:Organophosphate insecticides]]
[[Category:Organophosphate insecticides]]
[[Category:Anticholinesterases]]
[[Category:Thioethers]]
[[Category:Thioethers]]
[[Category:Phosphorothioates]]
[[Category:Organothiophosphate esters]]

[[es:Temefos]]
[[nl:Temefos]]

Latest revision as of 02:40, 11 February 2024

Temefos
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 Edit this at Wikidata
KEGG
MeSH Temefos
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 checkY
    Key: WWJZWCUNLNYYAU-UHFFFAOYSA-N checkY
  • 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
Appearance white, 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).
☒N verify (what is checkY☒N ?)

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.

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]

References

[edit]
  1. ^ a b c d e f g 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. doi:10.4269/ajtmh.2003.68.329. PMID 12685640.
[edit]

Bibliography

[edit]
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