profenofos
{{chembox
| Verifiedfields =
| Watchedfields =
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| ImageFile = Profenofos.svg
| ImageSize =
| PIN = O-(4-Bromo-2-chlorophenyl) O-ethyl S-propyl phosphorothioate
| OtherNames = Phosphorothioic acid, O-(4-bromo-2-chlorophenyl)O-ethylS-propyl ester
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref =
| ChemSpiderID = 35529
| InChI = 1S/C11H15BrClO3PS/c1-3-7-18-17(14,15-4-2)16-11-6-5-9(12)8-10(11)13/h5-6,8H,3-4,7H2,1-2H3
| InChIKey = QYMMJNLHFKGANY-UHFFFAOYSA-N
| SMILES1 = CCCSP(=O)(OCC)OC1=C(C=C(C=C1)Br)Cl
| StdInChI_Ref =
| StdInChI =
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 41198-08-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7J04O7BS4W
| PubChem = 38779
| SMILES =
}}
| Section2 = {{Chembox Properties
| C=11|H=15|Br=1|Cl=1|O=3|P=1|S=1
| Appearance = Pale yellow to amber liquid
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| Section3 = {{Chembox Hazards
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| Reference = {{pubchem|38779}}{{nist |name=Profenofos |id=41198-08-7 |accessdate=2015}}
}}
Profenofos is an organophosphate insecticide. It is a liquid with a pale yellow to amber color and a garlic-like odor. It was first registered in the United States in 1982.{{cite web|publisher=US Environmental Protection Agency Office of Pesticide Programs|title=Reregistration Eligibility Decision for Profenofos|url=http://www.epa.gov/oppsrrd1/reregistration/REDs/profenofos_red.pdf|website=United States Environmental Protection Agency|access-date=18 July 2015}}{{rp|1}} As of 2015, it was not approved in the European Union.{{cite web|title=EU Pesticides database|url=http://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/public/?event=activesubstance.detail&language=EN&selectedID=1755|website=European Commission|access-date=18 July 2015}}
Uses
Profenofos can be used on a variety of crops including cotton and vegetables such as maize, potato, soybean, and sugar beet.{{cite book|title=Pesticide residues in food--2007: toxicological evaluations|date=2009|publisher=World Health Organization|location=Geneva|isbn=9789241665230}}{{rp|404}} In the United States it is used exclusively on cotton and is primarily used against lepidopteran insects.{{rp|1}}
Mixed with phoxim, cypermethrin, beta-cypermethrin imidacloprid and deltamethrin, profenofos can be used against Cotton MealyBug, cabbage caterpillar, Plutella xylostella and asparagus caterpillars, as well as against wheat and cabbage aphids.{{citation needed|date=July 2015}}
Mechanism of action
Like other organophosphates, the profenofos mechanism of action is via the inhibition of the acetylcholinesterase enzyme. Although it is used in the form of a racemate, the S(-) isomer is a more potent inhibitor.{{rp|404}}
Synthesis
File:Profenophos_synthesis2.svg
Profenofos can be synthesized by reacting phosphorus oxychloride with sodium ethoxide and sodium 1-propanethiolate, followed by treatment with 4-bromo-2-chlorophenol.{{cite book|last1=Braun|first1=David B.|title=Pharmaceutical manufacturers an international directory|date=1995|publisher=Noyes Publications|location=Park Ridge, N.J., U.S.A.|isbn=9780815518532}}{{rp|332}}
Toxicity
A 2007 World Health Organization report found no adverse effects to workers of routine exposure to profenofos and no teratogenicity or carcinogenicity.{{rp|435–8}}
Based on a study of patients poisoned with profenofos and its close chemical relative prothiofos, the compound has been described as "of moderately severe toxicity", causing respiratory failure. Differences in chemical structure that distinguish these two compounds from more common organophosphate pesticides - namely, the presence of the S-alkyl group on the phosphorus atom where most OP compounds possess a methoxy or ethoxy group - underlie differences in their behavior as acetylcholinesterase enzyme inhibitors compared to the rest of the OP class.{{cite journal|last1=Eddleston|first1=M|last2=Worek|first2=F|last3=Eyer|first3=P|last4=Thiermann|first4=H|last5=Von Meyer|first5=L|last6=Jeganathan|first6=K|last7=Sheriff|first7=MH|last8=Dawson|first8=AH|last9=Buckley|first9=NA|title=Poisoning with the S-Alkyl organophosphorus insecticides profenofos and prothiofos|journal=QJM|date=November 2009|volume=102|issue=11|pages=785–92|pmid=19737786|doi=10.1093/qjmed/hcp119|pmc=2766103}}
In one study of a patient who died of profenofos poisoning, the major metabolites of profenofos were identified as des-S-propylated profenofos, two isomers of despropylated propenofos, and desethylated propenofos.{{cite journal|last1=Gotoh|first1=M|last2=Sakata|first2=M|last3=Endo|first3=T|last4=Hayashi|first4=H|last5=Seno|first5=H|last6=Suzuki|first6=O|title=Profenofos metabolites in human poisoning|journal=Forensic Science International|date=15 February 2001|volume=116|issue=2–3|pages=221–6|pmid=11182275|doi=10.1016/s0379-0738(00)00377-7}} A downstream, nontoxic metabolite, 4-bromo-2-chlorophenol, has been proposed as biomarker for exposure.{{cite journal|last1=Dadson|first1=OA|last2=Ellison|first2=CA|last3=Singleton|first3=ST|last4=Chi|first4=LH|last5=McGarrigle|first5=BP|last6=Lein|first6=PJ|last7=Farahat|first7=FM|last8=Farahat|first8=T|last9=Olson|first9=JR|title=Metabolism of profenofos to 4-bromo-2-chlorophenol, a specific and sensitive exposure biomarker|journal=Toxicology|date=5 April 2013|volume=306|pages=35–9|pmid=23415833|doi=10.1016/j.tox.2013.01.023|pmc=4751995}}
Environmental effects
A United States Environmental Protection Agency report identified profenofos as toxic to birds, small mammals, bees, fish, and aquatic invertebrates, noting several fish kill incidents in which profenofos exposure, primarily due to runoff, was implicated as a probable cause.{{rp|2–3}}
References
{{reflist}}
{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}
Category:Acetylcholinesterase inhibitors
Category:Organophosphate insecticides
Category:Chlorobenzene derivatives