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Revision as of 05:54, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|erro← Previous edit		Latest revision as of 16:28, 9 November 2024 edit undoSoumyapatra13 (talk | contribs)486 edits →IndiaTag: 2017 wikitext editor
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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 443817756
			| Watchedfields = changed
⚫	|ImageFile=Fenthion Structural Formulae .V.1.svg
		⚫	| verifiedrevid = 443818946
	|ImageSize=300px
		⚫	| ImageFile=Fenthion Structural Formulae .V.1.svg
	|IUPACName=''O,O''-Dimethyl ''O''- phosphorothioate
	|OtherNames=Dimethoxy--thioxophosphorane<br>''O,O''-Dimethyl ''O''- phosphorothioate<br>• ''O,O''-Dimethyl ''O''-4-methylthio-''m''-tolyl phosphorothioate		| PIN=''O'',''O''-Dimethyl ''O''- phosphorothioate
			| OtherNames=• Dimethoxy--thioxophosphorane<br />• ''O,O''-Dimethyl ''O''- phosphorothioate<br />• ''O,O''-Dimethyl ''O''-4-methylthio-''m''-tolyl phosphorothioate
	| Reference =<ref name=HSDB/>		| Reference =<ref name=HSDB/>
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 3229		| ChemSpiderID = 3229
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D07950		| KEGG = D07950
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1604375
	| InChI = 1/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3		| InChI = 1/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3
	| InChIKey = PNVJTZOFSHSLTO-UHFFFAOYAH		| InChIKey = PNVJTZOFSHSLTO-UHFFFAOYAH
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=55-38-9		| CASNo=55-38-9
	| PubChem=3346		| PubChem=3346
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 34761		| ChEBI = 34761
	| SMILES = S=P(OC)(OC)Oc1ccc(SC)c(c1)C		| SMILES = S=P(OC)(OC)Oc1ccc(SC)c(c1)C
⚫	| ATCvet = yes
⚫	| ATCCode_prefix = P53
⚫	| ATCCode_suffix = BB02
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| Formula=C<sub>10</sub>H<sub>15</sub>O<sub>3</sub>PS<sub>2</sub>		| Formula=C<sub>10</sub>H<sub>15</sub>O<sub>3</sub>PS<sub>2</sub>
	| MolarMass=278.33 g/mol		| MolarMass=278.33 g/mol
	| Appearance=colorless, almost odorless liquid; 95-98% pure fenthion is a brown oily liquid with a weak garlic odor		| Appearance=colorless, almost odorless liquid; 95-98% pure fenthion is a brown oily liquid with a weak garlic odor
	| Density=1.250 g/cm<sup>3</sup> (at 20 °C / 4 °C)		| Density=1.250 g/cm<sup>3</sup> (at 20 °C / 4 °C)
	| MeltingPt=7 °C		| MeltingPtC=7
	| BoilingPt=87 °C		| BoilingPtC=87
	| Boiling_notes=at 0.01 mmHg		| BoilingPt_notes =at 0.01&nbsp;mmHg
	| Solubility=54-56 ppm (at 20 °C)		| Solubility=54-56 ppm (at 20&nbsp;°C)
	| SolubleOther = soluble		| SolubleOther = soluble
	| Solvent = glyceride oils, methanol, ethanol, ether, acetone, and most organic solvents, especially chlorinated hydrocarbons		| Solvent = glyceride oils, methanol, ethanol, ether, acetone, and most organic solvents, especially chlorinated hydrocarbons
	| VaporPressure = 4 • 10<sup>-5</sup> mmHg (at 20 °C)		| VaporPressure = 4 • 10<sup>−5</sup> mmHg (at 20 °C)
	}}		}}
	|Section3= {{Chembox Hazards		|Section6={{Chembox Pharmacology
		⚫	| ATCvet = yes
⚫	| MainHazards=
		⚫	| ATCCode_prefix = P53
⚫	| FlashPt=
		⚫	| ATCCode_suffix = BB02
	| Autoignition=
			}}
			|Section7={{Chembox Hazards
		⚫	| MainHazards=
		⚫	| FlashPt=
			| AutoignitionPt =
			| PEL = none<ref name=PGCH>{{PGCH|0285}}</ref>
			| REL = None established<ref name=PGCH/>
			| IDLH = N.D.<ref name=PGCH/>
	}}		}}
	}}		}}
	'''Fenthion''' is an ] ], ], and ]. Like most other ]s, its mode of action is via ]. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in ] and ] toxicity class.<ref name=EXTOXNET> EXTOXNET. (2003). ''Pesticide information Profile for Fenthion''. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. Available at http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html Accessed April 25, 2009.</ref> <ref name=HSDB>HSDB. (2003). ''Hazardous Substance Data Bank: Fenthion''. National Library of Medicine: National Toxicology Program. Available at http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB Accessed April 29, 2009.</ref>		'''Fenthion''' is an ] ], ], and ]. Like most other ]s, its mode of action is via ]. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in ] and ] toxicity class.<ref name=HSDB>HSDB. (2003). ''Hazardous Substance Data Bank: Fenthion''. National Library of Medicine: National Toxicology Program. Available at http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB Accessed April 29, 2009.</ref><ref name=EXTOXNET>EXTOXNET. (2003). ''Pesticide information Profile for Fenthion''. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. Available at http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html Accessed April 25, 2009.</ref>
	== Uses ==		== Uses ==
	Fenthion is a contact and stomach insecticide used against many sucking, biting pests. It is particularly effective against fruit flies, leaf hoppers, cereal bugs, stem borers, mosquitoes, animal parasites, mites, aphids, codling moths, and weaver birds. It has been widely used in sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines.<ref name=EXTOXNET/>		Fenthion is a contact and stomach insecticide used against many biting insects. It is particularly effective against fruit flies, leaf hoppers, cereal bugs, stem borers, mosquitoes, animal parasites, mites, aphids, codling moths, and weaver birds. It has been widely used in sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines.<ref name=EXTOXNET/>
	Based on its high toxicity on birds, fenthion has been used to control weaver birds and other pest-birds in many parts of the world. Fenthion is also used in cattle, swine, and dogs to control lice, fleas, ticks, flies, and other external parasites.<ref name=EXTOXNET/><ref name=EPA>USEPA. (2001). ''Interim Reregeistration Eligibility Decision for Fenthion''. United States Environmental Protection Agency. Available at http://www.epa.gov/pesticides/reregistration/REDs/0290ired.pdf Accessed April 25, 2009.</ref><ref name=APVMA>APVMA. (2005). ''Fenthion Review - Frequently asked questions''. Australian Pesticides and Veterinary Medicines Authority. Available at http://www.apvma.gov.au/chemrev/fenthion_faq.shtml Accessed April 26, 2009.</ref>		Based on its high toxicity on birds, fenthion has been used to control weaver birds and other pest-birds in many parts of the world. Fenthion is also used in cattle, swine, and dogs to control lice, fleas, ticks, flies, and other external parasites.<ref name=EXTOXNET/><ref name=EPA>USEPA. (2001). ''Interim Reregeistration Eligibility Decision for Fenthion''. United States Environmental Protection Agency. Available at http://www.epa.gov/pesticides/reregistration/REDs/0290ired.pdf Accessed April 25, 2009.</ref><ref name=APVMA>APVMA. (2005). ''Fenthion Review - Frequently asked questions''. Australian Pesticides and Veterinary Medicines Authority. Available at http://www.apvma.gov.au/chemrev/fenthion_faq.shtml {{Webarchive|url=https://web.archive.org/web/20090519145031/http://www.apvma.gov.au/chemrev/fenthion_faq.shtml |date=2009-05-19 }} Accessed April 26, 2009.</ref>
	Amid concerns of harmful effects on environment, especially birds, ] no longer approves uses of fenthion. However, fenthion has been extensively used in Florida to control adult mosquitoes. After preliminary risk assessments on human health and environment in 1998 and its revision in 1999, USEPA issued an Interim Reregistration Eligibility Decision (IRED) for fenthion in January 2001. The EPA has classified fenthion as ] (RUP), and warrants special handling because of its toxicity.<ref name=ASTDR>ASTDR. (2005). ''Toxicologic Information about Insecticides Used for Eradicating Mosquitoes (West Nile Virus Control)''. Department of Health and Human Services: Agency for Toxic Substances and Disease Registry. Available at http://www.atsdr.cdc.gov/consultations/west_nile_virus/fenthion.html Accessed April 25, 2009.</ref>		Amid concerns of harmful effects on environment, especially birds, ] no longer approves uses of fenthion. However, fenthion has been extensively used in Florida to control adult mosquitoes. After preliminary risk assessments on human health and environment in 1998 and its revision in 1999, USEPA issued an Interim Reregistration Eligibility Decision (IRED) for fenthion in January 2001. The EPA has classified fenthion as ] (RUP), and warrants special handling because of its toxicity.<ref name=ASTDR>ASTDR. (2005). ''Toxicologic Information about Insecticides Used for Eradicating Mosquitoes (West Nile Virus Control)''. Department of Health and Human Services: Agency for Toxic Substances and Disease Registry. Available at Accessed April 25, 2009.</ref>
	Some common trade names for fenthion are Avigel, Avigrease, Entex, Baytex, Baycid, Dalf, DMPT, Mercaptophos, Prentox, Fenthion 4E, Queletox, and Lebaycid.<ref name=EXTOXNET/> Fenthion is available in dust, emulsifiable concentrate, granular, liquid concentrate, spray concentrate, ULV, and wettable powder formulations.		Some common trade names for fenthion are Avigel, Avigrease, Entex, Baytex, Baycid, Dalf, DMPT, Mercaptophos, Prentox, Fenthion 4E, Queletox, and Lebaycid.<ref name=EXTOXNET/> Fenthion is available in dust, emulsifiable concentrate, granular, liquid concentrate, spray concentrate, ULV, and wettable powder formulations.
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	== Synthesis ==		== Synthesis ==
	Fenthion can be synthesized by condensation of 4-methylmercapto-m-cresol and dimethylphosphorochloridothionate.<ref name=HSDB/>		Fenthion can be synthesized by condensation of 4-methylmercapto-m-cresol and ].<ref name=HSDB/>
	== Health effects ==		== Health effects ==
	Fenthion exposure to general population is quite limited based on its ]. Common form of fenthion exposure is occupation related, and occurs through dermal contact or inhalation of dust and sprays.<ref name=ASTDR/> Another likely means of contamination is through ingestion of food, especially, if it has been applied quite recently with fenthion. So far, ingestion is the most likely severe poisoning case on humans and animals.<ref name=HSDB/> To avoid this, crops applied with fenthion should be allowed enough degradation time before harvesting. Normally, 2 - 4 weeks time is enough depending upon the type of crop.		Fenthion exposure to general population is quite limited based on its ]. Common form of fenthion exposure is occupation related, and occurs through dermal contact or inhalation of dust and sprays.<ref name=ASTDR/> Another likely means of contamination is through ingestion of food, especially, if it has been applied quite recently with fenthion. So far, ingestion is the most likely severe poisoning case on humans and animals.<ref name=HSDB/> To avoid this, crops applied with fenthion should be allowed enough degradation time before harvesting. Normally, two to four weeks time is enough depending upon the type of crop.
	Fenthion poisoning is consistent with symptoms of other organophosphate effects on human health. Primarily, the effect is cholinesterase inhibition.		Fenthion poisoning is consistent with symptoms of other organophosphate effects on human health. Primarily, the effect is cholinesterase inhibition.
	===Acute toxicity===		===Acute toxicity===
	Acute poisoning of fenthion results into myosis (pinpoint pupils), headache, nausea/vomiting, dizziness, muscle weakness, drowsiness, lethargy, agitation, or anxiety. If the poisoning is moderate or severe, it results into chest tightness, breathing difficulty, hypertension, abdominal pain, diarrhea, heavy salivation, profuse sweating, or fasciculation. In extremely severe case, such as suicide attempt, the victim may get coma, respiratory arrest, seizures, loss of reflexes, and flaccid paralysis.<ref name=ASTDR/><ref name=EPA/>		Acute poisoning of fenthion results in miosis (pinpoint pupils), headache, nausea/vomiting, dizziness, muscle weakness, drowsiness, lethargy, agitation, or anxiety. If the poisoning is moderate or severe, it results in chest tightness, breathing difficulty, hypertension, abdominal pain, diarrhea, heavy salivation, profuse sweating, or fasciculation.<ref name=EPA/><ref name=ASTDR/>
	===Chronic toxicity===		===Chronic toxicity===
	Chronic effect of fenthion has not been reported.<ref name=ASTDR/>		Chronic effect of fenthion has not been reported.<ref name=ASTDR/>
	== Environmental effects==		== Environmental effects ==
	Despite short half-life in the environment, fenthion toxicity is highly significant to birds and estuarine/marine invertebrates.<ref name=EPA/> Even though some parts of the world use fenthion to control pest birds, such as weaver bird, many non-targeted wild birds are victim of fenthion poisoning. Acute symptoms of fenthion poisoning in birds include tearing of the eyes, foamy salivation, lack of movement, tremors, congestion of the windpipe, lack of coordination in walking, and an abnormally rapid rate of breathing or difficult breathing. Fenthion has been found toxic to fishes and other aquatic invertebrates. Bees are also found to be greatly affected by fenthion contamination.<ref name=EXTOXNET/>		Despite short half-life in the environment, fenthion toxicity is highly significant to birds and estuarine/marine invertebrates.<ref name=EPA/> Even though some parts of the world use fenthion to control pest birds, such as ], many non-targeted wild birds are victim of fenthion poisoning. Acute symptoms of fenthion poisoning in birds include tearing of the eyes, foamy salivation, lack of movement, tremors, congestion of the windpipe, lack of coordination in walking, and an abnormally rapid rate of breathing or difficult breathing. Fenthion has been found toxic to fishes and other aquatic invertebrates. Bees are also found to be greatly affected by fenthion contamination.<ref name=EXTOXNET/>
	== Degradation in nature ==		=== Degradation in nature ===
	] and ] are common mechanisms of fenthion degradation in the environment. In the atmosphere, vapor phase fenthion reacts rapidly with photochemically produced hydroxyl radicals, and its half-life is about 5 hours. In soil and water, photodegradation is again predominant mechanism if there is enough presence of sunlight.		] and ] are common mechanisms of fenthion degradation in the environment. In the atmosphere, vapor phase fenthion reacts rapidly with photochemically produced hydroxyl radicals, and its half-life is about 5 hours. In soil and water, photodegradation is again predominant mechanism if there is enough presence of sunlight.
	Under normal aquatic environment, half-life of fenthion in water is 2.9 to 21.1 days.<ref name=HSDB/> It may be photodynamically, chemically or biologically degraded. The degradation mechanisms can be hydrolysis, oxidation, and/or alkylation-dealkylation, which are dependent on the presence of light, temperature, alkali, or enzymatic activity.<ref name=Wang>Wang, T., Kadlac, T., and Lenahan, R. (1989). . Bull. Environ. Contam. Toxicol., 42 (3), 389-394. DOI: 10.1007/BF01699965</ref>		Under normal aquatic environment, half-life of fenthion in water is 2.9 to 21.1 days.<ref name=HSDB/> It may be photodynamically, chemically or biologically degraded. The degradation mechanisms can be hydrolysis, oxidation, and/or alkylation-dealkylation, which are dependent on the presence of light, temperature, alkali, or enzymatic activity.<ref name=Wang>{{Cite journal | doi = 10.1007/BF01699965| pmid = 2706349| title = Persistence of fenthion in the aquatic environment| journal = Bulletin of Environmental Contamination and Toxicology| volume = 42| issue = 3| pages = 389–94| year = 1989| last1 = Wang| first1 = T.| last2 = Kadlac| first2 = T.| last3 = Lenahan| first3 = R.| s2cid = 39628676}}</ref>
	In soil, fenthion degradation ranges from 4 to 6 weeks and it occurs through photodegradation as well as anaerobic or non-photolytic organisms. However, soil particles strongly adsorb fenthion that makes it less susceptible to percolate with water through the soil.<ref name=ASTDR/>		In soil, fenthion degradation ranges from four to six weeks and it occurs through photodegradation as well as anaerobic or non-photolytic organisms. However, soil particles strongly adsorb fenthion making it less susceptible to percolate with water through the soil.<ref name=ASTDR/>
	== References ==		== Regulation ==
			{{globalize section|date=April 2017}}
			===India===
⚫	<References/>
			{{seealso|List of banned and restricted pesticides in India}}
			Fenthion was used in India for more than 30 years as a larvicide for control of ] ]. The compound was on the review list of Central Insecticide Board in India and they decided to ban the product due to high toxicity concerns. All manufacture after January 2017 was banned. Subsequently a complete ban order, barring all import and usage was issued in August 2018.<ref>{{cite web |url=http://www.indianemployees.com/gazette-notifications/details/draft-order-banning-of-pesticides-order-2016 |title = DRAFT ORDER - Banning of Pesticides Order, 2016}}</ref>
			=== Australia ===
	{{insecticides}}
			Fenthion and dimethoate were widely used to combat the ], a species that has caused more than $28.5 million a year in damage to Australian fruit crops. However, it was banned in 2011 due to safety concerns.<ref>{{Cite journal|last1=Lloyd|first1=Annice C.|last2=Hamacek|first2=Edward L.|last3=Kopittke|first3=Rosemary A.|last4=Peek|first4=Thelma|last5=Wyatt|first5=Pauline M.|last6=Neale|first6=Christine J.|last7=Eelkema|first7=Marianne|last8=Gu|first8=Hainan|date=May 2010|title=Area-wide management of fruit flies (Diptera: Tephritidae) in the Central Burnett district of Queensland, Australia|journal=Crop Protection|volume=29|issue=5|pages=462–469|doi=10.1016/j.cropro.2009.11.003|issn=0261-2194}}</ref> Other insecticides and control techniques are being investigated to control the spread of this pest.
	{{Cholinergics}}
		⚫	== References ==
			{{reflist}}
			==External links==
			* {{PPDB|310}}
			{{Insecticides}}
			{{Acetylcholine metabolism and transport modulators}}
			]
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