Editing Fenitrothion

{{unbalanced|reason= Every pesticide that is approved for use has been judged to have an acceptable risk-benefit profile.  This article describes the risks, but not the benefits.|date=August 2018}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443755402
| ImageFile1 =Fenitrothion-Molecule-3D-balls-by-AHRLS-2013.png
| ImageSize1 =200px
| ImageFile =Phenitrothion.svg
| ImageSize =200px
| PIN =''O'',''O''-Dimethyl ''O''-(3-methyl-4-nitrophenyl) phosphorothioate
| OtherNames =• Dimethoxy-(3-methyl-4-nitrophenoxy)thioxophosphorane<br>''O,O''-Dimethyl ''O''-4-nitro-''m''-tolyl phosphorothioate
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 28941
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = W8M4X3Y7ZY
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14442
| InChI = 1/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3
| InChIKey = ZNOLGFHPUIJIMJ-UHFFFAOYAZ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 347698
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZNOLGFHPUIJIMJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =122-14-5
| PubChem =31200
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34757
| SMILES = S=P(Oc1cc(c(cc1)[N+]([O-])=O)C)(OC)OC
}}
|Section2={{Chembox Properties
| C=9 | H=12 | N=1 | O=5 | P=1 | S=1
| Appearance =Yellow-brown liquid
| Density = 1.3227 g/cm<sup>3</sup>
| MeltingPtC = 3.4
| BoilingPtC = 118
| BoilingPt_notes = at 0.05 mmHg
| Solubility = 38.0 mg/L
| SolubleOther = Readily soluble in dichloromethane, 2-propanol, toluene, hardly soluble in ''n''-hexane.<ref>{{cite book | title = Farm Chemicals Handbook | year = 1999 | location = Willoughby, OH | publisher = Meister Publishing Co. | page = 177 | isbn = 978-1-892829-02-3 | oclc = 50201739 }}</ref>
| LogP =3.30 (octanol/water)<ref>{{cite book | vauthors = Hansch C, Leo A, Hoekman D | title = Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. | location = Washington, DC | publisher = American Chemical Society | year = 1995 | pages = 60 | isbn = 978-0-8412-2993-8 | oclc = 924843801 }}</ref>
  }}
|Section3={{Chembox Hazards
| MainHazards =
| LD50 =Rat, oral: 500 mg/kg<ref>{{cite book | vauthors = Eckroth D, Grayson M, Kirk RE, Othmer DF | title = Kirk-Othmer Encyclopedia of Chemical Technology. | edition = 3rd | volume = 3 | location = New York, NY | publisher = John Wiley and Sons | page = 440 | year = 1981 | isbn = 978-0-471-02066-0 | oclc = 873939596 }}</ref><br>
Mouse (female), oral: 1416 mg/kg<ref>{{cite report | vauthors = Sekizawa J, Eto M, Miyamoto J, Matsuo M | publisher = World Health Organization | location = Geneva | title = Environ Health Criteria 133: Fenitrothion | page = 70 | year = 1992 | url = http://www.inchem.org/documents/ehc/ehc/ehc133.htm }}</ref>
| FlashPt =
| AutoignitionPt =
 }}
}}

'''Fenitrothion''' ([[IUPAC]] name: '''''O'',''O''-dimethyl ''O''-(3-methyl-4-nitrophenyl) phosphorothioate''') is a [[phosphorothioate]] ([[organophosphate]]) [[insecticide]] that is inexpensive and widely used worldwide. Trade names include ''Sumithion'', a 94.2% solution of fenitrothion.<ref name=pc>{{cite web | title = Fenitrothion | url = https://pubchem.ncbi.nlm.nih.gov/compound/fenitrothion | publisher = National Center for Biotechnology Information | work = PubChem Compound Database }}</ref>

==Health effects==
{{medref|section|date=August 2018}}
Fenitrothion at sublethal doses affected the motor movement of marsupials,<ref>{{cite journal | vauthors = Buttemer WA, Story PG, Fildes KJ, Baudinette RV, Astheimer LB | title = Fenitrothion, an organophosphate, affects running endurance but not aerobic capacity in fat-tailed dunnarts (Sminthopsis crassicaudata) | journal = Chemosphere | volume = 72 | issue = 9 | pages = 1315–20 | date = July 2008 | pmid = 18547601 | doi = 10.1016/j.chemosphere.2008.04.054 | bibcode = 2008Chmsp..72.1315B }}</ref> and at acute dose levels it reduced the energy of birds.<ref>{{cite journal | vauthors = Kitulagodage M, Isanhart J, Buttemer WA, Hooper MJ, Astheimer LB | title = Fipronil toxicity in northern bobwhite quail Colinus virginianus: reduced feeding behaviour and sulfone metabolite formation | journal = Chemosphere | volume = 83 | issue = 4 | pages = 524–30 | date = April 2011 | pmid = 21227481 | doi = 10.1016/j.chemosphere.2010.12.057 | bibcode = 2011Chmsp..83..524K }}</ref>

In chronic (low) dose tests, unexpectedly only the lowest concentration (0.011 microgram/liter) of fenitrothion depressed the growth of an algae, though all of the chronic dose levels used were toxic in other ways to the algae.<ref>{{cite journal | vauthors = Ferrando MD, Sancho E, Andreu-Moliner E | title = Chronic toxicity of fenitrothion to an algae (Nannochloris oculata), a rotifer (Brachionus calyciflorus), and the cladoceran (Daphnia magna) | journal = Ecotoxicology and Environmental Safety | volume = 35 | issue = 2 | pages = 112–20 | date = November 1996 | pmid = 8950533 | doi = 10.1006/eesa.1996.0090 | bibcode = 1996EcoES..35..112F }}</ref>

Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish).<ref>{{cite journal | vauthors = Saxena PK, Mani K | title = Effect of safe concentrations of some pesticides on thyroid in the freshwater murrel, Channa punctatus: a histopathological study | journal = Environmental Pollution | volume = 55 | issue = 2 | pages = 97–105 | year = 1988 | pmid = 15092506 | doi = 10.1016/0269-7491(88)90121-2 }}</ref>

Cases of non-specific [[encephalopathy]] and fatty visceral changes ([[Reye's syndrome]]) in children living in the vicinity of fenitrothion-spraying operations invoked the research described latterly in ''[[Science (journal)|Science]]'',<ref>{{cite journal | vauthors = Crocker JF, Ozere RL, Safe SH, Digout SC, Rozee KR, Hutzinger O | title = Lethal interaction of ubiquitous insecticide carriers with virus | journal = Science | volume = 192 | issue = 4246 | pages = 1351–3 | date = June 1976 | pmid = 179146 | doi = 10.1126/science.179146 | bibcode = 1976Sci...192.1351C }}</ref> and originally in ''[[The Lancet]]'':<ref>{{cite journal | vauthors = Crocker JF, Rozee KR, Ozere RL, Digout SC, Hutzinger O | title = Insecticide and viral interaction as a cause of fatty visceral changes and encephalopathy in the mouse | journal = Lancet | volume = 2 | issue = 7871 | pages = 22–4 | date = July 1974 | pmid = 4134409 | doi = 10.1016/S0140-6736(74)91351-8 }}</ref>
{{cquote|2-day-old mice were dosed topically for 11 days with fenitrothion, amongst other substances. After a further 2 days a sublethal dose of [[encephalomyocarditis]] virus was injected subcutaneously in known titre. Mortality-rates in the 10-day period after [[virus]] injection 4-9% in fenitrothion groups, and 0% in corn-oil controls. Fatty changes were noted in liver and kidney in the insecticide-virus groups. The encephalopathy showed no specific central-nervous system lesion, but death followed a sequence of paralysis and convulsions. The possible role of exposure to combinations of insecticides in human viral susceptibility requires further attention.}}

Further study showed that the illness was caused not by fenitrothion itself, but combinations which included the surfactants and the solvent (with or without the pesticide) clearly showed that pretreatment with these chemicals markedly increased the viral lethality in the test mice.<ref>{{cite journal |doi=10.1016/0045-6535(77)90075-3 |title=Analysis of an aromatic solvent used in a forest spray program |journal=Chemosphere |volume=6 |issue=10 |pages=641–651 |year=1977 | vauthors = Safe S, Plugge H, Crocker JF |bibcode=1977Chmsp...6..641S }}</ref>

==Resistance==
In an unusual demonstration of resistance to pesticides, 8% of insects in farm fields were found to carry a symbiotic gut microbe that can metabolize and detoxify fenitrothion; after in-vitro tests showed that the microbe significantly increased the survival of fenitrothion-treated insects.<ref>{{cite journal | vauthors = Kikuchi Y, Hayatsu M, Hosokawa T, Nagayama A, Tago K, Fukatsu T | title = Symbiont-mediated insecticide resistance | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 109 | issue = 22 | pages = 8618–22 | date = May 2012 | pmid = 22529384 | pmc = 3365206 | doi = 10.1073/pnas.1200231109 | bibcode = 2012PNAS..109.8618K | doi-access = free }}</ref>

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
*{{cite web | first = David | last = Folster | name-list-style = vanc | url = http://www.cbc.ca/archives/entry/canadas-trees-poison-mists | title = Poison mists from pesticides in New Brunswick | work = Five Nights | publisher = CBC Radio |date=14 May 1976 }} 
{{refend}}

== External links ==
*{{PPDB|299}}
*[http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB Hazardous Substances Data Bank (source of data)]
*[http://www.inchem.org/documents/ehc/ehc/ehc133.htm Inchem]
*[http://extoxnet.orst.edu/pips/fenitrot.htm Entox]
*[http://collection.nlc-bnc.ca/100/200/301/hcan-scan/pmra-arla/proposed_acceptability-e/pacr2003-08/pacr2003-08-e.pdf Re-evaluation of Fenitrothion] by the [[Pest Management Regulatory Agency]] of Canada

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

[[Category:Acetylcholinesterase inhibitors]]
[[Category:Organophosphate insecticides]]
[[Category:Nitrotoluene derivatives]]
[[Category:Organothiophosphate esters]]