Methamidophos: Difference between revisions

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Updating {{chembox}} (changes to verified and watched fields - updated 'UNII_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|bugs
m →‎Use in poisoning: -> →‎Consumer Toxicity: because "use in poisoning" makes it sound like a weapon of intrigue.
 
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| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 409136922
| verifiedrevid = 431612201
| Name = Methamidophos
| Name = Methamidophos
| ImageFile = Methamidophos.svg
| ImageFile = Methamidophos.svg
| ImageSize = 200px
| ImageSize = 200px
| ImageAlt = Skeletal formula of methamidophos
| ImageName = Methamidophos
| ImageFile1 = Methamidophos-3D-balls-2.png
| IUPACName = O,S-Dimethyl phosphoramidothioate
| ImageAlt1 = Ball-and-stick model of the methamidophos molecule
| Section1 = {{Chembox Identifiers
| PIN = ''O'',''S''-Dimethyl phosphoramidothioate
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|Section1={{Chembox Identifiers
| Beilstein = 1098870
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3954
| ChemSpiderID = 3954
| ChEBI_Ref = {{ebicite|correct|EBI}}
| InChI = 1/C2H8NO2PS/c1-5-6(3,4)7-2/h1-2H3,(H2,3,4)
| ChEBI = 38721
| InChIKey = NNKVPIKMPCQWCG-UHFFFAOYAA
| SMILES = O=P(OC)(SC)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 504888
| ChEMBL = 504888
| EC_number = 233-606-0
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 10265-92-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8Z083FM94W
| PubChem = 4096
| RTECS = TB4970000
| UNNumber = 3018 2783
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C18667
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H8NO2PS/c1-5-6(3,4)7-2/h1-2H3,(H2,3,4)
| StdInChI = 1S/C2H8NO2PS/c1-5-6(3,4)7-2/h1-2H3,(H2,3,4)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NNKVPIKMPCQWCG-UHFFFAOYSA-N
| StdInChIKey = NNKVPIKMPCQWCG-UHFFFAOYSA-N
| SMILES = O=P(OC)(SC)N
| CASNo_Ref = {{cascite|correct|CAS}}
}}
| CASNo = 10265-92-6
|Section2={{Chembox Properties
| PubChem = 4096
| Formula = C<sub>2</sub>H<sub>8</sub>NO<sub>2</sub>PS
| KEGG_Ref = {{keggcite|changed|kegg}}
| MolarMass = 141.1 g/mol
| KEGG = C18667
| Density = 1.31 g/cm<sup>3</sup>
| MeltingPtC = 44.5
| BoilingPt = thermally unstable
}}
}}
| Section2 = {{Chembox Properties
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS06}}{{GHS09}}
| Formula = C<sub>2</sub>H<sub>8</sub>N<sub></sub>O<sub>2</sub>PS
| GHSSignalWord = Danger
| MolarMass = 141.1 g/mol
| HPhrases = {{H-phrases|300|311|330|400}}
| Density = 1.31 g/cm³
| PPhrases = {{P-phrases|260|264|270|271|273|280|284|301+310|302+352|304+340|310|312|320|321|322|330|361|363|391|403+233|405|501}}
| MeltingPtC = 44.5
| BoilingPt = thermally unstable
}}
}}
}}
}}
'''Methamidophos''', trade name "Monitor," is an [[organophosphate]] [[insecticide]].


Crops grown with the use of methamidophos include potatoes<ref>{{cite web |url=http://pmep.cce.cornell.edu/profiles/insect-mite/fenitrothion-methylpara/methamidophos/insect-prof-methamidophos.html |url-status=dead |archive-url=https://web.archive.org/web/20000303012717/http://pmep.cce.cornell.edu/profiles/insect-mite/fenitrothion-methylpara/methamidophos/insect-prof-methamidophos.html |archive-date=2000-03-03 |title=methamidophos (Monitor) Page 1}}</ref> and some Latin American rice.<ref>[https://www.nytimes.com/2008/03/30/opinion/30stutchbury.html?em&ex=1207108800&en=110a4c484f3ed9f9&ei=5087%0A Did Your Shopping List Kill A Songbird?] Bridget Stutchbury, [[New York Times]] March 30, 2008</ref> Many nations have used methamidophos on crops, including developed nations such as [[Spain]], [[United States]], [[Japan]], and [[Australia]]. Due to its toxicity, the use of pesticides that contain methamidophos is currently being phased out in [[Brazil]]. In 2009, all uses in the United States were voluntarily canceled.<ref>{{Cite web|url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/frn_UG-2_23-Sep-2009.pdf|title=Federal Register / Vol. 74, No. 183 / Wednesday, September 23, 2009 / Notices|date=23 September 2009|website=US EPA|access-date=13 February 2018}}</ref>
'''Methamidophos''' is an [[organophosphate]] [[insecticide]].<ref name="http://www.alanwood.net/pesticides/class_insecticides.html">[http://www.alanwood.net/pesticides/class_insecticides.html http://www.alanwood.net/pesticides/class_insecticides.html]</ref>

Crops grown with the use of methamidophos include some Latin American rice.<ref>[http://www.nytimes.com/2008/03/30/opinion/30stutchbury.html?em&ex=1207108800&en=110a4c484f3ed9f9&ei=5087%0A Did Your Shopping List Kill A Songbird?] Bridget Stutchbury, [[New York Times]] March 30, 2008</ref> Many nations use methamidophos on crops, including developed nations such as [[Spain]], [[US]], [[Japan]], and [[Australia]].


==Toxicity==
==Toxicity==
{{LD50}} rates of 21 and 16 mg/kg for male and female rats, respectively. 10-30 mg/kg in [[rabbits]], and [[dermal]] LD50 of 50 mg/kg in rats. It is rapidly absorbed through the stomach, lungs, and skin in humans, and eliminated primarily through urine.<ref name="pic">[http://www.pic.int/INCs/CRC1/q17)/English/CRC%201-17%20methamidophos.pdf]</ref> It is a [[cholinesterase]] inhibitor.
{{LD50}} rates of 21 and 16&nbsp;mg/kg for male and female rats, respectively. 10–30&nbsp;mg/kg in [[rabbits]], and [[dermal]] LD50 of 50&nbsp;mg/kg in rats. It is rapidly absorbed through the stomach, lungs, and skin in humans, and eliminated primarily through urine.<ref name="pic">{{Cite web|url=http://www.pic.int/INCs/CRC1/q17)/English/CRC%201-17%20methamidophos.pdf|title = Rotterdam Convention Home Page}}</ref> It is a [[cholinesterase]] inhibitor.


Breakdown in soil is 6.1 days in sand, 309 days in water at pH 5.0, 27 days at pH 7.0, and 3 days at pH 9.0. Sunlight accelerates breakdown. It is uptaken through roots and leaves of plants.<ref name="pic"/>
Breakdown in soil is 6.1 days in sand, 309 days in water at pH 5.0, 27 days at pH 7.0, and 3 days at pH 9.0. Sunlight accelerates breakdown. It is uptaken through roots and leaves of plants.<ref name="pic"/>
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==Use==
==Use==
Methamidophos is used in great quantities in ricefields in China.<ref name="idrc">[http://www.idrc.ca/en/ev-27875-201-1-DO_TOPIC.html International Development Research Center]</ref> Rice–fish culture is common in the southern parts of China as well as in many other rice-producing countries (e.g., [[Thailand]], [[Malaysia]], and the [[Philippines]]). Brown rice (unpolished) in this study contained double the concentration of polished rice. Both plants and animals did not degrade the pesticide well, and fish for human consumption in these cases contains methamidophos in concentrations roughly similar to brown rice.<ref name="idrc"/>
Methamidophos is used in great quantities in ricefields in China.<ref name="idrc">{{Cite web|url=http://www.idrc.ca/en/ev-27875-201-1-DO_TOPIC.html|archiveurl=https://web.archive.org/web/20090314114543/http://www.idrc.ca/en/ev-27875-201-1-DO_TOPIC.html|url-status=dead|title=International Development Research Center|archivedate=Mar 14, 2009|accessdate=Jul 18, 2022}}</ref> Rice–fish culture is common in the southern parts of China as well as in many other rice-producing countries (e.g., [[Thailand]], [[Malaysia]], and the [[Philippines]]). Brown rice (unpolished) in this study contained double the concentration of polished rice. Both plants and animals did not degrade the pesticide well, and fish for human consumption in these cases contains methamidophos in concentrations roughly similar to brown rice.<ref name="idrc"/>


==Consumer Toxicity==
==Use in poisoning==
Methamidophos was found in dumplings ([[gyoza]]) manufactured in China for the Japanese market after a number of consumers became sick.<ref>Japan Times http://www.japantoday.com/category/crime/view/china-launches-contaminated-dumplings-probe</ref>
Methamidophos was found in dumplings ([[gyoza]]) manufactured in China for the Japanese market after a number of consumers became sick.<ref>{{Cite news|url=https://japantoday.com/category/crime/china-launches-contaminated-dumplings-probe|title=Chinese factory insiders suspected of tampering with dumplings|newspaper=[[Japan Today]]|accessdate=Jul 18, 2022}}</ref>

==See also==
*[[GS-7]]


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


==External links ==
{{insecticides}}
{{Cholinergics}}
* {{PPDB|453}}


{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}
{{Neurotoxins}}
{{Consumer Food Safety}}

[[Category:Acetylcholinesterase inhibitors]]
[[Category:Organophosphate insecticides]]
[[Category:Organophosphate insecticides]]
[[Category:Anticholinesterases]]
[[Category:Persistent organic pollutants]]
[[Category:Phosphoramidothioates]]
[[Category:Phosphoramidothioates]]
[[Category:Methoxy compounds]]

<!-- commercial name; it will probably be changed to the chemimcal name //-->

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