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Revision as of 16:55, 20 January 2011 editYobot (talk | contribs)Bots4,733,870 editsm Fixed/removed {{expand}} + WP:CHECKWIKI error fixes + general fixes, removed: {{expand|date=February 2010}} using AWB (7552)← Previous edit Latest revision as of 02:01, 28 May 2024 edit undoMfernflower (talk | contribs)Extended confirmed users7,772 edits →Safety and environmental considerations: Clarify about the Shasta pesticide spillTags: Mobile edit Mobile web edit Advanced mobile edit 
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{{chembox {{chembox
| verifiedrevid = 400306173 | verifiedrevid = 409002120
|Reference=<ref name="Merck">'']'', 11th Edition, '''5860'''.</ref> | Reference = <ref name="Merck">'']'', 11th Edition, '''5860'''.</ref>
|ImageFile=metham sodium.png | ImageFile = metham sodium.png
|ImageSize=150px | ImageSize = 160px
| ImageFile1 = Metham sodium 3D ball.png
|IUPACName=Sodium methylaminomethanedithioate
| ImageSize1 = 170
⚫ |OtherNames=Carbathion<br>Carbathione<br>Carbothion<br>Metamsodium<br>Metam-sodium
| ImageAlt1 = Ball-and-stick model of the component ions of metham sodium
| PIN = Sodium methylcarbamodithioate
⚫ | OtherNames = Metham sodium<br>Carbathion<br>Carbathione<br>Carbothion<br>Metamsodium<br>Metam-sodium
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2273119 | ChemSpiderID = 2273119
| InChI = 1/C2H5NS2.Na/c1-3-2(4)5;/h1H3,(H2,3,4,5);/q;+1/p-1
| InChIKey = AFCCDDWKHLHPDF-REWHXWOFAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5NS2.Na/c1-3-2(4)5;/h1H3,(H2,3,4,5);/q;+1/p-1 | StdInChI = 1S/C2H5NS2.Na/c1-3-2(4)5;/h1H3,(H2,3,4,5);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AFCCDDWKHLHPDF-UHFFFAOYSA-M | StdInChIKey = AFCCDDWKHLHPDF-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=137-42-8 | CASNo=137-42-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem=5366415
| UNII = 3CD7UKN224
⚫ | SMILES = .C(=S)NC
⚫ | PubChem = 5366415
⚫ }}
⚫ | SMILES = .C(=S)NC
⚫ }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>2</sub>H<sub>4</sub>NNaS<sub>2</sub> | Formula=C<sub>2</sub>H<sub>4</sub>NNaS<sub>2</sub>
| MolarMass=129.18 g/mol | MolarMass=129.18 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Metham sodium''' is a soil ] used as a ], ], and ]. It is one of the most widely used pesticides in the United States, with approximately 60 million pounds used in 2001.<ref>, U.S. Environmental Protection Agency</ref> Metham sodium is the ] ] of ]. '''Metam sodium''' is an ] with the formula {{chem2|CH3NHCS2Na}}. The compound is a sodium salt of a ]. The compound exists as a colorless dihydrate, but most commonly it is encountered as an aqueous solution.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a17_125.pub2|chapter=Nematicides |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2008 |last1=Hartwig |first1=Jürgen |last2=Sommer |first2=Herbert |last3=Müller |first3=Franz |isbn=978-3527306732 }}</ref> It is used as a soil ], ], ], and ]. It is one of the most widely used pesticides in the United States, with approximately 60 million pounds used in 2001.<ref> {{webarchive|url=https://web.archive.org/web/20090207095013/http://www.epa.gov/oppbead1/pestsales/01pestsales/usage2001_2.htm |date=2009-02-07 }}, U.S. Environmental Protection Agency</ref>


==Preparation and properties==
Metham sodium can be prepared from ], ], and ]; or from ] and ].<ref name="Merck"/> Metam sodium is prepared by combining ], ], and ]:<ref name=Ullmann/>
:{{chem2|CH3NH2 + CS2 + NaOH → CH3NHCS2Na + H2O}}
It also arises from the reaction of ] and ].<ref name="Merck"/>


Upon exposure to the environment, metam sodium decomposes to ] and other sulfur compounds.<ref name="pmid21740140">{{cite journal| author=Bretaudeau Deguigne M, Lagarce L, Boels D, Harry P| title=Metam sodium intoxication: the specific role of degradation products--methyl isothiocyanate and carbon disulphide--as a function of exposure. | journal=Clin Toxicol (Phila) | year= 2011 | volume= 49 | issue= 5 | pages= 416–22 | pmid=21740140 | doi=10.3109/15563650.2011.585472 | pmc= | url=https://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=21740140 }} </ref>
Upon exposure to the environment, metham sodium decomposes to form ].<ref>, Australian Pesticides and Veterinary Medicines Authority, June 1997</ref>

==Safety and environmental considerations==
Metam sodium is nonpersistent in the environment since it decomposes rather quickly to toxic ] and ].<ref name="pmid21740140">{{cite journal| author=Bretaudeau Deguigne M, Lagarce L, Boels D, Harry P| title=Metam sodium intoxication: the specific role of degradation products--methyl isothiocyanate and carbon disulphide--as a function of exposure. | journal=Clin Toxicol (Phila) | year= 2011 | volume= 49 | issue= 5 | pages= 416–22 | pmid=21740140 | doi=10.3109/15563650.2011.585472 | pmc= | url=https://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=21740140 }} </ref> In 1991 a ] into ] above ]. This killed all fish in a 41-mile stretch of the river. 20 years later the ] population had recovered.<ref>{{Cite web|url=https://dtsc.ca.gov/20th-anniversary-of-largest-chemical-spill-in-california-history/|title=Largest chemical spill in California history|website=dtsc.ca.gov|language=en|access-date=2017-12-11}}</ref>

==See also==
* ] - A related ] salt which is also used as a fungicide


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

==External links==
* {{PPDB|447}}


{{Herbicides}} {{Herbicides}}
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