Aminomethylphosphonic acid

Aminomethylphosphonic acid
Names
	IUPAC name (Aminomethyl)phosphonic acid
	Other names Aminomethanephosphonic acid
Identifiers
CAS Number	1066-51-9 ;
3D model (JSmol)	Interactive image;
Abbreviations	AMPA; AMeP
ChEBI	CHEBI:28812;
ChemSpider	13399;
ECHA InfoCard	100.152.014
PubChem CID	14017;
UNII	90825O5C1U ;
CompTox Dashboard (EPA)	DTXSID5037490 ;
	InChI InChI=1S/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5) Key: MGRVRXRGTBOSHW-UHFFFAOYSA-N; InChI=1/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5) Key: MGRVRXRGTBOSHW-UHFFFAOYAF;
	SMILES O=P(O)(O)CN;
Properties
Chemical formula	CH6NO3P
Molar mass	111.037 g·mol−1
Appearance	Solid
Melting point	338 to 344 °C (640 to 651 °F; 611 to 617 K)
Acidity (pKa)	0.4
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Aminomethylphosphonic acid (AMPA) is a weak organic acid with a phosphonic acid group. It is one of the primary degradation products of the herbicide glyphosate.[1] AMPA has toxicity which is comparable to that of glyphosate and it is therefore considered to be of similar toxicological concern (harmful in greater than 0.5 parts per billion) as glyphosate itself.[2] AMPA has the potential to be broken down further by manganese oxide in laboratory conditions, however in soil manganese oxide is usually only present in trace amounts.[3] Microbial degradation of AMPA is the more likely degradation pathway, where it degrades into phosphoric acid [4][5] and ultimately to carbon dioxide and inorganic phosphate.[6]

Structures of AMPA in different pH ranges[7]

References

Environmental Fate of Glyphosate Archived 2012-04-20 at the Wayback Machine, Jeff Schuette, Department of Pesticide Regulation, California
Pesticide Residues in Food - 1997, FAO Panel of Experts on Pesticide Residues in Food and the Environment and the WHO Core Assessment Group
K. A. Barrett and M. B. McBride. Oxidative Degradation of Glyphosate and Aminomethylphosphonate by Manganese Oxide. Environ. Sci. Technol., 2005, 39 (23), pp 9223–9228
Pipke R, Amrhein N. (1988) Isolation and characterization of a mutant of Arthrobacter sp. strain GLP-1 which utilizes the herbicide glyphosate as its sole source of phosphorus and nitrogen. Applied and Environmental Microbiology 54(11): 2868-2870.
Forlani G, Mangiagalli A, Nielsen E, Suardi CM. (1999) Degradation of the phosphonate herbicide glyphosate in soil: Evidence for a possible involvement of unculturable microorganisms. Soil Biology and Biochemistry 31: 991-997
Backgrounder: Glyphosate does not degrade to phosphorous acid in the environment. Monsanto. 2005
Zuliang Chen, Wenxiang He, Michael Beer, Mallavarapu Megharaj, Ravendra Naidu (2009-05-15). "Speciation of glyphosate, phosphate and aminomethylphosphonic acid in soil extracts by ion chromatography with inductively coupled plasma mass spectrometry with an octopole reaction system". Talanta. 78 (3): 852. doi:10.1016/j.talanta.2008.12.052.CS1 maint: multiple names: authors list (link)

External links

Concentrations of Glyphosate, Its Degradation Product, Aminomethylphosphonic Acid, and Glufosinate in Ground- and Surface-Water, Rainfall, and Soil Samples Collected in the United States, 2001-06, United States Geological Survey

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[1] Environmental Fate of Glyphosate Archived 2012-04-20 at the Wayback Machine, Jeff Schuette, Department of Pesticide Regulation, California

[2] Pesticide Residues in Food - 1997, FAO Panel of Experts on Pesticide Residues in Food and the Environment and the WHO Core Assessment Group

[3] K. A. Barrett and M. B. McBride. Oxidative Degradation of Glyphosate and Aminomethylphosphonate by Manganese Oxide. Environ. Sci. Technol., 2005, 39 (23), pp 9223–9228

[4] Pipke R, Amrhein N. (1988) Isolation and characterization of a mutant of Arthrobacter sp. strain GLP-1 which utilizes the herbicide glyphosate as its sole source of phosphorus and nitrogen. Applied and Environmental Microbiology 54(11): 2868-2870.

[5] Forlani G, Mangiagalli A, Nielsen E, Suardi CM. (1999) Degradation of the phosphonate herbicide glyphosate in soil: Evidence for a possible involvement of unculturable microorganisms. Soil Biology and Biochemistry 31: 991-997

[6] Backgrounder: Glyphosate does not degrade to phosphorous acid in the environment. Monsanto. 2005

[7] Zuliang Chen, Wenxiang He, Michael Beer, Mallavarapu Megharaj, Ravendra Naidu (2009-05-15). "Speciation of glyphosate, phosphate and aminomethylphosphonic acid in soil extracts by ion chromatography with inductively coupled plasma mass spectrometry with an octopole reaction system". Talanta. 78 (3): 852. doi:10.1016/j.talanta.2008.12.052.CS1 maint: multiple names: authors list (link)