N-Nitrosoglyphosate

N-Nitrosoglyphosate is the nitrosamine degradation product and synthetic impurity of glyphosate herbicide.

N-Nitrosoglyphosate
Names
IUPAC name
N-Nitroso-N-(phosphonomethyl)glycine
Systematic IUPAC name
[Nitroso(phosphonomethyl)amino]acetic acid
Other names
Nitrosoglyphosate, 56516-72-4, N-Nitrosoglyphosphate, 2-[nitroso(phosphonomethyl)amino]acetic acid, NNG
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C3H7N2O6P/c6-3(7)1-5(4-8)2-12(9,10)11/h1-2H2,(H,6,7)(H2,9,10,11) checkY
    Key: BJYYBQPCMQGLLZ-UHFFFAOYSA-N checkY
  • C(C(=O)O)N(CP(=O)(O)O)N=O
Properties
C3H7N2O6P
Molar mass 198.071 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The US EPA limits N-nitrosoglyphosate impurity to a maximum of 1 ppm in glyphosate formulated products.[1] N-Nitrosoglyphosate can also form from the reaction of nitrates and glyphosate. Formation of N-nitrosoglyphosate has been observed in soils treated with sodium nitrite and glyphosate at elevated levels, though formation in soil is not expected at under typical field conditions.[2]

References
  1. Pesticide Fact Sheet (Report). United States Environmental Protection Agency. June 1986. p. 4. Retrieved May 4, 2022.
  2. Khan, Shahamat U. (December 9, 1981). "N-Nitrosamine Formation in Soil from the Herbicide Glyphosate and its Uptake by Plants". N-Nitroso Compounds. ACS Symposium Series. Vol. 174. AMERICAN CHEMICAL SOCIETY. pp. 275–287. doi:10.1021/bk-1981-0174.ch019. ISBN 0-8412-0667-8.
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