N-Nitrosoglyphosate

{{Chembox

| Watchedfields =

| verifiedrevid =

| ImageFile = N-Nitrosoglyphosate.png

| ImageSize =

| IUPACName = N-Nitroso-N-(phosphonomethyl)glycine

| SystematicName = [Nitroso(phosphonomethyl)amino]acetic acid

| OtherNames = Nitrosoglyphosate, 56516-72-4, N-Nitrosoglyphosphate, 2-[nitroso(phosphonomethyl)amino]acetic acid, NNG

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|PubChem}}

| CASNo = 56516-72-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2HME3JQ5MM

| SMILES = C(C(=O)O)N(CP(=O)(O)O)N=O

| PubChem = 41910

| DTXSID = DTXSID30205066

| ChEMBL = 96010

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 38242

| StdInChI = 1S/C3H7N2O6P/c6-3(7)1-5(4-8)2-12(9,10)11/h1-2H2,(H,6,7)(H2,9,10,11)

| StdInChIKey = BJYYBQPCMQGLLZ-UHFFFAOYSA-N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=3 | H=7 | N=2 | O=6 | P=1

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|Section3={{Chembox Hazards

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

The US EPA limits N-nitrosoglyphosate impurity to a maximum of 1 ppm in glyphosate formulated products.{{Cite report |url=https://nepis.epa.gov/Exe/ZyNET.exe/91024L3C.txt?ZyActionD=ZyDocument&Client=EPA&Index=1986%20Thru%201990&Docs=&Query=%28NNG%29%20OR%20FNAME%3D%2291024L3C.txt%22%20AND%20FNAME%3D%2291024L3C.txt%22&Time=&EndTime=&SearchMethod=1&TocRestrict=n&Toc=&TocEntry=&QField=&QFieldYear=&QFieldMonth=&QFieldDay=&UseQField=&IntQFieldOp=0&ExtQFieldOp=0&XmlQuery=&File=D%3A%5CZYFILES%5CINDEX%20DATA%5C86THRU90%5CTXT%5C00000034%5C91024L3C.txt&User=ANONYMOUS&Password=anonymous&SortMethod=h%7C-&MaximumDocuments=1&FuzzyDegree=0&ImageQuality=r75g8/r75g8/x150y150g16/i425&Display=hpfr&DefSeekPage=x&SearchBack=ZyActionL&Back=ZyActionS&BackDesc=Results%20page&MaximumPages=1&ZyEntry=1 |title=Pesticide Fact Sheet |date=June 1986 |publisher=United States Environmental Protection Agency |page=4 |access-date=May 4, 2022 }} 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.

{{cite book |last= Khan |first= Shahamat U. |title= N-Nitroso Compounds |date= December 9, 1981 |chapter= N-Nitrosamine Formation in Soil from the Herbicide Glyphosate and its Uptake by Plants|volume= 174 |location= |publisher= AMERICAN CHEMICAL SOCIETY|pages= 275–287 |doi=10.1021/bk-1981-0174.ch019 | isbn= 0-8412-0667-8|series= ACS Symposium Series }}