Glyphosine

Glyphosine
Names
	Preferred IUPAC name N,N-bis(phosphonomethyl)glycine
Identifiers
CAS Number	2439-99-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:63484;
ChEMBL	ChEMBL265954;
ChemSpider	16196 ;
ECHA InfoCard	100.017.699
EC Number	219-468-4;
KEGG	C19132;
PubChem CID	17112;
UNII	2U96121SKR;
CompTox Dashboard (EPA)	DTXSID2044557 ;
	InChI InChI=1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13) Key: OXHDYFKENBXUEM-UHFFFAOYSA-N;
	SMILES C(C(=O)O)N(CP(=O)(O)O)CP(=O)(O)O;
Properties
Chemical formula	C4H11NO8P2
Molar mass	263.079 g·mol−1
Appearance	Colourless solid
Solubility in water	350 g/L
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	danger
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H318
Precautionary statements	P264+P265, P280, P305+P354+P338, P317
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3925 mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glyphosine is a plant growth regulator used on sugar beet and sugarcane. ᛁt inhibits fiber production, causing the plant to divert more dry matter to sucrose storage.^[1] 76,000 pounds (34,000 kg) of glyphosine were used in the US in 1974.^[3] It was first registered in 1972, though now is considered largely obsolete.^[1] In other plants, e.g. maize, it causes chlorosis by inhibiting plasmid RNA synthesis.^[4]It can be synthesized from chloroacetic acid and N,N-bis(phosphonomethyl)amine.^[5] Metals form complexes with glyphosine.^[6]^[7]

Chemically, glyphosine is a tertiary amine, a glycine derivative and a phosphonic acid.^[2]

It has been manufactured by CCA Biochemical and Monsanto, and sold under the "Polaris" trademark.^[1]

References

^ ^a ^b ^c ^d ^e Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
^ ^a ^b "Glyphosine". pubchem.ncbi.nlm.nih.gov.
^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
^ Slovin, Janet P.; Tobin, Elaine M. (12 August 1981). "Glyphosine, a plant growth regulator, affects chloroplast membrane proteins". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 637 (1): 177–184. doi:10.1016/0005-2728(81)90224-3.
^ "n2:0044-460X - Search Results". search.worldcat.org. Retrieved 2024-11-21.
^ Xuebing, Ma; Xiangkai, Fu (2004-02-02). "Synthesis of the novel layered amorphous and crystalline zirconium phosphate–phosphonates Zr(HPO4)[O3PCH2N(CH2CH2)2O]·nH2O, Zr(HPO4)[O3PCH2N(CH2CO2H)2]·nH2O, zirconium phosphonates Zr[(O3PCH2)NCH2CO2H]·nH2O and the catalytic activities of their palladium complexes in hydrogenation". Journal of Molecular Catalysis A: Chemical. 208 (1): 129–133. doi:10.1016/j.molcata.2003.07.004. ISSN 1381-1169.
^ Galanski, Mathea Sophia; Slaby, Susanna; Jakupec, Michael A.; Keppler, Bernhard K. (2003-11-06). "Synthesis, Characterization, and in Vitro Antitumor Activity of Osteotropic Diam(m)ineplatinum(II) Complexes Bearing a N , N -Bis(phosphonomethyl)glycine Ligand". Journal of Medicinal Chemistry. 46 (23): 4946–4951. doi:10.1021/jm0308040. ISSN 0022-2623. PMID 14584945.

Links

Glyphosine in the Pesticide Properties DataBase (PPDB)

[database-1] Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242

[pubchem-2] "Glyphosine". pubchem.ncbi.nlm.nih.gov.

[3] "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.

[4] Slovin, Janet P.; Tobin, Elaine M. (12 August 1981). "Glyphosine, a plant growth regulator, affects chloroplast membrane proteins". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 637 (1): 177–184. doi:10.1016/0005-2728(81)90224-3.

[5] "n2:0044-460X - Search Results". search.worldcat.org. Retrieved 2024-11-21.

[6] Xuebing, Ma; Xiangkai, Fu (2004-02-02). "Synthesis of the novel layered amorphous and crystalline zirconium phosphate–phosphonates Zr(HPO4)[O3PCH2N(CH2CH2)2O]·nH2O, Zr(HPO4)[O3PCH2N(CH2CO2H)2]·nH2O, zirconium phosphonates Zr[(O3PCH2)NCH2CO2H]·nH2O and the catalytic activities of their palladium complexes in hydrogenation". Journal of Molecular Catalysis A: Chemical. 208 (1): 129–133. doi:10.1016/j.molcata.2003.07.004. ISSN 1381-1169.

[7] Galanski, Mathea Sophia; Slaby, Susanna; Jakupec, Michael A.; Keppler, Bernhard K. (2003-11-06). "Synthesis, Characterization, and in Vitro Antitumor Activity of Osteotropic Diam(m)ineplatinum(II) Complexes Bearing a N , N -Bis(phosphonomethyl)glycine Ligand". Journal of Medicinal Chemistry. 46 (23): 4946–4951. doi:10.1021/jm0308040. ISSN 0022-2623. PMID 14584945.

[1]

[2]

[3]

[4]

[5]

[6]

[7]