Glyphosine

Glyphosine
Names
	Preferred IUPAC name N,N-bis(phosphonomethyl)glycine
Identifiers
CAS Number	2439-99-8;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.017.699
PubChem CID	17112;
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
	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]

Chemically, glyphosine is a tertiary amino, 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.

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.

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