Glyphosine

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Glyphosine
File:Glyphosine.svg
Names
Preferred IUPAC name
N,N-bis(phosphonomethyl)glycine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 219-468-4
KEGG
UNII
  • 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
  • C(C(=O)O)N(CP(=O)(O)O)CP(=O)(O)O
Properties
C4H11NO8P2
Molar mass 263.079 g·mol−1
Appearance Colourless solid[1]
350 g/L[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 danger
GHS labelling:[1]
GHS05: Corrosive
Warning
H318
P264+P265, P280, P305+P354+P338, P317
Lethal dose or concentration (LD, LC):
3925 mg/kg (rat, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ↑ 1.0 1.1 1.2 1.3 1.4 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
  2. ↑ 2.0 2.1 "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.

Links

  • Glyphosine in the Pesticide Properties DataBase (PPDB)
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