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:
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. It 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]