| Identification | Back Directory | [Name]
Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)- | [CAS]
35597-44-5 | [Synonyms]
L-Glufosinate
Phosphinothricine
L-Phosphinothricin
(S)-Phosphinothricin
Glufosinate Impurity 5
(S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid
(S)-4-[Hydroxy(methyl)phosphinyl]-2-aminobutyric acid
Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)- | [Molecular Formula]
C5H12NO4P | [MOL File]
35597-44-5.mol | [Molecular Weight]
181.13 |
| Chemical Properties | Back Directory | [Melting point ]
209-210 °C | [alpha ]
D25 +13.4° (c = 1 in water) | [Boiling point ]
519.1±45.0 °C(Predicted) | [density ]
1.378±0.06 g/cm3(Predicted) | [pka]
2.22±0.10(Predicted) | [InChI]
InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1 | [InChIKey]
IAJOBQBIJHVGMQ-BYPYZUCNSA-N | [SMILES]
C(CP(O)(=O)C)[C@H](N)C(=O)O |
| Hazard Information | Back Directory | [Chemical Properties]
A 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses. | [Definition]
ChEBI: Glufosinate-P is a 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid that has S configuration at position 2. A glutamine synthetase inhibitor, it is used (generally as the corresponding ammonium or sodium salts, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) as a herbicide to control annual weeds and grasses. It has a role as a herbicide, an EC 6.3.1.2 (glutamate--ammonia ligase) inhibitor and an agrochemical. It is an enantiomer of a (2R)-glufosinate. It is a tautomer of a glufosinate-P zwitterion. | [Production Methods]
The commercial production of glufosinate-P typically begins with the microbial fermentation of Streptomyces species, which naturally produce bialaphos, a tripeptide that can be hydrolysed to yield glufosinate. The racemic mixture is then subjected to chiral resolution or asymmetric synthesis to isolate the L-isomer, which exhibits the desired herbicidal activity. This process may involve acidification, crystallisation, and purification steps to achieve high enantiomeric purity. | [Biological Activity]
Through oxidative stress C. elegans, racemic glufosinate-ammonium l-glufosinate-ammonium (Glufosinate-P) both mediated developmental toxicity (shortened developmental cycle, reduced body length width, promoted aging and decreased longevity), neurotoxicity (inhibited head swinging, body bending frequency acetylcholinesterase [AchE] activity) reproductive toxicity (significant reductions in number eggs offspring in vivo induced apoptosis gonadal cells). The degradation rate of L-glufosinate-ammonium was faster than that of D-glufosinate-ammonium. Based on MDA content, protein content, and antioxidant enzyme (SOD CAT) activity, Meng et al. found that L-glufosinate-ammonium could cause more severe oxidative damage than rac-glufosinate-ammonium[1-2].
| [Mechanism of action]
Non-selective, contact with some systemic action. Glutamine synthetase inhibitor: accumulates ammonium ions, inhibits photosynthesis. | [References]
[1] Xu Zhao . “Comparison of the chronic and multigenerational toxicity of racemic glufosinate and l-glufosinate to Caenorhabditis elegans at environmental concentrations.” Chemosphere 316 (2023): Article 137863.
[2] Tianyou Feng. “Comparative analysis of toxicity and metabolomic profiling of rac-glufosinate and L-glufosinate in zebrafish.” Aquatic Toxicology 261 (2023): Article 106618. | [Pesticide Type]
Herbicide |
|
|