Phosphinothricin
Title: Phosphinothricin
CAS Registry Number: 35597-44-5
CAS Name: (2S)-2-Amino-4-(hydroxymethylphosphinyl)butanoic acid
Additional Names: 2-ammonio-4-methylphosphinicobutyrate; L-PPT
Molecular Formula: C5H12NO4P
Molecular Weight: 181.13
Percent Composition: C 33.15%, H 6.68%, N 7.73%, O 35.33%, P 17.10%
Literature References: First natural L-amino acid containing a phosphinic acid group. Isolated from the tripeptide antibiotic, bialaphos; inhibits glutamine synthetase. Isoln from S. viridochromogenes and synthesis of DL-form: E. Bayer et al., Helv. Chim. Acta 55, 224 (1972). Synthesis of DL-form: H. Gross, T. Gnauk, J. Prakt. Chem. 318, 157 (1976); of enantiomers: N. Minowa et al., Tetrahedron Lett. 25, 1147 (1984). Crystal structure: E. F. Paulus, S. Grabley, Z. Kristallogr. 160, 63 (1982). Determn in biological fluids: A. Suzuki, M. Kawana, Bull. Environ. Contam. Toxicol. 43, 17 (1989). Environmental impact in lakes: M. J. Faber et al., Environ. Toxicol. Chem. 17, 1291 (1998). Field trial in orchards and vineyards as herbicide: P. Langelüddeke et al., Meded. Fac. Landbouwwet. Rijksuniv. Gent 47, 95 (1982); on seed potato as desiccant: H. M. Lawson, J. S. Wiseman, Brighton Crop Prot. Conf. - Weeds 1991, 233. Review of syntheses, activities and uses: G. Hoerlein, Rev. Environ. Contam. Toxicol. 138, 73-145 (1994).
Properties: [a]D25 +13.4° (c = 1 in water).
Optical Rotation: [a]D25 +13.4° (c = 1 in water)
 
Derivative Type: D-Form
CAS Registry Number: 73679-07-9
Properties: [a]D25 -12.4° (c = 1 in water).
Optical Rotation: [a]D25 -12.4° (c = 1 in water)
 
Derivative Type: DL-Form
CAS Registry Number: 51276-47-2
Additional Names: Glufosinate
Properties: mp 229-231° (dec).
Melting point: mp 229-231° (dec)
 
Derivative Type: DL-Form monoammonium salt
CAS Registry Number: 77182-82-2
Additional Names: Glufosinate-ammonium; ammonium DL-homoalanine-4-yl(methyl)phosphinate
Manufacturers' Codes: HOE-661; HOE-39866
Trademarks: Basta (Bayer CropSci.); Liberty (Bayer CropSci.); Rely (Bayer CropSci.)
Molecular Formula: C5H15N2O4P
Molecular Weight: 198.16
Percent Composition: C 30.31%, H 7.63%, N 14.14%, O 32.30%, P 15.63%
Properties: Sol in water. LD50 in male, female mice, male, female rats (mg/kg): 431, 416, 2000, 1620 orally (Langelüddeke).
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 431, 416, 2000, 1620 orally (Langelüddeke)
 
Use: Postemergent herbicide; desiccant.

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