7339. Phosphinothricin

Nomenclature

CAS number: 35597-44-5
(2S)-2-Amino-4-(hydroxymethylphosphinyl)butanoic acid; 2-ammonio-4-methylphosphinicobutyrate; l-PPT.
C5H12NO4P; mol wt 181.13.
C 33.15%, H 6.68%, N 7.73%, O 35.33%, P 17.10%.

Description and 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).

Chemical structure

Properties

[α]D25 +13.4° (c = 1 in water).

Derivative

d-Form.

Nomenclature

CAS number: 73679-07-9

Properties

[α]D25 -12.4° (c = 1 in water).

Derivative

dl-Form.

Nomenclature

CAS number: 51276-47-2
Glufosinate.

Properties

mp 229-231° (dec).

Derivative

dl-Form monoammonium salt.

Nomenclature

CAS number: 77182-82-2
Glufosinate-ammonium; ammonium dl-homoalanine-4-yl(methyl)phosphinate; HOE-661; HOE-39866; Basta (Bayer CropSci.); Liberty (Bayer CropSci.); Rely (Bayer CropSci.).
C5H15N2O4P; mol wt 198.16.
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).

Use

Postemergent herbicide; desiccant.