| Identification | Back Directory | [Name]
BIALAPHOS | [CAS]
35597-43-4 | [Synonyms]
Herby
C06457
SF-1293
bilanafos
BIALOPHOS
BIALAPHOS
antibioticsf1293
BIALAPHOS USP/EP/BP
Phosphinothricylalanylalanine
Phosphinothricyclalanylalanine sodium
2-Amino-4-(methylphosphino)butyrylalanylalanine
4-(Methylhydroxyphosphinyl)-L-Abu-L-Ala-L-Ala-OH
TIANFUCHEM-- 35597-43-4--High purity BIALAPHOS in stock
4-(hydroxymethylphosphinyl)-l-2-aminobutanoyl-l-alanyl-l-alanin
γ--D-α-aminobutyryl-L-alanyl-L-alanine
γ--L-α-aminobutyryl-L-alanyl-L-alanine
L-Alanine, (2S)-2-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-
gamma-(hydroxymethylphosphinyl)-l-alpha-aminobutyryl-l-alanyl-l-alanin
gamma-(hydroxymethylphosphinyl)-l-alpha-aminobutyryl-l-alanyl-l-alanine
N-{(2S)-2-aMino-4-[hydroxy(Methyl)phosphoryl]butanoyl}-L-alanyl-L-alanine
L-2-AMINO-4-[(HYDROXY)(METHYL)PHOSPHINOYL]BUTYRYL-L-ALANYL-L-ALANINE SODIUM SALT
L-2-Amino-4-[(4-hydroxy)(methyl)phosphinoyl]butyryl-L-alanyl-L-alanine sodium salt | [Molecular Formula]
C11H22N3O6P | [MDL Number]
MFCD01939329 | [MOL File]
35597-43-4.mol | [Molecular Weight]
323.28 |
| Chemical Properties | Back Directory | [Melting point ]
159-161 C | [Boiling point ]
793.2±60.0 °C(Predicted) | [density ]
1.330±0.06 g/cm3(Predicted) | [storage temp. ]
Store dry at -4 | [pka]
2.86±0.50(Predicted) | [Sequence]
{phosphinothricin}-Ala-Ala |
| Hazard Information | Back Directory | [Description]
Bilanofos is a natural product formed during
the fermentation of Streptomyces hygroscopicus. It
is readily soluble in water and insoluble in organic
solvents such as acetone, ethanol, benzene, and
hexane (9).
Bilanophos is a GS inhibitor. In
the plant, bilanofos is metabolized to L-glufosinate,
which inhibits the enzyme GS. Ammonium ions
rapidly accumulate in the plant, and photosynthesis
is inhibited, leading to rapid death of the plant. It is
inactivated in soil. | [History]
Bialaphos[peptide derivative of PPT (PPT linked to
two L-alanine moieties)] was originally isolated from cultures
of Streptomyces viridochromogenes (87) and Streptomyces
hygroscopicus (88). L-PPT is the natural isomer,
and it was the first natural amino acid found to contain a
phosphinic group. PPT strongly inhibited glutamine synthetase
activity in E. coli (87), and Hoechst Ag patented
it as a herbicide after its phytotoxicity was discovered
(89). Bialaphos was patented as a herbicide (90) and
is marketed in Japan (91). Glufosinate (ammonium salt of
PPT) is the synthesized commercial product. Bialaphos is
hydrolyzed by plant and soil microbial peptidases to yield
the active herbicide (PPT) (92–94). PPT is also rapidly
degraded, with half-life of 4 to 7 days in soils (95). In a
test of 300 bacterial isolates from soil, all strains degraded
L-PPT to the 2-oxo analog of PPT via transamination (96). | [Definition]
ChEBI: A tripeptide comprising one L-phosphinothricyl and two L-alanyl units joined in sequence. | [Origin]
The compound was launched as a nonselective contact herbicide in 1984.
| [Synthesis]
Streptomyces hygroscopicus (Streptomyces hygroscopicus) SF-1293 was incubated in a culture solution containing glycerol, malt, soybean oil, and
trace amounts of cobalt chloride, nickel chloride, and sodium dihydrogen phosphate in culture medi | [Metabolic pathway]
When 14C-bialaphos [L-2-amino-4-
[(hydroxy)(methyl)phosphinoyl]butyryl-L-alanyl-L-
alanine] is administered in an aqueous solution to
mice, the metabolite of bialaphos which is identified as
2-amino-4-[(hydroxy)(methyl)phosphinoyl]butyric acid
is excreted in the feces and urine. | [Metabolism]
The major metabolite following
oral administration in the mouse was 2-amino-4-
(hydroxy)(methyl)phosphinyl)butyric acid, which was
eliminated in feces. |
| Questions And Answer | Back Directory | [Application]
(1) Scope of application: Orchards, vegetable gardens, no-till land and non-arable land. DT50 in soil lasts 20-30 days, with 80% degrading within 30-45 days.
(2) Target weeds: Mainly used on non-arable land to control annual and some perennial grass weeds and some broadleaf weeds such as shepherd's purse, cleavers, sedge, chickweed, bok choy, ice grass, wild oats, lambsquarters, sedge, barnyard grass, Kentucky bluegrass, purslane, foxtail grass, plantain, wormwood, field bindweed, horsetail, etc.
(3) Application technology: Diamylphosphonate loses its activity upon entering the soil and is only suitable for foliar treatment. Its weeding effect is faster than glyphosate but slower than paraquat. It is easily metabolized and biodegraded, therefore it is safe to use. Half-life: 20-30 days. It is mainly used for weed control between rows in orchards and vegetable gardens, with a dosage of 1000~3000 g(ai)/hm2. For controlling annual weeds in apple, citrus, and vineyards, the dosage of 32% SL is 5~7.5 L/hm2; for controlling perennial weeds, the dosage is 7.5~10 L/hm2; and for controlling annual weeds in vegetable fields, the dosage is 3~5 L/hm2. |
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