BIALAPHOS Chemical Properties

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

BIALAPHOS Usage And Synthesis

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.

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.

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.

BIALAPHOS(35597-43-4)Related Product Information

• Glufosinate-ammonium
• Bialaphos-sodium
• bialaphos N-acetylhydrolase
• BIALAPHOS SODIUM SALT
• BIALAPHOS