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(RS)-glufosin
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(RS)-glufosin

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Also known as glufosinate, DL-2-amino-4-(methylphosphino)butanoic acid, 3-amino-3-carboxypropylmethylphosphinic acid, phosphinothricin

Glufosinate (also known as phosphinothricin and often sold as an ammonium salt) is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Applicatio

Wikidata facts

Mass
181.05
Show 4 more facts
chemical formula
C₅H₁₂NO₄P
canonical SMILES
CP(=O)(CCC(C(=O)O)N)O
subject has role
herbicide
Commons category
Glufosinate
Sources (4)

via Wikidata · CC0

~6 min read

Encyclopedic overview

10 sections
Contents
  • Discovery
  • Use
  • Genetically modified crops
  • Mode of action
  • Toxicity
  • Exposure to humans in foods
  • Exposure limits
  • Regulation
  • References
  • External links

Glufosinate (also known as phosphinothricin and often sold as an ammonium salt) is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos and phosalacine, other naturally occurring herbicides, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

==Discovery== In the 1960s and early 1970s, scientists at University of Tübingen and at the Meiji Seika Kaisha Company independently discovered that species of Streptomyces bacteria produce a tripeptide they called bialaphos that inhibits bacteria; it consists of two alanine residues and a unique amino acid that is an analog of glutamate that they named "phosphinothricin". They determined that phosphinothricin irreversibly inhibits glutamine synthetase. Phosphinothricin was first synthesized by scientists at Hoechst in the 1970s as a racemic mixture; this racemic mixture is called glufosinate and is the commercially relevant version of the chemical.

Excerpted from Wikipedia’s “(RS)-glufosin” article, available under the CC BY-SA 4.0 licence.