Glufosinate (phosphinothricin), a natural amino acid with unexpected herbicidal properties

Abstract

Glufosinate ammonium (phosphinothricin ammonium) (GLA) is the active ingredient of Basta and several other herbicides used worldwide. It is produced as part of the tripeptide L-phosphinothricyl-L-alanyl-L-alanin, which was first isolated from Streptomyces viridichromogenes or Streptomyces hygroscopicus. Its structure is confirmed by degradation and synthesis. Several processes for the preparation of D,L- and L-phosphinothricin are described. Glufosinate is a structural analog of glutamate and inhibits the glutamine synthetase. The result is a rapid build-up of a high ammonia level and a concomitant depletion of glutamine and several other amino acids in the plant. These effects are accompanied by a rapid decline of photosynthetic CO2-fixation and are followed by chlorosis and desiccation. The results of numerous toxicological studies show that glufosinate ammonium and its commercial formulations are safe for users and consumers under the conditions of recommended use. The fast and complete degradation in soil and surface water prevents movement of residues into groundwater. The toxicological threshold levels for all the nontarget organisms tested are well above the potential exposure levels and therefore do not reflect any hazard for nontarget organisms in the ecosystem. Basta is a nonselective foliar applied herbicide for the control of undesirable mono- and dicotyledonous plants in orchards, vineyards, and plantations for minimum tillage, and as a harvest aid. A synthetic phosphinothricin acetyltransferase (PAT) gene has been introduced via Agrobacterium tumefaciens into dicot crops, such as like tobacco, tomato, spring and winter rapeseed, alfalfa, and several horticultural crops. The PAT gene was also successfully introduced into maize protoplasts that could be regenerated into fertile plants. All transgenic crop plants tolerated a two- to threefold field dosage of Basta.