Glufosinate
- 2-amino -4- (hydroxy -methyl- phosphoryl) butanoic acid
- (RS )-2- amino-4- (hydroxy -methyl- phosphoryl) butanoic acid
- (± )-2- amino-4- (hydroxy -methyl- phosphoryl) butanoic acid
- DL-2- amino-4- (hydroxy -methyl- phosphoryl) butanoic acid
- Phosphinothricin
- C5H12NO4P ( glufosinate)
- C5H15N2O4P ( glufosinate - ammonium salt)
- 51276-47-2 [( RS)- glufosinate ]
- 35597-44-5 [( S)- glufosinate ]
- 73679-07-9 [(R) - glufosinate ]
- 77182-82-2 [( RS)- glufosinate - ammonium salt ]
Colorless solid
1.4 g · cm -3 ( 20 ° C)
215 ° C
Well in water ( 1370 g · l-1 at 20 ° C)
Risk
Ammonium salt
Template: Infobox chemical / molecular formula search available
Glufosinate, and phosphinothricin, is an active ingredient for plant protection and first described in the literature, peptide- bound, naturally occurring amino acid with a phosphinic acid group.
Glufosinate was discovered in 1971 as part of the tripeptide bialaphos in Streptomyces. A special feature lies in the rarity of the carbon-phosphorus -carbon bond and the still not fully understood biosynthesis of these chemically stable grouping. Glufosinate is classified as toxic to reproduction by BMELV
- 3.1 Europe
Production
Various methods for the synthesis of racemic glufosinate [ 1:1 mixture of the enantiomers of (S) glufosinate and (R) - glufosinate ] are described in the literature.
Use
Herbicide
The racemic ammonium salt of phosphinothricin is included as an ingredient in various commercial herbicides and is used under several trade names other than (total ) herbicide with contact and teilsystemischer effect. The best known of these tradenames is Basta ®. Glufosinate acts against both monocotyledonous and dicotyledonous plants against. The recording is done not through the roots, but mainly through the green plant parts where it causes an inhibition of glutamine synthetase. This leads to the accumulation of ammonia in the leaf tissue of the plant and further to a lack of glutamine and other amino acids. This leads to inhibition of photosynthesis to chlorosis and ultimately to the death of the leaf tissue and, finally, the whole plant. Therefore the glufosinate herbicides aminosäureantagonistischen is also counted to the group.
Genetic resistance
It succeeded genetically to produce a resistance to the herbicide in crops such as maize, rice, canola or salad. , The gene for the enzyme phosphinothricin acetyl transferase (PAT enzyme) from the bacterium Streptomyces viridochromogenes was isolated. The bacterium that produces phosphinothricin itself, thus protects itself from its own venom, in which it transfers an acetyl group to phosphinothricin and thereby inactivated.
One example is the rice LL62. LL62 is against the Bayer broad spectrum herbicide Liberty resistant ( with active ingredient glufosinate - ammonium ). 2004, Bayer filed its application for approval for the import into the EU of an LL62. The application relates to the use as food, feed and for processing. In the USA, has been authorized for cultivation.
Regulation
Europe
In the European Union since 2007 is considered an admission of glufosinate for plant protection products, which expires September 30, 2017. At national level, glufosinate has been approved in 21 EU countries. In Switzerland and in Germany pesticides are approved with this drug, in Austria at present ( January 2014 ) is not.
The Permitted daily dose and the Acute Reference Dose are respectively 0.021 milligrams per kilogram of body weight per day, the Acceptable Operator Exposure is 0.0021 milligrams per kilogram of body weight per day.
The Implementing Regulation ( EU) No 365/2013 of April 22, 2013 laid down the grounds of alleged risks to mammals and non-target arthropods that only in strips or point herbicide glufosinate applications may be authorized, in doses not exceeding 750 g ai / ha ( treated surface ) per application and no more than two applications per year. Prohibition to implement the implementing or limited the BVL for certain crops, the application of glufosinate product Basta for the 13th November 2013.