Flurtamone
| Structural formula | ||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
||||||||||||||||
| Structural formula without stereochemistry | ||||||||||||||||
| General | ||||||||||||||||
| Surname | Flurtamone | |||||||||||||||
| other names |
|
|||||||||||||||
| Molecular formula | C 18 H 14 F 3 NO 2 | |||||||||||||||
| Brief description |
yellowish solid |
|||||||||||||||
| External identifiers / databases | ||||||||||||||||
|
||||||||||||||||
| properties | ||||||||||||||||
| Molar mass | 333.30 g mol −1 | |||||||||||||||
| Physical state |
firmly |
|||||||||||||||
| density |
1.375 g cm −3 |
|||||||||||||||
| Melting point |
148.5 ° C |
|||||||||||||||
| boiling point |
190 ° C (decomposition) |
|||||||||||||||
| solubility | ||||||||||||||||
| safety instructions | ||||||||||||||||
|
||||||||||||||||
| Toxicological data | ||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Flurtamone is a chemical compound from the furanone group. It is used as a herbicide in agriculture .
Stereochemistry
Flurtamone has a stereocenter and accordingly forms two enantiomers . The racemate is used , i.e. the 1: 1 mixture of the ( S ) and ( R ) form:
| Enantiomers of flurtamone | |
|---|---|
-Enantiomer_Flurtamone_structural_formula_V1.svg) ( S ) -enantiomer |
-Enantiomer_Flurtamone_structural_formula_V1.svg) ( R ) -enantiomer |
effect
The mode of action of flurtamone is assigned to the HRAC group F1. The herbicides of the HRAC group F1 influence the biosynthesis of carotenoids in the target organisms . The molecular characteristic of this group is the tetrafluorocarbon-phenyl partial structure.
Carotenoids play an important role in photosynthesis . They serve as accessory pigments . In the absence of these pigments, the light-harvesting complexes in the chloroplasts , the site of photosynthesis, are no longer effectively able to absorb different wavelengths , causing photosynthesis to decrease. In addition to the function of light absorption, the carotenoids in fruits and flowers also serve as colorants . Furthermore, carotenoids have the property of counteracting the photoinduced formation of reactive oxygen species . In this way, carotenoids protect the chlorophyll , which is responsible for the green color of leaves , from photooxidative destruction.
Flurtamone inhibits the enzyme phytoene desaturase (PDS) in carotenoid biosynthesis . PDS catalyzes the dehydrogenation of phytoene in the biosynthesis , which is necessary so that the final carotenoid synthesis can take place in further reaction steps.
In the presence of flurtamone, plants can no longer produce the vital carotenoids. This leads to the death of the organism. Due to the absence of carotenoids, more reactive oxygen compounds occur, which ensure that the chlorophylls in the plant are oxidized and the green color decreases. This is why herbicides that inhibit carotenoid synthesis are also known as bleach herbicides.
Admission
Flurtamon was approved in the European Economic Area since January 1, 2004 . However, the member states had to revoke the authorizations for plant protection products containing flurtamone as an active ingredient by 27 June 2019 at the latest. A use-by period of a maximum of nine months was granted.
In Switzerland there are also no more pesticides with this active ingredient on the market.
Trade names
- Bacara, Cadou
Individual evidence
- ↑ a b c d e f g Entry on Flurtamone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed January 15, 2018.
- ↑ a b c d Entry on Flurtamon in the GESTIS substance database of the IFA , accessed on January 15, 2018(JavaScript required) .
- ↑ Entry on Flurtamone (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 2, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ a b Flurtamone data sheet from Sigma-Aldrich , accessed on January 15, 2018 ( PDF ).
- ↑ European Food Safety Authority (EFSA): Peer review of the pesticide risk assessment of the active substance flurtamone . In: EFSA Journal. June 2016, doi: 10.2903 / j.efsa.2016.4498 , p. 7.
- ↑ Bacara® Forte. (PDF) Bayer Agrar Germany, accessed on January 15, 2018 . P. 1.
- ↑ a b c Thomas Seitz, Michael G. Hoffmann, Hansjörg Krähmer: Herbicides for agriculture: chemical weed control . In: Chemistry in our time, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 2013, doi: 10.1002 / ciuz.200300279 , pp. 112–126.
- ↑ Hans-Walter Heldt, Birgit Piechulla: Plant biochemistry . Springer-Verlag Berlin Heidelberg, 2015, doi: 10.1007 / 978-3-662-44398-9 , pp. 54-60.
- ^ A b Hans-Walter Heldt, Birgit Piechulla: Plant biochemistry . Springer-Verlag Berlin Heidelberg, 2015, doi: 10.1007 / 978-3-662-44398-9 , pp. 407-411.
- ↑ Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances
- ↑ Implementing Regulation (EU) 2018/1917 of the Commission of 6 December 2018 on the non-renewal of the approval for the active substance flurtamone according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Commission Implementing Regulation (EU) No. 540/2011
- ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Flurtamone in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.