Rotenone

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of Rotenone
General
Surname Rotenone
other names
  • (2 R , 6a S , 12a S ) -1,2,6,6a, 12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno [3,4- b ] furo [2,3- h ] chromene -6-on
  • (2 R -6a α , 12a α ) -1,2-dihydro-2-isopropenyl-8,9-dimethoxychromano [3,4- b ] furo [2,3- h ] chroman-6-one
  • Barbasco
  • Canex
  • Derrin
  • Dri-Kil
  • Fish-Tox
  • Noxfire
  • Rotacide
  • Rotocide
  • Synpren
  • Tubatoxin and others
Molecular formula C 23 H 22 O 6
Brief description

crystalline, orthorhombic plates

External identifiers / databases
CAS number 83-79-4
EC number 201-501-9
ECHA InfoCard 100.001.365
PubChem 6758
ChemSpider 6500
DrugBank DB11457
Wikidata Q412388
properties
Molar mass 394.42 g mol −1
Physical state

firmly

Melting point

165-166 ° C

solubility

Insoluble in water, well soluble in ethanol , benzene , acetone , very well soluble in chloroform
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 09 - Dangerous for the environment

danger

H and P phrases H: 301-315-319-335-410
P: 273-280-301 + 310 + 330-337 + 313-391-501
MAK

Switzerland: 5 mg m −3 (measured as inhalable dust )

Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rotenone is a furocoumarin derivative . It is the most famous representative of the Rotenoids . Rotenone is widespread in the Fabaceae family , e.g. B. in Derris eliptica ( tuba root ), Pachyrrhizus erosus , and in Lonchocarpus and Tephrosia species. Rotenone is used as an insecticide and acaricide , but it is also very poisonous for fish (less poisonous for mammals and bees) and is therefore traditionally used as an active ingredient in Barbasco in fishing .

origin

Tuba root ( Derris elliptica )

Rotenone is, inter alia, from the root of Deguelia utilis or Tubawurzel ( Derris elliptica ), an in Borneo domestic Schmetterlingsblütler obtained. The effects of these plants (and thus of the poison) had been known since the 17th century.

effect

The poisonous effect of the substance is based on a blockage of the respiratory chain located on the inner membrane of the mitochondria , where it attaches to complex I and thus prevents the transfer of electrons. As a result, the cell can no longer produce ATP and the metabolism finally comes to a standstill. Not only the fishermen of the Trobriand Islands made use of this property when fishing - with the Rotenone from crushed Derris roots, fish were anesthetized and then skewered. The plant is also used as a Barbasco in fishing in Mexico, Ecuador and Brazil .

Rotenone decomposes relatively quickly outdoors, but it is still dangerous because it can also enter the lungs through the skin or as dust. According to some studies, Rotenone is suspected to cause Parkinson's disease . The Technical University of Dresden demonstrated the triggering and strengthening effect of Rotenone on the protein alpha-synuclein in the intestine in mice, which is the cause of some types of Parkinson's. Some of the animals showed tissue changes in the brain that are similar to those found in Parkinson's patients.

operation area

Rotenone is not approved as an insecticide in either the EU or Switzerland, and there are no pesticides with Rotenone as an active ingredient on the market.

In Norway , Rotenone is successfully used to control a parasite ( Gyrodactylus salaris ) that threatens salmon stocks in some rivers. Originally 50 Norwegian rivers were infected with the parasite - today (as of December 2016) the parasite can only be found in seven rivers. Such treatments do not kill the parasite, but the host - in this case all salmon-like fish (in Norway these are salmon , trout and char ). Rotenone is not only used in Norway, but also z. B. UK , Spain , USA and Africa . In these countries, Rotenone is mainly used to eradicate introduced / invasive fish species and to prevent their spread. After the Rotenone treatment has been carried out, these waters have to be re-populated with new fish stocks.

swell

  • Burkhard Fugmann: Römpp-Lexikon Naturstoffe ; Thieme, New York, 1997
  • M. Wink: Handbook of poisonous and psychoactive plants ; Science Publishing company mbH 2008

Web links

Individual evidence

  1. ↑ a b c d e entry on Rotenone. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2014.
  2. ↑ a b Entry on Rotenone in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
  3. ↑ Entry on (2R, 6aS, 12aS) -1,2,6,6a, 12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno [3,4-b] furo [2,3-h] chromene -6-one Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 83-79-4 or Rotenone ), accessed on November 2, 2015.
  5. ^ Entry on Rotenone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  6. ↑ Pesticides can trigger Parkinson's. In: The world . December 5, 2012. Accessed December 5, 2012.
  7. ^ Francisco Pan-Montojo, Mathias Schwarz, Clemens Winkler, Mike Arnhold, Gregory A. O'Sullivan, Arun Pal, Jonas Said, Giovanni Marsico, Jean-Marc Verbavatz, Margarita Rodrigo-Angulo, Gabriele Gille, Richard HW Funk & Heinz Reichmann : Environmental toxins trigger PD-like progression via increased alpha-synuclein release from enteric neurons in mice. In: Scientific Reports. 2, 2012, doi: 10.1038 / srep00898 .
  8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Rotenone in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 3, 2018.
  9. ^ Gyrodactylus salaris. In: www.miljødirektoratet.no. Retrieved January 2, 2017 .
  10. ↑ Regioner infisert av Gyrodactylus salaris. In: www.miljødirektoratet.no. Retrieved January 2, 2017 .
  11. ↑ Frisk reported vassdrag. In: www.xn--miljdirektoratet-oxb.no. Retrieved January 2, 2017 .
  12. ↑ Marie Løvoll: Veso | Restoration and Eradication. In: www.veso.no. Retrieved January 2, 2017 .
  13. ↑ Matthew S. Recsetar, Scott A. Bonar: Effectiveness of Two Commercial Rotenone Formulations in the Eradication of Virile Crayfish Orconectes virilis . In: North American Journal of Fisheries Management . tape 35 , no. 3 , May 4, 2015, ISSN  0275-5947 , p. 616–620 , doi : 10.1080 / 02755947.2015.1017127 .
  14. ↑ Channa argus argus (northern snakehead). In: www.cabi.org. Retrieved January 2, 2017 .
  15. Jump up ↑ Olaf LF Weyl, Brian Finlayson, N. Dean Impson, Darragh J. Woodford, Jarle Steinkjer: Threatened Endemic Fishes in South Africa's Cape Floristic Region: A New Beginning for the Rondegat River . In: Fisheries . tape 39 , no. 6 , June 3, 2014, ISSN  0363-2415 , p. 270-279 , doi : 10.1080 / 03632415.2014.914924 .
  16. ↑ Manuel Ferreras-Romero, Joaquín Márquez-Rodríguez, Carlos Fernández-Delgado: Long-time effect of an invasive fish on the Odonata assemblage in a Mediterranean lake and early response after Rotenone treatment . In: ResearchGate . tape 45 , no. 1/2 , June 1, 2016, ISSN  0375-0183 , doi : 10.5281 / zenodo.50846 ( researchgate.net [accessed January 2, 2017]).