Cyfluthrin

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Structural formula
Structural formula of cyfluthrin
Mixture of eight stereoisomers , only one of which is shown
General
Surname Cyfluthrin
other names
  • beta-cyfluthrin
  • alpha-cyano-4-fluoro-3-phenoxybenzyl-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate
  • 3- (2,2-dichloroethenyl) -2,2-dimethyl-cyclopropane
Molecular formula C 22 H 18 Cl 2 FNO 3
Brief description

brown solid

External identifiers / databases
CAS number 68359-37-5
EC number 269-855-7
ECHA InfoCard 100,063,485
PubChem 104926
Wikidata Q61641151
Drug information
ATC code

P03 BA01

properties
Molar mass 434.29 g mol −1
Physical state

firmly

density

1.27 g cm −3

Melting point

60 ° C

boiling point

210 ° C (decomposition)

solubility

practically insoluble in water (0.002 mg l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
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: 300-331-410
P: 261-264-273-301 + 310-311-501
MAK

Switzerland: 0.01 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 .

Cyfluthrin is a mixture of several isomeric chemical compounds from the group of pyrethroids and nitriles . Cyfluthrin is a type II pyrethroid .

Extraction and presentation

Cyfluthrin can be obtained from 5-methyl- or 5-carboxy-2-fluorobromobenzene.

properties

Cyfluthrin is a flammable brown solid that is practically insoluble in water. The technical product is often a brownish oily liquid with a bitter almond odor. In water and air it breaks down via 4-fluoro-3-phenoxybenzaldehyde to 4-fluoro-3-phenoxybenzoic acid.

Stereoisomerism

Technical cyfluthrin consists of a mixture of four diastereomeric pairs of enantiomers (i.e. eight isomers ), which consist of two cis and two trans isomer pairs . Cyfluthrin is manufactured with a typical purity of 92% (sum of all isomers), whereby an additional six impurities can be identified.

In contrast to cyfluthrin, beta-cyfluthrin consists of only two pairs of enantiomers.

Pair of enantiomers CAS number Cyfluthrin [%] Beta-cyfluthrin [%]
(1 R , 3 R , α R ) + (1 S , 3 S , α S ) = 1: 1; cis 86560-92-1 23-27 <2
(1 R , 3 R , α S ) + (1 S , 3 S , α R ) = 1: 1; cis 86560-93-2 17-21 30-40
(1 R , 3 S , α R ) + (1 S , 3 R , α S ) = 1: 1; trans 86560-94-3 32-36 <3
(1 R , 3 S , α S ) + (1 S , 3 R , α R ) = 1: 1; trans 86560-95-4 21-25 53-67

use

Cyfluthrin is used as an active ingredient from the group of pyrethroids in plant protection products and wood preservatives. It was first approved in the United States in 1981.

Admission

Cyfluthrin is not approved in the EU countries including Germany and Austria. No pesticides containing this active ingredient are available in Switzerland either. However, cyfluthrin can be manufactured in the EU for export .

Beta-cyfluthrin is approved as an active ingredient in many EU countries, including Austria and Germany. The approval expires on October 31, 2020 due to various concerns of the European approval authority, e.g. B. use in greenhouses (tomato cultivation) or sowing beet seeds treated with beta-cyfluthrin. In Switzerland, there are no pesticides containing beta-cyfluthrin on the market.

Trade names

Baythroid, Baythroid H, Attatox, Contur, Laser, Responsar, Solfac, Tempo and Tempo H.

It is also offered as a combination product with Methamidophos (Baythroid TM) or Pyriproxyfen (Bolfo, as an environmental spray against fleas).

Web links

Individual evidence

  1. ↑ a b c d e f g h i Entry on cyfluthrin in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ EU: Review report for the active substance beta-cyfluthrin. (PDF; 364 kB) December 2, 2002, accessed on July 25, 2011 .
  3. ↑ Entry on α-cyano-4-fluoro-3-phenoxybenzyl 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016 . marketer can use the harmonized classification and labeling expand .
  4. ↑ Swiss Accident Insurance Fund (Suva): Limits - Current List of MAK and BAT Values (Search for 68359-37-5 or cyfluthrin ), accessed on November 2, 2015.
  5. ↑ Data sheet β-cyfluthrin from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  6. ↑ Bruce E. Smart, JC Tatlow: Organofluorine chemistry: principles and commercial applications . Springer US, 1994, ISBN 978-0-306-44610-8 ( page 250 in the Google book search).
  7. ↑ Cyfluthrin. Retrieved July 25, 2011 .
  8. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for Toxicological evaluation of certain veterinary drug residues in food , accessed on July 25, 2011.
  9. ↑ Entry on beta-cyfluthrin. In: Römpp Online . Georg Thieme Verlag, accessed on February 8, 2019.
  10. ↑ Pesticide Fact Sheet: Cyfluthrin. 1994, Retrieved July 25, 2011 .
  11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Cyfluthrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.
  12. ↑ Maurin Jost: Export of harmful pesticides: A lot of poison for abroad. In: taz.de . September 29, 2019, accessed October 1, 2019 .
  13. ↑ Implementing Regulation (EU) 2020/892 of the Commission of June 29, 2020 on the non-renewal of the approval for the active ingredient beta-cyfluthrin. European Commission, June 30, 2020, accessed on July 20, 2020 (German).
  14. ↑ General Directorate Health and Food Safety of the European Commission: Entry on beta-cyfluthrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.
  15. ↑ Extoxnet: cyfluthrin. Retrieved December 19, 2013 .