Cyfluthrin

Cyfluthrin
Names
Preferred IUPAC name
(R)-Cyano(4-fluoro-3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.063.485 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1 checkY
    Key: QQODLKZGRKWIFG-QSFXBCCZSA-N checkY
  • InChI=1/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1
    Key: QQODLKZGRKWIFG-QSFXBCCZBF
  • Cl/C(Cl)=C/[C@H]3[C@@H](C(=O)O[C@@H](C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C
Properties
C22H18Cl2FNO3
Molar mass 434.29 g·mol−1
Melting point 60 °C (140 °F; 333 K)
2 μg/L
Pharmacology
P03BA01 (WHO) QP53AC12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

Cyfluthrin is a pyrethroid insecticide and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of isomers. Like most pyrethroids (MoA 3a), it is highly toxic to fish and invertebrates, but it is far less toxic to humans. It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.

Preparation

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

Properties

Cyfluthrin is a flammable solid that is colorless in its pure form but otherwise brown, and is practically insoluble in water. The commercial product is often a brownish, oily liquid with an aromatic odor. In water and air, it degrades via 4-fluoro-3-phenoxybenzaldehyde to 4-fluoro-3-phenoxybenzoic acid.

Stereoisomerism

Commercial cyfluthrin consists of a mixture of four diastereomeric pairs of enantiomers (i.e., eight isomers), comprising two pairs of cis isomers and two pairs of trans isomers. Cyfluthrin is typically produced with a purity of 92% (total of all isomers), and six additional impurities can be identified.

Unlike cyfluthrin, beta-cyfluthrin consists of only two pairs of enantiomers.

Compound CAS number Cyfluthrin [%] Beta-cyfluthrin [%]
(1R,3R,αR) + (1S,3S,αS) = 1:1; cis86560-92-1 23–27< 2
(1R,3R,αS) + (1S,3S,αR) = 1:1; cis86560-93-2 17–2130–40
(1R,3S,αR) + (1S,3R,αS) = 1:1; trans86560-94-3 32–36< 3
(1R,3S,αS) + (1S,3R,αR) = 1:1; trans86560-95-4 21–2553–67

Uses

Cyfluthrin is used as an active ingredient in plant protection products and wood preservatives and belongs to the pyrethroid group.

Safety

In rats, the LD50s are 500, 800 (oral), and 600 (skin) mg/kg.

Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures. In humans, it is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, whose urinary excretion half-lives are in a range of 5–7 hours. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantification of cyfluthrin in blood or plasma.

Health and safety risks are controlled by right to know laws that exist in most developed countries. Cyfluthrin is regulated in the US by the EPA.

Approval

It was first approved in the United States in 1981.

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

Beta-cyfluthrin was approved as an active ingredient in many EU countries, including Austria and Germany. Its approval expired on October 31, 2020, due to various concerns raised by the European regulatory authority, including its use in greenhouses for tomato cultivation and the sowing of beet seeds treated with beta-cyfluthrin. No plant protection products containing beta-cyfluthrin are available on the Swiss market.

The European Pharmacopoeia sets the limit for cyfluthrin residues in herbal drugs at 0.1 mg·kg−1.

See also

References

  1. ↑ "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
  2. 1 2 Robert L. Metcalf (2002). "Insect Control". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_263. ISBN 9783527303854.
  3. ↑ Bruce E. Smart,J. C. Tatlow (1994), Organofluorine chemistry: principles and commercial applications, Springer US, p. 250, ISBN 978-0-306-44610-8
  4. 1 2 Record of Cyfluthrin in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  5. ↑ Richard P. Pohanish (2014), Sittig's Handbook of Pesticides and Agricultural Chemicals, William Andrew, p. 180, ISBN 978-1-4557-3157-2
  6. ↑ "891. Cyfluthrin (WHO Food Additives Series 39)". www.inchem.org. Retrieved 2026-10-23.
  7. ↑ Entry on Beta-Cyfluthrin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
  8. ↑ R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 388–389.
  9. ↑ "Pyrethroids and Pyrethrins". United States Environmental Protection Agency. Archived from the original on July 9, 2009.
  10. ↑ "Pesticide Fact Sheet: Cyfluthrin" (PDF). Retrieved 2011-07-25.
  11. ↑ "EU Pesticides Database". ec.europa.eu. Retrieved 2026-10-23.
  12. ↑ Maurin Jost (2019-09-29). "Export gesundheitsschädlicher Pestizide: Viel Gift fürs Ausland". Die Tageszeitung. Retrieved 2019-10-01.
  13. ↑ eur-lex.europa.eu https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32020R0892. Retrieved 2026-10-23. {{cite web}}: Missing or empty |title= (help)
  14. ↑ "EU Pesticides Database". ec.europa.eu. Retrieved 2026-10-23.
  15. ↑ Europäisches Arzneibuch 10.0, Deutscher Apotheker Verlag, 2020, p. 432, ISBN 978-3-7692-7515-5