Cyfluthrin

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, it is highly toxic to fish and invertebrates, but it is far less toxic to humans.[1] It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.

Cyfluthrin

Names
IUPAC name [(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
CAS Number	68359-37-5
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2104608
ChemSpider	45482
ECHA InfoCard	100.063.485
KEGG	C10982
PubChem CID	50153
UNII	SCM2QLZ6S0
CompTox Dashboard (EPA)	DTXSID5035957
InChI 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 Key: QQODLKZGRKWIFG-QSFXBCCZSA-N 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
SMILES 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
Chemical formula	C22H18Cl2FNO3
Molar mass	434.29 g·mol^−1
Melting point	60 °C (140 °F; 333 K)
Solubility in water	2 μg/L
Pharmacology
ATC code	P03BA01 (WHO) QP53AC12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Safety

In rats, the LD₅₀s are 500, 800 (oral), and 600 (skin) mg/kg.[1]

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.[2]

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.[3]

See also

• Cyhalothrin

References

1. Robert L. Metcalf (2002). "Insect Control". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_263.
2. R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 388–389.
3. "Pyrethroids and Pyrethrins". United States Environmental Protection Agency.