Transfluthrin

Transfluthrin is a fast-acting pyrethroid insecticide with low persistency. It has the molecular formula C15H12Cl2F4O2.

Transfluthrin
Names
Preferred IUPAC name
(2,3,5,6-Tetrafluorophenyl)methyl (1R,3S)-3-(2,2-dichloroethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
Other names
– CA: (1R-trans)-(2,3,5,6-tetrafluorophenyl)methyl 3-(2,2-dichloroethenyl)-2,2- dimethylcyclopropanecarboxylate[1]
– Common name transfluthrin: E-ISO (published).
– Synonym: benfluthrin (Bayer), NAK 4455[1]
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.100.666
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C15H12Cl2F4O2/c1-15(2)7(3-10(16)17)11(15)14(22)23-5-6-12(20)8(18)4-9(19)13(6)21/h3-4,7,11H,5H2,1-2H3/t7-,11+/m1/s1 Y
    Key: DDVNRFNDOPPVQJ-HQJQHLMTSA-N Y
  • InChI=1/C15H12Cl2F4O2/c1-15(2)7(3-10(16)17)11(15)14(22)23-5-6-12(20)8(18)4-9(19)13(6)21/h3-4,7,11H,5H2,1-2H3/t7-,11+/m1/s1
    Key: DDVNRFNDOPPVQJ-HQJQHLMTBF
SMILES
  • Cl/C(Cl)=C/[C@@H]2[C@@H](C(=O)OCc1c(F)c(F)cc(F)c1F)C2(C)C
Properties
Chemical formula
 C15H12Cl2F4O2
Molar mass 371.15 g·mol−1
Appearance Colorless crystals
Density 1.507 g/cm3 (23 °C)
Melting point 32 °C (90 °F; 305 K)
Boiling point 135 °C (275 °F; 408 K) at 0.1 mm Hg
~ 250 °C at 760 mm Hg
Solubility in water
 5.7×10−5 g/L = 57 µg/L
Solubility in hexane, isopropanol, toluene, dichloromethane very soluble
Vapor pressure Conflicting data: 1×10−4 Pa (20 °C; 15 μg/m3)[2]

or 9×10−4 Pa (20 °C)[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Transfluthrin can be used in the indoor environment against flies, mosquitoes, moths and cockroaches. It is a relatively volatile substance and acts as a contact and inhalation agent.[1][3]

Transfluthrin, if used contrary to product instructions, may cause symptoms of poisoning including nervousness, anxiety, tremor, convulsions, skin allergies, sneezing, running nose and irritation. Treatment depends on symptoms. No specific antidotes are known, but antihistamines may help to control any allergies.[4]

In experiments, transfluthrin was shown to kill 85 percent of mosquitos within one hour of exposure at concentrations below 0.3 µg/m3 (which was the detection limit) in air.[5] (The data suggests that transfluthrin is effective at these concentrations within much less than an hour of exposure.)

Various household transfluthrin products such as vaporizers and mosquito coils may result in concentrations of 15 µg/m3 to 40 µg/m3.[6] In the EU, the acceptable exposure level (AEL) for humans is 500 µg/m3.[6]

See also
  • Metofluthrin
  • Tefluthrin

References
  1. "WHO Specifications and evaluations for public health pesticides: Transfluthrin. WHO specification 741/2006 – Evaluation Report 741/2002 (November 2006)" (PDF). World Health Organization (WHO). November 2006. p. 20. Retrieved 15 May 2020.
  2. Pesticides properties database. K Lewis et al., DOI: 10.1080/10807039.2015.1133242
  3. Pates, H. V.; Lines, J. D.; Keto, A. J.; Miller, J. E. (September 2002). "Personal protection against mosquitoes in Dar es Salaam, Tanzania, by using a kerosene oil lamp to vaporize transfluthrin: Mosquito repellent vaporizing lamps". Medical and Veterinary Entomology. 16 (3): 277–284. doi:10.1046/j.1365-2915.2002.00375.x.
  4. Information on the leaflet supplied with the product: Good Knight Advanced (ACTIV+ System) Mosquito Repellent Vaporizer cartridge (UPC Code:8 901157 001143)
  5. N.J. Martin et al., The impact of transfluthrin on the spatial repellency of the primary malaria mosquito vectors in Vietnam: Anopheles dirus and Anopheles minimus.. Malar J 19, 9 (2020)
  6. Assessment report: Transfluthrin for EU regulation No. 528/2012 (2014)
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