Transfluthrin

Volatile pyrethroid insecticide used indoor against insects such as moths or mosquitoes
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
  • 118712-89-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:32253 checkY
ChemSpider
  • 570973 checkY
ECHA InfoCard 100.100.666 Edit this at Wikidata
KEGG
  • C13410 checkY
PubChem CID
  • 656612
UNII
  • QWL3SKA6EG checkY
CompTox Dashboard (EPA)
  • DTXSID4046812 Edit this at Wikidata
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 checkY
    Key: DDVNRFNDOPPVQJ-HQJQHLMTSA-N checkY
  • 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
  • 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).
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Infobox references
Chemical compound

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

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

References

  1. ^ a b c d "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. PMID 12243228. S2CID 32047931.
  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. ^ a b Assessment report: Transfluthrin for EU regulation No. 528/2012 (2014)

External links

  • Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V.N.; Gowariker, Sugha (22 December 2014). The Pesticide Encyclopedia. CABI. pp. see 486. ISBN 978-1-78064-014-3.
  • Vesin, Aude; Glorennec, Philippe; Le Bot, Barbara; Wortham, Henri; Bonvallot, Nathalie; Quivet, Etienne (2013). "Transfluthrin indoor air concentration and inhalation exposure during application of electric vaporizers" (PDF). Environment International. 60: 1–6. Bibcode:2013EnInt..60....1V. doi:10.1016/j.envint.2013.07.011. ISSN 0160-4120. PMID 23973617. S2CID 16608444.
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