Tralomethrin

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Tralomethrin
Names
IUPAC name
(1R,3S)-2,2-Dimethyl-3-(1,2,2,2-tetrabromoethyl)-1-cyclopropanecarboxylic acid [(S)-cyano-[3-(phenoxy)phenyl]methyl] ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.060.429 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C22H19Br4NO3/c1-21(2)17(19(23)22(24,25)26)18(21)20(28)30-16(12-27)13-7-6-10-15(11-13)29-14-8-4-3-5-9-14/h3-11,16-19H,1-2H3/t16-,17-,18+,19?/m1/s1 ☒N
    Key: YWSCPYYRJXKUDB-KAKFPZCNSA-N ☒N
  • InChI=1/C22H19Br4NO3/c1-21(2)17(19(23)22(24,25)26)18(21)20(28)30-16(12-27)13-7-6-10-15(11-13)29-14-8-4-3-5-9-14/h3-11,16-19H,1-2H3/t16-,17-,18+,19?/m1/s1
    Key: YWSCPYYRJXKUDB-KAKFPZCNBC
  • CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)c1cccc(Oc2ccccc2)c1
Properties
C22H19Br4NO3
Molar mass 665.014 g·mol−1
Appearance Colorless liquid
Density 1.70 g/cm3 at 20 °C
Melting point 138 to 148 °C (280 to 298 °F; 411 to 421 K)
Boiling point 594 °C (1,101 °F; 867 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tralomethrin is a pyrethroid insecticide.

Tralomethrin has potent insecticidal properties; it kills by modifying the gating kinetics of the sodium channels in neurons, increasing the length of time the channel remains open after a stimulus, thereby depolarizing the neuron for a longer period of time. This leads to uncontrolled spasming, paralysis, and eventual death. Insects with certain mutations in their sodium channel gene may be resistant to tralomethrin and other similar insecticides.

Effectiveness

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Tralomethrin is also effective against most members of class Arachnida as well as insects, in addition studies by the EPA on the ecotoxicity of tralomethrin shows results as follows:

Tralomethrin Ecotoxicity
Organism Group Effects Noted
Aquatic plants Accumulation
Crustaceans Intoxication, Population
Fish Accumulation, Mortality, Population
Insects Mortality, Population
Molluscs Intoxication
Zooplankton Intoxication, Mortality, Population

Impact on human health

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Tralomethrin is a pyrethroid insecticide. The symptoms of poisoning with pyrethroid compounds are all alike:

  • Irritation of skin and eyes.
  • Irritability to sound or touch, abnormal facial sensation, sensation of prickling, tingling or creeping on skin, numbness.
  • Headache, dizziness, nausea, vomiting, diarrhea, excessive salivation, fatigue.
  • In severe cases: fluid in the lungs and muscle twitching may develop. Seizures may occur and are more common with more toxic cyano-pyrethroids.

References

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