Tralomethrin

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
CAS Number	66841-25-6^Y
3D model (Jmol)	Interactive image
ChemSpider	43788^N
ECHA InfoCard	100.060.429
KEGG	C18413^Y
PubChem	48132
InChI 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
SMILES CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C(C(Br)(Br)Br)Br)C
Properties
Chemical formula	C₂₂H₁₉Br₄NO₃
Molar mass	665.01 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).
N verify (what is ^YN ?)
Infobox references

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

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

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

Pest control: Insecticides

Carbamates	Aldicarb Bendiocarb Carbaryl Carbofuran Ethienocarb Fenobucarb Oxamyl Methomyl Propoxur

Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green

Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Pyriproxyfen

Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Nitenpyram Nithiazine Thiacloprid Thiamethoxam

Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene

Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dicrotophos Diisopropyl fluorophosphate Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon

Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin

Ryanoids	Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine Ryanodol

Other chemicals	Afoxolaner Amitraz Azadirachtin Buprofezin Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Ryanodine Sarolaner Sesamex Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone

Metabolites	Oxon Malaoxon Paraoxon TCPy

Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paecilomyces fumosoroseus Paenibacillus popilliae Purpureocillium lilacinum

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