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Tralomethrin

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Name

Tralomethrin

EINECS 266-493-1
CAS No. 66841-25-6 Density 1.849g/cm3
PSA 59.32000 LogP 7.46098
Solubility 0.08 mg l-1 Melting Point 138-148oC
Formula C22H19 Br4 N O3 Boiling Point 594.316oC at 760 mmHg
Molecular Weight 665.014 Flash Point 313.231oC
Transport Information N/A Appearance N/A
Safety A poison by ingestion and inhalation routes. Moderately toxic by skin contact. When heated to decomposition it emits toxic vapors of NOx and Br. Risk Codes 22-36/38-50/53
Molecular Structure Molecular Structure of 66841-25-6 (TRALOMETHRIN) Hazard Symbols Xn,N
Synonyms

Bengal FireAnt Killer;HAG 107;RU 25472;SAGA;Scout;Scout X-tra;Tracker;Tralomethrin;

Article Data 6

Tralomethrin Chemical Properties

Molecule structure of Tralomethrin (CAS NO.66841-25-6) :

IUPAC Name: [(S)-cyano-(3-phenoxyphenyl)methyl](1R,3S)-2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylate 
Molecular Weight: 665.00716 g/mol
Molecular Formula: C22H19Br4NO3 
Density: 1.849 g/cm3 
Melting Point: 143 °C
Boiling Point: 594.3 °C at 760 mmHg 
Flash Point: 313.2 °C
Index of Refraction: 1.641
Molar Refractivity: 129.71 cm3
Molar Volume: 359.5 cm3
Polarizability: 51.42×10-24 cm3
Surface Tension: 59.3 dyne/cm 
Enthalpy of Vaporization: 88.59 kJ/mol 
log P (octanol-water): 7.560 
Water Solubility: 0.08 mg/L 
Vapor Pressure: 3.60E-11 mm Hg 
Henry's Law Constant: 3.94E-10 atm-m3/mole 
Atmospheric OH Rate Constant: 1.76E-11 cm3/molecule-sec
XLogP3: 8
H-Bond Acceptor: 4
Rotatable Bond Count: 7
Exact Mass: 664.805751
MonoIsotopic Mass: 660.809844
Topological Polar Surface Area: 59.3
Heavy Atom Count: 30
Complexity: 665
Defined Atom StereoCenter Count: 3
Undefined Atom StereoCenter Count: 1
Canonical SMILES: CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C(C(Br)(Br)Br)Br)C
Isomeric 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
InChIKey: YWSCPYYRJXKUDB-KAKFPZCNSA-N
EINECS: 266-493-1
Product Categories: insecticide 
Storage Temp.: 0-6 °C

Tralomethrin Uses

 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.

Tralomethrin Production

In the carbon tetrachloride solvent, deltamethric acid and bromine addition, reaction 1h at 20 °C, get cyano(3-phenoxyphenyl)methyl ester  , then change into fourbromotralomethrin chloride with  thionyl chloride inDMF and petroleum ether, then with α-cyano-4-phenoxy bromine methanol to synthesis Tralomethrin .

Tralomethrin Toxicity Data With Reference

1.    

orl-rat LD50:99 mg/kg

    PEMNDP    Pesticide Manual. 9 (1991),829.
2.    

ihl-rat LC50:2700 mg/m3

    FMCHA2    Farm Chemicals Handbook .(Meister Publishing,Willoughy, OH.: )1991,C271.
3.    

orl-dog LD50:>500 mg/kg

    PEMNDP    Pesticide Manual. 9 (1991),829.
4.    

skn-rbt LD50:>2 g/kg

    PEMNDP    Pesticide Manual. 9 (1991),829.
5.    

orl-qal LD50:>2150 mg/kg

    PEMNDP    Pesticide Manual. 9 (1991),829.

Tralomethrin Safety Profile

A poison by ingestion and inhalation routes. Moderately toxic by skin contact. When heated to decomposition it emits toxic vapors of NOx and Br.
RIDADR: 2588
HazardClass: 6.1(b)
PackingGroup: III

Tralomethrin Specification

 Tralomethrin (CAS NO.66841-25-6) is also called (S)-alpha-Cyano-3-phenoxybenzyl (1R)-cis-2,2-dimethyl-3-((RS)-1,2,2,2-tetrabromoethyl)-cyclopropanecarboxylate ; (S)-alpha-Cyano-3-phenoxybenzyl (1R,3S)-2,2-dimethyl-3-((RS)-1,2,2,2-tetrabromoethyl)-cyclopropanecarboxylate ; AI3-29694 ; Bengal Fire Ant Killer ; Caswell No. 861AA ; Cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropanecarboxylate ; EPA Pesticide Chemical Code 121501 ; HAG 107 ; HOE 107 ; HSDB 6740 ; RU 25472 ; SAGA ; Scout ; Tralomethrine . Tralomethrin (CAS NO.66841-25-6) is yellow to orange-yellow resin-like substance. It can be soluble in acetone, xylene, toluene, dichloromethane, DMSO, ethanol and other organic solvents. The water solubility is 70mg / L. Tralomethrin is light stable and non-corrosive. It will not decomposite  for 6 months when the temperature is 50 °C.

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