TRALOMETHRIN Chemical Properties

Melting point:

143℃

Boiling point:

185～190℃ (0.1mmHg)

Density 

1.70 g/cm3 (20℃)

vapor pressure 

4.8×10^-9 Pa (25 °C)

refractive index 

1.6300 (estimate)

storage temp. 

0-6°C

Water Solubility 

0.08 mg l^-1

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

InChIKey

YWSCPYYRJXKUDB-UHFFFAOYSA-N

SMILES

O=C(OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1)C3C(C(Br)C(Br)(Br)Br)C3(C)C

EPA Substance Registry System

Tralomethrin (66841-25-6)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36/38-50/53

Safety Statements 

26-60-61

RIDADR 

2588

WGK Germany 

3

HazardClass 

6.1(b)

PackingGroup 

III

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Skin Irrit. 2

Hazardous Substances Data

66841-25-6(Hazardous Substances Data)

TRALOMETHRIN Usage And Synthesis

Description

Orange-to-yellow resinous solid (technical grade >39%)

Chemical Properties

The prodrug is yellow to orange-yellow resin-like substance. Relative density 1.7 (20℃), vapor pressure 1.7Pa (1.73×10-11Pa) (25℃), [α]D+21 o～+27 o(50g/L toluene). Soluble in acetone, xylene, toluene, dichloromethane, dimethyl sulfoxide, ethanol and other organic solvents; solubility in water is 70mg/L. When 50 ℃, 6 months without decomposition, stable to light, non-corrosive.

Uses

Tralomethrin controls a range of insects, especially Lepidoptera, in cereals, coffee, cotton, fruit, maize, oilseed rape, rice, tobacco and vegetables. It is also effective for wood protection, household use, in public health, in stored grains and for ectoparasite control on animals.

Uses

Tralomethrin can be used as insecticide.

Definition

ChEBI: A carboxylic ester resulting from the formal condensation between (1R)-cis-2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropanecarboxylic acid and the alcoholic hydroxy group of (2S)-hydroxy(3-phenoxypheny )acetonitrile.

Agricultural Uses

Insecticide: Not approved for use in EU countries. Registered for use in the U.S.

Trade name

DETHMOR®; HAG-107®; RU-25472®; RU-25474®; SCOUT®; SCOUT® X-TRA Gel insecticide

Synthesis

The laboratory synthesis of Tralomethrin is a multi-step process. The final key step involves the bromination of its precursor, Deltamethrin. Deltamethrin itself is synthesized via the esterification of (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid with (S) cyano-(3-phenoxyphenyl)methanol.
step 1. Synthesis of Deltamethrin (Precursor)
Dissolve (S)-cyano-(3-phenoxyphenyl)methanol in anhydrous toluene in a reaction vessel equipped with a stirrer and under a nitrogen atmosphere. Cool the solution to a low temperature (e.g., -10°C). Slowly add a solution of (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride in anhydrous toluene to the cooled solution. Add a solution of pyridine in toluene dropwise to the reaction mixture. Allow the reaction to proceed at a controlled temperature (e.g., 20°C) for several hours. Upon completion, wash the reaction mixture with dilute hydrochloric acid, followed by a sodium bicarbonate solution. Dry the organic layer over anhydrous sodium sulfate and evaporate the solvent under reduced pressure to obtain crude Deltamethrin. Purify the crude product by a suitable method, such as crystallization or column chromatography.
step 2. Synthesis of Tralomethrin from Deltamethrin
Dissolve Deltamethrin in a suitable solvent in a reaction vessel protected from light. Cool the solution to a low temperature. Slowly add a solution of bromine in the same solvent to the Deltamethrin solution. Stir the reaction mixture at a controlled temperature until the reaction is complete. Remove any excess bromine, for example, by bubbling nitrogen through the solution or by washing with a solution of sodium thiosulfate. Evaporate the solvent under reduced pressure to yield crude Tralomethrin.

Metabolic pathway

Tralomethrin probably owes most of its action to rapid conversion by several mechanisms to deltamethrin. Information on its photodegradation, degradation in soil, and its metabolism in plants, insects and animals has been published and supports this conclusion.

Degradation

Tralomethrin is stable as a solid but is labile to base. Acidic media reduce the tendency to hydrolysis and epimerisation. It was readily debrominated when solutions or thin films were irradiated at 360 nm or by sunlight. Homolytic fission of a C-Br bond initiates this reaction, which affords deltamethrin (2). Some epimerisation to trans-tralomethrin and thence trans-deltamethrin also occurred. Dehydrobromination also affords deltamethrin and the tribromo derivative (8). Ester cleavage to the acid (3) and to the cyanohydrin (5) and thence to 3PBAl (6) and 3PBA (7) is important in the solid phase but not in solution (Ruzo and Casida, 1981). The products are shown in Scheme 1.

Toxicity evaluation

Acute oral LD₅₀ for rats: 99-3,000 mg/kg depending on the carrier used

TRALOMETHRIN(66841-25-6)Related Product Information

• 4-Bromobutyric acid
• Methyl 4-bromobutyrate
• BENZYL-2-METHYLBUTYRATE
• Mandelonitrile
• TRALOMETHRIN
• Ethyl cyclopropanecarboxylate
• Bromoform
• BENZYL 4-BROMOBUTANOATE
• (Bromomethyl)cyclopropane
• 5-Bromovaleric acid
• FEMA 2686
• 3-PHENOXYPHENYLACETONITRILE
• 1,1,2-TRIBROMOETHANE
• Methyl 6-bromohexanoate
• 6-Bromo-1-hexanol
• 1,1,2,2-TETRABROMOETHANE
• 3-PHENOXYBENZALDEHYDE CYANOHYDRIN, 70 WT% SOLUTION IN ETHER
• 1,2-DIBROMOHEXANE