Tefluthrin

Tefluthrin Basic information
Description References
Product Name:Tefluthrin
Synonyms:TEFLUTHRIN;(2,3,5,6-tetrafluoro-4-methylphenyl)methylester,(1-alpha,3-alpha(z))-(+-yl;forza;pp993;tefluthrine;2,3,5,6-tetrafluoro-4-methylbenzyl(z)-(1rs,3rs)-3-(2-chloro- 3,3,3-trifluoro-1-propenyl-2,2-dimethylcyclopropanecarboxylate;FORCE;FIREBAN
CAS:79538-32-2
MF:C17H14ClF7O2
MW:418.73
EINECS:616-699-6
Product Categories:Agro-Products;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;PyrethroidsPesticides&Metabolites;Alpha sort;Insecticides;Pesticides;Q-ZAlphabetic;TA - TE
Mol File:79538-32-2.mol
Tefluthrin Structure
Tefluthrin Chemical Properties
Melting point 44-46°C
Boiling point bp1.33hPa 156°
density 1.23
vapor pressure 8×10-3 Pa (20 °C)
storage temp. 0-6°C
solubility Chloroform (Slightly), Methanol (Slightly)
Water Solubility 0.02 mg l-1 (20 °C)
form neat
Merck 13,9192
BRN 8398039
LogP6.500
EPA Substance Registry SystemTefluthrin (79538-32-2)
Safety Information
Hazard Codes T+
Risk Statements 23/24-28
Safety Statements 22-28-36/37/39-45
RIDADR UN 3349
WGK Germany 3
RTECS GZ1227850
HazardClass 6.1(a)
PackingGroup I
HS Code 29162090
Hazardous Substances Data79538-32-2(Hazardous Substances Data)
ToxicityLD50 technical grade in rats (mg/kg): 35 orally; 200-1000 dermally (Marrs, Gordon)
MSDS Information
Tefluthrin Usage And Synthesis
DescriptionTefluthrin is a synthetic pyrethroid pesticide and is synthesized from the flower heads of chrysanthemum cinerariaefolium which contain the natural pyrethroids esters of chrysanthemumic acid or pyrethric acid. It  is approved in Germany for the use of controlling a wide range of soil pests including coleoptera, lepidoptera and diptera in crops such as maize, sugar beet, corn, grains, and cotton.
References[1] http://www.toxipedia.org/display/toxipedia/Tefluthrin
[2] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/617.htm
Chemical PropertiesPale Yellow Low Melting Solid
UsesTefluthrin is a pyrethroid based insecticide. Tefluthrin is used in the control of a broad range of soil pests, including members of the Coleoptera, Lepidoptera, and Diptera.
UsesTefluthrin is used as a soil insecticide to control Coleoptera, Lepidoptera and Diptera in maize, sugar beet and other crops.
DefinitionChEBI: A cyclopropanecarboxylate ester resulting from the formal condensation of the carboxy group of 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylic acid with the hydroxy group of 2,3,5,6-tetrafluoro-4-methylbe zyl alcohol.
Agricultural UsesInsecticide, Miticide: A U.S. EPA restricted use Pesticide (RUP). Registered in the U.S. for use on corn. Elsewhere it is registered for use on a variety of crops, e.g., peanuts, sweet potato, sugarcane, cabbage, radish, Brussels sprouts, and strawberries. Registered for use in EU countries.
Trade nameFORCE®; FORCE® ST; FORZA®; JF 6064®; KOMET-RP®; PP 993®; R 151993®
PharmacologyThe commercialized compound, tefluthrin, was recommended to control soil-inhabiting pests (28). The most salient feature of the compound, which justifies its use exclusively for better performance of tefluthrin as a soil insecticide compared with cyhalothrin, is its approximately four orders ofmagnitude higher vapor pressure (V.P. = 8.4 vs. 0.001 mPa; see Table 6). Beside the quick insecticidal action attributed to fast penetration, tefluthrin also displays toxic symptoms at its sublethal dose, which could play an important role in field performance (179). The most active configuration of tefluthrin, (Z)(1RS)-cis-isomer mixture, is the optically active (Z)(1R)-cis-isomer.
Metabolic pathwayWhen a goat is dosed with 14C-tefluthrin orally, extensive metabolism occurs in the goat by ester cleavage and oxidation at a variety of positions on the molecules. Low radioactive residues are detected in the milk, fat, and muscle, with tefluthrin as the largest individual component of the residue. Higher residues are present in the kidney and liver, and only a small percentage of this residue is due to tefluthrin. The remainder in the kidney and liver is a complex mixture of metabolites. In total, eight metabolites are identified in the feces and urine as well as other tissues such as fat, muscle, kidney, and liver.
DegradationTefluthrin is a stable compound, being resistant to hydrolysis at pH 5-7 for at least 30 days. At pH 9, 7% hydrolysis occurred in 30 days. It is readily hydrolysed at higher pH to afford the cyclopropanecarboxylic acid (2) and 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (3). Exposure in aqueous solution at pH 7 to sunlight causes about 30% degradation in 31 days. Conversion to the trans-isomer occurred and hydrolysis to cis- and trans-2 and 3 followed.
Tefluthrin Preparation Products And Raw materials
Cyhalothrin Tau-fluvalinate Cylopropylmethyl chloride (S)-(+)-2,2-DIMETHYLCYCLOPROPANE CARBOXYLIC ACID Lambda Cyhalotric Acid Transfluthrin Dimefluthrin ETHYL 5-CHLORO-5-HEXENOATE Tefluthrin,95%Tc,1.5%,3%Wdg,10%Ec,10%Sc 4-Fluorobenzaldehyde 1-(BENZYLOXY)-4-CHLOROBUTANE ACRINATHRIN Tefluthrin Epichlorohydrin FLUCYTHRINATE Polytetrafluorethylene wire rod [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-pro p-1-enyl-cyclopropane-1-carboxylate FENFLUTHRIN

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