Tefluthrin
tefluthrin (racemic)
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Names | |
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Preferred IUPAC name
rac-(2,3,5,6-Tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]cyclopropane-1-carboxylate | |
Other names
Tefluthrine
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.124.968 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties[1] | |
C17H14ClF7O2 | |
Molar mass | 418.74 g·mol−1 |
Appearance | colorless solid |
Density | 1.48 g/mL |
Melting point | 44.6 °C |
Boiling point | 156 °C at 1 mmHg |
0.02 mg/L in water
>500 g/L in acetone, hexane, toluene | |
log P | 6.4 |
Hazards[2] | |
GHS labelling: | |
Danger | |
H300, H310, H330, H410 | |
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tefluthrin is the
Synthesis
Tefluthrin (X=CH3) is manufactured by the
History
By 1974, a team of
Mechanism of action
Pyrethroid insecticides, including tefluthrin, disrupt the functioning of the nervous system in an organism. They are fast-acting
Formulations
Tefluthrin is made available to end-users only in
Usage
All pesticides are required to seek registration from appropriate authorities in the country in which they will be used.[22] In the United States, the Environmental Protection Agency (EPA) is responsible for regulating pesticides under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) and the Food Quality Protection Act (FQPA).[23] A pesticide can only be used legally according to the directions on the label that is included at the time of the sale of the pesticide. The purpose of the label is "to provide clear directions for effective product performance while minimizing risks to human health and the environment". A label is a legally binding document that mandates how the pesticide can and must be used and failure to follow the label as written when using the pesticide is a federal offense.[24] The current (2020) label for tefluthrin in the USA covers its use on field corn, popcorn, seed corn and sweetcorn and specifies the amount to be applied.[25] Within the European Union, a 2-tiered approach is used for the approval and authorisation of pesticides. Firstly, before a formulated product can be developed for market, the active substance must be approved for the European Union. After this has been achieved, authorisation for the specific product must be sought from every Member State that the applicant wants to sell it to. Afterwards, there is a monitoring programme to make sure the pesticide residues in food are below the limits set by the European Food Safety Authority.
The main use of tefluthrin is to control the larvae of corn rootworms (
Human safety
Tefluthrin is a restricted use pesticide. One consequence of this is that, in the US, it is a violation of Federal law to use the product in a manner inconsistent with its labelling and the labelling must be in possession of the user at the time of the application. It can be absorbed into the body by inhalation of dust or mist and by ingestion. It causes moderate eye irritation. Prolonged or frequently repeated skin contact may cause allergic reactions in some individuals. Skin exposure may result in a transient sensation described as a tingling, itching, burning, or prickly feeling. Onset may occur immediately to four hours after exposure and may last 2–30 hours, without apparent skin damage.[25] First aid measures are included with the label information.[25]
Metabolism
The mammalian
Environmental effects
Tefluthrin is very highly toxic to freshwater and estuarine fish and invertebrates.[25] Its properties and effects on the environment have been summarized in several publications.[1][2][28] Ultimately it is the regulatory authorities in each country who must weigh up the benefits to end users and balance these against the compound's inherent hazards and consequent risks to consumers and the wider environment. These authorities stipulate the conditions under which tefluthrin may be used.
Resistance management
Species have the ability to evolve and develop resistance to pyrethroids (and, indeed, almost all pesticides). This potential can be mitigated by careful management. Reports of individual pest species becoming resistant to tefluthrin are monitored by manufacturers, regulatory bodies such as the EPA and the Insecticide Resistance Action Committee (IRAC).[29] In some cases, the risks of resistance developing can be reduced by using a mixture of two or more insecticides which each have activity on relevant pests but with unrelated mechanisms of action. IRAC assigns insecticides into classes so as to facilitate this.
References
- ^ a b c d e f Pesticide Properties Database. "Tefluthrin". University of Hertfordshire.
- ^ a b "Tefluthrin". US National Library of Medicine. Retrieved 2020-02-02.
- ^ "Compendium of Pesticide Common Names: tefluthrin". BCPC.
- .
- ^ a b c McDonald, E.; Punja, N.; Jutsum, A. R. (1986). "Rationale in the invention and optimization of tefluthrin, a pyrethroid for use in soil". British Crop Protection Conference--Pests and Diseases, Proceedings (1): 199–206.
- ^ a b GB withdrawn 2085000, Crosby, John, "An improved process for the preparation of certain cyclopropane pyrethroid intermediates having a high cis-content", published 1982-04-21, assigned to ICI plc
- ^ US patent 4551546, Punja, N, assigned to ICI plc
- .
- .
- ISBN 978-0-8412-0368-6.
- ^ "Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre" (PDF). Syngenta. 2003. Archived from the original (PDF) on October 11, 2007.
- ^ "US4551546, Halogentated esters".
- ^ "EUR-Lex - 32008D0934 - EN". eur-lex.europa.eu. 2008-12-05.
- ^ "EUR-Lex - 02008D0934-20120101 - EN". 2012-01-01.
- ^ "EU Pesticides database - European Commission". ec.europa.eu.
- PMID 19026681.
- S2CID 89494224.
- PMID 11144347.
- PMID 20624410.
- ISBN 978-0-07-134721-1.
- ^ "Force 6.5g insecticide". Syngenta United States. Retrieved 2020-02-02.
- ^ Willson HR (1996). "Pesticide Regulations". In Radcliffe EB, Hutchison WD, Cancelado RE (eds.). Radcliffe's IPM World Textbook. St. Paul: University of Minnesota. Archived from the original on July 13, 2017.
- US EPA. 2015-08-20. Archived from the originalon January 14, 2014. Retrieved 2020-02-04.
- ^ EPA (27 February 2013). "The Pesticide Label". Retrieved 2020-02-04.
- ^ a b c d "Force 6.5g". Syngenta United States. Retrieved 2020-02-02.
- ^ US Geological Survey (2020-06-18). "Estimated Agricultural Use for tefluthrin, 2017". Retrieved 2020-09-04.
- ISBN 978-1-84973-300-7.
- ISBN 978-1-100-14618-8.
- ^ "IRAC website".
Further reading
- Leahy, J.P., ed. (1985). The Pyrethroid Insecticides. Taylor and Francis, London. p. 440. ISBN 0-85066-283-4.
- Naumann, Klaus (2013). Synthetic Pyrethroid Insecticides: Structures and Properties. Springer. p. 244. ISBN 978-3-642-74851-6.
- Naumann, Klaus (2012). Synthetic Pyrethroid Insecticides: Chemistry and Patents. Springer. p. 412. ISBN 978-3-642-74854-7.
External links
- PPDB pesticides properties database of tefluthrin
- MSDS of tefluthrin from Sigma-Aldrich
- Tefluthrin on Pubchem
- International Chemical safety information