Tetramethrin

Tetramethrin
Tetramethrin
Tetramethrin
3D model
3D model
Names
IUPAC name
(1,3-Dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Preferred IUPAC name
(1,3-Dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.028.829 Edit this at Wikidata
EC Number
  • 214-619-0
KEGG
RTECS number
  • GZ1730000
UNII
  • InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3 checkY
    Key: CXBMCYHAMVGWJQ-UHFFFAOYSA-N checkY
  • InChI=1/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3
    Key: CXBMCYHAMVGWJQ-UHFFFAOYAA
  • O=C1\C3=C(/C(=O)N1COC(=O)C2C(\C=C(/C)C)C2(C)C)CCCC3
Properties
C19H25NO4
Molar mass 331.406 g/mol
Appearance white crystalline solid
Odor strong, pyrethrum-like
Density 1.108 g/cm3
Melting point 65 to 80 °C (149 to 176 °F; 338 to 353 K)
0.00183 g/100 mL
Solubility soluble in methane, hexane
slightly soluble in acetone, n-octanol, ethanol
very slightly soluble in xylene
log P 4.73
Vapor pressure 10 Pa
1.5175
Pharmacology
P03BA04 (WHO) QP53AC13 (WHO)
Hazards
Lethal dose or concentration (LD, LC):
20,000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Tetramethrin is a potent synthetic insecticide belonging to the pyrethroid family that rapidly paralyzes flying and crawling insects immediately upon contact. It is inspired by the insecticidal properties of natural chrysanthemum flowers. While it has a relatively low toxicity for humans and mammals, it is heavily restricted in many regions due to being highly toxic to aquatic life and bees, as well as being classified as a suspected carcinogen.

History

Tetramethrin was the second pyrethroid to become commercially available. It was introduced by Sumitomo Chemical in 1965 as a non-systemic contact insecticide.

Tetramethrin was approved for use as an insecticide in Germany from 1977 to 1981.

Synthesis and preparation

Tetramethrin can be synthesized by reacting 1-cyclohexene-1,2-dicarboximide with formaldehyde to form a hemiaminal, followed by esterification with chrysanthemic acid.

A mixture enriched in the (1R)-cis and (1R)-trans isomers is marketed under the name d-tetramethrin.

Properties

It is a white crystalline solid with a melting point of 65–80 °C. The commercial product is a mixture of stereoisomers.

Uses

Tetramethrin is primarily used to control indoor pests such as flies, mosquitoes, and cockroaches. It is commonly used as an insecticide, and affects the insect's nervous system. It is found in many household insecticide products.

Approval

The use of tetramethrin as an active ingredient in plant protection products is not permitted in the European Union. No plant protection products containing this active ingredient are currently approved in Germany, Austria, or Switzerland. Until November 2005, tetramethrin was listed in Annex 1 (Active ingredients approved for use in plant protection products) of the Swiss Plant Protection Products Ordinance. A decision on its notification as a biocide in product type 18 (insecticides, acaricides, and products against other arthropods) is still pending.

Tetramethrin was classified as a Category 2 carcinogen in 2018 by Directorate-General for the Environment of the European Commission.

Degradation

Tetramethrin degrades rapidly in the environment. Its photolysis half-life in air, resulting from a reaction with ozone, is approximately 30 minutes. Its hydrolysis half-life depends on the pH and ranges from a few minutes to three weeks.

Tetramethrin has an expected half-life of 12.5–14 days in soil and 13–25 days in water.

References

  1. 1 2 3 Entry on Tetramethrin. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
  2. ↑ Zulassungshistorie des Bundesamt für Verbraucherschutz und Lebensmittelsicherheit
  3. ↑ Thomas A. Unger (1996), Pesticide Synthesis Handbook, William Andrew, p. 960, ISBN 0-81551853-6
  4. ↑ Tetramethrin in the Consumer Product Information Database[dead link]
  5. ↑ "Verordnung (EG) Nr. 2076/2002 der Kommission vom 20. November 2002". 2002. zur Verlängerung der Frist gemäß Artikel 8 Absatz 2 der Richtlinie 91/414/EWG des Rates und über die Nichtaufnahme bestimmter Wirkstoffe in Anhang I dieser Richtlinie sowie den Widerruf der Zulassungen von Pflanzenschutzmitteln mit diesen Wirkstoffen.
  6. ↑ "EU Pesticides Database". ec.europa.eu. Retrieved 2026-10-18.
  7. ↑ Verordnung über das Inverkehrbringen von Pflanzenschutzmitteln (Pflanzenschutzmittelverordnung, PSMV); Änderung vom 7. November 2005
  8. ↑ Konsolidierte Liste der notifizierten Wirkstoffe, 2020.
  9. ↑ "Commission Regulation (EU) 2018/1480 of 4 October 2018 amending, for the purposes of its adaptation to technical and scientific progress, Regulation (EC) No 1272/2008 of the European Parliament and of the Council on classification, labelling and packaging of substances and mixtures and correcting Commission Regulation (EU) 2017/776 (Text with EEA relevance.)". 4 October 2018.
  10. ↑ Halbwertszeit bei pH≈9: ca. 13 – 20 Minuten; pH≈7: ca. 21,5 – 26 Stunden; pH≈5: ca. 16 – 20 Tage
    "Reregistration Eligibility Decision (RED) for Tetramethrin" (PDF). Environmental Protection Agency. 2008-06-23. p. 19. Archived from the original (PDF) on 2014-10-16. Retrieved 2020-04-21.
  11. ↑ "Re-evaluation Decision RVD2018-01, Tetramethrin and Its Associated End-use Products". 23 February 2018.[dead link]