Icaridin

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Structural formula
Structural formulas of the four stereoisomers of icaridin
Mixture of four stereoisomers
General
Non-proprietary name Icaridin
other names
  • 1- (1-methylpropoxycarbonyl) -2- (2-hydroxyethyl) piperidine
  • HYDROXYETHYL ISOBUTYL PIPERIDINE CARBOXYLATE ( INCI )
  • Bayrepel
  • Picaridin
  • Saltidin
Molecular formula C 12 H 23 NO 3
External identifiers / databases
CAS number
  • 119515-38-7 ( mixture of stereoisomers)
  • 875811-91-9 [( R , R ) -isomer]
  • 875811-93-1 [( S , S ) -isomer]
  • 875811-92-0 [( R , S ) -isomer]
  • 875811-90-8 [( S , R ) -isomer]
EC number 423-210-8
ECHA InfoCard 100.102.177
PubChem 125098
ChemSpider 111359
DrugBank DB14074
Wikidata Q418792
Drug information
Drug class

Repellent

properties
Molar mass 229,32 g · mol -1
boiling point

296 ° C

solubility
  • practically insoluble in water
  • soluble in acetone
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

3500 mg kg −1 ( LD Loratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Icaridin is a repellent with a broad spectrum of action against insects . Lanxess AG owns the rights .

The name picaridin or hepidanin was originally proposed for the active ingredient (and is still used in various countries today), but the World Health Organization (WHO) has specified the name Icaridin as an international non-proprietary name (INN).

Extraction and presentation

Icaridine can be obtained by reacting carbonyldiimidazole with 2-butanol and 2-piperidineethanol in a solvent such as dichloromethane or acetonitrile .

properties

Icaridin is chiral and contains two stereocenters . The active ingredient is used as a mixture of the four stereoisomers , the racemate from the ( R , R ) - and the ( S , S ) form on the one hand and the racemate from the ( R , S ) - and the ( S , R ) - On the other hand, the shape is approximately 1: 1.

effect

The active ingredients DEET (diethyltoluamide), icaridin and para-menthane-3,8-diol are among the most effective active ingredients against insect bites. For this reason, products with these ingredients are recommended - especially for the defense against disease-transmitting insects. Which active ingredient is better is not clear due to partly contradicting sources. Due to the long-standing practical experience, DEET is recommended by the Stiftung Warentest in malaria areas. In a concentration of 30 to 50%, the active ingredient DEET is superior to Icaridin according to the source. In contrast, the WHO recommends Icaridin as the repellent of choice for the prevention of malaria infections (KBR3023 = Icaridin). In a field study in Burkina Faso, Icaridin (KBR 3023) proved to be superior to DEET in preventing stings from Anopheles gambiae .

Icaridin was examined in its effectiveness against various ectoparasites and compared with the classic repellent DEET. As with DEET, there was a broad spectrum of activity against, among other things, Anopheles mosquitoes, Aedes mosquitoes, Culex mosquitoes and the common wood tuck . According to Stiftung Warentest, the active ingredient Icaridin is preferable in areas that are not at risk of malaria, such as Germany and Europe. The test winner from Stiftung Warentest in May 2017 in the field of combination products also contains Icaridin.

In contrast to the DEET solvent, Icaridin does not attack plastics.

Ecological impact assessments

If Icaridin gets into water, it kills amphibian larvae in very small doses - as natural enemies of mosquitoes - as well as their food source. Icaridin is particularly damaging in the amphibian breeding season: if amphibians are exposed in sensitive life stages, entire cohorts can die while mosquitoes multiply. In their pure form, DEET and Icaridin are not water-soluble. However, additives in commercially available repellents change this.

Trade names

Icaridin can be found in insect repellants from Autan , Ballistol , Picaridin, Saltidin, Bayrepel, Doctan, S-quito free and Zeckito (classic, Baby & Kids, tropical, sun).

Individual evidence

  1. Entry on HYDROXYETHYL ISOBUTYL PIPERIDINE CARBOXYLATE in the CosIng database of the EU Commission, accessed on December 28, 2019.
  2. a b c WHO: WHO SPECIFICATIONS AND EVALUATIONS FOR PUBLIC HEALTH PESTICIDES: ICARIDIN ( EN , PDF; 150 kB) p. 18. Archived from the original on August 16, 2009. Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. Retrieved August 9, 2009. @1@ 2Template: Webachiv / IABot / www.who.int
  3. ^ A b Anna Wypych, George Wypych: Databook of Biocides . Elsevier, 2015, ISBN 978-1-927885-04-8 , pp. 392 ( books.google.de ).
  4. a b c CaymanChem: Picaridin , accessed December 27, 2019
  5. Jordan Moats, Dr. Martin Hulce: Increase in the rate of the synthesis of (P) icaridin ( Memento of the original dated August 6, 2017 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , Department of Chemistry, Creighton University, 2008 @1@ 2Template: Webachiv / IABot / hydrogen.creighton.edu
  6. ^ Stiftung Warentest: Insect repellants , June 2014, accessed on October 14, 2015.
  7. ^ Course book travel medicine: advice, prophylaxis, traveling with illnesses . Georg Thieme Verlag, 2012, ISBN 978-3-13-167171-4 , p. 76 ( books.google.de ).
  8. ^ World Health Organization: Report of the fourth WHOPES working group meeting: WHO / HQ, Geneva, December 4-5, 2000: review of: IR3535; KBR3023; (RS) -Methoprene 20% EC, pyriproxyfen 0.5% GR; and lambda-cyhalothrin 2.5% CS . 2001 ( who.int [accessed January 6, 2019]).
  9. Edith Ilboudo-Sanogo, Athanase Badolo, Carlo Costantini: Field evaluation of the efficacy and persistence of insect repellents DEET, IR3535, and KBR 3023 against Anopheles gambiae complex and other Afrotropical vector mosquitoes . In: Transactions of The Royal Society of Tropical Medicine and Hygiene . tape 98 , no. 11 , November 1, 2004, ISSN  0035-9203 , p. 644–652 , doi : 10.1016 / j.trstmh.2003.12.015 ( oup.com [accessed January 6, 2019]).
  10. Insect repellants (05/2017) , accessed on March 12, 2018.
  11. Ticks and mosquitoes: These remedies help against bloodsuckers (05/2017) , accessed on March 12, 2018.
  12. Pharmazeutische Zeitung Edition 32/2006: Successfully repelling insects - by Ralf Goebel and Martin Schulz , accessed on October 14, 2015.
  13. zecken-und-insektenschutz.de (HERMES Arzneimittel): Icaridin - effective insect repellent and very skin-friendly , accessed on October 14, 2015.
  14. Rafael Almeida et al .: The dark side of mosquito repellants . In: Royal Society Biology Letters , doi : 10.1098 / rsbl.2018.0526 .