Propoxur

Last updated
Propoxur
Propoxur.png
Propoxur-3D-balls.png
Names
Preferred IUPAC name
2-[(Propan-2-yl)oxy]phenyl methylcarbamate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.676 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C11H15NO3/c1-8(2)14-9-6-4-5-7-10(9)15-11(13)12-3/h4-8H,1-3H3,(H,12,13)
    Key: ISRUGXGCCGIOQO-UHFFFAOYSA-N
  • CC(C)Oc1ccccc1OC(=O)NC
Properties
C11H15NO3
Molar mass 209.245 g·mol−1
AppearanceWhite to tan crystalline powder [1]
Odor faint, characteristic [1]
Melting point 86 to 92 °C; 187 to 197 °F; 359 to 365 K
Boiling point decomposes [1]
0.2% (20°C) [1]
Vapor pressure 0.0000937 mmHg (20 °C) [1]
Pharmacology
QP53AE02 ( WHO )
Hazards
Flash point >149 °C; 300 °F; 422 K
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 0.5 mg/m3 [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propoxur is a carbamate, non-systemic, synthetic insecticide, produced from catechol, [2] and was introduced in 1959 by Bayer. [3]

Contents

Action

Carbamate insecticides kill insects by irreversibly inactivating the enzyme acetylcholinesterase, thus it is a Cholinesterase inhibitor.

It has a fast knockdown and long residual effect, and is used against turf, forestry, and household pests and fleas. It is also used in pest control for domestic animals, Anopheles mosquitoes, ants, gypsy moths, and other agricultural pests. [4] [5] It can also be used as a molluscicide. [5] [6] [7] It has been an ingredient in the consumer insecticide brand, Baygon.

Environmental effects

Propoxur is highly toxic to many bird species, although its toxicity varies by the species, and it is highly toxic to honeybees. [7] It is moderately to slightly toxic to fish and other aquatic species.

EFSA recommends that the active substance should be assessed for neurotoxicity, since propoxur acts by inhibition of acetyl cholinesterase. [3] Several U.S. states have petitioned the Environmental Protection Agency (EPA) to use propoxur against bedbug infestations, but the EPA has been reluctant to approve indoor use because of its potential toxicity to children after chronic exposure. [8]

Propoxur rapidly breaks down in alkaline solution. [9]

Regulation

The use of propoxur products ended in Europe after no manufacturer submitted an application for approval in 2002. [3] Manufacturers reached an agreement with the US EPA to withdraw propoxur from flea and tick collars during 2015-2016 due to concerns about exposure of the ingredient to children. [10]

References

  1. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0531". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   3527306730.
  3. 1 2 3 Anastassiadou, Maria; Bernasconi, Giovanni; Brancato, Alba; Carrasco Cabrera, Luis; Ferreira, Lucien; Greco, Luna; Jarrah, Samira; Kazocina, Aija; Leuschner, Renata; Magrans, Jose Oriol; Miron, Ileana; Nave, Stefanie; Pedersen, Ragnor; Reich, Hermine; Rojas, Alejandro; Sacchi, Angela; Santos, Miguel; Scarlato, Alessia Pia; Theobald, Anne; Vagenende, Benedicte; Verani, Alessia (January 2021). "Reasoned opinion on the toxicological properties and maximum residue levels for propoxur". EFSA Journal. 19 (1). doi:10.2903/j.efsa.2021.6374.
  4. ↑ ACGIH, 1991a[ full citation needed ]
  5. 1 2 Budavari, 1996a[ full citation needed ]
  6. ↑ Lewis, 1993a[ full citation needed ]
  7. 1 2 EXTOXNET Extension Toxicology Network. Pesticide Information Profile. Propoxur. June 1996.
  8. ↑ "In Search of a Bedbug Solution". New York Times . September 4, 2010.
  9. ↑ Propoxur (WHO Pesticide Residues Series 3): October 01, 2009.
  10. ↑ "Companies Agree to Stop Selling Pet Collars Containing Pesticide to Protect Children". US EPA. Retrieved 25 October 2025.
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