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Propoxur

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Propoxur
Skeletal formula of propoxur
Ball-and-stick model of the propoxur molecule
Names
Preferred IUPAC name 2-phenyl methylcarbamate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.676 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CC(C)Oc1ccccc1OC(=O)NC
Properties
Chemical formula C11H15NO3
Molar mass 209.245 g·mol
Appearance White to tan crystalline powder
Odor faint, characteristic
Melting point 86 to 92 °C; 187 to 197 °F; 359 to 365 K
Boiling point decomposes
Solubility in water 0.2% (20°C)
Vapor pressure 0.0000937 mmHg (20 °C)
Pharmacology
ATCvet code QP53AE02 (WHO)
Hazards
Flash point > 149 °C; 300 °F; 422 K
NIOSH (US health exposure limits):
PEL (Permissible) none
REL (Recommended) TWA 0.5 mg/m
IDLH (Immediate danger) N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Propoxur (Baygon) is a carbamate non-systemic insecticide, produced from catechol, and was introduced in 1959. 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. It can also be used as a molluscicide.

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.

Action

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

Environmental effects

Propoxur rapidly breaks down in alkaline solution. Propoxur is highly toxic to many bird species, although its toxicity varies by the species, and it is highly toxic to honeybees. It is moderately to slightly toxic to fish and other aquatic species.

References

  1. ^ 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. ACGIH, 1991a
  4. ^ Budavari, 1996a
  5. Lewis, 1993a
  6. ^ EXTOXNET Extension Toxicology Network. Pesticide Information Profile. Propoxur. June 1996.
  7. "In Search of a Bedbug Solution". New York Times. September 4, 2010.
  8. Propoxur (WHO Pesticide Residues Series 3): October 01, 2009.
Pest control: Insecticides
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Acetylcholine metabolism and transport modulators
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
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