Propoxur

Propoxur
Skeletal formula of propoxur
Ball-and-stick model of the propoxur molecule
Names
Preferred IUPAC name
2-[(Propan-2-yl)oxy]phenyl methylcarbamate
Identifiers
CAS Number
  • 114-26-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34938 ☒N
ChEMBL
  • ChEMBL446060 ☒N
ChemSpider
  • 4775 ☒N
ECHA InfoCard 100.003.676 Edit this at Wikidata
KEGG
  • C14334 checkY
PubChem CID
  • 4944
UNII
  • BFH029TL73 checkY
CompTox Dashboard (EPA)
  • DTXSID7021948 Edit this at Wikidata
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
  • CC(C)Oc1ccccc1OC(=O)NC
Properties
Chemical formula
C11H15NO3
Molar mass 209.245 g·mol−1
Appearance White 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]
Solubility in water
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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Infobox references
Chemical compound

Propoxur (Baygon) is a carbamate non-systemic insecticide, produced from catechol,[2] 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.[3][4] It can also be used as a molluscicide.[4][5][6]

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.[7]

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.[8] Propoxur is highly toxic to many bird species, although its toxicity varies by the species, and it is highly toxic to honeybees.[6] It is moderately to slightly toxic to fish and other aquatic species.

References

  1. ^ a b c d e f g h 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 (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.
  3. ^ ACGIH, 1991a[full citation needed]
  4. ^ a b Budavari, 1996a[full citation needed]
  5. ^ Lewis, 1993a[full citation needed]
  6. ^ a b 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.
  • v
  • t
  • e
CarbamatesInorganic compoundsInsect growth regulatorsNeonicotinoidsOrganochloridesOrganophosphorusPyrethroidsRyanoidsOther chemicalsMetabolitesBiopesticides
  • v
  • t
  • e
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
  • Inhibitors: 1-(-Benzoylethyl)pyridinium
  • 2-(α-Naphthoyl)ethyltrimethylammonium
  • 3-Chloro-4-stillbazole
  • 4-(1-Naphthylvinyl)pyridine
  • Acetylseco hemicholinium-3
  • Acryloylcholine
  • AF64A
  • B115
  • BETA
  • CM-54,903
  • N,N-Dimethylaminoethylacrylate
  • N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
  • SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E)
  • VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G)
Enhancers
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators