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Propoxur

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.676Edit this at Wikidata
KEGG
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 mass209.245 g·mol−1
AppearanceWhite to tan crystalline powder[1]
Odorfaint, characteristic[1]
Melting point86 to 92 °C; 187 to 197 °F; 359 to 365 K
Boiling pointdecomposes[1]
0.2% (20°C)[1]
Vapor pressure0.0000937 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Propoxur (Baygon) is acarbamate non-systemicinsecticide, produced fromcatechol,[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]

SeveralU.S. states have petitioned theEnvironmental Protection Agency (EPA) to use propoxur againstbedbug infestations, but the EPA has been reluctant to approve indoor use because of its potential toxicity to children after chronic exposure.[7]

Action

[edit]

Carbamate insecticides kill insects by irreversibly inactivating theenzymeacetylcholinesterase, thus it is aCholinesterase inhibitor.

Environmental effects

[edit]

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

[edit]
  1. ^abcdefghNIOSH 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[full citation needed]
  4. ^abBudavari, 1996a[full citation needed]
  5. ^Lewis, 1993a[full citation needed]
  6. ^abEXTOXNET 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.
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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