Propoxur

Names
Preferred IUPAC name

2-[(Propan-2-yl)oxy]phenyl methylcarbamate

Identifiers

CAS Number

* 114-26-1 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:34938 N

ChEMBL |

* ChEMBL446060 N

ChemSpider |

* 4775 N

KEGG |

* C14334 Y

PubChem CID

* 4944

UNII |

* BFH029TL73 Y

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−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
1=ATCvet code}  | 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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 NIOSH Pocket Guide to Chemical Hazards. "#0531". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0531.html.
2. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
3. ↑ ACGIH, 1991a[full citation needed]
4. ↑ 4.0 4.1 Budavari, 1996a[full citation needed]
5. ↑ Lewis, 1993a[full citation needed]
6. ↑ 6.0 6.1 EXTOXNET Extension Toxicology Network. Pesticide Information Profile. Propoxur. June 1996.
7. ↑ "In Search of a Bedbug Solution". New York Times. September 4, 2010. https://www.nytimes.com/2010/09/05/opinion/05sun3.html.
8. ↑ Propoxur (WHO Pesticide Residues Series 3): October 01, 2009.

* v
* t
* e

Pest control: Insecticides

Carbamates|

* Aldicarb
* Bendiocarb
* Carbaryl
* Carbofuran
* Ethienocarb
* Fenobucarb
* Oxamyl
* Methomyl
* Propoxur

Inorganic compounds|

* Aluminium phosphide
* Boric acid
* Chromated copper arsenate
* Copper(II) arsenate
* Copper(I) cyanide
* Cryolite
* Diatomaceous earth
* Lead hydrogen arsenate
* Paris Green
* Scheele's Green

Insect growth regulators|

* Benzoylureas
* Diflubenzuron
* Flufenoxuron
* Hydroprene
* Lufenuron
* Methoprene
* Pyriproxyfen

Neonicotinoids|

* Acetamiprid
* Clothianidin
* Dinotefuran
* Imidacloprid
* Nitenpyram
* Nithiazine
* Thiacloprid
* Thiamethoxam

Organochlorides|

* Aldrin
* Beta-HCH
* Carbon tetrachloride
* Chlordane
* Cyclodiene
* 1,2-DCB
* 1,4-DCB
* 1,1-DCE
* 1,2-DCE
* DDD
* DDE
* DDT
* Dicofol
* Dieldrin
* Endosulfan
* Endrin
* Heptachlor
* Kepone
* Lindane
* Methoxychlor
* Mirex
* Tetradifon
* Toxaphene

Organophosphorus|

* Acephate
* Azamethiphos
* Azinphos-methyl
* Bensulide
* Chlorethoxyfos
* Chlorfenvinphos
* Chlorpyrifos
* Chlorpyrifos-methyl
* Coumaphos
* Demeton-S-methyl
* Diazinon
* Dichlorvos
* Dicrotophos
* Diisopropyl fluorophosphate
* Dimefox
* Dimethoate
* Dioxathion
* Disulfoton
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fosthiazate
* Isoxathion
* Malathion
* Methamidophos
* Methidathion
* Mevinphos
* Mipafox
* Monocrotophos
* Naled
* Omethoate
* Oxydemeton-methyl
* Parathion
* Parathion-methyl
* Phenthoate
* Phorate
* Phosalone
* Phosmet
* Phoxim
* Pirimiphos-methyl
* Quinalphos
* Schradan
* Temefos
* Tebupirimfos
* Terbufos
* Tetrachlorvinphos
* Tribufos
* Trichlorfon

Pyrethroids|

* Acrinathrin
* Allethrins
* Bifenthrin
* Bioallethrin
* Cyfluthrin
* Cyhalothrin
* Cypermethrin
* Cyphenothrin
* Deltamethrin
* Empenthrin
* Esfenvalerate
* Etofenprox
* Fenpropathrin
* Fenvalerate
* Flumethrin
* Imiprothrin
* Metofluthrin
* Permethrin
* Phenothrin
* Prallethrin
* Pyrethrin (I, II; chrysanthemic acid)
* Pyrethrum
* Resmethrin
* Silafluofen
* Tefluthrin
* Tetramethrin
* Tralomethrin
* Transfluthrin

Ryanoids|

* Chlorantraniliprole
* Cyantraniliprole
* Flubendiamide
* Ryanodine
* Ryanodol

Other chemicals|

* Afoxolaner
* Amitraz
* Azadirachtin
* Buprofezin
* Chlordimeform
* Chlorfenapyr
* Cyromazine
* Fenazaquin
* Fenoxycarb
* Fipronil
* Fluralaner
* Hydramethylnon
* Indoxacarb
* Limonene
* Lotilaner
* Pyridaben
* Pyriprole
* Ryanodine
* Sarolaner
* Sesamex
* Spinosad
* Sulfluramid
* Tebufenozide
* Tebufenpyrad
* Veracevine
* Xanthone
* Metaflumizone

Metabolites|

* Oxon
* Malaoxon
* Paraoxon
* TCPy

Biopesticides|

* Bacillus thuringiensis
* Baculovirus
* Beauveria bassiana
* Beauveria brongniartii
* Metarhizium acridum
* Metarhizium anisopliae
* Nomuraea rileyi
* Lecanicillium lecanii
* Paecilomyces fumosoroseus
* Paenibacillus popilliae
* Purpureocillium lilacinum

* v
* t
* e

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)|

| ChAT|

* 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

|

AChE|

* Inhibitors: Reversible: Carbamates: Aldicarb
* Aminocarb
* Bendiocarb
* Bufencarb
* Carbaryl
* Carbendazim
* Carbetamide
* Carbofuran
* Carbosulfan
* Chlorbufam
* Chloropropham
* Dimetilan
* Ethienocarb
* Ethiofencarb
* Fenobucarb
* Formetanate
* Formparanate
* Methiocarb
* Methomyl
* Metolcarb
* Miotine
* Oxamyl
* Phenmedipham
* Pinmicarb
* Pirimicarb
* Propamocarb
* Propham
* Propoxur
* Thiofanox; Stigmines: Distigmine
* Eptastigmine
* Ganstigmine
* Neostigmine
* Phenserine
* Physostigmine
* Pyridostigmine
* Quilostigmine
* Rivastigmine
* Terestigmine; Others: Acotiamide
* Ambenonium
* Caffeine
* Donepezil
* EA-3990
* EA-4056
* Edrophonium
* Galantamine
* Huperzine A
* Ipidacrine
* Itopride
* Ladostigil
* Minaprine
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* T-1123
* TL-599
* TL-1238
* Tacrine
* Zanapezil

* Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Acephate
* Anatoxin-a(S)
* Armine
* Azinphos-ethyl
* Azinphos-methyl
* BAY-29952
* Bensulide
* Cadusafos
* Carbophenothion
* Chlorethoxyfos
* Chlorfenvinphos
* Chlorpyrifos
* Chlorpyrifos-methyl
* Coumaphos
* Crotylsarin
* Cyanophos
* Cyclosarin (GF)
* Demephion
* Demeton
* Demeton-S-methyl
* Dialifor
* Diazinon
* Dichlorvos
* Dicrotophos
* Diisopropyl fluorophosphate
* Diisopropylphosphate
* Dimefox
* Dimethoate
* Dimethyl 4-(methylthio)phenyl phosphate
* Dioxathion
* Disulfoton
* EA-2012
* EA-2054
* EA-2098
* EA-2192
* EA-2613
* EA-3148
* EA-4352
* Echothiophate
* Ethylsarin (GE)
* Endothion
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fluorotabun
* Fonofos
* Formothion
* Fosthiazate
* GD-42
* GH
* GT-45
* GV
* Hexaethyl tetraphosphate
* Isofluorophate
* Isoxathion
* Leptophos
* Malaoxon
* Malathion
* Methamidophos
* Methidathion
* Methyl phenkapton
* Methylfluorophosphonylcholine (MFPCh)
* Metrifonate
* Mevinphos
* Mipafox
* Monocrotophos
* Naled
* Novichok agent
* Omethoate
* Oxydemeton-methyl
* Paraoxon
* Parathion
* Parathion-methyl
* Phorate
* Phosalone
* Phosfolan
* Phosmet
* Phosphamidon
* Phoxim
* Pirimiphos-methyl
* Profenofos
* Prothoate
* Ro 3-0340
* Ro 3-0346
* Ro 3-0347
* Ro 3-0351
* Ro 3-0352
* Ro 3-0397
* Ro 3-0411
* Ro 3-0412
* Ro 3-0417
* Ro 3-0419
* Ro 3-0422
* Ro 3-0433
* Sarin (GB)
* Schradan
* Soman (GD)
* Tabun (GA)
* Tebupirimfos
* Temefos
* Terbufos
* Tetrachlorvinphos
* Tetraethyl pyrophosphate
* Triazofos
* Tribufos
* Trichlorfon
* Trichloronate
* Tricresyl phosphate
* VE
* VG
* VM
* VP
* VS
* VR
* VX; Others: Demecarium
* Fasciculins (green mamba toxins) (1, 2, 3, 4)
* Onchidal (Onchidella binneyi)
* Methanesulfonyl fluoride

* Unsorted: α-Pinene
* α-Viniferin
* Affinine
* Affinisine
* Arisugacin A
* Bulbocapnine
* Conodurine
* Coronaridine
* Corydaline
* Corynoline
* Crimidine
* Cyclanoline
* Cymserine
* Harmaline
* Kobophenol A
* Lactucopicrin
* Lycorine
* Phosacetim
* Rosmarinic acid
* Stercuronium iodide
* Taspine
* Tetrahydrocannabinol
* Ungeremine
* Ungiminorine
* Dimethylcarbamoyl fluoride
* BW284C51

* Reactivators: Asoxime chloride
* Methoxime
* Obidoxime
* Pralidoxime
* Trimedoxime bromide

BChE|

* Inhibitors: Affinine
* Affinisine
* Conodurine
* Cymserine
* Ladostigil
* Profenamine (ethopropazine)
* Rivastigmine
* Tacrine
* ZINC-12613047
* Many of the other AChE inhibitors listed above

Transporter
(modulators)|

| CHT|

* Inhibitors: Hemicholinium-3 (hemicholine)
* Triethylcholine

* Enhancers: Coluracetam

|

VAChT|

* Inhibitors: Vesamicol

Release
(modulators)|

| Inhibitors|

* SNAP-25 inactivators: Botulinum toxin (A, C, E)

* VAMP inactivators: Botulinum toxin (B, D, F, G)

* Others: [[Chemistry:BungaroBungarotoxins (Beta-Bungarotoxin|β-bungarotoxin]], γ-bungarotoxin)

|

Enhancers|

* LPHN agonists: α-Latrotoxin

* Others: Atracotoxins (e.g., robustoxin, versutoxin)
* Crotoxin

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Propoxur&oldid=3322989"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ChAT]: Choline acetyltransferase
*[AChE]: Acetylcholinesterase
*[BChE]: Butyrylcholinesterase
*[CHT]: Choline transporter
*[VAChT]: Vesicular acetylcholine transporter
*[SNAP-25]: Synaptosomal-associated protein 25
*[VAMP]: Vesicle-associated membrane protein
*[LPHN]: Latrophilin