Temefos

Names
Preferred IUPAC name

O-[4-({4-[(Dimethoxyphosphorothioyl)oxy]phenyl}sulfanyl)phenyl] O,O-dimethyl phosphorothioate

Other names

[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-
dimethoxy-sulfanylidene-phosphorane

Identifiers

CAS Number

* 3383-96-8 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:38954 Y

ChEMBL |

* ChEMBL1355821 N

ChemSpider |

* 5199 Y

KEGG |

* D06062 Y

MeSH | Temefos

PubChem CID

* 5392

UNII |

* ONP3ME32DL Y

InChI

* InChI=1S/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3 Y

Key: WWJZWCUNLNYYAU-UHFFFAOYSA-N Y

* InChI=1/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3

Key: WWJZWCUNLNYYAU-UHFFFAOYAC

SMILES

* S=P(OC)(OC)Oc2ccc(Sc1ccc(OP(=S)(OC)OC)cc1)cc2

Properties

Chemical formula

| C16H20O6P2S3
Molar mass | 466.46 g·mol−1
Appearance  | white, crystalline solid[1]
Density | 1.32 g cm−3
Melting point |  30 °C (86 °F; 303 K)
Boiling point |  120–125[1] °C (248–257 °F; 393–398 K) (decomposes)

Solubility in water

| insoluble[1]
Vapor pressure | 0.00000007 mmHg (20°C)[1]
Hazards
NIOSH (US health exposure limits):

PEL (Permissible)

| 15 mg/m3[1]

REL (Recommended)

| TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[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

Temefos or temephos (trade name Abate) is an organophosphate larvicide used to treat water infested with disease-carrying insects[2] including mosquitoes, midges, and black fly larvae.

As with other organophosphates, temephos affects the central nervous system through inhibition of cholinesterase. In larvae, this results in death before reaching the adult stage.

In the developing world where the vector-borne disease dengue fever is endemic, temephos is widely used and applied by both private and public pest control in areas of standing water where the Aedes aegypti mosquito breeds in order to reduce the population of this disease-carrying insect.[3] Temephos is also used in the Guinea worm eradication program to kill water fleas that carry guinea worm larvae.

Resistance to temephos by A. aegypti has been seen in Brazil . The Brazilian Aedes aegypti resistance monitoring program detected temephos resistance in A. aegypti populations from several localities in the country in 1999 (Funasa 2000, Lima et al. 2003). In 1999, mosquitoes from the city of Rio de Janeiro were already resistant to temephos.[4]

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 NIOSH Pocket Guide to Chemical Hazards. "#0589". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0589.html.
2. ↑ Abate Product Information
3. ↑ New York Times article covering its application in Africa
4. ↑ "Resistance of Aedes aegypti to organophosphates in several municipalities in the State of Rio de Janeiro and Espírito Santo, Brazil". Am. J. Trop. Med. Hyg. 68 (3): 329–33. 2003. PMID 12685640.

## External links

* NIOSH Pocket Guide to Chemical Hazards
* International Chemical Safety Cards
* Official product site
* Temefos in the Pesticide Properties DataBase (PPDB)

## Bibliography

* Dejous C & Elouard J.M (1977) Action de l'abate sur les invertébérs aquatiques ; cinétique de décrochement à court et moyen terme (in French).

* 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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Original source: https://en.wikipedia.org/wiki/Temefos. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Temefos&oldid=3181420"
*[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