Acephate

Names
Preferred IUPAC name

Dimethyl N-acetylphosphoramidothioate

Identifiers

CAS Number

* 30560-19-1 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:34520 Y

ChEMBL |

* ChEMBL2133249 N

ChemSpider |

* 1905 Y

ECHA InfoCard | 100.045.659
KEGG |

* C14426 Y

PubChem CID

* 1982

RTECS number |

* TB4760000

UNII |

* 3Y417O444D Y

CompTox Dashboard (EPA)

* DTXSID8023846

InChI

* InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7) Y

Key: YASYVMFAVPKPKE-UHFFFAOYSA-N Y

* InChI=1/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)

Key: YASYVMFAVPKPKE-UHFFFAOYAG

SMILES

* O=C(NP(=O)(OC)SC)C

Properties

Chemical formula

| C4H10NO3PS
Molar mass | 183.16 g·mol−1
Appearance  | colourless to white solid
Density | 1.35 g/cm3
Melting point | 88–90 °C (190–194 °F; 361–363 K)

Solubility in water

| 79 g/100 mL
Solubility | very soluble in acetone
soluble in ethanol
Vapor pressure | 2x10−6 mmHg
Pharmacology
Legal status |

* AU: S6 (Poison)

Hazards
GHS labelling:[1]

Pictograms

Signal word

| Warning

Hazard statements

| H302

Precautionary statements

| P264, P270, P301+P312, P330, P501

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

Chemical compound

Acephate is an organophosphate foliar and soil insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended use rate. It is used primarily for control of aphids, including resistant species, in vegetables (e.g. potatoes, carrots, greenhouse tomatoes, and lettuce) and in horticulture (e.g. on roses and greenhouse ornamentals). It also controls leaf miners, caterpillars, sawflies, thrips, and spider mites in the previously stated crops as well as turf, and forestry. By direct application to mounds, it is effective in destroying imported fire ants.

Acephate is sold as a soluble powder, as emulsifiable concentrates, as pressurized aerosol, and in tree injection systems and granular formulations.

As of 2012, the EPA no longer allows the usage of acephate on green beans grown in the United States.[2]

## Toxicology

[edit]

It is considered non-phytotoxic on many crop plants. Acephate and its primary metabolite, methamidophos, are toxic to Heliothis spp. that are considered resistant to other organophosphate insecticides. Acephate emits toxic fumes of various oxides of phosphorus, nitrogen, and sulfur when heated to decomposition. Symptoms of exposure to acephate include a slight irritation of eyes and skin.

The U.S. annually uses 4–5 million pounds of acephate.[3]

The EU classifies Acephate as an Annex III substance, meaning that it meets the requirements to be considered a health and environmental hazard. [4]

## References

[edit]

1. ^ "Acephate". PubChem. Archived from the original on 2021-03-07. Retrieved 2021-03-17.
2. ^ "Food and Pesticides". 21 February 2013. Archived from the original on 28 May 2023. Retrieved 28 May 2023.
3. ^ "Acephate Facts" (PDF). Retrieved 2024-07-03.
4. ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2023-10-31.

* U.S. EPA Office of Pesticide Programs.
* Extension Toxicology Network. Pesticide Information Profiles.
* Cooperative Extension Offices of Cornell University, Oregon State University, the University of Idaho, and the University of California at Davis.
* Institute for Environmental Toxicology, Michigan State University.

## External links

[edit]

* Acephate General Fact Sheet - National Pesticide Information Center
* Acephate Pesticide Information Profile - Extension Toxicology Network
* EPA Acephate Reregistration Eligibility Decision
* Acephate in the Pesticide Properties DataBase (PPDB)

* v
* t
* e

Pest control: Insecticides

Carbamates|

* Aldicarb
* Aminocarb
* Bendiocarb
* Butocarboxim
* Carbaryl
* Carbofuran
* Carbosulfan
* m-Cumenyl methylcarbamate
* Ethienocarb
* Fenobucarb
* Isoprocarb
* Methomyl
* Metolcarb
* Oxamyl
* Promecarb
* 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 (Bistrifluron, Diflubenzuron, Flufenoxuron, Lufenuron, Noviflumuron)
* Hydroprene
* Methoprene
* Pyriproxyfen

Neonicotinoids|

* Acetamiprid
* Clothianidin
* Dinotefuran
* Imidacloprid
* Imidaclothiz
* Nitenpyram
* Nithiazine
* Paichongding
* 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
* DFDT
* 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
* R-16661
* Schradan
* Temefos
* Tebupirimfos
* Terbufos
* Tetrachlorvinphos
* Tribufos
* Trichlorfon

Pyrethroids|

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

Diamides|

* Chlorantraniliprole
* Cyantraniliprole
* Flubendiamide

Other chemicals|

* Afoxolaner
* Amitraz
* Azadirachtin
* Bensultap
* Buprofezin
* Cartap
* Chlordimeform
* Chlorfenapyr
* Cyromazine
* Fenazaquin
* Fenoxycarb
* Fipronil
* Fluralaner
* Hydramethylnon
* Indoxacarb
* Limonene
* Lotilaner (+milbemycin oxime)
* Pyridaben
* Pyriprole
* Sarolaner
* Adjuvants (Piperonyl butoxide, Sesamex)
* Spinosad
* Sulfluramid
* Tebufenozide
* Tebufenpyrad
* Veracevine
* Xanthone
* Metaflumizone
* Ryanodine
* Ryanodol

Metabolites|

* Oxon
* Malaoxon
* Paraoxon
* TCPy

Biopesticides|

* Bacillus thuringiensis
* Baculovirus
* Beauveria bassiana
* Beauveria brongniartii
* Isaria fumosorosea
* Metarhizium acridum
* Metarhizium anisopliae
* Nomuraea rileyi
* Lecanicillium lecanii
* Paenibacillus popilliae
* Purpureocillium lilacinum
* Spinosad

* v
* t
* e

Acetylcholine metabolism and transport modulators

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|

* 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
* Promecarb
* Propamocarb
* Propham
* Propoxur
* Thiodicarb
* Thiofanox; Stigmines: Distigmine
* Eptastigmine
* Ganstigmine
* Neostigmine +glycopyrronium bromide
* Phenserine
* Physostigmine
* Pyridostigmine
* Quilostigmine
* Rivastigmine
* Terestigmine; Others: Acotiamide
* Ambenonium
* Caffeine
* Donepezil
* EA-3990
* EA-4056
* Edrophonium
* Galantamine
* Huperzine A
* Huprine W
* Huprine X
* Huprine Y
* Ipidacrine
* Itopride
* Ladostigil
* Minaprine
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* T-1123
* T-1152
* T-1194
* TL-599
* TL-1238
* Tacrine
* Zanapezil

* Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Acephate
* 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
* Dicyclohexyl phosphorofluoridate
* Diisopropylphosphate
* Diisopropyl fluorophosphate
* 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
* EPN
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fluorotabun
* Fonofos
* Formothion
* Fosthiazate
* GD-42
* GH
* GT-45
* GV
* Guanitoxin
* Hexaethyl tetraphosphate (HETP)
* Isofluorophate
* Isoxathion
* Leptophos
* Malaoxon
* Malathion
* Mazidox
* Methamidophos
* Methidathion
* Methyl phenkapton
* Methylfluorophosphonylcholine (MFPCh)
* Metrifonate
* Mevinphos
* Mipafox
* Monocrotophos
* MSPI
* Naled
* Novichok agent
* Omethoate
* Oxydemeton-methyl
* Paraoxon
* Parathion
* Parathion-methyl
* Phorate
* Phosalone
* Phosfolan
* Phosmet
* Phosphamidon
* Phoxim
* Pirimiphos-methyl
* Profenofos
* Prothoate
* R-16661
* 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
* Ronnel
* Sarin (GB)
* Schradan
* Soman (GD)
* Sulfotep (TEDP)
* Tabun (GA)
* Tebupirimfos
* Temefos
* Terbufos
* Tetrachlorvinphos
* Tetraethyl pyrophosphate (TEPP)
* 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
* TMTFA
* 3152 CT

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

BChETooltip Butyrylcholinesterase|

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

Transporter
(modulators)|

| CHTTooltip Choline transporter|

* Inhibitors: Hemicholinium-3 (hemicholine)
* Triethylcholine

* Enhancers: Coluracetam

|

VAChTTooltip Vesicular acetylcholine transporter|

* Inhibitors: Vesamicol

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)

* Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)

|

Enhancers|

* LPHNTooltip Latrophilin agonists: α-Latrotoxin

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

See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[AU]: Australia
*[H302]: H302: Harmful if swallowed
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P330]: P330: Rinse mouth.
*[P501]: P501: Dispose of contents/container to ...
*[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