Dimethoate

Dimethoate
Names
	Preferred IUPAC name O,O-Dimethyl S-[2-(methylamino)-2-oxoethyl] phosphorodithioate
	Other names O,O-dimethyl S-methylcarbamoylmethyl phosphorodithioate; Phosphorodithioic acid, O,O-Dimethyl S-(2-(methylamino)-2-oxoethylyl)ester
Identifiers
CAS Number	60-51-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34714 ;
ChEMBL	ChEMBL993408 ;
ChemSpider	2973 ;
ECHA InfoCard	100.000.437
KEGG	C14326 ;
PubChem CID	3082;
UNII	W6U08B045O ;
CompTox Dashboard (EPA)	DTXSID7020479 ;
	InChI InChI=1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7) Key: MCWXGJITAZMZEV-UHFFFAOYSA-N ; InChI=1/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7) Key: MCWXGJITAZMZEV-UHFFFAOYAB;
	SMILES O=C(NC)CSP(=S)(OC)OC;
Properties
Chemical formula	C5H12NO3PS2
Molar mass	229.26 g/mol
Appearance	Grey-white crystalline solid
Density	1.3 g/cm3, solid
Melting point	43 to 45 °C (109 to 113 °F; 316 to 318 K)
Boiling point	117 °C (243 °F; 390 K) at 10 Pa
Solubility in water	2.5 g/100 ml
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
	GHS labelling:
Pictograms
Hazard statements	H302, H312
Precautionary statements	P280
Flash point	107 °C (225 °F; 380 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related organophosphates	malathion
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dimethoate is a widely used organophosphate insecticide and acaricide. It was patented and introduced in the 1950s by American Cyanamid. Like other organophosphates, dimethoate is an acetylcholinesterase inhibitor which disables cholinesterase, an enzyme essential for central nervous system function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly.^[2] One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.^[3]

^ ^a ^b ^c Sigma-Aldrich Co., Dimethoate.
^ Dauterman WC, Viado GB, Casida JE, O'brien RD (1960). "Insecticide Residues, Persistence of Dimethoate and Metabolites Following Foliar Application to Plants". Journal of Agricultural and Food Chemistry. 8 (2): 115–9. doi:10.1021/jf60108a013.
^ Cite error: The named reference :3 was invoked but never defined (see the help page).

[sigma-1] Sigma-Aldrich Co., Dimethoate.

[2] Dauterman WC, Viado GB, Casida JE, O'brien RD (1960). "Insecticide Residues, Persistence of Dimethoate and Metabolites Following Foliar Application to Plants". Journal of Agricultural and Food Chemistry. 8 (2): 115–9. doi:10.1021/jf60108a013.

[:3-3] Cite error: The named reference :3 was invoked but never defined (see the help page).

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