Dimethoate

Dimethoate
Names
	IUPAC name O,O-dimethyl S-[2-(methylamino)-2-oxoethyl] dithiophosphate
	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
ChEBI	CHEBI:34714
ChEMBL	ChEMBL993408
ChemSpider	2973
Jmol interactive 3D	Image
KEGG	C14326
PubChem	3082
UNII	W6U08B045O
	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
Main hazards	Highly toxic
Safety data sheet	External MSDS
GHS pictograms
GHS hazard statements	H302 - H312
GHS precautionary statements	P280
Flash point	107 °C (225 °F; 380 K)
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, but is degraded relatively rapidly.^[2]

References[edit]

^ ^a ^b ^c Sigma-Aldrich Co., Dimethoate. Retrieved on 2013-07-20.
^ Dauterman, W. C.; Viado, G. B.; Casida, J. E.; O'Brien, R. D. (1960). "Insecticide Residues, Persistence of Dimethoate and Metabolites Following Foliar Application to Plants". Journal of Agricultural and Food Chemistry 8 (2): 115. doi:10.1021/jf60108a013.

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Names

IUPAC name O,O-dimethyl S-[2-(methylamino)-2-oxoethyl] dithiophosphate
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^Y
ChEBI	CHEBI:34714^Y
ChEMBL	ChEMBL993408^N
ChemSpider	2973^Y
Jmol interactive 3D	Image
KEGG	C14326^Y
PubChem	3082
UNII	W6U08B045O^Y
InChI InChI=1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7)^Y Key: MCWXGJITAZMZEV-UHFFFAOYSA-N^Y 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
Main hazards	Highly toxic
Safety data sheet	External MSDS
GHS pictograms	^[1]
GHS hazard statements	H302 - H312^[1]
GHS precautionary statements	P280^[1]
Flash point	107 °C (225 °F; 380 K)
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).
N verify (what is ^YN ?)
Infobox references