Dimethoate

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]

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34714^Y
ChEMBL	ChEMBL993408^N
ChemSpider	2973^Y
ECHA InfoCard	100.000.437
KEGG	C14326^Y
PubChem CID	3082
UNII	W6U08B045O^Y
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)^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/cm^3, 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

Fruit Fly Control Efforts

The Queensland fruit fly, or Bactrocera Tyroni, is a tephritid fly species that has caused more than $28.5 million a year in damage to Australian fruit crops. In order to combat infestation, farmers treated crops with dimethoate and fenthion. However, the use of these chemicals was banned in 2011 due to safety concerns.[3]

Trade names

• Rogor [4][5]

References

1. Sigma-Aldrich Co., Dimethoate. Retrieved on 2013-07-20.
2. 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): 115–9. doi:10.1021/jf60108a013.
3. Lloyd, Annice C.; Hamacek, Edward L.; Kopittke, Rosemary A.; Peek, Thelma; Wyatt, Pauline M.; Neale, Christine J.; Eelkema, Marianne; Gu, Hainan (May 2010). "Area-wide management of fruit flies (Diptera: Tephritidae) in the Central Burnett district of Queensland, Australia". Crop Protection. 29 (5): 462–469. doi:10.1016/j.cropro.2009.11.003. ISSN 0261-2194.
4. Padmasheela, N. C.; Delvi, M. R. (2004). "Effect of Dimethoate (Rogor 30% EC) on the brain neurosecretory cells of third instar grubs of Oryctes rhinoceros L. (Coleoptera : Scarabaeidae)". Journal of Environmental Biology. 25 (4): 451–5. PMID 15907075.
5. https://www.ravensdown.co.nz/products/agrochemicals/rogor%5B%5D

External links

• EPA Report on Dimethoate(dead link)