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Pirimiphos-methyl

From Wikipedia, the free encyclopedia
Pirimiphos-methyl
Names
Preferred IUPAC name
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl]O,O-dimethyl phosphorothioate
Other names
Pirimifos-methyl
Identifiers
3D model (JSmol)
755726
ChEBI
ChemSpider
ECHA InfoCard100.045.011Edit this at Wikidata
EC Number
  • 249-528-5
KEGG
UNII
UN number3082 2902
  • InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3 checkY
    Key: QHOQHJPRIBSPCY-UHFFFAOYSA-N checkY
  • InChI=1/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3
    Key: QHOQHJPRIBSPCY-UHFFFAOYAW
  • CCN(CC)c1nc(C)cc(OP(=S)(OC)OC)n1
Properties
C11H20N3O3PS
Molar mass305.33 g·mol−1
AppearanceStraw-colored liquid
Density1.147 g/mL (30 °C)
Melting point15 to 18 °C (59 to 64 °F; 288 to 291 K)
Boiling pointdecomposes before boiling
5.0 mg/L (30 °C)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302,H410
P264,P270,P273,P301+P312,P330,P391,P501
Flash point46 °C (115 °F; 319 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Pirimiphos-methyl, marketed as Actellic[1][2][3][4] and Sybol, is aphosphorothioate used as aninsecticide. It was originally developed byImperial Chemical Industries Ltd., nowSyngenta, at theirJealott's Hill site and first marketed in 1977, ten years after its discovery.[5][6]

This is one of several compounds used for vector control ofTriatoma. These insects are implicated in the transmission ofChagas disease in the Americas.[7] Pirimiphos-methyl can be applied as an interior surface paint additive, in order to achieve a residual pesticide effect.

Synthesis

[edit]

Pirimiphos methyl is manufactured in a two-step process in whichN,N-diethylguanidine is reacted withethyl acetoacetate to form apyrimidine ring and itshydroxy group is combined withdimethyl chlorothiophosphate to form the insecticide.[8]

Pyrimiphos-ethyl is a related insecticide in which themethoxy groups are replaced withethoxy groups.

References

[edit]
  1. ^"Actellic50EC".www3.syngenta.com. Retrieved2015-11-11.
  2. ^"Common Chemistry - Substance Details - 29232-93-7 : Phosphorothioic acid, O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]O,O-dimethyl ester".www.commonchemistry.org. Retrieved2015-11-11.
  3. ^"Actellic 50 EC".www3.syngenta.com. Retrieved2015-11-11.
  4. ^"ACTELLIC 50 EC: FIŞA CU DATE DE SECURITATE"(PDF) (in Romanian). Syngenta. 2013. Archived fromthe original(PDF) on 2016-09-10. Retrieved2015-11-11.
  5. ^"Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre"(PDF). Archived fromthe original(PDF) on October 11, 2007. RetrievedJune 26, 2012.
  6. ^Snell, B.K.; et al. (1978). "Chapter 11: Pyrimidine insecticides". In Peacock, F.C. (ed.).Jealott's Hill: Fifty years of Agricultural Research 1928-1978. Imperial Chemical Industries Ltd. pp. 98–109.ISBN 0901747017.
  7. ^"Chapter 3: Triatomine bugs",Vectors of Chagas Disease(PDF), World Health Organization
  8. ^Unger, Thomas A. (14 January 1997).Pesticide Synthesis Handbook. Elsevier Science. p. 561.ISBN 9780815514015.

External links

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Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
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Enzyme
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ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
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CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
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