Pirimiphos-methyl

Pirimiphos-methyl, marketed as Actellic,[1][2][3][4] and Sybol is a phosphorothioate used as an insecticide. It was originally developed by Imperial Chemical Industries Ltd., now Syngenta, at their Jealott's Hill site and first marketed in 1977, ten years after its discovery.[5][6]

Pirimiphos-methyl
Names
Preferred IUPAC name
O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-diethyl phosphorothioate
Other names
Pirimifos-methyl
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 755726
ChEBI
ChemSpider
ECHA InfoCard 100.045.011
EC Number
  • 249-528-5
KEGG
PubChem CID
UNII
UN number 3082 2902
InChI
  • 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 Y
    Key: QHOQHJPRIBSPCY-UHFFFAOYSA-N Y
  • 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
SMILES
  • CCN(CC)c1nc(C)cc(OP(=S)(OC)OC)n1
Properties
Chemical formula
 C11H20N3O3PS
Molar mass 305.33 g·mol−1
Appearance Straw-colored liquid
Density 1.147 g/mL (30 °C)
Melting point 15 to 18 °C (59 to 64 °F; 288 to 291 K)
Boiling point decomposes before boiling
Solubility in water
 5.0 mg/L (30 °C)
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H302, H410
Precautionary statements
 P264, P270, P273, P301+P312, P330, P391, P501
Flash point 46 °C (115 °F; 319 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Organophosphate insecticide with pirimiphos-methyl (no longer in production)

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

Pyrimiphos-ethyl is a related insecticide in which the methoxy groups are replaced with ethoxy groups.

References
  1. "Actellic50EC". www3.syngenta.com. Retrieved 2015-11-11.
  2. "Common Chemistry - Substance Details - 29232-93-7 : Phosphorothioic acid, O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]O,O-dimethyl ester". www.commonchemistry.org. Retrieved 2015-11-11.
  3. "Actellic 50 EC". www3.syngenta.com. Retrieved 2015-11-11.
  4. "ACTELLIC 50 EC: FIŞA CU DATE DE SECURITATE" (PDF) (in Romanian). Syngenta. 2013. Archived from the original (PDF) on 2016-09-10. Retrieved 2015-11-11.
  5. "Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre" (PDF). Archived from the original (PDF) on October 11, 2007. Retrieved June 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, World Health Organization


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