Pirimiphos-methyl

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 InfoCard 100.045.011 Edit this at Wikidata
EC Number
  • 249-528-5
KEGG
UNII
UN number 3082 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 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
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 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).

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]

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.

Synthesis

Pirimiphos methyl is manufactured in a two-step process in which N,N-diethylguanidine is reacted with ethyl acetoacetate to form a pyrimidine ring and its hydroxy group is combined with dimethyl chlorothiophosphate to form the insecticide.[8]

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 (PDF), World Health Organization
  8. ^ Unger, Thomas A. (14 January 1997). Pesticide Synthesis Handbook. Elsevier Science. p. 561. ISBN 9780815514015.