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Pirimiphos-methyl

Pirimiphos-methyl, marketed as Actellic 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.

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. 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. :[[File:Pirimiphos-methyl synthesis.svg|500px]] Pyrimiphos-ethyl is a related insecticide in which the methoxy groups are replaced with ethoxy groups.

References

References

  1. "Actellic50EC".
  2. "Common Chemistry - Substance Details - 29232-93-7 : Phosphorothioic acid, O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]O,O-dimethyl ester".
  3. "Actellic 50 EC".
  4. (2013). "ACTELLIC 50 EC: FIŞA CU DATE DE SECURITATE". Syngenta.
  5. "Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre".
  6. Snell, B.K.. (1978). "Jealott's Hill: Fifty years of Agricultural Research 1928-1978". Imperial Chemical Industries Ltd..
  7. "Vectors of Chagas Disease". World Health Organization.
  8. (14 January 1997). "Pesticide Synthesis Handbook". Elsevier Science.
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acetylcholinesterase-inhibitors organothiophosphate-esters pesticides aminopyrimidines diethylamino-compounds methoxy-compounds
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