Pirimiphos-methyl explained

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. 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.[7]

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

Notes and References

  1. Web site: Actellic50EC. www3.syngenta.com. 2015-11-11.
  2. Web site: Common Chemistry - Substance Details - 29232-93-7 : Phosphorothioic acid, O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]O,O-dimethyl ester]. www.commonchemistry.org. 2015-11-11.
  3. Web site: Actellic 50 EC. www3.syngenta.com. 2015-11-11.
  4. Web site: ACTELLIC 50 EC: FIŞA CU DATE DE SECURITATE. 2013. 2015-11-11. Syngenta. ro . dead . https://web.archive.org/web/20160910175632/http://www3.syngenta.com/country/ro/SiteCollectionDocuments/Protectia%20Plantelor/Fise%20de%20siguranta/2015/Fi%C8%99a%20de%20securitate%20Actellic.pdf . 2016-09-10.
  5. Web site: Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre . June 26, 2012 . dead . https://web.archive.org/web/20071011084649/http://www.syngenta.com/en/downloads/75jealott_brochure.pdf . October 11, 2007 .
  6. Book: Snell, B.K. . Jealott's Hill: Fifty years of Agricultural Research 1928-1978 . F.C. . Peacock . etal . Chapter 11: Pyrimidine insecticides . 98–109 . Imperial Chemical Industries Ltd. . 1978 . 0901747017 .
  7. Book: 9780815514015 . Pesticide Synthesis Handbook . Unger . Thomas A. . 14 January 1997 . 561 . Elsevier Science .

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