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-dimethyl phosphorothioate
Other names Pirimifos-methyl
Identifiers
CAS Number	29232-93-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	755726
ChEBI	CHEBI:38843 Y
ChemSpider	31773 Y
ECHA InfoCard	100.045.011
EC Number	249-528-5
KEGG	C18403 Y
PubChem CID	34526
UNII	2VQZ4PK548 Y
UN number	3082 2902
CompTox Dashboard (EPA)	DTXSID0024266
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

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.

External links

• Pirimiphos-methyl in the Pesticide Properties DataBase (PPDB)