pirimiphos-methyl

{{chembox

| ImageFile = Pirimiphos-methyl.svg

| PIN = O-[2-(Diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl phosphorothioate

| OtherNames = Pirimifos-methyl

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 29232-93-7

| Beilstein = 755726

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 38843

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 31773

| EC_number = 249-528-5

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C18403

| PubChem = 34526

| UNNumber = 3082 2902

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2VQZ4PK548

| SMILES = CCN(CC)c1nc(C)cc(OP(=S)(OC)OC)n1

| 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

| InChIKey = QHOQHJPRIBSPCY-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QHOQHJPRIBSPCY-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=11 | H=20 | N=3 | O=3 | P=1 | S=1

| Appearance = Straw-colored liquid

| Density = 1.147 g/mL (30 °C)

| MeltingPtC = 15 to 18

| MeltingPt_notes =

| BoilingPt = decomposes before boiling

| Solubility = 5.0 mg/L (30 °C)}}

|Section3={{Chembox Hazards

| MainHazards =

| GHSPictograms = {{GHS07}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|410}}

| PPhrases = {{P-phrases|264|270|273|301+312|330|391|501}}

| FlashPtC = 46

| AutoignitionPtC =

}}

}}

Pirimiphos-methyl, marketed as Actellic{{Cite web|title = Actellic50EC|url = http://www3.syngenta.com/country/uk/en/ProductGuide/Pages/Actellic50EC.aspx|website = www3.syngenta.com|access-date = 2015-11-11}}{{Cite web|title = Common Chemistry - Substance Details - 29232-93-7 : Phosphorothioic acid, O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]O,O-dimethyl ester|url = http://www.commonchemistry.org/ChemicalDetail.aspx?ref=29232-93-7|website = www.commonchemistry.org|access-date = 2015-11-11}}{{Cite web|title = Actellic 50 EC|url = http://www3.syngenta.com/country/ro/ro/produse/Pages/Actellic.aspx|website = www3.syngenta.com|access-date = 2015-11-11}}{{Cite web|url = http://www3.syngenta.com/country/ro/SiteCollectionDocuments/Protectia%20Plantelor/Fise%20de%20siguranta/2015/Fi%C8%99a%20de%20securitate%20Actellic.pdf|title = ACTELLIC 50 EC: FIŞA CU DATE DE SECURITATE|date = 2013|access-date = 2015-11-11|publisher = Syngenta|language=ro |url-status=dead |archive-url=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 |archive-date=2016-09-10}} 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.{{cite web |url=http://www2.syngenta.com/en/downloads/75jealott_brochure.pdf |title=Syngenta: Celebrating 75 years of scientific excellence at Jealott's Hill International Research Centre |access-date=June 26, 2012 |url-status=dead |archive-url=https://web.archive.org/web/20071011084649/http://www.syngenta.com/en/downloads/75jealott_brochure.pdf |archive-date=October 11, 2007 }}{{Cite book |title=Jealott's Hill: Fifty years of Agricultural Research 1928-1978 |editor-first=F.C. |editor-last1=Peacock |last=Snell |first=B.K. |display-authors=etal |chapter=Chapter 11: Pyrimidine insecticides |pages=98–109 |publisher=Imperial Chemical Industries Ltd. |year=1978 |isbn=0901747017 |url=https://archive.org/details/jealottshillfift0000peac/page/1 }}

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.{{citation | url = https://www.who.int/water_sanitation_health/resources/vector210to222.pdf | chapter = Chapter 3: Triatomine bugs | title = Vectors of Chagas Disease | publisher = World Health Organization }} 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.{{cite book |isbn=9780815514015 |title=Pesticide Synthesis Handbook |last1=Unger |first1=Thomas A. |date=14 January 1997 |page=561 |publisher=Elsevier Science |url=https://books.google.com/books?id=-9cHDi8OOO4C&q=pirimiphos }}

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

References

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