Structure via PubChem · Public domain (PubChem)
pirimiphos-methyl
Sign in to saveAlso known as Actellic, O-[2-(diethylamino)-6-methylpyrimidin-4-yl] O,O-dimethyl thiophosphate, Pirimifosmethyl, Pirimiphos methyl, Pyrimiphos methyl, Pirimiphosmethyl
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.
Chemical data
- Formula
- C11H20N3O3PS
- Molecular weight
- 305.34 g/mol
- IUPAC name
- 4-dimethoxyphosphinothioyloxy-N,N-diethyl-6-methylpyrimidin-2-amine
- SMILES
- CCN(CC)C1=NC(=CC(=N1)OP(=S)(OC)OC)C
- InChIKey
- QHOQHJPRIBSPCY-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 88.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
638 papers- Effects of Pirimiphos-Methyl on Non-Target Invertebrates.Biology · 2024
- DETERMINING A DIAGNOSTIC DOSE OF PIRIMIPHOS-METHYL FOR AEDES AEGYPTI USING TREATED BOTTLES1.Journal of the American Mosquito Control Association · 2024
- Being exposed to low concentrations of pirimiphos-methyl and chlorfenapyr has detrimental effects on the mobility of Trogoderma granarium.Pest management science · 2023
- Efficacy of deltamethrin and pirimiphos-methyl in proportionally layer-treated maize against the larger grain borer and the maize weevil.Journal of economic entomology · 2023
- Detection of Pirimiphos-Methyl in Wheat Using Surface-Enhanced Raman Spectroscopy and Chemometric Methods.Molecules (Basel, Switzerland) · 2019
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 305.096
- Has use
- insecticide
Show 3 more facts
- chemical formula
- C₁₁H₂₀N₃O₃PS
- canonical SMILES
- CCN(CC)C1=NC(=CC(=N1)OP(=S)(OC)OC)C
- Commons category
- Pirimiphos-methyl
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- References
- External links
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. 500px Pyrimiphos-ethyl is a related insecticide in which the methoxy groups are replaced with ethoxy groups.
Excerpted from Wikipedia’s “pirimiphos-methyl” article, available under the CC BY-SA 4.0 licence.