Structure via PubChem · Public domain (PubChem)
dimpylate
Sign in to saveAlso known as Basudin, Diazide, O,O-Diethyl-O-2-isopropyl-4-methyl-6-pyrimidinyl-phosphorothioate, Spectracide, O,O-diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphate, O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphate, O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphate
Diazinon (IUPAC name: '''O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate, INN - Dimpylate'''), a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the
Chemical data
- Formula
- C12H21N2O3PS
- Molecular weight
- 304.35 g/mol
- IUPAC name
- diethoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-lambda5-phosphane
- SMILES
- CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C
- InChIKey
- FHIVAFMUCKRCQO-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 85.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2,575 papers- In Vitro Activity of Beauvericin against All Developmental Stages of Sarcoptes scabiei.Antimicrobial agents and chemotherapy · 2020
- Atypical ocular bobbing in acute organophosphate poisoning.Archives of neurology · 1986
- Diazinon poisoning.Quarterly medical review · 1978
- Percutaneous organophosphate poisoning.Southern medical journal · 1987
- Severe post-dipping dermatitis.The Veterinary record · 1995
via PubMed
Wikidata facts
- Mass
- 304.101
Show 10 more facts
- MCN code
- 2933.59.32
- canonical SMILES
- CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C
- chemical formula
- C₁₂H₂₁N₂O₃PS
- Commons category
- Diazinon
- NIOSH Pocket Guide ID
- 0181
- density
- 1.12
- flash point
- 180
- solubility
- 0.004
- vapor pressure
- 0.0001
- time-weighted average exposure limit
- 0.1
via Wikidata · CC0
~12 min read
Article
9 sectionsContents
- History
- Synthesis
- Metabolism and mechanism of action
- Removal of diazinon
- Toxicity and effects on animals
- Symptoms in humans
- Efficacy and side effects
- References
- External links
Diazinon (IUPAC name: '''O,O-Diethyl O-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl] phosphorothioate, INN - Dimpylate), a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.
Routes of contact for diazinon include breathing, consuming, or contact with skin. Negative health effects from contact with diazinon include epiphora, drool or rhinorrhea, loss of appetite, vomiting, intense coughing, abdominal pain, headaches or muscle stiffness. Some other physiological effects include pinpoint pupils, increased heart rate, seizures, or coma. While diazinon has many different health risks, the US Agency for Toxic Substances and Disease Registry has not categorized it as a carcinogen.