ContaminantDB: Diazinon

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-03-27 02:15:30 UTC

Accession Number

CHEM000052

Identification

Common Name

Diazinon

Class

Small Molecule

Description

Nonsystemic insecticide for rice and fruit trees. Cholinesterase inhibitor. Diazinon is used against animal ectoparasites Diazinon has been shown to exhibit apoptotic and antibiotic functions (1, 2).

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2A
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Household Toxin
Insecticide
Metabolite
Organic Compound
Organophosphate
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dimpylate	ChEBI
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphate	ChEBI
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphate	ChEBI
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioate	ChEBI
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphate	ChEBI
Phosphorothioic acid, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) ester	ChEBI
New Z diazinon	Kegg
Optimizer insecticide	Kegg
Dimpylic acid	Generator
O,O-Diethyl 2-isopropyl-4-methylpyrimidyl-6-thiophosphoric acid	Generator
O,O-Diethyl O-(2-isopropyl-4-methyl-6-pyrimidyl) thionophosphoric acid	Generator
O,O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioic acid	Generator
O,O-Diethyl O-[6-methyl-2-(1-methylethyl)pyrimidin-4-yl] thiophosphoric acid	Generator
Phosphorothioate, O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) ester	Generator
Bazudine	MeSH
Neocidol	MeSH
Neotsidol	MeSH
Agridin 60	HMDB
Alfa-tox	HMDB
Antigal	HMDB
Antlak	HMDB
Bassadinon	HMDB
Basudin	HMDB
Bazuden	HMDB
Bazudin	HMDB
Ciazinon	HMDB
Compass	HMDB
Dacutox	HMDB
Dassitox	HMDB
Dazzel	HMDB
Delzinon	HMDB
Diagran	HMDB
Dianon	HMDB
Diazide	HMDB
Diazinone	HMDB
Diazitol	HMDB
Diazol	HMDB
Dicid	HMDB
Diethyl 2-isopropyl-4-methyl-6-pyrimidyl thionophosphate	HMDB
Diethyl dimpylatum	HMDB
Dimpylate, inn	HMDB
Dipofene	HMDB
Disonex	HMDB
Dizictol	HMDB
Diziktol	HMDB
Dizinil	HMDB
Dizinon	HMDB
Drawizon	HMDB
Dyzol	HMDB
Ektoband	HMDB
Exodin	HMDB
Fezudin	HMDB
Flytrol	HMDB
Galesan	HMDB
Gardentox	HMDB
Isopropylmethylpyrimidyl diethyl thiophosphate	HMDB
Kayazinon	HMDB
Kayazol	HMDB
Knox-out	HMDB
Meodinon	HMDB
Nedcidol	HMDB
Neodinon	HMDB
Nipsan	HMDB
Nucidol	HMDB
Oleodiazinon	HMDB
Optimizer	HMDB
Root guard	HMDB
Sarolex	HMDB
Spectracide	HMDB
Spertacide	HMDB
Srolex	HMDB
Terminator	HMDB

Chemical Formula

C₁₂H₂₁N₂O₃PS

Average Molecular Mass

304.346 g/mol

Monoisotopic Mass

304.101 g/mol

CAS Registry Number

333-41-5

IUPAC Name

O,O-diethyl O-6-methyl-2-(propan-2-yl)pyrimidin-4-yl phosphorothioate

Traditional Name

diazinon

SMILES

CCOP(=S)(OCC)OC1=NC(=NC(C)=C1)C(C)C

InChI Identifier

InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3

InChI Key

FHIVAFMUCKRCQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Pyrimidinyl phosphorothioates

Alternative Parents

Substituents

Pyrimidinyl phosphorothioate
Thiophosphate triester
Pyrimidine
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidines (CHEBI:34682 )
organic thiophosphate (CHEBI:34682 )
Organophosphorus insecticides (C14324 )
a small molecule (CPD-8965 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Liquid

Appearance

Colorless oil (pure) or pale to dark brown liquid (technical).

Experimental Properties

Property	Value
Melting Point	< 25°C
Boiling Point	Not Available
Solubility	0.04 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	4.45	ALOGPS
logP	4.19	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	4.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.47 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	80.76 m³·mol⁻¹	ChemAxon
Polarizability	31.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-3931000000-a70584cb463b92093849	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-3931000000-a70584cb463b92093849	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-2390000000-64dc2c6900828222f0d0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0009000000-d239df985b8529964c59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ldi-0915000000-ced91e8448a6f8b1969d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0900000000-48faf44580abfbba15e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0900000000-109fa8436bb829f5f481	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0900000000-49a403503b8e1237dddc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0900000000-373a091bd4e337f273ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0009000000-25cf20e874bc51155b11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0pvi-0905000000-89807ca393822677be3e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0900000000-95716b221cd9e83e7d05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-1900000000-3772ba2a27f51803e58a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0uxs-4900000000-ce1c6d19b36209036e3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0w2a-6900000000-8011c485731c42bd49f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0009000000-e92acd83cf908233bd11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0aor-0905000000-54dc7dc28ca7ec93789e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0900000000-cf4033176e3d7c36c589	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-1900000000-cb95f2a89d6871b4c0f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0uxs-3900000000-8d43918e6bdf5a791827	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0w2a-7900000000-37289512a80be0d06b70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0900000000-c242d24704a15f911a56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2398000000-292315df845ad237142a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002k-2490000000-b8c16809eaddcd92f2fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ko-9410000000-169637cf10237dcb2a0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ufr-0694000000-cdcbf19ad7bf249fbdb6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fs-0890000000-0b16a5fb1c0467d0de87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-0980000000-0e6aa8e81cb45755aac9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fbi-7920000000-dce70eb9e413a5f2e1a2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

Diazinon is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

LD50: 66 mg/kg (Oral, Rat) (9) LD50: 180 mg/kg (Dermal, Rat) (9) LD50: 65 mg/kg (Intraperitoneal, Rat) (9) LD50: 58 mg/kg (Subcutaneous, Mouse) (9) LD50: 180 mg/kg (Intravenous, Mouse) (9)

Lethal Dose

25 g for an adult human. (8)

Carcinogenicity (IARC Classification)

Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (4)

Uses/Sources

Diazinon is used as an insecticide in agriculture, mainly on fruit and vegetable field crops. (5)

Minimum Risk Level

Intermediate Inhalation: 0.01 mg/m3 (3) Acute Oral: 0.006 mg/kg/day (3) Intermediate Oral: 0.002 mg/kg/day (3) Chronic Oral: 0.0007 mg/kg/day (3)

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

The symptoms associated with diazinon poisoning in humans include weakness, headaches, tightness in the chest, blurred vision, nonreactive pinpoint pupils, excessive salivation, difficulty breathing, sweating, nausea, vomiting, diarrhea, abdominal cramps, and slurred speech. (6)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0032943

FooDB ID

FDB010928

Phenol Explorer ID

Not Available

KNApSAcK ID