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Details

Stereochemistry ACHIRAL
Molecular Formula C12H21N2O3PS
Molecular Weight 304.346
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMPYLATE

SMILES

CCOP(=S)(OCC)OC1=CC(C)=NC(=N1)C(C)C

InChI

InChIKey=FHIVAFMUCKRCQO-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C12H21N2O3PS
Molecular Weight 304.346
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Dimpylate (diazinon) is a nonsystemic organophosphate insecticide, an inhibitor of the enzyme acetylcholinesterase (AChE), which hydrolyzes the neurotransmitter acetylcholine (ACh) in cholinergic synapses and neuromuscular junctions. This results in abnormal accumulation of ACh in the nervous system. Dimpylate was first registered for use in the USA in 1956. It was developed as an insecticide, acaricide, and nematicide for use on a variety of pests for control of soil insects and pests of fruit, vegetables, and forage and field crops. It had been used extensively in home and garden applications, in formulations designed to prevent such pests as crickets or cockroaches from infesting homes or offices, and in pet collars. Due to the emerging health and ecological risks posed by diazinon, manufacturers agreed to phase out and cancel all residential products. Manufacturing of indoor use products containing dimpylatewas discontinued in 2001; manufacture of non-agricultural outdoor use products containing dimpylate was discontinued in 2003.

CNS Activity

Curator's Comment: Animal tissue studies and autopsy reports of human deaths from diazinon have shown that it is widely and rapidly distributed throughout the body. Rats exposed orally to 23 mg/kg diazinon had detectable levels of diazinon in the blood, adipose tissue, muscle, liver and brain.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1900.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Gross fluxes and estuarine behaviour of pesticides in the Scheldt estuary (1995-1997).
2001
Automated sampling of stormwater runoff in an urban watershed, north-central Texas.
2001
Agricultural use of organophosphate pesticides and the risk of non-Hodgkin's lymphoma among male farmers (United States).
2001 Aug
Influence of sebum and stratum corneum hydration on pesticide/herbicide collection efficiencies of the human hand.
2001 Aug
Joint acute toxicity of diazinon and ammonia to Ceriodaphnia dubia.
2001 Dec
Response of bobwhite quail and gray-tailed voles to granular and flowable diazinon applications.
2001 Feb
Effects of field exposure to diazinon on small mammals inhabiting a semienclosed prairie grassland ecosystem. I. Ecological and reproductive effects.
2001 Feb
Mechanistic aspects of organophosphorothionate toxicity in fish and humans.
2001 Jan
Effect of insulin resistance on serum paraoxonase activity in a nondiabetic population.
2001 Jul
Optimization of headspace solid-phase microextraction conditions for the determination of organophosphorus insecticides in natural waters.
2001 Jul 13
Inhibition and recovery of maternal and fetal cholinesterase enzyme activity following a single cutaneous dose of methyl parathion and diazinon, alone and in combination, in pregnant rats.
2001 Jul-Aug
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.
2001 Jun
Increasing uptake and bioactivation with development positively modulate diazinon toxicity in early life stage medaka (Oryzias latipes).
2001 Jun
New method for determination of ten pesticides in human blood.
2001 Mar-Apr
Determination of diazinon, chlorpyrifos, and their metabolites in rat plasma and urine by high-performance liquid chromatography.
2001 May
Considerations necessary in gathering occurrence data for selected unstable compounds in the USEPA Unregulated Contaminant Candidate List in USEPA Method 526.
2001 May 1
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
Evaluating environmental hazards of land applying composted diazinon using earthworm bioassays.
2001 Nov
Effect of diazinon on behavior of Japanese medaka (Oryzias latipes) and gene expression of tyrosine hydroxylase as a biomarker.
2001 Nov
A comparison of biomarker responses in the earthworm Aporrectodea caliginosa to the organophosphorus insecticides diazinon and chlorpyrifos.
2001 Nov
Estimation of cumulative exposure to organophosphate sheep dips in a study of chronic neurological health effects among United Kingdom sheep dippers.
2001 Nov
Diazinon is activated by CYP2C19 in human liver.
2001 Nov 15
Levels of persistent organic pollutants in several child day care centers.
2001 Nov-Dec
Toxicologic significance of the hyperglycemia caused by organophosphorous insecticides.
2001 Oct
Toxicity of cypermethrin and diazinon to Haematobia irritans (Diptera: Muscidae) in its American southern range.
2001 Oct 31
Developmental neurotoxicity of chlorpyrifos modeled in vitro: comparative effects of metabolites and other cholinesterase inhibitors on DNA synthesis in PC12 and C6 cells.
2001 Sep
Topical insecticide treatments to protect dogs from sand fly vectors of leishmaniasis.
2001 Sep-Oct
Pollutants in house dust as indicators of indoor contamination.
2002
Field studies on the susceptibility of housefly to certain insecticides in nine Egyptian governorates.
2002 Apr
Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks.
2002 Dec
Simple method for the determination of trace levels of pesticides in honeybees using matrix solid-phase dispersion and gas chromatography.
2002 Dec 27
Removal of organophosphate pesticides from wastewater by supercritical carbon dioxide extraction.
2002 Feb
Combined effects of lowered oxygen and toxicants (copper and diazinon) on the mayfly Ephoron virgo.
2002 Feb
Simple determination of 22 organophosphorous pesticides in human blood using headspace solid-phase microextraction and gas chromatography with mass spectrometric detection.
2002 Jan
Oxidation of organophosphorus pesticides for the sensitive detection by a cholinesterase-based biosensor.
2002 Jan
Concentration and loading of pesticide residues in Lake Biwa basin (Japan).
2002 Jan
Toxicity of stormwater runoff after dormant spray application of diazinon and esfenvalerate (Asana) in a French prune orchard, Glenn county, California, USA.
2002 Jan
Determination of insecticides in honey by matrix solid-phase dispersion and gas chromatography with nitrogen-phosphorus detection and mass spectrometric confirmation.
2002 Jan-Feb
Increased toxicity to invertebrates associated with a mixture of atrazine and organophosphate insecticides.
2002 Jul
Diazinon and its degradation products in agricultural water courses in British Columbia, Canada.
2002 Jul
Chronic diazinon exposure: pathologies of spleen, thymus, blood cells, and lymph nodes are modulated by dietary protein or lipid in the mouse.
2002 Mar 5
Residential pesticide use during pregnancy among a cohort of urban minority women.
2002 May
Interactions between pesticides and components of pesticide formulations in an in vitro neurotoxicity test.
2002 May 1
Ecological risk assessment of pesticide residues in coastal lagoons of Nicaragua.
2002 Oct
A multi-analyte method for the quantification of contemporary pesticides in human serum and plasma using high-resolution mass spectrometry.
2002 Oct 5
Prevalence of fetal exposure to environmental toxins as determined by meconium analysis.
2002 Sep
Histological examination of sublethal effects of diazinon on ovary of bluegill, Lepomis macrochirus.
2003
Biological targets of neurotoxic pesticides analysed by alteration of developmental events in the Mediterranean sea urchin, Paracentrotus lividus.
2003 Feb
Predicting children's short-term exposure to pesticides: results of a questionnaire screening approach.
2003 Jan
The effects of acute pesticide exposure on neuroblastoma cells chronically exposed to diazinon.
2003 Mar 14
Patents

Sample Use Guides

Dimpylate (diazinon) is a contact insecticide. It is administered by spraying the crops.
Route of Administration: Topical
The Ellman assay was used to test AchE inhibition activity. The assay is based on chromophores generated in situ after enzymatic cleavage of acetylthiocholine and the resulting thiocholine with Ellman’s reagent, DTNB (5,50-dithio-bis-2-nitrobenzoic acid). The plates were incubated at room temperature and the enzymatic activity was determined by spectrophotometric reading at 412 nm.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:44 GMT 2023
Record UNII
YUS1M1Q929
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMPYLATE
INN   MART.   WHO-DD  
INN  
Official Name English
DIETHYL 2-ISOPROPYL-4-METHYL-6-PYRIMIDYL THIONOPHOSPHATE
Common Name English
DIAZINON [ISO]
Common Name English
O,O-DIETHYL 2-ISOPROPYL-6-METHYL-4-PYRIMIDINYLPHOSPHOROTHIOATE
Systematic Name English
OPTIMIZER INSECTICIDE
Brand Name English
Dimpylate [WHO-DD]
Common Name English
dimpylate [INN]
Common Name English
DIAZINON [HSDB]
Common Name English
O,O-DIETHYL O-(6-METHYL-2-(1-METHYLETHYL)-4-PYRIMIDINYL) PHOSPHOROTHIOATE
Systematic Name English
DIAZINON [MI]
Common Name English
DIMPYLATE [MART.]
Common Name English
DIAZINON
HSDB   ISO   MI  
Systematic Name English
PHOSPHOROTHIOIC ACID O,O-DIETHYL O-(6-METHYL-2-(1-METHYLETHYL)-4-PYRIMIDINYL) ESTER
Systematic Name English
NSC-8938
Code English
NEW Z DIAZINON
Brand Name English
DIAZINON [IARC]
Common Name English
G-24480
Code English
Classification Tree Code System Code
WHO-VATC QP53AF03
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
EPA PESTICIDE CODE 57801
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
Code System Code Type Description
INN
2045
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PRIMARY
MESH
D003976
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PRIMARY
EPA CompTox
DTXSID9020407
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PRIMARY
CHEBI
34682
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PRIMARY
ALANWOOD
diazinon
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PRIMARY
WIKIPEDIA
DIAZINON
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
PUBCHEM
3017
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PRIMARY
HSDB
303
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PRIMARY
NSC
8938
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PRIMARY
CAS
333-41-5
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
EVMPD
SUB07189MIG
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PRIMARY
ECHA (EC/EINECS)
206-373-8
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PRIMARY
SMS_ID
100000082650
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
NCI_THESAURUS
C169912
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
FDA UNII
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
DAILYMED
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL388560
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY
MERCK INDEX
m4268
Created by admin on Fri Dec 15 15:10:44 GMT 2023 , Edited by admin on Fri Dec 15 15:10:44 GMT 2023
PRIMARY Merck Index
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