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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
Predicting insecticide resistance: mutagenesis, selection and response.
1998 Oct 29
Gross fluxes and estuarine behaviour of pesticides in the Scheldt estuary (1995-1997).
2001
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
Effect of insulin resistance on serum paraoxonase activity in a nondiabetic population.
2001 Jul
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
2001 May 15
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
Topical insecticide treatments to protect dogs from sand fly vectors of leishmaniasis.
2001 Sep-Oct
Pattern recognition of the movement tracks of medaka (Oryzias latipes) in response to sub-lethal treatments of an insecticide by using artificial neural networks.
2002
Sorption behaviour of acetochlor, atrazine, carbendazim, diazinon, imidacloprid and isoproturon on Hungarian agricultural soil.
2002 Aug
Vitamin C and E intake is associated with increased paraoxonase activity.
2002 Aug 1
Exposure to the organophosphate diazinon: data from a human volunteer study with oral and dermal doses.
2002 Aug 5
Biological monitoring of exposure to organophosphate pesticides.
2002 Aug 5
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
Size exclusion chromatographic cleanup for GC/MS determination of organophosphorus pesticide residues in household and vehicle dust.
2002 Jan-Feb
Oxidation of diazinon by anodic Fenton treatment.
2002 Jul
Herbicide and insecticide loadings from the Susquehanna River to the northern Chesapeake Bay.
2002 Jul 17
Paraoxonase (PON1) polymorphisms in farmers attributing ill health to sheep dip.
2002 Mar 2
Human blood and environmental media screening method for pesticides and polychlorinated biphenyl compounds using liquid extraction and gas chromatography-mass spectrometry analysis.
2002 Mar 25
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
Identification of alternatives for the management of foliar nematodes in floriculture.
2002 May
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:10:44 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
EPA PESTICIDE CODE 57801
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
Code System Code Type Description
INN
2045
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PRIMARY
MESH
D003976
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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 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
PUBCHEM
3017
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PRIMARY
HSDB
303
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PRIMARY
NSC
8938
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
CAS
333-41-5
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
EVMPD
SUB07189MIG
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-373-8
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
SMS_ID
100000082650
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
NCI_THESAURUS
C169912
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
FDA UNII
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
DAILYMED
YUS1M1Q929
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL388560
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY
MERCK INDEX
m4268
Created by admin on Fri Dec 15 15:10:44 UTC 2023 , Edited by admin on Fri Dec 15 15:10:44 UTC 2023
PRIMARY Merck Index
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ACTIVE MOIETY