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Details

Stereochemistry ACHIRAL
Molecular Formula C12H21N2O3PS
Molecular Weight 304.3471
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMPYLATE

SMILES

CCOP(=S)(OCC)Oc1cc(C)nc(C(C)C)n1

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 304.3471
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 nM [IC50]
PubMed

PubMed

TitleDatePubMed
MCE activities and malathion resistances in field populations of the australian sheep blowfly (Lucilia cuprina).
2000 Jan
[Evaluation of the effect of Knox-Out microencapsulated V.O. 240 and K-othrine powder on rat lice in two villages in the Betafo region].
2001
Exposure of California quail to organophosphorus insecticides in apple orchards in the Okanagan Valley, British Columbia.
2001 Apr
Impact of four insecticides on Japanese beetle (Coleoptera: Scarabaeidae) egg predators and white grubs in turfgrass.
2001 Feb
On predicting multi-route and multimedia residential exposure to chlorpyrifos and diazinon.
2001 Jan-Feb
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
Topical application as a method for comparing the effectiveness of insecticides against cat flea (Siphonaptera: Pulicidae).
2001 Mar
Evaluating environmental hazards of land applying composted diazinon using earthworm bioassays.
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
Toxicity of cypermethrin and diazinon to Haematobia irritans (Diptera: Muscidae) in its American southern range.
2001 Oct 31
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
Pollutants in house dust as indicators of indoor contamination.
2002
Acute toxicity and bioaccumulation of pesticide Diazinon in red tilapia (Oreochromis niloticus x Mossambicus albina).
2002
Subcritical water extraction to evaluate desorption behavior of organic pesticides in soil.
2002 Apr 10
Kynurenine formamidase: determination of primary structure and modeling-based prediction of tertiary structure and catalytic triad.
2002 Apr 29
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
Modeling of single-step and multistep adsorption isotherms of organic pesticides on soil.
2002 Dec 4
[The therapy is worse than the disease].
2002 Feb 15
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
Oxidation of diazinon by anodic Fenton treatment.
2002 Jul
Exposure apportionment: ranking food items by their contribution to dietary exposure.
2002 Jul
Diazinon and its degradation products in agricultural water courses in British Columbia, Canada.
2002 Jul
Effect of some organophosphorus pesticides on oxygen consumption of shrimp, Litopenaeus vannamei.
2002 Jun
Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells.
2002 Mar
Residential pesticide use during pregnancy among a cohort of urban minority women.
2002 May
Identification of alternatives for the management of foliar nematodes in floriculture.
2002 May
Validation of an SPME method, using PDMS, PA, PDMS-DVB, and CW-DVB SPME fiber coatings, for analysis of organophosphorus insecticides in natural waters.
2002 Nov
Ecological risk assessment of pesticide residues in coastal lagoons of Nicaragua.
2002 Oct
Sublethal responses of wolf spiders (Lycosidae) to organophosphorous insecticides.
2002 Oct
Persistence of methamidophos, diazinon, and malathion in tomatoes.
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
Susceptibility to diazinon in populations of the horn fly, Haematobia irritans (Diptera: Muscidae), in Central Brazil.
2002 Sep
Causes of ambient toxicity in the Calleguas Creek watershed of southern California.
2002 Sep
Convenient and rapid detection of pesticides in extracts of sheep wool.
2002 Sep
Cannabinoid CB1 receptor as a target for chlorpyrifos oxon and other organophosphorus pesticides.
2002 Sep 5
Determination of pesticide residues in nonfatty foods by supercritical fluid extraction and gas chromatography/mass spectrometry: collaborative study.
2002 Sep-Oct
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 Sat Jun 26 13:34:49 UTC 2021
Edited
by admin
on Sat Jun 26 13:34:49 UTC 2021
Record UNII
YUS1M1Q929
Record Status Validated (UNII)
Record Version
  • Download
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 [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
DIMPYLATE [WHO-DD]
Common Name 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 Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
EPA PESTICIDE CODE 57801
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
Code System Code Type Description
INN
2045
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
MESH
D003976
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
EPA CompTox
333-41-5
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
WIKIPEDIA
DIAZINON
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
PUBCHEM
3017
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
HSDB
303
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
CAS
333-41-5
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
EVMPD
SUB07189MIG
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-373-8
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
NCI_THESAURUS
C169912
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
FDA UNII
YUS1M1Q929
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL388560
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY
MERCK INDEX
M4268
Created by admin on Sat Jun 26 13:34:49 UTC 2021 , Edited by admin on Sat Jun 26 13:34:49 UTC 2021
PRIMARY Merck Index
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METABOLIC ENZYME -> SUBSTRATE
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ACTIVE MOIETY